#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/92/2219242.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_2219242
loop_
_publ_author_name
'Eckensberger, Urs David'
'Lerner, Hans-Wolfram'
'Bolte, Michael'
_publ_section_title
;
 4,4'-Dimethyl-2,2'-bipyridinium dichloride
;
_journal_coeditor_code           BI2297
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1806
_journal_paper_doi               10.1107/S1600536808026615
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H14 N2 2+, 2(Cl -)'
_chemical_formula_moiety         'C12 H14 N2 2+, 2 Cl-'
_chemical_formula_sum            'C12 H14 Cl2 N2'
_chemical_formula_weight         257.15
_chemical_name_systematic
;
4,4'-Dimethyl-2,2'-bipyridinium dichloride
;
_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                93.877(15)
_cell_angle_beta                 102.349(15)
_cell_angle_gamma                97.759(15)
_cell_formula_units_Z            1
_cell_length_a                   5.1999(10)
_cell_length_b                   7.2705(13)
_cell_length_c                   8.4785(15)
_cell_measurement_reflns_used    3157
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.6
_cell_volume                     308.71(10)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDSII two-circle'
_diffrn_measurement_method       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  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3382
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.58
_diffrn_reflns_theta_min         3.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_T_max  0.9334
_exptl_absorpt_correction_T_min  0.9024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             134
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         1147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0352
_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)+(0.0407P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                926
_reflns_number_total             1147
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2297.cif
_cod_data_source_block           I
_cod_database_code               2219242
_cod_database_fobs_code          2219242
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
Cl Cl1 0.97517(12) 0.22553(7) 0.26756(7) 0.02679(18) Uani d . 1
N N1 0.6763(4) 0.3002(2) 0.5264(2) 0.0219(4) Uani d . 1
H H1 0.749(6) 0.296(4) 0.444(4) 0.047(8) Uiso d . 1
C C1 0.5194(4) 0.4274(2) 0.5570(2) 0.0195(4) Uani d . 1
C C2 0.7255(5) 0.1636(3) 0.6223(3) 0.0254(5) Uani d . 1
H H2 0.8362 0.0774 0.5967 0.031 Uiso calc R 1
C C3 0.6195(5) 0.1455(3) 0.7564(3) 0.0273(5) Uani d . 1
H H3 0.6568 0.0483 0.8232 0.033 Uiso calc R 1
C C4 0.4553(4) 0.2725(3) 0.7936(3) 0.0223(5) Uani d . 1
C C5 0.4078(4) 0.4121(3) 0.6904(2) 0.0210(5) Uani d . 1
H H5 0.2957 0.4988 0.7125 0.025 Uiso calc R 1
C C6 0.3345(5) 0.2555(3) 0.9383(3) 0.0287(5) Uani d . 1
H H6A 0.2337 0.3585 0.9488 0.043 Uiso calc R 1
H H6B 0.4761 0.2605 1.0362 0.043 Uiso calc R 1
H H6C 0.2147 0.1365 0.9244 0.043 Uiso calc R 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
Cl1 0.0285(3) 0.0269(3) 0.0288(3) 0.00927(19) 0.0113(2) 0.00399(18)
N1 0.0236(10) 0.0228(8) 0.0223(10) 0.0070(7) 0.0082(8) 0.0064(7)
C1 0.0204(11) 0.0195(9) 0.0181(10) 0.0029(8) 0.0031(8) 0.0028(8)
C2 0.0262(12) 0.0238(9) 0.0293(12) 0.0086(8) 0.0081(10) 0.0084(8)
C3 0.0284(13) 0.0244(10) 0.0295(12) 0.0066(9) 0.0032(10) 0.0110(9)
C4 0.0231(11) 0.0217(9) 0.0204(10) -0.0012(8) 0.0035(9) 0.0039(8)
C5 0.0243(12) 0.0196(9) 0.0200(10) 0.0061(8) 0.0043(9) 0.0049(8)
C6 0.0350(14) 0.0301(11) 0.0218(11) 0.0040(10) 0.0076(10) 0.0075(9)
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'
Cl Cl 0.1484 0.1585 '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'
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
C2 N1 C1 . 121.9(2)
C2 N1 H1 . 113.5(19)
C1 N1 H1 . 124.6(19)
N1 C1 C5 . 118.08(18)
N1 C1 C1 2_666 117.0(2)
C5 C1 C1 2_666 124.9(2)
N1 C2 C3 . 121.46(17)
N1 C2 H2 . 119.3
C3 C2 H2 . 119.3
C2 C3 C4 . 119.17(19)
C2 C3 H3 . 120.4
C4 C3 H3 . 120.4
C5 C4 C3 . 117.6(2)
C5 C4 C6 . 121.92(17)
C3 C4 C6 . 120.46(19)
C1 C5 C4 . 121.78(17)
C1 C5 H5 . 119.1
C4 C5 H5 . 119.1
C4 C6 H6A . 109.5
C4 C6 H6B . 109.5
H6A C6 H6B . 109.5
C4 C6 H6C . 109.5
H6A C6 H6C . 109.5
H6B C6 H6C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.342(3)
N1 C1 . 1.360(2)
N1 H1 . 0.86(3)
C1 C5 . 1.382(3)
C1 C1 2_666 1.484(4)
C2 C3 . 1.372(3)
C2 H2 . 0.950
C3 C4 . 1.404(3)
C3 H3 . 0.950
C4 C5 . 1.397(3)
C4 C6 . 1.498(3)
C5 H5 . 0.950
C6 H6A . 0.980
C6 H6B . 0.980
C6 H6C . 0.980
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
N1 H1 Cl1 . 0.86(3) 2.17(3) 3.009(2) 165(3)
C2 H2 Cl1 2_756 0.95 2.75 3.496(2) 136
C5 H5 Cl1 2_666 0.95 2.62 3.554(2) 169
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
C2 N1 C1 C5 . . -0.5(3)
C2 N1 C1 C1 . 2_666 179.7(2)
C1 N1 C2 C3 . . 0.0(3)
N1 C2 C3 C4 . . 0.2(3)
C2 C3 C4 C5 . . 0.1(3)
C2 C3 C4 C6 . . 179.4(2)
N1 C1 C5 C4 . . 0.9(3)
C1 C1 C5 C4 2_666 . -179.3(2)
C3 C4 C5 C1 . . -0.7(3)
C6 C4 C5 C1 . . -180.0(2)
