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#$Date: 2020-03-04 08:13:23 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/61/7126113.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7126113
loop_
_publ_author_name
'Li, Hui-Hui'
'Wang, Chang-Feng'
'Wu, Ya-Xing'
'Jiang, Fan'
'Shi, Chao'
'Ye, Heng-Yun'
'Zhang, Yi'
_publ_section_title
;
 Halogen substitution regulates the phase transition temperature and band
 gap of semiconductor compounds.
;
_journal_issue                   11
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1697
_journal_page_last               1700
_journal_paper_doi               10.1039/c9cc09477f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C6 H24 Bi Cl6 N3'
_chemical_formula_weight         559.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-09-16 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.186(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.1620(15)
_cell_length_b                   7.9735(5)
_cell_length_c                   11.8046(7)
_cell_measurement_reflns_used    2820
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3200
_cell_measurement_theta_min      1.8970
_cell_volume                     1931.1(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10006
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.825
_diffrn_reflns_theta_min         1.985
_exptl_absorpt_coefficient_mu    9.945
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_refine_diff_density_max         0.848
_refine_diff_density_min         -2.307
_refine_diff_density_rms         0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0820P)²+6.2619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2332
_reflns_number_total             2959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09477f2.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7126113
_shelx_shelxl_version_number     2014/7
_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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
Bi1 Bi 0.16908(2) 0.0000 0.21726(3) 0.04435(16) Uani 1 2 d S TU P . .
Cl1 Cl 0.25722(13) 0.2417(4) 0.2762(3) 0.0824(8) Uani 1 1 d . U . . .
Cl2 Cl 0.07546(14) 0.2426(4) 0.1490(4) 0.1025(11) Uani 1 1 d . U . . .
Cl4 Cl 0.1831(2) 0.0000 -0.0088(3) 0.140(3) Uani 1 2 d S TU P . .
Cl5 Cl 0.1520(3) 0.0000 0.4289(4) 0.1095(17) Uani 1 2 d S TU P . .
N2 N 0.3271(6) 1.0000 -0.0465(10) 0.070(3) Uani 1 2 d S TU P . .
H2A H 0.3338 1.1013 -0.0730 0.106 Uiso 0.5 1 d R U P . .
H2B H 0.2850 0.9741 -0.0702 0.106 Uiso 0.5 1 d R U P . .
H2C H 0.3505 0.9246 -0.0739 0.106 Uiso 0.5 1 d R U P . .
C3 C 0.34919(3) 1.0000 0.0783(3) 0.135(9) Uani 1 2 d DS TU P . .
H3A H 0.3311 0.9017 0.1071 0.162 Uiso 0.5 1 d R U P . .
H3B H 0.3311 1.0983 0.1071 0.162 Uiso 0.5 1 d R U P . .
C4 C 0.42129(3) 1.0000 0.1310(3) 0.135(9) Uani 1 2 d DS TU P . .
H4A H 0.4382 0.8907 0.1213 0.203 Uiso 0.5 1 d R U P . .
H4B H 0.4316 1.0282 0.2125 0.203 Uiso 0.5 1 d R U P . .
H4C H 0.4405 1.0811 0.0895 0.203 Uiso 0.5 1 d R U P . .
C6 C 0.08497(4) 0.5000 0.49270(8) 0.192(13) Uani 1 2 d DS TU P . .
H3E H 0.1073 0.4590 0.5609 0.288 Uiso 0.5 1 d R U P . .
H3D H 0.0500 0.4365 0.4649 0.288 Uiso 0.5 1 d R U P . .
H3C H 0.0725 0.6044 0.5026 0.288 Uiso 0.5 1 d R U P . .
C5 C 0.13768(4) 0.5000 0.42781(8) 0.186(13) Uani 1 2 d DS TU P . .
H5A H 0.1232 0.5969 0.3786 0.223 Uiso 0.5 1 d R U P . .
H5B H 0.1232 0.4031 0.3786 0.223 Uiso 0.5 1 d R U P . .
N3 N 0.1888(10) 0.5000 0.4449(19) 0.177(8) Uani 1 2 d S TU P . .
H6A H 0.2013 0.4119 0.3994 0.266 Uiso 0.5 1 d R U P . .
H6B H 0.2090 0.4820 0.5262 0.266 Uiso 0.5 1 d R U P . .
H6C H 0.2026 0.6061 0.4209 0.266 Uiso 0.5 1 d R U P . .
C2 C 0.06589(9) 0.15046(11) 0.66118(11) 0.198(14) Uani 0.5 1 d D U P . .
H1C H 0.0660 0.1189 0.5880 0.297 Uiso 0.5 1 d R U P . .
H1D H 0.0370 0.2341 0.6584 0.297 Uiso 0.5 1 d R U P . .
H1E H 0.1059 0.1862 0.6984 0.297 Uiso 0.5 1 d R U P . .
C1 C 0.04820(9) 0.0000 0.72321(11) 0.177(8) Uani 1 2 d DS TU P . .
H1A H 0.0840 -0.0750 0.7258 0.213 Uiso 0.5 1 d R U P . .
H1B H 0.0104 -0.0554 0.6768 0.213 Uiso 0.5 1 d R U P . .
N1 N 0.0408(7) 0.0000 0.8407(12) 0.093(4) Uani 1 2 d S TU P . .
H2D H 0.0804 0.0351 0.8944 0.140 Uiso 0.5 1 d R U P . .
H2E H 0.0296 -0.1110 0.8606 0.140 Uiso 0.5 1 d R U P . .
H2F H 0.0062 0.0760 0.8451 0.140 Uiso 0.5 1 d R U P . .
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'
Bi Bi -4.1077 10.2566 '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'
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
Cl5 Bi1 Cl1 90.12(12) . . ?
Cl5 Bi1 Cl1 90.12(12) . 6 ?
Cl1 Bi1 Cl1 93.16(13) . 6 ?
Cl5 Bi1 Cl2 91.26(13) . . ?
Cl1 Bi1 Cl2 88.59(11) . . ?
Cl1 Bi1 Cl2 177.77(9) 6 . ?
Cl5 Bi1 Cl2 91.26(13) . 6 ?
Cl1 Bi1 Cl2 177.77(9) . 6 ?
Cl1 Bi1 Cl2 88.59(11) 6 6 ?
Cl2 Bi1 Cl2 89.62(15) . 6 ?
Cl5 Bi1 Cl4 178.27(14) . . ?
Cl1 Bi1 Cl4 91.06(9) . . ?
Cl1 Bi1 Cl4 91.06(9) 6 . ?
Cl2 Bi1 Cl4 87.52(11) . . ?
Cl2 Bi1 Cl4 87.52(11) 6 . ?
C3 N2 H2A 108.8 . . ?
C3 N2 H2B 111.9 . . ?
H2A N2 H2B 109.5 . . ?
C3 N2 H2C 107.7 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N2 C3 C4 118.0(5) . . ?
N2 C3 H3A 107.7 . . ?
C4 C3 H3A 107.6 . . ?
N2 C3 H3B 107.7 . . ?
C4 C3 H3B 107.6 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 112.0 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 107.6 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C6 H3E 99.6 . . ?
C5 C6 H3D 117.9 . . ?
H3E C6 H3D 109.5 . . ?
C5 C6 H3C 110.4 . . ?
H3E C6 H3C 109.5 . . ?
H3D C6 H3C 109.5 . . ?
N3 C5 C6 139.6(12) . . ?
N3 C5 H5A 105.9 . . ?
C6 C5 H5A 98.1 . . ?
N3 C5 H5B 105.9 . . ?
C6 C5 H5B 98.1 . . ?
H5A C5 H5B 105.6 . . ?
C5 N3 H6A 107.7 . . ?
C5 N3 H6B 112.2 . . ?
H6A N3 H6B 109.5 . . ?
C5 N3 H6C 108.5 . . ?
H6A N3 H6C 109.5 . . ?
H6B N3 H6C 109.5 . . ?
C1 C2 C2 36.89(5) . 6 ?
C1 C2 H1C 107.7 . . ?
C2 C2 H1C 73.8 6 . ?
C1 C2 H1D 111.2 . . ?
C2 C2 H1D 137.8 6 . ?
H1C C2 H1D 109.5 . . ?
C1 C2 H1E 109.4 . . ?
C2 C2 H1E 108.4 6 . ?
H1C C2 H1E 109.5 . . ?
H1D C2 H1E 109.5 . . ?
C2 C1 C2 106.22(11) 6 . ?
C2 C1 N1 124.89(13) 6 . ?
C2 C1 N1 124.89(14) . . ?
C2 C1 H1A 39.4 6 . ?
C2 C1 H1A 102.9 . . ?
N1 C1 H1A 104.0 . . ?
C2 C1 H1B 68.1 6 . ?
C2 C1 H1B 111.2 . . ?
N1 C1 H1B 106.2 . . ?
H1A C1 H1B 105.9 . . ?
C1 N1 H2D 110.7 . . ?
C1 N1 H2E 109.2 . . ?
H2D N1 H2E 109.5 . . ?
C1 N1 H2F 108.5 . . ?
H2D N1 H2F 109.5 . . ?
H2E N1 H2F 109.5 . . ?
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
Bi1 Cl5 2.611(4) . ?
Bi1 Cl1 2.654(2) . ?
Bi1 Cl1 2.654(2) 6 ?
Bi1 Cl2 2.745(3) . ?
Bi1 Cl2 2.745(3) 6 ?
Bi1 Cl4 2.756(4) . ?
N2 C3 1.431(13) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C3 C4 1.50000(13) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 C5 1.50000(11) . ?
C6 H3E 0.8900 . ?
C6 H3D 0.8900 . ?
C6 H3C 0.8900 . ?
C5 N3 1.05(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N3 H6A 0.9600 . ?
N3 H6B 0.9600 . ?
N3 H6C 0.9600 . ?
C2 C1 1.50000(7) . ?
C2 C2 2.3994(17) 6 ?
C2 H1C 0.9000 . ?
C2 H1D 0.9000 . ?
C2 H1E 0.9000 . ?
C1 C2 1.49998(7) 6 ?
C1 N1 1.433(14) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
N1 H2D 0.9600 . ?
N1 H2E 0.9600 . ?
N1 H2F 0.9599 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H6C Cl1 0.96 2.59 3.423(17) 145.7 6_565
N3 H6B Cl5 0.96 2.86 3.33(2) 111.3 7_556
N3 H6B Cl1 0.96 2.88 3.743(19) 149.5 7_556
N3 H6A Cl1 0.96 2.49 3.423(17) 164.0 .
C5 H5B Cl2 0.97 2.94 3.828(5) 152.2 .
C5 H5A Cl2 0.97 2.94 3.828(4) 152.2 6_565
N2 H2C Cl2 0.89 2.45 3.340(10) 173.3 4
N2 H2B Cl4 0.89 2.45 3.186(13) 140.7 1_565
N2 H2A Cl2 0.89 2.62 3.340(10) 138.1 7_565
N2 H2A Cl1 0.89 2.96 3.523(10) 122.7 7_565
N2 H2A Cl1 0.89 2.96 3.523(10) 122.7 7_565
N2 H2A Cl2 0.89 2.62 3.340(10) 138.1 7_565
N2 H2B Cl4 0.89 2.45 3.186(13) 140.7 1_565
N2 H2C Cl2 0.89 2.45 3.340(10) 173.3 4
C5 H5A Cl2 0.97 2.94 3.828(4) 152.2 6_565
C5 H5B Cl2 0.97 2.94 3.828(5) 152.2 .
N3 H6A Cl1 0.96 2.49 3.423(17) 164.0 .
N3 H6B Cl1 0.96 2.88 3.743(19) 149.5 7_556
N3 H6B Cl5 0.96 2.86 3.33(2) 111.3 7_556
N3 H6C Cl1 0.96 2.59 3.423(17) 145.7 6_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
C2 C2 C1 N1 158.3(7) 6 . . . ?
