# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_5cl5cl-br_autored
_database_code_depnum_ccdc_archive 'CCDC 2292879'
loop_
_audit_author_name
_audit_author_address
'Yu-Shuang Zhang'
;South China University of Technology
China
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-08-15
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H2.44 Br2.16 Cl11.4'
_chemical_formula_sum            'C19 H2.44 Br2.16 Cl11.40'
_chemical_formula_weight         807.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H Cl Br'
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'
Cl Cl 0.3639 0.7018 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.8567(3)
_cell_length_b                   11.4178(2)
_cell_length_c                   17.8798(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.116(2)
_cell_angle_gamma                90
_cell_volume                     2464.56(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9697
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.5150
_cell_measurement_theta_min      2.6280
_shelx_estimated_absorpt_T_max   0.298
_shelx_estimated_absorpt_T_min   0.231
_exptl_absorpt_coefficient_mu    15.960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    2.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1543
_exptl_crystal_size_max          0.13
_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  0.0944
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10584
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         5.269
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  22.00   0.50    1.50    --  -48.15  98.00 151.00  202
  2  ω    -22.00  79.00   0.50    1.50    --   48.15 -98.00  44.00  202
  3  ω   -106.00 -34.00   0.50    5.24    -- -104.00  98.00 151.00  144
  4  ω   -174.00 -86.00   0.50    5.24    -- -104.00 -98.00  44.00  176
  5  ω     36.00 105.00   0.50    5.24    --  106.53 -98.00  44.00  138
  6  ω     90.00 177.00   0.50    5.24    --  106.53  98.00 151.00  174
  7  ω    -24.00  26.00   0.50    1.50    --  -48.15  19.00-120.00  100
  8  ω    -24.00  26.00   0.50    1.50    --  -48.15  19.00-180.00  100
  9  ω    -41.00  24.00   0.50    1.50    --  -48.15  38.00 -90.00  130
 10  ω    -24.00  26.00   0.50    1.50    --  -48.15  19.00 150.00  100
 11  ω   -175.00 -90.00   0.50    5.24    -- -104.00 -57.00  90.00  170
 12  ω   -103.00 -32.00   0.50    5.24    -- -104.00  77.00 120.00  142
 13  ω   -103.00 -32.00   0.50    5.24    -- -104.00  77.00   0.00  142
 14  ω    -64.00 -32.00   0.50    5.24    -- -104.00  57.00 -30.00   64
 15  ω   -103.00 -32.00   0.50    5.24    -- -104.00  77.00 -90.00  142
 16  ω    -64.00 -32.00   0.50    5.24    -- -104.00  57.00   0.00   64
 17  ω    -64.00 -32.00   0.50    5.24    -- -104.00  57.00-180.00   64
 18  ω     34.00  68.00   0.50    5.24    --  106.53 -57.00  90.00   68
 19  ω     34.00  68.00   0.50    5.24    --  106.53 -57.00-180.00   68
 20  ω     85.00 178.00   0.50    5.24    --  106.53  77.00  30.00  186
 21  ω     34.00  68.00   0.50    5.24    --  106.53 -57.00  60.00   68
 22  ω     34.00  68.00   0.50    5.24    --  106.53 -57.00-120.00   68
 23  ω     34.00  68.00   0.50    5.24    --  106.53 -57.00-150.00   68
 24  ω   -119.00 -68.00   0.50    1.50    --  -48.15 -77.00 150.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0058308000
_diffrn_orient_matrix_UB_12      0.0176062000
_diffrn_orient_matrix_UB_13      0.0838964000
_diffrn_orient_matrix_UB_21      0.0421722000
_diffrn_orient_matrix_UB_22      -0.1260492000
_diffrn_orient_matrix_UB_23      0.0223029000
_diffrn_orient_matrix_UB_31      0.1202548000
_diffrn_orient_matrix_UB_32      0.0449366000
_diffrn_orient_matrix_UB_33      0.0296458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2123
_reflns_number_total             2175
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.099
_refine_diff_density_min         -1.571
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0964
_refine_ls_restrained_S_all      1.085
_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)+(0.1143P)²+54.4277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2460
_refine_ls_wR_factor_ref         0.2468
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{Br9, Cl1}
{Cl19, Br18}
{C4A, C4}
3. Uiso/Uaniso restraints and constraints
Uanis(C4A) = Uanis(C4)
Uanis(Br9) = Uanis(Cl1)
Uanis(Cl19) = Uanis(Br18)
4. Others
 Fixed Sof: Br18(0.72) Cl1(0.14) C4(0.28) Cl21(0.28) Br9(0.36) Cl19(0.28)
 C4A(0.72) H4A(0.72) C17A(0.5) H17A(0.5)
5.a Riding coordinates:
 C17A(H17A)
5.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A)
;
_atom_sites_solution_hydrogens   mixed
_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
Br18 Br 0.27703(12) 0.55753(15) 0.63830(8) 0.0667(6) Uani 0.72 1 d . . P A 1
Cl1 Cl 0.500000 0.9734(2) 0.750000 0.1221(15) Uani 0.28 2 d S T P A 1
Cl14 Cl 0.3220(2) 0.2355(2) 0.70310(15) 0.0538(7) Uani 1 1 d . . . . .
Cl3 Cl 0.4479(2) 0.1538(2) 0.44961(14) 0.0599(7) Uani 1 1 d . . . . .
Cl16 Cl 0.3010(2) 0.0965(2) 0.55032(16) 0.0606(7) Uani 1 1 d . . . . .
Cl6 Cl 0.6465(3) 0.4964(3) 0.65195(19) 0.0807(11) Uani 1 1 d . . . . .
Cl20 Cl 0.6164(3) 0.3590(3) 0.50109(18) 0.0819(11) Uani 1 1 d . . . . .
C13 C 0.3958(7) 0.2073(8) 0.5807(5) 0.0414(19) Uani 1 1 d . . . . .
C10 C 0.4060(7) 0.2714(8) 0.6481(5) 0.0395(19) Uani 1 1 d . . . . .
C8 C 0.500000 0.5606(12) 0.750000 0.047(3) Uani 1 2 d S T P A .
C11 C 0.4602(8) 0.2334(8) 0.5343(5) 0.0416(19) Uani 1 1 d . . . . .
C5 C 0.4831(8) 0.3634(8) 0.6742(5) 0.042(2) Uani 1 1 d . . . . .
C12 C 0.4103(8) 0.6279(10) 0.7036(5) 0.049(2) Uani 1 1 d . . . . .
C4 C 0.4081(9) 0.7475(9) 0.7015(6) 0.050(2) Uani 0.28 1 d . . P A 2
C7 C 0.5354(9) 0.3258(9) 0.5576(5) 0.047(2) Uani 1 1 d . . . . .
C15 C 0.5455(9) 0.3880(9) 0.6256(6) 0.050(2) Uani 1 1 d . . . . .
C2 C 0.500000 0.8084(12) 0.750000 0.053(3) Uani 1 2 d S T P . .
Cl21 Cl 0.2972(17) 0.8053(19) 0.6388(12) 0.139(8) Uani 0.28 1 d . . P A 2
Br9 Br 0.500000 0.9734(2) 0.750000 0.1221(15) Uani 0.72 2 d S T P A 2
Cl19 Cl 0.27703(12) 0.55753(15) 0.63830(8) 0.0667(6) Uani 0.28 1 d . . P A 2
C4A C 0.4081(9) 0.7475(9) 0.7015(6) 0.050(2) Uani 0.72 1 d . . P A 1
H4A H 0.345055 0.788159 0.667592 0.060 Uiso 0.72 1 calc R U P A 1
C17A C 0.5348(15) 0.4303(15) 0.7578(13) 0.043(4) Uani 0.5 1 d . . P A -2
H17A H 0.616748 0.430435 0.769844 0.052 Uiso 0.5 1 d R U P A -2


_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
Br18 C12 1.889(10) . ?
Cl1 C2 1.883(14) . ?
Cl14 C10 1.741(8) . ?
Cl3 C11 1.726(9) . ?
Cl16 C13 1.711(9) . ?
Cl6 C15 1.736(9) . ?
Cl20 C7 1.725(8) . ?
C13 C10 1.378(13) . ?
C13 C11 1.391(12) . ?
C10 C5 1.410(13) . ?
C8 C12 1.397(13) . ?
C8 C12 1.397(13) 2_656 ?
C8 C17A 1.55(2) . ?
C11 C7 1.395(14) . ?
C5 C15 1.398(11) . ?
C5 C17A 1.61(2) . ?
C12 C4 1.366(15) . ?
C12 Cl19 1.889(10) . ?
C12 C4A 1.366(15) . ?
C4 C2 1.388(12) . ?
C4 Cl21 1.62(2) . ?
C7 C15 1.375(13) . ?
C2 Br9 1.883(14) . ?
C2 C4A 1.388(12) . ?
C4A H4A 0.9500 . ?
C17A H17A 1.0000 . ?

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
C10 C13 Cl16 120.9(7) . . ?
C10 C13 C11 120.8(8) . . ?
C11 C13 Cl16 118.3(7) . . ?
C13 C10 Cl14 118.6(7) . . ?
C13 C10 C5 122.0(7) . . ?
C5 C10 Cl14 119.4(6) . . ?
C12 C8 C12 113.3(13) 2_656 . ?
C12 C8 C17A 137.5(11) . . ?
C12 C8 C17A 108.8(9) 2_656 . ?
C13 C11 Cl3 121.2(7) . . ?
C13 C11 C7 118.5(8) . . ?
C7 C11 Cl3 120.4(6) . . ?
C10 C5 C17A 132.9(9) . . ?
C15 C5 C10 115.7(8) . . ?
C15 C5 C17A 109.9(9) . . ?
C8 C12 Br18 121.4(8) . . ?
C8 C12 Cl19 121.4(8) . . ?
C4 C12 C8 124.8(10) . . ?
C4 C12 Cl19 113.8(8) . . ?
C4A C12 Br18 113.8(8) . . ?
C4A C12 C8 124.8(10) . . ?
C12 C4 C2 118.6(10) . . ?
C12 C4 Cl21 115.5(13) . . ?
C2 C4 Cl21 125.9(13) . . ?
C11 C7 Cl20 119.1(7) . . ?
C15 C7 Cl20 120.8(7) . . ?
C15 C7 C11 120.1(8) . . ?
C5 C15 Cl6 120.6(7) . . ?
C7 C15 Cl6 116.3(7) . . ?
C7 C15 C5 123.0(9) . . ?
C4 C2 C4 119.9(13) . 2_656 ?
C4 C2 Br9 120.1(6) . . ?
C4 C2 Br9 120.1(6) 2_656 . ?
C4A C2 Cl1 120.1(6) . . ?
C4A C2 C4 119.9(13) . 2_656 ?
C12 C4A C2 118.6(10) . . ?
C12 C4A H4A 120.7 . . ?
C2 C4A H4A 120.7 . . ?
C8 C17A C5 111.0(13) . . ?
C8 C17A H17A 105.6 . . ?
C5 C17A H17A 105.7 . . ?

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
Br18 C12 C4A C2 177.2(5) . . . . ?
Cl1 C2 C4A C12 -179.3(6) . . . . ?
Cl14 C10 C5 C15 -178.7(8) . . . . ?
Cl14 C10 C5 C17A 16.9(16) . . . . ?
Cl3 C11 C7 Cl20 -0.3(12) . . . . ?
Cl3 C11 C7 C15 -179.3(8) . . . . ?
Cl16 C13 C10 Cl14 1.2(11) . . . . ?
Cl16 C13 C10 C5 -179.7(7) . . . . ?
Cl16 C13 C11 Cl3 -1.8(11) . . . . ?
Cl16 C13 C11 C7 178.2(8) . . . . ?
Cl20 C7 C15 Cl6 -2.1(13) . . . . ?
Cl20 C7 C15 C5 -179.0(9) . . . . ?
C13 C10 C5 C15 2.2(14) . . . . ?
C13 C10 C5 C17A -162.2(12) . . . . ?
C13 C11 C7 Cl20 179.7(7) . . . . ?
C13 C11 C7 C15 0.7(15) . . . . ?
C10 C13 C11 Cl3 -179.9(7) . . . . ?
C10 C13 C11 C7 0.1(14) . . . . ?
C10 C5 C15 Cl6 -178.1(8) . . . . ?
C10 C5 C15 C7 -1.3(16) . . . . ?
C10 C5 C17A C8 -115.5(13) . . . . ?
C8 C12 C4 C2 -1.6(13) . . . . ?
C8 C12 C4 Cl21 176.4(8) . . . . ?
C8 C12 C4A C2 -1.6(13) . . . . ?
C11 C13 C10 Cl14 179.2(7) . . . . ?
C11 C13 C10 C5 -1.6(14) . . . . ?
C11 C7 C15 Cl6 176.8(8) . . . . ?
C11 C7 C15 C5 -0.1(17) . . . . ?
C12 C8 C12 Br18 -177.8(7) 2_656 . . . ?
C12 C8 C12 C4 0.8(7) 2_656 . . . ?
C12 C8 C12 Cl19 -177.8(7) 2_656 . . . ?
C12 C8 C12 C4A 0.8(7) 2_656 . . . ?
C12 C8 C17A C5 -141.6(9) 2_656 . . . ?
C12 C8 C17A C5 29.4(16) . . . . ?
C12 C4 C2 C4 0.7(6) . . . 2_656 ?
C12 C4 C2 Br9 -179.3(6) . . . . ?
C15 C5 C17A C8 79.4(12) . . . . ?
Cl21 C4 C2 C4 -177.0(12) . . . 2_656 ?
Cl21 C4 C2 Br9 3.0(12) . . . . ?
Cl19 C12 C4 C2 177.2(5) . . . . ?
Cl19 C12 C4 Cl21 -4.9(12) . . . . ?
C17A C8 C12 C4 -169.9(11) . . . . ?
C17A C8 C12 Cl19 11.5(13) . . . . ?
C17A C5 C15 Cl6 -10.2(14) . . . . ?
C17A C5 C15 C7 166.5(12) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 4.787
_oxdiff_exptl_absorpt_empirical_full_min 0.253
