# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_2469
_database_code_depnum_ccdc_archive 'CCDC 2385528'
loop_
_audit_author_name
_audit_author_address
'Wang Zhou'
;College of Chemsitry
China
;
_audit_update_record             
;
2024-09-21 deposited with the CCDC.	2024-12-31 downloaded from the CCDC.
;
_audit_creation_date             2022-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H14 Br2 O3 S'
_chemical_formula_sum            'C26 H14 Br2 O3 S'
_chemical_formula_weight         566.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O2 S1 Br2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   12.0340(4)
_cell_length_b                   17.0933(9)
_cell_length_c                   11.0048(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.379(3)
_cell_angle_gamma                90
_cell_volume                     2261.74(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3941
_cell_measurement_temperature    293(10)
_cell_measurement_theta_max      71.5630
_cell_measurement_theta_min      2.5590
_shelx_estimated_absorpt_T_max   0.399
_shelx_estimated_absorpt_T_min   0.283
_exptl_absorpt_coefficient_mu    5.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7666
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.579
_diffrn_reflns_theta_max         66.579
_diffrn_reflns_theta_min         3.676
_diffrn_ambient_temperature      293(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  64.00   1.00    1.00    --   34.23 -19.00 -60.00  100
  2  ω     31.00  68.00   1.00    1.00    --   34.23 -99.00   0.00   37
  3  ω     37.00  68.00   1.00    1.00    --   34.23-125.00 -30.00   31
  4  ω     79.00 128.00   1.00    3.49    --  105.88 -77.00 -90.00   49
  5  ω     42.00 132.00   1.00    3.49    --  105.88 -77.00-120.00   90
  6  ω     41.00 127.00   1.00    3.49    --  105.88 -30.00  60.00   86
  7  ω    127.00 171.00   1.00    3.49    --  105.88  61.00  30.00   44
  8  ω     89.00 124.00   1.00    3.49    --  105.88  61.00  30.00   35
  9  ω     88.00 159.00   1.00    3.49    --  105.88  61.00   0.00   71
 10  ω     42.00  71.00   1.00    3.49    --  105.88 -94.00  30.00   29
 11  ω     51.00  76.00   1.00    1.00    --   34.23-125.00 120.00   25
 12  ω     42.00 124.00   1.00    3.49    --  105.88 -30.00-150.00   82
 13  ω    -30.00  63.00   1.00    1.00    --   34.23 -19.00-150.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0718871000
_diffrn_orient_matrix_UB_12      -0.0663048000
_diffrn_orient_matrix_UB_13      0.0571914000
_diffrn_orient_matrix_UB_21      0.1002303000
_diffrn_orient_matrix_UB_22      0.0558171000
_diffrn_orient_matrix_UB_23      0.0111147000
_diffrn_orient_matrix_UB_31      -0.0353598000
_diffrn_orient_matrix_UB_32      0.0242812000
_diffrn_orient_matrix_UB_33      0.1273892000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3457
_reflns_number_total             3983
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.149
_refine_diff_density_min         -1.292
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0733
_refine_ls_restrained_S_all      1.078
_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)+(0.0729P)²+8.5881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1797
_refine_ls_wR_factor_ref         0.1860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.00800(6) 0.49046(7) 0.81961(8) 0.0849(4) Uani 1 1 d . . . . .
Br2 Br 0.73445(7) 0.37080(6) 0.06714(7) 0.0709(3) Uani 1 1 d . . . . .
S1 S 0.27320(14) 0.36636(12) 0.86517(16) 0.0586(5) Uani 1 1 d . . . . .
O1 O 0.3908(3) 0.3335(3) 0.5326(4) 0.0537(12) Uani 1 1 d . . . . .
O2 O 0.2747(5) 0.2035(3) 0.6545(6) 0.0738(15) Uani 1 1 d . . . . .
O3 O 0.2285(4) 0.4000(2) 0.5640(4) 0.0504(10) Uani 1 1 d . . . . .
C1 C 0.6564(4) 0.3709(4) 0.2134(5) 0.0425(13) Uani 1 1 d . . . . .
C2 C 0.5743(5) 0.3181(4) 0.2313(6) 0.0507(15) Uani 1 1 d . . . . .
H2 H 0.553970 0.282761 0.170018 0.061 Uiso 1 1 calc R . . . .
C3 C 0.5204(5) 0.3165(4) 0.3413(6) 0.0453(14) Uani 1 1 d . . . . .
H3 H 0.464593 0.280070 0.353549 0.054 Uiso 1 1 calc R . . . .
C4 C 0.5511(4) 0.3702(3) 0.4332(5) 0.0321(10) Uani 1 1 d . . . . .
C5 C 0.6326(4) 0.4263(3) 0.4094(5) 0.0370(11) Uani 1 1 d . . . . .
H5 H 0.651364 0.463571 0.468234 0.044 Uiso 1 1 calc R . . . .
C6 C 0.6850(4) 0.4273(3) 0.3011(5) 0.0403(12) Uani 1 1 d . . . . .
H6 H 0.738687 0.464885 0.286341 0.048 Uiso 1 1 calc R . . . .
C7 C 0.4936(4) 0.3697(3) 0.5493(5) 0.0346(11) Uani 1 1 d . . . . .
C8 C 0.5313(4) 0.3961(3) 0.6579(5) 0.0335(11) Uani 1 1 d . . . . .
C9 C 0.4543(4) 0.3928(3) 0.7583(5) 0.0358(11) Uani 1 1 d . . . . .
C10 C 0.4749(5) 0.4129(4) 0.8818(6) 0.0490(14) Uani 1 1 d . . . . .
H10 H 0.542677 0.431913 0.912760 0.059 Uiso 1 1 calc R . . . .
C11 C 0.3853(6) 0.4014(5) 0.9500(6) 0.0615(18) Uani 1 1 d . . . . .
H11 H 0.384640 0.411342 1.033047 0.074 Uiso 1 1 calc R . . . .
C12 C 0.6473(4) 0.4211(3) 0.6885(5) 0.0324(11) Uani 1 1 d . . . . .
C13 C 0.7340(5) 0.3674(4) 0.6855(6) 0.0469(14) Uani 1 1 d . . . . .
H13 H 0.719754 0.316780 0.657888 0.056 Uiso 1 1 calc R . . . .
C14 C 0.8401(5) 0.3881(4) 0.7226(6) 0.0513(16) Uani 1 1 d . . . . .
H14 H 0.897625 0.351876 0.719733 0.062 Uiso 1 1 calc R . . . .
C15 C 0.8610(5) 0.4629(4) 0.7642(5) 0.0462(14) Uani 1 1 d . . . . .
C16 C 0.7784(5) 0.5176(4) 0.7663(6) 0.0468(14) Uani 1 1 d . . . . .
H16 H 0.793676 0.568408 0.791921 0.056 Uiso 1 1 calc R . . . .
C17 C 0.6714(5) 0.4959(3) 0.7295(5) 0.0395(12) Uani 1 1 d . . . . .
H17 H 0.614360 0.532476 0.732450 0.047 Uiso 1 1 calc R . . . .
C18 C 0.3485(4) 0.3668(3) 0.7368(5) 0.0394(12) Uani 1 1 d . . . . .
C19 C 0.3050(4) 0.3427(3) 0.6148(5) 0.0376(12) Uani 1 1 d . . . . .
C20 C 0.2408(4) 0.2648(3) 0.6107(5) 0.0391(12) Uani 1 1 d . . . . .
C21 C 0.1342(5) 0.2817(4) 0.5514(6) 0.0469(14) Uani 1 1 d . . . . .
C22 C 0.1352(5) 0.3611(4) 0.5249(6) 0.0484(15) Uani 1 1 d . . . . .
C23 C 0.0490(6) 0.3985(5) 0.4631(7) 0.0650(19) Uani 1 1 d . . . . .
H23 H 0.050724 0.451713 0.445788 0.078 Uiso 1 1 calc R . . . .
C24 C -0.0391(6) 0.3524(7) 0.4291(9) 0.087(3) Uani 1 1 d . . . . .
H24 H -0.098321 0.375664 0.385824 0.105 Uiso 1 1 calc R . . . .
C25 C -0.0467(6) 0.2725(7) 0.4545(8) 0.083(3) Uani 1 1 d . . . . .
H25 H -0.109882 0.244292 0.430512 0.100 Uiso 1 1 calc R . . . .
C26 C 0.0429(7) 0.2358(6) 0.5171(8) 0.081(3) Uani 1 1 d . . . . .
H26 H 0.041280 0.182641 0.534869 0.097 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 C15 1.906(6) . ?
Br2 C1 1.897(6) . ?
S1 C11 1.717(7) . ?
S1 C18 1.710(6) . ?
O1 C7 1.388(6) . ?
O1 C19 1.410(7) . ?
O2 C20 1.217(7) . ?
O3 C19 1.442(7) . ?
O3 C22 1.359(8) . ?
C1 C2 1.358(9) . ?
C1 C6 1.398(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(8) . ?
C4 C5 1.403(7) . ?
C4 C7 1.478(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.339(8) . ?
C8 C9 1.473(7) . ?
C8 C12 1.485(7) . ?
C9 C10 1.413(8) . ?
C9 C18 1.360(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.353(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(8) . ?
C12 C17 1.381(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(10) . ?
C15 C16 1.366(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.479(8) . ?
C19 C20 1.538(7) . ?
C20 C21 1.444(8) . ?
C21 C22 1.388(10) . ?
C21 C26 1.390(9) . ?
C22 C23 1.374(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.361(12) . ?
C24 H24 0.9300 . ?
C24 C25 1.397(15) . ?
C25 H25 0.9300 . ?
C25 C26 1.403(14) . ?
C26 H26 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
C18 S1 C11 90.9(3) . . ?
C7 O1 C19 122.5(4) . . ?
C22 O3 C19 107.2(4) . . ?
C2 C1 Br2 120.7(5) . . ?
C2 C1 C6 121.2(5) . . ?
C6 C1 Br2 118.0(4) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(6) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C7 120.0(5) . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 C7 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.8(5) . . ?
C5 C6 H6 120.6 . . ?
O1 C7 C4 109.6(4) . . ?
C8 C7 O1 122.4(5) . . ?
C8 C7 C4 128.0(5) . . ?
C7 C8 C9 117.1(5) . . ?
C7 C8 C12 125.5(5) . . ?
C9 C8 C12 117.1(5) . . ?
C10 C9 C8 128.4(5) . . ?
C18 C9 C8 119.7(5) . . ?
C18 C9 C10 111.8(5) . . ?
C9 C10 H10 123.6 . . ?
C11 C10 C9 112.7(6) . . ?
C11 C10 H10 123.6 . . ?
S1 C11 H11 124.0 . . ?
C10 C11 S1 112.0(5) . . ?
C10 C11 H11 124.0 . . ?
C13 C12 C8 120.2(5) . . ?
C17 C12 C8 121.5(5) . . ?
C17 C12 C13 118.2(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(6) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 Br1 119.3(5) . . ?
C16 C15 Br1 119.5(5) . . ?
C16 C15 C14 121.2(5) . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.8(6) . . ?
C17 C16 H16 120.6 . . ?
C12 C17 C16 121.5(5) . . ?
C12 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C9 C18 S1 112.5(4) . . ?
C9 C18 C19 122.9(5) . . ?
C19 C18 S1 124.6(4) . . ?
O1 C19 O3 107.4(5) . . ?
O1 C19 C18 111.9(4) . . ?
O1 C19 C20 105.4(5) . . ?
O3 C19 C18 111.0(5) . . ?
O3 C19 C20 105.3(4) . . ?
C18 C19 C20 115.2(5) . . ?
O2 C20 C19 125.0(5) . . ?
O2 C20 C21 128.9(6) . . ?
C21 C20 C19 106.0(5) . . ?
C22 C21 C20 106.0(5) . . ?
C22 C21 C26 120.6(7) . . ?
C26 C21 C20 133.4(8) . . ?
O3 C22 C21 115.2(5) . . ?
O3 C22 C23 121.7(7) . . ?
C23 C22 C21 123.1(7) . . ?
C22 C23 H23 122.3 . . ?
C24 C23 C22 115.5(9) . . ?
C24 C23 H23 122.3 . . ?
C23 C24 H24 117.7 . . ?
C23 C24 C25 124.6(8) . . ?
C25 C24 H24 117.7 . . ?
C24 C25 H25 120.7 . . ?
C24 C25 C26 118.7(7) . . ?
C26 C25 H25 120.7 . . ?
C21 C26 C25 117.6(9) . . ?
C21 C26 H26 121.2 . . ?
C25 C26 H26 121.2 . . ?

_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 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.725
