# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_180508_wxy_1_191
_database_code_depnum_ccdc_archive 'CCDC 1877067'
loop_
_audit_author_name
_audit_author_address
'Jiyong Liu'
;Zhejiang University
China
;
_audit_update_record             
;
2018-11-05 deposited with the CCDC.	2021-06-01 downloaded from the CCDC.
;
_audit_creation_date             2018-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O2 S2'
_chemical_formula_sum            'C16 H14 O2 S2'
_chemical_formula_weight         302.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o s'
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'

_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1839(7)
_cell_length_b                   17.0403(12)
_cell_length_c                   21.7793(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3037.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3508
_cell_measurement_theta_min      3.0296
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18902
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.036
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   77.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
  2 omega  -58.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -77.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   77.0000  120.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0424153000
_diffrn_orient_matrix_UB_12      -0.0196740000
_diffrn_orient_matrix_UB_13      0.0238820000
_diffrn_orient_matrix_UB_21      0.0373831000
_diffrn_orient_matrix_UB_22      -0.0249925000
_diffrn_orient_matrix_UB_23      -0.0219415000
_diffrn_orient_matrix_UB_31      0.0656947000
_diffrn_orient_matrix_UB_32      0.0268556000
_diffrn_orient_matrix_UB_33      -0.0029347000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1994
_reflns_number_total             2777
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.255
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.035
_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)+(0.0644P)²+1.3936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1420
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Me refined with riding coordinates:
 C16(H16A,H16B,H16C)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C11(H11), C13(H13), C14(H14), C15(H15)
;
_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
S1 S 1.14820(11) 0.05878(6) 0.12784(3) 0.0801(3) Uani 1 1 d . . . . .
S2 S 0.78444(11) 0.10041(5) 0.53555(4) 0.0761(3) Uani 1 1 d . . . . .
O1 O 0.9701(3) 0.16673(14) 0.20613(9) 0.0874(7) Uani 1 1 d . . . . .
O2 O 1.1663(2) 0.14597(12) 0.49905(9) 0.0710(6) Uani 1 1 d . . . . .
C1 C 1.2694(5) -0.0216(2) 0.12616(17) 0.0878(11) Uani 1 1 d . . . . .
H1 H 1.304852 -0.045397 0.090136 0.105 Uiso 1 1 calc R . . . .
C2 C 1.3092(5) -0.0474(2) 0.18310(18) 0.0864(10) Uani 1 1 d . . . . .
H2 H 1.374652 -0.091007 0.190504 0.104 Uiso 1 1 calc R . . . .
C3 C 1.2403(4) -0.00071(17) 0.22981(13) 0.0691(8) Uani 1 1 d . . . . .
H3 H 1.255708 -0.009851 0.271512 0.083 Uiso 1 1 calc R . . . .
C4 C 1.1475(3) 0.06002(16) 0.20678(12) 0.0582(7) Uani 1 1 d . . . . .
C5 C 1.0553(3) 0.12269(17) 0.23735(13) 0.0616(7) Uani 1 1 d . . . . .
C6 C 1.0747(3) 0.13068(16) 0.30409(12) 0.0562(7) Uani 1 1 d . . . . .
H6 H 1.144087 0.094799 0.322913 0.067 Uiso 1 1 calc R . . . .
C7 C 1.0037(3) 0.18383(14) 0.34119(12) 0.0524(6) Uani 1 1 d . . . . .
C8 C 1.0406(3) 0.18215(14) 0.40674(12) 0.0520(6) Uani 1 1 d . . . . .
C9 C 1.1614(4) 0.12693(18) 0.43542(12) 0.0622(7) Uani 1 1 d . . . . .
H9A H 1.126988 0.072953 0.429678 0.075 Uiso 1 1 calc R . . . .
H9B H 1.268447 0.133591 0.417032 0.075 Uiso 1 1 calc R . . . .
C10 C 1.0432(3) 0.20377(16) 0.51251(12) 0.0592(7) Uani 1 1 d . . . . .
H10 H 1.096051 0.249624 0.531049 0.071 Uiso 1 1 calc R . . . .
C11 C 0.9778(3) 0.22642(15) 0.45129(12) 0.0551(6) Uani 1 1 d . . . . .
H11 H 0.902552 0.266473 0.444923 0.066 Uiso 1 1 calc R . . . .
C12 C 0.9190(3) 0.17245(14) 0.55642(12) 0.0536(6) Uani 1 1 d . . . . .
C13 C 0.8951(4) 0.19312(18) 0.61573(13) 0.0671(8) Uani 1 1 d . . . . .
H13 H 0.955695 0.231828 0.635415 0.081 Uiso 1 1 calc R . . . .
C14 C 0.7707(4) 0.1508(2) 0.64456(16) 0.0796(10) Uani 1 1 d . . . . .
H14 H 0.740310 0.158249 0.685284 0.096 Uiso 1 1 calc R . . . .
C15 C 0.7010(4) 0.0991(2) 0.60782(17) 0.0836(10) Uani 1 1 d . . . . .
H15 H 0.616586 0.065897 0.619710 0.100 Uiso 1 1 calc R . . . .
C16 C 0.8863(4) 0.24611(17) 0.31950(15) 0.0718(8) Uani 1 1 d . . . . .
H16A H 0.851503 0.277196 0.353851 0.108 Uiso 1 1 calc R . . . .
H16B H 0.939632 0.279172 0.289960 0.108 Uiso 1 1 calc R . . . .
H16C H 0.793035 0.221618 0.300865 0.108 Uiso 1 1 calc 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
S1 C1 1.691(4) . ?
S1 C4 1.719(3) . ?
S2 C12 1.711(3) . ?
S2 C15 1.716(4) . ?
O1 C5 1.230(3) . ?
O2 C9 1.424(3) . ?
O2 C10 1.439(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.356(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.409(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(4) . ?
C4 C5 1.467(4) . ?
C5 C6 1.468(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.345(4) . ?
C7 C8 1.460(4) . ?
C7 C16 1.508(3) . ?
C8 C9 1.501(4) . ?
C8 C11 1.332(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C11 1.488(4) . ?
C10 C12 1.494(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.353(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.320(5) . ?
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
C1 S1 C4 91.93(16) . . ?
C12 S2 C15 91.24(16) . . ?
C9 O2 C10 109.55(19) . . ?
S1 C1 H1 123.7 . . ?
C2 C1 S1 112.6(3) . . ?
C2 C1 H1 123.7 . . ?
C1 C2 H2 123.8 . . ?
C1 C2 C3 112.4(3) . . ?
C3 C2 H2 123.8 . . ?
C2 C3 H3 123.8 . . ?
C4 C3 C2 112.4(3) . . ?
C4 C3 H3 123.8 . . ?
C3 C4 S1 110.7(2) . . ?
C3 C4 C5 131.7(2) . . ?
C5 C4 S1 117.7(2) . . ?
O1 C5 C4 119.0(3) . . ?
O1 C5 C6 123.5(3) . . ?
C4 C5 C6 117.5(2) . . ?
C5 C6 H6 116.2 . . ?
C7 C6 C5 127.6(2) . . ?
C7 C6 H6 116.2 . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 C16 124.1(3) . . ?
C8 C7 C16 116.9(2) . . ?
C7 C8 C9 123.7(2) . . ?
C11 C8 C7 128.4(2) . . ?
C11 C8 C9 107.8(2) . . ?
O2 C9 C8 106.3(2) . . ?
O2 C9 H9A 110.5 . . ?
O2 C9 H9B 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
O2 C10 H10 108.7 . . ?
O2 C10 C11 104.3(2) . . ?
O2 C10 C12 111.2(2) . . ?
C11 C10 H10 108.7 . . ?
C11 C10 C12 114.9(2) . . ?
C12 C10 H10 108.7 . . ?
C8 C11 C10 111.5(2) . . ?
C8 C11 H11 124.2 . . ?
C10 C11 H11 124.2 . . ?
C10 C12 S2 121.61(19) . . ?
C13 C12 S2 110.3(2) . . ?
C13 C12 C10 128.1(3) . . ?
C12 C13 H13 123.2 . . ?
C12 C13 C14 113.6(3) . . ?
C14 C13 H13 123.2 . . ?
C13 C14 H14 123.6 . . ?
C15 C14 C13 112.8(3) . . ?
C15 C14 H14 123.6 . . ?
S2 C15 H15 124.0 . . ?
C14 C15 S2 112.1(3) . . ?
C14 C15 H15 124.0 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
