#------------------------------------------------------------------------------
#$Date: 2025-01-24 05:09:53 +0200 (Fri, 24 Jan 2025) $
#$Revision: 297453 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/33/2023361.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023361
loop_
_publ_author_name
'Kucheriv, Olesia I.'
'Ovdenko, Valeriia M.'
'Kuzevanova, Iryna S.'
'Golenya, Irina A.'
'Gural'skiy, Il'ya A.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of the
 organic--inorganic hybrid compound tris(2-iodoethylammonium)
 hexaiodidobismuthate(III)
;
_journal_coeditor_code           WM5745
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025000386
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          '(C2 H7 I N)3, [Bi I6]'
_chemical_formula_moiety         '3(C2 H7 I N +), Bi I6 3-'
_chemical_formula_sum            'C6 H21 Bi I9 N3'
_chemical_formula_weight         1486.34
_chemical_name_systematic
;
Tris(2-iodoethylammonium) hexaiodidobismuthate(III)
;
_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
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                107.689(2)
_cell_angle_beta                 107.067(2)
_cell_angle_gamma                92.749(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5014(2)
_cell_length_b                   12.8233(3)
_cell_length_c                   13.6364(3)
_cell_measurement_reflns_used    12539
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.2300
_cell_measurement_theta_min      2.5210
_cell_volume                     1338.49(6)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.820
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19499
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.422
_diffrn_reflns_theta_min         2.535
_exptl_absorpt_coefficient_mu    16.961
_exptl_absorpt_correction_T_max  0.506
_exptl_absorpt_correction_T_min  0.137
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_density_diffrn    3.688
_exptl_crystal_description       prism
_exptl_crystal_F_000             1276
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.384
_refine_diff_density_min         -1.944
_refine_ls_extinction_coef       0.00014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         6651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0247
_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)+(0.0173P)²+0.4063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0491
_reflns_number_gt                5947
_reflns_number_total             6651
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5745.cif
_cod_data_source_block           I
_cod_database_code               2023361
_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.
;
_shelx_estimated_absorpt_t_min   0.141
_shelx_estimated_absorpt_t_max   0.484
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi Bi1 0.16816(2) 0.69742(2) 0.33843(2) 0.01111(5) Uani d 1 . .
I I5 0.33222(3) 0.60094(2) 0.15861(2) 0.01361(7) Uani d 1 . .
I I4 -0.16844(3) 0.62750(2) 0.15397(2) 0.01349(7) Uani d 1 . .
I I1 0.11528(3) 0.46673(2) 0.36362(2) 0.01363(7) Uani d 1 . .
I I3 0.19810(4) 0.92705(2) 0.31390(2) 0.01440(7) Uani d 1 . .
I I2 0.51762(3) 0.76130(2) 0.50855(2) 0.01362(7) Uani d 1 . .
I I6 0.01073(3) 0.79056(3) 0.51288(2) 0.01571(7) Uani d 1 . .
I I8 0.58571(4) 0.31642(3) 0.11272(3) 0.01952(8) Uani d 1 . .
I I7 0.17041(4) 0.14625(3) 0.15984(3) 0.02642(9) Uani d 1 . .
I I9 0.66397(5) 1.02469(3) 0.16011(3) 0.03205(9) Uani d 1 . .
N N2 0.6922(4) 0.5384(3) 0.3540(3) 0.0149(8) Uani d 1 . .
H H2A 0.663(3) 0.5957(17) 0.390(2) 0.018 Uiso calc 1 . .
H H2B 0.684(3) 0.5409(14) 0.2918(18) 0.018 Uiso calc 1 . .
H H2C 0.791(3) 0.5349(12) 0.386(2) 0.018 Uiso calc 1 . .
N N3 0.6590(5) 0.9734(4) 0.3921(3) 0.0219(10) Uani d 1 . .
H H3C 0.556(3) 0.9749(17) 0.3818(15) 0.026 Uiso calc 1 . .
H H3D 0.704(4) 1.034(2) 0.3922(16) 0.026 Uiso calc 1 . .
H H3E 0.704(4) 0.9647(14) 0.453(2) 0.026 Uiso calc 1 . .
N N1 0.0028(5) 0.3580(3) 0.0687(3) 0.0183(9) Uani d 1 . .
H H1A 0.031(4) 0.3599(4) 0.141(2) 0.022 Uiso calc 1 . .
H H1B -0.086(3) 0.3978(13) 0.0535(17) 0.022 Uiso calc 1 . .
H H1C 0.095(3) 0.3901(12) 0.0579(18) 0.022 Uiso calc 1 . .
C C5 0.6821(6) 0.8794(4) 0.3028(4) 0.0204(11) Uani d 1 . .
H H5A 0.801517 0.884170 0.309359 0.025 Uiso calc 1 . .
H H5B 0.647553 0.808515 0.310931 0.025 Uiso calc 1 . .
C C4 0.6282(6) 0.3321(4) 0.2813(4) 0.0180(10) Uani d 1 . .
H H4A 0.562064 0.268387 0.284755 0.022 Uiso calc 1 . .
H H4B 0.747215 0.329848 0.316224 0.022 Uiso calc 1 . .
C C1 -0.0476(6) 0.2402(4) -0.0057(4) 0.0177(10) Uani d 1 . .
H H1D -0.089761 0.239060 -0.081909 0.021 Uiso calc 1 . .
H H1E -0.139406 0.205092 0.009941 0.021 Uiso calc 1 . .
C C3 0.5814(5) 0.4380(4) 0.3433(4) 0.0167(10) Uani d 1 . .
H H3A 0.464643 0.442694 0.305470 0.020 Uiso calc 1 . .
H H3B 0.588874 0.436813 0.416807 0.020 Uiso calc 1 . .
C C2 0.0940(6) 0.1740(4) 0.0064(4) 0.0207(11) Uani d 1 . .
H H2D 0.190098 0.213498 -0.001433 0.025 Uiso calc 1 . .
H H2E 0.059806 0.101576 -0.052859 0.025 Uiso calc 1 . .
C C6 0.5834(6) 0.8803(4) 0.1924(4) 0.0244(12) Uani d 1 . .
H H6A 0.464389 0.877912 0.186693 0.029 Uiso calc 1 . .
H H6B 0.594239 0.813096 0.136611 0.029 Uiso calc 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'
N N 0.0061 0.0033 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -18 5 0.0435
-3 18 -5 0.0486
-10 0 -3 0.0813
7 13 -1 0.0614
5 -17 6 0.0577
9 -10 5 0.0758
0 -3 18 0.0275
-11 -4 10 0.0907
-8 0 -8 0.0692
2 4 -19 0.0236
10 5 -15 0.0695
1 -13 16 0.0350
0 13 -16 0.0352
-2 12 -16 0.0416
11 7 -3 0.0794
0 -6 -14 0.0259
0 6 14 0.0342
4 2 13 0.0458
0 2 17 0.0254
7 -10 -11 0.0619
0 0 -17 0.0259
0 -2 -17 0.0238
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
I4 Bi1 I5 . . 86.834(9) ?
I4 Bi1 I1 . . 87.370(9) ?
I1 Bi1 I5 . . 91.043(9) ?
I3 Bi1 I5 . . 91.561(9) ?
I3 Bi1 I4 . . 90.279(9) ?
I3 Bi1 I1 . . 176.391(9) ?
I3 Bi1 I2 . . 89.461(9) ?
I2 Bi1 I5 . . 88.607(9) ?
I2 Bi1 I4 . . 175.425(10) ?
I2 Bi1 I1 . . 93.101(9) ?
I6 Bi1 I5 . . 179.779(10) ?
I6 Bi1 I4 . . 93.367(9) ?
I6 Bi1 I1 . . 88.876(9) ?
I6 Bi1 I3 . . 88.529(9) ?
I6 Bi1 I2 . . 91.192(9) ?
H2A N2 H2B . . 109.5 ?
H2A N2 H2C . . 109.5 ?
H2B N2 H2C . . 109.5 ?
C3 N2 H2A . . 109.5 ?
C3 N2 H2B . . 109.5 ?
C3 N2 H2C . . 109.5 ?
H3C N3 H3D . . 109.5 ?
H3C N3 H3E . . 109.5 ?
H3D N3 H3E . . 109.5 ?
C5 N3 H3C . . 109.5 ?
C5 N3 H3D . . 109.5 ?
C5 N3 H3E . . 109.5 ?
H1A N1 H1B . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C1 N1 H1A . . 109.5 ?
C1 N1 H1B . . 109.5 ?
C1 N1 H1C . . 109.5 ?
N3 C5 H5A . . 109.2 ?
N3 C5 H5B . . 109.2 ?
H5A C5 H5B . . 107.9 ?
C6 C5 N3 . . 112.2(4) ?
C6 C5 H5A . . 109.2 ?
C6 C5 H5B . . 109.2 ?
I8 C4 H4A . . 109.2 ?
I8 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
C3 C4 I8 . . 112.2(3) ?
C3 C4 H4A . . 109.2 ?
C3 C4 H4B . . 109.2 ?
N1 C1 H1D . . 109.1 ?
N1 C1 H1E . . 109.1 ?
N1 C1 C2 . . 112.5(4) ?
H1D C1 H1E . . 107.8 ?
C2 C1 H1D . . 109.1 ?
C2 C1 H1E . . 109.1 ?
N2 C3 C4 . . 112.2(4) ?
N2 C3 H3A . . 109.2 ?
N2 C3 H3B . . 109.2 ?
C4 C3 H3A . . 109.2 ?
C4 C3 H3B . . 109.2 ?
H3A C3 H3B . . 107.9 ?
I7 C2 H2D . . 109.0 ?
I7 C2 H2E . . 109.0 ?
C1 C2 I7 . . 113.0(3) ?
C1 C2 H2D . . 109.0 ?
C1 C2 H2E . . 109.0 ?
H2D C2 H2E . . 107.8 ?
I9 C6 H6A . . 109.1 ?
I9 C6 H6B . . 109.1 ?
C5 C6 I9 . . 112.3(3) ?
C5 C6 H6A . . 109.1 ?
C5 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Bi1 I6 . 3.0287(3) y
Bi1 I3 . 3.0698(3) y
Bi1 I2 . 3.0733(3) y
Bi1 I4 . 3.0786(3) y
Bi1 I1 . 3.1068(4) y
Bi1 I5 . 3.1333(3) y
I8 C4 . 2.163(5) ?
I7 C2 . 2.145(5) ?
I9 C6 . 2.155(5) ?
N2 H2A . 0.84(2) ?
N2 H2B . 0.84(2) ?
N2 H2C . 0.84(2) ?
N2 C3 . 1.502(6) ?
N3 H3C . 0.85(3) ?
N3 H3D . 0.85(3) ?
N3 H3E . 0.85(3) ?
N3 C5 . 1.499(6) ?
N1 H1A . 0.94(3) ?
N1 H1B . 0.94(3) ?
N1 H1C . 0.94(3) ?
N1 C1 . 1.498(6) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C5 C6 . 1.496(7) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C4 C3 . 1.506(7) ?
C1 H1D . 0.9900 ?
C1 H1E . 0.9900 ?
C1 C2 . 1.505(6) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C2 H2D . 0.9900 ?
C2 H2E . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A I1 . 0.94 2.77 3.639(4) 153.6 yes
N1 H1B I5 2_565 0.94 3.04 3.735(4) 132.3 yes
N1 H1C I5 . 0.94 2.97 3.726(4) 137.9 yes
N1 H1C I4 2_565 0.94 3.08 3.751(4) 130.1 yes
N2 H2A I2 . 0.84 2.83 3.660(4) 169.5 yes
N2 H2B I4 1_655 0.84 2.98 3.716(4) 147.8 yes
N2 H2C I1 1_655 0.84 3.00 3.730(4) 146.3 yes
N3 H3C I3 . 0.85 2.89 3.712(4) 166.5 yes
N3 H3D I6 2_676 0.85 2.91 3.659(4) 148.0 yes
N3 H3E I3 2_676 0.85 2.90 3.614(4) 143.5 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
I8 C4 C3 N2 . . . . -66.2(4) ?
N3 C5 C6 I9 . . . . 64.1(5) ?
N1 C1 C2 I7 . . . . 68.6(5) ?
