#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/98/4109854.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_4109854
loop_
_publ_author_name
'Tsuyoshi Murata'
'Yasushi Morita'
'Yumi Yakiyama'
'Kozo Fukui'
'Hideki Yamochi'
'Gunzi Saito'
'Kazuhiro Nakasuji'
_publ_contact_author_address
;
    ENTER ADDRESS
;
_publ_contact_author_email       morita@chem.sci.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6850-5395
_publ_contact_author_name        'Morita Yasushi'
_publ_contact_author_phone       +81-6-6850-5393
_publ_section_title
;
 Hydrogen-Bond Interaction in Organic Conductors: Redox Activation,
 Molecular Recognition, Structural Regulation, and Proton Transfer in
 Donor-Acceptor Charge-Transfer Complexes of TTF-Imidazole
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10837
_journal_page_last               10846
_journal_paper_doi               10.1021/ja072607m
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C9 H7 N2 S4 2+, C6 N2 O8 2-, C2 H3 N1'
_chemical_formula_sum            'C17 H10 N5 O8 S4'
_chemical_formula_weight         540.58
_chemical_name_common            TTFIm-NA
_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             'Sun Jun  4 00:33:40 2006'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                81.89(2)
_cell_angle_beta                 66.33(2)
_cell_angle_gamma                65.98(2)
_cell_formula_units_Z            2
_cell_length_a                   9.543(4)
_cell_length_b                   11.055(5)
_cell_length_c                   11.867(5)
_cell_measurement_reflns_used    2262
_cell_measurement_temperature    200.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      4.2
_cell_volume                     1047.0(8)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 2.0'
_computing_molecular_graphics    'Ortep-3 for Windows'
_computing_publication_material  'teXsan Ver. 2.0'
_computing_structure_refinement  'teXsan Ver. 2.0'
_computing_structure_solution    SHELXS86
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.9819
_diffrn_measured_fraction_theta_max 0.9819
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10299
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            BLACK
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             550.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.82
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.525
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3126
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.0021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.03000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                3126
_reflns_number_total             4716
_reflns_threshold_expression     F²>3.0σ(F²)
_cod_data_source_file            ja072607msi20070707_051907.cif
_cod_data_source_block           TTF2Im-NA
_cod_original_cell_volume        1046.9(8)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C17 H10 N5 O8 S4 '
_cod_database_code               4109854
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
S(1) S 0.2135(1) 0.82366(9) 0.59982(8) 0.0361(2) Uani 1.00 1 d
S(2) S 0.1036(1) 0.74847(8) 0.43297(8) 0.0335(2) Uani 1.00 1 d
S(3) S -0.1643(1) 1.01483(9) 0.75465(8) 0.0356(2) Uani 1.00 1 d
S(4) S -0.2781(1) 0.92547(9) 0.60174(9) 0.0412(2) Uani 1.00 1 d
O(1) O 0.6999(3) 0.6286(2) 0.1338(2) 0.0400(6) Uani 1.00 1 d
O(2) O 0.6235(3) 0.4245(2) 0.2385(2) 0.0342(6) Uani 1.00 1 d
O(3) O 0.6818(3) 0.2960(2) -0.1461(2) 0.0442(6) Uani 1.00 1 d
O(4) O 0.7902(3) 0.4851(2) -0.2527(2) 0.0428(6) Uani 1.00 1 d
O(5) O 0.5438(3) 0.2249(3) 0.2106(2) 0.0504(7) Uani 1.00 1 d
O(6) O 0.7054(4) 0.1233(2) 0.0362(2) 0.0521(7) Uani 1.00 1 d
O(7) O 0.9210(4) 0.6582(3) -0.2015(3) 0.0798(9) Uani 1.00 1 d
O(8) O 0.6859(3) 0.7888(3) -0.0770(3) 0.0525(7) Uani 1.00 1 d
N(1) N 0.6689(3) 0.6161(3) 0.3661(2) 0.0347(7) Uani 1.00 1 d
N(2) N 0.5886(3) 0.6564(3) 0.5602(2) 0.0332(7) Uani 1.00 1 d
N(3) N 0.6334(3) 0.2251(3) 0.1017(3) 0.0362(7) Uani 1.00 1 d
N(4) N 0.7872(4) 0.6778(3) -0.1169(3) 0.0409(8) Uani 1.00 1 d
N(5) N -0.8350(6) 1.1181(5) 0.7255(5) 0.099(2) Uani 1.00 1 d
C(1) C 0.8089(4) 0.5843(4) 0.3912(3) 0.0379(9) Uani 1.00 1 d
C(2) C 0.7596(4) 0.6091(3) 0.5114(3) 0.0363(8) Uani 1.00 1 d
C(3) C 0.5365(4) 0.6602(3) 0.4703(3) 0.0316(8) Uani 1.00 1 d
C(4) C 0.3636(4) 0.7076(3) 0.4827(3) 0.0308(8) Uani 1.00 1 d
C(5) C 0.3099(4) 0.6746(3) 0.4066(3) 0.0324(8) Uani 1.00 1 d
C(6) C 0.0517(4) 0.8397(3) 0.5619(3) 0.0294(7) Uani 1.00 1 d
C(7) C -0.1127(4) 0.9174(3) 0.6315(3) 0.0313(8) Uani 1.00 1 d
C(8) C -0.3754(4) 1.0719(3) 0.7953(3) 0.0405(9) Uani 1.00 1 d
C(9) C -0.4276(4) 1.0299(4) 0.7255(3) 0.0414(9) Uani 1.00 1 d
C(10) C 0.7014(4) 0.5514(3) 0.0654(3) 0.0329(8) Uani 1.00 1 d
C(11) C 0.6569(4) 0.4329(3) 0.1259(3) 0.0267(7) Uani 1.00 1 d
C(12) C 0.6623(4) 0.3423(3) 0.0488(3) 0.0310(8) Uani 1.00 1 d
C(13) C 0.6958(4) 0.3620(3) -0.0793(3) 0.0325(8) Uani 1.00 1 d
C(14) C 0.7504(4) 0.4762(3) -0.1403(3) 0.0339(8) Uani 1.00 1 d
C(15) C 0.7466(4) 0.5640(3) -0.0621(3) 0.0327(8) Uani 1.00 1 d
C(16) C -0.8736(5) 1.1434(5) 0.8249(5) 0.069(1) Uani 1.00 1 d
C(17) C -0.9155(5) 1.1742(5) 0.9510(5) 0.077(2) Uani 1.00 1 d
H(1) H 0.6668 0.6058 0.2882 0.0587 Uiso 1.00 1 calc
H(2) H 0.5193 0.6821 0.6445 0.0574 Uiso 1.00 1 calc
H(3) H 0.9197 0.5514 0.3332 0.0647 Uiso 1.00 1 calc
H(4) H 0.8281 0.5958 0.5561 0.0631 Uiso 1.00 1 calc
H(5) H 0.3842 0.6123 0.3400 0.0587 Uiso 1.00 1 calc
H(6) H -0.4505 1.1291 0.8660 0.0663 Uiso 1.00 1 calc
H(7) H -0.5422 1.0539 0.7436 0.0736 Uiso 1.00 1 calc
H(8) H -0.8278 1.1220 0.9772 0.1093 Uiso 1.00 1 calc
H(9) H -0.9354 1.2667 0.9586 0.1093 Uiso 1.00 1 calc
H(10) H -1.0138 1.1616 1.0029 0.1093 Uiso 1.00 1 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)
;
N N 0.006 0.003
;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)
;
O O 0.011 0.006
;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)
;
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(4) S(1) C(6) 94.9(2) yes
C(5) S(2) C(6) 94.9(2) yes
C(7) S(3) C(8) 95.7(2) yes
C(7) S(4) C(9) 95.3(2) yes
C(1) N(1) C(3) 108.2(3) yes
C(2) N(2) C(3) 108.7(3) yes
O(5) N(3) O(6) 120.8(3) yes
O(5) N(3) C(12) 120.7(3) yes
O(6) N(3) C(12) 118.4(3) yes
O(7) N(4) O(8) 122.8(3) yes
O(7) N(4) C(15) 118.4(3) yes
O(8) N(4) C(15) 118.8(3) yes
N(1) C(1) C(2) 107.8(3) yes
N(2) C(2) C(1) 106.9(3) yes
N(1) C(3) N(2) 108.4(3) yes
N(1) C(3) C(4) 125.5(3) yes
N(2) C(3) C(4) 126.1(3) yes
S(1) C(4) C(3) 118.0(3) yes
S(1) C(4) C(5) 116.4(2) yes
C(3) C(4) C(5) 125.5(3) yes
S(2) C(5) C(4) 117.9(2) yes
S(1) C(6) S(2) 115.9(2) yes
S(1) C(6) C(7) 122.7(3) yes
S(2) C(6) C(7) 121.4(3) yes
S(3) C(7) S(4) 114.9(2) yes
S(3) C(7) C(6) 121.7(3) yes
S(4) C(7) C(6) 123.5(3) yes
S(3) C(8) C(9) 116.7(3) yes
S(4) C(9) C(8) 117.3(3) yes
O(1) C(10) C(11) 117.2(3) yes
O(1) C(10) C(15) 124.2(3) yes
C(11) C(10) C(15) 118.6(3) yes
O(2) C(11) C(10) 115.7(3) yes
O(2) C(11) C(12) 126.5(3) yes
C(10) C(11) C(12) 117.8(3) yes
N(3) C(12) C(11) 118.9(3) yes
N(3) C(12) C(13) 118.2(3) yes
C(11) C(12) C(13) 122.9(3) yes
O(3) C(13) C(12) 125.2(3) yes
O(3) C(13) C(14) 116.2(3) yes
C(12) C(13) C(14) 118.6(3) yes
O(4) C(14) C(13) 117.2(3) yes
O(4) C(14) C(15) 125.7(3) yes
C(13) C(14) C(15) 117.1(3) yes
N(4) C(15) C(10) 117.4(3) yes
N(4) C(15) C(14) 118.0(3) yes
C(10) C(15) C(14) 124.6(3) yes
N(5) C(16) C(17) 177.5(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(4) 1.743(3) yes
S(1) C(6) 1.712(4) yes
S(2) C(5) 1.706(4) yes
S(2) C(6) 1.740(3) yes
S(3) C(7) 1.724(3) yes
S(3) C(8) 1.721(4) yes
S(4) C(7) 1.717(4) yes
S(4) C(9) 1.727(3) yes
O(1) C(10) 1.250(4) yes
O(2) C(11) 1.242(4) yes
O(3) C(13) 1.227(4) yes
O(4) C(14) 1.232(4) yes
O(5) N(3) 1.231(3) yes
O(6) N(3) 1.237(3) yes
O(7) N(4) 1.222(4) yes
O(8) N(4) 1.222(4) yes
N(1) C(1) 1.380(5) yes
N(1) C(3) 1.333(4) yes
N(2) C(2) 1.380(4) yes
N(2) C(3) 1.336(4) yes
N(3) C(12) 1.439(4) yes
N(4) C(15) 1.456(4) yes
N(5) C(16) 1.125(7) yes
C(1) C(2) 1.341(5) yes
C(3) C(4) 1.464(5) yes
C(4) C(5) 1.352(5) yes
C(6) C(7) 1.393(4) yes
C(8) C(9) 1.334(6) yes
C(10) C(11) 1.535(5) yes
C(10) C(15) 1.400(4) yes
C(11) C(12) 1.421(5) yes
C(12) C(13) 1.426(4) yes
C(13) C(14) 1.538(5) yes
C(14) C(15) 1.415(5) yes
C(16) C(17) 1.437(8) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
S(1) O(2) 3.327(2) 2_666
S(1) S(4) 3.483(1) 2_576
S(1) N(5) 3.553(5) 1_655
S(2) O(4) 3.155(3) 2_665
S(2) O(3) 3.175(2) 2_665
S(2) S(3) 3.270(1) 2_576
S(2) N(5) 3.506(5) 2_476
S(3) O(3) 3.022(3) 1_466
S(3) O(6) 3.276(3) 1_466
S(3) O(8) 3.389(3) 1_456
S(4) O(5) 3.465(3) 2_566
O(1) O(3) 3.335(4) 2_665
O(1) C(17) 3.372(6) 2_576
O(1) C(8) 3.407(4) 2_576
O(2) N(2) 2.755(3) 2_666
O(2) C(3) 3.341(4) 2_666
O(2) C(4) 3.452(4) 2_666
O(2) O(4) 3.593(4) 2_665
O(3) C(8) 2.968(5) 1_644
O(3) C(5) 3.035(4) 2_665
O(3) C(10) 3.124(4) 2_665
O(3) C(11) 3.344(4) 2_665
O(4) C(2) 3.009(4) 1_554
O(4) C(1) 3.293(4) 2_765
O(4) C(5) 3.323(5) 2_665
O(4) N(2) 3.390(4) 1_554
O(4) O(5) 3.397(4) 2_665
O(5) N(2) 2.758(4) 2_666
O(5) O(8) 3.236(4) 2_665
O(5) C(9) 3.317(5) 2_566
O(5) N(4) 3.477(5) 2_665
O(5) C(2) 3.513(4) 2_666
O(6) C(17) 3.097(6) 2_566
O(6) O(8) 3.294(4) 2_665
O(6) C(16) 3.299(6) 2_566
O(6) C(8) 3.417(5) 1_644
O(7) C(1) 3.212(4) 2_765
O(7) C(7) 3.225(4) 1_654
O(7) C(6) 3.332(4) 1_654
O(8) C(8) 3.212(4) 1_654
O(8) N(3) 3.240(5) 2_665
O(8) C(17) 3.277(6) 2_576
O(8) C(9) 3.419(5) 1_654
O(8) C(8) 3.480(4) 2_576
N(2) C(5) 3.391(4) 2_666
N(4) C(17) 3.539(7) 2_576
N(5) C(1) 3.450(7) 2_576
C(2) C(5) 3.397(5) 2_666
C(5) C(8) 3.509(5) 2_576
C(6) C(7) 3.358(4) 2_576
C(6) C(6) 3.541(6) 2_576
C(10) C(13) 3.449(5) 2_665
C(11) C(13) 3.421(5) 2_665
C(11) C(14) 3.533(5) 2_665
C(12) C(14) 3.386(5) 2_665
C(12) C(17) 3.435(6) 1_744
C(12) C(15) 3.547(5) 2_665
C(12) C(13) 3.569(4) 2_665
C(13) C(17) 3.577(6) 1_744
C(13) C(16) 3.600(5) 1_744
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N(1) H(1) O(1) . 0.956 1.730 2.643(4) 158.301 no
N(1) H(1) O(2) . 0.956 2.396 3.024(4) 122.949 no
N(2) H(2) S(1) . 0.956 2.922 3.156(3) 95.227 no
N(2) H(2) O(4) 1_556 0.956 3.180 3.390(4) 94.386 no
N(2) H(2) O(2) 2_666 0.956 2.122 2.755(3) 122.429 no
N(2) H(2) O(5) 2_666 0.956 1.880 2.758(4) 151.409 no
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(4) C(3) N(1) -152.4(3) yes
S(1) C(4) C(3) N(2) 26.0(5) yes
S(1) C(4) C(5) S(2) -0.2(4) yes
S(1) C(6) S(2) C(5) 2.4(2) yes
S(1) C(6) C(7) S(3) 5.5(4) yes
S(1) C(6) C(7) S(4) -175.1(2) yes
S(2) C(5) C(4) C(3) -176.5(3) yes
S(2) C(6) S(1) C(4) -2.4(2) yes
S(2) C(6) C(7) S(3) -176.6(2) yes
S(2) C(6) C(7) S(4) 2.8(4) yes
S(3) C(7) S(4) C(9) -3.1(2) yes
S(3) C(8) C(9) S(4) -0.9(4) yes
S(4) C(7) S(3) C(8) 2.7(2) yes
O(1) C(10) C(11) O(2) -0.2(4) yes
O(1) C(10) C(11) C(12) -178.4(3) yes
O(1) C(10) C(15) N(4) -2.8(5) yes
O(1) C(10) C(15) C(14) 179.3(3) yes
O(2) C(11) C(10) C(15) 177.6(3) yes
O(2) C(11) C(12) N(3) -2.6(5) yes
O(2) C(11) C(12) C(13) 177.6(3) yes
O(3) C(13) C(12) N(3) 9.7(5) yes
O(3) C(13) C(12) C(11) -170.5(3) yes
O(3) C(13) C(14) O(4) -6.4(4) yes
O(3) C(13) C(14) C(15) 172.0(3) yes
O(4) C(14) C(13) C(12) 174.8(3) yes
O(4) C(14) C(15) N(4) 2.3(5) yes
O(4) C(14) C(15) C(10) -179.8(3) yes
O(5) N(3) C(12) C(11) 29.2(5) yes
O(5) N(3) C(12) C(13) -151.0(3) yes
O(6) N(3) C(12) C(11) -148.2(3) yes
O(6) N(3) C(12) C(13) 31.6(5) yes
O(7) N(4) C(15) C(10) 125.5(4) yes
O(7) N(4) C(15) C(14) -56.4(5) yes
O(8) N(4) C(15) C(10) -55.0(5) yes
O(8) N(4) C(15) C(14) 123.1(4) yes
N(1) C(1) C(2) N(2) -0.1(4) yes
N(1) C(3) N(2) C(2) 0.4(4) yes
N(1) C(3) C(4) C(5) 23.8(5) yes
N(2) C(3) N(1) C(1) -0.4(4) yes
N(2) C(3) C(4) C(5) -157.8(3) yes
N(3) C(12) C(11) C(10) 175.3(3) yes
N(3) C(12) C(13) C(14) -171.7(3) yes
N(4) C(15) C(10) C(11) 179.6(3) yes
N(4) C(15) C(14) C(13) -176.0(3) yes
C(1) N(1) C(3) C(4) 178.2(3) yes
C(1) C(2) N(2) C(3) -0.2(4) yes
C(2) N(2) C(3) C(4) -178.2(3) yes
C(2) C(1) N(1) C(3) 0.3(4) yes
C(3) C(4) S(1) C(6) 178.1(3) yes
C(4) S(1) C(6) C(7) 175.6(3) yes
C(4) C(5) S(2) C(6) -1.3(3) yes
C(5) S(2) C(6) C(7) -175.7(3) yes
C(5) C(4) S(1) C(6) 1.6(3) yes
C(6) C(7) S(3) C(8) -177.8(3) yes
C(6) C(7) S(4) C(9) 177.5(3) yes
C(7) S(3) C(8) C(9) -1.1(3) yes
C(7) S(4) C(9) C(8) 2.4(3) yes
C(10) C(11) C(12) C(13) -4.4(5) yes
C(10) C(15) C(14) C(13) 1.9(5) yes
C(11) C(10) C(15) C(14) 1.7(5) yes
C(11) C(12) C(13) C(14) 8.1(5) yes
C(12) C(11) C(10) C(15) -0.6(4) yes
C(12) C(13) C(14) C(15) -6.7(4) yes
C(12) C(13) C(14) C(15) -6.7(4) yes
