# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_cll200912_1_223k
_audit_block_doi                 10.5517/ccdc.csd.cc29fx9z
_database_code_depnum_ccdc_archive 'CCDC 2128531'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2QI00964A 2022
loop_
_audit_author_name
_audit_author_address
'Tie Zhang'
;Southeast University
China
;
_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C5 H13 Cl N), Br4 Cd'
_chemical_formula_sum            'C10 H26 Br4 Cd Cl2 N2'
_chemical_formula_weight         677.27

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'
Cd Cd -0.8075 1.2024 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.5923(7)
_cell_length_b                   12.4120(7)
_cell_length_c                   23.9198(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4332.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    9747
_cell_measurement_theta_min      2.7230
_cell_measurement_theta_max      25.000

_exptl_crystal_description       sheet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.077
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2576
_exptl_absorpt_coefficient_mu    8.625
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22519
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3818
_reflns_number_gt                3222
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1179P)²+13.2203P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3818
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.86103(17) 0.4486(2) 0.59118(11) 0.0627(6) Uani 1 1 d . . .
Cd1 Cd 0.96773(4) 0.27221(4) 0.84238(2) 0.0329(2) Uani 1 1 d . . .
Br2 Br 0.98760(6) 0.24361(7) 0.73576(3) 0.0412(3) Uani 1 1 d . . .
Br1 Br 0.89151(6) 0.10982(7) 0.88959(4) 0.0491(3) Uani 1 1 d . . .
Br4 Br 0.87870(7) 0.44674(7) 0.86210(4) 0.0562(3) Uani 1 1 d . . .
Br3 Br 1.13190(6) 0.28308(8) 0.88068(4) 0.0533(3) Uani 1 1 d . . .
Cl2 Cl 0.62663(17) 0.6078(3) 0.52554(12) 0.0707(8) Uani 1 1 d . . .
N1 N 0.7349(4) 0.5281(5) 0.7132(2) 0.0335(13) Uani 1 1 d . . .
N2 N 0.3832(5) 0.7555(5) 0.5541(3) 0.0391(15) Uani 1 1 d . . .
C1 C 0.6897(5) 0.5661(6) 0.6603(3) 0.0380(17) Uani 1 1 d . . .
H1A H 0.7326 0.6073 0.6387 0.057 Uiso 1 1 calc R . .
H1B H 0.6378 0.6103 0.6695 0.057 Uiso 1 1 calc R . .
H1C H 0.6697 0.5050 0.6389 0.057 Uiso 1 1 calc R . .
C3 C 0.7687(6) 0.6257(6) 0.7451(4) 0.0426(18) Uani 1 1 d . . .
H3A H 0.7984 0.6028 0.7789 0.064 Uiso 1 1 calc R . .
H3B H 0.7177 0.6713 0.7543 0.064 Uiso 1 1 calc R . .
H3C H 0.8114 0.6651 0.7224 0.064 Uiso 1 1 calc R . .
C4 C 0.8112(5) 0.4498(6) 0.7018(3) 0.0418(18) Uani 1 1 d . . .
H4A H 0.7846 0.3842 0.6870 0.050 Uiso 1 1 calc R . .
H4B H 0.8400 0.4318 0.7371 0.050 Uiso 1 1 calc R . .
C2 C 0.6658(6) 0.4713(7) 0.7489(4) 0.051(2) Uani 1 1 d . . .
H2A H 0.6374 0.4148 0.7277 0.077 Uiso 1 1 calc R . .
H2B H 0.6200 0.5218 0.7609 0.077 Uiso 1 1 calc R . .
H2C H 0.6958 0.4410 0.7810 0.077 Uiso 1 1 calc R . .
C5 C 0.8840(5) 0.4873(7) 0.6623(4) 0.047(2) Uani 1 1 d . . .
H5A H 0.9425 0.4573 0.6737 0.056 Uiso 1 1 calc R . .
H5B H 0.8887 0.5652 0.6643 0.056 Uiso 1 1 calc R . .
C9 C 0.4770(6) 0.7040(8) 0.5632(4) 0.050(2) Uani 1 1 d . . .
H9A H 0.5154 0.7532 0.5843 0.060 Uiso 1 1 calc R . .
H9B H 0.4697 0.6389 0.5852 0.060 Uiso 1 1 calc R . .
C6 C 0.3901(7) 0.8567(7) 0.5215(4) 0.056(2) Uani 1 1 d . . .
H6A H 0.4121 0.8409 0.4846 0.084 Uiso 1 1 calc R . .
H6B H 0.4319 0.9050 0.5398 0.084 Uiso 1 1 calc R . .
H6C H 0.3308 0.8898 0.5191 0.084 Uiso 1 1 calc R . .
C7 C 0.3182(6) 0.6816(9) 0.5308(4) 0.058(2) Uani 1 1 d . . .
H7A H 0.2578 0.7121 0.5331 0.087 Uiso 1 1 calc R . .
H7B H 0.3199 0.6152 0.5513 0.087 Uiso 1 1 calc R . .
H7C H 0.3333 0.6681 0.4924 0.087 Uiso 1 1 calc R . .
C10 C 0.5244(7) 0.6761(10) 0.5082(4) 0.066(3) Uani 1 1 d . . .
H10A H 0.5380 0.7411 0.4873 0.079 Uiso 1 1 calc R . .
H10B H 0.4853 0.6304 0.4856 0.079 Uiso 1 1 calc R . .
C8 C 0.3519(8) 0.7835(10) 0.6127(4) 0.068(3) Uani 1 1 d . . .
H8A H 0.2948 0.8216 0.6108 0.102 Uiso 1 1 calc R . .
H8B H 0.3971 0.8281 0.6304 0.102 Uiso 1 1 calc R . .
H8C H 0.3440 0.7186 0.6339 0.102 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
Cl1 C5 1.798(10) . ?
Cd1 Br1 2.5642(9) . ?
Cd1 Br3 2.5684(11) . ?
Cd1 Br4 2.5696(10) . ?
Cd1 Br2 2.5910(10) . ?
Cl2 C10 1.765(10) . ?
N1 C4 1.502(9) . ?
N1 C2 1.497(10) . ?
N1 C1 1.503(9) . ?
N1 C3 1.515(9) . ?
N2 C7 1.433(12) . ?
N2 C6 1.482(11) . ?
N2 C8 1.513(11) . ?
N2 C9 1.526(11) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.498(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C9 C10 1.526(14) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
Br1 Cd1 Br3 106.78(3) . . ?
Br1 Cd1 Br4 111.25(4) . . ?
Br3 Cd1 Br4 111.21(4) . . ?
Br1 Cd1 Br2 111.98(3) . . ?
Br3 Cd1 Br2 104.71(3) . . ?
Br4 Cd1 Br2 110.66(4) . . ?
C4 N1 C2 107.4(6) . . ?
C4 N1 C1 112.1(6) . . ?
C2 N1 C1 109.4(6) . . ?
C4 N1 C3 111.5(6) . . ?
C2 N1 C3 107.9(6) . . ?
C1 N1 C3 108.4(6) . . ?
C7 N2 C6 112.5(7) . . ?
C7 N2 C8 107.9(8) . . ?
C6 N2 C8 108.2(7) . . ?
C7 N2 C9 112.4(7) . . ?
C6 N2 C9 111.7(7) . . ?
C8 N2 C9 103.6(7) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 116.1(6) . . ?
N1 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
N1 C4 H4B 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C5 Cl1 112.5(6) . . ?
C4 C5 H5A 109.1 . . ?
Cl1 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
Cl1 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C10 C9 N2 112.2(7) . . ?
C10 C9 H9A 109.2 . . ?
N2 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
N2 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 Cl2 106.8(7) . . ?
C9 C10 H10A 110.4 . . ?
Cl2 C10 H10A 110.4 . . ?
C9 C10 H10B 110.4 . . ?
Cl2 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.358
_refine_diff_density_min         -2.347
_refine_diff_density_rms         0.194
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc29fxc1
_database_code_depnum_ccdc_archive 'CCDC 2128533'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2QI00964A 2022
loop_
_audit_author_name
_audit_author_address
'Tie Zhang'
;Southeast University
China
;
_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C5 Cl N), Br4 Cd'
_chemical_formula_sum            'C10 H0 Br4 Cd Cl2 N2'
_chemical_formula_weight         651.06

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'
Cd Cd -0.8075 1.2024 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1247(5)
_cell_length_b                   14.5686(6)
_cell_length_c                   13.0976(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2313.56(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.1790
_cell_measurement_theta_max      21.0470

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    8.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      373(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57840
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2774
_reflns_number_gt                2062
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1625P)²+22.4069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2774
_refine_ls_number_parameters     128
_refine_ls_number_restraints     229
_refine_ls_R_factor_all          0.1991
_refine_ls_R_factor_gt           0.1618
_refine_ls_wR_factor_ref         0.4184
_refine_ls_wR_factor_gt          0.3952
_refine_ls_goodness_of_fit_ref   1.288
_refine_ls_restrained_S_all      1.268
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C7 C 0.680(2) 0.7500 0.0000 0.220(12) Uani 1 2 d DS TU P . .
Cd1 Cd 0.68796(15) 0.02777(13) 0.2500 0.0792(8) Uani 1 2 d S TU P . .
Br2 Br 0.7655(3) -0.1381(2) 0.2500 0.1130(12) Uani 1 2 d S TU P . .
Br3 Br 0.4763(2) 0.0110(3) 0.2500 0.1178(13) Uani 1 2 d S TU P . .
Br4 Br 0.7508(4) 0.1099(3) 0.0883(3) 0.1727(17) Uani 1 1 d . U . . .
N1 N 0.563(2) 0.7500 0.0000 0.213(12) Uani 1 2 d DS TU P . .
C1 C 0.732(2) 0.664(3) 0.045(8) 0.230(14) Uani 0.5 1 d D U P . .
C2 C 0.524(2) 0.764(7) 0.1003(15) 0.212(14) Uani 0.5 1 d D U P . .
N2 N 0.891(3) 0.371(2) 0.2500 0.220(13) Uani 1 2 d DS TU P . .
C3 C 0.905(5) 0.470(2) 0.2500 0.240(13) Uani 1 2 d DS TU P . .
C4 C 0.773(3) 0.356(4) 0.2500 0.228(15) Uani 1 2 d DS TU P . .
C5 C 0.930(3) 0.340(3) 0.1519(17) 0.239(15) Uani 1 1 d D U . . .
Cl1 Cl 0.869(2) 0.648(2) 0.059(3) 0.237(10) Uani 0.5 1 d D U P . .
Cl2 Cl 0.902(3) 0.614(2) 0.106(3) 0.271(13) Uani 0.5 1 d D U P . .
C6 C 0.957(4) 0.510(3) 0.156(4) 0.239(14) Uani 0.5 1 d D U P . .
C8 C 0.525(2) 0.665(3) -0.039(7) 0.220(14) Uani 0.5 1 d D U P . .
C9 C 0.526(2) 0.823(4) -0.064(6) 0.225(14) Uani 0.5 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
C7 N1 1.428(9) . ?
C7 C1 1.516(10) . ?
C7 C1 1.516(10) 3_565 ?
Cd1 Br4 2.548(3) 6_556 ?
Cd1 Br4 2.548(3) . ?
Cd1 Br3 2.578(3) . ?
Cd1 Br2 2.592(4) . ?
N1 C8 1.410(9) 3_565 ?
N1 C8 1.410(9) . ?
N1 C2 1.411(9) . ?
N1 C2 1.411(9) 3_565 ?
N1 C9 1.420(9) 3_565 ?
N1 C9 1.420(9) . ?
C1 Cl1 1.692(10) . ?
C2 C8 1.31(3) 3_565 ?
C2 C9 1.35(3) 3_565 ?
N2 C5 1.442(10) 6_556 ?
N2 C5 1.442(10) . ?
N2 C4 1.445(10) . ?
N2 C3 1.447(10) . ?
C3 C6 1.500(10) 6_556 ?
C3 C6 1.500(10) . ?
Cl2 C6 1.779(10) . ?
C8 C2 1.31(3) 3_565 ?
C8 C9 1.35(3) 3_565 ?
C9 C2 1.35(3) 3_565 ?
C9 C8 1.35(3) 3_565 ?

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
N1 C7 C1 114.5(9) . . ?
N1 C7 C1 114.5(9) . 3_565 ?
C1 C7 C1 131.0(18) . 3_565 ?
Br4 Cd1 Br4 112.4(2) 6_556 . ?
Br4 Cd1 Br3 110.00(12) 6_556 . ?
Br4 Cd1 Br3 110.00(12) . . ?
Br4 Cd1 Br2 109.21(12) 6_556 . ?
Br4 Cd1 Br2 109.21(12) . . ?
Br3 Cd1 Br2 105.81(13) . . ?
C8 N1 C8 142.1(15) 3_565 . ?
C8 N1 C2 55.4(12) 3_565 . ?
C8 N1 C2 110.5(9) . . ?
C8 N1 C2 110.5(9) 3_565 3_565 ?
C8 N1 C2 55.4(12) . 3_565 ?
C2 N1 C2 140.8(17) . 3_565 ?
C8 N1 C9 109.7(9) 3_565 3_565 ?
C8 N1 C9 57.2(11) . 3_565 ?
C2 N1 C9 56.7(11) . 3_565 ?
C2 N1 C9 109.7(9) 3_565 3_565 ?
C8 N1 C9 57.2(11) 3_565 . ?
C8 N1 C9 109.7(9) . . ?
C2 N1 C9 109.7(9) . . ?
C2 N1 C9 56.7(11) 3_565 . ?
C9 N1 C9 143.2(17) 3_565 . ?
C8 N1 C7 108.9(7) 3_565 . ?
C8 N1 C7 108.9(7) . . ?
C2 N1 C7 109.6(8) . . ?
C2 N1 C7 109.6(8) 3_565 . ?
C9 N1 C7 108.4(8) 3_565 . ?
C9 N1 C7 108.4(8) . . ?
C7 C1 Cl1 124.8(15) . . ?
C8 C2 C9 121.2(18) 3_565 3_565 ?
C8 C2 N1 62.3(8) 3_565 . ?
C9 C2 N1 62.0(8) 3_565 . ?
C5 N2 C5 126(3) 6_556 . ?
C5 N2 C4 106.1(9) 6_556 . ?
C5 N2 C4 106.1(9) . . ?
C5 N2 C3 105.8(9) 6_556 . ?
C5 N2 C3 105.8(9) . . ?
C4 N2 C3 105.6(10) . . ?
N2 C3 C6 115.8(11) . 6_556 ?
N2 C3 C6 115.8(11) . . ?
C6 C3 C6 110(6) 6_556 . ?
C3 C6 Cl2 118.2(15) . . ?
C2 C8 C9 120.5(18) 3_565 3_565 ?
C2 C8 N1 62.3(8) 3_565 . ?
C9 C8 N1 61.8(8) 3_565 . ?
C2 C9 C8 118.3(18) 3_565 3_565 ?
C2 C9 N1 61.3(8) 3_565 . ?
C8 C9 N1 61.0(8) 3_565 . ?

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 C7 N1 C8 132(6) . . . 3_565 ?
C1 C7 N1 C8 -48(6) 3_565 . . 3_565 ?
C1 C7 N1 C8 -48(6) . . . . ?
C1 C7 N1 C8 132(6) 3_565 . . . ?
C1 C7 N1 C2 74(6) . . . . ?
C1 C7 N1 C2 -106(6) 3_565 . . . ?
C1 C7 N1 C2 -106(6) . . . 3_565 ?
C1 C7 N1 C2 74(6) 3_565 . . 3_565 ?
C1 C7 N1 C9 13(6) . . . 3_565 ?
C1 C7 N1 C9 -167(6) 3_565 . . 3_565 ?
C1 C7 N1 C9 -167(6) . . . . ?
C1 C7 N1 C9 13(6) 3_565 . . . ?
N1 C7 C1 Cl1 -177(6) . . . . ?
C1 C7 C1 Cl1 3(6) 3_565 . . . ?
C8 N1 C2 C8 -140.0(17) . . . 3_565 ?
C2 N1 C2 C8 -80.0(11) 3_565 . . 3_565 ?
C9 N1 C2 C8 -160(2) 3_565 . . 3_565 ?
C9 N1 C2 C8 -18.9(18) . . . 3_565 ?
C7 N1 C2 C8 100.0(11) . . . 3_565 ?
C8 N1 C2 C9 160(2) 3_565 . . 3_565 ?
C8 N1 C2 C9 20.5(19) . . . 3_565 ?
C2 N1 C2 C9 80.4(12) 3_565 . . 3_565 ?
C9 N1 C2 C9 141.5(19) . . . 3_565 ?
C7 N1 C2 C9 -99.6(12) . . . 3_565 ?
C5 N2 C3 C6 2(4) 6_556 . . 6_556 ?
C5 N2 C3 C6 -133(4) . . . 6_556 ?
C4 N2 C3 C6 115(4) . . . 6_556 ?
C5 N2 C3 C6 133(4) 6_556 . . . ?
C5 N2 C3 C6 -2(4) . . . . ?
C4 N2 C3 C6 -115(4) . . . . ?
N2 C3 C6 Cl2 138(3) . . . . ?
C6 C3 C6 Cl2 -88(6) 6_556 . . . ?
C8 N1 C8 C2 78.8(12) 3_565 . . 3_565 ?
C2 N1 C8 C2 138.3(19) . . . 3_565 ?
C9 N1 C8 C2 158.7(19) 3_565 . . 3_565 ?
C9 N1 C8 C2 17.3(19) . . . 3_565 ?
C7 N1 C8 C2 -101.2(12) . . . 3_565 ?
C8 N1 C8 C9 -79.9(11) 3_565 . . 3_565 ?
C2 N1 C8 C9 -20.4(18) . . . 3_565 ?
C2 N1 C8 C9 -158.7(19) 3_565 . . 3_565 ?
C9 N1 C8 C9 -141.4(19) . . . 3_565 ?
C7 N1 C8 C9 100.1(11) . . . 3_565 ?
C8 N1 C9 C2 -157.1(19) 3_565 . . 3_565 ?
C8 N1 C9 C2 -17.0(19) . . . 3_565 ?
C2 N1 C9 C2 -138.5(19) . . . 3_565 ?
C9 N1 C9 C2 -78.2(12) 3_565 . . 3_565 ?
C7 N1 C9 C2 101.8(12) . . . 3_565 ?
C8 N1 C9 C8 140.0(17) . . . 3_565 ?
C2 N1 C9 C8 18.5(18) . . . 3_565 ?
C2 N1 C9 C8 157.1(19) 3_565 . . 3_565 ?
C9 N1 C9 C8 78.9(11) 3_565 . . 3_565 ?
C7 N1 C9 C8 -101.1(11) . . . 3_565 ?

_refine_diff_density_max         1.666
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.189

# start Validation Reply Form
_vrf_PLAT082_1                   
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: Excessive thermal vibration of atoms in high-temperature
;
_vrf_PLAT084_1                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.42 Report
RESPONSE: Excessive thermal vibration of atoms in high-temperature
;
_vrf_PLAT242_1                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Cd1 Check 
RESPONSE: The large thermal vibrations of the atoms around Cd cause
;
# end Validation Reply Form

####################################################################### 
# 
# 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_1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc29fxb0
_database_code_depnum_ccdc_archive 'CCDC 2128532'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2QI00964A 2022
loop_
_audit_author_name
_audit_author_address
'Tie Zhang'
;Southeast University
China
;
_audit_update_record             
;
2021-12-14 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H26 Br4 Cd Cl2 N2'
_chemical_formula_weight         677.27

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'
Cd Cd -0.8075 1.2024 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   14.4102(8)
_cell_length_b                   11.9573(5)
_cell_length_c                   12.9232(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2226.76(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    5778
_cell_measurement_theta_min      2.7190
_cell_measurement_theta_max      24.999

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.020
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    8.390
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10995
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.717
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3735
_reflns_number_gt                3163
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1032P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.019(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3735
_refine_ls_number_parameters     180
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1536
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl2 Cl 0.6414(3) 0.8851(3) 0.2966(3) 0.0919(10) Uani 1 1 d . . . . .
N2 N 0.7475(8) 0.5803(7) 0.3698(9) 0.075(3) Uani 1 1 d D . . . .
C9 C 0.7299(10) 0.7083(9) 0.3592(11) 0.074(4) Uani 1 1 d . . . . .
H9A H 0.7261 0.7410 0.4277 0.088 Uiso 1 1 calc R U . . .
H9B H 0.7822 0.7422 0.3239 0.088 Uiso 1 1 calc R U . . .
C6 C 0.6680(11) 0.5257(13) 0.4183(13) 0.134(8) Uani 1 1 d D . . . .
H6A H 0.6739 0.4461 0.4113 0.201 Uiso 1 1 calc R U . . .
H6B H 0.6119 0.5501 0.3852 0.201 Uiso 1 1 calc R U . . .
H6C H 0.6659 0.5451 0.4904 0.201 Uiso 1 1 calc R U . . .
C7 C 0.7624(11) 0.5261(10) 0.2672(12) 0.086(4) Uani 1 1 d . . . . .
H7A H 0.7709 0.4472 0.2766 0.129 Uiso 1 1 calc R U . . .
H7B H 0.8165 0.5574 0.2349 0.129 Uiso 1 1 calc R U . . .
H7C H 0.7092 0.5390 0.2240 0.129 Uiso 1 1 calc R U . . .
C8 C 0.8369(17) 0.5801(17) 0.4259(16) 0.145(7) Uani 1 1 d . U . . .
H8A H 0.8310 0.5364 0.4878 0.217 Uiso 1 1 calc R U . . .
H8B H 0.8536 0.6554 0.4436 0.217 Uiso 1 1 calc R U . . .
H8C H 0.8842 0.5483 0.3825 0.217 Uiso 1 1 calc R U . . .
C10 C 0.6437(11) 0.7354(11) 0.3016(14) 0.094(4) Uani 1 1 d . . . . .
H10A H 0.5896 0.7067 0.3375 0.113 Uiso 1 1 calc R U . . .
H10B H 0.6454 0.7039 0.2324 0.113 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6102(4) 0.9086(6) -0.0315(5) 0.160(2) Uani 1 1 d . U . . .
N1 N 0.3708(6) 0.8802(10) 0.1116(8) 0.081(3) Uani 1 1 d D U . . .
C5 C 0.5058(11) 0.9653(11) 0.0289(18) 0.126(6) Uani 1 1 d D U . . .
H5A H 0.5201 1.0097 0.0897 0.152 Uiso 1 1 calc R U . . .
H5B H 0.4693 1.0094 -0.0192 0.152 Uiso 1 1 calc R U . . .
C3 C 0.3754(14) 0.9305(13) 0.2137(11) 0.098(5) Uani 1 1 d . . . . .
H3A H 0.3844 1.0097 0.2069 0.147 Uiso 1 1 calc R U . . .
H3B H 0.4264 0.8987 0.2514 0.147 Uiso 1 1 calc R U . . .
H3C H 0.3186 0.9164 0.2501 0.147 Uiso 1 1 calc R U . . .
C2 C 0.3385(18) 0.7542(16) 0.123(2) 0.158(9) Uani 1 1 d . . . . .
H2A H 0.3675 0.7213 0.1821 0.238 Uiso 1 1 calc R U . . .
H2B H 0.3561 0.7134 0.0617 0.238 Uiso 1 1 calc R U . . .
H2C H 0.2723 0.7515 0.1306 0.238 Uiso 1 1 calc R U . . .
C1 C 0.2971(12) 0.9255(12) 0.0522(12) 0.095(4) Uani 1 1 d . . . . .
H1A H 0.2389 0.9038 0.0820 0.143 Uiso 1 1 calc R U . . .
H1B H 0.3010 0.8979 -0.0175 0.143 Uiso 1 1 calc R U . . .
H1C H 0.3017 1.0056 0.0517 0.143 Uiso 1 1 calc R U . . .
C4 C 0.4590(8) 0.8574(11) 0.0562(15) 0.137(6) Uani 1 1 d D U . . .
H4A H 0.4464 0.8152 -0.0064 0.164 Uiso 1 1 calc R U . . .
H4B H 0.4996 0.8130 0.0997 0.164 Uiso 1 1 calc R U . . .
Cd1 Cd 0.52661(5) 0.30878(6) 0.12377(6) 0.05554(18) Uani 1 1 d . . . . .
Br1 Br 0.60272(11) 0.26413(11) -0.05107(10) 0.0809(4) Uani 1 1 d . . . . .
Br2 Br 0.51011(8) 0.52237(9) 0.14475(13) 0.0749(3) Uani 1 1 d . . . . .
Br3 Br 0.61418(15) 0.21895(15) 0.27494(12) 0.1099(6) Uani 1 1 d . . . . .
Br4 Br 0.36020(10) 0.23065(11) 0.12060(13) 0.0897(4) Uani 1 1 d . . . . .


_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
Cl2 C10 1.792(14) . ?
N2 C6 1.461(12) . ?
N2 C8 1.48(2) . ?
N2 C7 1.491(18) . ?
N2 C9 1.557(13) . ?
C9 C10 1.48(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
Cl1 C5 1.825(17) . ?
N1 C1 1.418(17) . ?
N1 C3 1.451(18) . ?
N1 C4 1.485(11) . ?
N1 C2 1.58(2) . ?
C5 C4 1.498(12) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
Cd1 Br3 2.5617(17) . ?
Cd1 Br1 2.5677(15) . ?
Cd1 Br4 2.5740(15) . ?
Cd1 Br2 2.5793(12) . ?

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
C6 N2 C8 118.2(14) . . ?
C6 N2 C7 107.5(11) . . ?
C8 N2 C7 108.1(13) . . ?
C6 N2 C9 110.4(11) . . ?
C8 N2 C9 100.8(11) . . ?
C7 N2 C9 111.9(10) . . ?
C10 C9 N2 113.3(11) . . ?
C10 C9 H9A 108.9 . . ?
N2 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
N2 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C10 Cl2 104.5(10) . . ?
C9 C10 H10A 110.8 . . ?
Cl2 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
Cl2 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
C1 N1 C3 111.6(12) . . ?
C1 N1 C4 116.7(12) . . ?
C3 N1 C4 118.3(13) . . ?
C1 N1 C2 101.1(12) . . ?
C3 N1 C2 109.1(13) . . ?
C4 N1 C2 96.9(13) . . ?
C4 C5 Cl1 98.7(9) . . ?
C4 C5 H5A 112.0 . . ?
Cl1 C5 H5A 112.0 . . ?
C4 C5 H5B 112.0 . . ?
Cl1 C5 H5B 112.0 . . ?
H5A C5 H5B 109.7 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C4 C5 110.0(11) . . ?
N1 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
Br3 Cd1 Br1 111.93(6) . . ?
Br3 Cd1 Br4 108.60(7) . . ?
Br1 Cd1 Br4 107.97(6) . . ?
Br3 Cd1 Br2 112.36(6) . . ?
Br1 Cd1 Br2 109.74(5) . . ?
Br4 Cd1 Br2 105.97(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
C6 N2 C9 C10 -56.0(17) . . . . ?
C8 N2 C9 C10 178.3(15) . . . . ?
C7 N2 C9 C10 63.7(16) . . . . ?
N2 C9 C10 Cl2 -178.2(10) . . . . ?
C1 N1 C4 C5 71.0(18) . . . . ?
C3 N1 C4 C5 -66.8(19) . . . . ?
C2 N1 C4 C5 177.1(16) . . . . ?
Cl1 C5 C4 N1 177.9(12) . . . . ?

_refine_diff_density_max         0.970
_refine_diff_density_min         -1.373
_refine_diff_density_rms         0.153

####################################################################### 
# 
# 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_tmfe_cdbr_243k
_audit_block_doi                 10.5517/ccdc.csd.cc2bl5y2
_database_code_depnum_ccdc_archive 'CCDC 2162434'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D2QI00964A 2022
loop_
_audit_author_name
_audit_author_address
'Tie Zhang'
;Southeast University
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Br3 Cd, C5 H13 F N'
_chemical_formula_sum            'C5 H13 Br3 Cd F N'
_chemical_formula_weight         458.29

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.1761(5)
_cell_length_b                   15.8039(9)
_cell_length_c                   7.0554(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.275(4)
_cell_angle_gamma                90
_cell_volume                     1131.51(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    243(2)
_cell_measurement_reflns_used    4907
_cell_measurement_theta_min      2.3710
_cell_measurement_theta_max      27.500

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.690
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    12.485
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      243(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11080
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.385
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2600
_reflns_number_gt                2146
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.7093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2600
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cd1 Cd 0.25783(3) 0.75017(2) 0.08827(5) 0.02594(13) Uani 1 1 d . . . . .
Br2 Br 0.26795(5) 0.61567(3) -0.15931(6) 0.02864(14) Uani 1 1 d . . . . .
Br3 Br 0.43807(5) 0.82579(3) -0.13913(7) 0.02854(14) Uani 1 1 d . . . . .
Br1 Br 0.07144(5) 0.68243(3) 0.31664(7) 0.02933(14) Uani 1 1 d . . . . .
F1 F 0.2632(4) 0.3766(2) -0.1008(5) 0.0569(10) Uani 1 1 d . . . . .
N1 N 0.2200(4) 0.4118(3) 0.3045(5) 0.0253(8) Uani 1 1 d . . . . .
C3 C 0.2276(6) 0.3194(3) 0.3498(8) 0.0434(14) Uani 1 1 d . . . . .
H3A H 0.2180 0.2873 0.2341 0.065 Uiso 1 1 calc R U . . .
H3B H 0.1584 0.3046 0.4289 0.065 Uiso 1 1 calc R U . . .
H3C H 0.3114 0.3070 0.4155 0.065 Uiso 1 1 calc R U . . .
C2 C 0.2249(6) 0.4598(4) 0.4902(8) 0.0457(14) Uani 1 1 d . . . . .
H2A H 0.3045 0.4457 0.5652 0.068 Uiso 1 1 calc R U . . .
H2B H 0.1502 0.4446 0.5585 0.068 Uiso 1 1 calc R U . . .
H2C H 0.2231 0.5195 0.4650 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3335(5) 0.4408(3) 0.1977(7) 0.0353(12) Uani 1 1 d . . . . .
H4A H 0.3140 0.4973 0.1494 0.042 Uiso 1 1 calc R U . . .
H4B H 0.4106 0.4451 0.2866 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3677(6) 0.3864(4) 0.0351(9) 0.0472(15) Uani 1 1 d . . . . .
H5A H 0.4414 0.4115 -0.0241 0.057 Uiso 1 1 calc R U . . .
H5B H 0.3951 0.3312 0.0831 0.057 Uiso 1 1 calc R U . . .
C1 C 0.0913(5) 0.4303(4) 0.1968(9) 0.0492(16) Uani 1 1 d . . . . .
H1A H 0.0860 0.4897 0.1680 0.074 Uiso 1 1 calc R U . . .
H1B H 0.0205 0.4149 0.2725 0.074 Uiso 1 1 calc R U . . .
H1C H 0.0847 0.3984 0.0808 0.074 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
Cd1 Br2 2.7580(6) . ?
Cd1 Br2 2.7659(6) 4_576 ?
Cd1 Br1 2.7920(6) . ?
Cd1 Br3 2.7937(6) . ?
Cd1 Br1 2.8041(6) 4_575 ?
Cd1 Br3 2.8245(6) 4_576 ?
Br2 Cd1 2.7659(6) 4_575 ?
Br3 Cd1 2.8246(6) 4_575 ?
Br1 Cd1 2.8041(6) 4_576 ?
F1 C5 1.386(7) . ?
N1 C1 1.493(6) . ?
N1 C3 1.495(6) . ?
N1 C4 1.498(6) . ?
N1 C2 1.512(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 C5 1.496(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
Br2 Cd1 Br2 175.72(2) . 4_576 ?
Br2 Cd1 Br1 97.412(18) . . ?
Br2 Cd1 Br1 85.216(17) 4_576 . ?
Br2 Cd1 Br3 84.771(17) . . ?
Br2 Cd1 Br3 92.716(17) 4_576 . ?
Br1 Cd1 Br3 177.134(19) . . ?
Br2 Cd1 Br1 85.136(17) . 4_575 ?
Br2 Cd1 Br1 98.029(17) 4_576 4_575 ?
Br1 Cd1 Br1 94.938(19) . 4_575 ?
Br3 Cd1 Br1 83.372(16) . 4_575 ?
Br2 Cd1 Br3 92.908(17) . 4_576 ?
Br2 Cd1 Br3 84.042(16) 4_576 4_576 ?
Br1 Cd1 Br3 83.030(17) . 4_576 ?
Br3 Cd1 Br3 98.75(2) . 4_576 ?
Br1 Cd1 Br3 176.988(19) 4_575 4_576 ?
Cd1 Br2 Cd1 79.380(13) . 4_575 ?
Cd1 Br3 Cd1 77.789(14) . 4_575 ?
Cd1 Br1 Cd1 78.156(14) . 4_576 ?
C1 N1 C3 109.3(4) . . ?
C1 N1 C4 111.3(4) . . ?
C3 N1 C4 112.2(4) . . ?
C1 N1 C2 108.3(4) . . ?
C3 N1 C2 107.8(4) . . ?
C4 N1 C2 107.8(4) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C5 C4 N1 116.2(4) . . ?
C5 C4 H4A 108.2 . . ?
N1 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
N1 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
F1 C5 C4 112.6(5) . . ?
F1 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
F1 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         1.420
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.189

