# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_i18487
_database_code_depnum_ccdc_archive 'CCDC 2144520'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N'
_chemical_formula_sum            'C16 H13 N'
_chemical_formula_weight         219.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.07430(10)
_cell_length_b                   7.29170(10)
_cell_length_c                   12.6835(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.6020(10)
_cell_angle_gamma                90
_cell_volume                     552.187(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    7487
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      72.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.165
_exptl_absorpt_coefficient_mu    0.587
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8369
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8632
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.545
_diffrn_reflns_theta_max         72.608
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2104
_reflns_number_gt                2083
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.911
_reflns_Friedel_fraction_full    0.953

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.0996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 894 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2104
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.0083(2) 0.6090(2) 0.69185(11) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.8081(3) 0.5337(2) 0.70633(13) 0.0138(3) Uani 1 1 d . . . . .
C2 C 0.6337(3) 0.5002(2) 0.62301(13) 0.0131(3) Uani 1 1 d . . . . .
H2 H 0.496887 0.451444 0.636985 0.016 Uiso 1 1 calc R U . . .
C3 C 0.6579(3) 0.5385(2) 0.51616(13) 0.0137(4) Uani 1 1 d . . . . .
C4 C 0.4902(3) 0.4993(2) 0.42558(13) 0.0139(4) Uani 1 1 d . . . . .
H4 H 0.351573 0.448555 0.435751 0.017 Uiso 1 1 calc R U . . .
C6 C 0.7325(3) 0.6115(2) 0.30911(13) 0.0163(4) Uani 1 1 d . . . . .
H6 H 0.757397 0.635337 0.238614 0.020 Uiso 1 1 calc R U . . .
C5 C 0.5246(3) 0.5336(2) 0.32313(13) 0.0152(3) Uani 1 1 d . . . . .
C7 C 0.8965(3) 0.6527(2) 0.39468(13) 0.0158(4) Uani 1 1 d . . . . .
H7 H 1.032865 0.706135 0.383307 0.019 Uiso 1 1 calc R U . . .
C8 C 0.8639(3) 0.6159(2) 0.50062(13) 0.0135(3) Uani 1 1 d . . . . .
C9 C 1.0299(3) 0.6484(2) 0.59310(13) 0.0152(4) Uani 1 1 d . . . . .
H9 H 1.166717 0.702532 0.582904 0.018 Uiso 1 1 calc R U . . .
C10 C 0.3495(3) 0.4898(3) 0.22619(13) 0.0181(4) Uani 1 1 d . . . . .
H10A H 0.319814 0.599063 0.180793 0.027 Uiso 1 1 calc R U . . .
H10B H 0.211171 0.451264 0.249224 0.027 Uiso 1 1 calc R U . . .
H10C H 0.403350 0.390575 0.185420 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7953(3) 0.4812(2) 0.81817(12) 0.0139(4) Uani 1 1 d . . . . .
C12 C 0.9846(3) 0.4077(2) 0.88434(13) 0.0152(4) Uani 1 1 d . . . . .
H12 H 1.121559 0.398653 0.858646 0.018 Uiso 1 1 calc R U . . .
C13 C 0.9740(3) 0.3477(2) 0.98733(13) 0.0167(4) Uani 1 1 d . . . . .
H13 H 1.102035 0.294018 1.030606 0.020 Uiso 1 1 calc R U . . .
C14 C 0.7771(3) 0.3659(3) 1.02717(13) 0.0185(4) Uani 1 1 d . . . . .
H14 H 0.770482 0.326093 1.097828 0.022 Uiso 1 1 calc R U . . .
C15 C 0.5899(3) 0.4428(3) 0.96306(13) 0.0183(4) Uani 1 1 d . . . . .
H15 H 0.456034 0.457883 0.990772 0.022 Uiso 1 1 calc R U . . .
C16 C 0.5965(3) 0.4980(2) 0.85863(13) 0.0154(4) Uani 1 1 d . . . . .
H16 H 0.466102 0.546977 0.814742 0.018 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 C9 1.315(2) . ?
N1 C1 1.377(2) . ?
C1 C2 1.374(2) . ?
C1 C11 1.485(2) . ?
C2 C3 1.418(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.417(2) . ?
C3 C8 1.419(2) . ?
C4 C5 1.377(2) . ?
C4 H4 0.9500 . ?
C6 C7 1.365(2) . ?
C6 C5 1.425(2) . ?
C6 H6 0.9500 . ?
C5 C10 1.505(2) . ?
C7 C8 1.420(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(2) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.400(2) . ?
C11 C16 1.402(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 H16 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
C9 N1 C1 117.35(14) . . ?
C2 C1 N1 122.92(14) . . ?
C2 C1 C11 121.35(14) . . ?
N1 C1 C11 115.66(14) . . ?
C1 C2 C3 119.95(14) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 123.33(14) . . ?
C4 C3 C8 119.24(14) . . ?
C2 C3 C8 117.42(14) . . ?
C5 C4 C3 121.13(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C7 C6 C5 121.50(15) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C4 C5 C6 118.84(15) . . ?
C4 C5 C10 121.68(15) . . ?
C6 C5 C10 119.48(15) . . ?
C6 C7 C8 120.15(15) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C9 117.55(14) . . ?
C3 C8 C7 119.15(15) . . ?
C9 C8 C7 123.29(14) . . ?
N1 C9 C8 124.78(14) . . ?
N1 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.82(14) . . ?
C12 C11 C1 119.32(14) . . ?
C16 C11 C1 121.83(14) . . ?
C13 C12 C11 120.59(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.28(15) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.55(15) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.68(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.04(14) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_i18488
_database_code_depnum_ccdc_archive 'CCDC 2144523'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N'
_chemical_formula_sum            'C16 H13 N'
_chemical_formula_weight         219.27

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.14730(10)
_cell_length_b                   7.40040(10)
_cell_length_c                   24.6690(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1122.25(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      72.58

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.577
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8162
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23354
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.583
_diffrn_reflns_theta_max         72.572
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2211
_reflns_number_gt                2173
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.996

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.2451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2211
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.67352(19) 0.46422(16) 0.60579(5) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.4671(2) 0.39077(18) 0.60529(6) 0.0158(3) Uani 1 1 d . . . . .
C2 C 0.3430(2) 0.3827(2) 0.55893(6) 0.0158(3) Uani 1 1 d . . . . .
H2 H 0.201508 0.331160 0.560116 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4259(2) 0.45113(18) 0.50948(6) 0.0154(3) Uani 1 1 d . . . . .
C4 C 0.3117(2) 0.44632(19) 0.45944(6) 0.0178(3) Uani 1 1 d . . . . .
H4 H 0.170089 0.395217 0.457871 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4050(2) 0.51508(19) 0.41349(6) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.325794 0.511205 0.380452 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6175(3) 0.59233(19) 0.41366(6) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.7295(2) 0.59796(19) 0.46163(6) 0.0179(3) Uani 1 1 d . . . . .
H7 H 0.870802 0.649854 0.462543 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6377(2) 0.52747(19) 0.50996(6) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.7505(2) 0.52891(19) 0.56000(6) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.892088 0.580334 0.560529 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7119(3) 0.6660(2) 0.36179(6) 0.0234(3) Uani 1 1 d . . . . .
H10A H 0.716418 0.569996 0.334438 0.035 Uiso 1 1 calc R U . . .
H10B H 0.859725 0.710207 0.368555 0.035 Uiso 1 1 calc R U . . .
H10C H 0.621094 0.765576 0.348643 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3936(2) 0.31730(19) 0.65822(6) 0.0165(3) Uani 1 1 d . . . . .
C12 C 0.5460(2) 0.23506(19) 0.69204(6) 0.0181(3) Uani 1 1 d . . . . .
H12 H 0.692956 0.225696 0.680465 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4870(3) 0.1666(2) 0.74231(6) 0.0201(3) Uani 1 1 d . . . . .
H13 H 0.592146 0.108277 0.764428 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2730(3) 0.1837(2) 0.76025(6) 0.0212(3) Uani 1 1 d . . . . .
H14 H 0.232081 0.139186 0.794901 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1204(2) 0.2663(2) 0.72713(6) 0.0204(3) Uani 1 1 d . . . . .
H15 H -0.025186 0.279212 0.739469 0.024 Uiso 1 1 calc R U . . .
C16 C 0.1777(2) 0.3307(2) 0.67586(5) 0.0178(3) Uani 1 1 d . . . . .
H16 H 0.070609 0.383493 0.653044 0.021 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 C9 1.3150(19) . ?
N1 C1 1.3803(18) . ?
C1 C2 1.3761(19) . ?
C1 C11 1.4849(19) . ?
C2 C3 1.416(2) . ?
C2 H2 0.9500 . ?
C3 C8 1.4192(19) . ?
C3 C4 1.4205(19) . ?
C4 C5 1.369(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.426(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.370(2) . ?
C6 C10 1.507(2) . ?
C7 C8 1.4185(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.4159(19) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.394(2) . ?
C11 C16 1.400(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(2) . ?
C15 H15 0.9500 . ?
C16 H16 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
C9 N1 C1 117.80(12) . . ?
C2 C1 N1 122.30(13) . . ?
C2 C1 C11 123.10(13) . . ?
N1 C1 C11 114.58(12) . . ?
C1 C2 C3 120.04(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C8 117.74(13) . . ?
C2 C3 C4 124.17(13) . . ?
C8 C3 C4 118.08(12) . . ?
C5 C4 C3 120.21(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 122.05(13) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 118.38(13) . . ?
C7 C6 C10 121.92(13) . . ?
C5 C6 C10 119.70(13) . . ?
C6 C7 C8 120.99(14) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 122.36(13) . . ?
C9 C8 C3 117.36(13) . . ?
C7 C8 C3 120.28(13) . . ?
N1 C9 C8 124.74(13) . . ?
N1 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.81(13) . . ?
C12 C11 C1 118.79(13) . . ?
C16 C11 C1 122.39(13) . . ?
C13 C12 C11 121.22(14) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.84(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.45(13) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.90(14) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 119.74(13) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_i18491
_database_code_depnum_ccdc_archive 'CCDC 2150368'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2022-02-07 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N O'
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0705(2)
_cell_length_b                   7.47590(10)
_cell_length_c                   26.1572(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.4090(10)
_cell_angle_gamma                90
_cell_volume                     2340.66(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      72.33

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    0.658
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8211
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56392
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.408
_diffrn_reflns_theta_max         72.548
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4631
_reflns_number_gt                3559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0835P)²+0.0533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4631
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.30022(7) 0.76334(11) 0.91684(3) 0.0208(2) Uani 1 1 d . . . . .
O2 O 0.06135(7) 0.25297(10) 0.90809(3) 0.0202(2) Uani 1 1 d . . . . .
N1 N 0.28164(9) 0.68598(12) 0.68376(4) 0.0169(2) Uani 1 1 d . . . . .
N2 N 0.03715(8) 0.34575(12) 0.67558(4) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.38774(10) 0.75012(13) 0.68150(4) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.45691(10) 0.79990(14) 0.72533(4) 0.0161(2) Uani 1 1 d . . . . .
H2 H 0.529771 0.843725 0.722555 0.019 Uiso 1 1 calc R U . . .
C3 C 0.42018(10) 0.78617(14) 0.77431(4) 0.0158(2) Uani 1 1 d . . . . .
C4 C 0.48541(10) 0.83754(14) 0.82111(5) 0.0173(2) Uani 1 1 d . . . . .
H4 H 0.559573 0.879467 0.820649 0.021 Uiso 1 1 calc R U . . .
C5 C 0.44207(10) 0.82702(14) 0.86693(4) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.486021 0.864096 0.897865 0.022 Uiso 1 1 calc R U . . .
C6 C 0.33222(10) 0.76133(14) 0.86872(4) 0.0164(2) Uani 1 1 d . . . . .
C7 C 0.26783(10) 0.70373(14) 0.82463(5) 0.0168(2) Uani 1 1 d . . . . .
H7 H 0.195585 0.655190 0.826138 0.020 Uiso 1 1 calc R U . . .
C8 C 0.31097(10) 0.71790(13) 0.77680(4) 0.0153(2) Uani 1 1 d . . . . .
C9 C 0.24729(10) 0.67086(14) 0.72935(4) 0.0170(2) Uani 1 1 d . . . . .
H9 H 0.174274 0.624938 0.730524 0.020 Uiso 1 1 calc R U . . .
C10 C 0.18954(11) 0.70208(18) 0.92154(5) 0.0252(3) Uani 1 1 d . . . . .
H10A H 0.135274 0.773044 0.898925 0.038 Uiso 1 1 calc R U . . .
H10B H 0.174987 0.715461 0.957342 0.038 Uiso 1 1 calc R U . . .
H10C H 0.182633 0.575825 0.911557 0.038 Uiso 1 1 calc R U . . .
C11 C 0.42212(10) 0.75622(14) 0.62885(4) 0.0155(2) Uani 1 1 d . . . . .
C12 C 0.36260(10) 0.65817(14) 0.58886(5) 0.0184(3) Uani 1 1 d . . . . .
H12 H 0.299288 0.590337 0.595281 0.022 Uiso 1 1 calc R U . . .
C13 C 0.39515(10) 0.65895(15) 0.53979(5) 0.0203(3) Uani 1 1 d . . . . .
H13 H 0.354448 0.590720 0.513042 0.024 Uiso 1 1 calc R U . . .
C14 C 0.48684(11) 0.75890(15) 0.52964(5) 0.0215(3) Uani 1 1 d . . . . .
H14 H 0.508701 0.759756 0.496028 0.026 Uiso 1 1 calc R U . . .
C15 C 0.54644(10) 0.85778(16) 0.56908(5) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.609359 0.926118 0.562407 0.025 Uiso 1 1 calc R U . . .
C16 C 0.51413(10) 0.85684(15) 0.61828(4) 0.0182(2) Uani 1 1 d . . . . .
H16 H 0.554999 0.925247 0.644946 0.022 Uiso 1 1 calc R U . . .
C17 C 0.14054(10) 0.27340(14) 0.67185(5) 0.0163(2) Uani 1 1 d . . . . .
C18 C 0.20967(10) 0.21592(14) 0.71491(5) 0.0175(2) Uani 1 1 d . . . . .
H18 H 0.280667 0.166221 0.711275 0.021 Uiso 1 1 calc R U . . .
C19 C 0.17536(10) 0.23068(14) 0.76418(5) 0.0158(2) Uani 1 1 d . . . . .
C20 C 0.24005(10) 0.16906(14) 0.81030(5) 0.0179(3) Uani 1 1 d . . . . .
H20 H 0.312441 0.120819 0.808967 0.022 Uiso 1 1 calc R U . . .
C21 C 0.19858(10) 0.17903(14) 0.85622(5) 0.0181(3) Uani 1 1 d . . . . .
H21 H 0.241789 0.134608 0.886481 0.022 Uiso 1 1 calc R U . . .
C22 C 0.09159(10) 0.25485(14) 0.85968(5) 0.0173(3) Uani 1 1 d . . . . .
C23 C 0.02854(10) 0.32223(14) 0.81646(5) 0.0175(3) Uani 1 1 d . . . . .
H23 H -0.041322 0.377915 0.818912 0.021 Uiso 1 1 calc R U . . .
C24 C 0.06919(10) 0.30745(14) 0.76828(5) 0.0159(2) Uani 1 1 d . . . . .
C25 C 0.00492(10) 0.36159(14) 0.72144(4) 0.0166(2) Uani 1 1 d . . . . .
H25 H -0.066396 0.412868 0.723466 0.020 Uiso 1 1 calc R U . . .
C26 C -0.04282(11) 0.33673(17) 0.91464(5) 0.0248(3) Uani 1 1 d . . . . .
H26A H -0.040730 0.462711 0.904457 0.037 Uiso 1 1 calc R U . . .
H26B H -0.055075 0.328834 0.950890 0.037 Uiso 1 1 calc R U . . .
H26C H -0.103804 0.275866 0.893065 0.037 Uiso 1 1 calc R U . . .
C27 C 0.17089(10) 0.26211(14) 0.61855(5) 0.0167(2) Uani 1 1 d . . . . .
C28 C 0.11072(10) 0.36146(14) 0.57898(5) 0.0183(2) Uani 1 1 d . . . . .
H28 H 0.051894 0.437732 0.586400 0.022 Uiso 1 1 calc R U . . .
C29 C 0.13658(10) 0.34907(16) 0.52898(5) 0.0210(3) Uani 1 1 d . . . . .
H29 H 0.095671 0.417545 0.502343 0.025 Uiso 1 1 calc R U . . .
C30 C 0.22218(11) 0.23684(16) 0.51755(5) 0.0227(3) Uani 1 1 d . . . . .
H30 H 0.239320 0.227939 0.483196 0.027 Uiso 1 1 calc R U . . .
C31 C 0.28241(10) 0.13784(16) 0.55676(5) 0.0223(3) Uani 1 1 d . . . . .
H31 H 0.340995 0.061375 0.549175 0.027 Uiso 1 1 calc R U . . .
C32 C 0.25723(10) 0.15041(15) 0.60687(5) 0.0195(3) Uani 1 1 d . . . . .
H32 H 0.298864 0.082719 0.633468 0.023 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 C6 1.3636(14) . ?
O1 C10 1.4324(15) . ?
O2 C22 1.3624(14) . ?
O2 C26 1.4346(14) . ?
N1 C9 1.3170(15) . ?
N1 C1 1.3759(15) . ?
N2 C25 1.3133(15) . ?
N2 C17 1.3752(15) . ?
C1 C2 1.3796(16) . ?
C1 C11 1.4896(15) . ?
C2 C3 1.4125(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4204(16) . ?
C3 C8 1.4228(16) . ?
C4 C5 1.3703(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4204(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3740(16) . ?
C7 C8 1.4198(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4174(16) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3977(16) . ?
C11 C16 1.3982(16) . ?
C12 C13 1.3898(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3892(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3917(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3921(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.3810(17) . ?
C17 C27 1.4888(16) . ?
C18 C19 1.4079(16) . ?
C18 H18 0.9500 . ?
C19 C24 1.4207(16) . ?
C19 C20 1.4263(16) . ?
C20 C21 1.3616(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.4238(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.3744(16) . ?
C23 C24 1.4145(16) . ?
C23 H23 0.9500 . ?
C24 C25 1.4217(16) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.3988(16) . ?
C27 C32 1.3996(16) . ?
C28 C29 1.3864(16) . ?
C28 H28 0.9500 . ?
C29 C30 1.3931(17) . ?
C29 H29 0.9500 . ?
C30 C31 1.3915(17) . ?
C30 H30 0.9500 . ?
C31 C32 1.3863(16) . ?
C31 H31 0.9500 . ?
C32 H32 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
C6 O1 C10 116.99(9) . . ?
C22 O2 C26 116.78(9) . . ?
C9 N1 C1 118.18(10) . . ?
C25 N2 C17 118.61(10) . . ?
N1 C1 C2 121.69(11) . . ?
N1 C1 C11 114.97(10) . . ?
C2 C1 C11 123.32(11) . . ?
C1 C2 C3 120.47(11) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 123.92(11) . . ?
C2 C3 C8 117.94(10) . . ?
C4 C3 C8 118.13(11) . . ?
C5 C4 C3 120.43(11) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.80(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
O1 C6 C7 125.54(11) . . ?
O1 C6 C5 113.79(10) . . ?
C7 C6 C5 120.67(11) . . ?
C6 C7 C8 118.96(11) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 122.28(11) . . ?
C9 C8 C3 116.74(11) . . ?
C7 C8 C3 120.95(11) . . ?
N1 C9 C8 124.97(11) . . ?
N1 C9 H9 117.5 . . ?
C8 C9 H9 117.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.62(11) . . ?
C12 C11 C1 119.89(10) . . ?
C16 C11 C1 121.49(10) . . ?
C13 C12 C11 120.64(11) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.39(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.50(11) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.20(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.65(11) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
N2 C17 C18 121.52(11) . . ?
N2 C17 C27 115.08(10) . . ?
C18 C17 C27 123.39(11) . . ?
C17 C18 C19 120.27(11) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C24 118.39(10) . . ?
C18 C19 C20 123.72(11) . . ?
C24 C19 C20 117.87(11) . . ?
C21 C20 C19 120.32(11) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.17(11) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
O2 C22 C23 125.59(11) . . ?
O2 C22 C21 114.13(10) . . ?
C23 C22 C21 120.28(11) . . ?
C22 C23 C24 119.03(11) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C19 121.24(10) . . ?
C23 C24 C25 122.15(11) . . ?
C19 C24 C25 116.56(11) . . ?
N2 C25 C24 124.64(11) . . ?
N2 C25 H25 117.7 . . ?
C24 C25 H25 117.7 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C32 119.04(11) . . ?
C28 C27 C17 119.73(10) . . ?
C32 C27 C17 121.22(10) . . ?
C29 C28 C27 120.27(11) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 120.41(11) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C31 C30 C29 119.58(11) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C32 C31 C30 120.23(11) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C27 120.47(11) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.048

