#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/62/2226272.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_2226272
loop_
_publ_author_name
'Liu, Guang-Xiang'
_publ_section_title
;
 4,4'-Dimethyl-1,1'-(p-phenylenedimethylene)dipyridinium
 bis[7,7,8,8-tetracyanoquinodimethanide(1{-})]
;
_journal_coeditor_code           RZ2446
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1359
_journal_paper_doi               10.1107/S1600536810017113
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H22 N2 2+, 2C12 H4 N4 -'
_chemical_formula_moiety         'C20 H22 N2 2+, 2(C12 H4 N4 -)'
_chemical_formula_sum            'C44 H30 N10'
_chemical_formula_weight         698.78
_chemical_name_systematic
;
4,4'-Dimethyl-1,1'-(p-phenylenedimethylene)dipyridinium
bis[7,7,8,8-tetracyanoquinodimethanide(1-)]
;
_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                101.558(2)
_cell_angle_beta                 106.134(2)
_cell_angle_gamma                97.906(2)
_cell_formula_units_Z            1
_cell_length_a                   8.5904(12)
_cell_length_b                   8.6786(11)
_cell_length_c                   13.3016(17)
_cell_measurement_reflns_used    2212
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.52
_cell_volume                     913.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0347
_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       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6854
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            'Dark green'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0561P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                2243
_reflns_number_total             3353
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2446.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 
;
_cod_database_code               2226272
_cod_database_fobs_code          2226272
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
C C1 0.3619(2) 0.1249(2) -0.12031(15) 0.0513(5) Uani d . 1 . .
C C2 0.1730(3) 0.2868(2) -0.18890(17) 0.0594(5) Uani d . 1 . .
C C3 0.2953(2) 0.2639(2) -0.09960(15) 0.0505(5) Uani d . 1 . .
C C4 0.3415(2) 0.3713(2) 0.00302(15) 0.0464(4) Uani d . 1 . .
C C5 0.4625(2) 0.3502(2) 0.09308(15) 0.0482(5) Uani d . 1 . .
H H5 0.5125 0.2620 0.0849 0.058 Uiso calc R 1 . .
C C6 0.5072(2) 0.4564(2) 0.19137(15) 0.0502(5) Uani d . 1 . .
H H6 0.5873 0.4388 0.2489 0.060 Uiso calc R 1 . .
C C7 0.4357(2) 0.5930(2) 0.20912(15) 0.0488(4) Uani d . 1 . .
C C8 0.3129(2) 0.6118(2) 0.11922(16) 0.0553(5) Uani d . 1 . .
H H8 0.2618 0.6991 0.1277 0.066 Uiso calc R 1 . .
C C9 0.2674(2) 0.5063(2) 0.02115(16) 0.0550(5) Uani d . 1 . .
H H9 0.1854 0.5228 -0.0358 0.066 Uiso calc R 1 . .
C C10 0.4820(2) 0.7038(2) 0.31119(16) 0.0547(5) Uani d . 1 . .
C C11 0.5983(3) 0.6827(3) 0.40268(19) 0.0699(6) Uani d . 1 . .
C C12 0.4142(2) 0.8429(3) 0.32460(16) 0.0595(5) Uani d . 1 . .
C C13 0.7386(3) 0.2441(4) 0.4765(2) 0.1005(9) Uani d . 1 . .
H H13A 0.7287 0.3532 0.5007 0.151 Uiso calc R 1 . .
H H13B 0.7832 0.2031 0.5380 0.151 Uiso calc R 1 . .
H H13C 0.6314 0.1796 0.4344 0.151 Uiso calc R 1 . .
C C14 0.8517(2) 0.2386(3) 0.40876(15) 0.0615(6) Uani d . 1 . .
C C15 0.9129(2) 0.1013(3) 0.38115(16) 0.0603(5) Uani d . 1 . .
H H15 0.8838 0.0116 0.4054 0.072 Uiso calc R 1 . .
C C16 1.0148(2) 0.0970(2) 0.31919(15) 0.0516(5) Uani d . 1 . .
H H16 1.0558 0.0049 0.3019 0.062 Uiso calc R 1 . .
C C17 1.0016(2) 0.3596(2) 0.30954(15) 0.0541(5) Uani d . 1 . .
H H17 1.0331 0.4484 0.2851 0.065 Uiso calc R 1 . .
C C18 0.9013(2) 0.3681(3) 0.37146(16) 0.0608(5) Uani d . 1 . .
H H18 0.8649 0.4629 0.3894 0.073 Uiso calc R 1 . .
C C19 1.1638(2) 0.2155(2) 0.21295(15) 0.0556(5) Uani d . 1 . .
H H19A 1.2619 0.1790 0.2478 0.067 Uiso calc R 1 . .
H H19B 1.1990 0.3218 0.2043 0.067 Uiso calc R 1 . .
C C20 1.0766(2) 0.1027(2) 0.10308(15) 0.0463(4) Uani d . 1 . .
C C21 1.1573(2) -0.0062(2) 0.05873(16) 0.0536(5) Uani d . 1 . .
H H21 1.2635 -0.0118 0.0980 0.064 Uiso calc R 1 . .
C C22 0.9181(2) 0.1069(2) 0.04324(15) 0.0537(5) Uani d . 1 . .
H H22 0.8614 0.1788 0.0722 0.064 Uiso calc R 1 . .
N N1 0.4125(2) 0.0106(2) -0.13825(15) 0.0691(5) Uani d . 1 . .
N N2 0.0727(3) 0.3070(2) -0.25956(17) 0.0860(7) Uani d . 1 . .
N N3 0.3576(3) 0.9543(2) 0.33418(17) 0.0811(6) Uani d . 1 . .
N N4 0.6931(3) 0.6641(3) 0.47670(18) 0.1053(8) Uani d . 1 . .
N N5 1.05663(17) 0.22537(17) 0.28280(11) 0.0450(4) Uani d . 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'
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
N1 C1 C3 . . 178.6(2) ?
N2 C2 C3 . . 178.5(2) ?
C4 C3 C2 . . 121.18(16) ?
C4 C3 C1 . . 123.07(16) ?
C2 C3 C1 . . 115.72(17) ?
C3 C4 C5 . . 122.03(16) ?
C3 C4 C9 . . 121.27(16) ?
C5 C4 C9 . . 116.70(17) ?
C6 C5 C4 . . 121.22(16) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 122.16(17) ?
C5 C6 H6 . . 118.9 ?
C7 C6 H6 . . 118.9 ?
C8 C7 C10 . . 121.36(17) ?
C8 C7 C6 . . 116.30(17) ?
C10 C7 C6 . . 122.33(17) ?
C9 C8 C7 . . 121.90(17) ?
C9 C8 H8 . . 119.1 ?
C7 C8 H8 . . 119.1 ?
C8 C9 C4 . . 121.70(17) ?
C8 C9 H9 . . 119.1 ?
C4 C9 H9 . . 119.1 ?
C11 C10 C12 . . 117.16(18) ?
C11 C10 C7 . . 122.08(17) ?
C12 C10 C7 . . 120.74(18) ?
N4 C11 C10 . . 179.3(2) ?
N3 C12 C10 . . 179.1(2) ?
C14 C13 H13A . . 109.5 ?
C14 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C14 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C18 C14 C15 . . 116.78(18) ?
C18 C14 C13 . . 122.2(2) ?
C15 C14 C13 . . 121.1(2) ?
C16 C15 C14 . . 120.68(19) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
N5 C16 C15 . . 120.27(18) ?
N5 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
N5 C17 C18 . . 120.89(19) ?
N5 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C17 C18 C14 . . 121.10(19) ?
C17 C18 H18 . . 119.4 ?
C14 C18 H18 . . 119.4 ?
N5 C19 C20 . . 112.18(14) ?
N5 C19 H19A . . 109.2 ?
C20 C19 H19A . . 109.2 ?
N5 C19 H19B . . 109.2 ?
C20 C19 H19B . . 109.2 ?
H19A C19 H19B . . 107.9 ?
C22 C20 C21 . . 118.33(17) ?
C22 C20 C19 . . 121.95(17) ?
C21 C20 C19 . . 119.70(16) ?
C20 C21 C22 . 2_755 120.67(17) ?
C20 C21 H21 . . 119.7 ?
C22 C21 H21 2_755 . 119.7 ?
C20 C22 C21 . 2_755 121.00(17) ?
C20 C22 H22 . . 119.5 ?
C21 C22 H22 2_755 . 119.5 ?
C17 N5 C16 . . 120.25(16) ?
C17 N5 C19 . . 120.70(15) ?
C16 N5 C19 . . 119.05(15) ?
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
C1 N1 . 1.145(2) ?
C1 C3 . 1.415(3) ?
C2 N2 . 1.146(2) ?
C2 C3 . 1.419(3) ?
C3 C4 . 1.406(3) ?
C4 C5 . 1.413(2) ?
C4 C9 . 1.419(2) ?
C5 C6 . 1.359(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.416(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.412(3) ?
C7 C10 . 1.413(3) ?
C8 C9 . 1.353(3) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.406(3) ?
C10 C12 . 1.412(3) ?
C11 N4 . 1.146(3) ?
C12 N3 . 1.141(2) ?
C13 C14 . 1.497(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 C18 . 1.379(3) ?
C14 C15 . 1.391(3) ?
C15 C16 . 1.358(3) ?
C15 H15 . 0.9300 ?
C16 N5 . 1.344(2) ?
C16 H16 . 0.9300 ?
C17 N5 . 1.337(2) ?
C17 C18 . 1.347(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 N5 . 1.477(2) ?
C19 C20 . 1.507(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 C22 . 1.383(2) ?
C20 C21 . 1.380(2) ?
C21 C22 2_755 1.380(3) ?
C21 H21 . 0.9300 ?
C22 C21 2_755 1.380(3) ?
C22 H22 . 0.9300 ?
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
C16 H16 N3 1_645 0.93 2.62 3.320(3) 132
C17 H17 N2 2_665 0.93 2.47 3.204(3) 136
C19 H19A N3 1_645 0.97 2.57 3.394(3) 143
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
C2 C3 C4 C5 . . . . 179.72(17) ?
C1 C3 C4 C5 . . . . 1.8(3) ?
C2 C3 C4 C9 . . . . 0.1(3) ?
C1 C3 C4 C9 . . . . -177.77(18) ?
C3 C4 C5 C6 . . . . 179.13(17) ?
C9 C4 C5 C6 . . . . -1.2(2) ?
C4 C5 C6 C7 . . . . 0.0(3) ?
C5 C6 C7 C8 . . . . 1.0(3) ?
C5 C6 C7 C10 . . . . -179.94(18) ?
C10 C7 C8 C9 . . . . -179.89(19) ?
C6 C7 C8 C9 . . . . -0.8(3) ?
C7 C8 C9 C4 . . . . -0.4(3) ?
C3 C4 C9 C8 . . . . -178.94(18) ?
C5 C4 C9 C8 . . . . 1.4(3) ?
C8 C7 C10 C11 . . . . 176.93(19) ?
C6 C7 C10 C11 . . . . -2.1(3) ?
C8 C7 C10 C12 . . . . -4.2(3) ?
C6 C7 C10 C12 . . . . 176.78(18) ?
C18 C14 C15 C16 . . . . -0.8(3) ?
C13 C14 C15 C16 . . . . 179.7(2) ?
C14 C15 C16 N5 . . . . -0.6(3) ?
N5 C17 C18 C14 . . . . -0.3(3) ?
C15 C14 C18 C17 . . . . 1.3(3) ?
C13 C14 C18 C17 . . . . -179.2(2) ?
N5 C19 C20 C22 . . . . 46.7(2) ?
N5 C19 C20 C21 . . . . -134.85(17) ?
C22 C20 C21 C22 . . . 2_755 0.7(3) ?
C19 C20 C21 C22 . . . 2_755 -177.80(17) ?
C21 C20 C22 C21 . . . 2_755 -0.7(3) ?
C19 C20 C22 C21 . . . 2_755 177.76(17) ?
C18 C17 N5 C16 . . . . -1.2(3) ?
C18 C17 N5 C19 . . . . 178.69(17) ?
C15 C16 N5 C17 . . . . 1.7(3) ?
C15 C16 N5 C19 . . . . -178.25(16) ?
C20 C19 N5 C17 . . . . -110.79(18) ?
C20 C19 N5 C16 . . . . 69.1(2) ?
