# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2082831'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Nanchang University
China
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Cl N2 O2 S'
_chemical_formula_weight         384.86

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.8446(18)
_cell_length_b                   8.2197(8)
_cell_length_c                   23.165(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3778.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2626
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      21.81

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21437
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.758
_diffrn_reflns_theta_max         27.688
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4344
_reflns_number_gt                2528
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0873P)²] 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         4344
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1674
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
S1 S 0.62373(3) 0.27180(9) 0.50291(3) 0.0531(2) Uani 1 1 d . . . . .
Cl1 Cl 0.40203(6) 0.66642(13) 0.76476(4) 0.0951(4) Uani 1 1 d . . . . .
O1 O 0.32845(8) 0.0508(2) 0.59430(8) 0.0505(5) Uani 1 1 d . . . . .
N2 N 0.52411(9) 0.1648(3) 0.56333(8) 0.0380(5) Uani 1 1 d . . . . .
O2 O 0.28938(9) 0.1458(3) 0.50974(9) 0.0641(6) Uani 1 1 d . . . . .
N1 N 0.49478(11) 0.2784(3) 0.47226(9) 0.0468(6) Uani 1 1 d . . . . .
C15 C 0.58098(12) 0.1347(3) 0.59754(11) 0.0390(6) Uani 1 1 d . . . . .
C9 C 0.44186(11) 0.2787(3) 0.63141(10) 0.0373(6) Uani 1 1 d . . . . .
C4 C 0.40667(12) 0.1719(3) 0.53332(11) 0.0386(6) Uani 1 1 d . . . . .
C8 C 0.45415(11) 0.1510(3) 0.58440(10) 0.0366(6) Uani 1 1 d . . . . .
H8A H 0.447576 0.042386 0.600950 0.044 Uiso 1 1 calc R U . . .
C20 C 0.58326(13) 0.0616(3) 0.65110(11) 0.0455(6) Uani 1 1 d . . . . .
H20A H 0.544101 0.026906 0.669391 0.055 Uiso 1 1 calc R U . . .
C3 C 0.33618(13) 0.1252(3) 0.54224(12) 0.0432(6) Uani 1 1 d . . . . .
C7 C 0.53767(13) 0.2375(3) 0.51184(11) 0.0420(6) Uani 1 1 d . . . . .
C5 C 0.42771(13) 0.2404(3) 0.48304(12) 0.0435(6) Uani 1 1 d . . . . .
C10 C 0.42353(13) 0.2374(3) 0.68708(11) 0.0493(7) Uani 1 1 d . . . . .
H10A H 0.419092 0.128278 0.696976 0.059 Uiso 1 1 calc R U . . .
C14 C 0.44901(13) 0.4415(3) 0.61798(11) 0.0472(7) Uani 1 1 d . . . . .
H14A H 0.462136 0.471212 0.580908 0.057 Uiso 1 1 calc R U . . .
C16 C 0.64015(13) 0.1867(3) 0.57082(12) 0.0485(7) Uani 1 1 d . . . . .
C19 C 0.64579(14) 0.0416(4) 0.67681(12) 0.0572(8) Uani 1 1 d . . . . .
H19A H 0.648595 -0.009398 0.712563 0.069 Uiso 1 1 calc R U . . .
C12 C 0.41830(14) 0.5170(4) 0.71342(12) 0.0566(8) Uani 1 1 d . . . . .
C11 C 0.41169(15) 0.3556(4) 0.72830(12) 0.0589(8) Uani 1 1 d . . . . .
H11A H 0.399398 0.326507 0.765638 0.071 Uiso 1 1 calc R U . . .
C13 C 0.43703(15) 0.5609(4) 0.65859(13) 0.0570(8) Uani 1 1 d . . . . .
H13A H 0.441615 0.670167 0.648871 0.068 Uiso 1 1 calc R U . . .
C2 C 0.26180(13) -0.0137(4) 0.60614(14) 0.0615(8) Uani 1 1 d . . . . .
H2A H 0.250854 -0.099519 0.578977 0.074 Uiso 1 1 calc R U . . .
H2B H 0.228210 0.071495 0.602736 0.074 Uiso 1 1 calc R U . . .
C6 C 0.38270(14) 0.2859(4) 0.43332(12) 0.0598(8) Uani 1 1 d . . . . .
H6A H 0.409367 0.332037 0.402876 0.090 Uiso 1 1 calc R U . . .
H6B H 0.360037 0.190491 0.419350 0.090 Uiso 1 1 calc R U . . .
H6C H 0.349975 0.364079 0.446025 0.090 Uiso 1 1 calc R U . . .
C18 C 0.70389(15) 0.0957(5) 0.65048(14) 0.0701(9) Uani 1 1 d . . . . .
H18A H 0.745116 0.082747 0.669019 0.084 Uiso 1 1 calc R U . . .
C17 C 0.70157(14) 0.1683(4) 0.59722(15) 0.0679(9) Uani 1 1 d . . . . .
H17A H 0.740810 0.204396 0.579379 0.082 Uiso 1 1 calc R U . . .
C1 C 0.26305(16) -0.0790(5) 0.66623(15) 0.0838(11) Uani 1 1 d . . . . .
H1B H 0.219612 -0.122991 0.675688 0.126 Uiso 1 1 calc R U . . .
H1C H 0.296441 -0.163180 0.669012 0.126 Uiso 1 1 calc R U . . .
H1D H 0.273904 0.007033 0.692660 0.126 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 C7 1.743(3) . ?
S1 C16 1.752(3) . ?
Cl1 C12 1.740(3) . ?
O1 C3 1.361(3) . ?
O1 C2 1.451(3) . ?
N2 C7 1.361(3) . ?
N2 C15 1.401(3) . ?
N2 C8 1.476(3) . ?
O2 C3 1.208(3) . ?
N1 C7 1.296(3) . ?
N1 C5 1.390(3) . ?
C15 C20 1.379(4) . ?
C15 C16 1.395(3) . ?
C9 C10 1.382(3) . ?
C9 C14 1.381(3) . ?
C9 C8 1.532(3) . ?
C4 C5 1.359(4) . ?
C4 C3 1.465(3) . ?
C4 C8 1.522(3) . ?
C8 H8A 0.9800 . ?
C20 C19 1.386(4) . ?
C20 H20A 0.9300 . ?
C5 C6 1.505(4) . ?
C10 C11 1.382(4) . ?
C10 H10A 0.9300 . ?
C14 C13 1.380(4) . ?
C14 H14A 0.9300 . ?
C16 C17 1.372(4) . ?
C19 C18 1.378(4) . ?
C19 H19A 0.9300 . ?
C12 C13 1.372(4) . ?
C12 C11 1.376(4) . ?
C11 H11A 0.9300 . ?
C13 H13A 0.9300 . ?
C2 C1 1.492(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C18 C17 1.371(5) . ?
C18 H18A 0.9300 . ?
C17 H17A 0.9300 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C16 90.63(12) . . ?
C3 O1 C2 115.8(2) . . ?
C7 N2 C15 114.5(2) . . ?
C7 N2 C8 120.64(19) . . ?
C15 N2 C8 123.85(19) . . ?
C7 N1 C5 116.3(2) . . ?
C20 C15 C16 120.3(2) . . ?
C20 C15 N2 127.7(2) . . ?
C16 C15 N2 111.9(2) . . ?
C10 C9 C14 118.4(2) . . ?
C10 C9 C8 122.5(2) . . ?
C14 C9 C8 119.2(2) . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 C8 121.5(2) . . ?
C3 C4 C8 116.9(2) . . ?
N2 C8 C4 108.45(19) . . ?
N2 C8 C9 109.38(18) . . ?
C4 C8 C9 112.10(19) . . ?
N2 C8 H8A 109.0 . . ?
C4 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C15 C20 C19 117.9(2) . . ?
C15 C20 H20A 121.1 . . ?
C19 C20 H20A 121.1 . . ?
O2 C3 O1 121.9(2) . . ?
O2 C3 C4 127.6(3) . . ?
O1 C3 C4 110.5(2) . . ?
N1 C7 N2 127.2(2) . . ?
N1 C7 S1 121.2(2) . . ?
N2 C7 S1 111.64(18) . . ?
C4 C5 N1 122.8(2) . . ?
C4 C5 C6 125.2(2) . . ?
N1 C5 C6 112.0(2) . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C13 C14 C9 121.2(2) . . ?
C13 C14 H14A 119.4 . . ?
C9 C14 H14A 119.4 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 S1 127.5(2) . . ?
C15 C16 S1 111.4(2) . . ?
C18 C19 C20 121.4(3) . . ?
C18 C19 H19A 119.3 . . ?
C20 C19 H19A 119.3 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 Cl1 119.8(3) . . ?
C11 C12 Cl1 119.4(2) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
O1 C2 C1 107.0(2) . . ?
O1 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C18 C17 C16 118.6(3) . . ?
C18 C17 H17A 120.7 . . ?
C16 C17 H17A 120.7 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C15 C20 -179.2(2) . . . . ?
C8 N2 C15 C20 12.5(4) . . . . ?
C7 N2 C15 C16 0.0(3) . . . . ?
C8 N2 C15 C16 -168.3(2) . . . . ?
C7 N2 C8 C4 19.4(3) . . . . ?
C15 N2 C8 C4 -173.0(2) . . . . ?
C7 N2 C8 C9 -103.1(2) . . . . ?
C15 N2 C8 C9 64.5(3) . . . . ?
C5 C4 C8 N2 -17.9(3) . . . . ?
C3 C4 C8 N2 166.2(2) . . . . ?
C5 C4 C8 C9 103.0(3) . . . . ?
C3 C4 C8 C9 -72.9(3) . . . . ?
C10 C9 C8 N2 -119.9(2) . . . . ?
C14 C9 C8 N2 60.3(3) . . . . ?
C10 C9 C8 C4 119.8(3) . . . . ?
C14 C9 C8 C4 -60.0(3) . . . . ?
C16 C15 C20 C19 -0.3(4) . . . . ?
N2 C15 C20 C19 178.8(2) . . . . ?
C2 O1 C3 O2 4.8(4) . . . . ?
C2 O1 C3 C4 -175.0(2) . . . . ?
C5 C4 C3 O2 -3.4(4) . . . . ?
C8 C4 C3 O2 172.5(3) . . . . ?
C5 C4 C3 O1 176.4(2) . . . . ?
C8 C4 C3 O1 -7.7(3) . . . . ?
C5 N1 C7 N2 -1.6(4) . . . . ?
C5 N1 C7 S1 177.89(18) . . . . ?
C15 N2 C7 N1 179.9(2) . . . . ?
C8 N2 C7 N1 -11.4(4) . . . . ?
C15 N2 C7 S1 0.4(3) . . . . ?
C8 N2 C7 S1 169.06(17) . . . . ?
C16 S1 C7 N1 180.0(2) . . . . ?
C16 S1 C7 N2 -0.5(2) . . . . ?
C3 C4 C5 N1 -176.7(2) . . . . ?
C8 C4 C5 N1 7.6(4) . . . . ?
C3 C4 C5 C6 4.1(4) . . . . ?
C8 C4 C5 C6 -171.6(2) . . . . ?
C7 N1 C5 C4 3.4(4) . . . . ?
C7 N1 C5 C6 -177.3(2) . . . . ?
C14 C9 C10 C11 0.9(4) . . . . ?
C8 C9 C10 C11 -178.9(2) . . . . ?
C10 C9 C14 C13 -1.2(4) . . . . ?
C8 C9 C14 C13 178.6(2) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
N2 C15 C16 C17 -180.0(3) . . . . ?
C20 C15 C16 S1 178.9(2) . . . . ?
N2 C15 C16 S1 -0.3(3) . . . . ?
C7 S1 C16 C17 -179.9(3) . . . . ?
C7 S1 C16 C15 0.4(2) . . . . ?
C15 C20 C19 C18 1.3(4) . . . . ?
C13 C12 C11 C10 -0.6(4) . . . . ?
Cl1 C12 C11 C10 178.9(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
Cl1 C12 C13 C14 -179.2(2) . . . . ?
C9 C14 C13 C12 0.6(4) . . . . ?
C3 O1 C2 C1 -176.2(3) . . . . ?
C20 C19 C18 C17 -1.3(5) . . . . ?
C19 C18 C17 C16 0.3(5) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
S1 C16 C17 C18 -178.9(3) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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. 
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data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2083669'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O2 S'
_chemical_formula_weight         378.47

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'
O O 0.0106 0.0060 '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      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                   9.4948(18)
_cell_length_b                   9.5464(19)
_cell_length_c                   11.480(2)
_cell_angle_alpha                103.093(2)
_cell_angle_beta                 109.576(2)
_cell_angle_gamma                91.166(2)
_cell_volume                     949.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3273
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6748
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3516
_reflns_number_gt                2778
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0878P)²+0.7306P] 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         3516
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.3341(5) 1.1334(4) 0.3012(5) 0.0920(14) Uani 1 1 d . . . . .
H1A H 0.331980 1.236365 0.317951 0.138 Uiso 1 1 calc R U . . .
H1B H 0.306932 1.093456 0.210997 0.138 Uiso 1 1 calc R U . . .
H1C H 0.264012 1.092277 0.331296 0.138 Uiso 1 1 calc R U . . .
C2 C 0.4871(4) 1.0996(3) 0.3677(3) 0.0577(8) Uani 1 1 d . . . . .
H2A H 0.558328 1.141981 0.338220 0.069 Uiso 1 1 calc R U . . .
H2B H 0.515313 1.140799 0.458785 0.069 Uiso 1 1 calc R U . . .
C3 C 0.5560(3) 0.8809(3) 0.2601(2) 0.0359(6) Uani 1 1 d . . . . .
C4 C 0.5449(3) 0.7214(3) 0.2316(2) 0.0343(5) Uani 1 1 d . . . . .
C5 C 0.4188(3) 0.6358(3) 0.2113(3) 0.0398(6) Uani 1 1 d . . . . .
C6 C 0.2765(3) 0.6883(4) 0.2280(3) 0.0571(8) Uani 1 1 d . . . . .
H6A H 0.203965 0.606951 0.207768 0.086 Uiso 1 1 calc R U . . .
H6B H 0.298115 0.741365 0.314746 0.086 Uiso 1 1 calc R U . . .
H6C H 0.236905 0.750095 0.171951 0.086 Uiso 1 1 calc R U . . .
C7 C 0.6857(3) 0.6600(2) 0.2135(2) 0.0311(5) Uani 1 1 d . . . . .
H7A H 0.706960 0.700545 0.149235 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8244(3) 0.7026(2) 0.3365(2) 0.0334(5) Uani 1 1 d . . . . .
C9 C 0.9424(3) 0.7992(3) 0.3420(3) 0.0399(6) Uani 1 1 d . . . . .
C10 C 0.9428(3) 0.8612(3) 0.2325(3) 0.0512(7) Uani 1 1 d . . . . .
H10A H 0.852197 0.824524 0.160876 0.077 Uiso 1 1 calc R U . . .
H10B H 0.948304 0.964719 0.257835 0.077 Uiso 1 1 calc R U . . .
H10C H 1.028156 0.833842 0.208886 0.077 Uiso 1 1 calc R U . . .
C11 C 1.0660(3) 0.8406(3) 0.4550(3) 0.0534(8) Uani 1 1 d . . . . .
H11A H 1.144044 0.904545 0.459582 0.064 Uiso 1 1 calc R U . . .
C12 C 1.0755(4) 0.7893(4) 0.5593(3) 0.0592(9) Uani 1 1 d . . . . .
H12A H 1.158528 0.819114 0.634058 0.071 Uiso 1 1 calc R U . . .
C13 C 0.9611(4) 0.6934(3) 0.5527(3) 0.0545(8) Uani 1 1 d . . . . .
H13A H 0.968896 0.657553 0.623230 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8341(3) 0.6486(3) 0.4431(2) 0.0414(6) Uani 1 1 d . . . . .
C15 C 0.7151(4) 0.5430(3) 0.4457(3) 0.0546(8) Uani 1 1 d . . . . .
H15A H 0.633977 0.520765 0.365101 0.082 Uiso 1 1 calc R U . . .
H15B H 0.758001 0.455825 0.461221 0.082 Uiso 1 1 calc R U . . .
H15C H 0.677868 0.585156 0.512402 0.082 Uiso 1 1 calc R U . . .
C16 C 0.5205(3) 0.4302(3) 0.1482(2) 0.0371(6) Uani 1 1 d . . . . .
C17 C 0.7571(3) 0.4115(3) 0.1319(2) 0.0359(6) Uani 1 1 d . . . . .
C18 C 0.9014(3) 0.4515(3) 0.1367(3) 0.0410(6) Uani 1 1 d . . . . .
H18A H 0.938515 0.548443 0.159574 0.049 Uiso 1 1 calc R U . . .
C19 C 0.9885(4) 0.3439(3) 0.1068(3) 0.0510(7) Uani 1 1 d . . . . .
H19A H 1.085285 0.369255 0.110518 0.061 Uiso 1 1 calc R U . . .
C20 C 0.9334(4) 0.1989(3) 0.0714(3) 0.0582(8) Uani 1 1 d . . . . .
H20A H 0.993938 0.128453 0.052076 0.070 Uiso 1 1 calc R U . . .
C21 C 0.7899(4) 0.1578(3) 0.0644(3) 0.0527(8) Uani 1 1 d . . . . .
H21A H 0.752868 0.060659 0.039639 0.063 Uiso 1 1 calc R U . . .
C22 C 0.7021(3) 0.2646(3) 0.0950(2) 0.0422(6) Uani 1 1 d . . . . .
N1 N 0.4049(2) 0.4848(2) 0.1697(2) 0.0442(5) Uani 1 1 d . . . . .
N2 N 0.6532(2) 0.5015(2) 0.16172(19) 0.0336(5) Uani 1 1 d . . . . .
O1 O 0.4918(3) 0.9428(2) 0.3429(2) 0.0580(6) Uani 1 1 d . . . . .
O2 O 0.6203(3) 0.9503(2) 0.2136(2) 0.0567(6) Uani 1 1 d . . . . .
S1 S 0.51984(9) 0.24328(7) 0.09662(7) 0.0491(3) 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 1.478(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.463(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.208(3) . ?
C3 O1 1.332(3) . ?
C3 C4 1.476(3) . ?
C4 C5 1.357(4) . ?
C4 C7 1.530(3) . ?
C5 N1 1.401(3) . ?
C5 C6 1.506(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N2 1.479(3) . ?
C7 C8 1.538(3) . ?
C7 H7A 0.9800 . ?
C8 C14 1.409(4) . ?
C8 C9 1.412(4) . ?
C9 C11 1.395(4) . ?
C9 C10 1.507(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.371(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.392(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.511(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N1 1.297(3) . ?
C16 N2 1.365(3) . ?
C16 S1 1.747(3) . ?
C17 C18 1.394(4) . ?
C17 N2 1.399(3) . ?
C17 C22 1.404(4) . ?
C18 C19 1.386(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.389(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.381(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.388(4) . ?
C21 H21A 0.9300 . ?
C22 S1 1.745(3) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 110.0(3) . . ?
O1 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
O1 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O2 C3 O1 122.3(2) . . ?
O2 C3 C4 122.8(2) . . ?
O1 C3 C4 114.8(2) . . ?
C5 C4 C3 124.3(2) . . ?
C5 C4 C7 122.4(2) . . ?
C3 C4 C7 113.0(2) . . ?
C4 C5 N1 123.3(2) . . ?
C4 C5 C6 125.4(3) . . ?
N1 C5 C6 111.3(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C4 108.85(19) . . ?
N2 C7 C8 112.52(18) . . ?
C4 C7 C8 112.43(19) . . ?
N2 C7 H7A 107.6 . . ?
C4 C7 H7A 107.6 . . ?
C8 C7 H7A 107.6 . . ?
C14 C8 C9 120.0(2) . . ?
C14 C8 C7 121.2(2) . . ?
C9 C8 C7 118.8(2) . . ?
C11 C9 C8 118.6(3) . . ?
C11 C9 C10 117.7(3) . . ?
C8 C9 C10 123.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 121.7(3) . . ?
C12 C11 H11A 119.2 . . ?
C9 C11 H11A 119.2 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 H13A 119.1 . . ?
C14 C13 H13A 119.1 . . ?
C13 C14 C8 118.5(3) . . ?
C13 C14 C15 117.6(3) . . ?
C8 C14 C15 123.9(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 N2 128.0(2) . . ?
N1 C16 S1 120.72(19) . . ?
N2 C16 S1 111.27(19) . . ?
C18 C17 N2 128.0(2) . . ?
C18 C17 C22 119.8(2) . . ?
N2 C17 C22 112.2(2) . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18A 120.6 . . ?
C17 C18 H18A 120.6 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19A 119.5 . . ?
C20 C19 H19A 119.5 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C20 C21 C22 118.6(3) . . ?
C20 C21 H21A 120.7 . . ?
C22 C21 H21A 120.7 . . ?
C21 C22 C17 121.0(3) . . ?
C21 C22 S1 128.1(2) . . ?
C17 C22 S1 110.9(2) . . ?
C16 N1 C5 115.6(2) . . ?
C16 N2 C17 114.4(2) . . ?
C16 N2 C7 121.6(2) . . ?
C17 N2 C7 123.9(2) . . ?
C3 O1 C2 118.0(2) . . ?
C22 S1 C16 91.17(12) . . ?

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
O2 C3 C4 C5 -138.4(3) . . . . ?
O1 C3 C4 C5 42.7(4) . . . . ?
O2 C3 C4 C7 35.6(3) . . . . ?
O1 C3 C4 C7 -143.3(2) . . . . ?
C3 C4 C5 N1 172.1(2) . . . . ?
C7 C4 C5 N1 -1.4(4) . . . . ?
C3 C4 C5 C6 -6.9(4) . . . . ?
C7 C4 C5 C6 179.6(3) . . . . ?
C5 C4 C7 N2 4.9(3) . . . . ?
C3 C4 C7 N2 -169.31(19) . . . . ?
C5 C4 C7 C8 -120.5(3) . . . . ?
C3 C4 C7 C8 65.3(3) . . . . ?
N2 C7 C8 C14 -55.5(3) . . . . ?
C4 C7 C8 C14 67.8(3) . . . . ?
N2 C7 C8 C9 125.3(2) . . . . ?
C4 C7 C8 C9 -111.4(2) . . . . ?
C14 C8 C9 C11 -0.9(3) . . . . ?
C7 C8 C9 C11 178.3(2) . . . . ?
C14 C8 C9 C10 179.3(2) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C8 C9 C11 C12 0.4(4) . . . . ?
C10 C9 C11 C12 -179.8(3) . . . . ?
C9 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C12 C13 C14 C8 0.6(4) . . . . ?
C12 C13 C14 C15 180.0(3) . . . . ?
C9 C8 C14 C13 0.5(4) . . . . ?
C7 C8 C14 C13 -178.7(2) . . . . ?
C9 C8 C14 C15 -178.8(2) . . . . ?
C7 C8 C14 C15 2.0(4) . . . . ?
N2 C17 C18 C19 178.0(2) . . . . ?
C22 C17 C18 C19 -1.1(4) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C19 C20 C21 C22 -0.8(5) . . . . ?
C20 C21 C22 C17 0.3(4) . . . . ?
C20 C21 C22 S1 -179.0(2) . . . . ?
C18 C17 C22 C21 0.7(4) . . . . ?
N2 C17 C22 C21 -178.5(2) . . . . ?
C18 C17 C22 S1 -179.97(19) . . . . ?
N2 C17 C22 S1 0.8(3) . . . . ?
N2 C16 N1 C5 0.3(4) . . . . ?
S1 C16 N1 C5 179.63(18) . . . . ?
C4 C5 N1 C16 -1.6(4) . . . . ?
C6 C5 N1 C16 177.5(2) . . . . ?
N1 C16 N2 C17 179.4(2) . . . . ?
S1 C16 N2 C17 0.1(3) . . . . ?
N1 C16 N2 C7 3.9(4) . . . . ?
S1 C16 N2 C7 -175.42(16) . . . . ?
C18 C17 N2 C16 -179.7(2) . . . . ?
C22 C17 N2 C16 -0.6(3) . . . . ?
C18 C17 N2 C7 -4.3(4) . . . . ?
C22 C17 N2 C7 174.8(2) . . . . ?
C4 C7 N2 C16 -6.0(3) . . . . ?
C8 C7 N2 C16 119.4(2) . . . . ?
C4 C7 N2 C17 179.0(2) . . . . ?
C8 C7 N2 C17 -55.7(3) . . . . ?
O2 C3 O1 C2 6.1(4) . . . . ?
C4 C3 O1 C2 -175.0(2) . . . . ?
C1 C2 O1 C3 104.0(4) . . . . ?
C21 C22 S1 C16 178.6(3) . . . . ?
C17 C22 S1 C16 -0.6(2) . . . . ?
N1 C16 S1 C22 -179.1(2) . . . . ?
N2 C16 S1 C22 0.32(19) . . . . ?

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
C2 H2B O1 0.97 2.60 3.377(4) 137.5 2_676
C2 H2B O1 0.97 2.60 3.377(4) 137.5 2_676
C2 H2B O1 0.97 2.60 3.377(4) 137.5 2_676

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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 2083674'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 N2 O S'
_chemical_formula_weight         320.40

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   21.331(3)
_cell_length_b                   9.7246(13)
_cell_length_c                   7.5317(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1562.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4288
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.44

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8983
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3417
_reflns_number_gt                3196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component perfect 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)+(0.1989P)²+5.7617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as a perfect inversion twin. 
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3417
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.1192
_refine_ls_wR_factor_ref         0.3346
_refine_ls_wR_factor_gt          0.3310
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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 0.7434(5) 0.2841(10) 0.7945(17) 0.042(2) Uani 1 1 d . . . . .
H1A H 0.774941 0.218883 0.807218 0.050 Uiso 1 1 calc R U . . .
C2 C 0.7590(5) 0.4260(11) 0.8040(19) 0.046(3) Uani 1 1 d . . . . .
H2A H 0.799747 0.453741 0.828920 0.056 Uiso 1 1 calc R U . . .
C3 C 0.7119(4) 0.5225(9) 0.7753(16) 0.036(2) Uani 1 1 d . . . . .
H3A H 0.720735 0.616035 0.781573 0.044 Uiso 1 1 calc R U . . .
C4 C 0.6521(4) 0.4777(9) 0.7375(12) 0.0290(18) Uani 1 1 d . . . . .
C5 C 0.6372(4) 0.3409(9) 0.7301(13) 0.034(2) Uani 1 1 d . . . . .
C6 C 0.6833(5) 0.2415(10) 0.7672(19) 0.049(3) Uani 1 1 d . . . . .
H6A H 0.672977 0.148649 0.772946 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5458(4) 0.4932(9) 0.6790(15) 0.0316(18) Uani 1 1 d . . . . .
C8 C 0.6016(3) 0.7142(8) 0.6829(13) 0.0257(16) Uani 1 1 d . . . . .
H8A H 0.629741 0.753652 0.772314 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6271(3) 0.7474(8) 0.5005(11) 0.0229(16) Uani 1 1 d . . . . .
C10 C 0.6067(4) 0.6768(10) 0.3462(15) 0.036(2) Uani 1 1 d . . . . .
H10A H 0.579978 0.601760 0.357482 0.044 Uiso 1 1 calc R U . . .
C11 C 0.6262(5) 0.7184(11) 0.1777(16) 0.042(2) Uani 1 1 d . . . . .
H11A H 0.610646 0.674849 0.076953 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6698(5) 0.8270(12) 0.1610(14) 0.042(2) Uani 1 1 d . . . . .
H12A H 0.684011 0.853881 0.049608 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6905(5) 0.8912(10) 0.3083(14) 0.038(2) Uani 1 1 d . . . . .
H13A H 0.719263 0.962536 0.297048 0.046 Uiso 1 1 calc R U . . .
C14 C 0.6699(4) 0.8533(9) 0.4773(13) 0.0313(19) Uani 1 1 d . . . . .
H14A H 0.685159 0.899836 0.576140 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5358(4) 0.7687(9) 0.7146(12) 0.0272(17) Uani 1 1 d . . . . .
C16 C 0.4853(4) 0.6852(9) 0.6796(14) 0.0294(17) Uani 1 1 d . . . . .
C17 C 0.4173(4) 0.7302(11) 0.6739(16) 0.039(2) Uani 1 1 d . . . . .
H17A H 0.404676 0.760913 0.789624 0.058 Uiso 1 1 calc R U . . .
H17B H 0.391562 0.654227 0.638066 0.058 Uiso 1 1 calc R U . . .
H17C H 0.412711 0.804136 0.590397 0.058 Uiso 1 1 calc R U . . .
C18 C 0.5369(5) 0.9132(9) 0.7781(15) 0.035(2) Uani 1 1 d . . . . .
C19 C 0.4780(5) 0.9893(11) 0.8193(16) 0.040(2) Uani 1 1 d . . . . .
H19A H 0.488039 1.072576 0.881660 0.061 Uiso 1 1 calc R U . . .
H19B H 0.451433 0.933017 0.891972 0.061 Uiso 1 1 calc R U . . .
H19C H 0.456699 1.011445 0.710734 0.061 Uiso 1 1 calc R U . . .
N1 N 0.5997(3) 0.5629(7) 0.7070(12) 0.0270(14) Uani 1 1 d . . . . .
N2 N 0.4907(3) 0.5456(8) 0.6468(12) 0.0350(19) Uani 1 1 d . . . . .
O1 O 0.5870(3) 0.9721(7) 0.7953(11) 0.0411(18) Uani 1 1 d . . . . .
S1 S 0.55778(11) 0.3155(2) 0.6852(4) 0.0400(7) 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 C6 1.363(16) . ?
C1 C2 1.421(15) . ?
C1 H1A 0.9300 . ?
C2 C3 1.391(14) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(13) . ?
C3 H3A 0.9300 . ?
C4 C5 1.369(12) . ?
C4 N1 1.410(11) . ?
C5 C6 1.407(14) . ?
C5 S1 1.745(10) . ?
C6 H6A 0.9300 . ?
C7 N2 1.304(12) . ?
C7 N1 1.351(10) . ?
C7 S1 1.748(9) . ?
C8 N1 1.483(10) . ?
C8 C9 1.512(13) . ?
C8 C15 1.520(11) . ?
C8 H8A 0.9800 . ?
C9 C14 1.387(11) . ?
C9 C10 1.418(13) . ?
C10 C11 1.396(16) . ?
C10 H10A 0.9300 . ?
C11 C12 1.412(15) . ?
C11 H11A 0.9300 . ?
C12 C13 1.347(15) . ?
C12 H12A 0.9300 . ?
C13 C14 1.396(14) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.375(11) . ?
C15 C18 1.485(11) . ?
C16 N2 1.384(12) . ?
C16 C17 1.516(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O1 1.220(12) . ?
C18 C19 1.490(12) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.5(9) . . ?
C6 C1 H1A 119.2 . . ?
C2 C1 H1A 119.2 . . ?
C3 C2 C1 118.6(9) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C4 C3 C2 119.1(8) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C5 C4 C3 122.1(9) . . ?
C5 C4 N1 112.3(8) . . ?
C3 C4 N1 125.6(8) . . ?
C4 C5 C6 119.8(9) . . ?
C4 C5 S1 111.8(7) . . ?
C6 C5 S1 128.3(7) . . ?
C1 C6 C5 118.6(9) . . ?
C1 C6 H6A 120.7 . . ?
C5 C6 H6A 120.7 . . ?
N2 C7 N1 126.9(8) . . ?
N2 C7 S1 121.5(6) . . ?
N1 C7 S1 111.6(6) . . ?
N1 C8 C9 109.5(7) . . ?
N1 C8 C15 107.6(6) . . ?
C9 C8 C15 113.6(7) . . ?
N1 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C15 C8 H8A 108.7 . . ?
C14 C9 C10 117.3(8) . . ?
C14 C9 C8 120.6(8) . . ?
C10 C9 C8 122.1(7) . . ?
C11 C10 C9 120.9(8) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 119.6(9) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C13 C12 C11 119.3(9) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 121.7(9) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C13 C14 C9 121.2(8) . . ?
C13 C14 H14A 119.4 . . ?
C9 C14 H14A 119.4 . . ?
C16 C15 C18 129.3(8) . . ?
C16 C15 C8 119.2(7) . . ?
C18 C15 C8 111.5(7) . . ?
C15 C16 N2 123.3(7) . . ?
C15 C16 C17 125.7(8) . . ?
N2 C16 C17 111.0(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 C15 119.5(8) . . ?
O1 C18 C19 118.9(8) . . ?
C15 C18 C19 121.6(9) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 N1 C4 113.9(7) . . ?
C7 N1 C8 120.1(7) . . ?
C4 N1 C8 125.5(6) . . ?
C7 N2 C16 115.1(7) . . ?
C5 S1 C7 90.4(4) . . ?

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
C19 H19A S1 0.96 3.16 3.738(11) 120.4 1_565
C17 H17C S1 0.96 3.33 3.746(12) 108.7 2_664
C6 H6A O1 0.93 2.52 3.335(13) 146.8 1_545

_refine_diff_density_max         2.151
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.155

####################################################################### 
# 
# 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 2083529'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Nanchang University
China
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-06-30 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            'C42 H40 N4 O6 S2'
_chemical_formula_weight         760.90

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'
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                   8.3164(9)
_cell_length_b                   26.101(3)
_cell_length_c                   17.840(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.630(2)
_cell_angle_gamma                90
_cell_volume                     3792.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4269
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      23.99

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19223
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.560
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             6667
_reflns_number_gt                4473
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0675P)²+0.8190P] 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         6667
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.25523(10) 0.45031(3) 0.46242(4) 0.0588(2) Uani 1 1 d . . . . .
S2 S 0.71314(9) 0.20922(3) 0.96001(4) 0.0565(2) Uani 1 1 d . . . . .
N1 N 0.8075(2) 0.21064(7) 0.83161(10) 0.0374(5) Uani 1 1 d . . . . .
N3 N 0.3524(2) 0.44909(7) 0.33488(11) 0.0385(5) Uani 1 1 d . . . . .
O7 O 0.9719(2) 0.35537(6) 0.69862(10) 0.0503(4) Uani 1 1 d . . . . .
O5 O 0.2773(2) 0.19062(7) 0.52336(9) 0.0553(5) Uani 1 1 d . . . . .
N2 N 0.7730(2) 0.29290(7) 0.88371(11) 0.0426(5) Uani 1 1 d . . . . .
N4 N 0.3530(3) 0.53137(8) 0.39307(11) 0.0468(5) Uani 1 1 d . . . . .
C8 C 0.8366(3) 0.23013(8) 0.75788(12) 0.0358(5) Uani 1 1 d . . . . .
H8A H 0.9311 0.2120 0.7456 0.043 Uiso 1 1 calc R U . . .
O10 O 0.5584(2) 0.59055(7) 0.20966(10) 0.0565(5) Uani 1 1 d . . . . .
C7 C 0.7676(3) 0.24311(9) 0.88416(13) 0.0398(6) Uani 1 1 d . . . . .
C36 C 0.2518(3) 0.46095(8) 0.19650(13) 0.0383(5) Uani 1 1 d . . . . .
C15 C 0.6880(3) 0.22030(8) 0.69390(12) 0.0348(5) Uani 1 1 d . . . . .
C9 C 0.8790(3) 0.28678(8) 0.76730(13) 0.0350(5) Uani 1 1 d . . . . .
C18 C 0.4089(3) 0.20251(9) 0.58069(13) 0.0406(6) Uani 1 1 d . . . . .
C29 C 0.3959(3) 0.46774(9) 0.26346(13) 0.0403(6) Uani 1 1 d . . . . .
H29A H 0.4883 0.4473 0.2535 0.048 Uiso 1 1 calc R U . . .
C41 C 0.1000(3) 0.48099(10) 0.19888(14) 0.0481(6) Uani 1 1 d . . . . .
H41A H 0.0870 0.4995 0.2418 0.058 Uiso 1 1 calc R U . . .
O9 O 0.5870(2) 0.51026(7) 0.17265(11) 0.0641(5) Uani 1 1 d . . . . .
C31 C 0.4230(3) 0.55173(9) 0.33484(14) 0.0419(6) Uani 1 1 d . . . . .
C20 C 0.5381(3) 0.24213(9) 0.69790(13) 0.0442(6) Uani 1 1 d . . . . .
H20A H 0.5311 0.2633 0.7390 0.053 Uiso 1 1 calc R U . . .
C30 C 0.4514(3) 0.52345(9) 0.27503(13) 0.0389(6) Uani 1 1 d . . . . .
C28 C 0.3279(3) 0.48218(9) 0.39043(13) 0.0416(6) Uani 1 1 d . . . . .
C19 C 0.3988(3) 0.23329(9) 0.64256(13) 0.0443(6) Uani 1 1 d . . . . .
H19A H 0.2991 0.2479 0.6469 0.053 Uiso 1 1 calc R U . . .
C5 C 0.7468(3) 0.15112(10) 0.91775(14) 0.0483(6) Uani 1 1 d . . . . .
C11 C 0.8667(3) 0.37134(9) 0.83805(15) 0.0503(6) Uani 1 1 d . . . . .
H11A H 0.8288 0.3815 0.8832 0.075 Uiso 1 1 calc R U . . .
H11B H 0.9815 0.3790 0.8442 0.075 Uiso 1 1 calc R U . . .
H11C H 0.8066 0.3897 0.7947 0.075 Uiso 1 1 calc R U . . .
C26 C 0.2617(3) 0.39168(9) 0.41634(14) 0.0463(6) Uani 1 1 d . . . . .
O6 O 1.0153(2) 0.27508(7) 0.66558(11) 0.0633(5) Uani 1 1 d . . . . .
C12 C 0.9608(3) 0.30443(9) 0.70681(14) 0.0404(6) Uani 1 1 d . . . . .
C25 C 0.3160(3) 0.39792(9) 0.34770(13) 0.0408(6) Uani 1 1 d . . . . .
C10 C 0.8403(3) 0.31485(9) 0.82564(13) 0.0382(5) Uani 1 1 d . . . . .
C33 C 0.5374(3) 0.54002(10) 0.21534(15) 0.0450(6) Uani 1 1 d . . . . .
C4 C 0.7975(3) 0.15870(9) 0.84854(14) 0.0419(6) Uani 1 1 d . . . . .
C17 C 0.5585(3) 0.18217(10) 0.57422(14) 0.0513(7) Uani 1 1 d . . . . .
H17A H 0.5669 0.1625 0.5317 0.062 Uiso 1 1 calc R U . . .
C40 C -0.0343(3) 0.47457(10) 0.13954(14) 0.0534(7) Uani 1 1 d . . . . .
H40A H -0.1358 0.4884 0.1428 0.064 Uiso 1 1 calc R U . . .
C13 C 1.0523(3) 0.37220(10) 0.63807(16) 0.0597(7) Uani 1 1 d . . . . .
H13A H 0.9888 0.3619 0.5886 0.072 Uiso 1 1 calc R U . . .
H13B H 1.1607 0.3570 0.6445 0.072 Uiso 1 1 calc R U . . .
C3 C 0.8324(3) 0.11742(9) 0.80527(15) 0.0511(7) Uani 1 1 d . . . . .
H3A H 0.8660 0.1225 0.7592 0.061 Uiso 1 1 calc R U . . .
C32 C 0.4624(3) 0.60776(9) 0.34920(15) 0.0530(7) Uani 1 1 d . . . . .
H32A H 0.4297 0.6183 0.3955 0.080 Uiso 1 1 calc R U . . .
H32B H 0.5783 0.6130 0.3541 0.080 Uiso 1 1 calc R U . . .
H32C H 0.4041 0.6276 0.3071 0.080 Uiso 1 1 calc R U . . .
C16 C 0.6959(3) 0.19082(9) 0.63067(14) 0.0469(6) Uani 1 1 d . . . . .
H16A H 0.7958 0.1765 0.6259 0.056 Uiso 1 1 calc R U . . .
C6 C 0.7300(3) 0.10164(11) 0.94505(16) 0.0598(8) Uani 1 1 d . . . . .
H6A H 0.6963 0.0962 0.9911 0.072 Uiso 1 1 calc R U . . .
C24 C 0.3285(3) 0.35608(9) 0.30174(15) 0.0515(7) Uani 1 1 d . . . . .
H24A H 0.3651 0.3599 0.2561 0.062 Uiso 1 1 calc R U . . .
C23 C 0.2852(3) 0.30829(10) 0.32535(17) 0.0585(7) Uani 1 1 d . . . . .
H23A H 0.2914 0.2799 0.2946 0.070 Uiso 1 1 calc R U . . .
C34 C 0.6486(4) 0.60785(10) 0.15246(16) 0.0614(8) Uani 1 1 d . . . . .
H34A H 0.5931 0.5970 0.1018 0.074 Uiso 1 1 calc R U . . .
H34B H 0.7585 0.5935 0.1628 0.074 Uiso 1 1 calc R U . . .
C37 C 0.2684(3) 0.43398(10) 0.13169(15) 0.0544(7) Uani 1 1 d . . . . .
H37A H 0.3695 0.4199 0.1286 0.065 Uiso 1 1 calc R U . . .
C35 C 0.6563(4) 0.66475(10) 0.15671(17) 0.0646(8) Uani 1 1 d . . . . .
H35A H 0.7153 0.6775 0.1196 0.097 Uiso 1 1 calc R U . . .
H35B H 0.5469 0.6785 0.1463 0.097 Uiso 1 1 calc R U . . .
H35C H 0.7116 0.6750 0.2070 0.097 Uiso 1 1 calc R U . . .
O8 O -0.1388(3) 0.43875(9) 0.01372(12) 0.0879(7) Uani 1 1 d . . . . .
C14 C 1.0651(4) 0.42911(10) 0.64264(18) 0.0681(8) Uani 1 1 d . . . . .
H14A H 1.1181 0.4415 0.6031 0.102 Uiso 1 1 calc R U . . .
H14B H 0.9572 0.4437 0.6361 0.102 Uiso 1 1 calc R U . . .
H14C H 1.1283 0.4388 0.6917 0.102 Uiso 1 1 calc R U . . .
C27 C 0.2211(3) 0.34365(10) 0.44011(16) 0.0589(7) Uani 1 1 d . . . . .
H27A H 0.1869 0.3396 0.4863 0.071 Uiso 1 1 calc R U . . .
C38 C 0.1368(4) 0.42782(11) 0.07176(16) 0.0669(8) Uani 1 1 d . . . . .
H38A H 0.1505 0.4102 0.0281 0.080 Uiso 1 1 calc R U . . .
C1 C 0.7652(4) 0.06099(11) 0.90120(19) 0.0678(9) Uani 1 1 d . . . . .
H1A H 0.7546 0.0277 0.9182 0.081 Uiso 1 1 calc R U . . .
C22 C 0.2328(4) 0.30202(10) 0.39376(17) 0.0607(8) Uani 1 1 d . . . . .
H22A H 0.2053 0.2695 0.4085 0.073 Uiso 1 1 calc R U . . .
C39 C -0.0152(4) 0.44753(10) 0.07585(15) 0.0561(7) Uani 1 1 d . . . . .
C2 C 0.8158(4) 0.06851(10) 0.83278(18) 0.0632(8) Uani 1 1 d . . . . .
H2B H 0.8389 0.0403 0.8049 0.076 Uiso 1 1 calc R U . . .
C21 C 0.1197(3) 0.20556(12) 0.53441(17) 0.0663(8) Uani 1 1 d . . . . .
H21A H 0.0381 0.1953 0.4909 0.099 Uiso 1 1 calc R U . . .
H21B H 0.0978 0.1894 0.5797 0.099 Uiso 1 1 calc R U . . .
H21C H 0.1165 0.2421 0.5401 0.099 Uiso 1 1 calc R U . . .
C42 C -0.2960(4) 0.45984(16) 0.0144(2) 0.0976(12) Uani 1 1 d . . . . .
H42A H -0.3706 0.4509 -0.0322 0.146 Uiso 1 1 calc R U . . .
H42B H -0.3360 0.4464 0.0573 0.146 Uiso 1 1 calc R U . . .
H42C H -0.2876 0.4965 0.0185 0.146 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 C28 1.737(2) . ?
S1 C26 1.743(3) . ?
S2 C5 1.741(3) . ?
S2 C7 1.751(2) . ?
N1 C7 1.354(3) . ?
N1 C4 1.395(3) . ?
N1 C8 1.475(3) . ?
N3 C28 1.361(3) . ?
N3 C25 1.398(3) . ?
N3 C29 1.476(3) . ?
O7 C12 1.343(3) . ?
O7 C13 1.448(3) . ?
O5 C18 1.375(3) . ?
O5 C21 1.419(3) . ?
N2 C7 1.300(3) . ?
N2 C10 1.396(3) . ?
N4 C28 1.300(3) . ?
N4 C31 1.394(3) . ?
C8 C9 1.521(3) . ?
C8 C15 1.526(3) . ?
C8 H8A 0.9800 . ?
O10 C33 1.337(3) . ?
O10 C34 1.455(3) . ?
C36 C41 1.376(3) . ?
C36 C37 1.384(3) . ?
C36 C29 1.522(3) . ?
C15 C16 1.378(3) . ?
C15 C20 1.385(3) . ?
C9 C10 1.363(3) . ?
C9 C12 1.461(3) . ?
C18 C17 1.379(3) . ?
C18 C19 1.381(3) . ?
C29 C30 1.527(3) . ?
C29 H29A 0.9800 . ?
C41 C40 1.385(3) . ?
C41 H41A 0.9300 . ?
O9 C33 1.217(3) . ?
C31 C30 1.357(3) . ?
C31 C32 1.509(3) . ?
C20 C19 1.382(3) . ?
C20 H20A 0.9300 . ?
C30 C33 1.463(3) . ?
C19 H19A 0.9300 . ?
C5 C4 1.397(3) . ?
C5 C6 1.397(3) . ?
C11 C10 1.501(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C26 C27 1.387(3) . ?
C26 C25 1.397(3) . ?
O6 C12 1.211(3) . ?
C25 C24 1.382(3) . ?
C4 C3 1.390(3) . ?
C17 C16 1.381(3) . ?
C17 H17A 0.9300 . ?
C40 C39 1.374(4) . ?
C40 H40A 0.9300 . ?
C13 C14 1.490(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C3 C2 1.385(3) . ?
C3 H3A 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C16 H16A 0.9300 . ?
C6 C1 1.384(4) . ?
C6 H6A 0.9300 . ?
C24 C23 1.387(3) . ?
C24 H24A 0.9300 . ?
C23 C22 1.386(4) . ?
C23 H23A 0.9300 . ?
C34 C35 1.488(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C37 C38 1.376(4) . ?
C37 H37A 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
O8 C39 1.370(3) . ?
O8 C42 1.421(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C27 C22 1.381(4) . ?
C27 H27A 0.9300 . ?
C38 C39 1.381(4) . ?
C38 H38A 0.9300 . ?
C1 C2 1.383(4) . ?
C1 H1A 0.9300 . ?
C22 H22A 0.9300 . ?
C2 H2B 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 S1 C26 91.33(12) . . ?
C5 S2 C7 90.93(12) . . ?
C7 N1 C4 115.1(2) . . ?
C7 N1 C8 120.59(18) . . ?
C4 N1 C8 123.76(19) . . ?
C28 N3 C25 114.70(19) . . ?
C28 N3 C29 121.22(19) . . ?
C25 N3 C29 123.73(19) . . ?
C12 O7 C13 115.71(19) . . ?
C18 O5 C21 117.01(19) . . ?
C7 N2 C10 115.7(2) . . ?
C28 N4 C31 116.0(2) . . ?
N1 C8 C9 108.22(17) . . ?
N1 C8 C15 110.80(17) . . ?
C9 C8 C15 112.38(17) . . ?
N1 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C15 C8 H8A 108.4 . . ?
C33 O10 C34 116.9(2) . . ?
N2 C7 N1 127.4(2) . . ?
N2 C7 S2 121.63(18) . . ?
N1 C7 S2 110.89(17) . . ?
C41 C36 C37 117.8(2) . . ?
C41 C36 C29 120.9(2) . . ?
C37 C36 C29 121.3(2) . . ?
C16 C15 C20 117.7(2) . . ?
C16 C15 C8 122.7(2) . . ?
C20 C15 C8 119.6(2) . . ?
C10 C9 C12 127.7(2) . . ?
C10 C9 C8 121.4(2) . . ?
C12 C9 C8 110.91(19) . . ?
O5 C18 C17 116.6(2) . . ?
O5 C18 C19 123.9(2) . . ?
C17 C18 C19 119.5(2) . . ?
N3 C29 C36 110.37(18) . . ?
N3 C29 C30 108.52(18) . . ?
C36 C29 C30 112.69(18) . . ?
N3 C29 H29A 108.4 . . ?
C36 C29 H29A 108.4 . . ?
C30 C29 H29A 108.4 . . ?
C36 C41 C40 122.3(2) . . ?
C36 C41 H41A 118.9 . . ?
C40 C41 H41A 118.9 . . ?
C30 C31 N4 122.9(2) . . ?
C30 C31 C32 126.5(2) . . ?
N4 C31 C32 110.6(2) . . ?
C19 C20 C15 121.9(2) . . ?
C19 C20 H20A 119.1 . . ?
C15 C20 H20A 119.1 . . ?
C31 C30 C33 126.9(2) . . ?
C31 C30 C29 121.9(2) . . ?
C33 C30 C29 111.2(2) . . ?
N4 C28 N3 127.3(2) . . ?
N4 C28 S1 121.56(19) . . ?
N3 C28 S1 111.11(17) . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 S2 111.28(18) . . ?
C6 C5 S2 128.2(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 S1 128.1(2) . . ?
C25 C26 S1 110.92(18) . . ?
O6 C12 O7 121.2(2) . . ?
O6 C12 C9 122.4(2) . . ?
O7 C12 C9 116.4(2) . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 N3 127.8(2) . . ?
C26 C25 N3 111.9(2) . . ?
C9 C10 N2 122.5(2) . . ?
C9 C10 C11 126.2(2) . . ?
N2 C10 C11 111.2(2) . . ?
O9 C33 O10 121.1(2) . . ?
O9 C33 C30 123.0(2) . . ?
O10 C33 C30 115.9(2) . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 N1 127.2(2) . . ?
C5 C4 N1 111.8(2) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C39 C40 C41 119.0(2) . . ?
C39 C40 H40A 120.5 . . ?
C41 C40 H40A 120.5 . . ?
O7 C13 C14 107.5(2) . . ?
O7 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
O7 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 121.0 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C15 C16 C17 121.2(2) . . ?
C15 C16 H16A 119.4 . . ?
C17 C16 H16A 119.4 . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 H6A 121.2 . . ?
C5 C6 H6A 121.2 . . ?
C25 C24 C23 118.4(3) . . ?
C25 C24 H24A 120.8 . . ?
C23 C24 H24A 120.8 . . ?
C22 C23 C24 121.4(3) . . ?
C22 C23 H23A 119.3 . . ?
C24 C23 H23A 119.3 . . ?
O10 C34 C35 107.3(2) . . ?
O10 C34 H34A 110.3 . . ?
C35 C34 H34A 110.3 . . ?
O10 C34 H34B 110.3 . . ?
C35 C34 H34B 110.3 . . ?
H34A C34 H34B 108.5 . . ?
C38 C37 C36 120.7(3) . . ?
C38 C37 H37A 119.6 . . ?
C36 C37 H37A 119.6 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C39 O8 C42 118.0(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C22 C27 C26 118.5(3) . . ?
C22 C27 H27A 120.7 . . ?
C26 C27 H27A 120.7 . . ?
C37 C38 C39 120.6(3) . . ?
C37 C38 H38A 119.7 . . ?
C39 C38 H38A 119.7 . . ?
C2 C1 C6 121.8(3) . . ?
C2 C1 H1A 119.1 . . ?
C6 C1 H1A 119.1 . . ?
C27 C22 C23 120.5(3) . . ?
C27 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
O8 C39 C40 124.2(3) . . ?
O8 C39 C38 116.1(3) . . ?
C40 C39 C38 119.7(2) . . ?
C1 C2 C3 120.9(3) . . ?
C1 C2 H2B 119.5 . . ?
C3 C2 H2B 119.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O8 C42 H42A 109.5 . . ?
O8 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O8 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C8 C9 21.6(3) . . . . ?
C4 N1 C8 C9 -166.98(19) . . . . ?
C7 N1 C8 C15 -102.0(2) . . . . ?
C4 N1 C8 C15 69.4(3) . . . . ?
C10 N2 C7 N1 -5.6(3) . . . . ?
C10 N2 C7 S2 171.22(15) . . . . ?
C4 N1 C7 N2 177.0(2) . . . . ?
C8 N1 C7 N2 -10.9(3) . . . . ?
C4 N1 C7 S2 -0.1(2) . . . . ?
C8 N1 C7 S2 172.00(15) . . . . ?
C5 S2 C7 N2 -177.3(2) . . . . ?
C5 S2 C7 N1 0.06(17) . . . . ?
N1 C8 C15 C16 -119.6(2) . . . . ?
C9 C8 C15 C16 119.2(2) . . . . ?
N1 C8 C15 C20 61.3(3) . . . . ?
C9 C8 C15 C20 -59.9(3) . . . . ?
N1 C8 C9 C10 -19.3(3) . . . . ?
C15 C8 C9 C10 103.4(2) . . . . ?
N1 C8 C9 C12 161.24(18) . . . . ?
C15 C8 C9 C12 -76.1(2) . . . . ?
C21 O5 C18 C17 171.9(2) . . . . ?
C21 O5 C18 C19 -8.5(4) . . . . ?
C28 N3 C29 C36 -108.6(2) . . . . ?
C25 N3 C29 C36 64.3(3) . . . . ?
C28 N3 C29 C30 15.4(3) . . . . ?
C25 N3 C29 C30 -171.77(19) . . . . ?
C41 C36 C29 N3 54.5(3) . . . . ?
C37 C36 C29 N3 -124.7(2) . . . . ?
C41 C36 C29 C30 -66.9(3) . . . . ?
C37 C36 C29 C30 113.8(3) . . . . ?
C37 C36 C41 C40 0.6(4) . . . . ?
C29 C36 C41 C40 -178.7(2) . . . . ?
C28 N4 C31 C30 5.4(3) . . . . ?
C28 N4 C31 C32 -173.9(2) . . . . ?
C16 C15 C20 C19 2.7(4) . . . . ?
C8 C15 C20 C19 -178.2(2) . . . . ?
N4 C31 C30 C33 -174.0(2) . . . . ?
C32 C31 C30 C33 5.2(4) . . . . ?
N4 C31 C30 C29 5.0(3) . . . . ?
C32 C31 C30 C29 -175.8(2) . . . . ?
N3 C29 C30 C31 -14.5(3) . . . . ?
C36 C29 C30 C31 108.0(2) . . . . ?
N3 C29 C30 C33 164.61(18) . . . . ?
C36 C29 C30 C33 -72.9(2) . . . . ?
C31 N4 C28 N3 -4.5(4) . . . . ?
C31 N4 C28 S1 175.35(17) . . . . ?
C25 N3 C28 N4 179.4(2) . . . . ?
C29 N3 C28 N4 -7.1(4) . . . . ?
C25 N3 C28 S1 -0.5(2) . . . . ?
C29 N3 C28 S1 173.01(16) . . . . ?
C26 S1 C28 N4 -179.2(2) . . . . ?
C26 S1 C28 N3 0.74(18) . . . . ?
C15 C20 C19 C18 -1.1(4) . . . . ?
O5 C18 C19 C20 178.8(2) . . . . ?
C17 C18 C19 C20 -1.6(4) . . . . ?
C7 S2 C5 C4 0.01(18) . . . . ?
C7 S2 C5 C6 179.6(2) . . . . ?
C28 S1 C26 C27 179.1(3) . . . . ?
C28 S1 C26 C25 -0.85(19) . . . . ?
C13 O7 C12 O6 0.0(3) . . . . ?
C13 O7 C12 C9 -179.6(2) . . . . ?
C10 C9 C12 O6 166.8(2) . . . . ?
C8 C9 C12 O6 -13.8(3) . . . . ?
C10 C9 C12 O7 -13.6(3) . . . . ?
C8 C9 C12 O7 165.80(19) . . . . ?
C27 C26 C25 C24 0.7(4) . . . . ?
S1 C26 C25 C24 -179.33(19) . . . . ?
C27 C26 C25 N3 -179.2(2) . . . . ?
S1 C26 C25 N3 0.8(3) . . . . ?
C28 N3 C25 C24 179.9(2) . . . . ?
C29 N3 C25 C24 6.6(4) . . . . ?
C28 N3 C25 C26 -0.2(3) . . . . ?
C29 N3 C25 C26 -173.47(19) . . . . ?
C12 C9 C10 N2 -175.0(2) . . . . ?
C8 C9 C10 N2 5.6(3) . . . . ?
C12 C9 C10 C11 3.2(4) . . . . ?
C8 C9 C10 C11 -176.1(2) . . . . ?
C7 N2 C10 C9 8.0(3) . . . . ?
C7 N2 C10 C11 -170.4(2) . . . . ?
C34 O10 C33 O9 -2.4(4) . . . . ?
C34 O10 C33 C30 177.9(2) . . . . ?
C31 C30 C33 O9 164.9(2) . . . . ?
C29 C30 C33 O9 -14.2(3) . . . . ?
C31 C30 C33 O10 -15.5(4) . . . . ?
C29 C30 C33 O10 165.44(19) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
S2 C5 C4 C3 179.57(18) . . . . ?
C6 C5 C4 N1 -179.7(2) . . . . ?
S2 C5 C4 N1 -0.1(2) . . . . ?
C7 N1 C4 C3 -179.5(2) . . . . ?
C8 N1 C4 C3 8.7(4) . . . . ?
C7 N1 C4 C5 0.1(3) . . . . ?
C8 N1 C4 C5 -171.71(19) . . . . ?
O5 C18 C17 C16 -177.8(2) . . . . ?
C19 C18 C17 C16 2.5(4) . . . . ?
C36 C41 C40 C39 -0.4(4) . . . . ?
C12 O7 C13 C14 -175.2(2) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
N1 C4 C3 C2 179.5(2) . . . . ?
C20 C15 C16 C17 -1.7(4) . . . . ?
C8 C15 C16 C17 179.2(2) . . . . ?
C18 C17 C16 C15 -0.9(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
S2 C5 C6 C1 -179.5(2) . . . . ?
C26 C25 C24 C23 0.3(4) . . . . ?
N3 C25 C24 C23 -179.8(2) . . . . ?
C25 C24 C23 C22 -0.9(4) . . . . ?
C33 O10 C34 C35 -180.0(2) . . . . ?
C41 C36 C37 C38 0.3(4) . . . . ?
C29 C36 C37 C38 179.5(2) . . . . ?
C25 C26 C27 C22 -1.1(4) . . . . ?
S1 C26 C27 C22 178.9(2) . . . . ?
C36 C37 C38 C39 -1.4(4) . . . . ?
C5 C6 C1 C2 0.2(4) . . . . ?
C26 C27 C22 C23 0.5(4) . . . . ?
C24 C23 C22 C27 0.5(4) . . . . ?
C42 O8 C39 C40 1.4(4) . . . . ?
C42 O8 C39 C38 -177.9(3) . . . . ?
C41 C40 C39 O8 -179.9(3) . . . . ?
C41 C40 C39 C38 -0.7(4) . . . . ?
C37 C38 C39 O8 -179.1(3) . . . . ?
C37 C38 C39 C40 1.6(5) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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 2083677'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N3 O2 S'
_chemical_formula_weight         339.40

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'
S S 0.1246 0.1234 '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                   9.0493(9)
_cell_length_b                   9.3379(9)
_cell_length_c                   9.6639(9)
_cell_angle_alpha                86.8130(10)
_cell_angle_beta                 85.7700(10)
_cell_angle_gamma                82.6970(10)
_cell_volume                     806.90(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3315
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.51

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6443
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.274
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3439
_reflns_number_gt                2880
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0648P)²+0.3547P] 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         3439
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.9716(2) 0.2669(2) 0.5142(2) 0.0453(5) Uani 1 1 d . . . . .
H1A H 1.047652 0.196465 0.484468 0.054 Uiso 1 1 calc R U . . .
C2 C 0.9301(2) 0.2754(2) 0.6546(2) 0.0418(4) Uani 1 1 d . . . . .
H2A H 0.977975 0.209519 0.717430 0.050 Uiso 1 1 calc R U . . .
C3 C 0.8182(2) 0.38039(19) 0.70388(18) 0.0349(4) Uani 1 1 d . . . . .
H3A H 0.790803 0.385605 0.798303 0.042 Uiso 1 1 calc R U . . .
C4 C 0.74901(19) 0.47695(18) 0.60711(17) 0.0293(3) Uani 1 1 d . . . . .
C5 C 0.7889(2) 0.4664(2) 0.46535(18) 0.0336(4) Uani 1 1 d . . . . .
C6 C 0.9011(2) 0.3622(2) 0.4173(2) 0.0420(4) Uani 1 1 d . . . . .
H6A H 0.928342 0.356310 0.322893 0.050 Uiso 1 1 calc R U . . .
C7 C 0.58690(19) 0.66773(19) 0.51743(16) 0.0293(4) Uani 1 1 d . . . . .
C8 C 0.58716(18) 0.64085(18) 0.77444(15) 0.0266(3) Uani 1 1 d . . . . .
H8A H 0.554134 0.559334 0.831578 0.032 Uiso 1 1 calc R U . . .
C9 C 0.45648(18) 0.75990(18) 0.76303(16) 0.0278(3) Uani 1 1 d . . . . .
C10 C 0.41353(19) 0.82138(19) 0.64045(17) 0.0300(4) Uani 1 1 d . . . . .
C11 C 0.2889(2) 0.9422(2) 0.6213(2) 0.0399(4) Uani 1 1 d . . . . .
H11A H 0.281121 0.966157 0.523978 0.060 Uiso 1 1 calc R U . . .
H11B H 0.196595 0.912084 0.660570 0.060 Uiso 1 1 calc R U . . .
H11C H 0.309365 1.025454 0.667078 0.060 Uiso 1 1 calc R U . . .
C12 C 0.38854(19) 0.8026(2) 0.90253(17) 0.0318(4) Uani 1 1 d . . . . .
C13 C 0.71571(18) 0.69580(18) 0.84160(16) 0.0279(3) Uani 1 1 d . . . . .
C14 C 0.7732(2) 0.6265(2) 0.96105(19) 0.0419(4) Uani 1 1 d . . . . .
H14A H 0.731530 0.547255 1.002356 0.050 Uiso 1 1 calc R U . . .
C15 C 0.8922(3) 0.6756(3) 1.0183(2) 0.0535(6) Uani 1 1 d . . . . .
H15A H 0.930291 0.628989 1.098046 0.064 Uiso 1 1 calc R U . . .
C16 C 0.9548(2) 0.7932(3) 0.9579(2) 0.0527(6) Uani 1 1 d . . . . .
H16A H 1.036428 0.824218 0.995288 0.063 Uiso 1 1 calc R U . . .
C17 C 0.8956(2) 0.8648(2) 0.8415(2) 0.0449(5) Uani 1 1 d . . . . .
H17A H 0.936178 0.945353 0.801874 0.054 Uiso 1 1 calc R U . . .
C18 C 0.7758(2) 0.8168(2) 0.78369(18) 0.0342(4) Uani 1 1 d . . . . .
H18A H 0.735796 0.865915 0.705979 0.041 Uiso 1 1 calc R U . . .
N1 N 0.63681(16) 0.59221(15) 0.63353(13) 0.0285(3) Uani 1 1 d . . . . .
N2 N 0.48278(17) 0.77635(17) 0.51209(14) 0.0333(3) Uani 1 1 d . . . . .
N3 N 0.3592(2) 0.94308(18) 0.92367(17) 0.0448(4) Uani 1 1 d . . . . .
H3B H 0.323428 0.971736 1.003756 0.054 Uiso 1 1 calc R U . . .
H3C H 0.376067 1.005327 0.857256 0.054 Uiso 1 1 calc R U . . .
O1 O 0.36606(17) 0.70952(16) 0.99500(13) 0.0480(4) Uani 1 1 d . . . . .
O2 O 0.4510(2) 0.86309(19) 0.22919(17) 0.0569(5) Uani 1 1 d . . . . .
S1 S 0.68241(5) 0.59789(5) 0.36630(4) 0.03811(16) Uani 1 1 d . . . . .
H1O H 0.442(3) 0.834(3) 0.314(3) 0.059(7) Uiso 1 1 d . . . . .
H2O H 0.423(3) 0.801(3) 0.183(3) 0.070(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
C1 C2 1.385(3) . ?
C1 C6 1.388(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.396(2) . ?
C4 N1 1.403(2) . ?
C5 C6 1.387(3) . ?
C5 S1 1.748(2) . ?
C6 H6A 0.9300 . ?
C7 N2 1.295(2) . ?
C7 N1 1.366(2) . ?
C7 S1 1.7555(17) . ?
C8 N1 1.4796(19) . ?
C8 C9 1.522(2) . ?
C8 C13 1.529(2) . ?
C8 H8A 0.9800 . ?
C9 C10 1.349(2) . ?
C9 C12 1.493(2) . ?
C10 N2 1.409(2) . ?
C10 C11 1.505(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O1 1.236(2) . ?
C12 N3 1.329(2) . ?
C13 C18 1.388(2) . ?
C13 C14 1.393(2) . ?
C14 C15 1.386(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.381(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.383(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.389(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
N3 H3B 0.8600 . ?
N3 H3C 0.8600 . ?
O2 H1O 0.85(3) . ?
O2 H2O 0.83(3) . ?

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 120.77(19) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 C3 121.56(19) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C4 C3 C2 117.68(16) . . ?
C4 C3 H3A 121.2 . . ?
C2 C3 H3A 121.2 . . ?
C3 C4 C5 120.73(16) . . ?
C3 C4 N1 127.28(15) . . ?
C5 C4 N1 111.98(15) . . ?
C6 C5 C4 121.17(18) . . ?
C6 C5 S1 127.31(14) . . ?
C4 C5 S1 111.53(14) . . ?
C5 C6 C1 118.08(17) . . ?
C5 C6 H6A 121.0 . . ?
C1 C6 H6A 121.0 . . ?
N2 C7 N1 127.23(15) . . ?
N2 C7 S1 121.65(13) . . ?
N1 C7 S1 111.11(13) . . ?
N1 C8 C9 108.66(13) . . ?
N1 C8 C13 110.24(13) . . ?
C9 C8 C13 110.59(13) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C13 C8 H8A 109.1 . . ?
C10 C9 C12 125.23(16) . . ?
C10 C9 C8 122.95(15) . . ?
C12 C9 C8 111.77(14) . . ?
C9 C10 N2 122.46(16) . . ?
C9 C10 C11 125.94(16) . . ?
N2 C10 C11 111.60(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 N3 122.14(16) . . ?
O1 C12 C9 120.43(16) . . ?
N3 C12 C9 117.39(15) . . ?
C18 C13 C14 119.31(16) . . ?
C18 C13 C8 119.80(15) . . ?
C14 C13 C8 120.89(16) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 119.72(19) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C13 C18 C17 120.15(18) . . ?
C13 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C7 N1 C4 114.56(14) . . ?
C7 N1 C8 121.43(14) . . ?
C4 N1 C8 123.64(13) . . ?
C7 N2 C10 116.24(14) . . ?
C12 N3 H3B 120.0 . . ?
C12 N3 H3C 120.0 . . ?
H3B N3 H3C 120.0 . . ?
H1O O2 H2O 107(2) . . ?
C5 S1 C7 90.79(8) . . ?

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 -0.9(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C2 C3 C4 N1 -178.54(16) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
N1 C4 C5 C6 178.06(16) . . . . ?
C3 C4 C5 S1 178.66(13) . . . . ?
N1 C4 C5 S1 -1.49(18) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
S1 C5 C6 C1 -179.62(15) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C8 C9 C10 -9.2(2) . . . . ?
C13 C8 C9 C10 111.96(17) . . . . ?
N1 C8 C9 C12 173.28(13) . . . . ?
C13 C8 C9 C12 -65.59(17) . . . . ?
C12 C9 C10 N2 179.74(15) . . . . ?
C8 C9 C10 N2 2.5(3) . . . . ?
C12 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C10 C11 -178.05(15) . . . . ?
C10 C9 C12 O1 138.95(19) . . . . ?
C8 C9 C12 O1 -43.6(2) . . . . ?
C10 C9 C12 N3 -43.5(2) . . . . ?
C8 C9 C12 N3 133.98(17) . . . . ?
N1 C8 C13 C18 63.94(19) . . . . ?
C9 C8 C13 C18 -56.24(19) . . . . ?
N1 C8 C13 C14 -116.45(17) . . . . ?
C9 C8 C13 C14 123.37(17) . . . . ?
C18 C13 C14 C15 -2.1(3) . . . . ?
C8 C13 C14 C15 178.31(18) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 1.7(3) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C14 C13 C18 C17 2.4(3) . . . . ?
C8 C13 C18 C17 -178.01(16) . . . . ?
C16 C17 C18 C13 -0.6(3) . . . . ?
N2 C7 N1 C4 178.52(16) . . . . ?
S1 C7 N1 C4 -0.90(17) . . . . ?
N2 C7 N1 C8 -8.2(3) . . . . ?
S1 C7 N1 C8 172.41(11) . . . . ?
C3 C4 N1 C7 -178.61(16) . . . . ?
C5 C4 N1 C7 1.6(2) . . . . ?
C3 C4 N1 C8 8.3(3) . . . . ?
C5 C4 N1 C8 -171.58(14) . . . . ?
C9 C8 N1 C7 11.6(2) . . . . ?
C13 C8 N1 C7 -109.73(16) . . . . ?
C9 C8 N1 C4 -175.71(13) . . . . ?
C13 C8 N1 C4 62.96(19) . . . . ?
N1 C7 N2 C10 0.0(3) . . . . ?
S1 C7 N2 C10 179.38(12) . . . . ?
C9 C10 N2 C7 2.8(2) . . . . ?
C11 C10 N2 C7 -176.71(15) . . . . ?
C6 C5 S1 C7 -178.68(17) . . . . ?
C4 C5 S1 C7 0.84(13) . . . . ?
N2 C7 S1 C5 -179.44(15) . . . . ?
N1 C7 S1 C5 0.02(13) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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 2083670'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 N2 O S'
_chemical_formula_weight         318.38

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'
O O 0.0106 0.0060 '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      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                   7.8993(5)
_cell_length_b                   19.1467(13)
_cell_length_c                   19.7329(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2984.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4743
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.03

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.223
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16934
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.965
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3448
_reflns_number_gt                2701
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0505P)²+1.1948P] 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         3448
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.2210(3) 0.72778(10) 0.49083(10) 0.0466(5) Uani 1 1 d . . . . .
H1A H 0.295320 0.757667 0.464569 0.056 Uiso 1 1 calc R U . . .
H1B H 0.109326 0.748823 0.492206 0.056 Uiso 1 1 calc R U . . .
C2 C 0.2893(2) 0.71810(8) 0.56160(9) 0.0331(4) Uani 1 1 d . . . . .
C3 C 0.32312(19) 0.64464(8) 0.57087(8) 0.0273(3) Uani 1 1 d . . . . .
C4 C 0.2767(2) 0.60801(9) 0.51512(8) 0.0318(3) Uani 1 1 d . . . . .
C5 C 0.2124(3) 0.65460(10) 0.45949(9) 0.0446(4) Uani 1 1 d . . . . .
H5A H 0.097105 0.642582 0.447173 0.054 Uiso 1 1 calc R U . . .
H5B H 0.283619 0.651397 0.419578 0.054 Uiso 1 1 calc R U . . .
C6 C 0.39650(19) 0.61128(7) 0.63311(8) 0.0252(3) Uani 1 1 d . . . . .
H6A H 0.334300 0.627838 0.672965 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3200(2) 0.50518(8) 0.56583(8) 0.0293(3) Uani 1 1 d . . . . .
C8 C 0.39688(19) 0.48781(8) 0.67809(8) 0.0283(3) Uani 1 1 d . . . . .
C9 C 0.4408(2) 0.50426(8) 0.74402(8) 0.0366(4) Uani 1 1 d . . . . .
H9A H 0.457323 0.550365 0.757280 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4593(3) 0.44995(9) 0.78961(9) 0.0436(4) Uani 1 1 d . . . . .
H10A H 0.487434 0.459838 0.834362 0.052 Uiso 1 1 calc R U . . .
C11 C 0.4369(3) 0.38105(9) 0.76994(9) 0.0447(4) Uani 1 1 d . . . . .
H11A H 0.452016 0.345464 0.801432 0.054 Uiso 1 1 calc R U . . .
C12 C 0.3924(2) 0.36462(8) 0.70427(9) 0.0396(4) Uani 1 1 d . . . . .
H12A H 0.376783 0.318401 0.691200 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3713(2) 0.41874(8) 0.65808(8) 0.0309(3) Uani 1 1 d . . . . .
C14 C 0.5832(2) 0.62895(7) 0.64160(7) 0.0254(3) Uani 1 1 d . . . . .
C15 C 0.6279(2) 0.68754(8) 0.67921(8) 0.0324(4) Uani 1 1 d . . . . .
H15A H 0.544347 0.713200 0.701207 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7950(2) 0.70799(9) 0.68421(9) 0.0386(4) Uani 1 1 d . . . . .
H16A H 0.823429 0.747144 0.709671 0.046 Uiso 1 1 calc R U . . .
C17 C 0.9201(2) 0.67050(10) 0.65155(9) 0.0401(4) Uani 1 1 d . . . . .
H17A H 1.032588 0.684399 0.654832 0.048 Uiso 1 1 calc R U . . .
C18 C 0.8773(2) 0.61227(9) 0.61399(9) 0.0377(4) Uani 1 1 d . . . . .
H18A H 0.961187 0.587093 0.591728 0.045 Uiso 1 1 calc R U . . .
C19 C 0.7094(2) 0.59109(8) 0.60927(8) 0.0309(3) Uani 1 1 d . . . . .
H19A H 0.681537 0.551471 0.584388 0.037 Uiso 1 1 calc R U . . .
N1 N 0.2779(2) 0.53685(7) 0.50922(7) 0.0374(3) Uani 1 1 d . . . . .
N2 N 0.36790(17) 0.53526(6) 0.62525(6) 0.0268(3) Uani 1 1 d . . . . .
O1 O 0.30796(18) 0.76452(6) 0.60382(7) 0.0465(3) Uani 1 1 d . . . . .
S1 S 0.30782(6) 0.41458(2) 0.57323(2) 0.03681(13) 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 1.508(2) . ?
C1 C5 1.533(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O1 1.227(2) . ?
C2 C3 1.443(2) . ?
C3 C4 1.355(2) . ?
C3 C6 1.501(2) . ?
C4 N1 1.368(2) . ?
C4 C5 1.503(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N2 1.4811(17) . ?
C6 C14 1.522(2) . ?
C6 H6A 0.9800 . ?
C7 N1 1.314(2) . ?
C7 N2 1.3600(19) . ?
C7 S1 1.7435(16) . ?
C8 C9 1.383(2) . ?
C8 C13 1.395(2) . ?
C8 N2 1.4017(19) . ?
C9 C10 1.383(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.387(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.379(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.390(2) . ?
C12 H12A 0.9300 . ?
C13 S1 1.7496(17) . ?
C14 C19 1.388(2) . ?
C14 C15 1.391(2) . ?
C15 C16 1.381(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.390(2) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 106.08(14) . . ?
C2 C1 H1A 110.5 . . ?
C5 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
C5 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
O1 C2 C3 126.69(16) . . ?
O1 C2 C1 125.63(16) . . ?
C3 C2 C1 107.66(15) . . ?
C4 C3 C2 110.56(14) . . ?
C4 C3 C6 123.28(14) . . ?
C2 C3 C6 126.16(14) . . ?
C3 C4 N1 125.64(15) . . ?
C3 C4 C5 112.17(15) . . ?
N1 C4 C5 122.11(15) . . ?
C4 C5 C1 103.46(15) . . ?
C4 C5 H5A 111.1 . . ?
C1 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
C1 C5 H5B 111.1 . . ?
H5A C5 H5B 109.0 . . ?
N2 C6 C3 105.89(12) . . ?
N2 C6 C14 112.19(12) . . ?
C3 C6 C14 111.70(12) . . ?
N2 C6 H6A 109.0 . . ?
C3 C6 H6A 109.0 . . ?
C14 C6 H6A 109.0 . . ?
N1 C7 N2 127.45(14) . . ?
N1 C7 S1 121.08(12) . . ?
N2 C7 S1 111.37(11) . . ?
C9 C8 C13 121.23(14) . . ?
C9 C8 N2 126.38(14) . . ?
C13 C8 N2 112.35(14) . . ?
C8 C9 C10 117.87(15) . . ?
C8 C9 H9A 121.1 . . ?
C10 C9 H9A 121.1 . . ?
C9 C10 C11 121.31(16) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C12 C11 C10 120.85(16) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C11 C12 C13 118.47(15) . . ?
C11 C12 H12A 120.8 . . ?
C13 C12 H12A 120.8 . . ?
C12 C13 C8 120.25(15) . . ?
C12 C13 S1 128.90(12) . . ?
C8 C13 S1 110.82(12) . . ?
C19 C14 C15 118.98(15) . . ?
C19 C14 C6 121.94(13) . . ?
C15 C14 C6 118.93(14) . . ?
C16 C15 C14 120.63(15) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 120.23(16) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C18 C17 C16 119.66(16) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C17 C18 C19 120.35(16) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C14 C19 C18 120.14(15) . . ?
C14 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
C7 N1 C4 112.90(14) . . ?
C7 N2 C8 114.35(13) . . ?
C7 N2 C6 123.28(12) . . ?
C8 N2 C6 122.29(12) . . ?
C7 S1 C13 91.09(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
C5 C1 C2 O1 -176.82(17) . . . . ?
C5 C1 C2 C3 1.4(2) . . . . ?
O1 C2 C3 C4 175.62(17) . . . . ?
C1 C2 C3 C4 -2.62(19) . . . . ?
O1 C2 C3 C6 -3.4(3) . . . . ?
C1 C2 C3 C6 178.36(15) . . . . ?
C2 C3 C4 N1 -174.05(15) . . . . ?
C6 C3 C4 N1 5.0(3) . . . . ?
C2 C3 C4 C5 2.8(2) . . . . ?
C6 C3 C4 C5 -178.16(15) . . . . ?
C3 C4 C5 C1 -1.7(2) . . . . ?
N1 C4 C5 C1 175.22(16) . . . . ?
C2 C1 C5 C4 0.1(2) . . . . ?
C4 C3 C6 N2 -12.5(2) . . . . ?
C2 C3 C6 N2 166.37(14) . . . . ?
C4 C3 C6 C14 109.86(16) . . . . ?
C2 C3 C6 C14 -71.23(19) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
N2 C8 C9 C10 178.17(16) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C8 0.7(3) . . . . ?
C11 C12 C13 S1 -177.22(15) . . . . ?
C9 C8 C13 C12 -1.0(3) . . . . ?
N2 C8 C13 C12 -179.21(15) . . . . ?
C9 C8 C13 S1 177.26(13) . . . . ?
N2 C8 C13 S1 -0.93(17) . . . . ?
N2 C6 C14 C19 33.96(19) . . . . ?
C3 C6 C14 C19 -84.75(17) . . . . ?
N2 C6 C14 C15 -150.41(13) . . . . ?
C3 C6 C14 C15 90.88(16) . . . . ?
C19 C14 C15 C16 0.2(2) . . . . ?
C6 C14 C15 C16 -175.55(15) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C15 C14 C19 C18 -0.8(2) . . . . ?
C6 C14 C19 C18 174.85(14) . . . . ?
C17 C18 C19 C14 0.9(2) . . . . ?
N2 C7 N1 C4 -3.4(2) . . . . ?
S1 C7 N1 C4 172.92(12) . . . . ?
C3 C4 N1 C7 4.0(2) . . . . ?
C5 C4 N1 C7 -172.56(16) . . . . ?
N1 C7 N2 C8 176.84(16) . . . . ?
S1 C7 N2 C8 0.24(17) . . . . ?
N1 C7 N2 C6 -6.3(3) . . . . ?
S1 C7 N2 C6 177.05(11) . . . . ?
C9 C8 N2 C7 -177.61(16) . . . . ?
C13 C8 N2 C7 0.46(19) . . . . ?
C9 C8 N2 C6 5.5(2) . . . . ?
C13 C8 N2 C6 -176.40(13) . . . . ?
C3 C6 N2 C7 13.15(19) . . . . ?
C14 C6 N2 C7 -108.93(16) . . . . ?
C3 C6 N2 C8 -170.28(13) . . . . ?
C14 C6 N2 C8 67.63(18) . . . . ?
N1 C7 S1 C13 -177.50(15) . . . . ?
N2 C7 S1 C13 -0.65(12) . . . . ?
C12 C13 S1 C7 178.98(17) . . . . ?
C8 C13 S1 C7 0.89(13) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2083673'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 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            'C44 H40 N4 O2 S2'
_chemical_formula_weight         720.92

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'
S S 0.1246 0.1234 '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                   9.482(3)
_cell_length_b                   9.587(3)
_cell_length_c                   23.807(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                118.997(5)
_cell_volume                     1892.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    997
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      21.72

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9367
_diffrn_reflns_av_unetI/netI     0.1668
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         0.855
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             6585
_reflns_number_gt                2725
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0804P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6585
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1935
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_restrained_S_all      0.870
_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 1.2703(7) 1.2739(7) 0.4761(3) 0.0704(17) Uani 1 1 d . . . . .
H1A H 1.3738 1.3393 0.4898 0.084 Uiso 1 1 calc R U . . .
C2 C 1.1431(7) 1.2939(6) 0.4961(2) 0.0647(16) Uani 1 1 d . . . . .
H2A H 1.1621 1.3713 0.5230 0.078 Uiso 1 1 calc R U . . .
C3 C 0.9882(7) 1.1985(6) 0.4758(2) 0.0541(14) Uani 1 1 d . . . . .
H3A H 0.9025 1.2111 0.4888 0.065 Uiso 1 1 calc R U . . .
C4 C 0.9644(6) 1.0845(5) 0.4361(2) 0.0432(12) Uani 1 1 d . . . . .
C6 C 1.2457(7) 1.1583(7) 0.4363(3) 0.0661(16) Uani 1 1 d . . . . .
H6A H 1.3306 1.1443 0.4235 0.079 Uiso 1 1 calc R U . . .
C7 C 0.6641(5) 0.9817(5) 0.4179(2) 0.0422(12) Uani 1 1 d . . . . .
H7A H 0.6472 0.9944 0.4578 0.051 Uiso 1 1 calc R U . . .
C8 C 0.6745(5) 1.1235(5) 0.3855(2) 0.0417(12) Uani 1 1 d . . . . .
C9 C 0.6703(6) 1.2489(5) 0.4123(2) 0.0508(13) Uani 1 1 d . . . . .
H9A H 0.6624 1.2484 0.4513 0.061 Uiso 1 1 calc R U . . .
C10 C 0.6778(6) 1.3749(6) 0.3822(3) 0.0619(16) Uani 1 1 d . . . . .
H10A H 0.6740 1.4583 0.4008 0.074 Uiso 1 1 calc R U . . .
C11 C 0.6907(6) 1.3778(6) 0.3248(3) 0.0599(15) Uani 1 1 d . . . . .
H11A H 0.6972 1.4637 0.3046 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6941(6) 1.2544(6) 0.2974(2) 0.0561(14) Uani 1 1 d . . . . .
H12A H 0.7023 1.2556 0.2585 0.067 Uiso 1 1 calc R U . . .
C13 C 0.6852(6) 1.1283(5) 0.3277(2) 0.0497(13) Uani 1 1 d . . . . .
H13A H 0.6865 1.0441 0.3087 0.060 Uiso 1 1 calc R U . . .
C14 C 0.5289(6) 0.8243(5) 0.39764(19) 0.0397(12) Uani 1 1 d . . . . .
C15 C 0.5562(6) 0.7264(5) 0.3637(2) 0.0421(12) Uani 1 1 d . . . . .
C16 C 0.8284(6) 0.8724(6) 0.3748(2) 0.0439(13) Uani 1 1 d . . . . .
C17 C 0.3678(6) 0.7870(6) 0.4142(2) 0.0468(13) Uani 1 1 d . . . . .
C18 C 0.2301(6) 0.6327(6) 0.3920(2) 0.0536(14) Uani 1 1 d . . . . .
H18A H 0.1347 0.6451 0.3891 0.064 Uiso 1 1 calc R U . . .
H18B H 0.2071 0.5487 0.4191 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2611(6) 0.5801(5) 0.3351(2) 0.0501(13) Uani 1 1 d . . . . .
C20 C 0.2688(7) 0.6953(6) 0.2899(2) 0.0704(17) Uani 1 1 d . . . . .
H20A H 0.2883 0.6617 0.2542 0.106 Uiso 1 1 calc R U . . .
H20B H 0.1683 0.6968 0.2887 0.106 Uiso 1 1 calc R U . . .
H20C H 0.3546 0.8004 0.2983 0.106 Uiso 1 1 calc R U . . .
C21 C 0.1252(6) 0.4113(6) 0.3210(3) 0.0767(18) Uani 1 1 d . . . . .
H21A H 0.1200 0.3381 0.3495 0.115 Uiso 1 1 calc R U . . .
H21B H 0.0242 0.4117 0.3193 0.115 Uiso 1 1 calc R U . . .
H21C H 0.1467 0.3789 0.2853 0.115 Uiso 1 1 calc R U . . .
C22 C 0.4203(6) 0.5772(5) 0.3391(2) 0.0517(13) Uani 1 1 d . . . . .
H22A H 0.4041 0.4869 0.3620 0.062 Uiso 1 1 calc R U . . .
H22B H 0.4511 0.5614 0.3018 0.062 Uiso 1 1 calc R U . . .
C23 C 1.2698(7) 0.7747(7) 0.0241(3) 0.0697(17) Uani 1 1 d . . . . .
H23A H 1.3736 0.8405 0.0109 0.084 Uiso 1 1 calc R U . . .
C24 C 1.2440(7) 0.6583(6) 0.0634(2) 0.0634(16) Uani 1 1 d . . . . .
H24A H 1.3291 0.6444 0.0761 0.076 Uiso 1 1 calc R U . . .
C25 C 1.0904(6) 0.5635(5) 0.0834(2) 0.0488(13) Uani 1 1 d . . . . .
C26 C 0.9640(6) 0.5850(5) 0.0638(2) 0.0426(12) Uani 1 1 d . . . . .
C27 C 0.9878(6) 0.6984(5) 0.0237(2) 0.0509(13) Uani 1 1 d . . . . .
H27A H 0.9022 0.7101 0.0101 0.061 Uiso 1 1 calc R U . . .
C28 C 1.1445(7) 0.7948(6) 0.0044(2) 0.0613(15) Uani 1 1 d . . . . .
H28A H 1.1645 0.8735 -0.0222 0.074 Uiso 1 1 calc R U . . .
C29 C 0.8260(6) 0.3715(6) 0.1249(2) 0.0443(13) Uani 1 1 d . . . . .
C30 C 0.5558(6) 0.2262(5) 0.13626(19) 0.0403(12) Uani 1 1 d . . . . .
C31 C 0.5301(5) 0.3255(5) 0.10244(18) 0.0394(12) Uani 1 1 d . . . . .
C32 C 0.6745(5) 0.6236(5) 0.1147(2) 0.0407(12) Uani 1 1 d . . . . .
C33 C 0.6705(6) 0.7494(5) 0.0872(2) 0.0487(13) Uani 1 1 d . . . . .
H33A H 0.6627 0.7486 0.0482 0.058 Uiso 1 1 calc R U . . .
C34 C 0.6782(6) 0.8755(6) 0.1175(3) 0.0648(16) Uani 1 1 d . . . . .
H34A H 0.6743 0.9586 0.0987 0.078 Uiso 1 1 calc R U . . .
C35 C 0.6913(6) 0.8801(6) 0.1750(3) 0.0612(15) Uani 1 1 d . . . . .
H35A H 0.6995 0.9669 0.1950 0.073 Uiso 1 1 calc R U . . .
C36 C 0.6923(6) 0.7541(6) 0.2026(2) 0.0564(14) Uani 1 1 d . . . . .
H36A H 0.6986 0.7546 0.2416 0.068 Uiso 1 1 calc R U . . .
C37 C 0.6840(6) 0.6280(6) 0.1726(2) 0.0501(13) Uani 1 1 d . . . . .
H37A H 0.6848 0.5437 0.1917 0.060 Uiso 1 1 calc R U . . .
C38 C 0.4211(6) 0.0781(5) 0.1608(2) 0.0512(14) Uani 1 1 d . . . . .
H38A H 0.4521 0.0631 0.1982 0.061 Uiso 1 1 calc R U . . .
H38B H 0.4060 -0.0122 0.1382 0.061 Uiso 1 1 calc R U . . .
C39 C 0.2609(6) 0.0783(5) 0.1646(2) 0.0506(13) Uani 1 1 d . . . . .
C40 C 0.2706(7) 0.1957(6) 0.2104(2) 0.0754(17) Uani 1 1 d . . . . .
H40A H 0.3556 0.3007 0.2015 0.113 Uiso 1 1 calc R U . . .
H40B H 0.1699 0.1966 0.2123 0.113 Uiso 1 1 calc R U . . .
H40C H 0.2923 0.1630 0.2460 0.113 Uiso 1 1 calc R U . . .
C41 C 0.1263(6) -0.0877(6) 0.1789(3) 0.0763(18) Uani 1 1 d . . . . .
H41A H 0.0259 -0.0863 0.1812 0.114 Uiso 1 1 calc R U . . .
H41B H 0.1192 -0.1611 0.1501 0.114 Uiso 1 1 calc R U . . .
H41C H 0.1487 -0.1206 0.2143 0.114 Uiso 1 1 calc R U . . .
C42 C 0.2293(6) 0.1320(6) 0.1077(2) 0.0550(14) Uani 1 1 d . . . . .
H42A H 0.2061 0.0486 0.0803 0.066 Uiso 1 1 calc R U . . .
H42B H 0.1342 0.1448 0.1108 0.066 Uiso 1 1 calc R U . . .
C43 C 0.3661(6) 0.2848(5) 0.0863(2) 0.0461(13) Uani 1 1 d . . . . .
O2 O 0.3423(4) 0.3743(4) 0.05470(14) 0.0642(10) Uani 1 1 d . . . . .
C45 C 1.0907(6) 1.0649(5) 0.4163(2) 0.0500(13) Uani 1 1 d . . . . .
C46 C 0.6648(5) 0.4824(5) 0.08179(19) 0.0433(12) Uani 1 1 d . . . . .
H46A H 0.6484 0.4952 0.0419 0.052 Uiso 1 1 calc R U . . .
N1 N 0.8171(5) 0.9762(4) 0.41165(16) 0.0425(10) Uani 1 1 d . . . . .
N2 N 0.7073(5) 0.7526(5) 0.34884(17) 0.0488(11) Uani 1 1 d . . . . .
N3 N 0.8182(5) 0.4760(4) 0.08891(16) 0.0423(10) Uani 1 1 d . . . . .
N4 N 0.7103(5) 0.2533(5) 0.15122(17) 0.0493(11) Uani 1 1 d . . . . .
O1 O 0.3424(4) 0.8744(4) 0.44519(15) 0.0635(10) Uani 1 1 d . . . . .
S1 S 1.02555(17) 0.91018(16) 0.36796(6) 0.0624(5) Uani 1 1 d . . . . .
S2 S 1.02547(16) 0.41037(16) 0.13193(6) 0.0624(5) 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 C6 1.391(7) . ?
C1 C2 1.393(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.387(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(6) . ?
C3 H3A 0.9300 . ?
C4 C45 1.382(6) . ?
C4 N1 1.401(6) . ?
C6 C45 1.382(7) . ?
C6 H6A 0.9300 . ?
C7 N1 1.484(5) . ?
C7 C14 1.509(6) . ?
C7 C8 1.524(6) . ?
C7 H7A 0.9800 . ?
C8 C13 1.378(6) . ?
C8 C9 1.379(6) . ?
C9 C10 1.376(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.370(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.365(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(6) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.355(6) . ?
C14 C17 1.444(6) . ?
C15 N2 1.376(6) . ?
C15 C22 1.504(6) . ?
C16 N2 1.319(6) . ?
C16 N1 1.369(6) . ?
C16 S1 1.731(5) . ?
C17 O1 1.225(5) . ?
C17 C18 1.517(6) . ?
C18 C19 1.523(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.519(6) . ?
C19 C22 1.526(6) . ?
C19 C21 1.540(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C28 1.376(7) . ?
C23 C24 1.384(7) . ?
C23 H23A 0.9300 . ?
C24 C25 1.375(6) . ?
C24 H24A 0.9300 . ?
C25 C26 1.391(6) . ?
C25 S2 1.730(5) . ?
C26 C27 1.381(6) . ?
C26 N3 1.400(5) . ?
C27 C28 1.393(6) . ?
C27 H27A 0.9300 . ?
C28 H28A 0.9300 . ?
C29 N4 1.295(5) . ?
C29 N3 1.347(5) . ?
C29 S2 1.750(5) . ?
C30 C31 1.357(5) . ?
C30 N4 1.404(5) . ?
C30 C38 1.493(6) . ?
C31 C43 1.459(6) . ?
C31 C46 1.507(6) . ?
C32 C37 1.380(6) . ?
C32 C33 1.389(5) . ?
C32 C46 1.528(6) . ?
C33 C34 1.379(6) . ?
C33 H33A 0.9300 . ?
C34 C35 1.373(7) . ?
C34 H34A 0.9300 . ?
C35 C36 1.379(6) . ?
C35 H35A 0.9300 . ?
C36 C37 1.373(6) . ?
C36 H36A 0.9300 . ?
C37 H37A 0.9300 . ?
C38 C39 1.523(6) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C41 1.519(6) . ?
C39 C42 1.531(6) . ?
C39 C40 1.537(7) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C43 1.498(6) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 O2 1.242(5) . ?
C45 S1 1.738(5) . ?
C46 N3 1.495(5) . ?
C46 H46A 0.9800 . ?

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 C1 C2 121.4(6) . . ?
C6 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C3 C2 C1 120.1(6) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 118.4(5) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
C3 C4 C45 121.4(5) . . ?
C3 C4 N1 126.5(5) . . ?
C45 C4 N1 112.1(4) . . ?
C45 C6 C1 117.8(5) . . ?
C45 C6 H6A 121.1 . . ?
C1 C6 H6A 121.1 . . ?
N1 C7 C14 107.7(3) . . ?
N1 C7 C8 109.8(4) . . ?
C14 C7 C8 112.7(4) . . ?
N1 C7 H7A 108.8 . . ?
C14 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C13 C8 C9 117.7(4) . . ?
C13 C8 C7 120.4(4) . . ?
C9 C8 C7 121.8(4) . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C11 C10 C9 120.2(5) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C12 C11 C10 119.9(5) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C13 119.6(5) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C12 C13 C8 121.7(5) . . ?
C12 C13 H13A 119.2 . . ?
C8 C13 H13A 119.2 . . ?
C15 C14 C17 121.7(5) . . ?
C15 C14 C7 121.9(4) . . ?
C17 C14 C7 116.4(4) . . ?
C14 C15 N2 124.0(5) . . ?
C14 C15 C22 121.8(5) . . ?
N2 C15 C22 114.2(4) . . ?
N2 C16 N1 126.3(4) . . ?
N2 C16 S1 122.2(4) . . ?
N1 C16 S1 111.4(4) . . ?
O1 C17 C14 122.0(5) . . ?
O1 C17 C18 121.0(5) . . ?
C14 C17 C18 117.0(5) . . ?
C17 C18 C19 114.8(4) . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 109.8(4) . . ?
C20 C19 C22 111.0(4) . . ?
C18 C19 C22 107.6(4) . . ?
C20 C19 C21 109.3(4) . . ?
C18 C19 C21 110.2(4) . . ?
C22 C19 C21 109.0(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 C22 C19 114.0(4) . . ?
C15 C22 H22A 108.8 . . ?
C19 C22 H22A 108.8 . . ?
C15 C22 H22B 108.8 . . ?
C19 C22 H22B 108.8 . . ?
H22A C22 H22B 107.6 . . ?
C28 C23 C24 121.1(5) . . ?
C28 C23 H23A 119.4 . . ?
C24 C23 H23A 119.4 . . ?
C25 C24 C23 118.9(5) . . ?
C25 C24 H24A 120.5 . . ?
C23 C24 H24A 120.5 . . ?
C24 C25 C26 119.9(5) . . ?
C24 C25 S2 128.2(4) . . ?
C26 C25 S2 111.9(4) . . ?
C27 C26 C25 121.7(5) . . ?
C27 C26 N3 127.4(4) . . ?
C25 C26 N3 110.9(4) . . ?
C26 C27 C28 117.8(5) . . ?
C26 C27 H27A 121.1 . . ?
C28 C27 H27A 121.1 . . ?
C23 C28 C27 120.6(5) . . ?
C23 C28 H28A 119.7 . . ?
C27 C28 H28A 119.7 . . ?
N4 C29 N3 129.1(4) . . ?
N4 C29 S2 120.6(3) . . ?
N3 C29 S2 110.3(4) . . ?
C31 C30 N4 123.2(4) . . ?
C31 C30 C38 122.5(4) . . ?
N4 C30 C38 114.3(4) . . ?
C30 C31 C43 120.0(4) . . ?
C30 C31 C46 122.7(4) . . ?
C43 C31 C46 117.3(4) . . ?
C37 C32 C33 118.3(4) . . ?
C37 C32 C46 120.9(4) . . ?
C33 C32 C46 120.8(4) . . ?
C34 C33 C32 120.1(5) . . ?
C34 C33 H33A 119.9 . . ?
C32 C33 H33A 119.9 . . ?
C35 C34 C33 121.0(5) . . ?
C35 C34 H34A 119.5 . . ?
C33 C34 H34A 119.5 . . ?
C34 C35 C36 119.1(5) . . ?
C34 C35 H35A 120.5 . . ?
C36 C35 H35A 120.5 . . ?
C37 C36 C35 120.1(5) . . ?
C37 C36 H36A 119.9 . . ?
C35 C36 H36A 119.9 . . ?
C36 C37 C32 121.4(4) . . ?
C36 C37 H37A 119.3 . . ?
C32 C37 H37A 119.3 . . ?
C30 C38 C39 114.6(4) . . ?
C30 C38 H38A 108.6 . . ?
C39 C38 H38A 108.6 . . ?
C30 C38 H38B 108.6 . . ?
C39 C38 H38B 108.6 . . ?
H38A C38 H38B 107.6 . . ?
C41 C39 C38 110.1(4) . . ?
C41 C39 C42 110.4(4) . . ?
C38 C39 C42 107.8(4) . . ?
C41 C39 C40 109.3(4) . . ?
C38 C39 C40 109.7(4) . . ?
C42 C39 C40 109.5(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C39 114.3(4) . . ?
C43 C42 H42A 108.7 . . ?
C39 C42 H42A 108.7 . . ?
C43 C42 H42B 108.7 . . ?
C39 C42 H42B 108.7 . . ?
H42A C42 H42B 107.6 . . ?
O2 C43 C31 120.1(4) . . ?
O2 C43 C42 121.3(4) . . ?
C31 C43 C42 118.5(4) . . ?
C4 C45 C6 120.9(5) . . ?
C4 C45 S1 111.6(4) . . ?
C6 C45 S1 127.4(4) . . ?
N3 C46 C31 107.0(3) . . ?
N3 C46 C32 109.6(4) . . ?
C31 C46 C32 112.0(4) . . ?
N3 C46 H46A 109.4 . . ?
C31 C46 H46A 109.4 . . ?
C32 C46 H46A 109.4 . . ?
C16 N1 C4 113.8(4) . . ?
C16 N1 C7 120.8(4) . . ?
C4 N1 C7 124.9(4) . . ?
C16 N2 C15 115.3(4) . . ?
C29 N3 C26 115.8(4) . . ?
C29 N3 C46 120.5(4) . . ?
C26 N3 C46 123.4(3) . . ?
C29 N4 C30 113.9(4) . . ?
C16 S1 C45 91.0(3) . . ?
C25 S2 C29 91.1(2) . . ?

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 -0.6(7) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C3 C4 C45 -0.3(7) . . . . ?
C2 C3 C4 N1 178.9(4) . . . . ?
C2 C1 C6 C45 1.0(7) . . . . ?
N1 C7 C8 C13 66.1(6) . . . . ?
C14 C7 C8 C13 -54.0(6) . . . . ?
N1 C7 C8 C9 -115.2(5) . . . . ?
C14 C7 C8 C9 124.7(5) . . . . ?
C13 C8 C9 C10 -0.4(7) . . . . ?
C7 C8 C9 C10 -179.1(4) . . . . ?
C8 C9 C10 C11 -0.5(8) . . . . ?
C9 C10 C11 C12 0.9(8) . . . . ?
C10 C11 C12 C13 -0.3(8) . . . . ?
C11 C12 C13 C8 -0.6(8) . . . . ?
C9 C8 C13 C12 1.0(7) . . . . ?
C7 C8 C13 C12 179.7(4) . . . . ?
N1 C7 C14 C15 -19.4(5) . . . . ?
C8 C7 C14 C15 101.9(5) . . . . ?
N1 C7 C14 C17 163.3(3) . . . . ?
C8 C7 C14 C17 -75.4(5) . . . . ?
C17 C14 C15 N2 -176.8(4) . . . . ?
C7 C14 C15 N2 6.0(7) . . . . ?
C17 C14 C15 C22 3.1(6) . . . . ?
C7 C14 C15 C22 -174.1(4) . . . . ?
C15 C14 C17 O1 179.5(4) . . . . ?
C7 C14 C17 O1 -3.3(6) . . . . ?
C15 C14 C17 C18 0.0(6) . . . . ?
C7 C14 C17 C18 177.3(4) . . . . ?
O1 C17 C18 C19 150.8(4) . . . . ?
C14 C17 C18 C19 -29.7(6) . . . . ?
C17 C18 C19 C20 -68.0(5) . . . . ?
C17 C18 C19 C22 52.8(5) . . . . ?
C17 C18 C19 C21 171.6(4) . . . . ?
C14 C15 C22 C19 23.3(6) . . . . ?
N2 C15 C22 C19 -156.7(4) . . . . ?
C20 C19 C22 C15 71.0(5) . . . . ?
C18 C19 C22 C15 -49.1(5) . . . . ?
C21 C19 C22 C15 -168.6(4) . . . . ?
C28 C23 C24 C25 -1.1(8) . . . . ?
C23 C24 C25 C26 0.4(8) . . . . ?
C23 C24 C25 S2 179.7(4) . . . . ?
C24 C25 C26 C27 1.0(7) . . . . ?
S2 C25 C26 C27 -178.4(3) . . . . ?
C24 C25 C26 N3 179.4(4) . . . . ?
S2 C25 C26 N3 0.0(5) . . . . ?
C25 C26 C27 C28 -1.7(7) . . . . ?
N3 C26 C27 C28 -179.9(4) . . . . ?
C24 C23 C28 C27 0.3(8) . . . . ?
C26 C27 C28 C23 1.1(7) . . . . ?
N4 C30 C31 C43 176.6(4) . . . . ?
C38 C30 C31 C43 -3.5(7) . . . . ?
N4 C30 C31 C46 -5.6(7) . . . . ?
C38 C30 C31 C46 174.3(4) . . . . ?
C37 C32 C33 C34 0.9(7) . . . . ?
C46 C32 C33 C34 179.5(4) . . . . ?
C32 C33 C34 C35 0.6(8) . . . . ?
C33 C34 C35 C36 -1.8(8) . . . . ?
C34 C35 C36 C37 1.5(8) . . . . ?
C35 C36 C37 C32 0.0(8) . . . . ?
C33 C32 C37 C36 -1.2(7) . . . . ?
C46 C32 C37 C36 -179.8(4) . . . . ?
C31 C30 C38 C39 -22.5(7) . . . . ?
N4 C30 C38 C39 157.4(4) . . . . ?
C30 C38 C39 C41 168.7(4) . . . . ?
C30 C38 C39 C42 48.2(5) . . . . ?
C30 C38 C39 C40 -71.0(5) . . . . ?
C41 C39 C42 C43 -172.1(4) . . . . ?
C38 C39 C42 C43 -51.8(5) . . . . ?
C40 C39 C42 C43 67.5(5) . . . . ?
C30 C31 C43 O2 -179.0(4) . . . . ?
C46 C31 C43 O2 3.1(7) . . . . ?
C30 C31 C43 C42 -0.2(7) . . . . ?
C46 C31 C43 C42 -178.1(4) . . . . ?
C39 C42 C43 O2 -151.8(5) . . . . ?
C39 C42 C43 C31 29.5(6) . . . . ?
C3 C4 C45 C6 0.7(7) . . . . ?
N1 C4 C45 C6 -178.6(4) . . . . ?
C3 C4 C45 S1 178.6(3) . . . . ?
N1 C4 C45 S1 -0.7(5) . . . . ?
C1 C6 C45 C4 -1.0(7) . . . . ?
C1 C6 C45 S1 -178.5(4) . . . . ?
C30 C31 C46 N3 18.3(6) . . . . ?
C43 C31 C46 N3 -163.9(4) . . . . ?
C30 C31 C46 C32 -101.9(5) . . . . ?
C43 C31 C46 C32 75.9(5) . . . . ?
C37 C32 C46 N3 -65.5(5) . . . . ?
C33 C32 C46 N3 115.9(5) . . . . ?
C37 C32 C46 C31 53.2(6) . . . . ?
C33 C32 C46 C31 -125.4(4) . . . . ?
N2 C16 N1 C4 175.5(4) . . . . ?
S1 C16 N1 C4 -1.7(4) . . . . ?
N2 C16 N1 C7 -11.8(6) . . . . ?
S1 C16 N1 C7 171.0(3) . . . . ?
C3 C4 N1 C16 -177.7(4) . . . . ?
C45 C4 N1 C16 1.5(5) . . . . ?
C3 C4 N1 C7 10.0(7) . . . . ?
C45 C4 N1 C7 -170.8(4) . . . . ?
C14 C7 N1 C16 21.9(5) . . . . ?
C8 C7 N1 C16 -101.2(5) . . . . ?
C14 C7 N1 C4 -166.2(4) . . . . ?
C8 C7 N1 C4 70.6(5) . . . . ?
N1 C16 N2 C15 -4.4(6) . . . . ?
S1 C16 N2 C15 172.4(3) . . . . ?
C14 C15 N2 C16 7.3(6) . . . . ?
C22 C15 N2 C16 -172.6(4) . . . . ?
N4 C29 N3 C26 -175.6(5) . . . . ?
S2 C29 N3 C26 2.6(5) . . . . ?
N4 C29 N3 C46 10.3(7) . . . . ?
S2 C29 N3 C46 -171.5(3) . . . . ?
C27 C26 N3 C29 176.6(4) . . . . ?
C25 C26 N3 C29 -1.7(5) . . . . ?
C27 C26 N3 C46 -9.5(7) . . . . ?
C25 C26 N3 C46 172.2(4) . . . . ?
C31 C46 N3 C29 -20.3(5) . . . . ?
C32 C46 N3 C29 101.4(5) . . . . ?
C31 C46 N3 C26 166.1(4) . . . . ?
C32 C46 N3 C26 -72.2(5) . . . . ?
N3 C29 N4 C30 5.1(7) . . . . ?
S2 C29 N4 C30 -172.9(3) . . . . ?
C31 C30 N4 C29 -7.4(7) . . . . ?
C38 C30 N4 C29 172.7(4) . . . . ?
N2 C16 S1 C45 -176.2(4) . . . . ?
N1 C16 S1 C45 1.0(3) . . . . ?
C4 C45 S1 C16 -0.2(3) . . . . ?
C6 C45 S1 C16 177.5(5) . . . . ?
C24 C25 S2 C29 -178.2(5) . . . . ?
C26 C25 S2 C29 1.2(4) . . . . ?
N4 C29 S2 C25 176.2(4) . . . . ?
N3 C29 S2 C25 -2.1(4) . . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2083675'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N2 O2 S'
_chemical_formula_weight         322.37

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'
O O 0.0106 0.0060 '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      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                   7.5403(9)
_cell_length_b                   8.8750(10)
_cell_length_c                   12.4650(14)
_cell_angle_alpha                72.2060(10)
_cell_angle_beta                 81.9390(10)
_cell_angle_gamma                77.2670(10)
_cell_volume                     772.33(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3106
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.40

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6188
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.454
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3294
_reflns_number_gt                2676
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0606P)²+0.1736P] 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         3294
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.78962(6) 0.19856(6) 0.51202(4) 0.04905(16) Uani 1 1 d . . . . .
O2 O 0.40770(15) 0.04928(16) 0.12786(11) 0.0479(3) Uani 1 1 d . . . . .
O1 O 0.69109(16) -0.02492(16) 0.06029(10) 0.0501(3) Uani 1 1 d . . . . .
N1 N 0.55889(16) 0.17573(14) 0.38672(10) 0.0312(3) Uani 1 1 d . . . . .
N2 N 0.87215(17) 0.10381(17) 0.32587(12) 0.0416(3) Uani 1 1 d . . . . .
C8 C 0.63965(19) 0.07840(16) 0.22024(12) 0.0305(3) Uani 1 1 d . . . . .
C13 C 0.4009(2) 0.33120(17) 0.21525(11) 0.0325(3) Uani 1 1 d . . . . .
C4 C 0.4516(2) 0.23434(17) 0.47204(12) 0.0330(3) Uani 1 1 d . . . . .
C12 C 0.48545(19) 0.16395(17) 0.28601(11) 0.0288(3) Uani 1 1 d . . . . .
H12A H 0.390248 0.098516 0.311422 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5831(2) 0.02957(17) 0.13078(12) 0.0327(3) Uani 1 1 d . . . . .
C9 C 0.8184(2) 0.05681(18) 0.24056(13) 0.0359(3) Uani 1 1 d . . . . .
C7 C 0.7415(2) 0.15433(18) 0.39333(13) 0.0349(3) Uani 1 1 d . . . . .
C14 C 0.5074(3) 0.44827(19) 0.17021(13) 0.0430(4) Uani 1 1 d . . . . .
H14A H 0.630041 0.424423 0.183804 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2631(2) 0.2714(2) 0.48639(13) 0.0402(4) Uani 1 1 d . . . . .
H3A H 0.190882 0.256348 0.437262 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5579(2) 0.25623(19) 0.54749(13) 0.0390(4) Uani 1 1 d . . . . .
C2 C 0.1849(3) 0.3317(2) 0.57612(14) 0.0477(4) Uani 1 1 d . . . . .
H2B H 0.058578 0.357016 0.587030 0.057 Uiso 1 1 calc R U . . .
C18 C 0.2185(2) 0.3670(2) 0.19354(15) 0.0498(4) Uani 1 1 d . . . . .
H18A H 0.145616 0.289482 0.222924 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4780(3) 0.3169(2) 0.63665(14) 0.0496(4) Uani 1 1 d . . . . .
H6A H 0.549398 0.331531 0.686412 0.060 Uiso 1 1 calc R U . . .
C11 C 0.9786(2) -0.0210(2) 0.17781(16) 0.0513(4) Uani 1 1 d . . . . .
H11A H 1.089015 -0.021563 0.208107 0.077 Uiso 1 1 calc R U . . .
H11B H 0.967641 -0.129798 0.185925 0.077 Uiso 1 1 calc R U . . .
H11C H 0.981669 0.038326 0.099214 0.077 Uiso 1 1 calc R U . . .
C1 C 0.2910(3) 0.3550(2) 0.64985(15) 0.0530(5) Uani 1 1 d . . . . .
H1A H 0.235046 0.396817 0.708746 0.064 Uiso 1 1 calc R U . . .
C15 C 0.4328(3) 0.6006(2) 0.10509(15) 0.0596(5) Uani 1 1 d . . . . .
H15A H 0.505020 0.678520 0.075780 0.072 Uiso 1 1 calc R U . . .
C17 C 0.1451(3) 0.5204(3) 0.12717(18) 0.0706(7) Uani 1 1 d . . . . .
H17A H 0.023143 0.544774 0.111957 0.085 Uiso 1 1 calc R U . . .
C16 C 0.2526(4) 0.6359(3) 0.08404(16) 0.0701(7) Uani 1 1 d . . . . .
H16A H 0.202544 0.738043 0.040539 0.084 Uiso 1 1 calc R U . . .
H2 H 0.376(4) 0.036(3) 0.069(3) 0.107(10) 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
S1 C5 1.7429(18) . ?
S1 C7 1.7444(15) . ?
O2 C10 1.2995(18) . ?
O2 H2 0.85(3) . ?
O1 C10 1.2467(18) . ?
N1 C7 1.3587(19) . ?
N1 C4 1.4028(18) . ?
N1 C12 1.4812(17) . ?
N2 C7 1.297(2) . ?
N2 C9 1.391(2) . ?
C8 C9 1.367(2) . ?
C8 C10 1.4572(19) . ?
C8 C12 1.5246(19) . ?
C13 C14 1.387(2) . ?
C13 C18 1.388(2) . ?
C13 C12 1.5258(19) . ?
C4 C3 1.385(2) . ?
C4 C5 1.399(2) . ?
C12 H12A 0.9800 . ?
C9 C11 1.498(2) . ?
C14 C15 1.387(2) . ?
C14 H14A 0.9300 . ?
C3 C2 1.388(2) . ?
C3 H3A 0.9300 . ?
C5 C6 1.387(2) . ?
C2 C1 1.386(3) . ?
C2 H2B 0.9300 . ?
C18 C17 1.397(3) . ?
C18 H18A 0.9300 . ?
C6 C1 1.374(3) . ?
C6 H6A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C1 H1A 0.9300 . ?
C15 C16 1.369(3) . ?
C15 H15A 0.9300 . ?
C17 C16 1.380(3) . ?
C17 H17A 0.9300 . ?
C16 H16A 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
C5 S1 C7 91.05(7) . . ?
C10 O2 H2 113.6(19) . . ?
C7 N1 C4 114.37(12) . . ?
C7 N1 C12 120.89(12) . . ?
C4 N1 C12 123.93(12) . . ?
C7 N2 C9 115.80(13) . . ?
C9 C8 C10 122.79(13) . . ?
C9 C8 C12 122.04(13) . . ?
C10 C8 C12 115.10(12) . . ?
C14 C13 C18 119.36(15) . . ?
C14 C13 C12 120.02(13) . . ?
C18 C13 C12 120.61(14) . . ?
C3 C4 C5 120.11(14) . . ?
C3 C4 N1 127.88(13) . . ?
C5 C4 N1 112.00(14) . . ?
N1 C12 C8 108.24(11) . . ?
N1 C12 C13 110.14(11) . . ?
C8 C12 C13 112.64(11) . . ?
N1 C12 H12A 108.6 . . ?
C8 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
O1 C10 O2 121.23(13) . . ?
O1 C10 C8 124.01(13) . . ?
O2 C10 C8 114.75(13) . . ?
C8 C9 N2 122.70(14) . . ?
C8 C9 C11 125.62(14) . . ?
N2 C9 C11 111.67(13) . . ?
N2 C7 N1 127.86(14) . . ?
N2 C7 S1 120.72(12) . . ?
N1 C7 S1 111.40(11) . . ?
C13 C14 C15 120.69(18) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C4 C3 C2 118.16(15) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C6 C5 C4 121.11(16) . . ?
C6 C5 S1 127.79(14) . . ?
C4 C5 S1 111.09(12) . . ?
C1 C2 C3 121.51(17) . . ?
C1 C2 H2B 119.2 . . ?
C3 C2 H2B 119.2 . . ?
C13 C18 C17 119.44(19) . . ?
C13 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C1 C6 C5 118.54(16) . . ?
C1 C6 H6A 120.7 . . ?
C5 C6 H6A 120.7 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C1 C2 120.56(16) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C15 C16 C17 120.22(18) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 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
C7 N1 C4 C3 178.45(15) . . . . ?
C12 N1 C4 C3 8.7(2) . . . . ?
C7 N1 C4 C5 -0.83(18) . . . . ?
C12 N1 C4 C5 -170.57(12) . . . . ?
C7 N1 C12 C8 16.92(17) . . . . ?
C4 N1 C12 C8 -173.98(12) . . . . ?
C7 N1 C12 C13 -106.62(14) . . . . ?
C4 N1 C12 C13 62.47(17) . . . . ?
C9 C8 C12 N1 -14.34(18) . . . . ?
C10 C8 C12 N1 168.78(11) . . . . ?
C9 C8 C12 C13 107.68(15) . . . . ?
C10 C8 C12 C13 -69.20(16) . . . . ?
C14 C13 C12 N1 60.37(16) . . . . ?
C18 C13 C12 N1 -120.82(14) . . . . ?
C14 C13 C12 C8 -60.58(17) . . . . ?
C18 C13 C12 C8 118.23(15) . . . . ?
C9 C8 C10 O1 -5.3(2) . . . . ?
C12 C8 C10 O1 171.52(14) . . . . ?
C9 C8 C10 O2 175.72(14) . . . . ?
C12 C8 C10 O2 -7.43(19) . . . . ?
C10 C8 C9 N2 179.87(14) . . . . ?
C12 C8 C9 N2 3.2(2) . . . . ?
C10 C8 C9 C11 -1.4(2) . . . . ?
C12 C8 C9 C11 -178.01(15) . . . . ?
C7 N2 C9 C8 7.0(2) . . . . ?
C7 N2 C9 C11 -171.91(15) . . . . ?
C9 N2 C7 N1 -4.2(2) . . . . ?
C9 N2 C7 S1 173.76(11) . . . . ?
C4 N1 C7 N2 -179.17(15) . . . . ?
C12 N1 C7 N2 -9.1(2) . . . . ?
C4 N1 C7 S1 2.68(16) . . . . ?
C12 N1 C7 S1 172.76(10) . . . . ?
C5 S1 C7 N2 178.80(14) . . . . ?
C5 S1 C7 N1 -2.91(12) . . . . ?
C18 C13 C14 C15 0.8(2) . . . . ?
C12 C13 C14 C15 179.58(14) . . . . ?
C5 C4 C3 C2 0.7(2) . . . . ?
N1 C4 C3 C2 -178.57(15) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
N1 C4 C5 C6 178.51(14) . . . . ?
C3 C4 C5 S1 179.25(12) . . . . ?
N1 C4 C5 S1 -1.40(16) . . . . ?
C7 S1 C5 C6 -177.47(16) . . . . ?
C7 S1 C5 C4 2.43(12) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C14 C13 C18 C17 -0.3(2) . . . . ?
C12 C13 C18 C17 -179.10(15) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
S1 C5 C6 C1 -179.91(14) . . . . ?
C5 C6 C1 C2 0.6(3) . . . . ?
C3 C2 C1 C6 -0.8(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C13 C18 C17 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C18 C17 C16 C15 0.6(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
C11 H11A O2 0.96 2.60 3.367(2) 136.7 1_655
C11 H11A O2 0.96 2.60 3.367(2) 136.7 1_655
O2 H2 O1 0.85(3) 1.79(3) 2.6406(17) 175(3) 2_655

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2083671'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 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            'C8.50 H7.50 N1.50 O S'
_chemical_formula_weight         178.72

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'
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                   10.374(11)
_cell_length_b                   9.403(10)
_cell_length_c                   18.919(16)
_cell_angle_alpha                90
_cell_angle_beta                 116.50(4)
_cell_angle_gamma                90
_cell_volume                     1652(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5502
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.46

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.337
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11102
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_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             2908
_reflns_number_gt                2490
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0557P)²+0.9340P] 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         2908
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.63786(6) 0.01311(6) -0.10834(3) 0.04049(18) Uani 1 1 d . . . . .
S4 S 0.84534(7) 0.38434(6) 0.13351(4) 0.0471(2) Uani 1 1 d . . . . .
O1 O 1.20736(17) 0.20598(17) 0.20997(8) 0.0454(4) Uani 1 1 d . . . . .
O2 O 1.23606(17) 0.36179(18) 0.12869(9) 0.0475(4) Uani 1 1 d . . . . .
N1 N 0.82310(17) 0.05407(17) 0.03579(9) 0.0283(4) Uani 1 1 d . . . . .
N2 N 0.85798(19) 0.19273(19) -0.06023(9) 0.0372(4) Uani 1 1 d . . . . .
N3 N 0.8722(2) 0.1588(2) 0.21591(10) 0.0405(4) Uani 1 1 d . . . . .
C1 C 0.5359(3) -0.2647(3) 0.02316(14) 0.0476(6) Uani 1 1 d . . . . .
H1A H 0.4705 -0.3362 0.0182 0.057 Uiso 1 1 calc R U . . .
C2 C 0.6440(2) -0.2297(2) 0.09752(13) 0.0428(5) Uani 1 1 d . . . . .
H2B H 0.6500 -0.2785 0.1416 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7432(2) -0.1233(2) 0.10706(12) 0.0348(5) Uani 1 1 d . . . . .
H3B H 0.8146 -0.0994 0.1569 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7328(2) -0.0534(2) 0.04003(11) 0.0295(4) Uani 1 1 d . . . . .
C5 C 0.6242(2) -0.0883(2) -0.03457(11) 0.0349(5) Uani 1 1 d . . . . .
C6 C 0.5251(2) -0.1939(3) -0.04342(13) 0.0443(5) Uani 1 1 d . . . . .
H6B H 0.4527 -0.2168 -0.0931 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7895(2) 0.1000(2) -0.03883(11) 0.0318(4) Uani 1 1 d . . . . .
C8 C 0.9421(2) 0.1193(2) 0.10512(10) 0.0274(4) Uani 1 1 d . . . . .
H8A H 1.0034 0.0432 0.1387 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8866(2) 0.2069(2) 0.15340(11) 0.0295(4) Uani 1 1 d . . . . .
C10 C 0.8230(3) 0.2665(3) 0.24575(13) 0.0518(6) Uani 1 1 d . . . . .
H10A H 0.8037 0.2521 0.2887 0.062 Uiso 1 1 calc R U . . .
C11 C 0.8039(3) 0.3928(3) 0.21090(15) 0.0495(6) Uani 1 1 d . . . . .
H11 H 0.7725 0.4741 0.2266 0.059 Uiso 1 1 calc R U . . .
C12 C 1.0322(2) 0.2111(2) 0.07744(11) 0.0294(4) Uani 1 1 d . . . . .
C13 C 0.9857(2) 0.2462(2) -0.00047(11) 0.0319(4) Uani 1 1 d . . . . .
C14 C 1.0604(3) 0.3424(3) -0.03380(13) 0.0425(5) Uani 1 1 d . . . . .
H14A H 1.0456 0.3076 -0.0846 0.064 Uiso 1 1 calc R U . . .
H14B H 1.1616 0.3443 0.0012 0.064 Uiso 1 1 calc R U . . .
H14C H 1.0217 0.4367 -0.0393 0.064 Uiso 1 1 calc R U . . .
C15 C 1.1651(2) 0.2568(2) 0.14409(11) 0.0326(4) Uani 1 1 d . . . . .
C16 C 1.3645(3) 0.4147(3) 0.19510(14) 0.0542(7) Uani 1 1 d . . . . .
H16A H 1.4351 0.3393 0.2172 0.065 Uiso 1 1 calc R U . . .
H16B H 1.3409 0.4502 0.2361 0.065 Uiso 1 1 calc R U . . .
C17 C 1.4226(3) 0.5319(3) 0.16429(16) 0.0578(7) Uani 1 1 d . . . . .
H17A H 1.5087 0.5691 0.2064 0.087 Uiso 1 1 calc R U . . .
H17B H 1.3521 0.6062 0.1432 0.087 Uiso 1 1 calc R U . . .
H17C H 1.4443 0.4956 0.1234 0.087 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 C7 1.740(2) . ?
S1 C5 1.747(2) . ?
S4 C11 1.702(3) . ?
S4 C9 1.722(3) . ?
O1 C15 1.219(3) . ?
O2 C15 1.339(3) . ?
O2 C16 1.452(3) . ?
N1 C7 1.365(3) . ?
N1 C4 1.404(3) . ?
N1 C8 1.475(3) . ?
N2 C7 1.298(3) . ?
N2 C13 1.396(3) . ?
N3 C9 1.336(3) . ?
N3 C10 1.364(3) . ?
C1 C6 1.384(3) . ?
C1 C2 1.392(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.388(3) . ?
C2 H2B 0.9300 . ?
C3 C4 1.389(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.397(3) . ?
C5 C6 1.385(3) . ?
C6 H6B 0.9300 . ?
C8 C9 1.520(3) . ?
C8 C12 1.527(3) . ?
C8 H8A 0.9800 . ?
C10 C11 1.330(4) . ?
C10 H10A 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 C15 1.457(3) . ?
C13 C14 1.501(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C17 1.494(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C5 91.20(11) . . ?
C11 S4 C9 89.49(11) . . ?
C15 O2 C16 116.46(17) . . ?
C7 N1 C4 114.72(16) . . ?
C7 N1 C8 120.94(17) . . ?
C4 N1 C8 124.30(16) . . ?
C7 N2 C13 116.28(17) . . ?
C9 N3 C10 109.0(2) . . ?
C6 C1 C2 120.5(2) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2B 119.4 . . ?
C1 C2 H2B 119.4 . . ?
C2 C3 C4 118.12(19) . . ?
C2 C3 H3B 120.9 . . ?
C4 C3 H3B 120.9 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 N1 127.63(18) . . ?
C5 C4 N1 111.68(18) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 S1 127.96(17) . . ?
C4 C5 S1 111.26(17) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 H6B 120.6 . . ?
C1 C6 H6B 120.6 . . ?
N2 C7 N1 127.79(19) . . ?
N2 C7 S1 121.06(16) . . ?
N1 C7 S1 111.13(16) . . ?
N1 C8 C9 111.63(17) . . ?
N1 C8 C12 109.14(16) . . ?
C9 C8 C12 110.74(17) . . ?
N1 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C12 C8 H8A 108.4 . . ?
N3 C9 C8 124.79(19) . . ?
N3 C9 S4 113.99(15) . . ?
C8 C9 S4 121.14(14) . . ?
C11 C10 N3 117.3(2) . . ?
C11 C10 H10A 121.4 . . ?
N3 C10 H10A 121.4 . . ?
C10 C11 S4 110.22(18) . . ?
C10 C11 H11 124.9 . . ?
S4 C11 H11 124.9 . . ?
C13 C12 C15 127.06(19) . . ?
C13 C12 C8 121.94(18) . . ?
C15 C12 C8 110.96(17) . . ?
C12 C13 N2 122.39(19) . . ?
C12 C13 C14 126.6(2) . . ?
N2 C13 C14 110.97(18) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 O2 121.99(19) . . ?
O1 C15 C12 122.59(19) . . ?
O2 C15 C12 115.38(17) . . ?
O2 C16 C17 106.8(2) . . ?
O2 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O2 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C4 N1 -178.2(2) . . . . ?
C7 N1 C4 C3 177.91(19) . . . . ?
C8 N1 C4 C3 -4.6(3) . . . . ?
C7 N1 C4 C5 -1.3(2) . . . . ?
C8 N1 C4 C5 176.22(17) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
N1 C4 C5 C6 178.85(19) . . . . ?
C3 C4 C5 S1 -178.94(15) . . . . ?
N1 C4 C5 S1 0.3(2) . . . . ?
C7 S1 C5 C6 -177.9(2) . . . . ?
C7 S1 C5 C4 0.50(16) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
S1 C5 C6 C1 178.07(18) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C13 N2 C7 N1 3.9(3) . . . . ?
C13 N2 C7 S1 -174.20(14) . . . . ?
C4 N1 C7 N2 -176.62(19) . . . . ?
C8 N1 C7 N2 5.8(3) . . . . ?
C4 N1 C7 S1 1.6(2) . . . . ?
C8 N1 C7 S1 -175.94(13) . . . . ?
C5 S1 C7 N2 177.19(18) . . . . ?
C5 S1 C7 N1 -1.20(15) . . . . ?
C7 N1 C8 C9 109.8(2) . . . . ?
C4 N1 C8 C9 -67.5(2) . . . . ?
C7 N1 C8 C12 -12.9(2) . . . . ?
C4 N1 C8 C12 169.73(17) . . . . ?
C10 N3 C9 C8 178.57(19) . . . . ?
C10 N3 C9 S4 1.9(2) . . . . ?
N1 C8 C9 N3 94.2(2) . . . . ?
C12 C8 C9 N3 -143.98(19) . . . . ?
N1 C8 C9 S4 -89.31(18) . . . . ?
C12 C8 C9 S4 32.5(2) . . . . ?
C11 S4 C9 N3 -1.13(17) . . . . ?
C11 S4 C9 C8 -177.98(17) . . . . ?
C9 N3 C10 C11 -1.9(3) . . . . ?
N3 C10 C11 S4 1.1(3) . . . . ?
C9 S4 C11 C10 0.03(19) . . . . ?
N1 C8 C12 C13 12.4(3) . . . . ?
C9 C8 C12 C13 -110.8(2) . . . . ?
N1 C8 C12 C15 -169.68(15) . . . . ?
C9 C8 C12 C15 67.0(2) . . . . ?
C15 C12 C13 N2 177.99(18) . . . . ?
C8 C12 C13 N2 -4.5(3) . . . . ?
C15 C12 C13 C14 -1.5(3) . . . . ?
C8 C12 C13 C14 175.99(19) . . . . ?
C7 N2 C13 C12 -4.4(3) . . . . ?
C7 N2 C13 C14 175.20(18) . . . . ?
C16 O2 C15 O1 -1.5(3) . . . . ?
C16 O2 C15 C12 176.7(2) . . . . ?
C13 C12 C15 O1 -170.1(2) . . . . ?
C8 C12 C15 O1 12.2(3) . . . . ?
C13 C12 C15 O2 11.8(3) . . . . ?
C8 C12 C15 O2 -165.95(17) . . . . ?
C15 O2 C16 C17 -178.8(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
C3 H3B N3 0.93 2.63 3.257(4) 125.5 .
C11 H11 O1 0.93 2.45 3.329(4) 157.1 2_755
C14 H14B O2 0.96 2.19 2.794(4) 120.1 .

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 2083678'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 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            'C28 H25 N3 O S'
_chemical_formula_weight         451.57

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'
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                   11.1662(13)
_cell_length_b                   13.6070(16)
_cell_length_c                   16.1430(19)
_cell_angle_alpha                90
_cell_angle_beta                 105.550(2)
_cell_angle_gamma                90
_cell_volume                     2363.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2918
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.01

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11794
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.619
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4145
_reflns_number_gt                2809
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0667P)²+0.1626P] 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         4145
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_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 0.38859(6) 0.11602(4) 0.05234(3) 0.0636(2) Uani 1 1 d . . . . .
N3 N 0.43139(13) 0.26297(10) 0.15549(9) 0.0396(4) Uani 1 1 d . . . . .
O003 O 0.47709(16) 0.40274(10) 0.38178(9) 0.0704(5) Uani 1 1 d . . . . .
N2 N 0.44986(15) 0.10806(11) 0.22387(10) 0.0507(4) Uani 1 1 d . . . . .
C23 C 0.61885(16) 0.35180(13) 0.23487(11) 0.0403(4) Uani 1 1 d . . . . .
C6 C 0.59998(17) 0.29958(14) 0.63659(12) 0.0445(5) Uani 1 1 d . . . . .
C22 C 0.48802(16) 0.31849(13) 0.23403(11) 0.0389(4) Uani 1 1 d . . . . .
H22 H 0.4372 0.3769 0.2352 0.047 Uiso 1 1 calc R U . . .
N1 N 0.70004(19) 0.22502(15) 0.89965(11) 0.0725(6) Uani 1 1 d . . . . .
C21 C 0.39828(16) 0.30481(14) 0.07351(11) 0.0426(5) Uani 1 1 d . . . . .
C15 C 0.42877(16) 0.16352(14) 0.15687(12) 0.0448(5) Uani 1 1 d . . . . .
C12 C 0.48801(16) 0.25458(13) 0.31195(11) 0.0416(4) Uani 1 1 d . . . . .
C13 C 0.46997(17) 0.15649(14) 0.30308(12) 0.0456(5) Uani 1 1 d . . . . .
C7 C 0.63395(17) 0.20435(14) 0.66453(12) 0.0479(5) Uani 1 1 d . . . . .
H7 H 0.6338 0.1559 0.6239 0.057 Uiso 1 1 calc R U . . .
C8 C 0.66775(18) 0.17935(15) 0.75028(13) 0.0512(5) Uani 1 1 d . . . . .
H8 H 0.6907 0.1149 0.7662 0.061 Uiso 1 1 calc R U . . .
C24 C 0.69638(17) 0.29277(16) 0.20249(12) 0.0518(5) Uani 1 1 d . . . . .
H24 H 0.6673 0.2329 0.1772 0.062 Uiso 1 1 calc R U . . .
C3 C 0.66810(18) 0.24950(15) 0.81403(12) 0.0512(5) Uani 1 1 d . . . . .
C9 C 0.55794(17) 0.32794(15) 0.54701(12) 0.0498(5) Uani 1 1 d . . . . .
H9 H 0.5320 0.3928 0.5368 0.060 Uiso 1 1 calc R U . . .
C10 C 0.55136(18) 0.27361(15) 0.47720(12) 0.0511(5) Uani 1 1 d . . . . .
H10 H 0.5778 0.2086 0.4835 0.061 Uiso 1 1 calc R U . . .
C11 C 0.50308(18) 0.31469(15) 0.39063(12) 0.0490(5) Uani 1 1 d . . . . .
C16 C 0.37201(18) 0.23421(14) 0.00922(12) 0.0492(5) Uani 1 1 d . . . . .
C5 C 0.6036(2) 0.36910(15) 0.69998(13) 0.0562(5) Uani 1 1 d . . . . .
H5 H 0.5833 0.4339 0.6839 0.067 Uiso 1 1 calc R U . . .
C25 C 0.81664(19) 0.32168(18) 0.20719(13) 0.0618(6) Uani 1 1 d . . . . .
H25 H 0.8676 0.2814 0.1848 0.074 Uiso 1 1 calc R U . . .
C20 C 0.39113(18) 0.40316(14) 0.05315(12) 0.0538(5) Uani 1 1 d . . . . .
H20 H 0.4106 0.4508 0.0960 0.065 Uiso 1 1 calc R U . . .
C28 C 0.66448(19) 0.44041(15) 0.27195(14) 0.0576(6) Uani 1 1 d . . . . .
H28 H 0.6136 0.4817 0.2934 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6362(2) 0.34511(16) 0.78595(13) 0.0605(6) Uani 1 1 d . . . . .
H4 H 0.6369 0.3940 0.8263 0.073 Uiso 1 1 calc R U . . .
C26 C 0.8609(2) 0.40882(18) 0.24446(15) 0.0660(6) Uani 1 1 d . . . . .
H26 H 0.9419 0.4280 0.2475 0.079 Uiso 1 1 calc R U . . .
C19 C 0.3541(2) 0.42941(16) -0.03318(13) 0.0651(6) Uani 1 1 d . . . . .
H19 H 0.3473 0.4955 -0.0484 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4633(2) 0.08467(16) 0.37273(13) 0.0649(6) Uani 1 1 d . . . . .
H14A H 0.4075 0.0322 0.3484 0.097 Uiso 1 1 calc R U . . .
H14B H 0.4336 0.1177 0.4159 0.097 Uiso 1 1 calc R U . . .
H14C H 0.5446 0.0583 0.3983 0.097 Uiso 1 1 calc R U . . .
C18 C 0.3272(2) 0.35863(17) -0.09637(14) 0.0698(7) Uani 1 1 d . . . . .
H18 H 0.3024 0.3776 -0.1538 0.084 Uiso 1 1 calc R U . . .
C27 C 0.7862(2) 0.46808(17) 0.27733(16) 0.0705(7) Uani 1 1 d . . . . .
H27 H 0.8168 0.5272 0.3034 0.085 Uiso 1 1 calc R U . . .
C17 C 0.3365(2) 0.26077(16) -0.07614(13) 0.0635(6) Uani 1 1 d . . . . .
H17 H 0.3191 0.2133 -0.1191 0.076 Uiso 1 1 calc R U . . .
C1 C 0.7033(3) 0.12333(19) 0.92645(16) 0.0876(8) Uani 1 1 d . . . . .
H1A H 0.6237 0.0936 0.9020 0.131 Uiso 1 1 calc R U . . .
H1B H 0.7227 0.1201 0.9880 0.131 Uiso 1 1 calc R U . . .
H1C H 0.7657 0.0888 0.9071 0.131 Uiso 1 1 calc R U . . .
C2 C 0.6954(3) 0.2978(2) 0.96422(15) 0.0884(8) Uani 1 1 d . . . . .
H2A H 0.7430 0.3544 0.9571 0.133 Uiso 1 1 calc R U . . .
H2B H 0.7293 0.2705 1.0204 0.133 Uiso 1 1 calc R U . . .
H2C H 0.6106 0.3169 0.9579 0.133 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 C16 1.742(2) . ?
S1 C15 1.7493(19) . ?
N3 C15 1.354(2) . ?
N3 C21 1.396(2) . ?
N3 C22 1.466(2) . ?
O003 C11 1.232(2) . ?
N2 C15 1.288(2) . ?
N2 C13 1.402(2) . ?
C23 C28 1.381(3) . ?
C23 C24 1.382(3) . ?
C23 C22 1.526(2) . ?
C6 C5 1.386(3) . ?
C6 C7 1.391(3) . ?
C6 C9 1.448(2) . ?
C22 C12 1.529(2) . ?
C22 H22 0.9800 . ?
N1 C3 1.373(2) . ?
N1 C1 1.447(3) . ?
N1 C2 1.449(3) . ?
C21 C20 1.375(3) . ?
C21 C16 1.387(3) . ?
C12 C13 1.352(3) . ?
C12 C11 1.482(3) . ?
C13 C14 1.506(3) . ?
C7 C8 1.376(3) . ?
C7 H7 0.9300 . ?
C8 C3 1.403(3) . ?
C8 H8 0.9300 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9300 . ?
C3 C4 1.392(3) . ?
C9 C10 1.333(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.467(3) . ?
C10 H10 0.9300 . ?
C16 C17 1.376(3) . ?
C5 C4 1.376(3) . ?
C5 H5 0.9300 . ?
C25 C26 1.361(3) . ?
C25 H25 0.9300 . ?
C20 C19 1.390(3) . ?
C20 H20 0.9300 . ?
C28 C27 1.390(3) . ?
C28 H28 0.9300 . ?
C4 H4 0.9300 . ?
C26 C27 1.366(3) . ?
C26 H26 0.9300 . ?
C19 C18 1.376(3) . ?
C19 H19 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C18 C17 1.368(3) . ?
C18 H18 0.9300 . ?
C27 H27 0.9300 . ?
C17 H17 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 S1 C15 90.96(9) . . ?
C15 N3 C21 114.94(15) . . ?
C15 N3 C22 120.48(14) . . ?
C21 N3 C22 123.57(14) . . ?
C15 N2 C13 116.05(16) . . ?
C28 C23 C24 118.39(18) . . ?
C28 C23 C22 120.27(17) . . ?
C24 C23 C22 121.28(16) . . ?
C5 C6 C7 116.42(17) . . ?
C5 C6 C9 119.53(18) . . ?
C7 C6 C9 124.01(18) . . ?
N3 C22 C23 110.53(14) . . ?
N3 C22 C12 108.86(14) . . ?
C23 C22 C12 111.88(13) . . ?
N3 C22 H22 108.5 . . ?
C23 C22 H22 108.5 . . ?
C12 C22 H22 108.5 . . ?
C3 N1 C1 120.8(2) . . ?
C3 N1 C2 120.6(2) . . ?
C1 N1 C2 116.2(2) . . ?
C20 C21 C16 120.54(17) . . ?
C20 C21 N3 127.37(17) . . ?
C16 C21 N3 112.09(16) . . ?
N2 C15 N3 126.85(17) . . ?
N2 C15 S1 122.38(15) . . ?
N3 C15 S1 110.76(13) . . ?
C13 C12 C11 127.97(17) . . ?
C13 C12 C22 120.48(16) . . ?
C11 C12 C22 111.48(16) . . ?
C12 C13 N2 122.93(17) . . ?
C12 C13 C14 126.67(18) . . ?
N2 C13 C14 110.36(17) . . ?
C8 C7 C6 122.26(18) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C3 121.05(19) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C25 C24 C23 120.8(2) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
N1 C3 C4 121.96(19) . . ?
N1 C3 C8 121.50(19) . . ?
C4 C3 C8 116.54(18) . . ?
C10 C9 C6 128.76(19) . . ?
C10 C9 H9 115.6 . . ?
C6 C9 H9 115.6 . . ?
C9 C10 C11 121.11(19) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
O003 C11 C10 119.74(18) . . ?
O003 C11 C12 117.92(17) . . ?
C10 C11 C12 122.30(18) . . ?
C17 C16 C21 120.92(19) . . ?
C17 C16 S1 127.86(16) . . ?
C21 C16 S1 111.21(14) . . ?
C4 C5 C6 122.00(19) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C21 C20 C19 118.18(19) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C23 C28 C27 120.3(2) . . ?
C23 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C5 C4 C3 121.69(19) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C18 C17 C16 118.5(2) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N3 C22 C23 100.25(18) . . . . ?
C21 N3 C22 C23 -67.6(2) . . . . ?
C15 N3 C22 C12 -23.0(2) . . . . ?
C21 N3 C22 C12 169.10(15) . . . . ?
C28 C23 C22 N3 146.11(16) . . . . ?
C24 C23 C22 N3 -36.9(2) . . . . ?
C28 C23 C22 C12 -92.4(2) . . . . ?
C24 C23 C22 C12 84.6(2) . . . . ?
C15 N3 C21 C20 178.98(18) . . . . ?
C22 N3 C21 C20 -12.5(3) . . . . ?
C15 N3 C21 C16 -1.5(2) . . . . ?
C22 N3 C21 C16 166.98(16) . . . . ?
C13 N2 C15 N3 4.3(3) . . . . ?
C13 N2 C15 S1 -174.40(13) . . . . ?
C21 N3 C15 N2 -176.72(17) . . . . ?
C22 N3 C15 N2 14.4(3) . . . . ?
C21 N3 C15 S1 2.06(19) . . . . ?
C22 N3 C15 S1 -166.82(12) . . . . ?
C16 S1 C15 N2 177.26(17) . . . . ?
C16 S1 C15 N3 -1.59(14) . . . . ?
N3 C22 C12 C13 16.5(2) . . . . ?
C23 C22 C12 C13 -105.98(19) . . . . ?
N3 C22 C12 C11 -160.69(14) . . . . ?
C23 C22 C12 C11 76.85(19) . . . . ?
C11 C12 C13 N2 176.28(17) . . . . ?
C22 C12 C13 N2 -0.4(3) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C22 C12 C13 C14 -177.86(18) . . . . ?
C15 N2 C13 C12 -11.1(3) . . . . ?
C15 N2 C13 C14 166.71(17) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C9 C6 C7 C8 -176.81(17) . . . . ?
C6 C7 C8 C3 0.7(3) . . . . ?
C28 C23 C24 C25 0.1(3) . . . . ?
C22 C23 C24 C25 -176.98(17) . . . . ?
C1 N1 C3 C4 164.8(2) . . . . ?
C2 N1 C3 C4 3.2(3) . . . . ?
C1 N1 C3 C8 -16.1(3) . . . . ?
C2 N1 C3 C8 -177.7(2) . . . . ?
C7 C8 C3 N1 179.11(18) . . . . ?
C7 C8 C3 C4 -1.8(3) . . . . ?
C5 C6 C9 C10 177.7(2) . . . . ?
C7 C6 C9 C10 -4.7(3) . . . . ?
C6 C9 C10 C11 178.54(18) . . . . ?
C9 C10 C11 O003 5.7(3) . . . . ?
C9 C10 C11 C12 -176.47(18) . . . . ?
C13 C12 C11 O003 -156.0(2) . . . . ?
C22 C12 C11 O003 20.9(2) . . . . ?
C13 C12 C11 C10 26.2(3) . . . . ?
C22 C12 C11 C10 -156.92(17) . . . . ?
C20 C21 C16 C17 -1.0(3) . . . . ?
N3 C21 C16 C17 179.45(17) . . . . ?
C20 C21 C16 S1 179.78(15) . . . . ?
N3 C21 C16 S1 0.2(2) . . . . ?
C15 S1 C16 C17 -178.4(2) . . . . ?
C15 S1 C16 C21 0.76(15) . . . . ?
C7 C6 C5 C4 -1.4(3) . . . . ?
C9 C6 C5 C4 176.37(19) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C16 C21 C20 C19 1.6(3) . . . . ?
N3 C21 C20 C19 -178.97(18) . . . . ?
C24 C23 C28 C27 -0.9(3) . . . . ?
C22 C23 C28 C27 176.14(17) . . . . ?
C6 C5 C4 C3 0.4(3) . . . . ?
N1 C3 C4 C5 -179.64(19) . . . . ?
C8 C3 C4 C5 1.2(3) . . . . ?
C24 C25 C26 C27 -0.1(3) . . . . ?
C21 C20 C19 C18 -1.0(3) . . . . ?
C20 C19 C18 C17 -0.1(4) . . . . ?
C25 C26 C27 C28 -0.8(3) . . . . ?
C23 C28 C27 C26 1.3(3) . . . . ?
C19 C18 C17 C16 0.7(4) . . . . ?
C21 C16 C17 C18 -0.2(3) . . . . ?
S1 C16 C17 C18 178.93(18) . . . . ?

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_180705SUNQPBTA16_0m
_database_code_depnum_ccdc_archive 'CCDC 2083672'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Cl2 N2 O2 S'
_chemical_formula_weight         419.31

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'
S S 0.1246 0.1234 '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'

_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                   9.8686(11)
_cell_length_b                   17.2210(19)
_cell_length_c                   11.4936(13)
_cell_angle_alpha                90
_cell_angle_beta                 106.030(2)
_cell_angle_gamma                90
_cell_volume                     1877.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3267
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.63

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.476
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11247
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         27.720
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4333
_reflns_number_gt                3231
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0565P)²+1.1624P] 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         4333
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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 0.06527(6) 0.07980(4) 0.92711(6) 0.04439(17) Uani 1 1 d . . . . .
S1 S 0.59543(6) -0.13552(4) 0.85601(6) 0.04265(17) Uani 1 1 d . . . . .
Cl3 Cl 0.22993(6) -0.09156(4) 0.58862(6) 0.04646(18) Uani 1 1 d . . . . .
N1 N 0.39535(16) -0.03758(10) 0.84751(15) 0.0297(4) Uani 1 1 d . . . . .
N2 N 0.53899(18) -0.01152(12) 0.71558(18) 0.0386(5) Uani 1 1 d . . . . .
C15 C 0.14350(19) -0.00374(12) 0.75256(18) 0.0267(4) Uani 1 1 d . . . . .
C8 C 0.2946(2) 0.02669(12) 0.80381(19) 0.0281(4) Uani 1 1 d . . . . .
C4 C 0.3859(2) -0.09104(12) 0.93652(19) 0.0309(4) Uani 1 1 d . . . . .
C10 C 0.4614(2) 0.05543(14) 0.6766(2) 0.0351(5) Uani 1 1 d . . . . .
C7 C 0.5028(2) -0.05180(13) 0.7967(2) 0.0324(5) Uani 1 1 d . . . . .
O1 O 0.1841(2) 0.16613(10) 0.7412(2) 0.0660(6) Uani 1 1 d . . . . .
C16 C 0.0335(2) 0.01934(13) 0.80056(19) 0.0318(5) Uani 1 1 d . . . . .
C6 C 0.4982(3) -0.20761(14) 1.0377(2) 0.0461(6) Uani 1 1 d . . . . .
H6 H 0.568205 -0.245295 1.049605 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3464(2) 0.07577(12) 0.7139(2) 0.0313(5) Uani 1 1 d . . . . .
C3 C 0.2900(2) -0.09171(14) 1.0050(2) 0.0379(5) Uani 1 1 d . . . . .
H3 H 0.221481 -0.053333 0.995236 0.045 Uiso 1 1 calc R U . . .
C17 C -0.1045(2) -0.00498(15) 0.7531(2) 0.0418(6) Uani 1 1 d . . . . .
H17 H -0.174652 0.011975 0.787043 0.050 Uiso 1 1 calc R U . . .
C19 C -0.0330(2) -0.08016(15) 0.6061(2) 0.0439(6) Uani 1 1 d . . . . .
H19 H -0.054618 -0.114247 0.540761 0.053 Uiso 1 1 calc R U . . .
C18 C -0.1370(2) -0.05445(16) 0.6554(2) 0.0481(6) Uani 1 1 d . . . . .
H18 H -0.229606 -0.070569 0.622446 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2736(2) 0.14949(13) 0.6755(2) 0.0388(5) Uani 1 1 d . . . . .
O2 O 0.2876(2) 0.19206(11) 0.59583(18) 0.0580(5) Uani 1 1 d . . . . .
C20 C 0.1044(2) -0.05483(13) 0.65456(19) 0.0325(5) Uani 1 1 d . . . . .
C5 C 0.4886(2) -0.14944(13) 0.9530(2) 0.0365(5) Uani 1 1 d . . . . .
C2 C 0.2991(3) -0.15112(15) 1.0883(2) 0.0460(6) Uani 1 1 d . . . . .
H2 H 0.235069 -0.152455 1.134430 0.055 Uiso 1 1 calc R U . . .
C1 C 0.4008(3) -0.20836(15) 1.1047(2) 0.0504(6) Uani 1 1 d . . . . .
H1 H 0.403991 -0.247637 1.160874 0.060 Uiso 1 1 calc R U . . .
C11 C 0.5227(3) 0.10164(17) 0.5925(3) 0.0511(7) Uani 1 1 d . . . . .
H11A H 0.617899 0.085196 0.601166 0.077 Uiso 1 1 calc R U . . .
H11B H 0.521879 0.155804 0.612057 0.077 Uiso 1 1 calc R U . . .
H11C H 0.467388 0.093464 0.510497 0.077 Uiso 1 1 calc R U . . .
C13 C 0.1128(4) 0.24026(19) 0.7223(6) 0.121(2) Uani 1 1 d . . . . .
H13A H 0.139985 0.269382 0.797383 0.145 Uiso 1 1 calc R U . . .
H13B H 0.144723 0.269148 0.662376 0.145 Uiso 1 1 calc R U . . .
C14 C -0.0317(5) 0.2356(3) 0.6846(5) 0.140(2) Uani 1 1 d . . . . .
H14A H -0.060380 0.210055 0.607417 0.210 Uiso 1 1 calc R U . . .
H14B H -0.071112 0.286905 0.677445 0.210 Uiso 1 1 calc R U . . .
H14C H -0.064713 0.206477 0.742633 0.210 Uiso 1 1 calc R U . . .
H8 H 0.298(2) 0.0588(12) 0.8720(19) 0.024(5) 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 C16 1.745(2) . ?
S1 C7 1.742(2) . ?
S1 C5 1.749(2) . ?
Cl3 C20 1.740(2) . ?
N1 C7 1.366(2) . ?
N1 C4 1.399(3) . ?
N1 C8 1.480(3) . ?
N2 C7 1.290(3) . ?
N2 C10 1.388(3) . ?
C15 C20 1.397(3) . ?
C15 C16 1.404(3) . ?
C15 C8 1.536(3) . ?
C8 C9 1.528(3) . ?
C8 H8 0.95(2) . ?
C4 C3 1.387(3) . ?
C4 C5 1.403(3) . ?
C10 C9 1.365(3) . ?
C10 C11 1.502(3) . ?
O1 C12 1.342(3) . ?
O1 C13 1.445(4) . ?
C16 C17 1.385(3) . ?
C6 C5 1.382(3) . ?
C6 C1 1.387(4) . ?
C6 H6 0.9300 . ?
C9 C12 1.466(3) . ?
C3 C2 1.388(3) . ?
C3 H3 0.9300 . ?
C17 C18 1.376(4) . ?
C17 H17 0.9300 . ?
C19 C18 1.375(4) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C12 O2 1.210(3) . ?
C2 C1 1.382(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.373(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C5 91.09(10) . . ?
C7 N1 C4 114.28(17) . . ?
C7 N1 C8 121.12(18) . . ?
C4 N1 C8 124.49(16) . . ?
C7 N2 C10 116.24(18) . . ?
C20 C15 C16 115.07(18) . . ?
C20 C15 C8 123.12(17) . . ?
C16 C15 C8 121.80(18) . . ?
N1 C8 C9 108.93(15) . . ?
N1 C8 C15 111.41(16) . . ?
C9 C8 C15 113.58(17) . . ?
N1 C8 H8 106.7(13) . . ?
C9 C8 H8 107.1(13) . . ?
C15 C8 H8 108.8(12) . . ?
C3 C4 N1 127.89(19) . . ?
C3 C4 C5 119.9(2) . . ?
N1 C4 C5 112.22(19) . . ?
C9 C10 N2 122.9(2) . . ?
C9 C10 C11 125.7(2) . . ?
N2 C10 C11 111.34(19) . . ?
N2 C7 N1 128.0(2) . . ?
N2 C7 S1 120.50(16) . . ?
N1 C7 S1 111.51(16) . . ?
C12 O1 C13 118.2(2) . . ?
C17 C16 C15 122.9(2) . . ?
C17 C16 Cl1 116.06(17) . . ?
C15 C16 Cl1 121.04(16) . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
C10 C9 C12 120.6(2) . . ?
C10 C9 C8 122.2(2) . . ?
C12 C9 C8 117.08(18) . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
O2 C12 O1 121.8(2) . . ?
O2 C12 C9 127.2(2) . . ?
O1 C12 C9 111.1(2) . . ?
C19 C20 C15 123.0(2) . . ?
C19 C20 Cl3 116.44(18) . . ?
C15 C20 Cl3 120.60(15) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 S1 127.77(18) . . ?
C4 C5 S1 110.88(17) . . ?
C1 C2 C3 121.7(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C13 O1 114.6(3) . . ?
C14 C13 H13A 108.6 . . ?
O1 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
O1 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C8 C9 -8.2(2) . . . . ?
C4 N1 C8 C9 175.78(18) . . . . ?
C7 N1 C8 C15 117.8(2) . . . . ?
C4 N1 C8 C15 -58.2(2) . . . . ?
C20 C15 C8 N1 -60.2(3) . . . . ?
C16 C15 C8 N1 120.8(2) . . . . ?
C20 C15 C8 C9 63.2(3) . . . . ?
C16 C15 C8 C9 -115.7(2) . . . . ?
C7 N1 C4 C3 179.2(2) . . . . ?
C8 N1 C4 C3 -4.6(3) . . . . ?
C7 N1 C4 C5 -1.2(3) . . . . ?
C8 N1 C4 C5 175.07(18) . . . . ?
C7 N2 C10 C9 -4.7(3) . . . . ?
C7 N2 C10 C11 173.9(2) . . . . ?
C10 N2 C7 N1 1.5(3) . . . . ?
C10 N2 C7 S1 -178.15(16) . . . . ?
C4 N1 C7 N2 -178.0(2) . . . . ?
C8 N1 C7 N2 5.6(3) . . . . ?
C4 N1 C7 S1 1.6(2) . . . . ?
C8 N1 C7 S1 -174.74(14) . . . . ?
C5 S1 C7 N2 178.39(19) . . . . ?
C5 S1 C7 N1 -1.28(16) . . . . ?
C20 C15 C16 C17 -1.5(3) . . . . ?
C8 C15 C16 C17 177.5(2) . . . . ?
C20 C15 C16 Cl1 177.32(16) . . . . ?
C8 C15 C16 Cl1 -3.7(3) . . . . ?
N2 C10 C9 C12 176.3(2) . . . . ?
C11 C10 C9 C12 -2.1(4) . . . . ?
N2 C10 C9 C8 0.9(3) . . . . ?
C11 C10 C9 C8 -177.5(2) . . . . ?
N1 C8 C9 C10 5.3(3) . . . . ?
C15 C8 C9 C10 -119.5(2) . . . . ?
N1 C8 C9 C12 -170.25(17) . . . . ?
C15 C8 C9 C12 64.9(2) . . . . ?
N1 C4 C3 C2 179.5(2) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
Cl1 C16 C17 C18 -178.25(19) . . . . ?
C20 C19 C18 C17 -1.0(4) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C13 O1 C12 O2 -5.5(4) . . . . ?
C13 O1 C12 C9 174.6(3) . . . . ?
C10 C9 C12 O2 13.3(4) . . . . ?
C8 C9 C12 O2 -171.1(2) . . . . ?
C10 C9 C12 O1 -166.8(2) . . . . ?
C8 C9 C12 O1 8.8(3) . . . . ?
C18 C19 C20 C15 0.0(4) . . . . ?
C18 C19 C20 Cl3 178.9(2) . . . . ?
C16 C15 C20 C19 1.1(3) . . . . ?
C8 C15 C20 C19 -177.8(2) . . . . ?
C16 C15 C20 Cl3 -177.63(16) . . . . ?
C8 C15 C20 Cl3 3.4(3) . . . . ?
C1 C6 C5 C4 1.7(3) . . . . ?
C1 C6 C5 S1 -179.21(19) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
N1 C4 C5 C6 179.3(2) . . . . ?
C3 C4 C5 S1 179.86(17) . . . . ?
N1 C4 C5 S1 0.2(2) . . . . ?
C7 S1 C5 C6 -178.5(2) . . . . ?
C7 S1 C5 C4 0.63(16) . . . . ?
C4 C3 C2 C1 0.4(4) . . . . ?
C3 C2 C1 C6 0.4(4) . . . . ?
C5 C6 C1 C2 -1.5(4) . . . . ?
C12 O1 C13 C14 120.0(5) . . . . ?

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
C3 H3 Cl1 0.93 2.75 3.653(2) 163.2 .
C11 H11A Cl3 0.96 2.97 3.624(2) 126.3 3_656

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_CCDC10
_database_code_depnum_ccdc_archive 'CCDC 2083680'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36

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'

_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                   10.5026(15)
_cell_length_b                   9.5898(14)
_cell_length_c                   17.064(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.244(2)
_cell_angle_gamma                90
_cell_volume                     1708.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3135
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.41

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10022
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.401
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3869
_reflns_number_gt                2560
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0836P)²+0.3246P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3869
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
O3 O 0.71403(13) 0.46897(14) 0.42392(7) 0.0570(4) Uani 1 1 d . . . . .
N2 N 0.68481(13) 0.43402(14) 0.54906(8) 0.0393(3) Uani 1 1 d . . . . .
O1 O 0.38566(14) 0.10635(17) 0.63419(9) 0.0729(5) Uani 1 1 d . . . . .
O2 O 0.48468(16) 0.25849(18) 0.71793(9) 0.0766(5) Uani 1 1 d . . . . .
N1 N 0.55889(15) 0.30811(17) 0.44887(9) 0.0538(4) Uani 1 1 d . . . . .
C15 C 0.75211(15) 0.26996(17) 0.65534(9) 0.0384(4) Uani 1 1 d . . . . .
C8 C 0.64284(14) 0.35833(17) 0.61628(9) 0.0371(4) Uani 1 1 d . . . . .
H8A H 0.616959 0.425768 0.654690 0.045 Uiso 1 1 calc R U . . .
C4 C 0.78342(15) 0.53189(17) 0.54886(10) 0.0416(4) Uani 1 1 d . . . . .
C9 C 0.52729(15) 0.27005(17) 0.58591(10) 0.0406(4) Uani 1 1 d . . . . .
C3 C 0.85806(16) 0.60137(18) 0.60814(11) 0.0478(4) Uani 1 1 d . . . . .
H3A H 0.847615 0.587881 0.661029 0.057 Uiso 1 1 calc R U . . .
C10 C 0.49510(17) 0.24624(18) 0.50767(11) 0.0464(4) Uani 1 1 d . . . . .
C7 C 0.64605(17) 0.39651(19) 0.47403(10) 0.0452(4) Uani 1 1 d . . . . .
C12 C 0.46421(16) 0.2136(2) 0.65162(12) 0.0493(5) Uani 1 1 d . . . . .
C5 C 0.79982(18) 0.55318(19) 0.47071(11) 0.0502(5) Uani 1 1 d . . . . .
C20 C 0.79122(17) 0.15216(19) 0.61759(13) 0.0521(5) Uani 1 1 d . . . . .
H20A H 0.749625 0.126981 0.568738 0.062 Uiso 1 1 calc R U . . .
C16 C 0.81526(18) 0.3053(2) 0.72764(11) 0.0585(5) Uani 1 1 d . . . . .
H16A H 0.790235 0.383775 0.754121 0.070 Uiso 1 1 calc R U . . .
C2 C 0.94931(18) 0.6922(2) 0.58468(14) 0.0590(5) Uani 1 1 d . . . . .
H2A H 1.001947 0.740362 0.622872 0.071 Uiso 1 1 calc R U . . .
C11 C 0.38926(18) 0.1513(2) 0.47263(13) 0.0627(6) Uani 1 1 d . . . . .
H11A H 0.386090 0.152621 0.416198 0.094 Uiso 1 1 calc R U . . .
H11B H 0.405512 0.057979 0.491455 0.094 Uiso 1 1 calc R U . . .
H11C H 0.308850 0.182964 0.487941 0.094 Uiso 1 1 calc R U . . .
C6 C 0.8896(2) 0.6437(2) 0.44678(14) 0.0660(6) Uani 1 1 d . . . . .
H6A H 0.899663 0.657476 0.393853 0.079 Uiso 1 1 calc R U . . .
C19 C 0.8912(2) 0.0718(2) 0.65165(17) 0.0735(7) Uani 1 1 d . . . . .
H19A H 0.916207 -0.007451 0.625911 0.088 Uiso 1 1 calc R U . . .
C1 C 0.9641(2) 0.7131(2) 0.50643(16) 0.0693(6) Uani 1 1 d . . . . .
H1B H 1.025965 0.775725 0.493200 0.083 Uiso 1 1 calc R U . . .
C18 C 0.9537(2) 0.1085(3) 0.72343(17) 0.0792(8) Uani 1 1 d . . . . .
H18A H 1.021489 0.054677 0.746280 0.095 Uiso 1 1 calc R U . . .
C17 C 0.9163(2) 0.2238(3) 0.76096(13) 0.0800(8) Uani 1 1 d . . . . .
H17A H 0.958892 0.248557 0.809623 0.096 Uiso 1 1 calc R U . . .
C13 C 0.3240(2) 0.0464(3) 0.69825(17) 0.0859(8) Uani 1 1 d . . . . .
H13A H 0.269475 0.115006 0.719718 0.103 Uiso 1 1 calc R U . . .
H13B H 0.387766 0.015557 0.740055 0.103 Uiso 1 1 calc R U . . .
C14 C 0.2465(3) -0.0737(3) 0.6656(2) 0.1029(10) Uani 1 1 d . . . . .
H14A H 0.204160 -0.116056 0.706707 0.154 Uiso 1 1 calc R U . . .
H14B H 0.183717 -0.041909 0.624425 0.154 Uiso 1 1 calc R U . . .
H14C H 0.301482 -0.140914 0.644671 0.154 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
O3 C7 1.363(2) . ?
O3 C5 1.395(2) . ?
N2 C7 1.349(2) . ?
N2 C4 1.398(2) . ?
N2 C8 1.465(2) . ?
O1 C12 1.332(2) . ?
O1 C13 1.449(3) . ?
O2 C12 1.208(2) . ?
N1 C7 1.287(2) . ?
N1 C10 1.398(3) . ?
C15 C16 1.378(2) . ?
C15 C20 1.385(3) . ?
C15 C8 1.521(2) . ?
C8 C9 1.524(2) . ?
C8 H8A 0.9800 . ?
C4 C5 1.378(3) . ?
C4 C3 1.382(2) . ?
C9 C10 1.360(2) . ?
C9 C12 1.467(3) . ?
C3 C2 1.386(3) . ?
C3 H3A 0.9300 . ?
C10 C11 1.509(2) . ?
C5 C6 1.376(3) . ?
C20 C19 1.379(3) . ?
C20 H20A 0.9300 . ?
C16 C17 1.389(3) . ?
C16 H16A 0.9300 . ?
C2 C1 1.376(3) . ?
C2 H2A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C6 C1 1.385(3) . ?
C6 H6A 0.9300 . ?
C19 C18 1.372(4) . ?
C19 H19A 0.9300 . ?
C1 H1B 0.9300 . ?
C18 C17 1.357(4) . ?
C18 H18A 0.9300 . ?
C17 H17A 0.9300 . ?
C13 C14 1.483(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 C5 106.62(14) . . ?
C7 N2 C4 108.90(14) . . ?
C7 N2 C8 121.69(14) . . ?
C4 N2 C8 128.35(13) . . ?
C12 O1 C13 117.06(18) . . ?
C7 N1 C10 114.79(15) . . ?
C16 C15 C20 118.63(17) . . ?
C16 C15 C8 121.46(16) . . ?
C20 C15 C8 119.91(15) . . ?
N2 C8 C15 110.01(12) . . ?
N2 C8 C9 107.77(12) . . ?
C15 C8 C9 112.00(13) . . ?
N2 C8 H8A 109.0 . . ?
C15 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C5 C4 C3 121.08(17) . . ?
C5 C4 N2 105.80(15) . . ?
C3 C4 N2 133.11(16) . . ?
C10 C9 C12 127.13(16) . . ?
C10 C9 C8 122.07(16) . . ?
C12 C9 C8 110.75(14) . . ?
C4 C3 C2 116.54(19) . . ?
C4 C3 H3A 121.7 . . ?
C2 C3 H3A 121.7 . . ?
C9 C10 N1 123.08(16) . . ?
C9 C10 C11 125.72(18) . . ?
N1 C10 C11 111.19(16) . . ?
N1 C7 N2 128.50(17) . . ?
N1 C7 O3 121.93(16) . . ?
N2 C7 O3 109.57(16) . . ?
O2 C12 O1 121.83(18) . . ?
O2 C12 C9 122.37(17) . . ?
O1 C12 C9 115.77(16) . . ?
C4 C5 C6 122.8(2) . . ?
C4 C5 O3 109.10(16) . . ?
C6 C5 O3 128.06(19) . . ?
C19 C20 C15 120.7(2) . . ?
C19 C20 H20A 119.6 . . ?
C15 C20 H20A 119.6 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16A 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C1 C2 C3 121.8(2) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C6 C1 115.8(2) . . ?
C5 C6 H6A 122.1 . . ?
C1 C6 H6A 122.1 . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C2 C1 C6 121.9(2) . . ?
C2 C1 H1B 119.0 . . ?
C6 C1 H1B 119.0 . . ?
C17 C18 C19 119.7(2) . . ?
C17 C18 H18A 120.1 . . ?
C19 C18 H18A 120.1 . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
O1 C13 C14 107.3(2) . . ?
O1 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O1 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C8 C15 106.19(16) . . . . ?
C4 N2 C8 C15 -60.7(2) . . . . ?
C7 N2 C8 C9 -16.18(19) . . . . ?
C4 N2 C8 C9 176.97(14) . . . . ?
C16 C15 C8 N2 107.71(18) . . . . ?
C20 C15 C8 N2 -71.35(19) . . . . ?
C16 C15 C8 C9 -132.46(17) . . . . ?
C20 C15 C8 C9 48.5(2) . . . . ?
C7 N2 C4 C5 1.23(18) . . . . ?
C8 N2 C4 C5 169.42(15) . . . . ?
C7 N2 C4 C3 -178.46(18) . . . . ?
C8 N2 C4 C3 -10.3(3) . . . . ?
N2 C8 C9 C10 13.9(2) . . . . ?
C15 C8 C9 C10 -107.24(17) . . . . ?
N2 C8 C9 C12 -168.51(13) . . . . ?
C15 C8 C9 C12 70.36(17) . . . . ?
C5 C4 C3 C2 -0.1(2) . . . . ?
N2 C4 C3 C2 179.51(17) . . . . ?
C12 C9 C10 N1 178.11(16) . . . . ?
C8 C9 C10 N1 -4.7(3) . . . . ?
C12 C9 C10 C11 -2.4(3) . . . . ?
C8 C9 C10 C11 174.81(16) . . . . ?
C7 N1 C10 C9 -4.0(3) . . . . ?
C7 N1 C10 C11 176.39(15) . . . . ?
C10 N1 C7 N2 1.6(3) . . . . ?
C10 N1 C7 O3 -177.88(15) . . . . ?
C4 N2 C7 N1 179.10(17) . . . . ?
C8 N2 C7 N1 10.0(3) . . . . ?
C4 N2 C7 O3 -1.38(18) . . . . ?
C8 N2 C7 O3 -170.50(13) . . . . ?
C5 O3 C7 N1 -179.49(16) . . . . ?
C5 O3 C7 N2 0.95(18) . . . . ?
C13 O1 C12 O2 0.8(3) . . . . ?
C13 O1 C12 C9 178.73(19) . . . . ?
C10 C9 C12 O2 -166.91(19) . . . . ?
C8 C9 C12 O2 15.6(3) . . . . ?
C10 C9 C12 O1 15.1(3) . . . . ?
C8 C9 C12 O1 -162.30(15) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
N2 C4 C5 C6 -179.97(17) . . . . ?
C3 C4 C5 O3 179.09(15) . . . . ?
N2 C4 C5 O3 -0.64(18) . . . . ?
C7 O3 C5 C4 -0.16(19) . . . . ?
C7 O3 C5 C6 179.12(18) . . . . ?
C16 C15 C20 C19 0.1(3) . . . . ?
C8 C15 C20 C19 179.17(16) . . . . ?
C20 C15 C16 C17 0.3(3) . . . . ?
C8 C15 C16 C17 -178.74(18) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
O3 C5 C6 C1 -179.00(18) . . . . ?
C15 C20 C19 C18 -0.4(3) . . . . ?
C3 C2 C1 C6 -0.6(3) . . . . ?
C5 C6 C1 C2 0.2(3) . . . . ?
C20 C19 C18 C17 0.4(3) . . . . ?
C19 C18 C17 C16 0.0(4) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C12 O1 C13 C14 -177.7(2) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_180717SUNQPBTC6_0m
_database_code_depnum_ccdc_archive 'CCDC 2083679'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N2 O2 S'
_chemical_formula_weight         412.49

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'
O O 0.0106 0.0060 '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           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   29.055(3)
_cell_length_b                   8.4317(8)
_cell_length_c                   17.7462(17)
_cell_angle_alpha                90
_cell_angle_beta                 104.768(2)
_cell_angle_gamma                90
_cell_volume                     4204.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3975
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.59

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12217
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.522
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4700
_reflns_number_gt                3280
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0586P)²+3.9119P] 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         4700
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
S1 S 0.19570(2) 0.21540(9) 1.01561(3) 0.0605(2) Uani 1 1 d . . . . .
N1 N 0.12193(5) 0.31686(19) 0.91476(8) 0.0364(4) Uani 1 1 d . . . . .
N2 N 0.18744(6) 0.2513(2) 0.86321(9) 0.0446(4) Uani 1 1 d . . . . .
O1 O 0.03633(5) 0.3600(2) 0.68889(8) 0.0589(4) Uani 1 1 d . . . . .
C8 C 0.11094(6) 0.3113(2) 0.77605(10) 0.0362(4) Uani 1 1 d . . . . .
C4 C 0.10867(7) 0.3171(2) 0.98512(10) 0.0394(4) Uani 1 1 d . . . . .
C17 C 0.07387(7) 0.2910(3) 0.70355(11) 0.0443(5) Uani 1 1 d . . . . .
C10 C 0.16708(7) 0.2662(2) 0.92001(11) 0.0406(4) Uani 1 1 d . . . . .
C9 C 0.15749(7) 0.2674(2) 0.78902(11) 0.0376(4) Uani 1 1 d . . . . .
C7 C 0.09269(6) 0.3838(2) 0.84125(10) 0.0341(4) Uani 1 1 d . . . . .
H7 H 0.059609 0.350361 0.834871 0.041 Uiso 1 1 calc R U . . .
C20 C 0.09456(7) 0.5630(2) 0.84286(10) 0.0373(4) Uani 1 1 d . . . . .
C11 C 0.18194(7) 0.2344(2) 0.72653(11) 0.0402(4) Uani 1 1 d . . . . .
C3 C 0.06524(8) 0.3627(3) 0.99664(12) 0.0475(5) Uani 1 1 d . . . . .
H3 H 0.040930 0.399708 0.955554 0.057 Uiso 1 1 calc R U . . .
O2 O 0.08437(6) 0.1830(3) 0.65666(11) 0.0933(8) Uani 1 1 d . . . . .
C21 C 0.05293(8) 0.6500(3) 0.82844(12) 0.0496(5) Uani 1 1 d . . . . .
H21 H 0.023759 0.598295 0.819468 0.060 Uiso 1 1 calc R U . . .
C5 C 0.14517(8) 0.2635(3) 1.04671(12) 0.0475(5) Uani 1 1 d . . . . .
C6 C 0.13841(9) 0.2530(3) 1.12134(12) 0.0589(6) Uani 1 1 d . . . . .
H6 H 0.162643 0.216823 1.162749 0.071 Uiso 1 1 calc R U . . .
C12 C 0.17616(9) 0.3337(3) 0.66337(13) 0.0627(7) Uani 1 1 d . . . . .
H12 H 0.156299 0.421496 0.659180 0.075 Uiso 1 1 calc R U . . .
C1 C 0.09513(10) 0.2971(3) 1.13253(13) 0.0627(7) Uani 1 1 d . . . . .
H1 H 0.089986 0.290217 1.182045 0.075 Uiso 1 1 calc R U . . .
C16 C 0.21293(8) 0.1081(3) 0.73270(13) 0.0545(6) Uani 1 1 d . . . . .
H16 H 0.218597 0.042509 0.776239 0.065 Uiso 1 1 calc R U . . .
C25 C 0.13758(8) 0.6425(3) 0.85631(14) 0.0571(6) Uani 1 1 d . . . . .
H25 H 0.165887 0.585483 0.866203 0.068 Uiso 1 1 calc R U . . .
C2 C 0.05916(9) 0.3516(3) 1.07126(13) 0.0582(6) Uani 1 1 d . . . . .
H2 H 0.030238 0.381508 1.080356 0.070 Uiso 1 1 calc R U . . .
C13 C 0.19955(11) 0.3044(4) 0.60599(15) 0.0775(8) Uani 1 1 d . . . . .
H13 H 0.195205 0.372008 0.563347 0.093 Uiso 1 1 calc R U . . .
C15 C 0.23558(9) 0.0787(3) 0.67442(16) 0.0691(7) Uani 1 1 d . . . . .
H15 H 0.255508 -0.008829 0.678126 0.083 Uiso 1 1 calc R U . . .
C22 C 0.05462(11) 0.8141(3) 0.82736(16) 0.0709(7) Uani 1 1 d . . . . .
H22 H 0.026542 0.872307 0.817664 0.085 Uiso 1 1 calc R U . . .
C23 C 0.09741(13) 0.8909(3) 0.84048(17) 0.0792(8) Uani 1 1 d . . . . .
H23 H 0.098322 1.001112 0.839404 0.095 Uiso 1 1 calc R U . . .
C24 C 0.13862(11) 0.8064(3) 0.85509(17) 0.0766(8) Uani 1 1 d . . . . .
H24 H 0.167635 0.859186 0.864299 0.092 Uiso 1 1 calc R U . . .
C14 C 0.22900(9) 0.1765(4) 0.61187(15) 0.0718(8) Uani 1 1 d . . . . .
H14 H 0.244534 0.156326 0.573071 0.086 Uiso 1 1 calc R U . . .
C18 C 0.05032(13) 0.1571(7) 0.5827(2) 0.164(3) Uani 1 1 d . . . . .
H18A H 0.028156 0.075399 0.589214 0.196 Uiso 1 1 calc R U . . .
H18B H 0.032290 0.253933 0.567604 0.196 Uiso 1 1 calc R U . . .
C19 C 0.06914(18) 0.1153(7) 0.5267(2) 0.1510(19) Uani 1 1 d . . . . .
H19A H 0.088407 0.200380 0.515689 0.226 Uiso 1 1 calc R U . . .
H19B H 0.044350 0.091687 0.480824 0.226 Uiso 1 1 calc R U . . .
H19C H 0.088573 0.022921 0.542111 0.226 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 C10 1.7418(19) . ?
S1 C5 1.743(2) . ?
N1 C10 1.360(2) . ?
N1 C4 1.397(2) . ?
N1 C7 1.475(2) . ?
N2 C10 1.299(2) . ?
N2 C9 1.388(2) . ?
O1 C17 1.205(2) . ?
C8 C9 1.364(3) . ?
C8 C17 1.462(3) . ?
C8 C7 1.519(2) . ?
C4 C3 1.384(3) . ?
C4 C5 1.390(3) . ?
C17 O2 1.321(3) . ?
C9 C11 1.488(3) . ?
C7 C20 1.512(3) . ?
C7 H7 0.9800 . ?
C20 C21 1.381(3) . ?
C20 C25 1.385(3) . ?
C11 C12 1.375(3) . ?
C11 C16 1.381(3) . ?
C3 C2 1.383(3) . ?
C3 H3 0.9300 . ?
O2 C18 1.445(3) . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C1 1.374(3) . ?
C6 H6 0.9300 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C1 C2 1.381(3) . ?
C1 H1 0.9300 . ?
C16 C15 1.382(3) . ?
C16 H16 0.9300 . ?
C25 C24 1.383(4) . ?
C25 H25 0.9300 . ?
C2 H2 0.9300 . ?
C13 C14 1.364(4) . ?
C13 H13 0.9300 . ?
C15 C14 1.356(4) . ?
C15 H15 0.9300 . ?
C22 C23 1.368(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C14 H14 0.9300 . ?
C18 C19 1.300(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C5 91.12(10) . . ?
C10 N1 C4 114.83(16) . . ?
C10 N1 C7 120.59(15) . . ?
C4 N1 C7 124.17(15) . . ?
C10 N2 C9 115.30(16) . . ?
C9 C8 C17 126.37(17) . . ?
C9 C8 C7 120.30(16) . . ?
C17 C8 C7 113.30(15) . . ?
C3 C4 C5 121.08(18) . . ?
C3 C4 N1 127.01(18) . . ?
C5 C4 N1 111.91(17) . . ?
O1 C17 O2 122.63(18) . . ?
O1 C17 C8 123.80(18) . . ?
O2 C17 C8 113.48(17) . . ?
N2 C10 N1 126.85(17) . . ?
N2 C10 S1 122.24(15) . . ?
N1 C10 S1 110.89(14) . . ?
C8 C9 N2 122.81(17) . . ?
C8 C9 C11 124.50(17) . . ?
N2 C9 C11 112.68(16) . . ?
N1 C7 C20 110.84(15) . . ?
N1 C7 C8 106.59(14) . . ?
C20 C7 C8 113.48(15) . . ?
N1 C7 H7 108.6 . . ?
C20 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
C21 C20 C25 119.0(2) . . ?
C21 C20 C7 120.09(18) . . ?
C25 C20 C7 120.91(18) . . ?
C12 C11 C16 118.43(19) . . ?
C12 C11 C9 120.75(18) . . ?
C16 C11 C9 120.74(18) . . ?
C2 C3 C4 117.8(2) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C17 O2 C18 117.5(2) . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 S1 111.24(15) . . ?
C6 C5 S1 128.44(19) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C6 C1 C2 120.9(2) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C11 C16 C15 120.3(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C24 C25 C20 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C1 C2 C3 121.4(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C19 C18 O2 114.3(3) . . ?
C19 C18 H18A 108.7 . . ?
O2 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
O2 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C4 C3 179.9(2) . . . . ?
C7 N1 C4 C3 7.2(3) . . . . ?
C10 N1 C4 C5 -0.3(2) . . . . ?
C7 N1 C4 C5 -172.93(17) . . . . ?
C9 C8 C17 O1 -163.6(2) . . . . ?
C7 C8 C17 O1 18.7(3) . . . . ?
C9 C8 C17 O2 19.6(3) . . . . ?
C7 C8 C17 O2 -158.1(2) . . . . ?
C9 N2 C10 N1 -9.8(3) . . . . ?
C9 N2 C10 S1 168.22(15) . . . . ?
C4 N1 C10 N2 178.2(2) . . . . ?
C7 N1 C10 N2 -8.9(3) . . . . ?
C4 N1 C10 S1 -0.1(2) . . . . ?
C7 N1 C10 S1 172.87(13) . . . . ?
C5 S1 C10 N2 -178.05(19) . . . . ?
C5 S1 C10 N1 0.29(16) . . . . ?
C17 C8 C9 N2 -162.42(19) . . . . ?
C7 C8 C9 N2 15.1(3) . . . . ?
C17 C8 C9 C11 18.6(3) . . . . ?
C7 C8 C9 C11 -163.81(18) . . . . ?
C10 N2 C9 C8 6.3(3) . . . . ?
C10 N2 C9 C11 -174.68(18) . . . . ?
C10 N1 C7 C20 -97.3(2) . . . . ?
C4 N1 C7 C20 74.9(2) . . . . ?
C10 N1 C7 C8 26.6(2) . . . . ?
C4 N1 C7 C8 -161.13(16) . . . . ?
C9 C8 C7 N1 -29.5(2) . . . . ?
C17 C8 C7 N1 148.32(16) . . . . ?
C9 C8 C7 C20 92.7(2) . . . . ?
C17 C8 C7 C20 -89.4(2) . . . . ?
N1 C7 C20 C21 -125.37(18) . . . . ?
C8 C7 C20 C21 114.74(19) . . . . ?
N1 C7 C20 C25 56.6(2) . . . . ?
C8 C7 C20 C25 -63.3(2) . . . . ?
C8 C9 C11 C12 44.8(3) . . . . ?
N2 C9 C11 C12 -134.2(2) . . . . ?
C8 C9 C11 C16 -138.7(2) . . . . ?
N2 C9 C11 C16 42.3(3) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
N1 C4 C3 C2 179.1(2) . . . . ?
O1 C17 O2 C18 4.6(5) . . . . ?
C8 C17 O2 C18 -178.6(3) . . . . ?
C25 C20 C21 C22 0.2(3) . . . . ?
C7 C20 C21 C22 -177.84(19) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
N1 C4 C5 C6 -179.02(19) . . . . ?
C3 C4 C5 S1 -179.65(16) . . . . ?
N1 C4 C5 S1 0.5(2) . . . . ?
C10 S1 C5 C4 -0.45(17) . . . . ?
C10 S1 C5 C6 179.0(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
S1 C5 C6 C1 -179.70(19) . . . . ?
C16 C11 C12 C13 2.3(4) . . . . ?
C9 C11 C12 C13 178.9(2) . . . . ?
C5 C6 C1 C2 -0.3(4) . . . . ?
C12 C11 C16 C15 -3.2(4) . . . . ?
C9 C11 C16 C15 -179.8(2) . . . . ?
C21 C20 C25 C24 -0.1(3) . . . . ?
C7 C20 C25 C24 177.9(2) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C11 C16 C15 C14 2.3(4) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C20 C25 C24 C23 -0.2(4) . . . . ?
C16 C15 C14 C13 -0.4(4) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C17 O2 C18 C19 148.4(4) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_CCDC11
_database_code_depnum_ccdc_archive 'CCDC 2083683'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 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            'C29 H29 N3 O2 S'
_chemical_formula_weight         483.61

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'
S S 0.1246 0.1234 '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                   9.644(3)
_cell_length_b                   10.615(3)
_cell_length_c                   12.949(4)
_cell_angle_alpha                75.074(3)
_cell_angle_beta                 77.598(3)
_cell_angle_gamma                89.546(3)
_cell_volume                     1249.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2853
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.91

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9126
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.668
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4642
_reflns_number_gt                3333
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0587P)²+0.3354P] 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         4642
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
S1 S 1.04743(6) 0.62231(6) 0.07180(5) 0.0538(2) Uani 1 1 d . . . . .
N1 N 0.83027(16) 0.50673(15) 0.21724(13) 0.0383(4) Uani 1 1 d . . . . .
N2 N 0.78281(18) 0.70636(16) 0.10059(14) 0.0462(4) Uani 1 1 d . . . . .
O1 O 0.38132(18) 0.68431(16) 0.31794(15) 0.0737(5) Uani 1 1 d . . . . .
C10 C 0.5944(2) 0.59116(18) 0.25214(16) 0.0369(4) Uani 1 1 d . . . . .
C11 C 0.67923(18) 0.46798(18) 0.26807(16) 0.0363(4) Uani 1 1 d . . . . .
H11 H 0.6704 0.4302 0.3468 0.044 Uiso 1 1 calc R U . . .
C12 C 0.62895(18) 0.36442(18) 0.21970(16) 0.0369(5) Uani 1 1 d . . . . .
C20 C 0.1977(2) 0.3456(2) 0.55828(16) 0.0432(5) Uani 1 1 d . . . . .
C8 C 0.6489(2) 0.69840(18) 0.16825(16) 0.0400(5) Uani 1 1 d . . . . .
C13 C 0.6124(2) 0.3983(2) 0.11227(17) 0.0450(5) Uani 1 1 d . . . . .
H13 H 0.6299 0.4846 0.0708 0.054 Uiso 1 1 calc R U . . .
C4 C 0.9435(2) 0.4294(2) 0.24116(17) 0.0407(5) Uani 1 1 d . . . . .
C7 C 0.8664(2) 0.61446(19) 0.13253(16) 0.0403(5) Uani 1 1 d . . . . .
C31 C 0.4016(2) 0.4667(2) 0.41183(17) 0.0448(5) Uani 1 1 d . . . . .
H31 H 0.4599 0.3965 0.4225 0.054 Uiso 1 1 calc R U . . .
N3 N -0.0327(2) 0.0324(2) 0.80555(18) 0.0733(6) Uani 1 1 d . . . . .
C19 C 0.2705(2) 0.4560(2) 0.47422(17) 0.0459(5) Uani 1 1 d . . . . .
H19 H 0.2186 0.5305 0.4617 0.055 Uiso 1 1 calc R U . . .
C25 C 0.0558(2) 0.3538(2) 0.60887(17) 0.0486(5) Uani 1 1 d . . . . .
H25 H 0.0117 0.4315 0.5876 0.058 Uiso 1 1 calc R U . . .
C3 C 1.0718(2) 0.4801(2) 0.16807(18) 0.0469(5) Uani 1 1 d . . . . .
C18 C 0.4562(2) 0.5875(2) 0.32642(17) 0.0444(5) Uani 1 1 d . . . . .
C21 C 0.2591(2) 0.2270(2) 0.59426(18) 0.0507(6) Uani 1 1 d . . . . .
H21 H 0.3534 0.2170 0.5630 0.061 Uiso 1 1 calc R U . . .
C5 C 0.9386(2) 0.3194(2) 0.32660(19) 0.0525(6) Uani 1 1 d . . . . .
H5 H 0.8530 0.2861 0.3748 0.063 Uiso 1 1 calc R U . . .
C26 C 0.0413(2) 0.1343(2) 0.72495(17) 0.0501(5) Uani 1 1 d . . . . .
C24 C -0.0215(2) 0.2529(2) 0.68826(17) 0.0527(6) Uani 1 1 d . . . . .
H24 H -0.1163 0.2629 0.7182 0.063 Uiso 1 1 calc R U . . .
C17 C 0.5997(2) 0.23562(19) 0.28089(19) 0.0480(5) Uani 1 1 d . . . . .
H17 H 0.6092 0.2114 0.3532 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5563(2) 0.1430(2) 0.2345(2) 0.0592(7) Uani 1 1 d . . . . .
H16 H 0.5367 0.0569 0.2759 0.071 Uiso 1 1 calc R U . . .
C9 C 0.5741(3) 0.8237(2) 0.1399(2) 0.0562(6) Uani 1 1 d . . . . .
H9A H 0.6333 0.8842 0.0783 0.084 Uiso 1 1 calc R U . . .
H9B H 0.4860 0.8060 0.1219 0.084 Uiso 1 1 calc R U . . .
H9C H 0.5553 0.8606 0.2016 0.084 Uiso 1 1 calc R U . . .
C22 C 0.1843(2) 0.1255(2) 0.67415(19) 0.0560(6) Uani 1 1 d . . . . .
H22 H 0.2293 0.0483 0.6956 0.067 Uiso 1 1 calc R U . . .
C14 C 0.5703(3) 0.3053(2) 0.0663(2) 0.0572(6) Uani 1 1 d . . . . .
H14 H 0.5608 0.3289 -0.0061 0.069 Uiso 1 1 calc R U . . .
O29 O 0.3494(3) 0.8427(3) 0.4582(2) 0.1156(10) Uani 1 1 d . . . . .
C15 C 0.5421(3) 0.1776(2) 0.1275(2) 0.0610(6) Uani 1 1 d . . . . .
H15 H 0.5137 0.1150 0.0966 0.073 Uiso 1 1 calc R U . . .
C1AA C 1.1967(2) 0.4189(3) 0.1815(2) 0.0619(7) Uani 1 1 d . . . . .
H1AA H 1.2826 0.4516 0.1335 0.074 Uiso 1 1 calc R U . . .
C6 C 1.0650(3) 0.2599(2) 0.3386(2) 0.0635(7) Uani 1 1 d . . . . .
H6 H 1.0643 0.1858 0.3959 0.076 Uiso 1 1 calc R U . . .
C1 C 1.1919(3) 0.3094(3) 0.2665(2) 0.0694(7) Uani 1 1 d . . . . .
H1 H 1.2753 0.2679 0.2757 0.083 Uiso 1 1 calc R U . . .
C28 C -0.1794(3) 0.0429(3) 0.8568(2) 0.0874(9) Uani 1 1 d . . . . .
H28A H -0.2137 -0.0372 0.9109 0.131 Uiso 1 1 calc R U . . .
H28B H -0.1864 0.1134 0.8913 0.131 Uiso 1 1 calc R U . . .
H28C H -0.2356 0.0594 0.8023 0.131 Uiso 1 1 calc R U . . .
C27 C 0.0381(3) -0.0795(3) 0.8557(3) 0.0922(10) Uani 1 1 d . . . . .
H27A H -0.0306 -0.1403 0.9099 0.138 Uiso 1 1 calc R U . . .
H27B H 0.0847 -0.1208 0.8007 0.138 Uiso 1 1 calc R U . . .
H27C H 0.1072 -0.0519 0.8898 0.138 Uiso 1 1 calc R U . . .
C2 C 0.2524(5) 0.9388(4) 0.4391(4) 0.1028(12) Uani 1 1 d . . . . .
H2A H 0.249(6) 0.983(6) 0.498(5) 0.22(3) Uiso 1 1 d . . . . .
H2B H 0.276(4) 0.994(4) 0.365(4) 0.146(15) Uiso 1 1 d . . . . .
H29 H 0.343(4) 0.792(4) 0.420(3) 0.128(16) Uiso 1 1 d . . . . .
H2C H 0.136(7) 0.906(6) 0.473(6) 0.26(3) 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
S1 C3 1.744(2) . ?
S1 C7 1.747(2) . ?
N1 C7 1.352(2) . ?
N1 C4 1.401(2) . ?
N1 C11 1.477(2) . ?
N2 C7 1.302(2) . ?
N2 C8 1.386(3) . ?
O1 C18 1.246(2) . ?
C10 C8 1.371(3) . ?
C10 C18 1.461(3) . ?
C10 C11 1.529(2) . ?
C11 C12 1.526(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.388(3) . ?
C12 C17 1.389(3) . ?
C20 C25 1.397(3) . ?
C20 C21 1.399(3) . ?
C20 C19 1.442(3) . ?
C8 C9 1.507(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C4 C5 1.379(3) . ?
C4 C3 1.401(3) . ?
C31 C19 1.334(3) . ?
C31 C18 1.475(3) . ?
C31 H31 0.9300 . ?
N3 C26 1.371(3) . ?
N3 C27 1.442(3) . ?
N3 C28 1.444(3) . ?
C19 H19 0.9300 . ?
C25 C24 1.370(3) . ?
C25 H25 0.9300 . ?
C3 C1AA 1.386(3) . ?
C21 C22 1.368(3) . ?
C21 H21 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C26 C24 1.407(3) . ?
C26 C22 1.409(3) . ?
C24 H24 0.9300 . ?
C17 C16 1.386(3) . ?
C17 H17 0.9300 . ?
C16 C15 1.375(4) . ?
C16 H16 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C22 H22 0.9300 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
O29 C2 1.390(4) . ?
O29 H29 0.84(4) . ?
C15 H15 0.9300 . ?
C1AA C1 1.372(3) . ?
C1AA H1AA 0.9300 . ?
C6 C1 1.383(3) . ?
C6 H6 0.9300 . ?
C1 H1 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C2 H2A 0.98(6) . ?
C2 H2B 0.97(4) . ?
C2 H2C 1.14(7) . ?

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
C3 S1 C7 90.83(10) . . ?
C7 N1 C4 115.03(16) . . ?
C7 N1 C11 120.43(15) . . ?
C4 N1 C11 124.01(16) . . ?
C7 N2 C8 115.58(17) . . ?
C8 C10 C18 122.94(17) . . ?
C8 C10 C11 119.16(16) . . ?
C18 C10 C11 117.88(16) . . ?
N1 C11 C12 109.91(15) . . ?
N1 C11 C10 108.01(15) . . ?
C12 C11 C10 113.48(15) . . ?
N1 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C10 C11 H11 108.4 . . ?
C13 C12 C17 118.79(19) . . ?
C13 C12 C11 119.87(17) . . ?
C17 C12 C11 121.35(18) . . ?
C25 C20 C21 115.99(19) . . ?
C25 C20 C19 119.52(19) . . ?
C21 C20 C19 124.49(18) . . ?
C10 C8 N2 123.85(17) . . ?
C10 C8 C9 124.81(18) . . ?
N2 C8 C9 111.32(17) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C5 C4 N1 127.21(18) . . ?
C5 C4 C3 121.32(19) . . ?
N1 C4 C3 111.42(18) . . ?
N2 C7 N1 126.43(18) . . ?
N2 C7 S1 122.23(15) . . ?
N1 C7 S1 111.26(14) . . ?
C19 C31 C18 121.46(19) . . ?
C19 C31 H31 119.3 . . ?
C18 C31 H31 119.3 . . ?
C26 N3 C27 121.4(2) . . ?
C26 N3 C28 121.0(2) . . ?
C27 N3 C28 116.8(2) . . ?
C31 C19 C20 129.4(2) . . ?
C31 C19 H19 115.3 . . ?
C20 C19 H19 115.3 . . ?
C24 C25 C20 123.2(2) . . ?
C24 C25 H25 118.4 . . ?
C20 C25 H25 118.4 . . ?
C1AA C3 C4 119.6(2) . . ?
C1AA C3 S1 128.98(18) . . ?
C4 C3 S1 111.38(15) . . ?
O1 C18 C10 121.25(19) . . ?
O1 C18 C31 118.84(18) . . ?
C10 C18 C31 119.90(17) . . ?
C22 C21 C20 121.8(2) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C4 C5 C6 118.1(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N3 C26 C24 121.9(2) . . ?
N3 C26 C22 121.6(2) . . ?
C24 C26 C22 116.5(2) . . ?
C25 C24 C26 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C26 C24 H24 119.7 . . ?
C16 C17 C12 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C21 C22 C26 121.9(2) . . ?
C21 C22 H22 119.0 . . ?
C26 C22 H22 119.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C2 O29 H29 108(3) . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C1 C1AA C3 119.1(2) . . ?
C1 C1AA H1AA 120.4 . . ?
C3 C1AA H1AA 120.4 . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C1AA C1 C6 121.1(2) . . ?
C1AA C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
N3 C28 H28A 109.5 . . ?
N3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O29 C2 H2A 104(3) . . ?
O29 C2 H2B 112(2) . . ?
H2A C2 H2B 116(4) . . ?
O29 C2 H2C 116(3) . . ?
H2A C2 H2C 90(4) . . ?
H2B C2 H2C 116(4) . . ?

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 N1 C11 C12 96.8(2) . . . . ?
C4 N1 C11 C12 -74.5(2) . . . . ?
C7 N1 C11 C10 -27.5(2) . . . . ?
C4 N1 C11 C10 161.22(17) . . . . ?
C8 C10 C11 N1 23.1(2) . . . . ?
C18 C10 C11 N1 -158.28(17) . . . . ?
C8 C10 C11 C12 -99.0(2) . . . . ?
C18 C10 C11 C12 79.6(2) . . . . ?
N1 C11 C12 C13 -70.4(2) . . . . ?
C10 C11 C12 C13 50.7(2) . . . . ?
N1 C11 C12 C17 109.30(19) . . . . ?
C10 C11 C12 C17 -129.65(18) . . . . ?
C18 C10 C8 N2 176.42(19) . . . . ?
C11 C10 C8 N2 -5.1(3) . . . . ?
C18 C10 C8 C9 -1.4(3) . . . . ?
C11 C10 C8 C9 177.09(19) . . . . ?
C7 N2 C8 C10 -11.7(3) . . . . ?
C7 N2 C8 C9 166.37(18) . . . . ?
C17 C12 C13 C14 -1.2(3) . . . . ?
C11 C12 C13 C14 178.46(18) . . . . ?
C7 N1 C4 C5 175.8(2) . . . . ?
C11 N1 C4 C5 -12.6(3) . . . . ?
C7 N1 C4 C3 -1.8(2) . . . . ?
C11 N1 C4 C3 169.89(18) . . . . ?
C8 N2 C7 N1 7.6(3) . . . . ?
C8 N2 C7 S1 -168.93(15) . . . . ?
C4 N1 C7 N2 -174.0(2) . . . . ?
C11 N1 C7 N2 14.0(3) . . . . ?
C4 N1 C7 S1 2.8(2) . . . . ?
C11 N1 C7 S1 -169.21(14) . . . . ?
C3 S1 C7 N2 174.65(19) . . . . ?
C3 S1 C7 N1 -2.31(16) . . . . ?
C18 C31 C19 C20 177.7(2) . . . . ?
C25 C20 C19 C31 -175.9(2) . . . . ?
C21 C20 C19 C31 3.8(4) . . . . ?
C21 C20 C25 C24 -0.7(3) . . . . ?
C19 C20 C25 C24 179.1(2) . . . . ?
C5 C4 C3 C1AA 0.0(3) . . . . ?
N1 C4 C3 C1AA 177.7(2) . . . . ?
C5 C4 C3 S1 -177.78(17) . . . . ?
N1 C4 C3 S1 -0.1(2) . . . . ?
C7 S1 C3 C1AA -176.2(2) . . . . ?
C7 S1 C3 C4 1.33(17) . . . . ?
C8 C10 C18 O1 -1.3(3) . . . . ?
C11 C10 C18 O1 -179.9(2) . . . . ?
C8 C10 C18 C31 177.33(19) . . . . ?
C11 C10 C18 C31 -1.2(3) . . . . ?
C19 C31 C18 O1 5.1(3) . . . . ?
C19 C31 C18 C10 -173.59(19) . . . . ?
C25 C20 C21 C22 0.0(3) . . . . ?
C19 C20 C21 C22 -179.7(2) . . . . ?
N1 C4 C5 C6 -177.2(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C27 N3 C26 C24 -169.2(3) . . . . ?
C28 N3 C26 C24 -0.2(4) . . . . ?
C27 N3 C26 C22 11.1(4) . . . . ?
C28 N3 C26 C22 -180.0(2) . . . . ?
C20 C25 C24 C26 1.4(3) . . . . ?
N3 C26 C24 C25 178.9(2) . . . . ?
C22 C26 C24 C25 -1.3(3) . . . . ?
C13 C12 C17 C16 0.7(3) . . . . ?
C11 C12 C17 C16 -178.98(18) . . . . ?
C12 C17 C16 C15 0.1(3) . . . . ?
C20 C21 C22 C26 -0.1(4) . . . . ?
N3 C26 C22 C21 -179.5(2) . . . . ?
C24 C26 C22 C21 0.7(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C17 C16 C15 C14 -0.4(4) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C4 C3 C1AA C1 0.0(4) . . . . ?
S1 C3 C1AA C1 177.3(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C3 C1AA C1 C6 -0.2(4) . . . . ?
C5 C6 C1 C1AA 0.3(4) . . . . ?

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
O29 H29 O1 0.84(4) 1.93(4) 2.747(4) 165(4) .
C5 H5 O29 0.93 2.66 3.566(4) 165.8 2_666

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.318
_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_CCDC12
_database_code_depnum_ccdc_archive 'CCDC 2083681'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 F3 N2 O2 S'
_chemical_formula_weight         404.40

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'
F F 0.0171 0.0103 '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                   11.749(4)
_cell_length_b                   17.194(6)
_cell_length_c                   9.398(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.271(6)
_cell_angle_gamma                90
_cell_volume                     1862.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2326
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10513
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.767
_diffrn_reflns_theta_max         27.200
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4062
_reflns_number_gt                2135
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1058P)²+0.0740P] 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         4062
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
S001 S 0.31611(9) 0.44485(5) 0.31409(9) 0.0615(3) Uani 1 1 d . . . . .
F3 F 0.1541(2) 0.68362(12) 0.7141(3) 0.0808(7) Uani 1 1 d . . . . .
O1 O 0.1679(2) 0.57250(15) 0.9262(3) 0.0647(7) Uani 1 1 d . . . . .
N2 N 0.3664(2) 0.45458(14) 0.5933(3) 0.0421(6) Uani 1 1 d . . . . .
F1 F 0.1060(2) 0.66739(15) 0.4865(3) 0.1007(9) Uani 1 1 d . . . . .
F2 F 0.0143(2) 0.60626(15) 0.6278(3) 0.1026(9) Uani 1 1 d . . . . .
O2 O 0.3606(2) 0.58111(18) 0.9759(3) 0.0813(9) Uani 1 1 d . . . . .
N1 N 0.2079(3) 0.53388(16) 0.4807(3) 0.0552(8) Uani 1 1 d . . . . .
C9 C 0.2985(3) 0.39277(17) 0.7995(3) 0.0389(7) Uani 1 1 d . . . . .
C15 C 0.4476(3) 0.40198(17) 0.5566(3) 0.0420(8) Uani 1 1 d . . . . .
C3 C 0.2721(3) 0.56626(18) 0.8930(4) 0.0482(8) Uani 1 1 d . . . . .
C5 C 0.3488(3) 0.46587(16) 0.7430(3) 0.0397(7) Uani 1 1 d . . . . .
H5A H 0.423858 0.477351 0.805584 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2691(3) 0.53535(17) 0.7442(4) 0.0432(8) Uani 1 1 d . . . . .
C6 C 0.2896(3) 0.48334(18) 0.4778(3) 0.0473(8) Uani 1 1 d . . . . .
C7 C 0.2037(3) 0.56234(17) 0.6187(4) 0.0491(8) Uani 1 1 d . . . . .
C14 C 0.1999(3) 0.3595(2) 0.7195(4) 0.0526(9) Uani 1 1 d . . . . .
H14A H 0.163906 0.382271 0.632550 0.063 Uiso 1 1 calc R U . . .
C20 C 0.4327(3) 0.39039(18) 0.4077(3) 0.0488(8) Uani 1 1 d . . . . .
C10 C 0.3499(3) 0.3592(2) 0.9291(4) 0.0546(9) Uani 1 1 d . . . . .
H10A H 0.417181 0.380612 0.983563 0.066 Uiso 1 1 calc R U . . .
C16 C 0.5333(3) 0.36320(19) 0.6528(4) 0.0488(8) Uani 1 1 d . . . . .
H16A H 0.542567 0.370724 0.752381 0.059 Uiso 1 1 calc R U . . .
C13 C 0.1537(3) 0.2921(2) 0.7673(4) 0.0604(10) Uani 1 1 d . . . . .
H13A H 0.088103 0.269286 0.711535 0.073 Uiso 1 1 calc R U . . .
C19 C 0.5050(3) 0.3400(2) 0.3509(4) 0.0594(10) Uani 1 1 d . . . . .
H19A H 0.496195 0.332838 0.251234 0.071 Uiso 1 1 calc R U . . .
C12 C 0.2055(3) 0.2596(2) 0.8972(4) 0.0602(10) Uani 1 1 d . . . . .
H12A H 0.174931 0.214498 0.929391 0.072 Uiso 1 1 calc R U . . .
C17 C 0.6053(3) 0.3124(2) 0.5950(4) 0.0587(9) Uani 1 1 d . . . . .
H17A H 0.664095 0.285896 0.656867 0.070 Uiso 1 1 calc R U . . .
C8 C 0.1190(4) 0.6290(2) 0.6125(4) 0.0647(10) Uani 1 1 d . . . . .
C18 C 0.5900(3) 0.3010(2) 0.4462(4) 0.0623(10) Uani 1 1 d . . . . .
H18A H 0.638106 0.266271 0.410103 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3010(3) 0.2930(2) 0.9788(4) 0.0681(11) Uani 1 1 d . . . . .
H11A H 0.334049 0.271646 1.068264 0.082 Uiso 1 1 calc R U . . .
C2 C 0.1624(4) 0.6075(3) 1.0675(5) 0.0853(14) Uani 1 1 d . . . . .
H2A H 0.219990 0.583631 1.142956 0.102 Uiso 1 1 calc R U . . .
H2B H 0.178868 0.662705 1.065649 0.102 Uiso 1 1 calc R U . . .
C1 C 0.0504(5) 0.5957(6) 1.0970(9) 0.208(5) Uani 1 1 d . . . . .
H1B H 0.046182 0.618445 1.189114 0.312 Uiso 1 1 calc R U . . .
H1C H -0.006102 0.619827 1.022363 0.312 Uiso 1 1 calc R U . . .
H1D H 0.034895 0.540992 1.099437 0.312 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
S001 C20 1.748(4) . ?
S001 C6 1.757(3) . ?
F3 C8 1.346(4) . ?
O1 C3 1.325(4) . ?
O1 C2 1.470(4) . ?
N2 C6 1.362(4) . ?
N2 C15 1.405(4) . ?
N2 C5 1.474(4) . ?
F1 C8 1.338(4) . ?
F2 C8 1.324(5) . ?
O2 C3 1.199(4) . ?
N1 C6 1.299(4) . ?
N1 C7 1.396(4) . ?
C9 C10 1.376(4) . ?
C9 C14 1.376(4) . ?
C9 C5 1.527(4) . ?
C15 C16 1.385(4) . ?
C15 C20 1.391(4) . ?
C3 C4 1.490(5) . ?
C5 C4 1.519(4) . ?
C5 H5A 0.9800 . ?
C4 C7 1.357(5) . ?
C7 C8 1.512(5) . ?
C14 C13 1.390(5) . ?
C14 H14A 0.9300 . ?
C20 C19 1.391(5) . ?
C10 C11 1.396(5) . ?
C10 H10A 0.9300 . ?
C16 C17 1.398(5) . ?
C16 H16A 0.9300 . ?
C13 C12 1.372(5) . ?
C13 H13A 0.9300 . ?
C19 C18 1.379(5) . ?
C19 H19A 0.9300 . ?
C12 C11 1.357(5) . ?
C12 H12A 0.9300 . ?
C17 C18 1.388(5) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C11 H11A 0.9300 . ?
C2 C1 1.412(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 S001 C6 90.94(16) . . ?
C3 O1 C2 116.8(3) . . ?
C6 N2 C15 114.4(3) . . ?
C6 N2 C5 121.2(3) . . ?
C15 N2 C5 123.2(2) . . ?
C6 N1 C7 114.5(3) . . ?
C10 C9 C14 119.1(3) . . ?
C10 C9 C5 121.4(3) . . ?
C14 C9 C5 119.6(3) . . ?
C16 C15 C20 121.4(3) . . ?
C16 C15 N2 126.2(3) . . ?
C20 C15 N2 112.4(3) . . ?
O2 C3 O1 123.6(3) . . ?
O2 C3 C4 123.0(3) . . ?
O1 C3 C4 113.4(3) . . ?
N2 C5 C4 108.2(2) . . ?
N2 C5 C9 111.1(2) . . ?
C4 C5 C9 111.4(2) . . ?
N2 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C9 C5 H5A 108.7 . . ?
C7 C4 C3 126.8(3) . . ?
C7 C4 C5 120.5(3) . . ?
C3 C4 C5 112.7(3) . . ?
N1 C6 N2 127.1(3) . . ?
N1 C6 S001 121.9(3) . . ?
N2 C6 S001 111.0(2) . . ?
C4 C7 N1 124.8(3) . . ?
C4 C7 C8 123.3(3) . . ?
N1 C7 C8 111.9(3) . . ?
C9 C14 C13 120.7(3) . . ?
C9 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 S001 128.1(3) . . ?
C15 C20 S001 111.2(2) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C15 C16 C17 117.7(3) . . ?
C15 C16 H16A 121.1 . . ?
C17 C16 H16A 121.1 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C18 C19 C20 118.2(3) . . ?
C18 C19 H19A 120.9 . . ?
C20 C19 H19A 120.9 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
F2 C8 F1 107.1(3) . . ?
F2 C8 F3 106.9(3) . . ?
F1 C8 F3 104.5(3) . . ?
F2 C8 C7 113.0(3) . . ?
F1 C8 C7 111.6(3) . . ?
F3 C8 C7 113.1(3) . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18A 119.3 . . ?
C17 C18 H18A 119.3 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C1 C2 O1 109.0(4) . . ?
C1 C2 H2A 109.9 . . ?
O1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
O1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 C15 C16 -178.6(3) . . . . ?
C5 N2 C15 C16 -10.7(5) . . . . ?
C6 N2 C15 C20 0.3(4) . . . . ?
C5 N2 C15 C20 168.1(3) . . . . ?
C2 O1 C3 O2 6.7(5) . . . . ?
C2 O1 C3 C4 -176.0(3) . . . . ?
C6 N2 C5 C4 -21.8(4) . . . . ?
C15 N2 C5 C4 171.2(2) . . . . ?
C6 N2 C5 C9 100.7(3) . . . . ?
C15 N2 C5 C9 -66.3(4) . . . . ?
C10 C9 C5 N2 127.3(3) . . . . ?
C14 C9 C5 N2 -52.6(4) . . . . ?
C10 C9 C5 C4 -112.0(3) . . . . ?
C14 C9 C5 C4 68.1(4) . . . . ?
O2 C3 C4 C7 -130.7(4) . . . . ?
O1 C3 C4 C7 52.0(5) . . . . ?
O2 C3 C4 C5 50.2(4) . . . . ?
O1 C3 C4 C5 -127.1(3) . . . . ?
N2 C5 C4 C7 17.4(4) . . . . ?
C9 C5 C4 C7 -104.9(3) . . . . ?
N2 C5 C4 C3 -163.5(3) . . . . ?
C9 C5 C4 C3 74.2(3) . . . . ?
C7 N1 C6 N2 2.3(5) . . . . ?
C7 N1 C6 S001 -175.9(2) . . . . ?
C15 N2 C6 N1 -178.3(3) . . . . ?
C5 N2 C6 N1 13.6(5) . . . . ?
C15 N2 C6 S001 0.1(3) . . . . ?
C5 N2 C6 S001 -168.0(2) . . . . ?
C20 S001 C6 N1 178.2(3) . . . . ?
C20 S001 C6 N2 -0.3(2) . . . . ?
C3 C4 C7 N1 176.7(3) . . . . ?
C5 C4 C7 N1 -4.2(5) . . . . ?
C3 C4 C7 C8 -1.7(5) . . . . ?
C5 C4 C7 C8 177.4(3) . . . . ?
C6 N1 C7 C4 -6.9(5) . . . . ?
C6 N1 C7 C8 171.7(3) . . . . ?
C10 C9 C14 C13 -1.1(5) . . . . ?
C5 C9 C14 C13 178.8(3) . . . . ?
C16 C15 C20 C19 -0.9(5) . . . . ?
N2 C15 C20 C19 -179.8(3) . . . . ?
C16 C15 C20 S001 178.4(2) . . . . ?
N2 C15 C20 S001 -0.5(3) . . . . ?
C6 S001 C20 C19 179.7(3) . . . . ?
C6 S001 C20 C15 0.4(3) . . . . ?
C14 C9 C10 C11 -1.0(5) . . . . ?
C5 C9 C10 C11 179.1(3) . . . . ?
C20 C15 C16 C17 0.6(5) . . . . ?
N2 C15 C16 C17 179.4(3) . . . . ?
C9 C14 C13 C12 1.5(5) . . . . ?
C15 C20 C19 C18 1.2(5) . . . . ?
S001 C20 C19 C18 -178.0(3) . . . . ?
C14 C13 C12 C11 0.2(6) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C4 C7 C8 F2 -87.7(4) . . . . ?
N1 C7 C8 F2 93.6(4) . . . . ?
C4 C7 C8 F1 151.5(3) . . . . ?
N1 C7 C8 F1 -27.1(4) . . . . ?
C4 C7 C8 F3 34.0(5) . . . . ?
N1 C7 C8 F3 -144.6(3) . . . . ?
C20 C19 C18 C17 -1.3(5) . . . . ?
C16 C17 C18 C19 1.0(6) . . . . ?
C13 C12 C11 C10 -2.2(6) . . . . ?
C9 C10 C11 C12 2.6(6) . . . . ?
C3 O1 C2 C1 -168.6(6) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_CCDC13
_database_code_depnum_ccdc_archive 'CCDC 2083684'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3 O4 S'
_chemical_formula_weight         395.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.861(4)
_cell_length_b                   8.0720(17)
_cell_length_c                   23.601(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3783.6(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2783
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      21.13

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.203
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21444
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.681
_diffrn_reflns_theta_max         27.654
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4379
_reflns_number_gt                2457
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0958P)²+1.1019P] 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         4379
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1804
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_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 0.37965(4) 0.71847(10) 0.49818(3) 0.0508(2) Uani 1 1 d . . . . .
O2 O 0.67002(9) 0.9564(3) 0.40293(8) 0.0518(5) Uani 1 1 d . . . . .
N1 N 0.47599(10) 0.8343(3) 0.43751(9) 0.0364(5) Uani 1 1 d . . . . .
O1 O 0.71077(10) 0.8692(3) 0.48588(10) 0.0658(7) Uani 1 1 d . . . . .
N2 N 0.50876(12) 0.7242(3) 0.52651(9) 0.0453(6) Uani 1 1 d . . . . .
C15 C 0.55650(12) 0.7191(3) 0.37043(11) 0.0360(6) Uani 1 1 d . . . . .
C8 C 0.54480(11) 0.8521(3) 0.41548(10) 0.0346(6) Uani 1 1 d . . . . .
H8A H 0.549960 0.961876 0.398318 0.042 Uiso 1 1 calc R U . . .
C4 C 0.41831(12) 0.8565(3) 0.40416(11) 0.0382(6) Uani 1 1 d . . . . .
C9 C 0.59410(13) 0.8343(3) 0.46454(11) 0.0389(6) Uani 1 1 d . . . . .
N3 N 0.58916(17) 0.3345(5) 0.25229(14) 0.0782(9) Uani 1 1 d . . . . .
C7 C 0.46436(14) 0.7606(3) 0.48823(11) 0.0412(7) Uani 1 1 d . . . . .
C3 C 0.41407(14) 0.9288(4) 0.35127(11) 0.0463(7) Uani 1 1 d . . . . .
H3A H 0.452200 0.968843 0.332959 0.056 Uiso 1 1 calc R U . . .
C12 C 0.66334(14) 0.8853(3) 0.45430(12) 0.0437(7) Uani 1 1 d . . . . .
C5 C 0.36083(13) 0.7972(4) 0.43123(12) 0.0460(7) Uani 1 1 d . . . . .
C10 C 0.57451(14) 0.7668(3) 0.51470(12) 0.0428(7) Uani 1 1 d . . . . .
C16 C 0.54707(15) 0.5543(4) 0.38522(12) 0.0478(7) Uani 1 1 d . . . . .
H16A H 0.533769 0.527997 0.421909 0.057 Uiso 1 1 calc R U . . .
O3 O 0.57476(18) 0.1934(5) 0.26670(14) 0.1142(12) Uani 1 1 d . . . . .
C20 C 0.57597(14) 0.7562(4) 0.31561(11) 0.0483(7) Uani 1 1 d . . . . .
H20A H 0.581755 0.866079 0.304808 0.058 Uiso 1 1 calc R U . . .
C19 C 0.58691(15) 0.6303(5) 0.27663(12) 0.0574(9) Uani 1 1 d . . . . .
H19A H 0.600549 0.654534 0.239856 0.069 Uiso 1 1 calc R U . . .
C18 C 0.57725(14) 0.4703(4) 0.29332(13) 0.0530(8) Uani 1 1 d . . . . .
C17 C 0.55706(16) 0.4293(4) 0.34652(13) 0.0551(8) Uani 1 1 d . . . . .
H17A H 0.550157 0.319208 0.356537 0.066 Uiso 1 1 calc R U . . .
C2 C 0.35110(16) 0.9395(4) 0.32646(13) 0.0602(9) Uani 1 1 d . . . . .
H2B H 0.346811 0.989064 0.291067 0.072 Uiso 1 1 calc R U . . .
O4 O 0.6128(2) 0.3711(5) 0.20700(14) 0.1335(14) Uani 1 1 d . . . . .
C11 C 0.62077(15) 0.7249(5) 0.56268(13) 0.0582(8) Uani 1 1 d . . . . .
H11A H 0.595169 0.678863 0.593380 0.087 Uiso 1 1 calc R U . . .
H11B H 0.653529 0.645538 0.550133 0.087 Uiso 1 1 calc R U . . .
H11C H 0.643276 0.823483 0.575306 0.087 Uiso 1 1 calc R U . . .
C13 C 0.73581(15) 1.0242(5) 0.39033(14) 0.0660(10) Uani 1 1 d . . . . .
H13A H 0.770066 0.939394 0.394494 0.079 Uiso 1 1 calc R U . . .
H13B H 0.746141 1.114301 0.416095 0.079 Uiso 1 1 calc R U . . .
C6 C 0.29907(15) 0.8071(5) 0.40597(15) 0.0648(9) Uani 1 1 d . . . . .
H6A H 0.260911 0.766565 0.424126 0.078 Uiso 1 1 calc R U . . .
C1 C 0.29447(16) 0.8782(5) 0.35321(15) 0.0727(11) Uani 1 1 d . . . . .
H1A H 0.252832 0.885000 0.335330 0.087 Uiso 1 1 calc R U . . .
C14 C 0.73420(18) 1.0851(6) 0.33138(17) 0.0947(14) Uani 1 1 d . . . . .
H14A H 0.777287 1.130974 0.321713 0.142 Uiso 1 1 calc R U . . .
H14B H 0.724044 0.994869 0.306295 0.142 Uiso 1 1 calc R U . . .
H14C H 0.700222 1.169019 0.327803 0.142 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 C7 1.732(3) . ?
S1 C5 1.744(3) . ?
O2 C12 1.348(3) . ?
O2 C13 1.447(3) . ?
N1 C7 1.356(3) . ?
N1 C4 1.401(3) . ?
N1 C8 1.469(3) . ?
O1 C12 1.208(3) . ?
N2 C7 1.296(3) . ?
N2 C10 1.379(3) . ?
C15 C20 1.383(4) . ?
C15 C16 1.387(4) . ?
C15 C8 1.529(4) . ?
C8 C9 1.523(4) . ?
C8 H8A 0.9800 . ?
C4 C3 1.381(4) . ?
C4 C5 1.393(4) . ?
C9 C10 1.360(4) . ?
C9 C12 1.456(4) . ?
N3 O4 1.204(4) . ?
N3 O3 1.223(5) . ?
N3 C18 1.481(4) . ?
C3 C2 1.384(4) . ?
C3 H3A 0.9300 . ?
C5 C6 1.366(4) . ?
C10 C11 1.497(4) . ?
C16 C17 1.375(4) . ?
C16 H16A 0.9300 . ?
C20 C19 1.388(4) . ?
C20 H20A 0.9300 . ?
C19 C18 1.364(5) . ?
C19 H19A 0.9300 . ?
C18 C17 1.359(4) . ?
C17 H17A 0.9300 . ?
C2 C1 1.382(5) . ?
C2 H2B 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.476(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C6 C1 1.374(5) . ?
C6 H6A 0.9300 . ?
C1 H1A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C5 90.79(13) . . ?
C12 O2 C13 115.8(2) . . ?
C7 N1 C4 114.4(2) . . ?
C7 N1 C8 120.9(2) . . ?
C4 N1 C8 123.3(2) . . ?
C7 N2 C10 116.6(2) . . ?
C20 C15 C16 118.7(2) . . ?
C20 C15 C8 122.7(2) . . ?
C16 C15 C8 118.5(2) . . ?
N1 C8 C9 108.7(2) . . ?
N1 C8 C15 108.6(2) . . ?
C9 C8 C15 111.4(2) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C15 C8 H8A 109.4 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 N1 127.7(2) . . ?
C5 C4 N1 111.6(2) . . ?
C10 C9 C12 121.9(2) . . ?
C10 C9 C8 121.0(2) . . ?
C12 C9 C8 117.0(2) . . ?
O4 N3 O3 124.5(4) . . ?
O4 N3 C18 117.5(4) . . ?
O3 N3 C18 118.0(4) . . ?
N2 C7 N1 126.8(3) . . ?
N2 C7 S1 121.5(2) . . ?
N1 C7 S1 111.8(2) . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 H3A 121.2 . . ?
C2 C3 H3A 121.2 . . ?
O1 C12 O2 121.6(3) . . ?
O1 C12 C9 127.1(3) . . ?
O2 C12 C9 111.3(2) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 S1 127.5(2) . . ?
C4 C5 S1 111.4(2) . . ?
C9 C10 N2 123.1(2) . . ?
C9 C10 C11 125.0(3) . . ?
N2 C10 C11 111.8(2) . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C15 C20 C19 120.3(3) . . ?
C15 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C18 C19 C20 118.7(3) . . ?
C18 C19 H19A 120.7 . . ?
C20 C19 H19A 120.7 . . ?
C17 C18 C19 122.6(3) . . ?
C17 C18 N3 118.1(3) . . ?
C19 C18 N3 119.3(3) . . ?
C18 C17 C16 118.5(3) . . ?
C18 C17 H17A 120.7 . . ?
C16 C17 H17A 120.7 . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2B 119.3 . . ?
C3 C2 H2B 119.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C13 C14 107.5(3) . . ?
O2 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
O2 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 H6A 120.7 . . ?
C1 C6 H6A 120.7 . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C8 C9 -19.4(3) . . . . ?
C4 N1 C8 C9 175.0(2) . . . . ?
C7 N1 C8 C15 101.9(3) . . . . ?
C4 N1 C8 C15 -63.6(3) . . . . ?
C20 C15 C8 N1 123.5(3) . . . . ?
C16 C15 C8 N1 -56.4(3) . . . . ?
C20 C15 C8 C9 -116.9(3) . . . . ?
C16 C15 C8 C9 63.2(3) . . . . ?
C7 N1 C4 C3 179.2(3) . . . . ?
C8 N1 C4 C3 -14.4(4) . . . . ?
C7 N1 C4 C5 0.2(3) . . . . ?
C8 N1 C4 C5 166.6(2) . . . . ?
N1 C8 C9 C10 16.6(3) . . . . ?
C15 C8 C9 C10 -103.0(3) . . . . ?
N1 C8 C9 C12 -166.2(2) . . . . ?
C15 C8 C9 C12 74.2(3) . . . . ?
C10 N2 C7 N1 0.9(4) . . . . ?
C10 N2 C7 S1 -178.5(2) . . . . ?
C4 N1 C7 N2 179.2(3) . . . . ?
C8 N1 C7 N2 12.4(4) . . . . ?
C4 N1 C7 S1 -1.4(3) . . . . ?
C8 N1 C7 S1 -168.18(18) . . . . ?
C5 S1 C7 N2 -178.9(2) . . . . ?
C5 S1 C7 N1 1.7(2) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
N1 C4 C3 C2 -179.1(3) . . . . ?
C13 O2 C12 O1 -5.1(4) . . . . ?
C13 O2 C12 C9 175.1(2) . . . . ?
C10 C9 C12 O1 3.4(5) . . . . ?
C8 C9 C12 O1 -173.8(3) . . . . ?
C10 C9 C12 O2 -176.8(2) . . . . ?
C8 C9 C12 O2 6.1(3) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
N1 C4 C5 C6 179.9(3) . . . . ?
C3 C4 C5 S1 -178.0(2) . . . . ?
N1 C4 C5 S1 1.1(3) . . . . ?
C7 S1 C5 C6 179.7(3) . . . . ?
C7 S1 C5 C4 -1.6(2) . . . . ?
C12 C9 C10 N2 177.0(3) . . . . ?
C8 C9 C10 N2 -6.0(4) . . . . ?
C12 C9 C10 C11 -5.0(4) . . . . ?
C8 C9 C10 C11 172.1(3) . . . . ?
C7 N2 C10 C9 -3.9(4) . . . . ?
C7 N2 C10 C11 177.8(3) . . . . ?
C20 C15 C16 C17 0.3(4) . . . . ?
C8 C15 C16 C17 -179.8(3) . . . . ?
C16 C15 C20 C19 -1.1(4) . . . . ?
C8 C15 C20 C19 179.0(2) . . . . ?
C15 C20 C19 C18 0.8(4) . . . . ?
C20 C19 C18 C17 0.3(5) . . . . ?
C20 C19 C18 N3 -179.6(3) . . . . ?
O4 N3 C18 C17 -173.4(3) . . . . ?
O3 N3 C18 C17 6.1(5) . . . . ?
O4 N3 C18 C19 6.5(5) . . . . ?
O3 N3 C18 C19 -173.9(3) . . . . ?
C19 C18 C17 C16 -1.1(5) . . . . ?
N3 C18 C17 C16 178.8(3) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C4 C3 C2 C1 -0.9(5) . . . . ?
C12 O2 C13 C14 176.1(3) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
S1 C5 C6 C1 178.2(3) . . . . ?
C5 C6 C1 C2 -0.5(6) . . . . ?
C3 C2 C1 C6 1.2(6) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_CCDC14
_database_code_depnum_ccdc_archive 'CCDC 2083676'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2 O2 S'
_chemical_formula_weight         400.48

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'
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                   14.035(3)
_cell_length_b                   15.493(3)
_cell_length_c                   9.258(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.912(3)
_cell_angle_gamma                90
_cell_volume                     2010.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5409
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      26.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15798
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         27.597
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4443
_reflns_number_gt                3267
_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1006P)²+1.4817P] 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         4443
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1976
_refine_ls_wR_factor_gt          0.1771
_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 0.47388(5) 0.44050(5) -0.24887(8) 0.0527(2) Uani 1 1 d . . . . .
O1 O 0.21368(17) 0.36338(16) 0.3289(2) 0.0676(6) Uani 1 1 d . . . . .
O2 O 0.25271(18) 0.50261(14) 0.3256(2) 0.0641(6) Uani 1 1 d . . . . .
N1 N 0.36184(14) 0.50440(13) -0.0655(2) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.37711(16) 0.35153(14) -0.0574(2) 0.0449(5) Uani 1 1 d . . . . .
C1 C 0.4694(2) 0.6992(2) -0.3169(3) 0.0614(8) Uani 1 1 d . . . . .
H1A H 0.494824 0.741598 -0.374850 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3128(2) 0.26053(18) 0.1244(3) 0.0560(7) Uani 1 1 d . . . . .
H24A H 0.344377 0.220318 0.064108 0.084 Uiso 1 1 calc R U . . .
H24B H 0.340995 0.257954 0.220948 0.084 Uiso 1 1 calc R U . . .
H24C H 0.246324 0.246000 0.125747 0.084 Uiso 1 1 calc R U . . .
C2 C 0.4065(2) 0.7223(2) -0.2129(4) 0.0591(8) Uani 1 1 d . . . . .
H2B H 0.390109 0.780028 -0.202380 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3676(2) 0.66085(18) -0.1239(3) 0.0472(6) Uani 1 1 d . . . . .
H3A H 0.325385 0.676710 -0.054235 0.057 Uiso 1 1 calc R U . . .
C4 C 0.39306(17) 0.57595(17) -0.1415(3) 0.0383(5) Uani 1 1 d . . . . .
C5 C 0.45631(18) 0.55243(19) -0.2475(3) 0.0436(6) Uani 1 1 d . . . . .
C6 C 0.4945(2) 0.6141(2) -0.3354(3) 0.0555(8) Uani 1 1 d . . . . .
H6A H 0.536398 0.598490 -0.405607 0.067 Uiso 1 1 calc R U . . .
C7 C 0.39562(18) 0.42674(17) -0.1086(3) 0.0392(6) Uani 1 1 d . . . . .
C8 C 0.28792(17) 0.50896(15) 0.0418(3) 0.0362(5) Uani 1 1 d . . . . .
H8A H 0.303263 0.555783 0.110292 0.043 Uiso 1 1 calc R U . . .
C9 C 0.28747(18) 0.42312(16) 0.1230(3) 0.0374(5) Uani 1 1 d . . . . .
C10 C 0.32312(18) 0.35040(16) 0.0654(3) 0.0408(6) Uani 1 1 d . . . . .
C11 C 0.24684(19) 0.42374(18) 0.2661(3) 0.0447(6) Uani 1 1 d . . . . .
C12 C 0.2197(4) 0.5105(3) 0.4716(4) 0.0848(12) Uani 1 1 d . . . . .
H12A H 0.153825 0.491747 0.473600 0.102 Uiso 1 1 calc R U . . .
H12B H 0.258081 0.474352 0.537334 0.102 Uiso 1 1 calc R U . . .
C13 C 0.2278(4) 0.6002(3) 0.5160(4) 0.0933(14) Uani 1 1 d . . . . .
H13A H 0.206175 0.606245 0.612270 0.140 Uiso 1 1 calc R U . . .
H13B H 0.293158 0.618103 0.514394 0.140 Uiso 1 1 calc R U . . .
H13C H 0.189251 0.635440 0.450873 0.140 Uiso 1 1 calc R U . . .
C14 C 0.18929(19) 0.52679(17) -0.0369(3) 0.0431(6) Uani 1 1 d . . . . .
C15 C 0.0927(3) 0.7209(2) 0.1441(5) 0.0815(11) Uani 1 1 d . . . . .
H15A H 0.109152 0.758399 0.219692 0.098 Uiso 1 1 calc R U . . .
C16 C 0.0057(3) 0.7321(3) 0.0652(5) 0.0873(13) Uani 1 1 d . . . . .
H16A H -0.035322 0.776506 0.088624 0.105 Uiso 1 1 calc R U . . .
C17 C -0.0183(3) 0.6780(3) -0.0450(5) 0.0778(11) Uani 1 1 d . . . . .
H17A H -0.075496 0.686420 -0.098327 0.093 Uiso 1 1 calc R U . . .
C18 C 0.0415(2) 0.6092(2) -0.0807(3) 0.0556(8) Uani 1 1 d . . . . .
C19 C 0.1303(2) 0.59662(18) -0.0009(3) 0.0490(7) Uani 1 1 d . . . . .
C20 C 0.1543(3) 0.6551(2) 0.1116(4) 0.0618(8) Uani 1 1 d . . . . .
H20A H 0.212084 0.649343 0.164362 0.074 Uiso 1 1 calc R U . . .
C21 C 0.0141(2) 0.5499(2) -0.1936(4) 0.0652(9) Uani 1 1 d . . . . .
H21A H -0.043071 0.558053 -0.247107 0.078 Uiso 1 1 calc R U . . .
C22 C 0.0711(2) 0.4816(2) -0.2235(4) 0.0627(8) Uani 1 1 d . . . . .
H22A H 0.051616 0.442845 -0.295858 0.075 Uiso 1 1 calc R U . . .
C23 C 0.15844(19) 0.4689(2) -0.1466(3) 0.0475(6) Uani 1 1 d . . . . .
H23A H 0.196361 0.421853 -0.168270 0.057 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 C5 1.752(3) . ?
S1 C7 1.756(3) . ?
O1 C11 1.207(3) . ?
O2 C11 1.341(3) . ?
O2 C12 1.456(4) . ?
N1 C7 1.360(3) . ?
N1 C4 1.395(3) . ?
N1 C8 1.474(3) . ?
N2 C7 1.289(3) . ?
N2 C10 1.398(3) . ?
C1 C6 1.379(5) . ?
C1 C2 1.386(5) . ?
C1 H1A 0.9300 . ?
C24 C10 1.505(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C2 C3 1.389(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.404(3) . ?
C5 C6 1.381(4) . ?
C6 H6A 0.9300 . ?
C8 C9 1.528(3) . ?
C8 C14 1.556(4) . ?
C8 H8A 0.9800 . ?
C9 C10 1.353(4) . ?
C9 C11 1.468(3) . ?
C12 C13 1.452(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C23 1.407(4) . ?
C14 C19 1.412(4) . ?
C15 C20 1.379(5) . ?
C15 C16 1.402(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.349(6) . ?
C16 H16A 0.9300 . ?
C17 C18 1.406(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.430(4) . ?
C18 C21 1.429(5) . ?
C19 C20 1.408(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.364(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.400(4) . ?
C22 H22A 0.9300 . ?
C23 H23A 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
C5 S1 C7 91.22(12) . . ?
C11 O2 C12 116.2(2) . . ?
C7 N1 C4 115.6(2) . . ?
C7 N1 C8 120.52(19) . . ?
C4 N1 C8 123.46(19) . . ?
C7 N2 C10 116.0(2) . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C10 C24 H24A 109.5 . . ?
C10 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C10 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2B 119.3 . . ?
C3 C2 H2B 119.3 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 N1 127.6(2) . . ?
C3 C4 C5 120.6(2) . . ?
N1 C4 C5 111.8(2) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 S1 128.4(2) . . ?
C4 C5 S1 110.9(2) . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 H6A 120.7 . . ?
C1 C6 H6A 120.7 . . ?
N2 C7 N1 127.7(2) . . ?
N2 C7 S1 121.82(19) . . ?
N1 C7 S1 110.48(18) . . ?
N1 C8 C9 108.09(18) . . ?
N1 C8 C14 109.41(19) . . ?
C9 C8 C14 111.0(2) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C14 C8 H8A 109.4 . . ?
C10 C9 C11 121.9(2) . . ?
C10 C9 C8 121.3(2) . . ?
C11 C9 C8 116.7(2) . . ?
C9 C10 N2 122.4(2) . . ?
C9 C10 C24 125.6(2) . . ?
N2 C10 C24 111.9(2) . . ?
O1 C11 O2 121.7(3) . . ?
O1 C11 C9 127.4(3) . . ?
O2 C11 C9 111.0(2) . . ?
C13 C12 O2 108.6(3) . . ?
C13 C12 H12A 110.0 . . ?
O2 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
O2 C12 H12B 110.0 . . ?
H12A C12 H12B 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C23 C14 C19 119.8(3) . . ?
C23 C14 C8 117.3(2) . . ?
C19 C14 C8 122.9(2) . . ?
C20 C15 C16 121.1(4) . . ?
C20 C15 H15A 119.4 . . ?
C16 C15 H15A 119.4 . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 121.3(4) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 C21 121.2(3) . . ?
C19 C18 C21 119.0(3) . . ?
C20 C19 C14 123.1(3) . . ?
C20 C19 C18 117.6(3) . . ?
C14 C19 C18 119.3(3) . . ?
C15 C20 C19 120.5(4) . . ?
C15 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C22 C21 C18 120.6(3) . . ?
C22 C21 H21A 119.7 . . ?
C18 C21 H21A 119.7 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C22 C23 C14 120.5(3) . . ?
C22 C23 H23A 119.8 . . ?
C14 C23 H23A 119.8 . . ?

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 0.4(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 N1 -179.2(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C7 N1 C4 C3 177.5(2) . . . . ?
C8 N1 C4 C3 5.1(4) . . . . ?
C7 N1 C4 C5 -1.4(3) . . . . ?
C8 N1 C4 C5 -173.8(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
N1 C4 C5 C6 179.4(2) . . . . ?
C3 C4 C5 S1 -178.6(2) . . . . ?
N1 C4 C5 S1 0.4(3) . . . . ?
C7 S1 C5 C6 -178.4(3) . . . . ?
C7 S1 C5 C4 0.4(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
S1 C5 C6 C1 178.8(2) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C10 N2 C7 N1 -6.5(4) . . . . ?
C10 N2 C7 S1 172.42(18) . . . . ?
C4 N1 C7 N2 -179.3(2) . . . . ?
C8 N1 C7 N2 -6.7(4) . . . . ?
C4 N1 C7 S1 1.7(3) . . . . ?
C8 N1 C7 S1 174.31(16) . . . . ?
C5 S1 C7 N2 179.8(2) . . . . ?
C5 S1 C7 N1 -1.18(19) . . . . ?
C7 N1 C8 C9 19.3(3) . . . . ?
C4 N1 C8 C9 -168.7(2) . . . . ?
C7 N1 C8 C14 -101.8(2) . . . . ?
C4 N1 C8 C14 70.3(3) . . . . ?
N1 C8 C9 C10 -21.8(3) . . . . ?
C14 C8 C9 C10 98.3(3) . . . . ?
N1 C8 C9 C11 158.0(2) . . . . ?
C14 C8 C9 C11 -81.9(3) . . . . ?
C11 C9 C10 N2 -168.2(2) . . . . ?
C8 C9 C10 N2 11.6(4) . . . . ?
C11 C9 C10 C24 10.3(4) . . . . ?
C8 C9 C10 C24 -169.9(2) . . . . ?
C7 N2 C10 C9 3.7(4) . . . . ?
C7 N2 C10 C24 -175.0(2) . . . . ?
C12 O2 C11 O1 1.9(5) . . . . ?
C12 O2 C11 C9 -176.6(3) . . . . ?
C10 C9 C11 O1 -23.9(4) . . . . ?
C8 C9 C11 O1 156.3(3) . . . . ?
C10 C9 C11 O2 154.4(3) . . . . ?
C8 C9 C11 O2 -25.4(3) . . . . ?
C11 O2 C12 C13 -177.8(3) . . . . ?
N1 C8 C14 C23 56.0(3) . . . . ?
C9 C8 C14 C23 -63.2(3) . . . . ?
N1 C8 C14 C19 -125.2(2) . . . . ?
C9 C8 C14 C19 115.6(3) . . . . ?
C20 C15 C16 C17 -0.3(6) . . . . ?
C15 C16 C17 C18 1.3(6) . . . . ?
C16 C17 C18 C19 -1.1(5) . . . . ?
C16 C17 C18 C21 177.4(3) . . . . ?
C23 C14 C19 C20 177.2(3) . . . . ?
C8 C14 C19 C20 -1.6(4) . . . . ?
C23 C14 C19 C18 -2.4(4) . . . . ?
C8 C14 C19 C18 178.8(2) . . . . ?
C17 C18 C19 C20 -0.2(4) . . . . ?
C21 C18 C19 C20 -178.7(3) . . . . ?
C17 C18 C19 C14 179.4(3) . . . . ?
C21 C18 C19 C14 0.9(4) . . . . ?
C16 C15 C20 C19 -1.0(5) . . . . ?
C14 C19 C20 C15 -178.4(3) . . . . ?
C18 C19 C20 C15 1.2(4) . . . . ?
C17 C18 C21 C22 -177.5(3) . . . . ?
C19 C18 C21 C22 1.0(4) . . . . ?
C18 C21 C22 C23 -1.4(5) . . . . ?
C21 C22 C23 C14 -0.1(4) . . . . ?
C19 C14 C23 C22 2.0(4) . . . . ?
C8 C14 C23 C22 -179.1(2) . . . . ?

_refine_diff_density_max         0.651
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_CCDC15
_database_code_depnum_ccdc_archive 'CCDC 2083682'
loop_
_audit_author_name
_audit_author_address
'Shanshan Gong'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O S'
_chemical_formula_weight         332.41

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'
O O 0.0106 0.0060 '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      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                   8.0329(6)
_cell_length_b                   19.2813(13)
_cell_length_c                   20.7588(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3215.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4560
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      26.70

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18158
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.884
_diffrn_reflns_theta_max         27.558
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3705
_reflns_number_gt                2690
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0666P)²+1.9422P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0058(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3705
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
S1 S 0.66901(9) 1.09944(3) 0.58713(3) 0.0507(2) Uani 1 1 d . . . . .
N1 N 0.6572(2) 0.97444(8) 0.63043(7) 0.0334(4) Uani 1 1 d . . . . .
C8 C 0.6460(2) 0.89788(9) 0.63085(9) 0.0306(4) Uani 1 1 d . . . . .
H8A H 0.711152 0.880185 0.667234 0.037 Uiso 1 1 calc R U . . .
O1 O 0.7517(2) 0.76089(8) 0.61430(8) 0.0511(4) Uani 1 1 d . . . . .
N2 N 0.7322(3) 0.98533(9) 0.51964(8) 0.0464(5) Uani 1 1 d . . . . .
C7 C 0.6882(3) 1.01029(10) 0.57548(10) 0.0378(5) Uani 1 1 d . . . . .
C9 C 0.7232(2) 0.87147(10) 0.56873(9) 0.0323(4) Uani 1 1 d . . . . .
C4 C 0.6147(3) 1.01619(10) 0.68327(10) 0.0359(5) Uani 1 1 d . . . . .
C15 C 0.4654(2) 0.87491(10) 0.63913(8) 0.0306(4) Uani 1 1 d . . . . .
C5 C 0.6134(3) 1.08668(11) 0.66763(11) 0.0418(5) Uani 1 1 d . . . . .
C14 C 0.7554(3) 0.91448(11) 0.51817(10) 0.0376(5) Uani 1 1 d . . . . .
C10 C 0.7683(3) 0.79841(10) 0.56655(10) 0.0387(5) Uani 1 1 d . . . . .
C16 C 0.4247(3) 0.82262(11) 0.68220(10) 0.0395(5) Uani 1 1 d . . . . .
H16A H 0.507772 0.801455 0.706433 0.047 Uiso 1 1 calc R U . . .
C20 C 0.3401(3) 0.90564(11) 0.60309(10) 0.0404(5) Uani 1 1 d . . . . .
H20A H 0.366066 0.940576 0.573877 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5793(3) 0.99424(12) 0.74541(10) 0.0456(5) Uani 1 1 d . . . . .
H3A H 0.581268 0.947465 0.756316 0.055 Uiso 1 1 calc R U . . .
C13 C 0.8261(3) 0.88873(12) 0.45593(11) 0.0514(6) Uani 1 1 d . . . . .
H13A H 0.944127 0.899196 0.454692 0.062 Uiso 1 1 calc R U . . .
H13B H 0.773369 0.913306 0.420618 0.062 Uiso 1 1 calc R U . . .
C17 C 0.2603(3) 0.80177(13) 0.68924(12) 0.0496(6) Uani 1 1 d . . . . .
H17A H 0.233589 0.766752 0.718270 0.060 Uiso 1 1 calc R U . . .
C19 C 0.1766(3) 0.88443(13) 0.61050(12) 0.0492(6) Uani 1 1 d . . . . .
H19A H 0.092981 0.905257 0.586291 0.059 Uiso 1 1 calc R U . . .
C18 C 0.1371(3) 0.83258(14) 0.65359(12) 0.0515(6) Uani 1 1 d . . . . .
H18A H 0.027056 0.818525 0.658471 0.062 Uiso 1 1 calc R U . . .
C11 C 0.8434(4) 0.77112(13) 0.50533(12) 0.0551(6) Uani 1 1 d . . . . .
H11A H 0.963454 0.769806 0.510286 0.066 Uiso 1 1 calc R U . . .
H11B H 0.805537 0.723854 0.498928 0.066 Uiso 1 1 calc R U . . .
C1 C 0.5367(4) 1.11455(14) 0.77490(13) 0.0615(7) Uani 1 1 d . . . . .
H1A H 0.507962 1.147021 0.806109 0.074 Uiso 1 1 calc R U . . .
C6 C 0.5747(3) 1.13648(13) 0.71359(13) 0.0545(6) Uani 1 1 d . . . . .
H6A H 0.574420 1.183393 0.703186 0.065 Uiso 1 1 calc R U . . .
C12 C 0.8025(5) 0.81244(15) 0.44638(14) 0.0799(10) Uani 1 1 d . . . . .
H12A H 0.872715 0.797094 0.411146 0.096 Uiso 1 1 calc R U . . .
H12B H 0.687693 0.803657 0.434361 0.096 Uiso 1 1 calc R U . . .
C2 C 0.5406(4) 1.04482(14) 0.79083(12) 0.0566(7) Uani 1 1 d . . . . .
H2B H 0.516729 1.031479 0.832884 0.068 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 C7 1.743(2) . ?
S1 C5 1.747(2) . ?
N1 C7 1.357(2) . ?
N1 C4 1.403(2) . ?
N1 C8 1.479(2) . ?
C8 C9 1.519(3) . ?
C8 C15 1.527(3) . ?
C8 H8A 0.9800 . ?
O1 C10 1.234(3) . ?
N2 C7 1.304(3) . ?
N2 C14 1.379(3) . ?
C9 C14 1.362(3) . ?
C9 C10 1.455(3) . ?
C4 C3 1.387(3) . ?
C4 C5 1.397(3) . ?
C15 C20 1.387(3) . ?
C15 C16 1.387(3) . ?
C5 C6 1.389(3) . ?
C14 C13 1.496(3) . ?
C10 C11 1.502(3) . ?
C16 C17 1.388(3) . ?
C16 H16A 0.9300 . ?
C20 C19 1.385(3) . ?
C20 H20A 0.9300 . ?
C3 C2 1.392(3) . ?
C3 H3A 0.9300 . ?
C13 C12 1.496(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C17 C18 1.371(4) . ?
C17 H17A 0.9300 . ?
C19 C18 1.378(4) . ?
C19 H19A 0.9300 . ?
C18 H18A 0.9300 . ?
C11 C12 1.497(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C1 C6 1.375(4) . ?
C1 C2 1.385(4) . ?
C1 H1A 0.9300 . ?
C6 H6A 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 H2B 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
C7 S1 C5 90.94(10) . . ?
C7 N1 C4 114.17(16) . . ?
C7 N1 C8 121.65(16) . . ?
C4 N1 C8 123.61(15) . . ?
N1 C8 C9 107.75(15) . . ?
N1 C8 C15 110.35(15) . . ?
C9 C8 C15 112.73(15) . . ?
N1 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C15 C8 H8A 108.6 . . ?
C7 N2 C14 114.95(17) . . ?
N2 C7 N1 127.52(18) . . ?
N2 C7 S1 120.76(15) . . ?
N1 C7 S1 111.70(15) . . ?
C14 C9 C10 121.22(19) . . ?
C14 C9 C8 121.82(17) . . ?
C10 C9 C8 116.91(16) . . ?
C3 C4 C5 120.74(19) . . ?
C3 C4 N1 127.01(19) . . ?
C5 C4 N1 112.24(18) . . ?
C20 C15 C16 119.19(19) . . ?
C20 C15 C8 120.32(17) . . ?
C16 C15 C8 120.49(17) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 S1 128.10(18) . . ?
C4 C5 S1 110.92(16) . . ?
C9 C14 N2 124.10(19) . . ?
C9 C14 C13 122.35(19) . . ?
N2 C14 C13 113.51(18) . . ?
O1 C10 C9 121.04(19) . . ?
O1 C10 C11 121.15(19) . . ?
C9 C10 C11 117.74(19) . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C19 C20 C15 120.1(2) . . ?
C19 C20 H20A 119.9 . . ?
C15 C20 H20A 119.9 . . ?
C4 C3 C2 117.5(2) . . ?
C4 C3 H3A 121.2 . . ?
C2 C3 H3A 121.2 . . ?
C14 C13 C12 113.1(2) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C18 C19 C20 120.3(2) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18A 120.1 . . ?
C19 C18 H18A 120.1 . . ?
C12 C11 C10 114.6(2) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C6 C1 C2 121.0(2) . . ?
C6 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 H6A 120.9 . . ?
C5 C6 H6A 120.9 . . ?
C13 C12 C11 112.8(2) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2B 119.2 . . ?
C3 C2 H2B 119.2 . . ?

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 N1 C8 C9 16.4(2) . . . . ?
C4 N1 C8 C9 -172.76(17) . . . . ?
C7 N1 C8 C15 -107.1(2) . . . . ?
C4 N1 C8 C15 63.8(2) . . . . ?
C14 N2 C7 N1 -2.7(3) . . . . ?
C14 N2 C7 S1 175.16(17) . . . . ?
C4 N1 C7 N2 179.0(2) . . . . ?
C8 N1 C7 N2 -9.4(3) . . . . ?
C4 N1 C7 S1 1.0(2) . . . . ?
C8 N1 C7 S1 172.59(14) . . . . ?
C5 S1 C7 N2 -179.5(2) . . . . ?
C5 S1 C7 N1 -1.29(17) . . . . ?
N1 C8 C9 C14 -14.2(3) . . . . ?
C15 C8 C9 C14 107.8(2) . . . . ?
N1 C8 C9 C10 163.21(17) . . . . ?
C15 C8 C9 C10 -74.8(2) . . . . ?
C7 N1 C4 C3 -178.9(2) . . . . ?
C8 N1 C4 C3 9.6(3) . . . . ?
C7 N1 C4 C5 0.1(3) . . . . ?
C8 N1 C4 C5 -171.40(18) . . . . ?
N1 C8 C15 C20 46.1(2) . . . . ?
C9 C8 C15 C20 -74.4(2) . . . . ?
N1 C8 C15 C16 -134.61(18) . . . . ?
C9 C8 C15 C16 104.9(2) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
N1 C4 C5 C6 -179.8(2) . . . . ?
C3 C4 C5 S1 178.04(18) . . . . ?
N1 C4 C5 S1 -1.0(2) . . . . ?
C7 S1 C5 C6 180.0(2) . . . . ?
C7 S1 C5 C4 1.31(18) . . . . ?
C10 C9 C14 N2 -172.9(2) . . . . ?
C8 C9 C14 N2 4.5(3) . . . . ?
C10 C9 C14 C13 4.8(3) . . . . ?
C8 C9 C14 C13 -177.9(2) . . . . ?
C7 N2 C14 C9 5.0(3) . . . . ?
C7 N2 C14 C13 -172.8(2) . . . . ?
C14 C9 C10 O1 173.9(2) . . . . ?
C8 C9 C10 O1 -3.5(3) . . . . ?
C14 C9 C10 C11 -3.1(3) . . . . ?
C8 C9 C10 C11 179.47(19) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?
C8 C15 C16 C17 -179.68(19) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
C8 C15 C20 C19 179.7(2) . . . . ?
C5 C4 C3 C2 0.8(3) . . . . ?
N1 C4 C3 C2 179.7(2) . . . . ?
C9 C14 C13 C12 19.9(4) . . . . ?
N2 C14 C13 C12 -162.2(2) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C15 C20 C19 C18 -0.1(4) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C20 C19 C18 C17 -0.1(4) . . . . ?
O1 C10 C11 C12 159.6(3) . . . . ?
C9 C10 C11 C12 -23.4(3) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
S1 C5 C6 C1 -178.9(2) . . . . ?
C14 C13 C12 C11 -45.2(4) . . . . ?
C10 C11 C12 C13 47.4(4) . . . . ?
C6 C1 C2 C3 -1.4(4) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?

_refine_diff_density_max         1.027
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_CCDC16
_database_code_depnum_ccdc_archive 'CCDC 2083668'
_audit_update_record             
;
2021-05-19 deposited with the CCDC.	2021-06-30 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            'C11 H8 N2 O S'
_chemical_formula_weight         216.25

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'
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                   7.3929(11)
_cell_length_b                   11.9385(18)
_cell_length_c                   10.8700(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.511(2)
_cell_angle_gamma                90
_cell_volume                     946.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1905
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.311
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5354
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         27.652
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2129
_reflns_number_gt                1407
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0419P)²+0.6471P] 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         2129
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.220
_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
S1 S 0.40269(11) 1.00199(7) 0.19961(7) 0.0403(3) Uani 1 1 d . . . . .
N2 N 0.2275(3) 0.97427(19) -0.02478(19) 0.0299(6) Uani 1 1 d . . . . .
C5 C 0.3082(4) 0.9135(3) 0.0783(2) 0.0306(7) Uani 1 1 d . . . . .
N1 N 0.3179(3) 0.8061(2) 0.0880(2) 0.0385(6) Uani 1 1 d . . . . .
C6 C 0.2380(4) 1.0914(3) -0.0080(2) 0.0290(6) Uani 1 1 d . . . . .
C3 C 0.1645(4) 0.7981(3) -0.1233(3) 0.0405(8) Uani 1 1 d . . . . .
H3A H 0.1191 0.7539 -0.1919 0.049 Uiso 1 1 calc R U . . .
O1 O 0.0747(3) 0.9697(2) -0.22634(19) 0.0514(7) Uani 1 1 d . . . . .
C4 C 0.1481(4) 0.9162(3) -0.1353(3) 0.0363(7) Uani 1 1 d . . . . .
C11 C 0.3288(4) 1.1201(3) 0.1108(2) 0.0339(7) Uani 1 1 d . . . . .
C7 C 0.1694(4) 1.1738(3) -0.0921(3) 0.0372(7) Uani 1 1 d . . . . .
H7A H 0.1097 1.1554 -0.1717 0.045 Uiso 1 1 calc R U . . .
C2 C 0.2430(4) 0.7467(3) -0.0168(3) 0.0383(8) Uani 1 1 d . . . . .
C10 C 0.3527(4) 1.2306(3) 0.1468(3) 0.0411(8) Uani 1 1 d . . . . .
H10A H 0.4155 1.2494 0.2254 0.049 Uiso 1 1 calc R U . . .
C8 C 0.1919(4) 1.2846(3) -0.0546(3) 0.0441(8) Uani 1 1 d . . . . .
H8A H 0.1463 1.3413 -0.1098 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2812(4) 1.3123(3) 0.0635(3) 0.0459(8) Uani 1 1 d . . . . .
H9A H 0.2931 1.3873 0.0869 0.055 Uiso 1 1 calc R U . . .
C1 C 0.2508(5) 0.6223(3) -0.0026(3) 0.0541(10) Uani 1 1 d . . . . .
H1B H 0.3119 0.6034 0.0797 0.081 Uiso 1 1 calc R U . . .
H1C H 0.1284 0.5926 -0.0151 0.081 Uiso 1 1 calc R U . . .
H1D H 0.3169 0.5908 -0.0633 0.081 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 C5 1.743(3) . ?
S1 C11 1.745(3) . ?
N2 C5 1.385(3) . ?
N2 C6 1.410(4) . ?
N2 C4 1.427(3) . ?
C5 N1 1.287(4) . ?
N1 C2 1.378(4) . ?
C6 C7 1.381(4) . ?
C6 C11 1.397(4) . ?
C3 C2 1.353(4) . ?
C3 C4 1.420(4) . ?
C3 H3A 0.9300 . ?
O1 C4 1.226(3) . ?
C11 C10 1.379(4) . ?
C7 C8 1.386(4) . ?
C7 H7A 0.9300 . ?
C2 C1 1.494(5) . ?
C10 C9 1.376(4) . ?
C10 H10A 0.9300 . ?
C8 C9 1.383(4) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C11 91.25(14) . . ?
C5 N2 C6 114.1(2) . . ?
C5 N2 C4 119.3(2) . . ?
C6 N2 C4 126.6(2) . . ?
N1 C5 N2 126.8(3) . . ?
N1 C5 S1 122.1(2) . . ?
N2 C5 S1 111.1(2) . . ?
C5 N1 C2 115.8(3) . . ?
C7 C6 C11 120.3(3) . . ?
C7 C6 N2 127.9(2) . . ?
C11 C6 N2 111.8(2) . . ?
C2 C3 C4 123.2(3) . . ?
C2 C3 H3A 118.4 . . ?
C4 C3 H3A 118.4 . . ?
O1 C4 C3 127.7(3) . . ?
O1 C4 N2 119.5(3) . . ?
C3 C4 N2 112.8(2) . . ?
C10 C11 C6 121.1(3) . . ?
C10 C11 S1 127.1(2) . . ?
C6 C11 S1 111.8(2) . . ?
C8 C7 C6 118.2(3) . . ?
C8 C7 H7A 120.9 . . ?
C6 C7 H7A 120.9 . . ?
C3 C2 N1 122.1(3) . . ?
C3 C2 C1 122.9(3) . . ?
N1 C2 C1 115.0(3) . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 H10A 120.8 . . ?
C11 C10 H10A 120.8 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 C5 N1 -180.0(3) . . . . ?
C4 N2 C5 N1 -1.4(4) . . . . ?
C6 N2 C5 S1 -0.7(3) . . . . ?
C4 N2 C5 S1 177.85(19) . . . . ?
C11 S1 C5 N1 -179.7(3) . . . . ?
C11 S1 C5 N2 1.0(2) . . . . ?
N2 C5 N1 C2 1.4(4) . . . . ?
S1 C5 N1 C2 -177.7(2) . . . . ?
C5 N2 C6 C7 -179.2(3) . . . . ?
C4 N2 C6 C7 2.3(5) . . . . ?
C5 N2 C6 C11 0.0(3) . . . . ?
C4 N2 C6 C11 -178.5(2) . . . . ?
C2 C3 C4 O1 -177.7(3) . . . . ?
C2 C3 C4 N2 1.7(4) . . . . ?
C5 N2 C4 O1 179.2(3) . . . . ?
C6 N2 C4 O1 -2.4(4) . . . . ?
C5 N2 C4 C3 -0.2(4) . . . . ?
C6 N2 C4 C3 178.2(3) . . . . ?
C7 C6 C11 C10 -0.2(4) . . . . ?
N2 C6 C11 C10 -179.5(3) . . . . ?
C7 C6 C11 S1 -180.0(2) . . . . ?
N2 C6 C11 S1 0.8(3) . . . . ?
C5 S1 C11 C10 179.3(3) . . . . ?
C5 S1 C11 C6 -1.0(2) . . . . ?
C11 C6 C7 C8 -0.6(4) . . . . ?
N2 C6 C7 C8 178.6(3) . . . . ?
C4 C3 C2 N1 -1.7(5) . . . . ?
C4 C3 C2 C1 176.6(3) . . . . ?
C5 N1 C2 C3 0.1(4) . . . . ?
C5 N1 C2 C1 -178.3(3) . . . . ?
C6 C11 C10 C9 1.4(5) . . . . ?
S1 C11 C10 C9 -178.9(2) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C11 C10 C9 C8 -1.7(5) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.073

