#------------------------------------------------------------------------------
#$Date: 2020-03-04 08:13:23 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/61/7126111.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_7126111
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 Cl9 N3'
_chemical_formula_weight         663.29
_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                104.188(2)
_cell_angle_beta                 93.217(2)
_cell_angle_gamma                108.402(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1810(2)
_cell_length_b                   11.7216(4)
_cell_length_c                   11.8724(3)
_cell_measurement_reflns_used    8310
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      31.3740
_cell_measurement_theta_min      2.6320
_cell_volume                     1036.24(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.819
_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  0.0487
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16819
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.650
_diffrn_reflns_theta_min         2.652
_exptl_absorpt_coefficient_mu    9.659
_exptl_crystal_density_diffrn    2.126
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_refine_diff_density_max         1.021
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         6989
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0435P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4380
_reflns_number_total             6989
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09477f2.cif
_cod_data_source_block           c
_cod_original_cell_volume        1036.24(5)
_cod_database_code               7126111
_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
Bi1 Bi 0.15760(2) 0.33319(2) 0.21098(2) 0.03428(8) Uani 1 1 d . . . . .
Cl1 Cl 0.0190(2) 0.51436(17) 0.29321(14) 0.0575(4) Uani 1 1 d . . . . .
Cl2 Cl 0.1840(3) 0.3027(2) 0.42313(14) 0.0674(5) Uani 1 1 d . . . . .
Cl3 Cl -0.1582(2) 0.16035(17) 0.15791(17) 0.0629(4) Uani 1 1 d . . . . .
Cl4 Cl 0.2909(2) 0.15288(15) 0.11943(15) 0.0538(4) Uani 1 1 d . . . . .
Cl5 Cl 0.1007(2) 0.36039(14) -0.01374(12) 0.0466(3) Uani 1 1 d . . . . .
Cl6 Cl 0.49742(18) 0.50244(14) 0.26720(13) 0.0461(3) Uani 1 1 d . . . . .
Cl7 Cl 0.6605(3) 0.1592(2) 0.55348(18) 0.0789(6) Uani 1 1 d . . . . .
C1 C 0.6379(17) 0.2884(10) 0.4008(10) 0.121(4) Uani 1 1 d . . . . .
H1A H 0.7384 0.2867 0.3617 0.145 Uiso 1 1 calc DR U . . .
H1B H 0.5507 0.2875 0.3414 0.145 Uiso 1 1 calc R U . . .
C2 C 0.5725(14) 0.1681(9) 0.4199(8) 0.098(3) Uani 1 1 d . . . . .
H2A H 0.5963 0.1080 0.3567 0.118 Uiso 1 1 calc R U . . .
H2B H 0.4472 0.1443 0.4166 0.118 Uiso 1 1 calc R U . . .
N1 N 0.681(2) 0.3905(9) 0.4650(7) 0.191(7) Uani 1 1 d . . . . .
H1C H 0.5919 0.4014 0.5002 0.287 Uiso 1 1 calc R U . . .
H1D H 0.7159 0.4462 0.4244 0.287 Uiso 1 1 calc R U . . .
H1E H 0.7688 0.4009 0.5189 0.287 Uiso 1 1 calc DR U . . .
Cl9 Cl 0.4174(3) 0.88228(18) 0.13688(16) 0.0693(5) Uani 1 1 d . . . . .
C6 C 0.3787(9) 0.7249(6) 0.1434(5) 0.0523(15) Uani 1 1 d . . . . .
H6A H 0.4486 0.7259 0.2126 0.063 Uiso 1 1 calc R U . . .
H6B H 0.2571 0.6864 0.1499 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4222(8) 0.6507(6) 0.0385(5) 0.0442(13) Uani 1 1 d . . . . .
H5A H 0.4120 0.5692 0.0484 0.053 Uiso 1 1 calc R U . . .
H5B H 0.5422 0.6918 0.0302 0.053 Uiso 1 1 calc R U . . .
N3 N 0.3092(7) 0.6342(5) -0.0688(4) 0.0486(12) Uani 1 1 d . . . . .
H3A H 0.1996 0.5923 -0.0636 0.073 Uiso 1 1 calc R U . . .
H3B H 0.3430 0.5915 -0.1304 0.073 Uiso 1 1 calc R U . . .
H3C H 0.3165 0.7089 -0.0776 0.073 Uiso 1 1 calc R U . . .
Cl8 Cl 0.2371(3) 0.0978(3) 0.6275(2) 0.1020(8) Uani 1 1 d . . . . .
C4 C 0.0898(14) 0.1688(10) 0.6747(7) 0.093(3) Uani 1 1 d . . . . .
H4A H 0.1484 0.2474 0.7342 0.111 Uiso 1 1 calc R U . . .
H4B H 0.0344 0.1862 0.6096 0.111 Uiso 1 1 calc R U . . .
C3 C -0.0484(10) 0.0795(11) 0.7264(7) 0.086(3) Uani 1 1 d . . . . .
H3D H -0.1475 0.1079 0.7352 0.103 Uiso 1 1 calc R U . . .
H3E H -0.0888 -0.0037 0.6721 0.103 Uiso 1 1 calc R U . . .
N2 N 0.0207(8) 0.0737(6) 0.8403(5) 0.0610(14) Uani 1 1 d . . . . .
H2C H 0.1185 0.0559 0.8343 0.092 Uiso 1 1 calc R U . . .
H2D H -0.0572 0.0144 0.8629 0.092 Uiso 1 1 calc R U . . .
H2E H 0.0431 0.1472 0.8931 0.092 Uiso 1 1 calc R U . . .
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
Cl2 Bi1 Cl3 90.05(6) . . ?
Cl2 Bi1 Cl4 93.31(5) . . ?
Cl3 Bi1 Cl4 88.90(5) . . ?
Cl2 Bi1 Cl1 89.16(6) . . ?
Cl3 Bi1 Cl1 90.53(6) . . ?
Cl4 Bi1 Cl1 177.47(5) . . ?
Cl2 Bi1 Cl6 88.56(6) . . ?
Cl3 Bi1 Cl6 176.35(4) . . ?
Cl4 Bi1 Cl6 87.80(5) . . ?
Cl1 Bi1 Cl6 92.83(5) . . ?
Cl2 Bi1 Cl5 175.39(5) . . ?
Cl3 Bi1 Cl5 85.98(5) . . ?
Cl4 Bi1 Cl5 88.97(5) . . ?
Cl1 Bi1 Cl5 88.53(5) . . ?
Cl6 Bi1 Cl5 95.54(4) . . ?
N1 C1 C2 132.3(12) . . ?
N1 C1 H1A 104.2 . . ?
C2 C1 H1A 104.2 . . ?
N1 C1 H1B 104.2 . . ?
C2 C1 H1B 104.2 . . ?
H1A C1 H1B 105.5 . . ?
C1 C2 Cl7 114.2(7) . . ?
C1 C2 H2A 108.7 . . ?
Cl7 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
Cl7 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C5 C6 Cl9 111.1(4) . . ?
C5 C6 H6A 109.4 . . ?
Cl9 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
Cl9 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C5 N3 112.6(5) . . ?
C6 C5 H5A 109.1 . . ?
N3 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
N3 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
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 . . ?
C3 C4 Cl8 108.2(7) . . ?
C3 C4 H4A 110.1 . . ?
Cl8 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
Cl8 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N2 C3 C4 112.0(7) . . ?
N2 C3 H3D 109.2 . . ?
C4 C3 H3D 109.2 . . ?
N2 C3 H3E 109.2 . . ?
C4 C3 H3E 109.2 . . ?
H3D C3 H3E 107.9 . . ?
C3 N2 H2C 109.5 . . ?
C3 N2 H2D 109.5 . . ?
H2C N2 H2D 109.5 . . ?
C3 N2 H2E 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 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 Cl2 2.6356(15) . ?
Bi1 Cl3 2.6577(17) . ?
Bi1 Cl4 2.7021(14) . ?
Bi1 Cl1 2.7163(14) . ?
Bi1 Cl6 2.7875(15) . ?
Bi1 Cl5 2.7943(13) . ?
Cl7 C2 1.745(8) . ?
C1 N1 1.181(12) . ?
C1 C2 1.422(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
Cl9 C6 1.792(7) . ?
C6 C5 1.466(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 N3 1.466(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
Cl8 C4 1.715(8) . ?
C4 C3 1.548(13) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 N2 1.462(9) . ?
C3 H3D 0.9700 . ?
C3 H3E 0.9700 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?
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
N2 H2E Cl5 0.89 2.35 3.218(6) 164.3 1_556
N2 H2D Cl4 0.89 2.33 3.204(6) 167.7 2_556
N2 H2C Cl3 0.89 2.68 3.281(6) 126.0 2_556
C3 H3D Cl9 0.97 2.77 3.605(8) 145.2 2_566
C3 H3D Cl7 0.97 2.89 3.543(8) 125.8 1_455
N3 H3C Cl3 0.89 2.60 3.380(5) 146.6 2_565
N3 H3B Cl6 0.89 2.41 3.284(5) 166.0 2_665
N3 H3A Cl5 0.89 2.84 3.561(5) 139.5 2_565
N3 H3A Cl5 0.89 2.80 3.367(6) 122.7 .
N3 H3A Cl1 0.89 2.93 3.363(5) 112.0 2_565
C5 H5B Cl4 0.97 2.94 3.677(6) 134.0 2_665
C5 H5A Cl5 0.97 2.83 3.466(6) 124.2 .
C6 H6A Cl8 0.97 2.94 3.707(7) 136.5 2_666
C6 H6A Cl6 0.97 2.98 3.637(7) 125.7 .
N1 H1E Cl1 0.89 2.52 3.378(10) 161.2 2_666
N1 H1D Cl6 0.89 2.84 3.444(9) 126.1 .
N1 H1D Cl2 0.89 2.88 3.301(9) 110.5 2_666
N1 H1C Cl6 0.89 2.94 3.680(13) 141.5 2_666
C1 H1A Cl3 0.97 2.83 3.654(14) 142.9 1_655
N2 H2E Cl5 0.89 2.35 3.218(6) 164.3 1_556
N2 H2D Cl4 0.89 2.33 3.204(6) 167.7 2_556
N2 H2C Cl3 0.89 2.68 3.281(6) 126.0 2_556
C3 H3D Cl9 0.97 2.77 3.605(8) 145.2 2_566
C3 H3D Cl7 0.97 2.89 3.543(8) 125.8 1_455
N3 H3C Cl3 0.89 2.60 3.380(5) 146.6 2_565
N3 H3B Cl6 0.89 2.41 3.284(5) 166.0 2_665
N3 H3A Cl5 0.89 2.84 3.561(5) 139.5 2_565
N3 H3A Cl5 0.89 2.80 3.367(6) 122.7 .
N3 H3A Cl1 0.89 2.93 3.363(5) 112.0 2_565
C5 H5B Cl4 0.97 2.94 3.677(6) 134.0 2_665
C5 H5A Cl5 0.97 2.83 3.466(6) 124.2 .
C6 H6A Cl8 0.97 2.94 3.707(7) 136.5 2_666
C6 H6A Cl6 0.97 2.98 3.637(7) 125.7 .
N1 H1E Cl1 0.89 2.52 3.378(10) 161.2 2_666
N1 H1D Cl6 0.89 2.84 3.444(9) 126.1 .
N1 H1D Cl2 0.89 2.88 3.301(9) 110.5 2_666
N1 H1C Cl6 0.89 2.94 3.680(13) 141.5 2_666
C1 H1A Cl3 0.97 2.83 3.654(14) 142.9 1_655
C1 H1A Cl3 0.97 2.83 3.654(14) 142.9 1_655
N1 H1C Cl6 0.89 2.94 3.680(13) 141.5 2_666
N1 H1D Cl2 0.89 2.88 3.301(9) 110.5 2_666
N1 H1D Cl6 0.89 2.84 3.444(9) 126.1 .
N1 H1E Cl1 0.89 2.52 3.378(10) 161.2 2_666
C6 H6A Cl6 0.97 2.98 3.637(7) 125.7 .
C6 H6A Cl8 0.97 2.94 3.707(7) 136.5 2_666
C5 H5A Cl5 0.97 2.83 3.466(6) 124.2 .
C5 H5A Cl6 0.97 3.00 3.685(6) 128.9 .
C5 H5B Cl4 0.97 2.94 3.677(6) 134.0 2_665
N3 H3A Cl1 0.89 2.93 3.363(5) 112.0 2_565
N3 H3A Cl5 0.89 2.80 3.367(6) 122.7 .
N3 H3A Cl5 0.89 2.84 3.561(5) 139.5 2_565
N3 H3B Cl6 0.89 2.41 3.284(5) 166.0 2_665
N3 H3C Cl3 0.89 2.60 3.380(5) 146.6 2_565
C4 H4B Cl2 0.97 3.00 3.711(8) 131.3 .
C4 H4B Cl7 0.97 2.99 3.677(9) 128.6 1_455
C3 H3D Cl7 0.97 2.89 3.543(8) 125.8 1_455
C3 H3D Cl9 0.97 2.77 3.605(8) 145.2 2_566
N2 H2C Cl3 0.89 2.68 3.281(6) 126.0 2_556
N2 H2D Cl4 0.89 2.33 3.204(6) 167.7 2_556
N2 H2E Cl5 0.89 2.35 3.218(6) 164.3 1_556
C1 H1A Cl3 0.97 2.83 3.654(14) 142.9 1_655
N1 H1C Cl6 0.89 2.94 3.680(13) 141.5 2_666
N1 H1D Cl2 0.89 2.88 3.301(9) 110.5 2_666
N1 H1D Cl6 0.89 2.84 3.444(9) 126.1 .
N1 H1E Cl1 0.89 2.52 3.378(10) 161.2 2_666
C6 H6A Cl6 0.97 2.98 3.637(7) 125.7 .
C6 H6A Cl8 0.97 2.94 3.707(7) 136.5 2_666
C5 H5A Cl5 0.97 2.83 3.466(6) 124.2 .
C5 H5B Cl4 0.97 2.94 3.677(6) 134.0 2_665
N3 H3A Cl1 0.89 2.93 3.363(5) 112.0 2_565
N3 H3A Cl5 0.89 2.80 3.367(6) 122.7 .
N3 H3A Cl5 0.89 2.84 3.561(5) 139.5 2_565
N3 H3B Cl6 0.89 2.41 3.284(5) 166.0 2_665
N3 H3C Cl3 0.89 2.60 3.380(5) 146.6 2_565
C3 H3D Cl7 0.97 2.89 3.543(8) 125.8 1_455
C3 H3D Cl9 0.97 2.77 3.605(8) 145.2 2_566
N2 H2C Cl3 0.89 2.68 3.281(6) 126.0 2_556
N2 H2D Cl4 0.89 2.33 3.204(6) 167.7 2_556
N2 H2E Cl5 0.89 2.35 3.218(6) 164.3 1_556
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
N1 C1 C2 Cl7 -35(2) . . . . ?
Cl9 C6 C5 N3 -64.9(6) . . . . ?
Cl8 C4 C3 N2 73.1(9) . . . . ?
