# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_4483
_database_code_depnum_ccdc_archive 'CCDC 2393428'
_audit_update_record             
;
2025-01-30 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2025-01-29
_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         'C6 H2 Br3.856 Cl0.144'
_chemical_formula_sum            'C6 H2 Br3.86 Cl0.14'
_chemical_formula_weight         387.27
_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'
Cl Cl 0.1484 0.1585 '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                   4.0201(14)
_cell_length_b                   10.706(3)
_cell_length_c                   10.245(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.13(3)
_cell_angle_gamma                90
_cell_volume                     434.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    384
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5710
_cell_measurement_theta_min      5.4930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.963
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             351
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.1418
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1917
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_min         4.310
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  85.00   1.00    3.00    --   22.50  19.00  30.00   88
  2  ω     47.00  83.00   1.00    3.00    --   22.50 179.00-120.00   36
  3  ω     34.00  61.00   1.00    3.00    --   22.50 179.00 120.00   27
  4  ω      8.00  82.00   1.00    3.00    --   22.50  57.00-120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                578
_reflns_number_total             1030
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.212
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1028
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0672
_refine_ls_restrained_S_all      0.943
_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)+(0.0306P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.1127
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C2-Cl2 = C1-Cl1
 1.722 with sigma of 0.005
 Cl2-C1
 2.73 with sigma of 0.01
 Cl1-C2
 2.71 with sigma of 0.01
3. Restrained planarity
 C2, C1, C3, Cl2, Cl1, Br2, Br1
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Br1 \\sim Cl1: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
Br2 \\sim Cl2: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
5. Others
 Fixed Sof: Br1(0.964) Br2(0.964) Cl2(0.036) Cl1(0.036)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_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
C1 C -0.042(3) 0.6225(11) 0.9608(10) 0.040(3) Uani 1 1 d D . . . .
C2 C 0.054(2) 0.5360(10) 0.8732(9) 0.035(2) Uani 1 1 d D . . . .
C3 C 0.097(2) 0.4133(10) 0.9135(9) 0.035(3) Uani 1 1 d . . . . .
H3 H 0.163497 0.354095 0.856765 0.042 Uiso 1 1 calc R U . . .
Br1 Br -0.1101(4) 0.79235(12) 0.91032(13) 0.0505(4) Uani 0.964 1 d . U P . .
Br2 Br 0.1319(4) 0.57797(13) 0.70429(11) 0.0463(4) Uani 0.964 1 d . U P . .
Cl2 Cl 0.121(16) 0.577(4) 0.718(3) 0.0464(13) Uani 0.036 1 d D U P . .
Cl1 Cl -0.098(16) 0.7773(14) 0.917(5) 0.0505(13) Uani 0.036 1 d D U P . .


_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
C1 C2 1.390(14) . ?
C1 C3 1.399(13) 3_567 ?
C1 Br1 1.897(11) . ?
C1 Cl1 1.722(5) . ?
C2 C3 1.378(14) . ?
C2 Br2 1.868(9) . ?
C2 Cl2 1.722(5) . ?
C3 H3 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
C2 C1 C3 121.2(10) . 3_567 ?
C2 C1 Br1 120.4(8) . . ?
C2 C1 Cl1 120.8(12) . . ?
C3 C1 Br1 118.3(8) 3_567 . ?
C3 C1 Cl1 118.0(18) 3_567 . ?
Cl1 C1 Br1 1(2) . . ?
C1 C2 Br2 123.3(9) . . ?
C1 C2 Cl2 122.3(13) . . ?
C3 C2 C1 118.5(9) . . ?
C3 C2 Br2 118.2(8) . . ?
C3 C2 Cl2 119.3(16) . . ?
Cl2 C2 Br2 1.1(15) . . ?
C1 C3 H3 119.9 3_567 . ?
C2 C3 C1 120.3(9) . 3_567 ?
C2 C3 H3 119.9 . . ?

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
C1 C2 C3 C1 0.7(14) . . . 3_567 ?
C3 C1 C2 C3 -0.7(14) 3_567 . . . ?
C3 C1 C2 Br2 -179.9(7) 3_567 . . . ?
C3 C1 C2 Cl2 180(3) 3_567 . . . ?
Br1 C1 C2 C3 -179.4(7) . . . . ?
Br1 C1 C2 Br2 1.5(11) . . . . ?
Br1 C1 C2 Cl2 1(3) . . . . ?
Br2 C2 C3 C1 179.9(7) . . . 3_567 ?
Cl2 C2 C3 C1 -180(3) . . . 3_567 ?
Cl1 C1 C2 C3 180(2) . . . . ?
Cl1 C1 C2 Br2 0(3) . . . . ?
Cl1 C1 C2 Cl2 0(3) . . . . ?

_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
;
