#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:05:35 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180373 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/42/7204291.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_7204291
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         'C10 H8 O2 S6, C18 H10 N4'
_chemical_formula_sum            'C28 H18 N4 O2 S6'
_chemical_formula_weight         634.82
_chemical_name_common            (EOET)(H2TCNDQ)
_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                80.614(6)
_cell_angle_beta                 87.995(6)
_cell_angle_gamma                84.202(6)
_cell_formula_units_Z            1
_cell_length_a                   5.4850(5)
_cell_length_b                   9.0560(10)
_cell_length_c                   14.4370(16)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0
_cell_volume                     703.77(13)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_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    0.0276
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2668
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0636P)²+0.5323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1624
_reflns_number_gt                2188
_reflns_number_total             2668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b109503j.txt
_cod_data_source_block           (EOET)(H2TCNDQ)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204291
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
S1 S -0.13379(19) 0.13551(11) 0.60752(8) 0.0885(4) Uani 1 1 d . . .
S2 S 0.26840(19) -0.11001(11) 0.60358(8) 0.0852(3) Uani 1 1 d . . .
S3 S -0.0304(3) 0.1798(2) 0.78717(10) 0.0953(5) Uani 0.50 1 d P . .
O3 O -0.0304(3) 0.1798(2) 0.78717(10) 0.0953(5) Uani 0.50 1 d P . .
S4 S 0.4344(3) -0.08441(19) 0.77987(11) 0.0992(5) Uani 0.50 1 d P . .
O4 O 0.4344(3) -0.08441(19) 0.77987(11) 0.0992(5) Uani 0.50 1 d P . .
C5 C 0.1132(12) 0.0663(7) 0.8769(3) 0.1214(18) Uani 1 1 d . . .
H5A H 0.1059 0.1186 0.9298 0.146 Uiso 1 1 calc R . .
H5B H 0.0236 -0.0202 0.8940 0.146 Uiso 1 1 calc R . .
C6 C 0.3708(12) 0.0136(6) 0.8599(4) 0.128(2) Uani 1 1 d . . .
H6A H 0.4325 -0.0439 0.9176 0.154 Uiso 1 1 calc R . .
H6B H 0.4605 0.1005 0.8463 0.154 Uiso 1 1 calc R . .
C7 C 0.0528(7) 0.0854(4) 0.7051(3) 0.0759(9) Uani 1 1 d . . .
C8 C 0.2341(7) -0.0231(4) 0.7030(3) 0.0739(9) Uani 1 1 d . . .
C9 C 0.0278(6) 0.0054(4) 0.5438(3) 0.0706(8) Uani 1 1 d . . .
N10 N 1.0237(6) 0.6433(6) 0.8785(2) 0.1181(15) Uani 1 1 d . . .
N11 N 0.5285(9) 0.3107(5) 0.9575(2) 0.1100(13) Uani 1 1 d . . .
C12 C 0.8438(7) 0.6035(5) 0.8622(2) 0.0815(11) Uani 1 1 d . . .
C13 C 0.6082(6) 0.5519(4) 0.84158(19) 0.0646(8) Uani 1 1 d . . .
H13 H 0.4822 0.6282 0.8539 0.078 Uiso 1 1 calc R . .
C14 C 0.5653(7) 0.4151(5) 0.9068(2) 0.0785(10) Uani 1 1 d . . .
C15 C 0.5858(5) 0.5333(3) 0.73855(18) 0.0560(7) Uani 1 1 d . . .
C16 C 0.7380(6) 0.5980(4) 0.6691(2) 0.0639(8) Uani 1 1 d . . .
H16 H 0.8683 0.6521 0.6851 0.077 Uiso 1 1 calc R . .
C17 C 0.7033(5) 0.5853(4) 0.57617(19) 0.0608(7) Uani 1 1 d . . .
H17 H 0.8097 0.6320 0.5284 0.073 Uiso 1 1 calc R . .
C18 C 0.5184(5) 0.5066(3) 0.55024(16) 0.0468(6) Uani 1 1 d . . .
C19 C 0.3705(6) 0.4409(4) 0.62146(19) 0.0609(7) Uani 1 1 d . . .
H19 H 0.2421 0.3849 0.6062 0.073 Uiso 1 1 calc R . .
C20 C 0.4032(6) 0.4538(4) 0.71449(19) 0.0671(8) Uani 1 1 d . . .
H20 H 0.2975 0.4071 0.7625 0.081 Uiso 1 1 calc R . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C7 S1 C9 93.89(17) . . ?
C8 S2 C9 94.12(17) . . ?
C7 S3 C5 98.7(2) . . ?
C6 S4 C8 104.1(3) . . ?
C6 C5 S3 116.4(4) . . ?
C6 C5 H5A 108.2 . . ?
S3 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
S3 C5 H5B 108.2 . . ?
H5A C5 H5B 107.3 . . ?
C5 C6 S4 118.9(4) . . ?
C5 C6 H6A 107.6 . . ?
S4 C6 H6A 107.6 . . ?
C5 C6 H6B 107.6 . . ?
S4 C6 H6B 107.6 . . ?
H6A C6 H6B 107.0 . . ?
C8 C7 S3 129.4(3) . . ?
C8 C7 S1 118.4(3) . . ?
S3 C7 S1 112.2(2) . . ?
C7 C8 S4 128.3(3) . . ?
C7 C8 S2 118.1(3) . . ?
S4 C8 S2 113.7(2) . . ?
C9 C9 S2 122.0(4) 2_556 . ?
C9 C9 S1 122.6(4) 2_556 . ?
S2 C9 S1 115.5(2) . . ?
N10 C12 C13 179.6(4) . . ?
C14 C13 C12 109.6(3) . . ?
C14 C13 C15 112.6(3) . . ?
C12 C13 C15 113.4(3) . . ?
C14 C13 H13 107.0 . . ?
C12 C13 H13 107.0 . . ?
C15 C13 H13 107.0 . . ?
N11 C14 C13 178.9(5) . . ?
C20 C15 C16 119.1(2) . . ?
C20 C15 C13 119.0(3) . . ?
C16 C15 C13 121.8(3) . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 121.8(3) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 117.0(2) . . ?
C19 C18 C18 121.5(3) . 2_666 ?
C17 C18 C18 121.5(3) . 2_666 ?
C18 C19 C20 121.6(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C19 120.5(3) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
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
S1 C7 1.742(4) . ?
S1 C9 1.762(4) . ?
S2 C8 1.743(4) . ?
S2 C9 1.757(3) . ?
S3 C7 1.599(4) . ?
S3 C5 1.682(6) . ?
S4 C6 1.578(5) . ?
S4 C8 1.584(4) . ?
C5 C6 1.470(7) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C7 C8 1.329(5) . ?
C9 C9 1.332(7) 2_556 ?
N10 C12 1.129(4) . ?
N11 C14 1.128(5) . ?
C12 C13 1.473(4) . ?
C13 C14 1.463(5) . ?
C13 C15 1.535(4) . ?
C13 H13 0.9600 . ?
C15 C20 1.376(4) . ?
C15 C16 1.376(4) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9600 . ?
C17 C18 1.391(4) . ?
C17 H17 0.9600 . ?
C18 C19 1.382(4) . ?
C18 C18 1.497(5) 2_666 ?
C19 C20 1.387(4) . ?
C19 H19 0.9600 . ?
C20 H20 0.9600 . ?
