#------------------------------------------------------------------------------
#$Date: 2019-11-24 01:13:43 +0200 (Sun, 24 Nov 2019) $
#$Revision: 235933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/37/1553715.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_1553715
loop_
_publ_author_name
'Ueda, Akira'
'Mori, Hatsumi'
_publ_section_title
;
 A phenol-fused tetrathiafulvalene: modulation of hydrogen-bond patterns
 and electrical conductivity in the charge-transfer salt
;
_journal_issue                   3
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              566
_journal_paper_doi               10.1039/C7QM00574A
_journal_volume                  2
_journal_year                    2018
_chemical_formula_moiety         'C24 H16 Cl O6 S12'
_chemical_formula_sum            'C24 H16 Cl O6 S12'
_chemical_formula_weight         820.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-12-11 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.227(18)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   33.29(4)
_cell_length_b                   7.227(7)
_cell_length_c                   13.232(14)
_cell_measurement_reflns_used    2852
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.11
_cell_volume                     3072(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11375
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        27.400
_diffrn_reflns_theta_max         27.400
_diffrn_reflns_theta_min         3.109
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1668.00
_exptl_crystal_recrystallization_method electrocrystallization
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.00
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1869
_refine_ls_R_factor_gt           0.0754
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0800P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.2367
_reflns_number_gt                1365
_reflns_number_total             3476
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c7qm00574a1.cif
_cod_data_source_block           AU2329_ClO4_c
_cod_database_code               1553715
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cl7 Cl 0.5000 0.4771(5) 0.2500 0.0837(9) Uani 1 2 d S
S1 S 0.20987(5) 0.1202(2) 0.30739(13) 0.0530(5) Uani 1 1 d .
S2 S 0.24095(6) 0.1203(2) 0.11677(13) 0.0572(5) Uani 1 1 d .
S3 S 0.33462(5) 0.1208(2) 0.25498(13) 0.0544(5) Uani 1 1 d .
S4 S 0.30700(5) 0.1166(2) 0.44860(13) 0.0539(5) Uani 1 1 d .
S5 S 0.39171(6) 0.1159(3) 0.59117(15) 0.0703(6) Uani 1 1 d .
S6 S 0.42460(6) 0.1320(3) 0.35815(16) 0.0740(6) Uani 1 1 d .
O10 O 0.4652(2) 0.5867(10) 0.2523(6) 0.138(3) Uani 1 1 d .
O13 O 0.5104(2) 0.3662(11) 0.3422(6) 0.158(3) Uani 1 1 d .
O20 O 0.05890(17) 0.1361(7) 0.0700(5) 0.0989(19) Uani 1 1 d .
H20 H 0.0504 0.0354 0.0841 0.119 Uiso 1 1 calc R
C1 C 0.1859(2) 0.1216(8) 0.0965(5) 0.0473(15) Uani 1 1 d .
C2 C 0.36069(19) 0.1161(8) 0.4610(5) 0.0492(16) Uani 1 1 d .
C3 C 0.2529(2) 0.1191(8) 0.2529(5) 0.0458(15) Uani 1 1 d .
C4 C 0.37412(19) 0.1212(8) 0.3720(5) 0.0497(16) Uani 1 1 d .
C6 C 0.1716(2) 0.1201(7) 0.1877(5) 0.0465(15) Uani 1 1 d .
C8 C 0.2933(2) 0.1192(8) 0.3119(5) 0.0495(16) Uani 1 1 d .
C9 C 0.1153(2) 0.1269(9) -0.0115(6) 0.067(2) Uani 1 1 d .
H9 H 0.0963 0.1304 -0.0769 0.081 Uiso 1 1 calc R
C11 C 0.1019(2) 0.1254(9) 0.0799(6) 0.0585(18) Uani 1 1 d .
C12 C 0.4428(2) 0.0669(10) 0.5734(6) 0.079(2) Uani 1 1 d .
H12A H 0.4634 0.0872 0.6393 0.095 Uiso 1 1 calc R
H12B H 0.4440 -0.0627 0.5553 0.095 Uiso 1 1 calc R
C15 C 0.4540(2) 0.1828(10) 0.4899(5) 0.071(2) Uani 1 1 d .
H15A H 0.4834 0.1650 0.4946 0.085 Uiso 1 1 calc R
H15B H 0.4501 0.3122 0.5042 0.085 Uiso 1 1 calc R
C18 C 0.1285(2) 0.1219(7) 0.1786(5) 0.0507(16) Uani 1 1 d .
H18 H 0.1183 0.1207 0.2377 0.061 Uiso 1 1 calc R
C19 C 0.1572(2) 0.1229(8) -0.0026(5) 0.0523(17) Uani 1 1 d .
H19 H 0.1667 0.1210 -0.0627 0.063 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(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
O10 Cl7 O10 111.7(7) . 2_655
O10 Cl7 O13 108.6(4) . 2_655
O10 Cl7 O13 108.2(4) 2_655 2_655
O10 Cl7 O13 108.2(4) . .
O10 Cl7 O13 108.6(4) 2_655 .
O13 Cl7 O13 111.5(7) 2_655 .
C6 S1 C3 96.1(3) . .
C3 S2 C1 95.9(3) . .
C8 S3 C4 96.5(3) . .
C8 S4 C2 94.6(3) . .
C2 S5 C12 101.7(3) . .
C4 S6 C15 101.7(3) . .
C11 O20 H20 109.5 . .
C19 C1 C6 119.9(6) . .
C19 C1 S2 124.2(5) . .
C6 C1 S2 115.9(5) . .
C4 C2 S4 118.5(5) . .
C4 C2 S5 127.1(5) . .
S4 C2 S5 114.4(3) . .
C8 C3 S2 121.0(5) . .
C8 C3 S1 123.3(5) . .
S2 C3 S1 115.6(4) . .
C2 C4 S6 129.5(5) . .
C2 C4 S3 115.0(5) . .
S6 C4 S3 115.4(4) . .
C18 C6 C1 119.5(6) . .
C18 C6 S1 124.1(5) . .
C1 C6 S1 116.4(5) . .
C3 C8 S3 121.7(5) . .
C3 C8 S4 122.9(5) . .
S3 C8 S4 115.4(4) . .
C19 C9 C11 118.5(7) . .
C19 C9 H9 120.8 . .
C11 C9 H9 120.8 . .
C18 C11 C9 123.6(7) . .
C18 C11 O20 118.4(7) . .
C9 C11 O20 118.0(7) . .
C15 C12 S5 114.1(5) . .
C15 C12 H12A 108.7 . .
S5 C12 H12A 108.7 . .
C15 C12 H12B 108.7 . .
S5 C12 H12B 108.7 . .
H12A C12 H12B 107.6 . .
C12 C15 S6 114.8(5) . .
C12 C15 H15A 108.6 . .
S6 C15 H15A 108.6 . .
C12 C15 H15B 108.6 . .
S6 C15 H15B 108.6 . .
H15A C15 H15B 107.6 . .
C11 C18 C6 117.9(6) . .
C11 C18 H18 121.0 . .
C6 C18 H18 121.0 . .
C9 C19 C1 120.6(6) . .
C9 C19 H19 119.7 . .
C1 C19 H19 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl7 O10 1.410(6) .
Cl7 O10 1.410(6) 2_655
Cl7 O13 1.424(6) 2_655
Cl7 O13 1.424(6) .
S1 C6 1.752(7) .
S1 C3 1.766(6) .
S2 C3 1.740(6) .
S2 C1 1.781(7) .
S3 C8 1.733(6) .
S3 C4 1.749(7) .
S4 C8 1.746(7) .
S4 C2 1.752(7) .
S5 C2 1.761(7) .
S5 C12 1.812(7) .
S6 C4 1.740(6) .
S6 C15 1.799(7) .
O20 C11 1.406(8) .
O20 H20 0.8200 .
C1 C19 1.406(8) .
C1 C6 1.410(8) .
C2 C4 1.365(8) .
C3 C8 1.365(9) .
C6 C18 1.410(8) .
C9 C19 1.367(9) .
C9 C11 1.394(10) .
C9 H9 0.9300 .
C11 C18 1.371(9) .
C12 C15 1.510(9) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C18 H18 0.9300 .
C19 H19 0.9300 .
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_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O20 H20 O10 4_545 2.700(11) 0.820 2.385 103.8 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
C3 S2 C1 C19 180.0(5)
C3 S2 C1 C6 -0.4(5)
C8 S4 C2 C4 1.2(5)
C8 S4 C2 S5 179.4(3)
C12 S5 C2 C4 -13.4(7)
C12 S5 C2 S4 168.6(3)
C1 S2 C3 C8 -179.5(5)
C1 S2 C3 S1 -0.2(4)
C6 S1 C3 C8 179.9(5)
C6 S1 C3 S2 0.5(4)
S4 C2 C4 S6 177.0(3)
S5 C2 C4 S6 -1.0(9)
S4 C2 C4 S3 -1.8(7)
S5 C2 C4 S3 -179.7(3)
C15 S6 C4 C2 -11.4(7)
C15 S6 C4 S3 167.4(4)
C8 S3 C4 C2 1.3(5)
C8 S3 C4 S6 -177.6(3)
C19 C1 C6 C18 -0.7(8)
S2 C1 C6 C18 179.7(4)
C19 C1 C6 S1 -179.6(4)
S2 C1 C6 S1 0.8(6)
C3 S1 C6 C18 -179.6(5)
C3 S1 C6 C1 -0.8(5)
S2 C3 C8 S3 0.1(7)
S1 C3 C8 S3 -179.2(3)
S2 C3 C8 S4 -179.6(3)
S1 C3 C8 S4 1.1(8)
C4 S3 C8 C3 179.7(5)
C4 S3 C8 S4 -0.5(4)
C2 S4 C8 C3 179.5(5)
C2 S4 C8 S3 -0.2(4)
C19 C9 C11 C18 0.6(10)
C19 C9 C11 O20 177.8(5)
C2 S5 C12 C15 47.4(6)
S5 C12 C15 S6 -69.0(7)
C4 S6 C15 C12 45.8(6)
C9 C11 C18 C6 0.2(10)
O20 C11 C18 C6 -177.0(5)
C1 C6 C18 C11 -0.1(8)
S1 C6 C18 C11 178.7(5)
C11 C9 C19 C1 -1.4(9)
C6 C1 C19 C9 1.5(9)
S2 C1 C19 C9 -178.9(5)
