# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1883723'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-30 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         'C27 H25 N O3 S'
_chemical_formula_sum            'C27 H25 N O3 S'
_chemical_formula_weight         443.54

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                   7.8518(6)
_cell_length_b                   10.3592(7)
_cell_length_c                   14.2099(11)
_cell_angle_alpha                80.043(2)
_cell_angle_beta                 83.223(2)
_cell_angle_gamma                82.438(2)
_cell_volume                     1123.12(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6127
_cell_measurement_theta_min      2.63
_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    1.312
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17449
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.629
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5141
_reflns_number_gt                3391
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0591P)²+0.2134P] 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         5141
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
C1 C 0.4737(2) 0.11721(17) 0.64327(11) 0.0423(4) Uani 1 1 d . . . . .
C2 C 0.5877(3) 0.0975(2) 0.56372(13) 0.0545(5) Uani 1 1 d . . . . .
H2 H 0.5519 0.1246 0.5026 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7530(3) 0.0384(3) 0.57396(15) 0.0692(6) Uani 1 1 d . . . . .
H3 H 0.8276 0.0226 0.5203 0.083 Uiso 1 1 calc R U . . .
C4 C 0.8072(3) 0.0028(2) 0.66423(15) 0.0690(6) Uani 1 1 d . . . . .
H4 H 0.9188 -0.0377 0.6716 0.083 Uiso 1 1 calc R U . . .
C5 C 0.6969(2) 0.02692(19) 0.74426(13) 0.0512(5) Uani 1 1 d . . . . .
H5 H 0.7365 0.0055 0.8048 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5286(2) 0.08249(16) 0.73509(11) 0.0391(4) Uani 1 1 d . . . . .
C7 C 0.1697(2) 0.21585(17) 0.73667(11) 0.0402(4) Uani 1 1 d . . . . .
C8 C 0.2558(2) 0.17157(16) 0.81962(11) 0.0363(4) Uani 1 1 d . . . . .
C9 C 0.1712(2) 0.20306(15) 0.90719(10) 0.0345(4) Uani 1 1 d . . . . .
C10 C 0.2739(2) 0.17897(17) 0.99187(11) 0.0370(4) Uani 1 1 d . . . . .
C11 C 0.3939(3) 0.2840(2) 1.09848(14) 0.0627(6) Uani 1 1 d . . . . .
H11A H 0.3365 0.2477 1.1589 0.094 Uiso 1 1 calc R U . . .
H11B H 0.4195 0.3711 1.1015 0.094 Uiso 1 1 calc R U . . .
H11C H 0.4992 0.2289 1.0851 0.094 Uiso 1 1 calc R U . . .
C12 C -0.0933(2) 0.15510(17) 1.08208(12) 0.0424(4) Uani 1 1 d . . . . .
H12 H -0.0544 0.0731 1.0643 0.051 Uiso 1 1 calc R U . . .
C13 C -0.1587(2) 0.16281(19) 1.17564(12) 0.0467(5) Uani 1 1 d . . . . .
H13 H -0.1644 0.0856 1.2198 0.056 Uiso 1 1 calc R U . . .
C14 C -0.2159(2) 0.2826(2) 1.20516(12) 0.0466(5) Uani 1 1 d . . . . .
C15 C -0.2859(3) 0.2885(3) 1.30801(14) 0.0774(7) Uani 1 1 d . . . . .
H15A H -0.3957 0.2544 1.3205 0.116 Uiso 1 1 calc R U . . .
H15B H -0.2997 0.3783 1.3189 0.116 Uiso 1 1 calc R U . . .
H15C H -0.2069 0.2364 1.3501 0.116 Uiso 1 1 calc R U . . .
C16 C -0.2087(2) 0.39533(19) 1.13702(13) 0.0468(4) Uani 1 1 d . . . . .
H16 H -0.2468 0.4772 1.1550 0.056 Uiso 1 1 calc R U . . .
C17 C -0.1459(2) 0.38836(17) 1.04276(12) 0.0407(4) Uani 1 1 d . . . . .
H17 H -0.1448 0.4653 0.9980 0.049 Uiso 1 1 calc R U . . .
C18 C -0.0848(2) 0.26830(16) 1.01413(11) 0.0344(4) Uani 1 1 d . . . . .
C19 C -0.0008(2) 0.25735(16) 0.91506(11) 0.0345(4) Uani 1 1 d . . . . .
C20 C -0.0863(2) 0.29709(17) 0.83132(11) 0.0382(4) Uani 1 1 d . . . . .
C21 C 0.0054(2) 0.28310(17) 0.74142(11) 0.0400(4) Uani 1 1 d . . . . .
C22 C -0.0797(2) 0.3356(2) 0.65004(12) 0.0510(5) Uani 1 1 d . . . . .
H22A H -0.1313 0.2648 0.6316 0.061 Uiso 1 1 calc R U . . .
H22B H 0.0085 0.3625 0.5993 0.061 Uiso 1 1 calc R U . . .
C23 C -0.2179(2) 0.45163(19) 0.65805(12) 0.0474(5) Uani 1 1 d . . . . .
C24 C -0.3098(3) 0.4827(2) 0.56579(14) 0.0659(6) Uani 1 1 d . . . . .
H24A H -0.3980 0.5555 0.5703 0.099 Uiso 1 1 calc R U . . .
H24B H -0.3613 0.4068 0.5577 0.099 Uiso 1 1 calc R U . . .
H24C H -0.2277 0.5052 0.5117 0.099 Uiso 1 1 calc R U . . .
C25 C -0.1393(3) 0.5723(2) 0.67192(16) 0.0679(6) Uani 1 1 d . . . . .
H25A H -0.0852 0.5537 0.7307 0.102 Uiso 1 1 calc R U . . .
H25B H -0.2283 0.6449 0.6748 0.102 Uiso 1 1 calc R U . . .
H25C H -0.0547 0.5946 0.6191 0.102 Uiso 1 1 calc R U . . .
C26 C -0.3472(2) 0.4098(2) 0.74290(13) 0.0502(5) Uani 1 1 d . . . . .
H26A H -0.4226 0.4876 0.7568 0.060 Uiso 1 1 calc R U . . .
H26B H -0.4181 0.3508 0.7237 0.060 Uiso 1 1 calc R U . . .
C27 C -0.2733(2) 0.3426(2) 0.83389(12) 0.0482(5) Uani 1 1 d . . . . .
N1 N 0.41799(19) 0.10198(15) 0.81690(9) 0.0459(4) Uani 1 1 d . . . . .
H1 H 0.4547 0.0670 0.8713 0.055 Uiso 1 1 calc R U . . .
O1 O 0.34382(19) 0.07320(13) 1.02464(9) 0.0600(4) Uani 1 1 d . . . . .
O2 O 0.28309(15) 0.29007(12) 1.02334(8) 0.0452(3) Uani 1 1 d . . . . .
O3 O -0.37084(18) 0.3216(2) 0.90607(10) 0.0900(6) Uani 1 1 d . . . . .
S1 S 0.2535(7) 0.1667(6) 0.6261(3) 0.0456(15) Uani 0.43(3) 1 d . . P A 1
S1' S 0.2684(10) 0.1913(13) 0.6208(4) 0.0906(14) Uani 0.57(3) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(2) . ?
C1 C6 1.395(2) . ?
C1 S1' 1.733(5) . ?
C1 S1 1.770(6) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.394(2) . ?
C7 C21 1.383(2) . ?
C7 C8 1.406(2) . ?
C7 S1 1.762(4) . ?
C7 S1' 1.780(5) . ?
C8 N1 1.378(2) . ?
C8 C9 1.409(2) . ?
C9 C19 1.393(2) . ?
C9 C10 1.494(2) . ?
C10 O1 1.2018(19) . ?
C10 O2 1.318(2) . ?
C11 O2 1.443(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.379(2) . ?
C12 C18 1.388(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C16 1.385(3) . ?
C14 C15 1.508(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.499(2) . ?
C19 C20 1.408(2) . ?
C20 C21 1.411(2) . ?
C20 C27 1.480(2) . ?
C21 C22 1.515(2) . ?
C22 C23 1.519(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C25 1.516(3) . ?
C23 C26 1.523(2) . ?
C23 C24 1.536(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.501(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 O3 1.211(2) . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.99(17) . . ?
C2 C1 S1' 116.3(2) . . ?
C6 C1 S1' 123.7(2) . . ?
C2 C1 S1 118.18(19) . . ?
C6 C1 S1 121.3(2) . . ?
C3 C2 C1 120.77(17) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.41(18) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.64(18) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 N1 119.72(15) . . ?
C5 C6 C1 118.63(16) . . ?
N1 C6 C1 121.65(15) . . ?
C21 C7 C8 121.28(15) . . ?
C21 C7 S1 117.2(2) . . ?
C8 C7 S1 120.9(2) . . ?
C21 C7 S1' 117.01(19) . . ?
C8 C7 S1' 121.7(2) . . ?
N1 C8 C7 122.30(14) . . ?
N1 C8 C9 120.25(14) . . ?
C7 C8 C9 117.44(15) . . ?
C19 C9 C8 121.74(14) . . ?
C19 C9 C10 120.62(13) . . ?
C8 C9 C10 117.62(14) . . ?
O1 C10 O2 124.61(15) . . ?
O1 C10 C9 124.47(16) . . ?
O2 C10 C9 110.87(14) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C18 120.71(17) . . ?
C13 C12 H12 119.6 . . ?
C18 C12 H12 119.6 . . ?
C12 C13 C14 121.47(16) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C16 117.70(16) . . ?
C13 C14 C15 120.46(18) . . ?
C16 C14 C15 121.83(19) . . ?
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 . . ?
C17 C16 C14 121.22(17) . . ?
C17 C16 H16 119.4 . . ?
C14 C16 H16 119.4 . . ?
C16 C17 C18 120.81(16) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C12 118.06(15) . . ?
C17 C18 C19 122.51(14) . . ?
C12 C18 C19 119.32(15) . . ?
C9 C19 C20 119.14(14) . . ?
C9 C19 C18 117.02(13) . . ?
C20 C19 C18 123.83(14) . . ?
C19 C20 C21 119.18(15) . . ?
C19 C20 C27 122.62(14) . . ?
C21 C20 C27 117.99(14) . . ?
C7 C21 C20 120.17(14) . . ?
C7 C21 C22 119.84(15) . . ?
C20 C21 C22 119.91(15) . . ?
C21 C22 C23 114.28(15) . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C25 C23 C22 110.93(17) . . ?
C25 C23 C26 110.88(16) . . ?
C22 C23 C26 107.41(15) . . ?
C25 C23 C24 109.53(17) . . ?
C22 C23 C24 108.82(15) . . ?
C26 C23 C24 109.20(15) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C23 116.45(15) . . ?
C27 C26 H26A 108.2 . . ?
C23 C26 H26A 108.2 . . ?
C27 C26 H26B 108.2 . . ?
C23 C26 H26B 108.2 . . ?
H26A C26 H26B 107.3 . . ?
O3 C27 C20 122.21(16) . . ?
O3 C27 C26 118.53(16) . . ?
C20 C27 C26 119.16(15) . . ?
C8 N1 C6 126.69(13) . . ?
C8 N1 H1 116.7 . . ?
C6 N1 H1 116.7 . . ?
C10 O2 C11 116.92(14) . . ?
C7 S1 C1 102.4(2) . . ?
C1 S1' C7 103.2(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
N1 H1 O1 0.86 2.26 2.9117(18) 132.8 .
N1 H1 O1 0.86 2.45 3.2478(19) 154.6 2_657

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.045


####################################################################### 
# 
# 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_2g
_database_code_depnum_ccdc_archive 'CCDC 1883724'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-30 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         'C26 H22 Cl N O3 S'
_chemical_formula_sum            'C26 H22 Cl N O3 S'
_chemical_formula_weight         463.95

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                   5.9034(5)
_cell_length_b                   21.165(2)
_cell_length_c                   21.6677(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.308(3)
_cell_angle_gamma                90
_cell_volume                     2706.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4739
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      22.31

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             968
_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    0.242
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27612
_diffrn_reflns_av_unetI/netI     0.1132
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.691
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6228
_reflns_number_gt                2851
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0914P)²+1.6490P] 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         6228
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.2261
_refine_ls_wR_factor_gt          0.1912
_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
C1 C 0.0935(7) 0.56665(17) 0.40517(17) 0.0452(10) Uani 1 1 d . . . . .
C2 C -0.0966(7) 0.53233(18) 0.4187(2) 0.0526(11) Uani 1 1 d . . . . .
H2 H -0.1281 0.5240 0.4598 0.063 Uiso 1 1 calc R U . . .
C3 C -0.2401(8) 0.5102(2) 0.3736(2) 0.0640(12) Uani 1 1 d . . . . .
H3 H -0.3675 0.4868 0.3836 0.077 Uiso 1 1 calc R U . . .
C4 C -0.1937(8) 0.5229(2) 0.3133(2) 0.0709(14) Uani 1 1 d . . . . .
H4 H -0.2878 0.5069 0.2821 0.085 Uiso 1 1 calc R U . . .
C5 C -0.0093(8) 0.55921(19) 0.2984(2) 0.0597(12) Uani 1 1 d . . . . .
H5 H 0.0185 0.5682 0.2573 0.072 Uiso 1 1 calc R U . . .
C6 C 0.1346(6) 0.58231(18) 0.34409(18) 0.0467(10) Uani 1 1 d . . . . .
C7 C 0.4568(6) 0.64462(17) 0.43154(16) 0.0388(9) Uani 1 1 d . . . . .
C8 C 0.4600(6) 0.65347(17) 0.36663(16) 0.0397(9) Uani 1 1 d . . . . .
C9 C 0.6227(6) 0.69466(17) 0.34219(16) 0.0417(9) Uani 1 1 d . . . . .
C10 C 0.6351(8) 0.69831(18) 0.27386(18) 0.0515(10) Uani 1 1 d . . . . .
C11 C 0.8744(8) 0.7090(2) 0.18757(18) 0.0720(14) Uani 1 1 d . . . . .
H11A H 0.8379 0.6694 0.1681 0.108 Uiso 1 1 calc R U . . .
H11B H 1.0288 0.7198 0.1795 0.108 Uiso 1 1 calc R U . . .
H11C H 0.7758 0.7413 0.1713 0.108 Uiso 1 1 calc R U . . .
C12 C 0.4248(7) 0.6842(2) 0.57497(18) 0.0549(11) Uani 1 1 d . . . . .
H12 H 0.3101 0.7093 0.5580 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4201(8) 0.6682(2) 0.63640(19) 0.0620(12) Uani 1 1 d . . . . .
H13 H 0.3032 0.6822 0.6610 0.074 Uiso 1 1 calc R U . . .
C14 C 0.5891(8) 0.6314(2) 0.66085(17) 0.0515(11) Uani 1 1 d . . . . .
C15 C 0.7600(8) 0.60945(19) 0.62569(18) 0.0538(11) Uani 1 1 d . . . . .
H15 H 0.8729 0.5839 0.6429 0.065 Uiso 1 1 calc R U . . .
C16 C 0.7635(7) 0.62553(18) 0.56440(17) 0.0480(10) Uani 1 1 d . . . . .
H16 H 0.8799 0.6105 0.5402 0.058 Uiso 1 1 calc R U . . .
C17 C 0.5988(6) 0.66333(17) 0.53795(15) 0.0397(9) Uani 1 1 d . . . . .
C18 C 0.6020(6) 0.67832(17) 0.47038(16) 0.0400(9) Uani 1 1 d . . . . .
C19 C 0.7572(6) 0.72203(17) 0.44539(16) 0.0412(9) Uani 1 1 d . . . . .
C20 C 0.7674(6) 0.72988(16) 0.38119(16) 0.0400(9) Uani 1 1 d . . . . .
C21 C 0.9309(7) 0.77775(18) 0.35443(18) 0.0517(10) Uani 1 1 d . . . . .
H21A H 1.0621 0.7552 0.3397 0.062 Uiso 1 1 calc R U . . .
H21B H 0.8575 0.7977 0.3190 0.062 Uiso 1 1 calc R U . . .
C22 C 1.0123(6) 0.82914(18) 0.39847(18) 0.0490(10) Uani 1 1 d . . . . .
C23 C 0.8240(8) 0.8756(2) 0.4133(2) 0.0678(13) Uani 1 1 d . . . . .
H23A H 0.7672 0.8945 0.3757 0.102 Uiso 1 1 calc R U . . .
H23B H 0.8827 0.9079 0.4403 0.102 Uiso 1 1 calc R U . . .
H23C H 0.7035 0.8536 0.4331 0.102 Uiso 1 1 calc R U . . .
C24 C 1.2085(8) 0.8644(2) 0.3690(2) 0.0810(15) Uani 1 1 d . . . . .
H24A H 1.3303 0.8355 0.3617 0.121 Uiso 1 1 calc R U . . .
H24B H 1.2607 0.8974 0.3962 0.121 Uiso 1 1 calc R U . . .
H24C H 1.1577 0.8825 0.3304 0.121 Uiso 1 1 calc R U . . .
C25 C 1.0951(7) 0.7965(2) 0.45802(19) 0.0568(11) Uani 1 1 d . . . . .
H25A H 1.2184 0.7680 0.4487 0.068 Uiso 1 1 calc R U . . .
H25B H 1.1525 0.8280 0.4869 0.068 Uiso 1 1 calc R U . . .
C26 C 0.9094(7) 0.76038(19) 0.4870(2) 0.0543(11) Uani 1 1 d . . . . .
Cl1 Cl 0.5860(3) 0.61140(7) 0.73921(5) 0.0922(5) Uani 1 1 d . . . . .
N1 N 0.3156(6) 0.62115(16) 0.32834(14) 0.0570(9) Uani 1 1 d . . . . .
H1 H 0.3386 0.6251 0.2895 0.068 Uiso 1 1 calc R U . . .
O1 O 0.4743(6) 0.69474(18) 0.23862(14) 0.0871(11) Uani 1 1 d . . . . .
O2 O 0.8448(5) 0.70352(13) 0.25383(11) 0.0561(7) Uani 1 1 d . . . . .
O3 O 0.8831(6) 0.76352(16) 0.54216(14) 0.0822(10) Uani 1 1 d . . . . .
S1 S 0.28212(19) 0.58739(6) 0.46572(5) 0.0652(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(5) . ?
C1 C6 1.391(5) . ?
C1 S1 1.757(4) . ?
C2 C3 1.363(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 N1 1.396(5) . ?
C7 C18 1.385(5) . ?
C7 C8 1.420(5) . ?
C7 S1 1.765(4) . ?
C8 N1 1.360(5) . ?
C8 C9 1.409(5) . ?
C9 C20 1.402(5) . ?
C9 C10 1.486(5) . ?
C10 O1 1.207(5) . ?
C10 O2 1.326(5) . ?
C11 O2 1.455(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.375(6) . ?
C12 C17 1.389(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(6) . ?
C14 Cl1 1.750(4) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.498(5) . ?
C18 C19 1.419(5) . ?
C19 C20 1.404(5) . ?
C19 C26 1.497(5) . ?
C20 C21 1.523(5) . ?
C21 C22 1.518(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.523(6) . ?
C22 C24 1.531(6) . ?
C22 C25 1.534(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.486(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O3 1.212(5) . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.4(4) . . ?
C2 C1 S1 118.6(3) . . ?
C6 C1 S1 122.0(3) . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.7(4) . . ?
C5 C6 N1 119.7(4) . . ?
C1 C6 N1 121.6(3) . . ?
C18 C7 C8 120.8(3) . . ?
C18 C7 S1 117.2(3) . . ?
C8 C7 S1 121.8(3) . . ?
N1 C8 C9 120.3(3) . . ?
N1 C8 C7 121.0(3) . . ?
C9 C8 C7 118.6(3) . . ?
C20 C9 C8 120.9(3) . . ?
C20 C9 C10 122.0(3) . . ?
C8 C9 C10 117.1(3) . . ?
O1 C10 O2 121.7(4) . . ?
O1 C10 C9 124.8(4) . . ?
O2 C10 C9 113.5(3) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C17 C12 H12 119.6 . . ?
C14 C13 C12 119.1(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 121.6(4) . . ?
C15 C14 Cl1 119.0(3) . . ?
C13 C14 Cl1 119.5(3) . . ?
C14 C15 C16 119.0(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C17 121.5(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C12 118.0(3) . . ?
C16 C17 C18 120.4(3) . . ?
C12 C17 C18 121.5(3) . . ?
C7 C18 C19 120.0(3) . . ?
C7 C18 C17 117.6(3) . . ?
C19 C18 C17 122.2(3) . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 C26 119.6(3) . . ?
C18 C19 C26 120.6(3) . . ?
C9 C20 C19 119.7(3) . . ?
C9 C20 C21 120.4(3) . . ?
C19 C20 C21 119.9(3) . . ?
C22 C21 C20 115.6(3) . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 C23 111.9(3) . . ?
C21 C22 C24 108.6(3) . . ?
C23 C22 C24 109.6(4) . . ?
C21 C22 C25 107.2(3) . . ?
C23 C22 C25 109.5(3) . . ?
C24 C22 C25 110.0(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C22 111.2(3) . . ?
C26 C25 H25A 109.4 . . ?
C22 C25 H25A 109.4 . . ?
C26 C25 H25B 109.4 . . ?
C22 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
O3 C26 C25 120.0(4) . . ?
O3 C26 C19 122.4(4) . . ?
C25 C26 C19 117.6(4) . . ?
C8 N1 C6 128.3(3) . . ?
C8 N1 H1 115.9 . . ?
C6 N1 H1 115.9 . . ?
C10 O2 C11 117.6(3) . . ?
C1 S1 C7 102.98(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.02 2.677(4) 132.9 .

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_2n
_database_code_depnum_ccdc_archive 'CCDC 1883726'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-30 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         'C24 H18 Cl N O3 S'
_chemical_formula_sum            'C24 H18 Cl N O3 S'
_chemical_formula_weight         435.90

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'
Cl Cl 0.1484 0.1585 '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                   9.3704(5)
_cell_length_b                   10.2251(6)
_cell_length_c                   11.2595(6)
_cell_angle_alpha                76.2532(18)
_cell_angle_beta                 78.5679(16)
_cell_angle_gamma                75.2513(17)
_cell_volume                     1002.43(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8744
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.322
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14080
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0241
_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       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.101
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3920
_reflns_number_gt                3358
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0498P)²+0.3885P] 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         3920
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C1 C 0.10905(18) 0.31480(17) 1.07323(15) 0.0367(4) Uani 1 1 d . . . . .
C2 C 0.0784(2) 0.3553(2) 1.18627(16) 0.0446(4) Uani 1 1 d . . . . .
H2 H 0.0027 0.3265 1.2459 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1600(2) 0.4386(2) 1.21055(18) 0.0508(5) Uani 1 1 d . . . . .
H3 H 0.1415 0.4627 1.2876 0.061 Uiso 1 1 calc R U . . .
C4 C 0.2688(2) 0.4860(2) 1.12121(18) 0.0503(5) Uani 1 1 d . . . . .
H4 H 0.3224 0.5431 1.1377 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2983(2) 0.44881(19) 1.00717(17) 0.0464(4) Uani 1 1 d . . . . .
H5 H 0.3699 0.4827 0.9461 0.056 Uiso 1 1 calc R U . . .
C6 C 0.22075(19) 0.36059(18) 0.98367(15) 0.0387(4) Uani 1 1 d . . . . .
C7 C 0.10796(17) 0.25389(17) 0.83140(14) 0.0331(3) Uani 1 1 d . . . . .
C8 C 0.00696(17) 0.21587(16) 0.93766(14) 0.0328(3) Uani 1 1 d . . . . .
C9 C -0.11663(17) 0.16761(16) 0.92481(14) 0.0328(3) Uani 1 1 d . . . . .
C10 C -0.22429(18) 0.13530(17) 1.03834(15) 0.0360(4) Uani 1 1 d . . . . .
C11 C -0.4729(2) 0.1238(2) 1.12183(18) 0.0545(5) Uani 1 1 d . . . . .
H11A H -0.4420 0.0279 1.1576 0.082 Uiso 1 1 calc R U . . .
H11B H -0.5683 0.1398 1.0955 0.082 Uiso 1 1 calc R U . . .
H11C H -0.4804 0.1785 1.1822 0.082 Uiso 1 1 calc R U . . .
C12 C -0.13440(17) 0.15232(16) 0.80764(15) 0.0338(3) Uani 1 1 d . . . . .
C13 C -0.2537(2) 0.0830(2) 0.79366(17) 0.0464(4) Uani 1 1 d . . . . .
H13A H -0.2699 0.0132 0.8671 0.056 Uiso 1 1 calc R U . . .
H13B H -0.3467 0.1510 0.7865 0.056 Uiso 1 1 calc R U . . .
C14 C -0.2107(3) 0.0166(2) 0.68126(18) 0.0563(5) Uani 1 1 d . . . . .
H14A H -0.1220 -0.0564 0.6906 0.068 Uiso 1 1 calc R U . . .
H14B H -0.2907 -0.0237 0.6733 0.068 Uiso 1 1 calc R U . . .
C15 C -0.1812(2) 0.1236(2) 0.56744(17) 0.0528(5) Uani 1 1 d . . . . .
H15A H -0.1474 0.0793 0.4966 0.063 Uiso 1 1 calc R U . . .
H15B H -0.2735 0.1902 0.5535 0.063 Uiso 1 1 calc R U . . .
C16 C -0.06610(19) 0.19791(18) 0.57744(15) 0.0378(4) Uani 1 1 d . . . . .
C17 C -0.03617(17) 0.19635(16) 0.70291(14) 0.0325(3) Uani 1 1 d . . . . .
C18 C 0.08670(17) 0.24637(16) 0.71565(14) 0.0317(3) Uani 1 1 d . . . . .
C19 C 0.20613(17) 0.27830(16) 0.61028(14) 0.0324(3) Uani 1 1 d . . . . .
C20 C 0.2189(2) 0.41302(18) 0.55828(16) 0.0420(4) Uani 1 1 d . . . . .
H20 H 0.1474 0.4859 0.5848 0.050 Uiso 1 1 calc R U . . .
C21 C 0.3367(2) 0.44022(19) 0.46752(16) 0.0453(4) Uani 1 1 d . . . . .
H21 H 0.3445 0.5307 0.4331 0.054 Uiso 1 1 calc R U . . .
C22 C 0.44176(19) 0.3323(2) 0.42873(15) 0.0403(4) Uani 1 1 d . . . . .
C23 C 0.4317(2) 0.1984(2) 0.47837(17) 0.0474(4) Uani 1 1 d . . . . .
H23 H 0.5034 0.1261 0.4512 0.057 Uiso 1 1 calc R U . . .
C24 C 0.31360(19) 0.17179(18) 0.56960(16) 0.0425(4) Uani 1 1 d . . . . .
H24 H 0.3067 0.0810 0.6038 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl 0.59218(6) 0.36635(6) 0.31645(4) 0.06278(18) Uani 1 1 d . . . . .
N1 N 0.03101(17) 0.22477(16) 1.05153(12) 0.0424(4) Uani 1 1 d . . . . .
H1 H -0.0048 0.1706 1.1148 0.051 Uiso 1 1 calc R U . . .
O1 O -0.19238(14) 0.09442(15) 1.14172(11) 0.0504(3) Uani 1 1 d . . . . .
O2 O -0.36450(13) 0.16172(14) 1.01667(11) 0.0485(3) Uani 1 1 d . . . . .
O3 O -0.00557(16) 0.26210(16) 0.48452(11) 0.0573(4) Uani 1 1 d . . . . .
S1 S 0.27590(5) 0.29410(6) 0.84692(4) 0.05065(16) 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 1.385(2) . ?
C1 C6 1.392(2) . ?
C1 N1 1.401(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9300 . ?
C6 S1 1.7615(17) . ?
C7 C18 1.379(2) . ?
C7 C8 1.413(2) . ?
C7 S1 1.7744(16) . ?
C8 N1 1.372(2) . ?
C8 C9 1.413(2) . ?
C9 C12 1.411(2) . ?
C9 C10 1.489(2) . ?
C10 O1 1.209(2) . ?
C10 O2 1.332(2) . ?
C11 O2 1.446(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.403(2) . ?
C12 C13 1.518(2) . ?
C13 C14 1.514(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.504(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.503(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.215(2) . ?
C16 C17 1.490(2) . ?
C17 C18 1.417(2) . ?
C18 C19 1.497(2) . ?
C19 C24 1.381(2) . ?
C19 C20 1.388(2) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(3) . ?
C22 Cl1 1.7437(16) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.53(16) . . ?
C2 C1 N1 119.82(15) . . ?
C6 C1 N1 120.62(15) . . ?
C3 C2 C1 120.12(18) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.42(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.99(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.95(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.91(16) . . ?
C5 C6 S1 119.86(14) . . ?
C1 C6 S1 119.96(13) . . ?
C18 C7 C8 121.11(14) . . ?
C18 C7 S1 118.51(12) . . ?
C8 C7 S1 120.01(12) . . ?
N1 C8 C7 119.73(14) . . ?
N1 C8 C9 121.07(14) . . ?
C7 C8 C9 119.20(14) . . ?
C12 C9 C8 119.95(14) . . ?
C12 C9 C10 122.69(14) . . ?
C8 C9 C10 117.36(14) . . ?
O1 C10 O2 121.77(15) . . ?
O1 C10 C9 124.93(15) . . ?
O2 C10 C9 113.23(14) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C9 119.57(14) . . ?
C17 C12 C13 119.31(14) . . ?
C9 C12 C13 121.05(14) . . ?
C14 C13 C12 111.87(15) . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 109.53(17) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 112.61(15) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
O3 C16 C17 122.04(15) . . ?
O3 C16 C15 119.55(15) . . ?
C17 C16 C15 118.33(15) . . ?
C12 C17 C18 120.26(14) . . ?
C12 C17 C16 119.80(14) . . ?
C18 C17 C16 119.86(14) . . ?
C7 C18 C17 119.69(14) . . ?
C7 C18 C19 117.01(14) . . ?
C17 C18 C19 122.97(13) . . ?
C24 C19 C20 118.62(15) . . ?
C24 C19 C18 119.60(14) . . ?
C20 C19 C18 121.58(14) . . ?
C21 C20 C19 120.80(16) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 119.32(16) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C21 121.07(16) . . ?
C23 C22 Cl1 119.56(14) . . ?
C21 C22 Cl1 119.37(14) . . ?
C22 C23 C24 119.34(17) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C19 C24 C23 120.86(16) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C8 N1 C1 125.42(14) . . ?
C8 N1 H1 117.3 . . ?
C1 N1 H1 117.3 . . ?
C10 O2 C11 115.88(14) . . ?
C6 S1 C7 100.97(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.04 2.6690(18) 129.3 .

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.041


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

data_7a
_database_code_depnum_ccdc_archive 'CCDC 1884301'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2018-12-11 deposited with the CCDC.	2019-08-30 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         'C23 H17 N O4 S'
_chemical_formula_sum            'C23 H17 N O4 S'
_chemical_formula_weight         403.43

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                   7.8538(6)
_cell_length_b                   13.4956(10)
_cell_length_c                   17.2047(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.145(3)
_cell_angle_gamma                90
_cell_volume                     1789.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3361
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.214
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8079
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.413
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             3956
_reflns_number_gt                2921
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0549P)²+0.8653P] 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         3956
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.0559(3) 0.67008(15) 0.30470(12) 0.0187(5) Uani 1 1 d . . . . .
C2 C -0.0392(3) 0.71665(17) 0.35483(13) 0.0268(5) Uani 1 1 d . . . . .
H2 H 0.0097 0.7254 0.4081 0.032 Uiso 1 1 calc R U . . .
C3 C -0.2056(3) 0.74988(19) 0.32574(14) 0.0318(6) Uani 1 1 d . . . . .
H3 H -0.2668 0.7835 0.3588 0.038 Uiso 1 1 calc R U . . .
C4 C -0.2810(3) 0.73311(19) 0.24736(14) 0.0287(6) Uani 1 1 d . . . . .
H4 H -0.3948 0.7531 0.2284 0.034 Uiso 1 1 calc R U . . .
C5 C -0.1884(3) 0.68681(17) 0.19689(13) 0.0225(5) Uani 1 1 d . . . . .
H5 H -0.2408 0.6747 0.1445 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0169(3) 0.65834(15) 0.22438(12) 0.0169(4) Uani 1 1 d . . . . .
C7 C 0.2570(3) 0.52135(17) 0.27534(12) 0.0222(5) Uani 1 1 d . . . . .
H7A H 0.3654 0.4848 0.2864 0.027 Uiso 1 1 calc R U . . .
H7B H 0.1636 0.4766 0.2810 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2276(3) 0.56193(15) 0.19369(12) 0.0164(4) Uani 1 1 d . . . . .
C9 C 0.3241(3) 0.55263(15) 0.13649(12) 0.0160(4) Uani 1 1 d . . . . .
C10 C 0.4810(3) 0.49729(15) 0.13773(12) 0.0169(4) Uani 1 1 d . . . . .
C11 C 0.6903(3) 0.38500(19) 0.20212(14) 0.0323(6) Uani 1 1 d . . . . .
H11A H 0.6771 0.3447 0.1554 0.048 Uiso 1 1 calc R U . . .
H11B H 0.7145 0.3435 0.2482 0.048 Uiso 1 1 calc R U . . .
H11C H 0.7845 0.4305 0.2029 0.048 Uiso 1 1 calc R U . . .
C12 C 0.2443(3) 0.61300(15) 0.06421(11) 0.0142(4) Uani 1 1 d . . . . .
C13 C 0.0792(3) 0.66247(15) 0.08995(11) 0.0144(4) Uani 1 1 d . . . . .
C14 C 0.1174(3) 0.77320(15) 0.09371(11) 0.0154(4) Uani 1 1 d . . . . .
C15 C 0.0241(3) 0.85357(16) 0.10940(12) 0.0199(5) Uani 1 1 d . . . . .
H15 H -0.0855 0.8457 0.1215 0.024 Uiso 1 1 calc R U . . .
C16 C 0.0970(3) 0.94902(17) 0.10698(13) 0.0237(5) Uani 1 1 d . . . . .
H16 H 0.0331 1.0038 0.1172 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2591(3) 0.96357(16) 0.09006(13) 0.0231(5) Uani 1 1 d . . . . .
H17 H 0.3048 1.0272 0.0913 0.028 Uiso 1 1 calc R U . . .
C18 C 0.3570(3) 0.88229(16) 0.07075(12) 0.0174(4) Uani 1 1 d . . . . .
C19 C 0.5192(3) 0.88520(16) 0.04624(12) 0.0195(5) Uani 1 1 d . . . . .
H19 H 0.5800 0.9446 0.0478 0.023 Uiso 1 1 calc R U . . .
C20 C 0.5863(3) 0.80068(16) 0.02029(12) 0.0197(5) Uani 1 1 d . . . . .
H20 H 0.6895 0.8050 0.0016 0.024 Uiso 1 1 calc R U . . .
C21 C 0.5058(3) 0.70687(16) 0.02048(12) 0.0166(4) Uani 1 1 d . . . . .
H21 H 0.5537 0.6510 0.0015 0.020 Uiso 1 1 calc R U . . .
C22 C 0.3548(3) 0.70062(15) 0.04956(11) 0.0150(4) Uani 1 1 d . . . . .
C23 C 0.2806(3) 0.78792(15) 0.07228(11) 0.0153(4) Uani 1 1 d . . . . .
N1 N 0.0829(2) 0.61967(13) 0.17057(10) 0.0162(4) Uani 1 1 d . . . . .
O1 O 0.5618(2) 0.50077(11) 0.08415(9) 0.0229(4) Uani 1 1 d . . . . .
O2 O 0.5324(2) 0.43959(12) 0.20185(9) 0.0258(4) Uani 1 1 d . . . . .
O3 O 0.18624(18) 0.55307(11) -0.00405(8) 0.0181(3) Uani 1 1 d . . . . .
H3A H 0.2689 0.5390 -0.0246 0.027 Uiso 1 1 calc R U . . .
O4 O -0.07737(18) 0.64504(10) 0.03828(8) 0.0170(3) Uani 1 1 d . . . . .
H4A H -0.0824 0.5867 0.0246 0.025 Uiso 1 1 calc R U . . .
S1 S 0.26517(8) 0.62422(5) 0.34375(3) 0.02497(17) 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 1.395(3) . ?
C1 C6 1.399(3) . ?
C1 S1 1.763(2) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.423(3) . ?
C7 C8 1.484(3) . ?
C7 S1 1.813(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.359(3) . ?
C8 N1 1.372(3) . ?
C9 C10 1.437(3) . ?
C9 C12 1.517(3) . ?
C10 O1 1.217(2) . ?
C10 O2 1.347(2) . ?
C11 O2 1.442(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.426(2) . ?
C12 C22 1.516(3) . ?
C12 C13 1.595(3) . ?
C13 O4 1.391(2) . ?
C13 N1 1.498(3) . ?
C13 C14 1.523(3) . ?
C14 C15 1.365(3) . ?
C14 C23 1.415(3) . ?
C15 C16 1.414(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.415(3) . ?
C17 H17 0.9300 . ?
C18 C23 1.410(3) . ?
C18 C19 1.418(3) . ?
C19 C20 1.367(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.415(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.403(3) . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?

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 119.7(2) . . ?
C2 C1 S1 119.59(17) . . ?
C6 C1 S1 120.66(16) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.24(19) . . ?
C5 C6 N1 119.90(19) . . ?
C1 C6 N1 120.85(19) . . ?
C8 C7 S1 108.14(15) . . ?
C8 C7 H7A 110.1 . . ?
S1 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
S1 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 N1 112.91(18) . . ?
C9 C8 C7 130.2(2) . . ?
N1 C8 C7 116.92(18) . . ?
C8 C9 C10 129.31(19) . . ?
C8 C9 C12 110.12(17) . . ?
C10 C9 C12 120.57(18) . . ?
O1 C10 O2 121.7(2) . . ?
O1 C10 C9 122.66(19) . . ?
O2 C10 C9 115.66(18) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 C22 114.04(16) . . ?
O3 C12 C9 112.71(16) . . ?
C22 C12 C9 113.32(16) . . ?
O3 C12 C13 108.57(15) . . ?
C22 C12 C13 103.99(16) . . ?
C9 C12 C13 103.09(15) . . ?
O4 C13 N1 112.53(16) . . ?
O4 C13 C14 109.61(16) . . ?
N1 C13 C14 111.76(16) . . ?
O4 C13 C12 114.66(15) . . ?
N1 C13 C12 102.97(15) . . ?
C14 C13 C12 104.97(16) . . ?
C15 C14 C23 119.2(2) . . ?
C15 C14 C13 132.8(2) . . ?
C23 C14 C13 107.92(18) . . ?
C14 C15 C16 118.8(2) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 122.3(2) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C23 C18 C17 116.31(19) . . ?
C23 C18 C19 116.13(19) . . ?
C17 C18 C19 127.5(2) . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 123.1(2) . . ?
C19 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
C22 C21 C20 118.2(2) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C21 C22 C23 118.89(19) . . ?
C21 C22 C12 132.02(19) . . ?
C23 C22 C12 109.08(17) . . ?
C22 C23 C18 123.53(19) . . ?
C22 C23 C14 113.61(19) . . ?
C18 C23 C14 122.80(19) . . ?
C8 N1 C6 123.33(17) . . ?
C8 N1 C13 110.74(16) . . ?
C6 N1 C13 123.14(16) . . ?
C10 O2 C11 114.81(17) . . ?
C12 O3 H3A 109.5 . . ?
C13 O4 H4A 109.5 . . ?
C1 S1 C7 96.21(10) . . ?

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
O3 H3A O1 0.82 1.91 2.720(2) 172.2 3_665
O4 H4A O3 0.82 2.06 2.834(2) 157.6 3_565

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.067


####################################################################### 
# 
# 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_4f
_database_code_depnum_ccdc_archive 'CCDC 1883728'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-30 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         'C23 H16 N2 O5 S'
_chemical_formula_sum            'C23 H16 N2 O5 S'
_chemical_formula_weight         432.44

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                   13.0035(11)
_cell_length_b                   15.8463(12)
_cell_length_c                   9.5395(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.719(3)
_cell_angle_gamma                90
_cell_volume                     1924.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6329
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19161
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3772
_reflns_number_gt                2721
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0467P)²+1.2908P] 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         3772
_refine_ls_number_parameters     281
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.158
_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
C1 C 0.82424(17) -0.00293(14) 0.6408(2) 0.0351(5) Uani 1 1 d . . . . .
C2 C 0.91452(18) -0.04813(16) 0.6338(3) 0.0432(6) Uani 1 1 d . . . . .
H2 H 0.9728 -0.0202 0.6138 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9183(2) -0.13366(16) 0.6562(3) 0.0503(7) Uani 1 1 d . . . . .
H3 H 0.9780 -0.1639 0.6477 0.060 Uiso 1 1 calc R U . . .
C4 C 0.8338(2) -0.17492(16) 0.6915(3) 0.0510(7) Uani 1 1 d . . . . .
H4 H 0.8371 -0.2327 0.7085 0.061 Uiso 1 1 calc R U . . .
C5 C 0.74442(19) -0.13060(15) 0.7016(3) 0.0434(6) Uani 1 1 d . . . . .
H5 H 0.6879 -0.1584 0.7268 0.052 Uiso 1 1 calc R U . . .
C6 C 0.73859(17) -0.04462(14) 0.6742(2) 0.0349(5) Uani 1 1 d . . . . .
C7 C 0.66330(16) 0.11494(13) 0.6979(2) 0.0312(5) Uani 1 1 d . . . . .
C8 C 0.75596(16) 0.14199(14) 0.6535(2) 0.0322(5) Uani 1 1 d . . . . .
C9 C 0.77797(16) 0.22963(14) 0.6469(2) 0.0327(5) Uani 1 1 d . . . . .
C10 C 0.86597(17) 0.25768(15) 0.5805(3) 0.0394(6) Uani 1 1 d . . . . .
C11 C 0.9472(2) 0.37103(18) 0.4844(3) 0.0557(7) Uani 1 1 d . . . . .
H11A H 1.0144 0.3633 0.5466 0.083 Uiso 1 1 calc R U . . .
H11B H 0.9357 0.4300 0.4643 0.083 Uiso 1 1 calc R U . . .
H11C H 0.9454 0.3410 0.3965 0.083 Uiso 1 1 calc R U . . .
C12 C 0.48382(19) 0.12016(16) 0.9113(3) 0.0433(6) Uani 1 1 d . . . . .
H12 H 0.5430 0.1165 0.9844 0.052 Uiso 1 1 calc R U . . .
C13 C 0.38698(19) 0.09942(16) 0.9394(3) 0.0453(6) Uani 1 1 d . . . . .
H13 H 0.3803 0.0819 1.0302 0.054 Uiso 1 1 calc R U . . .
C14 C 0.30079(17) 0.10541(13) 0.8296(3) 0.0356(6) Uani 1 1 d . . . . .
C15 C 0.30861(18) 0.13027(16) 0.6945(3) 0.0417(6) Uani 1 1 d . . . . .
H15 H 0.2492 0.1334 0.6217 0.050 Uiso 1 1 calc R U . . .
C16 C 0.40624(18) 0.15062(15) 0.6685(3) 0.0396(6) Uani 1 1 d . . . . .
H16 H 0.4126 0.1674 0.5772 0.048 Uiso 1 1 calc R U . . .
C17 C 0.49477(16) 0.14622(13) 0.7771(2) 0.0304(5) Uani 1 1 d . . . . .
C18 C 0.59839(16) 0.17206(13) 0.7460(2) 0.0308(5) Uani 1 1 d . . . . .
C19 C 0.62769(16) 0.25770(14) 0.7532(2) 0.0313(5) Uani 1 1 d . . . . .
C20 C 0.57525(18) 0.32821(14) 0.8105(3) 0.0366(5) Uani 1 1 d . . . . .
C21 C 0.63281(18) 0.40795(14) 0.7882(3) 0.0397(6) Uani 1 1 d . . . . .
H21A H 0.6595 0.4355 0.8791 0.048 Uiso 1 1 calc R U . . .
H21B H 0.5863 0.4467 0.7269 0.048 Uiso 1 1 calc R U . . .
C22 C 0.72359(18) 0.38150(14) 0.7175(3) 0.0399(6) Uani 1 1 d . . . . .
H22A H 0.7176 0.4083 0.6248 0.048 Uiso 1 1 calc R U . . .
H22B H 0.7906 0.3967 0.7772 0.048 Uiso 1 1 calc R U . . .
C23 C 0.71341(16) 0.28655(13) 0.7015(2) 0.0319(5) Uani 1 1 d . . . . .
N1 N 0.82201(15) 0.08399(12) 0.6134(2) 0.0413(5) Uani 1 1 d . . . . .
H1 H 0.8671 0.1028 0.5664 0.050 Uiso 1 1 calc R U . . .
N2 N 0.19753(17) 0.08289(15) 0.8573(3) 0.0556(5) Uani 1 1 d . U . . .
O1 O 0.93156(16) 0.21178(12) 0.5495(3) 0.0775(7) Uani 1 1 d . . . . .
O2 O 0.86527(13) 0.33896(11) 0.5536(2) 0.0515(5) Uani 1 1 d . . . . .
O3 O 0.19227(16) 0.05468(15) 0.9742(2) 0.0749(6) Uani 1 1 d . U . . .
O4 O 0.12112(15) 0.09181(16) 0.7624(3) 0.0785(6) Uani 1 1 d . U . . .
O5 O 0.50002(13) 0.32389(11) 0.8678(2) 0.0532(5) Uani 1 1 d . . . . .
S1 S 0.61948(4) 0.00892(4) 0.67277(7) 0.0417(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.387(3) . ?
C1 C2 1.388(3) . ?
C1 N1 1.401(3) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.764(2) . ?
C7 C18 1.378(3) . ?
C7 C8 1.422(3) . ?
C7 S1 1.774(2) . ?
C8 N1 1.364(3) . ?
C8 C9 1.422(3) . ?
C9 C23 1.402(3) . ?
C9 C10 1.485(3) . ?
C10 O1 1.203(3) . ?
C10 O2 1.313(3) . ?
C11 O2 1.454(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.379(3) . ?
C12 C17 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(3) . ?
C14 N2 1.464(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.495(3) . ?
C18 C19 1.407(3) . ?
C19 C23 1.385(3) . ?
C19 C20 1.471(3) . ?
C20 O5 1.216(3) . ?
C20 C21 1.506(3) . ?
C21 C22 1.532(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.515(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N1 H1 0.8600 . ?
N2 O4 1.209(3) . ?
N2 O3 1.216(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
C6 C1 C2 119.4(2) . . ?
C6 C1 N1 121.6(2) . . ?
C2 C1 N1 119.0(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 S1 119.25(18) . . ?
C1 C6 S1 120.93(17) . . ?
C18 C7 C8 121.0(2) . . ?
C18 C7 S1 117.73(16) . . ?
C8 C7 S1 120.88(16) . . ?
N1 C8 C9 120.13(19) . . ?
N1 C8 C7 120.0(2) . . ?
C9 C8 C7 119.85(19) . . ?
C23 C9 C8 118.10(19) . . ?
C23 C9 C10 122.5(2) . . ?
C8 C9 C10 119.38(19) . . ?
O1 C10 O2 121.5(2) . . ?
O1 C10 C9 124.8(2) . . ?
O2 C10 C9 113.69(19) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C17 C12 H12 119.3 . . ?
C14 C13 C12 118.1(2) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C15 C14 C13 122.1(2) . . ?
C15 C14 N2 119.0(2) . . ?
C13 C14 N2 118.8(2) . . ?
C14 C15 C16 118.9(2) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 118.8(2) . . ?
C12 C17 C18 122.2(2) . . ?
C16 C17 C18 118.9(2) . . ?
C7 C18 C19 118.14(19) . . ?
C7 C18 C17 121.59(19) . . ?
C19 C18 C17 120.04(18) . . ?
C23 C19 C18 122.04(19) . . ?
C23 C19 C20 110.43(19) . . ?
C18 C19 C20 127.52(19) . . ?
O5 C20 C19 126.9(2) . . ?
O5 C20 C21 125.4(2) . . ?
C19 C20 C21 107.67(18) . . ?
C20 C21 C22 106.39(18) . . ?
C20 C21 H21A 110.5 . . ?
C22 C21 H21A 110.5 . . ?
C20 C21 H21B 110.5 . . ?
C22 C21 H21B 110.5 . . ?
H21A C21 H21B 108.6 . . ?
C23 C22 C21 104.86(18) . . ?
C23 C22 H22A 110.8 . . ?
C21 C22 H22A 110.8 . . ?
C23 C22 H22B 110.8 . . ?
C21 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
C19 C23 C9 120.4(2) . . ?
C19 C23 C22 110.62(19) . . ?
C9 C23 C22 128.99(19) . . ?
C8 N1 C1 126.91(19) . . ?
C8 N1 H1 116.5 . . ?
C1 N1 H1 116.5 . . ?
O4 N2 O3 122.6(2) . . ?
O4 N2 C14 118.7(2) . . ?
O3 N2 C14 118.6(2) . . ?
C10 O2 C11 117.06(19) . . ?
C6 S1 C7 101.36(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.94 2.618(3) 134.7 .

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.340
_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_3a
_database_code_depnum_ccdc_archive 'CCDC 1883727'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-30 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         'C24 H21 N O3 S'
_chemical_formula_sum            'C24 H21 N O3 S'
_chemical_formula_weight         403.48

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   7.3838(11)
_cell_length_b                   11.2551(15)
_cell_length_c                   24.298(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2019.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2984
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      23.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9464
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.467
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3870
_reflns_number_gt                2604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.950
_reflns_Friedel_fraction_full    0.947

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0448P)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_abs_structure_details 
; 
 Flack x determined using 745 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.38(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3870
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.2240(5) 0.8728(3) 1.08207(12) 0.0406(9) Uani 1 1 d . . . . .
C2 C 0.2548(6) 0.8487(4) 1.13716(13) 0.0546(11) Uani 1 1 d . . . . .
H2 H 0.2668 0.7705 1.1489 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2678(6) 0.9396(4) 1.17463(13) 0.0639(13) Uani 1 1 d . . . . .
H3 H 0.2859 0.9227 1.2117 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2540(6) 1.0549(4) 1.15756(14) 0.0664(13) Uani 1 1 d . . . . .
H4 H 0.2647 1.1163 1.1830 0.080 Uiso 1 1 calc R U . . .
C5 C 0.2242(6) 1.0808(4) 1.10236(14) 0.0606(12) Uani 1 1 d . . . . .
H5 H 0.2156 1.1595 1.0909 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2073(5) 0.9897(3) 1.06467(12) 0.0442(10) Uani 1 1 d . . . . .
C7 C 0.2331(5) 0.8926(3) 0.96028(11) 0.0372(9) Uani 1 1 d . . . . .
H7 H 0.3638 0.9034 0.9554 0.045 Uiso 1 1 calc R U . . .
C8 C 0.2050(5) 0.7760(3) 0.99024(11) 0.0346(8) Uani 1 1 d . . . . .
C9 C 0.2021(5) 0.6703(3) 0.96068(12) 0.0370(9) Uani 1 1 d . . . . .
C10 C 0.1927(5) 0.5572(3) 0.99030(14) 0.0442(9) Uani 1 1 d . . . . .
C11 C 0.1747(8) 0.3473(3) 0.98389(18) 0.0851(17) Uani 1 1 d . . . . .
H11A H 0.0659 0.3438 1.0055 0.128 Uiso 1 1 calc R U . . .
H11B H 0.2778 0.3356 1.0074 0.128 Uiso 1 1 calc R U . . .
H11C H 0.1719 0.2863 0.9563 0.128 Uiso 1 1 calc R U . . .
C12 C 0.2159(5) 0.6777(3) 0.90080(12) 0.0369(8) Uani 1 1 d . . . . .
C13 C 0.2496(6) 0.5763(3) 0.86126(12) 0.0465(10) Uani 1 1 d . . . . .
H13A H 0.1533 0.5178 0.8634 0.056 Uiso 1 1 calc R U . . .
H13B H 0.3641 0.5376 0.8691 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2534(7) 0.6353(3) 0.80490(13) 0.0559(11) Uani 1 1 d . . . . .
H14A H 0.3738 0.6307 0.7890 0.067 Uiso 1 1 calc R U . . .
H14B H 0.1687 0.5968 0.7801 0.067 Uiso 1 1 calc R U . . .
C15 C 0.1999(6) 0.7630(3) 0.81427(12) 0.0497(11) Uani 1 1 d . . . . .
C16 C 0.1946(5) 0.7823(3) 0.87388(11) 0.0396(9) Uani 1 1 d . . . . .
C17 C 0.1457(5) 0.8950(3) 0.90277(11) 0.0394(9) Uani 1 1 d . . . . .
H17 H 0.0140 0.8950 0.9079 0.047 Uiso 1 1 calc R U . . .
C18 C 0.1945(5) 1.0073(3) 0.87181(11) 0.0389(9) Uani 1 1 d . . . . .
C19 C 0.3732(6) 1.0355(3) 0.85910(13) 0.0529(10) Uani 1 1 d . . . . .
H19 H 0.4660 0.9857 0.8709 0.063 Uiso 1 1 calc R U . . .
C20 C 0.4146(6) 1.1366(3) 0.82913(14) 0.0585(12) Uani 1 1 d . . . . .
H20 H 0.5351 1.1541 0.8215 0.070 Uiso 1 1 calc R U . . .
C21 C 0.2818(7) 1.2114(3) 0.81057(13) 0.0533(11) Uani 1 1 d . . . . .
C22 C 0.3259(7) 1.3197(3) 0.77542(15) 0.0805(17) Uani 1 1 d . . . . .
H22A H 0.3936 1.2953 0.7436 0.121 Uiso 1 1 calc R U . . .
H22B H 0.3966 1.3749 0.7966 0.121 Uiso 1 1 calc R U . . .
H22C H 0.2155 1.3572 0.7639 0.121 Uiso 1 1 calc R U . . .
C23 C 0.1055(7) 1.1847(4) 0.82369(15) 0.0626(13) Uani 1 1 d . . . . .
H23 H 0.0133 1.2349 0.8119 0.075 Uiso 1 1 calc R U . . .
C24 C 0.0623(6) 1.0841(3) 0.85434(15) 0.0557(11) Uani 1 1 d . . . . .
H24 H -0.0581 1.0688 0.8631 0.067 Uiso 1 1 calc R U . . .
N1 N 0.2023(4) 0.7773(3) 1.04547(9) 0.0423(8) Uani 1 1 d . . . . .
H1 H 0.1847 0.7093 1.0608 0.051 Uiso 1 1 calc R U . . .
O1 O 0.1855(4) 0.5468(2) 1.04054(9) 0.0542(8) Uani 1 1 d . . . . .
O2 O 0.1877(4) 0.4627(2) 0.95750(9) 0.0631(9) Uani 1 1 d . . . . .
O3 O 0.1624(5) 0.8336(2) 0.77842(9) 0.0768(10) Uani 1 1 d . . . . .
S1 S 0.14825(16) 1.02173(8) 0.99634(3) 0.0554(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 1.385(4) . ?
C1 C6 1.388(5) . ?
C1 N1 1.405(4) . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 S1 1.754(3) . ?
C7 C8 1.515(4) . ?
C7 C17 1.540(4) . ?
C7 S1 1.809(3) . ?
C7 H7 0.9800 . ?
C8 N1 1.342(4) . ?
C8 C9 1.390(4) . ?
C9 C12 1.461(4) . ?
C9 C10 1.464(5) . ?
C10 O1 1.227(4) . ?
C10 O2 1.330(4) . ?
C11 O2 1.451(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C16 1.356(4) . ?
C12 C13 1.513(4) . ?
C13 C14 1.523(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.508(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O3 1.211(4) . ?
C15 C16 1.465(4) . ?
C16 C17 1.494(4) . ?
C17 C18 1.514(4) . ?
C17 H17 0.9800 . ?
C18 C24 1.371(5) . ?
C18 C19 1.392(5) . ?
C19 C20 1.386(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(6) . ?
C20 H20 0.9300 . ?
C21 C23 1.373(6) . ?
C21 C22 1.524(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.393(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.7(3) . . ?
C2 C1 N1 118.7(3) . . ?
C6 C1 N1 121.5(3) . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 S1 119.9(3) . . ?
C1 C6 S1 120.3(2) . . ?
C8 C7 C17 113.2(3) . . ?
C8 C7 S1 114.6(2) . . ?
C17 C7 S1 106.3(2) . . ?
C8 C7 H7 107.5 . . ?
C17 C7 H7 107.5 . . ?
S1 C7 H7 107.5 . . ?
N1 C8 C9 121.7(3) . . ?
N1 C8 C7 118.2(3) . . ?
C9 C8 C7 119.7(2) . . ?
C8 C9 C12 117.7(3) . . ?
C8 C9 C10 119.4(3) . . ?
C12 C9 C10 122.9(3) . . ?
O1 C10 O2 121.3(3) . . ?
O1 C10 C9 125.0(3) . . ?
O2 C10 C9 113.7(3) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C12 C9 121.5(3) . . ?
C16 C12 C13 111.6(3) . . ?
C9 C12 C13 126.9(3) . . ?
C12 C13 C14 104.2(3) . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C15 C14 C13 106.0(3) . . ?
C15 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
O3 C15 C16 127.4(3) . . ?
O3 C15 C14 125.2(3) . . ?
C16 C15 C14 107.3(3) . . ?
C12 C16 C15 110.2(3) . . ?
C12 C16 C17 122.6(3) . . ?
C15 C16 C17 126.6(3) . . ?
C16 C17 C18 114.7(3) . . ?
C16 C17 C7 108.1(3) . . ?
C18 C17 C7 111.5(3) . . ?
C16 C17 H17 107.4 . . ?
C18 C17 H17 107.4 . . ?
C7 C17 H17 107.4 . . ?
C24 C18 C19 117.6(3) . . ?
C24 C18 C17 120.7(4) . . ?
C19 C18 C17 121.7(3) . . ?
C20 C19 C18 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C23 117.9(4) . . ?
C20 C21 C22 121.6(5) . . ?
C23 C21 C22 120.5(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 C24 121.3(4) . . ?
C21 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C18 C24 C23 121.0(4) . . ?
C18 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C8 N1 C1 129.8(3) . . ?
C8 N1 H1 115.1 . . ?
C1 N1 H1 115.1 . . ?
C10 O2 C11 116.9(3) . . ?
C6 S1 C7 101.97(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.89 2.599(4) 138.3 .

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039


####################################################################### 
# 
# 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_2k
_database_code_depnum_ccdc_archive 'CCDC 1883725'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-30 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         'C24 H21 N O3 S2'
_chemical_formula_sum            'C24 H21 N O3 S2'
_chemical_formula_weight         435.54

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                   9.2819(8)
_cell_length_b                   23.5334(17)
_cell_length_c                   10.2751(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.152(3)
_cell_angle_gamma                90
_cell_volume                     2093.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4306
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      24.57

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             912
_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    0.281
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19598
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4110
_reflns_number_gt                2321
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0919P)²+1.7446P] 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         4110
_refine_ls_number_parameters     274
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.1995
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   1.017
_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
C1 C 0.7747(5) 1.08183(16) 0.6189(4) 0.0445(10) Uani 1 1 d . . . . .
C2 C 0.8232(5) 1.12097(17) 0.7257(5) 0.0512(11) Uani 1 1 d . . . . .
H2 H 0.8905 1.1097 0.8133 0.061 Uiso 1 1 calc R U . . .
C3 C 0.7734(6) 1.17642(18) 0.7044(5) 0.0575(12) Uani 1 1 d . . . . .
H3 H 0.8087 1.2028 0.7764 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6703(5) 1.19248(17) 0.5750(5) 0.0548(12) Uani 1 1 d . . . . .
H4 H 0.6359 1.2299 0.5596 0.066 Uiso 1 1 calc R U . . .
C5 C 0.6182(5) 1.15328(16) 0.4684(5) 0.0501(11) Uani 1 1 d . . . . .
H5 H 0.5476 1.1642 0.3820 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6705(5) 1.09766(16) 0.4895(4) 0.0427(10) Uani 1 1 d . . . . .
C7 C 0.7322(4) 0.97453(16) 0.5070(4) 0.0416(10) Uani 1 1 d . . . . .
C8 C 0.6308(4) 1.00132(15) 0.3854(4) 0.0395(10) Uani 1 1 d . . . . .
C9 C 0.5465(4) 0.96777(14) 0.2692(4) 0.0342(9) Uani 1 1 d . . . . .
C10 C 0.4329(4) 0.99693(15) 0.1472(4) 0.0369(9) Uani 1 1 d . . . . .
C11 C 0.1933(5) 0.99310(18) -0.0366(4) 0.0570(12) Uani 1 1 d . . . . .
H11A H 0.1610 1.0278 -0.0064 0.085 Uiso 1 1 calc R U . . .
H11B H 0.1061 0.9682 -0.0740 0.085 Uiso 1 1 calc R U . . .
H11C H 0.2352 1.0013 -0.1074 0.085 Uiso 1 1 calc R U . . .
C12 C 1.0074(8) 0.8509(2) 0.8677(5) 0.0839(17) Uani 1 1 d . U . . .
H12 H 1.0411 0.8359 0.9575 0.101 Uiso 1 1 calc R U . . .
C13 C 1.0984(7) 0.8593(2) 0.7964(6) 0.0827(16) Uani 1 1 d . U . . .
H13 H 1.2036 0.8514 0.8338 0.099 Uiso 1 1 calc R U . . .
C14 C 1.0257(4) 0.88131(14) 0.6573(4) 0.0333(8) Uani 1 1 d . U . . .
H14 H 1.0722 0.8882 0.5924 0.040 Uiso 1 1 calc R U . . .
C15 C 0.8657(5) 0.89061(16) 0.6391(4) 0.0443(10) Uani 1 1 d . U . . .
C16 C 0.7463(4) 0.91555(16) 0.5122(4) 0.0386(9) Uani 1 1 d . . . . .
C17 C 0.6663(4) 0.88239(15) 0.3937(4) 0.0370(9) Uani 1 1 d . . . . .
C18 C 0.5714(4) 0.90862(14) 0.2699(4) 0.0337(9) Uani 1 1 d . . . . .
C19 C 0.5068(5) 0.87376(14) 0.1383(4) 0.0387(9) Uani 1 1 d . . . . .
H19A H 0.4912 0.8982 0.0584 0.046 Uiso 1 1 calc R U . . .
H19B H 0.4069 0.8587 0.1311 0.046 Uiso 1 1 calc R U . . .
C20 C 0.6127(5) 0.82430(15) 0.1338(4) 0.0408(9) Uani 1 1 d . . . . .
C21 C 0.7676(5) 0.84603(18) 0.1351(5) 0.0534(11) Uani 1 1 d . . . . .
H21A H 0.8309 0.8144 0.1302 0.080 Uiso 1 1 calc R U . . .
H21B H 0.8184 0.8669 0.2196 0.080 Uiso 1 1 calc R U . . .
H21C H 0.7513 0.8705 0.0563 0.080 Uiso 1 1 calc R U . . .
C22 C 0.5328(5) 0.78987(18) 0.0014(4) 0.0573(12) Uani 1 1 d . . . . .
H22A H 0.5950 0.7574 0.0002 0.086 Uiso 1 1 calc R U . . .
H22B H 0.5196 0.8131 -0.0788 0.086 Uiso 1 1 calc R U . . .
H22C H 0.4337 0.7774 -0.0004 0.086 Uiso 1 1 calc R U . . .
C23 C 0.6347(5) 0.78778(16) 0.2615(4) 0.0485(11) Uani 1 1 d . . . . .
H23A H 0.5392 0.7675 0.2470 0.058 Uiso 1 1 calc R U . . .
H23B H 0.7137 0.7597 0.2689 0.058 Uiso 1 1 calc R U . . .
C24 C 0.6793(4) 0.81912(15) 0.3974(4) 0.0423(10) Uani 1 1 d . . . . .
N1 N 0.6187(4) 1.05970(13) 0.3791(3) 0.0582(10) Uani 1 1 d . . . . .
H1 H 0.5741 1.0742 0.2976 0.070 Uiso 1 1 calc R U . . .
O1 O 0.4469(3) 1.04506(11) 0.1124(3) 0.0550(8) Uani 1 1 d . . . . .
O2 O 0.3092(3) 0.96616(10) 0.0799(3) 0.0453(7) Uani 1 1 d . . . . .
O3 O 0.7196(4) 0.79296(12) 0.5072(3) 0.0613(9) Uani 1 1 d . . . . .
S1 S 0.85698(17) 1.01370(5) 0.64955(13) 0.0766(5) Uani 1 1 d . . . . .
S2 S 0.8262(2) 0.87008(6) 0.78013(14) 0.0856(5) Uani 1 1 d . 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
C1 C2 1.378(5) . ?
C1 C6 1.383(5) . ?
C1 S1 1.755(4) . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(5) . ?
C5 H5 0.9300 . ?
C6 N1 1.386(5) . ?
C7 C16 1.393(5) . ?
C7 C8 1.413(5) . ?
C7 S1 1.764(4) . ?
C8 N1 1.378(5) . ?
C8 C9 1.409(5) . ?
C9 C18 1.411(5) . ?
C9 C10 1.483(5) . ?
C10 O1 1.209(4) . ?
C10 O2 1.322(4) . ?
C11 O2 1.436(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.317(8) . ?
C12 S2 1.658(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.439(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.445(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.493(5) . ?
C15 S2 1.688(4) . ?
C16 C17 1.411(5) . ?
C17 C18 1.402(5) . ?
C17 C24 1.493(5) . ?
C18 C19 1.509(5) . ?
C19 C20 1.535(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C23 1.520(5) . ?
C20 C21 1.522(6) . ?
C20 C22 1.526(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.499(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O3 1.219(4) . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.0(4) . . ?
C2 C1 S1 118.1(3) . . ?
C6 C1 S1 121.8(3) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 N1 121.9(3) . . ?
C5 C6 N1 118.8(4) . . ?
C16 C7 C8 120.1(3) . . ?
C16 C7 S1 117.7(3) . . ?
C8 C7 S1 122.0(3) . . ?
N1 C8 C9 120.6(3) . . ?
N1 C8 C7 120.2(3) . . ?
C9 C8 C7 119.2(3) . . ?
C8 C9 C18 120.6(3) . . ?
C8 C9 C10 117.7(3) . . ?
C18 C9 C10 121.7(3) . . ?
O1 C10 O2 121.6(3) . . ?
O1 C10 C9 124.3(4) . . ?
O2 C10 C9 114.0(3) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 S2 112.7(4) . . ?
C13 C12 H12 123.7 . . ?
S2 C12 H12 123.7 . . ?
C12 C13 C14 116.2(5) . . ?
C12 C13 H13 121.9 . . ?
C14 C13 H13 121.9 . . ?
C13 C14 C15 105.9(4) . . ?
C13 C14 H14 127.0 . . ?
C15 C14 H14 127.0 . . ?
C14 C15 C16 125.2(3) . . ?
C14 C15 S2 112.1(3) . . ?
C16 C15 S2 122.7(3) . . ?
C7 C16 C17 120.3(3) . . ?
C7 C16 C15 117.1(3) . . ?
C17 C16 C15 122.0(3) . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 C24 118.7(3) . . ?
C16 C17 C24 121.1(3) . . ?
C17 C18 C9 119.2(3) . . ?
C17 C18 C19 119.3(3) . . ?
C9 C18 C19 121.4(3) . . ?
C18 C19 C20 112.8(3) . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C23 C20 C21 110.5(3) . . ?
C23 C20 C22 109.9(3) . . ?
C21 C20 C22 109.9(3) . . ?
C23 C20 C19 106.9(3) . . ?
C21 C20 C19 111.0(3) . . ?
C22 C20 C19 108.6(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C20 115.6(3) . . ?
C24 C23 H23A 108.4 . . ?
C20 C23 H23A 108.4 . . ?
C24 C23 H23B 108.4 . . ?
C20 C23 H23B 108.4 . . ?
H23A C23 H23B 107.4 . . ?
O3 C24 C17 121.4(4) . . ?
O3 C24 C23 120.2(3) . . ?
C17 C24 C23 118.3(3) . . ?
C8 N1 C6 127.3(3) . . ?
C8 N1 H1 116.3 . . ?
C6 N1 H1 116.3 . . ?
C10 O2 C11 116.2(3) . . ?
C1 S1 C7 102.45(19) . . ?
C12 S2 C15 93.0(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
N1 H1 O1 0.86 1.97 2.649(4) 135.6 .

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.500
_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_8a
_database_code_depnum_ccdc_archive 'CCDC 1884302'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan'
;Yangzhou University
China
;
_audit_update_record             
;
2018-12-11 deposited with the CCDC.	2019-08-30 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         'C20 H15 N O5 S'
_chemical_formula_sum            'C20 H15 N O5 S'
_chemical_formula_weight         381.39

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                   8.2024(4)
_cell_length_b                   10.5566(5)
_cell_length_c                   11.0975(5)
_cell_angle_alpha                68.8504(13)
_cell_angle_beta                 79.7504(14)
_cell_angle_gamma                71.2427(14)
_cell_volume                     846.51(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8110
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             396
_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    0.225
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12972
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.155
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3869
_reflns_number_gt                3295
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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+0.2820P] 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         3869
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.75577(17) 0.48550(13) 0.70668(13) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.59028(19) 0.53951(15) 0.66206(16) 0.0361(3) Uani 1 1 d . . . . .
H2 H 0.5683 0.5195 0.5925 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4591(2) 0.62255(18) 0.72079(19) 0.0474(4) Uani 1 1 d . . . . .
H3 H 0.3485 0.6562 0.6920 0.057 Uiso 1 1 calc R U . . .
C4 C 0.4913(2) 0.6557(2) 0.8216(2) 0.0567(5) Uani 1 1 d . . . . .
H4 H 0.4017 0.7088 0.8629 0.068 Uiso 1 1 calc R U . . .
C5 C 0.6568(2) 0.6101(2) 0.86160(18) 0.0509(4) Uani 1 1 d . . . . .
H5 H 0.6787 0.6357 0.9277 0.061 Uiso 1 1 calc R U . . .
C6 C 0.7908(2) 0.52640(15) 0.80376(14) 0.0332(3) Uani 1 1 d . . . . .
C7 C 1.11458(18) 0.45976(15) 0.70143(14) 0.0315(3) Uani 1 1 d . . . . .
H7A H 1.0882 0.5521 0.6352 0.038 Uiso 1 1 calc R U . . .
H7B H 1.2382 0.4266 0.7098 0.038 Uiso 1 1 calc R U . . .
C8 C 1.05808(16) 0.35911(13) 0.66489(12) 0.0235(3) Uani 1 1 d . . . . .
C9 C 1.15303(16) 0.23850(13) 0.63979(12) 0.0238(3) Uani 1 1 d . . . . .
C10 C 1.33832(16) 0.18307(14) 0.64472(13) 0.0265(3) Uani 1 1 d . . . . .
C11 C 1.58198(18) -0.00978(18) 0.63852(18) 0.0434(4) Uani 1 1 d . . . . .
H11A H 1.6412 0.0455 0.5666 0.065 Uiso 1 1 calc R U . . .
H11B H 1.6091 -0.1037 0.6345 0.065 Uiso 1 1 calc R U . . .
H11C H 1.6179 -0.0142 0.7180 0.065 Uiso 1 1 calc R U . . .
C12 C 0.85401(15) 0.25931(13) 0.64751(12) 0.0219(2) Uani 1 1 d . . . . .
C13 C 1.03638(15) 0.17754(13) 0.59988(12) 0.0227(3) Uani 1 1 d . . . . .
C14 C 1.04476(16) 0.02280(14) 0.67729(14) 0.0276(3) Uani 1 1 d . . . . .
C15 C 0.92846(17) 0.02220(14) 0.79476(13) 0.0291(3) Uani 1 1 d . . . . .
C16 C 0.9151(2) -0.09222(17) 0.90447(16) 0.0415(4) Uani 1 1 d . . . . .
H16 H 0.9879 -0.1825 0.9126 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7906(2) -0.06755(19) 1.00066(16) 0.0493(4) Uani 1 1 d . . . . .
H17 H 0.7792 -0.1422 1.0753 0.059 Uiso 1 1 calc R U . . .
C18 C 0.6817(2) 0.0674(2) 0.98782(16) 0.0472(4) Uani 1 1 d . . . . .
H18 H 0.5994 0.0816 1.0546 0.057 Uiso 1 1 calc R U . . .
C19 C 0.6931(2) 0.18131(17) 0.87765(14) 0.0358(3) Uani 1 1 d . . . . .
H19 H 0.6189 0.2712 0.8693 0.043 Uiso 1 1 calc R U . . .
C20 C 0.81847(16) 0.15741(14) 0.78002(12) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.88481(13) 0.38658(11) 0.65663(10) 0.0239(2) Uani 1 1 d . . . . .
O1 O 1.43222(13) 0.24329(12) 0.66238(12) 0.0431(3) Uani 1 1 d . . . . .
O2 O 1.39788(12) 0.05516(11) 0.63321(11) 0.0379(3) Uani 1 1 d . . . . .
O3 O 0.73323(11) 0.29426(10) 0.55931(9) 0.0283(2) Uani 1 1 d . . . . .
H3A H 0.6468 0.2712 0.5978 0.043 Uiso 1 1 calc R U . . .
O4 O 1.06040(12) 0.20395(11) 0.46547(9) 0.0301(2) Uani 1 1 d . . . . .
H4A H 0.9949 0.1730 0.4435 0.045 Uiso 1 1 calc R U . . .
O5 O 1.12249(14) -0.07767(11) 0.64157(12) 0.0417(3) Uani 1 1 d . . . . .
S1 S 1.00160(5) 0.47172(4) 0.85386(4) 0.04100(12) 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 1.397(2) . ?
C1 C6 1.398(2) . ?
C1 N1 1.4204(16) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9300 . ?
C6 S1 1.7611(16) . ?
C7 C8 1.4841(18) . ?
C7 S1 1.8047(15) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.3587(18) . ?
C8 N1 1.3691(16) . ?
C9 C10 1.4455(17) . ?
C9 C13 1.5095(17) . ?
C10 O1 1.2224(16) . ?
C10 O2 1.3252(17) . ?
C11 O2 1.4459(17) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.3874(14) . ?
C12 N1 1.4849(15) . ?
C12 C20 1.5206(17) . ?
C12 C13 1.5747(17) . ?
C13 O4 1.4043(15) . ?
C13 C14 1.5321(18) . ?
C14 O5 1.2113(17) . ?
C14 C15 1.471(2) . ?
C15 C16 1.389(2) . ?
C15 C20 1.3906(19) . ?
C16 C17 1.375(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.3889(19) . ?
C19 H19 0.9300 . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?

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 119.24(13) . . ?
C2 C1 N1 120.07(12) . . ?
C6 C1 N1 120.66(12) . . ?
C3 C2 C1 120.27(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.30(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.05(16) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.53(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.33(14) . . ?
C5 C6 S1 120.02(12) . . ?
C1 C6 S1 120.64(11) . . ?
C8 C7 S1 108.11(9) . . ?
C8 C7 H7A 110.1 . . ?
S1 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
S1 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 N1 112.96(11) . . ?
C9 C8 C7 129.70(12) . . ?
N1 C8 C7 117.32(11) . . ?
C8 C9 C10 124.44(11) . . ?
C8 C9 C13 109.43(11) . . ?
C10 C9 C13 126.06(11) . . ?
O1 C10 O2 122.36(12) . . ?
O1 C10 C9 124.72(13) . . ?
O2 C10 C9 112.87(11) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N1 112.09(10) . . ?
O3 C12 C20 114.42(10) . . ?
N1 C12 C20 112.09(10) . . ?
O3 C12 C13 110.45(10) . . ?
N1 C12 C13 103.45(9) . . ?
C20 C12 C13 103.41(10) . . ?
O4 C13 C9 109.47(10) . . ?
O4 C13 C14 113.08(10) . . ?
C9 C13 C14 115.71(10) . . ?
O4 C13 C12 114.52(10) . . ?
C9 C13 C12 100.98(9) . . ?
C14 C13 C12 102.45(10) . . ?
O5 C14 C15 127.18(13) . . ?
O5 C14 C13 125.40(13) . . ?
C15 C14 C13 107.17(11) . . ?
C16 C15 C20 121.80(14) . . ?
C16 C15 C14 128.31(13) . . ?
C20 C15 C14 109.79(12) . . ?
C17 C16 C15 117.82(15) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C16 C17 C18 120.87(15) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 121.42(15) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 118.11(15) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C19 C20 C15 119.96(13) . . ?
C19 C20 C12 129.44(12) . . ?
C15 C20 C12 110.52(11) . . ?
C8 N1 C1 123.76(11) . . ?
C8 N1 C12 108.13(10) . . ?
C1 N1 C12 122.48(10) . . ?
C10 O2 C11 116.88(11) . . ?
C12 O3 H3A 109.5 . . ?
C13 O4 H4A 109.5 . . ?
C6 S1 C7 97.06(7) . . ?

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
O3 H3A O1 0.82 1.85 2.6644(14) 170.5 1_455
O4 H4A O5 0.82 2.11 2.9157(14) 166.4 2_756

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.307
_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_5c
_database_code_depnum_ccdc_archive 'CCDC 1883729'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-30 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         'C37 H30 N2 O3 S2'
_chemical_formula_sum            'C37 H30 N2 O3 S2'
_chemical_formula_weight         614.75

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           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

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

_cell_length_a                   11.095(3)
_cell_length_b                   12.561(4)
_cell_length_c                   24.147(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.088(9)
_cell_angle_gamma                90
_cell_volume                     3360.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7091
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      24.31

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32324
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.981
_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             5908
_reflns_number_gt                3925
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1053P)²+7.0611P] 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         5908
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0827
_refine_ls_wR_factor_ref         0.2418
_refine_ls_wR_factor_gt          0.2280
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.3830(5) 0.4170(4) 0.3481(2) 0.0471(13) Uani 1 1 d . . . . .
C2 C 0.3120(6) 0.3932(5) 0.3921(2) 0.0633(17) Uani 1 1 d . . . . .
H2 H 0.3255 0.3307 0.4121 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2232(6) 0.4608(6) 0.4061(3) 0.071(2) Uani 1 1 d . . . . .
H3 H 0.1758 0.4436 0.4355 0.086 Uiso 1 1 calc R U . . .
C4 C 0.2021(5) 0.5552(6) 0.3773(3) 0.0689(19) Uani 1 1 d . . . . .
H4 H 0.1409 0.6010 0.3870 0.083 Uiso 1 1 calc R U . . .
C5 C 0.2724(5) 0.5796(5) 0.3346(2) 0.0540(15) Uani 1 1 d . . . . .
H5 H 0.2588 0.6426 0.3150 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3641(4) 0.5119(4) 0.31988(19) 0.0420(12) Uani 1 1 d . . . . .
C7 C 0.4860(4) 0.3623(4) 0.25481(17) 0.0334(11) Uani 1 1 d . . . . .
H7 H 0.4030 0.3461 0.2416 0.040 Uiso 1 1 calc R U . . .
C8 C 0.5059(4) 0.4798(4) 0.24710(17) 0.0318(10) Uani 1 1 d . . . . .
C9 C 0.5800(4) 0.5180(4) 0.20745(17) 0.0324(10) Uani 1 1 d . . . . .
C10 C 0.5876(4) 0.6312(4) 0.19847(18) 0.0367(11) Uani 1 1 d . . . . .
C11 C 0.5705(4) 0.2862(4) 0.22531(19) 0.0338(11) Uani 1 1 d . . . . .
H11 H 0.6377 0.2686 0.2517 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5015(4) 0.1837(4) 0.21240(19) 0.0360(11) Uani 1 1 d . . . . .
C13 C 0.4046(6) 0.1828(5) 0.1755(3) 0.0716(19) Uani 1 1 d . . . . .
H13 H 0.3820 0.2452 0.1570 0.086 Uiso 1 1 calc R U . . .
C14 C 0.3380(7) 0.0891(6) 0.1648(3) 0.087(2) Uani 1 1 d . . . . .
H14 H 0.2707 0.0903 0.1401 0.105 Uiso 1 1 calc R U . . .
C15 C 0.3722(6) -0.0043(5) 0.1908(3) 0.0709(19) Uani 1 1 d . . . . .
C16 C 0.3019(7) -0.1050(6) 0.1773(4) 0.110(3) Uani 1 1 d . . . . .
H16A H 0.3190 -0.1287 0.1407 0.165 Uiso 1 1 calc R U . . .
H16B H 0.2171 -0.0909 0.1787 0.165 Uiso 1 1 calc R U . . .
H16C H 0.3249 -0.1592 0.2038 0.165 Uiso 1 1 calc R U . . .
C17 C 0.4690(6) -0.0027(5) 0.2268(3) 0.0650(17) Uani 1 1 d . . . . .
H17 H 0.4931 -0.0653 0.2446 0.078 Uiso 1 1 calc R U . . .
C18 C 0.5330(5) 0.0887(4) 0.2378(2) 0.0507(14) Uani 1 1 d . . . . .
H18 H 0.5994 0.0866 0.2630 0.061 Uiso 1 1 calc R U . . .
C19 C 0.6230(4) 0.3359(4) 0.17552(18) 0.0329(11) Uani 1 1 d . . . . .
C20 C 0.6752(4) 0.2634(4) 0.1349(2) 0.0365(11) Uani 1 1 d . . . . .
C21 C 0.7789(6) 0.1000(4) 0.1241(3) 0.0663(18) Uani 1 1 d . . . . .
H21A H 0.7178 0.0793 0.0966 0.099 Uiso 1 1 calc R U . . .
H21B H 0.8041 0.0388 0.1457 0.099 Uiso 1 1 calc R U . . .
H21C H 0.8469 0.1289 0.1063 0.099 Uiso 1 1 calc R U . . .
C22 C 0.6316(4) 0.4423(4) 0.16901(18) 0.0309(10) Uani 1 1 d . . . . .
C23 C 0.6998(4) 0.4917(4) 0.12329(18) 0.0326(10) Uani 1 1 d . . . . .
H23 H 0.7609 0.4408 0.1121 0.039 Uiso 1 1 calc R U . . .
C24 C 0.7638(4) 0.5892(4) 0.14750(19) 0.0358(11) Uani 1 1 d . . . . .
H24 H 0.8035 0.5663 0.1827 0.043 Uiso 1 1 calc R U . . .
C25 C 0.5860(4) 0.6651(4) 0.06707(18) 0.0364(11) Uani 1 1 d . . . . .
C26 C 0.5299(5) 0.7175(4) 0.0210(2) 0.0487(13) Uani 1 1 d . . . . .
H26 H 0.5097 0.6803 -0.0114 0.058 Uiso 1 1 calc R U . . .
C27 C 0.5057(6) 0.8235(5) 0.0247(3) 0.0662(17) Uani 1 1 d . . . . .
H27 H 0.4672 0.8577 -0.0054 0.079 Uiso 1 1 calc R U . . .
C28 C 0.5363(6) 0.8812(5) 0.0715(3) 0.0645(17) Uani 1 1 d . . . . .
H28 H 0.5185 0.9535 0.0729 0.077 Uiso 1 1 calc R U . . .
C29 C 0.5939(5) 0.8312(4) 0.1169(2) 0.0498(14) Uani 1 1 d . . . . .
H29 H 0.6159 0.8699 0.1487 0.060 Uiso 1 1 calc R U . . .
C30 C 0.6187(4) 0.7226(4) 0.11440(18) 0.0336(11) Uani 1 1 d . . . . .
C31 C 0.8622(4) 0.6385(4) 0.11413(19) 0.0379(11) Uani 1 1 d . . . . .
C32 C 0.9023(5) 0.5906(5) 0.0677(2) 0.0585(16) Uani 1 1 d . . . . .
H32 H 0.8632 0.5302 0.0533 0.070 Uiso 1 1 calc R U . . .
C33 C 1.0009(6) 0.6316(5) 0.0418(3) 0.0672(18) Uani 1 1 d . . . . .
H33 H 1.0272 0.5975 0.0105 0.081 Uiso 1 1 calc R U . . .
C34 C 1.0605(5) 0.7206(5) 0.0610(3) 0.0591(16) Uani 1 1 d . . . . .
C35 C 1.1696(6) 0.7615(7) 0.0334(3) 0.095(3) Uani 1 1 d . . . . .
H35A H 1.1443 0.8042 0.0019 0.142 Uiso 1 1 calc R U . . .
H35B H 1.2166 0.7025 0.0214 0.142 Uiso 1 1 calc R U . . .
H35C H 1.2176 0.8039 0.0593 0.142 Uiso 1 1 calc R U . . .
C36 C 1.0173(5) 0.7701(5) 0.1069(3) 0.0678(18) Uani 1 1 d . . . . .
H36 H 1.0544 0.8320 0.1202 0.081 Uiso 1 1 calc R U . . .
C37 C 0.9192(5) 0.7291(5) 0.1336(2) 0.0544(15) Uani 1 1 d . . . . .
H37 H 0.8922 0.7634 0.1647 0.065 Uiso 1 1 calc R U . . .
N1 N 0.4399(3) 0.5432(3) 0.27776(16) 0.0400(10) Uani 1 1 d . . . . .
H1 H 0.4441 0.6103 0.2712 0.048 Uiso 1 1 calc R U . . .
N2 N 0.6733(3) 0.6687(3) 0.16174(15) 0.0345(9) Uani 1 1 d . . . . .
O1 O 0.6717(4) 0.2763(3) 0.08551(14) 0.0567(10) Uani 1 1 d . . . . .
O2 O 0.7306(3) 0.1800(3) 0.16034(14) 0.0443(9) Uani 1 1 d . . . . .
O3 O 0.5229(3) 0.6976(3) 0.21999(15) 0.0516(10) Uani 1 1 d . . . . .
S1 S 0.60300(11) 0.52600(10) 0.06246(5) 0.0386(3) Uani 1 1 d . . . . .
S2 S 0.49978(13) 0.33237(12) 0.32866(5) 0.0511(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.383(7) . ?
C1 C2 1.389(7) . ?
C1 S2 1.759(6) . ?
C2 C3 1.357(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(7) . ?
C5 H5 0.9300 . ?
C6 N1 1.411(6) . ?
C7 C8 1.505(6) . ?
C7 C11 1.540(6) . ?
C7 S2 1.821(4) . ?
C7 H7 0.9800 . ?
C8 N1 1.333(6) . ?
C8 C9 1.382(6) . ?
C9 C10 1.442(7) . ?
C9 C22 1.467(6) . ?
C10 O3 1.233(6) . ?
C10 N2 1.416(6) . ?
C11 C19 1.501(6) . ?
C11 C12 1.521(6) . ?
C11 H11 0.9800 . ?
C12 C13 1.359(7) . ?
C12 C18 1.378(7) . ?
C13 C14 1.407(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(10) . ?
C14 H14 0.9300 . ?
C15 C17 1.344(9) . ?
C15 C16 1.512(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.368(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C22 1.350(6) . ?
C19 C20 1.478(7) . ?
C20 O1 1.203(6) . ?
C20 O2 1.346(6) . ?
C21 O2 1.454(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.505(6) . ?
C23 C24 1.517(6) . ?
C23 S1 1.824(5) . ?
C23 H23 0.9800 . ?
C24 N2 1.470(6) . ?
C24 C31 1.523(6) . ?
C24 H24 0.9800 . ?
C25 C30 1.384(6) . ?
C25 C26 1.408(7) . ?
C25 S1 1.761(5) . ?
C26 C27 1.362(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.369(9) . ?
C27 H27 0.9300 . ?
C28 C29 1.389(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.393(7) . ?
C29 H29 0.9300 . ?
C30 N2 1.435(6) . ?
C31 C32 1.369(7) . ?
C31 C37 1.373(7) . ?
C32 C33 1.388(8) . ?
C32 H32 0.9300 . ?
C33 C34 1.366(9) . ?
C33 H33 0.9300 . ?
C34 C36 1.379(9) . ?
C34 C35 1.503(8) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.393(8) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.0(5) . . ?
C6 C1 S2 119.0(4) . . ?
C2 C1 S2 122.0(5) . . ?
C3 C2 C1 120.4(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.9(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.0(6) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.0(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.7(5) . . ?
C1 C6 N1 121.0(5) . . ?
C5 C6 N1 119.3(5) . . ?
C8 C7 C11 117.1(4) . . ?
C8 C7 S2 108.6(3) . . ?
C11 C7 S2 107.7(3) . . ?
C8 C7 H7 107.7 . . ?
C11 C7 H7 107.7 . . ?
S2 C7 H7 107.7 . . ?
N1 C8 C9 122.8(4) . . ?
N1 C8 C7 115.4(4) . . ?
C9 C8 C7 121.5(4) . . ?
C8 C9 C10 119.2(4) . . ?
C8 C9 C22 118.7(4) . . ?
C10 C9 C22 121.1(4) . . ?
O3 C10 N2 117.7(4) . . ?
O3 C10 C9 124.3(4) . . ?
N2 C10 C9 118.0(4) . . ?
C19 C11 C12 113.6(4) . . ?
C19 C11 C7 112.6(4) . . ?
C12 C11 C7 108.0(4) . . ?
C19 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
C7 C11 H11 107.4 . . ?
C13 C12 C18 117.3(5) . . ?
C13 C12 C11 120.8(5) . . ?
C18 C12 C11 121.9(4) . . ?
C12 C13 C14 121.1(6) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.1(6) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C17 C15 C14 118.3(6) . . ?
C17 C15 C16 122.5(7) . . ?
C14 C15 C16 119.2(7) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 121.8(6) . . ?
C15 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C12 121.5(5) . . ?
C17 C18 H18 119.2 . . ?
C12 C18 H18 119.2 . . ?
C22 C19 C20 120.0(4) . . ?
C22 C19 C11 122.6(4) . . ?
C20 C19 C11 117.3(4) . . ?
O1 C20 O2 123.2(5) . . ?
O1 C20 C19 125.6(4) . . ?
O2 C20 C19 111.2(4) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 C9 122.4(4) . . ?
C19 C22 C23 122.3(4) . . ?
C9 C22 C23 115.2(4) . . ?
C22 C23 C24 107.1(4) . . ?
C22 C23 S1 113.0(3) . . ?
C24 C23 S1 111.2(3) . . ?
C22 C23 H23 108.5 . . ?
C24 C23 H23 108.5 . . ?
S1 C23 H23 108.5 . . ?
N2 C24 C23 109.1(4) . . ?
N2 C24 C31 111.4(4) . . ?
C23 C24 C31 117.3(4) . . ?
N2 C24 H24 106.1 . . ?
C23 C24 H24 106.1 . . ?
C31 C24 H24 106.1 . . ?
C30 C25 C26 119.5(5) . . ?
C30 C25 S1 123.1(3) . . ?
C26 C25 S1 117.3(4) . . ?
C27 C26 C25 119.1(5) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C28 122.0(5) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C27 C28 C29 119.7(5) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C28 C29 C30 119.5(5) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C25 C30 C29 120.2(4) . . ?
C25 C30 N2 119.5(4) . . ?
C29 C30 N2 120.2(4) . . ?
C32 C31 C37 118.7(5) . . ?
C32 C31 C24 121.9(5) . . ?
C37 C31 C24 119.2(4) . . ?
C31 C32 C33 120.3(6) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C34 C33 C32 122.1(6) . . ?
C34 C33 H33 119.0 . . ?
C32 C33 H33 119.0 . . ?
C33 C34 C36 117.2(5) . . ?
C33 C34 C35 121.1(6) . . ?
C36 C34 C35 121.6(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 . . ?
C34 C36 C37 121.3(6) . . ?
C34 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C31 C37 C36 120.4(5) . . ?
C31 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C8 N1 C6 126.9(4) . . ?
C8 N1 H1 116.5 . . ?
C6 N1 H1 116.5 . . ?
C10 N2 C30 112.7(4) . . ?
C10 N2 C24 114.3(4) . . ?
C30 N2 C24 113.5(4) . . ?
C20 O2 C21 116.0(4) . . ?
C25 S1 C23 104.1(2) . . ?
C1 S2 C7 96.4(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 1.9(9) . . . . ?
S2 C1 C2 C3 179.5(5) . . . . ?
C1 C2 C3 C4 -0.7(10) . . . . ?
C2 C3 C4 C5 -0.2(10) . . . . ?
C3 C4 C5 C6 -0.2(9) . . . . ?
C2 C1 C6 C5 -2.3(8) . . . . ?
S2 C1 C6 C5 -180.0(4) . . . . ?
C2 C1 C6 N1 175.0(5) . . . . ?
S2 C1 C6 N1 -2.6(7) . . . . ?
C4 C5 C6 C1 1.4(8) . . . . ?
C4 C5 C6 N1 -175.9(5) . . . . ?
C11 C7 C8 N1 -173.2(4) . . . . ?
S2 C7 C8 N1 -51.1(5) . . . . ?
C11 C7 C8 C9 12.0(6) . . . . ?
S2 C7 C8 C9 134.1(4) . . . . ?
N1 C8 C9 C10 0.2(7) . . . . ?
C7 C8 C9 C10 174.6(4) . . . . ?
N1 C8 C9 C22 -169.0(4) . . . . ?
C7 C8 C9 C22 5.4(6) . . . . ?
C8 C9 C10 O3 -7.6(7) . . . . ?
C22 C9 C10 O3 161.3(5) . . . . ?
C8 C9 C10 N2 173.6(4) . . . . ?
C22 C9 C10 N2 -17.5(6) . . . . ?
C8 C7 C11 C19 -24.5(6) . . . . ?
S2 C7 C11 C19 -147.1(3) . . . . ?
C8 C7 C11 C12 -150.8(4) . . . . ?
S2 C7 C11 C12 86.7(4) . . . . ?
C19 C11 C12 C13 -59.4(6) . . . . ?
C7 C11 C12 C13 66.2(6) . . . . ?
C19 C11 C12 C18 121.3(5) . . . . ?
C7 C11 C12 C18 -113.0(5) . . . . ?
C18 C12 C13 C14 1.5(10) . . . . ?
C11 C12 C13 C14 -177.8(6) . . . . ?
C12 C13 C14 C15 -1.6(12) . . . . ?
C13 C14 C15 C17 0.8(11) . . . . ?
C13 C14 C15 C16 -177.9(7) . . . . ?
C14 C15 C17 C18 0.0(10) . . . . ?
C16 C15 C17 C18 178.7(6) . . . . ?
C15 C17 C18 C12 -0.1(10) . . . . ?
C13 C12 C18 C17 -0.6(9) . . . . ?
C11 C12 C18 C17 178.6(5) . . . . ?
C12 C11 C19 C22 145.5(4) . . . . ?
C7 C11 C19 C22 22.3(6) . . . . ?
C12 C11 C19 C20 -39.3(6) . . . . ?
C7 C11 C19 C20 -162.5(4) . . . . ?
C22 C19 C20 O1 -39.8(7) . . . . ?
C11 C19 C20 O1 144.9(5) . . . . ?
C22 C19 C20 O2 139.1(4) . . . . ?
C11 C19 C20 O2 -36.3(6) . . . . ?
C20 C19 C22 C9 179.1(4) . . . . ?
C11 C19 C22 C9 -5.9(7) . . . . ?
C20 C19 C22 C23 -3.9(7) . . . . ?
C11 C19 C22 C23 171.2(4) . . . . ?
C8 C9 C22 C19 -9.2(6) . . . . ?
C10 C9 C22 C19 -178.2(4) . . . . ?
C8 C9 C22 C23 173.5(4) . . . . ?
C10 C9 C22 C23 4.6(6) . . . . ?
C19 C22 C23 C24 -141.5(4) . . . . ?
C9 C22 C23 C24 35.8(5) . . . . ?
C19 C22 C23 S1 95.7(5) . . . . ?
C9 C22 C23 S1 -87.0(4) . . . . ?
C22 C23 C24 N2 -66.2(4) . . . . ?
S1 C23 C24 N2 57.7(4) . . . . ?
C22 C23 C24 C31 165.9(4) . . . . ?
S1 C23 C24 C31 -70.2(5) . . . . ?
C30 C25 C26 C27 -2.0(8) . . . . ?
S1 C25 C26 C27 174.4(5) . . . . ?
C25 C26 C27 C28 1.3(9) . . . . ?
C26 C27 C28 C29 0.1(10) . . . . ?
C27 C28 C29 C30 -0.7(9) . . . . ?
C26 C25 C30 C29 1.4(7) . . . . ?
S1 C25 C30 C29 -174.8(4) . . . . ?
C26 C25 C30 N2 178.6(4) . . . . ?
S1 C25 C30 N2 2.4(6) . . . . ?
C28 C29 C30 C25 0.0(8) . . . . ?
C28 C29 C30 N2 -177.2(5) . . . . ?
N2 C24 C31 C32 -134.5(5) . . . . ?
C23 C24 C31 C32 -7.7(7) . . . . ?
N2 C24 C31 C37 50.8(6) . . . . ?
C23 C24 C31 C37 177.6(5) . . . . ?
C37 C31 C32 C33 1.8(9) . . . . ?
C24 C31 C32 C33 -172.9(5) . . . . ?
C31 C32 C33 C34 -0.6(10) . . . . ?
C32 C33 C34 C36 -1.2(10) . . . . ?
C32 C33 C34 C35 178.0(6) . . . . ?
C33 C34 C36 C37 1.9(10) . . . . ?
C35 C34 C36 C37 -177.3(6) . . . . ?
C32 C31 C37 C36 -1.1(8) . . . . ?
C24 C31 C37 C36 173.7(5) . . . . ?
C34 C36 C37 C31 -0.8(9) . . . . ?
C9 C8 N1 C6 -178.5(4) . . . . ?
C7 C8 N1 C6 6.8(7) . . . . ?
C1 C6 N1 C8 24.4(7) . . . . ?
C5 C6 N1 C8 -158.2(5) . . . . ?
O3 C10 N2 C30 -61.2(6) . . . . ?
C9 C10 N2 C30 117.7(4) . . . . ?
O3 C10 N2 C24 167.3(4) . . . . ?
C9 C10 N2 C24 -13.9(6) . . . . ?
C25 C30 N2 C10 -89.9(5) . . . . ?
C29 C30 N2 C10 87.4(5) . . . . ?
C25 C30 N2 C24 42.1(6) . . . . ?
C29 C30 N2 C24 -140.7(4) . . . . ?
C23 C24 N2 C10 56.3(5) . . . . ?
C31 C24 N2 C10 -172.6(4) . . . . ?
C23 C24 N2 C30 -74.9(4) . . . . ?
C31 C24 N2 C30 56.2(5) . . . . ?
O1 C20 O2 C21 -4.7(7) . . . . ?
C19 C20 O2 C21 176.4(4) . . . . ?
C30 C25 S1 C23 -13.0(5) . . . . ?
C26 C25 S1 C23 170.7(4) . . . . ?
C22 C23 S1 C25 103.4(4) . . . . ?
C24 C23 S1 C25 -17.0(4) . . . . ?
C6 C1 S2 C7 -34.5(4) . . . . ?
C2 C1 S2 C7 147.9(5) . . . . ?
C8 C7 S2 C1 59.3(4) . . . . ?
C11 C7 S2 C1 -173.0(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
N1 H1 O3 0.86 1.90 2.587(5) 135.8 .

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.079



####################################################################### 
# 
# 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_9c
_database_code_depnum_ccdc_archive 'CCDC 1943416'
loop_
_audit_author_name
_audit_author_address
Yan 'Yangzhou University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2019-08-30 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         'C31 H26 N2 O4 S2'
_chemical_formula_sum            'C31 H26 N2 O4 S2'
_chemical_formula_weight         554.66

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                   8.9049(8)
_cell_length_b                   14.0612(12)
_cell_length_c                   22.343(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.263(3)
_cell_angle_gamma                90
_cell_volume                     2793.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3891
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      20.83

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26120
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.331
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5473
_reflns_number_gt                2410
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.1209P)²+1.1685P] 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         5473
_refine_ls_number_parameters     355
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.2165
_refine_ls_R_factor_gt           0.0930
_refine_ls_wR_factor_ref         0.2662
_refine_ls_wR_factor_gt          0.2271
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.069
_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 0.3485(6) 0.9027(4) 0.0009(2) 0.0676(14) Uani 1 1 d . . . . .
C2 C 0.4008(7) 0.9187(5) -0.0553(3) 0.0960(19) Uani 1 1 d . . . . .
H2 H 0.4756 0.8797 -0.0692 0.115 Uiso 1 1 calc R U . . .
C3 C 0.3437(8) 0.9916(7) -0.0909(3) 0.121(3) Uani 1 1 d . . . . .
H3 H 0.3758 1.0002 -0.1294 0.146 Uiso 1 1 calc R U . . .
C4 C 0.2394(9) 1.0510(6) -0.0688(4) 0.120(3) Uani 1 1 d . . . . .
H4 H 0.2024 1.1013 -0.0923 0.144 Uiso 1 1 calc R U . . .
C5 C 0.1877(7) 1.0381(5) -0.0125(3) 0.105(2) Uani 1 1 d . . . . .
H5 H 0.1180 1.0801 0.0022 0.126 Uiso 1 1 calc R U . . .
C6 C 0.2409(6) 0.9616(4) 0.0224(2) 0.0744(15) Uani 1 1 d . . . . .
C7 C 0.3170(7) 0.8806(4) 0.1278(2) 0.0865(18) Uani 1 1 d . . . . .
H7A H 0.3935 0.9283 0.1372 0.104 Uiso 1 1 calc R U . . .
H7B H 0.2863 0.8544 0.1653 0.104 Uiso 1 1 calc R U . . .
C8 C 0.3843(5) 0.8029(3) 0.0923(2) 0.0538(12) Uani 1 1 d . . . . .
C9 C 0.4303(5) 0.7210(3) 0.11881(18) 0.0465(11) Uani 1 1 d . . . . .
C10 C 0.5053(5) 0.6482(4) 0.0856(2) 0.0599(12) Uani 1 1 d . . . . .
C11 C 0.6080(8) 0.4926(4) 0.0881(2) 0.109(2) Uani 1 1 d . . . . .
H11A H 0.5336 0.4638 0.0611 0.164 Uiso 1 1 calc R U . . .
H11B H 0.6446 0.4464 0.1170 0.164 Uiso 1 1 calc R U . . .
H11C H 0.6901 0.5152 0.0659 0.164 Uiso 1 1 calc R U . . .
C12 C 0.4264(8) 0.7406(4) 0.3427(2) 0.0855(16) Uani 1 1 d . U . . .
C13 C 0.5742(9) 0.7369(4) 0.3637(2) 0.1020(17) Uani 1 1 d . U . . .
H13 H 0.6492 0.7211 0.3382 0.122 Uiso 1 1 calc R U . . .
C14 C 0.6102(11) 0.7574(5) 0.4242(3) 0.128(2) Uani 1 1 d . U . . .
H14 H 0.7098 0.7586 0.4392 0.154 Uiso 1 1 calc R U . . .
C15 C 0.4938(14) 0.7759(5) 0.4612(3) 0.140(3) Uani 1 1 d . U . . .
H15 H 0.5170 0.7881 0.5016 0.168 Uiso 1 1 calc R U . . .
C16 C 0.3473(13) 0.7769(5) 0.4407(3) 0.137(2) Uani 1 1 d . U . . .
H16 H 0.2736 0.7903 0.4673 0.164 Uiso 1 1 calc R U . . .
C17 C 0.3048(10) 0.7585(4) 0.3812(2) 0.1069(17) Uani 1 1 d . U . . .
C18 C 0.1410(7) 0.6541(4) 0.3064(3) 0.0972(19) Uani 1 1 d . . . . .
H18A H 0.1736 0.5994 0.3303 0.117 Uiso 1 1 calc R U . . .
H18B H 0.0454 0.6388 0.2856 0.117 Uiso 1 1 calc R U . . .
C19 C 0.2548(6) 0.6767(3) 0.2621(2) 0.0651(14) Uani 1 1 d . . . . .
C20 C 0.2572(5) 0.6618(3) 0.2017(2) 0.0540(12) Uani 1 1 d . . . . .
C21 C 0.1407(6) 0.6116(3) 0.1658(3) 0.0717(15) Uani 1 1 d . . . . .
C22 C 0.0783(9) 0.5318(6) 0.0769(3) 0.143(3) Uani 1 1 d . . . . .
H22A H 0.0632 0.4727 0.0973 0.215 Uiso 1 1 calc R U . . .
H22B H 0.1193 0.5194 0.0389 0.215 Uiso 1 1 calc R U . . .
H22C H -0.0163 0.5641 0.0707 0.215 Uiso 1 1 calc R U . . .
C23 C 0.3931(5) 0.7032(3) 0.18196(18) 0.0468(11) Uani 1 1 d . . . . .
C24 C 0.4714(5) 0.7396(3) 0.23061(19) 0.0478(11) Uani 1 1 d . . . . .
C25 C 0.6085(5) 0.7986(3) 0.23363(17) 0.0486(11) Uani 1 1 d . . . . .
C26 C 0.6091(6) 0.8895(3) 0.25611(19) 0.0572(12) Uani 1 1 d . . . . .
H26 H 0.5217 0.9143 0.2708 0.069 Uiso 1 1 calc R U . . .
C27 C 0.7365(6) 0.9442(4) 0.2571(2) 0.0653(14) Uani 1 1 d . . . . .
H27 H 0.7333 1.0059 0.2720 0.078 Uiso 1 1 calc R U . . .
C28 C 0.8683(6) 0.9103(4) 0.2369(2) 0.0654(14) Uani 1 1 d . . . . .
C29 C 1.0079(6) 0.9707(4) 0.2389(3) 0.098(2) Uani 1 1 d . . . . .
H29A H 1.0123 1.0051 0.2020 0.147 Uiso 1 1 calc R U . . .
H29B H 1.0950 0.9307 0.2444 0.147 Uiso 1 1 calc R U . . .
H29C H 1.0056 1.0147 0.2717 0.147 Uiso 1 1 calc R U . . .
C30 C 0.8663(5) 0.8193(4) 0.2136(2) 0.0676(14) Uani 1 1 d . . . . .
H30 H 0.9536 0.7946 0.1987 0.081 Uiso 1 1 calc R U . . .
C31 C 0.7396(5) 0.7648(3) 0.2118(2) 0.0598(13) Uani 1 1 d . . . . .
H31 H 0.7418 0.7039 0.1956 0.072 Uiso 1 1 calc R U . . .
N1 N 0.4039(4) 0.8233(3) 0.03344(16) 0.0616(10) Uani 1 1 d . . . . .
H1 H 0.4558 0.7832 0.0142 0.074 Uiso 1 1 calc R U . . .
N2 N 0.3856(5) 0.7216(3) 0.28125(15) 0.0606(11) Uani 1 1 d . . . . .
O1 O 0.5340(4) 0.6537(3) 0.03296(15) 0.0868(12) Uani 1 1 d . . . . .
O2 O 0.5413(4) 0.5717(2) 0.11870(14) 0.0700(10) Uani 1 1 d . . . . .
O3 O 0.0212(5) 0.5884(3) 0.1837(2) 0.1173(16) Uani 1 1 d . . . . .
O4 O 0.1798(4) 0.5897(3) 0.11227(19) 0.0963(13) Uani 1 1 d . . . . .
S1 S 0.1625(2) 0.93557(15) 0.09116(7) 0.1138(8) Uani 1 1 d . . . . .
S2 S 0.1200(3) 0.75552(14) 0.35399(9) 0.1279(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.374(7) . ?
C1 C2 1.383(7) . ?
C1 N1 1.405(6) . ?
C2 C3 1.378(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(8) . ?
C5 H5 0.9300 . ?
C6 S1 1.761(6) . ?
C7 C8 1.496(7) . ?
C7 S1 1.741(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.349(6) . ?
C8 N1 1.366(5) . ?
C9 C10 1.449(6) . ?
C9 C23 1.488(6) . ?
C10 O1 1.221(5) . ?
C10 O2 1.334(5) . ?
C11 O2 1.451(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.372(9) . ?
C12 N2 1.426(6) . ?
C12 C17 1.442(9) . ?
C13 C14 1.401(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.357(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(9) . ?
C16 H16 0.9300 . ?
C17 S2 1.722(9) . ?
C18 C19 1.489(6) . ?
C18 S2 1.796(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.367(6) . ?
C19 N2 1.373(6) . ?
C20 C23 1.436(6) . ?
C20 C21 1.457(7) . ?
C21 O3 1.203(6) . ?
C21 O4 1.301(6) . ?
C22 O4 1.422(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.358(6) . ?
C24 N2 1.423(5) . ?
C24 C25 1.475(6) . ?
C25 C26 1.373(6) . ?
C25 C31 1.376(6) . ?
C26 C27 1.369(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.368(7) . ?
C27 H27 0.9300 . ?
C28 C30 1.381(6) . ?
C28 C29 1.504(7) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.362(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.8(5) . . ?
C6 C1 N1 122.0(5) . . ?
C2 C1 N1 118.2(5) . . ?
C3 C2 C1 120.9(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.0(7) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 119.5(7) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 119.4(6) . . ?
C1 C6 S1 119.8(4) . . ?
C5 C6 S1 120.6(5) . . ?
C8 C7 S1 113.8(4) . . ?
C8 C7 H7A 108.8 . . ?
S1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
S1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 N1 123.4(4) . . ?
C9 C8 C7 120.7(4) . . ?
N1 C8 C7 115.8(4) . . ?
C8 C9 C10 121.0(4) . . ?
C8 C9 C23 118.8(4) . . ?
C10 C9 C23 120.0(4) . . ?
O1 C10 O2 121.9(4) . . ?
O1 C10 C9 125.2(5) . . ?
O2 C10 C9 112.9(4) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N2 120.6(6) . . ?
C13 C12 C17 122.7(6) . . ?
N2 C12 C17 116.6(6) . . ?
C12 C13 C14 119.0(7) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 118.4(9) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C16 C15 C14 122.6(8) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C17 121.7(8) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C12 115.5(8) . . ?
C16 C17 S2 123.1(6) . . ?
C12 C17 S2 121.4(5) . . ?
C19 C18 S2 108.8(4) . . ?
C19 C18 H18A 109.9 . . ?
S2 C18 H18A 109.9 . . ?
C19 C18 H18B 109.9 . . ?
S2 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C20 C19 N2 108.5(4) . . ?
C20 C19 C18 132.2(5) . . ?
N2 C19 C18 119.3(5) . . ?
C19 C20 C23 107.6(4) . . ?
C19 C20 C21 124.6(5) . . ?
C23 C20 C21 127.8(5) . . ?
O3 C21 O4 122.0(6) . . ?
O3 C21 C20 124.3(6) . . ?
O4 C21 C20 113.7(5) . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C20 108.1(4) . . ?
C24 C23 C9 124.3(4) . . ?
C20 C23 C9 126.6(4) . . ?
C23 C24 N2 107.2(4) . . ?
C23 C24 C25 129.4(4) . . ?
N2 C24 C25 123.0(4) . . ?
C26 C25 C31 117.8(4) . . ?
C26 C25 C24 121.8(4) . . ?
C31 C25 C24 120.4(4) . . ?
C27 C26 C25 121.0(4) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C28 C27 C26 121.7(4) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 C28 C30 117.0(4) . . ?
C27 C28 C29 121.1(5) . . ?
C30 C28 C29 121.8(5) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C28 121.7(5) . . ?
C31 C30 H30 119.2 . . ?
C28 C30 H30 119.2 . . ?
C30 C31 C25 120.9(4) . . ?
C30 C31 H31 119.6 . . ?
C25 C31 H31 119.6 . . ?
C8 N1 C1 127.1(4) . . ?
C8 N1 H1 116.4 . . ?
C1 N1 H1 116.4 . . ?
C19 N2 C24 108.6(4) . . ?
C19 N2 C12 123.5(4) . . ?
C24 N2 C12 127.9(5) . . ?
C10 O2 C11 116.7(4) . . ?
C21 O4 C22 116.8(5) . . ?
C7 S1 C6 99.3(3) . . ?
C17 S2 C18 95.7(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
N1 H1 O1 0.86 1.99 2.651(5) 133.5 .

_refine_diff_density_max         0.952
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.056





#=======================================================================================
####################################################################### 
# 
# 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_6c
_database_code_depnum_ccdc_archive 'CCDC 1883730'
loop_
_audit_author_name
_audit_author_address
'Chao-Guo Yan' 'Yangzhou University'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.	2019-08-30 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         'C35 H22 Cl2 N2 O3 S2'
_chemical_formula_sum            'C35 H22 Cl2 N2 O3 S2'
_chemical_formula_weight         653.56

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           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                   18.2890(10)
_cell_length_b                   13.2118(8)
_cell_length_c                   24.2095(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.1650(19)
_cell_angle_gamma                90
_cell_volume                     5848.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6995
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.59

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             2688
_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    0.407
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29555
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.902
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6729
_reflns_number_gt                3668
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0772P)²+8.1200P] 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         6729
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1565
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.1821
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.0799(2) 0.4854(3) 0.31783(16) 0.0566(11) Uani 1 1 d . . . . .
C2 C 0.0752(3) 0.4104(4) 0.35811(18) 0.0713(13) Uani 1 1 d . . . . .
H2 H 0.0860 0.3435 0.3496 0.086 Uiso 1 1 calc R U . . .
C3 C 0.0544(3) 0.4360(4) 0.41034(19) 0.0820(16) Uani 1 1 d . . . . .
H3 H 0.0518 0.3858 0.4372 0.098 Uiso 1 1 calc R U . . .
C4 C 0.0377(3) 0.5324(4) 0.42372(18) 0.0767(14) Uani 1 1 d . . . . .
H4 H 0.0228 0.5481 0.4592 0.092 Uiso 1 1 calc R U . . .
C5 C 0.0428(2) 0.6071(4) 0.38453(15) 0.0646(12) Uani 1 1 d . . . . .
H5 H 0.0317 0.6737 0.3937 0.078 Uiso 1 1 calc R U . . .
C6 C 0.0645(2) 0.5840(3) 0.33139(15) 0.0553(11) Uani 1 1 d . . . . .
C7 C 0.0997(2) 0.6584(3) 0.24179(14) 0.0460(10) Uani 1 1 d . . . . .
C8 C 0.1241(2) 0.5661(3) 0.21895(14) 0.0464(10) Uani 1 1 d . . . . .
C9 C 0.1563(2) 0.5652(3) 0.16818(15) 0.0503(10) Uani 1 1 d . . . . .
C10 C 0.1874(2) 0.4701(3) 0.14526(15) 0.0448(9) Uani 1 1 d . . . . .
C11 C 0.2618(2) 0.4574(3) 0.14412(15) 0.0492(10) Uani 1 1 d . . . . .
H11 H 0.2922 0.5057 0.1605 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2927(2) 0.3735(3) 0.11894(15) 0.0542(11) Uani 1 1 d . . . . .
H12 H 0.3432 0.3662 0.1182 0.065 Uiso 1 1 calc R U . . .
C13 C 0.2484(3) 0.3026(3) 0.09553(17) 0.0628(12) Uani 1 1 d . . . . .
C14 C 0.1739(3) 0.3119(4) 0.0976(2) 0.0777(14) Uani 1 1 d . . . . .
H14 H 0.1437 0.2621 0.0823 0.093 Uiso 1 1 calc R U . . .
C15 C 0.1437(3) 0.3958(4) 0.12254(19) 0.0669(12) Uani 1 1 d . . . . .
H15 H 0.0931 0.4021 0.1240 0.080 Uiso 1 1 calc R U . . .
C16 C 0.1917(2) 1.0216(3) 0.18676(15) 0.0479(10) Uani 1 1 d . . . . .
C17 C 0.2346(3) 1.1072(3) 0.19468(18) 0.0667(12) Uani 1 1 d . . . . .
H17 H 0.2790 1.1127 0.1768 0.080 Uiso 1 1 calc R U . . .
C18 C 0.2120(3) 1.1841(4) 0.2289(2) 0.0808(16) Uani 1 1 d . . . . .
H18 H 0.2407 1.2417 0.2336 0.097 Uiso 1 1 calc R U . . .
C19 C 0.1478(4) 1.1757(4) 0.25580(19) 0.0828(17) Uani 1 1 d . . . . .
H19 H 0.1340 1.2261 0.2803 0.099 Uiso 1 1 calc R U . . .
C20 C 0.1032(3) 1.0933(4) 0.24709(15) 0.0669(13) Uani 1 1 d . . . . .
H20 H 0.0584 1.0893 0.2645 0.080 Uiso 1 1 calc R U . . .
C21 C 0.1254(2) 1.0156(3) 0.21203(13) 0.0482(10) Uani 1 1 d . . . . .
C22 C 0.14693(18) 0.8454(3) 0.12885(12) 0.0337(8) Uani 1 1 d . . . . .
H22 H 0.1479 0.8301 0.0893 0.040 Uiso 1 1 calc R U . . .
C23 C 0.07590(19) 0.9013(3) 0.14108(12) 0.0339(8) Uani 1 1 d . . . . .
H23 H 0.0366 0.8512 0.1373 0.041 Uiso 1 1 calc R U . . .
C24 C 0.05347(18) 0.9901(2) 0.10509(12) 0.0323(8) Uani 1 1 d . . . . .
C25 C 0.0946(2) 1.0254(3) 0.06182(13) 0.0418(9) Uani 1 1 d . . . . .
H25 H 0.1409 0.9985 0.0563 0.050 Uiso 1 1 calc R U . . .
C26 C 0.0680(2) 1.1002(3) 0.02648(13) 0.0426(9) Uani 1 1 d . . . . .
H26 H 0.0961 1.1237 -0.0024 0.051 Uiso 1 1 calc R U . . .
C27 C 0.0001(2) 1.1384(2) 0.03489(13) 0.0377(9) Uani 1 1 d . . . . .
C28 C -0.0422(2) 1.1066(3) 0.07794(14) 0.0436(9) Uani 1 1 d . . . . .
H28 H -0.0881 1.1347 0.0835 0.052 Uiso 1 1 calc R U . . .
C29 C -0.0149(2) 1.0321(3) 0.11270(13) 0.0392(9) Uani 1 1 d . . . . .
H29 H -0.0431 1.0096 0.1418 0.047 Uiso 1 1 calc R U . . .
C30 C 0.0881(2) 0.8477(3) 0.23657(14) 0.0479(10) Uani 1 1 d . . . . .
C31 C 0.10724(19) 0.7488(3) 0.21222(13) 0.0403(9) Uani 1 1 d . . . . .
C32 C 0.14294(18) 0.7470(3) 0.16054(12) 0.0360(8) Uani 1 1 d . . . . .
C33 C 0.16794(18) 0.6574(3) 0.13968(13) 0.0368(8) Uani 1 1 d . . . . .
C34 C 0.2089(2) 0.6574(3) 0.08677(14) 0.0425(9) Uani 1 1 d . . . . .
C35 C 0.2192(3) 0.5799(3) -0.00052(16) 0.0724(14) Uani 1 1 d . . . . .
H35A H 0.2220 0.6422 -0.0208 0.109 Uiso 1 1 calc R U . . .
H35B H 0.1950 0.5296 -0.0230 0.109 Uiso 1 1 calc R U . . .
H35C H 0.2676 0.5571 0.0092 0.109 Uiso 1 1 calc R U . . .
Cl1 Cl 0.28658(10) 0.19826(10) 0.06300(6) 0.1071(6) Uani 1 1 d . . . . .
Cl2 Cl -0.03483(7) 1.22979(7) -0.01112(4) 0.0594(3) Uani 1 1 d . . . . .
N1 N 0.0708(2) 0.6626(3) 0.29385(12) 0.0667(11) Uani 1 1 d . . . . .
H1 H 0.0548 0.7206 0.3042 0.080 Uiso 1 1 calc R U . . .
N2 N 0.08011(16) 0.9290(2) 0.20049(10) 0.0424(8) Uani 1 1 d . . . . .
O1 O 0.08247(17) 0.8612(2) 0.28664(9) 0.0658(9) Uani 1 1 d . . . . .
O2 O 0.26267(16) 0.7068(2) 0.07909(11) 0.0610(8) Uani 1 1 d . . . . .
O3 O 0.17809(14) 0.59601(19) 0.04943(9) 0.0502(7) Uani 1 1 d . . . . .
S1 S 0.10549(8) 0.44904(9) 0.25082(5) 0.0784(4) Uani 1 1 d . . . . .
S2 S 0.22801(5) 0.92075(8) 0.14753(4) 0.0488(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 C6 1.375(6) . ?
C1 C2 1.394(5) . ?
C1 S1 1.764(4) . ?
C2 C3 1.370(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.352(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 N1 1.386(5) . ?
C7 N1 1.378(4) . ?
C7 C31 1.401(5) . ?
C7 C8 1.414(5) . ?
C8 C9 1.373(5) . ?
C8 S1 1.765(4) . ?
C9 C33 1.419(5) . ?
C9 C10 1.491(5) . ?
C10 C11 1.372(5) . ?
C10 C15 1.374(6) . ?
C11 C12 1.389(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.356(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(7) . ?
C13 Cl1 1.741(4) . ?
C14 C15 1.383(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.371(5) . ?
C16 C17 1.388(6) . ?
C16 S2 1.773(4) . ?
C17 C18 1.381(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.398(5) . ?
C20 H20 0.9300 . ?
C21 N2 1.436(5) . ?
C22 C32 1.512(5) . ?
C22 C23 1.529(5) . ?
C22 S2 1.835(4) . ?
C22 H22 0.9800 . ?
C23 N2 1.485(4) . ?
C23 C24 1.513(4) . ?
C23 H23 0.9800 . ?
C24 C25 1.383(4) . ?
C24 C29 1.383(5) . ?
C25 C26 1.389(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.359(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(5) . ?
C27 Cl2 1.755(3) . ?
C28 C29 1.382(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 O1 1.232(4) . ?
C30 N2 1.391(4) . ?
C30 C31 1.479(5) . ?
C31 C32 1.423(4) . ?
C32 C33 1.369(5) . ?
C33 C34 1.497(5) . ?
C34 O2 1.198(4) . ?
C34 O3 1.331(4) . ?
C35 O3 1.452(4) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.4(4) . . ?
C6 C1 S1 122.5(3) . . ?
C2 C1 S1 118.1(4) . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 N1 122.2(3) . . ?
C1 C6 C5 119.6(4) . . ?
N1 C6 C5 118.2(4) . . ?
N1 C7 C31 118.4(3) . . ?
N1 C7 C8 121.5(3) . . ?
C31 C7 C8 120.0(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 S1 118.3(3) . . ?
C7 C8 S1 121.3(3) . . ?
C8 C9 C33 120.0(3) . . ?
C8 C9 C10 120.9(3) . . ?
C33 C9 C10 118.7(3) . . ?
C11 C10 C15 118.2(4) . . ?
C11 C10 C9 119.9(4) . . ?
C15 C10 C9 121.8(4) . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 Cl1 119.7(4) . . ?
C14 C13 Cl1 119.8(4) . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 120.9(4) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C21 C16 C17 119.3(4) . . ?
C21 C16 S2 122.7(3) . . ?
C17 C16 S2 118.0(3) . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.0(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 119.7(5) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 119.9(4) . . ?
C16 C21 N2 118.1(3) . . ?
C20 C21 N2 122.0(4) . . ?
C32 C22 C23 105.5(3) . . ?
C32 C22 S2 112.9(2) . . ?
C23 C22 S2 112.1(2) . . ?
C32 C22 H22 108.8 . . ?
C23 C22 H22 108.8 . . ?
S2 C22 H22 108.8 . . ?
N2 C23 C24 112.0(3) . . ?
N2 C23 C22 106.2(3) . . ?
C24 C23 C22 119.0(3) . . ?
N2 C23 H23 106.3 . . ?
C24 C23 H23 106.3 . . ?
C22 C23 H23 106.3 . . ?
C25 C24 C29 118.2(3) . . ?
C25 C24 C23 123.5(3) . . ?
C29 C24 C23 118.0(3) . . ?
C24 C25 C26 121.1(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 118.8(3) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C28 122.0(3) . . ?
C26 C27 Cl2 118.8(3) . . ?
C28 C27 Cl2 119.2(3) . . ?
C27 C28 C29 118.5(4) . . ?
C27 C28 H28 120.8 . . ?
C29 C28 H28 120.8 . . ?
C28 C29 C24 121.4(3) . . ?
C28 C29 H29 119.3 . . ?
C24 C29 H29 119.3 . . ?
O1 C30 N2 119.7(3) . . ?
O1 C30 C31 123.1(3) . . ?
N2 C30 C31 117.1(3) . . ?
C7 C31 C32 119.1(3) . . ?
C7 C31 C30 121.6(3) . . ?
C32 C31 C30 118.8(3) . . ?
C33 C32 C31 120.1(3) . . ?
C33 C32 C22 122.4(3) . . ?
C31 C32 C22 117.4(3) . . ?
C32 C33 C9 120.6(3) . . ?
C32 C33 C34 119.5(3) . . ?
C9 C33 C34 119.9(3) . . ?
O2 C34 O3 124.3(3) . . ?
O2 C34 C33 124.0(4) . . ?
O3 C34 C33 111.7(3) . . ?
O3 C35 H35A 109.5 . . ?
O3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C7 N1 C6 127.4(3) . . ?
C7 N1 H1 116.3 . . ?
C6 N1 H1 116.3 . . ?
C30 N2 C21 116.1(3) . . ?
C30 N2 C23 114.9(3) . . ?
C21 N2 C23 113.8(3) . . ?
C34 O3 C35 115.9(3) . . ?
C1 S1 C8 102.76(19) . . ?
C16 S2 C22 103.29(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.97 2.639(5) 133.3 .

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.063





#=======================================================================================
####################################################################### 
# 
# 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_9b
_database_code_depnum_ccdc_archive 'CCDC 1943415'
loop_
_audit_author_name
_audit_author_address
Yan 'Yangzhou University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2019-08-30 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         'C32 H28 N2 O4 S2'
_chemical_formula_sum            'C32 H28 N2 O4 S2'
_chemical_formula_weight         568.68

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                   7.6623(5)
_cell_length_b                   10.2269(7)
_cell_length_c                   19.0080(13)
_cell_angle_alpha                102.840(2)
_cell_angle_beta                 91.559(2)
_cell_angle_gamma                103.009(2)
_cell_volume                     1410.30(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9136
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19596
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5485
_reflns_number_gt                4249
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0519P)²+3.5063P] 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         5485
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.1879
_refine_ls_wR_factor_gt          0.1780
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 1.1605(6) 0.6791(4) 0.0227(2) 0.0426(9) Uani 1 1 d . . . . .
C2 C 1.2815(7) 0.6019(5) -0.0031(2) 0.0562(11) Uani 1 1 d . . . . .
H2 H 1.3746 0.5973 0.0281 0.067 Uiso 1 1 calc R U . . .
C3 C 1.2652(7) 0.5311(5) -0.0752(3) 0.0620(13) Uani 1 1 d . . . . .
H3 H 1.3456 0.4776 -0.0920 0.074 Uiso 1 1 calc R U . . .
C4 C 1.1317(8) 0.5399(5) -0.1214(2) 0.0630(13) Uani 1 1 d . . . . .
H4 H 1.1197 0.4912 -0.1695 0.076 Uiso 1 1 calc R U . . .
C5 C 1.0144(7) 0.6208(5) -0.0970(2) 0.0591(12) Uani 1 1 d . . . . .
H5 H 0.9259 0.6288 -0.1291 0.071 Uiso 1 1 calc R U . . .
C6 C 1.0270(6) 0.6910(4) -0.0243(2) 0.0451(10) Uani 1 1 d . . . . .
C7 C 1.0261(6) 0.9151(4) 0.0790(2) 0.0449(9) Uani 1 1 d . . . . .
H7A H 1.1244 0.9651 0.0571 0.054 Uiso 1 1 calc R U . . .
H7B H 0.9640 0.9810 0.1055 0.054 Uiso 1 1 calc R U . . .
C8 C 1.0984(5) 0.8435(4) 0.1297(2) 0.0364(8) Uani 1 1 d . . . . .
C9 C 1.0972(5) 0.8860(3) 0.20305(19) 0.0334(8) Uani 1 1 d . . . . .
C10 C 1.1614(5) 0.8089(4) 0.2498(2) 0.0379(8) Uani 1 1 d . . . . .
C11 C 1.1996(9) 0.7863(5) 0.3699(2) 0.0701(15) Uani 1 1 d . . . . .
H11A H 1.3083 0.7550 0.3585 0.084 Uiso 1 1 calc R U . . .
H11B H 1.1010 0.7057 0.3650 0.084 Uiso 1 1 calc R U . . .
C12 C 1.2213(9) 0.8711(6) 0.4448(3) 0.0848(18) Uani 1 1 d . . . . .
H12A H 1.3238 0.9475 0.4502 0.127 Uiso 1 1 calc R U . . .
H12B H 1.2388 0.8158 0.4779 0.127 Uiso 1 1 calc R U . . .
H12C H 1.1156 0.9052 0.4551 0.127 Uiso 1 1 calc R U . . .
C13 C 0.7461(5) 1.1994(4) 0.34375(19) 0.0367(8) Uani 1 1 d . . . . .
C14 C 0.5687(5) 1.1260(4) 0.3344(2) 0.0423(9) Uani 1 1 d . . . . .
H14 H 0.5347 1.0417 0.3007 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4414(6) 1.1776(4) 0.3750(2) 0.0478(10) Uani 1 1 d . . . . .
H15 H 0.3228 1.1267 0.3694 0.057 Uiso 1 1 calc R U . . .
C16 C 0.4893(7) 1.3037(5) 0.4235(2) 0.0547(11) Uani 1 1 d . . . . .
H16 H 0.4033 1.3385 0.4504 0.066 Uiso 1 1 calc R U . . .
C17 C 0.6657(7) 1.3788(4) 0.4322(2) 0.0527(11) Uani 1 1 d . . . . .
H17 H 0.6977 1.4640 0.4652 0.063 Uiso 1 1 calc R U . . .
C18 C 0.7957(6) 1.3288(4) 0.3925(2) 0.0405(9) Uani 1 1 d . . . . .
C19 C 1.0488(7) 1.3861(4) 0.3043(2) 0.0538(11) Uani 1 1 d . . . . .
H19A H 0.9630 1.4171 0.2775 0.065 Uiso 1 1 calc R U . . .
H19B H 1.1689 1.4316 0.2956 0.065 Uiso 1 1 calc R U . . .
C20 C 1.0219(5) 1.2336(4) 0.2799(2) 0.0398(9) Uani 1 1 d . . . . .
C21 C 1.1189(5) 1.1533(4) 0.2379(2) 0.0378(8) Uani 1 1 d . . . . .
C22 C 1.2832(6) 1.2116(4) 0.2071(2) 0.0462(10) Uani 1 1 d . . . . .
C23 C 1.5277(7) 1.1657(6) 0.1412(3) 0.0715(15) Uani 1 1 d . . . . .
H23A H 1.6154 1.2289 0.1783 0.086 Uiso 1 1 calc R U . . .
H23B H 1.5027 1.2148 0.1054 0.086 Uiso 1 1 calc R U . . .
C24 C 1.5993(8) 1.0466(7) 0.1067(4) 0.095(2) Uani 1 1 d . . . . .
H24A H 1.6348 1.0040 0.1432 0.142 Uiso 1 1 calc R U . . .
H24B H 1.7016 1.0776 0.0814 0.142 Uiso 1 1 calc R U . . .
H24C H 1.5081 0.9809 0.0731 0.142 Uiso 1 1 calc R U . . .
C25 C 1.0341(5) 1.0113(3) 0.23615(18) 0.0332(8) Uani 1 1 d . . . . .
C26 C 0.8877(5) 1.0111(3) 0.27609(19) 0.0331(8) Uani 1 1 d . . . . .
C27 C 0.7786(5) 0.8918(4) 0.2982(2) 0.0381(8) Uani 1 1 d . . . . .
C28 C 0.6997(6) 0.7720(4) 0.2464(2) 0.0477(10) Uani 1 1 d . . . . .
H28 H 0.7042 0.7713 0.1975 0.057 Uiso 1 1 calc R U . . .
C29 C 0.6140(7) 0.6530(4) 0.2673(3) 0.0655(14) Uani 1 1 d . . . . .
H29 H 0.5625 0.5732 0.2323 0.079 Uiso 1 1 calc R U . . .
C30 C 0.6049(7) 0.6524(5) 0.3387(4) 0.0759(17) Uani 1 1 d . . . . .
H30 H 0.5479 0.5725 0.3524 0.091 Uiso 1 1 calc R U . . .
C31 C 0.6812(7) 0.7718(6) 0.3908(3) 0.0740(15) Uani 1 1 d . . . . .
H31 H 0.6766 0.7717 0.4396 0.089 Uiso 1 1 calc R U . . .
C32 C 0.7640(6) 0.8909(5) 0.3706(2) 0.0517(11) Uani 1 1 d . . . . .
H32 H 0.8105 0.9713 0.4060 0.062 Uiso 1 1 calc R U . . .
N1 N 1.1706(5) 0.7394(3) 0.09763(17) 0.0422(8) Uani 1 1 d . . . . .
H1 H 1.2292 0.7059 0.1257 0.051 Uiso 1 1 calc R U . . .
N2 N 0.8803(4) 1.1490(3) 0.30341(16) 0.0364(7) Uani 1 1 d . . . . .
O1 O 1.2080(5) 0.7011(3) 0.22931(15) 0.0590(9) Uani 1 1 d . . . . .
O2 O 1.1639(4) 0.8668(3) 0.32066(13) 0.0437(7) Uani 1 1 d . . . . .
O3 O 1.3407(5) 1.3328(3) 0.2106(2) 0.0795(11) Uani 1 1 d . . . . .
O4 O 1.3647(4) 1.1156(3) 0.17322(16) 0.0514(7) Uani 1 1 d . . . . .
S1 S 0.87188(16) 0.78912(12) 0.00889(6) 0.0534(3) Uani 1 1 d . . . . .
S2 S 1.01764(17) 1.42926(11) 0.40020(6) 0.0560(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 1.381(6) . ?
C1 C6 1.384(6) . ?
C1 N1 1.413(5) . ?
C2 C3 1.389(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(6) . ?
C5 H5 0.9300 . ?
C6 S1 1.765(4) . ?
C7 C8 1.497(5) . ?
C7 S1 1.816(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.345(5) . ?
C8 C9 1.365(5) . ?
C9 C10 1.455(5) . ?
C9 C25 1.486(5) . ?
C10 O1 1.221(4) . ?
C10 O2 1.343(4) . ?
C11 O2 1.434(5) . ?
C11 C12 1.477(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.383(5) . ?
C13 C18 1.402(5) . ?
C13 N2 1.420(5) . ?
C14 C15 1.385(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(6) . ?
C17 H17 0.9300 . ?
C18 S2 1.761(4) . ?
C19 C20 1.489(5) . ?
C19 S2 1.813(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.371(5) . ?
C20 N2 1.379(5) . ?
C21 C25 1.443(5) . ?
C21 C22 1.463(5) . ?
C22 O3 1.205(5) . ?
C22 O4 1.336(5) . ?
C23 O4 1.444(5) . ?
C23 C24 1.477(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.372(5) . ?
C26 N2 1.405(4) . ?
C26 C27 1.467(5) . ?
C27 C32 1.385(5) . ?
C27 C28 1.392(5) . ?
C28 C29 1.393(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.361(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.387(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(6) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.8(4) . . ?
C2 C1 N1 119.0(4) . . ?
C6 C1 N1 121.2(4) . . ?
C1 C2 C3 120.4(5) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 S1 119.6(3) . . ?
C5 C6 S1 121.3(4) . . ?
C8 C7 S1 109.8(3) . . ?
C8 C7 H7A 109.7 . . ?
S1 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
S1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C9 123.3(3) . . ?
N1 C8 C7 114.8(3) . . ?
C9 C8 C7 121.8(3) . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 C25 121.1(3) . . ?
C10 C9 C25 119.2(3) . . ?
O1 C10 O2 121.0(3) . . ?
O1 C10 C9 125.5(3) . . ?
O2 C10 C9 113.5(3) . . ?
O2 C11 C12 109.5(4) . . ?
O2 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
O2 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.8(4) . . ?
C14 C13 N2 121.7(3) . . ?
C18 C13 N2 118.5(3) . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.9(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 119.0(4) . . ?
C17 C18 S2 120.6(3) . . ?
C13 C18 S2 120.3(3) . . ?
C20 C19 S2 108.7(3) . . ?
C20 C19 H19A 110.0 . . ?
S2 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
S2 C19 H19B 110.0 . . ?
H19A C19 H19B 108.3 . . ?
C21 C20 N2 108.9(3) . . ?
C21 C20 C19 132.0(4) . . ?
N2 C20 C19 119.1(4) . . ?
C20 C21 C25 107.1(3) . . ?
C20 C21 C22 122.7(3) . . ?
C25 C21 C22 130.1(3) . . ?
O3 C22 O4 122.4(4) . . ?
O3 C22 C21 124.7(4) . . ?
O4 C22 C21 112.9(3) . . ?
O4 C23 C24 108.6(4) . . ?
O4 C23 H23A 110.0 . . ?
C24 C23 H23A 110.0 . . ?
O4 C23 H23B 110.0 . . ?
C24 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C21 107.6(3) . . ?
C26 C25 C9 124.5(3) . . ?
C21 C25 C9 127.8(3) . . ?
C25 C26 N2 107.8(3) . . ?
C25 C26 C27 126.2(3) . . ?
N2 C26 C27 125.0(3) . . ?
C32 C27 C28 118.4(4) . . ?
C32 C27 C26 121.4(3) . . ?
C28 C27 C26 120.0(3) . . ?
C27 C28 C29 120.4(4) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 120.6(5) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.4(4) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C32 C31 C30 120.4(5) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C27 120.7(4) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?
C8 N1 C1 126.9(3) . . ?
C8 N1 H1 116.6 . . ?
C1 N1 H1 116.6 . . ?
C20 N2 C26 108.6(3) . . ?
C20 N2 C13 123.1(3) . . ?
C26 N2 C13 128.1(3) . . ?
C10 O2 C11 116.5(3) . . ?
C22 O4 C23 116.0(3) . . ?
C6 S1 C7 96.3(2) . . ?
C18 S2 C19 95.6(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
N1 H1 O1 0.86 1.99 2.636(4) 130.8 .

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.064


