#------------------------------------------------------------------------------
#$Date: 2017-11-07 03:04:18 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/76/1547655.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_1547655
loop_
_publ_author_name
'Wang, Ya'
'Shi, Chao'
'Han, Xiang-Bin'
_publ_section_title
;
 Mixed Bromine--Chlorine Induced Great Dielectric and Second-Order
 Nonlinear Optical Properties Changes in Phase Transitions Compounds
 [H2mdap][BiBr5(1-x)Cl5x] (x = 0.00--1.00)
;
_journal_issue                   41
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              23039
_journal_paper_doi               10.1021/acs.jpcc.7b05126
_journal_volume                  121
_journal_year                    2017
_chemical_formula_sum            'C4 H14 Bi Br1.8 Cl3.2 N2'
_chemical_formula_weight         556.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.109(4)
_cell_length_b                   9.998(2)
_cell_length_c                   7.5855(15)
_cell_measurement_reflns_used    3151
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      3.035
_cell_volume                     1373.4(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0830
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9085
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.035
_exptl_absorpt_coefficient_mu    18.658
_exptl_absorpt_correction_T_max  0.005
_exptl_absorpt_correction_T_min  0.002
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    2.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1009.6
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         2.651
_refine_diff_density_min         -2.525
_refine_diff_density_rms         0.293
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       0.0051(6)
_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   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     125
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0603
_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)+(0.0703P)²+4.0194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2439
_reflns_number_total             3151
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp7b05126_si_002.cif
_cod_data_source_block           0.64_293K
_cod_depositor_comments
'Adding full bibliography for 1547653--1547662.cif.'
_cod_original_formula_sum        'C4 H14 Bi Br1.80 Cl3.20 N2 '
_cod_database_code               1547655
_publcif_datablock.id            {c5fadad5-3faf-412a-a2b2-021904282042}
_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'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 0.43535(4) 0.17082(7) 0.27723(6) 0.0270(3) Uani 1 1 d . U .
Cl1 Cl 0.30082(16) 0.0340(3) 0.2706(8) 0.0288(7) Uani 0.64 1 d . U P
Br1 Br 0.30082(16) 0.0340(3) 0.2706(8) 0.0288(7) Uani 0.36 1 d . U P
Cl2 Cl 0.3736(3) 0.3460(4) 0.0600(6) 0.0410(10) Uani 0.64 1 d . U P
Br2 Br 0.3736(3) 0.3460(4) 0.0600(6) 0.0410(10) Uani 0.36 1 d . U P
Cl3 Cl 0.3926(3) 0.3035(4) 0.5675(7) 0.0434(11) Uani 0.64 1 d . U P
Br3 Br 0.3926(3) 0.3035(4) 0.5675(7) 0.0434(11) Uani 0.36 1 d . U P
Cl4 Cl 0.5597(2) 0.3378(4) 0.2675(14) 0.0434(10) Uani 0.64 1 d . U P
Br4 Br 0.5597(2) 0.3378(4) 0.2675(14) 0.0434(10) Uani 0.36 1 d . U P
Cl5 Cl 0.5149(2) -0.0425(5) 0.4635(7) 0.0500(12) Uani 0.64 1 d . U P
Br5 Br 0.5149(2) -0.0425(5) 0.4635(7) 0.0500(12) Uani 0.36 1 d . U P
C3 C 0.2415(15) 0.157(3) 0.741(5) 0.055(8) Uani 1 1 d D U .
H3A H 0.2523 0.2523 0.7365 0.067 Uiso 1 1 calc R U .
H3B H 0.2326 0.1256 0.6222 0.067 Uiso 1 1 calc R U .
N1 N 0.0354(13) 0.126(2) 0.837(3) 0.046(6) Uani 1 1 d D U .
H1A H 0.0392 0.0371 0.8382 0.069 Uiso 1 1 calc R U .
H1B H -0.0037 0.1495 0.7729 0.069 Uiso 1 1 calc R U .
H1C H 0.0300 0.1558 0.9466 0.069 Uiso 1 1 calc R U .
C1 C 0.1034(14) 0.185(3) 0.758(5) 0.048(7) Uani 1 1 d D U .
H1D H 0.1011 0.2813 0.7670 0.057 Uiso 1 1 calc R U .
H1E H 0.1055 0.1615 0.6338 0.057 Uiso 1 1 calc R U .
N2 N 0.3040(11) 0.083(2) 0.822(3) 0.042(6) Uani 1 1 d D U .
H2A H 0.2998 0.0868 0.9390 0.051 Uiso 1 1 calc R U .
H2B H 0.3462 0.1230 0.7927 0.051 Uiso 1 1 calc R U .
C2 C 0.1764(15) 0.132(3) 0.854(4) 0.052(7) Uani 1 1 d D U .
H2C H 0.1824 0.1778 0.9655 0.062 Uiso 1 1 calc R U .
H2D H 0.1720 0.0371 0.8766 0.062 Uiso 1 1 calc R U .
C4 C 0.3067(13) -0.061(3) 0.765(6) 0.059(8) Uani 1 1 d D U .
H4A H 0.3546 -0.0972 0.7903 0.088 Uiso 1 1 calc R U .
H4B H 0.2973 -0.0667 0.6408 0.088 Uiso 1 1 calc R U .
H4C H 0.2698 -0.1110 0.8279 0.088 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'
Br Br -0.2901 2.4595 '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
Cl2 Bi1 Cl3 93.54(16) . .
Cl2 Bi1 Cl1 86.83(14) . .
Cl3 Bi1 Cl1 90.30(15) . .
Cl2 Bi1 Cl4 85.93(17) . .
Cl3 Bi1 Cl4 87.6(2) . .
Cl1 Bi1 Cl4 172.33(12) . .
Cl2 Bi1 Br5 84.95(15) . 2_654
Cl3 Bi1 Br5 176.90(14) . 2_654
Cl1 Bi1 Br5 92.32(15) . 2_654
Cl4 Bi1 Br5 89.5(2) . 2_654
Cl2 Bi1 Cl5 84.95(15) . 2_654
Cl3 Bi1 Cl5 176.90(14) . 2_654
Cl1 Bi1 Cl5 92.32(15) . 2_654
Cl4 Bi1 Cl5 89.5(2) . 2_654
Br5 Bi1 Cl5 0.0 2_654 2_654
Cl2 Bi1 Cl5 170.29(15) . .
Cl3 Bi1 Cl5 96.06(15) . .
Cl1 Bi1 Cl5 94.62(13) . .
Cl4 Bi1 Cl5 92.95(16) . .
Br5 Bi1 Cl5 85.4 2_654 .
Cl5 Bi1 Cl5 85.40(5) 2_654 .
Bi1 Cl5 Bi1 152.1(2) 2_655 .
C2 C3 N2 107(2) . .
C2 C3 H3A 110.4 . .
N2 C3 H3A 110.4 . .
C2 C3 H3B 110.4 . .
N2 C3 H3B 110.4 . .
H3A C3 H3B 108.6 . .
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 . .
N1 C1 C2 112(2) . .
N1 C1 H1D 109.2 . .
C2 C1 H1D 109.2 . .
N1 C1 H1E 109.2 . .
C2 C1 H1E 109.2 . .
H1D C1 H1E 107.9 . .
C3 N2 C4 113(2) . .
C3 N2 H2A 109.1 . .
C4 N2 H2A 109.1 . .
C3 N2 H2B 109.1 . .
C4 N2 H2B 109.1 . .
H2A N2 H2B 107.8 . .
C3 C2 C1 110(2) . .
C3 C2 H2C 109.6 . .
C1 C2 H2C 109.6 . .
C3 C2 H2D 109.6 . .
C1 C2 H2D 109.6 . .
H2C C2 H2D 108.2 . .
N2 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
N2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 Cl2 2.653(4) .
Bi1 Cl3 2.684(5) .
Bi1 Cl1 2.795(3) .
Bi1 Cl4 2.803(4) .
Bi1 Br5 2.850(5) 2_654
Bi1 Cl5 2.850(5) 2_654
Bi1 Cl5 2.936(4) .
Cl5 Bi1 2.850(5) 2_655
C3 C2 1.48(4) .
C3 N2 1.49(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
N1 C1 1.49(3) .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
N1 H1C 0.8900 .
C1 C2 1.60(4) .
C1 H1D 0.9700 .
C1 H1E 0.9700 .
N2 C4 1.51(3) .
N2 H2A 0.8900 .
N2 H2B 0.8900 .
C2 H2C 0.9700 .
C2 H2D 0.9700 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
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
C4 H4B Cl1 0.96 2.98 3.87(5) 154.3 .
C4 H4A Br5 0.96 3.04 3.71(3) 128.0 2_655
C4 H4A Cl4 0.96 2.87 3.68(3) 142.6 2_655
C2 H2D Cl3 0.97 2.99 3.87(3) 152.4 3_545
N2 H2B Cl5 0.89 2.94 3.48(2) 120.1 2_655
N2 H2B Cl3 0.89 2.62 3.34(2) 138.3 .
N2 H2A Cl1 0.89 2.57 3.44(2) 164.9 1_556
C1 H1E Cl4 0.97 2.90 3.81(4) 156.6 4_455
C1 H1D Br5 0.97 3.12 3.80(3) 128.7 3
C1 H1D Br1 0.97 3.09 3.90(3) 142.3 3
N1 H1C Br5 0.89 3.13 3.57(2) 113.0 3
N1 H1C Cl4 0.89 2.49 3.32(3) 153.9 4_456
N1 H1C Cl2 0.89 2.96 3.40(3) 112.0 4_456
N1 H1B Cl3 0.89 2.48 3.37(2) 173.2 4_455
N1 H1A Cl4 0.89 2.73 3.40(2) 132.4 3_545
C3 H3A Cl3 0.97 2.89 3.37(3) 111.5 .
C3 H3A Cl1 0.97 2.99 3.85(3) 148.7 3
C3 H3B Br1 0.97 3.08 3.93(3) 146.8 .
C4 H4B Br1 0.96 2.98 3.87(5) 154.3 .
C4 H4A Br5 0.96 3.04 3.71(3) 128.0 2_655
C4 H4A Cl4 0.96 2.87 3.68(3) 142.6 2_655
C2 H2D Cl3 0.97 2.99 3.87(3) 152.4 3_545
C2 H2D Br2 0.97 3.18 3.74(3) 118.3 3_545
N2 H2A Cl1 0.89 2.57 3.44(2) 164.9 1_556
N2 H2B Cl5 0.89 2.94 3.48(2) 120.1 2_655
N2 H2B Cl3 0.89 2.62 3.34(2) 138.3 .
C1 H1E Cl4 0.97 2.90 3.81(4) 156.6 4_455
C1 H1D Br5 0.97 3.12 3.80(3) 128.7 3
C1 H1D Br1 0.97 3.09 3.90(3) 142.3 3
N1 H1C Cl4 0.89 2.49 3.32(3) 153.9 4_456
N1 H1C Cl2 0.89 2.96 3.40(3) 112.0 4_456
N1 H1B Cl3 0.89 2.48 3.37(2) 173.2 4_455
N1 H1A Cl4 0.89 2.73 3.40(2) 132.4 3_545
C3 H3B Br1 0.97 3.08 3.93(3) 146.8 .
C3 H3A Cl3 0.97 2.89 3.37(3) 111.5 .
C3 H3A Br1 0.97 2.99 3.85(3) 148.7 3
C4 H4B Br1 0.96 2.98 3.87(5) 154.3 .
C4 H4A Br5 0.96 3.04 3.71(3) 128.0 2_655
C4 H4A Cl4 0.96 2.87 3.68(3) 142.6 2_655
C2 H2D Cl3 0.97 2.99 3.87(3) 152.4 3_545
C2 H2D Br2 0.97 3.18 3.74(3) 118.3 3_545
N2 H2A Cl1 0.89 2.57 3.44(2) 164.9 1_556
N2 H2B Cl5 0.89 2.94 3.48(2) 120.1 2_655
N2 H2B Cl3 0.89 2.62 3.34(2) 138.3 .
C1 H1E Cl4 0.97 2.90 3.81(4) 156.6 4_455
C1 H1D Br5 0.97 3.12 3.80(3) 128.7 3
C1 H1D Br1 0.97 3.09 3.90(3) 142.3 3
N1 H1C Cl4 0.89 2.49 3.32(3) 153.9 4_456
N1 H1C Cl2 0.89 2.96 3.40(3) 112.0 4_456
N1 H1B Cl3 0.89 2.48 3.37(2) 173.2 4_455
N1 H1A Cl4 0.89 2.73 3.40(2) 132.4 3_545
C3 H3A Cl3 0.97 2.89 3.37(3) 111.5 .
C3 H3A Br1 0.97 2.99 3.85(3) 148.7 3
C3 H3B Br1 0.97 3.08 3.93(3) 146.8 .
C3 H3A Br1 0.97 2.99 3.85(3) 148.7 3
C3 H3A Cl3 0.97 2.89 3.37(3) 111.5 .
C3 H3B Br1 0.97 3.08 3.93(3) 146.8 .
N1 H1A Br3 0.89 3.16 3.89(2) 140.6 3_545
N1 H1A Cl4 0.89 2.73 3.40(2) 132.4 3_545
N1 H1B Cl3 0.89 2.48 3.37(2) 173.2 4_455
N1 H1C Cl2 0.89 2.96 3.40(3) 112.0 4_456
N1 H1C Cl4 0.89 2.49 3.32(3) 153.9 4_456
N1 H1C Br5 0.89 3.13 3.57(2) 113.0 3
C1 H1D Br1 0.97 3.09 3.90(3) 142.3 3
C1 H1D Br5 0.97 3.12 3.80(3) 128.7 3
C1 H1E Cl4 0.97 2.90 3.81(4) 156.6 4_455
N2 H2A Cl1 0.89 2.57 3.44(2) 164.9 1_556
N2 H2B Br2 0.89 3.05 3.43(2) 107.4 1_556
N2 H2B Cl3 0.89 2.62 3.34(2) 138.3 .
N2 H2B Cl5 0.89 2.94 3.48(2) 120.1 2_655
C2 H2D Cl3 0.97 2.99 3.87(3) 152.4 3_545
C4 H4A Br4 0.96 2.87 3.68(3) 142.6 2_655
C4 H4A Br5 0.96 3.04 3.71(3) 128.0 2_655
C4 H4B Br1 0.96 2.98 3.87(5) 154.3 .
C4 H4B Br2 0.96 3.27 3.73(3) 111.5 3_545
C3 H3A Br1 0.97 2.99 3.85(3) 148.7 3
C3 H3A Cl3 0.97 2.89 3.37(3) 111.5 .
C3 H3B Br1 0.97 3.08 3.93(3) 146.8 .
N1 H1A Cl4 0.89 2.73 3.40(2) 132.4 3_545
N1 H1B Cl3 0.89 2.48 3.37(2) 173.2 4_455
N1 H1C Cl2 0.89 2.96 3.40(3) 112.0 4_456
N1 H1C Cl4 0.89 2.49 3.32(3) 153.9 4_456
C1 H1D Br1 0.97 3.09 3.90(3) 142.3 3
C1 H1D Br5 0.97 3.12 3.80(3) 128.7 3
C1 H1E Cl4 0.97 2.90 3.81(4) 156.6 4_455
N2 H2B Cl3 0.89 2.62 3.34(2) 138.3 .
N2 H2B Cl5 0.89 2.94 3.48(2) 120.1 2_655
N2 H2A Cl1 0.89 2.57 3.44(2) 164.9 1_556
C2 H2D Br2 0.97 3.18 3.74(3) 118.3 3_545
C2 H2D Cl3 0.97 2.99 3.87(3) 152.4 3_545
C4 H4A Cl4 0.96 2.87 3.68(3) 142.6 2_655
C4 H4A Br5 0.96 3.04 3.71(3) 128.0 2_655
C4 H4B Br1 0.96 2.98 3.87(5) 154.3 .
C3 H3A Cl1 0.97 2.99 3.85(3) 148.7 3
C3 H3A Cl3 0.97 2.89 3.37(3) 111.5 .
C3 H3B Br1 0.97 3.08 3.93(3) 146.8 .
N1 H1A Cl4 0.89 2.73 3.40(2) 132.4 3_545
N1 H1B Cl3 0.89 2.48 3.37(2) 173.2 4_455
N1 H1C Cl2 0.89 2.96 3.40(3) 112.0 4_456
N1 H1C Cl4 0.89 2.49 3.32(3) 153.9 4_456
N1 H1C Br5 0.89 3.13 3.57(2) 113.0 3
C1 H1D Br1 0.97 3.09 3.90(3) 142.3 3
C1 H1D Br5 0.97 3.12 3.80(3) 128.7 3
C1 H1E Cl4 0.97 2.90 3.81(4) 156.6 4_455
N2 H2B Cl3 0.89 2.62 3.34(2) 138.3 .
N2 H2B Cl5 0.89 2.94 3.48(2) 120.1 2_655
N2 H2A Cl1 0.89 2.57 3.44(2) 164.9 1_556
C2 H2D Br3 0.97 2.99 3.87(3) 152.4 3_545
C4 H4A Cl4 0.96 2.87 3.68(3) 142.6 2_655
C4 H4A Br5 0.96 3.04 3.71(3) 128.0 2_655
C4 H4B Cl1 0.96 2.98 3.87(5) 154.3 .
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
C2 C3 N2 C4 85(3)
N2 C3 C2 C1 -169(2)
N1 C1 C2 C3 162(2)
