# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2092483'
loop_
_audit_author_name
_audit_author_address
'Jie Zhou'
;Yun University
China
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 N3 S'
_chemical_formula_weight         251.30

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'
S S 0.3331 0.5567 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.51440(10)
_cell_length_b                   8.8611(2)
_cell_length_c                   17.9123(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.2480(10)
_cell_angle_gamma                90
_cell_volume                     1169.80(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    7950
_cell_measurement_theta_min      5.0349
_cell_measurement_theta_max      68.3460

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    2.309
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.675
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13564
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.035
_diffrn_reflns_theta_max         68.413
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2121
_reflns_number_gt                1818
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 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)+(0.0593P)²+0.6036P] 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         2121
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.1475(3) 0.7639(3) 0.57381(14) 0.0573(6) Uani 1 1 d . . . . .
C2 C 0.2889(3) 0.7752(2) 0.53012(12) 0.0488(5) Uani 1 1 d . . . . .
C3 C 0.4485(3) 0.6945(3) 0.55083(13) 0.0546(6) Uani 1 1 d . . . . .
H3 H 0.4678 0.6355 0.5946 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5794(3) 0.7016(3) 0.50633(12) 0.0502(5) Uani 1 1 d . . . . .
H4 H 0.6869 0.6480 0.5210 0.060 Uiso 1 1 calc R U . . .
C5 C 0.5532(3) 0.7876(2) 0.44005(11) 0.0407(4) Uani 1 1 d . . . . .
C6 C 0.3935(3) 0.8708(2) 0.42144(12) 0.0459(5) Uani 1 1 d . . . . .
H6 H 0.3748 0.9314 0.3782 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2623(3) 0.8657(2) 0.46560(13) 0.0495(5) Uani 1 1 d . . . . .
H7 H 0.1567 0.9225 0.4523 0.059 Uiso 1 1 calc R U . . .
C8 C 0.6900(3) 0.7916(2) 0.39047(11) 0.0404(4) Uani 1 1 d . . . . .
C9 C 0.8160(3) 0.6747(2) 0.39062(11) 0.0421(4) Uani 1 1 d . . . . .
H9 H 0.8158 0.5917 0.4224 0.050 Uiso 1 1 calc R U . . .
C10 C 0.9403(3) 0.6835(2) 0.34320(11) 0.0395(4) Uani 1 1 d . . . . .
C11 C 0.9450(3) 0.8076(2) 0.29455(11) 0.0406(4) Uani 1 1 d . . . . .
C12 C 0.8194(3) 0.9226(2) 0.29412(12) 0.0469(5) Uani 1 1 d . . . . .
H12 H 0.8190 1.0053 0.2621 0.056 Uiso 1 1 calc R U . . .
C13 C 0.6951(3) 0.9136(2) 0.34132(12) 0.0475(5) Uani 1 1 d . . . . .
H13 H 0.6117 0.9915 0.3405 0.057 Uiso 1 1 calc R U . . .
C14 C 1.1751(3) 0.6816(2) 0.26544(12) 0.0434(5) Uani 1 1 d . . . . .
N1 N 0.0333(3) 0.7556(3) 0.60744(15) 0.0762(7) Uani 1 1 d . . . . .
N2 N 1.0792(2) 0.80480(19) 0.25113(9) 0.0446(4) Uani 1 1 d . . . . .
N3 N 1.3148(3) 0.6427(2) 0.23282(12) 0.0598(5) Uani 1 1 d . . . . .
H3A H 1.3473 0.7010 0.1995 0.072 Uiso 1 1 calc R U . . .
H3B H 1.3717 0.5594 0.2452 0.072 Uiso 1 1 calc R U . . .
S1 S 1.11155(7) 0.55758(6) 0.33227(3) 0.0486(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.143(3) . ?
C1 C2 1.440(3) . ?
C2 C3 1.384(3) . ?
C2 C7 1.389(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 C8 1.484(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.399(3) . ?
C8 C9 1.403(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.408(3) . ?
C10 S1 1.743(2) . ?
C11 C12 1.388(3) . ?
C11 N2 1.389(2) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N2 1.306(3) . ?
C14 N3 1.342(2) . ?
C14 S1 1.758(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 178.9(3) . . ?
C3 C2 C7 119.88(19) . . ?
C3 C2 C1 120.8(2) . . ?
C7 C2 C1 119.3(2) . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 117.76(18) . . ?
C4 C5 C8 121.65(18) . . ?
C6 C5 C8 120.60(18) . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 119.5(2) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
C13 C8 C9 118.08(18) . . ?
C13 C8 C5 120.16(18) . . ?
C9 C8 C5 121.76(17) . . ?
C10 C9 C8 119.58(18) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.73(18) . . ?
C9 C10 S1 129.45(15) . . ?
C11 C10 S1 108.81(14) . . ?
C12 C11 N2 125.28(18) . . ?
C12 C11 C10 118.55(18) . . ?
N2 C11 C10 116.17(17) . . ?
C13 C12 C11 119.71(18) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 122.36(19) . . ?
C12 C13 H13 118.8 . . ?
C8 C13 H13 118.8 . . ?
N2 C14 N3 125.31(19) . . ?
N2 C14 S1 116.31(14) . . ?
N3 C14 S1 118.38(17) . . ?
C14 N2 C11 109.79(16) . . ?
C14 N3 H3A 120.0 . . ?
C14 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C10 S1 C14 88.91(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 -1.4(3) . . . . ?
C1 C2 C3 C4 177.2(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C3 C4 C5 C8 -177.8(2) . . . . ?
C4 C5 C6 C7 -1.9(3) . . . . ?
C8 C5 C6 C7 178.29(18) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C3 C2 C7 C6 1.9(3) . . . . ?
C1 C2 C7 C6 -176.7(2) . . . . ?
C4 C5 C8 C13 -157.3(2) . . . . ?
C6 C5 C8 C13 22.5(3) . . . . ?
C4 C5 C8 C9 23.3(3) . . . . ?
C6 C5 C8 C9 -156.91(19) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C5 C8 C9 C10 179.77(17) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C8 C9 C10 S1 179.28(15) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
S1 C10 C11 C12 -179.94(16) . . . . ?
C9 C10 C11 N2 178.46(17) . . . . ?
S1 C10 C11 N2 -0.7(2) . . . . ?
N2 C11 C12 C13 -178.52(19) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
C5 C8 C13 C12 -179.92(19) . . . . ?
N3 C14 N2 C11 179.5(2) . . . . ?
S1 C14 N2 C11 0.3(2) . . . . ?
C12 C11 N2 C14 179.5(2) . . . . ?
C10 C11 N2 C14 0.3(2) . . . . ?
C9 C10 S1 C14 -178.42(19) . . . . ?
C11 C10 S1 C14 0.69(15) . . . . ?
N2 C14 S1 C10 -0.59(17) . . . . ?
N3 C14 S1 C10 -179.86(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A N1 0.86 2.39 3.161(3) 149.1 4_775
N3 H3B N2 0.86 2.29 3.097(3) 157.5 2_745

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2098589'
loop_
_audit_author_name
_audit_author_address
'Jie Zhou'
;Yun University
China
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 F3 N2 S'
_chemical_formula_weight         294.29

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'
F F 0.0171 0.0103 '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                   12.0962(12)
_cell_length_b                   9.1516(9)
_cell_length_c                   11.7094(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.352(5)
_cell_angle_gamma                90
_cell_volume                     1285.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1650
_cell_measurement_theta_min      3.1864
_cell_measurement_theta_max      27.8625

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.278
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            8059
_diffrn_reflns_av_unetI/netI     0.1306
_diffrn_reflns_av_R_equivalents  0.1190
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.799
_diffrn_reflns_theta_max         25.145
_diffrn_reflns_theta_full        25.145
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             2210
_reflns_number_gt                966
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 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)+(0.0519P)²+0.0438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2210
_refine_ls_number_parameters     209
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1973
_refine_ls_R_factor_gt           0.0825
_refine_ls_wR_factor_ref         0.2110
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.195
_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
F1A F 0.9858(14) 0.3972(16) 0.1217(10) 0.083(5) Uani 0.475(14) 1 d . . P A 1
F2A F 0.9788(10) 0.6195(14) 0.1291(7) 0.087(4) Uani 0.475(14) 1 d . U P A 1
F3A F 0.8698(14) 0.5935(14) 0.0750(11) 0.087(4) Uani 0.475(14) 1 d . U P A 1
F1B F 0.887(2) 0.3611(12) 0.0700(11) 0.145(8) Uani 0.525(14) 1 d . . P A 2
F2B F 1.0067(12) 0.515(2) 0.1370(9) 0.116(5) Uani 0.525(14) 1 d . U P A 2
F3B F 0.8298(8) 0.516(2) 0.0513(7) 0.102(5) Uani 0.525(14) 1 d . . P A 2
N1 N 0.4061(5) 0.3604(6) 0.9148(4) 0.0749(19) Uani 1 1 d . . . . .
H1A H 0.4177 0.3903 0.9849 0.090 Uiso 1 1 calc R U . . .
H1B H 0.3469 0.3114 0.8912 0.090 Uiso 1 1 calc R U . . .
N2 N 0.5726(5) 0.4629(5) 0.8674(4) 0.0541(15) Uani 1 1 d . . . . .
S1 S 0.45393(17) 0.3279(2) 0.69793(13) 0.0736(7) Uani 1 1 d . . . . .
C1 C 0.4817(6) 0.3906(7) 0.8409(5) 0.0564(18) Uani 1 1 d . . . . .
C2 C 0.6308(5) 0.4721(6) 0.7723(4) 0.0453(16) Uani 1 1 d . . . . .
C3 C 0.5794(5) 0.4055(6) 0.6714(5) 0.0509(17) Uani 1 1 d . . . . .
C4 C 0.6279(6) 0.4053(7) 0.5703(5) 0.0554(18) Uani 1 1 d . . . . .
H4 H 0.5916 0.3608 0.5046 0.066 Uiso 1 1 calc R U . . .
C5 C 0.7300(6) 0.4709(6) 0.5673(4) 0.0486(16) Uani 1 1 d . . . . .
C6 C 0.7808(5) 0.5381(6) 0.6676(4) 0.0534(18) Uani 1 1 d . . . . .
H6 H 0.8495 0.5834 0.6665 0.064 Uiso 1 1 calc R U . . .
C7 C 0.7324(6) 0.5396(7) 0.7687(4) 0.0563(19) Uani 1 1 d . . . . .
H7 H 0.7682 0.5859 0.8339 0.068 Uiso 1 1 calc R U . . .
C8 C 0.7823(6) 0.4712(6) 0.4596(4) 0.0530(18) Uani 1 1 d . . . . .
C9 C 0.7607(7) 0.3626(7) 0.3788(5) 0.074(2) Uani 1 1 d . . . . .
H9 H 0.7173 0.2833 0.3950 0.088 Uiso 1 1 calc R U . . .
C10 C 0.8018(7) 0.3682(7) 0.2745(5) 0.077(2) Uani 1 1 d . . . . .
H10 H 0.7846 0.2941 0.2208 0.092 Uiso 1 1 calc R U . . .
C11 C 0.8675(6) 0.4820(7) 0.2495(5) 0.0550(18) Uani 1 1 d . . . . .
C12 C 0.8942(6) 0.5881(8) 0.3291(5) 0.072(2) Uani 1 1 d . . . . .
H12 H 0.9408 0.6645 0.3137 0.087 Uiso 1 1 calc R U . . .
C13 C 0.8516(6) 0.5825(7) 0.4334(5) 0.066(2) Uani 1 1 d . . . . .
H13 H 0.8703 0.6559 0.4873 0.079 Uiso 1 1 calc R U . . .
C14 C 0.9063(7) 0.4812(10) 0.1325(6) 0.073(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C14 1.250(11) . ?
F2A F3A 1.409(18) . ?
F2A C14 1.544(14) . ?
F3A C14 1.276(14) . ?
F1B C14 1.324(13) . ?
F1B F3B 1.59(2) . ?
F2B C14 1.247(13) . ?
F3B C14 1.280(11) . ?
N1 C1 1.365(7) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C1 1.287(8) . ?
N2 C2 1.395(6) . ?
S1 C3 1.739(6) . ?
S1 C1 1.761(6) . ?
C2 C7 1.380(8) . ?
C2 C3 1.402(8) . ?
C3 C4 1.387(7) . ?
C4 C5 1.377(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(8) . ?
C5 C8 1.483(7) . ?
C6 C7 1.387(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.374(7) . ?
C8 C13 1.378(8) . ?
C9 C10 1.377(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(8) . ?
C11 C14 1.505(8) . ?
C12 C13 1.386(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F3A F2A C14 51.0(7) . . ?
C14 F3A F2A 70.0(11) . . ?
C14 F1B F3B 51.2(8) . . ?
C14 F3B F1B 53.8(10) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C2 110.0(5) . . ?
C3 S1 C1 88.4(3) . . ?
N2 C1 N1 124.9(6) . . ?
N2 C1 S1 116.7(4) . . ?
N1 C1 S1 118.3(6) . . ?
C7 C2 N2 126.4(5) . . ?
C7 C2 C3 118.0(5) . . ?
N2 C2 C3 115.6(6) . . ?
C4 C3 C2 121.9(6) . . ?
C4 C3 S1 128.8(5) . . ?
C2 C3 S1 109.3(4) . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 118.1(5) . . ?
C4 C5 C8 120.3(5) . . ?
C6 C5 C8 121.6(6) . . ?
C7 C6 C5 122.2(6) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C2 C7 C6 119.7(5) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C13 116.7(5) . . ?
C9 C8 C5 121.3(6) . . ?
C13 C8 C5 121.9(5) . . ?
C8 C9 C10 121.7(6) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.6(5) . . ?
C12 C11 C14 123.7(7) . . ?
C10 C11 C14 116.7(6) . . ?
C11 C12 C13 119.7(7) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 121.9(6) . . ?
C8 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
F1A C14 F3A 131.4(9) . . ?
F2B C14 F3B 125.2(11) . . ?
F2B C14 F1B 109.1(13) . . ?
F3B C14 F1B 75.0(15) . . ?
F1A C14 C11 115.4(7) . . ?
F2B C14 C11 112.1(9) . . ?
F3A C14 C11 110.4(9) . . ?
F3B C14 C11 113.3(8) . . ?
F1B C14 C11 117.1(8) . . ?
F1A C14 F2A 93.1(10) . . ?
F3A C14 F2A 59.0(10) . . ?
C11 C14 F2A 105.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 179.2(6) . . . . ?
C2 N2 C1 S1 -1.1(7) . . . . ?
C3 S1 C1 N2 0.8(6) . . . . ?
C3 S1 C1 N1 -179.5(6) . . . . ?
C1 N2 C2 C7 -179.1(6) . . . . ?
C1 N2 C2 C3 0.9(8) . . . . ?
C7 C2 C3 C4 0.4(9) . . . . ?
N2 C2 C3 C4 -179.6(5) . . . . ?
C7 C2 C3 S1 179.7(5) . . . . ?
N2 C2 C3 S1 -0.4(7) . . . . ?
C1 S1 C3 C4 179.0(6) . . . . ?
C1 S1 C3 C2 -0.2(5) . . . . ?
C2 C3 C4 C5 0.5(10) . . . . ?
S1 C3 C4 C5 -178.6(5) . . . . ?
C3 C4 C5 C6 -0.9(9) . . . . ?
C3 C4 C5 C8 -180.0(5) . . . . ?
C4 C5 C6 C7 0.4(9) . . . . ?
C8 C5 C6 C7 179.5(5) . . . . ?
N2 C2 C7 C6 179.2(5) . . . . ?
C3 C2 C7 C6 -0.9(9) . . . . ?
C5 C6 C7 C2 0.5(10) . . . . ?
C4 C5 C8 C9 -27.8(10) . . . . ?
C6 C5 C8 C9 153.2(7) . . . . ?
C4 C5 C8 C13 149.9(7) . . . . ?
C6 C5 C8 C13 -29.2(10) . . . . ?
C13 C8 C9 C10 -3.1(11) . . . . ?
C5 C8 C9 C10 174.6(7) . . . . ?
C8 C9 C10 C11 1.3(12) . . . . ?
C9 C10 C11 C12 1.4(11) . . . . ?
C9 C10 C11 C14 -178.5(7) . . . . ?
C10 C11 C12 C13 -2.0(11) . . . . ?
C14 C11 C12 C13 177.9(7) . . . . ?
C9 C8 C13 C12 2.4(11) . . . . ?
C5 C8 C13 C12 -175.3(6) . . . . ?
C11 C12 C13 C8 0.1(11) . . . . ?
F2A F3A C14 F1A -64(2) . . . . ?
F2A F3A C14 C11 96.0(9) . . . . ?
F1B F3B C14 F2B 103.0(16) . . . . ?
F1B F3B C14 C11 -113.4(11) . . . . ?
F3B F1B C14 F2B -122.6(11) . . . . ?
F3B F1B C14 C11 108.8(12) . . . . ?
C12 C11 C14 F1A 101.8(15) . . . . ?
C10 C11 C14 F1A -78.3(15) . . . . ?
C12 C11 C14 F2B 43.6(16) . . . . ?
C10 C11 C14 F2B -136.5(13) . . . . ?
C12 C11 C14 F3A -61.4(13) . . . . ?
C10 C11 C14 F3A 118.5(12) . . . . ?
C12 C11 C14 F3B -104.9(15) . . . . ?
C10 C11 C14 F3B 75.1(15) . . . . ?
C12 C11 C14 F1B 170.7(16) . . . . ?
C10 C11 C14 F1B -9.4(18) . . . . ?
C12 C11 C14 F2A 0.7(11) . . . . ?
C10 C11 C14 F2A -179.4(8) . . . . ?
F3A F2A C14 F1A 137.7(10) . . . . ?
F3A F2A C14 C11 -105.0(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.86 2.18 3.003(6) 159.9 3_667
N1 H1A N2 0.86 2.18 3.003(6) 159.9 3_667
N1 H1A N2 0.86 2.18 3.003(6) 159.9 3_667
N1 H1A N2 0.86 2.18 3.003(6) 159.9 3_667
N1 H1A N2 0.86 2.18 3.003(6) 159.9 3_667
N1 H1A N2 0.86 2.18 3.003(6) 159.9 3_667
N1 H1A N2 0.86 2.18 3.003(6) 159.9 3_667
C7 H7 F3B 0.93 2.64 3.374(10) 136.6 1_556

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2092484'
loop_
_audit_author_name
_audit_author_address
'Jie Zhou'
;Yun University
China
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H8 F6 N2 S'
_chemical_formula_weight         362.29

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.5804(3)
_cell_length_b                   9.4893(4)
_cell_length_c                   10.4129(4)
_cell_angle_alpha                102.4300(10)
_cell_angle_beta                 109.290(2)
_cell_angle_gamma                107.080(2)
_cell_volume                     717.67(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      4.7959
_cell_measurement_theta_max      68.5712

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            PINK
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.691
_shelx_estimated_absorpt_T_min   0.480
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_T_max  0.650
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   sadabs
_diffrn_measurement_device_type  'Bruker APEX-III D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16178
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.796
_diffrn_reflns_theta_max         68.565
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2621
_reflns_number_gt                2282
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 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)+(0.1375P)²+0.9384P] 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         2621
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2403
_refine_ls_wR_factor_gt          0.2296
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
C1 C 0.4296(5) 1.2119(4) 0.3820(4) 0.0461(8) Uani 1 1 d . . . . .
H1 H 0.4692 1.3207 0.4170 0.055 Uiso 1 1 calc R U . . .
C2 C 0.4874(5) 1.1393(4) 0.2878(4) 0.0450(8) Uani 1 1 d . . . . .
C3 C 0.4288(5) 0.9774(4) 0.2362(4) 0.0436(8) Uani 1 1 d . . . . .
H3 H 0.4700 0.9313 0.1733 0.052 Uiso 1 1 calc R U . . .
C4 C 0.3094(5) 0.8818(4) 0.2762(4) 0.0411(8) Uani 1 1 d . . . . .
C5 C 0.2518(5) 0.9555(4) 0.3704(4) 0.0439(8) Uani 1 1 d . . . . .
H5 H 0.1719 0.8951 0.3991 0.053 Uiso 1 1 calc R U . . .
C6 C 0.3113(5) 1.1183(4) 0.4227(4) 0.0456(8) Uani 1 1 d . . . . .
C7 C 0.2471(6) 1.1937(5) 0.5247(5) 0.0541(10) Uani 1 1 d . . . . .
C8 C 0.6209(6) 1.2377(5) 0.2470(5) 0.0540(10) Uani 1 1 d . . . . .
C9 C 0.2507(5) 0.7070(4) 0.2214(4) 0.0410(8) Uani 1 1 d . . . . .
C10 C 0.2750(5) 0.6343(4) 0.1029(4) 0.0454(8) Uani 1 1 d . . . . .
H10 H 0.3234 0.6931 0.0542 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2262(5) 0.4726(4) 0.0581(4) 0.0428(8) Uani 1 1 d . . . . .
C12 C 0.1480(5) 0.3794(4) 0.1258(4) 0.0431(8) Uani 1 1 d . . . . .
C13 C 0.1240(6) 0.4531(5) 0.2434(4) 0.0507(9) Uani 1 1 d . . . . .
H13 H 0.0740 0.3944 0.2914 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1744(5) 0.6137(4) 0.2894(4) 0.0474(9) Uani 1 1 d . . . . .
H14 H 0.1570 0.6616 0.3684 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1486(5) 0.1905(4) -0.0412(4) 0.0455(8) Uani 1 1 d . . . . .
F1 F 0.6277(10) 1.1655(4) 0.1322(6) 0.180(3) Uani 1 1 d . . . . .
F2 F 0.7769(5) 1.2929(10) 0.3419(6) 0.227(4) Uani 1 1 d . . . . .
F3 F 0.5903(8) 1.3536(5) 0.2195(7) 0.151(2) Uani 1 1 d . . . . .
F4 F 0.3435(5) 1.3441(4) 0.5935(4) 0.1052(13) Uani 1 1 d . . . . .
F5 F 0.0783(4) 1.1779(5) 0.4572(4) 0.0941(11) Uani 1 1 d . . . . .
F6 F 0.2478(5) 1.1300(4) 0.6267(3) 0.0892(10) Uani 1 1 d . . . . .
N1 N 0.1045(4) 0.2195(4) 0.0673(3) 0.0473(7) Uani 1 1 d . . . . .
N2 N 0.1274(5) 0.0476(4) -0.1161(4) 0.0589(9) Uani 1 1 d . . . . .
H2A H 0.0823 -0.0321 -0.0938 0.071 Uiso 1 1 calc R U . . .
H2B H 0.1590 0.0353 -0.1867 0.071 Uiso 1 1 calc R U . . .
S1 S 0.24578(14) 0.35421(10) -0.08407(10) 0.0526(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(5) . ?
C1 C6 1.384(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(5) . ?
C2 C8 1.493(5) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(5) . ?
C4 C9 1.497(5) . ?
C5 C6 1.391(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(5) . ?
C7 F4 1.307(5) . ?
C7 F6 1.329(5) . ?
C7 F5 1.330(5) . ?
C8 F2 1.239(6) . ?
C8 F3 1.271(6) . ?
C8 F1 1.272(5) . ?
C9 C10 1.389(5) . ?
C9 C14 1.397(5) . ?
C10 C11 1.391(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.400(5) . ?
C11 S1 1.743(4) . ?
C12 N1 1.390(5) . ?
C12 C13 1.383(5) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N1 1.306(5) . ?
C15 N2 1.337(5) . ?
C15 S1 1.758(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.3(3) . . ?
C2 C1 H1 120.9 . . ?
C6 C1 H1 120.9 . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 C8 119.4(3) . . ?
C3 C2 C8 119.8(3) . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 C9 122.1(3) . . ?
C3 C4 C9 120.6(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 121.0(3) . . ?
C1 C6 C7 119.4(3) . . ?
C5 C6 C7 119.6(3) . . ?
F4 C7 F6 106.0(4) . . ?
F4 C7 F5 106.6(4) . . ?
F6 C7 F5 105.4(4) . . ?
F4 C7 C6 113.7(4) . . ?
F6 C7 C6 112.5(3) . . ?
F5 C7 C6 112.1(3) . . ?
F2 C8 F3 106.2(6) . . ?
F2 C8 F1 105.1(6) . . ?
F3 C8 F1 102.7(5) . . ?
F2 C8 C2 113.0(4) . . ?
F3 C8 C2 114.3(4) . . ?
F1 C8 C2 114.5(4) . . ?
C10 C9 C14 118.4(3) . . ?
C10 C9 C4 120.4(3) . . ?
C14 C9 C4 121.1(3) . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 122.1(3) . . ?
C10 C11 S1 128.3(3) . . ?
C12 C11 S1 109.6(3) . . ?
N1 C12 C13 126.5(3) . . ?
N1 C12 C11 115.3(3) . . ?
C13 C12 C11 118.2(3) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 122.2(3) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
N1 C15 N2 124.0(3) . . ?
N1 C15 S1 116.0(3) . . ?
N2 C15 S1 120.0(3) . . ?
C15 N1 C12 110.5(3) . . ?
C15 N2 H2A 120.0 . . ?
C15 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 S1 C15 88.60(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.2(6) . . . . ?
C6 C1 C2 C8 -177.5(4) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C8 C2 C3 C4 177.6(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 C9 -178.7(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C9 C4 C5 C6 178.5(3) . . . . ?
C2 C1 C6 C5 -0.1(6) . . . . ?
C2 C1 C6 C7 179.8(4) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C1 C6 C7 F4 -15.8(6) . . . . ?
C5 C6 C7 F4 164.0(4) . . . . ?
C1 C6 C7 F6 -136.3(4) . . . . ?
C5 C6 C7 F6 43.6(5) . . . . ?
C1 C6 C7 F5 105.2(4) . . . . ?
C5 C6 C7 F5 -75.0(5) . . . . ?
C1 C2 C8 F2 78.7(7) . . . . ?
C3 C2 C8 F2 -98.6(7) . . . . ?
C1 C2 C8 F3 -42.9(6) . . . . ?
C3 C2 C8 F3 139.8(5) . . . . ?
C1 C2 C8 F1 -161.0(5) . . . . ?
C3 C2 C8 F1 21.7(7) . . . . ?
C5 C4 C9 C10 164.8(3) . . . . ?
C3 C4 C9 C10 -16.7(5) . . . . ?
C5 C4 C9 C14 -16.7(6) . . . . ?
C3 C4 C9 C14 161.8(4) . . . . ?
C14 C9 C10 C11 -1.3(6) . . . . ?
C4 C9 C10 C11 177.3(3) . . . . ?
C9 C10 C11 C12 2.0(6) . . . . ?
C9 C10 C11 S1 -178.9(3) . . . . ?
C10 C11 C12 N1 179.2(3) . . . . ?
S1 C11 C12 N1 -0.1(4) . . . . ?
C10 C11 C12 C13 -1.8(6) . . . . ?
S1 C11 C12 C13 178.9(3) . . . . ?
N1 C12 C13 C14 179.8(4) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C12 C13 C14 C9 -0.3(6) . . . . ?
C10 C9 C14 C13 0.4(6) . . . . ?
C4 C9 C14 C13 -178.1(4) . . . . ?
N2 C15 N1 C12 178.1(4) . . . . ?
S1 C15 N1 C12 -0.5(4) . . . . ?
C13 C12 N1 C15 -178.6(4) . . . . ?
C11 C12 N1 C15 0.3(5) . . . . ?
C10 C11 S1 C15 -179.3(4) . . . . ?
C12 C11 S1 C15 -0.2(3) . . . . ?
N1 C15 S1 C11 0.4(3) . . . . ?
N2 C15 S1 C11 -178.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B F6 0.86 2.55 3.333(5) 152.1 1_544
N2 H2A N1 0.86 2.15 2.984(5) 162.3 2
N2 H2A N1 0.86 2.15 2.984(5) 162.3 2
N2 H2B F6 0.86 2.55 3.333(5) 152.1 1_544

_refine_diff_density_max         1.066
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.076



####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2259073'
loop_
_audit_author_name
_audit_author_address
'Yu-Qiang Zhao'
;Yunnan University 
China
;
_audit_update_record             
;
2023-04-26 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Br2 N4 S2'
_chemical_formula_weight         458.20

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'
Br Br -0.2901 2.4595 '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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.2218(7)
_cell_length_b                   4.0384(2)
_cell_length_c                   22.4366(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1560.43(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    9072
_cell_measurement_theta_min      2.9822
_cell_measurement_theta_max      28.3421

_exptl_crystal_description       slice
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    5.462
_shelx_estimated_absorpt_T_min   0.342
_shelx_estimated_absorpt_T_max   0.408
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.266
_exptl_absorpt_correction_T_max  0.336
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            30330
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.365
_diffrn_reflns_theta_max         28.361
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3714
_reflns_number_gt                3190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.936
_reflns_Friedel_fraction_full    0.993

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 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)+(0.1000P)²+0.2560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0097(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.161(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3714
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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
N1 N 0.5463(4) 0.492(2) 0.4490(4) 0.0382(16) Uani 1 1 d . . . . .
N2 N 0.6652(5) 0.242(3) 0.4319(4) 0.052(3) Uani 1 1 d . . . . .
H2A H 0.6809 0.2878 0.4674 0.062 Uiso 1 1 calc R U . . .
H2B H 0.6951 0.1373 0.4077 0.062 Uiso 1 1 calc R U . . .
N3 N 0.7095(4) 0.5041(19) 0.5523(3) 0.0366(18) Uani 1 1 d . . . . .
N4 N 0.5888(5) 0.752(2) 0.5677(4) 0.049(2) Uani 1 1 d . . . . .
H4A H 0.5721 0.6921 0.5332 0.059 Uiso 1 1 calc R U . . .
H4B H 0.5593 0.8627 0.5913 0.059 Uiso 1 1 calc R U . . .
S1 S 0.56110(14) 0.2387(7) 0.34234(12) 0.0409(6) Uani 1 1 d . . . . .
S2 S 0.69473(13) 0.7745(6) 0.65695(12) 0.0392(6) Uani 1 1 d . . . . .
Br1 Br 0.25580(6) 0.7195(2) 0.30342(5) 0.0510(4) Uani 1 1 d . . . . .
Br2 Br 1.00186(5) 0.3283(3) 0.69764(6) 0.0503(3) Uani 1 1 d . . . . .
C1 C 0.5947(5) 0.333(3) 0.4146(4) 0.040(2) Uani 1 1 d . . . . .
C2 C 0.4776(5) 0.554(2) 0.4177(4) 0.0343(18) Uani 1 1 d . . . . .
C3 C 0.4741(5) 0.433(2) 0.3595(4) 0.0341(19) Uani 1 1 d . . . . .
C4 C 0.4077(5) 0.475(2) 0.3246(3) 0.0331(17) Uani 1 1 d . . . . .
H4 H 0.4050 0.3918 0.2860 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3465(5) 0.644(2) 0.3496(4) 0.038(2) Uani 1 1 d . . . . .
C6 C 0.3492(6) 0.767(2) 0.4072(5) 0.041(2) Uani 1 1 d . . . . .
H6 H 0.3068 0.8803 0.4228 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4155(6) 0.721(3) 0.4416(4) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.4178 0.8026 0.4803 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6619(5) 0.670(3) 0.5850(4) 0.040(2) Uani 1 1 d . . . . .
C9 C 0.7792(5) 0.452(2) 0.5822(4) 0.0343(19) Uani 1 1 d . . . . .
C10 C 0.7828(5) 0.587(2) 0.6401(4) 0.0318(17) Uani 1 1 d . . . . .
C11 C 0.8482(5) 0.558(2) 0.6754(4) 0.037(2) Uani 1 1 d . . . . .
H11 H 0.8507 0.6486 0.7134 0.045 Uiso 1 1 calc R U . . .
C12 C 0.9103(5) 0.383(2) 0.6507(4) 0.0359(19) Uani 1 1 d . . . . .
C13 C 0.9090(6) 0.252(2) 0.5943(5) 0.040(2) Uani 1 1 d . . . . .
H13 H 0.9524 0.1433 0.5792 0.048 Uiso 1 1 calc R U . . .
C14 C 0.8434(5) 0.281(2) 0.5603(4) 0.038(2) Uani 1 1 d . . . . .
H14 H 0.8417 0.1864 0.5226 0.045 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 1.306(12) . ?
N1 C2 1.399(11) . ?
N2 C1 1.326(14) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 C8 1.287(12) . ?
N3 C9 1.391(10) . ?
N4 C8 1.357(13) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
S1 C3 1.735(9) . ?
S1 C1 1.763(10) . ?
S2 C10 1.736(9) . ?
S2 C8 1.763(10) . ?
Br1 C5 1.899(9) . ?
Br2 C12 1.909(9) . ?
C2 C7 1.372(13) . ?
C2 C3 1.396(12) . ?
C3 C4 1.396(12) . ?
C4 C5 1.376(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(15) . ?
C6 C7 1.391(15) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C14 1.392(13) . ?
C9 C10 1.410(11) . ?
C10 C11 1.383(12) . ?
C11 C12 1.395(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(14) . ?
C13 C14 1.367(14) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 109.3(8) . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C8 N3 C9 110.8(7) . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C3 S1 C1 89.0(5) . . ?
C10 S2 C8 88.6(4) . . ?
N1 C1 N2 123.2(9) . . ?
N1 C1 S1 116.1(7) . . ?
N2 C1 S1 120.7(8) . . ?
C7 C2 C3 120.3(9) . . ?
C7 C2 N1 123.4(8) . . ?
C3 C2 N1 116.3(8) . . ?
C4 C3 C2 121.2(8) . . ?
C4 C3 S1 129.6(7) . . ?
C2 C3 S1 109.2(7) . . ?
C5 C4 C3 117.3(8) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C4 C5 C6 122.2(9) . . ?
C4 C5 Br1 119.2(7) . . ?
C6 C5 Br1 118.6(8) . . ?
C5 C6 C7 119.8(10) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 119.2(9) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N3 C8 N4 123.7(9) . . ?
N3 C8 S2 116.2(7) . . ?
N4 C8 S2 120.0(7) . . ?
N3 C9 C14 126.2(8) . . ?
N3 C9 C10 115.0(8) . . ?
C14 C9 C10 118.8(8) . . ?
C11 C10 C9 121.9(8) . . ?
C11 C10 S2 128.6(7) . . ?
C9 C10 S2 109.4(6) . . ?
C10 C11 C12 116.2(8) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
C13 C12 C11 123.2(8) . . ?
C13 C12 Br2 118.6(7) . . ?
C11 C12 Br2 118.2(7) . . ?
C14 C13 C12 119.6(9) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C9 120.2(9) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 179.5(10) . . . . ?
C2 N1 C1 S1 -0.9(11) . . . . ?
C3 S1 C1 N1 0.4(9) . . . . ?
C3 S1 C1 N2 179.9(9) . . . . ?
C1 N1 C2 C7 -179.3(9) . . . . ?
C1 N1 C2 C3 1.2(12) . . . . ?
C7 C2 C3 C4 -0.8(14) . . . . ?
N1 C2 C3 C4 178.7(8) . . . . ?
C7 C2 C3 S1 179.5(8) . . . . ?
N1 C2 C3 S1 -1.0(11) . . . . ?
C1 S1 C3 C4 -179.3(9) . . . . ?
C1 S1 C3 C2 0.3(7) . . . . ?
C2 C3 C4 C5 0.9(13) . . . . ?
S1 C3 C4 C5 -179.4(7) . . . . ?
C3 C4 C5 C6 -0.6(14) . . . . ?
C3 C4 C5 Br1 178.2(6) . . . . ?
C4 C5 C6 C7 0.0(15) . . . . ?
Br1 C5 C6 C7 -178.7(7) . . . . ?
C3 C2 C7 C6 0.2(14) . . . . ?
N1 C2 C7 C6 -179.3(9) . . . . ?
C5 C6 C7 C2 0.1(15) . . . . ?
C9 N3 C8 N4 -178.7(9) . . . . ?
C9 N3 C8 S2 -1.6(11) . . . . ?
C10 S2 C8 N3 2.1(9) . . . . ?
C10 S2 C8 N4 179.3(9) . . . . ?
C8 N3 C9 C14 179.6(9) . . . . ?
C8 N3 C9 C10 0.1(11) . . . . ?
N3 C9 C10 C11 -179.7(8) . . . . ?
C14 C9 C10 C11 0.7(13) . . . . ?
N3 C9 C10 S2 1.4(10) . . . . ?
C14 C9 C10 S2 -178.1(7) . . . . ?
C8 S2 C10 C11 179.4(9) . . . . ?
C8 S2 C10 C9 -1.8(7) . . . . ?
C9 C10 C11 C12 -0.7(13) . . . . ?
S2 C10 C11 C12 178.0(7) . . . . ?
C10 C11 C12 C13 1.3(14) . . . . ?
C10 C11 C12 Br2 -179.1(6) . . . . ?
C11 C12 C13 C14 -2.0(15) . . . . ?
Br2 C12 C13 C14 178.4(7) . . . . ?
C12 C13 C14 C9 2.0(15) . . . . ?
N3 C9 C14 C13 179.2(9) . . . . ?
C10 C9 C14 C13 -1.4(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 Br1 0.93 3.11 3.566(9) 112.4 2_665
C4 H4 Br2 0.93 3.10 3.546(8) 111.4 3_654
N4 H4B Br2 0.86 2.87 3.691(9) 160.4 4_465
N4 H4A N1 0.86 2.10 2.954(12) 170.7 .
N2 H2B Br1 0.86 2.94 3.771(9) 163.0 4
N2 H2A N3 0.86 2.15 3.000(11) 167.8 .
N2 H2A N3 0.86 2.15 3.000(11) 167.8 .
N2 H2B Br1 0.86 2.94 3.771(9) 163.0 4
N4 H4A N1 0.86 2.10 2.954(12) 170.7 .
N4 H4B Br2 0.86 2.87 3.691(9) 160.4 4_465
C4 H4 Br2 0.93 3.10 3.546(8) 111.4 3_654
C11 H11 Br1 0.93 3.11 3.566(9) 112.4 2_665
N2 H2A N3 0.86 2.15 3.000(11) 167.8 .
N2 H2B Br1 0.86 2.94 3.771(9) 163.0 4
N4 H4A N1 0.86 2.10 2.954(12) 170.7 .
N4 H4B Br2 0.86 2.87 3.691(9) 160.4 4_465
C4 H4 Br2 0.93 3.10 3.546(8) 111.4 3_654
C11 H11 Br1 0.93 3.11 3.566(9) 112.4 2_665

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.122

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2108890'
loop_
_audit_author_name
_audit_author_address
'jie zhou'
;Yunnan University
China
;
_audit_update_record             
;
2021-09-09 deposited with the CCDC.	2023-06-09 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         ?
_chemical_formula_sum            'C25 H17 N3 S'
_chemical_formula_weight         391.47

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.7111(3)
_cell_length_b                   8.8354(3)
_cell_length_c                   21.0030(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.7500(10)
_cell_angle_gamma                90
_cell_volume                     1946.01(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.5090
_cell_measurement_theta_max      28.2788

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            24916
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.992
_diffrn_reflns_theta_max         25.147
_diffrn_reflns_theta_full        25.147
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3475
_reflns_number_gt                2595
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_publication_material  'SHELXT 2014/5 (Sheldrick, 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)+(0.0589P)²+0.6799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3475
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.34271(6) 0.06155(8) 0.08893(4) 0.0574(2) Uani 1 1 d . . . . .
N1 N 0.1499(2) -0.1195(2) 0.03207(11) 0.0578(6) Uani 1 1 d . . . . .
H1A H 0.071881 -0.139285 0.014504 0.069 Uiso 1 1 calc R U . . .
H1B H 0.206571 -0.189697 0.036082 0.069 Uiso 1 1 calc R U . . .
N2 N 0.62296(17) 0.9206(2) 0.30394(9) 0.0478(5) Uani 1 1 d . . . . .
N3 N 0.10372(16) 0.1336(2) 0.04903(9) 0.0417(5) Uani 1 1 d . . . . .
C1 C 0.1832(2) 0.0207(3) 0.05317(11) 0.0452(6) Uani 1 1 d . . . . .
C2 C 0.2977(2) 0.2483(3) 0.09929(11) 0.0420(5) Uani 1 1 d . . . . .
C3 C 0.3712(2) 0.3673(3) 0.12820(11) 0.0437(5) Uani 1 1 d . . . . .
H15 H 0.458114 0.354295 0.144116 0.052 Uiso 1 1 calc R U . . .
C4 C 0.3143(2) 0.5071(3) 0.13339(10) 0.0396(5) Uani 1 1 d . . . . .
C5 C 0.3907(2) 0.6301(3) 0.17072(11) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.3391(2) 0.7204(3) 0.21285(12) 0.0483(6) Uani 1 1 d . . . . .
H14 H 0.252395 0.714052 0.212741 0.058 Uiso 1 1 calc R U . . .
C7 C 0.4138(2) 0.8190(3) 0.25471(12) 0.0499(6) Uani 1 1 d . . . . .
H13 H 0.377539 0.877692 0.282924 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5425(2) 0.8315(3) 0.25514(11) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.6009(2) 1.0704(3) 0.31886(11) 0.0435(6) Uani 1 1 d . . . . .
C10 C 0.5233(2) 1.1765(3) 0.28209(13) 0.0547(6) Uani 1 1 d . . . . .
H12 H 0.474628 1.152187 0.241456 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5205(3) 1.3200(3) 0.30778(15) 0.0637(7) Uani 1 1 d . . . . .
H11 H 0.469245 1.393989 0.284060 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5936(3) 1.3556(3) 0.36886(16) 0.0677(8) Uani 1 1 d . . . . .
H1 H 0.588723 1.452418 0.385597 0.081 Uiso 1 1 calc R U . . .
C13 C 0.1659(2) 0.2635(2) 0.07492(10) 0.0381(5) Uani 1 1 d . . . . .
C14 C 0.1838(2) 0.5235(3) 0.10783(10) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.145632 0.617070 0.110762 0.048 Uiso 1 1 calc R U . . .
C15 C 0.1102(2) 0.4050(3) 0.07838(10) 0.0409(5) Uani 1 1 d . . . . .
H2 H 0.023982 0.419358 0.060971 0.049 Uiso 1 1 calc R U . . .
C16 C 0.5943(2) 0.7501(3) 0.21108(13) 0.0548(7) Uani 1 1 d . . . . .
H4 H 0.679663 0.762421 0.209139 0.066 Uiso 1 1 calc R U . . .
C17 C 0.5189(2) 0.6499(3) 0.16979(12) 0.0537(7) Uani 1 1 d . . . . .
H5 H 0.554855 0.594211 0.140538 0.064 Uiso 1 1 calc R U . . .
C18 C 0.6720(3) 1.2510(3) 0.40448(13) 0.0609(8) Uani 1 1 d . . . . .
H6 H 0.721622 1.277152 0.444638 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6771(2) 1.1048(3) 0.38025(11) 0.0477(6) Uani 1 1 d . . . . .
C20 C 0.7464(2) 0.9699(3) 0.40370(11) 0.0488(6) Uani 1 1 d . . . . .
C21 C 0.7106(2) 0.8583(3) 0.35565(12) 0.0469(6) Uani 1 1 d . . . . .
C22 C 0.7590(2) 0.7127(3) 0.36341(14) 0.0595(7) Uani 1 1 d . . . . .
H7 H 0.734352 0.639158 0.331650 0.071 Uiso 1 1 calc R U . . .
C23 C 0.8454(3) 0.6808(4) 0.42009(16) 0.0715(8) Uani 1 1 d . . . . .
H8 H 0.879133 0.583746 0.426487 0.086 Uiso 1 1 calc R U . . .
C24 C 0.8833(3) 0.7891(4) 0.46773(15) 0.0730(9) Uani 1 1 d . . . . .
H10 H 0.942766 0.764213 0.505017 0.088 Uiso 1 1 calc R U . . .
C25 C 0.8337(2) 0.9336(4) 0.46047(13) 0.0616(8) Uani 1 1 d . . . . .
H9 H 0.858023 1.005594 0.492903 0.074 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
S1 C2 1.745(2) . ?
S1 C1 1.758(2) . ?
N1 C1 1.339(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C9 1.392(3) . ?
N2 C21 1.396(3) . ?
N2 C8 1.433(3) . ?
N3 C1 1.302(3) . ?
N3 C13 1.382(3) . ?
C2 C3 1.378(3) . ?
C2 C13 1.406(3) . ?
C3 C4 1.391(3) . ?
C3 H15 0.9300 . ?
C4 C14 1.398(3) . ?
C4 C5 1.485(3) . ?
C5 C6 1.387(3) . ?
C5 C17 1.388(3) . ?
C6 C7 1.373(3) . ?
C6 H14 0.9300 . ?
C7 C8 1.381(3) . ?
C7 H13 0.9300 . ?
C8 C16 1.375(3) . ?
C9 C10 1.380(4) . ?
C9 C19 1.411(3) . ?
C10 C11 1.381(4) . ?
C10 H12 0.9300 . ?
C11 C12 1.396(4) . ?
C11 H11 0.9300 . ?
C12 C18 1.365(4) . ?
C12 H1 0.9300 . ?
C13 C15 1.393(3) . ?
C14 C15 1.379(3) . ?
C14 H3 0.9300 . ?
C15 H2 0.9300 . ?
C16 C17 1.379(3) . ?
C16 H4 0.9300 . ?
C17 H5 0.9300 . ?
C18 C19 1.394(4) . ?
C18 H6 0.9300 . ?
C19 C20 1.438(4) . ?
C20 C25 1.394(4) . ?
C20 C21 1.407(3) . ?
C21 C22 1.385(4) . ?
C22 C23 1.380(4) . ?
C22 H7 0.9300 . ?
C23 C24 1.384(4) . ?
C23 H8 0.9300 . ?
C24 C25 1.379(4) . ?
C24 H10 0.9300 . ?
C25 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C1 88.75(11) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 N2 C21 108.57(19) . . ?
C9 N2 C8 125.35(19) . . ?
C21 N2 C8 123.4(2) . . ?
C1 N3 C13 110.72(18) . . ?
N3 C1 N1 124.1(2) . . ?
N3 C1 S1 115.86(17) . . ?
N1 C1 S1 120.07(18) . . ?
C3 C2 C13 121.9(2) . . ?
C3 C2 S1 128.96(18) . . ?
C13 C2 S1 109.09(16) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H15 120.3 . . ?
C4 C3 H15 120.3 . . ?
C3 C4 C14 118.8(2) . . ?
C3 C4 C5 119.2(2) . . ?
C14 C4 C5 121.8(2) . . ?
C6 C5 C17 117.4(2) . . ?
C6 C5 C4 120.60(19) . . ?
C17 C5 C4 121.71(19) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H14 119.4 . . ?
C5 C6 H14 119.4 . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H13 119.8 . . ?
C8 C7 H13 119.8 . . ?
C16 C8 C7 119.5(2) . . ?
C16 C8 N2 120.2(2) . . ?
C7 C8 N2 120.2(2) . . ?
C10 C9 N2 129.1(2) . . ?
C10 C9 C19 122.4(2) . . ?
N2 C9 C19 108.5(2) . . ?
C9 C10 C11 117.6(3) . . ?
C9 C10 H12 121.2 . . ?
C11 C10 H12 121.2 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C18 C12 C11 121.2(3) . . ?
C18 C12 H1 119.4 . . ?
C11 C12 H1 119.4 . . ?
N3 C13 C15 126.02(19) . . ?
N3 C13 C2 115.57(19) . . ?
C15 C13 C2 118.4(2) . . ?
C15 C14 C4 121.9(2) . . ?
C15 C14 H3 119.0 . . ?
C4 C14 H3 119.0 . . ?
C14 C15 C13 119.5(2) . . ?
C14 C15 H2 120.3 . . ?
C13 C15 H2 120.3 . . ?
C8 C16 C17 119.6(2) . . ?
C8 C16 H4 120.2 . . ?
C17 C16 H4 120.2 . . ?
C16 C17 C5 121.8(2) . . ?
C16 C17 H5 119.1 . . ?
C5 C17 H5 119.1 . . ?
C12 C18 C19 119.5(3) . . ?
C12 C18 H6 120.2 . . ?
C19 C18 H6 120.2 . . ?
C18 C19 C9 118.3(3) . . ?
C18 C19 C20 134.4(2) . . ?
C9 C19 C20 107.3(2) . . ?
C25 C20 C21 119.3(3) . . ?
C25 C20 C19 133.9(3) . . ?
C21 C20 C19 106.8(2) . . ?
C22 C21 N2 129.4(2) . . ?
C22 C21 C20 121.7(2) . . ?
N2 C21 C20 108.9(2) . . ?
C23 C22 C21 117.4(3) . . ?
C23 C22 H7 121.3 . . ?
C21 C22 H7 121.3 . . ?
C22 C23 C24 121.9(3) . . ?
C22 C23 H8 119.0 . . ?
C24 C23 H8 119.0 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H10 119.7 . . ?
C23 C24 H10 119.7 . . ?
C24 C25 C20 118.9(3) . . ?
C24 C25 H9 120.5 . . ?
C20 C25 H9 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N3 C1 N1 179.9(2) . . . . ?
C13 N3 C1 S1 -0.2(2) . . . . ?
C2 S1 C1 N3 0.06(19) . . . . ?
C2 S1 C1 N1 179.9(2) . . . . ?
C1 S1 C2 C3 177.7(2) . . . . ?
C1 S1 C2 C13 0.11(17) . . . . ?
C13 C2 C3 C4 -0.3(3) . . . . ?
S1 C2 C3 C4 -177.64(18) . . . . ?
C2 C3 C4 C14 -1.2(3) . . . . ?
C2 C3 C4 C5 173.5(2) . . . . ?
C3 C4 C5 C6 -137.1(2) . . . . ?
C14 C4 C5 C6 37.5(3) . . . . ?
C3 C4 C5 C17 36.7(3) . . . . ?
C14 C4 C5 C17 -148.7(2) . . . . ?
C17 C5 C6 C7 -3.8(4) . . . . ?
C4 C5 C6 C7 170.2(2) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 C16 3.2(4) . . . . ?
C6 C7 C8 N2 -172.6(2) . . . . ?
C9 N2 C8 C16 131.7(3) . . . . ?
C21 N2 C8 C16 -69.0(3) . . . . ?
C9 N2 C8 C7 -52.5(3) . . . . ?
C21 N2 C8 C7 106.8(3) . . . . ?
C21 N2 C9 C10 178.9(2) . . . . ?
C8 N2 C9 C10 -19.1(4) . . . . ?
C21 N2 C9 C19 1.1(2) . . . . ?
C8 N2 C9 C19 163.0(2) . . . . ?
N2 C9 C10 C11 -178.5(2) . . . . ?
C19 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C18 1.4(4) . . . . ?
C1 N3 C13 C15 179.9(2) . . . . ?
C1 N3 C13 C2 0.3(3) . . . . ?
C3 C2 C13 N3 -178.1(2) . . . . ?
S1 C2 C13 N3 -0.3(2) . . . . ?
C3 C2 C13 C15 2.3(3) . . . . ?
S1 C2 C13 C15 -179.89(17) . . . . ?
C3 C4 C14 C15 0.7(3) . . . . ?
C5 C4 C14 C15 -173.9(2) . . . . ?
C4 C14 C15 C13 1.3(3) . . . . ?
N3 C13 C15 C14 177.7(2) . . . . ?
C2 C13 C15 C14 -2.7(3) . . . . ?
C7 C8 C16 C17 -4.0(4) . . . . ?
N2 C8 C16 C17 171.8(2) . . . . ?
C8 C16 C17 C5 0.9(4) . . . . ?
C6 C5 C17 C16 3.0(4) . . . . ?
C4 C5 C17 C16 -170.9(2) . . . . ?
C11 C12 C18 C19 -1.6(4) . . . . ?
C12 C18 C19 C9 0.5(3) . . . . ?
C12 C18 C19 C20 -180.0(2) . . . . ?
C10 C9 C19 C18 0.8(3) . . . . ?
N2 C9 C19 C18 178.8(2) . . . . ?
C10 C9 C19 C20 -178.9(2) . . . . ?
N2 C9 C19 C20 -0.9(2) . . . . ?
C18 C19 C20 C25 1.3(4) . . . . ?
C9 C19 C20 C25 -179.1(2) . . . . ?
C18 C19 C20 C21 -179.2(2) . . . . ?
C9 C19 C20 C21 0.3(2) . . . . ?
C9 N2 C21 C22 178.5(2) . . . . ?
C8 N2 C21 C22 16.1(4) . . . . ?
C9 N2 C21 C20 -0.9(2) . . . . ?
C8 N2 C21 C20 -163.25(19) . . . . ?
C25 C20 C21 C22 0.5(3) . . . . ?
C19 C20 C21 C22 -179.1(2) . . . . ?
C25 C20 C21 N2 179.9(2) . . . . ?
C19 C20 C21 N2 0.4(2) . . . . ?
N2 C21 C22 C23 -179.9(2) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 C25 1.1(4) . . . . ?
C23 C24 C25 C20 -1.2(4) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
C19 C20 C25 C24 179.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A N3 0.86 2.07 2.900(3) 161.1 3 yes
N1 H1A N3 0.86 2.07 2.900(3) 161.1 3 yes
N1 H1A N3 0.86 2.07 2.900(3) 161.1 3 yes

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.305
_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_1_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2098590'
loop_
_audit_author_name
_audit_author_address
'Jie Zhou'
;Yun University
China
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2023-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N3 S'
_chemical_formula_weight         393.49

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                   17.3606(13)
_cell_length_b                   10.3859(7)
_cell_length_c                   11.4467(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.743(3)
_cell_angle_gamma                90
_cell_volume                     2045.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2809
_cell_measurement_theta_min      2.2906
_cell_measurement_theta_max      26.4358

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            33908
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_av_R_equivalents  0.1287
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         25.149
_diffrn_reflns_theta_full        25.149
_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             3657
_reflns_number_gt                2367
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 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)+6.1872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3657
_refine_ls_number_parameters     270
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.1001
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1525
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_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 0.46943(9) 0.70565(14) 0.27126(13) 0.0554(4) Uani 1 1 d . . . . .
N1 N 0.1722(3) 0.4240(4) 0.8358(4) 0.0502(12) Uani 1 1 d . . . . .
N2 N 0.5149(3) 0.6703(5) 0.0571(5) 0.0603(14) Uani 1 1 d D . . . .
N3 N 0.4450(3) 0.5051(4) 0.1327(3) 0.0472(11) Uani 1 1 d . . . . .
C1 C 0.2217(4) 0.7229(8) 1.0802(7) 0.083(2) Uani 1 1 d . . . . .
H1 H 0.2337 0.7895 1.1339 0.099 Uiso 1 1 calc R U . . .
C2 C 0.1977(4) 0.7493(6) 0.9646(7) 0.084(2) Uani 1 1 d . . . . .
H12 H 0.1935 0.8343 0.9392 0.100 Uiso 1 1 calc R U . . .
C3 C 0.1798(4) 0.6515(5) 0.8855(5) 0.0634(17) Uani 1 1 d . . . . .
H9 H 0.1626 0.6706 0.8070 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1871(3) 0.5248(5) 0.9214(5) 0.0490(14) Uani 1 1 d . . . . .
C5 C 0.2144(3) 0.4297(4) 0.7373(4) 0.0408(12) Uani 1 1 d . . . . .
C6 C 0.1796(3) 0.3991(5) 0.6240(4) 0.0465(13) Uani 1 1 d . . . . .
H15 H 0.1277 0.3737 0.6111 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2223(3) 0.4065(5) 0.5305(4) 0.0485(14) Uani 1 1 d . . . . .
H16 H 0.1987 0.3842 0.4555 0.058 Uiso 1 1 calc R U . . .
C8 C 0.2994(3) 0.4462(5) 0.5455(4) 0.0418(12) Uani 1 1 d . . . . .
C9 C 0.3404(3) 0.4579(5) 0.4398(4) 0.0447(13) Uani 1 1 d . . . . .
C10 C 0.3839(3) 0.5670(5) 0.4220(4) 0.0466(13) Uani 1 1 d . . . . .
H3 H 0.3908 0.6319 0.4784 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4166(3) 0.5770(5) 0.3188(4) 0.0438(13) Uani 1 1 d . . . . .
C12 C 0.4775(3) 0.6176(5) 0.1418(4) 0.0490(14) Uani 1 1 d . . . . .
C13 C 0.4092(3) 0.4811(5) 0.2325(4) 0.0437(13) Uani 1 1 d . . . . .
C14 C 0.3656(3) 0.3723(5) 0.2499(5) 0.0501(14) Uani 1 1 d . . . . .
H2 H 0.3592 0.3071 0.1938 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3316(3) 0.3627(5) 0.3529(4) 0.0488(14) Uani 1 1 d . . . . .
H17 H 0.3019 0.2904 0.3642 0.059 Uiso 1 1 calc R U . . .
C16 C 0.1103(3) 0.3375(5) 0.8424(4) 0.0466(13) Uani 1 1 d . . . . .
C17 C 0.0538(3) 0.3659(6) 0.9133(5) 0.0668(17) Uani 1 1 d . . . . .
H8 H 0.0550 0.4445 0.9524 0.080 Uiso 1 1 calc R U . . .
C18 C -0.0039(4) 0.2788(9) 0.9260(7) 0.095(3) Uani 1 1 d . . . . .
H7 H -0.0414 0.2998 0.9738 0.114 Uiso 1 1 calc R U . . .
C19 C -0.0079(5) 0.1624(8) 0.8706(8) 0.099(3) Uani 1 1 d . . . . .
H4 H -0.0471 0.1040 0.8807 0.119 Uiso 1 1 calc R U . . .
C20 C 0.0479(4) 0.1334(7) 0.7988(6) 0.078(2) Uani 1 1 d . . . . .
H6 H 0.0454 0.0550 0.7592 0.093 Uiso 1 1 calc R U . . .
C21 C 0.1072(3) 0.2187(6) 0.7850(5) 0.0593(16) Uani 1 1 d . . . . .
H5 H 0.1449 0.1970 0.7377 0.071 Uiso 1 1 calc R U . . .
C22 C 0.2280(4) 0.5966(8) 1.1172(6) 0.079(2) Uani 1 1 d . . . . .
H10 H 0.2435 0.5784 1.1964 0.095 Uiso 1 1 calc R U . . .
C23 C 0.2115(3) 0.4958(6) 1.0377(5) 0.0660(17) Uani 1 1 d . . . . .
H11 H 0.2170 0.4107 1.0626 0.079 Uiso 1 1 calc R U . . .
C24 C 0.2919(3) 0.4692(5) 0.7529(4) 0.0447(13) Uani 1 1 d . . . . .
H13 H 0.3162 0.4894 0.8281 0.054 Uiso 1 1 calc R U . . .
C25 C 0.3329(3) 0.4784(5) 0.6577(4) 0.0453(13) Uani 1 1 d . . . . .
H14 H 0.3841 0.5070 0.6696 0.054 Uiso 1 1 calc R U . . .
H2NA H 0.543(2) 0.738(3) 0.070(4) 0.033(14) Uiso 1 1 d D . . . .
H2NB H 0.529(4) 0.622(5) 0.002(4) 0.10(3) Uiso 1 1 d 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
S1 C11 1.748(5) . ?
S1 C12 1.763(5) . ?
N1 C16 1.411(6) . ?
N1 C5 1.426(6) . ?
N1 C4 1.434(6) . ?
N2 C12 1.352(7) . ?
N2 H2NA 0.855(19) . ?
N2 H2NB 0.87(2) . ?
N3 C12 1.295(7) . ?
N3 C13 1.395(6) . ?
C1 C2 1.361(10) . ?
C1 C22 1.378(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(8) . ?
C2 H12 0.9300 . ?
C3 C4 1.379(8) . ?
C3 H9 0.9300 . ?
C4 C23 1.375(7) . ?
C5 C6 1.392(7) . ?
C5 C24 1.394(7) . ?
C6 C7 1.384(7) . ?
C6 H15 0.9300 . ?
C7 C8 1.389(7) . ?
C7 H16 0.9300 . ?
C8 C25 1.377(7) . ?
C8 C9 1.489(7) . ?
C9 C10 1.392(7) . ?
C9 C15 1.397(7) . ?
C10 C11 1.382(7) . ?
C10 H3 0.9300 . ?
C11 C13 1.397(7) . ?
C13 C14 1.390(7) . ?
C14 C15 1.391(7) . ?
C14 H2 0.9300 . ?
C15 H17 0.9300 . ?
C16 C17 1.386(7) . ?
C16 C21 1.397(7) . ?
C17 C18 1.372(9) . ?
C17 H8 0.9300 . ?
C18 C19 1.362(11) . ?
C18 H7 0.9300 . ?
C19 C20 1.385(10) . ?
C19 H4 0.9300 . ?
C20 C21 1.384(8) . ?
C20 H6 0.9300 . ?
C21 H5 0.9300 . ?
C22 C23 1.391(8) . ?
C22 H10 0.9300 . ?
C23 H11 0.9300 . ?
C24 C25 1.384(7) . ?
C24 H13 0.9300 . ?
C25 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 S1 C12 88.3(2) . . ?
C16 N1 C5 123.1(4) . . ?
C16 N1 C4 119.7(4) . . ?
C5 N1 C4 116.5(4) . . ?
C12 N2 H2NA 122(3) . . ?
C12 N2 H2NB 120(5) . . ?
H2NA N2 H2NB 113(5) . . ?
C12 N3 C13 109.4(4) . . ?
C2 C1 C22 119.4(6) . . ?
C2 C1 H1 120.3 . . ?
C22 C1 H1 120.3 . . ?
C1 C2 C3 120.4(7) . . ?
C1 C2 H12 119.8 . . ?
C3 C2 H12 119.8 . . ?
C2 C3 C4 120.5(6) . . ?
C2 C3 H9 119.7 . . ?
C4 C3 H9 119.7 . . ?
C23 C4 C3 120.1(5) . . ?
C23 C4 N1 120.4(5) . . ?
C3 C4 N1 119.5(5) . . ?
C6 C5 C24 118.5(5) . . ?
C6 C5 N1 121.5(5) . . ?
C24 C5 N1 120.0(4) . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H15 120.1 . . ?
C5 C6 H15 120.1 . . ?
C6 C7 C8 122.0(5) . . ?
C6 C7 H16 119.0 . . ?
C8 C7 H16 119.0 . . ?
C25 C8 C7 117.8(5) . . ?
C25 C8 C9 123.4(5) . . ?
C7 C8 C9 118.8(5) . . ?
C10 C9 C15 118.8(5) . . ?
C10 C9 C8 120.9(4) . . ?
C15 C9 C8 120.2(5) . . ?
C11 C10 C9 118.7(5) . . ?
C11 C10 H3 120.6 . . ?
C9 C10 H3 120.6 . . ?
C10 C11 C13 122.8(5) . . ?
C10 C11 S1 128.1(4) . . ?
C13 C11 S1 109.1(4) . . ?
N3 C12 N2 123.6(5) . . ?
N3 C12 S1 116.9(4) . . ?
N2 C12 S1 119.5(4) . . ?
C14 C13 N3 125.1(5) . . ?
C14 C13 C11 118.5(5) . . ?
N3 C13 C11 116.3(5) . . ?
C13 C14 C15 118.8(5) . . ?
C13 C14 H2 120.6 . . ?
C15 C14 H2 120.6 . . ?
C14 C15 C9 122.3(5) . . ?
C14 C15 H17 118.8 . . ?
C9 C15 H17 118.8 . . ?
C17 C16 C21 118.6(5) . . ?
C17 C16 N1 120.1(5) . . ?
C21 C16 N1 121.2(5) . . ?
C18 C17 C16 120.4(7) . . ?
C18 C17 H8 119.8 . . ?
C16 C17 H8 119.8 . . ?
C19 C18 C17 121.8(8) . . ?
C19 C18 H7 119.1 . . ?
C17 C18 H7 119.1 . . ?
C18 C19 C20 118.3(7) . . ?
C18 C19 H4 120.9 . . ?
C20 C19 H4 120.9 . . ?
C21 C20 C19 121.3(7) . . ?
C21 C20 H6 119.3 . . ?
C19 C20 H6 119.3 . . ?
C20 C21 C16 119.6(6) . . ?
C20 C21 H5 120.2 . . ?
C16 C21 H5 120.2 . . ?
C1 C22 C23 121.0(7) . . ?
C1 C22 H10 119.5 . . ?
C23 C22 H10 119.5 . . ?
C4 C23 C22 118.5(6) . . ?
C4 C23 H11 120.7 . . ?
C22 C23 H11 120.7 . . ?
C25 C24 C5 120.6(5) . . ?
C25 C24 H13 119.7 . . ?
C5 C24 H13 119.7 . . ?
C8 C25 C24 121.4(5) . . ?
C8 C25 H14 119.3 . . ?
C24 C25 H14 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 C1 C2 C3 0.2(11) . . . . ?
C1 C2 C3 C4 -1.1(10) . . . . ?
C2 C3 C4 C23 0.8(9) . . . . ?
C2 C3 C4 N1 -176.5(6) . . . . ?
C16 N1 C4 C23 66.1(7) . . . . ?
C5 N1 C4 C23 -123.3(6) . . . . ?
C16 N1 C4 C3 -116.7(6) . . . . ?
C5 N1 C4 C3 53.9(7) . . . . ?
C16 N1 C5 C6 30.0(8) . . . . ?
C4 N1 C5 C6 -140.2(5) . . . . ?
C16 N1 C5 C24 -151.2(5) . . . . ?
C4 N1 C5 C24 38.5(7) . . . . ?
C24 C5 C6 C7 0.9(7) . . . . ?
N1 C5 C6 C7 179.7(5) . . . . ?
C5 C6 C7 C8 -1.2(8) . . . . ?
C6 C7 C8 C25 0.1(8) . . . . ?
C6 C7 C8 C9 -177.0(5) . . . . ?
C25 C8 C9 C10 -44.2(8) . . . . ?
C7 C8 C9 C10 132.6(5) . . . . ?
C25 C8 C9 C15 139.9(5) . . . . ?
C7 C8 C9 C15 -43.3(7) . . . . ?
C15 C9 C10 C11 0.1(8) . . . . ?
C8 C9 C10 C11 -175.8(5) . . . . ?
C9 C10 C11 C13 -1.3(8) . . . . ?
C9 C10 C11 S1 176.6(4) . . . . ?
C12 S1 C11 C10 -178.9(5) . . . . ?
C12 S1 C11 C13 -0.8(4) . . . . ?
C13 N3 C12 N2 -177.9(5) . . . . ?
C13 N3 C12 S1 0.6(6) . . . . ?
C11 S1 C12 N3 0.1(5) . . . . ?
C11 S1 C12 N2 178.6(5) . . . . ?
C12 N3 C13 C14 176.7(5) . . . . ?
C12 N3 C13 C11 -1.3(7) . . . . ?
C10 C11 C13 C14 1.5(8) . . . . ?
S1 C11 C13 C14 -176.8(4) . . . . ?
C10 C11 C13 N3 179.6(5) . . . . ?
S1 C11 C13 N3 1.3(6) . . . . ?
N3 C13 C14 C15 -178.4(5) . . . . ?
C11 C13 C14 C15 -0.5(8) . . . . ?
C13 C14 C15 C9 -0.7(8) . . . . ?
C10 C9 C15 C14 0.9(8) . . . . ?
C8 C9 C15 C14 176.9(5) . . . . ?
C5 N1 C16 C17 -155.4(5) . . . . ?
C4 N1 C16 C17 14.5(8) . . . . ?
C5 N1 C16 C21 28.9(8) . . . . ?
C4 N1 C16 C21 -161.1(5) . . . . ?
C21 C16 C17 C18 -0.2(9) . . . . ?
N1 C16 C17 C18 -175.9(6) . . . . ?
C16 C17 C18 C19 0.1(12) . . . . ?
C17 C18 C19 C20 -0.6(13) . . . . ?
C18 C19 C20 C21 1.2(12) . . . . ?
C19 C20 C21 C16 -1.3(10) . . . . ?
C17 C16 C21 C20 0.8(8) . . . . ?
N1 C16 C21 C20 176.4(5) . . . . ?
C2 C1 C22 C23 1.1(11) . . . . ?
C3 C4 C23 C22 0.4(9) . . . . ?
N1 C4 C23 C22 177.7(5) . . . . ?
C1 C22 C23 C4 -1.4(10) . . . . ?
C6 C5 C24 C25 0.5(7) . . . . ?
N1 C5 C24 C25 -178.3(5) . . . . ?
C7 C8 C25 C24 1.4(8) . . . . ?
C9 C8 C25 C24 178.2(5) . . . . ?
C5 C24 C25 C8 -1.6(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2NB N3 0.87(2) 2.12(2) 2.988(7) 176(6) 3_665
N2 H2NB N3 0.87(2) 2.12(2) 2.988(7) 176(6) 3_665
N2 H2NB N3 0.87(2) 2.12(2) 2.988(7) 176(6) 3_665
N2 H2NB N3 0.87(2) 2.12(2) 2.988(7) 176(6) 3_665
N2 H2NB N3 0.87(2) 2.12(2) 2.988(7) 176(6) 3_665
N2 H2NB N3 0.87(2) 2.12(2) 2.988(7) 176(6) 3_665
N2 H2NB N3 0.87(2) 2.12(2) 2.988(7) 176(6) 3_665

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.063



