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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/03/8000399.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_8000399
loop_
_publ_author_name
'Takahashi, Yukihiro'
'Takehisa, Mika'
'Tanaka, Eri'
'Harada, Jun'
'Kumai, Reiji'
'Inabe, Tamotsu'
_publ_section_title
;
 Incorporating Spacer Molecules into the Tetrathiafulvalene-p-Chloranil
 Charge-Transfer Framework: Modulating the Neutral-Ionic Phase Transition.
;
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              1336
_journal_paper_doi               10.1021/acs.jpclett.9b03847
_journal_year                    2020
_chemical_formula_moiety         'C48 H24 Cl12 O6 S4'
_chemical_formula_sum            'C48 H24 Cl12 O6 S4'
_chemical_formula_weight         1250.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                96.1900(7)
_cell_angle_beta                 98.5690(7)
_cell_angle_gamma                92.3536(7)
_cell_formula_units_Z            1
_cell_length_a                   7.17380(10)
_cell_length_b                   7.67220(10)
_cell_length_c                   21.6585(7)
_cell_measurement_reflns_used    8544
_cell_measurement_temperature    50
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      2.69
_cell_volume                     1169.90(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      50
_diffrn_measured_fraction_theta_full 0.570
_diffrn_measured_fraction_theta_max 0.355
_diffrn_measurement_device_type  IPDSC
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.00000
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.570
_diffrn_reflns_Laue_measured_fraction_max 0.355
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            8108
_diffrn_reflns_point_group_measured_fraction_full 0.570
_diffrn_reflns_point_group_measured_fraction_max 0.355
_diffrn_reflns_theta_full        36.870
_diffrn_reflns_theta_max         72.194
_diffrn_reflns_theta_min         2.694
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             628.00
_refine_diff_density_max         1.04
_refine_diff_density_min         -1.03
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5042
_reflns_number_total             6016
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jz9b03847_si_002.cif
_cod_data_source_block           (TTF)(Ace)2(CA)3_50K
_cod_database_code               8000399
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 1.31889(13) 0.13309(5) 0.43644(2) 0.0241(4) Uani 1 1 d . .
Cl2 Cl 1.41192(13) 0.43540(6) 0.35263(2) 0.0243(4) Uani 1 1 d . .
Cl3 Cl 1.49654(14) -0.13628(6) 0.29706(2) 0.0248(4) Uani 1 1 d . .
Cl4 Cl 1.55575(14) 0.18686(6) 0.21946(2) 0.0253(4) Uani 1 1 d . .
Cl5 Cl 1.23951(15) -0.21041(6) 0.00522(2) 0.0329(4) Uani 1 1 d . .
Cl6 Cl 1.18578(14) -0.53364(6) 0.08252(2) 0.0291(4) Uani 1 1 d . .
S1 S 0.92996(14) 0.41407(6) 0.39908(2) 0.0271(4) Uani 1 1 d . .
S2 S 0.88303(14) 0.23864(6) 0.51112(2) 0.0263(4) Uani 1 1 d . .
O1 O 1.4037(4) 0.25556(18) 0.57038(6) 0.0259(9) Uani 1 1 d . .
O2 O 1.3092(4) -0.43903(18) 0.21691(6) 0.0275(8) Uani 1 1 d . .
O3 O 1.4131(4) 0.09919(18) 0.08614(7) 0.0301(9) Uani 1 1 d . .
C1 C 0.8233(6) 0.2025(2) 0.38716(9) 0.0293(13) Uani 1 1 d . .
H1 H 0.779889 0.147753 0.346841 0.035 Uiso 1 1 calc R U
C2 C 0.8057(5) 0.1214(2) 0.43768(9) 0.0275(12) Uani 1 1 d . .
H2 H 0.754264 0.006779 0.433819 0.033 Uiso 1 1 calc R U
C3 C 0.9616(6) 0.4270(2) 0.48132(9) 0.0283(13) Uani 1 1 d . .
C4 C 1.4522(5) 0.3657(2) 0.53828(8) 0.0218(13) Uani 1 1 d . .
C5 C 1.4149(5) 0.3352(2) 0.46826(8) 0.0228(12) Uani 1 1 d . .
C6 C 1.4550(5) 0.4622(2) 0.43268(8) 0.0244(12) Uani 1 1 d . .
C7 C 0.9853(6) -0.1086(2) 0.25366(9) 0.0218(11) Uani 1 1 d . .
C8 C 0.8958(5) -0.1843(2) 0.19373(9) 0.0253(12) Uani 1 1 d . .
C9 C 0.8200(6) -0.3576(2) 0.19371(9) 0.0259(12) Uani 1 1 d . .
C10 C 0.7305(6) -0.4464(2) 0.13826(9) 0.0289(12) Uani 1 1 d . .
H10 H 0.681038 -0.561016 0.136840 0.035 Uiso 1 1 calc R U
C11 C 0.7144(6) -0.3601(3) 0.08279(9) 0.0292(13) Uani 1 1 d . .
H11 H 0.653212 -0.420497 0.045221 0.035 Uiso 1 1 calc R U
C12 C 0.7860(6) -0.1905(2) 0.08261(9) 0.0270(12) Uani 1 1 d . .
H12 H 0.773002 -0.138456 0.045482 0.032 Uiso 1 1 calc R U
C13 C 0.8799(6) -0.0959(2) 0.13964(9) 0.0282(13) Uani 1 1 d . .
C14 C 0.9681(6) 0.0782(2) 0.14767(9) 0.0257(12) Uani 1 1 d . .
H14 H 0.966047 0.141710 0.113376 0.031 Uiso 1 1 calc R U
C15 C 1.0560(6) 0.1511(2) 0.20644(9) 0.0271(12) Uani 1 1 d . .
H15 H 1.111456 0.264388 0.210929 0.033 Uiso 1 1 calc R U
C16 C 1.0646(6) 0.0589(3) 0.26046(9) 0.0272(13) Uani 1 1 d . .
H16 H 1.123180 0.111698 0.299597 0.033 Uiso 1 1 calc R U
C17 C 0.9781(6) -0.2452(2) 0.29940(9) 0.0282(13) Uani 1 1 d . .
H17A H 0.916117 -0.201460 0.334353 0.034 Uiso 1 1 calc R U
H17B H 1.104279 -0.276099 0.315692 0.034 Uiso 1 1 calc R U
C18 C 0.8618(5) -0.4078(2) 0.25978(9) 0.0245(12) Uani 1 1 d . .
H18A H 0.934712 -0.511494 0.260619 0.029 Uiso 1 1 calc R U
H18B H 0.745609 -0.431477 0.276059 0.029 Uiso 1 1 calc R U
C19 C 1.3366(5) -0.3173(2) 0.18698(8) 0.0239(13) Uani 1 1 d . .
C20 C 1.2764(6) -0.3333(2) 0.11731(8) 0.0264(12) Uani 1 1 d . .
C21 C 1.3010(6) -0.1960(2) 0.08465(8) 0.0266(13) Uani 1 1 d . .
C22 C 1.3909(5) -0.0239(2) 0.11588(8) 0.0251(12) Uani 1 1 d . .
C23 C 1.4556(5) -0.0103(2) 0.18507(9) 0.0236(12) Uani 1 1 d . .
C24 C 1.4294(5) -0.1467(2) 0.21786(8) 0.0245(12) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
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 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.0000 0.0000
;
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
C1 S1 C3 94.70(11) . .
C2 S2 C3 95.02(11) . .
C2 C1 S1 117.95(17) . .
C2 C1 H1 121.0 . .
S1 C1 H1 121.0 . .
C1 C2 S2 117.39(19) . .
C1 C2 H2 121.3 . .
S2 C2 H2 121.3 . .
C3 C3 S2 122.8(2) 2_766 .
C3 C3 S1 122.3(2) 2_766 .
S2 C3 S1 114.89(13) . .
O1 C4 C6 121.41(17) . 2_866
O1 C4 C5 121.3(2) . .
C6 C4 C5 117.22(19) 2_866 .
C6 C5 C4 121.4(2) . .
C6 C5 Cl1 122.55(15) . .
C4 C5 Cl1 116.08(16) . .
C5 C6 C4 121.31(17) . 2_866
C5 C6 Cl2 123.28(18) . .
C4 C6 Cl2 115.36(15) 2_866 .
C16 C7 C8 119.22(18) . .
C16 C7 C17 132.5(2) . .
C8 C7 C17 108.2(2) . .
C13 C8 C7 123.7(2) . .
C13 C8 C9 123.3(2) . .
C7 C8 C9 113.07(18) . .
C10 C9 C8 118.86(18) . .
C10 C9 C18 132.7(2) . .
C8 C9 C18 108.5(2) . .
C9 C10 C11 118.8(2) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.6 . .
C12 C11 C10 122.6(2) . .
C12 C11 H11 118.7 . .
C10 C11 H11 118.7 . .
C11 C12 C13 119.53(18) . .
C11 C12 H12 120.2 . .
C13 C12 H12 120.2 . .
C8 C13 C12 116.9(2) . .
C8 C13 C14 116.1(2) . .
C12 C13 C14 127.00(18) . .
C15 C14 C13 119.88(18) . .
C15 C14 H14 120.1 . .
C13 C14 H14 120.1 . .
C14 C15 C16 122.3(2) . .
C14 C15 H15 118.8 . .
C16 C15 H15 118.8 . .
C7 C16 C15 118.8(2) . .
C7 C16 H16 120.6 . .
C15 C16 H16 120.6 . .
C7 C17 C18 104.93(18) . .
C7 C17 H17A 110.8 . .
C18 C17 H17A 110.8 . .
C7 C17 H17B 110.8 . .
C18 C17 H17B 110.8 . .
H17A C17 H17B 108.8 . .
C9 C18 C17 105.21(19) . .
C9 C18 H18A 110.7 . .
C17 C18 H18A 110.7 . .
C9 C18 H18B 110.7 . .
C17 C18 H18B 110.7 . .
H18A C18 H18B 108.8 . .
O2 C19 C24 121.73(18) . .
O2 C19 C20 121.1(2) . .
C24 C19 C20 117.16(17) . .
C21 C20 C19 120.9(2) . .
C21 C20 Cl6 122.86(16) . .
C19 C20 Cl6 116.20(14) . .
C20 C21 C22 121.86(18) . .
C20 C21 Cl5 122.30(18) . .
C22 C21 Cl5 115.80(14) . .
O3 C22 C21 121.52(18) . .
O3 C22 C23 121.4(2) . .
C21 C22 C23 117.03(16) . .
C24 C23 C22 121.2(2) . .
C24 C23 Cl4 122.69(16) . .
C22 C23 Cl4 116.09(14) . .
C23 C24 C19 121.84(18) . .
C23 C24 Cl3 122.95(19) . .
C19 C24 Cl3 115.20(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.701(2) .
Cl2 C6 1.7036(18) .
Cl3 C24 1.7034(19) .
Cl4 C23 1.693(2) .
Cl5 C21 1.7018(19) .
Cl6 C20 1.696(2) .
S1 C1 1.742(3) .
S1 C3 1.7532(19) .
S2 C2 1.742(2) .
S2 C3 1.751(3) .
O1 C4 1.222(3) .
O2 C19 1.218(3) .
O3 C22 1.217(3) .
C1 C2 1.335(3) .
C1 H1 0.9300 .
C2 H2 0.9300 .
C3 C3 1.354(5) 2_766
C4 C6 1.485(3) 2_866
C4 C5 1.491(2) .
C5 C6 1.353(3) .
C7 C16 1.368(4) .
C7 C8 1.412(3) .
C7 C17 1.523(3) .
C8 C13 1.409(3) .
C8 C9 1.415(4) .
C9 C10 1.370(3) .
C9 C18 1.512(3) .
C10 C11 1.426(3) .
C10 H10 0.9300 .
C11 C12 1.380(4) .
C11 H11 0.9300 .
C12 C13 1.423(4) .
C12 H12 0.9300 .
C13 C14 1.436(4) .
C14 C15 1.382(3) .
C14 H14 0.9300 .
C15 C16 1.426(3) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C18 1.568(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C24 1.487(4) .
C19 C20 1.497(3) .
C20 C21 1.350(3) .
C21 C22 1.491(3) .
C22 C23 1.492(3) .
C23 C24 1.349(3) .
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_4
C3 S1 C1 C2 -2.1(3) . .
S1 C1 C2 S2 2.5(4) . .
C3 S2 C2 C1 -1.5(3) . .
C2 S2 C3 C3 179.1(4) . 2_766
C2 S2 C3 S1 0.0(2) . .
C1 S1 C3 C3 -178.1(4) . 2_766
C1 S1 C3 S2 1.0(2) . .
O1 C4 C5 C6 174.7(3) . .
C6 C4 C5 C6 -3.3(5) 2_866 .
O1 C4 C5 Cl1 -5.0(4) . .
C6 C4 C5 Cl1 177.0(2) 2_866 .
C4 C5 C6 C4 3.5(6) . 2_866
Cl1 C5 C6 C4 -176.8(3) . 2_866
C4 C5 C6 Cl2 -179.0(3) . .
Cl1 C5 C6 Cl2 0.7(5) . .
C16 C7 C8 C13 -1.1(5) . .
C17 C7 C8 C13 -178.7(3) . .
C16 C7 C8 C9 -179.9(3) . .
C17 C7 C8 C9 2.5(4) . .
C13 C8 C9 C10 1.6(5) . .
C7 C8 C9 C10 -179.5(3) . .
C13 C8 C9 C18 -179.2(3) . .
C7 C8 C9 C18 -0.4(4) . .
C8 C9 C10 C11 -0.9(5) . .
C18 C9 C10 C11 -179.8(3) . .
C9 C10 C11 C12 0.2(6) . .
C10 C11 C12 C13 -0.1(6) . .
C7 C8 C13 C12 179.8(3) . .
C9 C8 C13 C12 -1.5(5) . .
C7 C8 C13 C14 2.5(5) . .
C9 C8 C13 C14 -178.8(3) . .
C11 C12 C13 C8 0.7(5) . .
C11 C12 C13 C14 177.7(3) . .
C8 C13 C14 C15 -2.1(5) . .
C12 C13 C14 C15 -179.2(3) . .
C13 C14 C15 C16 0.6(5) . .
C8 C7 C16 C15 -0.6(5) . .
C17 C7 C16 C15 176.3(3) . .
C14 C15 C16 C7 0.9(5) . .
C16 C7 C17 C18 179.5(4) . .
C8 C7 C17 C18 -3.4(4) . .
C10 C9 C18 C17 177.2(4) . .
C8 C9 C18 C17 -1.7(4) . .
C7 C17 C18 C9 3.1(3) . .
O2 C19 C20 C21 177.6(3) . .
C24 C19 C20 C21 -1.9(5) . .
O2 C19 C20 Cl6 -4.9(4) . .
C24 C19 C20 Cl6 175.6(3) . .
C19 C20 C21 C22 0.8(5) . .
Cl6 C20 C21 C22 -176.5(3) . .
C19 C20 C21 Cl5 178.4(3) . .
Cl6 C20 C21 Cl5 1.1(5) . .
C20 C21 C22 O3 179.8(3) . .
Cl5 C21 C22 O3 2.0(5) . .
C20 C21 C22 C23 0.9(5) . .
Cl5 C21 C22 C23 -176.9(2) . .
O3 C22 C23 C24 179.6(3) . .
C21 C22 C23 C24 -1.5(5) . .
O3 C22 C23 Cl4 1.5(4) . .
C21 C22 C23 Cl4 -179.6(2) . .
C22 C23 C24 C19 0.4(5) . .
Cl4 C23 C24 C19 178.4(3) . .
C22 C23 C24 Cl3 -178.7(2) . .
Cl4 C23 C24 Cl3 -0.7(5) . .
O2 C19 C24 C23 -178.3(3) . .
C20 C19 C24 C23 1.2(5) . .
O2 C19 C24 Cl3 0.9(5) . .
C20 C19 C24 Cl3 -179.6(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168344066
