#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:05:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180373 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/42/7204294.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_7204294
loop_
_publ_author_name
'Nishimura, Kazukuni'
'Khasanov, Salavat S.'
'Saito, Gunzi'
_publ_section_title
;
 Charge transfer, proton transfer and clathrate compounds of
 dihydrotetracyanodiphenoquinodimethane (H2TCNDQ) having highly acidic
 protonsElectronic supplementary information (ESI) available: elemental
 analysis results for H2TCNDQ complexes. See
 http://www.rsc.org/suppdata/jm/b1/b109503j/
;
_journal_issue                   6
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1693
_journal_paper_doi               10.1039/b109503j
_journal_volume                  12
_journal_year                    2002
_chemical_formula_moiety         'C16 H20 N2, 2(C18 H10 N4)'
_chemical_formula_sum            'C52 H40 N10'
_chemical_formula_weight         804.94
_chemical_name_common            (3,3,5,5-TMB)(H2TCNDQ)2
_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 (C-H) / difmap (N-H)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.515(11)
_cell_angle_beta                 97.681(13)
_cell_angle_gamma                92.765(10)
_cell_formula_units_Z            1
_cell_length_a                   7.5200(18)
_cell_length_b                   10.638(2)
_cell_length_c                   14.505(3)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0
_cell_volume                     1063.9(4)
_computing_cell_refinement       'MXC(MAC Science)'
_computing_data_collection       'MXC(MAC Science)'
_computing_data_reduction        Crystan
_computing_molecular_graphics    'ORTEP III'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Mac Science DIP-2020K'
_diffrn_measurement_method       theta/2theta
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3853
_diffrn_reflns_theta_full        26.13
_diffrn_reflns_theta_max         26.13
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    'noref (C-H) / refall (N-H)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0602P)²+0.4107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                2898
_reflns_number_total             3853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b109503j.txt
_cod_data_source_block           (3,3,5,5-TMB)(H2TCNDQ)2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204294
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2226(3) 0.78309(18) 0.17398(14) 0.0511(4) Uani 1 1 d . . .
H1A H 0.135(3) 0.742(2) 0.1196(17) 0.050 Uiso 1 1 d . . .
H1B H 0.312(3) 0.831(2) 0.1647(17) 0.050 Uiso 1 1 d . . .
C2 C 0.1572(3) 0.84675(18) 0.26460(13) 0.0418(4) Uani 1 1 d . . .
C3 C 0.2686(3) 0.94871(19) 0.34625(14) 0.0429(4) Uani 1 1 d . . .
C4 C 0.2047(3) 1.00631(18) 0.43683(14) 0.0430(4) Uani 1 1 d . . .
H4 H 0.2817 1.0761 0.4917 0.050 Uiso 1 1 calc R . .
C5 C 0.0339(3) 0.96749(17) 0.45171(13) 0.0388(4) Uani 1 1 d . . .
C6 C -0.0708(3) 0.86366(19) 0.36932(13) 0.0427(4) Uani 1 1 d . . .
H6 H -0.1882 0.8329 0.3768 0.050 Uiso 1 1 calc R . .
C7 C -0.0136(3) 0.80284(18) 0.27730(13) 0.0434(5) Uani 1 1 d . . .
C8 C -0.1367(3) 0.6921(2) 0.19274(16) 0.0612(6) Uani 1 1 d . . .
H8A H -0.2348 0.6625 0.2186 0.050 Uiso 1 1 calc R . .
H8B H -0.0701 0.6168 0.1630 0.050 Uiso 1 1 calc R . .
H8C H -0.1836 0.7265 0.1428 0.050 Uiso 1 1 calc R . .
C9 C 0.4534(3) 0.9959(2) 0.33483(17) 0.0580(6) Uani 1 1 d . . .
H9A H 0.4421 1.0429 0.2894 0.050 Uiso 1 1 calc R . .
H9B H 0.5191 0.9188 0.3087 0.050 Uiso 1 1 calc R . .
H9C H 0.5170 1.0561 0.3991 0.050 Uiso 1 1 calc R . .
C10 C 0.0214(3) 0.55331(19) 0.55160(14) 0.0433(5) Uani 1 1 d . . .
C11 C 0.0331(4) 0.6909(2) 0.56902(16) 0.0697(7) Uani 1 1 d . . .
H11 H 0.0143 0.7182 0.5126 0.050 Uiso 1 1 calc R . .
C12 C 0.0708(4) 0.7904(2) 0.66490(16) 0.0685(7) Uani 1 1 d . . .
H12 H 0.0780 0.8847 0.6739 0.050 Uiso 1 1 calc R . .
C13 C 0.0979(3) 0.7544(2) 0.74709(14) 0.0456(5) Uani 1 1 d . . .
C14 C 0.0898(3) 0.6190(2) 0.73236(15) 0.0517(5) Uani 1 1 d . . .
H14 H 0.1108 0.5926 0.7892 0.050 Uiso 1 1 calc R . .
C15 C 0.0517(3) 0.5199(2) 0.63604(15) 0.0523(5) Uani 1 1 d . . .
H15 H 0.0461 0.4258 0.6276 0.050 Uiso 1 1 calc R . .
C16 C 0.1286(3) 0.8622(2) 0.85446(15) 0.0491(5) Uani 1 1 d . . .
H16 H 0.1685 0.8191 0.9001 0.050 Uiso 1 1 calc R . .
C17 C 0.2661(3) 0.9746(3) 0.86936(17) 0.0607(6) Uani 1 1 d . . .
C18 C -0.0429(3) 0.9174(2) 0.87862(16) 0.0530(5) Uani 1 1 d . . .
N19 N 0.3723(4) 1.0598(3) 0.87836(19) 0.0914(8) Uani 1 1 d . . .
N20 N -0.1779(3) 0.9565(2) 0.89455(17) 0.0755(6) Uani 1 1 d . . .
C21 C 0.5188(2) 0.50335(18) 0.55268(13) 0.0389(4) Uani 1 1 d . . .
C22 C 0.5389(4) 0.6252(2) 0.63409(15) 0.0640(7) Uani 1 1 d . . .
H22 H 0.5295 0.7080 0.6223 0.050 Uiso 1 1 calc R . .
C23 C 0.5722(4) 0.6319(2) 0.73209(15) 0.0628(7) Uani 1 1 d . . .
H23 H 0.5839 0.7184 0.7868 0.050 Uiso 1 1 calc R . .
C24 C 0.5884(3) 0.51615(19) 0.75154(13) 0.0410(4) Uani 1 1 d . . .
C25 C 0.5710(4) 0.3939(2) 0.67215(16) 0.0634(7) Uani 1 1 d . . .
H25 H 0.5824 0.3117 0.6844 0.050 Uiso 1 1 calc R . .
C26 C 0.5368(4) 0.3881(2) 0.57412(15) 0.0661(7) Uani 1 1 d . . .
H26 H 0.5254 0.3014 0.5197 0.050 Uiso 1 1 calc R . .
C27 C 0.6266(3) 0.5211(2) 0.85948(14) 0.0455(5) Uani 1 1 d . . .
H27 H 0.6301 0.4296 0.8565 0.050 Uiso 1 1 calc R . .
C28 C 0.8015(3) 0.5981(2) 0.91342(15) 0.0532(5) Uani 1 1 d . . .
C29 C 0.4854(3) 0.5815(2) 0.91767(15) 0.0515(5) Uani 1 1 d . . .
N30 N 0.9364(3) 0.6575(3) 0.95472(15) 0.0799(7) Uani 1 1 d . . .
N31 N 0.3761(3) 0.6292(3) 0.96227(16) 0.0805(7) 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
C2 N1 H1A 114.3(14) . . ?
C2 N1 H1B 114.3(15) . . ?
H1A N1 H1B 115(2) . . ?
C7 C2 N1 120.60(18) . . ?
C7 C2 C3 119.23(17) . . ?
N1 C2 C3 120.00(19) . . ?
C4 C3 C2 119.26(18) . . ?
C4 C3 C9 120.58(18) . . ?
C2 C3 C9 120.16(17) . . ?
C3 C4 C5 123.18(17) . . ?
C3 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C6 115.69(17) . . ?
C4 C5 C5 122.5(2) . 2_576 ?
C6 C5 C5 121.8(2) . 2_576 ?
C7 C6 C5 123.44(19) . . ?
C7 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
C6 C7 C2 119.16(17) . . ?
C6 C7 C8 119.53(19) . . ?
C2 C7 C8 121.30(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 116.25(18) . . ?
C11 C10 C10 122.2(2) . 2_566 ?
C15 C10 C10 121.5(2) . 2_566 ?
C12 C11 C10 122.4(2) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 118.95(18) . . ?
C12 C13 C16 121.27(18) . . ?
C14 C13 C16 119.73(18) . . ?
C13 C14 C15 120.60(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 121.68(19) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C18 C16 C17 109.35(19) . . ?
C18 C16 C13 109.61(17) . . ?
C17 C16 C13 112.85(18) . . ?
C18 C16 H16 108.3 . . ?
C17 C16 H16 108.3 . . ?
C13 C16 H16 108.3 . . ?
N19 C17 C16 178.3(3) . . ?
N20 C18 C16 177.7(2) . . ?
C26 C21 C22 116.36(18) . . ?
C26 C21 C21 121.7(2) . 2_666 ?
C22 C21 C21 121.9(2) . 2_666 ?
C21 C22 C23 122.13(19) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C24 C23 C22 120.47(19) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 118.64(18) . . ?
C23 C24 C27 121.42(17) . . ?
C25 C24 C27 119.94(18) . . ?
C24 C25 C26 120.50(19) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 121.90(19) . . ?
C21 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C29 C27 C28 108.43(17) . . ?
C29 C27 C24 112.10(16) . . ?
C28 C27 C24 111.85(16) . . ?
C29 C27 H27 108.1 . . ?
C28 C27 H27 108.1 . . ?
C24 C27 H27 108.1 . . ?
N30 C28 C27 179.8(2) . . ?
N31 C29 C27 179.3(3) . . ?
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
N1 C2 1.407(2) . ?
N1 H1A 0.91(2) . ?
N1 H1B 0.88(2) . ?
C2 C7 1.404(3) . ?
C2 C3 1.409(3) . ?
C3 C4 1.392(3) . ?
C3 C9 1.506(3) . ?
C4 C5 1.398(3) . ?
C4 H4 0.9600 . ?
C5 C6 1.402(3) . ?
C5 C5 1.488(3) 2_576 ?
C6 C7 1.390(3) . ?
C6 H6 0.9600 . ?
C7 C8 1.510(3) . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9599 . ?
C8 H8C 0.9599 . ?
C9 H9A 0.9599 . ?
C9 H9B 0.9599 . ?
C9 H9C 0.9599 . ?
C10 C11 1.387(3) . ?
C10 C15 1.390(3) . ?
C10 C10 1.491(4) 2_566 ?
C11 C12 1.386(3) . ?
C11 H11 0.9600 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9600 . ?
C13 C14 1.374(3) . ?
C13 C16 1.537(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9600 . ?
C15 H15 0.9600 . ?
C16 C18 1.475(3) . ?
C16 C17 1.475(3) . ?
C16 H16 0.9600 . ?
C17 N19 1.137(3) . ?
C18 N20 1.136(3) . ?
C21 C26 1.379(3) . ?
C21 C22 1.382(3) . ?
C21 C21 1.491(3) 2_666 ?
C22 C23 1.385(3) . ?
C22 H22 0.9600 . ?
C23 C24 1.368(3) . ?
C23 H23 0.9600 . ?
C24 C25 1.371(3) . ?
C24 C27 1.535(2) . ?
C25 C26 1.389(3) . ?
C25 H25 0.9600 . ?
C26 H26 0.9600 . ?
C27 C29 1.470(3) . ?
C27 C28 1.471(3) . ?
C27 H27 0.9600 . ?
C28 N30 1.134(3) . ?
C29 N31 1.137(3) . ?
