# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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. 
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data_y
_database_code_depnum_ccdc_archive 'CCDC 2059266'
loop_
_audit_author_name
_audit_author_address
'Qun Cai'
;Wuhan University of Science and Technology
China
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br2 O2 S'
_chemical_formula_sum            'C15 H12 Br2 O2 S'
_chemical_formula_weight         416.13
_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'
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'

_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                   10.004(4)
_cell_length_b                   10.895(4)
_cell_length_c                   15.049(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.962(7)
_cell_angle_gamma                90
_cell_volume                     1591.8(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3925
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.83
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.623
_shelx_estimated_absorpt_T_min   0.508
_exptl_absorpt_coefficient_mu    5.221
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.3004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9345
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.500
_diffrn_reflns_theta_max         24.500
_diffrn_reflns_theta_min         2.098
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1799
_reflns_number_total             2659
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0788
_refine_ls_restrained_S_all      1.066
_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)+(0.1537P)²+0.7411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2457
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
Br1 Br 1.07494(13) 0.09195(16) 0.78934(8) 0.1033(7) Uani 1 1 d . . . . .
Br2 Br 0.97692(10) -0.29712(9) 0.44903(9) 0.0745(5) Uani 1 1 d . . . . .
C1 C 0.5955(14) 0.5519(10) 0.2782(8) 0.082(4) Uani 1 1 d . . . . .
H1A H 0.6189 0.6324 0.3030 0.124 Uiso 1 1 calc GR . . . .
H1B H 0.5093 0.5552 0.2332 0.124 Uiso 1 1 calc GR . . . .
H1C H 0.6662 0.5232 0.2500 0.124 Uiso 1 1 calc GR . . . .
C2 C 0.5832(11) 0.4651(8) 0.3543(7) 0.058(3) Uani 1 1 d . . . . .
C3 C 0.6626(11) 0.4849(8) 0.4423(7) 0.056(2) Uani 1 1 d . . . . .
H3 H 0.7199 0.5532 0.4542 0.067 Uiso 1 1 calc R . . . .
C4 C 0.6578(8) 0.4060(7) 0.5114(6) 0.043(2) Uani 1 1 d . . . . .
H4 H 0.7128 0.4189 0.5700 0.052 Uiso 1 1 calc R . . . .
C5 C 0.5698(8) 0.3064(6) 0.4933(5) 0.0330(18) Uani 1 1 d . . . . .
C6 C 0.4842(9) 0.2880(7) 0.4077(6) 0.042(2) Uani 1 1 d . . . . .
H6 H 0.4213 0.2236 0.3972 0.050 Uiso 1 1 calc R . . . .
C7 C 0.4939(10) 0.3683(9) 0.3372(6) 0.055(2) Uani 1 1 d . . . . .
H7 H 0.4395 0.3557 0.2784 0.066 Uiso 1 1 calc R . . . .
C8 C 0.6886(8) 0.0876(7) 0.5662(5) 0.0351(18) Uani 1 1 d . . . . .
H8 H 0.6664 0.0369 0.5151 0.042 Uiso 1 1 calc R . . . .
C9 C 0.8082(8) 0.0741(7) 0.6253(6) 0.0395(19) Uani 1 1 d . . . . .
H9 H 0.8255 0.1267 0.6754 0.047 Uiso 1 1 calc R . . . .
C10 C 0.9181(8) -0.0145(7) 0.6215(5) 0.0377(19) Uani 1 1 d . . . . .
C11 C 1.0398(10) -0.0141(9) 0.6861(6) 0.053(2) Uani 1 1 d . . . . .
C12 C 1.1465(10) -0.0973(11) 0.6808(8) 0.067(3) Uani 1 1 d . . . . .
H12 H 1.2296 -0.0946 0.7248 0.080 Uiso 1 1 calc R . . . .
C13 C 1.1283(9) -0.1817(9) 0.6113(7) 0.056(3) Uani 1 1 d . . . . .
H13 H 1.1976 -0.2370 0.6077 0.067 Uiso 1 1 calc R . . . .
C14 C 1.0045(9) -0.1822(7) 0.5473(6) 0.046(2) Uani 1 1 d . . . . .
C15 C 0.9009(8) -0.1003(7) 0.5514(6) 0.0399(19) Uani 1 1 d . . . . .
H15 H 0.8185 -0.1027 0.5066 0.048 Uiso 1 1 calc R . . . .
O1 O 0.4365(5) 0.1433(5) 0.5664(4) 0.0475(15) Uani 1 1 d . . . . .
O2 O 0.6243(6) 0.2576(6) 0.6683(4) 0.0472(15) Uani 1 1 d . . . . .
S1 S 0.57032(19) 0.19912(17) 0.58181(14) 0.0341(5) Uani 1 1 d . . . . .


_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 1.899(9) . ?
Br2 C14 1.906(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.513(14) . ?
C2 C3 1.388(14) . ?
C2 C7 1.366(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(11) . ?
C5 C6 1.379(11) . ?
C5 S1 1.771(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(13) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.315(11) . ?
C8 S1 1.750(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.474(10) . ?
C10 C11 1.363(11) . ?
C10 C15 1.390(12) . ?
C11 C12 1.417(13) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(13) . ?
C14 C15 1.380(11) . ?
C15 H15 0.9300 . ?
O1 S1 1.437(5) . ?
O2 S1 1.433(6) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 119.5(10) . . ?
C7 C2 C1 120.6(10) . . ?
C7 C2 C3 119.9(9) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(8) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(8) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 S1 119.0(6) . . ?
C6 C5 C4 121.3(8) . . ?
C6 C5 S1 119.7(6) . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.5(8) . . ?
C7 C6 H6 120.7 . . ?
C2 C7 C6 120.2(9) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 H8 119.3 . . ?
C9 C8 S1 121.4(6) . . ?
S1 C8 H8 119.3 . . ?
C8 C9 H9 116.1 . . ?
C8 C9 C10 127.8(8) . . ?
C10 C9 H9 116.1 . . ?
C11 C10 C9 121.1(8) . . ?
C11 C10 C15 118.0(8) . . ?
C15 C10 C9 120.9(7) . . ?
C10 C11 Br1 122.9(7) . . ?
C10 C11 C12 120.9(9) . . ?
C12 C11 Br1 116.2(7) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(9) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.0(8) . . ?
C14 C13 H13 121.0 . . ?
C13 C14 Br2 118.9(7) . . ?
C13 C14 C15 121.8(9) . . ?
C15 C14 Br2 119.3(7) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.8(8) . . ?
C14 C15 H15 119.6 . . ?
C8 S1 C5 103.7(3) . . ?
O1 S1 C5 108.9(4) . . ?
O1 S1 C8 108.6(4) . . ?
O2 S1 C5 108.8(4) . . ?
O2 S1 C8 108.2(4) . . ?
O2 S1 O1 117.8(4) . . ?

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 176.7(8) . . . . ?
Br2 C14 C15 C10 -179.3(6) . . . . ?
C1 C2 C3 C4 -177.5(9) . . . . ?
C1 C2 C7 C6 179.4(8) . . . . ?
C2 C3 C4 C5 -1.4(13) . . . . ?
C3 C2 C7 C6 -1.1(13) . . . . ?
C3 C4 C5 C6 -2.2(12) . . . . ?
C3 C4 C5 S1 176.6(6) . . . . ?
C4 C5 C6 C7 4.0(11) . . . . ?
C4 C5 S1 C8 -92.6(7) . . . . ?
C4 C5 S1 O1 152.0(6) . . . . ?
C4 C5 S1 O2 22.4(7) . . . . ?
C5 C6 C7 C2 -2.4(12) . . . . ?
C6 C5 S1 C8 86.3(7) . . . . ?
C6 C5 S1 O1 -29.2(7) . . . . ?
C6 C5 S1 O2 -158.8(6) . . . . ?
C7 C2 C3 C4 3.1(13) . . . . ?
C8 C9 C10 C11 177.1(8) . . . . ?
C8 C9 C10 C15 -2.4(12) . . . . ?
C9 C8 S1 C5 110.9(7) . . . . ?
C9 C8 S1 O1 -133.4(7) . . . . ?
C9 C8 S1 O2 -4.5(8) . . . . ?
C9 C10 C11 Br1 3.8(12) . . . . ?
C9 C10 C11 C12 -178.3(8) . . . . ?
C9 C10 C15 C14 179.2(7) . . . . ?
C10 C11 C12 C13 -1.3(16) . . . . ?
C11 C10 C15 C14 -0.3(12) . . . . ?
C11 C12 C13 C14 0.5(15) . . . . ?
C12 C13 C14 Br2 179.2(7) . . . . ?
C12 C13 C14 C15 0.4(13) . . . . ?
C13 C14 C15 C10 -0.6(12) . . . . ?
C15 C10 C11 Br1 -176.7(6) . . . . ?
C15 C10 C11 C12 1.2(13) . . . . ?
S1 C5 C6 C7 -174.8(6) . . . . ?
S1 C8 C9 C10 -179.7(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
