# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1963678'
loop_
_audit_author_name
_audit_author_address
'yun yu'
;wuhan university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_audit_creation_date             2019-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H14 N2 S)'
_chemical_formula_sum            'C40 H28 N4 S2'
_chemical_formula_weight         628.78
_chemical_absolute_configuration ?
_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'
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      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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   29.597(9)
_cell_length_b                   16.762(5)
_cell_length_c                   6.172(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3062.1(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2566
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      20.730
_cell_measurement_theta_min      2.396
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1553 before and 0.0756 after correction. The Ratio of minimum to maximum transmission is 0.6939. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            20084
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.591
_diffrn_reflns_theta_max         24.591
_diffrn_reflns_theta_min         1.376
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                3610
_reflns_number_total             5080
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1230 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5080
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.2756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1228
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C29(H29),
  C30(H30), C31(H31), C32(H32), C37(H37), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C40(H40A,H40B,H40C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.115
;
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 -0.26048(5) -0.29471(10) -0.3733(3) 0.0604(4) Uani 1 1 d . . . . .
N1 N -0.14770(13) -0.4200(2) -0.4720(7) 0.0395(10) Uani 1 1 d . . . . .
N2 N -0.20358(14) -0.4366(2) -0.2293(7) 0.0426(11) Uani 1 1 d . . . . .
C1 C -0.13272(15) -0.4760(3) -0.3206(9) 0.0393(12) Uani 1 1 d . . . . .
C2 C -0.09179(16) -0.5224(3) -0.3123(10) 0.0454(13) Uani 1 1 d . . . . .
C3 C -0.05630(19) -0.5187(3) -0.4619(12) 0.0632(17) Uani 1 1 d . . . . .
H3 H -0.0577 -0.4816 -0.5737 0.076 Uiso 1 1 calc R . . . .
C4 C -0.01938(19) -0.5685(4) -0.4481(14) 0.078(2) Uani 1 1 d . . . . .
H4 H 0.0039 -0.5655 -0.5492 0.093 Uiso 1 1 calc R . . . .
C5 C -0.0177(2) -0.6231(4) -0.2806(15) 0.081(2) Uani 1 1 d . . . . .
H5 H 0.0071 -0.6568 -0.2684 0.097 Uiso 1 1 calc R . . . .
C6 C -0.0515(2) -0.6282(3) -0.1341(13) 0.071(2) Uani 1 1 d . . . . .
H6 H -0.0494 -0.6663 -0.0251 0.085 Uiso 1 1 calc R . . . .
C7 C -0.08932(17) -0.5793(3) -0.1387(11) 0.0501(15) Uani 1 1 d . . . . .
C8 C -0.12581(17) -0.5864(3) 0.0216(10) 0.0480(14) Uani 1 1 d . . . . .
C9 C -0.1236(2) -0.6374(3) 0.2026(12) 0.0655(18) Uani 1 1 d . . . . .
H9 H -0.0980 -0.6688 0.2228 0.079 Uiso 1 1 calc R . . . .
C10 C -0.1581(3) -0.6420(4) 0.3495(12) 0.074(2) Uani 1 1 d . . . . .
H10 H -0.1557 -0.6768 0.4663 0.089 Uiso 1 1 calc R . . . .
C11 C -0.1962(2) -0.5960(3) 0.3269(10) 0.0623(17) Uani 1 1 d . . . . .
H11 H -0.2193 -0.5991 0.4288 0.075 Uiso 1 1 calc R . . . .
C12 C -0.20001(19) -0.5455(3) 0.1537(9) 0.0521(14) Uani 1 1 d . . . . .
H12 H -0.2260 -0.5151 0.1371 0.063 Uiso 1 1 calc R . . . .
C13 C -0.16522(18) -0.5391(3) 0.0012(9) 0.0434(13) Uani 1 1 d . . . . .
C14 C -0.16738(17) -0.4843(3) -0.1769(8) 0.0395(12) Uani 1 1 d . . . . .
C15 C -0.19065(15) -0.3998(3) -0.4092(9) 0.0372(12) Uani 1 1 d . . . . .
C16 C -0.22019(17) -0.3443(3) -0.5219(8) 0.0393(12) Uani 1 1 d . . . . .
C17 C -0.22372(18) -0.3239(3) -0.7347(9) 0.0494(14) Uani 1 1 d . . . . .
H17 H -0.2055 -0.3452 -0.8428 0.059 Uiso 1 1 calc R . . . .
C18 C -0.25798(19) -0.2670(3) -0.7744(11) 0.0590(16) Uani 1 1 d . . . . .
H18 H -0.2642 -0.2459 -0.9106 0.071 Uiso 1 1 calc R . . . .
C19 C -0.2806(2) -0.2466(4) -0.5944(11) 0.0612(17) Uani 1 1 d . . . . .
H19 H -0.3044 -0.2103 -0.5914 0.073 Uiso 1 1 calc R . . . .
C20 C -0.12204(17) -0.3816(3) -0.6440(9) 0.0479(14) Uani 1 1 d . . . . .
H20A H -0.0916 -0.3726 -0.5959 0.072 Uiso 1 1 calc GR . . . .
H20B H -0.1359 -0.3315 -0.6800 0.072 Uiso 1 1 calc GR . . . .
H20C H -0.1217 -0.4154 -0.7696 0.072 Uiso 1 1 calc GR . . . .
S2 S -0.10095(6) -0.85514(13) -0.2913(3) 0.0852(6) Uani 1 1 d . . . . .
N3 N 0.02567(14) -0.9015(2) -0.4432(7) 0.0432(11) Uani 1 1 d . . . . .
N4 N -0.00045(15) -0.8209(2) -0.1803(8) 0.0449(11) Uani 1 1 d . . . . .
C21 C 0.06194(16) -0.8867(3) -0.3040(9) 0.0424(12) Uani 1 1 d . . . . .
C22 C 0.10805(16) -0.9112(3) -0.3075(11) 0.0495(14) Uani 1 1 d . . . . .
C23 C 0.1282(2) -0.9561(3) -0.4706(13) 0.0668(18) Uani 1 1 d . . . . .
H23 H 0.1111 -0.9709 -0.5906 0.080 Uiso 1 1 calc R . . . .
C24 C 0.1730(2) -0.9793(4) -0.4587(16) 0.084(2) Uani 1 1 d . . . . .
H24 H 0.1856 -1.0113 -0.5657 0.100 Uiso 1 1 calc R . . . .
C25 C 0.1983(2) -0.9541(5) -0.2858(18) 0.094(3) Uani 1 1 d . . . . .
H25 H 0.2286 -0.9685 -0.2780 0.113 Uiso 1 1 calc R . . . .
C26 C 0.1805(2) -0.9093(4) -0.1281(15) 0.078(2) Uani 1 1 d . . . . .
H26 H 0.1987 -0.8945 -0.0119 0.094 Uiso 1 1 calc R . . . .
C27 C 0.13559(18) -0.8839(3) -0.1318(11) 0.0554(16) Uani 1 1 d . . . . .
C28 C 0.11754(18) -0.8302(3) 0.0328(10) 0.0515(15) Uani 1 1 d . . . . .
C29 C 0.1438(2) -0.7979(4) 0.2038(13) 0.0696(19) Uani 1 1 d . . . . .
H29 H 0.1741 -0.8118 0.2139 0.084 Uiso 1 1 calc R . . . .
C30 C 0.1265(3) -0.7482(4) 0.3507(13) 0.081(2) Uani 1 1 d . . . . .
H30 H 0.1450 -0.7280 0.4592 0.098 Uiso 1 1 calc R . . . .
C31 C 0.0817(2) -0.7260(4) 0.3453(11) 0.0710(19) Uani 1 1 d . . . . .
H31 H 0.0701 -0.6915 0.4495 0.085 Uiso 1 1 calc R . . . .
C32 C 0.05437(19) -0.7550(3) 0.1864(10) 0.0564(15) Uani 1 1 d . . . . .
H32 H 0.0240 -0.7407 0.1828 0.068 Uiso 1 1 calc R . . . .
C33 C 0.07177(18) -0.8063(3) 0.0285(10) 0.0488(14) Uani 1 1 d . . . . .
C34 C 0.04450(17) -0.8378(3) -0.1451(9) 0.0427(13) Uani 1 1 d . . . . .
C35 C -0.01059(16) -0.8599(3) -0.3621(10) 0.0432(13) Uani 1 1 d . . . . .
C36 C -0.05560(18) -0.8601(3) -0.4585(10) 0.0484(14) Uani 1 1 d . . . . .
C37 C -0.06850(19) -0.8596(3) -0.6766(10) 0.0560(15) Uani 1 1 d . . . . .
H37 H -0.0488 -0.8601 -0.7940 0.067 Uiso 1 1 calc R . . . .
C38 C -0.1163(2) -0.8584(4) -0.6903(13) 0.078(2) Uani 1 1 d . . . . .
H38 H -0.1316 -0.8576 -0.8220 0.094 Uiso 1 1 calc R . . . .
C39 C -0.1376(2) -0.8585(4) -0.5020(15) 0.080(2) Uani 1 1 d . . . . .
H39 H -0.1688 -0.8603 -0.4871 0.095 Uiso 1 1 calc R . . . .
C40 C 0.02373(19) -0.9590(3) -0.6190(10) 0.0563(15) Uani 1 1 d . . . . .
H40A H -0.0072 -0.9693 -0.6558 0.085 Uiso 1 1 calc GR . . . .
H40B H 0.0379 -1.0078 -0.5743 0.085 Uiso 1 1 calc GR . . . .
H40C H 0.0392 -0.9380 -0.7431 0.085 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C16 1.719(5) . ?
S1 C19 1.693(6) . ?
N1 C1 1.397(6) . ?
N1 C15 1.372(6) . ?
N1 C20 1.455(6) . ?
N2 C14 1.375(6) . ?
N2 C15 1.327(6) . ?
C1 C2 1.441(7) . ?
C1 C14 1.363(7) . ?
C2 C3 1.400(8) . ?
C2 C7 1.436(8) . ?
C3 C4 1.378(8) . ?
C4 C5 1.381(10) . ?
C5 C6 1.353(9) . ?
C6 C7 1.387(8) . ?
C7 C8 1.470(8) . ?
C8 C9 1.408(8) . ?
C8 C13 1.416(7) . ?
C9 C10 1.368(9) . ?
C10 C11 1.374(9) . ?
C11 C12 1.368(8) . ?
C12 C13 1.399(7) . ?
C13 C14 1.434(7) . ?
C15 C16 1.453(7) . ?
C16 C17 1.362(7) . ?
C17 C18 1.414(7) . ?
C18 C19 1.340(8) . ?
S2 C36 1.695(6) . ?
S2 C39 1.695(8) . ?
N3 C21 1.398(6) . ?
N3 C35 1.374(6) . ?
N3 C40 1.452(7) . ?
N4 C34 1.377(6) . ?
N4 C35 1.333(7) . ?
C21 C22 1.426(7) . ?
C21 C34 1.379(7) . ?
C22 C23 1.391(9) . ?
C22 C27 1.432(8) . ?
C23 C24 1.383(8) . ?
C24 C25 1.370(12) . ?
C25 C26 1.337(11) . ?
C26 C27 1.396(8) . ?
C27 C28 1.459(8) . ?
C28 C29 1.418(9) . ?
C28 C33 1.413(7) . ?
C29 C30 1.334(10) . ?
C30 C31 1.377(9) . ?
C31 C32 1.360(8) . ?
C32 C33 1.397(8) . ?
C33 C34 1.441(7) . ?
C35 C36 1.459(7) . ?
C36 C37 1.399(8) . ?
C37 C38 1.417(9) . ?
C38 C39 1.322(10) . ?

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
C19 S1 C16 92.5(3) . . ?
C1 N1 C20 128.3(4) . . ?
C15 N1 C1 105.7(4) . . ?
C15 N1 C20 125.5(4) . . ?
C15 N2 C14 104.0(4) . . ?
N1 C1 C2 130.8(5) . . ?
C14 C1 N1 105.4(4) . . ?
C14 C1 C2 123.7(5) . . ?
C3 C2 C1 125.7(5) . . ?
C3 C2 C7 118.9(5) . . ?
C7 C2 C1 115.3(5) . . ?
C4 C3 C2 121.8(6) . . ?
C3 C4 C5 118.4(7) . . ?
C6 C5 C4 121.1(6) . . ?
C5 C6 C7 123.1(6) . . ?
C2 C7 C8 121.2(4) . . ?
C6 C7 C2 116.7(6) . . ?
C6 C7 C8 122.1(5) . . ?
C9 C8 C7 123.3(5) . . ?
C9 C8 C13 116.7(6) . . ?
C13 C8 C7 120.0(5) . . ?
C10 C9 C8 121.7(6) . . ?
C9 C10 C11 120.9(6) . . ?
C12 C11 C10 119.6(6) . . ?
C11 C12 C13 120.9(6) . . ?
C8 C13 C14 117.6(5) . . ?
C12 C13 C8 120.2(5) . . ?
C12 C13 C14 122.2(5) . . ?
N2 C14 C13 126.0(5) . . ?
C1 C14 N2 112.0(4) . . ?
C1 C14 C13 122.0(5) . . ?
N1 C15 C16 125.5(5) . . ?
N2 C15 N1 112.9(4) . . ?
N2 C15 C16 121.6(4) . . ?
C15 C16 S1 118.1(4) . . ?
C17 C16 S1 109.8(4) . . ?
C17 C16 C15 132.0(5) . . ?
C16 C17 C18 113.1(5) . . ?
C19 C18 C17 112.7(5) . . ?
C18 C19 S1 111.8(4) . . ?
C39 S2 C36 92.2(4) . . ?
C21 N3 C40 127.5(4) . . ?
C35 N3 C21 106.6(4) . . ?
C35 N3 C40 125.3(5) . . ?
C35 N4 C34 104.4(4) . . ?
N3 C21 C22 132.4(5) . . ?
C34 C21 N3 104.8(4) . . ?
C34 C21 C22 122.8(5) . . ?
C21 C22 C27 116.2(5) . . ?
C23 C22 C21 125.3(6) . . ?
C23 C22 C27 118.5(5) . . ?
C24 C23 C22 121.6(7) . . ?
C25 C24 C23 118.6(7) . . ?
C26 C25 C24 121.7(7) . . ?
C25 C26 C27 122.2(8) . . ?
C22 C27 C28 121.1(5) . . ?
C26 C27 C22 117.2(6) . . ?
C26 C27 C28 121.7(6) . . ?
C29 C28 C27 123.6(5) . . ?
C33 C28 C27 120.9(5) . . ?
C33 C28 C29 115.5(6) . . ?
C30 C29 C28 122.2(6) . . ?
C29 C30 C31 121.5(7) . . ?
C32 C31 C30 119.5(7) . . ?
C31 C32 C33 120.3(6) . . ?
C28 C33 C34 116.6(5) . . ?
C32 C33 C28 121.0(5) . . ?
C32 C33 C34 122.5(5) . . ?
N4 C34 C21 111.8(5) . . ?
N4 C34 C33 125.7(5) . . ?
C21 C34 C33 122.5(5) . . ?
N3 C35 C36 124.3(5) . . ?
N4 C35 N3 112.4(4) . . ?
N4 C35 C36 123.3(5) . . ?
C35 C36 S2 118.3(5) . . ?
C37 C36 S2 111.7(4) . . ?
C37 C36 C35 129.9(5) . . ?
C36 C37 C38 109.3(6) . . ?
C39 C38 C37 115.0(7) . . ?
C38 C39 S2 111.7(5) . . ?

_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_t_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1963680'
loop_
_audit_author_name
_audit_author_address
'yun yu'
;wuhan university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_audit_creation_date             2019-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 N2 S'
_chemical_formula_sum            'C22 H18 N2 S'
_chemical_formula_weight         342.44
_chemical_absolute_configuration ?
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.895(3)
_cell_length_b                   7.3292(18)
_cell_length_c                   18.213(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.982(4)
_cell_angle_gamma                90
_cell_volume                     1677.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.453
_cell_measurement_theta_min      2.295
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1298 before and 0.0653 after correction. The Ratio of minimum to maximum transmission is 0.9108. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0932
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14462
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         1.621
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                4906
_reflns_number_total             7395
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7395
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      0.986
_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)+(0.0609P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1508
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C42(H42A,H42B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C33(H33),
  C34(H34), C35(H35), C36(H36), C39(H39), C40(H40), C41(H41)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.043
;
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 0.8422(4) 0.5513(10) 0.8061(3) 0.0604(18) Uani 1 1 d . . . . .
H1 H 0.828217 0.558418 0.853915 0.073 Uiso 1 1 calc R . . . .
C2 C 0.7627(4) 0.5006(9) 0.7462(3) 0.0516(14) Uani 1 1 d . . . . .
H2 H 0.695372 0.475022 0.754134 0.062 Uiso 1 1 calc R . . . .
C3 C 0.7805(4) 0.4863(7) 0.6735(2) 0.0390(12) Uani 1 1 d . . . . .
C4 C 0.8837(4) 0.5251(8) 0.6649(2) 0.0364(11) Uani 1 1 d . . . . .
C5 C 0.9424(4) 0.5919(9) 0.7965(3) 0.0540(15) Uani 1 1 d . . . . .
H5 H 0.995545 0.628232 0.837325 0.065 Uiso 1 1 calc R . . . .
C6 C 0.9630(4) 0.5783(8) 0.7260(3) 0.0474(14) Uani 1 1 d . . . . .
H6 H 1.030666 0.604871 0.719188 0.057 Uiso 1 1 calc R . . . .
C7 C 0.6973(3) 0.4329(8) 0.6078(2) 0.0386(11) Uani 1 1 d . . . . .
C8 C 0.7187(3) 0.4181(7) 0.5351(2) 0.0375(11) Uani 1 1 d . . . . .
C9 C 0.8262(3) 0.4542(7) 0.5296(2) 0.0346(11) Uani 1 1 d . . . . .
C10 C 0.9052(3) 0.5028(7) 0.5914(2) 0.0345(10) Uani 1 1 d . . . . .
C11 C 0.5949(4) 0.3856(8) 0.6162(3) 0.0497(14) Uani 1 1 d . . . . .
H11 H 0.579355 0.393370 0.663544 0.060 Uiso 1 1 calc R . . . .
C12 C 0.5175(4) 0.3285(9) 0.5561(3) 0.0574(16) Uani 1 1 d . . . . .
H12 H 0.450711 0.295872 0.563208 0.069 Uiso 1 1 calc R . . . .
C13 C 0.5379(4) 0.3193(9) 0.4861(3) 0.0524(15) Uani 1 1 d . . . . .
H13 H 0.484849 0.281250 0.445488 0.063 Uiso 1 1 calc R . . . .
C14 C 0.6358(4) 0.3656(8) 0.4752(3) 0.0441(13) Uani 1 1 d . . . . .
H14 H 0.647706 0.362198 0.426711 0.053 Uiso 1 1 calc R . . . .
C15 C 0.9819(4) 0.4873(7) 0.4999(3) 0.0381(11) Uani 1 1 d . . . . .
C16 C 1.0645(3) 0.4904(8) 0.4578(3) 0.0403(12) Uani 1 1 d . . . . .
C17 C 1.0634(4) 0.5316(8) 0.3840(3) 0.0473(13) Uani 1 1 d . . . . .
H17 H 1.002432 0.565315 0.348707 0.057 Uiso 1 1 calc R . . . .
C18 C 1.1651(4) 0.5171(9) 0.3677(3) 0.0537(15) Uani 1 1 d . . . . .
H18 H 1.178169 0.540570 0.320449 0.064 Uiso 1 1 calc R . . . .
C19 C 1.2409(4) 0.4663(9) 0.4272(3) 0.0541(15) Uani 1 1 d . . . . .
H19 H 1.311966 0.449730 0.425955 0.065 Uiso 1 1 calc R . . . .
C20 C 0.8327(4) 0.3913(7) 0.3928(2) 0.0386(12) Uani 1 1 d . . . . .
H20A H 0.781121 0.294586 0.392088 0.046 Uiso 1 1 calc R . . . .
H20B H 0.889063 0.343526 0.370871 0.046 Uiso 1 1 calc R . . . .
C21 C 0.7792(4) 0.5485(8) 0.3452(2) 0.0458(13) Uani 1 1 d . . . . .
H21A H 0.718130 0.588002 0.363890 0.055 Uiso 1 1 calc R . . . .
H21B H 0.828534 0.650095 0.350028 0.055 Uiso 1 1 calc R . . . .
C22 C 0.7433(5) 0.4978(10) 0.2632(3) 0.0694(19) Uani 1 1 d . . . . .
H22A H 0.694260 0.397590 0.258094 0.104 Uiso 1 1 calc GR . . . .
H22B H 0.803902 0.462810 0.243946 0.104 Uiso 1 1 calc GR . . . .
H22C H 0.708936 0.600598 0.235279 0.104 Uiso 1 1 calc GR . . . .
N1 N 0.8775(3) 0.4436(6) 0.47063(18) 0.0345(9) Uani 1 1 d . . . . .
N2 N 1.0010(3) 0.5239(6) 0.57275(19) 0.0387(10) Uani 1 1 d . . . . .
S1 S 1.19147(10) 0.4359(2) 0.50541(7) 0.0519(4) Uani 1 1 d . . . . .
C23 C 1.5495(4) -0.0023(7) 1.2113(2) 0.0407(11) Uani 1 1 d . . . . .
H23 H 1.479757 -0.005921 1.217122 0.049 Uiso 1 1 calc R . . . .
C24 C 1.6320(4) -0.0101(8) 1.2739(3) 0.0465(13) Uani 1 1 d . . . . .
H24 H 1.617229 -0.015727 1.321548 0.056 Uiso 1 1 calc R . . . .
C25 C 1.7362(4) -0.0097(7) 1.2671(3) 0.0433(12) Uani 1 1 d . . . . .
H25 H 1.791267 -0.016819 1.309843 0.052 Uiso 1 1 calc R . . . .
C26 C 1.7581(4) 0.0012(8) 1.1978(2) 0.0404(12) Uani 1 1 d . . . . .
H26 H 1.828424 0.001238 1.193183 0.049 Uiso 1 1 calc R . . . .
C27 C 1.6758(3) 0.0123(7) 1.1334(2) 0.0362(11) Uani 1 1 d . . . . .
C28 C 1.5691(3) 0.0110(7) 1.1379(2) 0.0338(10) Uani 1 1 d . . . . .
C29 C 1.4840(3) 0.0194(7) 1.0696(2) 0.0334(10) Uani 1 1 d . . . . .
C30 C 1.5072(4) 0.0261(7) 0.9977(3) 0.0360(11) Uani 1 1 d . . . . .
C31 C 1.6183(3) 0.0350(7) 0.9952(2) 0.0323(10) Uani 1 1 d . . . . .
C32 C 1.6981(3) 0.0303(7) 1.0595(2) 0.0356(11) Uani 1 1 d . . . . .
C33 C 1.3766(4) 0.0164(7) 1.0733(3) 0.0406(12) Uani 1 1 d . . . . .
H33 H 1.359852 0.012192 1.120375 0.049 Uiso 1 1 calc R . . . .
C34 C 1.2960(4) 0.0193(8) 1.0105(3) 0.0464(13) Uani 1 1 d . . . . .
H34 H 1.225619 0.020540 1.015018 0.056 Uiso 1 1 calc R . . . .
C35 C 1.3190(4) 0.0205(9) 0.9408(3) 0.0500(14) Uani 1 1 d . . . . .
H35 H 1.264048 0.018550 0.897810 0.060 Uiso 1 1 calc R . . . .
C36 C 1.4230(4) 0.0246(8) 0.9339(3) 0.0435(12) Uani 1 1 d . . . . .
H36 H 1.437722 0.026270 0.886211 0.052 Uiso 1 1 calc R . . . .
C37 C 1.7767(3) 0.0600(7) 0.9707(3) 0.0374(11) Uani 1 1 d . . . . .
C38 C 1.8620(4) 0.0927(7) 0.9310(3) 0.0408(12) Uani 1 1 d . . . . .
C39 C 1.8767(4) 0.0290(9) 0.8627(3) 0.0484(13) Uani 1 1 d . . . . .
H39 H 1.829221 -0.046181 0.830309 0.058 Uiso 1 1 calc R . . . .
C40 C 1.9737(4) 0.0936(10) 0.8489(3) 0.0638(18) Uani 1 1 d . . . . .
H40 H 1.997321 0.066004 0.805509 0.077 Uiso 1 1 calc R . . . .
C41 C 2.0289(4) 0.1996(9) 0.9051(3) 0.0568(15) Uani 1 1 d . . . . .
H41 H 2.094226 0.252807 0.904633 0.068 Uiso 1 1 calc R . . . .
C42 C 1.6254(4) 0.0889(7) 0.8577(2) 0.0382(11) Uani 1 1 d . . . . .
H42A H 1.676260 0.158815 0.837235 0.046 Uiso 1 1 calc R . . . .
H42B H 1.561783 0.162558 0.852987 0.046 Uiso 1 1 calc R . . . .
C43 C 1.5973(4) -0.0834(8) 0.8111(2) 0.0435(12) Uani 1 1 d . . . . .
H43A H 1.659155 -0.162316 0.818621 0.052 Uiso 1 1 calc R . . . .
H43B H 1.541459 -0.148369 0.828127 0.052 Uiso 1 1 calc R . . . .
C44 C 1.5601(5) -0.0405(12) 0.7279(3) 0.078(2) Uani 1 1 d . . . . .
H44A H 1.502531 0.045519 0.720741 0.117 Uiso 1 1 calc GR . . . .
H44B H 1.536170 -0.150591 0.700750 0.117 Uiso 1 1 calc GR . . . .
H44C H 1.617914 0.010650 0.709516 0.117 Uiso 1 1 calc GR . . . .
N3 N 1.6701(3) 0.0551(6) 0.93717(19) 0.0353(9) Uani 1 1 d . . . . .
N4 N 1.7965(3) 0.0456(6) 1.0442(2) 0.0384(10) Uani 1 1 d . . . . .
S2 S 1.96671(10) 0.2241(2) 0.97523(8) 0.0546(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 H1 0.9300 . ?
C1 C2 1.370(7) . ?
C1 C5 1.374(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(6) . ?
C3 C4 1.404(6) . ?
C3 C7 1.470(6) . ?
C4 C6 1.388(7) . ?
C4 C10 1.436(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.415(6) . ?
C7 C11 1.407(6) . ?
C8 C9 1.437(6) . ?
C8 C14 1.399(6) . ?
C9 C10 1.384(6) . ?
C9 N1 1.384(5) . ?
C10 N2 1.360(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.360(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.445(6) . ?
C15 N1 1.370(6) . ?
C15 N2 1.322(6) . ?
C16 C17 1.375(6) . ?
C16 S1 1.719(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.412(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.338(8) . ?
C19 H19 0.9300 . ?
C19 S1 1.700(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.512(7) . ?
C20 N1 1.456(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.508(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.376(6) . ?
C23 C28 1.418(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.376(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.356(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.396(6) . ?
C27 C28 1.398(6) . ?
C27 C32 1.444(6) . ?
C28 C29 1.463(6) . ?
C29 C30 1.408(6) . ?
C29 C33 1.402(6) . ?
C30 C31 1.445(6) . ?
C30 C36 1.401(6) . ?
C31 C32 1.374(6) . ?
C31 N3 1.380(5) . ?
C32 N4 1.363(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.363(6) . ?
C34 H34 0.9300 . ?
C34 C35 1.367(6) . ?
C35 H35 0.9300 . ?
C35 C36 1.376(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.466(6) . ?
C37 N3 1.374(6) . ?
C37 N4 1.310(6) . ?
C38 C39 1.380(6) . ?
C38 S2 1.707(5) . ?
C39 H39 0.9300 . ?
C39 C40 1.413(7) . ?
C40 H40 0.9300 . ?
C40 C41 1.354(8) . ?
C41 H41 0.9300 . ?
C41 S2 1.663(5) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.520(7) . ?
C42 N3 1.454(6) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 C44 1.516(7) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.5 . . ?
C2 C1 C5 121.0(5) . . ?
C5 C1 H1 119.5 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 116.9(4) . . ?
C2 C3 C7 123.1(4) . . ?
C4 C3 C7 119.9(4) . . ?
C3 C4 C10 117.9(4) . . ?
C6 C4 C3 120.8(4) . . ?
C6 C4 C10 121.2(4) . . ?
C1 C5 H5 120.4 . . ?
C6 C5 C1 119.2(5) . . ?
C6 C5 H5 120.4 . . ?
C4 C6 H6 119.7 . . ?
C5 C6 C4 120.6(5) . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C3 121.5(4) . . ?
C11 C7 C3 120.5(4) . . ?
C11 C7 C8 117.9(4) . . ?
C7 C8 C9 116.4(4) . . ?
C14 C8 C7 118.4(4) . . ?
C14 C8 C9 125.2(4) . . ?
C10 C9 C8 122.4(4) . . ?
N1 C9 C8 132.9(4) . . ?
N1 C9 C10 104.6(4) . . ?
C9 C10 C4 121.7(4) . . ?
N2 C10 C4 126.6(4) . . ?
N2 C10 C9 111.7(4) . . ?
C7 C11 H11 119.3 . . ?
C12 C11 C7 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(5) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.3(5) . . ?
C14 C13 H13 119.9 . . ?
C8 C14 H14 119.2 . . ?
C13 C14 C8 121.6(5) . . ?
C13 C14 H14 119.2 . . ?
N1 C15 C16 125.1(4) . . ?
N2 C15 C16 122.4(4) . . ?
N2 C15 N1 112.5(4) . . ?
C15 C16 S1 117.5(3) . . ?
C17 C16 C15 132.4(4) . . ?
C17 C16 S1 110.1(3) . . ?
C16 C17 H17 123.8 . . ?
C16 C17 C18 112.5(5) . . ?
C18 C17 H17 123.8 . . ?
C17 C18 H18 123.4 . . ?
C19 C18 C17 113.3(5) . . ?
C19 C18 H18 123.4 . . ?
C18 C19 H19 124.1 . . ?
C18 C19 S1 111.8(4) . . ?
S1 C19 H19 124.1 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
N1 C20 H20A 109.0 . . ?
N1 C20 H20B 109.0 . . ?
N1 C20 C21 112.8(4) . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 C20 112.3(5) . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C9 N1 C20 128.0(4) . . ?
C15 N1 C9 106.5(3) . . ?
C15 N1 C20 125.4(4) . . ?
C15 N2 C10 104.6(4) . . ?
C19 S1 C16 92.4(2) . . ?
C24 C23 H23 119.4 . . ?
C24 C23 C28 121.1(4) . . ?
C28 C23 H23 119.4 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 120.9(4) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.5(4) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C28 121.5(4) . . ?
C26 C27 C32 121.1(4) . . ?
C28 C27 C32 117.4(4) . . ?
C23 C28 C29 123.1(4) . . ?
C27 C28 C23 116.2(4) . . ?
C27 C28 C29 120.7(4) . . ?
C30 C29 C28 121.1(4) . . ?
C33 C29 C28 121.2(4) . . ?
C33 C29 C30 117.7(4) . . ?
C29 C30 C31 116.8(4) . . ?
C36 C30 C29 118.9(4) . . ?
C36 C30 C31 124.3(4) . . ?
C32 C31 C30 122.0(4) . . ?
C32 C31 N3 104.9(4) . . ?
N3 C31 C30 133.1(4) . . ?
C31 C32 C27 121.9(4) . . ?
N4 C32 C27 125.9(4) . . ?
N4 C32 C31 112.2(4) . . ?
C29 C33 H33 118.9 . . ?
C34 C33 C29 122.3(4) . . ?
C34 C33 H33 118.9 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.8(4) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 119.9 . . ?
C34 C35 C36 120.2(4) . . ?
C36 C35 H35 119.9 . . ?
C30 C36 H36 119.5 . . ?
C35 C36 C30 121.0(4) . . ?
C35 C36 H36 119.5 . . ?
N3 C37 C38 124.8(4) . . ?
N4 C37 C38 121.5(4) . . ?
N4 C37 N3 113.5(4) . . ?
C37 C38 S2 117.4(4) . . ?
C39 C38 C37 131.3(5) . . ?
C39 C38 S2 111.2(4) . . ?
C38 C39 H39 124.6 . . ?
C38 C39 C40 110.7(5) . . ?
C40 C39 H39 124.6 . . ?
C39 C40 H40 123.4 . . ?
C41 C40 C39 113.1(5) . . ?
C41 C40 H40 123.4 . . ?
C40 C41 H41 123.8 . . ?
C40 C41 S2 112.4(4) . . ?
S2 C41 H41 123.8 . . ?
H42A C42 H42B 107.7 . . ?
C43 C42 H42A 108.8 . . ?
C43 C42 H42B 108.8 . . ?
N3 C42 H42A 108.8 . . ?
N3 C42 H42B 108.8 . . ?
N3 C42 C43 114.0(4) . . ?
C42 C43 H43A 109.3 . . ?
C42 C43 H43B 109.3 . . ?
H43A C43 H43B 108.0 . . ?
C44 C43 C42 111.6(5) . . ?
C44 C43 H43A 109.3 . . ?
C44 C43 H43B 109.3 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C31 N3 C42 129.0(4) . . ?
C37 N3 C31 105.7(3) . . ?
C37 N3 C42 124.9(4) . . ?
C37 N4 C32 103.8(4) . . ?
C41 S2 C38 92.5(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
C1 C2 C3 C4 0.5(9) . . . . ?
C1 C2 C3 C7 -179.8(6) . . . . ?
C1 C5 C6 C4 0.4(9) . . . . ?
C2 C1 C5 C6 -1.1(10) . . . . ?
C2 C3 C4 C6 -1.2(8) . . . . ?
C2 C3 C4 C10 177.0(5) . . . . ?
C2 C3 C7 C8 -179.3(5) . . . . ?
C2 C3 C7 C11 -2.6(8) . . . . ?
C3 C4 C6 C5 0.8(9) . . . . ?
C3 C4 C10 C9 3.4(7) . . . . ?
C3 C4 C10 N2 -176.2(5) . . . . ?
C3 C7 C8 C9 1.3(7) . . . . ?
C3 C7 C8 C14 179.7(5) . . . . ?
C3 C7 C11 C12 -177.4(6) . . . . ?
C4 C3 C7 C8 0.4(8) . . . . ?
C4 C3 C7 C11 177.1(5) . . . . ?
C4 C10 N2 C15 179.2(5) . . . . ?
C5 C1 C2 C3 0.7(10) . . . . ?
C6 C4 C10 C9 -178.4(5) . . . . ?
C6 C4 C10 N2 2.0(8) . . . . ?
C7 C3 C4 C6 179.1(5) . . . . ?
C7 C3 C4 C10 -2.7(7) . . . . ?
C7 C8 C9 C10 -0.6(7) . . . . ?
C7 C8 C9 N1 175.8(5) . . . . ?
C7 C8 C14 C13 -3.7(8) . . . . ?
C7 C11 C12 C13 -1.2(9) . . . . ?
C8 C7 C11 C12 -0.6(8) . . . . ?
C8 C9 C10 C4 -1.7(7) . . . . ?
C8 C9 C10 N2 177.9(5) . . . . ?
C8 C9 N1 C15 -177.4(5) . . . . ?
C8 C9 N1 C20 0.8(8) . . . . ?
C9 C8 C14 C13 174.5(6) . . . . ?
C9 C10 N2 C15 -0.5(6) . . . . ?
C10 C4 C6 C5 -177.4(5) . . . . ?
C10 C9 N1 C15 -0.5(5) . . . . ?
C10 C9 N1 C20 177.7(5) . . . . ?
C11 C7 C8 C9 -175.5(5) . . . . ?
C11 C7 C8 C14 2.9(7) . . . . ?
C11 C12 C13 C14 0.5(9) . . . . ?
C12 C13 C14 C8 2.0(9) . . . . ?
C14 C8 C9 C10 -178.9(5) . . . . ?
C14 C8 C9 N1 -2.5(9) . . . . ?
C15 C16 C17 C18 179.6(6) . . . . ?
C15 C16 S1 C19 -179.9(5) . . . . ?
C16 C15 N1 C9 179.0(5) . . . . ?
C16 C15 N1 C20 0.7(8) . . . . ?
C16 C15 N2 C10 -178.6(5) . . . . ?
C16 C17 C18 C19 0.1(8) . . . . ?
C17 C16 S1 C19 -0.5(4) . . . . ?
C17 C18 C19 S1 -0.5(7) . . . . ?
C18 C19 S1 C16 0.5(5) . . . . ?
C21 C20 N1 C9 84.3(6) . . . . ?
C21 C20 N1 C15 -97.8(6) . . . . ?
N1 C9 C10 C4 -179.0(4) . . . . ?
N1 C9 C10 N2 0.6(5) . . . . ?
N1 C15 C16 C17 32.4(9) . . . . ?
N1 C15 C16 S1 -148.4(4) . . . . ?
N1 C15 N2 C10 0.1(6) . . . . ?
N1 C20 C21 C22 174.1(4) . . . . ?
N2 C15 C16 C17 -149.0(6) . . . . ?
N2 C15 C16 S1 30.2(7) . . . . ?
N2 C15 N1 C9 0.3(6) . . . . ?
N2 C15 N1 C20 -178.0(5) . . . . ?
S1 C16 C17 C18 0.3(6) . . . . ?
C23 C24 C25 C26 1.0(9) . . . . ?
C23 C28 C29 C30 -177.7(5) . . . . ?
C23 C28 C29 C33 0.6(8) . . . . ?
C24 C23 C28 C27 1.1(7) . . . . ?
C24 C23 C28 C29 179.9(5) . . . . ?
C24 C25 C26 C27 0.1(8) . . . . ?
C25 C26 C27 C28 -0.6(8) . . . . ?
C25 C26 C27 C32 177.8(5) . . . . ?
C26 C27 C28 C23 0.0(7) . . . . ?
C26 C27 C28 C29 -178.9(5) . . . . ?
C26 C27 C32 C31 177.7(5) . . . . ?
C26 C27 C32 N4 -2.8(8) . . . . ?
C27 C28 C29 C30 1.0(7) . . . . ?
C27 C28 C29 C33 179.4(5) . . . . ?
C27 C32 N4 C37 -179.4(5) . . . . ?
C28 C23 C24 C25 -1.6(8) . . . . ?
C28 C27 C32 C31 -3.8(7) . . . . ?
C28 C27 C32 N4 175.7(5) . . . . ?
C28 C29 C30 C31 -3.5(7) . . . . ?
C28 C29 C30 C36 176.8(5) . . . . ?
C28 C29 C33 C34 -178.3(5) . . . . ?
C29 C30 C31 C32 2.4(7) . . . . ?
C29 C30 C31 N3 -175.0(5) . . . . ?
C29 C30 C36 C35 1.4(8) . . . . ?
C29 C33 C34 C35 1.8(9) . . . . ?
C30 C29 C33 C34 0.1(8) . . . . ?
C30 C31 C32 C27 1.3(8) . . . . ?
C30 C31 C32 N4 -178.3(4) . . . . ?
C30 C31 N3 C37 178.0(5) . . . . ?
C30 C31 N3 C42 5.5(9) . . . . ?
C31 C30 C36 C35 -178.3(5) . . . . ?
C31 C32 N4 C37 0.1(6) . . . . ?
C32 C27 C28 C23 -178.5(4) . . . . ?
C32 C27 C28 C29 2.7(7) . . . . ?
C32 C31 N3 C37 0.3(5) . . . . ?
C32 C31 N3 C42 -172.2(5) . . . . ?
C33 C29 C30 C31 178.1(5) . . . . ?
C33 C29 C30 C36 -1.7(7) . . . . ?
C33 C34 C35 C36 -2.1(9) . . . . ?
C34 C35 C36 C30 0.5(9) . . . . ?
C36 C30 C31 C32 -177.9(5) . . . . ?
C36 C30 C31 N3 4.8(9) . . . . ?
C37 C38 C39 C40 -178.0(6) . . . . ?
C37 C38 S2 C41 178.3(4) . . . . ?
C38 C37 N3 C31 -175.5(5) . . . . ?
C38 C37 N3 C42 -2.7(8) . . . . ?
C38 C37 N4 C32 175.5(5) . . . . ?
C38 C39 C40 C41 0.5(8) . . . . ?
C39 C38 S2 C41 0.8(5) . . . . ?
C39 C40 C41 S2 0.1(7) . . . . ?
C40 C41 S2 C38 -0.5(5) . . . . ?
C43 C42 N3 C31 -89.0(6) . . . . ?
C43 C42 N3 C37 99.8(5) . . . . ?
N3 C31 C32 C27 179.3(4) . . . . ?
N3 C31 C32 N4 -0.3(6) . . . . ?
N3 C37 C38 C39 -41.7(9) . . . . ?
N3 C37 C38 S2 141.3(4) . . . . ?
N3 C37 N4 C32 0.0(6) . . . . ?
N3 C42 C43 C44 -175.1(4) . . . . ?
N4 C37 C38 C39 143.3(6) . . . . ?
N4 C37 C38 S2 -33.7(7) . . . . ?
N4 C37 N3 C31 -0.2(6) . . . . ?
N4 C37 N3 C42 172.6(5) . . . . ?
S2 C38 C39 C40 -0.9(7) . . . . ?

_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_t_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1970707'
loop_
_audit_author_name
_audit_author_address
'yun yu'
;wuhan university
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 N2 S'
_chemical_formula_sum            'C26 H26 N2 S'
_chemical_formula_weight         398.55
_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'
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                   22.385(5)
_cell_length_b                   5.0506(12)
_cell_length_c                   18.722(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.670(4)
_cell_angle_gamma                90
_cell_volume                     2065.2(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4344
_cell_measurement_temperature    276(2)
_cell_measurement_theta_max      26.727
_cell_measurement_theta_min      2.373
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1318 before and 0.0533 after correction. The Ratio of minimum to maximum transmission is 0.8736. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15487
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.817
_diffrn_reflns_theta_min         1.865
_diffrn_ambient_temperature      276(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3215
_reflns_number_total             4391
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.046
_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)+(0.0780P)²+0.4445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1515
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1-C23 \\sim S1A-C23A
 with sigma of 0.02
 S1-C26 \\sim S1A-C26A
 with sigma of 0.02
 C24-C23 \\sim C24A-C23A
 with sigma of 0.02
 C24-C25 \\sim C24A-C25A
 with sigma of 0.02
 C23-C22 \\sim C23A-C22
 with sigma of 0.02
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 S1-C24 \\sim S1A-C24A
 with sigma of 0.04
 S1-C22 \\sim S1A-C22
 with sigma of 0.04
 S1-C25 \\sim S1A-C25A
 with sigma of 0.04
 C24-C22 \\sim C24A-C22
 with sigma of 0.04
 C24-C26 \\sim C24A-C26A
 with sigma of 0.04
 C23-C25 \\sim C23A-C25A
 with sigma of 0.04
 C23-C26 \\sim C23A-C26A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C24A) = Uanis(S1)
Uanis(C23) = Uanis(C23A)
Uanis(S1A) = Uanis(C24)
Uanis(C25) = Uanis(C26A)
Uanis(C26) = Uanis(C25A)
4. Others
 Sof(S1A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(H25A)=Sof(C23A)=Sof(C24A)=
 Sof(H24A)=1-FVAR(1)
 Sof(S1)=Sof(C24)=Sof(H24)=Sof(C23)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C16(H16A,H16B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,
 H19B), C20(H20A,H20B)
5.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C12(H12), C11(H11), C10(H10), C6(H6), C3(H3), C5(H5), C25(H25),
 C26(H26), C4(H4), C9(H9), C26A(H26A), C25A(H25A), C24A(H24A)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.25686(7) 0.5798(3) 0.66437(6) 0.0418(4) Uani 0.524(3) 1 d D . P A 1
C24 C 0.1882(4) 0.538(3) 0.5382(6) 0.0678(6) Uani 0.524(3) 1 d D . P A 1
H24 H 0.1683 0.5646 0.4897 0.081 Uiso 0.524(3) 1 calc R . P A 1
N1 N 0.27516(7) 0.9265(3) 0.47838(7) 0.0302(3) Uani 1 1 d . . . . .
N2 N 0.31475(7) 1.0083(3) 0.59685(8) 0.0328(4) Uani 1 1 d . . . . .
C14 C 0.31864(8) 1.1250(3) 0.48078(9) 0.0287(4) Uani 1 1 d . . . . .
C12 C 0.31455(9) 1.2461(4) 0.34788(9) 0.0376(4) Uani 1 1 d . . . . .
H12 H 0.2860 1.1139 0.3312 0.045 Uiso 1 1 calc R . . . .
C2 C 0.38887(8) 1.3609(4) 0.57998(9) 0.0298(4) Uani 1 1 d . . . . .
C18 C 0.09387(10) 0.8820(5) 0.26320(11) 0.0460(5) Uani 1 1 d . . . . .
H18A H 0.0631 0.8925 0.2924 0.055 Uiso 1 1 calc R . . . .
H18B H 0.1037 1.0613 0.2512 0.055 Uiso 1 1 calc R . . . .
C7 C 0.40890(8) 1.5160(4) 0.52716(9) 0.0306(4) Uani 1 1 d . . . . .
C16 C 0.18168(9) 0.9136(4) 0.37585(10) 0.0380(4) Uani 1 1 d . . . . .
H16A H 0.1895 1.0923 0.3612 0.046 Uiso 1 1 calc R . . . .
H16B H 0.1546 0.9241 0.4097 0.046 Uiso 1 1 calc R . . . .
C23 C 0.2412(8) 0.647(2) 0.5732(15) 0.0273(18) Uani 0.524(3) 1 d D . P A 1
C22 C 0.27487(8) 0.8656(4) 0.54995(9) 0.0312(4) Uani 1 1 d D . . . .
C8 C 0.38244(8) 1.4752(4) 0.44861(9) 0.0308(4) Uani 1 1 d . . . . .
C13 C 0.33770(8) 1.2753(4) 0.42429(9) 0.0301(4) Uani 1 1 d . . . . .
C15 C 0.24190(8) 0.7838(4) 0.41368(9) 0.0317(4) Uani 1 1 d . . . . .
H15A H 0.2334 0.6057 0.4281 0.038 Uiso 1 1 calc R . . . .
H15B H 0.2680 0.7697 0.3788 0.038 Uiso 1 1 calc R . . . .
C11 C 0.33308(10) 1.4072(4) 0.29811(10) 0.0415(5) Uani 1 1 d . . . . .
H11 H 0.3169 1.3845 0.2483 0.050 Uiso 1 1 calc R . . . .
C1 C 0.34207(8) 1.1687(4) 0.55448(9) 0.0285(4) Uani 1 1 d . . . . .
C10 C 0.37589(10) 1.6040(4) 0.32183(11) 0.0460(5) Uani 1 1 d . . . . .
H10 H 0.3884 1.7142 0.2881 0.055 Uiso 1 1 calc R . . . .
C6 C 0.45446(9) 1.7065(4) 0.55239(11) 0.0414(5) Uani 1 1 d . . . . .
H6 H 0.4684 1.8118 0.5187 0.050 Uiso 1 1 calc R . . . .
C17 C 0.15104(9) 0.7531(4) 0.30847(10) 0.0431(5) Uani 1 1 d . . . . .
H17A H 0.1802 0.7271 0.2777 0.052 Uiso 1 1 calc R . . . .
H17B H 0.1403 0.5800 0.3243 0.052 Uiso 1 1 calc R . . . .
C3 C 0.41483(9) 1.3963(4) 0.65504(10) 0.0376(4) Uani 1 1 d . . . . .
H3 H 0.4018 1.2917 0.6896 0.045 Uiso 1 1 calc R . . . .
C5 C 0.47881(9) 1.7403(5) 0.62574(11) 0.0448(5) Uani 1 1 d . . . . .
H5 H 0.5087 1.8686 0.6411 0.054 Uiso 1 1 calc R . . . .
C25 C 0.1680(9) 0.366(4) 0.5919(12) 0.0506(15) Uani 0.524(3) 1 d D . P A 1
H25 H 0.1320 0.2683 0.5784 0.061 Uiso 0.524(3) 1 calc R . P A 1
C19 C 0.06712(10) 0.7346(5) 0.19282(11) 0.0495(5) Uani 1 1 d . . . . .
H19A H 0.0987 0.7143 0.1650 0.059 Uiso 1 1 calc R . . . .
H19B H 0.0550 0.5588 0.2050 0.059 Uiso 1 1 calc R . . . .
C26 C 0.2023(15) 0.352(7) 0.6609(12) 0.0488(15) Uani 0.524(3) 1 d D . P A 1
H26 H 0.1967 0.2392 0.6982 0.059 Uiso 0.524(3) 1 calc R . P A 1
C4 C 0.45914(9) 1.5840(4) 0.67724(11) 0.0422(5) Uani 1 1 d . . . . .
H4 H 0.4761 1.6071 0.7268 0.051 Uiso 1 1 calc R . . . .
C20 C 0.01251(12) 0.8707(6) 0.14532(13) 0.0672(7) Uani 1 1 d . . . . .
H20A H 0.0243 1.0481 0.1342 0.081 Uiso 1 1 calc R . . . .
H20B H -0.0195 0.8865 0.1726 0.081 Uiso 1 1 calc R . . . .
C9 C 0.39994(9) 1.6360(4) 0.39544(11) 0.0416(5) Uani 1 1 d . . . . .
H9 H 0.4288 1.7686 0.4106 0.050 Uiso 1 1 calc R . . . .
C21 C -0.01287(16) 0.7265(8) 0.07432(15) 0.0960(11) Uani 1 1 d . . . . .
H21A H -0.0471 0.8232 0.0465 0.144 Uiso 1 1 calc GR . . . .
H21B H -0.0260 0.5526 0.0848 0.144 Uiso 1 1 calc GR . . . .
H21C H 0.0183 0.7123 0.0466 0.144 Uiso 1 1 calc GR . . . .
S1A S 0.17180(10) 0.5236(6) 0.52732(13) 0.0678(6) Uani 0.476(3) 1 d D . P A 2
C26A C 0.1578(10) 0.316(4) 0.5904(14) 0.0506(15) Uani 0.476(3) 1 d D . P A 2
H26A H 0.1273 0.1883 0.5860 0.061 Uiso 0.476(3) 1 calc R . P A 2
C25A C 0.2018(17) 0.379(8) 0.6497(13) 0.0488(15) Uani 0.476(3) 1 d D . P A 2
H25A H 0.2017 0.3022 0.6948 0.059 Uiso 0.476(3) 1 calc R . P A 2
C23A C 0.2321(10) 0.689(3) 0.5766(16) 0.0273(18) Uani 0.476(3) 1 d D . P A 2
C24A C 0.2496(4) 0.5679(18) 0.6427(3) 0.0418(4) Uani 0.476(3) 1 d D . P A 2
H24A H 0.2856 0.5997 0.6773 0.050 Uiso 0.476(3) 1 calc R . 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
S1 C23 1.70(3) . ?
S1 C26 1.67(2) . ?
C24 C23 1.34(2) . ?
C24 C25 1.47(2) . ?
N1 C14 1.391(2) . ?
N1 C22 1.376(2) . ?
N1 C15 1.465(2) . ?
N2 C22 1.320(2) . ?
N2 C1 1.368(2) . ?
C14 C13 1.440(2) . ?
C14 C1 1.382(2) . ?
C12 C13 1.418(2) . ?
C12 C11 1.368(3) . ?
C2 C7 1.410(3) . ?
C2 C1 1.431(2) . ?
C2 C3 1.409(2) . ?
C18 C17 1.518(3) . ?
C18 C19 1.518(3) . ?
C7 C8 1.474(2) . ?
C7 C6 1.406(3) . ?
C16 C15 1.526(2) . ?
C16 C17 1.530(3) . ?
C23 C22 1.456(8) . ?
C22 C23A 1.473(8) . ?
C8 C13 1.425(3) . ?
C8 C9 1.405(3) . ?
C11 C10 1.384(3) . ?
C10 C9 1.375(3) . ?
C6 C5 1.373(3) . ?
C3 C4 1.369(3) . ?
C5 C4 1.390(3) . ?
C25 C26 1.353(11) . ?
C19 C20 1.510(3) . ?
C20 C21 1.513(4) . ?
S1A C26A 1.66(2) . ?
S1A C23A 1.68(3) . ?
C26A C25A 1.351(12) . ?
C25A C24A 1.46(2) . ?
C23A C24A 1.36(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
C26 S1 C23 96.4(8) . . ?
C23 C24 C25 106.3(12) . . ?
C14 N1 C15 127.33(14) . . ?
C22 N1 C14 106.39(14) . . ?
C22 N1 C15 125.83(15) . . ?
C22 N2 C1 105.09(14) . . ?
N1 C14 C13 132.37(15) . . ?
C1 C14 N1 104.88(15) . . ?
C1 C14 C13 122.71(16) . . ?
C11 C12 C13 121.80(19) . . ?
C7 C2 C1 117.71(15) . . ?
C3 C2 C7 120.26(17) . . ?
C3 C2 C1 122.03(16) . . ?
C19 C18 C17 113.47(19) . . ?
C2 C7 C8 120.15(16) . . ?
C6 C7 C2 117.61(16) . . ?
C6 C7 C8 122.25(16) . . ?
C15 C16 C17 110.21(16) . . ?
C24 C23 S1 111.9(7) . . ?
C24 C23 C22 128.8(19) . . ?
C22 C23 S1 116.5(16) . . ?
N1 C22 C23 125.0(11) . . ?
N1 C22 C23A 127.4(13) . . ?
N2 C22 N1 112.26(16) . . ?
N2 C22 C23 122.2(11) . . ?
N2 C22 C23A 120.0(12) . . ?
C13 C8 C7 121.21(16) . . ?
C9 C8 C7 120.83(17) . . ?
C9 C8 C13 117.95(16) . . ?
C12 C13 C14 125.76(17) . . ?
C12 C13 C8 118.14(16) . . ?
C8 C13 C14 116.07(15) . . ?
N1 C15 C16 114.17(15) . . ?
C12 C11 C10 120.02(18) . . ?
N2 C1 C14 111.37(15) . . ?
N2 C1 C2 126.55(15) . . ?
C14 C1 C2 122.07(16) . . ?
C9 C10 C11 119.83(18) . . ?
C5 C6 C7 121.39(19) . . ?
C18 C17 C16 113.82(17) . . ?
C4 C3 C2 120.22(18) . . ?
C6 C5 C4 120.44(19) . . ?
C26 C25 C24 119.2(11) . . ?
C20 C19 C18 113.7(2) . . ?
C25 C26 S1 104.9(11) . . ?
C3 C4 C5 120.08(18) . . ?
C19 C20 C21 113.4(3) . . ?
C10 C9 C8 122.2(2) . . ?
C26A S1A C23A 100.2(9) . . ?
C25A C26A S1A 102.6(12) . . ?
C26A C25A C24A 119.8(14) . . ?
C22 C23A S1A 128.2(19) . . ?
C24A C23A C22 120(2) . . ?
C24A C23A S1A 108.2(6) . . ?
C23A C24A C25A 107.8(13) . . ?

_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_t_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1970708'
loop_
_audit_author_name
_audit_author_address
'yun yu'
;wuhan university
China
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H28 N2 S'
_chemical_formula_sum            'C27 H28 N2 S'
_chemical_formula_weight         412.57
_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'
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                   23.057(3)
_cell_length_b                   5.0554(6)
_cell_length_c                   18.693(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.930(2)
_cell_angle_gamma                90
_cell_volume                     2146.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    276(2)
_cell_measurement_theta_max      31.795
_cell_measurement_theta_min      2.526
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1045 before and 0.0502 after correction. The Ratio of minimum to maximum transmission is 0.8738. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20932
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.902
_diffrn_reflns_theta_min         2.212
_diffrn_ambient_temperature      276(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5324
_reflns_number_total             6905
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         6905
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.097
_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)+(0.0555P)²+1.1875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1622
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1-C16 \\sim S1A-C16A
 with sigma of 0.02
 S1-C19 \\sim S1A-C19A
 with sigma of 0.02
 C15-C16 \\sim C15-C16A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 S1-C15 \\sim S1A-C15
 with sigma of 0.04
 S1-C17 \\sim S1A-C17A
 with sigma of 0.04
 S1-C18 \\sim S1A-C18A
 with sigma of 0.04
 C15-C17 \\sim C15-C17A
 with sigma of 0.04
 C16-C18 \\sim C16A-C18A
 with sigma of 0.04
 C16-C19 \\sim C16A-C19A
 with sigma of 0.04
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
3. Others
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=
 Sof(S1A)=1-FVAR(1)
 Sof(S1)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C17A(H17A), C18A(H18A), C19A(H19A)
4.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.044
;
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 0.17456(6) 0.3779(3) 0.50859(7) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.21643(5) 0.5759(2) 0.50820(6) 0.0281(2) Uani 1 1 d . . . . .
S1 S 0.3162(2) 0.9661(11) 0.4534(3) 0.0661(11) Uani 0.469(3) 1 d D . P A 1
C2 C 0.15577(6) 0.2287(3) 0.56597(7) 0.0275(3) Uani 1 1 d . . . . .
N2 N 0.17842(6) 0.4908(3) 0.39154(6) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.17856(7) 0.2596(3) 0.64105(8) 0.0344(3) Uani 1 1 d . . . . .
H3 H 0.2061 0.3916 0.6559 0.041 Uiso 1 1 calc R . . . .
C4 C 0.16065(8) 0.0978(4) 0.69227(8) 0.0393(4) Uani 1 1 d . . . . .
H4 H 0.1762 0.1208 0.7412 0.047 Uiso 1 1 calc R . . . .
C5 C 0.11958(8) -0.0989(4) 0.67112(9) 0.0427(4) Uani 1 1 d . . . . .
H5 H 0.1078 -0.2091 0.7058 0.051 Uiso 1 1 calc R . . . .
C6 C 0.09608(7) -0.1317(4) 0.59885(9) 0.0385(4) Uani 1 1 d . . . . .
H6 H 0.0682 -0.2636 0.5856 0.046 Uiso 1 1 calc R . . . .
C7 C 0.11299(6) 0.0285(3) 0.54439(8) 0.0283(3) Uani 1 1 d . . . . .
C8 C 0.08770(6) -0.0141(3) 0.46767(8) 0.0288(3) Uani 1 1 d . . . . .
C9 C 0.04411(7) -0.2053(4) 0.44515(9) 0.0388(4) Uani 1 1 d . . . . .
H9 H 0.0308 -0.3105 0.4798 0.047 Uiso 1 1 calc R . . . .
C10 C 0.02072(8) -0.2399(4) 0.37287(10) 0.0430(4) Uani 1 1 d . . . . .
H10 H -0.0080 -0.3680 0.3594 0.052 Uiso 1 1 calc R . . . .
C11 C 0.03961(7) -0.0854(4) 0.31991(9) 0.0394(4) Uani 1 1 d . . . . .
H11 H 0.0234 -0.1092 0.2712 0.047 Uiso 1 1 calc R . . . .
C12 C 0.08224(7) 0.1023(3) 0.33971(8) 0.0350(3) Uani 1 1 d . . . . .
H12 H 0.0949 0.2061 0.3043 0.042 Uiso 1 1 calc R . . . .
C13 C 0.10709(6) 0.1395(3) 0.41336(7) 0.0273(3) Uani 1 1 d . . . . .
C14 C 0.15208(6) 0.3320(3) 0.43586(7) 0.0269(3) Uani 1 1 d . . . . .
C15 C 0.21674(7) 0.6343(3) 0.43642(8) 0.0299(3) Uani 1 1 d D . . . .
C16 C 0.2515(10) 0.828(4) 0.4051(17) 0.032(3) Uani 0.469(3) 1 d D . P A 1
C17 C 0.2429(5) 0.931(3) 0.3395(5) 0.063(4) Uani 0.469(3) 1 d D . P A 1
H17 H 0.2121 0.8822 0.3030 0.076 Uiso 0.469(3) 1 calc R . P A 1
C18 C 0.2858(9) 1.123(4) 0.3304(9) 0.063(5) Uani 0.469(3) 1 d D . P A 1
H18 H 0.2856 1.2083 0.2863 0.076 Uiso 0.469(3) 1 calc R . P A 1
C19 C 0.3262(8) 1.175(4) 0.3886(7) 0.0438(19) Uani 0.469(3) 1 d D . P A 1
H19 H 0.3551 1.3050 0.3921 0.053 Uiso 0.469(3) 1 calc R . P A 1
C20 C 0.24711(6) 0.7237(3) 0.57071(7) 0.0297(3) Uani 1 1 d . . . . .
H20A H 0.2215 0.7371 0.6066 0.036 Uiso 1 1 calc R . . . .
H20B H 0.2545 0.9017 0.5551 0.036 Uiso 1 1 calc R . . . .
C21 C 0.30532(7) 0.6021(3) 0.60655(8) 0.0356(3) Uani 1 1 d . . . . .
H21A H 0.2987 0.4225 0.6215 0.043 Uiso 1 1 calc R . . . .
H21B H 0.3322 0.5958 0.5719 0.043 Uiso 1 1 calc R . . . .
C22 C 0.33250(7) 0.7647(4) 0.67233(9) 0.0391(4) Uani 1 1 d . . . . .
H22A H 0.3396 0.9426 0.6564 0.047 Uiso 1 1 calc R . . . .
H22B H 0.3044 0.7768 0.7053 0.047 Uiso 1 1 calc R . . . .
C23 C 0.38988(8) 0.6534(4) 0.71343(9) 0.0435(4) Uani 1 1 d . . . . .
H23A H 0.3841 0.4685 0.7242 0.052 Uiso 1 1 calc R . . . .
H23B H 0.4195 0.6624 0.6825 0.052 Uiso 1 1 calc R . . . .
C24 C 0.41248(8) 0.7976(4) 0.78376(10) 0.0446(4) Uani 1 1 d . . . . .
H24A H 0.3823 0.7941 0.8140 0.053 Uiso 1 1 calc R . . . .
H24B H 0.4196 0.9811 0.7729 0.053 Uiso 1 1 calc R . . . .
C25 C 0.46870(9) 0.6801(5) 0.82606(10) 0.0501(5) Uani 1 1 d . . . . .
H25A H 0.4623 0.4935 0.8339 0.060 Uiso 1 1 calc R . . . .
H25B H 0.4995 0.6941 0.7968 0.060 Uiso 1 1 calc R . . . .
C26 C 0.48975(10) 0.8092(6) 0.89836(11) 0.0623(6) Uani 1 1 d . . . . .
H26A H 0.4596 0.7908 0.9283 0.075 Uiso 1 1 calc R . . . .
H26B H 0.4954 0.9967 0.8908 0.075 Uiso 1 1 calc R . . . .
C27 C 0.54705(11) 0.6924(7) 0.93874(13) 0.0816(9) Uani 1 1 d . . . . .
H27A H 0.5773 0.7114 0.9097 0.122 Uiso 1 1 calc GR . . . .
H27B H 0.5414 0.5083 0.9481 0.122 Uiso 1 1 calc GR . . . .
H27C H 0.5585 0.7840 0.9840 0.122 Uiso 1 1 calc GR . . . .
C17A C 0.3025(5) 0.981(3) 0.4437(8) 0.060(3) Uani 0.531(3) 1 d D . P A 2
H17A H 0.3195 0.9792 0.4926 0.072 Uiso 0.531(3) 1 calc R . P A 2
C16A C 0.2552(9) 0.839(4) 0.4133(15) 0.030(3) Uani 0.531(3) 1 d D . P A 2
C18A C 0.3223(9) 1.135(4) 0.3883(8) 0.066(4) Uani 0.531(3) 1 d D . P A 2
H18A H 0.3576 1.2282 0.3975 0.079 Uiso 0.531(3) 1 calc R . P A 2
C19A C 0.2882(6) 1.139(3) 0.3229(7) 0.0389(17) Uani 0.531(3) 1 d D . P A 2
H19A H 0.2937 1.2472 0.2843 0.047 Uiso 0.531(3) 1 calc R . P A 2
S1A S 0.23397(11) 0.9200(5) 0.32177(12) 0.0409(4) Uani 0.531(3) 1 d 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 N1 1.3914(19) . ?
C1 C2 1.4380(19) . ?
C1 C14 1.3884(18) . ?
N1 C15 1.3750(18) . ?
N1 C20 1.4627(17) . ?
S1 C16 1.75(3) . ?
S1 C19 1.653(14) . ?
C2 C3 1.4198(19) . ?
C2 C7 1.422(2) . ?
N2 C14 1.3686(19) . ?
N2 C15 1.3249(19) . ?
C3 C4 1.375(2) . ?
C4 C5 1.383(3) . ?
C5 C6 1.376(2) . ?
C6 C7 1.407(2) . ?
C7 C8 1.468(2) . ?
C8 C9 1.406(2) . ?
C8 C13 1.410(2) . ?
C9 C10 1.377(2) . ?
C10 C11 1.389(3) . ?
C11 C12 1.370(2) . ?
C12 C13 1.409(2) . ?
C13 C14 1.432(2) . ?
C15 C16 1.449(9) . ?
C15 C16A 1.476(8) . ?
C16 C17 1.32(3) . ?
C17 C18 1.417(19) . ?
C18 C19 1.332(12) . ?
C20 C21 1.522(2) . ?
C21 C22 1.521(2) . ?
C22 C23 1.519(2) . ?
C23 C24 1.515(2) . ?
C24 C25 1.518(2) . ?
C25 C26 1.504(3) . ?
C26 C27 1.523(3) . ?
C17A C16A 1.35(3) . ?
C17A C18A 1.431(19) . ?
C16A S1A 1.74(2) . ?
C18A C19A 1.335(11) . ?
C19A S1A 1.669(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 132.83(12) . . ?
C14 C1 N1 104.91(12) . . ?
C14 C1 C2 122.21(13) . . ?
C1 N1 C20 127.14(12) . . ?
C15 N1 C1 106.26(11) . . ?
C15 N1 C20 125.93(13) . . ?
C19 S1 C16 95.2(8) . . ?
C3 C2 C1 124.89(14) . . ?
C3 C2 C7 118.62(13) . . ?
C7 C2 C1 116.44(12) . . ?
C15 N2 C14 104.76(12) . . ?
C4 C3 C2 121.22(16) . . ?
C3 C4 C5 120.09(15) . . ?
C6 C5 C4 120.10(16) . . ?
C5 C6 C7 121.97(17) . . ?
C2 C7 C8 121.37(13) . . ?
C6 C7 C2 117.99(14) . . ?
C6 C7 C8 120.63(14) . . ?
C9 C8 C7 122.44(14) . . ?
C9 C8 C13 117.50(14) . . ?
C13 C8 C7 120.06(13) . . ?
C10 C9 C8 121.34(16) . . ?
C9 C10 C11 120.67(16) . . ?
C12 C11 C10 119.70(15) . . ?
C11 C12 C13 120.52(15) . . ?
C8 C13 C14 117.78(12) . . ?
C12 C13 C8 120.26(14) . . ?
C12 C13 C14 121.96(13) . . ?
C1 C14 C13 122.04(13) . . ?
N2 C14 C1 111.41(13) . . ?
N2 C14 C13 126.55(12) . . ?
N1 C15 C16 129.4(13) . . ?
N1 C15 C16A 122.8(11) . . ?
N2 C15 N1 112.66(13) . . ?
N2 C15 C16 117.9(13) . . ?
N2 C15 C16A 124.6(11) . . ?
C15 C16 S1 122.8(18) . . ?
C17 C16 S1 107.4(7) . . ?
C17 C16 C15 130(2) . . ?
C16 C17 C18 112.9(13) . . ?
C19 C18 C17 116.2(17) . . ?
C18 C19 S1 107.9(16) . . ?
N1 C20 C21 114.43(12) . . ?
C22 C21 C20 110.28(13) . . ?
C23 C22 C21 114.22(14) . . ?
C24 C23 C22 113.58(16) . . ?
C23 C24 C25 113.50(17) . . ?
C26 C25 C24 114.36(19) . . ?
C25 C26 C27 113.3(2) . . ?
C16A C17A C18A 108.7(14) . . ?
C15 C16A S1A 111.7(15) . . ?
C17A C16A C15 137(2) . . ?
C17A C16A S1A 111.1(8) . . ?
C19A C18A C17A 117.4(16) . . ?
C18A C19A S1A 108.8(14) . . ?
C19A S1A C16A 93.5(7) . . ?

_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_mo_181127G_0m
_database_code_depnum_ccdc_archive 'CCDC 1963679'
loop_
_audit_author_name
_audit_author_address
'yun yu'
;wuhan university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N2 S'
_chemical_formula_weight         328.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.801(3)
_cell_length_b                   11.135(3)
_cell_length_c                   27.335(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3287.5(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2225
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      21.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22629
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.490
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3056
_reflns_number_gt                2138
_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)+(0.0875P)²+2.4446P] 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         3056
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1803
_refine_ls_wR_factor_gt          0.1591
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.3221(3) -0.0292(3) 0.43718(10) 0.0380(7) Uani 1 1 d . . . . .
C2 C 0.3557(3) 0.1061(3) 0.38009(10) 0.0356(7) Uani 1 1 d . . . . .
C3 C 0.4550(3) 0.0312(3) 0.38554(10) 0.0361(7) Uani 1 1 d . . . . .
C4 C 0.5664(3) 0.0440(3) 0.35781(10) 0.0371(7) Uani 1 1 d . . . . .
C5 C 0.6672(3) -0.0329(3) 0.36326(11) 0.0459(8) Uani 1 1 d . . . . .
H5 H 0.6615 -0.0979 0.3845 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7741(3) -0.0143(3) 0.33794(11) 0.0494(8) Uani 1 1 d . . . . .
H6 H 0.8406 -0.0665 0.3418 0.059 Uiso 1 1 calc R U . . .
C7 C 0.7836(3) 0.0823(3) 0.30657(12) 0.0524(9) Uani 1 1 d . . . . .
H7 H 0.8572 0.0958 0.2898 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6858(3) 0.1580(3) 0.29990(11) 0.0489(8) Uani 1 1 d . . . . .
H8 H 0.6942 0.2226 0.2786 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5722(3) 0.1410(3) 0.32451(10) 0.0383(7) Uani 1 1 d . . . . .
C10 C 0.4657(3) 0.2183(3) 0.31767(10) 0.0402(7) Uani 1 1 d . . . . .
C11 C 0.4682(3) 0.3120(3) 0.28292(12) 0.0538(9) Uani 1 1 d . . . . .
H11 H 0.5387 0.3219 0.2638 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3714(4) 0.3883(3) 0.27637(13) 0.0601(10) Uani 1 1 d . . . . .
H12 H 0.3768 0.4498 0.2535 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2648(4) 0.3740(3) 0.30392(12) 0.0589(10) Uani 1 1 d . . . . .
H13 H 0.1985 0.4262 0.2995 0.071 Uiso 1 1 calc R U . . .
C14 C 0.2565(3) 0.2833(3) 0.33767(11) 0.0478(8) Uani 1 1 d . . . . .
H14 H 0.1841 0.2743 0.3557 0.057 Uiso 1 1 calc R U . . .
C15 C 0.3555(3) 0.2036(3) 0.34548(10) 0.0387(7) Uani 1 1 d . . . . .
C16 C 0.2672(3) -0.0989(3) 0.47704(11) 0.0427(7) Uani 1 1 d . . . . .
C17 C 0.3342(3) -0.1325(3) 0.51932(11) 0.0508(8) Uani 1 1 d . . . . .
H17 H 0.4130 -0.1060 0.5278 0.061 Uiso 1 1 calc R U . . .
C18 C 0.2588(4) -0.2152(4) 0.54700(13) 0.0704(12) Uani 1 1 d . . . . .
H18 H 0.2844 -0.2482 0.5766 0.085 Uiso 1 1 calc R U . . .
C19 C 0.1488(4) -0.2409(4) 0.52669(13) 0.0625(10) Uani 1 1 d . . . . .
H19 H 0.0919 -0.2938 0.5404 0.075 Uiso 1 1 calc R U . . .
C20 C 0.1458(3) 0.1139(3) 0.42437(12) 0.0466(8) Uani 1 1 d . . . . .
H20A H 0.1485 0.2009 0.4233 0.056 Uiso 1 1 calc R U . . .
H20B H 0.1216 0.0903 0.4572 0.056 Uiso 1 1 calc R U . . .
C21 C 0.0508(3) 0.0694(4) 0.38851(16) 0.0717(12) Uani 1 1 d . . . . .
H21A H 0.0745 0.0925 0.3560 0.108 Uiso 1 1 calc R U . . .
H21B H -0.0283 0.1038 0.3962 0.108 Uiso 1 1 calc R U . . .
H21C H 0.0456 -0.0165 0.3904 0.108 Uiso 1 1 calc R U . . .
N1 N 0.2696(2) 0.0660(2) 0.41375(8) 0.0377(6) Uani 1 1 d . . . . .
N2 N 0.4348(2) -0.0537(2) 0.42108(9) 0.0394(6) Uani 1 1 d . . . . .
S1 S 0.12491(9) -0.16759(9) 0.47408(4) 0.0610(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 N2 1.322(4) . ?
C1 N1 1.362(4) . ?
C1 C16 1.463(4) . ?
C2 C3 1.367(4) . ?
C2 N1 1.383(4) . ?
C2 C15 1.440(4) . ?
C3 N2 1.373(4) . ?
C3 C4 1.429(4) . ?
C4 C5 1.394(4) . ?
C4 C9 1.414(4) . ?
C5 C6 1.362(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.413(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.449(4) . ?
C10 C11 1.411(4) . ?
C10 C15 1.422(4) . ?
C11 C12 1.359(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.405(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.414(4) . ?
C16 S1 1.719(3) . ?
C17 C18 1.444(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.342(5) . ?
C18 H18 0.9300 . ?
C19 S1 1.673(4) . ?
C19 H19 0.9300 . ?
C20 N1 1.468(4) . ?
C20 C21 1.503(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 112.8(3) . . ?
N2 C1 C16 120.8(3) . . ?
N1 C1 C16 126.4(3) . . ?
C3 C2 N1 104.9(2) . . ?
C3 C2 C15 122.2(3) . . ?
N1 C2 C15 132.8(3) . . ?
C2 C3 N2 111.9(2) . . ?
C2 C3 C4 122.8(3) . . ?
N2 C3 C4 125.3(3) . . ?
C5 C4 C9 120.2(3) . . ?
C5 C4 C3 122.7(3) . . ?
C9 C4 C3 117.1(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.7(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C4 116.6(3) . . ?
C8 C9 C10 123.3(3) . . ?
C4 C9 C10 120.1(3) . . ?
C11 C10 C15 117.4(3) . . ?
C11 C10 C9 120.8(3) . . ?
C15 C10 C9 121.8(3) . . ?
C12 C11 C10 122.4(3) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 118.9(3) . . ?
C14 C15 C2 125.2(3) . . ?
C10 C15 C2 115.9(3) . . ?
C17 C16 C1 122.8(3) . . ?
C17 C16 S1 112.2(2) . . ?
C1 C16 S1 124.3(2) . . ?
C16 C17 C18 108.0(3) . . ?
C16 C17 H17 126.0 . . ?
C18 C17 H17 126.0 . . ?
C19 C18 C17 114.8(3) . . ?
C19 C18 H18 122.6 . . ?
C17 C18 H18 122.6 . . ?
C18 C19 S1 112.8(3) . . ?
C18 C19 H19 123.6 . . ?
S1 C19 H19 123.6 . . ?
N1 C20 C21 111.9(3) . . ?
N1 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
N1 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
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 . . ?
C1 N1 C2 106.5(2) . . ?
C1 N1 C20 124.7(3) . . ?
C2 N1 C20 128.8(3) . . ?
C1 N2 C3 103.9(2) . . ?
C19 S1 C16 92.23(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.1(3) . . . . ?
C15 C2 C3 N2 179.1(2) . . . . ?
N1 C2 C3 C4 -178.6(3) . . . . ?
C15 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 -179.7(3) . . . . ?
N2 C3 C4 C5 2.0(5) . . . . ?
C2 C3 C4 C9 1.6(4) . . . . ?
N2 C3 C4 C9 -176.8(3) . . . . ?
C9 C4 C5 C6 2.0(5) . . . . ?
C3 C4 C5 C6 -176.7(3) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C8 C9 C4 2.3(4) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
C5 C4 C9 C8 -3.2(4) . . . . ?
C3 C4 C9 C8 175.6(3) . . . . ?
C5 C4 C9 C10 177.9(3) . . . . ?
C3 C4 C9 C10 -3.3(4) . . . . ?
C8 C9 C10 C11 4.2(4) . . . . ?
C4 C9 C10 C11 -177.0(3) . . . . ?
C8 C9 C10 C15 -175.6(3) . . . . ?
C4 C9 C10 C15 3.2(4) . . . . ?
C15 C10 C11 C12 1.6(5) . . . . ?
C9 C10 C11 C12 -178.2(3) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 C10 0.0(4) . . . . ?
C13 C14 C15 C2 179.8(3) . . . . ?
C11 C10 C15 C14 -1.0(4) . . . . ?
C9 C10 C15 C14 178.8(3) . . . . ?
C11 C10 C15 C2 179.2(3) . . . . ?
C9 C10 C15 C2 -1.0(4) . . . . ?
C3 C2 C15 C14 179.4(3) . . . . ?
N1 C2 C15 C14 -1.7(5) . . . . ?
C3 C2 C15 C10 -0.8(4) . . . . ?
N1 C2 C15 C10 178.1(3) . . . . ?
N2 C1 C16 C17 42.7(4) . . . . ?
N1 C1 C16 C17 -135.4(3) . . . . ?
N2 C1 C16 S1 -127.0(3) . . . . ?
N1 C1 C16 S1 54.8(4) . . . . ?
C1 C16 C17 C18 -171.2(3) . . . . ?
S1 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C17 C18 C19 S1 -1.1(5) . . . . ?
N2 C1 N1 C2 -0.4(3) . . . . ?
C16 C1 N1 C2 178.0(3) . . . . ?
N2 C1 N1 C20 -179.4(3) . . . . ?
C16 C1 N1 C20 -1.1(4) . . . . ?
C3 C2 N1 C1 0.2(3) . . . . ?
C15 C2 N1 C1 -178.8(3) . . . . ?
C3 C2 N1 C20 179.2(3) . . . . ?
C15 C2 N1 C20 0.1(5) . . . . ?
C21 C20 N1 C1 -99.2(4) . . . . ?
C21 C20 N1 C2 82.0(4) . . . . ?
N1 C1 N2 C3 0.3(3) . . . . ?
C16 C1 N2 C3 -178.1(3) . . . . ?
C2 C3 N2 C1 -0.1(3) . . . . ?
C4 C3 N2 C1 178.4(3) . . . . ?
C18 C19 S1 C16 0.7(3) . . . . ?
C17 C16 S1 C19 -0.2(3) . . . . ?
C1 C16 S1 C19 170.5(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
C21 H21C S1 0.96 2.97 3.616(5) 126.2 .
C20 H20B S1 0.97 2.91 3.424(4) 114.3 .
C19 H19 N2 0.93 2.62 3.551(4) 178.9 4_446
C21 H21C S1 0.96 2.97 3.616(5) 126.2 .
C20 H20B S1 0.97 2.91 3.424(4) 114.3 .
C19 H19 N2 0.93 2.62 3.551(4) 178.9 4_446
C21 H21C S1 0.96 2.97 3.616(5) 126.2 .
C20 H20B S1 0.97 2.91 3.424(4) 114.3 .
C19 H19 N2 0.93 2.62 3.551(4) 178.9 4_446
C19 H19 N2 0.93 2.62 3.551(4) 178.9 4_446
C20 H20B S1 0.97 2.91 3.424(4) 114.3 .
C21 H21C S1 0.96 2.97 3.616(5) 126.2 .
C19 H19 N2 0.93 2.62 3.551(4) 178.9 4_446
C20 H20B S1 0.97 2.91 3.424(4) 114.3 .
C21 H21C S1 0.96 2.97 3.616(5) 126.2 .
C19 H19 N2 0.93 2.62 3.551(4) 178.9 4_446
C20 H20B S1 0.97 2.91 3.424(4) 114.3 .
C21 H21C S1 0.96 2.97 3.616(5) 126.2 .

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.058



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

data_T
_database_code_depnum_ccdc_archive 'CCDC 1963683'
loop_
_audit_author_name
_audit_author_address
'yun yu'
;wuhan university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 N2 S'
_chemical_formula_weight         384.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.753(4)
_cell_length_b                   9.213(3)
_cell_length_c                   20.432(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.04(3)
_cell_angle_gamma                90
_cell_volume                     1987.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3226
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.90

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18431
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         29.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5358
_reflns_number_gt                3125
_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)+(0.0100P)²+2.0000P] 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         5358
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.34447(7) -0.21446(8) 0.69643(4) 0.0521(2) Uani 1 1 d . . . . .
N1 N 0.43926(18) 0.0821(2) 0.84285(10) 0.0324(4) Uani 1 1 d . . . . .
N2 N 0.58104(18) -0.0720(2) 0.83708(11) 0.0351(5) Uani 1 1 d . . . . .
C1 C 0.4697(2) -0.0113(3) 0.80096(13) 0.0331(5) Uani 1 1 d . . . . .
C2 C 0.5399(2) 0.0796(3) 0.91111(12) 0.0323(5) Uani 1 1 d . . . . .
C3 C 0.6250(2) -0.0164(3) 0.90559(13) 0.0338(5) Uani 1 1 d . . . . .
C4 C 0.7442(2) -0.0480(3) 0.96598(13) 0.0378(6) Uani 1 1 d . . . . .
C5 C 0.8308(2) -0.1424(3) 0.95943(16) 0.0486(7) Uani 1 1 d . . . . .
H5 H 0.8116 -0.1863 0.9148 0.058 Uiso 1 1 calc R U . . .
C6 C 0.9435(3) -0.1716(4) 1.01765(18) 0.0621(8) Uani 1 1 d . . . . .
H6 H 1.0008 -0.2353 1.0129 0.075 Uiso 1 1 calc R U . . .
C7 C 0.9719(3) -0.1055(4) 1.08399(18) 0.0659(9) Uani 1 1 d . . . . .
H7 H 1.0487 -0.1252 1.1239 0.079 Uiso 1 1 calc R U . . .
C8 C 0.8882(3) -0.0117(4) 1.09121(16) 0.0558(8) Uani 1 1 d . . . . .
H8 H 0.9092 0.0320 1.1361 0.067 Uiso 1 1 calc R U . . .
C9 C 0.7713(2) 0.0201(3) 1.03257(14) 0.0409(6) Uani 1 1 d . . . . .
C10 C 0.6786(3) 0.1197(3) 1.03858(13) 0.0404(6) Uani 1 1 d . . . . .
C11 C 0.7017(3) 0.1854(3) 1.10521(15) 0.0530(7) Uani 1 1 d . . . . .
H11 H 0.7760 0.1629 1.1462 0.064 Uiso 1 1 calc R U . . .
C12 C 0.6195(3) 0.2803(3) 1.11164(17) 0.0584(8) Uani 1 1 d . . . . .
H12 H 0.6380 0.3222 1.1566 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5087(3) 0.3153(3) 1.05206(17) 0.0587(8) Uani 1 1 d . . . . .
H13 H 0.4528 0.3817 1.0565 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4811(3) 0.2520(3) 0.98630(15) 0.0478(7) Uani 1 1 d . . . . .
H14 H 0.4059 0.2757 0.9462 0.057 Uiso 1 1 calc R U . . .
C15 C 0.5638(2) 0.1519(3) 0.97804(13) 0.0371(5) Uani 1 1 d . . . . .
C16 C 0.3888(2) -0.0391(3) 0.72466(13) 0.0358(5) Uani 1 1 d . . . . .
C17 C 0.3452(3) 0.0521(3) 0.66663(14) 0.0464(6) Uani 1 1 d . . . . .
H17 H 0.3593 0.1517 0.6704 0.056 Uiso 1 1 calc R U . . .
C18 C 0.2763(3) -0.0199(4) 0.60016(15) 0.0525(7) Uani 1 1 d . . . . .
H18 H 0.2398 0.0270 0.5553 0.063 Uiso 1 1 calc R U . . .
C19 C 0.2691(2) -0.1640(3) 0.60843(15) 0.0510(7) Uani 1 1 d . . . . .
H19 H 0.2273 -0.2281 0.5701 0.061 Uiso 1 1 calc R U . . .
C20 C 0.3176(2) 0.1560(3) 0.81858(14) 0.0367(5) Uani 1 1 d . . . . .
H20A H 0.2909 0.1517 0.8572 0.044 Uiso 1 1 calc R U . . .
H20B H 0.2550 0.1047 0.7769 0.044 Uiso 1 1 calc R U . . .
C21 C 0.3209(2) 0.3133(3) 0.79786(15) 0.0428(6) Uani 1 1 d . . . . .
H21A H 0.3434 0.3178 0.7575 0.051 Uiso 1 1 calc R U . . .
H21B H 0.3859 0.3641 0.8388 0.051 Uiso 1 1 calc R U . . .
C22 C 0.1944(3) 0.3893(3) 0.77612(16) 0.0535(7) Uani 1 1 d . . . . .
H22A H 0.1955 0.4803 0.7526 0.064 Uiso 1 1 calc R U . . .
H22B H 0.1281 0.3295 0.7407 0.064 Uiso 1 1 calc R U . . .
C23 C 0.1617(3) 0.4204(3) 0.83874(16) 0.0512(7) Uani 1 1 d . . . . .
H23A H 0.2317 0.4716 0.8766 0.061 Uiso 1 1 calc R U . . .
H23B H 0.1510 0.3290 0.8590 0.061 Uiso 1 1 calc R U . . .
C24 C 0.0421(3) 0.5099(4) 0.8164(2) 0.0745(10) Uani 1 1 d . . . . .
H24A H 0.0476 0.5947 0.7897 0.089 Uiso 1 1 calc R U . . .
H24B H -0.0300 0.4528 0.7839 0.089 Uiso 1 1 calc R U . . .
C25 C 0.0208(4) 0.5585(5) 0.8805(2) 0.0835(12) Uani 1 1 d . . . . .
H25A H 0.0136 0.4750 0.9065 0.125 Uiso 1 1 calc R U . . .
H25B H -0.0558 0.6144 0.8635 0.125 Uiso 1 1 calc R U . . .
H25C H 0.0909 0.6170 0.9122 0.125 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 C19 1.684(3) . ?
S1 C16 1.718(3) . ?
N1 C1 1.368(3) . ?
N1 C2 1.377(3) . ?
N1 C20 1.460(3) . ?
N2 C1 1.312(3) . ?
N2 C3 1.362(3) . ?
C1 C16 1.449(3) . ?
C2 C3 1.376(3) . ?
C2 C15 1.434(3) . ?
C3 C4 1.433(3) . ?
C4 C5 1.389(4) . ?
C4 C9 1.402(4) . ?
C5 C6 1.363(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.470(4) . ?
C10 C11 1.403(4) . ?
C10 C15 1.405(4) . ?
C11 C12 1.352(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.402(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.356(4) . ?
C17 C18 1.405(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.346(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.515(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.522(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.516(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.517(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.506(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 S1 C16 92.22(14) . . ?
C1 N1 C2 106.19(19) . . ?
C1 N1 C20 124.6(2) . . ?
C2 N1 C20 129.01(19) . . ?
C1 N2 C3 104.6(2) . . ?
N2 C1 N1 112.7(2) . . ?
N2 C1 C16 123.5(2) . . ?
N1 C1 C16 123.8(2) . . ?
C3 C2 N1 105.0(2) . . ?
C3 C2 C15 122.1(2) . . ?
N1 C2 C15 132.8(2) . . ?
N2 C3 C2 111.4(2) . . ?
N2 C3 C4 126.5(2) . . ?
C2 C3 C4 122.1(2) . . ?
C5 C4 C9 120.7(2) . . ?
C5 C4 C3 121.7(2) . . ?
C9 C4 C3 117.7(2) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 117.1(3) . . ?
C8 C9 C10 122.9(3) . . ?
C4 C9 C10 120.0(2) . . ?
C11 C10 C15 117.7(3) . . ?
C11 C10 C9 121.0(3) . . ?
C15 C10 C9 121.3(2) . . ?
C12 C11 C10 122.1(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 118.8(2) . . ?
C14 C15 C2 124.4(2) . . ?
C10 C15 C2 116.9(2) . . ?
C17 C16 C1 130.5(2) . . ?
C17 C16 S1 110.3(2) . . ?
C1 C16 S1 119.09(18) . . ?
C16 C17 C18 112.9(3) . . ?
C16 C17 H17 123.5 . . ?
C18 C17 H17 123.5 . . ?
C19 C18 C17 112.7(3) . . ?
C19 C18 H18 123.7 . . ?
C17 C18 H18 123.7 . . ?
C18 C19 S1 111.9(2) . . ?
C18 C19 H19 124.0 . . ?
S1 C19 H19 124.0 . . ?
N1 C20 C21 113.5(2) . . ?
N1 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
N1 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 112.3(2) . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C21 114.7(2) . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 113.2(3) . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 112.7(3) . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C3 N2 C1 N1 0.3(3) . . . . ?
C3 N2 C1 C16 179.5(2) . . . . ?
C2 N1 C1 N2 -0.2(3) . . . . ?
C20 N1 C1 N2 -175.0(2) . . . . ?
C2 N1 C1 C16 -179.3(2) . . . . ?
C20 N1 C1 C16 5.8(4) . . . . ?
C1 N1 C2 C3 0.0(2) . . . . ?
C20 N1 C2 C3 174.5(2) . . . . ?
C1 N1 C2 C15 -179.1(2) . . . . ?
C20 N1 C2 C15 -4.6(4) . . . . ?
C1 N2 C3 C2 -0.3(3) . . . . ?
C1 N2 C3 C4 -179.4(2) . . . . ?
N1 C2 C3 N2 0.2(3) . . . . ?
C15 C2 C3 N2 179.5(2) . . . . ?
N1 C2 C3 C4 179.4(2) . . . . ?
C15 C2 C3 C4 -1.4(4) . . . . ?
N2 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C4 C5 -178.5(2) . . . . ?
N2 C3 C4 C9 -179.5(2) . . . . ?
C2 C3 C4 C9 1.5(3) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
C3 C4 C5 C6 -179.6(3) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 C4 -0.3(4) . . . . ?
C7 C8 C9 C10 179.5(3) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C3 C4 C9 C8 179.9(2) . . . . ?
C5 C4 C9 C10 -179.9(2) . . . . ?
C3 C4 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 -2.0(4) . . . . ?
C4 C9 C10 C11 177.9(2) . . . . ?
C8 C9 C10 C15 178.3(2) . . . . ?
C4 C9 C10 C15 -1.9(4) . . . . ?
C15 C10 C11 C12 -2.1(4) . . . . ?
C9 C10 C11 C12 178.1(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C14 0.9(5) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C10 -1.6(4) . . . . ?
C13 C14 C15 C2 178.9(3) . . . . ?
C11 C10 C15 C14 2.7(4) . . . . ?
C9 C10 C15 C14 -177.5(2) . . . . ?
C11 C10 C15 C2 -177.8(2) . . . . ?
C9 C10 C15 C2 2.0(3) . . . . ?
C3 C2 C15 C14 179.1(2) . . . . ?
N1 C2 C15 C14 -1.9(4) . . . . ?
C3 C2 C15 C10 -0.4(3) . . . . ?
N1 C2 C15 C10 178.6(2) . . . . ?
N2 C1 C16 C17 -118.1(3) . . . . ?
N1 C1 C16 C17 61.0(4) . . . . ?
N2 C1 C16 S1 56.8(3) . . . . ?
N1 C1 C16 S1 -124.1(2) . . . . ?
C19 S1 C16 C17 0.0(2) . . . . ?
C19 S1 C16 C1 -175.8(2) . . . . ?
C1 C16 C17 C18 175.3(2) . . . . ?
S1 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 S1 0.3(3) . . . . ?
C16 S1 C19 C18 -0.2(2) . . . . ?
C1 N1 C20 C21 -101.8(3) . . . . ?
C2 N1 C20 C21 84.5(3) . . . . ?
N1 C20 C21 C22 -177.4(2) . . . . ?
C20 C21 C22 C23 71.9(3) . . . . ?
C21 C22 C23 C24 173.9(3) . . . . ?
C22 C23 C24 C25 -171.7(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
C17 H17 N2 0.93 2.66 3.579(4) 168.7 2_656
C21 H21A N2 0.97 2.66 3.583(3) 159.4 2_656

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.374
_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_t_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1963681'
loop_
_audit_author_name
_audit_author_address
'yun yu'
;wuhan university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_audit_creation_date             2018-11-28
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 S, 0.5(H2 O)'
_chemical_formula_sum            'C23 H21 N2 O0.50 S'
_chemical_formula_weight         365.49
_chemical_absolute_configuration ?
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'

_cell_length_a                   14.577(8)
_cell_length_b                   25.798(15)
_cell_length_c                   9.910(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3727(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1351
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.01
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1387 before and 0.0665 after correction. 
The Ratio of minimum to maximum transmission is 0.7536. 
The λ/2 correction factor is 0.0015. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1544
_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  0.0836
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12575
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.267
_diffrn_reflns_theta_min         1.579
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                1910
_reflns_number_total             3281
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
; 
 Flack x determined using 658 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.28(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1583P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2542
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H,H) groups 
2. Restrained distances 
 C1-C16 \\sim C1-C16' 
 with sigma of 0.01 
3. Uiso/Uaniso restraints and constraints 
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) 
\\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(C16') \\sim Ueq, Uanis(C17') \\sim Ueq, 
Uanis(C18') \\sim Ueq, Uanis(C19') \\sim Ueq, Uanis(S1') \\sim Ueq: with sigma 
of 0.01 and sigma for terminal atoms of 0.02 
Uanis(C17') \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for 
terminal atoms of 0.01 
Uanis(C16) \\sim Ueq, Uanis(C16') \\sim Ueq: with sigma of 0.005 and sigma for 
terminal atoms of 0.01 
Uanis(S1) = Uanis(S1') 
Uanis(C19) = Uanis(C19') 
Uanis(C18) = Uanis(C18') 
4. Same fragment restrains 
{C16, C17, C18, C19, S1} sigma for 1-2: 0.02, 1-3: 0.04 
as 
{C16', C17', C18', C19', S1'} 
5. Others 
 Sof(C16')=Sof(C17')=Sof(H17')=Sof(C18')=Sof(H18')=Sof(C19')=Sof(H19')= 
 Sof(S1')=1-FVAR(1) 
 Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(S1)=FVAR(1) 
 Fixed Sof: H1A(0.5) H1B(0.5) 
6.a Riding coordinates: 
 O1(H1A,H1B) 
6.b Secondary CH2 refined with riding coordinates: 
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B) 
6.c Aromatic/amide H refined with riding coordinates: 
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), 
 C17(H17), C18(H18), C19(H19), C17'(H17'), C18'(H18'), C19'(H19') 
6.d Idealised Me refined as rotating group: 
 C23(H23A,H23B,H23C) 
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.2414(6) 0.4491(3) 0.3929(9) 0.058(2) Uani 1 1 d D . . . .
C2 C 0.2263(5) 0.3846(3) 0.2503(9) 0.053(2) Uani 1 1 d . . . . .
C3 C 0.1446(5) 0.3962(3) 0.3110(8) 0.052(2) Uani 1 1 d . . . . .
C4 C 0.0632(5) 0.3663(3) 0.2880(8) 0.052(2) Uani 1 1 d . . . . .
C5 C -0.0177(5) 0.3750(3) 0.3576(9) 0.058(2) Uani 1 1 d . . . . .
H5 H -0.0202 0.4017 0.4206 0.069 Uiso 1 1 calc R . . . .
C6 C -0.0933(6) 0.3455(3) 0.3361(10) 0.068(2) Uani 1 1 d . . . . .
H6 H -0.1479 0.3528 0.3808 0.081 Uiso 1 1 calc R . . . .
C7 C -0.0881(7) 0.3047(4) 0.2470(11) 0.073(3) Uani 1 1 d . . . . .
H7 H -0.1392 0.2839 0.2321 0.087 Uiso 1 1 calc R . . . .
C8 C -0.0093(6) 0.2948(4) 0.1816(10) 0.069(2) Uani 1 1 d . . . . .
H8 H -0.0075 0.2668 0.1225 0.083 Uiso 1 1 calc R . . . .
C9 C 0.0702(5) 0.3244(3) 0.1977(8) 0.054(2) Uani 1 1 d . . . . .
C10 C 0.1559(5) 0.3123(3) 0.1310(8) 0.055(2) Uani 1 1 d . . . . .
C11 C 0.1627(6) 0.2706(4) 0.0416(10) 0.068(3) Uani 1 1 d . . . . .
H11 H 0.1113 0.2504 0.0234 0.081 Uiso 1 1 calc R . . . .
C12 C 0.2443(7) 0.2592(3) -0.0193(10) 0.076(3) Uani 1 1 d . . . . .
H12 H 0.2470 0.2312 -0.0781 0.091 Uiso 1 1 calc R . . . .
C13 C 0.3218(6) 0.2874(3) 0.0028(10) 0.062(2) Uani 1 1 d . . . . .
H13 H 0.3765 0.2787 -0.0401 0.074 Uiso 1 1 calc R . . . .
C14 C 0.3178(6) 0.3281(3) 0.0882(9) 0.059(2) Uani 1 1 d . . . . .
H14 H 0.3705 0.3476 0.1027 0.071 Uiso 1 1 calc R . . . .
C15 C 0.2356(5) 0.3422(3) 0.1568(8) 0.0504(19) Uani 1 1 d . . . . .
C16 C 0.2873(18) 0.4899(10) 0.472(4) 0.094(13) Uani 0.64(5) 1 d D U . A 1
C17 C 0.3724(9) 0.4858(8) 0.5527(18) 0.027(4) Uani 0.64(5) 1 d D U . A 1
H17 H 0.4151 0.4590 0.5516 0.032 Uiso 0.64(5) 1 calc R . . A 1
C18 C 0.3747(15) 0.5315(11) 0.631(3) 0.087(6) Uani 0.64(5) 1 d D U . A 1
H18 H 0.4251 0.5389 0.6855 0.104 Uiso 0.64(5) 1 calc R . . A 1
C19 C 0.3029(16) 0.5639(10) 0.627(3) 0.087(6) Uani 0.64(5) 1 d D U . A 1
H19 H 0.2964 0.5935 0.6793 0.104 Uiso 0.64(5) 1 calc R . . A 1
S1 S 0.2250(15) 0.5426(8) 0.510(2) 0.116(4) Uani 0.64(5) 1 d D U . A 1
C16' C 0.2763(18) 0.4914(9) 0.478(3) 0.029(9) Uani 0.36(5) 1 d D U . A 2
C17' C 0.3727(15) 0.4998(12) 0.525(3) 0.021(6) Uani 0.36(5) 1 d D U . A 2
H17' H 0.4243 0.4798 0.5071 0.025 Uiso 0.36(5) 1 calc R . . A 2
C18' C 0.366(3) 0.5466(17) 0.605(5) 0.087(6) Uani 0.36(5) 1 d D U . A 2
H18' H 0.4121 0.5558 0.6660 0.104 Uiso 0.36(5) 1 calc R . . A 2
C19' C 0.291(3) 0.5765(14) 0.587(6) 0.087(6) Uani 0.36(5) 1 d D U . A 2
H19' H 0.2868 0.6121 0.6006 0.104 Uiso 0.36(5) 1 calc R . . A 2
S1' S 0.2051(18) 0.5367(14) 0.533(5) 0.116(4) Uani 0.36(5) 1 d D U . A 2
C20 C 0.3848(5) 0.4260(3) 0.2650(9) 0.055(2) Uani 1 1 d . . . . .
H20A H 0.4045 0.4606 0.2903 0.066 Uiso 1 1 calc R . . . .
H20B H 0.3903 0.4230 0.1678 0.066 Uiso 1 1 calc R . . . .
C21 C 0.4482(6) 0.3861(3) 0.3320(10) 0.068(2) Uani 1 1 d . . . . .
H21A H 0.4511 0.3929 0.4282 0.081 Uiso 1 1 calc R . . . .
H21B H 0.4230 0.3517 0.3193 0.081 Uiso 1 1 calc R . . . .
C22 C 0.5421(6) 0.3880(5) 0.2748(14) 0.089(3) Uani 1 1 d . . . . .
H22A H 0.5687 0.4217 0.2943 0.107 Uiso 1 1 calc R . . . .
H22B H 0.5383 0.3845 0.1775 0.107 Uiso 1 1 calc R . . . .
C23 C 0.6051(8) 0.3463(5) 0.3292(15) 0.106(4) Uani 1 1 d . . . . .
H23A H 0.6022 0.3461 0.4260 0.159 Uiso 1 1 calc GR . . . .
H23B H 0.6669 0.3532 0.3011 0.159 Uiso 1 1 calc GR . . . .
H23C H 0.5862 0.3132 0.2951 0.159 Uiso 1 1 calc GR . . . .
N1 N 0.1530(5) 0.4366(2) 0.3996(8) 0.0590(18) Uani 1 1 d . . . . .
N2 N 0.2893(4) 0.4194(2) 0.3027(7) 0.0561(18) Uani 1 1 d . . . . .
O1 O 0.0000 0.5000 0.5293(15) 0.120(4) Uani 1 2 d S T P . .
H1A H -0.0340 0.4732 0.5311 0.181 Uiso 0.5 1 d R . . . .
H1B H 0.0525 0.4891 0.5536 0.181 Uiso 0.5 1 d R . . . .


_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 C16 1.475(14) . ?
C1 C16' 1.469(14) . ?
C1 N1 1.331(11) . ?
C1 N2 1.368(10) . ?
C2 C3 1.368(11) . ?
C2 C15 1.440(11) . ?
C2 N2 1.387(10) . ?
C3 C4 1.434(11) . ?
C3 N1 1.369(10) . ?
C4 C5 1.383(11) . ?
C4 C9 1.407(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.356(12) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.343(13) . ?
C8 H8 0.9300 . ?
C8 C9 1.397(12) . ?
C9 C10 1.447(11) . ?
C10 C11 1.398(12) . ?
C10 C15 1.418(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(13) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.351(13) . ?
C14 H14 0.9300 . ?
C14 C15 1.424(12) . ?
C16 C17 1.48(2) . ?
C16 S1 1.678(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.414(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.34(2) . ?
C19 H19 0.9300 . ?
C19 S1 1.709(19) . ?
C16' C17' 1.50(2) . ?
C16' S1' 1.66(2) . ?
C17' H17' 0.9300 . ?
C17' C18' 1.45(2) . ?
C18' H18' 0.9300 . ?
C18' C19' 1.36(3) . ?
C19' H19' 0.9300 . ?
C19' S1' 1.70(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.534(12) . ?
C20 N2 1.451(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.482(13) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.514(15) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O1 H1A 0.8501 . ?
O1 H1B 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C16 125.8(15) . . ?
N1 C1 C16' 119.1(13) . . ?
N1 C1 N2 113.1(7) . . ?
N2 C1 C16 121.1(15) . . ?
N2 C1 C16' 127.8(14) . . ?
C3 C2 C15 122.1(7) . . ?
C3 C2 N2 105.7(7) . . ?
N2 C2 C15 132.1(7) . . ?
C2 C3 C4 122.2(7) . . ?
C2 C3 N1 111.8(7) . . ?
N1 C3 C4 125.9(7) . . ?
C5 C4 C3 122.6(7) . . ?
C5 C4 C9 120.2(7) . . ?
C9 C4 C3 117.0(7) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.5(8) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.0(9) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(9) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 118.3 . . ?
C7 C8 C9 123.4(9) . . ?
C9 C8 H8 118.3 . . ?
C4 C9 C10 121.3(7) . . ?
C8 C9 C4 115.6(8) . . ?
C8 C9 C10 123.1(7) . . ?
C11 C10 C9 121.1(7) . . ?
C11 C10 C15 118.3(7) . . ?
C15 C10 C9 120.5(7) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(8) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 118.7 . . ?
C13 C12 C11 122.5(8) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.6(8) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.3(8) . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C2 116.8(7) . . ?
C10 C15 C14 117.7(7) . . ?
C14 C15 C2 125.5(7) . . ?
C1 C16 C17 128.1(17) . . ?
C1 C16 S1 116.9(15) . . ?
C17 C16 S1 113.1(11) . . ?
C16 C17 H17 127.6 . . ?
C18 C17 C16 104.9(12) . . ?
C18 C17 H17 127.6 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.9(14) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 125.0 . . ?
C18 C19 S1 110.0(12) . . ?
S1 C19 H19 125.0 . . ?
C16 S1 C19 93.0(10) . . ?
C1 C16' C17' 127.7(18) . . ?
C1 C16' S1' 119.8(18) . . ?
C17' C16' S1' 112.4(13) . . ?
C16' C17' H17' 128.2 . . ?
C18' C17' C16' 103.5(16) . . ?
C18' C17' H17' 128.2 . . ?
C17' C18' H18' 121.6 . . ?
C19' C18' C17' 117(2) . . ?
C19' C18' H18' 121.6 . . ?
C18' C19' H19' 126.4 . . ?
C18' C19' S1' 107(2) . . ?
S1' C19' H19' 126.4 . . ?
C16' S1' C19' 93.9(14) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
N2 C20 H20A 109.0 . . ?
N2 C20 H20B 109.0 . . ?
N2 C20 C21 112.8(7) . . ?
C20 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 C20 111.7(8) . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C21 C22 C23 113.6(9) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C3 103.8(6) . . ?
C1 N2 C2 105.6(6) . . ?
C1 N2 C20 126.3(7) . . ?
C2 N2 C20 128.0(7) . . ?
H1A O1 H1B 104.5 . . ?

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
C1 C16 C17 C18 -167(3) . . . . ?
C1 C16 S1 C19 167(3) . . . . ?
C1 C16' C17' C18' -180(4) . . . . ?
C1 C16' S1' C19' -168(3) . . . . ?
C2 C3 C4 C5 174.3(8) . . . . ?
C2 C3 C4 C9 -1.0(11) . . . . ?
C2 C3 N1 C1 -0.6(8) . . . . ?
C3 C2 C15 C10 -0.7(11) . . . . ?
C3 C2 C15 C14 179.1(8) . . . . ?
C3 C2 N2 C1 0.9(8) . . . . ?
C3 C2 N2 C20 -175.4(7) . . . . ?
C3 C4 C5 C6 -178.7(8) . . . . ?
C3 C4 C9 C8 177.6(8) . . . . ?
C3 C4 C9 C10 -0.2(11) . . . . ?
C4 C3 N1 C1 175.4(8) . . . . ?
C4 C5 C6 C7 2.8(13) . . . . ?
C4 C9 C10 C11 179.9(8) . . . . ?
C4 C9 C10 C15 0.9(12) . . . . ?
C5 C4 C9 C8 2.2(11) . . . . ?
C5 C4 C9 C10 -175.6(7) . . . . ?
C5 C6 C7 C8 -0.8(14) . . . . ?
C6 C7 C8 C9 -0.5(15) . . . . ?
C7 C8 C9 C4 -0.2(13) . . . . ?
C7 C8 C9 C10 177.5(9) . . . . ?
C8 C9 C10 C11 2.3(13) . . . . ?
C8 C9 C10 C15 -176.7(8) . . . . ?
C9 C4 C5 C6 -3.6(13) . . . . ?
C9 C10 C11 C12 -179.2(8) . . . . ?
C9 C10 C15 C2 -0.5(11) . . . . ?
C9 C10 C15 C14 179.8(7) . . . . ?
C10 C11 C12 C13 -0.2(15) . . . . ?
C11 C10 C15 C2 -179.5(7) . . . . ?
C11 C10 C15 C14 0.8(11) . . . . ?
C11 C12 C13 C14 0.0(14) . . . . ?
C12 C13 C14 C15 0.7(13) . . . . ?
C13 C14 C15 C2 179.2(8) . . . . ?
C13 C14 C15 C10 -1.0(12) . . . . ?
C15 C2 C3 C4 1.4(12) . . . . ?
C15 C2 C3 N1 177.6(7) . . . . ?
C15 C2 N2 C1 -176.6(8) . . . . ?
C15 C2 N2 C20 7.1(14) . . . . ?
C15 C10 C11 C12 -0.2(13) . . . . ?
C16 C1 N1 C3 -178(2) . . . . ?
C16 C1 N2 C2 178.2(19) . . . . ?
C16 C1 N2 C20 -5(2) . . . . ?
C16 C17 C18 C19 5(3) . . . . ?
C17 C16 S1 C19 1(3) . . . . ?
C17 C18 C19 S1 -4(3) . . . . ?
C18 C19 S1 C16 2(3) . . . . ?
S1 C16 C17 C18 -4(3) . . . . ?
C16' C1 N1 C3 -179.3(16) . . . . ?
C16' C1 N2 C2 179.1(18) . . . . ?
C16' C1 N2 C20 -4(2) . . . . ?
C16' C17' C18' C19' -18(5) . . . . ?
C17' C16' S1' C19' 12(4) . . . . ?
C17' C18' C19' S1' 27(6) . . . . ?
C18' C19' S1' C16' -22(4) . . . . ?
S1' C16' C17' C18' 0(4) . . . . ?
C20 C21 C22 C23 -175.0(10) . . . . ?
C21 C20 N2 C1 103.2(9) . . . . ?
C21 C20 N2 C2 -81.1(10) . . . . ?
N1 C1 C16 C17 130(3) . . . . ?
N1 C1 C16 S1 -33(4) . . . . ?
N1 C1 C16' C17' 156(3) . . . . ?
N1 C1 C16' S1' -23(4) . . . . ?
N1 C1 N2 C2 -1.4(9) . . . . ?
N1 C1 N2 C20 175.0(7) . . . . ?
N1 C3 C4 C5 -1.3(12) . . . . ?
N1 C3 C4 C9 -176.5(7) . . . . ?
N2 C1 C16 C17 -50(5) . . . . ?
N2 C1 C16 S1 147(2) . . . . ?
N2 C1 C16' C17' -25(4) . . . . ?
N2 C1 C16' S1' 156(3) . . . . ?
N2 C1 N1 C3 1.2(8) . . . . ?
N2 C2 C3 C4 -176.3(7) . . . . ?
N2 C2 C3 N1 -0.2(9) . . . . ?
N2 C2 C15 C10 176.5(8) . . . . ?
N2 C2 C15 C14 -3.8(14) . . . . ?
N2 C20 C21 C22 170.5(8) . . . . ?


_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_mo_181127f_0m
_database_code_depnum_ccdc_archive 'CCDC 1963682'
loop_
_audit_author_name
_audit_author_address
'yun yu'
;wuhan university
China
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_audit_creation_date             2018-12-06
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 N2 S'
_chemical_formula_sum            'C24 H22 N2 S'
_chemical_formula_weight         370.49
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.069(3)
_cell_length_b                   8.451(3)
_cell_length_c                   22.933(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.378(6)
_cell_angle_gamma                90
_cell_volume                     1905.9(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2312
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.31
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1810 before and 0.0840 after correction. 
The Ratio of minimum to maximum transmission is 0.4923. 
The λ/2 correction factor is 0.0015. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12786
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.075
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2329
_reflns_number_total             3326
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3326
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²+0.4681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1620
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2. Restrained distances 
 C1-C16 \\sim C1-C16' 
 with sigma of 0.01 
3. Restrained planarity 
 C16', C17', C18', C19', S1' 
 with sigma of 0.1 
 C16, C17, C18, C19, S1 
 with sigma of 0.1 
4. Uiso/Uaniso restraints and constraints 
Uanis(C17) = Uanis(S1') 
Uanis(S1) = Uanis(C17') 
Uanis(C16) = Uanis(C16') 
Uanis(C19) = Uanis(C18') 
Uanis(C18) = Uanis(C19') 
5. Same fragment restrains 
{C16, C17, C18, C19, S1} sigma for 1-2: 0.02, 1-3: 0.04 
as 
{C16', C17', C18', C19', S1'} 
6. Others 
 Sof(C16')=Sof(C17')=Sof(H17')=Sof(C18')=Sof(H18')=Sof(C19')=Sof(H19')= 
 Sof(S1')=1-FVAR(1) 
 Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(S1)=FVAR(1) 
7.a Secondary CH2 refined with riding coordinates: 
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B) 
7.b Aromatic/amide H refined with riding coordinates: 
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), 
 C17(H17), C18(H18), C19(H19), C17'(H17'), C18'(H18'), C19'(H19') 
7.c Idealised Me refined as rotating group: 
 C24(H24A,H24B,H24C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.45674(19) 0.5304(2) 0.26493(8) 0.0449(5) Uani 1 1 d . . . . .
N2 N 0.57308(18) 0.6072(3) 0.19748(8) 0.0468(5) Uani 1 1 d . . . . .
C1 C 0.5807(2) 0.5690(3) 0.25353(10) 0.0446(6) Uani 1 1 d D . . . .
C2 C 0.3626(2) 0.5502(3) 0.21175(10) 0.0432(6) Uani 1 1 d . . . . .
C3 C 0.4380(2) 0.5953(3) 0.17111(10) 0.0426(6) Uani 1 1 d . . . . .
C4 C 0.3777(2) 0.6215(3) 0.10972(10) 0.0458(6) Uani 1 1 d . . . . .
C5 C 0.4565(3) 0.6541(3) 0.06775(11) 0.0588(7) Uani 1 1 d . . . . .
H5 H 0.5507 0.6597 0.0798 0.071 Uiso 1 1 calc R . . . .
C6 C 0.3957(3) 0.6775(4) 0.00939(12) 0.0741(9) Uani 1 1 d . . . . .
H6 H 0.4487 0.6986 -0.0183 0.089 Uiso 1 1 calc R . . . .
C7 C 0.2573(3) 0.6700(4) -0.00879(13) 0.0777(9) Uani 1 1 d . . . . .
H7 H 0.2165 0.6874 -0.0487 0.093 Uiso 1 1 calc R . . . .
C8 C 0.1784(3) 0.6371(4) 0.03164(13) 0.0661(8) Uani 1 1 d . . . . .
H8 H 0.0845 0.6317 0.0186 0.079 Uiso 1 1 calc R . . . .
C9 C 0.2361(2) 0.6115(3) 0.09180(11) 0.0501(6) Uani 1 1 d . . . . .
C10 C 0.1545(2) 0.5732(3) 0.13601(12) 0.0495(6) Uani 1 1 d . . . . .
C11 C 0.0122(3) 0.5704(3) 0.12017(15) 0.0656(8) Uani 1 1 d . . . . .
H11 H -0.0305 0.5929 0.0809 0.079 Uiso 1 1 calc R . . . .
C12 C -0.0660(3) 0.5357(4) 0.16038(17) 0.0764(9) Uani 1 1 d . . . . .
H12 H -0.1603 0.5377 0.1488 0.092 Uiso 1 1 calc R . . . .
C13 C -0.0038(3) 0.4975(4) 0.21849(15) 0.0786(10) Uani 1 1 d . . . . .
H13 H -0.0567 0.4700 0.2456 0.094 Uiso 1 1 calc R . . . .
C14 C 0.1340(3) 0.4998(4) 0.23634(13) 0.0668(8) Uani 1 1 d . . . . .
H14 H 0.1741 0.4754 0.2757 0.080 Uiso 1 1 calc R . . . .
C15 C 0.2173(2) 0.5388(3) 0.19615(11) 0.0477(6) Uani 1 1 d . . . . .
C16 C 0.7049(6) 0.5793(12) 0.3001(4) 0.0433(13) Uani 0.760(4) 1 d D . P A 1
C17 C 0.7709(18) 0.4736(19) 0.3399(7) 0.0758(17) Uani 0.760(4) 1 d D . P A 1
H17 H 0.7348 0.3751 0.3459 0.091 Uiso 0.760(4) 1 calc R . P A 1
C18 C 0.8992(10) 0.5249(9) 0.3717(5) 0.0680(15) Uani 0.760(4) 1 d D . P A 1
H18 H 0.9580 0.4634 0.3995 0.082 Uiso 0.760(4) 1 calc R . P A 1
C19 C 0.9263(6) 0.6748(7) 0.3568(2) 0.0577(12) Uani 0.760(4) 1 d D . P A 1
H19 H 1.0042 0.7308 0.3743 0.069 Uiso 0.760(4) 1 calc R . P A 1
S1 S 0.79950(16) 0.74778(16) 0.30172(7) 0.0599(4) Uani 0.760(4) 1 d D . P A 1
C16' C 0.7136(19) 0.575(4) 0.2932(13) 0.0433(13) Uani 0.240(4) 1 d D . P A 2
C17' C 0.785(2) 0.708(3) 0.2962(11) 0.0599(4) Uani 0.240(4) 1 d D . P A 2
H17' H 0.7627 0.7933 0.2703 0.072 Uiso 0.240(4) 1 calc R . P A 2
C18' C 0.899(2) 0.703(3) 0.3436(10) 0.0577(12) Uani 0.240(4) 1 d D . P A 2
H18' H 0.9602 0.7861 0.3536 0.069 Uiso 0.240(4) 1 calc R . P A 2
C19' C 0.910(3) 0.562(3) 0.3734(17) 0.0680(15) Uani 0.240(4) 1 d D . P A 2
H19' H 0.9818 0.5347 0.4044 0.082 Uiso 0.240(4) 1 calc R . P A 2
S1' S 0.7742(15) 0.4421(15) 0.3465(6) 0.0758(17) Uani 0.240(4) 1 d D . P A 2
C20 C 0.4315(3) 0.4847(3) 0.32345(11) 0.0537(7) Uani 1 1 d . . . . .
H20A H 0.5146 0.4418 0.3477 0.064 Uiso 1 1 calc R . . . .
H20B H 0.3633 0.4019 0.3179 0.064 Uiso 1 1 calc R . . . .
C21 C 0.3844(3) 0.6202(3) 0.35612(11) 0.0555(7) Uani 1 1 d . . . . .
H21A H 0.3083 0.6723 0.3301 0.067 Uiso 1 1 calc R . . . .
H21B H 0.4573 0.6967 0.3669 0.067 Uiso 1 1 calc R . . . .
C22 C 0.3412(3) 0.5633(4) 0.41224(12) 0.0660(8) Uani 1 1 d . . . . .
H22A H 0.2649 0.4915 0.4009 0.079 Uiso 1 1 calc R . . . .
H22B H 0.4156 0.5048 0.4367 0.079 Uiso 1 1 calc R . . . .
C23 C 0.3014(3) 0.6955(4) 0.44852(12) 0.0711(8) Uani 1 1 d . . . . .
H23A H 0.3780 0.7668 0.4600 0.085 Uiso 1 1 calc R . . . .
H23B H 0.2276 0.7545 0.4239 0.085 Uiso 1 1 calc R . . . .
C24 C 0.2575(4) 0.6410(5) 0.50362(14) 0.0951(12) Uani 1 1 d . . . . .
H24A H 0.1792 0.5739 0.4926 0.143 Uiso 1 1 calc GR . . . .
H24B H 0.2351 0.7311 0.5251 0.143 Uiso 1 1 calc GR . . . .
H24C H 0.3302 0.5830 0.5285 0.143 Uiso 1 1 calc GR . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.368(3) . ?
N1 C2 1.385(3) . ?
N1 C20 1.470(3) . ?
N2 C1 1.311(3) . ?
N2 C3 1.368(3) . ?
C1 C16 1.463(4) . ?
C1 C16' 1.449(8) . ?
C2 C3 1.377(3) . ?
C2 C15 1.433(3) . ?
C3 C4 1.426(3) . ?
C4 C5 1.400(3) . ?
C4 C9 1.399(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.362(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(4) . ?
C9 C10 1.472(4) . ?
C10 C11 1.400(3) . ?
C10 C15 1.419(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.360(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.411(4) . ?
C16 C17 1.346(14) . ?
C16 S1 1.709(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.408(16) . ?
C18 H18 0.9300 . ?
C18 C19 1.355(6) . ?
C19 H19 0.9300 . ?
C19 S1 1.707(4) . ?
C16' C17' 1.33(2) . ?
C16' S1' 1.67(2) . ?
C17' H17' 0.9300 . ?
C17' C18' 1.40(2) . ?
C18' H18' 0.9300 . ?
C18' C19' 1.367(16) . ?
C19' H19' 0.9300 . ?
C19' S1' 1.704(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.500(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.522(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.498(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.497(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 106.44(19) . . ?
C1 N1 C20 125.45(19) . . ?
C2 N1 C20 128.05(19) . . ?
C1 N2 C3 105.01(18) . . ?
N1 C1 C16 123.2(4) . . ?
N1 C1 C16' 130.2(14) . . ?
N2 C1 N1 112.45(19) . . ?
N2 C1 C16 124.2(4) . . ?
N2 C1 C16' 117.3(13) . . ?
N1 C2 C15 132.9(2) . . ?
C3 C2 N1 104.89(19) . . ?
C3 C2 C15 122.1(2) . . ?
N2 C3 C2 111.2(2) . . ?
N2 C3 C4 126.7(2) . . ?
C2 C3 C4 122.1(2) . . ?
C5 C4 C3 121.6(2) . . ?
C9 C4 C3 118.2(2) . . ?
C9 C4 C5 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.5(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C10 119.7(2) . . ?
C8 C9 C4 117.6(3) . . ?
C8 C9 C10 122.7(2) . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 C15 117.8(2) . . ?
C15 C10 C9 121.1(2) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.3(3) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C2 116.6(2) . . ?
C14 C15 C2 124.8(2) . . ?
C14 C15 C10 118.6(2) . . ?
C1 C16 S1 116.8(5) . . ?
C17 C16 C1 132.6(10) . . ?
C17 C16 S1 110.2(8) . . ?
C16 C17 H17 122.9 . . ?
C16 C17 C18 114.3(12) . . ?
C18 C17 H17 122.9 . . ?
C17 C18 H18 124.2 . . ?
C19 C18 C17 111.7(8) . . ?
C19 C18 H18 124.2 . . ?
C18 C19 H19 124.3 . . ?
C18 C19 S1 111.4(5) . . ?
S1 C19 H19 124.3 . . ?
C19 S1 C16 92.3(3) . . ?
C1 C16' S1' 125.4(17) . . ?
C17' C16' C1 118.6(19) . . ?
C17' C16' S1' 114.8(10) . . ?
C16' C17' H17' 124.5 . . ?
C16' C17' C18' 111.0(17) . . ?
C18' C17' H17' 124.5 . . ?
C17' C18' H18' 123.9 . . ?
C19' C18' C17' 112(2) . . ?
C19' C18' H18' 123.9 . . ?
C18' C19' H19' 124.2 . . ?
C18' C19' S1' 111.5(19) . . ?
S1' C19' H19' 124.2 . . ?
C16' S1' C19' 90.2(12) . . ?
N1 C20 H20A 109.0 . . ?
N1 C20 H20B 109.0 . . ?
N1 C20 C21 113.0(2) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C20 C21 C22 111.1(2) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 C21 113.2(3) . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.7(3) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 C1 C16 C17 58.8(13) . . . . ?
N1 C1 C16 S1 -129.4(5) . . . . ?
N1 C1 C16' C17' -125.4(18) . . . . ?
N1 C1 C16' S1' 41(4) . . . . ?
N1 C2 C3 N2 -1.3(3) . . . . ?
N1 C2 C3 C4 177.5(2) . . . . ?
N1 C2 C15 C10 177.9(2) . . . . ?
N1 C2 C15 C14 -0.6(4) . . . . ?
N1 C20 C21 C22 172.2(2) . . . . ?
N2 C1 C16 C17 -126.7(11) . . . . ?
N2 C1 C16 S1 45.1(9) . . . . ?
N2 C1 C16' C17' 54(3) . . . . ?
N2 C1 C16' S1' -139(2) . . . . ?
N2 C3 C4 C5 4.2(4) . . . . ?
N2 C3 C4 C9 -176.8(2) . . . . ?
C1 N1 C2 C3 1.7(3) . . . . ?
C1 N1 C2 C15 -175.2(2) . . . . ?
C1 N1 C20 C21 96.6(3) . . . . ?
C1 N2 C3 C2 0.3(3) . . . . ?
C1 N2 C3 C4 -178.4(2) . . . . ?
C1 C16 C17 C18 171.2(11) . . . . ?
C1 C16 S1 C19 -174.2(8) . . . . ?
C1 C16' C17' C18' 170(3) . . . . ?
C1 C16' S1' C19' -171(3) . . . . ?
C2 N1 C1 N2 -1.7(3) . . . . ?
C2 N1 C1 C16 173.4(5) . . . . ?
C2 N1 C1 C16' 177.7(18) . . . . ?
C2 N1 C20 C21 -80.2(3) . . . . ?
C2 C3 C4 C5 -174.4(2) . . . . ?
C2 C3 C4 C9 4.6(4) . . . . ?
C3 N2 C1 N1 0.9(3) . . . . ?
C3 N2 C1 C16 -174.1(5) . . . . ?
C3 N2 C1 C16' -178.6(16) . . . . ?
C3 C2 C15 C10 1.4(3) . . . . ?
C3 C2 C15 C14 -177.1(3) . . . . ?
C3 C4 C5 C6 179.6(3) . . . . ?
C3 C4 C9 C8 -179.9(2) . . . . ?
C3 C4 C9 C10 -0.6(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C4 C9 C10 C11 176.6(2) . . . . ?
C4 C9 C10 C15 -3.0(3) . . . . ?
C5 C4 C9 C8 -0.9(4) . . . . ?
C5 C4 C9 C10 178.4(2) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
C8 C9 C10 C11 -4.1(4) . . . . ?
C8 C9 C10 C15 176.3(2) . . . . ?
C9 C4 C5 C6 0.6(4) . . . . ?
C9 C10 C11 C12 -179.8(3) . . . . ?
C9 C10 C15 C2 2.6(3) . . . . ?
C9 C10 C15 C14 -178.8(2) . . . . ?
C10 C11 C12 C13 -1.8(4) . . . . ?
C11 C10 C15 C2 -177.0(2) . . . . ?
C11 C10 C15 C14 1.6(4) . . . . ?
C11 C12 C13 C14 2.4(5) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C13 C14 C15 C2 177.4(3) . . . . ?
C13 C14 C15 C10 -1.0(4) . . . . ?
C15 C2 C3 N2 176.1(2) . . . . ?
C15 C2 C3 C4 -5.1(4) . . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
C16 C17 C18 C19 2.6(14) . . . . ?
C17 C16 S1 C19 -0.7(8) . . . . ?
C17 C18 C19 S1 -3.0(11) . . . . ?
C18 C19 S1 C16 2.2(7) . . . . ?
S1 C16 C17 C18 -1.0(12) . . . . ?
C16' C17' C18' C19' 2(2) . . . . ?
C17' C16' S1' C19' -4(3) . . . . ?
C17' C18' C19' S1' -4(3) . . . . ?
C18' C19' S1' C16' 4(3) . . . . ?
S1' C16' C17' C18' 1.7(19) . . . . ?
C20 N1 C1 N2 -179.1(2) . . . . ?
C20 N1 C1 C16 -4.0(6) . . . . ?
C20 N1 C1 C16' 0.3(19) . . . . ?
C20 N1 C2 C3 179.1(2) . . . . ?
C20 N1 C2 C15 2.1(4) . . . . ?
C20 C21 C22 C23 176.4(2) . . . . ?
C21 C22 C23 C24 179.5(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
