# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

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

data_i18082
_database_code_depnum_ccdc_archive 'CCDC 2082023'
loop_
_audit_author_name
_audit_author_address
'Kesatebrhan Haile Asressu'
;Academia Sinica
Taiwan
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-08-12 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         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   10.7445(3)
_cell_length_b                   19.4078(5)
_cell_length_c                   8.7809(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.9490(10)
_cell_angle_gamma                90
_cell_volume                     1686.13(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    7607
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.45

_exptl_crystal_description       niddle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24629
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.764
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             3652
_reflns_number_gt                3331
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    0.911

_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.
;

_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, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.6802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   2(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3652
_refine_ls_number_parameters     223
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.53057(17) 0.48640(9) 0.3924(2) 0.0171(4) Uani 1 1 d . . . . .
H1 H 0.521(3) 0.5163(14) 0.311(4) 0.030(7) Uiso 1 1 d . . . . .
N2 N 0.49254(18) 0.43381(8) 0.5938(2) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.45827(19) 0.48640(10) 0.4888(2) 0.0172(4) Uani 1 1 d . . . . .
C2 C 0.6145(2) 0.42955(10) 0.4339(2) 0.0180(4) Uani 1 1 d . . . . .
C3 C 0.5908(2) 0.39754(10) 0.5608(2) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.3619(2) 0.54176(11) 0.4802(2) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.2378(2) 0.52841(12) 0.4920(3) 0.0244(5) Uani 1 1 d . . . . .
C6 C 0.1545(3) 0.58469(13) 0.4837(3) 0.0342(6) Uani 1 1 d . . . . .
H6 H 0.069661 0.576997 0.490930 0.041 Uiso 1 1 calc R U . . .
C7 C 0.1920(3) 0.65125(14) 0.4652(4) 0.0389(6) Uani 1 1 d . . . . .
H7 H 0.133536 0.688563 0.461246 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3140(3) 0.66369(12) 0.4526(3) 0.0332(6) Uani 1 1 d . . . . .
H8 H 0.339639 0.709429 0.439295 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3989(2) 0.60904(11) 0.4594(3) 0.0245(5) Uani 1 1 d . . . . .
H9 H 0.482720 0.617328 0.449952 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1907(2) 0.45666(13) 0.5083(3) 0.0306(5) Uani 1 1 d . . . . .
H10A H 0.097769 0.458508 0.502215 0.046 Uiso 1 1 calc R U . . .
H10B H 0.249824 0.437033 0.614863 0.046 Uiso 1 1 calc R U . . .
H10C H 0.194050 0.427780 0.418406 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6982(2) 0.41303(11) 0.3409(2) 0.0191(4) Uani 1 1 d . . . . .
C12 C 0.7640(2) 0.46496(12) 0.2914(3) 0.0233(5) Uani 1 1 d . . . . .
H12 H 0.758525 0.511322 0.322907 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8376(2) 0.44924(13) 0.1960(3) 0.0289(5) Uani 1 1 d . . . . .
H13 H 0.882438 0.484829 0.162955 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8456(2) 0.38175(14) 0.1493(3) 0.0324(6) Uani 1 1 d . . . . .
H14 H 0.894711 0.371208 0.082745 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7823(2) 0.32986(13) 0.1991(3) 0.0298(5) Uani 1 1 d . . . . .
H15 H 0.789300 0.283533 0.168378 0.036 Uiso 1 1 calc R U . . .
C16 C 0.7084(2) 0.34501(12) 0.2938(3) 0.0245(5) Uani 1 1 d . . . . .
H16 H 0.664446 0.309029 0.326942 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6548(2) 0.33682(10) 0.6608(3) 0.0187(4) Uani 1 1 d . . . . .
C18 C 0.7901(2) 0.31962(11) 0.6971(3) 0.0227(4) Uani 1 1 d . . . . .
H18 H 0.843258 0.347884 0.657515 0.027 Uiso 1 1 calc R U . . .
C19 C 0.8469(2) 0.26162(11) 0.7905(3) 0.0272(5) Uani 1 1 d . . . . .
H19 H 0.938435 0.250219 0.813322 0.033 Uiso 1 1 calc R U . . .
C20 C 0.7716(2) 0.22002(11) 0.8511(3) 0.0276(5) Uani 1 1 d . . . . .
H20 H 0.810835 0.180094 0.914136 0.033 Uiso 1 1 calc R U . . .
C21 C 0.6388(2) 0.23722(12) 0.8189(3) 0.0264(5) Uani 1 1 d . . . . .
H21 H 0.586847 0.209211 0.860808 0.032 Uiso 1 1 calc R U . . .
C22 C 0.5810(2) 0.29514(11) 0.7257(3) 0.0215(4) Uani 1 1 d . . . . .
H22 H 0.490057 0.306718 0.705610 0.026 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 C1 1.354(3) . ?
N1 C2 1.381(3) . ?
N1 H1 0.90(3) . ?
N2 C1 1.327(3) . ?
N2 C3 1.390(3) . ?
C1 C4 1.473(3) . ?
C2 C3 1.383(3) . ?
C2 C11 1.467(3) . ?
C3 C17 1.470(3) . ?
C4 C9 1.397(3) . ?
C4 C5 1.402(3) . ?
C5 C6 1.396(3) . ?
C5 C10 1.507(3) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.394(3) . ?
C11 C16 1.400(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.400(3) . ?
C17 C18 1.402(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 H22 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
C1 N1 C2 108.00(17) . . ?
C1 N1 H1 125.8(17) . . ?
C2 N1 H1 126.0(17) . . ?
C1 N2 C3 105.82(16) . . ?
N2 C1 N1 111.27(17) . . ?
N2 C1 C4 126.55(18) . . ?
N1 C1 C4 122.06(18) . . ?
N1 C2 C3 105.40(17) . . ?
N1 C2 C11 120.41(18) . . ?
C3 C2 C11 134.09(19) . . ?
C2 C3 N2 109.48(17) . . ?
C2 C3 C17 130.60(18) . . ?
N2 C3 C17 119.88(17) . . ?
C9 C4 C5 120.6(2) . . ?
C9 C4 C1 117.27(19) . . ?
C5 C4 C1 122.09(19) . . ?
C6 C5 C4 117.4(2) . . ?
C6 C5 C10 119.8(2) . . ?
C4 C5 C10 122.8(2) . . ?
C7 C6 C5 121.9(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
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 118.79(19) . . ?
C12 C11 C2 120.75(19) . . ?
C16 C11 C2 120.40(19) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C22 C17 C18 118.12(19) . . ?
C22 C17 C3 119.93(18) . . ?
C18 C17 C3 121.93(19) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_i18259
_database_code_depnum_ccdc_archive 'CCDC 2098033'
loop_
_audit_author_name
_audit_author_address
'Kesatebrhan Haile Asressu'
;Academia Sinica
Taiwan
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2021-08-12 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         'C19 H20 N2'
_chemical_formula_sum            'C19 H20 N2'
_chemical_formula_weight         276.37

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'-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                   16.5878(5)
_cell_length_b                   9.2549(3)
_cell_length_c                   20.0075(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3071.52(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.73

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.167
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8011
_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     0.71073
_diffrn_radiation_type           MoK\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            61188
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.036
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3375
_reflns_number_gt                2731
_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, 2014)'
_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)+(0.0357P)²+1.4127P] 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         3375
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.30994(7) 0.60788(11) 0.27097(5) 0.0182(2) Uani 1 1 d . . . . .
N2 N 0.25898(7) 0.39119(11) 0.28928(5) 0.0179(2) Uani 1 1 d . . . . .
H2 H 0.226381 0.316405 0.286575 0.021 Uiso 1 1 calc R U . . .
C1 C 0.25052(8) 0.51756(13) 0.25631(6) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.35854(8) 0.53552(13) 0.31651(6) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.32785(8) 0.39981(13) 0.32805(6) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.17888(8) 0.55381(14) 0.21409(7) 0.0214(3) Uani 1 1 d . . . . .
H4A H 0.192489 0.638251 0.185887 0.026 Uiso 1 1 calc R U . . .
H4AB H 0.134032 0.582726 0.243876 0.026 Uiso 1 1 calc R U . . .
C5 C 0.14954(8) 0.43180(14) 0.16877(7) 0.0212(3) Uani 1 1 d . . . . .
H5A H 0.139687 0.344819 0.196383 0.025 Uiso 1 1 calc R U . . .
H5AB H 0.097527 0.460564 0.148474 0.025 Uiso 1 1 calc R U . . .
C6 C 0.20830(9) 0.39314(16) 0.11324(7) 0.0269(3) Uani 1 1 d . . . . .
H6A H 0.261471 0.370287 0.133071 0.032 Uiso 1 1 calc R U . . .
H6AB H 0.215208 0.477623 0.083430 0.032 Uiso 1 1 calc R U . . .
C7 C 0.17952(10) 0.26444(17) 0.07213(8) 0.0344(4) Uani 1 1 d . . . . .
H7A H 0.127869 0.287952 0.050982 0.052 Uiso 1 1 calc R U . . .
H7B H 0.172694 0.180457 0.101423 0.052 Uiso 1 1 calc R U . . .
H7C H 0.219483 0.242164 0.037561 0.052 Uiso 1 1 calc R U . . .
C8 C 0.42757(8) 0.61108(13) 0.34711(6) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.47322(8) 0.70834(14) 0.30932(7) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.460623 0.722811 0.263485 0.025 Uiso 1 1 calc R U . . .
C10 C 0.53673(8) 0.78403(14) 0.33792(7) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.567041 0.850199 0.311718 0.029 Uiso 1 1 calc R U . . .
C11 C 0.55596(8) 0.76317(15) 0.40463(7) 0.0250(3) Uani 1 1 d . . . . .
H11 H 0.599844 0.813954 0.424095 0.030 Uiso 1 1 calc R U . . .
C12 C 0.51087(8) 0.66789(14) 0.44282(7) 0.0242(3) Uani 1 1 d . . . . .
H12 H 0.523805 0.653870 0.488617 0.029 Uiso 1 1 calc R U . . .
C13 C 0.44696(8) 0.59285(14) 0.41460(7) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.416115 0.528545 0.441357 0.025 Uiso 1 1 calc R U . . .
C14 C 0.35372(8) 0.27544(13) 0.36838(6) 0.0180(3) Uani 1 1 d . . . . .
C15 C 0.43483(8) 0.23430(14) 0.37154(6) 0.0208(3) Uani 1 1 d . . . . .
H15 H 0.474618 0.291305 0.349827 0.025 Uiso 1 1 calc R U . . .
C16 C 0.45759(9) 0.11092(15) 0.40613(7) 0.0258(3) Uani 1 1 d . . . . .
H16 H 0.512807 0.083999 0.407971 0.031 Uiso 1 1 calc R U . . .
C17 C 0.40000(9) 0.02652(15) 0.43809(7) 0.0275(3) Uani 1 1 d . . . . .
H17 H 0.415581 -0.058853 0.461073 0.033 Uiso 1 1 calc R U . . .
C18 C 0.31982(9) 0.06766(15) 0.43623(7) 0.0254(3) Uani 1 1 d . . . . .
H18 H 0.280394 0.010849 0.458492 0.030 Uiso 1 1 calc R U . . .
C19 C 0.29659(8) 0.19145(14) 0.40202(6) 0.0210(3) Uani 1 1 d . . . . .
H19 H 0.241462 0.219263 0.401472 0.025 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 C1 1.3252(17) . ?
N1 C2 1.3889(16) . ?
N2 C1 1.3501(16) . ?
N2 C3 1.3831(16) . ?
N2 H2 0.8800 . ?
C1 C4 1.4960(18) . ?
C2 C3 1.3748(17) . ?
C2 C8 1.4746(18) . ?
C3 C14 1.4697(17) . ?
C4 C5 1.5278(18) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.521(2) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.524(2) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.3983(18) . ?
C8 C9 1.3984(18) . ?
C9 C10 1.3885(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3874(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.3983(19) . ?
C14 C15 1.3998(19) . ?
C15 C16 1.3876(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3890(18) . ?
C18 H18 0.9500 . ?
C19 H19 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
C1 N1 C2 105.83(10) . . ?
C1 N2 C3 108.05(11) . . ?
C1 N2 H2 126.0 . . ?
C3 N2 H2 126.0 . . ?
N1 C1 N2 111.16(11) . . ?
N1 C1 C4 125.05(11) . . ?
N2 C1 C4 123.56(12) . . ?
C3 C2 N1 109.61(11) . . ?
C3 C2 C8 130.63(11) . . ?
N1 C2 C8 119.63(11) . . ?
C2 C3 N2 105.34(11) . . ?
C2 C3 C14 134.39(12) . . ?
N2 C3 C14 120.25(11) . . ?
C1 C4 C5 114.98(11) . . ?
C1 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C1 C4 H4AB 108.5 . . ?
C5 C4 H4AB 108.5 . . ?
H4A C4 H4AB 107.5 . . ?
C6 C5 C4 113.79(11) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5AB 108.8 . . ?
C4 C5 H5AB 108.8 . . ?
H5A C5 H5AB 107.7 . . ?
C5 C6 C7 112.17(12) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6AB 109.2 . . ?
C7 C6 H6AB 109.2 . . ?
H6A C6 H6AB 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.37(12) . . ?
C13 C8 C2 121.48(12) . . ?
C9 C8 C2 120.08(11) . . ?
C10 C9 C8 120.85(13) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.08(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.70(13) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.43(13) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.55(13) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C19 C14 C15 118.59(12) . . ?
C19 C14 C3 120.12(12) . . ?
C15 C14 C3 121.23(12) . . ?
C16 C15 C14 120.52(13) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.34(13) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.57(13) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.45(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.51(13) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_i18116
_database_code_depnum_ccdc_archive 'CCDC 2082036'
loop_
_audit_author_name
_audit_author_address
'Kesatebrhan Haile Asressu'
;Academia Sinica
Taiwan
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-08-12 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         'C17 H12 N2 S2'
_chemical_formula_sum            'C17 H12 N2 S2'
_chemical_formula_weight         308.41

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'
S S 0.1246 0.1234 '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                   11.1404(4)
_cell_length_b                   14.6012(6)
_cell_length_c                   9.2447(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.4970(10)
_cell_angle_gamma                90
_cell_volume                     1455.89(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    7244
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.84

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.359
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9613
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42960
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.669
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3206
_reflns_number_gt                2634
_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, 2014)'
_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)+(0.0378P)²+1.7264P] 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         3206
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
S1 S 0.36499(5) 0.38289(4) 0.90631(6) 0.02401(15) Uani 1 1 d . . . . .
S2 S 0.41483(9) 0.46698(6) 0.27715(10) 0.0287(3) Uani 0.463(3) 1 d . . P A 1
C15 C 0.22956(9) 0.46729(7) 0.42686(10) 0.0337(3) Uani 0.463(3) 1 d . . P A 1
H15 H 0.180595 0.456685 0.495850 0.040 Uiso 0.463(3) 1 calc R U P A 1
S2' S 0.22956(9) 0.46729(7) 0.42686(10) 0.0337(3) Uani 0.537(3) 1 d . . P A 2
C15' C 0.41483(9) 0.46698(6) 0.27715(10) 0.0287(3) Uani 0.537(3) 1 d . . P A 2
H15' H 0.488881 0.455736 0.246765 0.034 Uiso 0.537(3) 1 calc R U P A 2
N1 N 0.52169(15) 0.26467(11) 0.69835(17) 0.0156(3) Uani 1 1 d . . . . .
H1 H 0.537703 0.233279 0.782260 0.019 Uiso 1 1 calc R U . . .
N2 N 0.54180(14) 0.32022(11) 0.48280(17) 0.0152(3) Uani 1 1 d . . . . .
C1 C 0.59125(18) 0.26585(13) 0.5978(2) 0.0150(4) Uani 1 1 d . . . . .
C2 C 0.42126(17) 0.32133(13) 0.6462(2) 0.0163(4) Uani 1 1 d . . . . .
C3 C 0.43542(18) 0.35566(13) 0.5123(2) 0.0158(4) Uani 1 1 d . . . . .
C4 C 0.70667(17) 0.21375(13) 0.6133(2) 0.0161(4) Uani 1 1 d . . . . .
C5 C 0.79329(19) 0.24422(15) 0.5378(2) 0.0209(4) Uani 1 1 d . . . . .
H5 H 0.777193 0.298013 0.478238 0.025 Uiso 1 1 calc R U . . .
C6 C 0.9021(2) 0.19638(17) 0.5494(2) 0.0280(5) Uani 1 1 d . . . . .
H6 H 0.959568 0.216534 0.495694 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9280(2) 0.11927(17) 0.6387(3) 0.0302(5) Uani 1 1 d . . . . .
H7 H 1.003907 0.087404 0.647838 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8436(2) 0.08860(15) 0.7146(2) 0.0264(5) Uani 1 1 d . . . . .
H8 H 0.861637 0.035736 0.776107 0.032 Uiso 1 1 calc R U . . .
C9 C 0.73201(19) 0.13508(14) 0.7011(2) 0.0204(4) Uani 1 1 d . . . . .
H9 H 0.673279 0.113132 0.751639 0.024 Uiso 1 1 calc R U . . .
C10 C 0.32739(19) 0.33514(13) 0.7298(2) 0.0180(4) Uani 1 1 d . . . . .
C11 C 0.2032(2) 0.31147(15) 0.6872(2) 0.0240(5) Uani 1 1 d . . . . .
H11 H 0.163995 0.284456 0.593861 0.029 Uiso 1 1 calc R U . . .
C12 C 0.1413(2) 0.33271(15) 0.8010(3) 0.0266(5) Uani 1 1 d . . . . .
H12 H 0.055668 0.321364 0.791111 0.032 Uiso 1 1 calc R U . . .
C13 C 0.2166(2) 0.37048(15) 0.9238(2) 0.0254(5) Uani 1 1 d . . . . .
H13 H 0.190326 0.388118 1.009905 0.031 Uiso 1 1 calc R U . . .
C14 C 0.36234(19) 0.42312(14) 0.4113(2) 0.0181(4) Uani 1 1 d . . . . .
C16 C 0.2118(2) 0.53417(17) 0.2856(3) 0.0343(6) Uani 1 1 d . . . . .
H16 H 0.140564 0.571921 0.253874 0.041 Uiso 1 1 calc R U . A 1
C17 C 0.3036(2) 0.53385(15) 0.2142(2) 0.0293(5) Uani 1 1 d . . . . .
H17 H 0.301062 0.572036 0.130300 0.035 Uiso 1 1 calc R U . A 1


_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
S1 C13 1.710(2) . ?
S1 C10 1.7265(19) . ?
S2 C17 1.571(3) . ?
S2 C14 1.629(2) . ?
C15 C16 1.603(3) . ?
C15 C14 1.653(2) . ?
C15 H15 0.9500 . ?
S2' C16 1.603(3) . ?
S2' C14 1.653(2) . ?
C15' C17 1.571(3) . ?
C15' C14 1.629(2) . ?
C15' H15' 0.9500 . ?
N1 C1 1.351(2) . ?
N1 C2 1.378(2) . ?
N1 H1 0.8800 . ?
N2 C1 1.330(2) . ?
N2 C3 1.381(2) . ?
C1 C4 1.470(3) . ?
C2 C3 1.381(3) . ?
C2 C10 1.462(3) . ?
C3 C14 1.458(3) . ?
C4 C9 1.394(3) . ?
C4 C5 1.398(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C11 C12 1.428(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.349(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C16 C17 1.349(4) . ?
C16 H16 0.9500 . ?
C17 H17 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
C13 S1 C10 92.01(10) . . ?
C17 S2 C14 97.24(12) . . ?
C16 C15 C14 95.60(12) . . ?
C16 C15 H15 132.2 . . ?
C14 C15 H15 132.2 . . ?
C16 S2' C14 95.60(12) . . ?
C17 C15' C14 97.24(12) . . ?
C17 C15' H15' 131.4 . . ?
C14 C15' H15' 131.4 . . ?
C1 N1 C2 107.87(15) . . ?
C1 N1 H1 126.1 . . ?
C2 N1 H1 126.1 . . ?
C1 N2 C3 105.66(15) . . ?
N2 C1 N1 111.30(17) . . ?
N2 C1 C4 124.35(17) . . ?
N1 C1 C4 124.35(17) . . ?
N1 C2 C3 105.46(16) . . ?
N1 C2 C10 121.57(17) . . ?
C3 C2 C10 132.98(18) . . ?
C2 C3 N2 109.71(17) . . ?
C2 C3 C14 130.45(18) . . ?
N2 C3 C14 119.73(16) . . ?
C9 C4 C5 119.24(18) . . ?
C9 C4 C1 121.90(18) . . ?
C5 C4 C1 118.87(18) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.0(2) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C2 127.68(18) . . ?
C11 C10 S1 111.02(15) . . ?
C2 C10 S1 121.27(15) . . ?
C10 C11 C12 111.62(19) . . ?
C10 C11 H11 124.2 . . ?
C12 C11 H11 124.2 . . ?
C13 C12 C11 113.3(2) . . ?
C13 C12 H12 123.4 . . ?
C11 C12 H12 123.4 . . ?
C12 C13 S1 112.07(16) . . ?
C12 C13 H13 124.0 . . ?
S1 C13 H13 124.0 . . ?
C3 C14 S2 120.27(15) . . ?
C3 C14 C15' 120.27(15) . . ?
C3 C14 C15 125.21(15) . . ?
S2 C14 C15 114.37(12) . . ?
C3 C14 S2' 125.21(15) . . ?
C15' C14 S2' 114.37(12) . . ?
C17 C16 C15 116.25(19) . . ?
C17 C16 S2' 116.25(19) . . ?
C17 C16 H16 121.9 . . ?
C15 C16 H16 121.9 . . ?
C16 C17 S2 116.47(18) . . ?
C16 C17 C15' 116.47(18) . . ?
C16 C17 H17 121.8 . . ?
S2 C17 H17 121.8 . . ?

_refine_diff_density_max         0.593
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_i18083
_database_code_depnum_ccdc_archive 'CCDC 2082025'
loop_
_audit_author_name
_audit_author_address
'Kesatebrhan Haile Asressu'
;Academia Sinica
Taiwan
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-08-12 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         'C23 H19 Br N2 O2'
_chemical_formula_sum            'C23 H19 Br N2 O2'
_chemical_formula_weight         435.31

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'
Br Br -0.2901 2.4595 '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                   9.2089(2)
_cell_length_b                   19.8306(3)
_cell_length_c                   10.4519(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.4920(10)
_cell_angle_gamma                90
_cell_volume                     1870.44(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      30.37

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    2.220
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9203
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            78302
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.054
_diffrn_reflns_theta_max         30.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5710
_reflns_number_gt                4848
_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, 2014)'
_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)+(0.0231P)²+1.2629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5710
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0603
_refine_ls_wR_factor_gt          0.0562
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
Br1 Br 0.06714(2) 0.70917(2) 0.37315(2) 0.01563(4) Uani 1 1 d . . . . .
O1 O 0.35295(13) 0.90293(5) 0.66112(10) 0.0192(2) Uani 1 1 d . . . . .
O2 O 0.45954(12) 0.82430(5) 0.85330(10) 0.0168(2) Uani 1 1 d . . . . .
N1 N 0.27095(14) 0.58394(6) 0.50626(12) 0.0137(2) Uani 1 1 d . . . . .
H1 H 0.292(2) 0.5988(10) 0.4354(19) 0.022(5) Uiso 1 1 d . . . . .
N2 N 0.23286(13) 0.58527(6) 0.70915(11) 0.0136(2) Uani 1 1 d . . . . .
C1 C 0.25918(15) 0.62254(7) 0.61140(13) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.22511(15) 0.51955(7) 0.66374(13) 0.0130(2) Uani 1 1 d . . . . .
C3 C 0.24821(15) 0.51771(7) 0.53698(13) 0.0130(2) Uani 1 1 d . . . . .
C4 C 0.27628(15) 0.69633(6) 0.61644(13) 0.0128(2) Uani 1 1 d . . . . .
C5 C 0.20854(15) 0.74037(7) 0.51925(13) 0.0132(2) Uani 1 1 d . . . . .
C6 C 0.23443(16) 0.80974(7) 0.52823(14) 0.0145(3) Uani 1 1 d . . . . .
H6 H 0.191923 0.838617 0.458222 0.017 Uiso 1 1 calc R U . . .
C7 C 0.32245(16) 0.83611(7) 0.63985(14) 0.0140(3) Uani 1 1 d . . . . .
C8 C 0.38447(15) 0.79287(7) 0.74337(13) 0.0135(2) Uani 1 1 d . . . . .
C9 C 0.36472(16) 0.72404(7) 0.72961(13) 0.0136(3) Uani 1 1 d . . . . .
H9 H 0.411567 0.694927 0.797611 0.016 Uiso 1 1 calc R U . . .
C10 C 0.3483(2) 0.94414(8) 0.54884(17) 0.0295(4) Uani 1 1 d . . . . .
H10A H 0.402465 0.921890 0.488877 0.044 Uiso 1 1 calc R U . . .
H10B H 0.394332 0.987826 0.575451 0.044 Uiso 1 1 calc R U . . .
H10C H 0.245048 0.951060 0.504922 0.044 Uiso 1 1 calc R U . . .
C11 C 0.55751(17) 0.78365(8) 0.94592(14) 0.0193(3) Uani 1 1 d . . . . .
H11A H 0.630086 0.761730 0.902668 0.029 Uiso 1 1 calc R U . . .
H11B H 0.500181 0.749200 0.981347 0.029 Uiso 1 1 calc R U . . .
H11C H 0.609280 0.812215 1.017109 0.029 Uiso 1 1 calc R U . . .
C12 C 0.19418(16) 0.46326(7) 0.74605(13) 0.0144(3) Uani 1 1 d . . . . .
C13 C 0.27647(17) 0.40368(7) 0.75352(14) 0.0175(3) Uani 1 1 d . . . . .
H13 H 0.353998 0.399717 0.706102 0.021 Uiso 1 1 calc R U . . .
C14 C 0.24569(18) 0.35012(8) 0.82990(15) 0.0220(3) Uani 1 1 d . . . . .
H14 H 0.301352 0.309588 0.833527 0.026 Uiso 1 1 calc R U . . .
C15 C 0.1339(2) 0.35576(8) 0.90078(15) 0.0240(3) Uani 1 1 d . . . . .
H15 H 0.112704 0.319157 0.952771 0.029 Uiso 1 1 calc R U . . .
C16 C 0.05310(19) 0.41530(8) 0.89529(16) 0.0249(3) Uani 1 1 d . . . . .
H16 H -0.022339 0.419574 0.944919 0.030 Uiso 1 1 calc R U . . .
C17 C 0.08192(18) 0.46846(7) 0.81783(15) 0.0195(3) Uani 1 1 d . . . . .
H17 H 0.024991 0.508646 0.813558 0.023 Uiso 1 1 calc R U . . .
C18 C 0.24300(15) 0.46285(7) 0.44158(13) 0.0133(2) Uani 1 1 d . . . . .
C19 C 0.13358(16) 0.41326(7) 0.43201(14) 0.0155(3) Uani 1 1 d . . . . .
H19 H 0.065296 0.414483 0.489161 0.019 Uiso 1 1 calc R U . . .
C20 C 0.12365(17) 0.36206(7) 0.33949(14) 0.0192(3) Uani 1 1 d . . . . .
H20 H 0.048824 0.328573 0.333547 0.023 Uiso 1 1 calc R U . . .
C21 C 0.22328(19) 0.36009(7) 0.25605(14) 0.0222(3) Uani 1 1 d . . . . .
H21 H 0.216690 0.325218 0.192839 0.027 Uiso 1 1 calc R U . . .
C22 C 0.33263(19) 0.40901(8) 0.26476(15) 0.0224(3) Uani 1 1 d . . . . .
H22 H 0.400679 0.407430 0.207421 0.027 Uiso 1 1 calc R U . . .
C23 C 0.34324(18) 0.46035(7) 0.35697(14) 0.0188(3) Uani 1 1 d . . . . .
H23 H 0.418382 0.493658 0.362508 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
Br1 C5 1.9022(13) . ?
O1 C7 1.3634(16) . ?
O1 C10 1.4237(19) . ?
O2 C8 1.3675(16) . ?
O2 C11 1.4328(17) . ?
N1 C1 1.3611(17) . ?
N1 C3 1.3780(17) . ?
N1 H1 0.85(2) . ?
N2 C1 1.3220(18) . ?
N2 C2 1.3839(17) . ?
C1 C4 1.4716(18) . ?
C2 C3 1.3835(19) . ?
C2 C12 1.4714(19) . ?
C3 C18 1.4700(18) . ?
C4 C5 1.3896(18) . ?
C4 C9 1.4073(18) . ?
C5 C6 1.3960(18) . ?
C6 C7 1.3838(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.4093(19) . ?
C8 C9 1.3807(18) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.397(2) . ?
C12 C13 1.397(2) . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.3973(19) . ?
C18 C23 1.401(2) . ?
C19 C20 1.3925(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(2) . ?
C22 H22 0.9500 . ?
C23 H23 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
C7 O1 C10 116.87(12) . . ?
C8 O2 C11 117.14(11) . . ?
C1 N1 C3 107.92(12) . . ?
C1 N1 H1 125.0(13) . . ?
C3 N1 H1 127.0(13) . . ?
C1 N2 C2 105.44(11) . . ?
N2 C1 N1 111.47(12) . . ?
N2 C1 C4 124.27(12) . . ?
N1 C1 C4 124.26(12) . . ?
C3 C2 N2 110.25(12) . . ?
C3 C2 C12 128.64(12) . . ?
N2 C2 C12 121.11(12) . . ?
N1 C3 C2 104.92(12) . . ?
N1 C3 C18 122.22(12) . . ?
C2 C3 C18 132.74(12) . . ?
C5 C4 C9 117.99(12) . . ?
C5 C4 C1 124.72(12) . . ?
C9 C4 C1 117.28(12) . . ?
C4 C5 C6 121.63(12) . . ?
C4 C5 Br1 121.21(10) . . ?
C6 C5 Br1 117.05(10) . . ?
C7 C6 C5 119.51(12) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O1 C7 C6 124.88(13) . . ?
O1 C7 C8 115.29(12) . . ?
C6 C7 C8 119.80(12) . . ?
O2 C8 C9 124.90(12) . . ?
O2 C8 C7 115.31(12) . . ?
C9 C8 C7 119.78(12) . . ?
C8 C9 C4 121.05(12) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
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 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.92(13) . . ?
C17 C12 C2 120.54(13) . . ?
C13 C12 C2 120.54(13) . . ?
C14 C13 C12 120.48(14) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.17(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.62(14) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.43(15) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 120.37(14) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C23 119.10(13) . . ?
C19 C18 C3 119.67(13) . . ?
C23 C18 C3 121.19(13) . . ?
C20 C19 C18 120.64(14) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 119.81(14) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.09(14) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 120.43(15) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 119.93(14) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_i18117
_database_code_depnum_ccdc_archive 'CCDC 2082032'
loop_
_audit_author_name
_audit_author_address
'Kesatebrhan Haile Asressu'
;Academia Sinica
Taiwan
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-08-12 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         'C38 H28 N4 O2'
_chemical_formula_sum            'C38 H28 N4 O2'
_chemical_formula_weight         572.64

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.9585(4)
_cell_length_b                   11.3947(5)
_cell_length_c                   28.7859(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2938.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    3336
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      62.85

_exptl_crystal_description       niddle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.644
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9329
_exptl_absorpt_correction_T_max  0.9621
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27891
_diffrn_reflns_av_unetI/netI     0.1014
_diffrn_reflns_av_R_equivalents  0.1401
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.070
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_full        66.595
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5125
_reflns_number_gt                3518
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.976

_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, 2014)'
_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)+(0.1560P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5125
_refine_ls_number_parameters     403
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0871
_refine_ls_wR_factor_ref         0.2411
_refine_ls_wR_factor_gt          0.2137
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.1603(7) 0.3907(5) 0.5150(2) 0.0362(15) Uani 1 1 d . . . . .
O2 O 0.5472(7) 0.6077(5) 0.4919(2) 0.0404(16) Uani 1 1 d . . . . .
N1 N 0.3283(8) 0.1445(6) 0.5762(2) 0.0279(16) Uani 1 1 d . . . . .
N2 N 0.1123(9) 0.2322(6) 0.5888(3) 0.0278(16) Uani 1 1 d . . . . .
H2 H 0.034(10) 0.282(8) 0.584(3) 0.033 Uiso 1 1 d . U . . .
N3 N 0.3780(9) 0.8541(7) 0.4306(2) 0.0341(18) Uani 1 1 d . . . . .
N4 N 0.5962(9) 0.7675(7) 0.4171(3) 0.0337(18) Uani 1 1 d . . . . .
H4 H 0.679(12) 0.722(9) 0.419(4) 0.040 Uiso 1 1 d . U . . .
C1 C 0.2351(10) 0.2299(8) 0.5627(3) 0.033(2) Uani 1 1 d . . . . .
C2 C 0.2570(9) 0.0889(7) 0.6133(3) 0.0254(18) Uani 1 1 d . . . . .
C3 C 0.1206(10) 0.1447(8) 0.6209(3) 0.0284(19) Uani 1 1 d . . . . .
C4 C 0.2628(10) 0.3023(7) 0.5219(3) 0.031(2) Uani 1 1 d . . . . .
C5 C 0.3612(11) 0.2976(9) 0.4877(3) 0.038(2) Uani 1 1 d . . . . .
H5 H 0.441158 0.243442 0.484441 0.046 Uiso 1 1 calc R U . . .
C6 C 0.3227(12) 0.3909(10) 0.4564(4) 0.046(3) Uani 1 1 d . . . . .
H6 H 0.373392 0.411609 0.428622 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2011(11) 0.4432(9) 0.4741(4) 0.042(2) Uani 1 1 d . . . . .
H7 H 0.150509 0.507504 0.460168 0.051 Uiso 1 1 calc R U . . .
C8 C 0.3310(10) -0.0078(7) 0.6384(3) 0.031(2) Uani 1 1 d . . . . .
C9 C 0.4331(10) -0.0788(8) 0.6145(3) 0.034(2) Uani 1 1 d . . . . .
H9 H 0.454334 -0.064115 0.582723 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5026(10) -0.1699(8) 0.6372(3) 0.036(2) Uani 1 1 d . . . . .
H10 H 0.570165 -0.218729 0.620664 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4757(11) -0.1918(8) 0.6840(4) 0.042(2) Uani 1 1 d . . . . .
H11 H 0.525317 -0.254115 0.699499 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3749(11) -0.1208(8) 0.7076(4) 0.040(2) Uani 1 1 d . . . . .
H12 H 0.355532 -0.134798 0.739557 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3035(11) -0.0311(8) 0.6852(3) 0.031(2) Uani 1 1 d . . . . .
H13 H 0.234096 0.015989 0.701829 0.038 Uiso 1 1 calc R U . . .
C14 C -0.0041(9) 0.1206(8) 0.6522(3) 0.0287(19) Uani 1 1 d . . . . .
C15 C -0.0585(10) 0.0058(8) 0.6587(4) 0.033(2) Uani 1 1 d . . . . .
H15 H -0.010220 -0.057905 0.643695 0.040 Uiso 1 1 calc R U . . .
C16 C -0.1799(10) -0.0154(9) 0.6864(3) 0.035(2) Uani 1 1 d . . . . .
H16 H -0.212003 -0.093805 0.691593 0.042 Uiso 1 1 calc R U . . .
C17 C -0.2559(11) 0.0768(8) 0.7068(4) 0.041(2) Uani 1 1 d . . . . .
H17 H -0.344357 0.062232 0.724039 0.049 Uiso 1 1 calc R U . . .
C18 C -0.2030(10) 0.1905(8) 0.7021(3) 0.034(2) Uani 1 1 d . . . . .
H18 H -0.251354 0.253277 0.717769 0.040 Uiso 1 1 calc R U . . .
C19 C -0.0789(9) 0.2123(8) 0.6744(3) 0.0293(19) Uani 1 1 d . . . . .
H19 H -0.044577 0.290546 0.670602 0.035 Uiso 1 1 calc R U . . .
C20 C 0.4720(10) 0.7714(7) 0.4443(3) 0.0294(19) Uani 1 1 d . . . . .
C21 C 0.4469(10) 0.9092(7) 0.3940(3) 0.030(2) Uani 1 1 d . . . . .
C22 C 0.5837(9) 0.8569(7) 0.3850(3) 0.0283(19) Uani 1 1 d . . . . .
C23 C 0.4481(10) 0.6968(8) 0.4840(3) 0.033(2) Uani 1 1 d . . . . .
C24 C 0.3439(11) 0.6995(9) 0.5188(3) 0.039(2) Uani 1 1 d . . . . .
H24 H 0.261734 0.751784 0.521284 0.047 Uiso 1 1 calc R U . . .
C25 C 0.3831(12) 0.6079(10) 0.5505(4) 0.046(3) Uani 1 1 d . . . . .
H25 H 0.334121 0.588892 0.578813 0.055 Uiso 1 1 calc R U . . .
C26 C 0.5028(12) 0.5545(8) 0.5324(3) 0.039(2) Uani 1 1 d . . . . .
H26 H 0.550811 0.488354 0.545766 0.047 Uiso 1 1 calc R U . . .
C27 C 0.3673(10) 1.0069(8) 0.3712(3) 0.032(2) Uani 1 1 d . . . . .
C28 C 0.2642(11) 1.0714(8) 0.3959(4) 0.038(2) Uani 1 1 d . . . . .
H28 H 0.248434 1.052784 0.427687 0.046 Uiso 1 1 calc R U . . .
C29 C 0.1827(11) 1.1622(8) 0.3764(3) 0.041(2) Uani 1 1 d . . . . .
H29 H 0.112788 1.205459 0.394365 0.049 Uiso 1 1 calc R U . . .
C30 C 0.2067(11) 1.1889(9) 0.3286(3) 0.039(2) Uani 1 1 d . . . . .
H30 H 0.150885 1.249584 0.314121 0.047 Uiso 1 1 calc R U . . .
C31 C 0.3109(10) 1.1268(8) 0.3036(3) 0.032(2) Uani 1 1 d . . . . .
H31 H 0.328650 1.145769 0.271898 0.039 Uiso 1 1 calc R U . . .
C32 C 0.3911(11) 1.0352(8) 0.3247(3) 0.032(2) Uani 1 1 d . . . . .
H32 H 0.462297 0.992250 0.307155 0.039 Uiso 1 1 calc R U . . .
C33 C 0.7041(10) 0.8817(8) 0.3516(3) 0.031(2) Uani 1 1 d . . . . .
C34 C 0.7492(10) 0.9985(8) 0.3427(3) 0.034(2) Uani 1 1 d . . . . .
H34 H 0.698257 1.062043 0.356967 0.040 Uiso 1 1 calc R U . . .
C35 C 0.8664(11) 1.0196(9) 0.3134(3) 0.036(2) Uani 1 1 d . . . . .
H35 H 0.895321 1.098286 0.307179 0.043 Uiso 1 1 calc R U . . .
C36 C 0.9441(11) 0.9280(9) 0.2925(3) 0.041(2) Uani 1 1 d . . . . .
H36 H 1.026634 0.943394 0.272672 0.049 Uiso 1 1 calc R U . . .
C37 C 0.8983(11) 0.8128(8) 0.3011(3) 0.035(2) Uani 1 1 d . . . . .
H37 H 0.949962 0.749466 0.286954 0.042 Uiso 1 1 calc R U . . .
C38 C 0.7807(10) 0.7904(8) 0.3296(3) 0.035(2) Uani 1 1 d . . . . .
H38 H 0.750170 0.711579 0.334707 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.371(12) . ?
O1 C4 1.377(10) . ?
O2 C23 1.368(11) . ?
O2 C26 1.372(11) . ?
N1 C1 1.339(11) . ?
N1 C2 1.398(11) . ?
N2 C1 1.332(12) . ?
N2 C3 1.361(12) . ?
N2 H2 0.91(10) . ?
N3 C20 1.324(12) . ?
N3 C21 1.374(11) . ?
N4 C20 1.362(12) . ?
N4 C22 1.380(12) . ?
N4 H4 0.90(11) . ?
C1 C4 1.458(12) . ?
C2 C3 1.395(12) . ?
C2 C8 1.474(12) . ?
C3 C14 1.461(12) . ?
C4 C5 1.323(13) . ?
C5 C6 1.435(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.341(15) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.397(12) . ?
C8 C9 1.402(13) . ?
C9 C10 1.375(12) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(13) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.397(12) . ?
C14 C15 1.408(12) . ?
C15 C16 1.369(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(12) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C23 1.441(13) . ?
C21 C22 1.387(12) . ?
C21 C27 1.476(13) . ?
C22 C33 1.473(12) . ?
C23 C24 1.368(14) . ?
C24 C25 1.431(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.339(15) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.378(13) . ?
C27 C32 1.392(13) . ?
C28 C29 1.386(13) . ?
C28 H28 0.9500 . ?
C29 C30 1.424(14) . ?
C29 H29 0.9500 . ?
C30 C31 1.376(13) . ?
C30 H30 0.9500 . ?
C31 C32 1.406(13) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C38 1.397(12) . ?
C33 C34 1.414(12) . ?
C34 C35 1.368(13) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(14) . ?
C35 H35 0.9500 . ?
C36 C37 1.397(14) . ?
C36 H36 0.9500 . ?
C37 C38 1.360(13) . ?
C37 H37 0.9500 . ?
C38 H38 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
C7 O1 C4 105.4(7) . . ?
C23 O2 C26 106.3(7) . . ?
C1 N1 C2 105.4(7) . . ?
C1 N2 C3 108.8(8) . . ?
C1 N2 H2 125(6) . . ?
C3 N2 H2 126(6) . . ?
C20 N3 C21 105.6(8) . . ?
C20 N4 C22 107.2(8) . . ?
C20 N4 H4 130(7) . . ?
C22 N4 H4 122(7) . . ?
N2 C1 N1 111.5(8) . . ?
N2 C1 C4 125.7(8) . . ?
N1 C1 C4 122.6(8) . . ?
C3 C2 N1 108.2(7) . . ?
C3 C2 C8 131.2(8) . . ?
N1 C2 C8 120.6(7) . . ?
N2 C3 C2 106.1(8) . . ?
N2 C3 C14 120.9(8) . . ?
C2 C3 C14 132.8(8) . . ?
C5 C4 O1 111.5(8) . . ?
C5 C4 C1 133.7(9) . . ?
O1 C4 C1 114.7(8) . . ?
C4 C5 C6 106.0(9) . . ?
C4 C5 H5 127.0 . . ?
C6 C5 H5 127.0 . . ?
C7 C6 C5 106.7(9) . . ?
C7 C6 H6 126.7 . . ?
C5 C6 H6 126.7 . . ?
C6 C7 O1 110.4(9) . . ?
C6 C7 H7 124.8 . . ?
O1 C7 H7 124.8 . . ?
C13 C8 C9 118.6(8) . . ?
C13 C8 C2 122.4(8) . . ?
C9 C8 C2 119.0(8) . . ?
C10 C9 C8 119.9(9) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 121.1(9) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 118.9(9) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.6(9) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 121.0(9) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C19 C14 C15 117.8(8) . . ?
C19 C14 C3 120.6(8) . . ?
C15 C14 C3 121.5(8) . . ?
C16 C15 C14 121.2(9) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.2(9) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.1(9) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 119.7(9) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 120.9(8) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
N3 C20 N4 111.8(8) . . ?
N3 C20 C23 124.2(8) . . ?
N4 C20 C23 124.0(8) . . ?
N3 C21 C22 110.1(8) . . ?
N3 C21 C27 118.0(8) . . ?
C22 C21 C27 131.9(8) . . ?
N4 C22 C21 105.3(8) . . ?
N4 C22 C33 121.3(8) . . ?
C21 C22 C33 133.4(8) . . ?
O2 C23 C24 109.8(8) . . ?
O2 C23 C20 118.2(8) . . ?
C24 C23 C20 131.9(9) . . ?
C23 C24 C25 106.5(9) . . ?
C23 C24 H24 126.8 . . ?
C25 C24 H24 126.8 . . ?
C26 C25 C24 106.1(9) . . ?
C26 C25 H25 126.9 . . ?
C24 C25 H25 126.9 . . ?
C25 C26 O2 111.3(9) . . ?
C25 C26 H26 124.3 . . ?
O2 C26 H26 124.3 . . ?
C28 C27 C32 118.4(9) . . ?
C28 C27 C21 119.7(8) . . ?
C32 C27 C21 121.9(8) . . ?
C27 C28 C29 122.8(9) . . ?
C27 C28 H28 118.6 . . ?
C29 C28 H28 118.6 . . ?
C28 C29 C30 118.1(9) . . ?
C28 C29 H29 121.0 . . ?
C30 C29 H29 121.0 . . ?
C31 C30 C29 119.9(9) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.1(8) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 120.7(9) . . ?
C27 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C38 C33 C34 118.6(8) . . ?
C38 C33 C22 120.8(8) . . ?
C34 C33 C22 120.5(8) . . ?
C35 C34 C33 119.8(9) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 121.2(9) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C37 118.7(9) . . ?
C35 C36 H36 120.6 . . ?
C37 C36 H36 120.6 . . ?
C38 C37 C36 120.8(9) . . ?
C38 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C37 C38 C33 120.8(8) . . ?
C37 C38 H38 119.6 . . ?
C33 C38 H38 119.6 . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_i18108
_database_code_depnum_ccdc_archive 'CCDC 2082029'
loop_
_audit_author_name
_audit_author_address
'Kesatebrhan Haile Asressu'
;Academia Sinica
Taiwan
;
_audit_update_record             
;
2021-05-06 deposited with the CCDC.	2021-08-12 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         '2(C23 H20 N2 O2), C H Cl3'
_chemical_formula_sum            'C47 H41 Cl3 N4 O4'
_chemical_formula_weight         832.19

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'
Cl Cl 0.1484 0.1585 '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'

_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                   10.2370(4)
_cell_length_b                   18.3683(6)
_cell_length_c                   22.3540(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.8070(10)
_cell_angle_gamma                90
_cell_volume                     4181.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9505
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             1736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            167934
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9215
_reflns_number_gt                7022
_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, 2014)'
_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)+(0.0969P)²+7.4717P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9215
_refine_ls_number_parameters     535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1928
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
Cl1 Cl 0.74956(11) 0.36009(6) 0.41472(4) 0.0496(3) Uani 1 1 d . . . . .
Cl2 Cl 0.82348(12) 0.49664(6) 0.47161(5) 0.0547(3) Uani 1 1 d . . . . .
Cl3 Cl 0.82071(12) 0.36653(6) 0.54311(5) 0.0567(3) Uani 1 1 d . . . . .
O1 O 0.12932(18) 0.70332(10) 0.72399(9) 0.0181(4) Uani 1 1 d . . . . .
O2 O 0.24107(18) 0.89612(10) 0.60556(8) 0.0182(4) Uani 1 1 d . . . . .
O3 O 0.5272(2) 0.44947(11) 0.56602(9) 0.0262(5) Uani 1 1 d . . . . .
O4 O 0.6993(2) 0.68146(10) 0.60279(9) 0.0200(4) Uani 1 1 d . . . . .
N1 N 0.6568(2) 0.86391(12) 0.76643(10) 0.0115(4) Uani 1 1 d . . . . .
N2 N 0.6260(2) 0.74970(11) 0.79270(9) 0.0117(4) Uani 1 1 d . . . . .
N3 N 0.5151(2) 0.60796(12) 0.80712(10) 0.0115(4) Uani 1 1 d . . . . .
N4 N 0.4032(2) 0.50806(11) 0.78090(10) 0.0120(4) Uani 1 1 d . . . . .
C1 C 0.5714(2) 0.80733(13) 0.76432(11) 0.0115(5) Uani 1 1 d . . . . .
C2 C 0.7732(2) 0.84178(13) 0.79797(11) 0.0122(5) Uani 1 1 d . . . . .
C3 C 0.7524(2) 0.77055(13) 0.81392(11) 0.0124(5) Uani 1 1 d . . . . .
C4 C 0.4389(2) 0.80740(13) 0.73202(11) 0.0115(5) Uani 1 1 d . . . . .
C5 C 0.3481(2) 0.75565(13) 0.74751(11) 0.0130(5) Uani 1 1 d . . . . .
H5 H 0.368804 0.723856 0.780630 0.016 Uiso 1 1 calc R U . . .
C6 C 0.2261(2) 0.75152(13) 0.71336(12) 0.0141(5) Uani 1 1 d . . . . .
C7 C 0.1945(2) 0.79814(13) 0.66560(12) 0.0140(5) Uani 1 1 d . . . . .
H7 H 0.112227 0.793832 0.642046 0.017 Uiso 1 1 calc R U . . .
C8 C 0.2835(2) 0.85137(13) 0.65216(11) 0.0135(5) Uani 1 1 d . . . . .
C9 C 0.4072(2) 0.85628(13) 0.68456(12) 0.0138(5) Uani 1 1 d . . . . .
H9 H 0.468545 0.891996 0.674657 0.017 Uiso 1 1 calc R U . . .
C10 C 0.1587(3) 0.65159(15) 0.77140(14) 0.0224(6) Uani 1 1 d . . . . .
H10A H 0.083579 0.618937 0.773441 0.034 Uiso 1 1 calc R U . . .
H10B H 0.176657 0.677355 0.809734 0.034 Uiso 1 1 calc R U . . .
H10C H 0.236006 0.623074 0.763446 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3269(3) 0.95426(15) 0.59226(14) 0.0225(6) Uani 1 1 d . . . . .
H11A H 0.409223 0.933990 0.580666 0.034 Uiso 1 1 calc R U . . .
H11B H 0.345444 0.985025 0.627933 0.034 Uiso 1 1 calc R U . . .
H11C H 0.284712 0.983541 0.559103 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8893(2) 0.88907(14) 0.80675(11) 0.0132(5) Uani 1 1 d . . . . .
C13 C 0.8789(3) 0.96158(14) 0.82506(12) 0.0162(5) Uani 1 1 d . . . . .
H13 H 0.796491 0.980015 0.834133 0.019 Uiso 1 1 calc R U . . .
C14 C 0.9883(3) 1.00668(15) 0.83003(13) 0.0206(6) Uani 1 1 d . . . . .
H14 H 0.980374 1.055732 0.842644 0.025 Uiso 1 1 calc R U . . .
C15 C 1.1089(3) 0.98060(15) 0.81673(13) 0.0220(6) Uani 1 1 d . . . . .
H15 H 1.183331 1.011737 0.819798 0.026 Uiso 1 1 calc R U . . .
C16 C 1.1204(3) 0.90851(15) 0.79883(13) 0.0198(6) Uani 1 1 d . . . . .
H16 H 1.203235 0.890284 0.790052 0.024 Uiso 1 1 calc R U . . .
C17 C 1.0119(3) 0.86334(14) 0.79379(12) 0.0160(5) Uani 1 1 d . . . . .
H17 H 1.020667 0.814265 0.781376 0.019 Uiso 1 1 calc R U . . .
C18 C 0.8394(2) 0.71873(14) 0.84868(12) 0.0156(5) Uani 1 1 d . . . . .
C19 C 0.9151(3) 0.73942(16) 0.90121(13) 0.0207(6) Uani 1 1 d . . . . .
H19 H 0.916806 0.788935 0.913527 0.025 Uiso 1 1 calc R U . . .
C20 C 0.9883(3) 0.68786(18) 0.93571(14) 0.0281(7) Uani 1 1 d . . . . .
H20 H 1.040132 0.702438 0.971339 0.034 Uiso 1 1 calc R U . . .
C21 C 0.9860(3) 0.61512(18) 0.91838(15) 0.0291(7) Uani 1 1 d . . . . .
H21 H 1.034947 0.579973 0.942424 0.035 Uiso 1 1 calc R U . . .
C22 C 0.9122(3) 0.59422(16) 0.86611(15) 0.0254(7) Uani 1 1 d . . . . .
H22 H 0.910920 0.544601 0.854078 0.030 Uiso 1 1 calc R U . . .
C23 C 0.8397(3) 0.64559(14) 0.83087(14) 0.0191(6) Uani 1 1 d . . . . .
H23 H 0.790206 0.630934 0.794616 0.023 Uiso 1 1 calc R U . . .
C24 C 0.4850(2) 0.55825(13) 0.76284(11) 0.0117(5) Uani 1 1 d . . . . .
C25 C 0.4475(2) 0.59019(13) 0.85544(11) 0.0112(5) Uani 1 1 d . . . . .
C26 C 0.3787(2) 0.52753(13) 0.83830(11) 0.0119(5) Uani 1 1 d . . . . .
C27 C 0.5319(2) 0.56093(13) 0.70310(11) 0.0126(5) Uani 1 1 d . . . . .
C28 C 0.5094(3) 0.50115(14) 0.66470(12) 0.0152(5) Uani 1 1 d . . . . .
H28 H 0.468360 0.458576 0.678026 0.018 Uiso 1 1 calc R U . . .
C29 C 0.5477(3) 0.50460(14) 0.60687(12) 0.0176(5) Uani 1 1 d . . . . .
C30 C 0.6100(3) 0.56585(14) 0.58705(12) 0.0174(5) Uani 1 1 d . . . . .
H30 H 0.635348 0.567704 0.547356 0.021 Uiso 1 1 calc R U . . .
C31 C 0.6350(3) 0.62441(14) 0.62582(12) 0.0149(5) Uani 1 1 d . . . . .
C32 C 0.5957(2) 0.62311(13) 0.68376(11) 0.0136(5) Uani 1 1 d . . . . .
H32 H 0.611743 0.663709 0.709786 0.016 Uiso 1 1 calc R U . . .
C33 C 0.4762(4) 0.38233(17) 0.58675(16) 0.0380(9) Uani 1 1 d . . . . .
H33A H 0.469872 0.346606 0.554028 0.057 Uiso 1 1 calc R U . . .
H33B H 0.388848 0.390725 0.599754 0.057 Uiso 1 1 calc R U . . .
H33C H 0.535041 0.363793 0.620641 0.057 Uiso 1 1 calc R U . . .
C34 C 0.7363(4) 0.74090(17) 0.64192(14) 0.0315(7) Uani 1 1 d . . . . .
H34A H 0.785374 0.776706 0.620603 0.047 Uiso 1 1 calc R U . . .
H34B H 0.791613 0.723026 0.677208 0.047 Uiso 1 1 calc R U . . .
H34C H 0.657372 0.763814 0.654822 0.047 Uiso 1 1 calc R U . . .
C35 C 0.4565(3) 0.63505(13) 0.91018(11) 0.0131(5) Uani 1 1 d . . . . .
C36 C 0.5761(3) 0.66514(14) 0.93330(12) 0.0152(5) Uani 1 1 d . . . . .
H36 H 0.652303 0.656802 0.913325 0.018 Uiso 1 1 calc R U . . .
C37 C 0.5850(3) 0.70722(14) 0.98524(12) 0.0187(5) Uani 1 1 d . . . . .
H37 H 0.667129 0.727358 1.000588 0.022 Uiso 1 1 calc R U . . .
C38 C 0.4745(3) 0.71981(15) 1.01463(12) 0.0197(6) Uani 1 1 d . . . . .
H38 H 0.480746 0.748231 1.050316 0.024 Uiso 1 1 calc R U . . .
C39 C 0.3547(3) 0.69081(15) 0.99181(13) 0.0204(6) Uani 1 1 d . . . . .
H39 H 0.278677 0.699871 1.011736 0.024 Uiso 1 1 calc R U . . .
C40 C 0.3451(3) 0.64852(14) 0.93994(12) 0.0169(5) Uani 1 1 d . . . . .
H40 H 0.262691 0.628736 0.924664 0.020 Uiso 1 1 calc R U . . .
C41 C 0.2829(2) 0.48534(13) 0.86946(11) 0.0119(5) Uani 1 1 d . . . . .
C42 C 0.3011(3) 0.46870(14) 0.93077(12) 0.0146(5) Uani 1 1 d . . . . .
H42 H 0.379151 0.483449 0.954273 0.018 Uiso 1 1 calc R U . . .
C43 C 0.2046(3) 0.43044(14) 0.95732(12) 0.0158(5) Uani 1 1 d . . . . .
H43 H 0.217324 0.419215 0.998989 0.019 Uiso 1 1 calc R U . . .
C44 C 0.0902(3) 0.40857(14) 0.92368(12) 0.0163(5) Uani 1 1 d . . . . .
H44 H 0.024272 0.383137 0.942257 0.020 Uiso 1 1 calc R U . . .
C45 C 0.0726(3) 0.42412(14) 0.86253(12) 0.0155(5) Uani 1 1 d . . . . .
H45 H -0.004930 0.408525 0.839049 0.019 Uiso 1 1 calc R U . . .
C46 C 0.1679(2) 0.46236(13) 0.83577(12) 0.0139(5) Uani 1 1 d . . . . .
H46 H 0.154926 0.473074 0.794019 0.017 Uiso 1 1 calc R U . . .
C47 C 0.7452(4) 0.4125(2) 0.47984(16) 0.0400(8) Uani 1 1 d . . . . .
H47 H 0.651381 0.421859 0.486201 0.048 Uiso 1 1 calc R U . . .
H1 H 0.641(3) 0.9021(19) 0.7513(14) 0.015(8) Uiso 1 1 d . . . . .
H3 H 0.548(3) 0.6433(19) 0.8034(15) 0.019(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C47 1.750(4) . ?
Cl2 C47 1.759(4) . ?
Cl3 C47 1.758(4) . ?
O1 C6 1.367(3) . ?
O1 C10 1.433(3) . ?
O2 C8 1.363(3) . ?
O2 C11 1.433(3) . ?
O3 C29 1.365(3) . ?
O3 C33 1.434(4) . ?
O4 C31 1.366(3) . ?
O4 C34 1.426(3) . ?
N1 C1 1.355(3) . ?
N1 C2 1.383(3) . ?
N1 H1 0.79(3) . ?
N2 C1 1.328(3) . ?
N2 C3 1.387(3) . ?
N3 C24 1.359(3) . ?
N3 C25 1.379(3) . ?
N3 H3 0.74(4) . ?
N4 C24 1.335(3) . ?
N4 C26 1.380(3) . ?
C1 C4 1.471(3) . ?
C2 C3 1.378(3) . ?
C2 C12 1.469(3) . ?
C3 C18 1.471(3) . ?
C4 C5 1.398(3) . ?
C4 C9 1.403(3) . ?
C5 C6 1.398(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(4) . ?
C7 C8 1.390(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(4) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.398(4) . ?
C12 C13 1.401(4) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.393(4) . ?
C18 C23 1.401(4) . ?
C19 C20 1.391(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C27 1.465(3) . ?
C25 C26 1.383(3) . ?
C25 C35 1.471(3) . ?
C26 C41 1.478(3) . ?
C27 C28 1.398(3) . ?
C27 C32 1.405(3) . ?
C28 C29 1.390(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(4) . ?
C30 C31 1.389(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.395(4) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.394(4) . ?
C35 C40 1.399(4) . ?
C36 C37 1.390(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.384(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.386(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.391(4) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C46 1.397(4) . ?
C41 C42 1.398(4) . ?
C42 C43 1.394(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.386(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.390(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.387(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 H47 1.0000 . ?

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 117.2(2) . . ?
C8 O2 C11 117.0(2) . . ?
C29 O3 C33 117.3(2) . . ?
C31 O4 C34 117.7(2) . . ?
C1 N1 C2 108.2(2) . . ?
C1 N1 H1 125(2) . . ?
C2 N1 H1 127(2) . . ?
C1 N2 C3 106.0(2) . . ?
C24 N3 C25 108.5(2) . . ?
C24 N3 H3 125(3) . . ?
C25 N3 H3 125(3) . . ?
C24 N4 C26 106.3(2) . . ?
N2 C1 N1 110.9(2) . . ?
N2 C1 C4 123.9(2) . . ?
N1 C1 C4 125.1(2) . . ?
C3 C2 N1 105.2(2) . . ?
C3 C2 C12 132.1(2) . . ?
N1 C2 C12 122.6(2) . . ?
C2 C3 N2 109.7(2) . . ?
C2 C3 C18 130.5(2) . . ?
N2 C3 C18 119.8(2) . . ?
C5 C4 C9 120.9(2) . . ?
C5 C4 C1 118.8(2) . . ?
C9 C4 C1 120.2(2) . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
O1 C6 C7 114.7(2) . . ?
O1 C6 C5 124.3(2) . . ?
C7 C6 C5 121.0(2) . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
O2 C8 C7 115.1(2) . . ?
O2 C8 C9 124.0(2) . . ?
C7 C8 C9 120.9(2) . . ?
C8 C9 C4 118.7(2) . . ?
C8 C9 H9 120.7 . . ?
C4 C9 H9 120.7 . . ?
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 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.6(2) . . ?
C17 C12 C2 120.2(2) . . ?
C13 C12 C2 121.1(2) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C19 C18 C23 119.0(2) . . ?
C19 C18 C3 121.6(2) . . ?
C23 C18 C3 119.3(2) . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.7(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
N4 C24 N3 110.3(2) . . ?
N4 C24 C27 124.9(2) . . ?
N3 C24 C27 124.8(2) . . ?
N3 C25 C26 105.2(2) . . ?
N3 C25 C35 121.7(2) . . ?
C26 C25 C35 133.1(2) . . ?
N4 C26 C25 109.7(2) . . ?
N4 C26 C41 119.6(2) . . ?
C25 C26 C41 130.5(2) . . ?
C28 C27 C32 120.1(2) . . ?
C28 C27 C24 119.0(2) . . ?
C32 C27 C24 120.9(2) . . ?
C29 C28 C27 119.4(2) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
O3 C29 C30 115.6(2) . . ?
O3 C29 C28 123.3(2) . . ?
C30 C29 C28 121.0(2) . . ?
C29 C30 C31 119.4(2) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
O4 C31 C30 115.1(2) . . ?
O4 C31 C32 124.0(2) . . ?
C30 C31 C32 120.9(2) . . ?
C31 C32 C27 119.1(2) . . ?
C31 C32 H32 120.5 . . ?
C27 C32 H32 120.5 . . ?
O3 C33 H33A 109.5 . . ?
O3 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O3 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O4 C34 H34A 109.5 . . ?
O4 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O4 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C40 118.7(2) . . ?
C36 C35 C25 120.6(2) . . ?
C40 C35 C25 120.6(2) . . ?
C37 C36 C35 120.8(2) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C38 C37 C36 120.1(3) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C39 119.8(2) . . ?
C37 C38 H38 120.1 . . ?
C39 C38 H38 120.1 . . ?
C38 C39 C40 120.5(3) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C39 C40 C35 120.2(3) . . ?
C39 C40 H40 119.9 . . ?
C35 C40 H40 119.9 . . ?
C46 C41 C42 118.9(2) . . ?
C46 C41 C26 117.8(2) . . ?
C42 C41 C26 123.2(2) . . ?
C43 C42 C41 119.9(2) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C44 C43 C42 120.8(2) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 119.5(2) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C46 C45 C44 120.1(2) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C41 120.8(2) . . ?
C45 C46 H46 119.6 . . ?
C41 C46 H46 119.6 . . ?
Cl1 C47 Cl3 111.0(2) . . ?
Cl1 C47 Cl2 110.3(2) . . ?
Cl3 C47 Cl2 109.8(2) . . ?
Cl1 C47 H47 108.6 . . ?
Cl3 C47 H47 108.6 . . ?
Cl2 C47 H47 108.6 . . ?

_refine_diff_density_max         1.274
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.092

