# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_dd21176_0m
_database_code_depnum_ccdc_archive 'CCDC 2084840'
loop_
_audit_author_name
_audit_author_address
'Zhang Xingguo'
;Wenzhou University
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O S'
_chemical_formula_weight         252.32

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.2215(3)
_cell_length_b                   8.8635(4)
_cell_length_c                   9.7122(4)
_cell_angle_alpha                91.3540(10)
_cell_angle_beta                 92.0140(10)
_cell_angle_gamma                92.341(2)
_cell_volume                     620.56(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6047
_cell_measurement_theta_min      6.151
_cell_measurement_theta_max      54.958

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6267
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            8960
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.076
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2401
_reflns_number_gt                2160
_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-2013 (Sheldrick, 2013)'
_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)+(0.0637P)²+0.1056P] 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         2401
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_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 0.33503(5) 0.65704(5) 0.34331(4) 0.05308(18) Uani 1 1 d . . . . .
O1 O 0.07761(16) 0.54053(18) 0.18437(14) 0.0770(4) Uani 1 1 d . . . . .
C1 C 0.2414(2) 0.52982(19) 0.21312(15) 0.0511(4) Uani 1 1 d . . . . .
C2 C 0.3610(2) 0.42211(16) 0.14808(14) 0.0453(3) Uani 1 1 d . . . . .
C3 C 0.2808(2) 0.32640(19) 0.04350(17) 0.0569(4) Uani 1 1 d . . . . .
H3 H 0.1562 0.3338 0.0180 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3844(3) 0.22211(19) -0.02138(18) 0.0637(5) Uani 1 1 d . . . . .
H4 H 0.3299 0.1584 -0.0901 0.076 Uiso 1 1 calc R U . . .
C5 C 0.5705(3) 0.21133(19) 0.01527(18) 0.0634(5) Uani 1 1 d . . . . .
H5 H 0.6403 0.1397 -0.0283 0.076 Uiso 1 1 calc R U . . .
C6 C 0.6521(2) 0.30625(18) 0.11577(17) 0.0555(4) Uani 1 1 d . . . . .
H6 H 0.7777 0.2992 0.1382 0.067 Uiso 1 1 calc R U . . .
C7 C 0.5501(2) 0.41340(16) 0.18516(14) 0.0437(3) Uani 1 1 d . . . . .
C8 C 0.64397(19) 0.50951(16) 0.28934(15) 0.0449(3) Uani 1 1 d . . . . .
H8 H 0.7693 0.4943 0.3060 0.054 Uiso 1 1 calc R U . . .
C9 C 0.56997(18) 0.61843(16) 0.36476(14) 0.0406(3) Uani 1 1 d . . . . .
C10 C 0.67494(19) 0.71635(16) 0.46856(14) 0.0417(3) Uani 1 1 d . . . . .
C11 C 0.8664(2) 0.7091(2) 0.48540(19) 0.0635(5) Uani 1 1 d . . . . .
H11 H 0.9292 0.6418 0.4310 0.076 Uiso 1 1 calc R U . . .
C12 C 0.9645(2) 0.8005(2) 0.58184(19) 0.0671(5) Uani 1 1 d . . . . .
H12 H 1.0924 0.7933 0.5907 0.081 Uiso 1 1 calc R U . . .
C13 C 0.8787(2) 0.90190(18) 0.66533(16) 0.0531(4) Uani 1 1 d . . . . .
C14 C 0.6893(2) 0.90842(19) 0.65039(17) 0.0572(4) Uani 1 1 d . . . . .
H14 H 0.6273 0.9748 0.7062 0.069 Uiso 1 1 calc R U . . .
C15 C 0.5893(2) 0.81806(18) 0.55381(17) 0.0522(4) Uani 1 1 d . . . . .
H15 H 0.4613 0.8256 0.5458 0.063 Uiso 1 1 calc R U . . .
C16 C 0.9889(3) 1.0002(2) 0.7707(2) 0.0732(5) Uani 1 1 d . . . . .
H16A H 0.9459 1.1012 0.7685 0.110 Uiso 1 1 calc R U . . .
H16B H 1.1179 1.0013 0.7496 0.110 Uiso 1 1 calc R U . . .
H16C H 0.9730 0.9605 0.8608 0.110 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 C9 1.7507(14) . ?
S1 C1 1.7714(16) . ?
O1 C1 1.2137(18) . ?
C1 C2 1.461(2) . ?
C2 C3 1.402(2) . ?
C2 C7 1.405(2) . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.400(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.4398(19) . ?
C8 C9 1.338(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.4817(19) . ?
C10 C15 1.388(2) . ?
C10 C11 1.391(2) . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(2) . ?
C13 C16 1.511(2) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C9 S1 C1 106.49(7) . . ?
O1 C1 C2 124.65(14) . . ?
O1 C1 S1 115.63(13) . . ?
C2 C1 S1 119.71(10) . . ?
C3 C2 C7 119.98(14) . . ?
C3 C2 C1 117.35(13) . . ?
C7 C2 C1 122.66(13) . . ?
C4 C3 C2 120.51(15) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.05(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.17(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.34(16) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C2 117.93(13) . . ?
C6 C7 C8 118.58(13) . . ?
C2 C7 C8 123.48(13) . . ?
C9 C8 C7 126.91(13) . . ?
C9 C8 H8 116.5 . . ?
C7 C8 H8 116.5 . . ?
C8 C9 C10 124.46(12) . . ?
C8 C9 S1 120.74(11) . . ?
C10 C9 S1 114.79(10) . . ?
C15 C10 C11 116.75(13) . . ?
C15 C10 C9 122.45(13) . . ?
C11 C10 C9 120.79(13) . . ?
C12 C11 C10 120.86(15) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 122.05(15) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 117.40(14) . . ?
C14 C13 C16 121.51(16) . . ?
C12 C13 C16 121.08(16) . . ?
C13 C14 C15 121.20(15) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 121.72(14) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C9 S1 C1 O1 179.99(13) . . . . ?
C9 S1 C1 C2 -0.27(14) . . . . ?
O1 C1 C2 C3 1.1(2) . . . . ?
S1 C1 C2 C3 -178.58(11) . . . . ?
O1 C1 C2 C7 -179.75(15) . . . . ?
S1 C1 C2 C7 0.5(2) . . . . ?
C7 C2 C3 C4 1.2(2) . . . . ?
C1 C2 C3 C4 -179.61(14) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
C5 C6 C7 C8 -179.96(14) . . . . ?
C3 C2 C7 C6 -0.7(2) . . . . ?
C1 C2 C7 C6 -179.78(13) . . . . ?
C3 C2 C7 C8 178.70(13) . . . . ?
C1 C2 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 179.31(14) . . . . ?
C2 C7 C8 C9 -0.1(2) . . . . ?
C7 C8 C9 C10 -178.51(12) . . . . ?
C7 C8 C9 S1 0.3(2) . . . . ?
C1 S1 C9 C8 -0.13(15) . . . . ?
C1 S1 C9 C10 178.80(10) . . . . ?
C8 C9 C10 C15 -173.64(14) . . . . ?
S1 C9 C10 C15 7.48(19) . . . . ?
C8 C9 C10 C11 5.9(2) . . . . ?
S1 C9 C10 C11 -172.99(13) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C9 C10 C11 C12 179.86(15) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C11 C12 C13 C16 179.69(17) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C16 C13 C14 C15 -179.96(15) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C11 C10 C15 C14 0.3(2) . . . . ?
C9 C10 C15 C14 179.86(13) . . . . ?

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
C8 H8 O1 0.93 2.58 3.3300(19) 138.1 1_655

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4



