#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:25:37 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179630 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/94/4509408.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509408
loop_
_publ_author_name
'Hudson, Timothy A.'
'Robson, Richard'
_publ_section_title
;
 A New Class of TCNQ Derivatives Easily Generated from TCNQH2Containing
 Discrete TCNQ2−Anions and Noncoordinating Cations
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1658
_journal_paper_doi               10.1021/cg801400j
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         '(C12 H4 N4 2-), (C12 H12 N2 2+)'
_chemical_formula_sum            'C24 H16 N6'
_chemical_formula_weight         388.43
_chemical_name_systematic
;
 ?
;
_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                101.318(4)
_cell_angle_beta                 100.927(4)
_cell_angle_gamma                113.272(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7203(4)
_cell_length_b                   9.7795(4)
_cell_length_c                   12.7972(6)
_cell_measurement_reflns_used    4612
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      72.89
_cell_measurement_theta_min      3.69
_cell_volume                     938.85(9)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.0711
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'XCalibur - Oxford Diffraction'
_diffrn_measurement_method       'φ & ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6723
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         3.69
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            BLACK
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'IRREGULAR BLOCK'
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0770P)²+0.0895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                3010
_reflns_number_total             3498
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg801400jsup5.cif
_cod_data_source_block           tcndiqu
_cod_original_cell_volume        938.85(7)
_cod_database_code               4509408
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C -0.28727(17) 0.20697(15) 0.95911(11) 0.0320(3) Uani 1 1 d .
C2 C -0.14076(17) 0.20185(16) 0.93087(11) 0.0330(3) Uani 1 1 d .
C3 C -0.05956(17) 0.30798(17) 0.87605(12) 0.0373(3) Uani 1 1 d .
C4 C -0.07092(16) 0.09832(15) 0.96445(10) 0.0308(3) Uani 1 1 d .
C5 C -0.14121(16) 0.00542(15) 1.03061(11) 0.0318(3) Uani 1 1 d .
H5 H -0.2370 0.0075 1.0514 0.038 Uiso 1 1 calc R
C6 C -0.07249(16) -0.08882(15) 1.06561(11) 0.0320(3) Uani 1 1 d .
H6 H -0.1221 -0.1474 1.1101 0.038 Uiso 1 1 calc R
C13 C 0.4076(2) 0.51031(17) 0.82796(12) 0.0394(3) Uani 1 1 d .
H13 H 0.2956 0.4551 0.8324 0.047 Uiso 1 1 calc R
C14 C 0.5368(2) 0.46921(18) 0.86651(12) 0.0437(3) Uani 1 1 d .
H14 H 0.5124 0.3855 0.8955 0.052 Uiso 1 1 calc R
C15 C 0.7029(2) 0.55427(18) 0.86131(12) 0.0434(4) Uani 1 1 d .
H15 H 0.7924 0.5298 0.8886 0.052 Uiso 1 1 calc R
C16 C 0.73619(19) 0.67605(17) 0.81542(12) 0.0384(3) Uani 1 1 d .
H16 H 0.8480 0.7333 0.8115 0.046 Uiso 1 1 calc R
C17 C 0.60293(17) 0.71257(15) 0.77542(10) 0.0317(3) Uani 1 1 d .
C18 C 0.62920(16) 0.83713(15) 0.72218(10) 0.0310(3) Uani 1 1 d .
C19 C 0.76526(17) 0.89333(17) 0.67743(11) 0.0366(3) Uani 1 1 d .
H19 H 0.8455 0.8526 0.6805 0.044 Uiso 1 1 calc R
C20 C 0.78238(19) 1.01003(18) 0.62805(12) 0.0408(3) Uani 1 1 d .
H20 H 0.8741 1.0479 0.5979 0.049 Uiso 1 1 calc R
C21 C 0.66337(19) 1.07026(18) 0.62359(12) 0.0419(3) Uani 1 1 d .
H21 H 0.6740 1.1490 0.5906 0.050 Uiso 1 1 calc R
C22 C 0.52869(19) 1.01233(17) 0.66856(12) 0.0382(3) Uani 1 1 d .
H22 H 0.4477 1.0521 0.6661 0.046 Uiso 1 1 calc R
C23 C 0.37179(18) 0.84240(17) 0.76812(12) 0.0351(3) Uani 1 1 d .
H23A H 0.2804 0.8701 0.7395 0.042 Uiso 1 1 calc R
H23B H 0.4173 0.8906 0.8483 0.042 Uiso 1 1 calc R
C24 C 0.29896(17) 0.66835(16) 0.74139(12) 0.0350(3) Uani 1 1 d .
H24A H 0.2071 0.6294 0.7759 0.042 Uiso 1 1 calc R
H24B H 0.2493 0.6200 0.6613 0.042 Uiso 1 1 calc R
N1 N -0.40909(16) 0.20734(15) 0.98176(11) 0.0412(3) Uani 1 1 d .
N2 N 0.00659(18) 0.39578(17) 0.83031(13) 0.0503(3) Uani 1 1 d .
N5 N 0.44169(14) 0.62898(13) 0.78412(9) 0.0322(3) Uani 1 1 d .
N6 N 0.51354(14) 0.89862(13) 0.71600(9) 0.0316(3) Uani 1 1 d .
C7 C 0.03356(18) 0.29150(16) 0.51480(12) 0.0361(3) Uani 1 1 d .
C8 C 0.20062(17) 0.30254(16) 0.55737(12) 0.0354(3) Uani 1 1 d .
C9 C 0.21420(17) 0.20436(17) 0.62119(12) 0.0376(3) Uani 1 1 d .
C10 C 0.35216(17) 0.40336(16) 0.52863(11) 0.0333(3) Uani 1 1 d .
C11 C 0.34361(18) 0.50755(17) 0.46916(11) 0.0351(3) Uani 1 1 d .
H11 H 0.2392 0.5140 0.4478 0.042 Uiso 1 1 calc R
C12 C 0.51355(17) 0.39928(16) 0.55844(11) 0.0345(3) Uani 1 1 d .
H12 H 0.5244 0.3317 0.5980 0.041 Uiso 1 1 calc R
N3 N -0.10402(16) 0.28149(16) 0.47947(12) 0.0461(3) Uani 1 1 d .
N4 N 0.22847(17) 0.12477(16) 0.67509(12) 0.0467(3) 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 0.0181 0.0091 '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 0.0311 0.0180 '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
N1 C1 C2 178.36(14) . .
C3 C2 C1 116.52(12) . .
C3 C2 C4 122.16(12) . .
C1 C2 C4 121.18(12) . .
N2 C3 C2 179.54(16) . .
C5 C4 C6 116.40(12) . 2_557
C5 C4 C2 121.71(12) . .
C6 C4 C2 121.87(12) 2_557 .
C6 C5 C4 122.05(12) . .
C5 C6 C4 121.54(12) . 2_557
N5 C13 C14 120.66(14) . .
C15 C14 C13 118.87(14) . .
C14 C15 C16 119.89(13) . .
C15 C16 C17 119.89(14) . .
N5 C17 C16 118.83(13) . .
N5 C17 C18 118.89(11) . .
C16 C17 C18 122.27(13) . .
N6 C18 C19 118.61(12) . .
N6 C18 C17 118.60(12) . .
C19 C18 C17 122.78(12) . .
C18 C19 C20 120.02(13) . .
C21 C20 C19 119.91(13) . .
C22 C21 C20 119.06(14) . .
N6 C22 C21 120.33(13) . .
N6 C23 C24 108.61(11) . .
N5 C24 C23 108.91(11) . .
C13 N5 C17 121.83(12) . .
C13 N5 C24 119.35(11) . .
C17 N5 C24 118.81(11) . .
C22 N6 C18 122.06(12) . .
C22 N6 C23 119.46(11) . .
C18 N6 C23 118.42(11) . .
N3 C7 C8 179.58(17) . .
C9 C8 C7 117.43(12) . .
C9 C8 C10 121.02(12) . .
C7 C8 C10 121.37(12) . .
N4 C9 C8 178.81(16) . .
C11 C10 C12 116.45(12) . .
C11 C10 C8 121.99(12) . .
C12 C10 C8 121.56(13) . .
C12 C11 C10 121.52(12) 2_666 .
C11 C12 C10 122.03(13) 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.1541(17) .
C1 C2 1.4085(18) .
C2 C3 1.4016(19) .
C2 C4 1.4627(19) .
C3 N2 1.1604(19) .
C4 C5 1.4059(18) .
C4 C6 1.4074(17) 2_557
C5 C6 1.3805(19) .
C6 C4 1.4074(17) 2_557
C13 N5 1.3401(18) .
C13 C14 1.379(2) .
C14 C15 1.378(2) .
C15 C16 1.383(2) .
C16 C17 1.3836(18) .
C17 N5 1.3581(17) .
C17 C18 1.4713(19) .
C18 N6 1.3612(16) .
C18 C19 1.3798(19) .
C19 C20 1.381(2) .
C20 C21 1.379(2) .
C21 C22 1.375(2) .
C22 N6 1.3423(18) .
C23 N6 1.4813(16) .
C23 C24 1.5008(19) .
C24 N5 1.4832(16) .
C7 N3 1.1565(18) .
C7 C8 1.4080(18) .
C8 C9 1.401(2) .
C8 C10 1.4666(19) .
C9 N4 1.1627(19) .
C10 C11 1.402(2) .
C10 C12 1.4052(19) .
C11 C12 1.3794(19) 2_666
C12 C11 1.3794(19) 2_666
