# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2101306'
loop_
_audit_author_name
_audit_author_address
M-MeO
;Shaanxi Normal University
China
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 O2 S'
_chemical_formula_sum            'C21 H16 N2 O2 S'
_chemical_formula_weight         360.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   27.4596(18)
_cell_length_b                   11.0411(7)
_cell_length_c                   5.5352(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1678.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8456
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      60.510
_cell_measurement_theta_min      2.800
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    1.218
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0838 after correction.
The Ratio of minimum to maximum transmission is 0.8315.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16088
_diffrn_reflns_point_group_measured_fraction_full 0.857
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.577
_diffrn_reflns_theta_min         2.800
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.678
_reflns_Friedel_fraction_max     0.628
_reflns_number_gt                2912
_reflns_number_total             3191
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 933 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.1013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0739
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C7(H7), C3(H3), C10(H10), C20(H20), C13(H13), C12(H12),
 C17(H17), C11(H11), C14(H14), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42826(2) 0.71931(4) 1.15264(12) 0.03190(14) Uani 1 1 d . . . . .
O1 O 0.47519(6) 0.15070(12) 0.8716(3) 0.0324(4) Uani 1 1 d . . . . .
O2 O 0.34847(6) 0.29967(12) 0.3413(4) 0.0417(4) Uani 1 1 d . . . . .
N2 N 0.37496(6) 0.47141(14) 0.5302(4) 0.0259(4) Uani 1 1 d . . . . .
H2 H 0.371906 0.550729 0.526607 0.031 Uiso 1 1 calc R U . . .
N1 N 0.37950(6) 0.68789(15) 0.7571(3) 0.0276(4) Uani 1 1 d . . . . .
C6 C 0.40737(7) 0.42634(16) 0.7034(4) 0.0238(4) Uani 1 1 d . . . . .
C5 C 0.42416(7) 0.50497(17) 0.8875(4) 0.0241(4) Uani 1 1 d . . . . .
C15 C 0.40827(7) 0.63200(17) 0.9072(4) 0.0247(4) Uani 1 1 d . . . . .
C9 C 0.31524(7) 0.48696(16) 0.2101(4) 0.0249(4) Uani 1 1 d . . . . .
C8 C 0.34747(7) 0.40973(17) 0.3661(4) 0.0268(4) Uani 1 1 d . . . . .
C4 C 0.45660(7) 0.45888(18) 1.0590(4) 0.0286(5) Uani 1 1 d . . . . .
H4 H 0.467932 0.510761 1.183849 0.034 Uiso 1 1 calc R U . . .
C16 C 0.37062(7) 0.80591(17) 0.8322(4) 0.0269(4) Uani 1 1 d . . . . .
C7 C 0.42394(7) 0.30621(17) 0.6952(4) 0.0269(5) Uani 1 1 d . . . . .
H7 H 0.413061 0.253251 0.571131 0.032 Uiso 1 1 calc R U . . .
C3 C 0.47267(8) 0.34086(18) 1.0531(5) 0.0297(4) Uani 1 1 d . . . . .
H3 H 0.494545 0.311517 1.172492 0.036 Uiso 1 1 calc R U . . .
C10 C 0.30435(8) 0.60762(18) 0.2613(4) 0.0292(5) Uani 1 1 d . . . . .
H10 H 0.317237 0.644597 0.402508 0.035 Uiso 1 1 calc R U . . .
C21 C 0.39455(7) 0.83957(17) 1.0443(4) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.45630(7) 0.26533(16) 0.8692(4) 0.0266(4) Uani 1 1 d . . . . .
C20 C 0.38873(8) 0.95512(17) 1.1435(6) 0.0359(5) Uani 1 1 d . . . . .
H20 H 0.405072 0.977496 1.288063 0.043 Uiso 1 1 calc R U . . .
C13 C 0.26625(8) 0.50139(19) -0.1508(5) 0.0334(5) Uani 1 1 d . . . . .
H13 H 0.253217 0.464921 -0.292177 0.040 Uiso 1 1 calc R U . . .
C12 C 0.25590(8) 0.62098(19) -0.0987(5) 0.0340(5) Uani 1 1 d . . . . .
H12 H 0.235814 0.666846 -0.204382 0.041 Uiso 1 1 calc R U . . .
C17 C 0.34032(8) 0.88895(18) 0.7143(5) 0.0353(5) Uani 1 1 d . . . . .
H17 H 0.324082 0.867775 0.568790 0.042 Uiso 1 1 calc R U . . .
C11 C 0.27479(8) 0.67384(18) 0.1072(5) 0.0339(5) Uani 1 1 d . . . . .
H11 H 0.267493 0.755971 0.143285 0.041 Uiso 1 1 calc R U . . .
C14 C 0.29568(8) 0.43444(18) 0.0033(4) 0.0300(5) Uani 1 1 d . . . . .
H14 H 0.302528 0.352066 -0.032831 0.036 Uiso 1 1 calc R U . . .
C18 C 0.33462(9) 1.00264(19) 0.8153(5) 0.0391(6) Uani 1 1 d . . . . .
H18 H 0.313762 1.059499 0.738607 0.047 Uiso 1 1 calc R U . . .
C1 C 0.46483(8) 0.07523(18) 0.6689(6) 0.0375(5) Uani 1 1 d . . . . .
H1A H 0.483155 -0.000589 0.683107 0.056 Uiso 1 1 calc R U . . .
H1B H 0.474323 0.117051 0.519993 0.056 Uiso 1 1 calc R U . . .
H1C H 0.429878 0.057395 0.664267 0.056 Uiso 1 1 calc R U . . .
C19 C 0.35860(9) 1.03570(19) 1.0256(5) 0.0392(6) Uani 1 1 d . . . . .
H19 H 0.354226 1.114854 1.089291 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.754(2) . ?
S1 C21 1.726(2) . ?
O1 C2 1.368(2) . ?
O1 C1 1.426(3) . ?
O2 C8 1.223(2) . ?
N2 H2 0.8800 . ?
N2 C6 1.400(3) . ?
N2 C8 1.363(3) . ?
N1 C15 1.302(3) . ?
N1 C16 1.389(3) . ?
C6 C5 1.416(3) . ?
C6 C7 1.403(2) . ?
C5 C15 1.473(3) . ?
C5 C4 1.398(3) . ?
C9 C8 1.502(3) . ?
C9 C10 1.395(3) . ?
C9 C14 1.391(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.376(3) . ?
C16 C21 1.396(3) . ?
C16 C17 1.400(3) . ?
C7 H7 0.9500 . ?
C7 C2 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.391(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C21 C20 1.398(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.381(3) . ?
C13 C14 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.382(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(3) . ?
C11 H11 0.9500 . ?
C14 H14 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.386(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 S1 C15 89.18(10) . . ?
C2 O1 C1 117.19(17) . . ?
C6 N2 H2 115.4 . . ?
C8 N2 H2 115.4 . . ?
C8 N2 C6 129.11(16) . . ?
C15 N1 C16 111.12(18) . . ?
N2 C6 C5 118.83(16) . . ?
N2 C6 C7 121.33(19) . . ?
C7 C6 C5 119.84(19) . . ?
C6 C5 C15 122.73(19) . . ?
C4 C5 C6 118.23(17) . . ?
C4 C5 C15 119.03(19) . . ?
N1 C15 S1 115.07(15) . . ?
N1 C15 C5 125.7(2) . . ?
C5 C15 S1 119.20(16) . . ?
C10 C9 C8 123.49(19) . . ?
C14 C9 C8 117.65(17) . . ?
C14 C9 C10 118.86(19) . . ?
O2 C8 N2 123.98(19) . . ?
O2 C8 C9 120.83(19) . . ?
N2 C8 C9 115.19(16) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 C5 122.2(2) . . ?
C3 C4 H4 118.9 . . ?
N1 C16 C21 114.76(18) . . ?
N1 C16 C17 125.4(2) . . ?
C21 C16 C17 119.83(19) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 C6 119.6(2) . . ?
C2 C7 H7 120.2 . . ?
C4 C3 H3 120.6 . . ?
C4 C3 C2 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C16 C21 S1 109.87(15) . . ?
C16 C21 C20 121.3(2) . . ?
C20 C21 S1 128.81(19) . . ?
O1 C2 C7 123.46(19) . . ?
O1 C2 C3 115.15(19) . . ?
C7 C2 C3 121.38(17) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 C21 118.1(2) . . ?
C19 C20 H20 120.9 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 H17 120.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.33(19) . . ?
C12 C11 H11 119.8 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.56(19) . . ?
C13 C14 H14 119.7 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.6(2) . . ?
C19 C18 H18 119.2 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?

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
S1 C21 C20 C19 -178.3(2) . . . . ?
N2 C6 C5 C15 1.1(3) . . . . ?
N2 C6 C5 C4 -179.85(18) . . . . ?
N2 C6 C7 C2 179.53(19) . . . . ?
N1 C16 C21 S1 -0.7(2) . . . . ?
N1 C16 C21 C20 -179.3(2) . . . . ?
N1 C16 C17 C18 178.8(2) . . . . ?
C6 N2 C8 O2 -2.4(4) . . . . ?
C6 N2 C8 C9 178.3(2) . . . . ?
C6 C5 C15 S1 176.07(15) . . . . ?
C6 C5 C15 N1 -3.2(3) . . . . ?
C6 C5 C4 C3 0.4(3) . . . . ?
C6 C7 C2 O1 -178.41(19) . . . . ?
C6 C7 C2 C3 0.2(3) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?
C15 S1 C21 C16 0.10(17) . . . . ?
C15 S1 C21 C20 178.5(2) . . . . ?
C15 N1 C16 C21 1.2(3) . . . . ?
C15 N1 C16 C17 -178.4(2) . . . . ?
C15 C5 C4 C3 179.4(2) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C8 N2 C6 C5 -166.9(2) . . . . ?
C8 N2 C6 C7 14.2(3) . . . . ?
C8 C9 C10 C11 179.2(2) . . . . ?
C8 C9 C14 C13 -178.9(2) . . . . ?
C4 C5 C15 S1 -2.9(3) . . . . ?
C4 C5 C15 N1 177.8(2) . . . . ?
C4 C3 C2 O1 177.97(19) . . . . ?
C4 C3 C2 C7 -0.8(3) . . . . ?
C16 N1 C15 S1 -1.1(2) . . . . ?
C16 N1 C15 C5 178.17(19) . . . . ?
C16 C21 C20 C19 -0.1(3) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C7 C6 C5 C15 -179.94(19) . . . . ?
C7 C6 C5 C4 -0.9(3) . . . . ?
C10 C9 C8 O2 165.7(2) . . . . ?
C10 C9 C8 N2 -15.0(3) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C21 S1 C15 N1 0.60(18) . . . . ?
C21 S1 C15 C5 -178.73(17) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?
C21 C20 C19 C18 0.3(4) . . . . ?
C13 C12 C11 C10 0.4(4) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C17 C16 C21 S1 178.88(18) . . . . ?
C17 C16 C21 C20 0.3(3) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C14 C9 C8 O2 -14.7(3) . . . . ?
C14 C9 C8 N2 164.57(19) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C14 C13 C12 C11 -0.1(4) . . . . ?
C1 O1 C2 C7 7.1(3) . . . . ?
C1 O1 C2 C3 -171.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2101308'
loop_
_audit_author_name
_audit_author_address
M-Me
;Shaanxi Normal University
China
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 O S'
_chemical_formula_sum            'C21 H16 N2 O S'
_chemical_formula_weight         344.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0592(8)
_cell_length_b                   18.9863(12)
_cell_length_c                   7.3256(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.779(3)
_cell_angle_gamma                90
_cell_volume                     1629.00(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      62.610
_cell_measurement_theta_min      3.858
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    1.207
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.5542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1409 before and 0.0763 after correction.
The Ratio of minimum to maximum transmission is 0.7367.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13065
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         63.327
_diffrn_reflns_theta_min         3.858
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3034
_reflns_number_total             3901
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.4904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1264
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C3(H3), C9(H9), C17(H17), C2(H2A), C4(H4), C18(H18),
 C12(H12), C19(H19), C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.48425(4) 0.65906(2) 0.57203(6) 0.03099(14) Uani 1 1 d . . . . .
O1 O 0.52451(11) 0.32493(7) 0.9341(2) 0.0408(3) Uani 1 1 d . . . . .
N2 N 0.47531(12) 0.43618(8) 0.8248(2) 0.0296(3) Uani 1 1 d . . . . .
H2 H 0.420358 0.467298 0.817619 0.036 Uiso 1 1 d R U . . .
N1 N 0.37886(13) 0.55959(8) 0.7036(2) 0.0299(3) Uani 1 1 d . . . . .
C15 C 0.45291(15) 0.37050(9) 0.8824(2) 0.0292(4) Uani 1 1 d . . . . .
C6 C 0.29921(15) 0.61191(9) 0.6399(2) 0.0285(4) Uani 1 1 d . . . . .
C8 C 0.58109(15) 0.53224(9) 0.7281(2) 0.0281(4) Uani 1 1 d . . . . .
C7 C 0.47891(15) 0.57656(9) 0.6763(2) 0.0284(4) Uani 1 1 d . . . . .
C14 C 0.57985(15) 0.46320(9) 0.8026(2) 0.0285(4) Uani 1 1 d . . . . .
C16 C 0.32979(15) 0.35712(9) 0.8812(2) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.34055(15) 0.66990(9) 0.5587(2) 0.0294(4) Uani 1 1 d . . . . .
C13 C 0.68131(16) 0.42514(10) 0.8493(3) 0.0346(4) Uani 1 1 d . . . . .
H13 H 0.681561 0.379118 0.900350 0.042 Uiso 1 1 calc R U . . .
C5 C 0.18481(16) 0.60950(10) 0.6482(3) 0.0346(4) Uani 1 1 d . . . . .
H5 H 0.156186 0.570875 0.705525 0.042 Uiso 1 1 calc R U . . .
C3 C 0.15582(17) 0.72116(10) 0.4851(3) 0.0366(4) Uani 1 1 d . . . . .
H3 H 0.105119 0.757888 0.430806 0.044 Uiso 1 1 calc R U . . .
C9 C 0.68506(15) 0.55876(10) 0.7038(2) 0.0313(4) Uani 1 1 d . . . . .
H9 H 0.686421 0.604800 0.653646 0.038 Uiso 1 1 calc R U . . .
C10 C 0.78564(16) 0.52087(10) 0.7497(3) 0.0344(4) Uani 1 1 d . . . . .
C17 C 0.24022(17) 0.39928(10) 0.7867(3) 0.0354(4) Uani 1 1 d . . . . .
H17 H 0.255219 0.439085 0.717782 0.042 Uiso 1 1 calc R U . . .
C2 C 0.26855(16) 0.72480(10) 0.4775(3) 0.0333(4) Uani 1 1 d . . . . .
H2A H 0.296464 0.763388 0.419041 0.040 Uiso 1 1 calc R U . . .
C4 C 0.11430(16) 0.66444(10) 0.5712(3) 0.0366(4) Uani 1 1 d . . . . .
H4 H 0.036383 0.663782 0.576676 0.044 Uiso 1 1 calc R U . . .
C18 C 0.12878(17) 0.38332(11) 0.7929(3) 0.0410(5) Uani 1 1 d . . . . .
H18 H 0.067827 0.412518 0.729121 0.049 Uiso 1 1 calc R U . . .
C12 C 0.78160(16) 0.45353(10) 0.8223(3) 0.0362(4) Uani 1 1 d . . . . .
H12 H 0.849605 0.426332 0.854148 0.043 Uiso 1 1 calc R U . . .
C19 C 0.10619(18) 0.32508(12) 0.8916(3) 0.0429(5) Uani 1 1 d . . . . .
H19 H 0.029798 0.314092 0.894694 0.051 Uiso 1 1 calc R U . . .
C21 C 0.30622(17) 0.29849(10) 0.9800(3) 0.0343(4) Uani 1 1 d . . . . .
H21 H 0.366824 0.269051 1.043891 0.041 Uiso 1 1 calc R U . . .
C20 C 0.19486(18) 0.28293(11) 0.9857(3) 0.0402(5) Uani 1 1 d . . . . .
H20 H 0.179435 0.243167 1.054371 0.048 Uiso 1 1 calc R U . . .
C11 C 0.89576(17) 0.55100(12) 0.7208(3) 0.0456(5) Uani 1 1 d . . . . .
H11A H 0.918170 0.525631 0.618686 0.068 Uiso 1 1 calc R U . . .
H11B H 0.955653 0.545967 0.836741 0.068 Uiso 1 1 calc R U . . .
H11C H 0.885073 0.600991 0.688022 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.7504(18) . ?
S1 C1 1.7247(18) . ?
O1 C15 1.217(2) . ?
N2 H2 0.8800 . ?
N2 C15 1.364(2) . ?
N2 C14 1.406(2) . ?
N1 C6 1.383(2) . ?
N1 C7 1.310(2) . ?
C15 C16 1.504(2) . ?
C6 C1 1.398(2) . ?
C6 C5 1.396(2) . ?
C8 C7 1.465(3) . ?
C8 C14 1.421(2) . ?
C8 C9 1.401(2) . ?
C14 C13 1.392(3) . ?
C16 C17 1.389(3) . ?
C16 C21 1.394(2) . ?
C1 C2 1.396(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.375(3) . ?
C3 C4 1.400(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(3) . ?
C10 C12 1.390(3) . ?
C10 C11 1.507(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C2 H2A 0.9500 . ?
C4 H4 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.383(3) . ?
C12 H12 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.381(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.385(3) . ?
C20 H20 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C7 89.46(8) . . ?
C15 N2 H2 115.5 . . ?
C15 N2 C14 128.20(15) . . ?
C14 N2 H2 115.5 . . ?
C7 N1 C6 111.26(14) . . ?
O1 C15 N2 124.62(16) . . ?
O1 C15 C16 120.51(16) . . ?
N2 C15 C16 114.86(15) . . ?
N1 C6 C1 114.81(15) . . ?
N1 C6 C5 125.16(16) . . ?
C5 C6 C1 120.02(17) . . ?
C14 C8 C7 122.96(16) . . ?
C9 C8 C7 118.90(16) . . ?
C9 C8 C14 118.14(16) . . ?
N1 C7 S1 114.70(13) . . ?
N1 C7 C8 124.57(16) . . ?
C8 C7 S1 120.72(13) . . ?
N2 C14 C8 118.21(16) . . ?
C13 C14 N2 122.82(16) . . ?
C13 C14 C8 118.97(16) . . ?
C17 C16 C15 123.69(16) . . ?
C17 C16 C21 119.24(17) . . ?
C21 C16 C15 117.07(16) . . ?
C6 C1 S1 109.71(13) . . ?
C2 C1 S1 128.90(14) . . ?
C2 C1 C6 121.37(16) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.71(18) . . ?
C12 C13 H13 119.6 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.50(17) . . ?
C4 C5 H5 120.8 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.33(18) . . ?
C4 C3 H3 119.3 . . ?
C8 C9 H9 118.6 . . ?
C10 C9 C8 122.85(17) . . ?
C10 C9 H9 118.6 . . ?
C9 C10 C12 117.60(17) . . ?
C9 C10 C11 121.36(18) . . ?
C12 C10 C11 121.03(18) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.10(18) . . ?
C18 C17 H17 120.0 . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 C1 117.76(17) . . ?
C3 C2 H2A 121.1 . . ?
C5 C4 C3 120.96(17) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.27(19) . . ?
C19 C18 H18 119.9 . . ?
C13 C12 C10 121.72(18) . . ?
C13 C12 H12 119.1 . . ?
C10 C12 H12 119.1 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.89(19) . . ?
C20 C19 H19 120.1 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.33(18) . . ?
C20 C21 H21 119.8 . . ?
C19 C20 C21 120.17(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 179.92(15) . . . . ?
O1 C15 C16 C17 -165.04(18) . . . . ?
O1 C15 C16 C21 14.4(2) . . . . ?
N2 C15 C16 C17 15.8(2) . . . . ?
N2 C15 C16 C21 -164.77(16) . . . . ?
N2 C14 C13 C12 178.99(17) . . . . ?
N1 C6 C1 S1 -2.34(19) . . . . ?
N1 C6 C1 C2 175.95(16) . . . . ?
N1 C6 C5 C4 -177.13(17) . . . . ?
C15 N2 C14 C8 175.76(16) . . . . ?
C15 N2 C14 C13 -3.8(3) . . . . ?
C15 C16 C17 C18 -179.92(17) . . . . ?
C15 C16 C21 C20 179.84(16) . . . . ?
C6 N1 C7 S1 0.72(19) . . . . ?
C6 N1 C7 C8 -179.92(15) . . . . ?
C6 C1 C2 C3 2.0(3) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C8 C14 C13 C12 -0.6(3) . . . . ?
C8 C9 C10 C12 0.2(3) . . . . ?
C8 C9 C10 C11 179.70(17) . . . . ?
C7 S1 C1 C6 2.19(13) . . . . ?
C7 S1 C1 C2 -175.93(18) . . . . ?
C7 N1 C6 C1 1.1(2) . . . . ?
C7 N1 C6 C5 179.69(16) . . . . ?
C7 C8 C14 N2 0.9(2) . . . . ?
C7 C8 C14 C13 -179.49(16) . . . . ?
C7 C8 C9 C10 179.67(16) . . . . ?
C14 N2 C15 O1 4.0(3) . . . . ?
C14 N2 C15 C16 -176.87(15) . . . . ?
C14 C8 C7 S1 -176.13(13) . . . . ?
C14 C8 C7 N1 4.5(3) . . . . ?
C14 C8 C9 C10 -0.2(3) . . . . ?
C14 C13 C12 C10 0.6(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C16 C21 C20 C19 0.7(3) . . . . ?
C1 S1 C7 N1 -1.75(14) . . . . ?
C1 S1 C7 C8 178.86(14) . . . . ?
C1 C6 C5 C4 1.4(3) . . . . ?
C5 C6 C1 S1 178.97(14) . . . . ?
C5 C6 C1 C2 -2.7(3) . . . . ?
C9 C8 C7 S1 4.0(2) . . . . ?
C9 C8 C7 N1 -175.35(16) . . . . ?
C9 C8 C14 N2 -179.20(15) . . . . ?
C9 C8 C14 C13 0.4(2) . . . . ?
C9 C10 C12 C13 -0.4(3) . . . . ?
C17 C16 C21 C20 -0.7(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C4 C3 C2 C1 0.0(3) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
C11 C10 C12 C13 -179.88(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2101307'
loop_
_audit_author_name
_audit_author_address
M-CN
;Shaanxi Normal University
China
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-04-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 N3 O S'
_chemical_formula_sum            'C21 H13 N3 O S'
_chemical_formula_weight         355.40
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5048(7)
_cell_length_b                   18.8823(10)
_cell_length_c                   7.2768(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.626(2)
_cell_angle_gamma                90
_cell_volume                     1646.36(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5108
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.449
_cell_measurement_theta_min      2.157
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1324 before and 0.0774 after correction.
The Ratio of minimum to maximum transmission is 0.8953.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15162
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.013
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3043
_reflns_number_total             3788
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.5598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1256
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C13(H13), C17(H17), C10(H10), C4(H4), C21(H21), C12(H12),
 C11(H11), C20(H20), C3(H3A), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.48327(4) 0.66150(2) 0.57074(7) 0.02299(14) Uani 1 1 d . . . . .
O1 O 0.51823(11) 0.32507(7) 0.9342(2) 0.0320(3) Uani 1 1 d . . . . .
N3 N 0.47179(12) 0.43687(7) 0.8174(2) 0.0218(3) Uani 1 1 d . . . . .
H3 H 0.416244 0.465605 0.783693 0.026 Uiso 1 1 calc R U . . .
N2 N 0.37957(13) 0.56108(7) 0.6914(2) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.57638(15) 0.53269(9) 0.7312(3) 0.0204(4) Uani 1 1 d . . . . .
C14 C 0.30198(15) 0.61424(9) 0.6245(3) 0.0210(4) Uani 1 1 d . . . . .
C9 C 0.34309(15) 0.67344(9) 0.5484(3) 0.0213(4) Uani 1 1 d . . . . .
C16 C 0.32835(15) 0.35888(9) 0.8679(3) 0.0217(4) Uani 1 1 d . . . . .
C15 C 0.44848(15) 0.37099(9) 0.8765(3) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.57333(15) 0.46318(9) 0.8050(3) 0.0207(4) Uani 1 1 d . . . . .
C8 C 0.47712(15) 0.57820(9) 0.6719(3) 0.0202(4) Uani 1 1 d . . . . .
C7 C 0.67804(15) 0.55861(10) 0.7158(3) 0.0236(4) Uani 1 1 d . . . . .
H7 H 0.680796 0.603696 0.665967 0.028 Uiso 1 1 calc R U . . .
C13 C 0.19077(15) 0.61231(9) 0.6263(3) 0.0255(4) Uani 1 1 d . . . . .
H13 H 0.163193 0.573797 0.678146 0.031 Uiso 1 1 calc R U . . .
C2 C 0.77486(16) 0.51873(10) 0.7732(3) 0.0268(4) Uani 1 1 d . . . . .
C17 C 0.30533(17) 0.30032(9) 0.9663(3) 0.0268(4) Uani 1 1 d . . . . .
H17 H 0.362979 0.270386 1.030612 0.032 Uiso 1 1 calc R U . . .
C10 C 0.27320(16) 0.72942(10) 0.4668(3) 0.0252(4) Uani 1 1 d . . . . .
H10 H 0.299817 0.767741 0.412633 0.030 Uiso 1 1 calc R U . . .
C4 C 0.67209(16) 0.42377(10) 0.8614(3) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.670514 0.378328 0.909800 0.033 Uiso 1 1 calc R U . . .
C21 C 0.24126(16) 0.40278(10) 0.7706(3) 0.0275(4) Uani 1 1 d . . . . .
H21 H 0.255705 0.441747 0.703292 0.033 Uiso 1 1 calc R U . . .
C12 C 0.12274(16) 0.66857(10) 0.5496(3) 0.0276(4) Uani 1 1 d . . . . .
H12 H 0.048688 0.668278 0.551477 0.033 Uiso 1 1 calc R U . . .
C11 C 0.16337(16) 0.72641(10) 0.4686(3) 0.0284(4) Uani 1 1 d . . . . .
H11 H 0.115345 0.763365 0.415202 0.034 Uiso 1 1 calc R U . . .
C20 C 0.13299(17) 0.38870(11) 0.7736(3) 0.0344(5) Uani 1 1 d . . . . .
H20 H 0.075001 0.418178 0.708170 0.041 Uiso 1 1 calc R U . . .
C3 C 0.77135(17) 0.45077(10) 0.8467(3) 0.0297(4) Uani 1 1 d . . . . .
H3A H 0.836135 0.423789 0.885750 0.036 Uiso 1 1 calc R U . . .
C18 C 0.19717(18) 0.28634(11) 0.9692(3) 0.0326(5) Uani 1 1 d . . . . .
H18 H 0.182343 0.247069 1.035059 0.039 Uiso 1 1 calc R U . . .
C19 C 0.11100(18) 0.33078(11) 0.8741(3) 0.0358(5) Uani 1 1 d . . . . .
H19 H 0.038484 0.321772 0.877533 0.043 Uiso 1 1 calc R U . . .
N1 N 0.96270(17) 0.56795(13) 0.7489(4) 0.0572(6) Uani 1 1 d . . . . .
C1 C 0.87914(18) 0.54667(12) 0.7589(3) 0.0362(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.7283(18) . ?
S1 C8 1.7475(17) . ?
O1 C15 1.216(2) . ?
N3 H3 0.8600 . ?
N3 C15 1.374(2) . ?
N3 C5 1.390(2) . ?
N2 C14 1.384(2) . ?
N2 C8 1.308(2) . ?
C6 C5 1.423(2) . ?
C6 C8 1.469(2) . ?
C6 C7 1.396(2) . ?
C14 C9 1.409(2) . ?
C14 C13 1.395(2) . ?
C9 C10 1.392(3) . ?
C16 C15 1.503(2) . ?
C16 C17 1.392(2) . ?
C16 C21 1.390(3) . ?
C5 C4 1.399(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.385(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.375(3) . ?
C2 C3 1.396(3) . ?
C2 C1 1.438(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.374(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.404(3) . ?
C11 H11 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.386(3) . ?
C3 H3A 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.385(3) . ?
C19 H19 0.9300 . ?
N1 C1 1.141(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
C9 S1 C8 89.51(8) . . ?
C15 N3 H3 115.7 . . ?
C15 N3 C5 128.55(15) . . ?
C5 N3 H3 115.7 . . ?
C8 N2 C14 111.36(14) . . ?
C5 C6 C8 122.59(15) . . ?
C7 C6 C5 118.49(16) . . ?
C7 C6 C8 118.92(16) . . ?
N2 C14 C9 114.57(15) . . ?
N2 C14 C13 125.34(15) . . ?
C13 C14 C9 120.09(16) . . ?
C14 C9 S1 109.51(13) . . ?
C10 C9 S1 129.46(14) . . ?
C10 C9 C14 121.01(16) . . ?
C17 C16 C15 116.81(17) . . ?
C21 C16 C15 123.96(16) . . ?
C21 C16 C17 119.23(17) . . ?
O1 C15 N3 123.91(16) . . ?
O1 C15 C16 121.02(16) . . ?
N3 C15 C16 115.06(15) . . ?
N3 C5 C6 118.55(16) . . ?
N3 C5 C4 122.47(16) . . ?
C4 C5 C6 118.98(16) . . ?
N2 C8 S1 115.02(13) . . ?
N2 C8 C6 123.99(15) . . ?
C6 C8 S1 120.98(12) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 C6 121.53(17) . . ?
C2 C7 H7 119.2 . . ?
C14 C13 H13 120.7 . . ?
C12 C13 C14 118.60(16) . . ?
C12 C13 H13 120.7 . . ?
C7 C2 C3 119.65(17) . . ?
C7 C2 C1 120.77(18) . . ?
C3 C2 C1 119.59(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.41(19) . . ?
C18 C17 H17 119.8 . . ?
C9 C10 H10 121.0 . . ?
C11 C10 C9 118.07(16) . . ?
C11 C10 H10 121.0 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.42(18) . . ?
C3 C4 H4 119.3 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.27(18) . . ?
C20 C21 H21 119.9 . . ?
C13 C12 H12 119.5 . . ?
C13 C12 C11 121.01(18) . . ?
C11 C12 H12 119.5 . . ?
C10 C11 C12 121.16(18) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 119.9 . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 C2 119.94(18) . . ?
C4 C3 H3A 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.07(18) . . ?
C19 C18 H18 120.0 . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.89(19) . . ?
C18 C19 H19 120.1 . . ?
N1 C1 C2 179.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C9 C10 C11 -179.44(15) . . . . ?
N3 C5 C4 C3 179.60(17) . . . . ?
N2 C14 C9 S1 -2.0(2) . . . . ?
N2 C14 C9 C10 176.66(16) . . . . ?
N2 C14 C13 C12 -178.20(18) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
C6 C7 C2 C3 0.5(3) . . . . ?
C6 C7 C2 C1 -179.10(18) . . . . ?
C14 N2 C8 S1 0.4(2) . . . . ?
C14 N2 C8 C6 179.54(16) . . . . ?
C14 C9 C10 C11 2.2(3) . . . . ?
C14 C13 C12 C11 0.9(3) . . . . ?
C9 S1 C8 N2 -1.27(15) . . . . ?
C9 S1 C8 C6 179.52(15) . . . . ?
C9 C14 C13 C12 1.1(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C16 C21 C20 C19 0.1(3) . . . . ?
C15 N3 C5 C6 177.26(17) . . . . ?
C15 N3 C5 C4 -2.4(3) . . . . ?
C15 C16 C17 C18 178.53(17) . . . . ?
C15 C16 C21 C20 -178.47(17) . . . . ?
C5 N3 C15 O1 2.3(3) . . . . ?
C5 N3 C15 C16 -178.48(16) . . . . ?
C5 C6 C8 S1 -176.76(14) . . . . ?
C5 C6 C8 N2 4.1(3) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C8 S1 C9 C14 1.75(14) . . . . ?
C8 S1 C9 C10 -176.75(18) . . . . ?
C8 N2 C14 C9 1.1(2) . . . . ?
C8 N2 C14 C13 -179.63(18) . . . . ?
C8 C6 C5 N3 1.5(3) . . . . ?
C8 C6 C5 C4 -178.90(17) . . . . ?
C8 C6 C7 C2 178.65(17) . . . . ?
C7 C6 C5 N3 -178.95(16) . . . . ?
C7 C6 C5 C4 0.7(3) . . . . ?
C7 C6 C8 S1 3.7(2) . . . . ?
C7 C6 C8 N2 -175.49(17) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C13 C14 C9 S1 178.68(14) . . . . ?
C13 C14 C9 C10 -2.7(3) . . . . ?
C13 C12 C11 C10 -1.4(3) . . . . ?
C17 C16 C15 O1 13.7(3) . . . . ?
C17 C16 C15 N3 -165.49(16) . . . . ?
C17 C16 C21 C20 0.7(3) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C21 C16 C15 O1 -167.08(19) . . . . ?
C21 C16 C15 N3 13.7(3) . . . . ?
C21 C16 C17 C18 -0.7(3) . . . . ?
C21 C20 C19 C18 -0.9(3) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
