# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_wzk
_database_code_depnum_ccdc_archive 'CCDC 2165685'
loop_
_audit_author_name
_audit_author_address
'Zongkang Wang'
;East China Normal University
China
;
_audit_update_record             
;
2022-04-10 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-23
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14.051 H10.102 N S0.949'
_chemical_formula_sum            'C14.05 H10.10 N S0.95'
_chemical_formula_weight         223.39
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   10.6100(7)
_cell_length_b                   8.4073(5)
_cell_length_c                   12.0322(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.775(2)
_cell_angle_gamma                90
_cell_volume                     1042.42(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9110
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      72.31
_cell_measurement_theta_min      5.00
_shelx_estimated_absorpt_T_max   0.718
_shelx_estimated_absorpt_T_min   0.518
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8169.
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    1.423
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25614
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.456
_diffrn_reflns_theta_min         4.290
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1977
_reflns_number_total             2049
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0062(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2049
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.407
_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)+(0.0537P)²+0.3912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C15-C7 \\sim C7-C14 \\sim C15-C4 \\sim C13-C14 \\sim S1-C7 \\sim S2-C7 \\sim
S1-C4 \\sim S2-C13
 with sigma of 0.02
3. Rigid bond restraints
 C14
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C15, S1, C14, S2
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C14: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within
2A
C15 \\sim S1 \\sim C14 \\sim S2: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
Uanis(C14) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C15) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(S2)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(S2)=1-FVAR(1)
 Sof(C14)=Sof(H14a)=Sof(H14b)=FVAR(1)
 Sof(C15)=Sof(H15a)=Sof(H15b)=1-FVAR(2)
 Sof(S1)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C15(H15a,H15b)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C6(H6), C9(H9), C10(H10), C1(H1), C2(H2), C11(H11)
;
_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 0.56729(10) 0.45214(14) 0.26449(11) 0.0292(3) Uani 0.712(4) 1 d D U P A 1
C14 C 0.2897(7) 0.5060(11) 0.2053(8) 0.0411(19) Uani 0.763(4) 1 d D U P A 1
H14A H 0.261412 0.395926 0.200428 0.049 Uiso 0.763(4) 1 calc R U P A 1
H14B H 0.281056 0.548121 0.128790 0.049 Uiso 0.763(4) 1 calc R U P A 1
N1 N 0.42780(11) 0.62590(13) 0.36683(9) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.55446(13) 0.65773(15) 0.42802(11) 0.0250(3) Uani 1 1 d . . . . .
C8 C 0.30378(13) 0.67781(15) 0.36814(11) 0.0244(3) Uani 1 1 d . . . . .
C4 C 0.64254(14) 0.57035(16) 0.38141(12) 0.0283(3) Uani 1 1 d D . . . .
C13 C 0.21603(13) 0.60643(16) 0.27434(11) 0.0277(3) Uani 1 1 d D . . . .
C7 C 0.42165(15) 0.52318(16) 0.27497(12) 0.0301(3) Uani 1 1 d D . . . .
C3 C 0.77518(14) 0.58057(18) 0.42975(13) 0.0343(3) Uani 1 1 d . . . . .
H3 H 0.833896 0.522150 0.399894 0.041 Uiso 1 1 calc R U . . .
C12 C 0.08395(14) 0.63982(18) 0.25671(13) 0.0338(3) Uani 1 1 d . . . . .
H12 H 0.024411 0.593979 0.195751 0.041 Uiso 1 1 calc R U . . .
C6 C 0.59759(14) 0.75746(16) 0.52123(11) 0.0295(3) Uani 1 1 d . . . . .
H6 H 0.539385 0.816433 0.551342 0.035 Uiso 1 1 calc R U . . .
C9 C 0.26269(14) 0.77957(16) 0.44360(12) 0.0290(3) Uani 1 1 d . . . . .
H9 H 0.321426 0.825242 0.505183 0.035 Uiso 1 1 calc R U . . .
C10 C 0.13114(15) 0.81021(18) 0.42353(13) 0.0352(3) Uani 1 1 d . . . . .
H10 H 0.100856 0.877713 0.472637 0.042 Uiso 1 1 calc R U . . .
C1 C 0.73023(15) 0.76652(18) 0.56817(12) 0.0344(3) Uani 1 1 d . . . . .
H1 H 0.761136 0.832136 0.630978 0.041 Uiso 1 1 calc R U . . .
C2 C 0.81798(14) 0.67923(19) 0.52301(13) 0.0370(4) Uani 1 1 d . . . . .
H2 H 0.906387 0.687439 0.556000 0.044 Uiso 1 1 calc R U . . .
C11 C 0.04262(14) 0.74169(18) 0.33078(14) 0.0366(4) Uani 1 1 d . . . . .
H11 H -0.045252 0.765116 0.318901 0.044 Uiso 1 1 calc R U . . .
S2 S 0.2864(5) 0.4786(9) 0.2028(6) 0.0333(9) Uani 0.237(4) 1 d D U P A 2
C15 C 0.5652(10) 0.4776(18) 0.2793(12) 0.039(3) Uani 0.288(4) 1 d D U P A 2
H15A H 0.578884 0.364044 0.290472 0.047 Uiso 0.288(4) 1 calc R U P A 2
H15B H 0.589118 0.508885 0.209468 0.047 Uiso 0.288(4) 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
S1 C4 1.7519(18) . ?
S1 C7 1.6892(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.524(7) . ?
C14 C7 1.458(7) . ?
N1 C5 1.3958(17) . ?
N1 C8 1.3900(17) . ?
N1 C7 1.3919(17) . ?
C5 C4 1.4062(19) . ?
C5 C6 1.3878(19) . ?
C8 C13 1.4143(19) . ?
C8 C9 1.3911(19) . ?
C4 C3 1.392(2) . ?
C4 C15 1.520(10) . ?
C13 C12 1.395(2) . ?
C13 S2 1.661(6) . ?
C7 S2 1.536(6) . ?
C7 C15 1.560(11) . ?
C3 H3 0.9300 . ?
C3 C2 1.382(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.381(2) . ?
C6 H6 0.9300 . ?
C6 C1 1.388(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.400(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.393(2) . ?
C2 H2 0.9300 . ?
C11 H11 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C7 S1 C4 89.40(8) . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14A 111.7 . . ?
C13 C14 H14B 111.7 . . ?
C7 C14 H14A 111.7 . . ?
C7 C14 H14B 111.7 . . ?
C7 C14 C13 100.3(5) . . ?
C8 N1 C5 136.80(11) . . ?
C8 N1 C7 109.77(11) . . ?
C7 N1 C5 113.27(11) . . ?
N1 C5 C4 109.71(12) . . ?
C6 C5 N1 129.26(12) . . ?
C6 C5 C4 121.03(13) . . ?
N1 C8 C13 107.63(11) . . ?
N1 C8 C9 130.18(12) . . ?
C9 C8 C13 122.19(12) . . ?
C5 C4 S1 113.43(11) . . ?
C5 C4 C15 108.0(4) . . ?
C3 C4 S1 126.36(12) . . ?
C3 C4 C5 120.20(13) . . ?
C3 C4 C15 131.8(4) . . ?
C8 C13 C14 110.2(3) . . ?
C8 C13 S2 113.4(2) . . ?
C12 C13 C14 130.9(3) . . ?
C12 C13 C8 118.85(13) . . ?
C12 C13 S2 127.6(2) . . ?
C14 C7 S1 133.8(3) . . ?
N1 C7 S1 114.07(11) . . ?
N1 C7 C14 112.0(3) . . ?
N1 C7 S2 117.5(2) . . ?
N1 C7 C15 105.4(4) . . ?
S2 C7 C15 137.1(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.71(14) . . ?
C2 C3 H3 120.6 . . ?
C13 C12 H12 120.4 . . ?
C11 C12 C13 119.25(13) . . ?
C11 C12 H12 120.4 . . ?
C5 C6 H6 121.0 . . ?
C5 C6 C1 117.98(13) . . ?
C1 C6 H6 121.0 . . ?
C8 C9 H9 121.3 . . ?
C10 C9 C8 117.44(13) . . ?
C10 C9 H9 121.3 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.35(14) . . ?
C11 C10 H10 119.3 . . ?
C6 C1 H1 119.4 . . ?
C6 C1 C2 121.28(14) . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 120.78(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C12 C11 C10 120.92(14) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C7 S2 C13 91.4(3) . . ?
C4 C15 C7 103.6(7) . . ?
C4 C15 H15A 111.0 . . ?
C4 C15 H15B 111.0 . . ?
C7 C15 H15A 111.0 . . ?
C7 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 -179.35(12) . . . . ?
C14 C13 C12 C11 -177.2(5) . . . . ?
N1 C5 C4 S1 -0.08(15) . . . . ?
N1 C5 C4 C3 -178.85(12) . . . . ?
N1 C5 C4 C15 1.6(7) . . . . ?
N1 C5 C6 C1 179.04(12) . . . . ?
N1 C8 C13 C14 -2.2(4) . . . . ?
N1 C8 C13 C12 179.94(12) . . . . ?
N1 C8 C13 S2 4.3(3) . . . . ?
N1 C8 C9 C10 -179.93(13) . . . . ?
N1 C7 S2 C13 6.2(5) . . . . ?
N1 C7 C15 C4 -0.9(10) . . . . ?
C5 N1 C8 C13 174.71(13) . . . . ?
C5 N1 C8 C9 -5.7(2) . . . . ?
C5 N1 C7 S1 3.82(15) . . . . ?
C5 N1 C7 C14 -173.7(4) . . . . ?
C5 N1 C7 S2 179.2(4) . . . . ?
C5 N1 C7 C15 1.9(7) . . . . ?
C5 C4 C3 C2 -0.7(2) . . . . ?
C5 C4 C15 C7 -0.4(10) . . . . ?
C5 C6 C1 C2 0.4(2) . . . . ?
C8 N1 C5 C4 -176.97(13) . . . . ?
C8 N1 C5 C6 3.0(2) . . . . ?
C8 N1 C7 S1 179.96(10) . . . . ?
C8 N1 C7 C14 2.5(5) . . . . ?
C8 N1 C7 S2 -4.7(4) . . . . ?
C8 N1 C7 C15 178.1(7) . . . . ?
C8 C13 C12 C11 0.2(2) . . . . ?
C8 C13 S2 C7 -6.0(4) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C4 S1 C7 C14 173.6(6) . . . . ?
C4 S1 C7 N1 -3.16(12) . . . . ?
C4 C5 C6 C1 -0.95(19) . . . . ?
C4 C3 C2 C1 0.2(2) . . . . ?
C13 C14 C7 S1 179.70(15) . . . . ?
C13 C14 C7 N1 -3.5(6) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
C13 C12 C11 C10 -0.6(2) . . . . ?
C7 S1 C4 C5 1.83(12) . . . . ?
C7 S1 C4 C3 -179.48(13) . . . . ?
C7 C14 C13 C8 3.4(6) . . . . ?
C7 C14 C13 C12 -179.1(2) . . . . ?
C7 N1 C5 C4 -2.29(15) . . . . ?
C7 N1 C5 C6 177.72(13) . . . . ?
C7 N1 C8 C13 -0.11(14) . . . . ?
C7 N1 C8 C9 179.51(13) . . . . ?
C3 C4 C15 C7 -179.9(3) . . . . ?
C12 C13 S2 C7 178.82(16) . . . . ?
C6 C5 C4 S1 179.92(11) . . . . ?
C6 C5 C4 C3 1.1(2) . . . . ?
C6 C5 C4 C15 -178.4(7) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C9 C8 C13 C14 178.2(4) . . . . ?
C9 C8 C13 C12 0.3(2) . . . . ?
C9 C8 C13 S2 -175.3(3) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
S2 C13 C12 C11 175.1(4) . . . . ?
S2 C7 C15 C4 -177.3(5) . . . . ?
C15 C4 C3 C2 178.7(9) . . . . ?
C15 C7 S2 C13 -177.7(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
