#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/97/2209726.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_2209726
loop_
_publ_author_name
'Wang, Peng-Fei'
'Liu, Guang-Xiang'
'Chen, You-Cun'
_publ_section_title
;
 An ion-pair complex composed of two
 N-(4-cyanobenzyl)quinolinium cations, two
 7,7,8,8-tetracyanoquinodimethane anions and one neutral
 7,7,8,8-tetracyanoquinodimethane molecule
;
_journal_coeditor_code           AT2050
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3256
_journal_page_last               o3258
_journal_paper_doi               10.1107/S1600536806025736
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '2C17 H13 N2 + , 2C12 H4 N4 1-, C12 H4 N4'
_chemical_formula_moiety         '2C17 H13 N2 + , 2C12 H4 N4 1-, C12 H4 N4'
_chemical_formula_sum            'C70 H38 N16'
_chemical_formula_weight         1103.16
_chemical_name_systematic
;
N-(4-cyanobenzyl)quinolinium--7,7,8,8-tetracyanoquinodimethane (2/3)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.327(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.083(3)
_cell_length_b                   10.8627(17)
_cell_length_c                   17.099(3)
_cell_measurement_reflns_used    3296
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.29
_cell_volume                     2722.0(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14142
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0561
_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)+0.5287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1382
_reflns_number_gt                4175
_reflns_number_total             5321
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2050.cif
_cod_data_source_block           I
_cod_original_cell_volume        2722.0(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209726
_cod_database_fobs_code          2209726
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.34564(13) 0.9686(2) 0.22175(12) 0.0796(6) Uani d . 1
N N2 0.19916(14) 1.0214(2) -0.04701(12) 0.0762(6) Uani d . 1
N N3 0.62204(14) 0.7121(2) -0.14023(15) 0.0821(7) Uani d . 1
N N4 0.77818(14) 0.6509(2) 0.13440(16) 0.0897(7) Uani d . 1
N N5 0.35809(13) 0.62120(19) 0.17934(12) 0.0719(6) Uani d . 1
N N6 0.22321(11) 0.71195(19) -0.09163(12) 0.0653(5) Uani d . 1
N N7 -0.11670(13) 0.04670(18) 0.49120(12) 0.0656(5) Uani d . 1
N N8 0.05696(9) 0.42992(13) 0.22015(9) 0.0379(3) Uani d . 1
C C1 -0.10134(13) 0.11791(19) 0.45041(12) 0.0487(5) Uani d . 1
C C2 -0.08183(12) 0.20649(17) 0.39781(10) 0.0414(4) Uani d . 1
C C3 0.00496(12) 0.21083(17) 0.39901(11) 0.0435(4) Uani d . 1
H H3 0.0511 0.1607 0.4363 0.052 Uiso calc R 1
C C4 0.02212(11) 0.28969(17) 0.34475(10) 0.0407(4) Uani d . 1
H H4 0.0803 0.2928 0.3457 0.049 Uiso calc R 1
C C5 -0.04558(11) 0.36437(16) 0.28893(10) 0.0369(4) Uani d . 1
C C6 -0.13159(12) 0.36175(18) 0.29008(12) 0.0452(4) Uani d . 1
H H6 -0.1774 0.4135 0.2539 0.054 Uiso calc R 1
C C7 -0.14914(12) 0.28339(18) 0.34417(12) 0.0477(5) Uani d . 1
H H7 -0.2067 0.2821 0.3446 0.057 Uiso calc R 1
C C8 -0.03095(12) 0.45028(17) 0.22680(12) 0.0430(4) Uani d . 1
H H8A -0.0804 0.4397 0.1705 0.052 Uiso calc R 1
H H8B -0.0331 0.5345 0.2448 0.052 Uiso calc R 1
C C9 0.12390(13) 0.50912(18) 0.25719(11) 0.0460(5) Uani d . 1
H H9 0.1147 0.5752 0.2873 0.055 Uiso calc R 1
C C10 0.20756(13) 0.4967(2) 0.25259(12) 0.0534(5) Uani d . 1
H H10 0.2534 0.5546 0.2783 0.064 Uiso calc R 1
C C11 0.22158(12) 0.3999(2) 0.21045(12) 0.0529(5) Uani d . 1
H H11 0.2772 0.3913 0.2064 0.063 Uiso calc R 1
C C12 0.15313(11) 0.31195(18) 0.17266(11) 0.0436(4) Uani d . 1
C C13 0.16457(15) 0.2080(2) 0.12908(13) 0.0586(6) Uani d . 1
H H13 0.2200 0.1956 0.1253 0.070 Uiso calc R 1
C C14 0.09696(16) 0.1265(2) 0.09297(14) 0.0614(6) Uani d . 1
H H14 0.1059 0.0578 0.0649 0.074 Uiso calc R 1
C C15 0.01301(14) 0.14448(19) 0.09735(12) 0.0537(5) Uani d . 1
H H15 -0.0335 0.0875 0.0717 0.064 Uiso calc R 1
C C16 -0.00195(12) 0.24336(17) 0.13821(11) 0.0426(4) Uani d . 1
H H16 -0.0583 0.2543 0.1403 0.051 Uiso calc R 1
C C17 0.06793(11) 0.32850(16) 0.17706(10) 0.0369(4) Uani d . 1
C C18 0.26579(14) 0.9889(2) 0.00643(13) 0.0514(5) Uani d . 1
C C19 0.34683(12) 0.94830(18) 0.07388(11) 0.0446(4) Uani d . 1
C C20 0.34779(13) 0.9590(2) 0.15652(13) 0.0528(5) Uani d . 1
C C21 0.41926(11) 0.89603(18) 0.05936(11) 0.0440(4) Uani d . 1
C C22 0.41549(12) 0.88743(18) -0.02445(12) 0.0469(5) Uani d . 1
H H22 0.3648 0.9182 -0.0704 0.056 Uiso calc R 1
C C23 0.48412(13) 0.83532(19) -0.03940(12) 0.0495(5) Uani d . 1
H H23 0.4793 0.8302 -0.0954 0.059 Uiso calc R 1
C C24 0.56275(12) 0.78871(19) 0.02838(13) 0.0511(5) Uani d . 1
C C25 0.56641(12) 0.7975(2) 0.11217(13) 0.0549(5) Uani d . 1
H H25 0.6170 0.7666 0.1581 0.066 Uiso calc R 1
C C26 0.49794(12) 0.8497(2) 0.12725(12) 0.0518(5) Uani d . 1
H H26 0.5029 0.8552 0.1833 0.062 Uiso calc R 1
C C27 0.63346(13) 0.7336(2) 0.01285(14) 0.0583(6) Uani d . 1
C C28 0.62766(14) 0.7221(2) -0.07184(17) 0.0630(6) Uani d . 1
C C29 0.71356(15) 0.6878(2) 0.08023(17) 0.0678(7) Uani d . 1
C C30 0.42493(11) 0.54602(17) -0.06944(11) 0.0408(4) Uani d . 1
H H30 0.3747 0.5772 -0.1155 0.049 Uiso calc R 1
C C31 0.42811(11) 0.55431(16) 0.01501(11) 0.0386(4) Uani d . 1
C C32 0.50671(11) 0.50611(17) 0.08362(11) 0.0405(4) Uani d . 1
H H32 0.5109 0.5108 0.1394 0.049 Uiso calc R 1
C C33 0.35852(11) 0.60989(18) 0.02995(12) 0.0434(4) Uani d . 1
C C34 0.28253(12) 0.66475(19) -0.03757(13) 0.0481(5) Uani d . 1
C C35 0.35867(12) 0.61575(19) 0.11309(13) 0.0504(5) 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
C9 N8 C17 . 121.33(14)
C9 N8 C8 . 118.82(15)
C17 N8 C8 . 119.84(14)
N7 C1 C2 . 179.0(2)
C7 C2 C3 . 119.96(16)
C7 C2 C1 . 120.60(16)
C3 C2 C1 . 119.39(17)
C4 C3 C2 . 119.50(17)
C4 C3 H3 . 120.3
C2 C3 H3 . 120.3
C3 C4 C5 . 120.96(15)
C3 C4 H4 . 119.5
C5 C4 H4 . 119.5
C4 C5 C6 . 118.98(16)
C4 C5 C8 . 123.08(14)
C6 C5 C8 . 117.93(15)
C7 C6 C5 . 120.32(17)
C7 C6 H6 . 119.8
C5 C6 H6 . 119.8
C6 C7 C2 . 120.22(16)
C6 C7 H7 . 119.9
C2 C7 H7 . 119.9
N8 C8 C5 . 113.19(14)
N8 C8 H8A . 108.9
C5 C8 H8A . 108.9
N8 C8 H8B . 108.9
C5 C8 H8B . 108.9
H8A C8 H8B . 107.8
N8 C9 C10 . 121.94(18)
N8 C9 H9 . 119.0
C10 C9 H9 . 119.0
C11 C10 C9 . 119.12(18)
C11 C10 H10 . 120.4
C9 C10 H10 . 120.4
C10 C11 C12 . 120.51(16)
C10 C11 H11 . 119.7
C12 C11 H11 . 119.7
C11 C12 C13 . 122.90(17)
C11 C12 C17 . 118.96(18)
C13 C12 C17 . 118.13(18)
C14 C13 C12 . 121.09(17)
C14 C13 H13 . 119.5
C12 C13 H13 . 119.5
C13 C14 C15 . 120.14(19)
C13 C14 H14 . 119.9
C15 C14 H14 . 119.9
C16 C15 C14 . 121.3(2)
C16 C15 H15 . 119.4
C14 C15 H15 . 119.4
C15 C16 C17 . 119.44(16)
C15 C16 H16 . 120.3
C17 C16 H16 . 120.3
N8 C17 C16 . 122.00(14)
N8 C17 C12 . 118.08(16)
C16 C17 C12 . 119.92(16)
N2 C18 C19 . 178.5(2)
C21 C19 C18 . 122.40(16)
C21 C19 C20 . 122.78(17)
C18 C19 C20 . 114.76(15)
N1 C20 C19 . 177.8(2)
C19 C21 C26 . 121.72(16)
C19 C21 C22 . 120.88(17)
C26 C21 C22 . 117.40(15)
C23 C22 C21 . 121.42(18)
C23 C22 H22 . 119.3
C21 C22 H22 . 119.3
C22 C23 C24 . 121.26(17)
C22 C23 H23 . 119.4
C24 C23 H23 . 119.4
C27 C24 C23 . 121.30(18)
C27 C24 C25 . 121.46(19)
C23 C24 C25 . 117.23(16)
C26 C25 C24 . 121.59(19)
C26 C25 H25 . 119.2
C24 C25 H25 . 119.2
C25 C26 C21 . 121.10(18)
C25 C26 H26 . 119.5
C21 C26 H26 . 119.5
C24 C27 C28 . 120.9(2)
C24 C27 C29 . 122.11(19)
C28 C27 C29 . 117.02(17)
N3 C28 C27 . 179.2(2)
N4 C29 C27 . 179.9(3)
C32 C30 C31 3_665 121.20(16)
C32 C30 H30 3_665 119.4
C31 C30 H30 . 119.4
C33 C31 C32 . 121.26(16)
C33 C31 C30 . 121.30(16)
C32 C31 C30 . 117.42(14)
C30 C32 C31 3_665 121.38(16)
C30 C32 H32 3_665 119.3
C31 C32 H32 . 119.3
C31 C33 C34 . 121.53(16)
C31 C33 C35 . 122.36(17)
C34 C33 C35 . 116.11(15)
N6 C34 C33 . 177.8(2)
N5 C35 C33 . 179.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C20 . 1.135(2)
N2 C18 . 1.141(3)
N3 C28 . 1.140(3)
N4 C29 . 1.143(3)
N5 C35 . 1.138(2)
N6 C34 . 1.141(2)
N7 C1 . 1.135(2)
N8 C9 . 1.319(2)
N8 C17 . 1.376(2)
N8 C8 . 1.481(2)
C1 C2 . 1.437(3)
C2 C7 . 1.376(3)
C2 C3 . 1.388(2)
C3 C4 . 1.372(2)
C3 H3 . 0.9300
C4 C5 . 1.378(2)
C4 H4 . 0.9300
C5 C6 . 1.392(2)
C5 C8 . 1.504(2)
C6 C7 . 1.369(2)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.386(3)
C9 H9 . 0.9300
C10 C11 . 1.346(3)
C10 H10 . 0.9300
C11 C12 . 1.398(3)
C11 H11 . 0.9300
C12 C13 . 1.406(3)
C12 C17 . 1.414(2)
C13 C14 . 1.339(3)
C13 H13 . 0.9300
C14 C15 . 1.396(3)
C14 H14 . 0.9300
C15 C16 . 1.356(3)
C15 H15 . 0.9300
C16 C17 . 1.395(2)
C16 H16 . 0.9300
C18 C19 . 1.409(3)
C19 C21 . 1.407(2)
C19 C20 . 1.412(2)
C21 C26 . 1.411(3)
C21 C22 . 1.412(2)
C22 C23 . 1.355(2)
C22 H22 . 0.9300
C23 C24 . 1.411(3)
C23 H23 . 0.9300
C24 C27 . 1.404(3)
C24 C25 . 1.413(3)
C25 C26 . 1.355(2)
C25 H25 . 0.9300
C26 H26 . 0.9300
C27 C28 . 1.418(3)
C27 C29 . 1.418(3)
C30 C32 3_665 1.345(2)
C30 C31 . 1.427(2)
C30 H30 . 0.9300
C31 C33 . 1.385(2)
C31 C32 . 1.424(2)
C32 C30 3_665 1.345(2)
C32 H32 . 0.9300
C33 C34 . 1.421(3)
C33 C35 . 1.422(3)
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
C32 H32 N1 2_645 0.93 2.58 3.220(3) 126.4
C16 H16 N6 3_565 0.93 2.46 3.346(2) 159.9
C11 H11 N3 3_665 0.93 2.58 3.426(3) 150.7
C4 H4 N8 . 0.93 2.51 2.856(2) 102.2
C3 H3 N7 3_556 0.93 2.58 3.435(3) 153.5
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_4
_geom_torsion
C7 C2 C3 C4 . . -1.8(3)
C1 C2 C3 C4 . . 175.76(16)
C2 C3 C4 C5 . . -0.2(3)
C3 C4 C5 C6 . . 2.0(3)
C3 C4 C5 C8 . . -178.58(17)
C4 C5 C6 C7 . . -1.9(3)
C8 C5 C6 C7 . . 178.66(17)
C5 C6 C7 C2 . . 0.0(3)
C3 C2 C7 C6 . . 1.9(3)
C1 C2 C7 C6 . . -175.62(18)
C9 N8 C8 C5 . . -105.13(18)
C17 N8 C8 C5 . . 73.8(2)
C4 C5 C8 N8 . . 10.8(2)
C6 C5 C8 N8 . . -169.85(15)
C17 N8 C9 C10 . . 2.0(3)
C8 N8 C9 C10 . . -179.11(16)
N8 C9 C10 C11 . . -1.3(3)
C9 C10 C11 C12 . . -0.8(3)
C10 C11 C12 C13 . . -178.98(18)
C10 C11 C12 C17 . . 2.0(3)
C11 C12 C13 C14 . . -179.31(19)
C17 C12 C13 C14 . . -0.3(3)
C12 C13 C14 C15 . . 0.7(3)
C13 C14 C15 C16 . . -0.4(3)
C14 C15 C16 C17 . . -0.4(3)
C9 N8 C17 C16 . . 179.43(16)
C8 N8 C17 C16 . . 0.5(2)
C9 N8 C17 C12 . . -0.7(2)
C8 N8 C17 C12 . . -179.58(14)
C15 C16 C17 N8 . . -179.34(15)
C15 C16 C17 C12 . . 0.8(2)
C11 C12 C17 N8 . . -1.3(2)
C13 C12 C17 N8 . . 179.64(15)
C11 C12 C17 C16 . . 178.62(15)
C13 C12 C17 C16 . . -0.5(2)
C18 C19 C21 C26 . . -176.51(19)
C20 C19 C21 C26 . . 0.4(3)
C18 C19 C21 C22 . . 3.2(3)
C20 C19 C21 C22 . . -179.88(18)
C19 C21 C22 C23 . . -178.83(19)
C26 C21 C22 C23 . . 0.9(3)
C21 C22 C23 C24 . . -0.7(3)
C22 C23 C24 C27 . . 179.34(19)
C22 C23 C24 C25 . . 0.7(3)
C27 C24 C25 C26 . . -179.5(2)
C23 C24 C25 C26 . . -0.8(3)
C24 C25 C26 C21 . . 1.0(3)
C19 C21 C26 C25 . . 178.71(19)
C22 C21 C26 C25 . . -1.0(3)
C23 C24 C27 C28 . . -0.5(3)
C25 C24 C27 C28 . . 178.10(19)
C23 C24 C27 C29 . . 179.1(2)
C25 C24 C27 C29 . . -2.3(3)
C32 C30 C31 C33 3_665 . 178.86(18)
C32 C30 C31 C32 3_665 . 0.5(3)
C33 C31 C32 C30 . 3_665 -178.86(18)
C30 C31 C32 C30 . 3_665 -0.5(3)
C32 C31 C33 C34 . . 176.15(17)
C30 C31 C33 C34 . . -2.2(3)
C32 C31 C33 C35 . . -3.8(3)
C30 C31 C33 C35 . . 177.91(17)
