# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_190830-bxh01-pwy
_database_code_depnum_ccdc_archive 'CCDC 2006122'
loop_
_audit_author_name
_audit_author_address
'Yu Wang'
;NENU
China
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             2020-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 O4 S2'
_chemical_formula_sum            'C23 H22 O4 S2'
_chemical_formula_weight         426.52
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8162(5)
_cell_length_b                   9.9355(5)
_cell_length_c                   12.7903(7)
_cell_angle_alpha                88.965(4)
_cell_angle_beta                 85.831(4)
_cell_angle_gamma                70.437(5)
_cell_volume                     1052.86(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2284
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2220
_cell_measurement_theta_min      4.2090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7729
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.361
_diffrn_reflns_theta_min         3.790
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  35.00   1.00    5.00    --   11.01 -73.00  46.00   83
  2  ω    -19.00  84.00   1.00    5.00    --   11.01  73.00 175.00  103
  3  ω     -6.00  73.00   1.00    5.00    --   11.01  57.00 -30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0590517000
_diffrn_orient_matrix_UB_12      0.0633062000
_diffrn_orient_matrix_UB_13      -0.0165053000
_diffrn_orient_matrix_UB_21      0.0152737000
_diffrn_orient_matrix_UB_22      0.0382613000
_diffrn_orient_matrix_UB_23      0.0419797000
_diffrn_orient_matrix_UB_31      0.0600546000
_diffrn_orient_matrix_UB_32      0.0163977000
_diffrn_orient_matrix_UB_33      -0.0325135000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3557
_reflns_number_total             4789
_reflns_odcompleteness_completeness 99.33
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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         0.331
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.049
_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+0.3020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1312
_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:
 C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q)
2.b Idealised Me refined as rotating group:
 C00R(H00A,H00E,H00I), C00S(H00N,H00R,H00S), C00T(H00T,H00U,H00V)
;
_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
S01 S 0.80034(6) 0.30109(6) 0.09528(4) 0.03920(16) Uani 1 1 d . . . . .
S02 S 0.39741(7) 0.28665(6) 0.31114(4) 0.04398(17) Uani 1 1 d . . . . .
O003 O 0.7062(2) 0.28876(18) 0.01213(11) 0.0542(4) Uani 1 1 d . . . . .
O004 O 0.95930(19) 0.20130(17) 0.10136(12) 0.0527(4) Uani 1 1 d . . . . .
O005 O 0.4516(2) 0.2952(2) 0.41211(12) 0.0603(5) Uani 1 1 d . . . . .
O006 O 0.2488(2) 0.38893(18) 0.28252(15) 0.0625(5) Uani 1 1 d . . . . .
C007 C 0.7806(3) 0.2820(2) 0.31438(15) 0.0381(4) Uani 1 1 d . . . . .
C008 C 0.8054(2) 0.4758(2) 0.09763(14) 0.0363(4) Uani 1 1 d . . . . .
C009 C 0.6899(3) 0.2921(2) 0.21979(15) 0.0386(5) Uani 1 1 d . . . . .
C00A C 0.3908(2) 0.1141(2) 0.29258(15) 0.0391(5) Uani 1 1 d . . . . .
C00B C 0.5412(3) 0.2956(2) 0.21006(16) 0.0444(5) Uani 1 1 d . . . . .
H00B H 0.507940 0.303729 0.142187 0.053 Uiso 1 1 calc R . . . .
C00C C 0.9046(3) 0.1583(2) 0.33363(16) 0.0481(5) Uani 1 1 d . . . . .
H00C H 0.926719 0.080015 0.289180 0.058 Uiso 1 1 calc R . . . .
C00D C 0.3000(3) 0.0888(2) 0.21627(17) 0.0462(5) Uani 1 1 d . . . . .
H00D H 0.245703 0.162108 0.172459 0.055 Uiso 1 1 calc R . . . .
C00E C 0.9674(3) 0.2628(3) 0.48512(16) 0.0522(6) Uani 1 1 d . . . . .
C00F C 0.9319(3) 0.5033(3) 0.14013(17) 0.0488(5) Uani 1 1 d . . . . .
H00F H 1.016641 0.429585 0.166059 0.059 Uiso 1 1 calc R . . . .
C00G C 0.2908(3) -0.0460(3) 0.20567(18) 0.0491(5) Uani 1 1 d . . . . .
H00G H 0.231173 -0.063225 0.153586 0.059 Uiso 1 1 calc R . . . .
C00H C 0.6805(3) 0.5855(3) 0.05831(18) 0.0496(6) Uani 1 1 d . . . . .
H00H H 0.596734 0.566134 0.028712 0.060 Uiso 1 1 calc R . . . .
C00I C 0.3687(3) -0.1563(2) 0.27118(17) 0.0485(5) Uani 1 1 d . . . . .
C00J C 0.4735(3) 0.0045(3) 0.35671(18) 0.0513(6) Uani 1 1 d . . . . .
H00J H 0.537439 0.020596 0.406478 0.062 Uiso 1 1 calc R . . . .
C00K C 0.8423(3) 0.3852(3) 0.46716(19) 0.0602(7) Uani 1 1 d . . . . .
H00K H 0.819181 0.462668 0.512585 0.072 Uiso 1 1 calc R . . . .
C00L C 0.7495(3) 0.3956(3) 0.38222(18) 0.0550(6) Uani 1 1 d . . . . .
H00L H 0.665704 0.479906 0.371077 0.066 Uiso 1 1 calc R . . . .
C00M C 0.9961(3) 0.1491(3) 0.41763(17) 0.0546(6) Uani 1 1 d . . . . .
H00M H 1.079032 0.064310 0.429190 0.065 Uiso 1 1 calc R . . . .
C00N C 0.8044(3) 0.7545(3) 0.10604(18) 0.0552(6) Uani 1 1 d . . . . .
C00O C 0.9292(3) 0.6430(3) 0.14309(19) 0.0587(7) Uani 1 1 d . . . . .
H00O H 1.014222 0.662545 0.170940 0.070 Uiso 1 1 calc R . . . .
C00P C 0.6811(3) 0.7235(3) 0.06325(19) 0.0578(6) Uani 1 1 d . . . . .
H00P H 0.596556 0.797259 0.037191 0.069 Uiso 1 1 calc R . . . .
C00Q C 0.4604(3) -0.1284(3) 0.34622(19) 0.0575(6) Uani 1 1 d . . . . .
H00Q H 0.514187 -0.201405 0.390457 0.069 Uiso 1 1 calc R . . . .
C00R C 0.3518(4) -0.3013(3) 0.2622(2) 0.0683(7) Uani 1 1 d . . . . .
H00A H 0.312057 -0.327264 0.328703 0.102 Uiso 1 1 calc GR . . . .
H00E H 0.455102 -0.370353 0.241929 0.102 Uiso 1 1 calc GR . . . .
H00I H 0.277448 -0.298670 0.210383 0.102 Uiso 1 1 calc GR . . . .
C00S C 1.0723(4) 0.2525(4) 0.5752(2) 0.0854(10) Uani 1 1 d . . . . .
H00N H 1.180488 0.240956 0.548213 0.128 Uiso 1 1 calc GR . . . .
H00R H 1.072670 0.171918 0.617791 0.128 Uiso 1 1 calc GR . . . .
H00S H 1.030503 0.338239 0.616765 0.128 Uiso 1 1 calc GR . . . .
C00T C 0.8029(5) 0.9063(3) 0.1128(2) 0.0872(10) Uani 1 1 d . . . . .
H00T H 0.745249 0.949279 0.176983 0.131 Uiso 1 1 calc GR . . . .
H00U H 0.750637 0.959484 0.054396 0.131 Uiso 1 1 calc GR . . . .
H00V H 0.911710 0.906744 0.111232 0.131 Uiso 1 1 calc GR . . . .


_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
S01 O003 1.4272(15) . ?
S01 O004 1.4267(16) . ?
S01 C008 1.753(2) . ?
S01 C009 1.822(2) . ?
S02 O005 1.4228(16) . ?
S02 O006 1.4309(17) . ?
S02 C00A 1.755(2) . ?
S02 C00B 1.766(2) . ?
C007 C009 1.482(3) . ?
C007 C00C 1.376(3) . ?
C007 C00L 1.377(3) . ?
C008 C00F 1.382(3) . ?
C008 C00H 1.382(3) . ?
C009 C00B 1.314(3) . ?
C00A C00D 1.383(3) . ?
C00A C00J 1.384(3) . ?
C00C C00M 1.373(3) . ?
C00D C00G 1.378(3) . ?
C00E C00K 1.370(3) . ?
C00E C00M 1.377(3) . ?
C00E C00S 1.510(3) . ?
C00F C00O 1.382(3) . ?
C00G C00I 1.386(3) . ?
C00H C00P 1.375(3) . ?
C00I C00Q 1.387(3) . ?
C00I C00R 1.503(3) . ?
C00J C00Q 1.373(3) . ?
C00K C00L 1.389(3) . ?
C00N C00O 1.379(4) . ?
C00N C00P 1.375(4) . ?
C00N C00T 1.508(3) . ?

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
O003 S01 C008 108.79(9) . . ?
O003 S01 C009 108.66(10) . . ?
O004 S01 O003 119.44(10) . . ?
O004 S01 C008 109.90(10) . . ?
O004 S01 C009 106.61(9) . . ?
C008 S01 C009 102.02(9) . . ?
O005 S02 O006 119.42(11) . . ?
O005 S02 C00A 108.92(10) . . ?
O005 S02 C00B 111.76(10) . . ?
O006 S02 C00A 108.94(10) . . ?
O006 S02 C00B 104.66(11) . . ?
C00A S02 C00B 101.65(10) . . ?
C00C C007 C009 119.81(18) . . ?
C00C C007 C00L 118.26(19) . . ?
C00L C007 C009 121.87(19) . . ?
C00F C008 S01 120.06(17) . . ?
C00F C008 C00H 120.7(2) . . ?
C00H C008 S01 119.26(16) . . ?
C007 C009 S01 115.62(15) . . ?
C00B C009 S01 113.67(15) . . ?
C00B C009 C007 130.72(19) . . ?
C00D C00A S02 120.26(16) . . ?
C00D C00A C00J 120.2(2) . . ?
C00J C00A S02 119.50(17) . . ?
C009 C00B S02 127.44(16) . . ?
C00M C00C C007 120.9(2) . . ?
C00G C00D C00A 119.5(2) . . ?
C00K C00E C00M 117.9(2) . . ?
C00K C00E C00S 121.3(2) . . ?
C00M C00E C00S 120.8(3) . . ?
C00O C00F C008 118.3(2) . . ?
C00D C00G C00I 121.3(2) . . ?
C00P C00H C008 119.5(2) . . ?
C00G C00I C00Q 118.1(2) . . ?
C00G C00I C00R 120.9(2) . . ?
C00Q C00I C00R 121.0(2) . . ?
C00Q C00J C00A 119.4(2) . . ?
C00E C00K C00L 121.1(2) . . ?
C007 C00L C00K 120.5(2) . . ?
C00C C00M C00E 121.4(2) . . ?
C00O C00N C00T 120.8(3) . . ?
C00P C00N C00O 118.3(2) . . ?
C00P C00N C00T 120.9(3) . . ?
C00N C00O C00F 122.1(2) . . ?
C00N C00P C00H 121.2(2) . . ?
C00J C00Q C00I 121.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.052
_oxdiff_exptl_absorpt_empirical_full_min 0.946
