#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/74/1507443.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_1507443
loop_
_publ_author_name
'Morita, Yasushi'
'Maki, Suguru'
'Ohmoto, Makoto'
'Kitagawa, Hiroshi'
'Okubo, Takashi'
'Mitani, Tadaoki'
'Nakasuji, Kazuhiro'
_publ_section_title
;
 Hydrogen-Bonded Charge-Transfer Complexes of TTF Containing a Uracil
 Moiety:  Crystal Structures and Electronic Properties of the
 Hydrogen Cyananilate and TCNQ Complexes
;
_journal_issue                   13
_journal_name_full               'Organic Letters'
_journal_page_first              2185
_journal_paper_doi               10.1021/ol020081z
_journal_volume                  4
_journal_year                    2002
_chemical_formula_moiety
'C14 H14 N2 O2 S4 1+, C8 H N2 O4 1-, C2 H3 N''
_chemical_formula_sum            'C24 H18 N5 O6 S4'
_chemical_formula_weight         600.69
_chemical_melting_point          471.0(10)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Wed Feb 13 22:08:45 2002'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                106.198(2)
_cell_angle_beta                 91.656(6)
_cell_angle_gamma                108.415(4)
_cell_formula_units_Z            2
_cell_length_a                   11.1052(7)
_cell_length_b                   13.194(1)
_cell_length_c                   9.958(1)
_cell_measurement_reflns_used    4760
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      1.7
_cell_volume                     1318.39(19)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9866
_diffrn_measured_fraction_theta_max 0.9866
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8239
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.360
_refine_ls_number_parameters     397
_refine_ls_number_reflns         2755
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.2551
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00031|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                2755
_reflns_number_total             5960
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol020081z.cif
_cod_data_source_block           TnbU-HCNAL
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '470-472' was changed to '471.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1318.3(2)
_cod_original_sg_symbol_H-M      'P -1         '
_cod_original_formula_sum        'C24 H18 N5 O6 S4 '
_cod_database_code               1507443
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_calc_flag
S(1) S 0.7950(1) 0.2981(1) 0.4612(2) 0.0449(4) Uani 1.00 d
S(2) S 0.9966(1) 0.5288(1) 0.2382(2) 0.0501(5) Uani 1.00 d
S(3) S 0.7763(1) 0.5119(1) 0.4502(2) 0.0445(4) Uani 1.00 d
S(4) S 1.0154(1) 0.3197(1) 0.2632(2) 0.0531(5) Uani 1.00 d
O(1) O 0.3769(3) 0.0788(3) 0.8422(4) 0.060(1) Uani 1.00 d
O(2) O 0.6659(4) 0.0993(3) 0.0803(4) 0.061(1) Uani 1.00 d
O(4) O 0.6693(3) 0.4431(3) 0.0396(4) 0.061(1) Uani 1.00 d
O(6) O 0.4871(3) 0.1013(3) 0.2552(4) 0.058(1) Uani 1.00 d
O(7) O 0.6800(4) 0.1221(3) 0.5461(4) 0.065(1) Uani 1.00 d
O(8) O 0.4887(3) 0.4496(3) 0.2174(4) 0.062(1) Uani 1.00 d
N(5) N 0.4358(4) 0.2400(3) 0.7797(4) 0.042(1) Uani 1.00 d
N(6) N 0.5281(4) 0.1034(3) 0.6935(5) 0.048(1) Uani 1.00 d
N(7) N 0.3248(5) 0.2949(4) 0.4256(5) 0.073(2) Uani 1.00 d
N(8) N 0.8486(5) 0.2760(4) -0.1075(5) 0.067(2) Uani 1.00 d
N(9) N 0.1302(7) 0.1437(6) 0.0712(9) 0.132(3) Uani 1.00 d
C(1) C 0.5236(4) 0.1832(4) 0.2100(5) 0.041(2) Uani 1.00 d
C(2) C 0.7699(5) 0.2707(4) -0.0358(6) 0.044(2) Uani 1.00 d
C(3) C 0.4427(5) 0.1356(4) 0.7752(6) 0.045(2) Uani 1.00 d
C(4) C 0.5143(5) 0.3048(4) 0.7104(6) 0.041(2) Uani 1.00 d
C(5) C 0.6794(4) 0.3434(4) 0.5536(5) 0.035(1) Uani 1.00 d
C(6) C 0.5261(5) 0.3680(4) 0.1888(5) 0.045(2) Uani 1.00 d
C(7) C 0.6755(4) 0.4430(4) 0.5473(6) 0.042(2) Uani 1.00 d
C(9) C 0.9424(4) 0.4200(4) 0.3084(5) 0.040(2) Uani 1.00 d
C(10) C 0.8487(4) 0.4119(4) 0.3980(5) 0.040(2) Uani 1.00 d
C(11) C 0.3926(5) 0.2816(4) 0.3429(6) 0.048(2) Uani 1.00 d
C(12) C 0.4812(5) 0.2760(4) 0.2435(5) 0.042(2) Uani 1.00 d
C(13) C 0.6275(4) 0.3656(4) 0.0869(5) 0.044(2) Uani 1.00 d
C(14) C 0.6723(5) 0.2698(4) 0.0554(5) 0.041(2) Uani 1.00 d
C(16) C 0.6085(5) 0.1623(4) 0.6152(6) 0.046(2) Uani 1.00 d
C(17) C 0.3423(6) 0.2825(4) 0.8596(6) 0.048(2) Uani 1.00 d
C(18) C 0.2303(6) 0.2778(5) 0.7648(7) 0.055(2) Uani 1.00 d
C(19) C 1.1078(5) 0.4792(5) 0.1493(6) 0.054(2) Uani 1.00 d
C(20) C 1.1149(5) 0.3837(5) 0.1588(6) 0.057(2) Uani 1.00 d
C(21) C 0.1554(6) 0.1647(6) 0.6698(8) 0.070(3) Uani 1.00 d
C(22) C 0.1379(7) 0.0761(6) 0.1189(9) 0.096(3) Uani 1.00 d
C(24) C 0.1531(7) -0.0044(6) 0.1848(10) 0.124(4) Uani 1.00 d
C(25) C 0.0397(8) 0.1668(6) 0.580(1) 0.088(3) Uani 1.00 d
C(26) C 0.5992(4) 0.2726(4) 0.6288(5) 0.038(2) Uani 1.00 d
C(27) C 0.6238(5) 0.1840(4) 0.1102(5) 0.042(2) Uani 1.00 d
H(1) H 1.150(5) 0.522(4) 0.095(5) 0.0731 Uiso 1.00 calc
H(2) H 1.165(5) 0.342(4) 0.117(5) 0.0731 Uiso 1.00 calc
H(3) H 0.615(5) 0.484(4) 0.602(5) 0.0731 Uiso 1.00 calc
H(4) H 0.504(5) 0.373(4) 0.719(5) 0.0731 Uiso 1.00 calc
H(5) H 0.532(5) 0.040(4) 0.693(6) 0.0731 Uiso 1.00 calc
H(6) H 0.305(5) 0.234(4) 0.908(5) 0.0731 Uiso 1.00 calc
H(7) H 0.377(5) 0.353(4) 0.897(6) 0.0731 Uiso 1.00 calc
H(8) H 0.168(5) 0.305(4) 0.832(5) 0.0731 Uiso 1.00 calc
H(9) H 0.262(5) 0.333(4) 0.710(5) 0.0731 Uiso 1.00 calc
H(10) H 0.127(5) 0.110(4) 0.727(5) 0.0731 Uiso 1.00 calc
H(11) H 0.215(5) 0.142(4) 0.616(6) 0.0731 Uiso 1.00 calc
H(12) H 0.070(5) 0.208(4) 0.528(6) 0.0731 Uiso 1.00 calc
H(13) H -0.016(5) 0.188(4) 0.632(6) 0.0731 Uiso 1.00 calc
H(14) H -0.003(5) 0.097(5) 0.515(6) 0.0731 Uiso 1.00 calc
H(15) H 0.1357 0.0164 0.2803 0.1435 Uiso 1.00 calc
H(16) H 0.0960 -0.0764 0.1356 0.1435 Uiso 1.00 calc
H(17) H 0.2390 -0.0045 0.1851 0.1435 Uiso 1.00 calc
H(18) H 0.636(5) 0.053(4) 0.131(6) 0.0731 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(5) S(1) C(10) 95.0(2) yes
C(9) S(2) C(19) 94.7(3) yes
C(7) S(3) C(10) 95.0(2) yes
C(9) S(4) C(20) 94.7(3) yes
C(3) N(5) C(4) 120.8(4) yes
C(3) N(5) C(17) 120.4(4) yes
C(4) N(5) C(17) 118.8(4) yes
C(3) N(6) C(16) 128.0(4) yes
O(6) C(1) C(12) 126.1(4) yes
O(6) C(1) C(27) 117.1(4) yes
C(12) C(1) C(27) 116.8(4) yes
N(8) C(2) C(14) 177.2(5) yes
O(1) C(3) N(5) 121.4(4) yes
O(1) C(3) N(6) 123.5(4) yes
N(5) C(3) N(6) 115.0(4) yes
N(5) C(4) C(26) 124.0(4) yes
S(1) C(5) C(7) 114.9(3) yes
S(1) C(5) C(26) 118.5(3) yes
C(7) C(5) C(26) 126.6(4) yes
O(8) C(6) C(12) 124.5(5) yes
O(8) C(6) C(13) 117.8(4) yes
C(12) C(6) C(13) 117.7(4) yes
S(3) C(7) C(5) 119.3(4) yes
S(2) C(9) S(4) 115.4(3) yes
S(2) C(9) C(10) 123.8(3) yes
S(4) C(9) C(10) 120.8(3) yes
S(1) C(10) S(3) 115.8(3) yes
S(1) C(10) C(9) 121.6(3) yes
S(3) C(10) C(9) 122.6(3) yes
N(7) C(11) C(12) 174.8(5) yes
C(1) C(12) C(6) 124.1(4) yes
C(1) C(12) C(11) 118.6(4) yes
C(6) C(12) C(11) 117.2(4) yes
O(4) C(13) C(6) 119.7(4) yes
O(4) C(13) C(14) 122.8(4) yes
C(6) C(13) C(14) 117.5(4) yes
C(2) C(14) C(13) 116.8(4) yes
C(2) C(14) C(27) 121.8(4) yes
C(13) C(14) C(27) 121.4(4) yes
O(7) C(16) N(6) 120.4(4) yes
O(7) C(16) C(26) 125.7(4) yes
N(6) C(16) C(26) 113.9(4) yes
N(5) C(17) C(18) 112.7(5) yes
C(17) C(18) C(21) 115.1(5) yes
S(2) C(19) C(20) 117.6(4) yes
S(4) C(20) C(19) 117.4(4) yes
C(18) C(21) C(25) 111.6(6) yes
N(9) C(22) C(24) 177(1) yes
C(4) C(26) C(5) 122.2(4) yes
C(4) C(26) C(16) 118.2(4) yes
C(5) C(26) C(16) 119.6(4) yes
O(2) C(27) C(1) 117.5(4) yes
O(2) C(27) C(14) 120.1(4) yes
C(1) C(27) C(14) 122.5(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(5) 1.762(4) yes
S(1) C(10) 1.730(4) yes
S(2) C(9) 1.716(5) yes
S(2) C(19) 1.729(6) yes
S(3) C(7) 1.710(4) yes
S(3) C(10) 1.723(5) yes
S(4) C(9) 1.725(5) yes
S(4) C(20) 1.726(5) yes
O(1) C(3) 1.224(5) yes
O(2) C(27) 1.308(5) yes
O(4) C(13) 1.211(5) yes
O(6) C(1) 1.241(5) yes
O(7) C(16) 1.215(5) yes
O(8) C(6) 1.237(5) yes
N(5) C(3) 1.395(6) yes
N(5) C(4) 1.363(5) yes
N(5) C(17) 1.480(6) yes
N(6) C(3) 1.359(6) yes
N(6) C(16) 1.395(6) yes
N(7) C(11) 1.145(6) yes
N(8) C(2) 1.143(6) yes
N(9) C(22) 1.142(9) yes
C(1) C(12) 1.403(6) yes
C(1) C(27) 1.512(6) yes
C(2) C(14) 1.433(6) yes
C(4) C(26) 1.355(6) yes
C(5) C(7) 1.344(6) yes
C(5) C(26) 1.460(6) yes
C(6) C(12) 1.421(6) yes
C(6) C(13) 1.541(6) yes
C(9) C(10) 1.389(6) yes
C(11) C(12) 1.422(7) yes
C(13) C(14) 1.460(6) yes
C(14) C(27) 1.358(6) yes
C(16) C(26) 1.462(6) yes
C(17) C(18) 1.516(8) yes
C(18) C(21) 1.479(9) yes
C(19) C(20) 1.311(8) yes
C(21) C(25) 1.55(1) yes
C(22) C(24) 1.44(1) yes
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_publ_flag
S(1) C(5) C(7) S(3) 1.6(6) yes
S(1) C(5) C(26) C(4) 175.1(4) yes
S(1) C(5) C(26) C(16) -5.6(7) yes
S(1) C(10) S(3) C(7) -0.8(4) yes
S(1) C(10) C(9) S(2) 178.3(3) yes
S(1) C(10) C(9) S(4) -3.2(6) yes
S(2) C(9) S(4) C(20) -0.7(4) yes
S(2) C(9) C(10) S(3) -0.6(7) yes
S(2) C(19) C(20) S(4) -1.6(8) yes
S(3) C(7) C(5) C(26) -178.8(4) yes
S(3) C(10) S(1) C(5) 1.5(4) yes
S(3) C(10) C(9) S(4) 178.0(3) yes
S(4) C(9) S(2) C(19) 0.0(4) yes
O(1) C(3) N(5) C(4) 176.5(5) yes
O(1) C(3) N(5) C(17) -3.8(8) yes
O(1) C(3) N(6) C(16) -179.0(6) yes
O(2) C(27) C(1) O(6) -0.9(8) yes
O(2) C(27) C(1) C(12) 178.7(5) yes
O(2) C(27) C(14) C(2) -0.2(9) yes
O(2) C(27) C(14) C(13) -179.8(5) yes
O(4) C(13) C(6) O(8) 1.2(8) yes
O(4) C(13) C(6) C(12) -179.1(5) yes
O(4) C(13) C(14) C(2) 0.2(9) yes
O(4) C(13) C(14) C(27) 179.8(6) yes
O(6) C(1) C(12) C(6) 179.9(6) yes
O(6) C(1) C(12) C(11) 3.1(9) yes
O(6) C(1) C(27) C(14) -179.2(5) yes
O(7) C(16) N(6) C(3) -179.8(6) yes
O(7) C(16) C(26) C(4) -179.6(6) yes
O(7) C(16) C(26) C(5) 1.1(9) yes
O(8) C(6) C(12) C(1) 179.7(6) yes
O(8) C(6) C(12) C(11) -3.4(9) yes
O(8) C(6) C(13) C(14) 179.2(5) yes
N(5) C(3) N(6) C(16) 0.0(9) yes
N(5) C(4) C(26) C(5) 178.4(5) yes
N(5) C(4) C(26) C(16) -0.8(8) yes
N(5) C(17) C(18) C(21) 58.5(7) yes
N(6) C(3) N(5) C(4) -2.5(8) yes
N(6) C(3) N(5) C(17) 177.2(5) yes
N(6) C(16) C(26) C(4) -1.5(8) yes
N(6) C(16) C(26) C(5) 179.2(5) yes
N(7) C(11) C(12) C(1) 153(6) yes
N(7) C(11) C(12) C(6) -23(7) yes
N(8) C(2) C(14) C(13) 13(12) yes
N(8) C(2) C(14) C(27) -166(12) yes
C(1) C(12) C(6) C(13) 0.0(8) yes
C(1) C(27) C(14) C(2) 178.1(5) yes
C(1) C(27) C(14) C(13) -1.5(9) yes
C(2) C(14) C(13) C(6) -177.8(5) yes
C(3) N(5) C(4) C(26) 3.0(8) yes
C(3) N(5) C(17) C(18) -105.7(6) yes
C(3) N(6) C(16) C(26) 2.0(8) yes
C(4) N(5) C(17) C(18) 74.0(6) yes
C(4) C(26) C(5) C(7) -4.4(9) yes
C(5) S(1) C(10) C(9) -177.5(4) yes
C(5) C(7) S(3) C(10) -0.5(5) yes
C(6) C(12) C(1) C(27) 0.4(8) yes
C(6) C(13) C(14) C(27) 1.8(8) yes
C(7) S(3) C(10) C(9) 178.1(5) yes
C(7) C(5) S(1) C(10) -1.8(5) yes
C(7) C(5) C(26) C(16) 174.8(5) yes
C(9) S(2) C(19) C(20) 1.0(6) yes
C(9) S(4) C(20) C(19) 1.4(6) yes
C(10) S(1) C(5) C(26) 178.6(4) yes
C(10) C(9) S(2) C(19) 178.6(5) yes
C(10) C(9) S(4) C(20) -179.3(5) yes
C(11) C(12) C(1) C(27) -176.5(5) yes
C(11) C(12) C(6) C(13) 176.9(5) yes
C(12) C(1) C(27) C(14) 0.4(8) yes
C(12) C(6) C(13) C(14) -1.1(7) yes
C(17) N(5) C(4) C(26) -176.7(6) yes
C(17) C(18) C(21) C(25) 178.0(5) yes
C(17) C(18) C(21) C(25) 178.0(5) yes
