#------------------------------------------------------------------------------
#$Date: 2019-11-24 11:34:57 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/76/7237621.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_7237621
loop_
_publ_author_name
'Szklarz, Przemysław'
'Gągor, Anna'
'Jakubas, Ryszard'
'Zieliński, Piotr'
'Piecha-Bisiorek, Anna'
'Cichos, Jakub'
'Karbowiak, Mirosław'
'Bator, Grażyna'
'Ciżman, Agnieszka'
_publ_section_title
;
 Lead-free hybrid ferroelectric material based on formamidine:
 [NH2CHNH2]3Bi2I9
;
_journal_issue                   10
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3003
_journal_paper_doi               10.1039/C8TC06458J
_journal_volume                  7
_journal_year                    2019
_chemical_formula_sum            'C3 H15 Bi2 I9 N6'
_chemical_formula_weight         1695.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-14 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6920(2)
_cell_length_b                   15.0550(2)
_cell_length_c                   21.9675(6)
_cell_measurement_reflns_used    5047
_cell_measurement_temperature    189.9(2)
_cell_measurement_theta_max      25.6400
_cell_measurement_theta_min      2.8950
_cell_volume                     2874.62(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      189.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12711
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         29.343
_diffrn_reflns_theta_min         2.782
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    21.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    3.917
_exptl_crystal_description       prism
_exptl_crystal_F_000             2872
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.189
_refine_diff_density_min         -2.722
_refine_diff_density_rms         0.346
_refine_ls_abs_structure_details
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0631
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1200P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.2060
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                3157
_reflns_number_total             3803
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc06458j2.cif
_cod_data_source_block           cmc21
_cod_database_code               7237621
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.630
_oxdiff_exptl_absorpt_empirical_full_max 1.674
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, 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 0.5000 0.15715(16) 0.13913(17) 0.0445(5) Uani 1 2 d S T P
Bi2 Bi 0.5000 0.17589(17) 0.32837(17) 0.0464(5) Uani 1 2 d S T P
I1 I 0.7477(5) 0.0662(4) 0.0693(2) 0.0937(15) Uani 1 1 d . . .
I2 I 0.5000 0.3128(4) 0.0610(3) 0.0679(13) Uani 1 2 d S T P
I3 I 0.5000 0.0013(4) 0.2414(3) 0.0595(12) Uani 1 2 d S T P
I4 I 0.2512(3) 0.2480(3) 0.2295(2) 0.0668(11) Uani 1 1 d . . .
I5 I 0.2518(4) 0.1030(4) 0.4039(2) 0.0814(12) Uani 1 1 d . . .
I6 I 0.5000 0.3486(5) 0.3934(3) 0.099(2) Uani 1 2 d S T P
C11 C 0.0000 -0.024(5) 0.276(2) 0.081(17) Uiso 0.5 2 d DS . P
H11 H 0.0153 -0.0717 0.3021 0.098 Uiso 0.25 1 calc R U P
C12 C 0.0000 0.050(4) 0.220(3) 0.081(17) Uiso 0.5 2 d DS . P
H12 H -0.0154 0.0844 0.1855 0.098 Uiso 0.25 1 calc R U P
N12 N 0.023(10) -0.035(4) 0.218(2) 0.081(17) Uiso 0.5 1 d D . P
H12A H 0.0368 -0.0646 0.2508 0.098 Uiso 0.5 1 calc R U P
H12B H 0.0242 -0.0616 0.1832 0.098 Uiso 0.5 1 calc R U P
N21 N 0.0000 0.058(6) 0.295(3) 0.081(17) Uiso 0.5 2 d DS . P
H21A H -0.0145 0.1004 0.2691 0.098 Uiso 0.25 1 calc R U P
H21B H 0.0145 0.0694 0.3325 0.098 Uiso 0.25 1 calc R U P
N22 N 0.0000 0.085(5) 0.274(4) 0.081(17) Uiso 0.5 2 d DS . P
H22A H 0.0146 0.0515 0.3058 0.098 Uiso 0.25 1 calc R U P
H22B H -0.0146 0.1409 0.2791 0.098 Uiso 0.25 1 calc R U P
C2 C 0.5000 0.108(8) -0.061(5) 0.17(3) Uiso 1 2 d DS . P
H2 H 0.5000 0.0645 -0.0309 0.210 Uiso 1 2 calc R U P
C3 C 0.5000 -0.167(5) 0.068(3) 0.14(2) Uiso 1 2 d DS . P
H3 H 0.5000 -0.1486 0.0277 0.166 Uiso 1 2 calc R U P
N4 N 0.5000 -0.108(5) 0.111(4) 0.14(2) Uiso 1 2 d DS . P
H4A H 0.5000 -0.1247 0.1489 0.166 Uiso 1 2 calc R U P
H4B H 0.5000 -0.0522 0.1027 0.166 Uiso 1 2 calc R U P
N3 N 0.6294(8) 0.139(6) -0.082(3) 0.17(3) Uiso 1 1 d D . .
H3A H 0.6293 0.1790 -0.1096 0.210 Uiso 1 1 calc R U .
H3B H 0.7151 0.1185 -0.0681 0.210 Uiso 1 1 calc R U .
N5 N 0.5000 -0.251(5) 0.081(4) 0.14(2) Uiso 1 2 d DS . P
H5A H 0.5000 -0.2675 0.1189 0.166 Uiso 1 2 calc R U P
H5B H 0.5000 -0.2897 0.0528 0.166 Uiso 1 2 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
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 '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
I2 Bi1 I1 93.83(12) . 4_655
I2 Bi1 I1 93.83(12) . .
I1 Bi1 I1 92.7(2) 4_655 .
I2 Bi1 I4 91.23(13) . .
I1 Bi1 I4 91.56(14) 4_655 .
I1 Bi1 I4 173.18(12) . .
I2 Bi1 I4 91.23(13) . 4_655
I1 Bi1 I4 173.18(12) 4_655 4_655
I1 Bi1 I4 91.56(14) . 4_655
I4 Bi1 I4 83.75(16) . 4_655
I2 Bi1 I3 172.45(17) . .
I1 Bi1 I3 91.38(12) 4_655 .
I1 Bi1 I3 91.38(12) . .
I4 Bi1 I3 83.17(11) . .
I4 Bi1 I3 83.17(11) 4_655 .
I5 Bi2 I5 94.66(19) . 4_655
I5 Bi2 I6 93.18(14) . .
I5 Bi2 I6 93.18(14) 4_655 .
I5 Bi2 I3 91.72(13) . .
I5 Bi2 I3 91.72(13) 4_655 .
I6 Bi2 I3 172.77(17) . .
I5 Bi2 I4 172.53(12) . 4_655
I5 Bi2 I4 90.77(11) 4_655 4_655
I6 Bi2 I4 91.64(14) . 4_655
I3 Bi2 I4 82.97(12) . 4_655
I5 Bi2 I4 90.77(11) . .
I5 Bi2 I4 172.53(12) 4_655 .
I6 Bi2 I4 91.65(14) . .
I3 Bi2 I4 82.97(12) . .
I4 Bi2 I4 83.38(13) 4_655 .
Bi2 I3 Bi1 79.78(14) . .
Bi1 I4 Bi2 79.88(6) . .
N21 C11 N12 115.4(9) . 4
N21 C11 H11 122.5 . .
N12 C11 H11 122.1 4 .
N12 C12 N22 115.6(9) . .
N12 C12 H12 122.2 . .
N22 C12 H12 122.2 . .
C12 N12 H12A 120.0 . .
C12 N12 H12B 120.0 . .
H12A N12 H12B 120.0 . .
C11 N21 H21A 120.2 . .
C11 N21 H21B 119.8 . .
H21A N21 H21B 120.0 . .
C12 N22 H22A 120.0 . .
C12 N22 H22B 120.0 . .
H22A N22 H22B 120.0 . .
N3 C2 N3 119.9(16) . 4_655
N3 C2 H2 120.1 . .
N3 C2 H2 120.1 4_655 .
N5 C3 N4 120.0(14) . .
N5 C3 H3 120.0 . .
N4 C3 H3 120.0 . .
C3 N4 H4A 120.0 . .
C3 N4 H4B 120.0 . .
H4A N4 H4B 120.0 . .
C2 N3 H3A 120.0 . .
C2 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
C3 N5 H5A 120.0 . .
C3 N5 H5B 120.0 . .
H5A N5 H5B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 I2 2.904(6) .
Bi1 I1 2.977(3) 4_655
Bi1 I1 2.977(3) .
Bi1 I4 3.239(3) .
Bi1 I4 3.239(3) 4_655
Bi1 I3 3.248(5) .
Bi2 I5 2.934(3) .
Bi2 I5 2.934(3) 4_655
Bi2 I6 2.967(7) .
Bi2 I3 3.249(6) .
Bi2 I4 3.251(3) 4_655
Bi2 I4 3.251(3) .
C11 N21 1.300(7) .
C11 N12 1.301(7) 4
C11 H11 0.9300 .
C12 N12 1.300(7) .
C12 N22 1.300(7) .
C12 H12 0.9300 .
N12 H12A 0.8600 .
N12 H12B 0.8600 .
N21 H21A 0.8600 .
N21 H21B 0.8600 .
N22 H22A 0.8600 .
N22 H22B 0.8600 .
C2 N3 1.299(7) .
C2 N3 1.299(7) 4_655
C2 H2 0.9300 .
C3 N5 1.299(7) .
C3 N4 1.299(7) .
C3 H3 0.9300 .
N4 H4A 0.8600 .
N4 H4B 0.8600 .
N3 H3A 0.8600 .
N3 H3B 0.8600 .
N5 H5A 0.8600 .
N5 H5B 0.8600 .
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
N21 H21A I4 0.86 3.15 3.88(9) 143.4 4
N4 H4B I1 0.86 2.89 3.52(6) 131.1 .
N4 H4B I1 0.86 2.89 3.52(6) 131.1 4_655
N3 H3B I6 0.86 2.66 3.272(14) 128.9 6_654
