# 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. 
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data_mo241106a
_database_code_depnum_ccdc_archive 'CCDC 2409406'
loop_
_audit_author_name
_audit_author_address
'XINXIN SHAO'
;Hangzhou normal university
China
;
_audit_update_record             
;
2024-12-11 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_audit_creation_date             2024-12-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 Br D3 O2 S Se'
_chemical_formula_sum            'C7 H4 Br D3 O2 S Se'
_chemical_formula_weight         317.07
_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'
D D 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'
Se Se -0.0929 2.2259 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.1508(3)
_cell_length_b                   18.5489(7)
_cell_length_c                   8.7739(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.1050(10)
_cell_angle_gamma                90
_cell_volume                     1001.02(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3502
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.322
_cell_measurement_theta_min      3.490
_shelx_estimated_absorpt_T_max   0.450
_shelx_estimated_absorpt_T_min   0.383
_exptl_absorpt_coefficient_mu    7.909
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0891 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.7729.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.104
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17844
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.726
_diffrn_reflns_theta_min         2.196
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1919
_reflns_number_total             2514
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.025
_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)+(0.0286P)²+0.6473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0761
_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), C2(H2), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(D7A,D7B,D7C)
;
_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
Se1 Se 0.90242(5) 0.29083(2) 0.27950(4) 0.04898(12) Uani 1 1 d . . . . .
Br1 Br 0.23479(7) 0.59707(2) 0.06422(4) 0.07003(15) Uani 1 1 d . . . . .
S1 S 0.74611(12) 0.36043(4) 0.45371(8) 0.04429(18) Uani 1 1 d . . . . .
O2 O 0.9241(4) 0.39384(13) 0.5321(3) 0.0607(6) Uani 1 1 d . . . . .
O1 O 0.5910(4) 0.31851(13) 0.5371(3) 0.0653(6) Uani 1 1 d . . . . .
C1 C 0.6018(5) 0.42748(15) 0.3523(3) 0.0399(6) Uani 1 1 d . . . . .
C3 C 0.5891(6) 0.54374(16) 0.2380(4) 0.0520(7) Uani 1 1 d . . . . .
H3 H 0.652767 0.588162 0.217392 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3844(5) 0.52830(17) 0.1840(3) 0.0480(7) Uani 1 1 d . . . . .
C2 C 0.6997(5) 0.49286(16) 0.3230(3) 0.0468(7) Uani 1 1 d . . . . .
H2 H 0.838396 0.502597 0.360087 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3951(5) 0.41268(18) 0.3002(4) 0.0519(7) Uani 1 1 d . . . . .
H6 H 0.329195 0.368876 0.323065 0.062 Uiso 1 1 calc R U . . .
C5 C 0.2869(5) 0.46340(18) 0.2140(4) 0.0549(8) Uani 1 1 d . . . . .
H5 H 0.148542 0.453660 0.176328 0.066 Uiso 1 1 calc R U . . .
C7 C 0.6446(7) 0.2429(2) 0.2068(5) 0.0711(10) Uani 1 1 d . . . . .
D7A D 0.685159 0.203202 0.142721 0.107 Uiso 1 1 calc R U . . .
D7B D 0.557705 0.276320 0.149419 0.107 Uiso 1 1 calc R U . . .
D7C D 0.562355 0.225373 0.291950 0.107 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
Se1 S1 2.2210(8) . ?
Se1 C7 1.926(4) . ?
Br1 C4 1.891(3) . ?
S1 O2 1.433(2) . ?
S1 O1 1.433(2) . ?
S1 C1 1.768(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(5) . ?
C3 C2 1.381(4) . ?
C4 C5 1.371(5) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.378(4) . ?
C5 H5 0.9300 . ?
C7 D7A 0.9600 . ?
C7 D7B 0.9600 . ?
C7 D7C 0.9600 . ?

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 Se1 S1 97.99(13) . . ?
O2 S1 Se1 104.50(11) . . ?
O2 S1 O1 119.91(16) . . ?
O2 S1 C1 108.66(14) . . ?
O1 S1 Se1 109.00(11) . . ?
O1 S1 C1 107.74(15) . . ?
C1 S1 Se1 106.27(9) . . ?
C2 C1 S1 119.6(2) . . ?
C6 C1 S1 119.3(2) . . ?
C6 C1 C2 121.1(3) . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C3 C4 Br1 119.7(2) . . ?
C5 C4 Br1 119.1(2) . . ?
C5 C4 C3 121.2(3) . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C1 C6 H6 120.3 . . ?
C1 C6 C5 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
Se1 C7 D7A 109.5 . . ?
Se1 C7 D7B 109.5 . . ?
Se1 C7 D7C 109.5 . . ?
D7A C7 D7B 109.5 . . ?
D7A C7 D7C 109.5 . . ?
D7B C7 D7C 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
Se1 S1 C1 C2 -93.8(2) . . . . ?
Se1 S1 C1 C6 84.5(2) . . . . ?
Br1 C4 C5 C6 179.5(3) . . . . ?
S1 C1 C2 C3 177.2(2) . . . . ?
S1 C1 C6 C5 -176.5(3) . . . . ?
O2 S1 C1 C2 18.1(3) . . . . ?
O2 S1 C1 C6 -163.6(2) . . . . ?
O1 S1 C1 C2 149.5(2) . . . . ?
O1 S1 C1 C6 -32.2(3) . . . . ?
C1 C6 C5 C4 -1.4(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C3 C2 C1 -0.1(4) . . . . ?
C2 C1 C6 C5 1.8(5) . . . . ?
C2 C3 C4 Br1 -178.8(2) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
