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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/7/12/61/7126116.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_7126116
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 Br6 N3'
_chemical_formula_weight         826.66
_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                 104.248(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.444(3)
_cell_length_b                   8.1886(8)
_cell_length_c                   11.9852(14)
_cell_measurement_reflns_used    1680
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.8500
_cell_measurement_theta_min      2.2970
_cell_volume                     2134.9(4)
_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 0.999
_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  0.0643
_diffrn_reflns_av_unetI/netI     0.0911
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8129
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.872
_exptl_absorpt_coefficient_mu    19.475
_exptl_crystal_density_diffrn    2.572
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_refine_diff_density_max         1.280
_refine_diff_density_min         -1.834
_refine_diff_density_rms         0.352
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0862P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1257
_reflns_number_total             2025
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09477f2.cif
_cod_data_source_block           a_CCDC1
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7126116
_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 0.16718(4) 0.0000 0.21675(7) 0.0406(3) Uani 1 2 d S TU P . .
Br1 Br 0.25646(8) 0.2461(2) 0.27886(16) 0.0678(6) Uani 1 1 d . U . . .
Br2 Br 0.07399(9) 0.2495(2) 0.14302(19) 0.0787(7) Uani 1 1 d . U . . .
Br4 Br 0.18283(13) 0.0000 -0.0176(2) 0.1066(14) Uani 1 2 d S TU P . .
Br5 Br 0.14865(15) 0.0000 0.4371(2) 0.0888(10) Uani 1 2 d S TU P . .
N2 N 0.3277(7) 0.0000 -0.0377(15) 0.065(6) Uani 1 2 d S TU P . .
H2A H 0.3344 0.1013 -0.0643 0.098 Uiso 0.5 1 d R U P . .
H2B H 0.2856 -0.0259 -0.0615 0.098 Uiso 0.5 1 d R U P . .
H2C H 0.3512 -0.0754 -0.0652 0.098 Uiso 0.5 1 d R U P . .
C3 C 0.34997(3) 0.0000 0.0910(4) 0.127(12) Uani 1 2 d DS TU P . .
H3A H 0.3319 -0.0983 0.1199 0.152 Uiso 0.5 1 d R U P . .
H3B H 0.3319 0.0983 0.1199 0.152 Uiso 0.5 1 d R U P . .
C4 C 0.41831(3) 0.0000 0.1391(4) 0.138(15) Uani 1 2 d DS TU P . .
H4A H 0.4352 -0.1093 0.1294 0.208 Uiso 0.5 1 d R U P . .
H4B H 0.4286 0.0282 0.2207 0.208 Uiso 0.5 1 d R U P . .
H4C H 0.4375 0.0811 0.0976 0.208 Uiso 0.5 1 d R U P . .
C6 C 0.08750(4) 0.5000 0.49786(7) 0.180(16) Uani 1 2 d DS TU P . .
H3E H 0.1098 0.4590 0.5661 0.269 Uiso 0.5 1 d R U P . .
H3D H 0.0525 0.4365 0.4701 0.269 Uiso 0.5 1 d R U P . .
H3C H 0.0750 0.6044 0.5078 0.269 Uiso 0.5 1 d R U P . .
C5 C 0.13260(4) 0.5000 0.42398(7) 0.155(14) Uani 1 2 d DS TU P . .
H5A H 0.1182 0.5969 0.3748 0.186 Uiso 0.5 1 d R U P . .
H5B H 0.1182 0.4031 0.3748 0.186 Uiso 0.5 1 d R U P . .
N3 N 0.1848(12) 0.5000 0.453(2) 0.138(8) Uani 1 2 d S TU P . .
H6A H 0.1979 0.4035 0.4197 0.206 Uiso 0.5 1 d R U P . .
H6B H 0.2028 0.5000 0.5340 0.206 Uiso 1 2 d R U P . .
H6C H 0.1978 0.5949 0.4178 0.206 Uiso 0.5 1 d R U P . .
C2 C 0.06411(6) 0.14270(11) 0.66416(11) 0.138(8) Uani 0.5 1 d D U P . .
H1C H 0.0642 0.1111 0.5910 0.206 Uiso 0.5 1 d R U P . .
H1D H 0.0352 0.2264 0.6613 0.206 Uiso 0.5 1 d R U P . .
H1E H 0.1042 0.1784 0.7014 0.206 Uiso 0.5 1 d R U P . .
C1 C 0.03842(6) 0.0000 0.71542(11) 0.138(8) Uani 1 2 d DS TU P . .
H1A H 0.0742 -0.0750 0.7180 0.165 Uiso 0.5 1 d R U P . .
H1B H 0.0006 -0.0554 0.6690 0.165 Uiso 0.5 1 d R U P . .
N1 N 0.0411(9) 0.0000 0.8422(18) 0.087(7) Uani 1 2 d S TU P . .
H2D H 0.0807 0.0351 0.8959 0.131 Uiso 0.5 1 d R U P . .
H2E H 0.0300 -0.1110 0.8622 0.131 Uiso 0.5 1 d R U P . .
H2F H 0.0066 0.0760 0.8466 0.131 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'
Br Br -0.2901 2.4595 '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
Br5 Bi1 Br1 90.69(6) . . ?
Br5 Bi1 Br1 90.69(6) . 6 ?
Br1 Bi1 Br1 91.64(8) . 6 ?
Br5 Bi1 Br2 91.39(7) . . ?
Br1 Bi1 Br2 89.39(6) . . ?
Br1 Bi1 Br2 177.67(6) 6 . ?
Br5 Bi1 Br2 91.39(7) . 6 ?
Br1 Bi1 Br2 177.67(6) . 6 ?
Br1 Bi1 Br2 89.39(6) 6 6 ?
Br2 Bi1 Br2 89.51(8) . 6 ?
Br5 Bi1 Br4 178.35(8) . . ?
Br1 Bi1 Br4 90.46(6) . . ?
Br1 Bi1 Br4 90.46(6) 6 . ?
Br2 Bi1 Br4 87.44(6) . . ?
Br2 Bi1 Br4 87.44(6) 6 . ?
C3 N2 H2A 108.4 . . ?
C3 N2 H2B 111.5 . . ?
H2A N2 H2B 109.8 . . ?
C3 N2 H2C 107.0 . . ?
H2A N2 H2C 109.0 . . ?
H2B N2 H2C 111.1 . . ?
N2 C3 C4 116.5(7) . . ?
N2 C3 H3A 107.1 . . ?
C4 C3 H3A 109.3 . . ?
N2 C3 H3B 107.1 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.1 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 109.2 . . ?
C3 C4 H4C 109.7 . . ?
H4A C4 H4C 108.7 . . ?
H4B C4 H4C 108.6 . . ?
C5 C6 H3E 103.2 . . ?
C5 C6 H3D 114.9 . . ?
H3E C6 H3D 110.1 . . ?
C5 C6 H3C 110.4 . . ?
H3E C6 H3C 110.2 . . ?
H3D C6 H3C 108.0 . . ?
N3 C5 C6 128.1(14) . . ?
N3 C5 H5A 109.9 . . ?
C6 C5 H5A 100.5 . . ?
N3 C5 H5B 109.9 . . ?
C6 C5 H5B 100.5 . . ?
H5A C5 H5B 105.9 . . ?
C5 N3 H6A 105.8 . . ?
C5 N3 H6B 116.8 . . ?
H6A N3 H6B 108.8 . . ?
C5 N3 H6C 105.6 . . ?
H6A N3 H6C 109.5 . . ?
H6B N3 H6C 110.1 . . ?
C1 C2 H1C 105.3 . . ?
C1 C2 H1D 104.6 . . ?
H1C C2 H1D 109.7 . . ?
C1 C2 H1E 117.6 . . ?
H1C C2 H1E 108.2 . . ?
H1D C2 H1E 111.1 . . ?
C2 C1 C2 102.34(11) 6 . ?
C2 C1 N1 119.3(3) 6 . ?
C2 C1 N1 119.3(3) . . ?
C2 C1 H1A 32.0 6 . ?
C2 C1 H1A 95.9 . . ?
N1 C1 H1A 97.8 . . ?
C2 C1 H1B 77.2 6 . ?
C2 C1 H1B 118.9 . . ?
N1 C1 H1B 112.3 . . ?
H1A C1 H1B 107.6 . . ?
C1 N1 H2D 117.2 . . ?
C1 N1 H2E 107.1 . . ?
H2D N1 H2E 110.2 . . ?
C1 N1 H2F 102.3 . . ?
H2D N1 H2F 111.2 . . ?
H2E N1 H2F 108.3 . . ?
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 Br5 2.772(3) . ?
Bi1 Br1 2.8101(17) . ?
Bi1 Br1 2.8101(17) 6 ?
Bi1 Br2 2.9015(18) . ?
Bi1 Br2 2.9015(18) 6 ?
Bi1 Br4 2.915(3) . ?
N2 C3 1.500(18) . ?
N2 H2A 0.9138 . ?
N2 H2B 0.9412 . ?
N2 H2C 0.9232 . ?
C3 C4 1.5000(2) . ?
C3 H3A 1.0008 . ?
C3 H3B 1.0008 . ?
C4 H4A 0.9906 . ?
C4 H4B 0.9749 . ?
C4 H4C 0.9902 . ?
C6 C5 1.50000(18) . ?
C6 H3E 0.9114 . ?
C6 H3D 0.9317 . ?
C6 H3C 0.9167 . ?
C5 N3 1.14(3) . ?
C5 H5A 0.9942 . ?
C5 H5B 0.9942 . ?
N3 H6A 0.9600 . ?
N3 H6B 0.9599 . ?
N3 H6C 0.9600 . ?
C2 C1 1.50000(11) . ?
C2 H1C 0.9146 . ?
C2 H1D 0.9382 . ?
C2 H1E 0.9462 . ?
C1 C2 1.50000(11) 6 ?
C1 N1 1.51(2) . ?
C1 H1A 1.0060 . ?
C1 H1B 1.0020 . ?
N1 H2D 1.0024 . ?
N1 H2E 0.9875 . ?
N1 H2F 1.0048 . ?
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
N1 H2F Br2 1.00 2.33 3.332(16) 179.4 2_556
N1 H2E Br2 0.99 2.58 3.332(16) 132.8 5_556
N1 H2D Br4 1.00 2.29 3.211(18) 152.3 1_556
C2 H1E Br1 0.95 3.14 4.020(2) 155.4 7_556
C2 H1C Br5 0.91 3.09 3.862(3) 143.4 .
N3 H6C Br1 0.96 2.70 3.59(2) 154.7 6_565
N3 H6B Br1 0.96 2.99 3.75(2) 137.6 4_556
N3 H6B Br1 0.96 2.99 3.75(2) 137.6 7_556
N3 H6A Br1 0.96 2.71 3.59(2) 153.0 .
C5 H5B Br2 0.99 2.99 3.886(2) 150.8 .
C5 H5A Br2 0.99 2.99 3.886(2) 150.8 6_565
C3 H3B Br1 1.00 3.09 3.983(4) 149.2 .
C3 H3A Br1 1.00 3.09 3.983(4) 149.2 6
N2 H2C Br2 0.92 2.55 3.470(15) 172.0 4_545
N2 H2B Br4 0.94 2.50 3.319(17) 145.8 .
N2 H2A Br2 0.91 2.75 3.470(15) 136.4 7
N2 H2A Br1 0.91 3.12 3.682(14) 121.3 7
