#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/10/2201047.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_2201047
loop_
_publ_author_name
'Jonathan P. H. Charmant'
'Nicholas C. Norman'
'Jonathan Starbuck'
_publ_section_title
;
 A bis[pentaiodobismuthate(III)] salt of 4-hydroxypyridinium
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m144
_journal_page_last               m146
_journal_paper_doi               10.1107/S1600536802003136
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          '(C5 H6 N O)4 [Bi2 I10], 4C5 H5 N O'
_chemical_formula_moiety         '4C5 H6 N O 1+, Bi2 I10 4-, 4C5 H5 N O'
_chemical_formula_sum            'C40 H44 Bi2 I10 N8 O8'
_chemical_formula_weight         2451.80
_chemical_name_systematic
;
 tetra(4-hydroxypyridinium) bis((μ₂-iodo)tetraiodobismuthate(III))
 4-pyridone tetrasolvate
;
_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                116.212(13)
_cell_angle_beta                 95.05(2)
_cell_angle_gamma                92.914(16)
_cell_formula_units_Z            1
_cell_length_a                   10.366(3)
_cell_length_b                   12.362(3)
_cell_length_c                   13.504(5)
_cell_measurement_reflns_used    5958
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1538.7(8)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SHELXTL (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scans with 0.3° frames'
_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  0.0610
_diffrn_reflns_av_sigmaI/netI    0.1019
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15998
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.777
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.872
_refine_diff_density_min         -2.670
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0457
_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)+(0.0377P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                4015
_reflns_number_total             6960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6149.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1538.6(8)
_cod_database_code               2201047
_cod_database_fobs_code          2201047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Bi1 0.53154(5) 0.58465(4) 0.69033(4) 0.02469(12) Uani d . 1 . . Bi
I1 0.53293(9) 0.47302(8) 0.84481(7) 0.0426(2) Uani d . 1 . . I
I2 0.23164(8) 0.57258(7) 0.69094(6) 0.03209(19) Uani d . 1 . . I
I3 0.57605(8) 0.84204(7) 0.86969(6) 0.0377(2) Uani d . 1 . . I
I4 0.82569(8) 0.58151(7) 0.69141(6) 0.03154(19) Uani d . 1 . . I
I5 0.50680(8) 0.68685(6) 0.50912(6) 0.02954(19) Uani d . 1 . . I
N1 0.3262(11) 0.8174(10) 1.1491(9) 0.047(3) Uani d . 1 . . N
H1A 0.2549 0.7852 1.1018 0.057 Uiso calc R 1 . . H
N2 0.9281(10) 1.1400(8) 1.1014(7) 0.035(2) Uani d . 1 . . N
H2A 0.9411 1.1776 1.0605 0.042 Uiso calc R 1 . . H
N3 1.0039(12) 0.7018(8) 1.5359(7) 0.042(3) Uani d . 1 . . N
H3A 0.9945 0.6597 1.5734 0.050 Uiso calc R 1 . . H
N4 -0.1625(11) 0.5816(9) 1.1423(8) 0.040(3) Uani d . 1 . . N
H4A -0.2176 0.5483 1.1693 0.049 Uiso calc R 1 . . H
O1 0.6488(9) 0.9703(8) 1.3745(7) 0.054(3) Uani d . 1 . . O
H1 0.7164 0.9555 1.3428 0.081 Uiso calc R 1 . . H
O2 0.8628(8) 0.9674(7) 1.2917(7) 0.038(2) Uani d . 1 . . O
O3 1.0549(8) 0.9018(7) 1.3715(7) 0.042(2) Uani d . 1 . . O
H3 0.9837 0.9229 1.3548 0.063 Uiso calc R 1 . . H
O4 0.0948(8) 0.7446(7) 1.0290(6) 0.040(2) Uani d . 1 . . O
C1 0.4414(13) 0.8066(11) 1.1124(11) 0.041(3) Uani d . 1 . . C
H1B 0.4468 0.7659 1.0347 0.050 Uiso calc R 1 . . H
C2 0.5537(13) 0.8542(11) 1.1862(11) 0.043(3) Uani d . 1 . . C
H2B 0.6365 0.8429 1.1600 0.051 Uiso calc R 1 . . H
C3 0.5447(13) 0.9189(11) 1.2993(11) 0.040(3) Uani d . 1 . . C
C4 0.4227(13) 0.9296(13) 1.3361(11) 0.048(3) Uani d . 1 . . C
H4B 0.4130 0.9720 1.4128 0.058 Uiso calc R 1 . . H
C5 0.3184(13) 0.8769(12) 1.2575(11) 0.049(4) Uani d . 1 . . C
H5A 0.2345 0.8828 1.2814 0.058 Uiso calc R 1 . . H
C6 1.0309(13) 1.0989(10) 1.1419(10) 0.037(3) Uani d . 1 . . C
H6A 1.1162 1.1102 1.1252 0.045 Uiso calc R 1 . . H
C7 1.0097(12) 1.0423(10) 1.2059(9) 0.036(3) Uani d . 1 . . C
H7A 1.0812 1.0157 1.2351 0.043 Uiso calc R 1 . . H
C8 0.8838(12) 1.0222(9) 1.2299(9) 0.028(3) Uani d . 1 . . C
C9 0.7810(13) 1.0674(10) 1.1878(11) 0.044(3) Uani d . 1 . . C
H9A 0.6947 1.0589 1.2039 0.053 Uiso calc R 1 . . H
C10 0.8078(12) 1.1223(10) 1.1248(10) 0.035(3) Uani d . 1 . . C
H10A 0.7380 1.1503 1.0950 0.042 Uiso calc R 1 . . H
C11 1.1226(14) 0.7230(11) 1.5131(11) 0.045(3) Uani d . 1 . . C
H11A 1.1948 0.6913 1.5357 0.054 Uiso calc R 1 . . H
C12 1.1394(12) 0.7899(10) 1.4574(9) 0.035(3) Uani d . 1 . . C
H12A 1.2240 0.8063 1.4422 0.042 Uiso calc R 1 . . H
C13 1.0347(13) 0.8343(10) 1.4226(9) 0.033(3) Uani d . 1 . . C
C14 0.9087(12) 0.8083(10) 1.4466(9) 0.037(3) Uani d . 1 . . C
H14A 0.8342 0.8366 1.4230 0.045 Uiso calc R 1 . . H
C15 0.8980(13) 0.7425(10) 1.5039(9) 0.037(3) Uani d . 1 . . C
H15A 0.8152 0.7249 1.5215 0.044 Uiso calc R 1 . . H
C16 -0.0347(13) 0.5774(10) 1.1645(9) 0.032(3) Uani d . 1 . . C
H16A -0.0061 0.5363 1.2063 0.038 Uiso calc R 1 . . H
C17 0.0542(13) 0.6312(9) 1.1281(9) 0.035(3) Uani d . 1 . . C
H17A 0.1445 0.6292 1.1461 0.042 Uiso calc R 1 . . H
C18 0.0128(12) 0.6913(10) 1.0624(9) 0.031(3) Uani d . 1 . . C
C19 -0.1247(12) 0.6886(10) 1.0416(9) 0.035(3) Uani d . 1 . . C
H19A -0.1584 0.7265 0.9985 0.042 Uiso calc R 1 . . H
C20 -0.2099(13) 0.6342(11) 1.0807(10) 0.042(3) Uani d . 1 . . C
H20A -0.3011 0.6335 1.0648 0.050 Uiso calc R 1 . . H
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'
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
I1 Bi1 I3 . 95.43(4) yes
I1 Bi1 I4 . 91.10(3) yes
I3 Bi1 I4 . 88.77(4) yes
I1 Bi1 I2 . 85.81(3) yes
I3 Bi1 I2 . 93.51(4) yes
I4 Bi1 I2 . 176.31(3) yes
I1 Bi1 I5 . 174.51(3) yes
I3 Bi1 I5 . 88.65(4) yes
I4 Bi1 I5 . 92.67(3) yes
I2 Bi1 I5 . 90.28(3) yes
I1 Bi1 I5 2_666 86.95(4) yes
I3 Bi1 I5 2_666 177.04(3) yes
I4 Bi1 I5 2_666 89.43(4) yes
I2 Bi1 I5 2_666 88.40(4) yes
I5 Bi1 I5 2_666 89.09(4) yes
Bi1 I5 Bi1 2_666 90.91(4) yes
C1 N1 C5 . 119.8(12) no
C1 N1 H1A . 120.1 no
C5 N1 H1A . 120.1 no
C10 N2 C6 . 119.6(10) no
C10 N2 H2A . 120.2 no
C6 N2 H2A . 120.2 no
C11 N3 C15 . 122.6(10) no
C11 N3 H3A . 118.7 no
C15 N3 H3A . 118.7 no
C20 N4 C16 . 122.9(11) no
C20 N4 H4A . 118.6 no
C16 N4 H4A . 118.6 no
C3 O1 H1 . 109.5 no
C13 O3 H3 . 109.5 no
N1 C1 C2 . 120.4(13) no
N1 C1 H1B . 119.8 no
C2 C1 H1B . 119.8 no
C1 C2 C3 . 119.4(12) no
C1 C2 H2B . 120.3 no
C3 C2 H2B . 120.3 no
O1 C3 C4 . 118.2(12) no
O1 C3 C2 . 122.5(12) no
C4 C3 C2 . 119.2(12) no
C5 C4 C3 . 116.9(13) no
C5 C4 H4B . 121.5 no
C3 C4 H4B . 121.5 no
N1 C5 C4 . 124.1(13) no
N1 C5 H5A . 117.9 no
C4 C5 H5A . 117.9 no
C7 C6 N2 . 119.5(12) no
C7 C6 H6A . 120.2 no
N2 C6 H6A . 120.2 no
C6 C7 C8 . 121.3(12) no
C6 C7 H7A . 119.3 no
C8 C7 H7A . 119.3 no
O2 C8 C7 . 121.5(11) no
O2 C8 C9 . 121.1(11) no
C7 C8 C9 . 117.3(11) no
C10 C9 C8 . 118.6(12) no
C10 C9 H9A . 120.7 no
C8 C9 H9A . 120.7 no
C9 C10 N2 . 123.5(12) no
C9 C10 H10A . 118.2 no
N2 C10 H10A . 118.2 no
N3 C11 C12 . 119.6(12) no
N3 C11 H11A . 120.2 no
C12 C11 H11A . 120.2 no
C11 C12 C13 . 120.5(12) no
C11 C12 H12A . 119.8 no
C13 C12 H12A . 119.8 no
O3 C13 C12 . 119.0(12) no
O3 C13 C14 . 122.5(11) no
C12 C13 C14 . 118.6(10) no
C15 C14 C13 . 118.4(12) no
C15 C14 H14A . 120.8 no
C13 C14 H14A . 120.8 no
N3 C15 C14 . 120.4(12) no
N3 C15 H15A . 119.8 no
C14 C15 H15A . 119.8 no
N4 C16 C17 . 120.7(11) no
N4 C16 H16A . 119.6 no
C17 C16 H16A . 119.6 no
C16 C17 C18 . 120.5(12) no
C16 C17 H17A . 119.8 no
C18 C17 H17A . 119.8 no
O4 C18 C19 . 124.0(11) no
O4 C18 C17 . 121.6(11) no
C19 C18 C17 . 114.4(11) no
C20 C19 C18 . 122.9(11) no
C20 C19 H19A . 118.6 no
C18 C19 H19A . 118.6 no
N4 C20 C19 . 118.6(12) no
N4 C20 H20A . 120.7 no
C19 C20 H20A . 120.7 no
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 I1 . 2.9657(12) yes
Bi1 I3 . 3.0082(12) yes
Bi1 I4 . 3.0502(13) yes
Bi1 I2 . 3.1056(13) yes
Bi1 I5 . 3.2099(12) yes
Bi1 I5 2_666 3.2197(12) yes
I5 Bi1 2_666 3.2197(12) yes
N1 C1 . 1.324(15) yes
N1 C5 . 1.329(15) yes
N1 H1A . 0.880 no
N2 C10 . 1.343(14) yes
N2 C6 . 1.374(15) yes
N2 H2A . 0.880 no
N3 C11 . 1.335(16) yes
N3 C15 . 1.345(15) yes
N3 H3A . 0.880 no
N4 C20 . 1.340(14) yes
N4 C16 . 1.341(15) yes
N4 H4A . 0.880 no
O1 C3 . 1.329(14) yes
O1 H1 . 0.840 no
O2 C8 . 1.311(13) yes
O3 C13 . 1.317(13) yes
O3 H3 . 0.840 no
O4 C18 . 1.279(13) yes
C1 C2 . 1.379(17) yes
C1 H1B . 0.950 no
C2 C3 . 1.391(16) yes
C2 H2B . 0.950 no
C3 C4 . 1.390(17) yes
C4 C5 . 1.355(17) yes
C4 H4B . 0.950 no
C5 H5A . 0.950 no
C6 C7 . 1.355(15) yes
C6 H6A . 0.950 no
C7 C8 . 1.408(16) yes
C7 H7A . 0.950 no
C8 C9 . 1.416(16) yes
C9 C10 . 1.341(16) yes
C9 H9A . 0.950 no
C10 H10A . 0.950 no
C11 C12 . 1.356(16) yes
C11 H11A . 0.950 no
C12 C13 . 1.377(16) yes
C12 H12A . 0.950 no
C13 C14 . 1.427(16) yes
C14 C15 . 1.355(16) yes
C14 H14A . 0.950 no
C15 H15A . 0.950 no
C16 C17 . 1.357(16) yes
C16 H16A . 0.950 no
C17 C18 . 1.439(15) yes
C17 H17A . 0.950 no
C18 C19 . 1.424(16) yes
C19 C20 . 1.359(16) yes
C19 H19A . 0.950 no
C20 H20A . 0.950 no
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 O4 . 0.88 1.78 2.646(14) 168 yes
N2 H2A O4 2_677 0.88 1.87 2.715(12) 160 yes
N3 H3A I2 1_656 0.88 3.29 3.870(11) 126 yes
N3 H3A I4 1_556 0.88 2.87 3.633(10) 147 yes
N4 H4A I1 2_567 0.88 3.25 3.898(11) 133 yes
N4 H4A I2 2_567 0.88 2.89 3.627(9) 144 yes
O1 H1 O2 . 0.84 1.75 2.567(12) 164 yes
O3 H3 O2 . 0.84 1.70 2.518(11) 163 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_4
_geom_torsion
_geom_torsion_publ_flag
I3 Bi1 I5 Bi1 . 2_666 178.09(3) no
I4 Bi1 I5 Bi1 . 2_666 89.39(3) no
I2 Bi1 I5 Bi1 . 2_666 -88.40(3) no
I5 Bi1 I5 Bi1 2_666 2_666 0.000(2) no
C5 N1 C1 C2 . . 1.6(18) no
N1 C1 C2 C3 . . -3.2(18) no
C1 C2 C3 O1 . . -177.9(11) no
C1 C2 C3 C4 . . 2.9(18) no
O1 C3 C4 C5 . . 179.6(12) no
C2 C3 C4 C5 . . -1.0(19) no
C1 N1 C5 C4 . . 0(2) no
C3 C4 C5 N1 . . -1(2) no
C10 N2 C6 C7 . . -0.7(17) no
N2 C6 C7 C8 . . 1.4(18) no
C6 C7 C8 O2 . . 179.9(11) no
C6 C7 C8 C9 . . -2.2(17) no
O2 C8 C9 C10 . . -179.8(11) no
C7 C8 C9 C10 . . 2.3(17) no
C8 C9 C10 N2 . . -1.8(19) no
C6 N2 C10 C9 . . 1.0(18) no
C15 N3 C11 C12 . . 1.3(19) no
N3 C11 C12 C13 . . -1.1(19) no
C11 C12 C13 O3 . . 178.1(11) no
C11 C12 C13 C14 . . 0.0(18) no
O3 C13 C14 C15 . . -177.2(11) no
C12 C13 C14 C15 . . 0.9(17) no
C11 N3 C15 C14 . . -0.4(18) no
C13 C14 C15 N3 . . -0.7(17) no
C20 N4 C16 C17 . . 2.4(17) no
N4 C16 C17 C18 . . -1.5(17) no
C16 C17 C18 O4 . . 178.7(11) no
C16 C17 C18 C19 . . 0.3(16) no
O4 C18 C19 C20 . . -178.1(11) no
C17 C18 C19 C20 . . 0.2(17) no
C16 N4 C20 C19 . . -1.8(18) no
C18 C19 C20 N4 . . 0.5(18) no
