#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238917.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_2238917
loop_
_publ_author_name
'Elfaleh, Nizar'
'Chouaib, Hassen'
'Kamoun, Slaheddine'
_publ_section_title
;
 Bis(3-azaniumylpropyl)azanium hexachloridobismuthate(III) monohydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m666
_journal_paper_doi               10.1107/S1600536813030900
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '(C6 H20 N3) [Bi Cl6], H2 O'
_chemical_formula_moiety         'C6 H20 N3 3+, Bi Cl6 3-, H2 O'
_chemical_formula_sum            'C6 H22 Bi Cl6 N3 O'
_chemical_formula_weight         573.95
_chemical_melting_point          430
_chemical_name_systematic
;
Bis(3-azaniumylpropyl)azanium hexachloridobismuthate(III) monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.3490(10)
_cell_angle_beta                 108.5090(10)
_cell_angle_gamma                109.3870(10)
_cell_formula_units_Z            2
_cell_length_a                   7.68910(10)
_cell_length_b                   10.86420(10)
_cell_length_c                   11.98670(10)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      1.8
_cell_volume                     880.541(19)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material
;
WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11734
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         1.82
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    10.912
_exptl_absorpt_correction_T_max  0.349
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_density_meas      2.160
_exptl_crystal_density_method    Flotation
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.895
_refine_ls_extinction_coef       0.0132(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         5325
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0212
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0323P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0567
_reflns_number_gt                4009
_reflns_number_total             5325
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz5091.cif
_cod_data_source_block           I
_cod_database_code               2238917
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Bi Bi1 0.5000 1.0000 0.5000 0.02401(5) Uani d S 1 2
Bi Bi2 0.5000 0.5000 0.0000 0.02614(6) Uani d S 1 2
Cl Cl1 0.32827(12) 1.00845(8) 0.66539(8) 0.03793(18) Uani d . 1 1
Cl Cl2 0.19824(12) 1.02948(9) 0.32564(8) 0.04104(19) Uani d . 1 1
Cl Cl3 0.31297(13) 0.73550(8) 0.42359(10) 0.0451(2) Uani d . 1 1
Cl Cl4 0.43949(12) 0.52414(10) 0.20718(8) 0.0461(2) Uani d . 1 1
Cl Cl5 0.12577(12) 0.47555(9) -0.12177(9) 0.0468(2) Uani d . 1 1
Cl Cl6 0.36405(14) 0.23214(9) -0.03209(11) 0.0523(3) Uani d . 1 1
N N1 1.1331(4) 0.2550(3) 0.6613(2) 0.0383(6) Uani d . 1 1
H H1A 1.2346 0.3229 0.7126 0.057 Uiso calc R 1 1
H H1B 1.1303 0.1800 0.6881 0.057 Uiso calc R 1 1
H H1C 1.0211 0.2667 0.6541 0.057 Uiso calc R 1 1
C C1 1.1551(5) 0.2473(3) 0.5432(3) 0.0351(7) Uani d . 1 1
H H1E 1.0550 0.1664 0.4906 0.042 Uiso calc R 1 1
H H1D 1.2834 0.2440 0.5526 0.042 Uiso calc R 1 1
C C2 1.1357(5) 0.3649(3) 0.4873(3) 0.0368(7) Uani d . 1 1
H H2E 1.2356 0.4457 0.5403 0.044 Uiso calc R 1 1
H H2D 1.0074 0.3681 0.4782 0.044 Uiso calc R 1 1
C C3 1.1583(5) 0.3592(3) 0.3652(3) 0.0378(8) Uani d . 1 1
H H3E 1.1698 0.4437 0.3396 0.045 Uiso calc R 1 1
H H3D 1.2784 0.3441 0.3720 0.045 Uiso calc R 1 1
N N2 0.9871(4) 0.2518(2) 0.2741(2) 0.0316(6) Uani d . 1 1
H H2A 0.9784 0.1738 0.2983 0.038 Uiso calc R 1 1
H H2B 0.8761 0.2653 0.2702 0.038 Uiso calc R 1 1
C C4 0.9967(5) 0.2418(3) 0.1523(3) 0.0328(7) Uani d . 1 1
H H4E 1.1114 0.2220 0.1539 0.039 Uiso calc R 1 1
H H4D 1.0091 0.3258 0.1254 0.039 Uiso calc R 1 1
C C5 0.8107(5) 0.1329(3) 0.0668(3) 0.0408(8) Uani d . 1 1
H H5E 0.6966 0.1481 0.0734 0.049 Uiso calc R 1 1
H H5D 0.8065 0.0483 0.0903 0.049 Uiso calc R 1 1
C C6 0.7976(5) 0.1254(4) -0.0631(3) 0.0472(9) Uani d . 1 1
H H6E 0.9246 0.1324 -0.0670 0.057 Uiso calc R 1 1
H H6D 0.7013 0.0398 -0.1090 0.057 Uiso calc R 1 1
N N3 0.7405(4) 0.2322(3) -0.1174(3) 0.0479(8) Uani d . 1 1
H H3A 0.6490 0.2444 -0.0925 0.072 Uiso calc R 1 1
H H3B 0.6922 0.2089 -0.1968 0.072 Uiso calc R 1 1
H H3C 0.8461 0.3071 -0.0955 0.072 Uiso calc R 1 1
O OW 0.6532(5) 0.2968(4) 0.2841(4) 0.0799(11) Uani d D 1 1
H H1W 0.576(7) 0.300(7) 0.217(3) 0.15(3) Uiso d D 1 1
H H2W 0.597(8) 0.252(6) 0.328(5) 0.16(3) Uiso d D 1 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'
O O 0.0106 0.0060 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
Cl3 Bi1 Cl3 . 2_676 180.0
Cl3 Bi1 Cl2 . . 87.59(3)
Cl3 Bi1 Cl2 2_676 . 92.41(3)
Cl3 Bi1 Cl2 . 2_676 92.41(3)
Cl3 Bi1 Cl2 2_676 2_676 87.59(3)
Cl2 Bi1 Cl2 . 2_676 180.0
Cl3 Bi1 Cl1 . 2_676 85.80(3)
Cl3 Bi1 Cl1 2_676 2_676 94.20(3)
Cl2 Bi1 Cl1 . 2_676 87.82(3)
Cl2 Bi1 Cl1 2_676 2_676 92.18(3)
Cl3 Bi1 Cl1 . . 94.20(3)
Cl3 Bi1 Cl1 2_676 . 85.80(3)
Cl2 Bi1 Cl1 . . 92.18(3)
Cl2 Bi1 Cl1 2_676 . 87.82(3)
Cl1 Bi1 Cl1 2_676 . 180.0
Cl4 Bi2 Cl4 2_665 . 180.00(4)
Cl4 Bi2 Cl5 2_665 . 89.74(3)
Cl4 Bi2 Cl5 . . 90.26(3)
Cl4 Bi2 Cl5 2_665 2_665 90.26(3)
Cl4 Bi2 Cl5 . 2_665 89.74(3)
Cl5 Bi2 Cl5 . 2_665 180.00(6)
Cl4 Bi2 Cl6 2_665 . 86.87(3)
Cl4 Bi2 Cl6 . . 93.13(3)
Cl5 Bi2 Cl6 . . 87.00(3)
Cl5 Bi2 Cl6 2_665 . 93.00(3)
Cl4 Bi2 Cl6 2_665 2_665 93.13(3)
Cl4 Bi2 Cl6 . 2_665 86.87(3)
Cl5 Bi2 Cl6 . 2_665 93.00(3)
Cl5 Bi2 Cl6 2_665 2_665 87.00(3)
Cl6 Bi2 Cl6 . 2_665 180.00(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 . . 111.4(3)
N1 C1 H1E . . 109.4
C2 C1 H1E . . 109.4
N1 C1 H1D . . 109.4
C2 C1 H1D . . 109.4
H1E C1 H1D . . 108.0
C1 C2 C3 . . 112.3(3)
C1 C2 H2E . . 109.1
C3 C2 H2E . . 109.1
C1 C2 H2D . . 109.1
C3 C2 H2D . . 109.1
H2E C2 H2D . . 107.9
N2 C3 C2 . . 111.4(3)
N2 C3 H3E . . 109.4
C2 C3 H3E . . 109.4
N2 C3 H3D . . 109.4
C2 C3 H3D . . 109.4
H3E C3 H3D . . 108.0
C4 N2 C3 . . 114.5(3)
C4 N2 H2A . . 108.6
C3 N2 H2A . . 108.6
C4 N2 H2B . . 108.6
C3 N2 H2B . . 108.6
H2A N2 H2B . . 107.6
N2 C4 C5 . . 109.4(3)
N2 C4 H4E . . 109.8
C5 C4 H4E . . 109.8
N2 C4 H4D . . 109.8
C5 C4 H4D . . 109.8
H4E C4 H4D . . 108.2
C4 C5 C6 . . 113.0(3)
C4 C5 H5E . . 109.0
C6 C5 H5E . . 109.0
C4 C5 H5D . . 109.0
C6 C5 H5D . . 109.0
H5E C5 H5D . . 107.8
N3 C6 C5 . . 112.2(3)
N3 C6 H6E . . 109.2
C5 C6 H6E . . 109.2
N3 C6 H6D . . 109.2
C5 C6 H6D . . 109.2
H6E C6 H6D . . 107.9
C6 N3 H3A . . 109.5
C6 N3 H3B . . 109.5
H3A N3 H3B . . 109.5
C6 N3 H3C . . 109.5
H3A N3 H3C . . 109.5
H3B N3 H3C . . 109.5
H1W OW H2W . . 115(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Bi1 Cl3 . 2.6976(8)
Bi1 Cl3 2_676 2.6976(8)
Bi1 Cl2 . 2.7105(8)
Bi1 Cl2 2_676 2.7105(8)
Bi1 Cl1 2_676 2.7209(8)
Bi1 Cl1 . 2.7209(8)
Bi2 Cl4 2_665 2.6816(8)
Bi2 Cl4 . 2.6817(8)
Bi2 Cl5 . 2.6948(8)
Bi2 Cl5 2_665 2.6948(8)
Bi2 Cl6 . 2.7025(9)
Bi2 Cl6 2_665 2.7025(9)
N1 C1 . 1.478(4)
N1 H1A . 0.8900
N1 H1B . 0.8900
N1 H1C . 0.8900
C1 C2 . 1.506(5)
C1 H1E . 0.9700
C1 H1D . 0.9700
C2 C3 . 1.528(5)
C2 H2E . 0.9700
C2 H2D . 0.9700
C3 N2 . 1.485(4)
C3 H3E . 0.9700
C3 H3D . 0.9700
N2 C4 . 1.485(4)
N2 H2A . 0.9000
N2 H2B . 0.9000
C4 C5 . 1.517(4)
C4 H4E . 0.9700
C4 H4D . 0.9700
C5 C6 . 1.524(5)
C5 H5E . 0.9700
C5 H5D . 0.9700
C6 N3 . 1.485(5)
C6 H6E . 0.9700
C6 H6D . 0.9700
N3 H3A . 0.8900
N3 H3B . 0.8900
N3 H3C . 0.8900
OW H1W . 0.844(19)
OW H2W . 0.857(19)
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 Cl4 2_766 0.89 2.34 3.174(3) 155.7 yes
N1 H1B Cl2 2_666 0.89 2.73 3.339(3) 126.5 yes
N1 H1B Cl1 1_645 0.89 2.82 3.474(3) 131.5 yes
N1 H1C Cl3 2_666 0.89 2.43 3.293(3) 163.4 yes
N2 H2B OW . 0.90 1.91 2.804(4) 172.5 yes
N2 H2A Cl2 1_645 0.90 2.63 3.316(3) 134.1 yes
N2 H2A Cl1 2_666 0.90 2.71 3.347(3) 129.1 yes
N3 H3A Cl6 . 0.89 2.48 3.362(3) 169.1 yes
N3 H3B Cl1 1_544 0.89 2.81 3.412(3) 126.1 yes
N3 H3B Cl3 2_665 0.89 2.81 3.612(3) 150.6 yes
N3 H3C Cl5 1_655 0.89 2.44 3.269(3) 154.9 yes
OW H1W Cl6 . 0.844(19) 2.83(3) 3.620(4) 157(6) yes
OW H2W Cl3 2_666 0.857(19) 2.82(4) 3.478(4) 135(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
N1 C1 C2 C3 179.9(3)
C1 C2 C3 N2 69.7(4)
C2 C3 N2 C4 178.8(3)
C3 N2 C4 C5 -177.7(3)
N2 C4 C5 C6 173.8(3)
C4 C5 C6 N3 -76.5(4)
