#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/16/2221654.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_2221654
loop_
_publ_author_name
'Hu, Tuoping'
_publ_section_title
;
 1,1'-Dimethyl-4,4'-bipyridinium bis(triiodide)
;
_journal_coeditor_code           EZ2167
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1162
_journal_paper_doi               10.1107/S1600536809015207
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H14 N2 2+, 2I3 -'
_chemical_formula_moiety         'C12 H14 N2 2+, 2(I3 -)'
_chemical_formula_sum            'C12 H14 I6 N2'
_chemical_formula_weight         947.65
_chemical_name_systematic
;
1,1'-Dimethyl-4,4'-bipyridinium bis(triiodide)
;
_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
_cell_angle_alpha                90.306(5)
_cell_angle_beta                 94.192(4)
_cell_angle_gamma                102.332(5)
_cell_formula_units_Z            1
_cell_length_a                   7.5457(4)
_cell_length_b                   7.9541(6)
_cell_length_c                   9.3029(6)
_cell_measurement_reflns_used    4412
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.6
_cell_volume                     543.88(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.052
_diffrn_reflns_av_sigmaI/netI    0.047
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12956
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.3
_diffrn_reflns_theta_min         3.9
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.562
_exptl_absorpt_correction_T_max  0.504
_exptl_absorpt_correction_T_min  0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.893
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.97
_refine_diff_density_min         -0.86
_refine_ls_extinction_coef       0.0028(3)
_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   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.102
_refine_ls_R_factor_gt           0.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.005P)²+2.2853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.058
_refine_ls_wR_factor_ref         0.073
_reflns_number_gt                1468
_reflns_number_total             2683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2167.cif
_cod_data_source_block           I
_cod_database_code               2221654
_cod_database_fobs_code          2221654
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_disorder_assembly
_atom_site_disorder_group
I I1 0.11371(7) 0.64766(7) 0.84204(6) 0.0705(2) Uani d . 1 . .
I I2 0.19121(6) 0.80427(6) 0.56237(6) 0.05927(17) Uani d . 1 . .
I I3 0.25337(8) 0.96496(8) 0.28546(6) 0.0816(2) Uani d . 1 . .
N N1 0.3773(9) 0.2800(7) 0.8128(7) 0.0588(16) Uani d . 1 . .
C C1 0.3276(13) 0.1852(11) 0.9438(9) 0.085(3) Uani d . 1 . .
H H1A 0.4248 0.2166 1.0179 0.128 Uiso calc R 1 . .
H H1B 0.3064 0.0638 0.9235 0.128 Uiso calc R 1 . .
H H1C 0.2190 0.2131 0.9758 0.128 Uiso calc R 1 . .
C C2 0.5358(12) 0.3875(11) 0.8116(9) 0.074(2) Uani d . 1 . .
H H2 0.6149 0.4034 0.8944 0.088 Uiso calc R 1 . .
C C3 0.2652(11) 0.2566(10) 0.6956(10) 0.072(2) Uani d . 1 . .
H H3 0.1526 0.1813 0.6969 0.086 Uiso calc R 1 . .
C C4 0.5864(9) 0.4764(10) 0.6903(8) 0.061(2) Uani d . 1 . .
H H4 0.6984 0.5532 0.6924 0.074 Uiso calc R 1 . .
C C5 0.3120(10) 0.3414(10) 0.5722(8) 0.066(2) Uani d . 1 . .
H H5 0.2309 0.3216 0.4906 0.079 Uiso calc R 1 . .
C C6 0.4743(8) 0.4540(7) 0.5658(7) 0.0396(14) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.0689(4) 0.0899(4) 0.0576(3) 0.0291(3) 0.0010(3) 0.0076(3)
I2 0.0503(3) 0.0648(3) 0.0672(3) 0.0224(2) 0.0040(2) 0.0045(2)
I3 0.0838(4) 0.0895(4) 0.0816(4) 0.0335(3) 0.0267(3) 0.0292(3)
N1 0.066(4) 0.051(4) 0.063(4) 0.016(3) 0.016(4) 0.010(3)
C1 0.106(7) 0.076(6) 0.075(6) 0.017(5) 0.017(5) 0.015(5)
C2 0.071(6) 0.088(6) 0.061(5) 0.020(5) -0.011(4) 0.015(5)
C3 0.062(5) 0.066(5) 0.078(6) -0.010(4) 0.011(5) -0.003(5)
C4 0.039(4) 0.077(5) 0.058(5) -0.004(4) -0.016(3) 0.006(4)
C5 0.052(5) 0.080(6) 0.054(5) -0.007(4) -0.003(4) -0.001(4)
C6 0.031(3) 0.032(3) 0.054(4) 0.005(3) -0.002(3) -0.003(3)
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'
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
I3 I2 I1 . . 177.49(2) y
C2 N1 C3 . . 119.7(7) ?
C2 N1 C1 . . 119.8(7) ?
C3 N1 C1 . . 120.5(7) ?
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C4 . . 121.0(7) ?
N1 C2 H2 . . 119.5 ?
C4 C2 H2 . . 119.5 ?
N1 C3 C5 . . 120.9(7) ?
N1 C3 H3 . . 119.5 ?
C5 C3 H3 . . 119.5 ?
C2 C4 C6 . . 121.0(6) ?
C2 C4 H4 . . 119.5 ?
C6 C4 H4 . . 119.5 ?
C6 C5 C3 . . 121.6(7) ?
C6 C5 H5 . . 119.2 ?
C3 C5 H5 . . 119.2 ?
C5 C6 C4 . . 115.9(6) ?
C5 C6 C6 . 2_666 122.1(7) ?
C4 C6 C6 . 2_666 122.1(7) ?
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
I1 I2 . 2.9341(8) y
I2 I3 . 2.9061(8) y
N1 C2 . 1.314(9) ?
N1 C3 . 1.317(9) ?
N1 C1 . 1.467(9) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C4 . 1.370(10) ?
C2 H2 . 0.9300 ?
C3 C5 . 1.364(10) ?
C3 H3 . 0.9300 ?
C4 C6 . 1.371(8) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.359(9) ?
C5 H5 . 0.9300 ?
C6 C6 2_666 1.464(12) ?
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
C3 H3 I3 2_566 0.93 3.05 3.951(8) 162.8
C2 H2 I1 2_667 0.93 3.16 4.066(8) 164.4
C5 H5 I2 2_566 0.93 3.13 3.839(7) 134.5
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
C3 N1 C2 C4 . . . . 0.3(12) ?
C1 N1 C2 C4 . . . . 179.4(7) ?
C2 N1 C3 C5 . . . . 0.6(12) ?
C1 N1 C3 C5 . . . . -178.5(7) ?
N1 C2 C4 C6 . . . . -1.0(12) ?
N1 C3 C5 C6 . . . . -0.7(13) ?
C3 C5 C6 C4 . . . . 0.0(11) ?
C3 C5 C6 C6 . . . 2_666 -179.8(8) ?
C2 C4 C6 C5 . . . . 0.9(11) ?
C2 C4 C6 C6 . . . 2_666 -179.3(8) ?
