# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_exp_185_pl
_database_code_depnum_ccdc_archive 'CCDC 1580057'
_audit_update_record             
;
2017-10-14 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;
_audit_creation_date             2016-10-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.10.10 svn.r3347 for OlexSys, GUI svn.r5252)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N O3'
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H21 N O3'
_chemical_oxdiff_usercomment     Czerwieniec_YAN166
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.0221(2)
_cell_length_b                   8.5085(2)
_cell_length_c                   23.2424(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1586.43(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7013
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.4310
_cell_measurement_theta_min      3.7490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.23t (Agilent, 2014)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 10 0.0380
3 3 7 0.0346
-3 -3 -7 0.0846
-1 5 2 0.0506
0 -5 1 0.0410
5 -1 -2 0.0426
-4 3 2 0.1239
2 5 -3 0.0068
-1 5 -1 0.0478
-2 4 8 0.0771
4 -1 -9 0.0301
-4 1 9 0.1151
-5 0 -7 0.1233
4 0 8 0.0464
-1 5 -7 0.0457
1 4 -8 0.0235
-1 3 -12 0.0480
-1 -3 13 0.0884

_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.077
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
-0.0000 4.0000 10.0001 0.4039 -0.8765 -0.1825
3.0000 3.0000 7.0001 0.3308 -0.7376 0.4337
-3.0000 -3.0000 -7.0001 -0.3308 0.7376 -0.4337
-1.0000 5.0000 2.0002 -0.1731 -0.8634 -0.3158
0.0000 -5.0000 0.9998 0.3415 0.8356 0.0984
5.0000 -1.0000 -2.0000 0.0290 0.0597 0.9838
-4.0000 3.0000 2.0001 -0.1208 -0.4316 -0.8384
2.0000 5.0000 -2.9998 -0.4274 -0.8569 0.2980
-1.0000 5.0000 -0.9998 -0.3612 -0.8056 -0.2870
-2.0000 4.0000 8.0001 0.2391 -0.7781 -0.5405
4.0000 -1.0000 -9.0000 -0.4295 0.2245 0.8625
-4.0000 1.0000 9.0000 0.4295 -0.2245 -0.8625
-5.0000 -0.0000 -7.0000 -0.5375 0.2846 -0.8757
4.0000 0.0000 8.0000 0.5804 -0.2739 0.6775
-1.0000 5.0000 -6.9998 -0.7373 -0.6900 -0.2293
1.0000 4.0000 -7.9998 -0.7048 -0.5597 0.1791
-1.0000 3.0000 -11.9999 -0.9393 -0.2518 -0.1381
-1.0000 -3.0000 12.9999 0.9625 0.2924 -0.2487

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16588
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.410
_diffrn_reflns_theta_min         3.804
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_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   -116.00 -17.00   1.00    5.00    --  -41.23 -37.00-120.00   99
  2  ω   -114.00 -13.00   1.00    5.00    --  -41.23 -57.00 150.00  101
  3  ω    -69.00  32.00   1.00    5.00    --  -41.23  57.00 -60.00  101
  4  ω     30.00 139.00   1.00   25.00    --  106.46 -77.00-180.00  109
  5  ω     33.00 121.00   1.00   25.00    --  106.46-125.00  60.00   88
  6  ω     30.00 139.00   1.00   25.00    --  106.46 -77.00  30.00  109
  7  ω     77.00 158.00   1.00   25.00    --  106.46  61.00   0.00   81
  8  ω     32.00 137.00   1.00   25.00    --  106.46-154.00  51.00  105
  9  ω     33.00  77.00   1.00   25.00    --  106.46 -45.00  30.00   44
 10  ω     33.00 121.00   1.00   25.00    --  106.46-125.00-150.00   88
 11  ω     54.00 158.00   1.00   25.00    --  106.46  15.00-150.00  104
 12  ω     30.00  69.00   1.00   25.00    --  106.46 -30.00   0.00   39
 13  ω     74.00 158.00   1.00   25.00    --  106.46  77.00  30.00   84
 14  ω   -117.00  -9.00   1.00    5.00    --  -41.23 -77.00 120.00  108
 15  ω   -117.00  -9.00   1.00    5.00    --  -41.23 -77.00  30.00  108
 16  ω    -97.00  -2.00   1.00    5.00    --  -41.23 125.00  60.00   95
 17  ω     81.00 158.00   1.00   25.00    --  106.46  45.00-120.00   77
 18  ω     77.00 158.00   1.00   25.00    --  106.46  61.00  90.00   81
 19  ω     81.00 144.00   1.00   25.00    --  106.46  45.00 -30.00   63
 20  ω     78.00 158.00   1.00   25.00    --  106.46  30.00 -60.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0197267000
_diffrn_orient_matrix_UB_12      -0.0557544000
_diffrn_orient_matrix_UB_13      0.0626899000
_diffrn_orient_matrix_UB_21      -0.0299514000
_diffrn_orient_matrix_UB_22      -0.1709643000
_diffrn_orient_matrix_UB_23      -0.0192637000
_diffrn_orient_matrix_UB_31      0.1885988000
_diffrn_orient_matrix_UB_32      -0.0215952000
_diffrn_orient_matrix_UB_33      -0.0096108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2903
_reflns_number_total             3165
_reflns_odcompleteness_completeness 99.93
_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 1.171.38.23t (Agilent, 2014)'
_computing_data_collection       'CrysAlisPro 1.171.38.23t (Agilent, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.38.23t (Agilent, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.044
_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)+(0.0411P)²+0.1696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0784
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(2) 0.1(2)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C7(H7A), C5(H5), C8(H8), C2(H2), C6(H6), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O2 O 0.23505(17) 0.88946(15) 0.08828(5) 0.0275(3) Uani 1 1 d . . . . .
O1 O 0.50253(18) 0.94180(17) 0.14058(6) 0.0313(3) Uani 1 1 d . . . . .
O3 O -0.0928(2) 1.15492(18) 0.00605(7) 0.0411(4) Uani 1 1 d . . . . .
N7 N -0.0716(2) 0.84487(19) 0.04545(6) 0.0247(3) Uani 1 1 d . . . . .
C11 C 0.2044(2) 0.7711(2) 0.12126(7) 0.0237(4) Uani 1 1 d . . . . .
C13 C -0.0760(2) 0.7204(2) 0.08047(8) 0.0244(4) Uani 1 1 d . . . . .
C9 C 0.4665(2) 0.8161(2) 0.17365(8) 0.0253(4) Uani 1 1 d . . . . .
C10 C 0.3259(2) 0.7301(2) 0.16502(8) 0.0264(4) Uani 1 1 d . . . . .
H10 H 0.3069 0.6422 0.1879 0.032 Uiso 1 1 calc R . . . .
C1 C 0.8593(2) 0.8219(2) 0.26838(8) 0.0258(4) Uani 1 1 d . . . . .
C12 C 0.0558(2) 0.6825(2) 0.11657(8) 0.0252(4) Uani 1 1 d . . . . .
H12 H 0.0458 0.5929 0.1392 0.030 Uiso 1 1 calc R . . . .
C15 C -0.2146(2) 0.9038(2) 0.01337(8) 0.0279(4) Uani 1 1 d . . . . .
H15A H -0.2972 0.9447 0.0399 0.033 Uiso 1 1 calc R . . . .
H15B H -0.2651 0.8186 -0.0082 0.033 Uiso 1 1 calc R . . . .
C7 C 0.7316(2) 0.8552(2) 0.22482(7) 0.0271(4) Uani 1 1 d . . . . .
H7A H 0.7537 0.9364 0.1991 0.033 Uiso 1 1 calc R . . . .
C16 C -0.1612(2) 1.0315(2) -0.02726(8) 0.0277(4) Uani 1 1 d . . . . .
H16A H -0.0786 0.9916 -0.0540 0.033 Uiso 1 1 calc R . . . .
H16B H -0.2562 1.0693 -0.0491 0.033 Uiso 1 1 calc R . . . .
C5 C 1.1483(3) 0.8369(3) 0.29770(9) 0.0356(5) Uani 1 1 d . . . . .
H5 H 1.2569 0.8698 0.2905 0.043 Uiso 1 1 calc R . . . .
C8 C 0.5869(2) 0.7798(2) 0.21866(8) 0.0275(4) Uani 1 1 d . . . . .
H8 H 0.5615 0.6998 0.2445 0.033 Uiso 1 1 calc R . . . .
C2 C 0.8249(3) 0.7379(2) 0.31884(8) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.7167 0.7044 0.3263 0.038 Uiso 1 1 calc R . . . .
C14 C -0.2304(3) 0.6220(2) 0.07954(9) 0.0318(4) Uani 1 1 d . . . . .
H14A H -0.3244 0.6851 0.0905 0.048 Uiso 1 1 calc GR . . . .
H14B H -0.2185 0.5362 0.1060 0.048 Uiso 1 1 calc GR . . . .
H14C H -0.2477 0.5815 0.0414 0.048 Uiso 1 1 calc GR . . . .
C6 C 1.0220(2) 0.8735(3) 0.25908(8) 0.0306(4) Uani 1 1 d . . . . .
H6 H 1.0462 0.9331 0.2266 0.037 Uiso 1 1 calc R . . . .
C3 C 0.9509(3) 0.7043(2) 0.35778(9) 0.0354(5) Uani 1 1 d . . . . .
H3 H 0.9265 0.6496 0.3914 0.043 Uiso 1 1 calc R . . . .
C4 C 1.1130(3) 0.7518(3) 0.34681(9) 0.0354(5) Uani 1 1 d . . . . .
H4 H 1.1978 0.7265 0.3725 0.043 Uiso 1 1 calc R . . . .
C17 C -0.0532(4) 1.2886(3) -0.02727(14) 0.0567(7) Uani 1 1 d . . . . .
H17A H 0.031(4) 1.252(3) -0.0563(12) 0.045(7) Uiso 1 1 d . . . . .
H17B H -0.151(4) 1.329(4) -0.0530(15) 0.075(10) Uiso 1 1 d . . . . .
H17C H -0.009(5) 1.371(4) 0.0001(15) 0.076(10) Uiso 1 1 d . . . . .
H7 H 0.014(4) 0.905(3) 0.0490(11) 0.043(7) Uiso 1 1 d . . . . .
H1 H 0.406(4) 0.951(3) 0.1156(13) 0.052(8) Uiso 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
O2 C11 1.289(2) . ?
O1 C9 1.349(2) . ?
O1 H1 0.97(3) . ?
O3 C16 1.415(2) . ?
O3 C17 1.412(3) . ?
N7 C13 1.336(2) . ?
N7 C15 1.457(2) . ?
N7 H7 0.86(3) . ?
C11 C10 1.451(3) . ?
C11 C12 1.415(3) . ?
C13 C12 1.387(3) . ?
C13 C14 1.496(3) . ?
C9 C10 1.359(3) . ?
C9 C8 1.457(2) . ?
C10 H10 0.9300 . ?
C1 C7 1.468(3) . ?
C1 C2 1.401(3) . ?
C1 C6 1.394(3) . ?
C12 H12 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.502(3) . ?
C7 H7A 0.9300 . ?
C7 C8 1.334(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C5 C4 1.381(3) . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.386(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C17 H17A 1.00(3) . ?
C17 H17B 1.05(3) . ?
C17 H17C 1.01(4) . ?

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
C9 O1 H1 103.6(17) . . ?
C17 O3 C16 112.63(18) . . ?
C13 N7 C15 124.34(16) . . ?
C13 N7 H7 115.7(18) . . ?
C15 N7 H7 118.3(18) . . ?
O2 C11 C10 118.49(17) . . ?
O2 C11 C12 122.06(16) . . ?
C12 C11 C10 119.45(16) . . ?
N7 C13 C12 122.15(17) . . ?
N7 C13 C14 117.16(17) . . ?
C12 C13 C14 120.69(16) . . ?
O1 C9 C10 121.37(16) . . ?
O1 C9 C8 115.80(17) . . ?
C10 C9 C8 122.84(17) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 C11 122.08(17) . . ?
C9 C10 H10 119.0 . . ?
C2 C1 C7 122.59(18) . . ?
C6 C1 C7 119.04(17) . . ?
C6 C1 C2 118.36(18) . . ?
C11 C12 H12 117.8 . . ?
C13 C12 C11 124.41(16) . . ?
C13 C12 H12 117.8 . . ?
N7 C15 H15A 109.6 . . ?
N7 C15 H15B 109.6 . . ?
N7 C15 C16 110.27(16) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C1 C7 H7A 117.0 . . ?
C8 C7 C1 126.04(18) . . ?
C8 C7 H7A 117.0 . . ?
O3 C16 C15 107.66(15) . . ?
O3 C16 H16A 110.2 . . ?
O3 C16 H16B 110.2 . . ?
C15 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 C9 123.52(17) . . ?
C7 C8 H8 118.2 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.54(19) . . ?
C3 C2 H2 119.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.82(19) . . ?
C5 C6 H6 119.6 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.86(19) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
O3 C17 H17A 105.8(16) . . ?
O3 C17 H17B 114.2(19) . . ?
O3 C17 H17C 107(2) . . ?
H17A C17 H17B 103(2) . . ?
H17A C17 H17C 113(3) . . ?
H17B C17 H17C 113(3) . . ?

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 C11 C10 C9 2.7(3) . . . . ?
O2 C11 C12 C13 -5.8(3) . . . . ?
O1 C9 C10 C11 -2.0(3) . . . . ?
O1 C9 C8 C7 -5.6(3) . . . . ?
N7 C13 C12 C11 1.5(3) . . . . ?
N7 C15 C16 O3 -60.9(2) . . . . ?
C13 N7 C15 C16 -172.78(16) . . . . ?
C10 C11 C12 C13 173.22(17) . . . . ?
C10 C9 C8 C7 174.52(19) . . . . ?
C1 C7 C8 C9 -178.57(17) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C12 C11 C10 C9 -176.32(17) . . . . ?
C15 N7 C13 C12 -170.19(17) . . . . ?
C15 N7 C13 C14 9.6(3) . . . . ?
C7 C1 C2 C3 177.64(19) . . . . ?
C7 C1 C6 C5 -176.45(18) . . . . ?
C8 C9 C10 C11 177.83(17) . . . . ?
C2 C1 C7 C8 -19.1(3) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
C2 C3 C4 C5 1.8(3) . . . . ?
C14 C13 C12 C11 -178.32(17) . . . . ?
C6 C1 C7 C8 159.95(19) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C17 O3 C16 C15 -174.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-18
_olex2_date_sample_submission    2016-10-12
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id 'YAN 156'
_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.762
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(2)
2 0.1(2)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_p148
_database_code_depnum_ccdc_archive 'CCDC 1580058'
_audit_update_record             
;
2017-10-14 deposited with the CCDC.
2018-06-11 downloaded from the CCDC.
;
_audit_creation_date             2016-10-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.10.04 svn.r3343 for OlexSys, GUI svn.r5250)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C24 H27 N O3)'
_chemical_formula_sum            'C48 H54 N2 O6'
_chemical_formula_weight         754.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H27 N1 O3'
_chemical_oxdiff_usercomment     Czerwieniec_Y-05
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                   22.0779(2)
_cell_length_b                   7.22350(10)
_cell_length_c                   25.3699(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.5190(10)
_cell_angle_gamma                90
_cell_volume                     4033.41(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    32994
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.4010
_cell_measurement_theta_min      5.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 -2 -7 0.0705
-12 2 7 0.0705
-5 0 -15 0.0541
5 0 15 0.0541
12 0 9 0.0377
-12 0 -9 0.0443
9 3 5 0.0812
-10 2 -8 0.0499
11 -1 9 0.0434
10 2 -9 0.0779
-11 -2 10 0.0858
0 5 0 0.0981
-10 3 9 0.0676
13 2 -1 0.0537
13 -2 1 0.0561
9 3 -8 0.0756
-4 -3 -11 0.0615
-1 3 -13 0.0732
3 1 15 0.0553
9 0 12 0.0328
1 -4 5 0.1047

_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.082
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
11.9915 -2.0006 -7.0088 -0.2321 -0.9372 -0.2834
-11.9915 2.0006 7.0088 0.2321 0.9372 0.2834
-5.0047 0.0009 -14.9975 0.9561 -0.3019 0.0486
5.0047 -0.0009 14.9975 -0.9561 0.3019 -0.0486
12.0014 -0.0011 8.9931 -0.9999 -0.2770 0.0432
-12.0014 0.0011 -8.9931 0.9999 0.2770 -0.0432
9.0066 2.9996 4.9966 -0.6668 -0.1726 0.6747
-9.9973 2.0012 -7.9930 0.8567 0.2789 0.3883
10.9995 -1.0011 8.9930 -0.9523 -0.2594 -0.1755
9.9993 2.0000 -9.0051 -0.0425 -0.7762 0.5550
-10.9988 -2.0000 10.0058 0.0419 0.8642 -0.5690
0.0103 5.0006 0.0031 -0.0013 0.1667 1.0533
-9.9890 3.0006 9.0082 0.0412 0.9429 0.4982
13.0017 1.9995 -1.0067 -0.5682 -0.6322 0.5318
12.9942 -2.0010 0.9909 -0.6631 -0.6913 -0.3227
9.0019 3.0002 -8.0039 -0.0433 -0.6549 0.7517
-4.0096 -2.9997 -10.9998 0.7177 -0.3044 -0.5990
-0.9984 3.0010 -12.9980 0.6700 -0.3313 0.7009
3.0071 0.9993 14.9994 -0.8617 0.4371 0.1460
9.0030 -0.0010 11.9950 -1.0017 -0.0130 0.0013
0.9934 -4.0008 4.9971 -0.2861 0.0012 -0.8642

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            86784
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.556
_diffrn_reflns_theta_min         3.495
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_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      4.00  33.00   1.00    3.50    --   40.00  88.00-114.76   29
  2  ω      3.00  32.00   1.00    3.50    --   40.00  90.00  94.75   29
  3  ω   -116.00 -17.00   1.00    3.50    --  -41.23 -37.00-150.00   99
  4  ω   -116.00 -17.00   1.00    3.50    --  -41.23 -37.00 -60.00   99
  5  ω   -116.00 -17.00   1.00    3.50    --  -41.23 -37.00 120.00   99
  6  ω    -97.00  -2.00   1.00    3.50    --  -41.23 125.00 -60.00   95
  7  ω   -114.00 -13.00   1.00    3.50    --  -41.23 -57.00  60.00  101
  8  ω      2.00  97.00   1.00    3.50    --   41.23-125.00-150.00   95
  9  ω      7.00  33.00   1.00    3.50    --   44.00  89.00 -24.26   26
 10  ω      7.00  33.00   1.00    3.50    --   44.00  89.00-173.86   26
 11  ω     18.00  45.00   1.00    3.50    --   52.00  82.00  -8.09   27
 12  ω     23.00 132.00   1.00    3.50    --   56.00  77.00 -43.26  109
 13  ω     23.00  49.00   1.00    3.50    --   56.00  78.00-102.16   26
 14  ω     32.00 140.00   1.00    3.50    --   64.00  76.00-173.65  108
 15  ω     31.00 140.00   1.00    3.50    --   64.00  77.00 110.60  109
 16  ω     31.00 140.00   1.00    3.50    --   64.00  77.00 148.82  109
 17  ω     36.00 143.00   1.00    3.50    --   68.00  75.00  63.30  107
 18  ω     35.00 144.00   1.00    3.50    --   68.00  77.00-160.04  109
 19  ω     35.00 144.00   1.00    3.50    --   68.00  77.00  25.12  109
 20  ω     35.00 144.00   1.00    3.50    --   68.00  77.00  25.12  109
 21  ω     39.00 148.00   1.00    3.50    --   72.00  77.00-119.39  109
 22  ω     74.00 158.00   1.00   30.00    --  106.46  77.00 150.00   84
 23  ω     74.00 158.00   1.00   30.00    --  106.46  77.00  30.00   84
 24  ω     74.00 158.00   1.00   30.00    --  106.46  77.00 -60.00   84
 25  ω     77.00 158.00   1.00   30.00    --  106.46  61.00  90.00   81
 26  ω     34.00 136.00   1.00   30.00    --  106.46 -61.00-180.00  102
 27  ω     77.00 158.00   1.00   30.00    --  106.46  61.00  60.00   81
 28  ω     74.00 158.00   1.00   30.00    --  106.46  77.00 -30.00   84
 29  ω     74.00 158.00   1.00   30.00    --  106.46  77.00-120.00   84
 30  ω     77.00 158.00   1.00   30.00    --  106.46  61.00 120.00   81
 31  ω     24.00 109.00   1.00   30.00    --  106.46 -94.00 -90.00   85
 32  ω     24.00 109.00   1.00   30.00    --  106.46 -94.00  60.00   85
 33  ω     74.00 158.00   1.00   30.00    --  106.46  77.00   0.00   84
 34  ω     77.00 109.00   1.00   30.00    --  106.46  61.00   0.00   32
 35  ω     74.00 142.00   1.00   30.00    --  106.46  77.00-180.00   68
 36  ω     74.00 154.00   1.00   30.00    --  106.46  77.00  60.00   80
 37  ω     24.00  98.00   1.00   30.00    --  106.46 -94.00   0.00   74
 38  ω     74.00 150.00   1.00   30.00    --  106.46  77.00 -90.00   76
 39  ω     74.00 144.00   1.00   30.00    --  106.46  77.00 120.00   70
 40  ω     42.00  71.00   1.00   30.00    --  106.46 -45.00  30.00   29
 41  ω     34.00 101.00   1.00   30.00    --  106.46 -94.00 120.00   67
 42  ω     39.00  77.00   1.00   30.00    --  106.46 -45.00 -30.00   38
 43  ω     78.00 103.00   1.00   30.00    --  106.46  61.00 -90.00   25
 44  ω     74.00 154.00   1.00   30.00    --  106.46  77.00-150.00   80
 45  ω     39.00 109.00   1.00   30.00    --  106.46 -94.00-180.00   70
 46  ω     74.00 101.00   1.00   30.00    --  106.46  77.00  90.00   27
 47  ω     88.00 121.00   1.00   30.00    --  106.46-125.00   0.00   33
 48  ω     78.00 136.00   1.00   30.00    --  106.46  61.00 150.00   58
 49  ω     40.00  68.00   1.00   30.00    --  106.46 -45.00  90.00   28
 50  ω     33.00  81.00   1.00   30.00    --  106.46-125.00   0.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0473925000
_diffrn_orient_matrix_UB_12      -0.0001291000
_diffrn_orient_matrix_UB_13      -0.0479375000
_diffrn_orient_matrix_UB_21      -0.0508864000
_diffrn_orient_matrix_UB_22      0.0334125000
_diffrn_orient_matrix_UB_23      0.0371146000
_diffrn_orient_matrix_UB_31      0.0080522000
_diffrn_orient_matrix_UB_32      0.2106159000
_diffrn_orient_matrix_UB_33      -0.0059152000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6959
_reflns_number_total             8076
_reflns_odcompleteness_completeness 99.95
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8076
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.024
_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)+(0.0480P)²+1.2437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0961
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C22(H22A,H22B), C46(H46A,H46B), C47(H47A,H47B), C23(H23A,H23B), C39(H39A,
 H39B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C29(H29), C34(H34), C38(H38), C27(H27), C13(H13), C10(H10),
 C11(H11), C14(H14), C32(H32), C5(H5A), C31(H31), C37(H37), C35(H35), C7(H7),
 C3(H3), C8(H8), C45(H45), C41(H41), C44(H44), C17(H17), C21(H21), C42(H42),
 C43(H43), C20(H20), C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C48(H48A,H48B,H48C), C24(H24A,H24B,H24C), C2(H2B,H2C,H2D)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A), 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
O4 O 0.27175(3) 0.21094(11) 0.46808(3) 0.02171(17) Uani 1 1 d . . . . .
O1 O 0.52444(3) 0.37778(11) 0.22613(3) 0.02192(17) Uani 1 1 d . . . . .
O6 O 0.33474(3) 0.28458(12) 0.88745(3) 0.02352(17) Uani 1 1 d . . . . .
O3 O 0.57620(3) 0.06767(11) 0.63812(3) 0.02308(17) Uani 1 1 d . . . . .
O2 O 0.51590(4) 0.40195(12) 0.32269(3) 0.02687(19) Uani 1 1 d . . . . .
H2A H 0.5085 0.4214 0.2910 0.040 Uiso 1 1 calc GR . . . .
O5 O 0.26264(4) 0.14517(13) 0.56202(3) 0.02812(19) Uani 1 1 d . . . . .
H5 H 0.2556 0.1396 0.5298 0.042 Uiso 1 1 calc GR . . . .
N2 N 0.29238(4) 0.25058(13) 0.36843(3) 0.02012(19) Uani 1 1 d . . . . .
H2 H 0.2677 0.2139 0.3909 0.024 Uiso 1 1 calc R . . . .
N1 N 0.54255(4) 0.36371(14) 0.12399(3) 0.0219(2) Uani 1 1 d . . . . .
H1 H 0.5171 0.3899 0.1469 0.026 Uiso 1 1 calc R . . . .
C28 C 0.31659(5) 0.32270(15) 0.47957(4) 0.0181(2) Uani 1 1 d . . . . .
C9 C 0.55145(5) 0.21415(15) 0.47882(4) 0.0194(2) Uani 1 1 d . . . . .
C4 C 0.57100(5) 0.27044(15) 0.23407(4) 0.0193(2) Uani 1 1 d . . . . .
C25 C 0.33661(5) 0.36668(15) 0.38605(4) 0.0193(2) Uani 1 1 d . . . . .
C30 C 0.30800(5) 0.26444(15) 0.57376(4) 0.0196(2) Uani 1 1 d . . . . .
C29 C 0.33548(5) 0.35530(15) 0.53480(4) 0.0193(2) Uani 1 1 d . . . . .
H29 H 0.3666 0.4389 0.5438 0.023 Uiso 1 1 calc R . . . .
C33 C 0.30434(5) 0.22453(15) 0.72418(4) 0.0190(2) Uani 1 1 d . . . . .
C12 C 0.56455(5) 0.11928(15) 0.58649(4) 0.0194(2) Uani 1 1 d . . . . .
C36 C 0.32103(5) 0.26109(15) 0.83438(4) 0.0190(2) Uani 1 1 d . . . . .
C34 C 0.35880(5) 0.29556(15) 0.74836(4) 0.0198(2) Uani 1 1 d . . . . .
H34 H 0.3896 0.3316 0.7276 0.024 Uiso 1 1 calc R . . . .
C38 C 0.25943(5) 0.16996(15) 0.75671(4) 0.0211(2) Uani 1 1 d . . . . .
H38 H 0.2235 0.1195 0.7414 0.025 Uiso 1 1 calc R . . . .
C27 C 0.34782(5) 0.40804(15) 0.43929(4) 0.0193(2) Uani 1 1 d . . . . .
H27 H 0.3773 0.4962 0.4491 0.023 Uiso 1 1 calc R . . . .
C6 C 0.56238(5) 0.28319(15) 0.32976(4) 0.0199(2) Uani 1 1 d . . . . .
C13 C 0.51253(5) 0.21154(16) 0.56614(4) 0.0216(2) Uani 1 1 d . . . . .
H13 H 0.4821 0.2422 0.5879 0.026 Uiso 1 1 calc R . . . .
C10 C 0.60338(5) 0.12015(15) 0.50035(4) 0.0206(2) Uani 1 1 d . . . . .
H10 H 0.6338 0.0885 0.4786 0.025 Uiso 1 1 calc R . . . .
C11 C 0.60992(5) 0.07416(15) 0.55321(4) 0.0209(2) Uani 1 1 d . . . . .
H11 H 0.6447 0.0127 0.5668 0.025 Uiso 1 1 calc R . . . .
C14 C 0.50674(5) 0.25721(16) 0.51277(4) 0.0217(2) Uani 1 1 d . . . . .
H14 H 0.4719 0.3185 0.4992 0.026 Uiso 1 1 calc R . . . .
C32 C 0.29300(5) 0.20891(15) 0.66692(4) 0.0207(2) Uani 1 1 d . . . . .
H32 H 0.2602 0.1359 0.6547 0.025 Uiso 1 1 calc R . . . .
C5 C 0.59140(5) 0.21930(16) 0.28779(4) 0.0209(2) Uani 1 1 d . . . . .
H5A H 0.6248 0.1416 0.2938 0.025 Uiso 1 1 calc R . . . .
C31 C 0.32476(5) 0.28833(16) 0.62994(4) 0.0209(2) Uani 1 1 d . . . . .
H31 H 0.3584 0.3606 0.6406 0.025 Uiso 1 1 calc R . . . .
C37 C 0.26686(5) 0.18895(16) 0.81144(4) 0.0206(2) Uani 1 1 d . . . . .
H37 H 0.2360 0.1539 0.8323 0.025 Uiso 1 1 calc R . . . .
C35 C 0.36722(5) 0.31261(16) 0.80255(4) 0.0204(2) Uani 1 1 d . . . . .
H35 H 0.4037 0.3585 0.8180 0.025 Uiso 1 1 calc R . . . .
C7 C 0.57772(5) 0.22523(16) 0.38416(4) 0.0212(2) Uani 1 1 d . . . . .
H7 H 0.6130 0.1570 0.3921 0.025 Uiso 1 1 calc R . . . .
C22 C 0.53405(5) 0.12498(16) 0.67538(4) 0.0211(2) Uani 1 1 d . . . . .
H22A H 0.4947 0.0681 0.6669 0.025 Uiso 1 1 calc R . . . .
H22B H 0.5291 0.2584 0.6744 0.025 Uiso 1 1 calc R . . . .
C1 C 0.58928(5) 0.25302(16) 0.13925(4) 0.0224(2) Uani 1 1 d . . . . .
C3 C 0.60262(5) 0.20256(16) 0.19150(4) 0.0224(2) Uani 1 1 d . . . . .
H3 H 0.6342 0.1192 0.1992 0.027 Uiso 1 1 calc R . . . .
C46 C 0.28963(5) 0.23848(16) 0.92324(4) 0.0207(2) Uani 1 1 d . . . . .
H46A H 0.2788 0.1086 0.9201 0.025 Uiso 1 1 calc R . . . .
H46B H 0.2533 0.3124 0.9157 0.025 Uiso 1 1 calc R . . . .
C8 C 0.54246(5) 0.26742(15) 0.42323(4) 0.0207(2) Uani 1 1 d . . . . .
H8 H 0.5083 0.3390 0.4138 0.025 Uiso 1 1 calc R . . . .
C47 C 0.31838(5) 0.28022(17) 0.97803(4) 0.0230(2) Uani 1 1 d . . . . .
H47A H 0.3293 0.4102 0.9801 0.028 Uiso 1 1 calc R . . . .
H47B H 0.3554 0.2083 0.9841 0.028 Uiso 1 1 calc R . . . .
C40 C 0.23801(5) 0.02129(17) 0.31407(4) 0.0222(2) Uani 1 1 d . . . . .
C16 C 0.48491(5) 0.59404(17) 0.07101(4) 0.0240(2) Uani 1 1 d . . . . .
C23 C 0.56001(5) 0.06403(18) 0.72933(4) 0.0259(2) Uani 1 1 d . . . . .
H23A H 0.6017 0.1062 0.7349 0.031 Uiso 1 1 calc R . . . .
H23B H 0.5602 -0.0701 0.7309 0.031 Uiso 1 1 calc R . . . .
C45 C 0.25844(5) -0.15456(17) 0.32910(4) 0.0268(2) Uani 1 1 d . . . . .
H45 H 0.2997 -0.1748 0.3373 0.032 Uiso 1 1 calc R . . . .
C26 C 0.37526(5) 0.44791(18) 0.34617(4) 0.0272(3) Uani 1 1 d . . . . .
H26A H 0.3999 0.3525 0.3325 0.041 Uiso 1 1 calc GR . . . .
H26B H 0.4010 0.5420 0.3626 0.041 Uiso 1 1 calc GR . . . .
H26C H 0.3497 0.5014 0.3178 0.041 Uiso 1 1 calc GR . . . .
C39 C 0.28218(6) 0.18044(18) 0.31435(4) 0.0268(2) Uani 1 1 d . . . . .
H39A H 0.3203 0.1391 0.3018 0.032 Uiso 1 1 calc R . . . .
H39B H 0.2658 0.2780 0.2911 0.032 Uiso 1 1 calc R . . . .
C48 C 0.27636(5) 0.23629(19) 1.02112(4) 0.0291(3) Uani 1 1 d . . . . .
H48A H 0.2390 0.3036 1.0146 0.044 Uiso 1 1 calc GR . . . .
H48B H 0.2956 0.2716 1.0549 0.044 Uiso 1 1 calc GR . . . .
H48C H 0.2679 0.1059 1.0211 0.044 Uiso 1 1 calc GR . . . .
C41 C 0.17625(6) 0.04867(19) 0.30184(5) 0.0305(3) Uani 1 1 d . . . . .
H41 H 0.1620 0.1655 0.2918 0.037 Uiso 1 1 calc R . . . .
C15 C 0.53186(6) 0.44302(19) 0.07115(4) 0.0292(3) Uani 1 1 d . . . . .
H15A H 0.5180 0.3470 0.0463 0.035 Uiso 1 1 calc R . . . .
H15B H 0.5695 0.4932 0.0600 0.035 Uiso 1 1 calc R . . . .
C24 C 0.52359(6) 0.14009(19) 0.77319(5) 0.0301(3) Uani 1 1 d . . . . .
H24A H 0.4825 0.0962 0.7683 0.045 Uiso 1 1 calc GR . . . .
H24B H 0.5238 0.2729 0.7720 0.045 Uiso 1 1 calc GR . . . .
H24C H 0.5415 0.0990 0.8069 0.045 Uiso 1 1 calc GR . . . .
C44 C 0.21782(6) -0.29970(19) 0.33193(5) 0.0333(3) Uani 1 1 d . . . . .
H44 H 0.2319 -0.4168 0.3421 0.040 Uiso 1 1 calc R . . . .
C2 C 0.62882(6) 0.18791(19) 0.09760(5) 0.0325(3) Uani 1 1 d . . . . .
H2B H 0.6040 0.1345 0.0688 0.049 Uiso 1 1 calc GR . . . .
H2C H 0.6568 0.0966 0.1124 0.049 Uiso 1 1 calc GR . . . .
H2D H 0.6510 0.2909 0.0849 0.049 Uiso 1 1 calc GR . . . .
C17 C 0.50294(6) 0.7779(2) 0.07523(5) 0.0356(3) Uani 1 1 d . . . . .
H17 H 0.5441 0.8073 0.0783 0.043 Uiso 1 1 calc R . . . .
C21 C 0.42358(6) 0.5516(2) 0.06719(5) 0.0363(3) Uani 1 1 d . . . . .
H21 H 0.4112 0.4287 0.0649 0.044 Uiso 1 1 calc R . . . .
C42 C 0.13549(6) -0.0978(2) 0.30457(5) 0.0376(3) Uani 1 1 d . . . . .
H42 H 0.0942 -0.0787 0.2962 0.045 Uiso 1 1 calc R . . . .
C43 C 0.15647(6) -0.2709(2) 0.31970(5) 0.0360(3) Uani 1 1 d . . . . .
H43 H 0.1293 -0.3685 0.3217 0.043 Uiso 1 1 calc R . . . .
C20 C 0.38066(6) 0.6913(3) 0.06680(6) 0.0500(4) Uani 1 1 d . . . . .
H20 H 0.3395 0.6619 0.0642 0.060 Uiso 1 1 calc R . . . .
C19 C 0.39872(8) 0.8742(3) 0.07033(6) 0.0541(5) Uani 1 1 d . . . . .
H19 H 0.3698 0.9681 0.0696 0.065 Uiso 1 1 calc R . . . .
C18 C 0.46009(8) 0.9174(2) 0.07492(7) 0.0517(4) Uani 1 1 d . . . . .
H18 H 0.4724 1.0403 0.0778 0.062 Uiso 1 1 calc R . . . .


_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
O4 C28 1.2928(13) . ?
O1 C4 1.2907(13) . ?
O6 C36 1.3673(13) . ?
O6 C46 1.4386(12) . ?
O3 C12 1.3668(13) . ?
O3 C22 1.4385(12) . ?
O2 H2A 0.8200 . ?
O2 C6 1.3387(13) . ?
O5 H5 0.8200 . ?
O5 C30 1.3367(13) . ?
N2 H2 0.8600 . ?
N2 C25 1.3371(14) . ?
N2 C39 1.4634(13) . ?
N1 H1 0.8600 . ?
N1 C1 1.3381(15) . ?
N1 C15 1.4597(14) . ?
C28 C29 1.4493(14) . ?
C28 C27 1.4181(15) . ?
C9 C10 1.4055(15) . ?
C9 C14 1.3951(15) . ?
C9 C8 1.4602(14) . ?
C4 C5 1.4493(15) . ?
C4 C3 1.4189(15) . ?
C25 C27 1.3864(15) . ?
C25 C26 1.4941(15) . ?
C30 C29 1.3675(15) . ?
C30 C31 1.4542(14) . ?
C29 H29 0.9300 . ?
C33 C34 1.4033(15) . ?
C33 C38 1.3959(15) . ?
C33 C32 1.4589(14) . ?
C12 C13 1.3914(15) . ?
C12 C11 1.3982(15) . ?
C36 C37 1.3895(15) . ?
C36 C35 1.4001(15) . ?
C34 H34 0.9300 . ?
C34 C35 1.3783(15) . ?
C38 H38 0.9300 . ?
C38 C37 1.3921(15) . ?
C27 H27 0.9300 . ?
C6 C5 1.3655(15) . ?
C6 C7 1.4564(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.3896(15) . ?
C10 H10 0.9300 . ?
C10 C11 1.3781(15) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C32 H32 0.9300 . ?
C32 C31 1.3435(15) . ?
C5 H5A 0.9300 . ?
C31 H31 0.9300 . ?
C37 H37 0.9300 . ?
C35 H35 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.3427(15) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.5073(15) . ?
C1 C3 1.3838(16) . ?
C1 C2 1.4986(15) . ?
C3 H3 0.9300 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 C47 1.5121(15) . ?
C8 H8 0.9300 . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C48 1.5220(15) . ?
C40 C45 1.3912(17) . ?
C40 C39 1.5073(16) . ?
C40 C41 1.3883(16) . ?
C16 C15 1.5046(17) . ?
C16 C17 1.3880(19) . ?
C16 C21 1.3843(17) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.5257(15) . ?
C45 H45 0.9300 . ?
C45 C44 1.3851(18) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C41 H41 0.9300 . ?
C41 C42 1.394(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C44 H44 0.9300 . ?
C44 C43 1.381(2) . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.383(2) . ?
C42 H42 0.9300 . ?
C42 C43 1.377(2) . ?
C43 H43 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.386(3) . ?
C18 H18 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
C36 O6 C46 118.83(8) . . ?
C12 O3 C22 117.95(8) . . ?
C6 O2 H2A 109.5 . . ?
C30 O5 H5 109.5 . . ?
C25 N2 H2 117.1 . . ?
C25 N2 C39 125.80(9) . . ?
C39 N2 H2 117.1 . . ?
C1 N1 H1 117.8 . . ?
C1 N1 C15 124.44(9) . . ?
C15 N1 H1 117.8 . . ?
O4 C28 C29 118.45(9) . . ?
O4 C28 C27 121.07(9) . . ?
C27 C28 C29 120.47(9) . . ?
C10 C9 C8 123.18(10) . . ?
C14 C9 C10 117.57(10) . . ?
C14 C9 C8 119.25(10) . . ?
O1 C4 C5 118.99(9) . . ?
O1 C4 C3 121.50(10) . . ?
C3 C4 C5 119.51(10) . . ?
N2 C25 C27 122.03(10) . . ?
N2 C25 C26 117.45(9) . . ?
C27 C25 C26 120.50(10) . . ?
O5 C30 C29 121.03(10) . . ?
O5 C30 C31 115.03(9) . . ?
C29 C30 C31 123.94(10) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.70(10) . . ?
C30 C29 H29 119.6 . . ?
C34 C33 C32 122.51(10) . . ?
C38 C33 C34 117.96(10) . . ?
C38 C33 C32 119.52(10) . . ?
O3 C12 C13 125.01(10) . . ?
O3 C12 C11 115.18(9) . . ?
C13 C12 C11 119.81(10) . . ?
O6 C36 C37 125.13(10) . . ?
O6 C36 C35 114.84(9) . . ?
C37 C36 C35 120.01(10) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.81(10) . . ?
C35 C34 H34 119.6 . . ?
C33 C38 H38 119.0 . . ?
C37 C38 C33 121.90(10) . . ?
C37 C38 H38 119.0 . . ?
C28 C27 H27 118.4 . . ?
C25 C27 C28 123.29(10) . . ?
C25 C27 H27 118.4 . . ?
O2 C6 C5 120.92(10) . . ?
O2 C6 C7 115.46(9) . . ?
C5 C6 C7 123.60(10) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.02(10) . . ?
C14 C13 H13 120.5 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.95(10) . . ?
C11 C10 H10 119.5 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.42(10) . . ?
C10 C11 H11 119.8 . . ?
C9 C14 H14 118.9 . . ?
C13 C14 C9 122.23(10) . . ?
C13 C14 H14 118.9 . . ?
C33 C32 H32 116.4 . . ?
C31 C32 C33 127.18(10) . . ?
C31 C32 H32 116.4 . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 C4 121.13(10) . . ?
C6 C5 H5A 119.4 . . ?
C30 C31 H31 119.1 . . ?
C32 C31 C30 121.82(10) . . ?
C32 C31 H31 119.1 . . ?
C36 C37 C38 118.99(10) . . ?
C36 C37 H37 120.5 . . ?
C38 C37 H37 120.5 . . ?
C36 C35 H35 119.9 . . ?
C34 C35 C36 120.29(10) . . ?
C34 C35 H35 119.9 . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 121.95(10) . . ?
C8 C7 H7 119.0 . . ?
O3 C22 H22A 110.3 . . ?
O3 C22 H22B 110.3 . . ?
O3 C22 C23 107.05(9) . . ?
H22A C22 H22B 108.6 . . ?
C23 C22 H22A 110.3 . . ?
C23 C22 H22B 110.3 . . ?
N1 C1 C3 122.40(10) . . ?
N1 C1 C2 117.52(10) . . ?
C3 C1 C2 120.06(10) . . ?
C4 C3 H3 118.1 . . ?
C1 C3 C4 123.89(10) . . ?
C1 C3 H3 118.1 . . ?
O6 C46 H46A 110.6 . . ?
O6 C46 H46B 110.6 . . ?
O6 C46 C47 105.82(8) . . ?
H46A C46 H46B 108.7 . . ?
C47 C46 H46A 110.6 . . ?
C47 C46 H46B 110.6 . . ?
C9 C8 H8 116.2 . . ?
C7 C8 C9 127.63(10) . . ?
C7 C8 H8 116.2 . . ?
C46 C47 H47A 109.1 . . ?
C46 C47 H47B 109.1 . . ?
C46 C47 C48 112.53(9) . . ?
H47A C47 H47B 107.8 . . ?
C48 C47 H47A 109.1 . . ?
C48 C47 H47B 109.1 . . ?
C45 C40 C39 119.96(10) . . ?
C41 C40 C45 118.87(11) . . ?
C41 C40 C39 121.07(11) . . ?
C17 C16 C15 120.01(11) . . ?
C21 C16 C15 120.64(12) . . ?
C21 C16 C17 119.35(12) . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C22 C23 C24 111.88(10) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C40 C45 H45 119.7 . . ?
C44 C45 C40 120.53(11) . . ?
C44 C45 H45 119.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C39 C40 108.68(9) . . ?
N2 C39 H39A 110.0 . . ?
N2 C39 H39B 110.0 . . ?
C40 C39 H39A 110.0 . . ?
C40 C39 H39B 110.0 . . ?
H39A C39 H39B 108.3 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C40 C41 H41 119.8 . . ?
C40 C41 C42 120.47(13) . . ?
C42 C41 H41 119.8 . . ?
N1 C15 C16 110.38(9) . . ?
N1 C15 H15A 109.6 . . ?
N1 C15 H15B 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C45 C44 H44 119.9 . . ?
C43 C44 C45 120.11(13) . . ?
C43 C44 H44 119.9 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
C1 C2 H2D 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.35(14) . . ?
C18 C17 H17 119.8 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.31(15) . . ?
C20 C21 H21 119.8 . . ?
C41 C42 H42 120.0 . . ?
C43 C42 C41 119.91(12) . . ?
C43 C42 H42 120.0 . . ?
C44 C43 H43 119.9 . . ?
C42 C43 C44 120.12(12) . . ?
C42 C43 H43 119.9 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.21(14) . . ?
C19 C20 H20 119.9 . . ?
C20 C19 H19 120.1 . . ?
C20 C19 C18 119.73(14) . . ?
C18 C19 H19 120.1 . . ?
C17 C18 C19 120.03(16) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-06
_olex2_date_sample_submission    2016-09-30
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id Y-05
_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 1.161
_oxdiff_exptl_absorpt_empirical_full_min 0.866
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       Luminescent
