# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_190621_wdg_0ma
_database_code_depnum_ccdc_archive 'CCDC 1938235'
loop_
_audit_author_name
_audit_author_address
'wang dungai'
;zhejiang University
China
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N S2'
_chemical_formula_sum            'C14 H11 N S2'
_chemical_formula_weight         257.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   27.604(2)
_cell_length_b                   7.7285(6)
_cell_length_c                   5.8633(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1250.85(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8130
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1095 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.8811.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13139
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.415
_diffrn_reflns_theta_min         2.737
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2405
_reflns_number_total             2562
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1009 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.069
_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)+(0.0358P)²+0.3965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0773
_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:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22526(2) 0.67528(8) 0.15550(12) 0.02848(17) Uani 1 1 d . . . . .
S2 S 0.27318(2) 0.47492(8) 0.13886(13) 0.02911(18) Uani 1 1 d . . . . .
N1 N 0.47514(10) 0.6405(4) 0.8645(6) 0.0545(8) Uani 1 1 d . . . . .
C1 C 0.18236(10) 0.5221(4) 0.5401(5) 0.0271(6) Uani 1 1 d . . . . .
H1 H 0.213843 0.493749 0.593861 0.033 Uiso 1 1 calc R . . . .
C2 C 0.14191(10) 0.4814(3) 0.6699(5) 0.0291(6) Uani 1 1 d . . . . .
H2 H 0.146193 0.423211 0.811180 0.035 Uiso 1 1 calc R . . . .
C3 C 0.09517(10) 0.5235(3) 0.5990(5) 0.0301(6) Uani 1 1 d . . . . .
C4 C 0.09037(10) 0.6068(4) 0.3896(6) 0.0318(6) Uani 1 1 d . . . . .
H4 H 0.058987 0.638276 0.337523 0.038 Uiso 1 1 calc R . . . .
C5 C 0.13025(10) 0.6450(4) 0.2555(5) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.125940 0.698971 0.111335 0.035 Uiso 1 1 calc R . . . .
C6 C 0.17665(9) 0.6043(3) 0.3313(5) 0.0247(6) Uani 1 1 d . . . . .
C7 C 0.05169(11) 0.4811(4) 0.7435(6) 0.0412(7) Uani 1 1 d . . . . .
H7A H 0.033979 0.384265 0.675068 0.062 Uiso 1 1 calc GR . . . .
H7B H 0.030440 0.582447 0.752396 0.062 Uiso 1 1 calc GR . . . .
H7C H 0.062360 0.449014 0.897241 0.062 Uiso 1 1 calc GR . . . .
C8 C 0.32160(9) 0.5310(3) 0.3249(5) 0.0247(6) Uani 1 1 d . . . . .
C9 C 0.36743(10) 0.4738(3) 0.2560(5) 0.0294(6) Uani 1 1 d . . . . .
H9 H 0.371176 0.414794 0.115021 0.035 Uiso 1 1 calc R . . . .
C10 C 0.40715(10) 0.5034(4) 0.3932(6) 0.0314(6) Uani 1 1 d . . . . .
H10 H 0.438286 0.464390 0.347162 0.038 Uiso 1 1 calc R . . . .
C11 C 0.40153(9) 0.5909(3) 0.6000(5) 0.0293(6) Uani 1 1 d . . . . .
C12 C 0.35593(9) 0.6494(3) 0.6675(6) 0.0279(6) Uani 1 1 d . . . . .
H12 H 0.352231 0.709919 0.807440 0.034 Uiso 1 1 calc R . . . .
C13 C 0.31596(9) 0.6188(4) 0.5296(5) 0.0261(6) Uani 1 1 d . . . . .
H13 H 0.284804 0.657873 0.575251 0.031 Uiso 1 1 calc R . . . .
C14 C 0.44283(10) 0.6197(4) 0.7464(6) 0.0375(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 S2 2.0389(9) . ?
S1 C6 1.779(3) . ?
S2 C8 1.779(3) . ?
N1 C14 1.141(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(4) . ?
C1 C6 1.388(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(4) . ?
C3 C4 1.393(4) . ?
C3 C7 1.505(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.400(4) . ?
C8 C13 1.388(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(4) . ?
C11 C12 1.395(4) . ?
C11 C14 1.444(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 S2 106.44(9) . . ?
C8 S2 S1 105.85(9) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.7(2) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.9(3) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C7 121.3(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 C7 121.4(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 S1 124.5(2) . . ?
C1 C6 C5 119.3(3) . . ?
C5 C6 S1 116.1(2) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S2 115.2(2) . . ?
C13 C8 S2 124.4(2) . . ?
C13 C8 C9 120.4(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C14 120.2(3) . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 C14 119.6(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 119.9(2) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N1 C14 C11 178.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
