# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c10
_database_code_depnum_ccdc_archive 'CCDC 2089012'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-11-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H17 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0443(8)
_cell_length_b                   10.1586(5)
_cell_length_c                   12.3923(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.530(9)
_cell_angle_gamma                90
_cell_volume                     1356.58(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8470
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      66.9280
_cell_measurement_theta_min      4.0150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -3 -1 0.1701
-3 -6 2 0.2002
4 -4 3 0.1677
6 1 2 0.1671
0 6 -3 0.1922
-4 4 -3 0.1368
-2 -3 -5 0.1339
3 3 5 0.1692
-8 -1 3 0.1779
7 -1 -5 0.2791
1 -3 -7 0.1681
0 1 -7 0.1366
-6 -3 6 0.2317
0 7 0 0.1970
-1 -6 0 0.1909
6 -2 1 0.1793
3 -6 1 0.1978
0 6 3 0.2069
-7 3 2 0.1764
-2 -5 -3 0.1603
0 -6 -3 0.1532
7 0 0 0.1890
2 5 3 0.1767
-6 3 6 0.2520
3 3 4 0.1489
8 2 -2 0.2346

_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.305
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.8662 -3.2263 -0.5098 0.1918 -0.0072 -0.9814
-2.5114 -6.1455 2.3668 0.8882 -0.0246 -0.4588
3.6441 -3.5776 3.3454 0.8253 -0.0208 0.5644
6.0211 1.3889 1.5665 0.1284 -0.0013 0.9917
0.0689 5.9225 -3.1870 -0.9979 0.0267 0.0593
-3.6790 3.5408 -3.3389 -0.8211 0.0206 -0.5703
-1.5488 -3.0952 -5.4877 0.0151 0.6295 -0.7769
2.5995 3.0076 4.7526 -0.0119 -0.5152 0.8570
-7.7357 -0.6391 2.7953 -0.0158 -0.5233 -0.8520
7.4509 -0.7360 -5.4469 0.0235 0.8384 0.5445
1.2506 -3.0420 -6.8622 0.0219 0.8629 -0.5049
-0.4113 1.3044 -6.8529 -0.6238 0.5909 -0.5116
-5.5336 -3.4680 5.9341 0.6435 -0.6126 -0.4590
0.2983 6.5853 -0.4249 -0.9045 -0.2668 0.3326
-1.3783 -6.4805 0.1815 0.8361 0.2462 -0.4902
5.9481 -1.9061 1.4395 0.5623 0.1681 0.8097
2.5029 -5.9285 0.9872 0.9523 0.2819 0.1166
-0.1603 5.8796 3.3436 -0.5878 -0.6172 0.5231
-6.7909 3.0277 1.8022 -0.5392 -0.5696 -0.6203
-2.4025 -5.1139 -2.8777 0.4216 0.4414 -0.7921
0.1256 -5.8743 -3.3402 0.5860 0.6153 -0.5272
7.0327 -0.0168 -0.0938 0.2496 0.2657 0.9312
2.4051 5.1127 2.8770 -0.4214 -0.4412 0.7923
-6.0166 2.9316 6.0673 -0.2289 -0.9532 -0.1974
3.4355 3.3957 3.7254 -0.0990 -0.4033 0.9097
7.5185 1.5048 -2.3662 -0.0818 0.4315 0.8984

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14375
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.982
_diffrn_reflns_theta_max         66.982
_diffrn_reflns_theta_min         4.102
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00 115.00   1.00    2.50    --   41.64  57.00  30.00  102
  2  ω     17.00 116.00   1.00    2.50    --   41.64  37.00 -60.00   99
  3  ω     76.00 166.00   1.00    5.00    --   92.50 125.00 120.00   90
  4  ω     19.00  87.00   1.00    5.00    --   92.50-125.00 150.00   68
  5  ω     19.00  87.00   1.00    5.00    --   92.50-125.00   0.00   68
  6  ω     16.00 125.00   1.00    5.00    --   92.50 -77.00 -30.00  109
  7  ω     80.00 169.00   1.00    5.00    --   92.50  77.00 -30.00   89
  8  ω     10.00  81.00   1.00    5.00    --   92.50 -94.00-180.00   71
  9  ω     19.00 118.00   1.00    5.00    --   92.50 -45.00 -30.00   99
 10  ω     19.00  87.00   1.00    5.00    --   92.50-125.00 -60.00   68
 11  ω     16.00 125.00   1.00    5.00    --   92.50 -77.00 -60.00  109
 12  ω     64.00 169.00   1.00    5.00    --   92.50  30.00  30.00  105
 13  ω     12.00 127.00   1.00    5.00    --   92.50 -84.00 111.04  115
 14  ω     19.00 118.00   1.00    5.00    --   92.50 -45.00-180.00   99
 15  ω     11.00 145.00   1.00    5.00    --   92.50 -15.00-150.00  134
 16  ω     63.00 165.00   1.00    5.00    --   92.50  61.00  60.00  102
 17  ω    -98.00 -49.00   1.00    2.50    --  -41.64 125.00 150.00   49
 18  ω     13.00 115.00   1.00    2.50    --   41.64  57.00-180.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0360128000
_diffrn_orient_matrix_UB_12      -0.1349128000
_diffrn_orient_matrix_UB_13      0.0631795000
_diffrn_orient_matrix_UB_21      0.0363643000
_diffrn_orient_matrix_UB_22      -0.0484553000
_diffrn_orient_matrix_UB_23      -0.0976367000
_diffrn_orient_matrix_UB_31      0.1335385000
_diffrn_orient_matrix_UB_32      0.0493693000
_diffrn_orient_matrix_UB_33      0.0760339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2285
_reflns_number_total             2410
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0063(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.3905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.14263(8) 0.59392(9) 1.00269(7) 0.0323(2) Uani 1 1 d . . . . .
H1 H 0.207850 0.564314 1.007061 0.048 Uiso 1 1 calc R U . . .
O2 O 0.30648(8) 0.54402(9) 0.93556(7) 0.0303(2) Uani 1 1 d . . . . .
N1 N 0.70890(9) 0.62012(10) 0.53244(9) 0.0266(3) Uani 1 1 d . . . . .
C1 C 0.08547(11) 0.66544(12) 0.90091(10) 0.0260(3) Uani 1 1 d . . . . .
C2 C -0.02772(12) 0.72370(13) 0.87719(12) 0.0331(3) Uani 1 1 d . . . . .
H2 H -0.062631 0.710169 0.929768 0.040 Uiso 1 1 calc R U . . .
C3 C -0.08829(12) 0.80101(13) 0.77677(12) 0.0326(3) Uani 1 1 d . . . . .
H3 H -0.163524 0.840083 0.762152 0.039 Uiso 1 1 calc R U . . .
C4 C -0.03769(11) 0.82115(12) 0.69685(11) 0.0295(3) Uani 1 1 d . . . . .
H4 H -0.078214 0.874603 0.629556 0.035 Uiso 1 1 calc R U . . .
C5 C 0.07255(11) 0.76157(12) 0.71791(10) 0.0254(3) Uani 1 1 d . . . . .
H5 H 0.105089 0.774373 0.663323 0.030 Uiso 1 1 calc R U . . .
C6 C 0.13740(10) 0.68206(11) 0.81932(10) 0.0226(3) Uani 1 1 d . . . . .
C7 C 0.25521(10) 0.61544(11) 0.84386(10) 0.0237(3) Uani 1 1 d . . . . .
C8 C 0.31175(11) 0.63352(12) 0.76295(10) 0.0251(3) Uani 1 1 d . . . . .
H8 H 0.275293 0.690794 0.697899 0.030 Uiso 1 1 calc R U . . .
C9 C 0.41617(11) 0.56864(11) 0.78065(10) 0.0247(3) Uani 1 1 d . . . . .
H9 H 0.445983 0.508042 0.843518 0.030 Uiso 1 1 calc R U . . .
C10 C 0.48679(10) 0.58247(11) 0.71333(10) 0.0230(3) Uani 1 1 d . . . . .
C11 C 0.45906(10) 0.67431(11) 0.62013(10) 0.0242(3) Uani 1 1 d . . . . .
H11 H 0.389132 0.727169 0.597310 0.029 Uiso 1 1 calc R U . . .
C12 C 0.53172(10) 0.68853(11) 0.56178(10) 0.0246(3) Uani 1 1 d . . . . .
H12 H 0.511003 0.751488 0.501367 0.030 Uiso 1 1 calc R U . . .
C13 C 0.63812(10) 0.60864(11) 0.59213(10) 0.0227(3) Uani 1 1 d . . . . .
C14 C 0.66738(11) 0.51726(11) 0.68668(11) 0.0256(3) Uani 1 1 d . . . . .
H14 H 0.737392 0.464389 0.710223 0.031 Uiso 1 1 calc R U . . .
C15 C 0.59339(11) 0.50570(11) 0.74421(10) 0.0253(3) Uani 1 1 d . . . . .
H15 H 0.614845 0.444511 0.806139 0.030 Uiso 1 1 calc R U . . .
C16 C 0.67667(11) 0.71504(12) 0.43594(11) 0.0300(3) Uani 1 1 d . . . . .
H16A H 0.595831 0.695064 0.372712 0.045 Uiso 1 1 calc R U . . .
H16B H 0.736586 0.711180 0.404702 0.045 Uiso 1 1 calc R U . . .
H16C H 0.676228 0.801830 0.466399 0.045 Uiso 1 1 calc R U . . .
C17 C 0.81229(11) 0.53178(12) 0.55838(12) 0.0311(3) Uani 1 1 d . . . . .
H17A H 0.873459 0.543745 0.640390 0.047 Uiso 1 1 calc R U . . .
H17B H 0.848537 0.550667 0.505066 0.047 Uiso 1 1 calc R U . . .
H17C H 0.783322 0.442420 0.546849 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.3480(14) . ?
O2 C7 1.2538(14) . ?
N1 C13 1.3604(15) . ?
N1 C16 1.4478(15) . ?
N1 C17 1.4497(15) . ?
C1 C2 1.3919(18) . ?
C1 C6 1.4166(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.3736(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3904(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.3740(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.4018(17) . ?
C6 C7 1.4760(16) . ?
C7 C8 1.4535(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.3483(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.4399(16) . ?
C10 C11 1.4041(16) . ?
C10 C15 1.4015(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3692(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.4184(16) . ?
C13 C14 1.4106(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.3725(17) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C13 N1 C16 120.29(10) . . ?
C13 N1 C17 120.74(10) . . ?
C16 N1 C17 118.83(10) . . ?
O1 C1 C2 118.00(10) . . ?
O1 C1 C6 121.89(11) . . ?
C2 C1 C6 120.11(11) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.54(11) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.34(12) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.58(11) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.89(11) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 119.25(10) . . ?
C5 C6 C1 117.50(11) . . ?
C5 C6 C7 123.25(10) . . ?
O2 C7 C6 119.41(10) . . ?
O2 C7 C8 120.36(11) . . ?
C8 C7 C6 120.23(10) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.09(11) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 116.3 . . ?
C8 C9 C10 127.41(11) . . ?
C10 C9 H9 116.3 . . ?
C11 C10 C9 123.81(10) . . ?
C15 C10 C9 119.58(10) . . ?
C15 C10 C11 116.53(10) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.09(10) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.96(10) . . ?
C13 C12 H12 119.5 . . ?
N1 C13 C12 121.21(10) . . ?
N1 C13 C14 121.55(10) . . ?
C14 C13 C12 117.24(10) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.56(11) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 118.7 . . ?
C14 C15 C10 122.59(11) . . ?
C14 C15 H15 118.7 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.78 2.5120(11) 147.2 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 177.98(11) . . . . ?
O1 C1 C6 C5 -178.09(10) . . . . ?
O1 C1 C6 C7 2.25(17) . . . . ?
O2 C7 C8 C9 3.74(17) . . . . ?
N1 C13 C14 C15 -178.82(11) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C1 C6 C7 O2 0.90(16) . . . . ?
C1 C6 C7 C8 -178.55(10) . . . . ?
C2 C1 C6 C5 1.90(17) . . . . ?
C2 C1 C6 C7 -177.76(11) . . . . ?
C2 C3 C4 C5 0.98(19) . . . . ?
C3 C4 C5 C6 -1.05(18) . . . . ?
C4 C5 C6 C1 -0.38(17) . . . . ?
C4 C5 C6 C7 179.26(11) . . . . ?
C5 C6 C7 O2 -178.75(10) . . . . ?
C5 C6 C7 C8 1.81(17) . . . . ?
C6 C1 C2 C3 -2.02(19) . . . . ?
C6 C7 C8 C9 -176.82(10) . . . . ?
C7 C8 C9 C10 -175.76(10) . . . . ?
C8 C9 C10 C11 3.66(19) . . . . ?
C8 C9 C10 C15 -179.59(11) . . . . ?
C9 C10 C11 C12 177.01(11) . . . . ?
C9 C10 C15 C14 -177.62(10) . . . . ?
C10 C11 C12 C13 1.04(17) . . . . ?
C11 C10 C15 C14 -0.63(17) . . . . ?
C11 C12 C13 N1 178.37(10) . . . . ?
C11 C12 C13 C14 -1.74(16) . . . . ?
C12 C13 C14 C15 1.28(16) . . . . ?
C13 C14 C15 C10 -0.12(18) . . . . ?
C15 C10 C11 C12 0.16(16) . . . . ?
C16 N1 C13 C12 0.02(16) . . . . ?
C16 N1 C13 C14 -179.87(11) . . . . ?
C17 N1 C13 C12 -175.63(10) . . . . ?
C17 N1 C13 C14 4.48(16) . . . . ?


_olex2_date_sample_data_collection 2020-11-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C10
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.832
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_at527
_database_code_depnum_ccdc_archive 'CCDC 2089023'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N O2'
_chemical_formula_sum            'C23 H23 N O2'
_chemical_formula_weight         345.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H23 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2451(5)
_cell_length_b                   9.5049(6)
_cell_length_c                   23.4203(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.132(5)
_cell_angle_gamma                90
_cell_volume                     1828.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7152
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.7950
_cell_measurement_theta_min      3.6610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 12 0.0482
0 -4 -12 0.0482
4 -2 6 0.1099
-1 -5 9 0.1149
1 5 -9 0.1477
-5 1 -4 0.1491
5 2 -3 0.1840
-5 -2 3 0.1840

_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.096
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1509 3.8196 11.8354 0.6773 0.7137 -0.1787
-0.1509 -3.8196 -11.8354 -0.6773 -0.7137 0.1787
4.4732 -2.0423 5.5161 0.3198 -0.3011 -0.8984
-0.8300 -4.7960 9.4392 0.7242 -0.6880 0.0481
0.8217 4.7963 -9.4423 -0.7242 0.6880 -0.0465
-4.9611 1.1016 -3.7654 -0.1785 0.1667 0.9697
4.9325 2.2822 -3.0847 -0.3339 0.3197 -0.8867
-4.9325 -2.2822 3.0847 0.3339 -0.3197 0.8867

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19766
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.886
_diffrn_reflns_theta_max         66.886
_diffrn_reflns_theta_min         3.790
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  18.00   1.00    2.00    --  -41.64  77.00 -30.00   92
  2  ω    -31.00  70.00   1.00    2.00    --   41.64 -57.00  90.00  101
  3  ω    -33.00  66.00   1.00    2.00    --   41.64 -37.00 -30.00   99
  4  ω      9.00 129.00   1.00    5.51    --   92.50 -88.00  54.63  120
  5  ω     19.00  87.00   1.00    5.51    --   92.50-125.00  60.00   68
  6  ω     64.00 169.00   1.00    5.51    --   92.50  30.00  60.00  105
  7  ω     76.00 166.00   1.00    5.51    --   92.50 125.00-120.00   90
  8  ω     11.00 128.00   1.00    5.51    --   92.50 -86.00  99.52  117
  9  ω      9.00 129.00   1.00    5.51    --   92.50 -88.00 -28.98  120
 10  ω     80.00 169.00   1.00    5.51    --   92.50  77.00-180.00   89
 11  ω     80.00 169.00   1.00    5.51    --   92.50  77.00   0.00   89
 12  ω     10.00  81.00   1.00    5.51    --   92.50 -94.00 -90.00   71
 13  ω     19.00  87.00   1.00    5.51    --   92.50-125.00-180.00   68
 14  ω     19.00  87.00   1.00    5.51    --   92.50-125.00   0.00   68
 15  ω     10.00  81.00   1.00    5.51    --   92.50 -94.00-180.00   71
 16  ω     16.00 121.00   1.00    5.51    --   92.50 -30.00-120.00  105
 17  ω   -115.00 -13.00   1.00    2.00    --  -41.64 -57.00 120.00  102
 18  ω     12.00  90.00   1.00    2.00    --   41.64  65.00-129.38   78
 19  ω     13.00 115.00   1.00    2.00    --   41.64  57.00 -30.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0175846000
_diffrn_orient_matrix_UB_12      -0.0213287000
_diffrn_orient_matrix_UB_13      0.0643351000
_diffrn_orient_matrix_UB_21      -0.0043007000
_diffrn_orient_matrix_UB_22      0.1608225000
_diffrn_orient_matrix_UB_23      0.0084526000
_diffrn_orient_matrix_UB_31      -0.1866015000
_diffrn_orient_matrix_UB_32      -0.0016978000
_diffrn_orient_matrix_UB_33      -0.0121729000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2668
_reflns_number_total             3230
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²+0.3946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1320
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.92920(13) -0.09224(11) 0.36699(5) 0.0410(3) Uani 1 1 d . . . . .
H1 H 0.856200 -0.099606 0.388394 0.062 Uiso 1 1 calc R U . . .
O2 O 0.66579(13) -0.04020(12) 0.40667(5) 0.0455(3) Uani 1 1 d . . . . .
N1 N -0.24130(15) 0.33626(14) 0.44174(6) 0.0408(3) Uani 1 1 d . . . . .
C1 C 0.73843(18) 0.07512(15) 0.32373(6) 0.0341(3) Uani 1 1 d . . . . .
C2 C 1.2586(2) -0.01864(19) 0.24747(7) 0.0451(4) Uani 1 1 d . . . . .
H2 H 1.357316 -0.066478 0.249445 0.054 Uiso 1 1 calc R U . . .
C3 C -0.00898(19) 0.19196(17) 0.47451(6) 0.0408(4) Uani 1 1 d . . . . .
H3 H -0.060135 0.164615 0.506548 0.049 Uiso 1 1 calc R U . . .
C4 C 0.88643(18) 0.00264(15) 0.32616(6) 0.0339(3) Uani 1 1 d . . . . .
C5 C -0.3145(2) 0.44827(18) 0.40531(8) 0.0478(4) Uani 1 1 d . . . . .
H5A H -0.431717 0.445534 0.406603 0.057 Uiso 1 1 calc R U . . .
H5B H -0.291609 0.430671 0.366029 0.057 Uiso 1 1 calc R U . . .
C6 C 0.99966(18) 0.02626(15) 0.28443(6) 0.0345(3) Uani 1 1 d . . . . .
C7 C 0.7037(2) 0.17293(18) 0.27826(7) 0.0441(4) Uani 1 1 d . . . . .
H7 H 0.605269 0.221273 0.275778 0.053 Uiso 1 1 calc R U . . .
C8 C 0.62749(18) 0.04941(15) 0.36830(6) 0.0352(3) Uani 1 1 d . . . . .
C9 C -0.3288(2) 0.2919(2) 0.49001(7) 0.0490(4) Uani 1 1 d . . . . .
H9A H -0.313488 0.191433 0.495359 0.059 Uiso 1 1 calc R U . . .
H9B H -0.444108 0.308296 0.480448 0.059 Uiso 1 1 calc R U . . .
C10 C 0.22414(18) 0.17296(15) 0.41885(6) 0.0341(3) Uani 1 1 d . . . . .
C11 C -0.2776(3) 0.3652(3) 0.54617(9) 0.0795(8) Uani 1 1 d . . . . .
H11A H -0.294102 0.464696 0.541737 0.119 Uiso 1 1 calc R U . . .
H11B H -0.164588 0.346698 0.556992 0.119 Uiso 1 1 calc R U . . .
H11C H -0.341823 0.330547 0.575398 0.119 Uiso 1 1 calc R U . . .
C12 C -0.08746(18) 0.28820(16) 0.43562(6) 0.0354(3) Uani 1 1 d . . . . .
C13 C 0.9614(2) 0.12538(17) 0.24064(7) 0.0405(4) Uani 1 1 d . . . . .
C14 C 0.37771(18) 0.10686(16) 0.41120(6) 0.0357(3) Uani 1 1 d . . . . .
H14 H 0.414399 0.042295 0.439274 0.043 Uiso 1 1 calc R U . . .
C15 C 1.0769(2) 0.15059(19) 0.20070(7) 0.0476(4) Uani 1 1 d . . . . .
H15 H 1.053877 0.216257 0.171666 0.057 Uiso 1 1 calc R U . . .
C16 C 0.14077(19) 0.13769(17) 0.46630(6) 0.0400(4) Uani 1 1 d . . . . .
H16 H 0.188921 0.075074 0.493240 0.048 Uiso 1 1 calc R U . . .
C17 C 0.8099(2) 0.19765(19) 0.23853(7) 0.0492(4) Uani 1 1 d . . . . .
H17 H 0.783392 0.262651 0.209506 0.059 Uiso 1 1 calc R U . . .
C18 C 0.00004(18) 0.32873(17) 0.38894(7) 0.0390(4) Uani 1 1 d . . . . .
H18 H -0.044641 0.395436 0.363066 0.047 Uiso 1 1 calc R U . . .
C19 C 1.2214(2) 0.08021(19) 0.20407(7) 0.0469(4) Uani 1 1 d . . . . .
H19 H 1.295773 0.098057 0.177351 0.056 Uiso 1 1 calc R U . . .
C20 C 0.47508(18) 0.12613(16) 0.36882(6) 0.0354(3) Uani 1 1 d . . . . .
H20 H 0.444614 0.189290 0.339473 0.042 Uiso 1 1 calc R U . . .
C21 C -0.2537(3) 0.5939(2) 0.42258(11) 0.0708(6) Uani 1 1 d . . . . .
H21A H -0.308337 0.662641 0.397717 0.106 Uiso 1 1 calc R U . . .
H21B H -0.138505 0.599177 0.419526 0.106 Uiso 1 1 calc R U . . .
H21C H -0.275673 0.612318 0.461453 0.106 Uiso 1 1 calc R U . . .
C22 C 1.15012(19) -0.04519(17) 0.28701(7) 0.0408(4) Uani 1 1 d . . . . .
H22 H 1.175726 -0.110874 0.315844 0.049 Uiso 1 1 calc R U . . .
C23 C 0.14864(18) 0.27200(16) 0.38106(6) 0.0373(4) Uani 1 1 d . . . . .
H23 H 0.201440 0.300173 0.349509 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C4 1.3386(18) . ?
O2 C8 1.2577(18) . ?
N1 C5 1.461(2) . ?
N1 C9 1.457(2) . ?
N1 C12 1.368(2) . ?
C1 C4 1.398(2) . ?
C1 C7 1.423(2) . ?
C1 C8 1.469(2) . ?
C2 H2 0.9300 . ?
C2 C19 1.398(3) . ?
C2 C22 1.367(2) . ?
C3 H3 0.9300 . ?
C3 C12 1.407(2) . ?
C3 C16 1.368(2) . ?
C4 C6 1.429(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C21 1.515(3) . ?
C6 C13 1.408(2) . ?
C6 C22 1.411(2) . ?
C7 H7 0.9300 . ?
C7 C17 1.354(2) . ?
C8 C20 1.454(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C11 1.514(3) . ?
C10 C14 1.439(2) . ?
C10 C16 1.399(2) . ?
C10 C23 1.399(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C18 1.416(2) . ?
C13 C15 1.414(2) . ?
C13 C17 1.423(2) . ?
C14 H14 0.9300 . ?
C14 C20 1.344(2) . ?
C15 H15 0.9300 . ?
C15 C19 1.363(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C23 1.366(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 109.5 . . ?
C9 N1 C5 117.19(13) . . ?
C12 N1 C5 121.39(13) . . ?
C12 N1 C9 120.85(14) . . ?
C4 C1 C7 117.95(13) . . ?
C4 C1 C8 119.08(13) . . ?
C7 C1 C8 122.97(13) . . ?
C19 C2 H2 119.9 . . ?
C22 C2 H2 119.9 . . ?
C22 C2 C19 120.16(15) . . ?
C12 C3 H3 119.2 . . ?
C16 C3 H3 119.2 . . ?
C16 C3 C12 121.53(14) . . ?
O1 C4 C1 122.29(13) . . ?
O1 C4 C6 116.63(13) . . ?
C1 C4 C6 121.08(14) . . ?
N1 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
N1 C5 C21 113.61(16) . . ?
H5A C5 H5B 107.7 . . ?
C21 C5 H5A 108.8 . . ?
C21 C5 H5B 108.8 . . ?
C13 C6 C4 119.08(13) . . ?
C13 C6 C22 119.51(14) . . ?
C22 C6 C4 121.40(14) . . ?
C1 C7 H7 119.0 . . ?
C17 C7 C1 121.91(15) . . ?
C17 C7 H7 119.0 . . ?
O2 C8 C1 119.20(13) . . ?
O2 C8 C20 119.72(13) . . ?
C20 C8 C1 121.08(13) . . ?
N1 C9 H9A 108.5 . . ?
N1 C9 H9B 108.5 . . ?
N1 C9 C11 115.00(16) . . ?
H9A C9 H9B 107.5 . . ?
C11 C9 H9A 108.5 . . ?
C11 C9 H9B 108.5 . . ?
C16 C10 C14 119.65(14) . . ?
C16 C10 C23 116.18(14) . . ?
C23 C10 C14 124.16(13) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C3 121.77(14) . . ?
N1 C12 C18 122.09(14) . . ?
C3 C12 C18 116.11(14) . . ?
C6 C13 C15 118.36(14) . . ?
C6 C13 C17 119.17(14) . . ?
C15 C13 C17 122.46(15) . . ?
C10 C14 H14 115.7 . . ?
C20 C14 C10 128.53(14) . . ?
C20 C14 H14 115.7 . . ?
C13 C15 H15 119.5 . . ?
C19 C15 C13 121.05(16) . . ?
C19 C15 H15 119.5 . . ?
C3 C16 C10 122.37(15) . . ?
C3 C16 H16 118.8 . . ?
C10 C16 H16 118.8 . . ?
C7 C17 C13 120.80(15) . . ?
C7 C17 H17 119.6 . . ?
C13 C17 H17 119.6 . . ?
C12 C18 H18 119.3 . . ?
C23 C18 C12 121.45(14) . . ?
C23 C18 H18 119.3 . . ?
C2 C19 H19 119.8 . . ?
C15 C19 C2 120.38(15) . . ?
C15 C19 H19 119.8 . . ?
C8 C20 H20 119.6 . . ?
C14 C20 C8 120.78(14) . . ?
C14 C20 H20 119.6 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C22 C6 120.53(16) . . ?
C2 C22 H22 119.7 . . ?
C6 C22 H22 119.7 . . ?
C10 C23 H23 118.9 . . ?
C18 C23 C10 122.26(14) . . ?
C18 C23 H23 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C6 C13 -179.71(13) . . . . ?
O1 C4 C6 C22 -1.2(2) . . . . ?
O2 C8 C20 C14 2.9(2) . . . . ?
N1 C12 C18 C23 -175.12(14) . . . . ?
C1 C4 C6 C13 0.7(2) . . . . ?
C1 C4 C6 C22 179.20(13) . . . . ?
C1 C7 C17 C13 0.3(3) . . . . ?
C1 C8 C20 C14 -176.89(13) . . . . ?
C3 C12 C18 C23 3.0(2) . . . . ?
C4 C1 C7 C17 -0.7(2) . . . . ?
C4 C1 C8 O2 -2.1(2) . . . . ?
C4 C1 C8 C20 177.66(13) . . . . ?
C4 C6 C13 C15 178.12(14) . . . . ?
C4 C6 C13 C17 -1.0(2) . . . . ?
C4 C6 C22 C2 -178.41(14) . . . . ?
C5 N1 C9 C11 -93.4(2) . . . . ?
C5 N1 C12 C3 172.68(14) . . . . ?
C5 N1 C12 C18 -9.4(2) . . . . ?
C6 C13 C15 C19 0.5(3) . . . . ?
C6 C13 C17 C7 0.6(3) . . . . ?
C7 C1 C4 O1 -179.41(13) . . . . ?
C7 C1 C4 C6 0.2(2) . . . . ?
C7 C1 C8 O2 179.02(14) . . . . ?
C7 C1 C8 C20 -1.2(2) . . . . ?
C8 C1 C4 O1 1.7(2) . . . . ?
C8 C1 C4 C6 -178.73(12) . . . . ?
C8 C1 C7 C17 178.18(16) . . . . ?
C9 N1 C5 C21 93.46(18) . . . . ?
C9 N1 C12 C3 1.6(2) . . . . ?
C9 N1 C12 C18 179.56(14) . . . . ?
C10 C14 C20 C8 179.86(14) . . . . ?
C12 N1 C5 C21 -77.9(2) . . . . ?
C12 N1 C9 C11 78.1(2) . . . . ?
C12 C3 C16 C10 -0.6(2) . . . . ?
C12 C18 C23 C10 -1.1(2) . . . . ?
C13 C6 C22 C2 0.1(2) . . . . ?
C13 C15 C19 C2 -0.2(3) . . . . ?
C14 C10 C16 C3 -176.91(14) . . . . ?
C14 C10 C23 C18 177.75(14) . . . . ?
C15 C13 C17 C7 -178.55(17) . . . . ?
C16 C3 C12 N1 175.97(14) . . . . ?
C16 C3 C12 C18 -2.1(2) . . . . ?
C16 C10 C14 C20 179.82(15) . . . . ?
C16 C10 C23 C18 -1.7(2) . . . . ?
C17 C13 C15 C19 179.61(16) . . . . ?
C19 C2 C22 C6 0.2(2) . . . . ?
C22 C2 C19 C15 -0.2(3) . . . . ?
C22 C6 C13 C15 -0.4(2) . . . . ?
C22 C6 C13 C17 -179.61(15) . . . . ?
C23 C10 C14 C20 0.4(3) . . . . ?
C23 C10 C16 C3 2.5(2) . . . . ?


_olex2_date_sample_data_collection 2021-02-03
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id AT527
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.421
_oxdiff_exptl_absorpt_empirical_full_min 0.692
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_at528
_database_code_depnum_ccdc_archive 'CCDC 2089024'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N O2'
_chemical_formula_sum            'C22 H19 N O2'
_chemical_formula_weight         329.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H19 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.0991(17)
_cell_length_b                   15.5571(19)
_cell_length_c                   15.216(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.917(11)
_cell_angle_gamma                90
_cell_volume                     3305.7(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4018
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.9930
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.1006
-1 -1 0 0.0788
1 1 2 0.1272
-2 -3 -9 0.1323
-6 7 1 0.0911
-2 6 -7 0.1324
6 -8 0 0.0918
2 -6 7 0.1173
9 -2 1 0.1018
-9 2 -1 0.1049
-3 3 -8 0.1247
4 9 -3 0.1151
4 9 2 0.1016
-3 -9 -4 0.0919
-1 -6 -8 0.1300

_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.179
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0028 1.0016 -0.0055 0.0440 0.1380 -0.0320
-1.0028 -1.0016 0.0055 -0.0440 -0.1380 0.0320
1.0026 1.0002 1.9878 0.0844 0.1916 0.1607
-2.3598 -3.3250 -8.5213 -0.2273 -0.6362 -0.7373
-6.1794 7.4286 1.3543 -0.9315 0.3300 0.1528
-1.7707 6.1154 -7.2945 -0.6240 0.2230 -0.7490
5.9406 -7.6557 -0.3110 0.9416 -0.3338 -0.0446
1.7761 -6.1196 7.2890 0.6246 -0.2232 0.7484
8.7141 -2.3934 0.6175 0.9563 0.2830 -0.0733
-8.5581 2.4863 -1.2411 -0.9589 -0.2836 0.0089
-3.3065 2.6257 -8.2661 -0.6123 -0.1794 -0.7700
4.4316 8.6088 -2.6678 -0.0707 0.8905 -0.4495
3.5546 8.9590 1.9340 -0.0780 0.9969 0.0072
-2.9950 -8.5611 -3.6378 0.0762 -0.9793 -0.1873
-0.8575 -5.8465 -7.7764 0.0571 -0.7477 -0.6616

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9835
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.942
_diffrn_reflns_theta_max         66.942
_diffrn_reflns_theta_min         4.254
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -51.00   1.00    4.00    --  -41.64 125.00-120.00   27
  2  ω    -67.00 -10.00   1.00    4.00    --  -41.64  77.00 -30.00   57
  3  ω     17.00  60.00   1.00    4.00    --   41.64  37.00 -90.00   43
  4  ω     72.00 114.00   1.00    4.00    --   41.64  37.00 -90.00   42
  5  ω     17.00  83.00   1.00    4.00    --   41.64  37.00  30.00   66
  6  ω     82.00 107.00   1.00   15.00    --   92.50 125.00 -30.00   25
  7  ω     20.00  47.00   1.00   15.00    --   92.50-125.00 120.00   27
  8  ω    104.00 139.00   1.00   15.00    --   92.50  30.00 -90.00   35
  9  ω     83.00 146.00   1.00   15.00    --   92.50  61.00 -90.00   63
 10  ω     10.00  44.00   1.00   15.00    --   92.50 -94.00  60.00   34
 11  ω     89.00 116.00   1.00   15.00    --   92.50  61.00 120.00   27
 12  ω     48.00  75.00   1.00   15.00    --   92.50-125.00 120.00   27
 13  ω     42.00  80.00   1.00   15.00    --   92.50 -94.00-120.00   38
 14  ω    121.00 159.00   1.00   15.00    --   92.50 125.00 -30.00   38
 15  ω     76.00 109.00   1.00   15.00    --   92.50 -87.00  55.02   33
 16  ω     54.00  81.00   1.00   15.00    --   92.50-125.00   0.00   27
 17  ω     27.00  54.00   1.00   15.00    --   92.50-125.00 150.00   27
 18  ω     41.00  68.00   1.00   15.00    --   92.50 -94.00   0.00   27
 19  ω     24.00  80.00   1.00   15.00    --   92.50-125.00-180.00   56
 20  ω     48.00  81.00   1.00   15.00    --   92.50 -94.00  60.00   33
 21  ω     63.00 142.00   1.00   15.00    --   92.50  61.00-180.00   79
 22  ω     20.00  72.00   1.00   15.00    --   92.50-125.00  60.00   52
 23  ω     87.00 116.00   1.00   15.00    --   92.50 -88.00 108.87   29
 24  ω     16.00  72.00   1.00   15.00    --   92.50 -88.00 108.87   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0944271000
_diffrn_orient_matrix_UB_12      -0.0505422000
_diffrn_orient_matrix_UB_13      0.0202435000
_diffrn_orient_matrix_UB_21      0.0536789000
_diffrn_orient_matrix_UB_22      0.0841591000
_diffrn_orient_matrix_UB_23      0.0269578000
_diffrn_orient_matrix_UB_31      -0.0187281000
_diffrn_orient_matrix_UB_32      -0.0126297000
_diffrn_orient_matrix_UB_33      0.0966355000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2543
_reflns_number_total             2921
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00059(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0991P)²+0.9654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1532
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C19(H19), C21(H21), C22(H22)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26619(8) 0.68095(7) 0.59635(7) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.14924(7) 0.64076(7) 0.69505(7) 0.0350(3) Uani 1 1 d . . . . .
H2 H 0.171738 0.666650 0.655764 0.052 Uiso 1 1 calc R U . . .
N1 N 0.78477(10) 0.67894(9) 0.38775(9) 0.0397(4) Uani 1 1 d . . . . .
C1 C 0.29619(10) 0.56380(10) 0.69474(9) 0.0298(4) Uani 1 1 d . . . . .
C2 C 0.07032(11) 0.49257(11) 0.89856(10) 0.0375(4) Uani 1 1 d . . . . .
H2A H 0.014061 0.504054 0.921899 0.045 Uiso 1 1 calc R U . . .
C3 C 0.60334(11) 0.60811(11) 0.51925(10) 0.0345(4) Uani 1 1 d . . . . .
H3 H 0.596225 0.567462 0.562680 0.041 Uiso 1 1 calc R U . . .
C4 C 0.18193(10) 0.52670(10) 0.79703(9) 0.0299(4) Uani 1 1 d . . . . .
C5 C 0.62337(11) 0.72666(10) 0.38691(10) 0.0346(4) Uani 1 1 d . . . . .
H5 H 0.629112 0.765248 0.341265 0.042 Uiso 1 1 calc R U . . .
C6 C 0.24135(11) 0.45757(10) 0.83071(9) 0.0319(4) Uani 1 1 d . . . . .
C7 C 0.68801(11) 0.61218(10) 0.48549(10) 0.0350(4) Uani 1 1 d . . . . .
H7 H 0.737579 0.574823 0.506200 0.042 Uiso 1 1 calc R U . . .
C8 C 0.20942(10) 0.57843(10) 0.72719(9) 0.0298(4) Uani 1 1 d . . . . .
C9 C 0.21144(12) 0.40559(11) 0.89809(10) 0.0373(4) Uani 1 1 d . . . . .
H9 H 0.248858 0.359159 0.920250 0.045 Uiso 1 1 calc R U . . .
C10 C 0.70055(11) 0.67316(10) 0.41900(10) 0.0318(4) Uani 1 1 d . . . . .
C11 C 0.53942(11) 0.72208(10) 0.42285(10) 0.0347(4) Uani 1 1 d . . . . .
H11 H 0.489491 0.758951 0.401822 0.042 Uiso 1 1 calc R U . . .
C12 C 0.09628(11) 0.54360(11) 0.83290(9) 0.0330(4) Uani 1 1 d . . . . .
H12 H 0.057627 0.589589 0.811654 0.040 Uiso 1 1 calc R U . . .
C13 C 0.41384(11) 0.61206(11) 0.59291(10) 0.0342(4) Uani 1 1 d . . . . .
H13 H 0.455958 0.569263 0.616377 0.041 Uiso 1 1 calc R U . . .
C14 C 0.35407(10) 0.49376(10) 0.73072(10) 0.0334(4) Uani 1 1 d . . . . .
H14 H 0.411483 0.482895 0.709150 0.040 Uiso 1 1 calc R U . . .
C15 C 0.86948(11) 0.62480(11) 0.40152(10) 0.0344(4) Uani 1 1 d . . . . .
H15A H 0.856900 0.564624 0.387858 0.041 Uiso 1 1 calc R U . . .
H15B H 0.907320 0.631591 0.459356 0.041 Uiso 1 1 calc R U . . .
C16 C 0.32308(11) 0.62184(10) 0.62579(9) 0.0317(4) Uani 1 1 d . . . . .
C17 C 0.90835(11) 0.67528(11) 0.32680(10) 0.0370(4) Uani 1 1 d . . . . .
H17A H 0.965168 0.708907 0.346790 0.044 Uiso 1 1 calc R U . . .
H17B H 0.917228 0.640486 0.275665 0.044 Uiso 1 1 calc R U . . .
C18 C 0.52658(11) 0.66344(10) 0.49041(9) 0.0319(4) Uani 1 1 d . . . . .
C19 C 0.43857(11) 0.66405(10) 0.52863(10) 0.0339(4) Uani 1 1 d . . . . .
H19 H 0.393505 0.705026 0.506452 0.041 Uiso 1 1 calc R U . . .
C20 C 0.81498(11) 0.72802(11) 0.31485(10) 0.0348(4) Uani 1 1 d . . . . .
H20A H 0.824237 0.788807 0.327397 0.042 Uiso 1 1 calc R U . . .
H20B H 0.775322 0.718996 0.258275 0.042 Uiso 1 1 calc R U . . .
C21 C 0.12776(12) 0.42311(11) 0.93099(10) 0.0399(4) Uani 1 1 d . . . . .
H21 H 0.108992 0.388453 0.975323 0.048 Uiso 1 1 calc R U . . .
C22 C 0.32815(11) 0.44242(11) 0.79541(10) 0.0350(4) Uani 1 1 d . . . . .
H22 H 0.367476 0.396935 0.816869 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.2612(19) . ?
O2 H2 0.8200 . ?
O2 C8 1.3361(19) . ?
N1 C10 1.342(2) . ?
N1 C15 1.453(2) . ?
N1 C20 1.4578(19) . ?
C1 C8 1.400(2) . ?
C1 C14 1.425(2) . ?
C1 C16 1.473(2) . ?
C2 H2A 0.9300 . ?
C2 C12 1.365(2) . ?
C2 C21 1.399(3) . ?
C3 H3 0.9300 . ?
C3 C7 1.365(2) . ?
C3 C18 1.405(2) . ?
C4 C6 1.415(2) . ?
C4 C8 1.429(2) . ?
C4 C12 1.417(2) . ?
C5 H5 0.9300 . ?
C5 C10 1.403(2) . ?
C5 C11 1.372(2) . ?
C6 C9 1.415(2) . ?
C6 C22 1.422(2) . ?
C7 H7 0.9300 . ?
C7 C10 1.416(2) . ?
C9 H9 0.9300 . ?
C9 C21 1.371(2) . ?
C11 H11 0.9300 . ?
C11 C18 1.405(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C16 1.445(2) . ?
C13 C19 1.352(2) . ?
C14 H14 0.9300 . ?
C14 C22 1.356(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C17 1.543(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C20 1.540(2) . ?
C18 C19 1.441(2) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 109.5 . . ?
C10 N1 C15 131.32(13) . . ?
C10 N1 C20 132.10(13) . . ?
C15 N1 C20 95.33(11) . . ?
C8 C1 C14 118.10(13) . . ?
C8 C1 C16 118.35(14) . . ?
C14 C1 C16 123.55(13) . . ?
C12 C2 H2A 119.8 . . ?
C12 C2 C21 120.46(14) . . ?
C21 C2 H2A 119.8 . . ?
C7 C3 H3 119.0 . . ?
C7 C3 C18 122.01(14) . . ?
C18 C3 H3 119.0 . . ?
C6 C4 C8 119.32(13) . . ?
C6 C4 C12 119.66(14) . . ?
C12 C4 C8 121.01(14) . . ?
C10 C5 H5 120.0 . . ?
C11 C5 H5 120.0 . . ?
C11 C5 C10 120.05(14) . . ?
C4 C6 C22 119.10(14) . . ?
C9 C6 C4 118.43(14) . . ?
C9 C6 C22 122.47(15) . . ?
C3 C7 H7 119.9 . . ?
C3 C7 C10 120.14(14) . . ?
C10 C7 H7 119.9 . . ?
O2 C8 C1 122.06(13) . . ?
O2 C8 C4 117.22(13) . . ?
C1 C8 C4 120.72(14) . . ?
C6 C9 H9 119.7 . . ?
C21 C9 C6 120.56(16) . . ?
C21 C9 H9 119.7 . . ?
N1 C10 C5 121.25(14) . . ?
N1 C10 C7 120.13(14) . . ?
C5 C10 C7 118.62(14) . . ?
C5 C11 H11 119.0 . . ?
C5 C11 C18 122.04(14) . . ?
C18 C11 H11 119.0 . . ?
C2 C12 C4 120.19(15) . . ?
C2 C12 H12 119.9 . . ?
C4 C12 H12 119.9 . . ?
C16 C13 H13 119.4 . . ?
C19 C13 H13 119.4 . . ?
C19 C13 C16 121.11(15) . . ?
C1 C14 H14 118.9 . . ?
C22 C14 C1 122.15(14) . . ?
C22 C14 H14 118.9 . . ?
N1 C15 H15A 114.0 . . ?
N1 C15 H15B 114.0 . . ?
N1 C15 C17 88.11(11) . . ?
H15A C15 H15B 111.2 . . ?
C17 C15 H15A 114.0 . . ?
C17 C15 H15B 114.0 . . ?
O1 C16 C1 119.12(13) . . ?
O1 C16 C13 120.27(14) . . ?
C13 C16 C1 120.61(14) . . ?
C15 C17 H17A 113.9 . . ?
C15 C17 H17B 113.9 . . ?
H17A C17 H17B 111.1 . . ?
C20 C17 C15 88.49(11) . . ?
C20 C17 H17A 113.9 . . ?
C20 C17 H17B 113.9 . . ?
C3 C18 C19 123.16(14) . . ?
C11 C18 C3 117.07(13) . . ?
C11 C18 C19 119.74(14) . . ?
C13 C19 C18 127.62(15) . . ?
C13 C19 H19 116.2 . . ?
C18 C19 H19 116.2 . . ?
N1 C20 C17 88.03(11) . . ?
N1 C20 H20A 114.0 . . ?
N1 C20 H20B 114.0 . . ?
C17 C20 H20A 114.0 . . ?
C17 C20 H20B 114.0 . . ?
H20A C20 H20B 111.2 . . ?
C2 C21 H21 119.7 . . ?
C9 C21 C2 120.68(14) . . ?
C9 C21 H21 119.7 . . ?
C6 C22 H22 119.7 . . ?
C14 C22 C6 120.56(15) . . ?
C14 C22 H22 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C15 C17 C20 -1.48(12) . . . . ?
C1 C14 C22 C6 -0.6(2) . . . . ?
C3 C7 C10 N1 177.95(15) . . . . ?
C3 C7 C10 C5 -2.2(2) . . . . ?
C3 C18 C19 C13 -2.8(3) . . . . ?
C4 C6 C9 C21 -1.3(2) . . . . ?
C4 C6 C22 C14 0.4(2) . . . . ?
C5 C11 C18 C3 -0.9(2) . . . . ?
C5 C11 C18 C19 177.14(15) . . . . ?
C6 C4 C8 O2 177.35(12) . . . . ?
C6 C4 C8 C1 -2.9(2) . . . . ?
C6 C4 C12 C2 -1.1(2) . . . . ?
C6 C9 C21 C2 0.1(2) . . . . ?
C7 C3 C18 C11 1.9(2) . . . . ?
C7 C3 C18 C19 -176.13(15) . . . . ?
C8 C1 C14 C22 -0.9(2) . . . . ?
C8 C1 C16 O1 -2.1(2) . . . . ?
C8 C1 C16 C13 177.15(13) . . . . ?
C8 C4 C6 C9 -178.19(13) . . . . ?
C8 C4 C6 C22 1.3(2) . . . . ?
C8 C4 C12 C2 178.86(13) . . . . ?
C9 C6 C22 C14 179.90(14) . . . . ?
C10 N1 C15 C17 169.67(18) . . . . ?
C10 N1 C20 C17 -169.52(18) . . . . ?
C10 C5 C11 C18 -1.5(2) . . . . ?
C11 C5 C10 N1 -177.05(15) . . . . ?
C11 C5 C10 C7 3.1(2) . . . . ?
C11 C18 C19 C13 179.22(15) . . . . ?
C12 C2 C21 C9 0.6(2) . . . . ?
C12 C4 C6 C9 1.8(2) . . . . ?
C12 C4 C6 C22 -178.68(13) . . . . ?
C12 C4 C8 O2 -2.6(2) . . . . ?
C12 C4 C8 C1 177.14(13) . . . . ?
C14 C1 C8 O2 -177.63(13) . . . . ?
C14 C1 C8 C4 2.6(2) . . . . ?
C14 C1 C16 O1 178.31(13) . . . . ?
C14 C1 C16 C13 -2.4(2) . . . . ?
C15 N1 C10 C5 -171.04(16) . . . . ?
C15 N1 C10 C7 8.8(3) . . . . ?
C15 N1 C20 C17 -1.57(12) . . . . ?
C15 C17 C20 N1 1.48(12) . . . . ?
C16 C1 C8 O2 2.8(2) . . . . ?
C16 C1 C8 C4 -177.00(12) . . . . ?
C16 C1 C14 C22 178.72(14) . . . . ?
C16 C13 C19 C18 178.69(14) . . . . ?
C18 C3 C7 C10 -0.3(2) . . . . ?
C19 C13 C16 O1 -1.8(2) . . . . ?
C19 C13 C16 C1 178.90(14) . . . . ?
C20 N1 C10 C5 -7.1(3) . . . . ?
C20 N1 C10 C7 172.78(16) . . . . ?
C20 N1 C15 C17 1.57(12) . . . . ?
C21 C2 C12 C4 -0.1(2) . . . . ?
C22 C6 C9 C21 179.21(15) . . . . ?


_olex2_date_sample_data_collection 2021-02-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id AT528
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.608
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c15
_database_code_depnum_ccdc_archive 'CCDC 2089016'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H14 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   25.3047(16)
_cell_length_b                   3.9444(2)
_cell_length_c                   12.5302(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1250.66(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7795
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.6320
_cell_measurement_theta_min      3.8800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 -6 0.1296
4 1 6 0.1296
-10 2 -5 0.2265
10 -2 5 0.2265
-9 1 6 0.1369
9 -1 -6 0.1369
2 2 -4 0.2165
-2 -2 4 0.2165
-5 2 2 0.2072
5 -2 -2 0.2072
-14 -1 -1 0.1514
14 1 1 0.1514

_exptl_crystal_size_max          0.489
_exptl_crystal_size_mid          0.364
_exptl_crystal_size_min          0.259
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.7793 -1.4550 -6.4121 0.9596 0.1769 0.2189
3.7793 1.4550 6.4121 -0.9596 -0.1769 -0.2189
-9.5930 1.5130 -4.5428 0.4401 0.0833 -0.8941
9.5930 -1.5130 4.5428 -0.4401 -0.0833 0.8941
-8.9791 0.7207 6.4168 -0.4536 -0.8205 -0.3478
8.9791 -0.7207 -6.4168 0.4536 0.8205 0.3478
1.7417 2.2767 -3.6387 -0.1130 0.5964 -0.7947
-1.7417 -2.2767 3.6387 0.1130 -0.5964 0.7947
-5.0842 2.3806 1.6793 -0.4208 -0.1077 -0.9007
5.0842 -2.3806 -1.6793 0.4208 0.1077 0.9007
-13.8544 -1.3595 -0.5247 0.6968 -0.7165 0.0343
13.8544 1.3595 0.5247 -0.6968 0.7165 -0.0343

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10990
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.879
_diffrn_reflns_theta_max         66.879
_diffrn_reflns_theta_min         4.967
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -22.00   1.00    1.00    --  -41.64 125.00-180.00   76
  2  ω    -33.00  66.00   1.00    1.00    --   41.64 -37.00 -30.00   99
  3  ω      1.00  87.00   1.00    1.00    --   41.64-125.00-180.00   86
  4  ω     80.00 169.00   1.00    2.56    --   92.50  77.00  30.00   89
  5  ω     10.00  81.00   1.00    2.56    --   92.50 -94.00 -60.00   71
  6  ω     16.00  83.00   1.00    2.56    --   92.50-111.00  -6.00   67
  7  ω     10.00  81.00   1.00    2.56    --   92.50 -94.00 150.00   71
  8  ω     80.00 169.00   1.00    2.56    --   92.50  77.00-180.00   89
  9  ω     15.00 125.00   1.00    2.56    --   92.50 -79.00   2.04  110
 10  ω     67.00 166.00   1.00    2.56    --   92.50  45.00  90.00   99
 11  ω     76.00 166.00   1.00    2.56    --   92.50 125.00 -90.00   90
 12  ω     20.00 122.00   1.00    2.56    --   92.50 -61.00   0.00  102
 13  ω     20.00 122.00   1.00    2.56    --   92.50 -61.00-150.00  102
 14  ω     10.00  81.00   1.00    2.56    --   92.50 -94.00 120.00   71
 15  ω      9.00 128.00   1.00    2.56    --   92.50 -87.00 -92.96  119
 16  ω     91.00 118.00   1.00    2.56    --   92.50 -45.00-120.00   27
 17  ω     50.00  76.00   1.00    2.56    --   92.50 -83.00  74.76   26
 18  ω     87.00 113.00   1.00    2.56    --   92.50 -83.00  74.76   26
 19  ω     11.00  28.00   1.00    2.56    --   92.50 -94.00-150.00   17
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0296344000
_diffrn_orient_matrix_UB_12      -0.1748097000
_diffrn_orient_matrix_UB_13      -0.0925173000
_diffrn_orient_matrix_UB_21      0.0444188000
_diffrn_orient_matrix_UB_22      0.1042268000
_diffrn_orient_matrix_UB_23      -0.0774247000
_diffrn_orient_matrix_UB_31      0.0292708000
_diffrn_orient_matrix_UB_32      -0.3328665000
_diffrn_orient_matrix_UB_33      0.0241388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2146
_reflns_number_total             2198
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 971 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(17)
_refine_ls_extinction_coef       0.0055(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²+0.1836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20779(7) 0.8279(5) 0.74733(16) 0.0327(5) Uani 1 1 d . . . . .
H1 H 0.237729 0.750811 0.753507 0.049 Uiso 1 1 calc R U . . .
O2 O 0.29830(7) 0.6389(5) 0.68803(16) 0.0318(5) Uani 1 1 d . . . . .
O3 O 0.54136(8) 0.2353(5) 0.25208(16) 0.0296(5) Uani 1 1 d . . . . .
C1 C 0.20184(10) 0.9588(7) 0.6495(2) 0.0256(6) Uani 1 1 d . . . . .
C2 C 0.15418(10) 1.1201(7) 0.6255(2) 0.0298(6) Uani 1 1 d . . . . .
H2 H 0.127745 1.132633 0.676890 0.036 Uiso 1 1 calc R U . . .
C3 C 0.14606(11) 1.2600(6) 0.5268(2) 0.0293(6) Uani 1 1 d . . . . .
H3 H 0.114160 1.366998 0.511839 0.035 Uiso 1 1 calc R U . . .
C4 C 0.18524(11) 1.2435(6) 0.4482(2) 0.0284(6) Uani 1 1 d . . . . .
H4 H 0.179636 1.339980 0.381409 0.034 Uiso 1 1 calc R U . . .
C5 C 0.23209(10) 1.0832(6) 0.4709(2) 0.0254(6) Uani 1 1 d . . . . .
H5 H 0.258106 1.071986 0.418590 0.030 Uiso 1 1 calc R U . . .
C6 C 0.24173(10) 0.9359(6) 0.57086(19) 0.0223(5) Uani 1 1 d . . . . .
C7 C 0.29128(10) 0.7534(6) 0.5966(2) 0.0244(5) Uani 1 1 d . . . . .
C8 C 0.33119(10) 0.7019(6) 0.5136(2) 0.0259(6) Uani 1 1 d . . . . .
H8 H 0.325537 0.787768 0.445383 0.031 Uiso 1 1 calc R U . . .
C9 C 0.37568(10) 0.5324(6) 0.5350(2) 0.0251(6) Uani 1 1 d . . . . .
H9 H 0.379638 0.453868 0.604520 0.030 Uiso 1 1 calc R U . . .
C10 C 0.41865(9) 0.4571(6) 0.46131(19) 0.0231(6) Uani 1 1 d . . . . .
C11 C 0.41687(10) 0.5439(6) 0.3526(2) 0.0258(5) Uani 1 1 d . . . . .
H11 H 0.387275 0.653552 0.325307 0.031 Uiso 1 1 calc R U . . .
C12 C 0.45836(10) 0.4684(7) 0.2864(2) 0.0269(6) Uani 1 1 d . . . . .
H12 H 0.456832 0.528893 0.214727 0.032 Uiso 1 1 calc R U . . .
C13 C 0.50284(9) 0.3015(6) 0.3258(2) 0.0242(6) Uani 1 1 d . . . . .
C14 C 0.50565(10) 0.2136(6) 0.4320(2) 0.0264(6) Uani 1 1 d . . . . .
H14 H 0.535350 0.103748 0.458791 0.032 Uiso 1 1 calc R U . . .
C15 C 0.46350(10) 0.2915(6) 0.4986(2) 0.0255(5) Uani 1 1 d . . . . .
H15 H 0.465314 0.231082 0.570301 0.031 Uiso 1 1 calc R U . . .
C16 C 0.58755(10) 0.0676(7) 0.2896(2) 0.0299(6) Uani 1 1 d . . . . .
H16A H 0.611696 0.035517 0.231355 0.045 Uiso 1 1 calc R U . . .
H16B H 0.578023 -0.148756 0.318897 0.045 Uiso 1 1 calc R U . . .
H16C H 0.604091 0.203026 0.343768 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.339(3) . ?
O2 C7 1.244(4) . ?
O3 C13 1.368(3) . ?
O3 C16 1.423(3) . ?
C1 C2 1.396(4) . ?
C1 C6 1.413(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(4) . ?
C6 C7 1.481(4) . ?
C7 C8 1.465(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.337(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.457(3) . ?
C10 C11 1.405(4) . ?
C10 C15 1.391(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(4) . ?
C13 C14 1.378(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C13 O3 C16 116.8(2) . . ?
O1 C1 C2 118.0(2) . . ?
O1 C1 C6 122.2(2) . . ?
C2 C1 C6 119.7(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.7(2) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 118.9(2) . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 122.9(2) . . ?
O2 C7 C6 119.9(2) . . ?
O2 C7 C8 120.4(2) . . ?
C8 C7 C6 119.7(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 116.5 . . ?
C8 C9 C10 127.1(2) . . ?
C10 C9 H9 116.5 . . ?
C11 C10 C9 122.7(2) . . ?
C15 C10 C9 119.4(2) . . ?
C15 C10 C11 117.8(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
O3 C13 C12 115.2(2) . . ?
O3 C13 C14 124.6(2) . . ?
C14 C13 C12 120.2(2) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 H15 119.0 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.7(2) . . . . ?
O1 C1 C6 C5 -179.5(2) . . . . ?
O1 C1 C6 C7 1.6(4) . . . . ?
O2 C7 C8 C9 -0.2(4) . . . . ?
O3 C13 C14 C15 -179.2(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C6 C7 O2 -3.7(4) . . . . ?
C1 C6 C7 C8 174.8(2) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C1 C6 C7 -177.9(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 178.3(2) . . . . ?
C5 C6 C7 O2 177.4(2) . . . . ?
C5 C6 C7 C8 -4.1(3) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C6 C7 C8 C9 -178.8(2) . . . . ?
C7 C8 C9 C10 179.3(2) . . . . ?
C8 C9 C10 C11 -3.5(4) . . . . ?
C8 C9 C10 C15 176.8(2) . . . . ?
C9 C10 C11 C12 179.9(2) . . . . ?
C9 C10 C15 C14 -180.0(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C11 C12 C13 O3 179.1(2) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C15 C10 C11 C12 -0.4(4) . . . . ?
C16 O3 C13 C12 179.5(2) . . . . ?
C16 O3 C13 C14 -0.8(3) . . . . ?


_olex2_date_sample_data_collection 2020-11-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.783
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c12
_database_code_depnum_ccdc_archive 'CCDC 2089026'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-11-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 O3'
_chemical_formula_sum            'C20 H16 O3'
_chemical_formula_weight         304.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.1108(17)
_cell_length_b                   9.3204(8)
_cell_length_c                   21.004(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2958.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6702
_cell_measurement_temperature    150.02(11)
_cell_measurement_theta_max      66.8750
_cell_measurement_theta_min      5.0800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -2 1 0.0518
2 2 -1 0.0518
-1 1 1 0.0541
1 -1 -1 0.0541
6 -2 10 0.0477
-6 2 -10 0.0477
0 -5 9 0.0435
0 5 -9 0.0435

_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.087
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9942 -2.0016 0.9770 -0.1592 -0.3407 0.1217
1.9942 2.0016 -0.9770 0.1592 0.3407 -0.1217
-1.0014 0.9954 0.9995 0.0074 0.0054 -0.2067
1.0014 -0.9954 -0.9995 -0.0074 -0.0054 0.2067
6.0158 -1.8534 9.9589 -0.8696 0.4159 0.2661
-6.0158 1.8534 -9.9589 0.8696 -0.4159 -0.2661
-0.1029 -4.6209 8.7959 -0.8725 -0.3602 0.3303
0.1029 4.6209 -8.7959 0.8725 0.3602 -0.3303

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16672
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.011
_diffrn_reflns_theta_max         67.011
_diffrn_reflns_theta_min         4.210
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.02(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00  -1.00   1.00    8.76    --  -41.64 -19.00-150.00  121
  2  ω     10.00 117.00   1.00    8.76    --   41.64  74.00  19.83  107
  3  ω     19.00  87.00   1.00   35.02    --   92.50-125.00-120.00   68
  4  ω     67.00 166.00   1.00   35.02    --   92.50  45.00 150.00   99
  5  ω     19.00  87.00   1.00   35.02    --   92.50-125.00 -90.00   68
  6  ω     80.00 169.00   1.00   35.02    --   92.50  77.00  30.00   89
  7  ω     63.00 165.00   1.00   35.02    --   92.50  61.00   0.00  102
  8  ω     10.00  81.00   1.00   35.02    --   92.50 -94.00-150.00   71
  9  ω     13.00  43.00   1.00   35.02    --   92.50 -94.00 -60.00   30
 10  ω     39.00  68.00   1.00   35.02    --   92.50-125.00  60.00   29
 11  ω     84.00 122.00   1.00   35.02    --   92.50  77.00-150.00   38
 12  ω     15.00  68.00   1.00   35.02    --   92.50 -15.00  30.00   53
 13  ω    117.00 144.00   1.00   35.02    --   92.50 -15.00  30.00   27
 14  ω     75.00 106.00   1.00   35.02    --   92.50 -82.00  12.92   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0142335000
_diffrn_orient_matrix_UB_12      0.0608236000
_diffrn_orient_matrix_UB_13      -0.0674030000
_diffrn_orient_matrix_UB_21      0.0865134000
_diffrn_orient_matrix_UB_22      0.0867722000
_diffrn_orient_matrix_UB_23      0.0056497000
_diffrn_orient_matrix_UB_31      0.0521821000
_diffrn_orient_matrix_UB_32      -0.1266412000
_diffrn_orient_matrix_UB_33      -0.0283710000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2264
_reflns_number_total             2616
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²+0.7309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1328
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15159(8) 0.54666(12) 0.40841(6) 0.0396(3) Uani 1 1 d . . . . .
H1 H 0.192255 0.590025 0.425674 0.059 Uiso 1 1 calc R U . . .
O2 O 0.30847(7) 0.60991(12) 0.43506(6) 0.0395(3) Uani 1 1 d . . . . .
O3 O 0.86155(7) 0.56861(13) 0.40838(6) 0.0427(3) Uani 1 1 d . . . . .
C1 C 0.77169(10) 0.57668(16) 0.41393(8) 0.0342(4) Uani 1 1 d . . . . .
C2 C 0.72805(11) 0.66184(17) 0.45765(8) 0.0380(4) Uani 1 1 d . . . . .
H2 H 0.759715 0.719422 0.485731 0.046 Uiso 1 1 calc R U . . .
C3 C 0.63625(11) 0.66016(17) 0.45901(8) 0.0375(4) Uani 1 1 d . . . . .
H3 H 0.606951 0.717681 0.488419 0.045 Uiso 1 1 calc R U . . .
C4 C 0.58675(11) 0.57567(16) 0.41804(7) 0.0335(4) Uani 1 1 d . . . . .
C5 C 0.63269(11) 0.49209(18) 0.37348(8) 0.0369(4) Uani 1 1 d . . . . .
H5 H 0.601212 0.435685 0.344824 0.044 Uiso 1 1 calc R U . . .
C6 C 0.72355(11) 0.49233(18) 0.37153(8) 0.0392(4) Uani 1 1 d . . . . .
H6 H 0.753035 0.435957 0.341784 0.047 Uiso 1 1 calc R U . . .
C7 C 0.49080(11) 0.57791(17) 0.42230(8) 0.0350(4) Uani 1 1 d . . . . .
H7 H 0.466785 0.640857 0.451996 0.042 Uiso 1 1 calc R U . . .
C8 C 0.43306(10) 0.50063(17) 0.38878(8) 0.0357(4) Uani 1 1 d . . . . .
H8 H 0.453989 0.433321 0.359775 0.043 Uiso 1 1 calc R U . . .
C9 C 0.33743(11) 0.51917(16) 0.39654(7) 0.0334(4) Uani 1 1 d . . . . .
C10 C 0.27551(10) 0.43244(15) 0.35895(7) 0.0322(4) Uani 1 1 d . . . . .
C11 C 0.18469(10) 0.45209(15) 0.36677(8) 0.0321(4) Uani 1 1 d . . . . .
C12 C 0.12268(10) 0.37097(16) 0.33025(7) 0.0318(4) Uani 1 1 d . . . . .
C13 C 0.03041(11) 0.38710(17) 0.33857(8) 0.0365(4) Uani 1 1 d . . . . .
H13 H 0.009037 0.453010 0.368046 0.044 Uiso 1 1 calc R U . . .
C14 C -0.02757(11) 0.30694(17) 0.30379(8) 0.0384(4) Uani 1 1 d . . . . .
H14 H -0.088145 0.318534 0.309694 0.046 Uiso 1 1 calc R U . . .
C15 C 0.00368(12) 0.20707(17) 0.25916(8) 0.0396(4) Uani 1 1 d . . . . .
H15 H -0.036290 0.152389 0.235820 0.048 Uiso 1 1 calc R U . . .
C16 C 0.09257(11) 0.18969(16) 0.24978(8) 0.0379(4) Uani 1 1 d . . . . .
H16 H 0.112534 0.123607 0.219872 0.045 Uiso 1 1 calc R U . . .
C17 C 0.15436(11) 0.27089(16) 0.28497(7) 0.0329(4) Uani 1 1 d . . . . .
C18 C 0.24720(11) 0.25270(17) 0.27744(8) 0.0363(4) Uani 1 1 d . . . . .
H18 H 0.268737 0.187418 0.247751 0.044 Uiso 1 1 calc R U . . .
C19 C 0.30436(10) 0.32997(17) 0.31328(8) 0.0348(4) Uani 1 1 d . . . . .
H19 H 0.364787 0.315519 0.307841 0.042 Uiso 1 1 calc R U . . .
C20 C 0.91306(11) 0.64970(19) 0.45271(8) 0.0427(4) Uani 1 1 d . . . . .
H20A H 0.974814 0.636717 0.443640 0.064 Uiso 1 1 calc R U . . .
H20B H 0.900740 0.617304 0.495183 0.064 Uiso 1 1 calc R U . . .
H20C H 0.898227 0.749514 0.449078 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C11 1.3388(19) . ?
O2 C9 1.250(2) . ?
O3 C1 1.365(2) . ?
O3 C20 1.430(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.393(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(2) . ?
C4 C5 1.402(2) . ?
C4 C7 1.453(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.333(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.464(2) . ?
C9 C10 1.467(2) . ?
C10 C11 1.394(2) . ?
C10 C19 1.422(2) . ?
C11 C12 1.428(2) . ?
C12 C13 1.413(2) . ?
C12 C17 1.415(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.403(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.411(2) . ?
C17 C18 1.422(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.353(2) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 H1 109.5 . . ?
C1 O3 C20 117.19(12) . . ?
O3 C1 C2 124.29(14) . . ?
O3 C1 C6 115.71(14) . . ?
C2 C1 C6 120.00(15) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.98(15) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.22(15) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 117.59(15) . . ?
C3 C4 C7 119.49(14) . . ?
C5 C4 C7 122.92(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.94(15) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.26(15) . . ?
C5 C6 H6 119.9 . . ?
C4 C7 H7 116.1 . . ?
C8 C7 C4 127.82(15) . . ?
C8 C7 H7 116.1 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.57(15) . . ?
C9 C8 H8 119.2 . . ?
O2 C9 C8 119.83(15) . . ?
O2 C9 C10 119.87(14) . . ?
C8 C9 C10 120.30(14) . . ?
C11 C10 C9 119.47(14) . . ?
C11 C10 C19 118.00(14) . . ?
C19 C10 C9 122.51(14) . . ?
O1 C11 C10 122.09(14) . . ?
O1 C11 C12 117.03(13) . . ?
C10 C11 C12 120.88(14) . . ?
C13 C12 C11 121.65(14) . . ?
C13 C12 C17 119.14(14) . . ?
C17 C12 C11 119.21(14) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.62(15) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.34(15) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.37(15) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.74(15) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C18 119.14(14) . . ?
C16 C17 C12 118.79(15) . . ?
C16 C17 C18 122.05(15) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.29(15) . . ?
C19 C18 H18 119.9 . . ?
C10 C19 H19 118.8 . . ?
C18 C19 C10 122.48(15) . . ?
C18 C19 H19 118.8 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.78 2.5061(16) 147.3 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C13 -1.4(2) . . . . ?
O1 C11 C12 C17 179.19(13) . . . . ?
O2 C9 C10 C11 -0.1(2) . . . . ?
O2 C9 C10 C19 178.46(14) . . . . ?
O3 C1 C2 C3 -179.54(15) . . . . ?
O3 C1 C6 C5 179.58(15) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C2 C3 C4 C7 179.47(15) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C3 C4 C7 C8 -177.32(16) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C7 C8 C9 -177.34(15) . . . . ?
C5 C4 C7 C8 3.3(3) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C7 C4 C5 C6 -179.42(15) . . . . ?
C7 C8 C9 O2 0.5(2) . . . . ?
C7 C8 C9 C10 -179.98(14) . . . . ?
C8 C9 C10 C11 -179.69(14) . . . . ?
C8 C9 C10 C19 -1.1(2) . . . . ?
C9 C10 C11 O1 -1.0(2) . . . . ?
C9 C10 C11 C12 179.06(13) . . . . ?
C9 C10 C19 C18 -178.22(15) . . . . ?
C10 C11 C12 C13 178.53(14) . . . . ?
C10 C11 C12 C17 -0.9(2) . . . . ?
C11 C10 C19 C18 0.4(2) . . . . ?
C11 C12 C13 C14 -179.04(14) . . . . ?
C11 C12 C17 C16 179.07(14) . . . . ?
C11 C12 C17 C18 0.6(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C12 C17 C18 C19 0.2(2) . . . . ?
C13 C12 C17 C16 -0.4(2) . . . . ?
C13 C12 C17 C18 -178.83(14) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C12 0.0(2) . . . . ?
C15 C16 C17 C18 178.40(15) . . . . ?
C16 C17 C18 C19 -178.25(15) . . . . ?
C17 C12 C13 C14 0.4(2) . . . . ?
C17 C18 C19 C10 -0.7(2) . . . . ?
C19 C10 C11 O1 -179.68(14) . . . . ?
C19 C10 C11 C12 0.4(2) . . . . ?
C20 O3 C1 C2 2.7(2) . . . . ?
C20 O3 C1 C6 -177.73(14) . . . . ?


_olex2_date_sample_data_collection 2020-11-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.122
_oxdiff_exptl_absorpt_empirical_full_min 0.799
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c5
_database_code_depnum_ccdc_archive 'CCDC 2089013'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-11-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H21 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7822(7)
_cell_length_b                   16.9997(13)
_cell_length_c                   10.4535(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.025(7)
_cell_angle_gamma                90
_cell_volume                     1531.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8573
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      66.8800
_cell_measurement_theta_min      4.8940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -9 -2 0.0563
-3 9 2 0.0348
5 6 -1 0.1108
2 1 6 0.2126
-3 -5 5 0.1609
-5 -5 -1 0.1710
1 3 -6 0.1816
5 6 -3 0.1214
1 11 1 0.0535
-1 11 -1 0.0514
-5 6 1 0.0700
-2 9 -2 0.0916
4 -8 0 0.0885
-4 2 -4 0.1284
-1 -11 -2 0.1287
2 -10 -2 0.0623

_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.092
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.2948 -8.6076 -2.2917 0.0770 -0.9876 -0.1366
-3.2817 8.6343 2.2726 -0.0771 0.9882 0.1326
4.9182 5.6089 -1.1741 0.6120 0.0496 -0.7893
2.2316 0.7410 5.6056 0.9558 0.0742 0.2844
-3.3449 -5.1082 5.2000 0.0700 0.0033 0.9975
-4.8015 -4.8409 -1.0141 -0.8362 -0.0666 0.5444
1.2912 3.2851 -6.4760 -0.5207 -0.0389 -0.8529
4.5642 5.7723 -3.0193 0.3548 0.0298 -0.9345
0.6109 10.9076 0.6028 0.2945 0.8336 -0.4674
-0.5644 10.7779 -1.1454 -0.0679 0.8530 -0.5175
-4.7948 5.9294 1.0576 -0.4582 0.8461 0.2723
-1.8958 9.2009 -2.4992 -0.4254 0.7822 -0.4552
4.0004 -7.5979 0.2455 0.4767 -0.8790 -0.0096
-3.8768 2.1980 -3.8141 -0.9380 0.3324 -0.0983
-0.5975 -10.5933 -1.6000 -0.4026 -0.8413 0.3609
2.4928 -9.5602 -2.1291 -0.0266 -0.9996 -0.0090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16326
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         5.035
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  18.00   1.00    2.50    --  -41.64  77.00-150.00   92
  2  ω      1.00  87.00   1.00    2.50    --   41.64-125.00 120.00   86
  3  ω    -33.00  66.00   1.00    2.50    --   41.64 -37.00 150.00   99
  4  ω     19.00  87.00   1.00    5.00    --   92.50-125.00-150.00   68
  5  ω     19.00  87.00   1.00    5.00    --   92.50-125.00  90.00   68
  6  ω     19.00  87.00   1.00    5.00    --   92.50-125.00-120.00   68
  7  ω      9.00 129.00   1.00    5.00    --   92.50 -88.00  76.75  120
  8  ω     19.00 118.00   1.00    5.00    --   92.50 -45.00 -90.00   99
  9  ω      9.00 128.00   1.00    5.00    --   92.50 -87.00-109.73  119
 10  ω     64.00 169.00   1.00    5.00    --   92.50  30.00 150.00  105
 11  ω     80.00 169.00   1.00    5.00    --   92.50  77.00  90.00   89
 12  ω     19.00 118.00   1.00    5.00    --   92.50 -45.00 -30.00   99
 13  ω     20.00 122.00   1.00    5.00    --   92.50 -61.00  90.00  102
 14  ω     80.00 169.00   1.00    5.00    --   92.50  77.00-120.00   89
 15  ω     80.00 169.00   1.00    5.00    --   92.50  77.00  60.00   89
 16  ω     63.00 165.00   1.00    5.00    --   92.50  61.00   0.00  102
 17  ω   -115.00 -13.00   1.00    2.50    --  -41.64 -57.00-120.00  102
 18  ω     10.00  79.00   1.00    2.50    --   41.64  72.00 105.38   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1368829000
_diffrn_orient_matrix_UB_12      0.0130191000
_diffrn_orient_matrix_UB_13      0.1142979000
_diffrn_orient_matrix_UB_21      -0.0721551000
_diffrn_orient_matrix_UB_22      0.0787178000
_diffrn_orient_matrix_UB_23      0.0315545000
_diffrn_orient_matrix_UB_31      -0.0895544000
_diffrn_orient_matrix_UB_32      -0.0429188000
_diffrn_orient_matrix_UB_33      0.0920678000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2356
_reflns_number_total             2721
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.3904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1112
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.01826(12) 0.35494(6) -0.28836(9) 0.0327(3) Uani 1 1 d . . . . .
H1 H -0.045924 0.374131 -0.224544 0.049 Uiso 1 1 calc R U . . .
O2 O -0.01852(11) 0.37858(7) -0.04939(9) 0.0320(3) Uani 1 1 d . . . . .
N1 N 0.48192(13) 0.45913(7) 0.70944(11) 0.0241(3) Uani 1 1 d . . . . .
C1 C 0.09673(15) 0.30262(8) -0.24876(13) 0.0242(3) Uani 1 1 d . . . . .
C2 C 0.15764(16) 0.26296(9) -0.34419(13) 0.0274(3) Uani 1 1 d . . . . .
H2 H 0.121667 0.274347 -0.431778 0.033 Uiso 1 1 calc R U . . .
C3 C 0.27105(16) 0.20693(9) -0.30893(14) 0.0280(3) Uani 1 1 d . . . . .
H3 H 0.311844 0.180792 -0.372924 0.034 Uiso 1 1 calc R U . . .
C4 C 0.32507(16) 0.18912(8) -0.17827(14) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.398830 0.149804 -0.155122 0.032 Uiso 1 1 calc R U . . .
C5 C 0.26895(15) 0.22992(8) -0.08326(13) 0.0233(3) Uani 1 1 d . . . . .
H5 H 0.307178 0.218478 0.003962 0.028 Uiso 1 1 calc R U . . .
C6 C 0.15534(14) 0.28838(8) -0.11537(12) 0.0217(3) Uani 1 1 d . . . . .
C7 C 0.09948(15) 0.33661(8) -0.01616(13) 0.0239(3) Uani 1 1 d . . . . .
C8 C 0.18569(16) 0.33812(8) 0.11692(13) 0.0248(3) Uani 1 1 d . . . . .
H8 H 0.267558 0.303237 0.141898 0.030 Uiso 1 1 calc R U . . .
C9 C 0.14906(15) 0.38930(8) 0.20508(13) 0.0236(3) Uani 1 1 d . . . . .
H9 H 0.061524 0.420142 0.177254 0.028 Uiso 1 1 calc R U . . .
C10 C 0.22918(15) 0.40180(8) 0.33671(13) 0.0223(3) Uani 1 1 d . . . . .
C11 C 0.36141(16) 0.35910(8) 0.39483(13) 0.0246(3) Uani 1 1 d . . . . .
H11 H 0.395390 0.317980 0.348719 0.030 Uiso 1 1 calc R U . . .
C12 C 0.44150(15) 0.37611(8) 0.51685(13) 0.0246(3) Uani 1 1 d . . . . .
H12 H 0.527685 0.345947 0.552087 0.030 Uiso 1 1 calc R U . . .
C13 C 0.39638(15) 0.43872(8) 0.59118(12) 0.0216(3) Uani 1 1 d . . . . .
C14 C 0.25992(16) 0.47963(8) 0.53538(13) 0.0238(3) Uani 1 1 d . . . . .
H14 H 0.223165 0.519386 0.582544 0.029 Uiso 1 1 calc R U . . .
C15 C 0.18058(15) 0.46161(8) 0.41247(13) 0.0233(3) Uani 1 1 d . . . . .
H15 H 0.091596 0.490016 0.378240 0.028 Uiso 1 1 calc R U . . .
C16 C 0.62390(15) 0.41735(8) 0.76568(13) 0.0254(3) Uani 1 1 d . . . . .
H16A H 0.689370 0.452101 0.826225 0.030 Uiso 1 1 calc R U . . .
H16B H 0.679340 0.404586 0.696555 0.030 Uiso 1 1 calc R U . . .
C17 C 0.59742(18) 0.34211(9) 0.83667(15) 0.0339(4) Uani 1 1 d . . . . .
H17A H 0.532018 0.307397 0.777807 0.051 Uiso 1 1 calc R U . . .
H17B H 0.548279 0.354436 0.908710 0.051 Uiso 1 1 calc R U . . .
H17C H 0.695219 0.316950 0.868349 0.051 Uiso 1 1 calc R U . . .
C18 C 0.42843(17) 0.52036(8) 0.78850(13) 0.0271(3) Uani 1 1 d . . . . .
H18A H 0.390327 0.564501 0.732670 0.033 Uiso 1 1 calc R U . . .
H18B H 0.515995 0.538732 0.852614 0.033 Uiso 1 1 calc R U . . .
C19 C 0.30115(18) 0.49352(10) 0.85875(14) 0.0341(4) Uani 1 1 d . . . . .
H19A H 0.212660 0.476662 0.795982 0.051 Uiso 1 1 calc R U . . .
H19B H 0.271933 0.536377 0.908802 0.051 Uiso 1 1 calc R U . . .
H19C H 0.338466 0.450582 0.915837 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C1 1.3499(17) . ?
O2 C7 1.2514(17) . ?
N1 C13 1.3631(17) . ?
N1 C16 1.4575(17) . ?
N1 C18 1.4615(17) . ?
C1 C2 1.393(2) . ?
C1 C6 1.4119(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.4027(19) . ?
C6 C7 1.4775(19) . ?
C7 C8 1.4513(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.3503(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.4365(19) . ?
C10 C11 1.4053(19) . ?
C10 C15 1.4045(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.3646(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.4182(19) . ?
C13 C14 1.4116(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.3740(19) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.519(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.520(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C13 N1 C16 121.50(11) . . ?
C13 N1 C18 120.88(11) . . ?
C16 N1 C18 117.49(11) . . ?
O1 C1 C2 117.81(12) . . ?
O1 C1 C6 121.73(12) . . ?
C2 C1 C6 120.46(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.03(13) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.47(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.77(13) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.36(12) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 119.39(12) . . ?
C5 C6 C1 117.78(12) . . ?
C5 C6 C7 122.80(12) . . ?
O2 C7 C6 119.35(12) . . ?
O2 C7 C8 120.56(12) . . ?
C8 C7 C6 120.02(12) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.12(13) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 116.1 . . ?
C8 C9 C10 127.74(13) . . ?
C10 C9 H9 116.1 . . ?
C11 C10 C9 123.41(12) . . ?
C15 C10 C9 120.08(12) . . ?
C15 C10 C11 116.45(12) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.02(13) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.54(12) . . ?
C13 C12 H12 119.2 . . ?
N1 C13 C12 121.65(12) . . ?
N1 C13 C14 121.76(12) . . ?
C14 C13 C12 116.58(12) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.01(12) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 118.9 . . ?
C14 C15 C10 122.29(12) . . ?
C14 C15 H15 118.9 . . ?
N1 C16 H16A 108.7 . . ?
N1 C16 H16B 108.7 . . ?
N1 C16 C17 114.09(11) . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 108.8 . . ?
N1 C18 H18B 108.8 . . ?
N1 C18 C19 113.89(12) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.80 2.5306(14) 147.2 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.60(13) . . . . ?
O1 C1 C6 C5 176.60(12) . . . . ?
O1 C1 C6 C7 -5.38(19) . . . . ?
O2 C7 C8 C9 -5.6(2) . . . . ?
N1 C13 C14 C15 175.74(12) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C6 C7 O2 13.47(19) . . . . ?
C1 C6 C7 C8 -163.39(12) . . . . ?
C2 C1 C6 C5 -3.89(19) . . . . ?
C2 C1 C6 C7 174.13(12) . . . . ?
C2 C3 C4 C5 -2.5(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C4 C5 C6 C1 1.80(19) . . . . ?
C4 C5 C6 C7 -176.16(12) . . . . ?
C5 C6 C7 O2 -168.60(13) . . . . ?
C5 C6 C7 C8 14.53(19) . . . . ?
C6 C1 C2 C3 2.9(2) . . . . ?
C6 C7 C8 C9 171.19(12) . . . . ?
C7 C8 C9 C10 -175.26(13) . . . . ?
C8 C9 C10 C11 -1.3(2) . . . . ?
C8 C9 C10 C15 175.68(13) . . . . ?
C9 C10 C11 C12 175.21(13) . . . . ?
C9 C10 C15 C14 -175.21(13) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C11 C10 C15 C14 2.0(2) . . . . ?
C11 C12 C13 N1 -175.62(13) . . . . ?
C11 C12 C13 C14 3.3(2) . . . . ?
C12 C13 C14 C15 -3.19(19) . . . . ?
C13 N1 C16 C17 -83.08(16) . . . . ?
C13 N1 C18 C19 77.14(16) . . . . ?
C13 C14 C15 C10 0.6(2) . . . . ?
C15 C10 C11 C12 -1.9(2) . . . . ?
C16 N1 C13 C12 -0.24(19) . . . . ?
C16 N1 C13 C14 -179.12(12) . . . . ?
C16 N1 C18 C19 -98.75(14) . . . . ?
C18 N1 C13 C12 -175.96(12) . . . . ?
C18 N1 C13 C14 5.16(19) . . . . ?
C18 N1 C16 C17 92.78(15) . . . . ?


_olex2_date_sample_data_collection 2020-11-05
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C5
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.850
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c3
_database_code_depnum_ccdc_archive 'CCDC 2089025'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-10-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O2'
_chemical_formula_sum            'C23 H21 N O2'
_chemical_formula_weight         343.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H21 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.2455(10)
_cell_length_b                   15.1719(12)
_cell_length_c                   16.1994(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.197(8)
_cell_angle_gamma                90
_cell_volume                     3491.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7086
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      66.5450
_cell_measurement_theta_min      4.2270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.0950
1 1 0 0.0721
0 1 2 0.0870
0 -1 -2 0.1774
2 -1 0 0.0654
-2 1 0 0.0654
2 -4 9 0.1043
-4 4 -8 0.1541
4 1 -10 0.1895
0 9 -4 0.1263
4 -8 -4 0.1271
0 -9 4 0.1138
0 -10 0 0.1033

_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.131
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -1.0000 0.0003 -0.0942 0.1023 0.0524
1.0000 1.0000 -0.0003 0.0942 -0.1023 -0.0524
-0.0002 1.0008 1.9994 0.1028 -0.1025 0.1596
0.0002 -1.0008 -1.9994 -0.1028 0.1025 -0.1596
2.0001 -1.0004 0.0006 -0.1159 -0.1886 -0.0921
-2.0001 1.0004 -0.0006 0.1159 0.1886 0.0921
1.7537 -3.6282 9.4023 -0.3743 -0.6073 0.7007
-3.9413 4.3001 -7.9769 0.4592 0.7466 -0.4814
3.8798 0.9395 -9.8020 0.0607 0.0949 -0.9936
-0.0146 8.9257 -4.4055 0.9022 0.1677 -0.3974
4.0960 -8.1087 -4.0525 -0.8544 -0.1569 -0.4953
0.0175 -8.9276 4.4008 -0.9024 -0.1677 0.3969
0.2103 -9.8368 0.1179 -0.9988 0.0265 0.0407

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18525
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.041
_diffrn_reflns_theta_max         67.041
_diffrn_reflns_theta_min         4.263
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -22.00   1.00   10.00    --  -41.64 125.00 -90.00   76
  2  ω      1.00  87.00   1.00   10.00    --   41.64-125.00  60.00   86
  3  ω     17.00 116.00   1.00   10.00    --   41.64  37.00 150.00   99
  4  ω      9.00 129.00   1.00   40.00    --   92.50 -88.00 108.28  120
  5  ω     67.00 166.00   1.00   40.00    --   92.50  45.00 150.00   99
  6  ω     19.00  87.00   1.00   40.00    --   92.50-125.00 -30.00   68
  7  ω      9.00 129.00   1.00   40.00    --   92.50 -88.00  15.97  120
  8  ω     16.00 121.00   1.00   40.00    --   92.50 -30.00 120.00  105
  9  ω     40.00 174.00   1.00   40.00    --   92.50  15.00-180.00  134
 10  ω     19.00 118.00   1.00   40.00    --   92.50 -45.00 -90.00   99
 11  ω     19.00  87.00   1.00   40.00    --   92.50-125.00  30.00   68
 12  ω     19.00 118.00   1.00   40.00    --   92.50 -45.00   0.00   99
 13  ω     40.00 174.00   1.00   40.00    --   92.50  15.00 -90.00  134
 14  ω     20.00 122.00   1.00   40.00    --   92.50 -61.00 -30.00  102
 15  ω      9.00 129.00   1.00   40.00    --   92.50 -88.00 -38.18  120
 16  ω     13.00 114.00   1.00   40.00    --   92.50 -88.00-124.52  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0072222000
_diffrn_orient_matrix_UB_12      0.1013924000
_diffrn_orient_matrix_UB_13      0.0006622000
_diffrn_orient_matrix_UB_21      -0.0969528000
_diffrn_orient_matrix_UB_22      -0.0053496000
_diffrn_orient_matrix_UB_23      -0.0485741000
_diffrn_orient_matrix_UB_31      -0.0481751000
_diffrn_orient_matrix_UB_32      -0.0041817000
_diffrn_orient_matrix_UB_33      0.0819006000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2643
_reflns_number_total             3092
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0843P)²+1.2695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C20(H20), C21(H21)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13970(7) 0.62779(7) 0.69001(6) 0.0436(3) Uani 1 1 d . . . . .
H1 H 0.162301 0.653463 0.651573 0.065 Uiso 1 1 calc R U . . .
O2 O 0.25638(8) 0.66702(7) 0.59115(7) 0.0467(3) Uani 1 1 d . . . . .
N1 N 0.77269(9) 0.68304(8) 0.37451(8) 0.0415(3) Uani 1 1 d . . . . .
C1 C 0.28961(10) 0.55712(10) 0.69166(9) 0.0390(3) Uani 1 1 d . . . . .
C2 C 0.20248(10) 0.57053(9) 0.72396(9) 0.0379(3) Uani 1 1 d . . . . .
C3 C 0.51853(10) 0.65867(10) 0.48782(10) 0.0418(4) Uani 1 1 d . . . . .
C4 C 0.69083(10) 0.67401(9) 0.41062(9) 0.0389(3) Uani 1 1 d . . . . .
C5 C 0.31519(10) 0.61165(10) 0.62193(9) 0.0411(4) Uani 1 1 d . . . . .
C6 C 0.17777(10) 0.52587(9) 0.79683(9) 0.0378(3) Uani 1 1 d . . . . .
C7 C 0.09334(10) 0.54472(10) 0.83390(9) 0.0410(4) Uani 1 1 d . . . . .
H7 H 0.052126 0.586778 0.810337 0.049 Uiso 1 1 calc R U . . .
C8 C 0.59916(11) 0.61070(10) 0.51589(10) 0.0434(4) Uani 1 1 d . . . . .
H8 H 0.595588 0.572570 0.560506 0.052 Uiso 1 1 calc R U . . .
C9 C 0.24083(10) 0.46224(10) 0.83359(9) 0.0414(4) Uani 1 1 d . . . . .
C10 C 0.68266(11) 0.61825(10) 0.47978(10) 0.0421(4) Uani 1 1 d . . . . .
H10 H 0.734724 0.586326 0.500949 0.051 Uiso 1 1 calc R U . . .
C11 C 0.60934(11) 0.72026(10) 0.38045(10) 0.0439(4) Uani 1 1 d . . . . .
H11 H 0.611609 0.756168 0.334106 0.053 Uiso 1 1 calc R U . . .
C12 C 0.35108(11) 0.49298(10) 0.73058(10) 0.0443(4) Uani 1 1 d . . . . .
H12 H 0.408843 0.482289 0.709209 0.053 Uiso 1 1 calc R U . . .
C13 C 0.40717(11) 0.60439(10) 0.58947(9) 0.0435(4) Uani 1 1 d . . . . .
H13 H 0.450203 0.563473 0.612314 0.052 Uiso 1 1 calc R U . . .
C14 C 0.43113(11) 0.65611(10) 0.52666(10) 0.0437(4) Uani 1 1 d . . . . .
H14 H 0.385050 0.695210 0.505774 0.052 Uiso 1 1 calc R U . . .
C15 C 0.52720(11) 0.71288(10) 0.41854(10) 0.0449(4) Uani 1 1 d . . . . .
H15 H 0.475081 0.744970 0.397780 0.054 Uiso 1 1 calc R U . . .
C16 C 0.32766(11) 0.44703(11) 0.79804(10) 0.0460(4) Uani 1 1 d . . . . .
H16 H 0.369073 0.404971 0.821307 0.055 Uiso 1 1 calc R U . . .
C17 C 0.86052(10) 0.63960(10) 0.40184(10) 0.0424(4) Uani 1 1 d . . . . .
H17A H 0.851700 0.576463 0.406674 0.051 Uiso 1 1 calc R U . . .
H17B H 0.885548 0.662623 0.454820 0.051 Uiso 1 1 calc R U . . .
C18 C 0.07178(11) 0.50170(11) 0.90402(10) 0.0453(4) Uani 1 1 d . . . . .
H18 H 0.016590 0.515423 0.928536 0.054 Uiso 1 1 calc R U . . .
C19 C 0.92527(11) 0.66102(11) 0.33412(10) 0.0470(4) Uani 1 1 d . . . . .
H19A H 0.989965 0.666244 0.356774 0.056 Uiso 1 1 calc R U . . .
H19B H 0.921787 0.615553 0.291907 0.056 Uiso 1 1 calc R U . . .
C20 C 0.13223(12) 0.43709(11) 0.93922(10) 0.0490(4) Uani 1 1 d . . . . .
H20 H 0.116378 0.407162 0.986337 0.059 Uiso 1 1 calc R U . . .
C21 C 0.21432(11) 0.41775(11) 0.90478(10) 0.0471(4) Uani 1 1 d . . . . .
H21 H 0.253624 0.374376 0.928695 0.057 Uiso 1 1 calc R U . . .
C22 C 0.78473(11) 0.74607(11) 0.30810(10) 0.0457(4) Uani 1 1 d . . . . .
H22A H 0.762224 0.803949 0.322690 0.055 Uiso 1 1 calc R U . . .
H22B H 0.750754 0.727077 0.257115 0.055 Uiso 1 1 calc R U . . .
C23 C 0.88985(12) 0.74785(11) 0.29871(11) 0.0486(4) Uani 1 1 d . . . . .
H23A H 0.902706 0.753000 0.240929 0.058 Uiso 1 1 calc R U . . .
H23B H 0.919270 0.796833 0.329151 0.058 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C2 1.3361(18) . ?
O2 C5 1.2629(19) . ?
N1 C4 1.349(2) . ?
N1 C17 1.4542(19) . ?
N1 C22 1.4590(19) . ?
C1 C2 1.397(2) . ?
C1 C5 1.467(2) . ?
C1 C12 1.425(2) . ?
C2 C6 1.427(2) . ?
C3 C8 1.407(2) . ?
C3 C14 1.436(2) . ?
C3 C15 1.404(2) . ?
C4 C10 1.415(2) . ?
C4 C11 1.413(2) . ?
C5 C13 1.451(2) . ?
C6 C7 1.412(2) . ?
C6 C9 1.420(2) . ?
C7 H7 0.9300 . ?
C7 C18 1.364(2) . ?
C8 H8 0.9300 . ?
C8 C10 1.368(2) . ?
C9 C16 1.421(2) . ?
C9 C21 1.411(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C15 1.367(2) . ?
C12 H12 0.9300 . ?
C12 C16 1.358(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.348(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C19 1.519(2) . ?
C18 H18 0.9300 . ?
C18 C20 1.399(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C23 1.509(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.364(2) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.516(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C4 N1 C17 125.00(12) . . ?
C4 N1 C22 122.57(12) . . ?
C17 N1 C22 112.12(12) . . ?
C2 C1 C5 118.94(13) . . ?
C2 C1 C12 117.89(14) . . ?
C12 C1 C5 123.12(14) . . ?
O1 C2 C1 121.79(13) . . ?
O1 C2 C6 116.81(13) . . ?
C1 C2 C6 121.36(13) . . ?
C8 C3 C14 123.91(14) . . ?
C15 C3 C8 116.35(14) . . ?
C15 C3 C14 119.73(14) . . ?
N1 C4 C10 121.84(13) . . ?
N1 C4 C11 120.92(13) . . ?
C11 C4 C10 117.24(14) . . ?
O2 C5 C1 118.95(13) . . ?
O2 C5 C13 119.86(14) . . ?
C13 C5 C1 121.18(14) . . ?
C7 C6 C2 121.66(14) . . ?
C7 C6 C9 119.45(14) . . ?
C9 C6 C2 118.88(13) . . ?
C6 C7 H7 119.7 . . ?
C18 C7 C6 120.52(15) . . ?
C18 C7 H7 119.7 . . ?
C3 C8 H8 118.9 . . ?
C10 C8 C3 122.23(14) . . ?
C10 C8 H8 118.9 . . ?
C6 C9 C16 118.90(14) . . ?
C21 C9 C6 117.97(14) . . ?
C21 C9 C16 123.13(14) . . ?
C4 C10 H10 119.6 . . ?
C8 C10 C4 120.85(14) . . ?
C8 C10 H10 119.6 . . ?
C4 C11 H11 119.6 . . ?
C15 C11 C4 120.80(14) . . ?
C15 C11 H11 119.6 . . ?
C1 C12 H12 119.1 . . ?
C16 C12 C1 121.82(14) . . ?
C16 C12 H12 119.1 . . ?
C5 C13 H13 119.5 . . ?
C14 C13 C5 120.95(15) . . ?
C14 C13 H13 119.5 . . ?
C3 C14 H14 115.8 . . ?
C13 C14 C3 128.45(15) . . ?
C13 C14 H14 115.8 . . ?
C3 C15 H15 118.8 . . ?
C11 C15 C3 122.49(14) . . ?
C11 C15 H15 118.8 . . ?
C9 C16 H16 119.5 . . ?
C12 C16 C9 121.01(14) . . ?
C12 C16 H16 119.5 . . ?
N1 C17 H17A 111.0 . . ?
N1 C17 H17B 111.0 . . ?
N1 C17 C19 103.74(12) . . ?
H17A C17 H17B 109.0 . . ?
C19 C17 H17A 111.0 . . ?
C19 C17 H17B 111.0 . . ?
C7 C18 H18 119.8 . . ?
C7 C18 C20 120.35(15) . . ?
C20 C18 H18 119.8 . . ?
C17 C19 H19A 110.8 . . ?
C17 C19 H19B 110.8 . . ?
H19A C19 H19B 108.8 . . ?
C23 C19 C17 104.92(13) . . ?
C23 C19 H19A 110.8 . . ?
C23 C19 H19B 110.8 . . ?
C18 C20 H20 119.8 . . ?
C21 C20 C18 120.31(15) . . ?
C21 C20 H20 119.8 . . ?
C9 C21 H21 119.3 . . ?
C20 C21 C9 121.34(15) . . ?
C20 C21 H21 119.3 . . ?
N1 C22 H22A 110.8 . . ?
N1 C22 H22B 110.8 . . ?
N1 C22 C23 104.82(12) . . ?
H22A C22 H22B 108.9 . . ?
C23 C22 H22A 110.8 . . ?
C23 C22 H22B 110.8 . . ?
C19 C23 C22 104.57(13) . . ?
C19 C23 H23A 110.8 . . ?
C19 C23 H23B 110.8 . . ?
C22 C23 H23A 110.8 . . ?
C22 C23 H23B 110.8 . . ?
H23A C23 H23B 108.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.73 2.4640(14) 148.2 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C6 C7 -3.3(2) . . . . ?
O1 C2 C6 C9 177.93(12) . . . . ?
O2 C5 C13 C14 0.1(2) . . . . ?
N1 C4 C10 C8 179.40(14) . . . . ?
N1 C4 C11 C15 -178.18(14) . . . . ?
N1 C17 C19 C23 27.98(16) . . . . ?
N1 C22 C23 C19 22.74(17) . . . . ?
C1 C2 C6 C7 174.43(13) . . . . ?
C1 C2 C6 C9 -4.3(2) . . . . ?
C1 C5 C13 C14 -178.42(13) . . . . ?
C1 C12 C16 C9 -1.0(2) . . . . ?
C2 C1 C5 O2 -2.5(2) . . . . ?
C2 C1 C5 C13 176.00(13) . . . . ?
C2 C1 C12 C16 -1.3(2) . . . . ?
C2 C6 C7 C18 -179.36(13) . . . . ?
C2 C6 C9 C16 1.8(2) . . . . ?
C2 C6 C9 C21 -178.93(13) . . . . ?
C3 C8 C10 C4 -1.4(2) . . . . ?
C4 N1 C17 C19 172.12(14) . . . . ?
C4 N1 C22 C23 168.60(14) . . . . ?
C4 C11 C15 C3 -1.1(2) . . . . ?
C5 C1 C2 O1 4.1(2) . . . . ?
C5 C1 C2 C6 -173.57(12) . . . . ?
C5 C1 C12 C16 176.14(14) . . . . ?
C5 C13 C14 C3 179.16(14) . . . . ?
C6 C7 C18 C20 -1.2(2) . . . . ?
C6 C9 C16 C12 0.8(2) . . . . ?
C6 C9 C21 C20 -2.2(2) . . . . ?
C7 C6 C9 C16 -176.92(13) . . . . ?
C7 C6 C9 C21 2.3(2) . . . . ?
C7 C18 C20 C21 1.4(2) . . . . ?
C8 C3 C14 C13 -6.3(2) . . . . ?
C8 C3 C15 C11 -0.9(2) . . . . ?
C9 C6 C7 C18 -0.6(2) . . . . ?
C10 C4 C11 C15 1.9(2) . . . . ?
C11 C4 C10 C8 -0.6(2) . . . . ?
C12 C1 C2 O1 -178.33(13) . . . . ?
C12 C1 C2 C6 4.0(2) . . . . ?
C12 C1 C5 O2 -179.93(13) . . . . ?
C12 C1 C5 C13 -1.4(2) . . . . ?
C14 C3 C8 C10 -176.61(14) . . . . ?
C14 C3 C15 C11 177.92(14) . . . . ?
C15 C3 C8 C10 2.1(2) . . . . ?
C15 C3 C14 C13 175.04(15) . . . . ?
C16 C9 C21 C20 176.99(15) . . . . ?
C17 N1 C4 C10 -1.2(2) . . . . ?
C17 N1 C4 C11 178.85(14) . . . . ?
C17 N1 C22 C23 -5.30(17) . . . . ?
C17 C19 C23 C22 -31.53(17) . . . . ?
C18 C20 C21 C9 0.4(2) . . . . ?
C21 C9 C16 C12 -178.43(15) . . . . ?
C22 N1 C4 C10 -174.30(14) . . . . ?
C22 N1 C4 C11 5.7(2) . . . . ?
C22 N1 C17 C19 -14.15(17) . . . . ?


_olex2_date_sample_data_collection 2020-10-16
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C3
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.760
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c20
_database_code_depnum_ccdc_archive 'CCDC 2089018'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H23 N1 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.1591(2)
_cell_length_b                   22.5328(10)
_cell_length_c                   14.6030(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.692(4)
_cell_angle_gamma                90
_cell_volume                     1686.03(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11523
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.9900
_cell_measurement_theta_min      4.8460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 -1 0.1636
0 11 6 0.1767
3 3 -1 0.3053
2 10 3 0.2382
-3 -2 2 0.3363
0 -9 8 0.1676
0 9 -8 0.1078
3 -4 0 0.3092
-3 0 3 0.3479
-3 9 -1 0.2967
0 -12 5 0.1563
3 -9 1 0.2741
0 -14 2 0.1312
0 14 -2 0.1361
-2 -11 -1 0.2914
1 -13 -5 0.1726
0 3 9 0.1451
0 -3 -9 0.1619

_exptl_crystal_size_max          0.685
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.277
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0004 -1.8893 -1.0835 -0.1495 0.0812 0.0315
-0.4807 11.1050 6.1401 0.8084 -0.4966 -0.3161
3.2762 3.0197 -1.2913 0.2730 -0.1651 0.9478
1.9602 10.0011 3.4498 0.7653 -0.4684 0.4415
-3.3066 -2.0388 1.8231 -0.2014 0.1211 -0.9720
-0.0390 -8.8023 7.5263 0.5154 0.8409 -0.1653
0.0243 8.8116 -7.5175 -0.5158 -0.8415 0.1609
3.2189 -3.9191 -0.3459 0.1945 0.3133 0.9295
-3.2370 0.2459 3.4888 0.0206 0.0377 -0.9991
-2.5185 9.0442 -1.3461 -0.1670 -0.6879 -0.7063
-0.0011 -12.0246 5.3512 0.2327 0.9681 -0.0928
2.6394 -8.5422 0.9942 0.1569 0.6456 0.7474
0.0818 -14.4055 1.5620 -0.1817 0.9829 0.0285
0.1582 14.3486 -1.7950 0.1817 -0.9823 0.0451
-2.1888 -10.5476 -1.4207 -0.6049 0.5729 -0.5531
0.5545 -12.6872 -4.6056 -0.6901 0.6564 0.3049
-0.2704 2.5791 9.3279 0.9357 0.1723 -0.3077
0.1204 -2.5814 -9.3032 -0.9483 -0.1748 0.2648

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17423
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        67.059
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         3.624
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -22.00   1.00    5.00    --  -41.64 125.00-120.00   76
  2  ω    -33.00  66.00   1.00    5.00    --   41.64 -37.00 -90.00   99
  3  ω     17.00 116.00   1.00    5.00    --   41.64  37.00  90.00   99
  4  ω     19.00  87.00   1.00   10.00    --   92.50-125.00 -30.00   68
  5  ω     20.00 122.00   1.00   10.00    --   92.50 -61.00 -90.00  102
  6  ω     19.00  87.00   1.00   10.00    --   92.50-125.00  90.00   68
  7  ω     19.00  87.00   1.00   10.00    --   92.50-125.00-150.00   68
  8  ω     63.00 165.00   1.00   10.00    --   92.50  63.00 -26.96  102
  9  ω     16.00 121.00   1.00   10.00    --   92.50 -30.00   0.00  105
 10  ω     20.00 122.00   1.00   10.00    --   92.50 -61.00  90.00  102
 11  ω     80.00 169.00   1.00   10.00    --   92.50  77.00-180.00   89
 12  ω     19.00 118.00   1.00   10.00    --   92.50 -45.00-120.00   99
 13  ω     67.00 166.00   1.00   10.00    --   92.50  45.00 -60.00   99
 14  ω      9.00 129.00   1.00   10.00    --   92.50 -88.00 -70.64  120
 15  ω     10.00  81.00   1.00   10.00    --   92.50 -94.00 -90.00   71
 16  ω     80.00 169.00   1.00   10.00    --   92.50  77.00-150.00   89
 17  ω      9.00 129.00   1.00   10.00    --   92.50 -88.00-155.96  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0996141000
_diffrn_orient_matrix_UB_12      0.0236582000
_diffrn_orient_matrix_UB_13      0.0966628000
_diffrn_orient_matrix_UB_21      0.0232352000
_diffrn_orient_matrix_UB_22      -0.0641042000
_diffrn_orient_matrix_UB_23      0.0368725000
_diffrn_orient_matrix_UB_31      0.2825755000
_diffrn_orient_matrix_UB_32      -0.0029746000
_diffrn_orient_matrix_UB_33      -0.0239749000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.790
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                5237
_reflns_number_total             5359
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 2146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(17)
_refine_ls_extinction_coef       0.0045(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         5359
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0831P)²+0.3287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C37(H37A,H37B), C39(H39A,H39B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C23(H23), C24(H24), C27(H27), C29(H29), C30(H30), C32(H32), C33(H33),
  C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.5559(4) 0.56468(10) -0.25628(15) 0.0335(5) Uani 1 1 d . . . . .
O2 O 1.2478(4) 0.67106(10) -0.00899(15) 0.0333(5) Uani 1 1 d . . . . .
H2 H 1.151653 0.666774 0.031432 0.050 Uiso 1 1 calc R U . . .
O3 O 0.9238(4) 0.62166(10) 0.08015(15) 0.0335(5) Uani 1 1 d . . . . .
N1 N -0.1490(5) 0.36281(12) 0.21489(17) 0.0283(6) Uani 1 1 d . . . . .
C1 C 1.7211(6) 0.61307(16) -0.2736(2) 0.0337(7) Uani 1 1 d . . . . .
H1A H 1.817148 0.603280 -0.324022 0.051 Uiso 1 1 calc R U . . .
H1B H 1.840609 0.620822 -0.219499 0.051 Uiso 1 1 calc R U . . .
H1C H 1.616724 0.647725 -0.288965 0.051 Uiso 1 1 calc R U . . .
C2 C 1.4075(5) 0.57070(15) -0.1857(2) 0.0279(6) Uani 1 1 d . . . . .
C3 C 1.4048(5) 0.62047(14) -0.1309(2) 0.0264(6) Uani 1 1 d . . . . .
H3 H 1.510053 0.652862 -0.140478 0.032 Uiso 1 1 calc R U . . .
C4 C 1.2425(5) 0.62173(13) -0.0608(2) 0.0253(6) Uani 1 1 d . . . . .
C5 C 1.0795(5) 0.57364(13) -0.04524(19) 0.0241(6) Uani 1 1 d . . . . .
C6 C 1.0916(6) 0.52371(14) -0.1022(2) 0.0273(6) Uani 1 1 d . . . . .
H6 H 0.987404 0.491052 -0.093150 0.033 Uiso 1 1 calc R U . . .
C7 C 1.2518(6) 0.52146(14) -0.1708(2) 0.0302(6) Uani 1 1 d . . . . .
H7 H 1.257073 0.487627 -0.206991 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9119(6) 0.57702(13) 0.0293(2) 0.0256(6) Uani 1 1 d . . . . .
C9 C 0.7336(6) 0.52873(13) 0.0440(2) 0.0263(6) Uani 1 1 d . . . . .
H9 H 0.723380 0.496072 0.004797 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5840(6) 0.53064(13) 0.1130(2) 0.0274(6) Uani 1 1 d . . . . .
H10 H 0.601674 0.564321 0.150019 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3983(5) 0.48680(13) 0.1372(2) 0.0260(6) Uani 1 1 d . . . . .
C12 C 0.3488(6) 0.43363(15) 0.0891(2) 0.0283(6) Uani 1 1 d . . . . .
H12 H 0.437681 0.425596 0.038625 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1720(6) 0.39291(14) 0.1144(2) 0.0278(6) Uani 1 1 d . . . . .
H13 H 0.143947 0.358037 0.080638 0.033 Uiso 1 1 calc R U . . .
C14 C 0.0320(5) 0.40282(13) 0.1905(2) 0.0252(6) Uani 1 1 d . . . . .
C15 C 0.0844(5) 0.45597(13) 0.2396(2) 0.0264(6) Uani 1 1 d . . . . .
H15 H -0.000829 0.463953 0.290962 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2607(6) 0.49632(14) 0.2125(2) 0.0271(6) Uani 1 1 d . . . . .
H16 H 0.289098 0.531372 0.245747 0.032 Uiso 1 1 calc R U . . .
C17 C -0.1932(6) 0.30675(15) 0.1670(2) 0.0326(7) Uani 1 1 d . . . . .
H17A H -0.185170 0.313230 0.101732 0.039 Uiso 1 1 calc R U . . .
H17B H -0.367790 0.293021 0.174325 0.039 Uiso 1 1 calc R U . . .
C18 C 0.0000(8) 0.25855(16) 0.2002(3) 0.0420(8) Uani 1 1 d . . . . .
H18A H -0.029936 0.224254 0.161464 0.063 Uiso 1 1 calc R U . . .
H18B H -0.022032 0.248103 0.262599 0.063 Uiso 1 1 calc R U . . .
H18C H 0.174476 0.272769 0.197739 0.063 Uiso 1 1 calc R U . . .
C19 C -0.2787(6) 0.37226(16) 0.2972(2) 0.0328(7) Uani 1 1 d . . . . .
H19A H -0.432626 0.347261 0.293701 0.039 Uiso 1 1 calc R U . . .
H19B H -0.336052 0.413226 0.298328 0.039 Uiso 1 1 calc R U . . .
C20 C -0.1071(7) 0.35893(16) 0.3860(2) 0.0375(8) Uani 1 1 d . . . . .
H20A H -0.053230 0.318144 0.386258 0.056 Uiso 1 1 calc R U . . .
H20B H -0.203147 0.366071 0.437431 0.056 Uiso 1 1 calc R U . . .
H20C H 0.043955 0.384113 0.390754 0.056 Uiso 1 1 calc R U . . .
O4 O 0.4471(5) 0.31001(10) 0.94476(15) 0.0352(5) Uani 1 1 d . . . . .
O5 O 0.1265(4) 0.33394(11) 0.62883(16) 0.0368(5) Uani 1 1 d . . . . .
H5 H 0.166934 0.349400 0.581684 0.055 Uiso 1 1 calc R U . . .
O6 O 0.3699(5) 0.40131(12) 0.53339(16) 0.0407(6) Uani 1 1 d . . . . .
N2 N 1.3573(5) 0.67573(12) 0.40075(18) 0.0309(6) Uani 1 1 d . . . . .
C21 C 0.2568(7) 0.26486(15) 0.9542(2) 0.0350(7) Uani 1 1 d . . . . .
H21A H 0.280161 0.232944 0.912344 0.052 Uiso 1 1 calc R U . . .
H21B H 0.084981 0.281221 0.940159 0.052 Uiso 1 1 calc R U . . .
H21C H 0.277776 0.250134 1.016266 0.052 Uiso 1 1 calc R U . . .
C22 C 0.4517(6) 0.33499(13) 0.8608(2) 0.0277(6) Uani 1 1 d . . . . .
C23 C 0.6549(6) 0.37540(15) 0.8533(2) 0.0305(6) Uani 1 1 d . . . . .
H23 H 0.773359 0.384144 0.904552 0.037 Uiso 1 1 calc R U . . .
C24 C 0.6783(6) 0.40184(14) 0.7707(2) 0.0284(6) Uani 1 1 d . . . . .
H24 H 0.813316 0.428722 0.766726 0.034 Uiso 1 1 calc R U . . .
C25 C 0.5047(6) 0.38981(12) 0.6910(2) 0.0260(6) Uani 1 1 d . . . . .
C26 C 0.3012(6) 0.34894(13) 0.7004(2) 0.0262(6) Uani 1 1 d . . . . .
C27 C 0.2748(6) 0.32232(13) 0.7848(2) 0.0281(6) Uani 1 1 d . . . . .
H27 H 0.138243 0.296052 0.790105 0.034 Uiso 1 1 calc R U . . .
C28 C 0.5271(6) 0.41642(14) 0.6010(2) 0.0288(6) Uani 1 1 d . . . . .
C29 C 0.7263(6) 0.46116(14) 0.5888(2) 0.0283(6) Uani 1 1 d . . . . .
H29 H 0.853705 0.470386 0.637129 0.034 Uiso 1 1 calc R U . . .
C30 C 0.7229(6) 0.48872(13) 0.5071(2) 0.0265(6) Uani 1 1 d . . . . .
H30 H 0.592479 0.476780 0.461415 0.032 Uiso 1 1 calc R U . . .
C31 C 0.8963(6) 0.53457(14) 0.4811(2) 0.0266(6) Uani 1 1 d . . . . .
C32 C 1.1142(6) 0.55536(15) 0.5383(2) 0.0291(6) Uani 1 1 d . . . . .
H32 H 1.157334 0.537798 0.595671 0.035 Uiso 1 1 calc R U . . .
C33 C 1.2654(6) 0.60079(14) 0.5121(2) 0.0288(6) Uani 1 1 d . . . . .
H33 H 1.407177 0.613583 0.552392 0.035 Uiso 1 1 calc R U . . .
C34 C 1.2117(5) 0.62884(13) 0.4252(2) 0.0262(6) Uani 1 1 d . . . . .
C35 C 1.0009(6) 0.60617(14) 0.3662(2) 0.0286(6) Uani 1 1 d . . . . .
H35 H 0.964050 0.621858 0.307215 0.034 Uiso 1 1 calc R U . . .
C36 C 0.8475(6) 0.56110(14) 0.3940(2) 0.0275(6) Uani 1 1 d . . . . .
H36 H 0.706732 0.547827 0.353591 0.033 Uiso 1 1 calc R U . . .
C37 C 1.5748(7) 0.69933(16) 0.4615(2) 0.0357(7) Uani 1 1 d . . . . .
H37A H 1.693148 0.719523 0.424971 0.043 Uiso 1 1 calc R U . . .
H37B H 1.669306 0.666770 0.493507 0.043 Uiso 1 1 calc R U . . .
C38 C 1.4883(9) 0.74240(19) 0.5321(3) 0.0549(10) Uani 1 1 d . . . . .
H38A H 1.398499 0.775253 0.500898 0.082 Uiso 1 1 calc R U . . .
H38B H 1.638472 0.756690 0.570893 0.082 Uiso 1 1 calc R U . . .
H38C H 1.373403 0.722469 0.569244 0.082 Uiso 1 1 calc R U . . .
C39 C 1.2726(7) 0.71099(15) 0.3195(2) 0.0348(7) Uani 1 1 d . . . . .
H39A H 1.330462 0.751596 0.330398 0.042 Uiso 1 1 calc R U . . .
H39B H 1.083364 0.711206 0.309766 0.042 Uiso 1 1 calc R U . . .
C40 C 1.3749(7) 0.68846(16) 0.2331(2) 0.0387(8) Uani 1 1 d . . . . .
H40A H 1.324205 0.715231 0.183067 0.058 Uiso 1 1 calc R U . . .
H40B H 1.303790 0.649826 0.218118 0.058 Uiso 1 1 calc R U . . .
H40C H 1.561848 0.686002 0.243221 0.058 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.425(4) . ?
O1 C2 1.361(4) . ?
O2 H2 0.8200 . ?
O2 C4 1.343(4) . ?
O3 C8 1.247(4) . ?
N1 C14 1.374(4) . ?
N1 C17 1.449(4) . ?
N1 C19 1.458(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.379(5) . ?
C2 C7 1.402(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(4) . ?
C4 C5 1.406(4) . ?
C5 C6 1.405(4) . ?
C5 C8 1.469(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.457(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.340(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.448(4) . ?
C11 C12 1.397(4) . ?
C11 C16 1.393(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.412(4) . ?
C14 C15 1.406(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.515(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.513(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O4 C21 1.431(4) . ?
O4 C22 1.351(4) . ?
O5 H5 0.8200 . ?
O5 C26 1.341(4) . ?
O6 C28 1.250(4) . ?
N2 C34 1.368(4) . ?
N2 C37 1.448(4) . ?
N2 C39 1.453(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.402(5) . ?
C22 C27 1.382(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.364(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.409(4) . ?
C25 C26 1.415(4) . ?
C25 C28 1.462(4) . ?
C26 C27 1.392(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.465(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.344(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.446(4) . ?
C31 C32 1.401(4) . ?
C31 C36 1.401(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.368(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.415(4) . ?
C34 C35 1.403(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.378(4) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.520(5) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.511(5) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.3(2) . . ?
C4 O2 H2 109.5 . . ?
C14 N1 C17 121.4(3) . . ?
C14 N1 C19 120.6(3) . . ?
C17 N1 C19 117.6(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.4(3) . . ?
O1 C2 C7 115.0(3) . . ?
C3 C2 C7 120.6(3) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
O2 C4 C3 117.1(3) . . ?
O2 C4 C5 121.4(3) . . ?
C3 C4 C5 121.6(3) . . ?
C4 C5 C8 119.6(3) . . ?
C6 C5 C4 116.9(3) . . ?
C6 C5 C8 123.5(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.3(3) . . ?
C7 C6 H6 118.9 . . ?
C2 C7 H7 120.4 . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 H7 120.4 . . ?
O3 C8 C5 119.4(3) . . ?
O3 C8 C9 120.2(3) . . ?
C9 C8 C5 120.4(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 115.9 . . ?
C9 C10 C11 128.1(3) . . ?
C11 C10 H10 115.9 . . ?
C12 C11 C10 123.3(3) . . ?
C16 C11 C10 120.0(3) . . ?
C16 C11 C12 116.7(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.5(3) . . ?
C14 C13 H13 119.3 . . ?
N1 C14 C13 121.7(3) . . ?
N1 C14 C15 121.5(3) . . ?
C15 C14 C13 116.8(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 118.7 . . ?
C15 C16 C11 122.7(3) . . ?
C15 C16 H16 118.7 . . ?
N1 C17 H17A 108.7 . . ?
N1 C17 H17B 108.7 . . ?
N1 C17 C18 114.2(3) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 108.9 . . ?
N1 C19 H19B 108.9 . . ?
N1 C19 C20 113.5(3) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 O4 C21 117.9(2) . . ?
C26 O5 H5 109.5 . . ?
C34 N2 C37 122.2(3) . . ?
C34 N2 C39 120.9(3) . . ?
C37 N2 C39 116.0(3) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 C23 115.7(3) . . ?
O4 C22 C27 124.2(3) . . ?
C27 C22 C23 120.1(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 118.9 . . ?
C23 C24 C25 122.2(3) . . ?
C25 C24 H24 118.9 . . ?
C24 C25 C26 116.9(3) . . ?
C24 C25 C28 123.6(3) . . ?
C26 C25 C28 119.4(3) . . ?
O5 C26 C25 121.8(3) . . ?
O5 C26 C27 117.1(3) . . ?
C27 C26 C25 121.1(3) . . ?
C22 C27 C26 119.9(3) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
O6 C28 C25 119.1(3) . . ?
O6 C28 C29 119.4(3) . . ?
C25 C28 C29 121.4(3) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 C28 119.3(3) . . ?
C30 C29 H29 120.4 . . ?
C29 C30 H30 115.9 . . ?
C29 C30 C31 128.2(3) . . ?
C31 C30 H30 115.9 . . ?
C32 C31 C30 124.1(3) . . ?
C32 C31 C36 116.5(3) . . ?
C36 C31 C30 119.5(3) . . ?
C31 C32 H32 119.1 . . ?
C33 C32 C31 121.8(3) . . ?
C33 C32 H32 119.1 . . ?
C32 C33 H33 119.1 . . ?
C32 C33 C34 121.8(3) . . ?
C34 C33 H33 119.1 . . ?
N2 C34 C33 121.5(3) . . ?
N2 C34 C35 122.1(3) . . ?
C35 C34 C33 116.4(3) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 C34 121.2(3) . . ?
C36 C35 H35 119.4 . . ?
C31 C36 H36 118.9 . . ?
C35 C36 C31 122.2(3) . . ?
C35 C36 H36 118.9 . . ?
N2 C37 H37A 109.1 . . ?
N2 C37 H37B 109.1 . . ?
N2 C37 C38 112.5(3) . . ?
H37A C37 H37B 107.8 . . ?
C38 C37 H37A 109.1 . . ?
C38 C37 H37B 109.1 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 C39 H39A 108.9 . . ?
N2 C39 H39B 108.9 . . ?
N2 C39 C40 113.4(3) . . ?
H39A C39 H39B 107.7 . . ?
C40 C39 H39A 108.9 . . ?
C40 C39 H39B 108.9 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 179.4(3) . . . . ?
O1 C2 C7 C6 -178.8(3) . . . . ?
O2 C4 C5 C6 -179.0(3) . . . . ?
O2 C4 C5 C8 -0.3(4) . . . . ?
O3 C8 C9 C10 -1.5(4) . . . . ?
N1 C14 C15 C16 -178.0(3) . . . . ?
C1 O1 C2 C3 0.7(4) . . . . ?
C1 O1 C2 C7 -179.1(3) . . . . ?
C2 C3 C4 O2 179.7(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C2 C7 C6 1.4(4) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C3 C4 C5 C8 -180.0(2) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C4 C5 C8 O3 -2.7(4) . . . . ?
C4 C5 C8 C9 177.4(2) . . . . ?
C5 C6 C7 C2 -0.7(4) . . . . ?
C5 C8 C9 C10 178.5(3) . . . . ?
C6 C5 C8 O3 175.9(3) . . . . ?
C6 C5 C8 C9 -4.0(4) . . . . ?
C7 C2 C3 C4 -0.8(4) . . . . ?
C8 C5 C6 C7 -179.3(3) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C9 C10 C11 C16 179.5(3) . . . . ?
C10 C11 C12 C13 179.6(3) . . . . ?
C10 C11 C16 C15 -179.1(3) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C12 C13 C14 N1 178.6(3) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C14 N1 C17 C18 82.5(4) . . . . ?
C14 N1 C19 C20 -75.5(4) . . . . ?
C14 C15 C16 C11 -1.1(4) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C17 N1 C14 C13 3.9(4) . . . . ?
C17 N1 C14 C15 -176.9(3) . . . . ?
C17 N1 C19 C20 97.0(3) . . . . ?
C19 N1 C14 C13 176.1(3) . . . . ?
C19 N1 C14 C15 -4.7(4) . . . . ?
C19 N1 C17 C18 -89.9(3) . . . . ?
O4 C22 C23 C24 178.6(3) . . . . ?
O4 C22 C27 C26 -177.8(3) . . . . ?
O5 C26 C27 C22 178.7(3) . . . . ?
O6 C28 C29 C30 5.5(4) . . . . ?
N2 C34 C35 C36 -176.3(3) . . . . ?
C21 O4 C22 C23 -174.9(3) . . . . ?
C21 O4 C22 C27 4.1(4) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?
C23 C22 C27 C26 1.1(4) . . . . ?
C23 C24 C25 C26 0.4(4) . . . . ?
C23 C24 C25 C28 -178.7(3) . . . . ?
C24 C25 C26 O5 -179.5(3) . . . . ?
C24 C25 C26 C27 0.3(4) . . . . ?
C24 C25 C28 O6 177.2(3) . . . . ?
C24 C25 C28 C29 -4.0(4) . . . . ?
C25 C26 C27 C22 -1.1(4) . . . . ?
C25 C28 C29 C30 -173.3(3) . . . . ?
C26 C25 C28 O6 -1.9(4) . . . . ?
C26 C25 C28 C29 176.9(3) . . . . ?
C27 C22 C23 C24 -0.4(5) . . . . ?
C28 C25 C26 O5 -0.3(4) . . . . ?
C28 C25 C26 C27 179.5(3) . . . . ?
C28 C29 C30 C31 178.7(3) . . . . ?
C29 C30 C31 C32 4.5(5) . . . . ?
C29 C30 C31 C36 -175.0(3) . . . . ?
C30 C31 C32 C33 -176.9(3) . . . . ?
C30 C31 C36 C35 178.1(3) . . . . ?
C31 C32 C33 C34 -0.8(5) . . . . ?
C32 C31 C36 C35 -1.4(4) . . . . ?
C32 C33 C34 N2 177.4(3) . . . . ?
C32 C33 C34 C35 -2.2(4) . . . . ?
C33 C34 C35 C36 3.3(4) . . . . ?
C34 N2 C37 C38 -82.5(4) . . . . ?
C34 N2 C39 C40 -90.7(3) . . . . ?
C34 C35 C36 C31 -1.6(4) . . . . ?
C36 C31 C32 C33 2.6(4) . . . . ?
C37 N2 C34 C33 0.3(4) . . . . ?
C37 N2 C34 C35 179.9(3) . . . . ?
C37 N2 C39 C40 99.8(3) . . . . ?
C39 N2 C34 C33 -168.5(3) . . . . ?
C39 N2 C34 C35 11.1(4) . . . . ?
C39 N2 C37 C38 86.8(4) . . . . ?


_olex2_date_sample_data_collection 2021-03-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.675
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_at525
_database_code_depnum_ccdc_archive 'CCDC 2089019'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O3'
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H19 N1 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0731(10)
_cell_length_b                   12.6166(9)
_cell_length_c                   12.3419(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.002(10)
_cell_angle_gamma                90
_cell_volume                     1598.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8426
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.9690
_cell_measurement_theta_min      4.7090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -1 0 0.1399
7 1 0 0.1399
-5 0 7 0.1035
5 0 -7 0.1035
0 -7 4 0.0917
0 7 -4 0.0917
2 -6 -6 0.1209
-2 6 6 0.1209
2 1 -8 0.1224
-2 -1 8 0.1224
-5 -4 -2 0.1210
5 4 2 0.1210
-6 -4 3 0.1126
6 4 -3 0.1126

_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.183
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.6721 -1.4533 0.3813 0.0776 -0.9934 0.0848
6.6721 1.4533 -0.3813 -0.0776 0.9934 -0.0848
-4.9232 -0.3078 7.4627 0.0396 -0.4816 -0.8755
4.9232 0.3078 -7.4627 -0.0396 0.4816 0.8755
0.2617 -7.1406 3.5198 -0.9050 -0.0717 -0.4193
-0.2617 7.1406 -3.5198 0.9050 0.0717 0.4193
2.1486 -5.6082 -5.8463 -0.6557 -0.0497 0.7534
-2.1486 5.6082 5.8463 0.6557 0.0497 -0.7534
1.6957 0.5978 -7.9063 0.1245 0.0119 0.9922
-1.6957 -0.5978 7.9063 -0.1245 -0.0119 -0.9922
-4.8572 -3.6783 -2.2935 -0.2140 -0.8858 0.4118
4.8572 3.6783 2.2935 0.2140 0.8858 -0.4118
-6.4343 -3.5589 3.2916 -0.2236 -0.9320 -0.2852
6.4343 3.5589 -3.2916 0.2236 0.9320 0.2852

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17200
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.974
_diffrn_reflns_theta_max         66.974
_diffrn_reflns_theta_min         4.584
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -22.00   1.00    2.50    --  -41.64 125.00-180.00   76
  2  ω    -74.00  18.00   1.00    2.50    --  -41.64  77.00-150.00   92
  3  ω     13.00 115.00   1.00    2.50    --   41.64  57.00 150.00  102
  4  ω      1.00  87.00   1.00    2.50    --   41.64-125.00-120.00   86
  5  ω     19.00  87.00   1.00   10.00    --   92.50-125.00-180.00   68
  6  ω     19.00 118.00   1.00   10.00    --   92.50 -45.00   0.00   99
  7  ω     80.00 169.00   1.00   10.00    --   92.50  77.00 -60.00   89
  8  ω     12.00 127.00   1.00   10.00    --   92.50 -84.00   3.94  115
  9  ω     11.00 128.00   1.00   10.00    --   92.50 -85.00 -43.13  117
 10  ω     11.00 128.00   1.00   10.00    --   92.50 -85.00-107.56  117
 11  ω     20.00 122.00   1.00   10.00    --   92.50 -61.00 -60.00  102
 12  ω     80.00 169.00   1.00   10.00    --   92.50  77.00 -30.00   89
 13  ω      9.00 129.00   1.00   10.00    --   92.50 -88.00 -67.66  120
 14  ω      9.00 129.00   1.00   10.00    --   92.50 -88.00  -4.47  120
 15  ω     80.00 168.00   1.00   10.00    --   92.50  77.00 150.00   88
 16  ω     29.00  55.00   1.00   10.00    --   92.50 -94.00-180.00   26
 17  ω     20.00  73.00   1.00   10.00    --   92.50-125.00  60.00   53
 18  ω     71.00 101.00   1.00   10.00    --   92.50 -30.00-180.00   30
 19  ω    101.00 164.00   1.00   10.00    --   92.50  61.00  90.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0381732000
_diffrn_orient_matrix_UB_12      0.1179441000
_diffrn_orient_matrix_UB_13      -0.0150147000
_diffrn_orient_matrix_UB_21      0.1439541000
_diffrn_orient_matrix_UB_22      0.0309542000
_diffrn_orient_matrix_UB_23      0.0317124000
_diffrn_orient_matrix_UB_31      -0.0188195000
_diffrn_orient_matrix_UB_32      -0.0060468000
_diffrn_orient_matrix_UB_33      -0.1299824000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2466
_reflns_number_total             2829
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+0.3645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C15(H15A,H15B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C13(H13), C14(H14), C16(H16), C18(H18),
 C19(H19)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.95085(10) 0.61659(8) 0.60008(8) 0.0322(3) Uani 1 1 d . . . . .
O2 O 0.97430(10) 0.66795(8) 0.80338(8) 0.0339(3) Uani 1 1 d . . . . .
H2 H 0.992730 0.639267 0.751961 0.051 Uiso 1 1 calc R U . . .
O3 O 0.62968(10) 0.86135(9) 0.85216(9) 0.0399(3) Uani 1 1 d . . . . .
N1 N 0.59580(12) 0.57976(11) -0.13225(10) 0.0358(3) Uani 1 1 d . . . . .
C1 C 0.85762(13) 0.71533(11) 0.75552(11) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.46709(15) 0.60551(12) -0.21743(12) 0.0352(3) Uani 1 1 d . . . . .
H2A H 0.453744 0.680492 -0.235304 0.042 Uiso 1 1 calc R U . . .
H2B H 0.396049 0.575832 -0.199317 0.042 Uiso 1 1 calc R U . . .
C3 C 0.66650(14) 0.76696(12) 0.59176(12) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.618754 0.768942 0.511708 0.038 Uiso 1 1 calc R U . . .
C4 C 0.84373(13) 0.66399(10) 0.55599(11) 0.0266(3) Uani 1 1 d . . . . .
C5 C 0.63842(15) 0.65431(11) 0.16547(12) 0.0310(3) Uani 1 1 d . . . . .
H5 H 0.594716 0.692771 0.203783 0.037 Uiso 1 1 calc R U . . .
C6 C 0.78803(13) 0.71602(10) 0.63308(11) 0.0263(3) Uani 1 1 d . . . . .
C7 C 0.61614(14) 0.81375(13) 0.66552(12) 0.0350(3) Uani 1 1 d . . . . .
H7 H 0.534784 0.846073 0.635720 0.042 Uiso 1 1 calc R U . . .
C8 C 0.64675(14) 0.58613(11) -0.01434(12) 0.0287(3) Uani 1 1 d . . . . .
C9 C 0.70465(16) 0.87725(14) 0.97361(13) 0.0401(4) Uani 1 1 d . . . . .
H9A H 0.778591 0.921052 0.982251 0.060 Uiso 1 1 calc R U . . .
H9B H 0.733958 0.810006 1.010486 0.060 Uiso 1 1 calc R U . . .
H9C H 0.651758 0.911386 1.009654 0.060 Uiso 1 1 calc R U . . .
C10 C 0.80828(13) 0.76479(11) 0.83128(11) 0.0288(3) Uani 1 1 d . . . . .
H10 H 0.856236 0.765382 0.911323 0.035 Uiso 1 1 calc R U . . .
C11 C 0.68782(14) 0.81279(12) 0.78646(12) 0.0310(3) Uani 1 1 d . . . . .
C12 C 0.75974(14) 0.60885(10) 0.23133(11) 0.0268(3) Uani 1 1 d . . . . .
C13 C 0.58273(15) 0.64359(12) 0.04651(12) 0.0323(3) Uani 1 1 d . . . . .
H13 H 0.502143 0.674407 0.005545 0.039 Uiso 1 1 calc R U . . .
C14 C 0.77511(14) 0.66768(11) 0.42965(11) 0.0290(3) Uani 1 1 d . . . . .
H14 H 0.698250 0.706345 0.398518 0.035 Uiso 1 1 calc R U . . .
C15 C 0.63064(15) 0.50984(12) -0.20963(11) 0.0334(3) Uani 1 1 d . . . . .
H15A H 0.635767 0.435620 -0.187849 0.040 Uiso 1 1 calc R U . . .
H15B H 0.707755 0.531901 -0.223132 0.040 Uiso 1 1 calc R U . . .
C16 C 0.82038(14) 0.61646(11) 0.35701(12) 0.0280(3) Uani 1 1 d . . . . .
H16 H 0.899866 0.581982 0.391709 0.034 Uiso 1 1 calc R U . . .
C17 C 0.50159(16) 0.54099(13) -0.30840(12) 0.0392(4) Uani 1 1 d . . . . .
H17A H 0.443678 0.481689 -0.341330 0.047 Uiso 1 1 calc R U . . .
H17B H 0.512632 0.583862 -0.369278 0.047 Uiso 1 1 calc R U . . .
C18 C 0.82126(13) 0.55102(11) 0.16994(12) 0.0293(3) Uani 1 1 d . . . . .
H18 H 0.901303 0.519526 0.211287 0.035 Uiso 1 1 calc R U . . .
C19 C 0.76735(14) 0.53914(11) 0.05036(12) 0.0302(3) Uani 1 1 d . . . . .
H19 H 0.810838 0.499953 0.012398 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2558(17) . ?
O2 H2 0.8200 . ?
O2 C1 1.3430(17) . ?
O3 C9 1.4297(18) . ?
O3 C11 1.3559(17) . ?
N1 C2 1.4558(19) . ?
N1 C8 1.3518(18) . ?
N1 C15 1.4544(18) . ?
C1 C6 1.4160(18) . ?
C1 C10 1.3946(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C17 1.546(2) . ?
C3 H3 0.9300 . ?
C3 C6 1.404(2) . ?
C3 C7 1.367(2) . ?
C4 C6 1.4684(19) . ?
C4 C14 1.4571(19) . ?
C5 H5 0.9300 . ?
C5 C12 1.406(2) . ?
C5 C13 1.370(2) . ?
C7 H7 0.9300 . ?
C7 C11 1.404(2) . ?
C8 C13 1.411(2) . ?
C8 C19 1.405(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.378(2) . ?
C12 C16 1.4442(19) . ?
C12 C18 1.3991(19) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C16 1.345(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C17 1.542(2) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.3772(19) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 109.5 . . ?
C11 O3 C9 118.11(12) . . ?
C8 N1 C2 131.68(13) . . ?
C8 N1 C15 129.54(12) . . ?
C15 N1 C2 95.16(11) . . ?
O2 C1 C6 121.42(12) . . ?
O2 C1 C10 117.28(12) . . ?
C10 C1 C6 121.30(13) . . ?
N1 C2 H2A 114.0 . . ?
N1 C2 H2B 114.0 . . ?
N1 C2 C17 88.02(11) . . ?
H2A C2 H2B 111.2 . . ?
C17 C2 H2A 114.0 . . ?
C17 C2 H2B 114.0 . . ?
C6 C3 H3 119.0 . . ?
C7 C3 H3 119.0 . . ?
C7 C3 C6 122.05(13) . . ?
O1 C4 C6 119.34(12) . . ?
O1 C4 C14 120.54(12) . . ?
C14 C4 C6 120.12(12) . . ?
C12 C5 H5 119.0 . . ?
C13 C5 H5 119.0 . . ?
C13 C5 C12 121.91(13) . . ?
C1 C6 C4 119.74(12) . . ?
C3 C6 C1 117.06(12) . . ?
C3 C6 C4 123.20(12) . . ?
C3 C7 H7 120.2 . . ?
C3 C7 C11 119.68(13) . . ?
C11 C7 H7 120.2 . . ?
N1 C8 C13 120.87(13) . . ?
N1 C8 C19 120.75(12) . . ?
C19 C8 C13 118.32(12) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10 120.3 . . ?
C11 C10 C1 119.40(12) . . ?
C11 C10 H10 120.3 . . ?
O3 C11 C7 115.21(13) . . ?
O3 C11 C10 124.30(12) . . ?
C10 C11 C7 120.49(13) . . ?
C5 C12 C16 123.58(12) . . ?
C18 C12 C5 116.96(12) . . ?
C18 C12 C16 119.44(13) . . ?
C5 C13 C8 120.46(13) . . ?
C5 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C4 C14 H14 119.2 . . ?
C16 C14 C4 121.52(13) . . ?
C16 C14 H14 119.2 . . ?
N1 C15 H15A 113.9 . . ?
N1 C15 H15B 113.9 . . ?
N1 C15 C17 88.23(11) . . ?
H15A C15 H15B 111.1 . . ?
C17 C15 H15A 113.9 . . ?
C17 C15 H15B 113.9 . . ?
C12 C16 H16 116.3 . . ?
C14 C16 C12 127.47(13) . . ?
C14 C16 H16 116.3 . . ?
C2 C17 H17A 114.0 . . ?
C2 C17 H17B 114.0 . . ?
C15 C17 C2 88.17(10) . . ?
C15 C17 H17A 114.0 . . ?
C15 C17 H17B 114.0 . . ?
H17A C17 H17B 111.2 . . ?
C12 C18 H18 118.9 . . ?
C19 C18 C12 122.24(13) . . ?
C19 C18 H18 118.9 . . ?
C8 C19 H19 120.0 . . ?
C18 C19 C8 120.09(12) . . ?
C18 C19 H19 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.82 1.78 2.5090(13) 147.7 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C6 C1 2.20(19) . . . . ?
O1 C4 C6 C3 -177.29(13) . . . . ?
O1 C4 C14 C16 3.4(2) . . . . ?
O2 C1 C6 C3 179.55(12) . . . . ?
O2 C1 C6 C4 0.04(19) . . . . ?
O2 C1 C10 C11 -178.81(12) . . . . ?
N1 C2 C17 C15 4.68(11) . . . . ?
N1 C8 C13 C5 -176.53(14) . . . . ?
N1 C8 C19 C18 176.58(13) . . . . ?
N1 C15 C17 C2 -4.69(11) . . . . ?
C1 C10 C11 O3 178.74(13) . . . . ?
C1 C10 C11 C7 -1.2(2) . . . . ?
C2 N1 C8 C13 -13.7(2) . . . . ?
C2 N1 C8 C19 168.81(15) . . . . ?
C2 N1 C15 C17 5.00(12) . . . . ?
C3 C7 C11 O3 179.90(14) . . . . ?
C3 C7 C11 C10 -0.2(2) . . . . ?
C4 C14 C16 C12 176.68(12) . . . . ?
C5 C12 C16 C14 -1.4(2) . . . . ?
C5 C12 C18 C19 0.5(2) . . . . ?
C6 C1 C10 C11 1.8(2) . . . . ?
C6 C3 C7 C11 0.9(2) . . . . ?
C6 C4 C14 C16 -176.69(12) . . . . ?
C7 C3 C6 C1 -0.3(2) . . . . ?
C7 C3 C6 C4 179.22(13) . . . . ?
C8 N1 C2 C17 -164.41(16) . . . . ?
C8 N1 C15 C17 165.10(16) . . . . ?
C9 O3 C11 C7 -170.85(13) . . . . ?
C9 O3 C11 C10 9.2(2) . . . . ?
C10 C1 C6 C3 -1.10(19) . . . . ?
C10 C1 C6 C4 179.39(12) . . . . ?
C12 C5 C13 C8 -0.3(2) . . . . ?
C12 C18 C19 C8 0.2(2) . . . . ?
C13 C5 C12 C16 -178.65(13) . . . . ?
C13 C5 C12 C18 -0.5(2) . . . . ?
C13 C8 C19 C18 -1.0(2) . . . . ?
C14 C4 C6 C1 -177.71(12) . . . . ?
C14 C4 C6 C3 2.8(2) . . . . ?
C15 N1 C2 C17 -4.98(12) . . . . ?
C15 N1 C8 C13 -166.72(14) . . . . ?
C15 N1 C8 C19 15.8(2) . . . . ?
C16 C12 C18 C19 178.77(13) . . . . ?
C18 C12 C16 C14 -179.52(13) . . . . ?
C19 C8 C13 C5 1.0(2) . . . . ?


_olex2_date_sample_data_collection 2021-02-05
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id AT525
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.826
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c24
_database_code_depnum_ccdc_archive 'CCDC 2089021'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O4'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H16 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1891(6)
_cell_length_b                   9.2697(6)
_cell_length_c                   17.1760(7)
_cell_angle_alpha                101.119(4)
_cell_angle_beta                 91.071(4)
_cell_angle_gamma                101.323(5)
_cell_volume                     1405.22(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18064
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      66.8660
_cell_measurement_theta_min      4.8220
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.665
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -11 0.1278
1 0 11 0.0923
4 -5 1 0.2217
2 -5 -5 0.1742
-3 5 0 0.2487
-2 4 7 0.1548
6 0 0 0.0836
-6 0 0 0.0653
4 4 -4 0.2011
-1 -5 6 0.2644
4 -5 5 0.2328
5 0 -7 0.1108
2 4 -9 0.2111
4 1 7 0.1070

_exptl_crystal_size_max          0.567
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.15
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9499 -0.0659 -10.6420 -0.7893 0.4851 0.3763
0.7705 0.3411 10.5770 0.8046 -0.4944 -0.3290
3.5090 -5.4449 0.8464 -0.3344 0.2028 -0.9204
2.4696 -4.6351 -4.8351 -0.6942 0.4244 -0.5814
-3.4027 5.4203 0.1283 0.4044 -0.2459 0.8809
-1.9306 4.0277 6.5127 0.7736 -0.4735 0.4211
5.8743 -0.1430 -0.4352 0.4583 0.7490 -0.4785
-5.8810 0.1846 0.3921 -0.4564 -0.7460 0.4849
3.7201 3.6823 -4.2463 0.5086 0.8281 0.2358
-1.4032 -5.1448 5.5544 -0.4092 -0.6645 -0.6253
3.6911 -4.9868 4.8802 0.0045 0.0115 -0.9999
4.7735 0.4473 -6.7139 0.0260 0.9895 -0.1420
1.8340 3.5796 -8.9551 0.0239 0.8583 0.5125
4.0828 0.8742 6.5472 0.8923 0.1640 -0.4206

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37745
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.104
_diffrn_reflns_theta_max         67.104
_diffrn_reflns_theta_min         4.917
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  22.00   1.00    1.50    --   28.00  82.00 -80.54   28
  2  ω     -5.00  22.00   1.00    1.50    --   28.00  80.00 124.61   27
  3  ω     -5.00  22.00   1.00    1.50    --   28.00  80.00  38.01   27
  4  ω    -98.00 -22.00   1.00    1.50    --  -41.64 125.00  30.00   76
  5  ω      1.00  87.00   1.00    1.50    --   41.64-125.00   0.00   86
  6  ω     17.00 116.00   1.00    1.50    --   41.64  37.00-180.00   99
  7  ω     16.00 124.00   1.00    1.50    --   48.00  76.00 -46.46  108
  8  ω     16.00 124.00   1.00    1.50    --   48.00  76.00  92.67  108
  9  ω     20.00 127.00   1.00    1.50    --   52.00  75.00 135.36  107
 10  ω     20.00 127.00   1.00    1.50    --   52.00  75.00-141.20  107
 11  ω     24.00 132.00   1.00    1.50    --   56.00  76.00   8.48  108
 12  ω     28.00 136.00   1.00    1.50    --   60.00  76.00 -38.60  108
 13  ω     28.00 135.00   1.00    1.50    --   60.00  74.00 178.94  107
 14  ω     32.00 139.00   1.00    1.50    --   64.00  75.00 -10.19  107
 15  ω     32.00 139.00   1.00    1.50    --   64.00  75.00-127.88  107
 16  ω     32.00 139.00   1.00    1.50    --   64.00  74.00 111.05  107
 17  ω     32.00 140.00   1.00    1.50    --   64.00  76.00  36.97  108
 18  ω     32.00 140.00   1.00    1.50    --   64.00  76.00-165.68  108
 19  ω     36.00 144.00   1.00    5.00    --   68.00  76.00-100.93  108
 20  ω     36.00 144.00   1.00    5.00    --   68.00  76.00   9.24  108
 21  ω     36.00 143.00   1.00    5.00    --   68.00  75.00  71.99  107
 22  ω     48.00 156.00   1.00    5.00    --   80.00  76.00 129.17  108
 23  ω     53.00  84.00   1.00    5.00    --   84.00  69.00-177.03   31
 24  ω    126.00 165.00   1.00    5.00    --   92.50 125.00 -30.00   39
 25  ω     89.00 164.00   1.00    5.00    --   92.50  77.00   0.00   75
 26  ω     33.00 117.00   1.00    5.00    --   92.50 -88.00 -67.46   84
 27  ω     11.00  59.00   1.00    5.00    --   92.50 -87.00  96.13   48
 28  ω     92.00 117.00   1.00    5.00    --   92.50 -87.00 -26.80   25
 29  ω    103.00 158.00   1.00    5.00    --   92.50  76.00 -35.91   55
 30  ω     21.00  69.00   1.00    5.00    --   92.50 -87.00 -26.80   48
 31  ω     63.00 147.00   1.00    5.00    --   92.50  61.00-180.00   84
 32  ω     60.00  94.00   1.00    5.00    --   92.50  76.00 -35.91   34
 33  ω    118.00 167.00   1.00    5.00    --   92.50  77.00 120.00   49
 34  ω     63.00 103.00   1.00    5.00    --   92.50  61.00 -30.00   40
 35  ω     63.00 142.00   1.00    5.00    --   92.50  61.00  90.00   79
 36  ω     87.00 113.00   1.00    5.00    --   92.50  77.00 120.00   26
 37  ω     61.00  87.00   1.00    5.00    --   92.50  72.00-124.81   26
 38  ω     74.00 126.00   1.00    5.00    --   92.50 -85.00  49.57   52
 39  ω    111.00 147.00   1.00    5.00    --   92.50  61.00 -60.00   36
 40  ω     19.00  67.00   1.00    5.00    --   92.50 -85.00  49.57   48
 41  ω    104.00 158.00   1.00    5.00    --   92.50  61.00 150.00   54
 42  ω     63.00 101.00   1.00    5.00    --   92.50  61.00 -60.00   38
 43  ω     63.00  96.00   1.00    5.00    --   92.50  61.00 150.00   33
 44  ω     63.00  91.00   1.00    5.00    --   92.50  61.00-120.00   28
 45  ω     97.00 148.00   1.00    5.00    --   92.50  61.00-120.00   51
 46  ω    134.00 164.00   1.00    5.00    --   92.50  61.00  60.00   30
 47  ω     41.00  67.00   1.00    5.00    --   92.50  15.00 120.00   26
 48  ω    109.00 174.00   1.00    5.00    --   92.50  15.00 120.00   65
 49  ω     64.00 125.00   1.00    5.00    --   92.50  61.00  60.00   61
 50  ω    115.00 141.00   1.00    5.00    --   92.50  61.00   0.00   26
 51  ω     70.00  97.00   1.00    5.00    --   92.50 -87.00  96.13   27
 52  ω    138.00 164.00   1.00    5.00    --   92.50  61.00  30.00   26
 53  ω     72.00  98.00   1.00    5.00    --   92.50  61.00   0.00   26
 54  ω     63.00 106.00   1.00    5.00    --   92.50  61.00  30.00   43
 55  ω     66.00 148.00   1.00    5.00    --   92.50  61.00 -90.00   82
 56  ω     22.00  78.00   1.00    5.00    --   92.50-125.00 150.00   56
 57  ω    105.00 131.00   1.00    5.00    --   92.50  61.00 120.00   26
 58  ω     63.00 104.00   1.00    5.00    --   92.50  61.00 120.00   41
 59  ω     22.00  48.00   1.00    5.00    --   92.50 -45.00 -90.00   26
 60  ω     72.00 128.00   1.00    5.00    --   92.50 -87.00 164.23   56
 61  ω    109.00 161.00   1.00    5.00    --   92.50  61.00-150.00   52
 62  ω     89.00 115.00   1.00    5.00    --   92.50 -88.00 137.31   26
 63  ω      9.00  42.00   1.00    5.00    --   92.50 -87.00 164.23   33
 64  ω     78.00 114.00   1.00    5.00    --   92.50 -45.00 -90.00   36
 65  ω     64.00 104.00   1.00    5.00    --   92.50  61.00-150.00   40
 66  ω     23.00  54.00   1.00    5.00    --   92.50 -94.00-180.00   31
 67  ω     20.00  63.00   1.00    5.00    --   92.50-125.00 -60.00   43
 68  ω     51.00  77.00   1.00    5.00    --   92.50 -64.00  85.43   26
 69  ω     86.00 116.00   1.00    5.00    --   92.50 -64.00  85.43   30
 70  ω     18.00  43.00   1.00    5.00    --   92.50 -88.00 137.31   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0859730000
_diffrn_orient_matrix_UB_12      0.1270285000
_diffrn_orient_matrix_UB_13      0.0657102000
_diffrn_orient_matrix_UB_21      0.1241241000
_diffrn_orient_matrix_UB_22      0.0339089000
_diffrn_orient_matrix_UB_23      -0.0568745000
_diffrn_orient_matrix_UB_31      -0.0808504000
_diffrn_orient_matrix_UB_32      0.1124461000
_diffrn_orient_matrix_UB_33      -0.0288424000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4177
_reflns_number_total             4938
_reflns_odcompleteness_completeness 98.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         4938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+0.3115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1175
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C30(H30),
 C32(H32), C33(H33), C3(H3A), C4(H4), C7(H7A), C9(H9), C10(H10), C12(H12),
 C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C34(H34A,H34B,H34C), C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.86763(10) 0.72099(11) 0.71050(5) 0.0314(2) Uani 1 1 d . . . . .
O2 O 0.50900(12) 0.63840(12) 0.24869(6) 0.0411(3) Uani 1 1 d . . . . .
O3 O 0.48621(12) 0.70703(13) 0.11388(6) 0.0413(3) Uani 1 1 d . . . . .
H3 H 0.464413 0.661030 0.149686 0.062 Uiso 1 1 calc R U . . .
O4 O 0.87047(12) 1.08324(12) 0.04931(6) 0.0391(3) Uani 1 1 d . . . . .
C18 C 0.77171(18) 0.66796(19) 0.76804(8) 0.0406(4) Uani 1 1 d . . . . .
H18A H 0.721441 0.566339 0.747227 0.061 Uiso 1 1 calc R U . . .
H18B H 0.699783 0.730322 0.779738 0.061 Uiso 1 1 calc R U . . .
H18C H 0.829518 0.671618 0.815778 0.061 Uiso 1 1 calc R U . . .
C19 C 0.80454(14) 0.71706(14) 0.63768(7) 0.0245(3) Uani 1 1 d . . . . .
C20 C 0.65429(14) 0.67013(15) 0.61655(7) 0.0259(3) Uani 1 1 d . . . . .
H20 H 0.587428 0.642165 0.653576 0.031 Uiso 1 1 calc R U . . .
C21 C 0.60538(14) 0.66557(14) 0.53945(7) 0.0251(3) Uani 1 1 d . . . . .
H21 H 0.504272 0.634172 0.525321 0.030 Uiso 1 1 calc R U . . .
C22 C 0.70141(14) 0.70610(14) 0.48201(7) 0.0251(3) Uani 1 1 d . . . . .
C23 C 0.85291(15) 0.75739(15) 0.50563(8) 0.0284(3) Uani 1 1 d . . . . .
H23 H 0.919802 0.787730 0.469110 0.034 Uiso 1 1 calc R U . . .
C24 C 0.90294(14) 0.76307(15) 0.58208(8) 0.0280(3) Uani 1 1 d . . . . .
H24 H 1.003416 0.797916 0.597051 0.034 Uiso 1 1 calc R U . . .
C25 C 0.64021(15) 0.69591(15) 0.40184(8) 0.0269(3) Uani 1 1 d . . . . .
H25 H 0.539865 0.652150 0.391739 0.032 Uiso 1 1 calc R U . . .
C26 C 0.71106(15) 0.74188(16) 0.34128(8) 0.0299(3) Uani 1 1 d . . . . .
H26 H 0.812277 0.783487 0.347776 0.036 Uiso 1 1 calc R U . . .
C27 C 0.63109(15) 0.72766(16) 0.26413(8) 0.0299(3) Uani 1 1 d . . . . .
C28 C 0.69329(15) 0.81874(15) 0.20799(7) 0.0275(3) Uani 1 1 d . . . . .
C29 C 0.61671(15) 0.80488(16) 0.13413(8) 0.0297(3) Uani 1 1 d . . . . .
C30 C 0.67229(16) 0.89061(16) 0.07919(8) 0.0312(3) Uani 1 1 d . . . . .
H30 H 0.620611 0.879159 0.030589 0.037 Uiso 1 1 calc R U . . .
C31 C 0.80523(16) 0.99305(16) 0.09761(8) 0.0306(3) Uani 1 1 d . . . . .
C32 C 0.88268(16) 1.01092(17) 0.17081(8) 0.0341(3) Uani 1 1 d . . . . .
H32 H 0.971581 1.080837 0.183153 0.041 Uiso 1 1 calc R U . . .
C33 C 0.82766(16) 0.92582(16) 0.22387(8) 0.0313(3) Uani 1 1 d . . . . .
H33 H 0.880444 0.938670 0.272283 0.038 Uiso 1 1 calc R U . . .
C34 C 0.8012(2) 1.0682(2) -0.02751(8) 0.0436(4) Uani 1 1 d . . . . .
H34A H 0.793248 0.967199 -0.056502 0.065 Uiso 1 1 calc R U . . .
H34B H 0.859890 1.136728 -0.055640 0.065 Uiso 1 1 calc R U . . .
H34C H 0.703727 1.090480 -0.022179 0.065 Uiso 1 1 calc R U . . .
O5 O 0.18540(11) 0.75956(11) 0.28502(5) 0.0350(3) Uani 1 1 d . . . . .
O6 O 0.45041(11) 0.85785(11) 0.76202(5) 0.0337(3) Uani 1 1 d . . . . .
O7 O 0.47289(11) 0.78612(13) 0.89570(6) 0.0382(3) Uani 1 1 d . . . . .
H7 H 0.492707 0.834835 0.860812 0.057 Uiso 1 1 calc R U . . .
O8 O 0.10453(12) 0.38601(12) 0.95119(6) 0.0392(3) Uani 1 1 d . . . . .
C1 C 0.1726(2) 0.40228(19) 1.02843(8) 0.0437(4) Uani 1 1 d . . . . .
H1A H 0.272417 0.386230 1.023817 0.066 Uiso 1 1 calc R U . . .
H1B H 0.116778 0.329891 1.055408 0.066 Uiso 1 1 calc R U . . .
H1C H 0.174455 0.501670 1.058130 0.066 Uiso 1 1 calc R U . . .
C2 C 0.16859(16) 0.47960(16) 0.90426(8) 0.0301(3) Uani 1 1 d . . . . .
C3 C 0.09354(16) 0.45998(16) 0.83013(8) 0.0332(3) Uani 1 1 d . . . . .
H3A H 0.006541 0.387683 0.816604 0.040 Uiso 1 1 calc R U . . .
C4 C 0.14872(15) 0.54739(16) 0.77796(8) 0.0293(3) Uani 1 1 d . . . . .
H4 H 0.098457 0.533006 0.728689 0.035 Uiso 1 1 calc R U . . .
C5 C 0.27942(15) 0.65890(15) 0.79616(7) 0.0264(3) Uani 1 1 d . . . . .
C6 C 0.35008(15) 0.67835(16) 0.87206(8) 0.0286(3) Uani 1 1 d . . . . .
C7 C 0.29646(16) 0.58831(16) 0.92545(8) 0.0312(3) Uani 1 1 d . . . . .
H7A H 0.346030 0.601093 0.974777 0.037 Uiso 1 1 calc R U . . .
C8 C 0.34158(14) 0.75193(15) 0.74100(8) 0.0268(3) Uani 1 1 d . . . . .
C9 C 0.28088(15) 0.71871(16) 0.65795(7) 0.0280(3) Uani 1 1 d . . . . .
H9 H 0.215442 0.628188 0.638254 0.034 Uiso 1 1 calc R U . . .
C10 C 0.31854(14) 0.81652(15) 0.61096(7) 0.0263(3) Uani 1 1 d . . . . .
H10 H 0.378825 0.907763 0.634924 0.032 Uiso 1 1 calc R U . . .
C11 C 0.27791(14) 0.79980(15) 0.52680(7) 0.0244(3) Uani 1 1 d . . . . .
C12 C 0.31832(15) 0.92300(15) 0.49126(8) 0.0291(3) Uani 1 1 d . . . . .
H12 H 0.366246 1.013956 0.522603 0.035 Uiso 1 1 calc R U . . .
C13 C 0.29016(16) 0.91594(15) 0.41105(8) 0.0305(3) Uani 1 1 d . . . . .
H13 H 0.318697 1.000481 0.388943 0.037 Uiso 1 1 calc R U . . .
C14 C 0.21873(14) 0.78072(15) 0.36435(7) 0.0263(3) Uani 1 1 d . . . . .
C15 C 0.17539(14) 0.65546(15) 0.39866(8) 0.0266(3) Uani 1 1 d . . . . .
H15 H 0.126365 0.564992 0.367290 0.032 Uiso 1 1 calc R U . . .
C16 C 0.20445(14) 0.66453(15) 0.47828(7) 0.0263(3) Uani 1 1 d . . . . .
H16 H 0.175105 0.580025 0.500314 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2423(2) 0.88001(19) 0.24628(9) 0.0433(4) Uani 1 1 d . . . . .
H17A H 0.221228 0.847503 0.189957 0.065 Uiso 1 1 calc R U . . .
H17B H 0.347832 0.910232 0.257398 0.065 Uiso 1 1 calc R U . . .
H17C H 0.196052 0.963375 0.265382 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C18 1.4301(17) . ?
O1 C19 1.3597(15) . ?
O2 C27 1.2463(17) . ?
O3 H3 0.8200 . ?
O3 C29 1.3481(17) . ?
O4 C31 1.3551(17) . ?
O4 C34 1.4243(17) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.3826(18) . ?
C19 C24 1.3962(18) . ?
C20 H20 0.9300 . ?
C20 C21 1.3806(18) . ?
C21 H21 0.9300 . ?
C21 C22 1.3923(18) . ?
C22 C23 1.4047(18) . ?
C22 C25 1.4564(17) . ?
C23 H23 0.9300 . ?
C23 C24 1.3711(18) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.3323(19) . ?
C26 H26 0.9300 . ?
C26 C27 1.4736(18) . ?
C27 C28 1.4542(19) . ?
C28 C29 1.4105(18) . ?
C28 C33 1.4092(19) . ?
C29 C30 1.389(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.381(2) . ?
C31 C32 1.3981(19) . ?
C32 H32 0.9300 . ?
C32 C33 1.359(2) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O5 C14 1.3588(15) . ?
O5 C17 1.4258(17) . ?
O6 C8 1.2485(16) . ?
O7 H7 0.8200 . ?
O7 C6 1.3492(17) . ?
O8 C1 1.4244(17) . ?
O8 C2 1.3550(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.3994(19) . ?
C2 C7 1.381(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.3610(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.4081(19) . ?
C5 C6 1.4089(18) . ?
C5 C8 1.4524(19) . ?
C6 C7 1.390(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.4745(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.3276(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.4573(17) . ?
C11 C12 1.3877(19) . ?
C11 C16 1.4022(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.3836(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3838(19) . ?
C14 C15 1.3948(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.3716(18) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O1 C18 117.27(10) . . ?
C29 O3 H3 109.5 . . ?
C31 O4 C34 118.22(11) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C20 124.59(12) . . ?
O1 C19 C24 115.48(11) . . ?
C20 C19 C24 119.93(12) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.76(12) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 118.7 . . ?
C20 C21 C22 122.61(12) . . ?
C22 C21 H21 118.7 . . ?
C21 C22 C23 117.46(11) . . ?
C21 C22 C25 118.86(11) . . ?
C23 C22 C25 123.67(12) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.53(12) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.65(12) . . ?
C23 C24 H24 119.7 . . ?
C22 C25 H25 116.2 . . ?
C26 C25 C22 127.65(13) . . ?
C26 C25 H25 116.2 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.84(13) . . ?
C27 C26 H26 119.6 . . ?
O2 C27 C26 118.88(13) . . ?
O2 C27 C28 120.99(12) . . ?
C28 C27 C26 120.12(12) . . ?
C29 C28 C27 120.05(12) . . ?
C33 C28 C27 123.27(12) . . ?
C33 C28 C29 116.66(12) . . ?
O3 C29 C28 121.11(12) . . ?
O3 C29 C30 117.22(12) . . ?
C30 C29 C28 121.67(12) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 C29 119.22(12) . . ?
C31 C30 H30 120.4 . . ?
O4 C31 C30 124.78(12) . . ?
O4 C31 C32 114.76(12) . . ?
C30 C31 C32 120.46(13) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.79(13) . . ?
C33 C32 H32 120.1 . . ?
C28 C33 H33 118.9 . . ?
C32 C33 C28 122.20(12) . . ?
C32 C33 H33 118.9 . . ?
O4 C34 H34A 109.5 . . ?
O4 C34 H34B 109.5 . . ?
O4 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C14 O5 C17 117.44(10) . . ?
C6 O7 H7 109.5 . . ?
C2 O8 C1 117.73(12) . . ?
O8 C1 H1A 109.5 . . ?
O8 C1 H1B 109.5 . . ?
O8 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O8 C2 C3 114.61(12) . . ?
O8 C2 C7 124.71(12) . . ?
C7 C2 C3 120.68(13) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 C2 119.57(13) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.13(12) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 116.84(12) . . ?
C4 C5 C8 123.10(11) . . ?
C6 C5 C8 120.07(12) . . ?
O7 C6 C5 120.94(12) . . ?
O7 C6 C7 117.39(12) . . ?
C7 C6 C5 121.67(12) . . ?
C2 C7 C6 119.08(12) . . ?
C2 C7 H7A 120.5 . . ?
C6 C7 H7A 120.5 . . ?
O6 C8 C5 120.84(11) . . ?
O6 C8 C9 118.74(12) . . ?
C5 C8 C9 120.37(12) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.77(12) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 115.7 . . ?
C9 C10 C11 128.57(12) . . ?
C11 C10 H10 115.7 . . ?
C12 C11 C10 118.59(11) . . ?
C12 C11 C16 117.45(11) . . ?
C16 C11 C10 123.92(12) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 C11 122.63(12) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.75(12) . . ?
C14 C13 H13 120.6 . . ?
O5 C14 C13 124.25(12) . . ?
O5 C14 C15 115.91(11) . . ?
C13 C14 C15 119.84(12) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.58(12) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.74(12) . . ?
C15 C16 H16 119.6 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C19 C20 C21 -177.27(12) . . . . ?
O1 C19 C24 C23 177.03(12) . . . . ?
O2 C27 C28 C29 -1.2(2) . . . . ?
O2 C27 C28 C33 177.23(14) . . . . ?
O3 C29 C30 C31 179.59(13) . . . . ?
O4 C31 C32 C33 -179.79(13) . . . . ?
C18 O1 C19 C20 2.2(2) . . . . ?
C18 O1 C19 C24 -177.08(12) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C20 C19 C24 C23 -2.3(2) . . . . ?
C20 C21 C22 C23 -1.9(2) . . . . ?
C20 C21 C22 C25 179.20(12) . . . . ?
C21 C22 C23 C24 1.6(2) . . . . ?
C21 C22 C25 C26 173.41(14) . . . . ?
C22 C23 C24 C19 0.4(2) . . . . ?
C22 C25 C26 C27 -177.96(12) . . . . ?
C23 C22 C25 C26 -5.4(2) . . . . ?
C24 C19 C20 C21 1.96(19) . . . . ?
C25 C22 C23 C24 -179.56(13) . . . . ?
C25 C26 C27 O2 -18.9(2) . . . . ?
C25 C26 C27 C28 160.05(13) . . . . ?
C26 C27 C28 C29 179.92(12) . . . . ?
C26 C27 C28 C33 -1.6(2) . . . . ?
C27 C28 C29 O3 -0.6(2) . . . . ?
C27 C28 C29 C30 179.64(13) . . . . ?
C27 C28 C33 C32 -179.19(14) . . . . ?
C28 C29 C30 C31 -0.6(2) . . . . ?
C29 C28 C33 C32 -0.7(2) . . . . ?
C29 C30 C31 O4 -179.77(13) . . . . ?
C29 C30 C31 C32 -0.3(2) . . . . ?
C30 C31 C32 C33 0.7(2) . . . . ?
C31 C32 C33 C28 -0.2(2) . . . . ?
C33 C28 C29 O3 -179.10(13) . . . . ?
C33 C28 C29 C30 1.1(2) . . . . ?
C34 O4 C31 C30 -2.7(2) . . . . ?
C34 O4 C31 C32 177.83(13) . . . . ?
O5 C14 C15 C16 179.64(12) . . . . ?
O6 C8 C9 C10 -14.2(2) . . . . ?
O7 C6 C7 C2 178.17(13) . . . . ?
O8 C2 C3 C4 -179.55(13) . . . . ?
O8 C2 C7 C6 -179.33(13) . . . . ?
C1 O8 C2 C3 -178.33(13) . . . . ?
C1 O8 C2 C7 1.0(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C3 C4 C5 C8 179.04(13) . . . . ?
C4 C5 C6 O7 -177.61(13) . . . . ?
C4 C5 C6 C7 2.2(2) . . . . ?
C4 C5 C8 O6 173.86(13) . . . . ?
C4 C5 C8 C9 -8.7(2) . . . . ?
C5 C6 C7 C2 -1.7(2) . . . . ?
C5 C8 C9 C10 168.31(12) . . . . ?
C6 C5 C8 O6 -6.0(2) . . . . ?
C6 C5 C8 C9 171.47(12) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C8 C5 C6 O7 2.2(2) . . . . ?
C8 C5 C6 C7 -177.95(13) . . . . ?
C8 C9 C10 C11 175.76(12) . . . . ?
C9 C10 C11 C12 173.76(14) . . . . ?
C9 C10 C11 C16 -8.6(2) . . . . ?
C10 C11 C12 C13 177.17(12) . . . . ?
C10 C11 C16 C15 -177.15(12) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C11 C16 C15 0.53(19) . . . . ?
C12 C13 C14 O5 -179.79(13) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
C16 C11 C12 C13 -0.6(2) . . . . ?
C17 O5 C14 C13 7.2(2) . . . . ?
C17 O5 C14 C15 -173.23(13) . . . . ?


_olex2_date_sample_data_collection 2021-03-08
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.208
_oxdiff_exptl_absorpt_empirical_full_min 0.762
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c8
_database_code_depnum_ccdc_archive 'CCDC 2089014'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-10-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H17 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8738(10)
_cell_length_b                   15.8093(19)
_cell_length_c                   10.3070(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.799(11)
_cell_angle_gamma                90
_cell_volume                     1420.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4413
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      28.6520
_cell_measurement_theta_min      2.8850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 18 1 0.0956
5 -20 -2 0.0866
-11 -6 -4 0.2544
11 5 4 0.2124
2 1 -15 0.2283
9 14 3 0.2309
-7 -9 11 0.1892
-10 -14 4 0.2174
9 12 -9 0.2623
-4 -7 -12 0.2687
-6 12 -9 0.1503
2 -19 7 0.1073
11 -1 -9 0.2182

_exptl_crystal_size_max          0.603
_exptl_crystal_size_mid          0.466
_exptl_crystal_size_min          0.226
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.0067 18.4244 1.2708 -0.0777 0.9925 0.0939
4.8294 -20.4314 -2.3568 0.0736 -0.9468 -0.3133
-10.5690 -5.5682 -4.4721 -0.0305 0.3640 -0.9309
10.5892 5.4690 4.4596 0.0309 -0.3684 0.9292
1.7727 0.7767 -14.5118 0.9270 0.0734 -0.3677
9.0586 13.5473 2.7244 0.1721 0.0117 0.9850
-7.3932 -9.3522 11.4577 -0.9528 -0.0742 -0.2943
-9.7197 -13.6300 4.3480 -0.6164 -0.0470 -0.7860
8.7855 11.7143 -8.7922 0.8459 0.0654 0.5294
-3.9690 -7.2641 -11.8562 0.5577 0.0453 -0.8288
-5.7959 12.3572 -8.6009 0.4938 0.8066 -0.3250
2.3211 -18.7745 6.7094 -0.5195 -0.8469 -0.1130
10.9459 -1.1497 -9.2474 0.8091 -0.4967 0.3141

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12533
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.666
_diffrn_reflns_theta_min         2.668
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  31.00   1.00    7.72    --  -10.40 -19.00-150.00  121
  2  ω    -39.00  63.00   1.00    7.72    --  -10.40  57.00-150.00  102
  3  ω      1.00  52.00   1.00    7.72    --   11.34 -99.00 150.00   51
  4  ω    -99.00 -41.00   1.00    7.72    --  -10.40-178.00-120.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0237508000
_diffrn_orient_matrix_UB_12      0.0089880000
_diffrn_orient_matrix_UB_13      -0.0604995000
_diffrn_orient_matrix_UB_21      -0.0493750000
_diffrn_orient_matrix_UB_22      0.0357273000
_diffrn_orient_matrix_UB_23      -0.0091782000
_diffrn_orient_matrix_UB_31      0.0601658000
_diffrn_orient_matrix_UB_32      0.0256290000
_diffrn_orient_matrix_UB_33      0.0340592000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2494
_reflns_number_total             3455
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0791P)²+0.5366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1765
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.00283(16) 0.64881(9) 0.85110(13) 0.0452(4) Uani 1 1 d . . . . .
H1 H 1.024047 0.623918 0.787067 0.068 Uiso 1 1 calc R U . . .
O2 O 0.98921(16) 0.61096(9) 0.61217(13) 0.0438(4) Uani 1 1 d . . . . .
N1 N 0.5469(2) 0.56760(11) -0.17972(15) 0.0432(4) Uani 1 1 d . . . . .
C1 C 0.82304(19) 0.71362(11) 0.67516(17) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.7104(2) 0.77626(12) 0.64106(18) 0.0345(4) Uani 1 1 d . . . . .
H2 H 0.669176 0.785585 0.552429 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8868(2) 0.70371(12) 0.81020(17) 0.0336(4) Uani 1 1 d . . . . .
C4 C 0.8755(2) 0.65890(12) 0.57616(18) 0.0339(4) Uani 1 1 d . . . . .
C5 C 0.7554(2) 0.59638(11) 0.21486(17) 0.0328(4) Uani 1 1 d . . . . .
C6 C 0.8114(2) 0.53834(12) 0.13204(18) 0.0344(4) Uani 1 1 d . . . . .
H6 H 0.897077 0.505984 0.166553 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5574(2) 0.63483(12) 0.02882(18) 0.0357(4) Uani 1 1 d . . . . .
H7 H 0.471580 0.667108 -0.005550 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6150(2) 0.57653(11) -0.05262(17) 0.0340(4) Uani 1 1 d . . . . .
C9 C 0.7936(2) 0.65889(12) 0.44125(18) 0.0348(4) Uani 1 1 d . . . . .
H9 H 0.713987 0.697241 0.416123 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8296(2) 0.60453(12) 0.35045(18) 0.0342(4) Uani 1 1 d . . . . .
H10 H 0.911778 0.568363 0.379118 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6264(2) 0.64447(12) 0.15783(17) 0.0347(4) Uani 1 1 d . . . . .
H11 H 0.587028 0.683923 0.209570 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7440(2) 0.52787(12) 0.00226(17) 0.0354(4) Uani 1 1 d . . . . .
H12 H 0.783444 0.488572 -0.049632 0.042 Uiso 1 1 calc R U . . .
C13 C 0.8315(2) 0.75049(13) 0.90554(18) 0.0378(4) Uani 1 1 d . . . . .
H13 H 0.870904 0.741505 0.994606 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7186(2) 0.81000(13) 0.86845(19) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.681528 0.840926 0.932515 0.048 Uiso 1 1 calc R U . . .
C15 C 0.6598(2) 0.82406(13) 0.73554(19) 0.0394(4) Uani 1 1 d . . . . .
H15 H 0.586255 0.865806 0.710606 0.047 Uiso 1 1 calc R U . . .
C16 C 0.4278(2) 0.61702(13) -0.26223(18) 0.0391(4) Uani 1 1 d . . . . .
H16A H 0.450984 0.676868 -0.265175 0.047 Uiso 1 1 calc R U . . .
H16B H 0.325842 0.607967 -0.243510 0.047 Uiso 1 1 calc R U . . .
C17 C 0.5901(2) 0.52008(12) -0.28787(17) 0.0383(4) Uani 1 1 d . . . . .
H17A H 0.574456 0.459537 -0.282647 0.046 Uiso 1 1 calc R U . . .
H17B H 0.692245 0.532796 -0.303172 0.046 Uiso 1 1 calc R U . . .
C18 C 0.4610(2) 0.56633(13) -0.38204(18) 0.0426(5) Uani 1 1 d . . . . .
H18A H 0.377446 0.529771 -0.422276 0.051 Uiso 1 1 calc R U . . .
H18B H 0.496909 0.600792 -0.447957 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C3 1.352(2) . ?
O2 C4 1.261(2) . ?
N1 C8 1.343(2) . ?
N1 C16 1.454(3) . ?
N1 C17 1.454(2) . ?
C1 C2 1.404(3) . ?
C1 C3 1.410(2) . ?
C1 C4 1.478(3) . ?
C2 H2 0.9300 . ?
C2 C15 1.373(3) . ?
C3 C13 1.391(3) . ?
C4 C9 1.443(3) . ?
C5 C6 1.406(2) . ?
C5 C10 1.435(2) . ?
C5 C11 1.408(3) . ?
C6 H6 0.9300 . ?
C6 C12 1.369(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.406(3) . ?
C7 C11 1.364(2) . ?
C8 C12 1.407(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.352(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C18 1.546(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.540(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C8 N1 C16 131.22(16) . . ?
C8 N1 C17 131.81(17) . . ?
C16 N1 C17 95.54(14) . . ?
C2 C1 C3 117.45(16) . . ?
C2 C1 C4 122.78(16) . . ?
C3 C1 C4 119.77(16) . . ?
C1 C2 H2 119.2 . . ?
C15 C2 C1 121.51(17) . . ?
C15 C2 H2 119.2 . . ?
O1 C3 C1 121.38(16) . . ?
O1 C3 C13 118.04(16) . . ?
C13 C3 C1 120.58(17) . . ?
O2 C4 C1 119.12(16) . . ?
O2 C4 C9 120.96(17) . . ?
C9 C4 C1 119.89(16) . . ?
C6 C5 C10 120.00(17) . . ?
C6 C5 C11 116.82(16) . . ?
C11 C5 C10 123.18(16) . . ?
C5 C6 H6 118.9 . . ?
C12 C6 C5 122.18(17) . . ?
C12 C6 H6 118.9 . . ?
C8 C7 H7 119.7 . . ?
C11 C7 H7 119.7 . . ?
C11 C7 C8 120.57(17) . . ?
N1 C8 C7 120.24(17) . . ?
N1 C8 C12 121.21(16) . . ?
C7 C8 C12 118.54(16) . . ?
C4 C9 H9 119.2 . . ?
C10 C9 C4 121.67(17) . . ?
C10 C9 H9 119.2 . . ?
C5 C10 H10 116.3 . . ?
C9 C10 C5 127.31(18) . . ?
C9 C10 H10 116.3 . . ?
C5 C11 H11 119.1 . . ?
C7 C11 C5 121.85(17) . . ?
C7 C11 H11 119.1 . . ?
C6 C12 C8 120.02(17) . . ?
C6 C12 H12 120.0 . . ?
C8 C12 H12 120.0 . . ?
C3 C13 H13 119.9 . . ?
C14 C13 C3 120.17(17) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.20(18) . . ?
C15 C14 H14 119.9 . . ?
C2 C15 C14 119.93(18) . . ?
C2 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N1 C16 H16A 114.0 . . ?
N1 C16 H16B 114.0 . . ?
N1 C16 C18 87.82(14) . . ?
H16A C16 H16B 111.2 . . ?
C18 C16 H16A 114.0 . . ?
C18 C16 H16B 114.0 . . ?
N1 C17 H17A 114.0 . . ?
N1 C17 H17B 114.0 . . ?
N1 C17 C18 88.05(14) . . ?
H17A C17 H17B 111.2 . . ?
C18 C17 H17A 114.0 . . ?
C18 C17 H17B 114.0 . . ?
C16 C18 H18A 113.9 . . ?
C16 C18 H18B 113.9 . . ?
C17 C18 C16 88.48(14) . . ?
C17 C18 H18A 113.9 . . ?
C17 C18 H18B 113.9 . . ?
H18A C18 H18B 111.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.82 1.78 2.5150(19) 147.8 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C13 C14 176.91(17) . . . . ?
O2 C4 C9 C10 3.8(3) . . . . ?
N1 C8 C12 C6 179.89(18) . . . . ?
N1 C16 C18 C17 -2.43(14) . . . . ?
N1 C17 C18 C16 2.43(14) . . . . ?
C1 C2 C15 C14 -1.0(3) . . . . ?
C1 C3 C13 C14 -3.1(3) . . . . ?
C1 C4 C9 C10 -174.17(17) . . . . ?
C2 C1 C3 O1 -175.62(16) . . . . ?
C2 C1 C3 C13 4.4(3) . . . . ?
C2 C1 C4 O2 171.77(16) . . . . ?
C2 C1 C4 C9 -10.2(3) . . . . ?
C3 C1 C2 C15 -2.4(3) . . . . ?
C3 C1 C4 O2 -8.3(3) . . . . ?
C3 C1 C4 C9 169.69(16) . . . . ?
C3 C13 C14 C15 -0.4(3) . . . . ?
C4 C1 C2 C15 177.54(17) . . . . ?
C4 C1 C3 O1 4.5(3) . . . . ?
C4 C1 C3 C13 -175.50(16) . . . . ?
C4 C9 C10 C5 178.25(17) . . . . ?
C5 C6 C12 C8 0.5(3) . . . . ?
C6 C5 C10 C9 177.62(18) . . . . ?
C6 C5 C11 C7 0.7(3) . . . . ?
C7 C8 C12 C6 -0.5(3) . . . . ?
C8 N1 C16 C18 169.8(2) . . . . ?
C8 N1 C17 C18 -169.7(2) . . . . ?
C8 C7 C11 C5 -0.8(3) . . . . ?
C10 C5 C6 C12 179.58(17) . . . . ?
C10 C5 C11 C7 -179.45(18) . . . . ?
C11 C5 C6 C12 -0.6(3) . . . . ?
C11 C5 C10 C9 -2.2(3) . . . . ?
C11 C7 C8 N1 -179.75(18) . . . . ?
C11 C7 C8 C12 0.7(3) . . . . ?
C13 C14 C15 C2 2.4(3) . . . . ?
C16 N1 C8 C7 9.6(3) . . . . ?
C16 N1 C8 C12 -170.81(19) . . . . ?
C16 N1 C17 C18 -2.59(15) . . . . ?
C17 N1 C8 C7 172.50(19) . . . . ?
C17 N1 C8 C12 -7.9(3) . . . . ?
C17 N1 C16 C18 2.58(15) . . . . ?


_olex2_date_sample_data_collection 2020-10-21
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C8
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.103
_oxdiff_exptl_absorpt_empirical_full_min 0.875
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c4
_database_code_depnum_ccdc_archive 'CCDC 2089020'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O3'
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_weight         323.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H21 N1 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.6857(16)
_cell_length_b                   10.0690(9)
_cell_length_c                   13.1089(13)
_cell_angle_alpha                90
_cell_angle_beta                 113.007(13)
_cell_angle_gamma                90
_cell_volume                     1662.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8853
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2600
_cell_measurement_theta_min      3.7220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
15 -3 5 0.2302
-15 3 -5 0.1002
10 5 -17 0.1349
-10 -5 17 0.1349
-1 -9 -13 0.0513
1 9 13 0.0513
2 -12 9 0.2292

_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.103
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
14.5413 -3.4150 4.9815 0.1545 0.6363 0.7558
-14.5413 3.4150 -4.9815 -0.1545 -0.6363 -0.7558
10.0961 4.8471 -17.0783 0.1472 0.6195 -0.7711
-10.0961 -4.8471 17.0783 -0.1472 -0.6195 0.7711
-0.8576 -9.1860 -12.5963 0.8657 -0.2073 -0.4556
0.8576 9.1860 12.5963 -0.8657 0.2073 0.4556
2.4397 -11.6484 8.5968 0.5289 -0.1286 0.8389

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22942
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.644
_diffrn_reflns_theta_min         3.122
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  31.00   1.00   30.20    --  -10.40 -19.00 120.00  121
  2  ω    -85.00  14.00   1.00   30.20    --  -10.40 -37.00   0.00   99
  3  ω    -21.00  39.00   1.00   30.20    --   11.34  77.00-120.00   60
  4  ω    -21.00  39.00   1.00   30.20    --   11.34  77.00 120.00   60
  5  ω    -35.00  64.00   1.00   30.20    --  -10.40  37.00 150.00   99
  6  ω      1.00  26.00   1.00   30.20    --   11.34 -99.00  60.00   25
  7  ω    -18.00  44.00   1.00   30.20    --   11.34 -77.00 -90.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0041902000
_diffrn_orient_matrix_UB_12      -0.0620600000
_diffrn_orient_matrix_UB_13      -0.0237571000
_diffrn_orient_matrix_UB_21      0.0490270000
_diffrn_orient_matrix_UB_22      0.0201435000
_diffrn_orient_matrix_UB_23      -0.0015741000
_diffrn_orient_matrix_UB_31      0.0273131000
_diffrn_orient_matrix_UB_32      -0.0266403000
_diffrn_orient_matrix_UB_33      0.0537344000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3171
_reflns_number_total             4211
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0826P)²+0.5131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1748
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67894(9) 0.55078(12) 0.61015(9) 0.0374(3) Uani 1 1 d . . . . .
O2 O 0.81249(10) 0.59293(14) 0.80202(10) 0.0422(3) Uani 1 1 d . . . . .
H2 H 0.760744 0.558717 0.753529 0.063 Uiso 1 1 calc R U . . .
O0 O 1.10757(11) 0.86727(15) 0.84553(10) 0.0527(4) Uani 1 1 d . . . . .
N1 N 0.34592(11) 0.62658(14) -0.07482(11) 0.0347(3) Uani 1 1 d . . . . .
C1 C 0.56383(12) 0.67518(16) 0.19476(13) 0.0322(4) Uani 1 1 d . . . . .
H1 H 0.626445 0.723758 0.224807 0.039 Uiso 1 1 calc R U . . .
C2 C 0.82582(12) 0.68861(16) 0.63889(13) 0.0306(3) Uani 1 1 d . . . . .
C3 C 0.40730(12) 0.61349(16) 0.03440(13) 0.0308(3) Uani 1 1 d . . . . .
C4 C 0.68145(12) 0.64703(17) 0.44778(13) 0.0328(4) Uani 1 1 d . . . . .
H4 H 0.714175 0.705788 0.416332 0.039 Uiso 1 1 calc R U . . .
C5 C 0.72620(12) 0.62480(16) 0.56734(13) 0.0314(3) Uani 1 1 d . . . . .
C6 C 0.53442(12) 0.59268(16) 0.26487(13) 0.0308(3) Uani 1 1 d . . . . .
C7 C 0.86418(13) 0.66859(17) 0.75504(13) 0.0333(4) Uani 1 1 d . . . . .
C8 C 0.59254(13) 0.58222(16) 0.38299(13) 0.0325(4) Uani 1 1 d . . . . .
H8 H 0.565096 0.522912 0.419350 0.039 Uiso 1 1 calc R U . . .
C9 C 0.37817(13) 0.52901(17) 0.10371(13) 0.0340(4) Uani 1 1 d . . . . .
H9 H 0.316261 0.479055 0.073858 0.041 Uiso 1 1 calc R U . . .
C10 C 0.50316(13) 0.68602(16) 0.08394(14) 0.0333(4) Uani 1 1 d . . . . .
H10 H 0.525089 0.741791 0.040403 0.040 Uiso 1 1 calc R U . . .
C11 C 0.44048(13) 0.51985(17) 0.21503(13) 0.0339(4) Uani 1 1 d . . . . .
H11 H 0.419470 0.463247 0.258753 0.041 Uiso 1 1 calc R U . . .
C12 C 0.88696(13) 0.76957(17) 0.59889(13) 0.0340(4) Uani 1 1 d . . . . .
H12 H 0.863740 0.784002 0.522991 0.041 Uiso 1 1 calc R U . . .
C13 C 0.37243(13) 0.71279(17) -0.14967(13) 0.0353(4) Uani 1 1 d . . . . .
H13A H 0.433817 0.679479 -0.161232 0.042 Uiso 1 1 calc R U . . .
H13B H 0.387019 0.802493 -0.120660 0.042 Uiso 1 1 calc R U . . .
C14 C 0.95766(14) 0.72826(18) 0.82587(14) 0.0379(4) Uani 1 1 d . . . . .
H14 H 0.981642 0.715214 0.901997 0.045 Uiso 1 1 calc R U . . .
C15 C 1.01464(14) 0.80685(17) 0.78274(14) 0.0382(4) Uani 1 1 d . . . . .
C16 C 0.97950(14) 0.82770(18) 0.66827(14) 0.0391(4) Uani 1 1 d . . . . .
H16 H 1.018623 0.880433 0.639745 0.047 Uiso 1 1 calc R U . . .
C17 C 0.25216(13) 0.54544(18) -0.13187(14) 0.0376(4) Uani 1 1 d . . . . .
H17A H 0.194679 0.570311 -0.109938 0.045 Uiso 1 1 calc R U . . .
H17B H 0.267900 0.451956 -0.115940 0.045 Uiso 1 1 calc R U . . .
C18 C 0.22317(14) 0.57454(19) -0.25496(14) 0.0415(4) Uani 1 1 d . . . . .
H18A H 0.251409 0.506615 -0.288346 0.050 Uiso 1 1 calc R U . . .
H18B H 0.146761 0.578685 -0.294749 0.050 Uiso 1 1 calc R U . . .
C19 C 0.27395(15) 0.7090(2) -0.25657(15) 0.0458(5) Uani 1 1 d . . . . .
H19A H 0.292771 0.716297 -0.320415 0.055 Uiso 1 1 calc R U . . .
H19B H 0.225939 0.780828 -0.258745 0.055 Uiso 1 1 calc R U . . .
C20 C 1.1471(2) 0.8490(2) 0.96281(16) 0.0623(7) Uani 1 1 d . . . . .
H20A H 1.151822 0.755735 0.979379 0.093 Uiso 1 1 calc R U . . .
H20B H 1.099785 0.890419 0.991293 0.093 Uiso 1 1 calc R U . . .
H20C H 1.216212 0.888445 0.996589 0.093 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.2540(19) . ?
O2 H2 0.8200 . ?
O2 C7 1.3418(19) . ?
O0 C15 1.359(2) . ?
O0 C20 1.428(2) . ?
N1 C3 1.354(2) . ?
N1 C13 1.458(2) . ?
N1 C17 1.457(2) . ?
C1 H1 0.9300 . ?
C1 C6 1.409(2) . ?
C1 C10 1.367(2) . ?
C2 C5 1.467(2) . ?
C2 C7 1.418(2) . ?
C2 C12 1.408(2) . ?
C3 C9 1.411(2) . ?
C3 C10 1.418(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.460(2) . ?
C4 C8 1.349(2) . ?
C6 C8 1.442(2) . ?
C6 C11 1.400(2) . ?
C7 C14 1.390(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C11 1.376(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C16 1.369(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C19 1.518(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(2) . ?
C15 C16 1.401(2) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.532(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.526(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2 109.5 . . ?
C15 O0 C20 117.72(15) . . ?
C3 N1 C13 123.71(13) . . ?
C3 N1 C17 123.10(14) . . ?
C17 N1 C13 112.90(13) . . ?
C6 C1 H1 119.0 . . ?
C10 C1 H1 119.0 . . ?
C10 C1 C6 122.04(15) . . ?
C7 C2 C5 119.08(14) . . ?
C12 C2 C5 123.68(14) . . ?
C12 C2 C7 117.24(15) . . ?
N1 C3 C9 121.67(14) . . ?
N1 C3 C10 120.99(14) . . ?
C9 C3 C10 117.34(14) . . ?
C5 C4 H4 120.1 . . ?
C8 C4 H4 120.1 . . ?
C8 C4 C5 119.90(15) . . ?
O1 C5 C2 119.16(14) . . ?
O1 C5 C4 119.88(15) . . ?
C4 C5 C2 120.96(14) . . ?
C1 C6 C8 124.41(14) . . ?
C11 C6 C1 116.65(14) . . ?
C11 C6 C8 118.91(14) . . ?
O2 C7 C2 122.23(15) . . ?
O2 C7 C14 116.85(14) . . ?
C14 C7 C2 120.92(15) . . ?
C4 C8 C6 128.62(15) . . ?
C4 C8 H8 115.7 . . ?
C6 C8 H8 115.7 . . ?
C3 C9 H9 119.7 . . ?
C11 C9 C3 120.63(15) . . ?
C11 C9 H9 119.7 . . ?
C1 C10 C3 120.97(15) . . ?
C1 C10 H10 119.5 . . ?
C3 C10 H10 119.5 . . ?
C6 C11 H11 118.8 . . ?
C9 C11 C6 122.36(15) . . ?
C9 C11 H11 118.8 . . ?
C2 C12 H12 119.0 . . ?
C16 C12 C2 122.03(15) . . ?
C16 C12 H12 119.0 . . ?
N1 C13 H13A 111.0 . . ?
N1 C13 H13B 111.0 . . ?
N1 C13 C19 103.98(13) . . ?
H13A C13 H13B 109.0 . . ?
C19 C13 H13A 111.0 . . ?
C19 C13 H13B 111.0 . . ?
C7 C14 H14 120.2 . . ?
C15 C14 C7 119.67(15) . . ?
C15 C14 H14 120.2 . . ?
O0 C15 C14 123.67(16) . . ?
O0 C15 C16 115.46(15) . . ?
C14 C15 C16 120.87(16) . . ?
C12 C16 C15 119.26(16) . . ?
C12 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
N1 C17 H17A 110.9 . . ?
N1 C17 H17B 110.9 . . ?
N1 C17 C18 104.30(14) . . ?
H17A C17 H17B 108.9 . . ?
C18 C17 H17A 110.9 . . ?
C18 C17 H17B 110.9 . . ?
C17 C18 H18A 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
C19 C18 C17 104.62(14) . . ?
C19 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
C13 C19 C18 104.74(14) . . ?
C13 C19 H19A 110.8 . . ?
C13 C19 H19B 110.8 . . ?
C18 C19 H19A 110.8 . . ?
C18 C19 H19B 110.8 . . ?
H19A C19 H19B 108.9 . . ?
O0 C20 H20A 109.5 . . ?
O0 C20 H20B 109.5 . . ?
O0 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C14 C15 179.80(16) . . . . ?
O0 C15 C16 C12 179.51(16) . . . . ?
N1 C3 C9 C11 -178.36(15) . . . . ?
N1 C3 C10 C1 178.42(15) . . . . ?
N1 C13 C19 C18 -27.37(19) . . . . ?
N1 C17 C18 C19 -22.34(18) . . . . ?
C1 C6 C8 C4 1.0(3) . . . . ?
C1 C6 C11 C9 -1.1(2) . . . . ?
C2 C7 C14 C15 -0.7(3) . . . . ?
C2 C12 C16 C15 -0.3(3) . . . . ?
C3 N1 C13 C19 -172.12(16) . . . . ?
C3 N1 C17 C18 -168.68(15) . . . . ?
C3 C9 C11 C6 0.1(3) . . . . ?
C5 C2 C7 O2 0.1(2) . . . . ?
C5 C2 C7 C14 -179.36(15) . . . . ?
C5 C2 C12 C16 179.88(15) . . . . ?
C5 C4 C8 C6 178.07(14) . . . . ?
C6 C1 C10 C3 -0.2(3) . . . . ?
C7 C2 C5 O1 -2.2(2) . . . . ?
C7 C2 C5 C4 177.45(14) . . . . ?
C7 C2 C12 C16 -0.3(2) . . . . ?
C7 C14 C15 O0 -178.92(17) . . . . ?
C7 C14 C15 C16 0.1(3) . . . . ?
C8 C4 C5 O1 -3.6(2) . . . . ?
C8 C4 C5 C2 176.75(14) . . . . ?
C8 C6 C11 C9 177.07(15) . . . . ?
C9 C3 C10 C1 -0.8(2) . . . . ?
C10 C1 C6 C8 -176.91(15) . . . . ?
C10 C1 C6 C11 1.2(2) . . . . ?
C10 C3 C9 C11 0.8(2) . . . . ?
C11 C6 C8 C4 -177.03(16) . . . . ?
C12 C2 C5 O1 177.67(15) . . . . ?
C12 C2 C5 C4 -2.7(2) . . . . ?
C12 C2 C7 O2 -179.75(15) . . . . ?
C12 C2 C7 C14 0.8(2) . . . . ?
C13 N1 C3 C9 179.81(15) . . . . ?
C13 N1 C3 C10 0.7(2) . . . . ?
C13 N1 C17 C18 5.37(19) . . . . ?
C14 C15 C16 C12 0.4(3) . . . . ?
C17 N1 C3 C9 -6.8(3) . . . . ?
C17 N1 C3 C10 174.07(15) . . . . ?
C17 N1 C13 C19 13.88(19) . . . . ?
C17 C18 C19 C13 30.94(19) . . . . ?
C20 O0 C15 C14 -0.8(3) . . . . ?
C20 O0 C15 C16 -179.86(18) . . . . ?


_olex2_date_sample_data_collection 2020-10-30
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C4
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.661
_oxdiff_exptl_absorpt_empirical_full_min 0.717
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_at526
_database_code_depnum_ccdc_archive 'CCDC 2089022'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-02-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H19 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9885(12)
_cell_length_b                   11.7602(11)
_cell_length_c                   16.0667(12)
_cell_angle_alpha                77.958(7)
_cell_angle_beta                 85.456(9)
_cell_angle_gamma                74.512(10)
_cell_volume                     1600.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6110
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.4300
_cell_measurement_theta_min      5.0430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -2 0.0623
0 1 2 0.0623
0 -1 0 0.0663
1 2 0 0.0881
1 0 0 0.0749
-1 2 0 0.0923
-1 0 0 0.0962
-1 -1 0 0.1011
1 6 -5 0.0850
-3 -2 9 0.0887
3 1 -9 0.0860
0 -2 9 0.0675
0 2 -9 0.0706
3 3 9 0.0640
-3 -5 -8 0.0804
-3 0 -8 0.0938
3 6 8 0.0749
5 5 3 0.0680

_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.125
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0017 -0.9939 -1.9908 0.0897 0.1708 -0.0971
-0.0017 0.9939 1.9908 -0.0897 -0.1708 0.0971
0.0012 -0.9961 0.0025 -0.0169 0.0117 -0.1366
0.9977 1.9932 -0.0055 0.1792 -0.0976 0.2026
1.0000 0.0011 -0.0005 0.1454 -0.0743 -0.0706
-1.0024 1.9911 -0.0045 -0.1115 0.0509 0.3439
-1.0000 -0.0011 0.0005 -0.1454 0.0743 0.0706
-0.9989 -0.9971 0.0030 -0.1623 0.0859 -0.0660
0.8983 5.7495 -5.0625 0.4988 0.2686 0.8240
-2.6209 -1.5471 8.5224 -0.8624 -0.4673 -0.1945
2.7135 1.0727 -8.6063 0.8723 0.4728 0.1245
0.4538 -1.9234 9.2374 -0.4602 -0.7483 -0.4778
-0.4752 2.1197 -9.0930 0.4527 0.7360 0.5034
3.4622 2.7522 8.8396 0.0779 -0.9961 -0.0423
-2.8980 -5.2658 -8.1837 -0.0737 0.9319 -0.3550
-3.4547 0.3190 -8.0084 -0.0689 0.8923 0.4462
2.7912 5.5284 8.0029 0.0723 -0.9127 0.4021
5.1971 5.0708 2.6931 0.6978 -0.6619 0.2738

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16841
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.282
_diffrn_reflns_theta_max         67.282
_diffrn_reflns_theta_min         3.977
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -97.00 -26.00   1.00    6.92    --  -41.64 125.00 -90.00   71
  2  ω     10.00 121.00   1.00    6.92    --   41.64  19.00-180.00  111
  3  ω     52.00  78.00   1.00    6.92    --   41.64-125.00-180.00   26
  4  ω    -27.00  55.00   1.00    6.92    --   41.64 -37.00   0.00   82
  5  ω     80.00 106.00   1.00   21.00    --   92.50  30.00 -90.00   26
  6  ω    136.00 162.00   1.00   21.00    --   92.50  30.00 -90.00   26
  7  ω     75.00 101.00   1.00   21.00    --   92.50 -88.00  94.35   26
  8  ω     22.00  58.00   1.00   21.00    --   92.50-125.00-180.00   36
  9  ω     17.00  61.00   1.00   21.00    --   92.50 -30.00 -90.00   44
 10  ω     49.00  75.00   1.00   21.00    --   92.50 -83.00  -2.64   26
 11  ω     20.00  87.00   1.00   21.00    --   92.50 -45.00 150.00   67
 12  ω    121.00 168.00   1.00   21.00    --   92.50  30.00 150.00   47
 13  ω     52.00 123.00   1.00   21.00    --   92.50 -88.00 -59.52   71
 14  ω     10.00  64.00   1.00   21.00    --   92.50 -88.00  37.85   54
 15  ω    129.00 155.00   1.00   21.00    --   92.50  61.00-150.00   26
 16  ω    108.00 152.00   1.00   21.00    --   92.50  77.00 -30.00   44
 17  ω     31.00  57.00   1.00   21.00    --   92.50-125.00 -90.00   26
 18  ω     94.00 120.00   1.00   21.00    --   92.50 125.00 -90.00   26
 19  ω    125.00 151.00   1.00   21.00    --   92.50 125.00 -90.00   26
 20  ω     18.00  47.00   1.00   21.00    --   92.50 -83.00  -2.64   29
 21  ω     48.00  74.00   1.00   21.00    --   92.50 -61.00 150.00   26
 22  ω     63.00  98.00   1.00   21.00    --   92.50 -87.00-110.32   35
 23  ω     25.00  94.00   1.00   21.00    --   92.50 -61.00  30.00   69
 24  ω     18.00 114.00   1.00   21.00    --   92.50 -86.00 129.02   96
 25  ω     89.00 163.00   1.00   21.00    --   92.50  45.00  30.00   74
 26  ω     62.00 121.00   1.00   21.00    --   92.50 -61.00-180.00   59
 27  ω     84.00 134.00   1.00   21.00    --   92.50  77.00  90.00   50
 28  ω     20.00  59.00   1.00   21.00    --   92.50 -45.00  30.00   39
 29  ω     22.00  49.00   1.00   21.00    --   92.50 -61.00 -90.00   27
 30  ω     74.00 100.00   1.00   21.00    --   92.50 -61.00 -90.00   26
 31  ω     77.00 106.00   1.00   21.00    --   92.50 -88.00  37.85   29
 32  ω    109.00 135.00   1.00   21.00    --   92.50  77.00-180.00   26
 33  ω     21.00  59.00   1.00   21.00    --   92.50-125.00 -60.00   38
 34  ω     77.00 127.00   1.00   21.00    --   92.50 125.00-150.00   50
 35  ω     96.00 123.00   1.00   21.00    --   92.50 -88.00 169.99   27
 36  ω     38.00  66.00   1.00   21.00    --   92.50 -88.00 169.99   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1453292000
_diffrn_orient_matrix_UB_12      0.0170251000
_diffrn_orient_matrix_UB_13      -0.0534139000
_diffrn_orient_matrix_UB_21      -0.0742788000
_diffrn_orient_matrix_UB_22      -0.0119985000
_diffrn_orient_matrix_UB_23      -0.0798541000
_diffrn_orient_matrix_UB_31      -0.0708002000
_diffrn_orient_matrix_UB_32      0.1370255000
_diffrn_orient_matrix_UB_33      -0.0197152000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4434
_reflns_number_total             5629
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         5629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0944P)²+0.2772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1587
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C31(H31), C34(H34), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75115(14) 0.29500(11) 0.36124(8) 0.0405(3) Uani 1 1 d . . . . .
O2 O 0.59847(14) 0.31067(11) 0.23621(8) 0.0401(3) Uani 1 1 d . . . . .
H2 H 0.619421 0.325483 0.280893 0.060 Uiso 1 1 calc R U . . .
N1 N 1.43246(19) 0.03702(14) 0.72628(10) 0.0434(4) Uani 1 1 d . . . . .
C1 C 1.5728(2) -0.05557(19) 0.71939(14) 0.0511(5) Uani 1 1 d . . . . .
H1A H 1.547616 -0.129539 0.718091 0.077 Uiso 1 1 calc R U . . .
H1B H 1.635664 -0.066772 0.767505 0.077 Uiso 1 1 calc R U . . .
H1C H 1.628346 -0.031980 0.667987 0.077 Uiso 1 1 calc R U . . .
C2 C 1.4166(3) 0.1017(2) 0.79516(14) 0.0508(5) Uani 1 1 d . . . . .
H2A H 1.440229 0.177707 0.774275 0.076 Uiso 1 1 calc R U . . .
H2B H 1.486489 0.055339 0.839316 0.076 Uiso 1 1 calc R U . . .
H2C H 1.312515 0.115004 0.817613 0.076 Uiso 1 1 calc R U . . .
C3 C 1.3269(2) 0.07432(16) 0.66346(12) 0.0362(4) Uani 1 1 d . . . . .
C4 C 1.1987(2) 0.17364(16) 0.66459(12) 0.0373(4) Uani 1 1 d . . . . .
H4A H 1.184901 0.215522 0.708911 0.045 Uiso 1 1 calc R U . . .
C5 C 1.0941(2) 0.20893(15) 0.60081(11) 0.0355(4) Uani 1 1 d . . . . .
H5 H 1.010778 0.275271 0.602764 0.043 Uiso 1 1 calc R U . . .
C6 C 1.1075(2) 0.14943(15) 0.53313(11) 0.0328(4) Uani 1 1 d . . . . .
C7 C 1.2348(2) 0.04981(16) 0.53278(11) 0.0375(4) Uani 1 1 d . . . . .
H7 H 1.246798 0.007418 0.488825 0.045 Uiso 1 1 calc R U . . .
C8 C 1.3414(2) 0.01344(16) 0.59517(12) 0.0391(4) Uani 1 1 d . . . . .
H8 H 1.424929 -0.052545 0.592638 0.047 Uiso 1 1 calc R U . . .
C9 C 0.9936(2) 0.19347(15) 0.46801(11) 0.0331(4) Uani 1 1 d . . . . .
H9 H 0.912490 0.258101 0.477252 0.040 Uiso 1 1 calc R U . . .
C10 C 0.9877(2) 0.15468(15) 0.39613(11) 0.0349(4) Uani 1 1 d . . . . .
H10 H 1.066301 0.091519 0.382170 0.042 Uiso 1 1 calc R U . . .
C11 C 0.85802(19) 0.21152(14) 0.33957(11) 0.0320(4) Uani 1 1 d . . . . .
C12 C 0.84797(19) 0.17281(14) 0.26053(10) 0.0297(4) Uani 1 1 d . . . . .
C13 C 0.96639(19) 0.08291(14) 0.22981(11) 0.0316(4) Uani 1 1 d . . . . .
H13 H 1.056478 0.049215 0.260415 0.038 Uiso 1 1 calc R U . . .
C14 C 0.9525(2) 0.04491(15) 0.15789(11) 0.0329(4) Uani 1 1 d . . . . .
H14 H 1.032604 -0.013603 0.139590 0.039 Uiso 1 1 calc R U . . .
C15 C 0.8160(2) 0.09384(15) 0.11000(11) 0.0314(4) Uani 1 1 d . . . . .
C16 C 0.7940(2) 0.05314(16) 0.03659(11) 0.0373(4) Uani 1 1 d . . . . .
H16 H 0.871819 -0.006190 0.017470 0.045 Uiso 1 1 calc R U . . .
C17 C 0.6604(2) 0.09960(18) -0.00661(13) 0.0445(5) Uani 1 1 d . . . . .
H17 H 0.647595 0.071212 -0.054727 0.053 Uiso 1 1 calc R U . . .
C18 C 0.5415(2) 0.18991(18) 0.02041(13) 0.0439(5) Uani 1 1 d . . . . .
H18 H 0.450349 0.220458 -0.009504 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5597(2) 0.23295(16) 0.09069(12) 0.0379(4) Uani 1 1 d . . . . .
H19 H 0.481766 0.294051 0.107737 0.046 Uiso 1 1 calc R U . . .
C20 C 0.69627(19) 0.18495(15) 0.13736(11) 0.0311(4) Uani 1 1 d . . . . .
C21 C 0.71491(19) 0.22459(14) 0.21251(11) 0.0313(4) Uani 1 1 d . . . . .
O3 O -0.01723(15) 0.76953(11) 0.12842(8) 0.0411(3) Uani 1 1 d . . . . .
O4 O -0.13682(14) 0.75857(11) -0.00177(8) 0.0392(3) Uani 1 1 d . . . . .
H4 H -0.129310 0.780358 0.042638 0.059 Uiso 1 1 calc R U . . .
N2 N 0.64685(17) 0.62118(13) 0.49888(10) 0.0377(4) Uani 1 1 d . . . . .
C22 C 0.7808(2) 0.51939(18) 0.50529(13) 0.0451(5) Uani 1 1 d . . . . .
H22A H 0.747994 0.446378 0.514359 0.068 Uiso 1 1 calc R U . . .
H22B H 0.841505 0.517953 0.552220 0.068 Uiso 1 1 calc R U . . .
H22C H 0.841780 0.526277 0.453548 0.068 Uiso 1 1 calc R U . . .
C23 C 0.6196(2) 0.69115(18) 0.56525(13) 0.0434(5) Uani 1 1 d . . . . .
H23A H 0.630742 0.770583 0.541832 0.065 Uiso 1 1 calc R U . . .
H23B H 0.692999 0.653036 0.609328 0.065 Uiso 1 1 calc R U . . .
H23C H 0.516893 0.696293 0.588648 0.065 Uiso 1 1 calc R U . . .
C24 C 0.54610(19) 0.64578(15) 0.43511(11) 0.0313(4) Uani 1 1 d . . . . .
C25 C 0.5692(2) 0.57194(15) 0.37394(11) 0.0358(4) Uani 1 1 d . . . . .
H25 H 0.655399 0.506668 0.376973 0.043 Uiso 1 1 calc R U . . .
C26 C 0.4669(2) 0.59489(15) 0.31035(11) 0.0359(4) Uani 1 1 d . . . . .
H26 H 0.485126 0.544370 0.271122 0.043 Uiso 1 1 calc R U . . .
C27 C 0.3351(2) 0.69212(15) 0.30226(11) 0.0323(4) Uani 1 1 d . . . . .
C28 C 0.3139(2) 0.76540(15) 0.36263(11) 0.0329(4) Uani 1 1 d . . . . .
H28 H 0.228130 0.831146 0.358784 0.039 Uiso 1 1 calc R U . . .
C29 C 0.4141(2) 0.74433(15) 0.42711(11) 0.0341(4) Uani 1 1 d . . . . .
H29 H 0.395214 0.795301 0.466057 0.041 Uiso 1 1 calc R U . . .
C30 C 0.2240(2) 0.71680(15) 0.23720(11) 0.0335(4) Uani 1 1 d . . . . .
H30 H 0.136869 0.779821 0.240412 0.040 Uiso 1 1 calc R U . . .
C31 C 0.2308(2) 0.65987(16) 0.17231(11) 0.0352(4) Uani 1 1 d . . . . .
H31 H 0.316798 0.597653 0.165179 0.042 Uiso 1 1 calc R U . . .
C32 C 0.1050(2) 0.69442(14) 0.11294(11) 0.0331(4) Uani 1 1 d . . . . .
C33 C 0.11902(19) 0.64274(14) 0.03688(11) 0.0298(4) Uani 1 1 d . . . . .
C34 C 0.2537(2) 0.55720(15) 0.01462(11) 0.0340(4) Uani 1 1 d . . . . .
H34 H 0.338090 0.532851 0.049972 0.041 Uiso 1 1 calc R U . . .
C35 C 0.2624(2) 0.51048(15) -0.05612(11) 0.0353(4) Uani 1 1 d . . . . .
H35 H 0.351839 0.454510 -0.068462 0.042 Uiso 1 1 calc R U . . .
C36 C 0.1362(2) 0.54619(15) -0.11172(11) 0.0335(4) Uani 1 1 d . . . . .
C37 C 0.1401(2) 0.49932(17) -0.18590(12) 0.0421(4) Uani 1 1 d . . . . .
H37 H 0.227671 0.442607 -0.199453 0.051 Uiso 1 1 calc R U . . .
C38 C 0.0173(3) 0.53608(19) -0.23779(12) 0.0475(5) Uani 1 1 d . . . . .
H38 H 0.021663 0.504071 -0.286462 0.057 Uiso 1 1 calc R U . . .
C39 C -0.1161(3) 0.62166(18) -0.21904(12) 0.0459(5) Uani 1 1 d . . . . .
H39 H -0.199180 0.646179 -0.255346 0.055 Uiso 1 1 calc R U . . .
C40 C -0.1243(2) 0.66891(16) -0.14793(11) 0.0386(4) Uani 1 1 d . . . . .
H40 H -0.212875 0.725775 -0.135708 0.046 Uiso 1 1 calc R U . . .
C41 C 0.0013(2) 0.63169(15) -0.09275(11) 0.0324(4) Uani 1 1 d . . . . .
C42 C -0.0061(2) 0.67940(14) -0.01765(11) 0.0311(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.262(2) . ?
O2 H2 0.8200 . ?
O2 C21 1.341(2) . ?
N1 C1 1.443(3) . ?
N1 C2 1.446(3) . ?
N1 C3 1.362(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.407(3) . ?
C3 C8 1.410(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.368(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(2) . ?
C6 C7 1.403(3) . ?
C6 C9 1.439(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.364(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.337(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.460(2) . ?
C11 C12 1.452(2) . ?
C12 C13 1.424(2) . ?
C12 C21 1.399(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.349(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.419(2) . ?
C15 C16 1.408(2) . ?
C15 C20 1.416(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.359(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.404(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.367(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.410(2) . ?
C20 C21 1.418(3) . ?
O3 C32 1.257(2) . ?
O4 H4 0.8200 . ?
O4 C42 1.334(2) . ?
N2 C22 1.446(2) . ?
N2 C23 1.446(2) . ?
N2 C24 1.355(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.411(2) . ?
C24 C29 1.413(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.365(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.402(2) . ?
C27 C28 1.397(2) . ?
C27 C30 1.435(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.367(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.341(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.455(2) . ?
C32 C33 1.457(2) . ?
C33 C34 1.427(2) . ?
C33 C42 1.399(2) . ?
C34 H34 0.9300 . ?
C34 C35 1.350(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.418(3) . ?
C36 C37 1.408(3) . ?
C36 C41 1.412(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.357(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.402(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.360(3) . ?
C40 H40 0.9300 . ?
C40 C41 1.409(3) . ?
C41 C42 1.423(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 H2 109.5 . . ?
C1 N1 C2 118.31(17) . . ?
C3 N1 C1 120.98(17) . . ?
C3 N1 C2 120.10(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 121.56(17) . . ?
N1 C3 C8 121.00(17) . . ?
C4 C3 C8 117.44(16) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 C3 120.36(17) . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.60(16) . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C7 116.78(16) . . ?
C5 C6 C9 119.07(16) . . ?
C7 C6 C9 124.14(16) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.77(17) . . ?
C8 C7 H7 119.1 . . ?
C3 C8 H8 119.5 . . ?
C7 C8 C3 121.05(17) . . ?
C7 C8 H8 119.5 . . ?
C6 C9 H9 115.4 . . ?
C10 C9 C6 129.20(16) . . ?
C10 C9 H9 115.4 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.95(16) . . ?
C11 C10 H10 120.0 . . ?
O1 C11 C10 118.60(15) . . ?
O1 C11 C12 119.69(15) . . ?
C12 C11 C10 121.69(15) . . ?
C13 C12 C11 123.16(15) . . ?
C21 C12 C11 118.80(15) . . ?
C21 C12 C13 118.03(15) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 C12 122.30(15) . . ?
C14 C13 H13 118.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.29(15) . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 122.13(16) . . ?
C16 C15 C20 118.49(16) . . ?
C20 C15 C14 119.37(15) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.72(17) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.88(18) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.04(17) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.16(17) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C21 119.18(15) . . ?
C19 C20 C15 119.68(16) . . ?
C19 C20 C21 121.13(16) . . ?
O2 C21 C12 122.01(16) . . ?
O2 C21 C20 117.17(15) . . ?
C12 C21 C20 120.79(15) . . ?
C42 O4 H4 109.5 . . ?
C23 N2 C22 117.83(15) . . ?
C24 N2 C22 120.77(15) . . ?
C24 N2 C23 121.31(14) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 C25 120.62(15) . . ?
N2 C24 C29 122.17(16) . . ?
C25 C24 C29 117.21(16) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 120.99(16) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 118.9 . . ?
C25 C26 C27 122.15(16) . . ?
C27 C26 H26 118.9 . . ?
C26 C27 C30 123.31(16) . . ?
C28 C27 C26 116.49(16) . . ?
C28 C27 C30 120.19(15) . . ?
C27 C28 H28 118.7 . . ?
C29 C28 C27 122.61(16) . . ?
C29 C28 H28 118.7 . . ?
C24 C29 H29 119.7 . . ?
C28 C29 C24 120.55(16) . . ?
C28 C29 H29 119.7 . . ?
C27 C30 H30 116.1 . . ?
C31 C30 C27 127.76(16) . . ?
C31 C30 H30 116.1 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.69(16) . . ?
C32 C31 H31 119.7 . . ?
O3 C32 C31 118.91(16) . . ?
O3 C32 C33 120.14(15) . . ?
C31 C32 C33 120.95(15) . . ?
C34 C33 C32 123.64(15) . . ?
C42 C33 C32 118.25(15) . . ?
C42 C33 C34 118.10(15) . . ?
C33 C34 H34 118.9 . . ?
C35 C34 C33 122.12(16) . . ?
C35 C34 H34 118.9 . . ?
C34 C35 H35 119.8 . . ?
C34 C35 C36 120.42(16) . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 122.32(17) . . ?
C37 C36 C41 118.27(17) . . ?
C41 C36 C35 119.41(16) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 C36 120.65(18) . . ?
C38 C37 H37 119.7 . . ?
C37 C38 H38 119.5 . . ?
C37 C38 C39 120.91(18) . . ?
C39 C38 H38 119.5 . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.19(18) . . ?
C40 C39 H39 119.9 . . ?
C39 C40 H40 120.0 . . ?
C39 C40 C41 119.99(18) . . ?
C41 C40 H40 120.0 . . ?
C36 C41 C42 119.33(16) . . ?
C40 C41 C36 119.99(16) . . ?
C40 C41 C42 120.68(16) . . ?
O4 C42 C33 122.25(15) . . ?
O4 C42 C41 117.13(15) . . ?
C33 C42 C41 120.61(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.82 1.74 2.4699(17) 147.7 . yes
O4 H4 O3 0.82 1.73 2.4679(17) 147.9 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C13 177.30(15) . . . . ?
O1 C11 C12 C21 -3.7(2) . . . . ?
N1 C3 C4 C5 -179.75(16) . . . . ?
N1 C3 C8 C7 179.19(16) . . . . ?
C1 N1 C3 C4 -172.56(17) . . . . ?
C1 N1 C3 C8 8.3(3) . . . . ?
C2 N1 C3 C4 -1.7(3) . . . . ?
C2 N1 C3 C8 179.18(16) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C4 C5 C6 C9 -179.11(16) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C5 C6 C9 C10 176.36(17) . . . . ?
C6 C7 C8 C3 0.6(3) . . . . ?
C6 C9 C10 C11 178.53(16) . . . . ?
C7 C6 C9 C10 -2.7(3) . . . . ?
C8 C3 C4 C5 -0.6(3) . . . . ?
C9 C6 C7 C8 178.48(17) . . . . ?
C9 C10 C11 O1 -1.8(3) . . . . ?
C9 C10 C11 C12 179.44(15) . . . . ?
C10 C11 C12 C13 -3.9(3) . . . . ?
C10 C11 C12 C21 175.06(15) . . . . ?
C11 C12 C13 C14 177.44(15) . . . . ?
C11 C12 C21 O2 1.7(2) . . . . ?
C11 C12 C21 C20 -176.50(14) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C12 C21 O2 -179.30(15) . . . . ?
C13 C12 C21 C20 2.5(2) . . . . ?
C13 C14 C15 C16 -177.25(16) . . . . ?
C13 C14 C15 C20 1.5(2) . . . . ?
C14 C15 C16 C17 178.26(16) . . . . ?
C14 C15 C20 C19 -179.25(15) . . . . ?
C14 C15 C20 C21 -0.5(2) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C15 C20 C21 O2 -179.78(14) . . . . ?
C15 C20 C21 C12 -1.5(2) . . . . ?
C16 C15 C20 C19 -0.5(2) . . . . ?
C16 C15 C20 C21 178.29(15) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
C18 C19 C20 C15 1.4(3) . . . . ?
C18 C19 C20 C21 -177.27(16) . . . . ?
C19 C20 C21 O2 -1.1(2) . . . . ?
C19 C20 C21 C12 177.19(15) . . . . ?
C20 C15 C16 C17 -0.5(3) . . . . ?
C21 C12 C13 C14 -1.6(2) . . . . ?
O3 C32 C33 C34 179.90(16) . . . . ?
O3 C32 C33 C42 0.2(2) . . . . ?
N2 C24 C25 C26 178.87(16) . . . . ?
N2 C24 C29 C28 -179.09(16) . . . . ?
C22 N2 C24 C25 0.5(3) . . . . ?
C22 N2 C24 C29 179.90(17) . . . . ?
C23 N2 C24 C25 -175.88(16) . . . . ?
C23 N2 C24 C29 3.5(3) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C25 C24 C29 C28 0.3(2) . . . . ?
C25 C26 C27 C28 0.3(3) . . . . ?
C25 C26 C27 C30 -178.62(16) . . . . ?
C26 C27 C28 C29 -0.6(3) . . . . ?
C26 C27 C30 C31 -4.9(3) . . . . ?
C27 C28 C29 C24 0.3(3) . . . . ?
C27 C30 C31 C32 178.19(16) . . . . ?
C28 C27 C30 C31 176.19(17) . . . . ?
C29 C24 C25 C26 -0.6(3) . . . . ?
C30 C27 C28 C29 178.41(16) . . . . ?
C30 C31 C32 O3 -7.5(3) . . . . ?
C30 C31 C32 C33 172.85(15) . . . . ?
C31 C32 C33 C34 -0.5(3) . . . . ?
C31 C32 C33 C42 179.88(14) . . . . ?
C32 C33 C34 C35 179.56(15) . . . . ?
C32 C33 C42 O4 -0.6(2) . . . . ?
C32 C33 C42 C41 -179.90(14) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C34 C33 C42 O4 179.70(15) . . . . ?
C34 C33 C42 C41 0.4(2) . . . . ?
C34 C35 C36 C37 -179.65(16) . . . . ?
C34 C35 C36 C41 0.3(3) . . . . ?
C35 C36 C37 C38 -179.70(16) . . . . ?
C35 C36 C41 C40 179.34(15) . . . . ?
C35 C36 C41 C42 -0.7(2) . . . . ?
C36 C37 C38 C39 0.1(3) . . . . ?
C36 C41 C42 O4 -179.01(14) . . . . ?
C36 C41 C42 C33 0.3(2) . . . . ?
C37 C36 C41 C40 -0.7(2) . . . . ?
C37 C36 C41 C42 179.31(15) . . . . ?
C37 C38 C39 C40 -0.2(3) . . . . ?
C38 C39 C40 C41 -0.1(3) . . . . ?
C39 C40 C41 C36 0.6(3) . . . . ?
C39 C40 C41 C42 -179.39(16) . . . . ?
C40 C41 C42 O4 1.0(2) . . . . ?
C40 C41 C42 C33 -179.73(15) . . . . ?
C41 C36 C37 C38 0.3(3) . . . . ?
C42 C33 C34 C35 -0.8(3) . . . . ?


_olex2_date_sample_data_collection 2021-02-08
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id AT256
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.200
_oxdiff_exptl_absorpt_empirical_full_min 0.877
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c2
_database_code_depnum_ccdc_archive 'CCDC 2089015'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-10-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H19 N1 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1158(17)
_cell_length_b                   9.9987(11)
_cell_length_c                   12.9251(19)
_cell_angle_alpha                90
_cell_angle_beta                 117.486(18)
_cell_angle_gamma                90
_cell_volume                     1503.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6173
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2730
_cell_measurement_theta_min      3.6070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -14 -3 0.2229
-1 14 3 0.2229
-17 -2 14 0.1491
17 2 -14 0.1491
-7 2 -11 0.1477
7 -2 11 0.1477
-3 -11 -9 0.2139
3 11 9 0.2139
-6 11 -6 0.1995
6 -11 6 0.1995
-10 -12 6 0.2273
10 12 -6 0.2273
11 -11 -10 0.1996
-11 11 10 0.1996

_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.295
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9694 -13.8993 -3.0499 -0.0058 -0.0022 -1.0000
-0.9694 13.8993 3.0499 0.0058 0.0022 1.0000
-17.0162 -1.7350 13.7566 -0.9969 -0.0783 -0.0087
17.0162 1.7350 -13.7566 0.9969 0.0783 0.0087
-7.1685 2.2584 -11.4024 -0.0781 0.9963 0.0354
7.1685 -2.2584 11.4024 0.0781 -0.9963 -0.0354
-2.7257 -11.0900 -8.5196 -0.0414 0.5039 -0.8628
2.7257 11.0900 8.5196 0.0414 -0.5039 0.8628
-5.6563 11.2898 -5.6676 -0.0524 0.6866 0.7251
5.6563 -11.2898 5.6676 0.0524 -0.6866 -0.7251
-9.7249 -11.8938 6.0970 -0.6185 -0.0499 -0.7842
9.7249 11.8938 -6.0970 0.6185 0.0499 0.7842
10.5151 -10.5407 -10.3809 0.5641 0.0428 -0.8246
-10.5151 10.5407 10.3809 -0.5641 -0.0428 0.8246

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10749
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.480
_diffrn_reflns_theta_min         2.739
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00  76.00   1.00   33.02    --  -10.24   0.00-180.00  174
  2  ω    -17.00  78.00   1.00   33.02    --   11.34  57.00  30.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0428035000
_diffrn_orient_matrix_UB_12      0.0074802000
_diffrn_orient_matrix_UB_13      -0.0185775000
_diffrn_orient_matrix_UB_21      -0.0434053000
_diffrn_orient_matrix_UB_22      0.0098874000
_diffrn_orient_matrix_UB_23      -0.0581313000
_diffrn_orient_matrix_UB_31      0.0013712000
_diffrn_orient_matrix_UB_32      0.0698738000
_diffrn_orient_matrix_UB_33      0.0098740000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2947
_reflns_number_total             3708
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²+0.5164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C17(H17),
 C18(H18), C19(H19)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28847(10) 0.54220(13) 0.93837(10) 0.0376(3) Uani 1 1 d . . . . .
O2 O 0.14870(11) 0.60694(13) 1.01252(10) 0.0404(3) Uani 1 1 d . . . . .
H2 H 0.203208 0.567668 1.011708 0.061 Uiso 1 1 calc R U . . .
N1 N 0.66612(11) 0.62720(14) 0.56600(12) 0.0326(3) Uani 1 1 d . . . . .
C1 C 0.13930(13) 0.69479(16) 0.83393(13) 0.0296(3) Uani 1 1 d . . . . .
C2 C 0.45843(13) 0.58774(16) 0.73243(14) 0.0300(3) Uani 1 1 d . . . . .
C3 C 0.24387(13) 0.62062(16) 0.85310(13) 0.0301(3) Uani 1 1 d . . . . .
C4 C 0.07954(14) 0.77866(17) 0.73726(14) 0.0336(4) Uani 1 1 d . . . . .
H4 H 0.105407 0.787057 0.681602 0.040 Uiso 1 1 calc R U . . .
C5 C 0.59906(13) 0.61287(16) 0.61918(14) 0.0301(3) Uani 1 1 d . . . . .
C6 C 0.29558(14) 0.64019(16) 0.77662(14) 0.0314(4) Uani 1 1 d . . . . .
H6 H 0.261085 0.697941 0.713375 0.038 Uiso 1 1 calc R U . . .
C7 C 0.39373(14) 0.57542(16) 0.79592(14) 0.0317(4) Uani 1 1 d . . . . .
H7 H 0.422531 0.515649 0.858065 0.038 Uiso 1 1 calc R U . . .
C8 C 0.56319(14) 0.51882(16) 0.77157(14) 0.0323(4) Uani 1 1 d . . . . .
H8 H 0.586688 0.463235 0.836246 0.039 Uiso 1 1 calc R U . . .
C9 C 0.63213(13) 0.53025(16) 0.71822(14) 0.0323(4) Uani 1 1 d . . . . .
H9 H 0.701063 0.483327 0.747412 0.039 Uiso 1 1 calc R U . . .
C10 C 0.42561(13) 0.66885(16) 0.63316(14) 0.0310(4) Uani 1 1 d . . . . .
H10 H 0.356440 0.715226 0.604236 0.037 Uiso 1 1 calc R U . . .
C11 C 0.09690(14) 0.68422(17) 0.91636(14) 0.0329(4) Uani 1 1 d . . . . .
C12 C 0.49256(14) 0.68156(16) 0.57777(14) 0.0320(4) Uani 1 1 d . . . . .
H12 H 0.467937 0.735888 0.512201 0.038 Uiso 1 1 calc R U . . .
C13 C 0.63663(14) 0.71187(16) 0.46400(14) 0.0322(4) Uani 1 1 d . . . . .
H13A H 0.618410 0.802045 0.477762 0.039 Uiso 1 1 calc R U . . .
H13B H 0.571577 0.675651 0.395891 0.039 Uiso 1 1 calc R U . . .
C14 C 0.77262(13) 0.55302(17) 0.60001(14) 0.0339(4) Uani 1 1 d . . . . .
H14A H 0.761228 0.458342 0.607428 0.041 Uiso 1 1 calc R U . . .
H14B H 0.832732 0.585673 0.673615 0.041 Uiso 1 1 calc R U . . .
C15 C 0.80317(14) 0.57824(18) 0.50141(15) 0.0365(4) Uani 1 1 d . . . . .
H15A H 0.885746 0.585061 0.531181 0.044 Uiso 1 1 calc R U . . .
H15B H 0.774421 0.506879 0.444181 0.044 Uiso 1 1 calc R U . . .
C16 C 0.74467(15) 0.71017(19) 0.44835(17) 0.0393(4) Uani 1 1 d . . . . .
H16A H 0.725315 0.714515 0.366362 0.047 Uiso 1 1 calc R U . . .
H16B H 0.794169 0.785080 0.488507 0.047 Uiso 1 1 calc R U . . .
C17 C -0.01658(15) 0.84879(18) 0.72306(16) 0.0392(4) Uani 1 1 d . . . . .
H17 H -0.054391 0.904467 0.658839 0.047 Uiso 1 1 calc R U . . .
C18 C -0.00105(16) 0.7547(2) 0.90024(17) 0.0428(4) Uani 1 1 d . . . . .
H18 H -0.028811 0.746592 0.954423 0.051 Uiso 1 1 calc R U . . .
C19 C -0.05675(16) 0.8361(2) 0.80486(17) 0.0452(5) Uani 1 1 d . . . . .
H19 H -0.121854 0.883012 0.794980 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2557(19) . ?
O2 H2 0.8200 . ?
O2 C11 1.351(2) . ?
N1 C5 1.351(2) . ?
N1 C13 1.461(2) . ?
N1 C14 1.459(2) . ?
C1 C3 1.476(2) . ?
C1 C4 1.405(2) . ?
C1 C11 1.415(2) . ?
C2 C7 1.432(2) . ?
C2 C8 1.406(2) . ?
C2 C10 1.407(2) . ?
C3 C6 1.447(2) . ?
C4 H4 0.9300 . ?
C4 C17 1.379(2) . ?
C5 C9 1.413(2) . ?
C5 C12 1.421(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.357(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.372(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C12 1.371(2) . ?
C11 C18 1.394(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C16 1.521(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.523(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.521(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C19 1.388(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(3) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 H2 109.5 . . ?
C5 N1 C13 123.87(13) . . ?
C5 N1 C14 123.41(13) . . ?
C14 N1 C13 112.62(13) . . ?
C4 C1 C3 122.88(15) . . ?
C4 C1 C11 117.53(15) . . ?
C11 C1 C3 119.58(14) . . ?
C8 C2 C7 119.38(15) . . ?
C8 C2 C10 116.58(14) . . ?
C10 C2 C7 124.01(15) . . ?
O1 C3 C1 118.78(14) . . ?
O1 C3 C6 120.57(15) . . ?
C6 C3 C1 120.63(14) . . ?
C1 C4 H4 119.3 . . ?
C17 C4 C1 121.49(16) . . ?
C17 C4 H4 119.3 . . ?
N1 C5 C9 121.55(14) . . ?
N1 C5 C12 120.98(15) . . ?
C9 C5 C12 117.46(14) . . ?
C3 C6 H6 119.5 . . ?
C7 C6 C3 120.91(15) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 H7 116.0 . . ?
C6 C7 C2 128.03(15) . . ?
C6 C7 H7 116.0 . . ?
C2 C8 H8 118.7 . . ?
C9 C8 C2 122.67(15) . . ?
C9 C8 H8 118.7 . . ?
C5 C9 H9 119.8 . . ?
C8 C9 C5 120.40(14) . . ?
C8 C9 H9 119.8 . . ?
C2 C10 H10 119.0 . . ?
C12 C10 C2 121.98(15) . . ?
C12 C10 H10 119.0 . . ?
O2 C11 C1 122.01(14) . . ?
O2 C11 C18 117.66(15) . . ?
C18 C11 C1 120.32(16) . . ?
C5 C12 H12 119.5 . . ?
C10 C12 C5 120.90(15) . . ?
C10 C12 H12 119.5 . . ?
N1 C13 H13A 111.0 . . ?
N1 C13 H13B 111.0 . . ?
N1 C13 C16 103.81(13) . . ?
H13A C13 H13B 109.0 . . ?
C16 C13 H13A 111.0 . . ?
C16 C13 H13B 111.0 . . ?
N1 C14 H14A 110.9 . . ?
N1 C14 H14B 110.9 . . ?
N1 C14 C15 104.41(13) . . ?
H14A C14 H14B 108.9 . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C16 C15 C14 104.36(14) . . ?
C16 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C13 C16 H16A 110.8 . . ?
C13 C16 H16B 110.8 . . ?
C15 C16 C13 104.88(14) . . ?
C15 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
H16A C16 H16B 108.8 . . ?
C4 C17 H17 120.1 . . ?
C4 C17 C19 119.83(16) . . ?
C19 C17 H17 120.1 . . ?
C11 C18 H18 119.8 . . ?
C19 C18 C11 120.37(17) . . ?
C19 C18 H18 119.8 . . ?
C17 C19 H19 119.8 . . ?
C18 C19 C17 120.45(17) . . ?
C18 C19 H19 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C6 C7 -0.6(2) . . . . ?
O2 C11 C18 C19 179.28(17) . . . . ?
N1 C5 C9 C8 179.12(15) . . . . ?
N1 C5 C12 C10 -178.78(15) . . . . ?
N1 C13 C16 C15 26.59(18) . . . . ?
N1 C14 C15 C16 24.73(17) . . . . ?
C1 C3 C6 C7 177.93(14) . . . . ?
C1 C4 C17 C19 -0.7(3) . . . . ?
C1 C11 C18 C19 -0.6(3) . . . . ?
C2 C8 C9 C5 -0.5(2) . . . . ?
C2 C10 C12 C5 -0.2(2) . . . . ?
C3 C1 C4 C17 -178.64(15) . . . . ?
C3 C1 C11 O2 -0.6(2) . . . . ?
C3 C1 C11 C18 179.31(15) . . . . ?
C3 C6 C7 C2 -177.00(15) . . . . ?
C4 C1 C3 O1 -176.18(14) . . . . ?
C4 C1 C3 C6 5.2(2) . . . . ?
C4 C1 C11 O2 -179.55(15) . . . . ?
C4 C1 C11 C18 0.3(2) . . . . ?
C4 C17 C19 C18 0.4(3) . . . . ?
C5 N1 C13 C16 172.19(15) . . . . ?
C5 N1 C14 C15 168.02(15) . . . . ?
C7 C2 C8 C9 -177.16(15) . . . . ?
C7 C2 C10 C12 177.43(15) . . . . ?
C8 C2 C7 C6 175.33(16) . . . . ?
C8 C2 C10 C12 -0.7(2) . . . . ?
C9 C5 C12 C10 0.8(2) . . . . ?
C10 C2 C7 C6 -2.7(3) . . . . ?
C10 C2 C8 C9 1.0(2) . . . . ?
C11 C1 C3 O1 4.9(2) . . . . ?
C11 C1 C3 C6 -173.69(14) . . . . ?
C11 C1 C4 C17 0.3(2) . . . . ?
C11 C18 C19 C17 0.3(3) . . . . ?
C12 C5 C9 C8 -0.4(2) . . . . ?
C13 N1 C5 C9 -179.56(15) . . . . ?
C13 N1 C5 C12 0.0(2) . . . . ?
C13 N1 C14 C15 -8.39(18) . . . . ?
C14 N1 C5 C9 4.4(2) . . . . ?
C14 N1 C5 C12 -176.05(15) . . . . ?
C14 N1 C13 C16 -11.42(18) . . . . ?
C14 C15 C16 C13 -31.98(18) . . . . ?


_olex2_date_sample_data_collection 2020-10-21
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.666
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c7
_database_code_depnum_ccdc_archive 'CCDC 2089017'
loop_
_audit_author_name
_audit_author_address
'Erwann Jeanneau'
;universite de Lyon
France
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-08-01 downloaded from the CCDC.
;
_audit_creation_date             2020-10-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O3'
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H19 N1 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2227(7)
_cell_length_b                   12.1794(8)
_cell_length_c                   13.3210(8)
_cell_angle_alpha                91.336(5)
_cell_angle_beta                 91.101(5)
_cell_angle_gamma                112.224(6)
_cell_volume                     1534.22(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15691
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.1100
_cell_measurement_theta_min      3.5060
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -4 -16 0.2564
3 0 18 0.1396
6 7 13 0.2141
3 10 -13 0.2860
13 -13 -3 0.1017
-14 10 3 0.2224
-7 17 3 0.2829
11 6 0 0.2552
-11 -6 0 0.3740
11 -11 10 0.0852
-12 8 -10 0.2585
-8 14 -9 0.2778
0 -9 16 0.2062
-8 -4 14 0.2418
-3 7 17 0.2037
-6 2 17 0.1929
7 1 -16 0.2253
4 -6 -17 0.2388

_exptl_crystal_size_max          0.791
_exptl_crystal_size_mid          0.451
_exptl_crystal_size_min          0.36
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.4783 -3.6405 -16.2065 0.1993 0.8248 0.5292
3.0442 0.1677 18.1168 -0.2261 -0.9384 -0.2613
5.5639 6.9226 12.7499 -0.1534 -0.6318 -0.7598
2.7852 9.8888 -13.3863 0.1754 0.7355 -0.6544
12.7589 -12.6949 -3.0378 -0.9715 0.2334 0.0416
-13.9796 9.5286 2.7342 0.9512 -0.2282 0.2075
-7.1605 16.7243 3.0155 0.7932 -0.1917 -0.5780
10.8666 5.5415 -0.3597 -0.4049 0.0956 -0.9094
-10.8334 -5.5982 0.3486 0.4017 -0.0948 0.9108
10.8587 -10.7450 10.1808 -0.8786 -0.4768 -0.0280
-11.7634 8.1727 -10.1165 0.8564 0.4651 0.2241
-8.2002 14.2544 -9.3042 0.8323 0.4511 -0.3221
0.2685 -8.5451 16.2328 -0.3071 -0.8648 0.3972
-7.6315 -3.5632 14.0697 0.2353 -0.7979 0.5549
-2.9856 7.1127 16.9001 0.2691 -0.9075 -0.3225
-5.7677 2.3212 17.3507 0.2822 -0.9540 0.1013
7.1140 1.3410 -15.7688 -0.2606 0.8824 -0.3917
3.8817 -5.8082 -17.3652 -0.2783 0.9392 0.2011

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40547
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.661
_diffrn_reflns_theta_min         3.061
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -35.00   1.00   10.00    --  -10.40 178.00  30.00   63
  2  ω    -99.00 -39.00   1.00   10.00    --  -10.40-178.00  90.00   60
  3  ω    -43.00  39.00   1.00   10.00    --  -10.40  77.00 -90.00   82
  4  ω    -21.00  39.00   1.00   10.00    --   11.34  77.00   0.00   60
  5  ω    -21.00  39.00   1.00   10.00    --   11.34  77.00-150.00   60
  6  ω    -13.00  86.00   1.00   10.00    --   11.34  37.00 150.00   99
  7  ω    -62.00  39.00   1.00   10.00    --   11.34 -57.00   0.00  101
  8  ω    -82.00 -20.00   1.00   10.00    --  -10.40 149.00 109.00   62
  9  ω    -62.00  39.00   1.00   10.00    --   11.34 -57.00-180.00  101
 10  ω    -21.00  39.00   1.00   10.00    --   11.34  77.00 -90.00   60
 11  ω    -18.00  44.00   1.00   10.00    --   11.34 -77.00  60.00   62
 12  ω    -21.00  39.00   1.00   10.00    --   11.34  77.00  90.00   60
 13  ω    -17.00  84.00   1.00   10.00    --   11.34  57.00 -30.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0508636000
_diffrn_orient_matrix_UB_12      0.0264056000
_diffrn_orient_matrix_UB_13      -0.0041762000
_diffrn_orient_matrix_UB_21      0.0065864000
_diffrn_orient_matrix_UB_22      0.0008970000
_diffrn_orient_matrix_UB_23      -0.0529132000
_diffrn_orient_matrix_UB_31      -0.0547046000
_diffrn_orient_matrix_UB_32      -0.0571320000
_diffrn_orient_matrix_UB_33      -0.0047006000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5878
_reflns_number_total             7773
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0087(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7773
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0888P)²+1.0381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.2039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C16(H16),
 C17(H17), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C32(H32),
  C34(H34), C35(H35)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C36(H36A,H36B,H36C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41488(16) 0.57497(13) 0.58787(12) 0.0377(4) Uani 1 1 d . . . . .
O2 O 0.43519(17) 0.77948(13) 0.64011(12) 0.0404(4) Uani 1 1 d . . . . .
H2 H 0.449910 0.727666 0.607385 0.061 Uiso 1 1 calc R U . . .
O3 O 0.13841(16) 0.82241(12) 0.89760(12) 0.0378(4) Uani 1 1 d . . . . .
N1 N 0.0625(2) -0.17515(15) 0.57693(14) 0.0374(4) Uani 1 1 d . . . . .
C1 C -0.0520(3) -0.2419(2) 0.64017(18) 0.0437(5) Uani 1 1 d . . . . .
H1A H -0.029431 -0.212706 0.708447 0.065 Uiso 1 1 calc R U . . .
H1B H -0.065356 -0.324241 0.636074 0.065 Uiso 1 1 calc R U . . .
H1C H -0.137252 -0.232975 0.617973 0.065 Uiso 1 1 calc R U . . .
C2 C 0.1110(3) -0.2399(2) 0.50344(19) 0.0445(6) Uani 1 1 d . . . . .
H2A H 0.094221 -0.218056 0.437074 0.067 Uiso 1 1 calc R U . . .
H2B H 0.060536 -0.323597 0.510251 0.067 Uiso 1 1 calc R U . . .
H2C H 0.210374 -0.220924 0.514377 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1171(2) -0.05418(17) 0.58073(15) 0.0298(4) Uani 1 1 d . . . . .
C4 C 0.2292(2) 0.01171(18) 0.52012(16) 0.0336(4) Uani 1 1 d . . . . .
H4 H 0.267991 -0.027594 0.476388 0.040 Uiso 1 1 calc R U . . .
C5 C 0.2821(2) 0.13391(18) 0.52500(16) 0.0334(4) Uani 1 1 d . . . . .
H5 H 0.355871 0.175131 0.483768 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2290(2) 0.19878(17) 0.58983(14) 0.0281(4) Uani 1 1 d . . . . .
C7 C 0.1183(2) 0.13211(18) 0.65112(15) 0.0321(4) Uani 1 1 d . . . . .
H7 H 0.081002 0.171691 0.695680 0.038 Uiso 1 1 calc R U . . .
C8 C 0.0639(2) 0.01041(18) 0.64708(15) 0.0322(4) Uani 1 1 d . . . . .
H8 H -0.009488 -0.030527 0.688744 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2878(2) 0.32663(17) 0.59138(15) 0.0299(4) Uani 1 1 d . . . . .
H9 H 0.363658 0.362449 0.550176 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2434(2) 0.39982(17) 0.64697(15) 0.0306(4) Uani 1 1 d . . . . .
H10 H 0.166075 0.367067 0.687606 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3134(2) 0.52808(17) 0.64476(15) 0.0288(4) Uani 1 1 d . . . . .
C12 C 0.2663(2) 0.60435(16) 0.71027(15) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.3308(2) 0.72873(17) 0.70431(15) 0.0288(4) Uani 1 1 d . . . . .
C14 C 0.2899(2) 0.80419(16) 0.76544(15) 0.0299(4) Uani 1 1 d . . . . .
H14 H 0.333024 0.886001 0.759938 0.036 Uiso 1 1 calc R U . . .
C15 C 0.1852(2) 0.75687(17) 0.83414(15) 0.0294(4) Uani 1 1 d . . . . .
C16 C 0.1201(2) 0.63344(17) 0.84272(16) 0.0328(4) Uani 1 1 d . . . . .
H16 H 0.050086 0.601566 0.889248 0.039 Uiso 1 1 calc R U . . .
C17 C 0.1606(2) 0.56026(17) 0.78187(16) 0.0302(4) Uani 1 1 d . . . . .
H17 H 0.116771 0.478598 0.788033 0.036 Uiso 1 1 calc R U . . .
C18 C 0.2060(2) 0.94857(18) 0.89457(18) 0.0373(5) Uani 1 1 d . . . . .
H18A H 0.198315 0.973415 0.827603 0.056 Uiso 1 1 calc R U . . .
H18B H 0.304009 0.972329 0.914056 0.056 Uiso 1 1 calc R U . . .
H18C H 0.161201 0.984734 0.940029 0.056 Uiso 1 1 calc R U . . .
O4 O 0.05354(15) -0.07042(12) 0.11451(11) 0.0337(3) Uani 1 1 d . . . . .
O5 O 0.02663(16) -0.27768(12) 0.15121(12) 0.0356(3) Uani 1 1 d . . . . .
H5A H 0.008118 -0.223955 0.126629 0.053 Uiso 1 1 calc R U . . .
O6 O 0.38278(17) -0.33525(13) 0.35388(13) 0.0420(4) Uani 1 1 d . . . . .
N2 N 0.4799(2) 0.67110(15) 0.08698(14) 0.0379(4) Uani 1 1 d . . . . .
C19 C 0.4219(3) 0.7382(2) 0.02399(19) 0.0434(5) Uani 1 1 d . . . . .
H19A H 0.402455 0.702554 -0.042449 0.065 Uiso 1 1 calc R U . . .
H19B H 0.488878 0.818419 0.020941 0.065 Uiso 1 1 calc R U . . .
H19C H 0.335886 0.738144 0.051793 0.065 Uiso 1 1 calc R U . . .
C20 C 0.6105(3) 0.73585(19) 0.14297(19) 0.0425(5) Uani 1 1 d . . . . .
H20A H 0.594577 0.726442 0.213598 0.064 Uiso 1 1 calc R U . . .
H20B H 0.642441 0.818484 0.128152 0.064 Uiso 1 1 calc R U . . .
H20C H 0.680960 0.705528 0.124252 0.064 Uiso 1 1 calc R U . . .
C21 C 0.4119(2) 0.55174(17) 0.09535(15) 0.0299(4) Uani 1 1 d . . . . .
C22 C 0.2804(2) 0.48810(17) 0.04624(15) 0.0315(4) Uani 1 1 d . . . . .
H22 H 0.237254 0.528111 0.007413 0.038 Uiso 1 1 calc R U . . .
C23 C 0.2155(2) 0.36745(17) 0.05535(15) 0.0300(4) Uani 1 1 d . . . . .
H23 H 0.129166 0.327744 0.021813 0.036 Uiso 1 1 calc R U . . .
C24 C 0.2740(2) 0.30184(16) 0.11296(15) 0.0285(4) Uani 1 1 d . . . . .
C25 C 0.4043(2) 0.36619(17) 0.16242(16) 0.0322(4) Uani 1 1 d . . . . .
H25 H 0.446175 0.325907 0.202037 0.039 Uiso 1 1 calc R U . . .
C26 C 0.4715(2) 0.48623(17) 0.15415(16) 0.0327(4) Uani 1 1 d . . . . .
H26 H 0.557837 0.525442 0.187827 0.039 Uiso 1 1 calc R U . . .
C27 C 0.2040(2) 0.17459(17) 0.11682(15) 0.0291(4) Uani 1 1 d . . . . .
H27 H 0.118090 0.140466 0.081476 0.035 Uiso 1 1 calc R U . . .
C28 C 0.2498(2) 0.09992(17) 0.16614(15) 0.0301(4) Uani 1 1 d . . . . .
H28 H 0.334167 0.130684 0.203727 0.036 Uiso 1 1 calc R U . . .
C29 C 0.1704(2) -0.02778(17) 0.16198(15) 0.0283(4) Uani 1 1 d . . . . .
C30 C 0.2263(2) -0.10740(16) 0.21173(14) 0.0271(4) Uani 1 1 d . . . . .
C31 C 0.1512(2) -0.23120(16) 0.20375(14) 0.0277(4) Uani 1 1 d . . . . .
C32 C 0.2006(2) -0.30972(16) 0.24990(15) 0.0305(4) Uani 1 1 d . . . . .
H32 H 0.149156 -0.391033 0.243584 0.037 Uiso 1 1 calc R U . . .
C33 C 0.3263(2) -0.26665(17) 0.30514(16) 0.0323(4) Uani 1 1 d . . . . .
C34 C 0.4046(2) -0.14398(18) 0.31417(18) 0.0370(5) Uani 1 1 d . . . . .
H34 H 0.489889 -0.114943 0.350676 0.044 Uiso 1 1 calc R U . . .
C35 C 0.3544(2) -0.06748(17) 0.26886(16) 0.0326(4) Uani 1 1 d . . . . .
H35 H 0.406465 0.013670 0.275952 0.039 Uiso 1 1 calc R U . . .
C36 C 0.2981(3) -0.45877(18) 0.35980(18) 0.0398(5) Uani 1 1 d . . . . .
H36A H 0.274051 -0.493579 0.293239 0.060 Uiso 1 1 calc R U . . .
H36B H 0.213176 -0.468379 0.394476 0.060 Uiso 1 1 calc R U . . .
H36C H 0.350133 -0.497328 0.395664 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.257(2) . ?
O2 H2 0.8200 . ?
O2 C13 1.347(2) . ?
O3 C15 1.361(2) . ?
O3 C18 1.429(2) . ?
N1 C1 1.446(3) . ?
N1 C2 1.451(3) . ?
N1 C3 1.363(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.407(3) . ?
C3 C8 1.416(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.406(3) . ?
C6 C7 1.406(3) . ?
C6 C9 1.441(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.355(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.453(3) . ?
C11 C12 1.474(3) . ?
C12 C13 1.410(3) . ?
C12 C17 1.411(3) . ?
C13 C14 1.397(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 C16 1.404(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O4 C29 1.258(2) . ?
O5 H5A 0.8200 . ?
O5 C31 1.354(2) . ?
O6 C33 1.353(2) . ?
O6 C36 1.429(2) . ?
N2 C19 1.450(3) . ?
N2 C20 1.449(3) . ?
N2 C21 1.362(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.411(3) . ?
C21 C26 1.414(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.399(3) . ?
C24 C25 1.405(3) . ?
C24 C27 1.443(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.368(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.348(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.456(3) . ?
C29 C30 1.463(3) . ?
C30 C31 1.410(2) . ?
C30 C35 1.411(3) . ?
C31 C32 1.389(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.379(3) . ?
C33 C34 1.404(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.368(3) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 H2 109.5 . . ?
C15 O3 C18 117.23(16) . . ?
C1 N1 C2 118.29(18) . . ?
C3 N1 C1 121.18(18) . . ?
C3 N1 C2 120.37(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 121.69(19) . . ?
N1 C3 C8 121.08(19) . . ?
C4 C3 C8 117.22(18) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.58(19) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.61(19) . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C7 116.36(18) . . ?
C5 C6 C9 120.26(18) . . ?
C7 C6 C9 123.38(18) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 121.91(19) . . ?
C8 C7 H7 119.0 . . ?
C3 C8 H8 119.3 . . ?
C7 C8 C3 121.31(19) . . ?
C7 C8 H8 119.3 . . ?
C6 C9 H9 116.8 . . ?
C10 C9 C6 126.43(19) . . ?
C10 C9 H9 116.8 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.76(19) . . ?
C11 C10 H10 119.1 . . ?
O1 C11 C10 120.55(18) . . ?
O1 C11 C12 119.44(17) . . ?
C10 C11 C12 120.00(17) . . ?
C13 C12 C11 119.52(17) . . ?
C13 C12 C17 116.79(18) . . ?
C17 C12 C11 123.67(17) . . ?
O2 C13 C12 121.28(18) . . ?
O2 C13 C14 117.36(17) . . ?
C14 C13 C12 121.36(17) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.78(17) . . ?
C15 C14 H14 120.1 . . ?
O3 C15 C14 124.45(17) . . ?
O3 C15 C16 115.29(17) . . ?
C14 C15 C16 120.26(18) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.40(18) . . ?
C17 C16 H16 120.3 . . ?
C12 C17 H17 118.8 . . ?
C16 C17 C12 122.41(18) . . ?
C16 C17 H17 118.8 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C31 O5 H5A 109.5 . . ?
C33 O6 C36 117.66(17) . . ?
C20 N2 C19 117.73(17) . . ?
C21 N2 C19 121.16(19) . . ?
C21 N2 C20 121.09(18) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 122.01(18) . . ?
N2 C21 C26 120.85(19) . . ?
C22 C21 C26 117.14(17) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.49(18) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 118.6 . . ?
C22 C23 C24 122.75(19) . . ?
C24 C23 H23 118.6 . . ?
C23 C24 C25 116.32(17) . . ?
C23 C24 C27 120.44(18) . . ?
C25 C24 C27 123.20(18) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 C24 122.09(18) . . ?
C26 C25 H25 119.0 . . ?
C21 C26 H26 119.4 . . ?
C25 C26 C21 121.20(19) . . ?
C25 C26 H26 119.4 . . ?
C24 C27 H27 116.5 . . ?
C28 C27 C24 126.98(19) . . ?
C28 C27 H27 116.5 . . ?
C27 C28 H28 119.2 . . ?
C27 C28 C29 121.58(19) . . ?
C29 C28 H28 119.2 . . ?
O4 C29 C28 119.98(18) . . ?
O4 C29 C30 119.57(17) . . ?
C28 C29 C30 120.44(17) . . ?
C31 C30 C29 119.90(17) . . ?
C31 C30 C35 116.57(17) . . ?
C35 C30 C29 123.53(17) . . ?
O5 C31 C30 120.77(17) . . ?
O5 C31 C32 117.57(16) . . ?
C32 C31 C30 121.66(18) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.76(17) . . ?
C33 C32 H32 120.1 . . ?
O6 C33 C32 124.45(18) . . ?
O6 C33 C34 115.35(18) . . ?
C32 C33 C34 120.20(18) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 C33 119.50(19) . . ?
C35 C34 H34 120.2 . . ?
C30 C35 H35 118.9 . . ?
C34 C35 C30 122.30(18) . . ?
C34 C35 H35 118.9 . . ?
O6 C36 H36A 109.5 . . ?
O6 C36 H36B 109.5 . . ?
O6 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C13 3.3(3) . . . . ?
O1 C11 C12 C17 -175.16(19) . . . . ?
O2 C13 C14 C15 -178.71(18) . . . . ?
O3 C15 C16 C17 -179.92(18) . . . . ?
N1 C3 C4 C5 179.7(2) . . . . ?
N1 C3 C8 C7 -179.93(19) . . . . ?
C1 N1 C3 C4 179.5(2) . . . . ?
C1 N1 C3 C8 0.2(3) . . . . ?
C2 N1 C3 C4 -5.3(3) . . . . ?
C2 N1 C3 C8 175.4(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C3 C8 C7 0.8(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C4 C5 C6 C9 -179.62(19) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C9 C10 177.3(2) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C6 C9 C10 C11 178.22(18) . . . . ?
C7 C6 C9 C10 -2.9(3) . . . . ?
C8 C3 C4 C5 -1.0(3) . . . . ?
C9 C6 C7 C8 179.36(19) . . . . ?
C9 C10 C11 O1 2.6(3) . . . . ?
C9 C10 C11 C12 -176.87(18) . . . . ?
C10 C11 C12 C13 -177.20(17) . . . . ?
C10 C11 C12 C17 4.3(3) . . . . ?
C11 C12 C13 O2 -0.3(3) . . . . ?
C11 C12 C13 C14 -179.61(18) . . . . ?
C11 C12 C17 C16 179.18(19) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C12 C17 C16 0.6(3) . . . . ?
C13 C14 C15 O3 179.51(18) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C12 0.1(3) . . . . ?
C17 C12 C13 O2 178.34(18) . . . . ?
C17 C12 C13 C14 -1.0(3) . . . . ?
C18 O3 C15 C14 -2.1(3) . . . . ?
C18 O3 C15 C16 177.33(18) . . . . ?
O4 C29 C30 C31 1.8(3) . . . . ?
O4 C29 C30 C35 -178.21(19) . . . . ?
O5 C31 C32 C33 -179.34(18) . . . . ?
O6 C33 C34 C35 -178.9(2) . . . . ?
N2 C21 C22 C23 179.23(19) . . . . ?
N2 C21 C26 C25 -179.6(2) . . . . ?
C19 N2 C21 C22 -2.1(3) . . . . ?
C19 N2 C21 C26 177.8(2) . . . . ?
C20 N2 C21 C22 176.1(2) . . . . ?
C20 N2 C21 C26 -4.0(3) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C22 C23 C24 C27 -177.60(18) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C23 C24 C27 C28 177.72(19) . . . . ?
C24 C25 C26 C21 0.4(3) . . . . ?
C24 C27 C28 C29 -178.46(18) . . . . ?
C25 C24 C27 C28 0.0(3) . . . . ?
C26 C21 C22 C23 -0.7(3) . . . . ?
C27 C24 C25 C26 177.17(19) . . . . ?
C27 C28 C29 O4 -2.6(3) . . . . ?
C27 C28 C29 C30 176.65(18) . . . . ?
C28 C29 C30 C31 -177.44(17) . . . . ?
C28 C29 C30 C35 2.5(3) . . . . ?
C29 C30 C31 O5 -0.6(3) . . . . ?
C29 C30 C31 C32 -179.95(17) . . . . ?
C29 C30 C35 C34 -179.7(2) . . . . ?
C30 C31 C32 C33 0.0(3) . . . . ?
C31 C30 C35 C34 0.3(3) . . . . ?
C31 C32 C33 O6 179.22(19) . . . . ?
C31 C32 C33 C34 -0.5(3) . . . . ?
C32 C33 C34 C35 0.8(3) . . . . ?
C33 C34 C35 C30 -0.8(3) . . . . ?
C35 C30 C31 O5 179.41(18) . . . . ?
C35 C30 C31 C32 0.1(3) . . . . ?
C36 O6 C33 C32 -8.8(3) . . . . ?
C36 O6 C33 C34 170.9(2) . . . . ?


_olex2_date_sample_data_collection 2020-10-22
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id C7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.718
