# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2052600'
loop_
_audit_author_name
_audit_author_address
'Xinying Zhang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-12-27 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;
_audit_creation_date             2020-08-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N2 O'
_chemical_formula_sum            'C23 H24 N2 O'
_chemical_formula_weight         344.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   15.2849(6)
_cell_length_b                   7.3266(3)
_cell_length_c                   18.6240(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.556(5)
_cell_angle_gamma                90
_cell_volume                     1952.84(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3239
_cell_measurement_temperature    296.2(4)
_cell_measurement_theta_max      70.9300
_cell_measurement_theta_min      4.9200
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8198
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.486
_diffrn_reflns_theta_min         4.926
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.2(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  34.00   1.00    4.26    --  -35.62  29.00-121.00   92
  2  ω   -102.00 -15.00   1.00    4.26    --  -35.62 -29.00  77.00   87
  3  ω    -12.00  13.00   1.00    4.26    --   35.62 -29.00  77.00   25
  4  ω     35.00  60.00   1.00    4.26    --   35.62  29.00-121.00   25
  5  ω    107.00 176.00   1.00   17.02    --  107.12  29.00-121.00   69
  6  ω     41.00 128.00   1.00   17.02    --  107.12 -29.00  77.00   87
  7  ω    -65.00 -39.00   1.00    4.26    --  -35.62-178.00 -30.00   26
  8  ω    -35.00  59.00   1.00    4.26    --   35.62 -19.00 -30.00   94
  9  ω     82.00 108.00   1.00    4.26    --   35.62-178.00-150.00   26
 10  ω     74.00 105.00   1.00    4.26    --   35.62 178.00  60.00   31
 11  ω     68.00  94.00   1.00    4.26    --   35.62 178.00 120.00   26
 12  ω    137.00 176.00   1.00   17.02    --  107.12 111.00 120.00   39
 13  ω     85.00 135.00   1.00   17.02    --  107.12 178.00-150.00   50
 14  ω     93.00 159.00   1.00   17.02    --  107.12  45.00 -30.00   66
 15  ω     43.00 125.00   1.00   17.02    --  107.12 -45.00   0.00   82
 16  ω     52.00  78.00   1.00   17.02    --  107.12 -95.00-150.00   26
 17  ω     49.00 126.00   1.00   17.02    --  107.12 -30.00 -90.00   77
 18  ω     44.00 109.00   1.00   17.02    --  107.12 -95.00  30.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0948434000
_diffrn_orient_matrix_UB_12      0.0752373000
_diffrn_orient_matrix_UB_13      0.0525991000
_diffrn_orient_matrix_UB_21      0.0397628000
_diffrn_orient_matrix_UB_22      -0.0262303000
_diffrn_orient_matrix_UB_23      -0.0648178000
_diffrn_orient_matrix_UB_31      -0.0313476000
_diffrn_orient_matrix_UB_32      0.1946355000
_diffrn_orient_matrix_UB_33      -0.0290256000
_diffrn_oxdiff_digest_frames     
;
01b9620baace3d2e34ee8852d94ac233d100028958f
;
_diffrn_oxdiff_digest_hkl        
;
01c9cf87a6fd275160c388acc0bff1de3e1ed7
;
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2996
_reflns_number_total             3702
_reflns_odcompleteness_completeness 99.66
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.086
_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)+(0.0543P)²+0.4431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1408
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.18808(11) 0.4445(2) 0.67588(10) 0.0358(4) Uani 1 1 d . . . . .
H1 H 0.1255 0.4928 0.6481 0.043 Uiso 1 1 calc R . . . .
N1 N 0.18994(11) 0.2213(2) 0.59241(9) 0.0445(4) Uani 1 1 d . . . . .
O1 O 0.15016(13) 0.0067(3) 0.49753(11) 0.0819(6) Uani 1 1 d . . . . .
C2 C 0.22987(12) 0.5337(2) 0.75268(10) 0.0375(4) Uani 1 1 d . . . . .
N2 N 0.18944(9) 0.24370(19) 0.66977(8) 0.0362(3) Uani 1 1 d . . . . .
C3 C 0.20174(14) 0.5403(3) 0.81561(11) 0.0481(4) Uani 1 1 d . . . . .
H3 H 0.1499 0.4741 0.8158 0.058 Uiso 1 1 calc R . . . .
C4 C 0.25140(16) 0.6463(3) 0.87838(12) 0.0549(5) Uani 1 1 d . . . . .
H4 H 0.2337 0.6485 0.9213 0.066 Uiso 1 1 calc R . . . .
C5 C 0.32716(16) 0.7488(3) 0.87755(12) 0.0541(5) Uani 1 1 d . . . . .
H5 H 0.3592 0.8208 0.9197 0.065 Uiso 1 1 calc R . . . .
C6 C 0.35588(13) 0.7453(3) 0.81453(11) 0.0449(4) Uani 1 1 d . . . . .
H6 H 0.4068 0.8144 0.8141 0.054 Uiso 1 1 calc R . . . .
C7 C 0.30731(11) 0.6372(2) 0.75239(10) 0.0362(4) Uani 1 1 d . . . . .
C8 C 0.32327(11) 0.6049(2) 0.67943(9) 0.0353(4) Uani 1 1 d . . . . .
C9 C 0.25510(12) 0.4948(2) 0.63598(9) 0.0364(4) Uani 1 1 d . . . . .
C10 C 0.24063(13) 0.3681(3) 0.56860(10) 0.0444(4) Uani 1 1 d . . . . .
C11 C 0.1770(2) 0.4498(4) 0.49277(13) 0.0780(8) Uani 1 1 d . . . . .
H11A H 0.1603 0.3569 0.4539 0.117 Uiso 1 1 calc GR . . . .
H11B H 0.2092 0.5468 0.4778 0.117 Uiso 1 1 calc GR . . . .
H11C H 0.1215 0.4970 0.4989 0.117 Uiso 1 1 calc GR . . . .
C12 C 0.33090(16) 0.2927(4) 0.56269(15) 0.0667(7) Uani 1 1 d . . . . .
H12A H 0.3689 0.2424 0.6113 0.100 Uiso 1 1 calc GR . . . .
H12B H 0.3644 0.3892 0.5488 0.100 Uiso 1 1 calc GR . . . .
H12C H 0.3163 0.1989 0.5243 0.100 Uiso 1 1 calc GR . . . .
C13 C 0.15158(14) 0.0646(3) 0.55988(13) 0.0557(5) Uani 1 1 d . . . . .
C14 C 0.11294(16) -0.0244(3) 0.61539(15) 0.0613(6) Uani 1 1 d . . . . .
H14A H 0.1541 -0.1207 0.6439 0.074 Uiso 1 1 calc R . . . .
H14B H 0.0516 -0.0757 0.5886 0.074 Uiso 1 1 calc R . . . .
C15 C 0.10727(13) 0.1304(3) 0.66887(12) 0.0475(4) Uani 1 1 d . . . . .
C16 C 0.01438(14) 0.2306(3) 0.63493(16) 0.0675(7) Uani 1 1 d . . . . .
H16A H 0.0123 0.3296 0.6681 0.101 Uiso 1 1 calc GR . . . .
H16B H -0.0360 0.1476 0.6301 0.101 Uiso 1 1 calc GR . . . .
H16C H 0.0083 0.2776 0.5853 0.101 Uiso 1 1 calc GR . . . .
C17 C 0.1233(2) 0.0642(4) 0.74977(15) 0.0787(8) Uani 1 1 d . . . . .
H17A H 0.1842 0.0102 0.7709 0.118 Uiso 1 1 calc GR . . . .
H17B H 0.0768 -0.0250 0.7485 0.118 Uiso 1 1 calc GR . . . .
H17C H 0.1190 0.1655 0.7810 0.118 Uiso 1 1 calc GR . . . .
C18 C 0.40486(12) 0.6756(2) 0.66292(10) 0.0380(4) Uani 1 1 d . . . . .
C19 C 0.39242(15) 0.7746(3) 0.59704(11) 0.0557(5) Uani 1 1 d . . . . .
H19 H 0.3323 0.7999 0.5635 0.067 Uiso 1 1 calc R . . . .
C20 C 0.46898(18) 0.8365(4) 0.58042(13) 0.0698(7) Uani 1 1 d . . . . .
H20 H 0.4602 0.9030 0.5359 0.084 Uiso 1 1 calc R . . . .
C21 C 0.55772(16) 0.7996(3) 0.62981(14) 0.0620(6) Uani 1 1 d . . . . .
H21 H 0.6090 0.8387 0.6180 0.074 Uiso 1 1 calc R . . . .
C22 C 0.57131(14) 0.7052(3) 0.69652(13) 0.0539(5) Uani 1 1 d . . . . .
H22 H 0.6316 0.6825 0.7303 0.065 Uiso 1 1 calc R . . . .
C23 C 0.49493(13) 0.6435(2) 0.71361(11) 0.0435(4) Uani 1 1 d . . . . .
H23 H 0.5041 0.5806 0.7590 0.052 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
C1 H1 0.9800 . ?
C1 C2 1.496(2) . ?
C1 N2 1.476(2) . ?
C1 C9 1.507(2) . ?
N1 N2 1.453(2) . ?
N1 C10 1.481(2) . ?
N1 C13 1.334(2) . ?
O1 C13 1.229(3) . ?
C2 C3 1.384(3) . ?
C2 C7 1.407(2) . ?
N2 C15 1.501(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(2) . ?
C7 C8 1.481(2) . ?
C8 C9 1.341(2) . ?
C8 C18 1.479(2) . ?
C9 C10 1.513(2) . ?
C10 C11 1.528(3) . ?
C10 C12 1.526(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.507(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.532(3) . ?
C15 C16 1.525(3) . ?
C15 C17 1.519(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.380(3) . ?
C18 C23 1.389(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.372(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(3) . ?
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
C2 C1 H1 110.9 . . ?
C2 C1 C9 103.21(13) . . ?
N2 C1 H1 110.9 . . ?
N2 C1 C2 119.75(14) . . ?
N2 C1 C9 100.08(13) . . ?
C9 C1 H1 110.9 . . ?
N2 N1 C10 113.59(13) . . ?
C13 N1 N2 113.15(16) . . ?
C13 N1 C10 132.97(17) . . ?
C3 C2 C1 132.02(17) . . ?
C3 C2 C7 119.77(17) . . ?
C7 C2 C1 108.00(15) . . ?
C1 N2 C15 121.19(14) . . ?
N1 N2 C1 101.20(13) . . ?
N1 N2 C15 102.83(13) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.52(19) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.44(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.85(18) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.73(18) . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C8 109.10(14) . . ?
C6 C7 C2 120.68(16) . . ?
C6 C7 C8 130.22(16) . . ?
C9 C8 C7 107.83(15) . . ?
C9 C8 C18 128.20(16) . . ?
C18 C8 C7 123.85(14) . . ?
C1 C9 C10 109.39(14) . . ?
C8 C9 C1 111.60(15) . . ?
C8 C9 C10 136.51(17) . . ?
N1 C10 C9 97.85(14) . . ?
N1 C10 C11 109.33(17) . . ?
N1 C10 C12 109.86(18) . . ?
C9 C10 C11 112.74(18) . . ?
C9 C10 C12 114.17(16) . . ?
C12 C10 C11 111.9(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 106.06(18) . . ?
O1 C13 N1 125.8(2) . . ?
O1 C13 C14 128.1(2) . . ?
C13 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
C13 C14 C15 104.52(17) . . ?
H14A C14 H14B 108.9 . . ?
C15 C14 H14A 110.8 . . ?
C15 C14 H14B 110.8 . . ?
N2 C15 C14 100.30(15) . . ?
N2 C15 C16 113.08(17) . . ?
N2 C15 C17 108.83(17) . . ?
C16 C15 C14 110.13(18) . . ?
C17 C15 C14 112.5(2) . . ?
C17 C15 C16 111.5(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C8 120.40(16) . . ?
C19 C18 C23 119.20(17) . . ?
C23 C18 C8 120.41(16) . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.40(19) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.94(19) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.09(18) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?

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
C1 C2 C3 C4 -175.23(19) . . . . ?
C1 C2 C7 C6 175.45(16) . . . . ?
C1 C2 C7 C8 -5.23(18) . . . . ?
C1 N2 C15 C14 146.39(17) . . . . ?
C1 N2 C15 C16 29.2(2) . . . . ?
C1 N2 C15 C17 -95.4(2) . . . . ?
C1 C9 C10 N1 -18.18(17) . . . . ?
C1 C9 C10 C11 96.7(2) . . . . ?
C1 C9 C10 C12 -134.15(18) . . . . ?
N1 N2 C15 C14 34.63(18) . . . . ?
N1 N2 C15 C16 -82.6(2) . . . . ?
N1 N2 C15 C17 152.84(18) . . . . ?
N1 C13 C14 C15 17.8(2) . . . . ?
O1 C13 C14 C15 -163.1(2) . . . . ?
C2 C1 N2 N1 -151.96(14) . . . . ?
C2 C1 N2 C15 95.42(19) . . . . ?
C2 C1 C9 C8 -3.10(19) . . . . ?
C2 C1 C9 C10 162.06(14) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C2 C7 C8 C9 3.29(19) . . . . ?
C2 C7 C8 C18 -173.11(16) . . . . ?
N2 C1 C2 C3 -70.5(3) . . . . ?
N2 C1 C2 C7 114.96(17) . . . . ?
N2 C1 C9 C8 -127.11(15) . . . . ?
N2 C1 C9 C10 38.04(17) . . . . ?
N2 N1 C10 C9 -9.19(18) . . . . ?
N2 N1 C10 C11 -126.69(19) . . . . ?
N2 N1 C10 C12 110.10(18) . . . . ?
N2 N1 C13 O1 -173.8(2) . . . . ?
N2 N1 C13 C14 5.3(2) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C3 C2 C7 C8 179.45(16) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
C5 C6 C7 C8 -178.65(18) . . . . ?
C6 C7 C8 C9 -177.47(18) . . . . ?
C6 C7 C8 C18 6.1(3) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
C7 C8 C9 C1 0.06(19) . . . . ?
C7 C8 C9 C10 -159.4(2) . . . . ?
C7 C8 C18 C19 -127.3(2) . . . . ?
C7 C8 C18 C23 52.6(2) . . . . ?
C8 C9 C10 N1 141.6(2) . . . . ?
C8 C9 C10 C11 -103.6(3) . . . . ?
C8 C9 C10 C12 25.6(3) . . . . ?
C8 C18 C19 C20 -178.2(2) . . . . ?
C8 C18 C23 C22 177.88(17) . . . . ?
C9 C1 C2 C3 179.53(19) . . . . ?
C9 C1 C2 C7 5.00(18) . . . . ?
C9 C1 N2 N1 -40.31(14) . . . . ?
C9 C1 N2 C15 -152.93(15) . . . . ?
C9 C8 C18 C19 57.0(3) . . . . ?
C9 C8 C18 C23 -123.1(2) . . . . ?
C10 N1 N2 C1 32.87(18) . . . . ?
C10 N1 N2 C15 158.78(15) . . . . ?
C10 N1 C13 O1 -0.6(4) . . . . ?
C10 N1 C13 C14 178.5(2) . . . . ?
C13 N1 N2 C1 -152.56(16) . . . . ?
C13 N1 N2 C15 -26.7(2) . . . . ?
C13 N1 C10 C9 177.6(2) . . . . ?
C13 N1 C10 C11 60.1(3) . . . . ?
C13 N1 C10 C12 -63.1(3) . . . . ?
C13 C14 C15 N2 -32.4(2) . . . . ?
C13 C14 C15 C16 87.0(2) . . . . ?
C13 C14 C15 C17 -147.84(19) . . . . ?
C18 C8 C9 C1 176.26(16) . . . . ?
C18 C8 C9 C10 16.8(3) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C18 C23 C22 -2.2(3) . . . . ?
C19 C20 C21 C22 -1.5(4) . . . . ?
C20 C21 C22 C23 1.2(3) . . . . ?
C21 C22 C23 C18 0.6(3) . . . . ?
C23 C18 C19 C20 1.9(3) . . . . ?


_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 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.314
####################################################################### 
# 
# 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_V
_database_code_depnum_ccdc_archive 'CCDC 2052601'
loop_
_audit_author_name
_audit_author_address
'Xinying Zhang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-12-27 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;
_audit_creation_date             2020-08-29
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 N2 O2, H2 O'
_chemical_formula_sum            'C23 H28 N2 O3'
_chemical_formula_weight         380.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   7.0249(3)
_cell_length_b                   24.9828(10)
_cell_length_c                   12.0067(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.724(4)
_cell_angle_gamma                90
_cell_volume                     2106.24(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4826
_cell_measurement_temperature    294.98(11)
_cell_measurement_theta_max      71.1680
_cell_measurement_theta_min      4.0700
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9870
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.714
_diffrn_reflns_theta_min         3.538
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  31.00   1.00    3.78    --  -35.62  64.00-161.00   86
  2  ω   -102.00 -16.00   1.00    3.78    --  -35.62 -64.00  62.00   86
  3  ω    -31.00  55.00   1.00    3.78    --   35.62 -64.00  62.00   86
  4  ω     16.00 102.00   1.00    3.78    --   35.62  64.00-161.00   86
  5  ω     75.00 119.00   1.00   15.13    --  107.12 -64.00  62.00   44
  6  ω     98.00 170.00   1.00   15.13    --  107.12  64.00-161.00   72
  7  ω   -102.00 -35.00   1.00    3.78    --  -35.62-178.00 150.00   67
  8  ω   -104.00 -18.00   1.00    3.78    --  -35.62 -38.00  90.00   86
  9  ω   -106.00 -38.00   1.00    3.78    --  -35.62-178.00-120.00   68
 10  ω     37.00 125.00   1.00   15.13    --  107.12 -30.00  60.00   88
 11  ω    124.00 164.00   1.00   15.13    --  107.12  45.00 120.00   40
 12  ω     50.00  77.00   1.00   15.13    --  107.12 -95.00  60.00   27
 13  ω     41.00 113.00   1.00   15.13    --  107.12 -61.00-180.00   72
 14  ω     43.00  85.00   1.00   15.13    --  107.12 -95.00  90.00   42
 15  ω     38.00 107.00   1.00   15.13    --  107.12 -95.00 -30.00   69
 16  ω    102.00 165.00   1.00   15.13    --  107.12 111.00 150.00   63
 17  ω     39.00  67.00   1.00   15.13    --  107.12-111.00 -60.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1035521000
_diffrn_orient_matrix_UB_12      -0.0295404000
_diffrn_orient_matrix_UB_13      -0.0968595000
_diffrn_orient_matrix_UB_21      0.1034919000
_diffrn_orient_matrix_UB_22      0.0353153000
_diffrn_orient_matrix_UB_23      -0.0841839000
_diffrn_orient_matrix_UB_31      0.1633804000
_diffrn_orient_matrix_UB_32      -0.0410362000
_diffrn_orient_matrix_UB_33      -0.0027953000
_diffrn_oxdiff_digest_frames     
;
0158eb5fa07cf8164d79f8a9264d8ee881000272e98
;
_diffrn_oxdiff_digest_hkl        
;
01941e7c0aed5eb3b46a2762ce216f79c56746
;
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3191
_reflns_number_total             4019
_reflns_odcompleteness_completeness 99.46
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0785
_refine_ls_restrained_S_all      1.220
_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)+10.1040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2362
_refine_ls_wR_factor_ref         0.2420
_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, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C1(H1A)
2.c Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.7376(5) 0.19661(15) 0.2663(3) 0.0438(9) Uani 1 1 d . . . . .
O2 O 0.1902(5) 0.34485(14) 0.5080(3) 0.0400(9) Uani 1 1 d . . . . .
H2 H 0.2657 0.3225 0.4858 0.060 Uiso 1 1 calc GR . . . .
N1 N 0.5928(5) 0.26286(16) 0.3641(3) 0.0312(9) Uani 1 1 d . . . . .
H1 H 0.6839 0.2675 0.4127 0.037 Uiso 1 1 calc R . . . .
N2 N 0.4226(5) 0.29390(15) 0.3641(3) 0.0272(8) Uani 1 1 d . . . . .
C1 C 0.4670(6) 0.34904(18) 0.3248(4) 0.0273(9) Uani 1 1 d . . . . .
H1A H 0.5786 0.3606 0.3695 0.033 Uiso 1 1 calc R . . . .
C2 C 0.5168(6) 0.35937(19) 0.2039(4) 0.0301(10) Uani 1 1 d . . . . .
C3 C 0.6507(7) 0.3366(2) 0.1358(4) 0.0414(12) Uani 1 1 d . . . . .
H3 H 0.7263 0.3082 0.1611 0.050 Uiso 1 1 calc R . . . .
C4 C 0.6693(9) 0.3571(3) 0.0291(5) 0.0536(16) Uani 1 1 d . . . . .
H4 H 0.7574 0.3420 -0.0180 0.064 Uiso 1 1 calc R . . . .
C5 C 0.5584(10) 0.3995(3) -0.0079(5) 0.0594(17) Uani 1 1 d . . . . .
H5 H 0.5717 0.4124 -0.0799 0.071 Uiso 1 1 calc R . . . .
C6 C 0.4280(9) 0.4231(2) 0.0606(4) 0.0495(14) Uani 1 1 d . . . . .
H6 H 0.3551 0.4521 0.0358 0.059 Uiso 1 1 calc R . . . .
C7 C 0.4082(7) 0.4029(2) 0.1666(4) 0.0333(11) Uani 1 1 d . . . . .
C8 C -0.0233(9) 0.4622(2) 0.1929(6) 0.0624(19) Uani 1 1 d . . . . .
H8 H -0.0696 0.4279 0.1789 0.075 Uiso 1 1 calc R . . . .
C9 C -0.1386(11) 0.5058(3) 0.1698(7) 0.077(2) Uani 1 1 d . . . . .
H9 H -0.2622 0.5008 0.1420 0.092 Uiso 1 1 calc R . . . .
C10 C -0.0712(11) 0.5562(3) 0.1877(6) 0.068(2) Uani 1 1 d . . . . .
H10 H -0.1487 0.5856 0.1716 0.082 Uiso 1 1 calc R . . . .
C11 C 0.1089(11) 0.5639(2) 0.2292(5) 0.0586(18) Uani 1 1 d . . . . .
H11 H 0.1546 0.5984 0.2410 0.070 Uiso 1 1 calc R . . . .
C12 C 0.2251(8) 0.5200(2) 0.2542(5) 0.0438(13) Uani 1 1 d . . . . .
H12 H 0.3479 0.5254 0.2830 0.053 Uiso 1 1 calc R . . . .
C13 C 0.1597(8) 0.46855(19) 0.2364(4) 0.0357(11) Uani 1 1 d . . . . .
C14 C 0.2846(7) 0.42140(18) 0.2560(4) 0.0321(10) Uani 1 1 d . . . . .
C15 C 0.3126(7) 0.39026(18) 0.3464(4) 0.0290(10) Uani 1 1 d . . . . .
C16 C 0.2358(8) 0.3964(2) 0.4630(4) 0.0402(12) Uani 1 1 d . . . . .
C17 C 0.0496(12) 0.4273(3) 0.4650(6) 0.087(3) Uani 1 1 d . . . . .
H17A H -0.0398 0.4121 0.4119 0.130 Uiso 1 1 calc GR . . . .
H17B H 0.0724 0.4641 0.4462 0.130 Uiso 1 1 calc GR . . . .
H17C H -0.0013 0.4254 0.5382 0.130 Uiso 1 1 calc GR . . . .
C18 C 0.3889(13) 0.4214(3) 0.5390(6) 0.094(3) Uani 1 1 d . . . . .
H18A H 0.3430 0.4240 0.6133 0.141 Uiso 1 1 calc GR . . . .
H18B H 0.4189 0.4566 0.5123 0.141 Uiso 1 1 calc GR . . . .
H18C H 0.5012 0.3996 0.5394 0.141 Uiso 1 1 calc GR . . . .
C19 C 0.6014(7) 0.22619(19) 0.2837(4) 0.0324(10) Uani 1 1 d . . . . .
C20 C 0.4127(7) 0.2274(2) 0.2197(4) 0.0372(11) Uani 1 1 d . . . . .
H20A H 0.3646 0.1915 0.2063 0.045 Uiso 1 1 calc R . . . .
H20B H 0.4239 0.2457 0.1489 0.045 Uiso 1 1 calc R . . . .
C21 C 0.2838(7) 0.25869(19) 0.2982(4) 0.0339(11) Uani 1 1 d . . . . .
C22 C 0.1988(8) 0.2201(2) 0.3829(5) 0.0471(14) Uani 1 1 d . . . . .
H22A H 0.2997 0.2016 0.4223 0.071 Uiso 1 1 calc GR . . . .
H22B H 0.1182 0.1947 0.3445 0.071 Uiso 1 1 calc GR . . . .
H22C H 0.1253 0.2400 0.4349 0.071 Uiso 1 1 calc GR . . . .
C23 C 0.1259(7) 0.2895(2) 0.2373(5) 0.0452(14) Uani 1 1 d . . . . .
H23A H 0.0553 0.3097 0.2901 0.068 Uiso 1 1 calc GR . . . .
H23B H 0.0422 0.2649 0.1990 0.068 Uiso 1 1 calc GR . . . .
H23C H 0.1805 0.3134 0.1845 0.068 Uiso 1 1 calc GR . . . .
O3 O -0.1780(6) 0.3059(2) 0.5380(3) 0.0643(13) Uani 1 1 d . . . . .
H3A H -0.0677 0.3196 0.5339 0.096 Uiso 1 1 d G . . . .
H3B H -0.2077 0.3105 0.6054 0.096 Uiso 1 1 d G . . . .


_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 C19 1.232(6) . ?
O2 H2 0.8200 . ?
O2 C16 1.436(6) . ?
N1 H1 0.8600 . ?
N1 N2 1.425(5) . ?
N1 C19 1.334(6) . ?
N2 C1 1.492(6) . ?
N2 C21 1.518(5) . ?
C1 H1A 0.9800 . ?
C1 C2 1.525(6) . ?
C1 C15 1.524(6) . ?
C2 C3 1.387(7) . ?
C2 C7 1.394(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(7) . ?
C7 C14 1.475(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(9) . ?
C8 C13 1.382(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.360(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.359(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(7) . ?
C13 C14 1.483(7) . ?
C14 C15 1.346(6) . ?
C15 C16 1.523(7) . ?
C16 C17 1.521(8) . ?
C16 C18 1.524(9) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.512(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.540(7) . ?
C21 C22 1.535(7) . ?
C21 C23 1.520(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O3 H3A 0.8503 . ?
O3 H3B 0.8501 . ?

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
C16 O2 H2 109.5 . . ?
N2 N1 H1 122.3 . . ?
C19 N1 H1 122.3 . . ?
C19 N1 N2 115.5(4) . . ?
N1 N2 C1 108.6(3) . . ?
N1 N2 C21 102.2(3) . . ?
C1 N2 C21 120.5(3) . . ?
N2 C1 H1A 105.6 . . ?
N2 C1 C2 120.9(4) . . ?
N2 C1 C15 114.4(4) . . ?
C2 C1 H1A 105.6 . . ?
C15 C1 H1A 105.6 . . ?
C15 C1 C2 103.5(4) . . ?
C3 C2 C1 132.1(5) . . ?
C3 C2 C7 120.4(5) . . ?
C7 C2 C1 107.4(4) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.4(5) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(5) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.7 . . ?
C7 C6 C5 118.6(6) . . ?
C7 C6 H6 120.7 . . ?
C2 C7 C14 109.9(4) . . ?
C6 C7 C2 120.8(5) . . ?
C6 C7 C14 129.3(5) . . ?
C9 C8 H8 119.4 . . ?
C9 C8 C13 121.2(6) . . ?
C13 C8 H8 119.4 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(7) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(6) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C14 120.5(5) . . ?
C12 C13 C8 117.9(5) . . ?
C12 C13 C14 121.5(5) . . ?
C7 C14 C13 119.5(4) . . ?
C15 C14 C7 109.3(4) . . ?
C15 C14 C13 131.2(5) . . ?
C14 C15 C1 109.9(4) . . ?
C14 C15 C16 129.5(4) . . ?
C16 C15 C1 119.9(4) . . ?
O2 C16 C15 110.2(4) . . ?
O2 C16 C17 104.4(5) . . ?
O2 C16 C18 107.7(5) . . ?
C15 C16 C18 109.2(5) . . ?
C17 C16 C15 113.2(5) . . ?
C17 C16 C18 111.9(6) . . ?
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 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 N1 125.9(4) . . ?
O1 C19 C20 126.8(4) . . ?
N1 C19 C20 107.2(4) . . ?
C19 C20 H20A 111.2 . . ?
C19 C20 H20B 111.2 . . ?
C19 C20 C21 102.8(4) . . ?
H20A C20 H20B 109.1 . . ?
C21 C20 H20A 111.2 . . ?
C21 C20 H20B 111.2 . . ?
N2 C21 C20 103.5(4) . . ?
N2 C21 C22 106.0(4) . . ?
N2 C21 C23 113.9(4) . . ?
C22 C21 C20 109.6(4) . . ?
C23 C21 C20 113.4(4) . . ?
C23 C21 C22 110.1(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H3A O3 H3B 104.5 . . ?

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 163.8(5) . . . . ?
N1 N2 C1 C2 69.3(5) . . . . ?
N1 N2 C1 C15 -166.0(3) . . . . ?
N1 N2 C21 C20 -28.7(4) . . . . ?
N1 N2 C21 C22 86.6(4) . . . . ?
N1 N2 C21 C23 -152.2(4) . . . . ?
N1 C19 C20 C21 -15.4(5) . . . . ?
N2 N1 C19 O1 177.3(5) . . . . ?
N2 N1 C19 C20 -3.5(6) . . . . ?
N2 C1 C2 C3 -52.8(7) . . . . ?
N2 C1 C2 C7 132.2(4) . . . . ?
N2 C1 C15 C14 -136.6(4) . . . . ?
N2 C1 C15 C16 51.8(6) . . . . ?
C1 N2 C21 C20 91.6(5) . . . . ?
C1 N2 C21 C22 -153.1(4) . . . . ?
C1 N2 C21 C23 -31.9(6) . . . . ?
C1 C2 C3 C4 -176.4(5) . . . . ?
C1 C2 C7 C6 177.4(5) . . . . ?
C1 C2 C7 C14 -1.3(5) . . . . ?
C1 C15 C16 O2 -47.8(6) . . . . ?
C1 C15 C16 C17 -164.4(5) . . . . ?
C1 C15 C16 C18 70.3(6) . . . . ?
C2 C1 C15 C14 -3.0(5) . . . . ?
C2 C1 C15 C16 -174.6(4) . . . . ?
C2 C3 C4 C5 0.7(9) . . . . ?
C2 C7 C14 C13 178.2(4) . . . . ?
C2 C7 C14 C15 -0.6(6) . . . . ?
C3 C2 C7 C6 1.8(7) . . . . ?
C3 C2 C7 C14 -177.0(4) . . . . ?
C3 C4 C5 C6 0.8(10) . . . . ?
C4 C5 C6 C7 -1.0(10) . . . . ?
C5 C6 C7 C2 -0.2(8) . . . . ?
C5 C6 C7 C14 178.2(5) . . . . ?
C6 C7 C14 C13 -0.4(8) . . . . ?
C6 C7 C14 C15 -179.2(5) . . . . ?
C7 C2 C3 C4 -2.0(7) . . . . ?
C7 C14 C15 C1 2.4(5) . . . . ?
C7 C14 C15 C16 172.9(5) . . . . ?
C8 C9 C10 C11 -0.5(13) . . . . ?
C8 C13 C14 C7 90.0(7) . . . . ?
C8 C13 C14 C15 -91.5(8) . . . . ?
C9 C8 C13 C12 -1.2(10) . . . . ?
C9 C8 C13 C14 -177.2(7) . . . . ?
C9 C10 C11 C12 -0.3(11) . . . . ?
C10 C11 C12 C13 0.4(9) . . . . ?
C11 C12 C13 C8 0.3(9) . . . . ?
C11 C12 C13 C14 176.3(5) . . . . ?
C12 C13 C14 C7 -85.9(6) . . . . ?
C12 C13 C14 C15 92.7(7) . . . . ?
C13 C8 C9 C10 1.4(13) . . . . ?
C13 C14 C15 C1 -176.3(5) . . . . ?
C13 C14 C15 C16 -5.8(9) . . . . ?
C14 C15 C16 O2 142.4(5) . . . . ?
C14 C15 C16 C17 25.9(8) . . . . ?
C14 C15 C16 C18 -99.5(7) . . . . ?
C15 C1 C2 C3 177.5(5) . . . . ?
C15 C1 C2 C7 2.6(5) . . . . ?
C19 N1 N2 C1 -107.2(4) . . . . ?
C19 N1 N2 C21 21.1(5) . . . . ?
C19 C20 C21 N2 27.1(5) . . . . ?
C19 C20 C21 C22 -85.6(5) . . . . ?
C19 C20 C21 C23 151.0(4) . . . . ?
C21 N2 C1 C2 -47.8(6) . . . . ?
C21 N2 C1 C15 76.9(5) . . . . ?


_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 1.647
_oxdiff_exptl_absorpt_empirical_full_min 0.589
