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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/7/12/61/7126112.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_7126112
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 H21 Bi Br6 Cl3 N3'
_chemical_formula_weight         929.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                104.697(2)
_cell_angle_beta                 108.110(2)
_cell_angle_gamma                93.253(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3218(2)
_cell_length_b                   12.1968(3)
_cell_length_c                   12.2353(4)
_cell_measurement_reflns_used    7470
_cell_measurement_temperature    289(2)
_cell_measurement_theta_max      31.3980
_cell_measurement_theta_min      2.6010
_cell_volume                     1129.25(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      289(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.826
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19802
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.508
_diffrn_reflns_theta_min         2.604
_exptl_absorpt_coefficient_mu    18.769
_exptl_crystal_density_diffrn    2.735
_exptl_crystal_description       block
_exptl_crystal_F_000             844
_refine_diff_density_max         1.990
_refine_diff_density_min         -1.238
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       0.00051(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         7521
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0462
_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)+(0.0503P)²+4.4780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4477
_reflns_number_total             7521
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09477f2.cif
_cod_data_source_block           1
_cod_database_code               7126112
_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'
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
Cl3 Cl 0.7309(3) 0.1258(3) 0.0915(3) 0.0803(8) Uani 1 1 d . U . . .
Bi1 Bi 0.34247(3) 0.28980(2) 0.66943(3) 0.03411(11) Uani 1 1 d . U . . .
Br1 Br 0.39637(10) 0.51966(6) 0.63890(7) 0.04315(19) Uani 1 1 d . U . . .
Br2 Br -0.00312(10) 0.23107(7) 0.49562(8) 0.0448(2) Uani 1 1 d . U . . .
Br3 Br 0.19501(11) 0.38241(8) 0.84861(8) 0.0512(2) Uani 1 1 d . U . . .
Br4 Br 0.66793(11) 0.35056(9) 0.84787(9) 0.0555(2) Uani 1 1 d . U . . .
Br5 Br 0.48728(12) 0.20599(8) 0.48666(9) 0.0552(2) Uani 1 1 d . U . . .
Br6 Br 0.31444(14) 0.07179(7) 0.69995(10) 0.0630(3) Uani 1 1 d . U . . .
Cl2 Cl 0.9227(3) 0.64564(15) 0.88198(17) 0.0441(4) Uani 1 1 d . U . . .
Cl1 Cl 0.1553(4) 1.0524(2) 0.1604(2) 0.0740(7) Uani 1 1 d . U . . .
N2 N 0.8106(9) 0.4405(6) 0.6406(7) 0.0451(16) Uani 1 1 d . U . . .
H2A H 0.8173 0.4368 0.7135 0.068 Uiso 1 1 calc R U . . .
H2B H 0.8431 0.3782 0.6024 0.068 Uiso 1 1 calc R U . . .
H2C H 0.7032 0.4448 0.5995 0.068 Uiso 1 1 calc R U . . .
C3 C 0.9228(10) 0.5427(7) 0.6508(8) 0.0445(18) Uani 1 1 d . U . . .
H3D H 0.9107 0.5492 0.5714 0.053 Uiso 1 1 calc R U . . .
H3E H 1.0409 0.5353 0.6896 0.053 Uiso 1 1 calc R U . . .
N3 N 0.5116(11) 0.3362(7) 0.0714(7) 0.067(2) Uani 1 1 d . U . . .
H3A H 0.5264 0.3874 0.1413 0.100 Uiso 1 1 calc R U . . .
H3B H 0.4383 0.3569 0.0125 0.100 Uiso 1 1 calc R U . . .
H3C H 0.6114 0.3326 0.0591 0.100 Uiso 1 1 calc R U . . .
N1 N 0.1630(18) 0.9711(8) 0.3878(11) 0.110(4) Uani 1 1 d . U . . .
H1A H 0.1032 1.0269 0.3721 0.132 Uiso 1 1 calc R U . A 1
H1B H 0.2715 1.0009 0.4304 0.132 Uiso 1 1 calc R U . A 1
H1C H 0.1195 0.9355 0.4296 0.132 Uiso 1 1 calc R U . A 1
C4 C 0.8783(12) 0.6489(7) 0.7227(8) 0.052(2) Uani 1 1 d . U . . .
H4A H 0.7583 0.6537 0.6868 0.063 Uiso 1 1 calc R U . . .
H4B H 0.9451 0.7161 0.7216 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4434(15) 0.2228(10) 0.0734(15) 0.098(4) Uani 1 1 d . U . . .
H5A H 0.4037 0.1711 -0.0074 0.118 Uiso 1 1 calc R U . B 2
H5B H 0.3463 0.2299 0.1014 0.118 Uiso 1 1 calc R U . B 2
C2 C 0.069(2) 0.9215(11) 0.1697(14) 0.102(4) Uani 1 1 d . U . . .
H2D H -0.0507 0.9240 0.1619 0.122 Uiso 1 1 calc R U . C 1
H2E H 0.0726 0.8606 0.1024 0.122 Uiso 1 1 calc R U . C 1
C6' C 0.591(2) 0.1679(9) 0.1626(14) 0.112(5) Uani 1 1 d . U . D 2
H6'A H 0.5378 0.1030 0.1777 0.135 Uiso 1 1 calc R U . D 2
H6'B H 0.6490 0.2250 0.2387 0.135 Uiso 1 1 calc R U . D 2
C1 C 0.155(2) 0.8933(10) 0.2809(14) 0.104(4) Uani 1 1 d . U . E 1
H1D H 0.0981 0.8199 0.2766 0.125 Uiso 1 1 calc R U . E 1
H1E H 0.2711 0.8834 0.2839 0.125 Uiso 1 1 calc R U . E 1
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'
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
Br6 Bi1 Br4 90.89(3) . . ?
Br6 Bi1 Br5 89.59(3) . . ?
Br4 Bi1 Br5 91.55(3) . . ?
Br6 Bi1 Br3 92.85(3) . . ?
Br4 Bi1 Br3 89.10(3) . . ?
Br5 Bi1 Br3 177.47(3) . . ?
Br6 Bi1 Br2 88.93(3) . . ?
Br4 Bi1 Br2 176.68(3) . . ?
Br5 Bi1 Br2 91.76(3) . . ?
Br3 Bi1 Br2 87.60(3) . . ?
Br6 Bi1 Br1 176.16(3) . . ?
Br4 Bi1 Br1 86.17(3) . . ?
Br5 Bi1 Br1 88.03(3) . . ?
Br3 Bi1 Br1 89.57(3) . . ?
Br2 Bi1 Br1 94.14(2) . . ?
C3 N2 H2A 109.5 . . ?
C3 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C3 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N2 C3 C4 110.5(7) . . ?
N2 C3 H3D 109.5 . . ?
C4 C3 H3D 109.5 . . ?
N2 C3 H3E 109.5 . . ?
C4 C3 H3E 109.5 . . ?
H3D C3 H3E 108.1 . . ?
C5 N3 H3A 109.5 . . ?
C5 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C5 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 C4 Cl2 110.5(6) . . ?
C3 C4 H4A 109.6 . . ?
Cl2 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
Cl2 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N3 C5 C6' 111.5(10) . . ?
N3 C5 H5A 109.3 . . ?
C6' C5 H5A 109.3 . . ?
N3 C5 H5B 109.3 . . ?
C6' C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C1 C2 Cl1 114.7(10) . . ?
C1 C2 H2D 108.6 . . ?
Cl1 C2 H2D 108.6 . . ?
C1 C2 H2E 108.6 . . ?
Cl1 C2 H2E 108.6 . . ?
H2D C2 H2E 107.6 . . ?
C5 C6' Cl3 107.3(9) . . ?
C5 C6' H6'A 110.3 . . ?
Cl3 C6' H6'A 110.3 . . ?
C5 C6' H6'B 110.3 . . ?
Cl3 C6' H6'B 110.3 . . ?
H6'A C6' H6'B 108.5 . . ?
N1 C1 C2 117.2(13) . . ?
N1 C1 H1D 108.0 . . ?
C2 C1 H1D 108.0 . . ?
N1 C1 H1E 108.0 . . ?
C2 C1 H1E 108.0 . . ?
H1D C1 H1E 107.3 . . ?
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
Cl3 C6' 1.688(13) . ?
Bi1 Br6 2.7842(9) . ?
Bi1 Br4 2.8154(9) . ?
Bi1 Br5 2.8554(9) . ?
Bi1 Br3 2.8567(9) . ?
Bi1 Br2 2.9150(8) . ?
Bi1 Br1 2.9484(8) . ?
Cl2 C4 1.878(9) . ?
Cl1 C2 1.759(13) . ?
N2 C3 1.469(10) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C3 C4 1.505(12) . ?
C3 H3D 0.9700 . ?
C3 H3E 0.9700 . ?
N3 C5 1.474(14) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N1 C1 1.389(17) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6' 1.67(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 C1 1.46(2) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
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
C1 H1E Br4 0.97 3.06 3.613(14) 117.9 2_666
C1 H1D Br3 0.97 3.08 3.952(15) 151.0 2_566
C6' H6'A Br6 0.97 3.01 3.732(11) 132.1 2_656
C5 H5B Cl1 0.97 2.98 3.653(14) 127.9 1_545
C5 H5B Cl2 0.97 2.81 3.647(12) 145.5 2_666
C4 H4B Br2 0.97 3.06 3.728(9) 127.5 2_666
N1 H1C Br2 0.89 2.68 3.533(10) 161.3 2_566
N1 H1B Br5 0.89 2.79 3.505(10) 137.9 1_565
N1 H1A Br2 0.89 2.91 3.635(12) 140.3 1_565
N3 H3C Br4 0.89 2.83 3.410(9) 124.6 1_554
N3 H3B Br3 0.89 2.47 3.343(8) 168.5 1_554
N3 H3A Br1 0.89 2.50 3.353(9) 161.9 2_666
C3 H3E Br3 0.97 3.08 3.782(8) 130.8 1_655
C3 H3D Br2 0.97 3.12 3.784(8) 127.2 2_666
C3 H3D Br1 0.97 2.90 3.571(8) 126.9 2_666
N2 H2C Br5 0.89 3.07 3.494(7) 111.2 .
N2 H2C Br1 0.89 2.93 3.488(7) 122.6 2_666
N2 H2C Br1 0.89 2.90 3.627(7) 140.4 .
N2 H2B Br2 0.89 2.58 3.455(7) 166.5 1_655
N2 H2A Cl2 0.89 2.73 3.182(7) 112.6 .
N2 H2A Br4 0.89 2.71 3.491(7) 146.8 .
N2 H2A Br4 0.89 2.71 3.491(7) 146.8 .
N2 H2A Br4 0.89 2.71 3.491(7) 146.8 .
N2 H2A Cl2 0.89 2.73 3.182(7) 112.6 .
N2 H2B Br2 0.89 2.58 3.455(7) 166.5 1_655
N2 H2C Br1 0.89 2.90 3.627(7) 140.4 .
N2 H2C Br1 0.89 2.93 3.488(7) 122.6 2_666
N2 H2C Br5 0.89 3.07 3.494(7) 111.2 .
C3 H3D Br1 0.97 2.90 3.571(8) 126.9 2_666
C3 H3D Br2 0.97 3.12 3.784(8) 127.2 2_666
C3 H3E Br3 0.97 3.08 3.782(8) 130.8 1_655
N3 H3A Br1 0.89 2.50 3.353(9) 161.9 2_666
N3 H3B Br3 0.89 2.47 3.343(8) 168.5 1_554
N3 H3C Br4 0.89 2.83 3.410(9) 124.6 1_554
N1 H1A Br2 0.89 2.91 3.635(12) 140.3 1_565
N1 H1B Br5 0.89 2.79 3.505(10) 137.9 1_565
N1 H1C Br2 0.89 2.68 3.533(10) 161.3 2_566
C4 H4B Br2 0.97 3.06 3.728(9) 127.5 2_666
C5 H5B Cl2 0.97 2.81 3.647(12) 145.5 2_666
C5 H5B Cl1 0.97 2.98 3.653(14) 127.9 1_545
C6' H6'A Br6 0.97 3.01 3.732(11) 132.1 2_656
C1 H1D Br3 0.97 3.08 3.952(15) 151.0 2_566
C1 H1E Br4 0.97 3.06 3.613(14) 117.9 2_666
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
N2 C3 C4 Cl2 65.2(8) . . . . ?
N3 C5 C6' Cl3 -73.3(12) . . . . ?
Cl1 C2 C1 N1 58.2(19) . . . . ?
