#------------------------------------------------------------------------------
#$Date: 2017-01-18 12:57:26 +0200 (Wed, 18 Jan 2017) $
#$Revision: 190646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/74/7227465.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_7227465
loop_
_publ_author_name
'Kanetou, Tomoaki'
'Tsunashima, Ryo'
'Hoshino, Norihisa'
'Akutagawa, Tomoyuki'
_publ_section_title
;
 Solid-state structure and electronic states of hydrogen-bonded dimer of
 pyridyl-substituted tetrathiafulvalene salted with PF6−
;
_journal_issue                   11
_journal_name_full               'RSC Adv.'
_journal_page_first              6236
_journal_paper_doi               10.1039/C6RA27814K
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C22 H15 F6 N2 P S8'
_chemical_formula_sum            'C22 H15 F6 N2 P S8'
_chemical_formula_weight         708.82
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-11-30 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 114.9637(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   29.2197(6)
_cell_length_b                   6.08065(11)
_cell_length_c                   16.8443(3)
_cell_measurement_reflns_used    9075
_cell_measurement_temperature    323
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      3.34
_cell_volume                     2713.21(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      323
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14411
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.215
_exptl_absorpt_correction_T_max  0.486
_exptl_absorpt_correction_T_min  0.433
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1432.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.842
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1066P)²+2.4928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                2069
_reflns_number_total             2480
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c6ra27814k2.cif
_cod_data_source_block           ttfpy2hpf6_50degree
_cod_database_code               7227465
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+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
S1 S 0.34746(3) 0.56238(13) 0.54775(5) 0.0660(3) Uani 1.0 8 d .
S2 S 0.33725(3) 0.97227(14) 0.44746(5) 0.0684(3) Uani 1.0 8 d .
S3 S 0.22904(2) 0.82359(12) 0.30443(4) 0.0613(3) Uani 1.0 8 d .
S4 S 0.23402(3) 0.41468(12) 0.40156(5) 0.0634(3) Uani 1.0 8 d .
P1 P 0.0000 0.19948(18) 0.2500 0.0623(3) Uani 1.0 4 d .
F1 F 0.0000 -0.0597(4) 0.2500 0.1054(11) Uani 1.0 4 d .
F2 F 0.01195(9) 0.2013(5) 0.35047(13) 0.1090(9) Uani 1.0 8 d .
F3 F 0.05926(7) 0.1992(4) 0.27414(14) 0.0875(6) Uani 1.0 8 d .
F4 F 0.0000 0.4592(5) 0.2500 0.1014(10) Uani 1.0 4 d .
N1 N 0.04105(9) 0.9118(5) 0.06363(15) 0.0675(7) Uani 1.0 8 d .
C1 C 0.39429(11) 0.7613(6) 0.59121(19) 0.0710(8) Uani 1.0 8 d .
C2 C 0.38996(11) 0.9443(6) 0.5466(2) 0.0687(8) Uani 1.0 8 d .
C3 C 0.30949(9) 0.7215(5) 0.45604(16) 0.0534(6) Uani 1.0 8 d .
C4 C 0.26393(9) 0.6612(5) 0.39692(16) 0.0522(6) Uani 1.0 8 d .
C5 C 0.17724(10) 0.4805(5) 0.31698(17) 0.0568(7) Uani 1.0 8 d .
C6 C 0.17333(9) 0.6674(5) 0.27190(16) 0.0508(6) Uani 1.0 8 d .
C7 C 0.12764(9) 0.7506(5) 0.20003(16) 0.0518(6) Uani 1.0 8 d .
C8 C 0.08172(11) 0.6393(6) 0.1712(2) 0.0683(8) Uani 1.0 8 d .
C9 C 0.04016(11) 0.7254(7) 0.1045(2) 0.0750(9) Uani 1.0 8 d .
C10 C 0.08428(11) 1.0202(7) 0.0911(2) 0.0740(9) Uani 1.0 8 d .
C11 C 0.12808(10) 0.9476(6) 0.15849(19) 0.0656(8) Uani 1.0 8 d .
H1 H 0.4218 0.7391 0.6447 0.0851 Uiso 1.0 8 calc R
H2 H 0.4143 1.0544 0.5674 0.0825 Uiso 1.0 8 calc R
H3 H 0.1495 0.3881 0.3025 0.0682 Uiso 1.0 8 calc R
H4 H 0.0795 0.5075 0.1973 0.0819 Uiso 1.0 8 calc R
H5 H 0.0097 0.6502 0.0866 0.0900 Uiso 1.0 8 calc R
H6 H 0.1576 1.0295 0.1760 0.0787 Uiso 1.0 8 calc R
H7 H 0.0851 1.1517 0.0635 0.0888 Uiso 1.0 8 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 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.2955 0.4335
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 S1 C3 94.56(14) yes . .
C2 S2 C3 95.08(14) yes . .
C4 S3 C6 94.98(12) yes . .
C4 S4 C5 95.10(13) yes . .
F1 P1 F2 90.40(11) yes . .
F1 P1 F2 90.40(11) yes . 2_555
F1 P1 F3 89.93(9) yes . .
F1 P1 F3 89.93(9) yes . 2_555
F1 P1 F4 180.000 yes . .
F2 P1 F2 179.21(17) yes . 2_555
F2 P1 F3 90.09(13) yes . .
F2 P1 F3 89.91(13) yes . 2_555
F2 P1 F4 89.60(11) yes . .
F2 P1 F3 89.91(13) yes 2_555 .
F2 P1 F3 90.09(13) yes 2_555 2_555
F2 P1 F4 89.60(11) yes 2_555 .
F3 P1 F3 179.87(14) yes . 2_555
F3 P1 F4 90.07(9) yes . .
F3 P1 F4 90.07(9) yes 2_555 .
C9 N1 C10 117.9(3) yes . .
S1 C1 C2 118.5(2) yes . .
S2 C2 C1 117.6(3) yes . .
S1 C3 S2 113.94(13) yes . .
S1 C3 C4 124.3(3) yes . .
S2 C3 C4 121.7(2) yes . .
S3 C4 S4 113.93(12) yes . .
S3 C4 C3 121.9(3) yes . .
S4 C4 C3 124.1(2) yes . .
S4 C5 C6 119.2(2) yes . .
S3 C6 C5 115.67(17) yes . .
S3 C6 C7 118.2(2) yes . .
C5 C6 C7 126.2(3) yes . .
C6 C7 C8 121.9(3) yes . .
C6 C7 C11 121.0(3) yes . .
C8 C7 C11 117.1(3) yes . .
C7 C8 C9 119.5(4) yes . .
N1 C9 C8 123.2(3) yes . .
N1 C10 C11 123.1(4) yes . .
C7 C11 C10 119.2(3) yes . .
S1 C1 H1 120.740 no . .
C2 C1 H1 120.731 no . .
S2 C2 H2 121.196 no . .
C1 C2 H2 121.194 no . .
S4 C5 H3 120.395 no . .
C6 C5 H3 120.403 no . .
C7 C8 H4 120.258 no . .
C9 C8 H4 120.263 no . .
N1 C9 H5 118.403 no . .
C8 C9 H5 118.397 no . .
N1 C10 H7 118.438 no . .
C11 C10 H7 118.418 no . .
C7 C11 H6 120.381 no . .
C10 C11 H6 120.385 no . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
S1 C1 1.739(4) yes .
S1 C3 1.763(3) yes .
S2 C2 1.737(3) yes .
S2 C3 1.761(3) yes .
S3 C4 1.761(3) yes .
S3 C6 1.761(3) yes .
S4 C4 1.753(3) yes .
S4 C5 1.717(3) yes .
P1 F1 1.576(3) yes .
P1 F2 1.577(3) yes .
P1 F2 1.577(3) yes 2_555
P1 F3 1.603(2) yes .
P1 F3 1.603(2) yes 2_555
P1 F4 1.579(4) yes .
N1 C9 1.332(5) yes .
N1 C10 1.323(4) yes .
C1 C2 1.319(5) yes .
C3 C4 1.334(3) yes .
C5 C6 1.344(4) yes .
C6 C7 1.463(3) yes .
C7 C8 1.394(4) yes .
C7 C11 1.390(5) yes .
C8 C9 1.364(4) yes .
C10 C11 1.377(4) yes .
C1 H1 0.930 no .
C2 H2 0.930 no .
C5 H3 0.930 no .
C8 H4 0.930 no .
C9 H5 0.930 no .
C10 H7 0.930 no .
C11 H6 0.930 no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_2
S1 S4 3.3118(10) no .
S2 S3 3.1920(9) no .
S3 C11 3.032(3) no .
N1 C7 2.781(3) no .
C5 C8 2.994(4) no .
C8 C10 2.697(6) no .
C9 C11 2.698(5) no .
S1 F3 3.472(2) no 7_556
S2 C7 3.499(4) no 6_555
F1 F4 2.925(4) no 1_545
F1 C1 3.350(3) no 7_556
F1 C1 3.350(3) no 8_454
F1 C9 3.394(4) no 1_545
F1 C9 3.394(4) no 2_545
F2 N1 3.079(5) no 2_545
F2 N1 3.393(4) no 4_565
F2 C2 3.417(4) no 7_566
F2 C9 3.499(5) no 2_545
F2 C10 3.525(5) no 2_545
F3 S1 3.472(2) no 7_556
F3 C1 3.497(4) no 7_556
F3 C2 3.499(4) no 7_566
F3 C8 3.400(5) no .
F4 F1 2.925(4) no 1_565
F4 C1 3.551(4) no 7_566
F4 C1 3.551(4) no 8_464
F4 C8 3.367(4) no .
F4 C8 3.367(4) no 2_555
F4 C9 3.526(5) no .
F4 C9 3.526(5) no 2_555
N1 F2 3.079(5) no 2_565
N1 F2 3.393(4) no 4_564
N1 N1 2.676(3) no 3_575
N1 C9 3.584(4) no 3_575
N1 C10 3.510(4) no 3_575
C1 F1 3.350(3) no 7_556
C1 F3 3.497(4) no 7_556
C1 F4 3.551(4) no 7_566
C1 C5 3.457(5) no 7_566
C2 F2 3.417(4) no 7_566
C2 F3 3.499(4) no 7_566
C3 C11 3.577(5) no 6_545
C5 C1 3.457(5) no 7_566
C7 S2 3.499(4) no 6_545
C8 F3 3.400(5) no .
C8 F4 3.367(4) no .
C9 F1 3.394(4) no 1_565
C9 F2 3.499(5) no 2_565
C9 F4 3.526(5) no .
C9 N1 3.584(4) no 3_575
C10 F2 3.525(5) no 2_565
C10 N1 3.510(4) no 3_575
C11 C3 3.577(5) no 6_555
S1 H2 3.5103 no .
S2 H1 3.4965 no .
S3 H3 3.5143 no .
S3 H6 2.6057 no .
N1 H4 3.2001 no .
N1 H6 3.2026 no .
C3 H1 3.4751 no .
C3 H2 3.4840 no .
C4 H3 3.4604 no .
C5 H4 2.7190 no .
C6 H4 2.6720 no .
C6 H6 2.6535 no .
C7 H3 2.7049 no .
C7 H5 3.2156 no .
C7 H7 3.2198 no .
C8 H3 2.7299 no .
C8 H6 3.2253 no .
C9 H7 3.1122 no .
C10 H5 3.1107 no .
C11 H4 3.2240 no .
H1 H2 2.2756 no .
H3 H4 2.1903 no .
H4 H5 2.2749 no .
H6 H7 2.2897 no .
S1 H2 3.5937 no 1_545
S1 H7 3.2874 no 6_545
S2 H6 3.4440 no 6_545
S2 H7 3.0552 no 6_545
P1 H1 3.4725 no 7_556
P1 H1 3.4725 no 8_454
P1 H2 3.3871 no 7_566
P1 H2 3.3871 no 8_464
P1 H4 3.3799 no .
P1 H4 3.3799 no 2_555
F1 H1 2.4772 no 7_556
F1 H1 2.4772 no 8_454
F1 H5 3.3804 no 1_545
F1 H5 3.3804 no 2_545
F2 H1 3.2853 no 7_556
F2 H2 2.5007 no 7_566
F2 H4 3.0713 no 2_555
F2 H5 3.0889 no 2_555
F3 H1 2.9387 no 7_556
F3 H2 2.8677 no 7_566
F3 H3 2.7275 no .
F3 H4 2.4864 no .
F4 H1 2.8833 no 7_566
F4 H1 2.8833 no 8_464
F4 H2 3.0395 no 7_566
F4 H2 3.0395 no 8_464
F4 H4 2.8289 no .
F4 H4 2.8289 no 2_555
F4 H5 3.1087 no .
F4 H5 3.1087 no 2_555
N1 H5 3.5397 no 3_575
N1 H7 3.4151 no 3_575
C1 H3 3.3649 no 7_566
C1 H4 3.5983 no 7_566
C1 H5 3.4483 no 8_565
C1 H7 2.9874 no 6_545
C2 H3 3.3623 no 7_566
C2 H5 3.3221 no 8_565
C2 H7 2.8768 no 6_545
C3 H6 3.0067 no 6_545
C3 H7 3.2603 no 6_545
C4 H6 3.1275 no 6_545
C5 H6 3.5128 no 1_545
C7 H1 3.4806 no 7_566
C8 H1 3.2305 no 7_566
C8 H7 3.4992 no 1_545
C10 H4 3.4949 no 1_565
C11 H3 3.4884 no 1_565
H1 P1 3.4725 no 7_556
H1 F1 2.4772 no 7_556
H1 F2 3.2853 no 7_556
H1 F3 2.9387 no 7_556
H1 F4 2.8833 no 7_566
H1 C7 3.4806 no 7_566
H1 C8 3.2305 no 7_566
H1 H3 3.4398 no 7_566
H1 H4 3.0881 no 7_566
H1 H5 3.1839 no 8_565
H1 H7 3.4689 no 6_545
H2 S1 3.5937 no 1_565
H2 P1 3.3871 no 7_566
H2 F2 2.5007 no 7_566
H2 F3 2.8677 no 7_566
H2 F4 3.0395 no 7_566
H2 H3 3.4407 no 7_566
H2 H5 2.9447 no 8_565
H2 H7 3.3009 no 6_545
H3 F3 2.7275 no .
H3 C1 3.3649 no 7_566
H3 C2 3.3623 no 7_566
H3 C11 3.4884 no 1_545
H3 H1 3.4398 no 7_566
H3 H2 3.4407 no 7_566
H3 H6 3.1269 no 1_545
H4 P1 3.3799 no .
H4 F2 3.0713 no 2_555
H4 F3 2.4864 no .
H4 F4 2.8289 no .
H4 C1 3.5983 no 7_566
H4 C10 3.4949 no 1_545
H4 H1 3.0881 no 7_566
H4 H7 3.1781 no 1_545
H5 F1 3.3804 no 1_565
H5 F2 3.0889 no 2_555
H5 F4 3.1087 no .
H5 N1 3.5397 no 3_575
H5 C1 3.4483 no 8_464
H5 C2 3.3221 no 8_464
H5 H1 3.1839 no 8_464
H5 H2 2.9447 no 8_464
H5 H5 3.2820 no 3_565
H5 H7 3.1000 no 3_575
H6 S2 3.4440 no 6_555
H6 C3 3.0067 no 6_555
H6 C4 3.1275 no 6_555
H6 C5 3.5128 no 1_565
H6 H3 3.1269 no 1_565
H7 S1 3.2874 no 6_555
H7 S2 3.0552 no 6_555
H7 N1 3.4151 no 3_575
H7 C1 2.9874 no 6_555
H7 C2 2.8768 no 6_555
H7 C3 3.2603 no 6_555
H7 C8 3.4992 no 1_565
H7 H1 3.4689 no 6_555
H7 H2 3.3009 no 6_555
H7 H4 3.1781 no 1_565
H7 H5 3.1000 no 3_575
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
C1 S1 C3 S2 5.2(3) no
C1 S1 C3 C4 -175.4(3) no
C3 S1 C1 C2 -3.4(3) no
C2 S2 C3 S1 -5.1(3) no
C2 S2 C3 C4 175.5(3) no
C3 S2 C2 C1 3.0(3) no
C4 S3 C6 C5 -7.3(3) no
C4 S3 C6 C7 172.4(2) no
C6 S3 C4 S4 10.5(2) no
C6 S3 C4 C3 -171.0(3) no
C4 S4 C5 C6 5.2(3) no
C5 S4 C4 S3 -9.9(2) no
C5 S4 C4 C3 171.7(3) no
C9 N1 C10 C11 1.0(6) no
C10 N1 C9 C8 -1.7(6) no
S1 C1 C2 S2 0.3(5) no
S1 C3 C4 S3 -177.48(18) no
S1 C3 C4 S4 0.8(5) no
S2 C3 C4 S3 1.9(4) no
S2 C3 C4 S4 -179.83(18) no
S4 C5 C6 S3 1.5(4) no
S4 C5 C6 C7 -178.2(2) no
S3 C6 C7 C8 -178.81(19) no
S3 C6 C7 C11 -0.1(4) no
C5 C6 C7 C8 0.8(5) no
C5 C6 C7 C11 179.6(3) no
C6 C7 C8 C9 179.4(3) no
C6 C7 C11 C10 180.0(3) no
C8 C7 C11 C10 -1.2(5) no
C11 C7 C8 C9 0.6(5) no
C7 C8 C9 N1 0.9(6) no
N1 C10 C11 C7 0.5(6) no
