# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_7241
_audit_block_doi                 10.5517/ccdc.csd.cc29b09z
_database_code_depnum_ccdc_archive 'CCDC 2124780'
loop_
_audit_author_name
_audit_author_address
'Jian Hao'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2021-11-28 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2021-05-19
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            2H-thiete
_chemical_name_systematic        
;
Dimethyl 4-(4-bromophenyl)-2H-thiete-2,3-dicarboxylate 1,1-dioxide 
;
_chemical_formula_moiety         'C13 H11 Br O6 S'
_chemical_formula_sum            'C13 H11 Br O6 S'
_chemical_formula_weight         375.19
_chemical_melting_point          '149-150 deg'
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'
Br Br -0.2901 2.4595 '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      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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   5.7150(3)
_cell_length_b                   13.2605(6)
_cell_length_c                   18.8559(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.277(4)
_cell_angle_gamma                90.00
_cell_volume                     1422.90(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1571
_cell_measurement_temperature    115.7(3)
_cell_measurement_theta_max      28.1530
_cell_measurement_theta_min      3.9450
_exptl_absorpt_coefficient_mu    3.059
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5296
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      115.7(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.8175
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0070  -99.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -26.00   15.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852    0.0000  -90.0000 111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0494611000
_diffrn_orient_matrix_UB_12      -0.0346679000
_diffrn_orient_matrix_UB_13      -0.0231003000
_diffrn_orient_matrix_UB_21      -0.0037412000
_diffrn_orient_matrix_UB_22      0.0373563000
_diffrn_orient_matrix_UB_23      -0.0269598000
_diffrn_orient_matrix_UB_31      0.1144563000
_diffrn_orient_matrix_UB_32      0.0161375000
_diffrn_orient_matrix_UB_33      0.0128843000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2248
_reflns_number_total             2710
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.089
_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     192
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0284P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0749
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.30592(5) 0.20910(3) 0.034875(16) 0.02175(12) Uani 1 1 d . . .
S1 S -0.40420(12) 0.14781(6) -0.30450(4) 0.01360(18) Uani 1 1 d . . .
C10 C 0.1114(5) 0.2164(2) -0.10938(16) 0.0184(7) Uani 1 1 d . . .
H10 H 0.2423 0.2579 -0.1170 0.022 Uiso 1 1 calc R . .
O2 O -0.4656(3) 0.25225(16) -0.31149(11) 0.0186(5) Uani 1 1 d . . .
O4 O -0.7405(3) -0.01018(17) -0.42486(11) 0.0214(5) Uani 1 1 d . . .
O1 O -0.2111(3) 0.11194(17) -0.34121(10) 0.0192(5) Uani 1 1 d . . .
O3 O -0.5151(4) -0.10020(17) -0.34312(11) 0.0264(5) Uani 1 1 d . . .
C13 C -0.2738(5) 0.0945(2) -0.08593(15) 0.0156(7) Uani 1 1 d . . .
H13 H -0.4051 0.0535 -0.0778 0.019 Uiso 1 1 calc R . .
C1 C -0.6572(5) 0.0639(2) -0.31275(15) 0.0139(7) Uani 1 1 d . . .
H1 H -0.8095 0.1000 -0.3244 0.017 Uiso 1 1 calc R . .
C4 C -0.6268(5) -0.0267(2) -0.36064(15) 0.0158(7) Uani 1 1 d . . .
C11 C 0.0811(5) 0.1792(2) -0.04239(16) 0.0154(7) Uani 1 1 d . . .
C8 C -0.2460(5) 0.1299(2) -0.15409(15) 0.0136(7) Uani 1 1 d . . .
C12 C -0.1087(5) 0.1192(2) -0.02940(15) 0.0155(7) Uani 1 1 d . . .
H12 H -0.1262 0.0952 0.0173 0.019 Uiso 1 1 calc R . .
C9 C -0.0543(5) 0.1918(2) -0.16530(16) 0.0173(7) Uani 1 1 d . . .
H9 H -0.0373 0.2172 -0.2117 0.021 Uiso 1 1 calc R . .
O6 O -0.9223(3) -0.05826(16) -0.23356(11) 0.0173(5) Uani 1 1 d . . .
O5 O -0.7124(3) -0.03390(16) -0.12772(11) 0.0199(5) Uani 1 1 d . . .
C5 C -0.7450(5) -0.0198(2) -0.19090(16) 0.0144(7) Uani 1 1 d . . .
C2 C -0.6006(5) 0.0457(2) -0.23337(15) 0.0131(7) Uani 1 1 d . . .
C7 C -1.0830(5) -0.1216(2) -0.19847(16) 0.0187(7) Uani 1 1 d . . .
H7A H -1.2107 -0.1438 -0.2332 0.028 Uiso 1 1 calc R . .
H7B H -1.1486 -0.0832 -0.1605 0.028 Uiso 1 1 calc R . .
H7C H -0.9986 -0.1806 -0.1779 0.028 Uiso 1 1 calc R . .
C3 C -0.4086(5) 0.1029(2) -0.21578(15) 0.0126(6) Uani 1 1 d . . .
C6 C -0.7179(6) -0.0898(3) -0.47632(17) 0.0308(9) Uani 1 1 d . . .
H6A H -0.8148 -0.0739 -0.5205 0.046 Uiso 1 1 calc R . .
H6B H -0.7706 -0.1538 -0.4571 0.046 Uiso 1 1 calc R . .
H6C H -0.5532 -0.0959 -0.4862 0.046 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
Br1 C11 1.894(3) . ?
S1 O2 1.432(2) . ?
S1 O1 1.437(2) . ?
S1 C1 1.820(3) . ?
S1 C2 2.273(3) . ?
S1 C3 1.778(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(4) . ?
C10 C9 1.390(4) . ?
O4 C4 1.339(3) . ?
O4 C6 1.448(4) . ?
O3 C4 1.195(4) . ?
C13 H13 0.9500 . ?
C13 C8 1.391(4) . ?
C13 C12 1.396(4) . ?
C1 H1 1.0000 . ?
C1 C4 1.522(4) . ?
C1 C2 1.521(4) . ?
C11 C12 1.385(4) . ?
C8 C9 1.400(4) . ?
C8 C3 1.465(4) . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
O6 C5 1.336(3) . ?
O6 C7 1.449(3) . ?
O5 C5 1.203(3) . ?
C5 C2 1.483(4) . ?
C2 C3 1.350(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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
O2 S1 O1 117.94(13) . . ?
O2 S1 C1 113.43(13) . . ?
O2 S1 C2 120.02(12) . . ?
O2 S1 C3 112.70(13) . . ?
O1 S1 C1 113.31(13) . . ?
O1 S1 C2 122.00(12) . . ?
O1 S1 C3 114.86(12) . . ?
C1 S1 C2 41.82(11) . . ?
C3 S1 C1 78.23(13) . . ?
C3 S1 C2 36.41(11) . . ?
C11 C10 H10 120.8 . . ?
C11 C10 C9 118.4(3) . . ?
C9 C10 H10 120.8 . . ?
C4 O4 C6 114.9(3) . . ?
C8 C13 H13 120.0 . . ?
C8 C13 C12 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
S1 C1 H1 113.2 . . ?
C4 C1 S1 113.6(2) . . ?
C4 C1 H1 113.2 . . ?
C2 C1 S1 85.24(17) . . ?
C2 C1 H1 113.2 . . ?
C2 C1 C4 115.7(2) . . ?
O4 C4 C1 109.6(3) . . ?
O3 C4 O4 125.9(3) . . ?
O3 C4 C1 124.5(3) . . ?
C10 C11 Br1 119.7(2) . . ?
C10 C11 C12 122.2(3) . . ?
C12 C11 Br1 118.1(2) . . ?
C13 C8 C9 119.6(3) . . ?
C13 C8 C3 122.3(3) . . ?
C9 C8 C3 118.1(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 C13 119.0(3) . . ?
C11 C12 H12 120.5 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C5 O6 C7 115.1(2) . . ?
O6 C5 C2 109.1(2) . . ?
O5 C5 O6 125.2(3) . . ?
O5 C5 C2 125.6(3) . . ?
C1 C2 S1 52.93(14) . . ?
C5 C2 S1 175.6(2) . . ?
C5 C2 C1 123.1(2) . . ?
C3 C2 S1 51.39(15) . . ?
C3 C2 C1 104.3(2) . . ?
C3 C2 C5 132.6(3) . . ?
O6 C7 H7A 109.5 . . ?
O6 C7 H7B 109.5 . . ?
O6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C3 S1 127.1(2) . . ?
C2 C3 S1 92.20(19) . . ?
C2 C3 C8 140.7(3) . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
Br1 C11 C12 C13 -178.6(2) . . . . ?
S1 C1 C4 O4 -100.6(2) . . . . ?
S1 C1 C4 O3 78.4(3) . . . . ?
S1 C1 C2 C5 177.7(3) . . . . ?
S1 C1 C2 C3 -0.5(2) . . . . ?
S1 C2 C3 C8 179.1(5) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
O2 S1 C1 C4 134.5(2) . . . . ?
O2 S1 C1 C2 -109.47(18) . . . . ?
O2 S1 C2 C1 92.5(2) . . . . ?
O2 S1 C2 C5 67(3) . . . . ?
O2 S1 C2 C3 -88.1(2) . . . . ?
O2 S1 C3 C8 -69.0(3) . . . . ?
O2 S1 C3 C2 110.27(19) . . . . ?
O1 S1 C1 C4 -3.4(3) . . . . ?
O1 S1 C1 C2 112.57(18) . . . . ?
O1 S1 C2 C1 -90.08(19) . . . . ?
O1 S1 C2 C5 -116(3) . . . . ?
O1 S1 C2 C3 89.3(2) . . . . ?
O1 S1 C3 C8 69.9(3) . . . . ?
O1 S1 C3 C2 -110.83(19) . . . . ?
C13 C8 C9 C10 1.5(4) . . . . ?
C13 C8 C3 S1 176.2(2) . . . . ?
C13 C8 C3 C2 -2.7(6) . . . . ?
C1 S1 C2 C5 -26(3) . . . . ?
C1 S1 C2 C3 179.4(3) . . . . ?
C1 S1 C3 C8 -179.7(3) . . . . ?
C1 S1 C3 C2 -0.41(19) . . . . ?
C1 C2 C3 S1 0.5(2) . . . . ?
C1 C2 C3 C8 179.6(4) . . . . ?
C4 C1 C2 S1 113.9(2) . . . . ?
C4 C1 C2 C5 -68.4(3) . . . . ?
C4 C1 C2 C3 113.4(3) . . . . ?
C11 C10 C9 C8 -0.6(5) . . . . ?
C8 C13 C12 C11 0.1(4) . . . . ?
C12 C13 C8 C9 -1.2(4) . . . . ?
C12 C13 C8 C3 177.5(3) . . . . ?
C9 C10 C11 Br1 178.9(2) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C9 C8 C3 S1 -5.1(4) . . . . ?
C9 C8 C3 C2 176.0(4) . . . . ?
O6 C5 C2 S1 25(3) . . . . ?
O6 C5 C2 C1 0.7(4) . . . . ?
O6 C5 C2 C3 178.3(3) . . . . ?
O5 C5 C2 S1 -153(3) . . . . ?
O5 C5 C2 C1 -177.4(3) . . . . ?
O5 C5 C2 C3 0.2(5) . . . . ?
C5 C2 C3 S1 -177.4(3) . . . . ?
C5 C2 C3 C8 1.7(6) . . . . ?
C2 S1 C1 C4 -116.0(3) . . . . ?
C2 S1 C3 C8 -179.3(4) . . . . ?
C2 C1 C4 O4 163.1(2) . . . . ?
C2 C1 C4 O3 -17.9(4) . . . . ?
C7 O6 C5 O5 0.0(4) . . . . ?
C7 O6 C5 C2 -178.1(2) . . . . ?
C3 S1 C1 C4 -115.6(2) . . . . ?
C3 S1 C1 C2 0.36(16) . . . . ?
C3 S1 C2 C1 -179.4(3) . . . . ?
C3 S1 C2 C5 155(3) . . . . ?
C3 C8 C9 C10 -177.3(3) . . . . ?
C6 O4 C4 O3 -1.1(4) . . . . ?
C6 O4 C4 C1 178.0(2) . . . . ?
