# Supplementary Information (SI) 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. 
# 
#######################################################################

data_exp_14273_auto
_database_code_depnum_ccdc_archive 'CCDC 2353212'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Hubei Normal University
China
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_audit_creation_date             2024-04-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Br O2 S'
_chemical_formula_sum            'C14 H9 Br O2 S'
_chemical_formula_weight         321.18
_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                   9.4078(8)
_cell_length_b                   13.1508(11)
_cell_length_c                   10.7940(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.573(9)
_cell_angle_gamma                90
_cell_volume                     1273.11(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1527
_cell_measurement_temperature    296.15(10)
_cell_measurement_theta_max      24.5520
_cell_measurement_theta_min      3.0980
_shelx_estimated_absorpt_T_max   0.687
_shelx_estimated_absorpt_T_min   0.631
_exptl_absorpt_coefficient_mu    3.382
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
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    1.676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5746
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.214
_diffrn_reflns_theta_min         2.271
_diffrn_ambient_temperature      296.15(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  45.00   1.00    4.50    --   17.12 -77.00-180.00   76
  2  ω      3.00  85.00   1.00    4.50    --   17.12  57.00 -60.00   82
  3  ω    -16.00   9.00   1.00    4.50    --  -17.59 -77.00 -90.00   25
  4  ω    -30.00   7.00   1.00    4.50    --  -17.59 -77.00  60.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147337000
_diffrn_orient_matrix_UB_12      -0.0494010000
_diffrn_orient_matrix_UB_13      0.0272726000
_diffrn_orient_matrix_UB_21      0.0168810000
_diffrn_orient_matrix_UB_22      -0.0170108000
_diffrn_orient_matrix_UB_23      -0.0562986000
_diffrn_orient_matrix_UB_31      0.0758609000
_diffrn_orient_matrix_UB_32      0.0133570000
_diffrn_orient_matrix_UB_33      0.0289575000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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                2037
_reflns_number_total             2933
_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 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.022
_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)+(0.0310P)²+0.6126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C10(H10), C11(H11), C6(H6), C3(H3), C5(H5), C4(H4)
;
_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
Br1 Br -0.05785(4) 0.33922(3) 0.09065(3) 0.05816(15) Uani 1 1 d . . . . .
S1 S 0.46527(10) 0.49920(8) 0.66592(8) 0.0571(3) Uani 1 1 d . . . . .
O1 O 0.2618(2) 0.64775(15) 0.60250(19) 0.0447(5) Uani 1 1 d . . . . .
O2 O 0.2854(3) 0.79347(18) 0.7040(2) 0.0595(6) Uani 1 1 d . . . . .
C9 C 0.1925(3) 0.4922(2) 0.4866(3) 0.0374(7) Uani 1 1 d . . . . .
C12 C 0.0465(3) 0.4002(2) 0.2519(3) 0.0391(7) Uani 1 1 d . . . . .
C13 C 0.0895(3) 0.5011(2) 0.2540(3) 0.0437(8) Uani 1 1 d . . . . .
H13 H 0.069400 0.537941 0.177079 0.052 Uiso 1 1 calc R U . . .
C2 C 0.4416(3) 0.6610(2) 0.8196(3) 0.0411(7) Uani 1 1 d . . . . .
C8 C 0.2736(3) 0.5392(2) 0.6153(3) 0.0393(7) Uani 1 1 d . . . . .
H8 H 0.226352 0.517111 0.680174 0.047 Uiso 1 1 calc R U . . .
C1 C 0.3253(3) 0.7062(3) 0.7085(3) 0.0425(7) Uani 1 1 d . . . . .
C14 C 0.1626(3) 0.5465(2) 0.3718(3) 0.0435(8) Uani 1 1 d . . . . .
H14 H 0.191898 0.614206 0.373757 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5166(3) 0.5712(3) 0.8100(3) 0.0438(8) Uani 1 1 d . . . . .
C10 C 0.1479(4) 0.3912(2) 0.4816(3) 0.0484(8) Uani 1 1 d . . . . .
H10 H 0.167499 0.354054 0.558266 0.058 Uiso 1 1 calc R U . . .
C11 C 0.0749(4) 0.3450(2) 0.3644(3) 0.0486(8) Uani 1 1 d . . . . .
H11 H 0.045475 0.277323 0.362067 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6347(3) 0.5386(3) 0.9145(3) 0.0531(9) Uani 1 1 d . . . . .
H6 H 0.685649 0.479220 0.907991 0.064 Uiso 1 1 calc R U . . .
C3 C 0.4844(4) 0.7159(3) 0.9353(3) 0.0527(9) Uani 1 1 d . . . . .
H3 H 0.434579 0.775658 0.942736 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6759(4) 0.5942(3) 1.0272(3) 0.0590(10) Uani 1 1 d . . . . .
H5 H 0.755633 0.572527 1.096472 0.071 Uiso 1 1 calc R U . . .
C4 C 0.6004(4) 0.6820(3) 1.0392(3) 0.0596(10) Uani 1 1 d . . . . .
H4 H 0.627705 0.718127 1.116844 0.072 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
Br1 C12 1.899(3) . ?
S1 C8 1.798(3) . ?
S1 C7 1.759(3) . ?
O1 C8 1.435(3) . ?
O1 C1 1.358(4) . ?
O2 C1 1.204(4) . ?
C9 C8 1.502(4) . ?
C9 C14 1.383(4) . ?
C9 C10 1.389(4) . ?
C12 C13 1.385(4) . ?
C12 C11 1.370(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(4) . ?
C2 C1 1.482(4) . ?
C2 C7 1.396(4) . ?
C2 C3 1.393(4) . ?
C8 H8 0.9800 . ?
C14 H14 0.9300 . ?
C7 C6 1.391(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.371(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(5) . ?
C4 H4 0.9300 . ?

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
C7 S1 C8 95.37(14) . . ?
C1 O1 C8 118.7(2) . . ?
C14 C9 C8 121.7(3) . . ?
C14 C9 C10 118.8(3) . . ?
C10 C9 C8 119.5(3) . . ?
C13 C12 Br1 119.1(2) . . ?
C11 C12 Br1 119.8(2) . . ?
C11 C12 C13 121.0(3) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C7 C2 C1 123.1(3) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 C7 119.4(3) . . ?
S1 C8 H8 109.0 . . ?
O1 C8 S1 111.2(2) . . ?
O1 C8 C9 108.5(2) . . ?
O1 C8 H8 109.0 . . ?
C9 C8 S1 110.1(2) . . ?
C9 C8 H8 109.0 . . ?
O1 C1 C2 119.0(3) . . ?
O2 C1 O1 116.9(3) . . ?
O2 C1 C2 124.1(3) . . ?
C9 C14 C13 120.6(3) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C2 C7 S1 120.7(2) . . ?
C6 C7 S1 119.4(3) . . ?
C6 C7 C2 119.9(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C7 C6 H6 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?

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 C12 C13 C14 178.5(2) . . . . ?
Br1 C12 C11 C10 -178.5(2) . . . . ?
S1 C7 C6 C5 179.9(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C12 C13 C14 C9 -0.1(5) . . . . ?
C13 C12 C11 C10 -0.1(5) . . . . ?
C2 C7 C6 C5 0.8(5) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C8 S1 C7 C2 -27.9(3) . . . . ?
C8 S1 C7 C6 153.0(3) . . . . ?
C8 O1 C1 O2 -163.3(3) . . . . ?
C8 O1 C1 C2 18.9(4) . . . . ?
C8 C9 C14 C13 179.1(3) . . . . ?
C8 C9 C10 C11 -179.0(3) . . . . ?
C1 O1 C8 S1 -59.9(3) . . . . ?
C1 O1 C8 C9 178.8(2) . . . . ?
C1 C2 C7 S1 -5.5(4) . . . . ?
C1 C2 C7 C6 173.6(3) . . . . ?
C1 C2 C3 C4 -174.8(3) . . . . ?
C14 C9 C8 S1 -101.3(3) . . . . ?
C14 C9 C8 O1 20.6(4) . . . . ?
C14 C9 C10 C11 0.0(5) . . . . ?
C7 S1 C8 O1 58.0(2) . . . . ?
C7 S1 C8 C9 178.3(2) . . . . ?
C7 C2 C1 O1 16.7(5) . . . . ?
C7 C2 C1 O2 -161.0(3) . . . . ?
C7 C2 C3 C4 0.4(5) . . . . ?
C7 C6 C5 C4 0.7(5) . . . . ?
C10 C9 C8 S1 77.7(3) . . . . ?
C10 C9 C8 O1 -160.4(3) . . . . ?
C10 C9 C14 C13 0.1(4) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C6 C5 C4 C3 -1.7(6) . . . . ?
C3 C2 C1 O1 -168.3(3) . . . . ?
C3 C2 C1 O2 14.0(5) . . . . ?
C3 C2 C7 S1 179.6(2) . . . . ?
C3 C2 C7 C6 -1.3(5) . . . . ?

_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 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.807
