#------------------------------------------------------------------------------
#$Date: 2019-11-24 12:54:40 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237952 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/35/00/4350032.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_4350032
loop_
_publ_author_name
'Yang, Tao'
'Teng, Bing'
'Han, Shiguo'
'Li, Maofan'
'Xu, Zhiyun'
'Li, Yaobin'
'Liu, Yi'
'Luo, Junhua'
'Sun, Zhihua'
_publ_section_title
;
 Structural phase transition and dielectric anisotropy properties of a
 lead-free organic--inorganic hybrid
;
_journal_issue                   7
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              1761
_journal_paper_doi               10.1039/C9QI00365G
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C9 H24 Bi Br6 N3'
_chemical_formula_weight         862.75
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-01-18 deposited with the CCDC.	2019-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.8660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.2211(5)
_cell_length_b                   8.3379(2)
_cell_length_c                   12.2913(3)
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.98
_cell_volume                     2210.94(9)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22778
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_min         2.221
_exptl_absorpt_coefficient_mu    18.811
_exptl_crystal_density_diffrn    2.592
_exptl_crystal_description       Flake
_exptl_crystal_F_000             1568
_refine_diff_density_max         1.515
_refine_diff_density_min         -1.876
_refine_diff_density_rms         0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0471
_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)+(0.0824P)²+7.9235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2085
_reflns_number_total             2717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9qi00365g2.cif
_cod_data_source_block           11
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               4350032
_shelx_shelxl_version_number     2018/3
_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
Bi1 Bi 0.33105(2) 0.500000 0.27715(3) 0.04595(18) Uani 1 2 d S T P
Br1 Br 0.24447(5) 0.25154(13) 0.21340(10) 0.0775(3) Uani 1 1 d . . .
Br3 Br 0.42659(5) 0.73941(13) 0.35770(11) 0.0781(3) Uani 1 1 d . . .
Br4 Br 0.35051(8) 0.500000 0.06171(12) 0.0857(5) Uani 1 2 d S T P
Br2 Br 0.30864(7) 0.500000 0.50050(13) 0.0962(7) Uani 1 2 d S T P
C4 C 0.0700(12) 0.000000 0.2533(13) 0.170(12) Uani 1 2 d DS T P
H4 H 0.106359 -0.068040 0.256945 0.204 Uiso 0.5 1 d R U P
C5 C 0.0649(12) 0.144(2) 0.180(2) 0.155(19) Uani 0.5 1 d D . P
H5A H 0.048653 0.246282 0.197291 0.186 Uiso 0.5 1 d R U P
H5B H 0.098753 0.152042 0.142391 0.186 Uiso 0.5 1 d R U P
N1 N 0.1947(9) 0.500000 -0.0437(17) 0.158(10) Uani 1 2 d DS T P
H1A H 0.206557 0.536204 -0.103500 0.238 Uiso 0.5 1 calc R U P
H1B H 0.208784 0.400579 -0.028361 0.238 Uiso 0.5 1 calc R U P
H1C H 0.210060 0.563217 0.014671 0.238 Uiso 0.5 1 calc R U P
C3 C 0.0891(14) 0.500000 0.017(2) 0.212(10) Uani 1 2 d DS TU P
H3A H 0.090849 0.401950 0.060479 0.255 Uiso 0.5 1 d R U P
H3B H 0.090849 0.598050 0.060509 0.255 Uiso 0.5 1 d R U P
C6 C 0.0263(15) 0.000000 0.141(2) 0.25(3) Uani 1 2 d DS T P
H6B H 0.036135 -0.069990 0.084229 0.305 Uiso 0.5 1 d R U P
H6A H -0.017625 0.013570 0.135689 0.305 Uiso 0.5 1 d R U P
C2 C 0.0588(10) 0.500000 -0.105(2) 0.217(10) Uani 1 2 d DS TU P
H2D H 0.036960 0.598070 -0.132958 0.260 Uiso 0.5 1 d R U P
H2E H 0.036960 0.401930 -0.132958 0.260 Uiso 0.5 1 d R U P
C1 C 0.1268(9) 0.500000 -0.067(3) 0.214(10) Uani 1 2 d DS TU P
H1 H 0.126822 0.382460 -0.066883 0.257 Uiso 0.5 1 d R U P
N2 N 0.0476(6) 0.000000 0.3589(10) 0.078(4) Uani 1 2 d DS T P
H2A H 0.041718 0.100559 0.378282 0.117 Uiso 0.5 1 calc R U P
H2B H 0.075748 -0.046852 0.413385 0.117 Uiso 0.5 1 calc R U P
H2C H 0.012032 -0.053707 0.347658 0.117 Uiso 0.5 1 calc R U P
C8 C 0.0793(6) 0.500000 0.3783(18) 0.097(6) Uani 1 2 d DS T P
H8A H 0.062802 0.579090 0.321042 0.117 Uiso 0.5 1 d R U P
H8B H 0.052182 0.472110 0.426552 0.117 Uiso 0.5 1 d R U P
C7 C 0.1476(7) 0.500000 0.4257(12) 0.175(17) Uani 1 2 d DS T P
H7 H 0.170120 0.579050 0.391725 0.210 Uiso 0.5 1 d R U P
C9 C 0.1185(9) 0.365(3) 0.353(2) 0.21(3) Uani 0.5 1 d D . P
H9B H 0.115579 0.260304 0.385832 0.248 Uiso 0.5 1 d R U P
H9A H 0.127029 0.362734 0.279162 0.248 Uiso 0.5 1 d R U P
N3 N 0.1689(6) 0.500000 0.5505(10) 0.081(4) Uani 1 2 d DS T P
H3D H 0.141490 0.447882 0.579566 0.122 Uiso 0.5 1 calc R U P
H3C H 0.172376 0.600615 0.575389 0.122 Uiso 0.5 1 calc R U P
H3E H 0.205566 0.451502 0.570901 0.122 Uiso 0.5 1 calc 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'
N N 0.0061 0.0033 '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'
Bi Bi -4.1077 10.2566 '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
Br4 Bi1 Br1 89.24(4) . .
Br4 Bi1 Br1 89.24(4) . 6_565
Br1 Bi1 Br1 95.08(5) . 6_565
Br4 Bi1 Br2 179.09(5) . .
Br1 Bi1 Br2 90.15(3) . .
Br1 Bi1 Br2 90.15(3) 6_565 .
Br4 Bi1 Br3 93.25(4) . 6_565
Br1 Bi1 Br3 89.09(4) . 6_565
Br1 Bi1 Br3 175.18(4) 6_565 6_565
Br2 Bi1 Br3 87.41(3) . 6_565
Br4 Bi1 Br3 93.25(4) . .
Br1 Bi1 Br3 175.18(4) . .
Br1 Bi1 Br3 89.09(4) 6_565 .
Br2 Bi1 Br3 87.41(3) . .
Br3 Bi1 Br3 86.65(5) 6_565 .
C6 C4 C5 59.9(5) . .
C6 C4 C5 59.9(5) . 6
C5 C4 C5 107(2) . 6
C6 C4 N2 122(2) . .
C5 C4 N2 122.3(16) . .
C5 C4 N2 122.3(16) 6 .
C6 C5 C4 59.9(5) . .
C1 C3 C2 59.3(5) . .
C5 C6 C5 108(2) . 6
C5 C6 C4 60.2(5) . .
C5 C6 C4 60.2(5) 6 .
C1 C2 C3 59.9(5) . .
N1 C1 C2 173(3) . .
N1 C1 C3 126(3) . .
C2 C1 C3 60.8(5) . .
C7 C8 C9 59.6(5) . .
C7 C8 C9 59.6(5) . 6_565
C9 C8 C9 97(2) . 6_565
C9 C7 C9 99(2) 6_565 .
C9 C7 C8 60.6(5) 6_565 .
C9 C7 C8 60.6(5) . .
C9 C7 N3 127.1(15) 6_565 .
C9 C7 N3 127.1(15) . .
C8 C7 N3 116.4(15) . .
C7 C9 C8 59.8(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 Br4 2.7835(15) .
Bi1 Br1 2.8080(10) .
Bi1 Br1 2.8080(10) 6_565
Bi1 Br2 2.9052(15) .
Bi1 Br3 2.9093(10) 6_565
Bi1 Br3 2.9093(10) .
C4 C6 1.489(10) .
C4 C5 1.493(10) .
C4 C5 1.493(10) 6
C4 N2 1.497(10) .
C5 C6 1.489(10) .
N1 C1 1.467(10) .
C3 C1 1.481(10) .
C3 C2 1.495(10) .
C2 C1 1.472(10) .
C8 C7 1.489(10) .
C8 C9 1.502(10) .
C8 C9 1.502(10) 6_565
C7 C9 1.486(10) 6_565
C7 C9 1.486(10) .
C7 N3 1.492(10) .
