#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:44:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180353 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/22/7202256.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7202256
loop_
_publ_author_name
'Liu, Guang-Xiang'
'Xu, Heng'
'Ren, Xiao-Ming'
'Sun, Wei-Yin'
_publ_section_title
;
 A series of novel ion-pair complexes based on TCNQ: syntheses, crystal
 structures and properties
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1574
_journal_paper_doi               10.1039/b808390h
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C12 H13 N2, C12 H4 N4'
_chemical_formula_sum            'C24 H17 N6'
_chemical_formula_weight         389.44
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.082(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.702(4)
_cell_length_b                   8.678(3)
_cell_length_c                   22.271(7)
_cell_measurement_reflns_used    4476
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.68
_cell_measurement_theta_min      2.46
_cell_volume                     2080.6(12)
_computing_cell_refinement       'SAINT-PLUS, Ver. 6.0, 1997'
_computing_data_collection       'SMART, 1998'
_computing_data_reduction        'SAINT-PLUS, Ver. 6.0, 1997'
_computing_molecular_graphics    'XP, Ver. 6.10, Bruker AXS Inc., 2000'
_computing_publication_material  'SHELXTL-Bruker AXS Inc., 1998'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart Aepex 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  0.0618
_diffrn_reflns_av_sigmaI/netI    0.1190
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9945
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0587
_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)+(0.0803P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1705
_reflns_number_gt                2814
_reflns_number_total             3660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b808390h.txt
_cod_data_source_block           TQ3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7202256
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18011(11) 1.12991(15) 0.74730(6) 0.1078(9) Uani 1 1 d . . .
H1 H 0.2430 1.1863 0.7786 0.129 Uiso 1 1 calc R . .
C2 C 0.05749(11) 1.18297(15) 0.72425(6) 0.169(2) Uani 1 1 d R . .
H2 H 0.0385 1.2757 0.7392 0.203 Uiso 1 1 d R . .
C3 C -0.03352(11) 1.09681(15) 0.67970(6) 0.191(2) Uani 1 1 d R . .
H3 H -0.1156 1.1295 0.6656 0.229 Uiso 1 1 d R . .
C4 C -0.00843(11) 0.96999(15) 0.65642(6) 0.1603(18) Uani 1 1 d R . .
H4 H -0.0721 0.9153 0.6248 0.192 Uiso 1 1 d R . .
C5 C 0.11208(11) 0.91558(15) 0.67813(6) 0.1081(9) Uani 1 1 d R . .
H5 H 0.1290 0.8239 0.6616 0.130 Uiso 1 1 d R . .
C6 C 0.20727(11) 0.99730(15) 0.72431(6) 0.0644(5) Uani 1 1 d R . .
C7 C 0.33818(16) 0.9378(2) 0.74784(10) 0.0660(5) Uani 1 1 d . . .
H7A H 0.3550 0.9028 0.7107 0.079 Uiso 1 1 calc R . .
H7B H 0.3954 1.0210 0.7687 0.079 Uiso 1 1 calc R . .
C8 C 0.38156(16) 0.6646(2) 0.77971(8) 0.0560(4) Uani 1 1 d . . .
H8 H 0.3860 0.6470 0.7395 0.067 Uiso 1 1 calc R . .
C9 C 0.39724(16) 0.5452(2) 0.82065(8) 0.0558(4) Uani 1 1 d . . .
H9 H 0.4134 0.4476 0.8087 0.067 Uiso 1 1 calc R . .
C10 C 0.38932(13) 0.56699(19) 0.88140(7) 0.0496(4) Uani 1 1 d . . .
C11 C 0.37119(16) 0.7203(2) 0.89698(8) 0.0580(5) Uani 1 1 d . . .
H11 H 0.3687 0.7423 0.9373 0.070 Uiso 1 1 calc R . .
C12 C 0.35744(17) 0.8352(2) 0.85387(8) 0.0581(5) Uani 1 1 d . . .
H12 H 0.3461 0.9355 0.8653 0.070 Uiso 1 1 calc R . .
C13 C 0.33573(14) 1.04385(19) 0.99107(8) 0.0483(4) Uani 1 1 d . . .
C14 C 0.37712(14) 0.87013(18) 1.08221(8) 0.0506(4) Uani 1 1 d . . .
C15 C 0.29072(14) 0.93665(17) 1.02383(7) 0.0456(4) Uani 1 1 d . . .
C16 C 0.16381(13) 0.88763(17) 0.99686(7) 0.0432(4) Uani 1 1 d . . .
C17 C 0.12121(13) 0.76769(18) 1.02515(7) 0.0477(4) Uani 1 1 d . . .
H17 H 0.1771 0.7181 1.0620 0.057 Uiso 1 1 calc R . .
C18 C 0.00000(14) 0.72219(17) 0.99996(8) 0.0488(4) Uani 1 1 d . . .
H18 H -0.0253 0.6428 1.0200 0.059 Uiso 1 1 calc R . .
C19 C -0.08839(13) 0.79410(17) 0.94352(7) 0.0436(4) Uani 1 1 d . . .
C20 C -0.04504(14) 0.91169(19) 0.91419(7) 0.0505(4) Uani 1 1 d . . .
H20 H -0.1004 0.9593 0.8766 0.061 Uiso 1 1 calc R . .
C21 C 0.07663(14) 0.95743(18) 0.93967(7) 0.0495(4) Uani 1 1 d . . .
H21 H 0.1025 1.0354 0.9192 0.059 Uiso 1 1 calc R . .
C22 C -0.21540(14) 0.74820(19) 0.91734(7) 0.0475(4) Uani 1 1 d . . .
C23 C -0.25995(14) 0.63389(19) 0.94732(8) 0.0505(4) Uani 1 1 d . . .
C24 C -0.30110(15) 0.80849(19) 0.85767(8) 0.0529(4) Uani 1 1 d . . .
N1 N 0.35970(12) 0.80861(16) 0.79487(7) 0.0517(4) Uani 1 1 d . . .
N2 N 0.39642(14) 0.45085(17) 0.92135(8) 0.0678(5) Uani 1 1 d . . .
H2A H 0.4062 0.3583 0.9104 0.081 Uiso 1 1 calc R . .
H2B H 0.3912 0.4680 0.9582 0.081 Uiso 1 1 calc R . .
N3 N 0.36892(15) 1.12874(19) 0.96161(8) 0.0671(5) Uani 1 1 d . . .
N4 N 0.44544(14) 0.81610(18) 1.13006(8) 0.0689(5) Uani 1 1 d . . .
N5 N -0.29552(15) 0.54040(18) 0.97272(9) 0.0707(5) Uani 1 1 d . . .
N6 N -0.36923(15) 0.8566(2) 0.80864(8) 0.0707(5) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.2 . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 118.9 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 121.5 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.6 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 118.7 . . ?
C1 C6 C7 121.40(10) . . ?
C5 C6 C7 119.87(10) . . ?
N1 C7 C6 111.88(14) . . ?
N1 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 N1 122.31(15) . . ?
C9 C8 H8 118.8 . . ?
N1 C8 H8 118.8 . . ?
C8 C9 C10 120.45(16) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
N2 C10 C9 122.28(16) . . ?
N2 C10 C11 121.85(15) . . ?
C9 C10 C11 115.87(16) . . ?
C12 C11 C10 120.61(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N1 C12 C11 121.71(16) . . ?
N1 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
N3 C13 C15 176.88(16) . . ?
N4 C14 C15 178.65(18) . . ?
C13 C15 C14 117.85(14) . . ?
C13 C15 C16 121.14(13) . . ?
C14 C15 C16 120.86(14) . . ?
C17 C16 C21 117.53(13) . . ?
C17 C16 C15 121.61(13) . . ?
C21 C16 C15 120.85(14) . . ?
C18 C17 C16 121.65(14) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 121.05(15) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 117.30(14) . . ?
C20 C19 C22 121.36(13) . . ?
C18 C19 C22 121.34(15) . . ?
C21 C20 C19 121.53(13) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C16 120.91(15) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C23 C22 C24 116.69(14) . . ?
C23 C22 C19 121.67(14) . . ?
C24 C22 C19 121.53(15) . . ?
N5 C23 C22 179.16(18) . . ?
N6 C24 C22 178.71(19) . . ?
C12 N1 C8 118.93(15) . . ?
C12 N1 C7 119.74(15) . . ?
C8 N1 C7 121.34(15) . . ?
C10 N2 H2A 120.0 . . ?
C10 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3473 . ?
C1 C2 1.3989 . ?
C1 H1 0.9300 . ?
C2 C3 1.3598 . ?
C2 H2 0.9300 . ?
C3 C4 1.2983 . ?
C3 H3 0.9300 . ?
C4 C5 1.3824 . ?
C4 H4 0.9300 . ?
C5 C6 1.3795 . ?
C5 H5 0.9300 . ?
C6 C7 1.503(2) . ?
C7 N1 1.487(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.344(2) . ?
C8 N1 1.345(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.405(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.325(2) . ?
C10 C11 1.412(2) . ?
C11 C12 1.349(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.345(2) . ?
C12 H12 0.9300 . ?
C13 N3 1.151(2) . ?
C13 C15 1.406(2) . ?
C14 N4 1.1519(19) . ?
C14 C15 1.420(2) . ?
C15 C16 1.431(2) . ?
C16 C17 1.405(2) . ?
C16 C21 1.418(2) . ?
C17 C18 1.363(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.421(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.409(2) . ?
C19 C22 1.424(2) . ?
C20 C21 1.369(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.405(2) . ?
C22 C24 1.414(2) . ?
C23 N5 1.156(2) . ?
C24 N6 1.149(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.6 . . . . ?
C1 C2 C3 C4 -2.6 . . . . ?
C2 C3 C4 C5 2.3 . . . . ?
C3 C4 C5 C6 -0.9 . . . . ?
C2 C1 C6 C5 -0.3 . . . . ?
C2 C1 C6 C7 179.65(10) . . . . ?
C4 C5 C6 C1 -0.1 . . . . ?
C4 C5 C6 C7 179.98(10) . . . . ?
C1 C6 C7 N1 103.30(13) . . . . ?
C5 C6 C7 N1 -76.79(15) . . . . ?
N1 C8 C9 C10 1.0(3) . . . . ?
C8 C9 C10 N2 175.66(15) . . . . ?
C8 C9 C10 C11 -3.3(2) . . . . ?
N2 C10 C11 C12 -176.31(16) . . . . ?
C9 C10 C11 C12 2.7(2) . . . . ?
C10 C11 C12 N1 0.4(3) . . . . ?
N3 C13 C15 C14 142(3) . . . . ?
N3 C13 C15 C16 -34(3) . . . . ?
N4 C14 C15 C13 145(7) . . . . ?
N4 C14 C15 C16 -39(8) . . . . ?
C13 C15 C16 C17 172.44(14) . . . . ?
C14 C15 C16 C17 -3.0(2) . . . . ?
C13 C15 C16 C21 -6.6(2) . . . . ?
C14 C15 C16 C21 178.02(14) . . . . ?
C21 C16 C17 C18 -1.8(2) . . . . ?
C15 C16 C17 C18 179.17(15) . . . . ?
C16 C17 C18 C19 0.4(2) . . . . ?
C17 C18 C19 C20 1.2(2) . . . . ?
C17 C18 C19 C22 -179.35(14) . . . . ?
C18 C19 C20 C21 -1.4(2) . . . . ?
C22 C19 C20 C21 179.18(16) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C17 C16 C21 C20 1.6(2) . . . . ?
C15 C16 C21 C20 -179.35(15) . . . . ?
C20 C19 C22 C23 -178.27(14) . . . . ?
C18 C19 C22 C23 2.3(2) . . . . ?
C20 C19 C22 C24 5.8(2) . . . . ?
C18 C19 C22 C24 -173.63(15) . . . . ?
C24 C22 C23 N5 -153(13) . . . . ?
C19 C22 C23 N5 31(13) . . . . ?
C23 C22 C24 N6 -122(9) . . . . ?
C19 C22 C24 N6 54(9) . . . . ?
C11 C12 N1 C8 -2.9(3) . . . . ?
C11 C12 N1 C7 177.11(16) . . . . ?
C9 C8 N1 C12 2.2(3) . . . . ?
C9 C8 N1 C7 -177.78(15) . . . . ?
C6 C7 N1 C12 -67.3(2) . . . . ?
C6 C7 N1 C8 112.72(18) . . . . ?
