#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:23:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180391 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/60/7206029.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_7206029
loop_
_publ_author_name
'Murata, Tsuyoshi'
'Yakiyama, Yumi'
'Nakasuji, Kazuhiro'
'Morita, Yasushi'
_publ_section_title
;
 Proton-transfer salts between an EDT-TTF derivative having
 imidazole-ring and anilic acids: multi-dimensional networks by
 acid--base hydrogen-bonds, π-stacks and chalcogen atom interactions
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3689
_journal_paper_doi               10.1039/c1ce05326d
_journal_volume                  13
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H9 N2 S6, C8 N2 O4'
_chemical_formula_sum            'C15 H9 N3 O2 S6'
_chemical_formula_weight         455.61
_chemical_name_common            (EDTTTFImH)2(CNA)
_chemical_name_systematic
;
(EDTTTFImH)2(CNA)
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-03-16T19:25:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                92.16(3)
_cell_angle_beta                 114.66(2)
_cell_angle_gamma                112.01(2)
_cell_formula_units_Z            2
_cell_length_a                   9.762(5)
_cell_length_b                   10.467(8)
_cell_length_c                   10.572(7)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     885.7(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8728
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.4
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0505P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                3198
_reflns_number_total             3992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05326d.txt
_cod_data_source_block           texray
_cod_database_code               7206029
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
O1 O 0.72838(18) 0.45401(17) 0.44786(16) 0.0248(3) Uani 1 1 d . . .
O2 O 0.59972(18) 0.62786(16) 0.31580(16) 0.0251(3) Uani 1 1 d . . .
C12 C 0.6259(2) 0.4746(2) 0.4762(2) 0.0208(5) Uani 1 1 d . . .
C15 C 0.6444(3) 0.3219(2) 0.6454(2) 0.0258(5) Uani 1 1 d . . .
N3 N 0.7019(3) 0.2500(2) 0.7069(2) 0.0389(5) Uani 1 1 d . . .
C13 C 0.5483(2) 0.5704(2) 0.3980(2) 0.0200(4) Uani 1 1 d . . .
C14 C 0.5739(2) 0.4115(2) 0.5742(2) 0.0201(4) Uani 1 1 d . . .
S1 S 0.35253(6) 0.25905(6) 0.17515(6) 0.02290(15) Uani 1 1 d . . .
S4 S -0.17926(6) 0.10643(6) 0.05357(6) 0.02228(15) Uani 1 1 d . . .
S3 S 0.12728(6) 0.19771(6) 0.32950(6) 0.02538(15) Uani 1 1 d . . .
S2 S 0.06145(6) 0.18183(6) -0.10965(6) 0.02372(15) Uani 1 1 d . . .
S6 S -0.40788(7) 0.04813(7) 0.18078(6) 0.03269(17) Uani 1 1 d . . .
S5 S -0.04197(7) 0.16697(8) 0.50985(6) 0.03529(18) Uani 1 1 d . . .
C7 C 0.0396(2) 0.1769(2) 0.1433(2) 0.0186(4) Uani 1 1 d . . .
C6 C 0.1357(2) 0.2047(2) 0.0766(2) 0.0195(4) Uani 1 1 d . . .
C3 C 0.5649(3) 0.3599(2) 0.0566(2) 0.0197(4) Uani 1 1 d . . .
N2 N 0.7010(2) 0.42041(19) 0.1840(2) 0.0229(4) Uani 1 1 d . . .
H2 H 0.7007 0.4314 0.2783 0.027 Uiso 1 1 calc R . .
C5 C 0.2577(3) 0.2585(2) -0.0997(2) 0.0224(5) Uani 1 1 d . . .
H5 H 0.2712 0.2738 -0.1874 0.027 Uiso 1 1 calc R . .
C9 C -0.2015(3) 0.1096(2) 0.2110(2) 0.0214(5) Uani 1 1 d . . .
C4 C 0.3923(2) 0.2972(2) 0.0303(2) 0.0202(4) Uani 1 1 d . . .
C8 C -0.0611(3) 0.1532(2) 0.3372(2) 0.0232(5) Uani 1 1 d . . .
C11 C -0.3828(3) 0.0843(3) 0.3592(3) 0.0285(5) Uani 1 1 d . . .
H7A H -0.3502 0.1874 0.3897 0.034 Uiso 1 1 calc R . .
H7B H -0.4924 0.03 0.358 0.034 Uiso 1 1 calc R . .
C10 C -0.2524(3) 0.0456(3) 0.4679(2) 0.0288(5) Uani 1 1 d . . .
H6A H -0.2734 -0.0523 0.4293 0.035 Uiso 1 1 calc R . .
H6B H -0.2638 0.0454 0.5576 0.035 Uiso 1 1 calc R . .
C2 C 0.8417(3) 0.4653(2) 0.1647(3) 0.0277(5) Uani 1 1 d . . .
H4 H 0.9603 0.5138 0.2413 0.033 Uiso 1 1 calc R . .
C1 C 0.7887(3) 0.4313(3) 0.0232(2) 0.0282(5) Uani 1 1 d . . .
H3 H 0.8611 0.4498 -0.0249 0.034 Uiso 1 1 calc R . .
N1 N 0.6163(2) 0.3661(2) -0.0436(2) 0.0256(4) Uani 1 1 d . . .
H1 H 0.5421 0.3296 -0.149 0.031 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 0 '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 0.006 '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
O1 C12 C14 123.2(2) . . ?
O1 C12 C13 118.33(18) . . ?
C14 C12 C13 118.46(18) . . ?
N3 C15 C14 178.1(2) . . ?
O2 C13 C14 124.7(2) . 2_666 ?
O2 C13 C12 117.13(18) . . ?
C14 C13 C12 118.13(17) 2_666 . ?
C13 C14 C12 123.40(19) 2_666 . ?
C13 C14 C15 118.13(18) 2_666 . ?
C12 C14 C15 118.44(18) . . ?
C4 S1 C6 94.71(10) . . ?
C7 S4 C9 95.04(10) . . ?
C7 S3 C8 95.57(10) . . ?
C5 S2 C6 95.03(10) . . ?
C9 S6 C11 102.37(11) . . ?
C8 S5 C10 99.33(11) . . ?
C6 C7 S3 121.16(17) . . ?
C6 C7 S4 123.94(17) . . ?
S3 C7 S4 114.75(11) . . ?
C7 C6 S2 125.27(17) . . ?
C7 C6 S1 120.42(17) . . ?
S2 C6 S1 114.21(11) . . ?
N2 C3 N1 107.63(18) . . ?
N2 C3 C4 126.56(19) . . ?
N1 C3 C4 125.8(2) . . ?
C3 N2 C2 109.21(18) . . ?
C3 N2 H2 125.4 . . ?
C2 N2 H2 125.4 . . ?
C4 C5 S2 118.03(17) . . ?
C4 C5 H5 121 . . ?
S2 C5 H5 121 . . ?
C8 C9 S6 128.32(17) . . ?
C8 C9 S4 117.36(16) . . ?
S6 C9 S4 114.27(12) . . ?
C5 C4 C3 124.88(19) . . ?
C5 C4 S1 116.76(16) . . ?
C3 C4 S1 118.27(16) . . ?
C9 C8 S5 128.25(17) . . ?
C9 C8 S3 116.81(17) . . ?
S5 C8 S3 114.91(12) . . ?
C10 C11 S6 113.10(15) . . ?
C10 C11 H7A 109 . . ?
S6 C11 H7A 109 . . ?
C10 C11 H7B 109 . . ?
S6 C11 H7B 109 . . ?
H7A C11 H7B 107.8 . . ?
C11 C10 S5 112.40(17) . . ?
C11 C10 H6A 109.1 . . ?
S5 C10 H6A 109.1 . . ?
C11 C10 H6B 109.1 . . ?
S5 C10 H6B 109.1 . . ?
H6A C10 H6B 107.9 . . ?
C1 C2 N2 106.89(19) . . ?
C1 C2 H4 126.6 . . ?
N2 C2 H4 126.6 . . ?
C2 C1 N1 107.60(19) . . ?
C2 C1 H3 126.2 . . ?
N1 C1 H3 126.2 . . ?
C3 N1 C1 108.67(19) . . ?
C3 N1 H1 125.7 . . ?
C1 N1 H1 125.7 . . ?
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
O1 C12 1.243(2) . ?
O2 C13 1.243(2) . ?
C12 C14 1.416(3) . ?
C12 C13 1.540(3) . ?
C15 N3 1.163(3) . ?
C15 C14 1.423(3) . ?
C13 C14 1.415(3) 2_666 ?
C14 C13 1.415(3) 2_666 ?
S1 C4 1.755(2) . ?
S1 C6 1.761(2) . ?
S4 C7 1.756(2) . ?
S4 C9 1.766(2) . ?
S3 C7 1.754(2) . ?
S3 C8 1.758(2) . ?
S2 C5 1.732(2) . ?
S2 C6 1.762(2) . ?
S6 C9 1.747(2) . ?
S6 C11 1.804(3) . ?
S5 C8 1.750(2) . ?
S5 C10 1.809(2) . ?
C7 C6 1.351(3) . ?
C3 N2 1.339(3) . ?
C3 N1 1.342(3) . ?
C3 C4 1.455(3) . ?
N2 C2 1.381(3) . ?
N2 H2 1 . ?
C5 C4 1.353(3) . ?
C5 H5 1 . ?
C9 C8 1.352(3) . ?
C11 C10 1.519(3) . ?
C11 H7A 1 . ?
C11 H7B 1 . ?
C10 H6A 1 . ?
C10 H6B 1 . ?
C2 C1 1.344(3) . ?
C2 H4 1 . ?
C1 N1 1.382(3) . ?
C1 H3 1 . ?
N1 H1 1 . ?
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
O1 C12 C13 O2 -3.7(3) . . . . ?
C14 C12 C13 O2 177.9(2) . . . . ?
O1 C12 C13 C14 177.20(19) . . . 2_666 ?
C14 C12 C13 C14 -1.2(3) . . . 2_666 ?
O1 C12 C14 C13 -177.1(2) . . . 2_666 ?
C13 C12 C14 C13 1.3(3) . . . 2_666 ?
O1 C12 C14 C15 1.1(3) . . . . ?
C13 C12 C14 C15 179.38(18) . . . . ?
C8 S3 C7 C6 177.38(19) . . . . ?
C8 S3 C7 S4 -6.98(14) . . . . ?
C9 S4 C7 C6 -178.2(2) . . . . ?
C9 S4 C7 S3 6.32(14) . . . . ?
S3 C7 C6 S2 177.59(12) . . . . ?
S4 C7 C6 S2 2.4(3) . . . . ?
S3 C7 C6 S1 1.5(3) . . . . ?
S4 C7 C6 S1 -173.76(11) . . . . ?
C5 S2 C6 C7 173.4(2) . . . . ?
C5 S2 C6 S1 -10.29(13) . . . . ?
C4 S1 C6 C7 -172.31(19) . . . . ?
C4 S1 C6 S2 11.17(13) . . . . ?
N1 C3 N2 C2 -0.4(2) . . . . ?
C4 C3 N2 C2 179.1(2) . . . . ?
C6 S2 C5 C4 4.93(19) . . . . ?
C11 S6 C9 C8 8.8(3) . . . . ?
C11 S6 C9 S4 -173.85(12) . . . . ?
C7 S4 C9 C8 -2.9(2) . . . . ?
C7 S4 C9 S6 179.39(12) . . . . ?
S2 C5 C4 C3 178.62(16) . . . . ?
S2 C5 C4 S1 2.2(2) . . . . ?
N2 C3 C4 C5 168.3(2) . . . . ?
N1 C3 C4 C5 -12.4(3) . . . . ?
N2 C3 C4 S1 -15.4(3) . . . . ?
N1 C3 C4 S1 163.92(17) . . . . ?
C6 S1 C4 C5 -8.12(19) . . . . ?
C6 S1 C4 C3 175.26(16) . . . . ?
S6 C9 C8 S5 -2.2(4) . . . . ?
S4 C9 C8 S5 -179.55(13) . . . . ?
S6 C9 C8 S3 175.80(13) . . . . ?
S4 C9 C8 S3 -1.5(3) . . . . ?
C10 S5 C8 C9 21.7(2) . . . . ?
C10 S5 C8 S3 -156.37(14) . . . . ?
C7 S3 C8 C9 5.1(2) . . . . ?
C7 S3 C8 S5 -176.59(13) . . . . ?
C9 S6 C11 C10 -43.3(2) . . . . ?
S6 C11 C10 S5 72.5(2) . . . . ?
C8 S5 C10 C11 -55.81(18) . . . . ?
C3 N2 C2 C1 0.2(3) . . . . ?
N2 C2 C1 N1 0.1(3) . . . . ?
N2 C3 N1 C1 0.4(2) . . . . ?
C4 C3 N1 C1 -179.0(2) . . . . ?
C2 C1 N1 C3 -0.3(3) . . . . ?
