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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mo_yey_4mco_150k_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2163417'
loop_
_audit_author_name
_audit_author_address
'Chengyong Yang'
;Sichuan University
China
;
_audit_update_record             
;
2022-03-30 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_audit_creation_date             2021-05-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O2 S2'
_chemical_formula_sum            'C16 H15 N O2 S2'
_chemical_formula_weight         317.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9599(3)
_cell_length_b                   11.6425(4)
_cell_length_c                   15.6846(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.3910(10)
_cell_angle_gamma                90
_cell_volume                     1447.11(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7670
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.466
_cell_measurement_theta_min      3.110
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.857
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1159 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.9374.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39620
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         3.110
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2517
_reflns_number_total             3292
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.049
_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)+(0.0374P)²+1.0380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.9 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
S3 \\sim N2: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.001 within 1.7A
4. Others
 Sof(S1A)=1-FVAR(1)
 Sof(S1)=FVAR(1)
 Sof(C13A)=Sof(H13A)=1-FVAR(2)
 Sof(C13)=Sof(H13)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C13A(H13A)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S3 S 0.49176(6) 0.86762(4) 0.63400(3) 0.02467(13) Uani 1 1 d . U . . .
O1 O 0.20515(18) 0.48072(12) 0.42354(8) 0.0301(3) Uani 1 1 d . . . . .
N2 N 0.4902(2) 0.84220(15) 0.72661(10) 0.0273(3) Uani 1 1 d D U . . .
H2 H 0.559(2) 0.7810(11) 0.7348(14) 0.033 Uiso 1 1 d D U . . .
O3 O 0.6504(2) 0.89620(15) 0.59604(11) 0.0437(4) Uani 1 1 d . . . . .
C17 C 0.1876(2) 0.69680(17) 0.68063(11) 0.0227(4) Uani 1 1 d . . . . .
C16 C 0.0117(2) 0.75762(17) 0.79010(12) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.1010(2) 0.66047(17) 0.82068(12) 0.0237(4) Uani 1 1 d . . . . .
C1 C 0.2650(3) 0.45775(19) 0.34215(13) 0.0332(5) Uani 1 1 d . . . . .
H1A H 0.2440 0.5247 0.3048 0.050 Uiso 1 1 calc R U . . .
H1B H 0.2055 0.3909 0.3161 0.050 Uiso 1 1 calc R U . . .
H1C H 0.3863 0.4419 0.3498 0.050 Uiso 1 1 calc R U . . .
C2 C 0.2725(2) 0.57265(17) 0.46821(12) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.2090(2) 0.59222(17) 0.54667(12) 0.0241(4) Uani 1 1 d . . . . .
H3 H 0.1247 0.5424 0.5647 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2662(2) 0.68279(17) 0.59901(11) 0.0216(4) Uani 1 1 d . . . . .
C5 C -0.1002(3) 0.81245(19) 0.84029(15) 0.0336(5) Uani 1 1 d . . . . .
H5 H -0.1624 0.8779 0.8195 0.040 Uiso 1 1 calc R U . . .
C6 C -0.1181(3) 0.7694(2) 0.92056(15) 0.0378(5) Uani 1 1 d . . . . .
H6 H -0.1921 0.8064 0.9559 0.045 Uiso 1 1 calc R U . . .
C7 C -0.0298(3) 0.6726(2) 0.95067(13) 0.0347(5) Uani 1 1 d . . . . .
H7 H -0.0454 0.6441 1.0061 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0794(3) 0.61726(19) 0.90189(13) 0.0298(5) Uani 1 1 d . . . . .
H8 H 0.1391 0.5509 0.9230 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3930(2) 0.75457(17) 0.57112(12) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.3606(3) 0.98761(18) 0.61370(14) 0.0323(5) Uani 1 1 d . . . . .
H10A H 0.2484 0.9710 0.6315 0.048 Uiso 1 1 calc R U . . .
H10B H 0.3511 1.0051 0.5523 0.048 Uiso 1 1 calc R U . . .
H10C H 0.4090 1.0538 0.6459 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4530(2) 0.73447(18) 0.49234(12) 0.0258(4) Uani 1 1 d . . . . .
H11 H 0.5371 0.7839 0.4737 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3941(2) 0.64454(17) 0.43988(12) 0.0256(4) Uani 1 1 d . . . . .
H12 H 0.4360 0.6326 0.3859 0.031 Uiso 1 1 calc R U . . .
S1 S 0.0423(4) 0.8057(3) 0.6907(2) 0.0230(7) Uani 0.534(10) 1 d . . P A 1
S1A S 0.2416(5) 0.5999(3) 0.75860(15) 0.0257(8) Uani 0.466(10) 1 d . . P A 2
C13 C 0.1969(16) 0.6288(10) 0.7496(7) 0.0285(19) Uani 0.49(3) 1 d . . P A 1
H13 H 0.2644 0.5614 0.7522 0.034 Uiso 0.49(3) 1 calc R U P A 1
C13A C 0.0683(17) 0.7772(12) 0.7021(7) 0.025(2) Uani 0.51(3) 1 d . . P A 2
H13A H 0.0272 0.8378 0.6653 0.030 Uiso 0.51(3) 1 calc R U 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
S3 N2 1.4835(17) . ?
S3 O3 1.4836(16) . ?
S3 C9 1.782(2) . ?
S3 C10 1.755(2) . ?
O1 C1 1.429(2) . ?
O1 C2 1.361(2) . ?
N2 H2 0.8995(10) . ?
C17 C4 1.486(3) . ?
C17 S1 1.733(4) . ?
C17 S1A 1.690(4) . ?
C17 C13 1.337(12) . ?
C17 C13A 1.397(15) . ?
C16 C15 1.396(3) . ?
C16 C5 1.397(3) . ?
C16 S1 1.695(4) . ?
C16 C13A 1.508(12) . ?
C15 C8 1.395(3) . ?
C15 S1A 1.704(4) . ?
C15 C13 1.456(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.392(3) . ?
C2 C12 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 C9 1.411(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(3) . ?
C8 H8 0.9500 . ?
C9 C11 1.386(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13A H13A 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
N2 S3 O3 121.55(10) . . ?
N2 S3 C9 110.53(10) . . ?
N2 S3 C10 106.08(10) . . ?
O3 S3 C9 106.94(9) . . ?
O3 S3 C10 105.24(10) . . ?
C10 S3 C9 105.27(10) . . ?
C2 O1 C1 117.30(15) . . ?
S3 N2 H2 103.7(14) . . ?
C4 C17 S1 119.83(18) . . ?
C4 C17 S1A 116.83(18) . . ?
C13 C17 C4 129.6(6) . . ?
C13 C17 S1 110.2(5) . . ?
C13A C17 C4 129.2(5) . . ?
C13A C17 S1A 113.9(5) . . ?
C15 C16 C5 120.48(18) . . ?
C15 C16 S1 118.10(18) . . ?
C15 C16 C13A 104.5(6) . . ?
C5 C16 S1 121.4(2) . . ?
C5 C16 C13A 135.0(6) . . ?
C16 C15 S1A 118.64(19) . . ?
C16 C15 C13 103.2(6) . . ?
C8 C15 C16 120.22(18) . . ?
C8 C15 S1A 121.1(2) . . ?
C8 C15 C13 136.5(6) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 115.17(17) . . ?
O1 C2 C12 124.32(17) . . ?
C12 C2 C3 120.50(18) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.44(18) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C17 116.90(17) . . ?
C3 C4 C9 118.12(17) . . ?
C9 C4 C17 124.98(17) . . ?
C16 C5 H5 120.8 . . ?
C6 C5 C16 118.4(2) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.26(19) . . ?
C8 C7 H7 119.4 . . ?
C15 C8 H8 120.7 . . ?
C7 C8 C15 118.6(2) . . ?
C7 C8 H8 120.7 . . ?
C4 C9 S3 123.85(14) . . ?
C11 C9 S3 116.55(15) . . ?
C11 C9 C4 119.51(18) . . ?
S3 C10 H10A 109.5 . . ?
S3 C10 H10B 109.5 . . ?
S3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11 119.0 . . ?
C9 C11 C12 122.09(18) . . ?
C12 C11 H11 119.0 . . ?
C2 C12 C11 118.30(17) . . ?
C2 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C16 S1 C17 89.8(2) . . ?
C17 S1A C15 90.1(2) . . ?
C17 C13 C15 118.5(10) . . ?
C17 C13 H13 120.8 . . ?
C15 C13 H13 120.8 . . ?
C17 C13A C16 112.8(9) . . ?
C17 C13A H13A 123.6 . . ?
C16 C13A H13A 123.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S3 C9 C11 C12 175.87(16) . . . . ?
O1 C2 C3 C4 179.95(17) . . . . ?
O1 C2 C12 C11 -179.36(18) . . . . ?
N2 S3 C9 C4 27.69(19) . . . . ?
N2 S3 C9 C11 -148.96(15) . . . . ?
O3 S3 C9 C4 161.96(16) . . . . ?
O3 S3 C9 C11 -14.69(18) . . . . ?
C17 C4 C9 S3 5.3(3) . . . . ?
C17 C4 C9 C11 -178.18(18) . . . . ?
C16 C15 C8 C7 -0.4(3) . . . . ?
C16 C15 S1A C17 -2.7(2) . . . . ?
C16 C15 C13 C17 3.9(8) . . . . ?
C16 C5 C6 C7 -1.2(3) . . . . ?
C15 C16 C5 C6 0.9(3) . . . . ?
C15 C16 S1 C17 -1.1(2) . . . . ?
C15 C16 C13A C17 -0.7(9) . . . . ?
C1 O1 C2 C3 179.37(18) . . . . ?
C1 O1 C2 C12 0.0(3) . . . . ?
C2 C3 C4 C17 178.99(17) . . . . ?
C2 C3 C4 C9 -0.8(3) . . . . ?
C3 C2 C12 C11 1.4(3) . . . . ?
C3 C4 C9 S3 -174.99(14) . . . . ?
C3 C4 C9 C11 1.6(3) . . . . ?
C4 C17 S1 C16 176.68(17) . . . . ?
C4 C17 S1A C15 -175.60(16) . . . . ?
C4 C17 C13 C15 -177.5(4) . . . . ?
C4 C17 C13A C16 176.2(4) . . . . ?
C4 C9 C11 C12 -0.9(3) . . . . ?
C5 C16 C15 C8 -0.1(3) . . . . ?
C5 C16 C15 S1A -177.64(18) . . . . ?
C5 C16 C15 C13 178.4(4) . . . . ?
C5 C16 S1 C17 179.35(18) . . . . ?
C5 C16 C13A C17 179.3(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C15 0.2(3) . . . . ?
C8 C15 S1A C17 179.78(18) . . . . ?
C8 C15 C13 C17 -178.0(4) . . . . ?
C9 C11 C12 C2 -0.5(3) . . . . ?
C10 S3 C9 C4 -86.44(18) . . . . ?
C10 S3 C9 C11 96.90(17) . . . . ?
C12 C2 C3 C4 -0.7(3) . . . . ?
S1 C17 C4 C3 -105.0(2) . . . . ?
S1 C17 C4 C9 74.7(3) . . . . ?
S1 C17 C13 C15 -4.9(9) . . . . ?
S1 C16 C15 C8 -179.6(2) . . . . ?
S1 C16 C15 C13 -1.2(5) . . . . ?
S1 C16 C5 C6 -179.6(2) . . . . ?
S1A C17 C4 C3 72.7(2) . . . . ?
S1A C17 C4 C9 -107.5(2) . . . . ?
S1A C17 C13A C16 -1.2(10) . . . . ?
S1A C15 C8 C7 177.05(18) . . . . ?
C13 C17 C4 C3 67.0(6) . . . . ?
C13 C17 C4 C9 -113.3(6) . . . . ?
C13 C17 S1 C16 3.3(5) . . . . ?
C13 C15 C8 C7 -178.3(6) . . . . ?
C13A C17 C4 C3 -104.6(7) . . . . ?
C13A C17 C4 C9 75.2(7) . . . . ?
C13A C17 S1A C15 2.1(6) . . . . ?
C13A C16 C15 C8 179.9(5) . . . . ?
C13A C16 C15 S1A 2.4(5) . . . . ?
C13A C16 C5 C6 -179.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
