# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_123
_database_code_depnum_ccdc_archive 'CCDC 2163566'
loop_
_audit_author_name
_audit_author_address
'Hongyuan Ren'
;Nanjing University
China
;
_audit_update_record             
;
2022-03-31 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1-Hydroxyindolin-2-one
_chemical_formula_moiety         'C8 H7 N O2'
_chemical_formula_sum            'C8 H7 N O2'
_chemical_formula_weight         149.15
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   11.8514(10)
_cell_length_b                   30.185(3)
_cell_length_c                   7.5330(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2694.8(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1479
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      53.65
_cell_measurement_theta_min      5.10
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6014
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0937 before and 0.0366 after correction.
The Ratio of minimum to maximum transmission is 0.8012.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2527
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.950
_diffrn_reflns_theta_min         5.099
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1017
_reflns_number_total             1151
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1151
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      0.928
_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)+(0.0596P)²+3.1452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          
'Refined as a 2-component perfect inversion twin.,Twin'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6222(2) 0.70658(8) 0.3307(3) 0.0395(7) Uani 1 1 d . . . . .
H1 H 0.592134 0.722951 0.253903 0.059 Uiso 1 1 calc R U . . .
O2 O 0.4862(2) 0.75790(7) 0.5623(4) 0.0379(6) Uani 1 1 d . . . . .
N1 N 0.5406(2) 0.69114(8) 0.4456(4) 0.0288(6) Uani 1 1 d . . . . .
C1 C 0.4429(3) 0.64094(10) 0.6064(4) 0.0274(7) Uani 1 1 d . . . . .
C2 C 0.5227(3) 0.64550(10) 0.4722(4) 0.0272(8) Uani 1 1 d . . . . .
C3 C 0.5710(3) 0.61018(11) 0.3848(5) 0.0329(8) Uani 1 1 d . . . . .
H3 H 0.626279 0.614313 0.294968 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5346(3) 0.56811(11) 0.4347(5) 0.0363(9) Uani 1 1 d . . . . .
H4 H 0.565246 0.542798 0.377315 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4545(3) 0.56260(10) 0.5664(5) 0.0357(9) Uani 1 1 d . . . . .
H5 H 0.431000 0.533534 0.597537 0.043 Uiso 1 1 calc R U . . .
C6 C 0.4078(3) 0.59879(10) 0.6543(5) 0.0315(8) Uani 1 1 d . . . . .
H6 H 0.353024 0.594698 0.745007 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4109(3) 0.68643(10) 0.6717(5) 0.0316(8) Uani 1 1 d . . . . .
H7A H 0.429405 0.690008 0.799049 0.038 Uiso 1 1 calc R U . . .
H7B H 0.329435 0.692127 0.654070 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4818(3) 0.71691(10) 0.5579(5) 0.0302(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 N1 1.379(4) . ?
O2 C8 1.239(4) . ?
N1 C2 1.408(4) . ?
N1 C8 1.344(4) . ?
C1 C2 1.391(5) . ?
C1 C6 1.387(5) . ?
C1 C7 1.507(4) . ?
C2 C3 1.378(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(5) . ?

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
N1 O1 H1 109.5 . . ?
O1 N1 C2 121.7(3) . . ?
C8 N1 O1 124.3(3) . . ?
C8 N1 C2 113.5(3) . . ?
C2 C1 C7 108.5(3) . . ?
C6 C1 C2 119.0(3) . . ?
C6 C1 C7 132.5(3) . . ?
C1 C2 N1 107.6(3) . . ?
C3 C2 N1 128.8(3) . . ?
C3 C2 C1 123.6(3) . . ?
C2 C3 H3 121.7 . . ?
C2 C3 C4 116.6(3) . . ?
C4 C3 H3 121.7 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C1 C7 H7A 111.1 . . ?
C1 C7 H7B 111.1 . . ?
C1 C7 C8 103.3(3) . . ?
H7A C7 H7B 109.1 . . ?
C8 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
O2 C8 N1 125.0(3) . . ?
O2 C8 C7 128.0(3) . . ?
N1 C8 C7 107.0(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
O1 N1 C2 C1 174.6(3) . . . . ?
O1 N1 C2 C3 -6.3(5) . . . . ?
O1 N1 C8 O2 6.5(5) . . . . ?
O1 N1 C8 C7 -174.2(3) . . . . ?
N1 C2 C3 C4 -177.8(3) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C1 C7 C8 O2 -179.3(3) . . . . ?
C1 C7 C8 N1 1.4(3) . . . . ?
C2 N1 C8 O2 178.1(3) . . . . ?
C2 N1 C8 C7 -2.5(4) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C1 C7 C8 0.2(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C6 C1 C2 N1 178.0(3) . . . . ?
C6 C1 C2 C3 -1.1(5) . . . . ?
C6 C1 C7 C8 -179.4(3) . . . . ?
C7 C1 C2 N1 -1.6(3) . . . . ?
C7 C1 C2 C3 179.2(3) . . . . ?
C7 C1 C6 C5 179.9(3) . . . . ?
C8 N1 C2 C1 2.7(4) . . . . ?
C8 N1 C2 C3 -178.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_123_sq
_database_code_depnum_ccdc_archive 'CCDC 2163569'
loop_
_audit_author_name
_audit_author_address
'Hongyuan Ren'
;Nanjing University
China
;
_audit_update_record             
;
2022-03-31 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        4-(Phenylethynyl)indolin-2-one
_chemical_formula_moiety         'C16 H11 N O, [+ solvents]0.3[H2O]'
_chemical_formula_sum            'C16 H11 N O'
_chemical_formula_weight         233.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   35.383(2)
_cell_length_b                   35.383(2)
_cell_length_c                   5.2350(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5675.8(8)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      53.89
_cell_measurement_theta_min      3.76
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5699
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0708 after correction.
The Ratio of minimum to maximum transmission is 0.7593.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2196
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            21591
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.031
_diffrn_reflns_theta_min         2.173
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2015
_reflns_number_total             2310
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.097
_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)+(0.0817P)²+9.2845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.1862
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C4(H4), C16(H16), C15(H15), C14(H14), C13(H13),
 C12(H12)
2.c Fitted hexagon refined as free rotating group:
 C11(C16,C15,C14,C13,C12)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.39119(6) 0.18571(6) 1.0645(3) 0.0600(5) Uani 1 1 d . . . . .
N1 N 0.34100(6) 0.20312(6) 0.9166(4) 0.0496(5) Uani 1 1 d . . . . .
H1 H 0.319627 0.187059 1.022854 0.059 Uiso 1 1 calc R U . . .
C9 C 0.42635(9) 0.30118(7) 0.2559(4) 0.0456(6) Uani 1 1 d . . . . .
C1 C 0.37776(8) 0.24997(7) 0.5919(4) 0.0454(6) Uani 1 1 d . . . . .
C2 C 0.33862(7) 0.23002(7) 0.7283(4) 0.0464(6) Uani 1 1 d . . . . .
C6 C 0.38333(8) 0.27859(7) 0.3951(4) 0.0496(6) Uani 1 1 d . . . . .
C8 C 0.38002(8) 0.20475(7) 0.9159(4) 0.0479(6) Uani 1 1 d . . . . .
C7 C 0.40684(8) 0.23462(8) 0.6971(4) 0.0496(6) Uani 1 1 d . . . . .
H7A H 0.434570 0.259387 0.760186 0.060 Uiso 1 1 calc R U . . .
H7B H 0.413382 0.218424 0.566784 0.060 Uiso 1 1 calc R U . . .
C3 C 0.30497(8) 0.23763(8) 0.6758(5) 0.0555(6) Uani 1 1 d . . . . .
H3 H 0.278754 0.224183 0.772631 0.067 Uiso 1 1 calc R U . . .
C10 C 0.45852(12) 0.31838(10) 0.1785(5) 0.0638(8) Uani 1 1 d . . . . .
C5 C 0.34890(9) 0.28603(8) 0.3376(5) 0.0562(7) Uani 1 1 d . . . . .
H5 H 0.351972 0.305250 0.202268 0.067 Uiso 1 1 calc R U . . .
C4 C 0.31078(9) 0.26580(9) 0.4752(5) 0.0602(7) Uani 1 1 d . . . . .
H4 H 0.287802 0.271179 0.432258 0.072 Uiso 1 1 calc R U . . .
C11 C 0.50420(5) 0.34272(6) 0.0810(4) 0.0613(7) Uani 1 1 d G . . . .
C16 C 0.51523(7) 0.36984(7) -0.1312(4) 0.0763(9) Uani 1 1 d G . . . .
H16 H 0.493252 0.372311 -0.221258 0.092 Uiso 1 1 calc R U . . .
C15 C 0.55841(8) 0.39335(7) -0.2115(4) 0.0900(11) Uani 1 1 d G . . . .
H15 H 0.565941 0.411887 -0.356518 0.108 Uiso 1 1 calc R U . . .
C14 C 0.59056(6) 0.38974(8) -0.0797(5) 0.0965(12) Uani 1 1 d G . . . .
H14 H 0.620070 0.405809 -0.134630 0.116 Uiso 1 1 calc R U . . .
C13 C 0.57953(6) 0.36262(9) 0.1324(5) 0.1027(12) Uani 1 1 d G . . . .
H13 H 0.601511 0.360155 0.222520 0.123 Uiso 1 1 calc R U . . .
C12 C 0.53636(7) 0.33911(7) 0.2128(4) 0.0809(9) Uani 1 1 d G . . . .
H12 H 0.528822 0.320579 0.357785 0.097 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.217(3) . ?
N1 H1 0.8800 . ?
N1 C2 1.402(3) . ?
N1 C8 1.353(3) . ?
C9 C6 1.506(4) . ?
C9 C10 1.067(4) . ?
C1 C2 1.396(3) . ?
C1 C6 1.388(3) . ?
C1 C7 1.488(3) . ?
C2 C3 1.374(3) . ?
C6 C5 1.402(3) . ?
C8 C7 1.525(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C4 1.390(4) . ?
C10 C11 1.491(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.373(4) . ?
C4 H4 0.9500 . ?
C11 C16 1.3900 . ?
C11 C12 1.3900 . ?
C16 H16 0.9500 . ?
C16 C15 1.3900 . ?
C15 H15 0.9500 . ?
C15 C14 1.3900 . ?
C14 H14 0.9500 . ?
C14 C13 1.3900 . ?
C13 H13 0.9500 . ?
C13 C12 1.3900 . ?
C12 H12 0.9500 . ?

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 N1 H1 124.0 . . ?
C8 N1 H1 124.0 . . ?
C8 N1 C2 112.06(19) . . ?
C10 C9 C6 173.4(3) . . ?
C2 C1 C7 108.54(19) . . ?
C6 C1 C2 119.5(2) . . ?
C6 C1 C7 132.0(2) . . ?
C1 C2 N1 108.8(2) . . ?
C3 C2 N1 128.8(2) . . ?
C3 C2 C1 122.4(2) . . ?
C1 C6 C9 118.9(2) . . ?
C1 C6 C5 118.5(2) . . ?
C5 C6 C9 122.6(2) . . ?
O1 C8 N1 125.5(2) . . ?
O1 C8 C7 127.0(2) . . ?
N1 C8 C7 107.44(19) . . ?
C1 C7 C8 103.11(18) . . ?
C1 C7 H7A 111.1 . . ?
C1 C7 H7B 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.4(2) . . ?
C4 C3 H3 121.3 . . ?
C9 C10 C11 177.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C16 C11 C10 121.42(16) . . ?
C16 C11 C12 120.0 . . ?
C12 C11 C10 118.54(16) . . ?
C11 C16 H16 120.0 . . ?
C11 C16 C15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 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
O1 C8 C7 C1 -177.3(2) . . . . ?
N1 C2 C3 C4 -179.5(2) . . . . ?
N1 C8 C7 C1 2.5(2) . . . . ?
C9 C6 C5 C4 -177.8(2) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C1 C6 C5 C4 0.7(4) . . . . ?
C2 N1 C8 O1 177.5(2) . . . . ?
C2 N1 C8 C7 -2.4(3) . . . . ?
C2 C1 C6 C9 177.7(2) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C7 C8 -1.9(2) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C6 C1 C2 N1 -179.5(2) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C1 C7 C8 178.3(2) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C8 N1 C2 C1 1.2(3) . . . . ?
C8 N1 C2 C3 -178.2(2) . . . . ?
C7 C1 C2 N1 0.6(2) . . . . ?
C7 C1 C2 C3 -180.0(2) . . . . ?
C7 C1 C6 C9 -2.4(4) . . . . ?
C7 C1 C6 C5 179.0(2) . . . . ?
C10 C11 C16 C15 177.6(2) . . . . ?
C10 C11 C12 C13 -177.7(2) . . . . ?
C11 C16 C15 C14 0.0 . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  
;
A solvent mask was calculated and 78 electrons were 
found in a volume of 263Å³ in 2 voids per unit cell. 
This is consistent with the presence of 
[+ solvents]0.3[H2O] per Asymmetric Unit 
which account for 54 electrons 
per unit cell.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.023 89 26 '18 ?'
2 0.333 0.667 0.258 87 26 '2.7 H2O'
3 0.667 0.333 -0.075 87 26 '2.7 H2O'

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_123_a
_database_code_depnum_ccdc_archive 'CCDC 2163568'
loop_
_audit_author_name
_audit_author_address
'Hongyuan Ren'
;Nanjing University
China
;
_audit_update_record             
;
2022-03-31 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2-(4-(1,2,2-Triphenylvinyl)phenyl)-1H-indole
_chemical_formula_moiety         'C34 H25 N'
_chemical_formula_sum            'C34 H25 N'
_chemical_formula_weight         447.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.9280(19)
_cell_length_b                   9.4716(18)
_cell_length_c                   52.455(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.791(6)
_cell_angle_gamma                90
_cell_volume                     4932.1(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4697
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1039 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.8550.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_unetI/netI     0.1079
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       68
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            46913
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.083
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4657
_reflns_number_total             11557
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0077(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         11557
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.1877
_refine_ls_R_factor_gt           0.0702
_refine_ls_restrained_S_all      0.993
_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)+(0.1028P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1797
_refine_ls_wR_factor_ref         0.2298
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N1-C6 \\sim N2-C41
 with sigma of 0.02
3. Rigid bond restraints
 N2, C41
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N2, C43
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C43) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C42) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
 C34(H34), N2(H2A), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C45(H45),
 C46(H46), C48(H48), C49(H49), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56),
  C59(H59), C60(H60), C61(H61), C62(H62), C63(H63), C66(H66), C67(H67),
 C68(H68), C69(H69), C70(H70)
;
_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
N1 N 0.6328(2) 0.3859(3) 0.49189(5) 0.0610(7) Uani 1 1 d D . . . .
H1 H 0.629350 0.458295 0.501755 0.073 Uiso 1 1 calc R U . . .
C1 C 0.6336(3) 0.2508(3) 0.45699(6) 0.0586(8) Uani 1 1 d . . . . .
C2 C 0.6235(3) 0.2261(4) 0.43081(7) 0.0770(10) Uani 1 1 d . . . . .
H2 H 0.636610 0.135871 0.424285 0.092 Uiso 1 1 calc R U . . .
C3 C 0.5936(4) 0.3376(5) 0.41474(7) 0.0857(11) Uani 1 1 d . . . . .
H3 H 0.586320 0.322044 0.397265 0.103 Uiso 1 1 calc R U . . .
C4 C 0.5744(4) 0.4724(5) 0.42432(7) 0.0846(11) Uani 1 1 d . . . . .
H4 H 0.552077 0.545310 0.413157 0.101 Uiso 1 1 calc R U . . .
C5 C 0.5874(3) 0.5007(4) 0.44985(7) 0.0730(10) Uani 1 1 d . . . . .
H5 H 0.575813 0.591669 0.456126 0.088 Uiso 1 1 calc R U . . .
C6 C 0.6182(3) 0.3899(3) 0.46588(6) 0.0569(8) Uani 1 1 d D . . . .
C7 C 0.6537(3) 0.1649(3) 0.47885(6) 0.0620(8) Uani 1 1 d . . . . .
H7 H 0.664777 0.067401 0.478742 0.074 Uiso 1 1 calc R U . . .
C8 C 0.6540(3) 0.2479(3) 0.50000(6) 0.0530(7) Uani 1 1 d . . . . .
C9 C 0.6706(3) 0.2124(3) 0.52690(6) 0.0533(7) Uani 1 1 d . . . . .
C10 C 0.6327(3) 0.0794(3) 0.53559(6) 0.0640(9) Uani 1 1 d . . . . .
H10 H 0.595780 0.014405 0.524188 0.077 Uiso 1 1 calc R U . . .
C11 C 0.6491(3) 0.0430(3) 0.56078(6) 0.0634(9) Uani 1 1 d . . . . .
H11 H 0.621591 -0.046026 0.566078 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7056(3) 0.1350(3) 0.57862(6) 0.0520(7) Uani 1 1 d . . . . .
C13 C 0.7409(3) 0.2678(3) 0.56975(6) 0.0594(8) Uani 1 1 d . . . . .
H13 H 0.776934 0.333277 0.581158 0.071 Uiso 1 1 calc R U . . .
C14 C 0.7241(3) 0.3054(3) 0.54465(6) 0.0595(8) Uani 1 1 d . . . . .
H14 H 0.749249 0.395361 0.539460 0.071 Uiso 1 1 calc R U . . .
C15 C 0.7287(3) 0.0939(3) 0.60560(6) 0.0528(7) Uani 1 1 d . . . . .
C16 C 0.6132(3) 0.0278(3) 0.61900(6) 0.0536(7) Uani 1 1 d . . . . .
C17 C 0.3739(3) 0.0134(4) 0.62677(7) 0.0744(10) Uani 1 1 d . . . . .
H17 H 0.286844 0.046041 0.623749 0.089 Uiso 1 1 calc R U . . .
C18 C 0.3965(4) -0.0987(4) 0.64311(7) 0.0846(11) Uani 1 1 d . . . . .
H18 H 0.324625 -0.139984 0.651496 0.102 Uiso 1 1 calc R U . . .
C19 C 0.5244(4) -0.1493(4) 0.64702(7) 0.0846(11) Uani 1 1 d . . . . .
H19 H 0.538729 -0.225309 0.657950 0.101 Uiso 1 1 calc R U . . .
C20 C 0.6313(3) -0.0886(3) 0.63491(6) 0.0672(9) Uani 1 1 d . . . . .
H20 H 0.717250 -0.125659 0.637354 0.081 Uiso 1 1 calc R U . . .
C21 C 0.8524(3) 0.1124(3) 0.61673(6) 0.0550(8) Uani 1 1 d . . . . .
C22 C 0.8806(3) 0.1036(3) 0.64467(6) 0.0560(8) Uani 1 1 d . . . . .
C23 C 0.9961(3) 0.0359(3) 0.65348(6) 0.0678(9) Uani 1 1 d . . . . .
H23 H 1.052332 -0.007493 0.641799 0.081 Uiso 1 1 calc R U . . .
C24 C 1.0297(4) 0.0310(4) 0.67877(8) 0.0891(12) Uani 1 1 d . . . . .
H24 H 1.106864 -0.017101 0.684026 0.107 Uiso 1 1 calc R U . . .
C25 C 0.9525(5) 0.0949(5) 0.69618(8) 0.1056(15) Uani 1 1 d . . . . .
H25 H 0.977347 0.093042 0.713338 0.127 Uiso 1 1 calc R U . . .
C26 C 0.8352(5) 0.1639(4) 0.68843(8) 0.0998(14) Uani 1 1 d . . . . .
H26 H 0.780755 0.206896 0.700445 0.120 Uiso 1 1 calc R U . . .
C27 C 0.7991(4) 0.1687(4) 0.66259(7) 0.0807(10) Uani 1 1 d . . . . .
H27 H 0.720933 0.215145 0.657381 0.097 Uiso 1 1 calc R U . . .
C28 C 0.9714(3) 0.1431(3) 0.60122(6) 0.0556(8) Uani 1 1 d . . . . .
C29 C 1.0516(3) 0.2615(4) 0.60603(7) 0.0695(9) Uani 1 1 d . . . . .
H29 H 1.029618 0.322647 0.619212 0.083 Uiso 1 1 calc R U . . .
C30 C 1.1615(4) 0.2883(5) 0.59160(8) 0.0917(12) Uani 1 1 d . . . . .
H30 H 1.212738 0.368809 0.594721 0.110 Uiso 1 1 calc R U . . .
C31 C 1.1973(4) 0.1975(6) 0.57248(8) 0.1010(15) Uani 1 1 d . . . . .
H31 H 1.273386 0.215808 0.562871 0.121 Uiso 1 1 calc R U . . .
C32 C 1.1206(4) 0.0794(5) 0.56751(7) 0.0903(12) Uani 1 1 d . . . . .
H32 H 1.145084 0.017957 0.554537 0.108 Uiso 1 1 calc R U . . .
C33 C 1.0072(3) 0.0516(4) 0.58173(6) 0.0679(9) Uani 1 1 d . . . . .
H33 H 0.955210 -0.027954 0.578262 0.081 Uiso 1 1 calc R U . . .
C34 C 0.4816(3) 0.0763(3) 0.61499(6) 0.0636(8) Uani 1 1 d . . . . .
H34 H 0.466455 0.152615 0.604160 0.076 Uiso 1 1 calc R U . . .
N2 N 0.7761(3) 0.6710(3) 0.56886(5) 0.0677(6) Uani 1 1 d D U . . .
H2A H 0.697724 0.671938 0.575652 0.081 Uiso 1 1 calc R U . . .
C36 C 0.9403(3) 0.6757(4) 0.54016(6) 0.0653(9) Uani 1 1 d . . . . .
C37 C 0.9988(4) 0.6857(5) 0.51633(7) 0.1076(15) Uani 1 1 d . . . . .
H37 H 1.091097 0.673937 0.514416 0.129 Uiso 1 1 calc R U . . .
C38 C 0.9160(4) 0.7138(5) 0.49552(7) 0.1057(14) Uani 1 1 d . . . . .
H38 H 0.953103 0.720899 0.479388 0.127 Uiso 1 1 calc R U . . .
C39 C 0.7791(4) 0.7313(4) 0.49842(7) 0.0796(11) Uani 1 1 d . . . . .
H39 H 0.725816 0.751464 0.484161 0.096 Uiso 1 1 calc R U . . .
C40 C 0.7198(3) 0.7197(3) 0.52164(6) 0.0655(9) Uani 1 1 d . . . . .
H40 H 0.627276 0.730855 0.523319 0.079 Uiso 1 1 calc R U . . .
C41 C 0.8020(3) 0.6907(3) 0.54281(6) 0.0544(7) Uani 1 1 d D U . . .
C42 C 0.9953(3) 0.6526(3) 0.56424(5) 0.0561(8) Uani 1 1 d . U . . .
H42 H 1.086531 0.640586 0.567840 0.067 Uiso 1 1 calc R U . . .
C43 C 0.8961(3) 0.6500(3) 0.58175(6) 0.0584(7) Uani 1 1 d . U . . .
C44 C 0.9147(3) 0.6326(3) 0.60899(5) 0.0512(7) Uani 1 1 d . . . . .
C45 C 0.8145(3) 0.5759(3) 0.62411(6) 0.0556(8) Uani 1 1 d . . . . .
H45 H 0.734513 0.545667 0.616473 0.067 Uiso 1 1 calc R U . . .
C46 C 0.8306(3) 0.5633(3) 0.65007(6) 0.0547(8) Uani 1 1 d . . . . .
H46 H 0.760947 0.526089 0.659641 0.066 Uiso 1 1 calc R U . . .
C47 C 0.9500(3) 0.6056(3) 0.66238(5) 0.0493(7) Uani 1 1 d . . . . .
C48 C 1.0494(3) 0.6620(3) 0.64701(6) 0.0592(8) Uani 1 1 d . . . . .
H48 H 1.129937 0.691575 0.654560 0.071 Uiso 1 1 calc R U . . .
C49 C 1.0332(3) 0.6757(3) 0.62121(6) 0.0607(8) Uani 1 1 d . . . . .
H49 H 1.102372 0.714272 0.611665 0.073 Uiso 1 1 calc R U . . .
C50 C 0.9645(3) 0.5959(3) 0.69066(5) 0.0492(7) Uani 1 1 d . . . . .
C51 C 0.8396(3) 0.6286(3) 0.70515(5) 0.0508(7) Uani 1 1 d . . . . .
C52 C 0.7704(3) 0.7541(3) 0.70138(6) 0.0611(8) Uani 1 1 d . . . . .
H52 H 0.799450 0.817543 0.689087 0.073 Uiso 1 1 calc R U . . .
C53 C 0.6587(3) 0.7858(4) 0.71572(7) 0.0701(9) Uani 1 1 d . . . . .
H53 H 0.615087 0.871894 0.713456 0.084 Uiso 1 1 calc R U . . .
C54 C 0.6116(3) 0.6908(4) 0.73333(6) 0.0723(10) Uani 1 1 d . . . . .
H54 H 0.536157 0.712226 0.742919 0.087 Uiso 1 1 calc R U . . .
C55 C 0.6761(3) 0.5655(4) 0.73659(6) 0.0726(9) Uani 1 1 d . . . . .
H55 H 0.643608 0.500600 0.748294 0.087 Uiso 1 1 calc R U . . .
C56 C 0.7896(3) 0.5332(3) 0.72273(6) 0.0587(8) Uani 1 1 d . . . . .
H56 H 0.832697 0.447052 0.725220 0.070 Uiso 1 1 calc R U . . .
C57 C 1.0808(3) 0.5602(3) 0.70288(5) 0.0498(7) Uani 1 1 d . . . . .
C59 C 1.1860(3) 0.3915(3) 0.67250(6) 0.0647(9) Uani 1 1 d . . . . .
H59 H 1.102012 0.349937 0.669965 0.078 Uiso 1 1 calc R U . . .
C60 C 1.2952(4) 0.3410(4) 0.65963(7) 0.0832(11) Uani 1 1 d . . . . .
H60 H 1.284148 0.266876 0.648168 0.100 Uiso 1 1 calc R U . . .
C61 C 1.4208(4) 0.3986(4) 0.66349(7) 0.0811(11) Uani 1 1 d . . . . .
H61 H 1.494159 0.364210 0.654566 0.097 Uiso 1 1 calc R U . . .
C62 C 1.4374(3) 0.5070(4) 0.68058(7) 0.0690(9) Uani 1 1 d . . . . .
H62 H 1.522398 0.545478 0.683518 0.083 Uiso 1 1 calc R U . . .
C63 C 1.3275(3) 0.5587(3) 0.69337(6) 0.0587(8) Uani 1 1 d . . . . .
H63 H 1.339345 0.631837 0.705020 0.070 Uiso 1 1 calc R U . . .
C64 C 1.1996(3) 0.5037(3) 0.68919(5) 0.0506(7) Uani 1 1 d . . . . .
C65 C 1.0985(3) 0.5731(3) 0.73112(5) 0.0521(7) Uani 1 1 d . . . . .
C66 C 1.0598(3) 0.6933(3) 0.74424(6) 0.0642(9) Uani 1 1 d . . . . .
H66 H 1.023074 0.769040 0.735266 0.077 Uiso 1 1 calc R U . . .
C67 C 1.0750(3) 0.7023(4) 0.77054(7) 0.0787(10) Uani 1 1 d . . . . .
H67 H 1.047471 0.783087 0.779083 0.094 Uiso 1 1 calc R U . . .
C68 C 1.1309(4) 0.5916(5) 0.78392(7) 0.0822(11) Uani 1 1 d . . . . .
H68 H 1.140826 0.597017 0.801545 0.099 Uiso 1 1 calc R U . . .
C69 C 1.1719(3) 0.4733(4) 0.77118(7) 0.0764(10) Uani 1 1 d . . . . .
H69 H 1.210189 0.398596 0.780217 0.092 Uiso 1 1 calc R U . . .
C70 C 1.1570(3) 0.4641(3) 0.74505(6) 0.0637(9) Uani 1 1 d . . . . .
H70 H 1.186605 0.383637 0.736648 0.076 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.8600 . ?
N1 C6 1.370(4) . ?
N1 C8 1.390(4) . ?
C1 C2 1.395(4) . ?
C1 C6 1.407(4) . ?
C1 C7 1.418(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(4) . ?
C8 C9 1.458(4) . ?
C9 C10 1.394(4) . ?
C9 C14 1.382(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(4) . ?
C12 C13 1.388(4) . ?
C12 C15 1.483(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.491(4) . ?
C15 C21 1.363(4) . ?
C16 C20 1.392(4) . ?
C16 C34 1.399(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C17 C34 1.378(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.369(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.491(4) . ?
C21 C28 1.473(4) . ?
C22 C23 1.388(4) . ?
C22 C27 1.393(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.364(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.345(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.391(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.398(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.396(4) . ?
C28 C33 1.390(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.360(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.372(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(6) . ?
C32 H32 0.9300 . ?
C32 C33 1.384(5) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N2 H2A 0.8600 . ?
N2 C41 1.406(4) . ?
N2 C43 1.377(4) . ?
C36 C37 1.389(4) . ?
C36 C41 1.389(4) . ?
C36 C42 1.386(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.383(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.380(5) . ?
C39 H39 0.9300 . ?
C39 C40 1.365(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.396(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.356(4) . ?
C43 C44 1.448(4) . ?
C44 C45 1.389(4) . ?
C44 C49 1.393(4) . ?
C45 H45 0.9300 . ?
C45 C46 1.374(4) . ?
C46 H46 0.9300 . ?
C46 C47 1.400(4) . ?
C47 C48 1.390(4) . ?
C47 C50 1.491(4) . ?
C48 H48 0.9300 . ?
C48 C49 1.367(4) . ?
C49 H49 0.9300 . ?
C50 C51 1.496(4) . ?
C50 C57 1.355(4) . ?
C51 C52 1.386(4) . ?
C51 C56 1.387(4) . ?
C52 H52 0.9300 . ?
C52 C53 1.382(4) . ?
C53 H53 0.9300 . ?
C53 C54 1.376(5) . ?
C54 H54 0.9300 . ?
C54 C55 1.358(5) . ?
C55 H55 0.9300 . ?
C55 C56 1.383(4) . ?
C56 H56 0.9300 . ?
C57 C64 1.489(4) . ?
C57 C65 1.494(4) . ?
C59 H59 0.9300 . ?
C59 C60 1.372(4) . ?
C59 C64 1.382(4) . ?
C60 H60 0.9300 . ?
C60 C61 1.373(5) . ?
C61 H61 0.9300 . ?
C61 C62 1.372(5) . ?
C62 H62 0.9300 . ?
C62 C63 1.379(4) . ?
C63 H63 0.9300 . ?
C63 C64 1.388(4) . ?
C65 C66 1.387(4) . ?
C65 C70 1.387(4) . ?
C66 H66 0.9300 . ?
C66 C67 1.388(4) . ?
C67 H67 0.9300 . ?
C67 C68 1.374(5) . ?
C68 H68 0.9300 . ?
C68 C69 1.369(5) . ?
C69 H69 0.9300 . ?
C69 C70 1.379(4) . ?
C70 H70 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
C6 N1 H1 124.9 . . ?
C6 N1 C8 110.1(2) . . ?
C8 N1 H1 124.9 . . ?
C2 C1 C6 118.5(3) . . ?
C2 C1 C7 135.0(3) . . ?
C6 C1 C7 106.5(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.7(3) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C1 107.1(3) . . ?
N1 C6 C5 130.5(3) . . ?
C5 C6 C1 122.4(3) . . ?
C1 C7 H7 125.5 . . ?
C8 C7 C1 109.1(3) . . ?
C8 C7 H7 125.5 . . ?
N1 C8 C9 121.9(3) . . ?
C7 C8 N1 107.2(3) . . ?
C7 C8 C9 130.9(3) . . ?
C10 C9 C8 119.9(3) . . ?
C14 C9 C8 122.8(3) . . ?
C14 C9 C10 117.3(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 118.9 . . ?
C10 C11 C12 122.1(3) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C15 122.2(3) . . ?
C13 C12 C11 116.3(3) . . ?
C13 C12 C15 121.4(3) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 C12 121.9(3) . . ?
C14 C13 H13 119.0 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.5(3) . . ?
C13 C14 H14 119.3 . . ?
C12 C15 C16 116.8(2) . . ?
C21 C15 C12 120.1(3) . . ?
C21 C15 C16 123.1(3) . . ?
C20 C16 C15 121.4(3) . . ?
C20 C16 C34 117.6(3) . . ?
C34 C16 C15 120.9(3) . . ?
C18 C17 H17 120.3 . . ?
C34 C17 H17 120.3 . . ?
C34 C17 C18 119.4(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C16 C20 H20 119.5 . . ?
C19 C20 C16 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C21 C22 124.7(3) . . ?
C15 C21 C28 120.9(3) . . ?
C28 C21 C22 114.4(2) . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 C27 117.7(3) . . ?
C27 C22 C21 122.4(3) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 C22 122.0(3) . . ?
C24 C23 H23 119.0 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(4) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.7(4) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.1(4) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 119.8(4) . . ?
C22 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C29 C28 C21 121.2(3) . . ?
C33 C28 C21 119.9(3) . . ?
C33 C28 C29 118.9(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.6(4) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.5(4) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0(4) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.3(4) . . ?
C33 C32 H32 119.9 . . ?
C28 C33 H33 120.1 . . ?
C32 C33 C28 119.7(3) . . ?
C32 C33 H33 120.1 . . ?
C16 C34 H34 119.4 . . ?
C17 C34 C16 121.3(3) . . ?
C17 C34 H34 119.4 . . ?
C41 N2 H2A 125.4 . . ?
C43 N2 H2A 125.4 . . ?
C43 N2 C41 109.1(3) . . ?
C37 C36 C41 120.6(3) . . ?
C42 C36 C37 131.8(3) . . ?
C42 C36 C41 107.6(3) . . ?
C36 C37 H37 120.9 . . ?
C38 C37 C36 118.2(4) . . ?
C38 C37 H37 120.9 . . ?
C37 C38 H38 119.6 . . ?
C39 C38 C37 120.8(4) . . ?
C39 C38 H38 119.6 . . ?
C38 C39 H39 119.1 . . ?
C40 C39 C38 121.8(3) . . ?
C40 C39 H39 119.1 . . ?
C39 C40 H40 120.9 . . ?
C39 C40 C41 118.1(3) . . ?
C41 C40 H40 120.9 . . ?
C36 C41 N2 106.1(2) . . ?
C36 C41 C40 120.5(3) . . ?
C40 C41 N2 133.3(3) . . ?
C36 C42 H42 125.1 . . ?
C43 C42 C36 109.9(3) . . ?
C43 C42 H42 125.1 . . ?
N2 C43 C44 126.8(3) . . ?
C42 C43 N2 107.2(3) . . ?
C42 C43 C44 125.9(3) . . ?
C45 C44 C43 121.7(3) . . ?
C45 C44 C49 117.2(3) . . ?
C49 C44 C43 121.1(3) . . ?
C44 C45 H45 119.2 . . ?
C46 C45 C44 121.7(3) . . ?
C46 C45 H45 119.2 . . ?
C45 C46 H46 119.4 . . ?
C45 C46 C47 121.2(3) . . ?
C47 C46 H46 119.4 . . ?
C46 C47 C50 120.7(3) . . ?
C48 C47 C46 116.5(3) . . ?
C48 C47 C50 122.8(3) . . ?
C47 C48 H48 118.8 . . ?
C49 C48 C47 122.4(3) . . ?
C49 C48 H48 118.8 . . ?
C44 C49 H49 119.5 . . ?
C48 C49 C44 121.0(3) . . ?
C48 C49 H49 119.5 . . ?
C47 C50 C51 115.1(2) . . ?
C57 C50 C47 123.8(3) . . ?
C57 C50 C51 121.2(3) . . ?
C52 C51 C50 121.2(3) . . ?
C52 C51 C56 118.2(3) . . ?
C56 C51 C50 120.7(3) . . ?
C51 C52 H52 119.7 . . ?
C53 C52 C51 120.6(3) . . ?
C53 C52 H52 119.7 . . ?
C52 C53 H53 119.8 . . ?
C54 C53 C52 120.4(3) . . ?
C54 C53 H53 119.8 . . ?
C53 C54 H54 120.3 . . ?
C55 C54 C53 119.4(3) . . ?
C55 C54 H54 120.3 . . ?
C54 C55 H55 119.6 . . ?
C54 C55 C56 120.9(3) . . ?
C56 C55 H55 119.6 . . ?
C51 C56 H56 119.8 . . ?
C55 C56 C51 120.4(3) . . ?
C55 C56 H56 119.8 . . ?
C50 C57 C64 122.5(3) . . ?
C50 C57 C65 122.5(3) . . ?
C64 C57 C65 115.1(2) . . ?
C60 C59 H59 119.7 . . ?
C60 C59 C64 120.6(3) . . ?
C64 C59 H59 119.7 . . ?
C59 C60 H60 119.6 . . ?
C59 C60 C61 120.8(3) . . ?
C61 C60 H60 119.6 . . ?
C60 C61 H61 120.2 . . ?
C62 C61 C60 119.6(3) . . ?
C62 C61 H61 120.2 . . ?
C61 C62 H62 120.2 . . ?
C61 C62 C63 119.7(3) . . ?
C63 C62 H62 120.2 . . ?
C62 C63 H63 119.4 . . ?
C62 C63 C64 121.2(3) . . ?
C64 C63 H63 119.4 . . ?
C59 C64 C57 120.7(3) . . ?
C59 C64 C63 118.0(3) . . ?
C63 C64 C57 121.2(3) . . ?
C66 C65 C57 121.9(3) . . ?
C66 C65 C70 117.8(3) . . ?
C70 C65 C57 120.3(3) . . ?
C65 C66 H66 119.5 . . ?
C65 C66 C67 121.1(3) . . ?
C67 C66 H66 119.5 . . ?
C66 C67 H67 120.1 . . ?
C68 C67 C66 119.9(3) . . ?
C68 C67 H67 120.1 . . ?
C67 C68 H68 120.1 . . ?
C69 C68 C67 119.7(3) . . ?
C69 C68 H68 120.1 . . ?
C68 C69 H69 119.7 . . ?
C68 C69 C70 120.5(3) . . ?
C70 C69 H69 119.7 . . ?
C65 C70 H70 119.5 . . ?
C69 C70 C65 121.0(3) . . ?
C69 C70 H70 119.5 . . ?

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
N1 C8 C9 C10 151.5(3) . . . . ?
N1 C8 C9 C14 -29.0(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C7 C8 N1 0.7(3) . . . . ?
C1 C7 C8 C9 180.0(3) . . . . ?
C2 C1 C6 N1 -179.8(3) . . . . ?
C2 C1 C6 C5 3.1(4) . . . . ?
C2 C1 C7 C8 -179.5(3) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 N1 -177.6(3) . . . . ?
C4 C5 C6 C1 -1.3(5) . . . . ?
C6 N1 C8 C7 0.5(3) . . . . ?
C6 N1 C8 C9 -178.9(2) . . . . ?
C6 C1 C2 C3 -2.5(5) . . . . ?
C6 C1 C7 C8 -1.5(3) . . . . ?
C7 C1 C2 C3 175.4(3) . . . . ?
C7 C1 C6 N1 1.8(3) . . . . ?
C7 C1 C6 C5 -175.3(3) . . . . ?
C7 C8 C9 C10 -27.7(5) . . . . ?
C7 C8 C9 C14 151.8(3) . . . . ?
C8 N1 C6 C1 -1.4(3) . . . . ?
C8 N1 C6 C5 175.4(3) . . . . ?
C8 C9 C10 C11 179.1(3) . . . . ?
C8 C9 C14 C13 -178.7(3) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C9 C14 C13 0.8(4) . . . . ?
C10 C11 C12 C13 2.0(5) . . . . ?
C10 C11 C12 C15 -177.4(3) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C11 C12 C15 C16 -49.4(4) . . . . ?
C11 C12 C15 C21 128.3(3) . . . . ?
C12 C13 C14 C9 0.2(5) . . . . ?
C12 C15 C16 C20 137.5(3) . . . . ?
C12 C15 C16 C34 -39.2(4) . . . . ?
C12 C15 C21 C22 166.7(3) . . . . ?
C12 C15 C21 C28 -13.5(4) . . . . ?
C13 C12 C15 C16 131.3(3) . . . . ?
C13 C12 C15 C21 -51.0(4) . . . . ?
C14 C9 C10 C11 -0.4(4) . . . . ?
C15 C12 C13 C14 177.8(3) . . . . ?
C15 C16 C20 C19 -179.5(3) . . . . ?
C15 C16 C34 C17 178.2(3) . . . . ?
C15 C21 C22 C23 138.6(3) . . . . ?
C15 C21 C22 C27 -45.4(4) . . . . ?
C15 C21 C28 C29 125.1(3) . . . . ?
C15 C21 C28 C33 -56.3(4) . . . . ?
C16 C15 C21 C22 -15.7(4) . . . . ?
C16 C15 C21 C28 164.0(3) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C18 C17 C34 C16 0.8(5) . . . . ?
C18 C19 C20 C16 1.8(6) . . . . ?
C20 C16 C34 C17 1.4(5) . . . . ?
C21 C15 C16 C20 -40.1(4) . . . . ?
C21 C15 C16 C34 143.2(3) . . . . ?
C21 C22 C23 C24 176.8(3) . . . . ?
C21 C22 C27 C26 -176.1(3) . . . . ?
C21 C28 C29 C30 179.8(3) . . . . ?
C21 C28 C33 C32 -178.8(3) . . . . ?
C22 C21 C28 C29 -55.1(4) . . . . ?
C22 C21 C28 C33 123.5(3) . . . . ?
C22 C23 C24 C25 -1.4(6) . . . . ?
C23 C22 C27 C26 -0.1(5) . . . . ?
C23 C24 C25 C26 1.6(6) . . . . ?
C24 C25 C26 C27 -1.1(6) . . . . ?
C25 C26 C27 C22 0.3(6) . . . . ?
C27 C22 C23 C24 0.6(5) . . . . ?
C28 C21 C22 C23 -41.1(4) . . . . ?
C28 C21 C22 C27 134.8(3) . . . . ?
C28 C29 C30 C31 -1.6(6) . . . . ?
C29 C28 C33 C32 -0.1(5) . . . . ?
C29 C30 C31 C32 1.0(6) . . . . ?
C30 C31 C32 C33 0.0(6) . . . . ?
C31 C32 C33 C28 -0.4(5) . . . . ?
C33 C28 C29 C30 1.1(5) . . . . ?
C34 C16 C20 C19 -2.7(5) . . . . ?
C34 C17 C18 C19 -1.8(5) . . . . ?
N2 C43 C44 C45 28.3(5) . . . . ?
N2 C43 C44 C49 -150.1(3) . . . . ?
C36 C37 C38 C39 0.0(7) . . . . ?
C36 C42 C43 N2 0.3(4) . . . . ?
C36 C42 C43 C44 -178.0(3) . . . . ?
C37 C36 C41 N2 178.4(4) . . . . ?
C37 C36 C41 C40 -1.6(5) . . . . ?
C37 C36 C42 C43 -179.3(4) . . . . ?
C37 C38 C39 C40 -1.0(7) . . . . ?
C38 C39 C40 C41 0.6(5) . . . . ?
C39 C40 C41 N2 -179.3(3) . . . . ?
C39 C40 C41 C36 0.7(5) . . . . ?
C41 N2 C43 C42 -1.6(3) . . . . ?
C41 N2 C43 C44 176.7(3) . . . . ?
C41 C36 C37 C38 1.2(6) . . . . ?
C41 C36 C42 C43 1.1(4) . . . . ?
C42 C36 C37 C38 -178.2(4) . . . . ?
C42 C36 C41 N2 -2.0(3) . . . . ?
C42 C36 C41 C40 178.0(3) . . . . ?
C42 C43 C44 C45 -153.8(3) . . . . ?
C42 C43 C44 C49 27.8(5) . . . . ?
C43 N2 C41 C36 2.2(3) . . . . ?
C43 N2 C41 C40 -177.8(3) . . . . ?
C43 C44 C45 C46 -178.0(3) . . . . ?
C43 C44 C49 C48 178.6(3) . . . . ?
C44 C45 C46 C47 -0.9(4) . . . . ?
C45 C44 C49 C48 0.1(4) . . . . ?
C45 C46 C47 C48 0.8(4) . . . . ?
C45 C46 C47 C50 177.9(3) . . . . ?
C46 C47 C48 C49 -0.3(4) . . . . ?
C46 C47 C50 C51 -36.6(4) . . . . ?
C46 C47 C50 C57 143.3(3) . . . . ?
C47 C48 C49 C44 -0.2(5) . . . . ?
C47 C50 C51 C52 -54.1(4) . . . . ?
C47 C50 C51 C56 125.7(3) . . . . ?
C47 C50 C57 C64 -10.6(4) . . . . ?
C47 C50 C57 C65 170.2(3) . . . . ?
C48 C47 C50 C51 140.3(3) . . . . ?
C48 C47 C50 C57 -39.8(4) . . . . ?
C49 C44 C45 C46 0.4(4) . . . . ?
C50 C47 C48 C49 -177.3(3) . . . . ?
C50 C51 C52 C53 -177.0(3) . . . . ?
C50 C51 C56 C55 178.2(3) . . . . ?
C50 C57 C64 C59 -50.9(4) . . . . ?
C50 C57 C64 C63 131.1(3) . . . . ?
C50 C57 C65 C66 -46.4(4) . . . . ?
C50 C57 C65 C70 134.6(3) . . . . ?
C51 C50 C57 C64 169.3(3) . . . . ?
C51 C50 C57 C65 -9.9(4) . . . . ?
C51 C52 C53 C54 -2.4(5) . . . . ?
C52 C51 C56 C55 -2.0(4) . . . . ?
C52 C53 C54 C55 0.2(5) . . . . ?
C53 C54 C55 C56 1.0(5) . . . . ?
C54 C55 C56 C51 -0.1(5) . . . . ?
C56 C51 C52 C53 3.2(4) . . . . ?
C57 C50 C51 C52 126.0(3) . . . . ?
C57 C50 C51 C56 -54.2(4) . . . . ?
C57 C65 C66 C67 178.9(3) . . . . ?
C57 C65 C70 C69 -178.9(3) . . . . ?
C59 C60 C61 C62 0.6(6) . . . . ?
C60 C59 C64 C57 179.0(3) . . . . ?
C60 C59 C64 C63 -2.9(5) . . . . ?
C60 C61 C62 C63 -1.1(5) . . . . ?
C61 C62 C63 C64 -0.4(5) . . . . ?
C62 C63 C64 C57 -179.6(3) . . . . ?
C62 C63 C64 C59 2.4(5) . . . . ?
C64 C57 C65 C66 134.3(3) . . . . ?
C64 C57 C65 C70 -44.7(4) . . . . ?
C64 C59 C60 C61 1.5(5) . . . . ?
C65 C57 C64 C59 128.3(3) . . . . ?
C65 C57 C64 C63 -49.6(4) . . . . ?
C65 C66 C67 C68 0.9(5) . . . . ?
C66 C65 C70 C69 2.1(4) . . . . ?
C66 C67 C68 C69 0.4(6) . . . . ?
C67 C68 C69 C70 -0.3(5) . . . . ?
C68 C69 C70 C65 -1.0(5) . . . . ?
C70 C65 C66 C67 -2.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_preparation       
'Luminescent,Aggregation-Induced Emission (AIE)'
####################################################################### 
# 
# 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_123_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2163570'
loop_
_audit_author_name
_audit_author_address
'Hongyuan Ren'
;Nanjing University
China
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-04-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.0103(13)
_cell_length_b                   35.603(3)
_cell_length_c                   11.3760(13)
_cell_angle_alpha                90
_cell_angle_beta                 117.174(3)
_cell_angle_gamma                90
_cell_volume                     5048.1(9)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    5724
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6024
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1418 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.8079.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23828
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.011
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                6420
_reflns_number_total             8815
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.0029(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         8815
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0729
_refine_ls_restrained_S_all      1.041
_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)+(0.1309P)²+3.1219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2247
_refine_special_details          
'Refined as a 2-component perfect inversion twin.,Twin'
_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
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C41(H41A,H41B), C62(H62A,H62B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C7(H7), C10(H10), C12(H12), C14(H14), C17(H17),
 N2(H2), C25(H25), C26(H26), C28(H28), C31(H31), C33(H33), C35(H35), C38(H38),
 N3(H3), C46(H46), C47(H47), C49(H49), C52(H52), C54(H54), C56(H56), C59(H59)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C42(H42A,H42B,H42C), C57(H57A,H57B,H57C), C58(H58A,
 H58B,H58C), C63(H63A,H63B,H63C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7562(3) 0.71447(11) 0.9492(5) 0.0365(10) Uani 1 1 d . . . . .
O2 O 0.8088(4) 0.78529(12) 1.0415(5) 0.0439(11) Uani 1 1 d . . . . .
O3 O 0.8985(4) 0.76361(11) 1.2506(5) 0.0370(10) Uani 1 1 d . . . . .
N1 N 0.7335(4) 0.56298(13) 0.9428(5) 0.0326(11) Uani 1 1 d . . . . .
H1 H 0.702232 0.546753 0.880887 0.039 Uiso 1 1 calc R U . . .
C1 C 0.7919(5) 0.61759(16) 1.0494(6) 0.0285(12) Uani 1 1 d . . . . .
C2 C 0.7960(5) 0.65769(14) 1.0523(6) 0.0262(12) Uani 1 1 d . . . . .
C3 C 0.7429(5) 0.67620(15) 0.9319(7) 0.0335(14) Uani 1 1 d . . . . .
C4 C 0.6852(5) 0.65937(15) 0.8091(6) 0.0361(14) Uani 1 1 d . . . . .
H4 H 0.651612 0.673671 0.732566 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6794(5) 0.62060(17) 0.8050(6) 0.0363(14) Uani 1 1 d . . . . .
H5 H 0.643154 0.607932 0.725144 0.044 Uiso 1 1 calc R U . . .
C6 C 0.7297(5) 0.60092(16) 0.9248(6) 0.0303(13) Uani 1 1 d . . . . .
C7 C 0.8321(5) 0.58824(15) 1.1432(6) 0.0302(13) Uani 1 1 d . . . . .
H7 H 0.875354 0.590919 1.233572 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7948(5) 0.55437(16) 1.0747(6) 0.0296(13) Uani 1 1 d . . . . .
C9 C 0.8133(5) 0.51589(16) 1.1249(7) 0.0334(14) Uani 1 1 d . . . . .
C10 C 0.8835(5) 0.50898(16) 1.2571(6) 0.0323(13) Uani 1 1 d . . . . .
H10 H 0.917100 0.529090 1.312965 0.039 Uiso 1 1 calc R U . . .
C11 C 0.9044(5) 0.47285(17) 1.3070(6) 0.0335(13) Uani 1 1 d . . . . .
C12 C 0.8531(5) 0.44300(17) 1.2217(7) 0.0387(15) Uani 1 1 d . . . . .
H12 H 0.866285 0.418578 1.254197 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7828(5) 0.44899(15) 1.0894(7) 0.0347(14) Uani 1 1 d . . . . .
C14 C 0.7628(5) 0.48525(17) 1.0413(6) 0.0323(13) Uani 1 1 d . . . . .
H14 H 0.715513 0.489464 0.952818 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7313(6) 0.41581(17) 0.9992(8) 0.0473(18) Uani 1 1 d . . . . .
H15A H 0.756324 0.414530 0.933603 0.071 Uiso 1 1 calc R U . . .
H15B H 0.654722 0.418783 0.956590 0.071 Uiso 1 1 calc R U . . .
H15C H 0.750099 0.393085 1.050266 0.071 Uiso 1 1 calc R U . . .
C16 C 0.9806(6) 0.4655(2) 1.4482(8) 0.0486(18) Uani 1 1 d . . . . .
H16A H 1.038541 0.450151 1.453153 0.073 Uiso 1 1 calc R U . . .
H16B H 0.943697 0.452825 1.489931 0.073 Uiso 1 1 calc R U . . .
H16C H 1.008515 0.488964 1.492410 0.073 Uiso 1 1 calc R U . . .
C17 C 0.8445(5) 0.68658(16) 1.1482(7) 0.0311(13) Uani 1 1 d . . . . .
H17 H 0.886126 0.683306 1.238679 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8186(5) 0.71951(16) 1.0827(7) 0.0337(14) Uani 1 1 d . . . . .
C19 C 0.8406(5) 0.75939(16) 1.1206(7) 0.0317(13) Uani 1 1 d . . . . .
C20 C 0.9225(6) 0.80269(16) 1.2924(7) 0.0413(16) Uani 1 1 d . . . . .
H20A H 0.856577 0.816769 1.265752 0.050 Uiso 1 1 calc R U . . .
H20B H 0.963427 0.814175 1.252421 0.050 Uiso 1 1 calc R U . . .
C21 C 0.9868(7) 0.80269(19) 1.4408(8) 0.0519(19) Uani 1 1 d . . . . .
H21A H 1.053750 0.790018 1.465665 0.078 Uiso 1 1 calc R U . . .
H21B H 0.947199 0.789951 1.478960 0.078 Uiso 1 1 calc R U . . .
H21C H 1.000323 0.828117 1.472306 0.078 Uiso 1 1 calc R U . . .
O4 O 0.9377(3) 0.75015(11) 0.8234(4) 0.0369(11) Uani 1 1 d . . . . .
O5 O 0.8096(4) 0.76126(12) 0.5634(5) 0.0472(12) Uani 1 1 d . . . . .
O6 O 0.7815(4) 0.69974(12) 0.5294(5) 0.0433(11) Uani 1 1 d . . . . .
N2 N 1.1512(4) 0.67714(14) 1.2887(6) 0.0353(12) Uani 1 1 d . . . . .
H2 H 1.190133 0.684471 1.368640 0.042 Uiso 1 1 calc R U . . .
C22 C 1.0454(5) 0.67759(15) 1.0688(6) 0.0278(12) Uani 1 1 d . . . . .
C23 C 0.9894(4) 0.69665(15) 0.9474(7) 0.0300(13) Uani 1 1 d . . . . .
C24 C 0.9976(5) 0.73588(16) 0.9480(7) 0.0331(14) Uani 1 1 d . . . . .
C25 C 1.0573(6) 0.75742(17) 1.0599(7) 0.0433(17) Uani 1 1 d . . . . .
H25 H 1.059034 0.783459 1.054655 0.052 Uiso 1 1 calc R U . . .
C26 C 1.1130(5) 0.73945(16) 1.1768(8) 0.0404(16) Uani 1 1 d . . . . .
H26 H 1.155572 0.752969 1.252914 0.048 Uiso 1 1 calc R U . . .
C27 C 1.1057(5) 0.70000(16) 1.1818(7) 0.0331(14) Uani 1 1 d . . . . .
C28 C 1.0595(5) 0.64006(15) 1.1143(6) 0.0287(12) Uani 1 1 d . . . . .
H28 H 1.029669 0.618929 1.062318 0.034 Uiso 1 1 calc R U . . .
C29 C 1.1250(5) 0.64009(16) 1.2492(7) 0.0318(13) Uani 1 1 d . . . . .
C30 C 1.1679(5) 0.60879(16) 1.3420(7) 0.0311(13) Uani 1 1 d . . . . .
C31 C 1.1480(5) 0.57215(17) 1.2929(7) 0.0356(14) Uani 1 1 d . . . . .
H31 H 1.103743 0.568183 1.203323 0.043 Uiso 1 1 calc R U . . .
C32 C 1.1933(5) 0.54146(17) 1.3757(7) 0.0365(14) Uani 1 1 d . . . . .
C33 C 1.2581(5) 0.54765(17) 1.5095(7) 0.0351(14) Uani 1 1 d . . . . .
H33 H 1.288558 0.527263 1.565395 0.042 Uiso 1 1 calc R U . . .
C34 C 1.2784(5) 0.58406(17) 1.5617(7) 0.0348(14) Uani 1 1 d . . . . .
C35 C 1.2331(5) 0.61390(17) 1.4769(7) 0.0354(14) Uani 1 1 d . . . . .
H35 H 1.246606 0.638176 1.510773 0.042 Uiso 1 1 calc R U . . .
C36 C 1.3523(7) 0.5907(2) 1.7065(8) 0.0531(19) Uani 1 1 d . . . . .
H36A H 1.364600 0.567437 1.753808 0.080 Uiso 1 1 calc R U . . .
H36B H 1.319848 0.608392 1.741197 0.080 Uiso 1 1 calc R U . . .
H36C H 1.419399 0.600577 1.716594 0.080 Uiso 1 1 calc R U . . .
C37 C 1.1750(6) 0.50201(19) 1.3205(8) 0.0508(19) Uani 1 1 d . . . . .
H37A H 1.108801 0.492481 1.314469 0.076 Uiso 1 1 calc R U . . .
H37B H 1.233130 0.486167 1.377758 0.076 Uiso 1 1 calc R U . . .
H37C H 1.171366 0.502336 1.234161 0.076 Uiso 1 1 calc R U . . .
C38 C 0.9192(5) 0.68690(16) 0.8115(6) 0.0304(13) Uani 1 1 d . . . . .
H38 H 0.897686 0.662901 0.777247 0.036 Uiso 1 1 calc R U . . .
C39 C 0.8909(5) 0.71972(17) 0.7440(7) 0.0351(14) Uani 1 1 d . . . . .
C40 C 0.8245(6) 0.73002(19) 0.6062(8) 0.0427(16) Uani 1 1 d . . . . .
C41 C 0.7166(7) 0.7076(2) 0.3913(7) 0.0509(19) Uani 1 1 d . . . . .
H41A H 0.759412 0.720281 0.356232 0.061 Uiso 1 1 calc R U . . .
H41B H 0.657554 0.723917 0.379649 0.061 Uiso 1 1 calc R U . . .
C42 C 0.6749(8) 0.6722(2) 0.3201(8) 0.062(2) Uani 1 1 d . . . . .
H42A H 0.627137 0.677511 0.229162 0.094 Uiso 1 1 calc R U . . .
H42B H 0.636750 0.658973 0.359122 0.094 Uiso 1 1 calc R U . . .
H42C H 0.733433 0.657084 0.325556 0.094 Uiso 1 1 calc R U . . .
O7 O 1.5075(3) 0.57541(10) 1.5461(4) 0.0325(9) Uani 1 1 d . . . . .
O8 O 1.5904(4) 0.51597(12) 1.7102(5) 0.0429(11) Uani 1 1 d . . . . .
O9 O 1.5193(3) 0.47613(11) 1.5389(5) 0.0355(10) Uani 1 1 d . . . . .
N3 N 1.2922(4) 0.65431(12) 1.0961(5) 0.0287(11) Uani 1 1 d . . . . .
H3 H 1.283625 0.677968 1.079251 0.034 Uiso 1 1 calc R U . . .
C43 C 1.3497(4) 0.59949(15) 1.2047(6) 0.0267(12) Uani 1 1 d . . . . .
C44 C 1.4063(4) 0.57910(14) 1.3215(6) 0.0262(12) Uani 1 1 d . . . . .
C45 C 1.4575(5) 0.59886(16) 1.4401(6) 0.0296(12) Uani 1 1 d . . . . .
C46 C 1.4561(5) 0.63814(16) 1.4547(7) 0.0370(14) Uani 1 1 d . . . . .
H46 H 1.488910 0.649707 1.537041 0.044 Uiso 1 1 calc R U . . .
C47 C 1.4030(5) 0.65843(15) 1.3391(7) 0.0338(14) Uani 1 1 d . . . . .
H47 H 1.401561 0.684529 1.340978 0.041 Uiso 1 1 calc R U . . .
C48 C 1.3514(5) 0.63909(15) 1.2192(7) 0.0298(13) Uani 1 1 d . . . . .
C49 C 1.2850(5) 0.59181(15) 1.0713(6) 0.0296(13) Uani 1 1 d . . . . .
H49 H 1.268754 0.568015 1.033494 0.036 Uiso 1 1 calc R U . . .
C50 C 1.2484(5) 0.62608(17) 1.0031(7) 0.0337(14) Uani 1 1 d . . . . .
C51 C 1.1813(5) 0.63366(17) 0.8649(6) 0.0314(13) Uani 1 1 d . . . . .
C52 C 1.1674(5) 0.66935(17) 0.8120(7) 0.0358(14) Uani 1 1 d . . . . .
H52 H 1.202276 0.689384 0.867559 0.043 Uiso 1 1 calc R U . . .
C53 C 1.1026(5) 0.67634(16) 0.6773(7) 0.0372(15) Uani 1 1 d . . . . .
C54 C 1.0534(6) 0.64645(19) 0.5964(8) 0.0419(15) Uani 1 1 d . . . . .
H54 H 1.010363 0.650750 0.506756 0.050 Uiso 1 1 calc R U . . .
C55 C 1.0662(5) 0.60913(18) 0.6450(7) 0.0354(14) Uani 1 1 d . . . . .
C56 C 1.1282(5) 0.60356(17) 0.7778(7) 0.0352(14) Uani 1 1 d . . . . .
H56 H 1.135739 0.579360 0.811658 0.042 Uiso 1 1 calc R U . . .
C57 C 1.0138(6) 0.57737(18) 0.5505(8) 0.0440(16) Uani 1 1 d . . . . .
H57A H 0.939831 0.583343 0.494839 0.066 Uiso 1 1 calc R U . . .
H57B H 1.018393 0.554866 0.599346 0.066 Uiso 1 1 calc R U . . .
H57C H 1.049737 0.573568 0.497038 0.066 Uiso 1 1 calc R U . . .
C58 C 1.0885(7) 0.71558(19) 0.6229(9) 0.052(2) Uani 1 1 d . . . . .
H58A H 1.023211 0.726071 0.616581 0.078 Uiso 1 1 calc R U . . .
H58B H 1.085204 0.714903 0.536752 0.078 Uiso 1 1 calc R U . . .
H58C H 1.148131 0.730798 0.680599 0.078 Uiso 1 1 calc R U . . .
C59 C 1.4317(4) 0.54022(15) 1.3604(6) 0.0290(12) Uani 1 1 d . . . . .
H59 H 1.410852 0.519421 1.304824 0.035 Uiso 1 1 calc R U . . .
C60 C 1.4919(5) 0.54000(16) 1.4937(6) 0.0297(13) Uani 1 1 d . . . . .
C61 C 1.5388(5) 0.51021(16) 1.5919(7) 0.0306(13) Uani 1 1 d . . . . .
C62 C 1.5652(5) 0.44509(16) 1.6337(7) 0.0368(15) Uani 1 1 d . . . . .
H62A H 1.535450 0.444848 1.695659 0.044 Uiso 1 1 calc R U . . .
H62B H 1.642530 0.447740 1.682788 0.044 Uiso 1 1 calc R U . . .
C63 C 1.5366(6) 0.40941(17) 1.5533(8) 0.0440(17) Uani 1 1 d . . . . .
H63A H 1.569772 0.409467 1.495802 0.066 Uiso 1 1 calc R U . . .
H63B H 1.460098 0.407899 1.501400 0.066 Uiso 1 1 calc R U . . .
H63C H 1.561600 0.388161 1.611472 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.377(7) . ?
O1 C18 1.375(8) . ?
O2 C19 1.221(7) . ?
O3 C19 1.331(8) . ?
O3 C20 1.459(7) . ?
N1 H1 0.8600 . ?
N1 C6 1.364(7) . ?
N1 C8 1.381(8) . ?
C1 C2 1.429(7) . ?
C1 C6 1.412(8) . ?
C1 C7 1.414(8) . ?
C2 C3 1.390(9) . ?
C2 C17 1.426(8) . ?
C3 C4 1.390(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.401(8) . ?
C8 C9 1.461(8) . ?
C9 C10 1.393(9) . ?
C9 C14 1.408(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(8) . ?
C11 C12 1.397(9) . ?
C11 C16 1.490(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(10) . ?
C13 C14 1.380(8) . ?
C13 C15 1.514(9) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.347(8) . ?
C18 C19 1.475(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.507(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O4 C24 1.373(8) . ?
O4 C39 1.371(7) . ?
O5 C40 1.194(8) . ?
O6 C40 1.344(8) . ?
O6 C41 1.438(8) . ?
N2 H2 0.8600 . ?
N2 C27 1.357(8) . ?
N2 C29 1.388(7) . ?
C22 C23 1.412(9) . ?
C22 C27 1.417(8) . ?
C22 C28 1.414(7) . ?
C23 C24 1.401(8) . ?
C23 C38 1.446(8) . ?
C24 C25 1.391(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.356(10) . ?
C26 H26 0.9300 . ?
C26 C27 1.411(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.382(9) . ?
C29 C30 1.463(8) . ?
C30 C31 1.396(8) . ?
C30 C35 1.393(9) . ?
C31 H31 0.9300 . ?
C31 C32 1.392(9) . ?
C32 C33 1.389(9) . ?
C32 C37 1.512(9) . ?
C33 H33 0.9300 . ?
C33 C34 1.400(9) . ?
C34 C35 1.379(8) . ?
C34 C36 1.511(10) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38 0.9300 . ?
C38 C39 1.354(9) . ?
C39 C40 1.458(10) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.465(11) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
O7 C45 1.367(7) . ?
O7 C60 1.369(7) . ?
O8 C61 1.219(8) . ?
O9 C61 1.327(7) . ?
O9 C62 1.471(7) . ?
N3 H3 0.8600 . ?
N3 C48 1.371(8) . ?
N3 C50 1.383(8) . ?
C43 C44 1.400(8) . ?
C43 C48 1.418(7) . ?
C43 C49 1.394(8) . ?
C44 C45 1.395(8) . ?
C44 C59 1.447(7) . ?
C45 C46 1.410(8) . ?
C46 H46 0.9300 . ?
C46 C47 1.383(9) . ?
C47 H47 0.9300 . ?
C47 C48 1.399(9) . ?
C49 H49 0.9300 . ?
C49 C50 1.411(8) . ?
C50 C51 1.441(9) . ?
C51 C52 1.381(8) . ?
C51 C56 1.418(8) . ?
C52 H52 0.9300 . ?
C52 C53 1.401(10) . ?
C53 C54 1.370(10) . ?
C53 C58 1.504(8) . ?
C54 H54 0.9300 . ?
C54 C55 1.419(9) . ?
C55 C56 1.370(9) . ?
C55 C57 1.500(9) . ?
C56 H56 0.9300 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 H59 0.9300 . ?
C59 C60 1.357(9) . ?
C60 C61 1.461(8) . ?
C62 H62A 0.9700 . ?
C62 H62B 0.9700 . ?
C62 C63 1.509(9) . ?
C63 H63A 0.9600 . ?
C63 H63B 0.9600 . ?
C63 H63C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C3 105.3(5) . . ?
C19 O3 C20 113.8(5) . . ?
C6 N1 H1 124.9 . . ?
C6 N1 C8 110.2(5) . . ?
C8 N1 H1 124.9 . . ?
C6 C1 C2 116.3(5) . . ?
C6 C1 C7 107.3(5) . . ?
C7 C1 C2 136.3(6) . . ?
C3 C2 C1 116.9(6) . . ?
C3 C2 C17 105.4(5) . . ?
C17 C2 C1 137.6(6) . . ?
O1 C3 C2 110.6(6) . . ?
O1 C3 C4 123.3(6) . . ?
C4 C3 C2 126.1(5) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.6(6) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.0(6) . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C1 107.6(5) . . ?
N1 C6 C5 127.5(6) . . ?
C5 C6 C1 124.8(5) . . ?
C1 C7 H7 126.3 . . ?
C8 C7 C1 107.3(5) . . ?
C8 C7 H7 126.3 . . ?
N1 C8 C7 107.6(5) . . ?
N1 C8 C9 123.0(5) . . ?
C7 C8 C9 129.4(6) . . ?
C10 C9 C8 120.0(6) . . ?
C10 C9 C14 118.8(6) . . ?
C14 C9 C8 121.2(6) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(6) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 118.5(6) . . ?
C10 C11 C16 121.2(6) . . ?
C12 C11 C16 120.3(6) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.5(5) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C15 119.8(6) . . ?
C14 C13 C12 119.3(6) . . ?
C14 C13 C15 120.9(6) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(6) . . ?
C13 C14 H14 119.7 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C17 H17 126.6 . . ?
C18 C17 C2 106.9(6) . . ?
C18 C17 H17 126.6 . . ?
O1 C18 C19 113.0(5) . . ?
C17 C18 O1 111.9(5) . . ?
C17 C18 C19 135.1(6) . . ?
O2 C19 O3 124.4(5) . . ?
O2 C19 C18 123.7(6) . . ?
O3 C19 C18 111.9(5) . . ?
O3 C20 H20A 110.3 . . ?
O3 C20 H20B 110.3 . . ?
O3 C20 C21 107.2(5) . . ?
H20A C20 H20B 108.5 . . ?
C21 C20 H20A 110.3 . . ?
C21 C20 H20B 110.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C39 O4 C24 105.7(5) . . ?
C40 O6 C41 115.2(5) . . ?
C27 N2 H2 125.3 . . ?
C27 N2 C29 109.5(5) . . ?
C29 N2 H2 125.3 . . ?
C23 C22 C27 116.8(5) . . ?
C23 C22 C28 137.3(6) . . ?
C28 C22 C27 105.9(5) . . ?
C22 C23 C38 137.2(5) . . ?
C24 C23 C22 117.8(6) . . ?
C24 C23 C38 105.0(6) . . ?
O4 C24 C23 110.7(5) . . ?
O4 C24 C25 124.7(5) . . ?
C25 C24 C23 124.6(6) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 C24 118.3(6) . . ?
C26 C25 H25 120.9 . . ?
C25 C26 H26 120.4 . . ?
C25 C26 C27 119.3(7) . . ?
C27 C26 H26 120.4 . . ?
N2 C27 C22 108.4(5) . . ?
N2 C27 C26 128.3(7) . . ?
C26 C27 C22 123.2(6) . . ?
C22 C28 H28 125.8 . . ?
C29 C28 C22 108.4(5) . . ?
C29 C28 H28 125.8 . . ?
N2 C29 C30 122.0(6) . . ?
C28 C29 N2 107.7(6) . . ?
C28 C29 C30 130.3(6) . . ?
C31 C30 C29 118.8(6) . . ?
C35 C30 C29 122.8(6) . . ?
C35 C30 C31 118.3(6) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 C30 121.1(6) . . ?
C32 C31 H31 119.5 . . ?
C31 C32 C37 120.6(6) . . ?
C33 C32 C31 119.0(6) . . ?
C33 C32 C37 120.3(6) . . ?
C32 C33 H33 119.4 . . ?
C32 C33 C34 121.1(6) . . ?
C34 C33 H33 119.5 . . ?
C33 C34 C36 120.9(6) . . ?
C35 C34 C33 118.5(6) . . ?
C35 C34 C36 120.6(6) . . ?
C30 C35 H35 119.0 . . ?
C34 C35 C30 122.1(6) . . ?
C34 C35 H35 119.0 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C23 C38 H38 126.9 . . ?
C39 C38 C23 106.2(5) . . ?
C39 C38 H38 126.9 . . ?
O4 C39 C40 112.9(5) . . ?
C38 C39 O4 112.4(6) . . ?
C38 C39 C40 134.8(6) . . ?
O5 C40 O6 122.7(7) . . ?
O5 C40 C39 125.4(7) . . ?
O6 C40 C39 111.9(6) . . ?
O6 C41 H41A 109.8 . . ?
O6 C41 H41B 109.8 . . ?
O6 C41 C42 109.3(6) . . ?
H41A C41 H41B 108.3 . . ?
C42 C41 H41A 109.8 . . ?
C42 C41 H41B 109.8 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C45 O7 C60 105.3(5) . . ?
C61 O9 C62 115.1(5) . . ?
C48 N3 H3 124.9 . . ?
C48 N3 C50 110.1(5) . . ?
C50 N3 H3 124.9 . . ?
C44 C43 C48 115.7(6) . . ?
C49 C43 C44 137.4(5) . . ?
C49 C43 C48 106.8(5) . . ?
C43 C44 C59 137.7(6) . . ?
C45 C44 C43 118.4(5) . . ?
C45 C44 C59 103.9(5) . . ?
O7 C45 C44 112.0(5) . . ?
O7 C45 C46 122.1(6) . . ?
C44 C45 C46 125.8(6) . . ?
C45 C46 H46 122.1 . . ?
C47 C46 C45 115.9(6) . . ?
C47 C46 H46 122.1 . . ?
C46 C47 H47 120.5 . . ?
C46 C47 C48 119.0(5) . . ?
C48 C47 H47 120.5 . . ?
N3 C48 C43 107.7(6) . . ?
N3 C48 C47 127.1(5) . . ?
C47 C48 C43 125.2(6) . . ?
C43 C49 H49 125.6 . . ?
C43 C49 C50 108.7(5) . . ?
C50 C49 H49 125.6 . . ?
N3 C50 C49 106.5(6) . . ?
N3 C50 C51 122.6(6) . . ?
C49 C50 C51 130.8(6) . . ?
C52 C51 C50 122.6(6) . . ?
C52 C51 C56 117.8(6) . . ?
C56 C51 C50 119.6(6) . . ?
C51 C52 H52 118.9 . . ?
C51 C52 C53 122.1(6) . . ?
C53 C52 H52 118.9 . . ?
C52 C53 C58 120.9(6) . . ?
C54 C53 C52 118.2(6) . . ?
C54 C53 C58 120.9(7) . . ?
C53 C54 H54 119.0 . . ?
C53 C54 C55 122.0(7) . . ?
C55 C54 H54 119.0 . . ?
C54 C55 C57 119.6(6) . . ?
C56 C55 C54 118.0(6) . . ?
C56 C55 C57 122.5(6) . . ?
C51 C56 H56 119.1 . . ?
C55 C56 C51 121.8(6) . . ?
C55 C56 H56 119.1 . . ?
C55 C57 H57A 109.5 . . ?
C55 C57 H57B 109.5 . . ?
C55 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C53 C58 H58A 109.5 . . ?
C53 C58 H58B 109.5 . . ?
C53 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C44 C59 H59 126.6 . . ?
C60 C59 C44 106.7(5) . . ?
C60 C59 H59 126.6 . . ?
O7 C60 C61 114.1(5) . . ?
C59 C60 O7 112.0(5) . . ?
C59 C60 C61 133.8(5) . . ?
O8 C61 O9 123.4(6) . . ?
O8 C61 C60 123.7(5) . . ?
O9 C61 C60 112.9(6) . . ?
O9 C62 H62A 110.4 . . ?
O9 C62 H62B 110.4 . . ?
O9 C62 C63 106.4(5) . . ?
H62A C62 H62B 108.6 . . ?
C63 C62 H62A 110.4 . . ?
C63 C62 H62B 110.4 . . ?
C62 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
C62 C63 H63C 109.5 . . ?
H63A C63 H63B 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 178.9(6) . . . . ?
O1 C18 C19 O2 -1.5(9) . . . . ?
O1 C18 C19 O3 178.2(5) . . . . ?
N1 C8 C9 C10 174.3(6) . . . . ?
N1 C8 C9 C14 -4.4(9) . . . . ?
C1 C2 C3 O1 -178.3(5) . . . . ?
C1 C2 C3 C4 0.8(9) . . . . ?
C1 C2 C17 C18 177.7(7) . . . . ?
C1 C7 C8 N1 0.0(6) . . . . ?
C1 C7 C8 C9 179.8(6) . . . . ?
C2 C1 C6 N1 -178.5(5) . . . . ?
C2 C1 C6 C5 4.9(9) . . . . ?
C2 C1 C7 C8 177.5(7) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C2 C17 C18 O1 -0.2(7) . . . . ?
C2 C17 C18 C19 179.2(7) . . . . ?
C3 O1 C18 C17 0.1(7) . . . . ?
C3 O1 C18 C19 -179.4(5) . . . . ?
C3 C2 C17 C18 0.2(7) . . . . ?
C3 C4 C5 C6 1.5(9) . . . . ?
C4 C5 C6 N1 179.8(6) . . . . ?
C4 C5 C6 C1 -4.1(9) . . . . ?
C6 N1 C8 C7 -0.4(6) . . . . ?
C6 N1 C8 C9 179.7(5) . . . . ?
C6 C1 C2 C3 -3.0(8) . . . . ?
C6 C1 C2 C17 179.6(6) . . . . ?
C6 C1 C7 C8 0.4(6) . . . . ?
C7 C1 C2 C3 -179.9(6) . . . . ?
C7 C1 C2 C17 2.8(13) . . . . ?
C7 C1 C6 N1 -0.7(6) . . . . ?
C7 C1 C6 C5 -177.4(6) . . . . ?
C7 C8 C9 C10 -5.4(10) . . . . ?
C7 C8 C9 C14 175.8(6) . . . . ?
C8 N1 C6 C1 0.7(6) . . . . ?
C8 N1 C6 C5 177.3(6) . . . . ?
C8 C9 C10 C11 -178.7(6) . . . . ?
C8 C9 C14 C13 178.6(6) . . . . ?
C9 C10 C11 C12 -0.1(9) . . . . ?
C9 C10 C11 C16 179.3(6) . . . . ?
C10 C9 C14 C13 -0.2(9) . . . . ?
C10 C11 C12 C13 0.2(10) . . . . ?
C11 C12 C13 C14 -0.3(10) . . . . ?
C11 C12 C13 C15 178.2(6) . . . . ?
C12 C13 C14 C9 0.3(9) . . . . ?
C14 C9 C10 C11 0.1(9) . . . . ?
C15 C13 C14 C9 -178.2(6) . . . . ?
C16 C11 C12 C13 -179.2(6) . . . . ?
C17 C2 C3 O1 -0.1(7) . . . . ?
C17 C2 C3 C4 179.0(6) . . . . ?
C17 C18 C19 O2 179.1(7) . . . . ?
C17 C18 C19 O3 -1.2(10) . . . . ?
C18 O1 C3 C2 0.0(7) . . . . ?
C18 O1 C3 C4 -179.1(6) . . . . ?
C19 O3 C20 C21 179.3(5) . . . . ?
C20 O3 C19 O2 -0.5(9) . . . . ?
C20 O3 C19 C18 179.8(5) . . . . ?
O4 C24 C25 C26 -179.8(6) . . . . ?
O4 C39 C40 O5 -0.7(10) . . . . ?
O4 C39 C40 O6 178.5(5) . . . . ?
N2 C29 C30 C31 -172.8(5) . . . . ?
N2 C29 C30 C35 3.3(9) . . . . ?
C22 C23 C24 O4 -179.1(5) . . . . ?
C22 C23 C24 C25 0.1(9) . . . . ?
C22 C23 C38 C39 178.5(6) . . . . ?
C22 C28 C29 N2 0.6(7) . . . . ?
C22 C28 C29 C30 -176.9(6) . . . . ?
C23 C22 C27 N2 178.4(5) . . . . ?
C23 C22 C27 C26 -1.1(9) . . . . ?
C23 C22 C28 C29 -179.1(7) . . . . ?
C23 C24 C25 C26 1.0(10) . . . . ?
C23 C38 C39 O4 0.9(7) . . . . ?
C23 C38 C39 C40 179.1(7) . . . . ?
C24 O4 C39 C38 -0.8(7) . . . . ?
C24 O4 C39 C40 -179.4(5) . . . . ?
C24 C23 C38 C39 -0.6(6) . . . . ?
C24 C25 C26 C27 -2.1(11) . . . . ?
C25 C26 C27 N2 -177.2(6) . . . . ?
C25 C26 C27 C22 2.3(10) . . . . ?
C27 N2 C29 C28 -1.4(7) . . . . ?
C27 N2 C29 C30 176.3(5) . . . . ?
C27 C22 C23 C24 0.0(8) . . . . ?
C27 C22 C23 C38 -179.1(6) . . . . ?
C27 C22 C28 C29 0.4(6) . . . . ?
C28 C22 C23 C24 179.4(6) . . . . ?
C28 C22 C23 C38 0.4(12) . . . . ?
C28 C22 C27 N2 -1.2(6) . . . . ?
C28 C22 C27 C26 179.2(6) . . . . ?
C28 C29 C30 C31 4.3(9) . . . . ?
C28 C29 C30 C35 -179.5(6) . . . . ?
C29 N2 C27 C22 1.6(7) . . . . ?
C29 N2 C27 C26 -178.9(6) . . . . ?
C29 C30 C31 C32 175.3(6) . . . . ?
C29 C30 C35 C34 -175.8(5) . . . . ?
C30 C31 C32 C33 0.8(9) . . . . ?
C30 C31 C32 C37 -177.4(6) . . . . ?
C31 C30 C35 C34 0.3(9) . . . . ?
C31 C32 C33 C34 -0.1(9) . . . . ?
C32 C33 C34 C35 -0.5(9) . . . . ?
C32 C33 C34 C36 -177.7(6) . . . . ?
C33 C34 C35 C30 0.4(9) . . . . ?
C35 C30 C31 C32 -1.0(9) . . . . ?
C36 C34 C35 C30 177.6(6) . . . . ?
C37 C32 C33 C34 178.2(6) . . . . ?
C38 C23 C24 O4 0.2(6) . . . . ?
C38 C23 C24 C25 179.4(6) . . . . ?
C38 C39 C40 O5 -178.9(7) . . . . ?
C38 C39 C40 O6 0.3(11) . . . . ?
C39 O4 C24 C23 0.3(6) . . . . ?
C39 O4 C24 C25 -178.9(6) . . . . ?
C40 O6 C41 C42 -179.8(7) . . . . ?
C41 O6 C40 O5 0.5(10) . . . . ?
C41 O6 C40 C39 -178.7(6) . . . . ?
O7 C45 C46 C47 179.7(5) . . . . ?
O7 C60 C61 O8 -2.2(8) . . . . ?
O7 C60 C61 O9 177.8(5) . . . . ?
N3 C50 C51 C52 9.1(9) . . . . ?
N3 C50 C51 C56 -172.2(5) . . . . ?
C43 C44 C45 O7 178.6(4) . . . . ?
C43 C44 C45 C46 1.3(9) . . . . ?
C43 C44 C59 C60 179.9(6) . . . . ?
C43 C49 C50 N3 0.5(6) . . . . ?
C43 C49 C50 C51 179.1(6) . . . . ?
C44 C43 C48 N3 -179.8(5) . . . . ?
C44 C43 C48 C47 -1.1(9) . . . . ?
C44 C43 C49 C50 177.9(6) . . . . ?
C44 C45 C46 C47 -3.2(9) . . . . ?
C44 C59 C60 O7 0.5(6) . . . . ?
C44 C59 C60 C61 177.4(6) . . . . ?
C45 O7 C60 C59 -1.8(6) . . . . ?
C45 O7 C60 C61 -179.4(4) . . . . ?
C45 C44 C59 C60 1.0(6) . . . . ?
C45 C46 C47 C48 2.8(9) . . . . ?
C46 C47 C48 N3 177.7(6) . . . . ?
C46 C47 C48 C43 -0.8(9) . . . . ?
C48 N3 C50 C49 -1.9(6) . . . . ?
C48 N3 C50 C51 179.4(5) . . . . ?
C48 C43 C44 C45 0.8(8) . . . . ?
C48 C43 C44 C59 -177.9(6) . . . . ?
C48 C43 C49 C50 1.0(6) . . . . ?
C49 C43 C44 C45 -176.0(6) . . . . ?
C49 C43 C44 C59 5.3(12) . . . . ?
C49 C43 C48 N3 -2.1(7) . . . . ?
C49 C43 C48 C47 176.7(5) . . . . ?
C49 C50 C51 C52 -169.3(6) . . . . ?
C49 C50 C51 C56 9.4(9) . . . . ?
C50 N3 C48 C43 2.5(7) . . . . ?
C50 N3 C48 C47 -176.2(5) . . . . ?
C50 C51 C52 C53 179.5(6) . . . . ?
C50 C51 C56 C55 -177.9(6) . . . . ?
C51 C52 C53 C54 -1.2(9) . . . . ?
C51 C52 C53 C58 179.6(6) . . . . ?
C52 C51 C56 C55 0.9(9) . . . . ?
C52 C53 C54 C55 0.2(10) . . . . ?
C53 C54 C55 C56 1.3(10) . . . . ?
C53 C54 C55 C57 -177.6(6) . . . . ?
C54 C55 C56 C51 -1.9(9) . . . . ?
C56 C51 C52 C53 0.7(9) . . . . ?
C57 C55 C56 C51 177.1(5) . . . . ?
C58 C53 C54 C55 179.4(6) . . . . ?
C59 C44 C45 O7 -2.2(6) . . . . ?
C59 C44 C45 C46 -179.5(6) . . . . ?
C59 C60 C61 O8 -179.1(6) . . . . ?
C59 C60 C61 O9 1.0(9) . . . . ?
C60 O7 C45 C44 2.5(6) . . . . ?
C60 O7 C45 C46 179.9(5) . . . . ?
C61 O9 C62 C63 -178.4(5) . . . . ?
C62 O9 C61 O8 -0.3(8) . . . . ?
C62 O9 C61 C60 179.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
