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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/8/00/04/8000403.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_8000403
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         'C6 H4 S4, 3(C6 Cl4 O2), 2(C12 H10)'
_chemical_formula_sum            'C48 H24 Cl12 O6 S4'
_chemical_formula_weight         1250.31
_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     dual
_audit_creation_date             2017-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_cell_angle_alpha                96.2006(16)
_cell_angle_beta                 98.4849(17)
_cell_angle_gamma                93.0166(17)
_cell_formula_units_Z            1
_cell_length_a                   7.3358(8)
_cell_length_b                   7.7383(8)
_cell_length_c                   21.822(2)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    300
_cell_measurement_theta_max      29.992
_cell_measurement_theta_min      2.65
_cell_volume                     1215.1(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2 2014.1-1 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27372
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.004
_diffrn_reflns_theta_min         1.900
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1388 before and 0.0444 after correction. The Ratio of minimum to maximum transmission is 0.8143. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         7080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0439P)²+0.3673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6157
_reflns_number_total             7080
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz9b03847_si_002.cif
_cod_data_source_block           (TTF)(Ace)2(CA)3_300K
_cod_database_code               8000403
_shelxl_version_number           2014/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.645
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
S1 S 0.92763(5) 0.91480(5) 0.40012(2) 0.03969(9) Uani 1 1 d .
S2 S 0.88511(5) 0.74066(4) 0.51095(2) 0.04029(9) Uani 1 1 d .
C1 C 0.96053(18) 0.92809(15) 0.48138(6) 0.0316(2) Uani 1 1 d .
C2 C 0.8255(2) 0.7042(2) 0.38856(7) 0.0447(3) Uani 1 1 d .
H2 H 0.7847 0.6485 0.3486 0.054 Uiso 1 1 calc R
C3 C 0.8074(2) 0.62539(18) 0.43840(8) 0.0439(3) Uani 1 1 d .
H3 H 0.7547 0.5120 0.4346 0.053 Uiso 1 1 calc R
Cl1 Cl 0.32128(5) 0.63710(4) 0.43587(2) 0.04233(9) Uani 1 1 d .
Cl2 Cl 0.41080(5) 0.93995(5) 0.35420(2) 0.04372(9) Uani 1 1 d .
O1 O 0.40974(17) 0.75420(14) 0.56826(5) 0.0474(3) Uani 1 1 d .
C4 C 0.45410(17) 0.86446(15) 0.53721(6) 0.0311(2) Uani 1 1 d .
C5 C 0.41675(16) 0.83757(15) 0.46798(6) 0.0296(2) Uani 1 1 d .
C6 C 0.45528(17) 0.96415(16) 0.43345(5) 0.0301(2) Uani 1 1 d .
Cl3 Cl 0.18576(8) -0.02922(6) 0.08397(2) 0.06445(13) Uani 1 1 d .
Cl4 Cl 0.23847(10) 0.29025(8) 0.00761(2) 0.07944(18) Uani 1 1 d .
Cl5 Cl 0.55089(6) 0.68567(5) 0.21936(2) 0.05623(11) Uani 1 1 d .
Cl6 Cl 0.49241(6) 0.36587(5) 0.29597(2) 0.04833(10) Uani 1 1 d .
O2 O 0.30923(18) 0.06551(14) 0.21635(5) 0.0500(3) Uani 1 1 d .
O3 O 0.4096(2) 0.59691(16) 0.08764(6) 0.0631(4) Uani 1 1 d .
C7 C 0.33481(19) 0.18511(17) 0.18686(6) 0.0345(3) Uani 1 1 d .
C8 C 0.2769(2) 0.16991(18) 0.11820(7) 0.0384(3) Uani 1 1 d .
C9 C 0.3003(2) 0.3046(2) 0.08621(7) 0.0426(3) Uani 1 1 d .
C10 C 0.3887(2) 0.47585(18) 0.11673(7) 0.0414(3) Uani 1 1 d .
C11 C 0.45096(19) 0.48923(17) 0.18524(7) 0.0369(3) Uani 1 1 d .
C12 C 0.42613(18) 0.35484(17) 0.21746(6) 0.0341(2) Uani 1 1 d .
C13 C 0.8192(2) 0.14488(19) 0.19351(7) 0.0419(3) Uani 1 1 d .
C14 C 0.7304(3) 0.0573(2) 0.13915(8) 0.0517(4) Uani 1 1 d .
H14 H 0.6811 -0.0565 0.1379 0.062 Uiso 1 1 calc R
C15 C 0.7141(3) 0.1418(2) 0.08462(8) 0.0541(4) Uani 1 1 d .
H15 H 0.6526 0.0815 0.0475 0.065 Uiso 1 1 calc R
C16 C 0.7847(2) 0.3082(2) 0.08405(8) 0.0498(4) Uani 1 1 d .
H16 H 0.7711 0.3590 0.0471 0.060 Uiso 1 1 calc R
C17 C 0.9638(2) 0.5756(2) 0.14820(8) 0.0466(3) Uani 1 1 d .
H17 H 0.9603 0.6393 0.1143 0.056 Uiso 1 1 calc R
C18 C 1.0504(2) 0.6477(2) 0.20553(9) 0.0516(4) Uani 1 1 d .
H18 H 1.1045 0.7606 0.2098 0.062 Uiso 1 1 calc R
C19 C 1.0611(2) 0.5574(2) 0.25893(8) 0.0487(3) Uani 1 1 d .
H19 H 1.1209 0.6102 0.2975 0.058 Uiso 1 1 calc R
C20 C 0.98201(19) 0.39132(19) 0.25274(7) 0.0394(3) Uani 1 1 d .
C21 C 0.89307(19) 0.31648(18) 0.19364(7) 0.0363(3) Uani 1 1 d .
C22 C 0.8789(2) 0.40356(19) 0.13990(7) 0.0403(3) Uani 1 1 d .
C23 C 0.8610(3) 0.0959(2) 0.25910(8) 0.0517(4) Uani 1 1 d .
H23A H 0.9329 -0.0057 0.2599 0.062 Uiso 1 1 calc R
H23B H 0.7476 0.0707 0.2754 0.062 Uiso 1 1 calc R
C24 C 0.9726(2) 0.2566(2) 0.29782(8) 0.0520(4) Uani 1 1 d .
H24A H 0.9110 0.2998 0.3322 0.062 Uiso 1 1 calc R
H24B H 1.0956 0.2272 0.3145 0.062 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C2 S1 C1 94.76(7) . .
C3 S2 C1 94.88(7) . .
S1 C1 S2 114.74(7) . .
C1 C1 S1 122.68(13) 2_776 .
C1 C1 S2 122.58(13) 2_776 .
S1 C2 H2 121.0 . .
C3 C2 S1 117.92(11) . .
C3 C2 H2 121.0 . .
S2 C3 H3 121.2 . .
C2 C3 S2 117.69(11) . .
C2 C3 H3 121.2 . .
O1 C4 C5 121.75(11) . .
O1 C4 C6 121.46(12) . 2_676
C5 C4 C6 116.77(10) . 2_676
C4 C5 Cl1 115.56(9) . .
C6 C5 Cl1 122.65(10) . .
C6 C5 C4 121.79(10) . .
C4 C6 Cl2 115.37(9) 2_676 .
C5 C6 Cl2 123.25(10) . .
C5 C6 C4 121.37(11) . 2_676
O2 C7 C8 121.68(13) . .
O2 C7 C12 121.51(13) . .
C12 C7 C8 116.81(11) . .
C7 C8 Cl3 115.70(10) . .
C9 C8 Cl3 123.00(12) . .
C9 C8 C7 121.29(13) . .
C8 C9 Cl4 122.33(12) . .
C8 C9 C10 122.15(13) . .
C10 C9 Cl4 115.48(11) . .
O3 C10 C9 121.88(15) . .
O3 C10 C11 121.71(15) . .
C9 C10 C11 116.41(11) . .
C10 C11 Cl5 115.80(10) . .
C12 C11 Cl5 122.67(12) . .
C12 C11 C10 121.52(13) . .
C7 C12 Cl6 115.27(9) . .
C11 C12 Cl6 122.94(11) . .
C11 C12 C7 121.78(12) . .
C14 C13 C21 118.99(14) . .
C14 C13 C23 132.85(15) . .
C21 C13 C23 108.16(14) . .
C13 C14 H14 120.5 . .
C13 C14 C15 118.93(16) . .
C15 C14 H14 120.5 . .
C14 C15 H15 118.6 . .
C16 C15 C14 122.73(16) . .
C16 C15 H15 118.6 . .
C15 C16 H16 120.0 . .
C15 C16 C22 119.96(15) . .
C22 C16 H16 120.0 . .
C18 C17 H17 119.8 . .
C18 C17 C22 120.36(15) . .
C22 C17 H17 119.8 . .
C17 C18 H18 118.7 . .
C17 C18 C19 122.60(15) . .
C19 C18 H18 118.7 . .
C18 C19 H19 120.6 . .
C20 C19 C18 118.76(16) . .
C20 C19 H19 120.6 . .
C19 C20 C21 118.77(14) . .
C19 C20 C24 133.13(15) . .
C21 C20 C24 108.06(13) . .
C13 C21 C22 123.21(14) . .
C20 C21 C13 113.09(13) . .
C20 C21 C22 123.70(14) . .
C16 C22 C17 128.00(14) . .
C21 C22 C16 116.18(14) . .
C21 C22 C17 115.81(14) . .
C13 C23 H23A 110.7 . .
C13 C23 H23B 110.7 . .
C13 C23 C24 105.31(13) . .
H23A C23 H23B 108.8 . .
C24 C23 H23A 110.7 . .
C24 C23 H23B 110.7 . .
C20 C24 C23 105.33(13) . .
C20 C24 H24A 110.7 . .
C20 C24 H24B 110.7 . .
C23 C24 H24A 110.7 . .
C23 C24 H24B 110.7 . .
H24A C24 H24B 108.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7450(13) .
S1 C2 1.7340(15) .
S2 C1 1.7461(13) .
S2 C3 1.7327(16) .
C1 C1 1.354(2) 2_776
C2 H2 0.9300 .
C2 C3 1.323(2) .
C3 H3 0.9300 .
Cl1 C5 1.7012(12) .
Cl2 C6 1.6999(12) .
O1 C4 1.2057(15) .
C4 C5 1.4848(17) .
C4 C6 1.4862(16) 2_676
C5 C6 1.3417(17) .
C6 C4 1.4863(16) 2_676
Cl3 C8 1.6956(14) .
Cl4 C9 1.6982(15) .
Cl5 C11 1.6970(14) .
Cl6 C12 1.7021(14) .
O2 C7 1.2050(16) .
O3 C10 1.2026(17) .
C7 C8 1.4858(19) .
C7 C12 1.4852(19) .
C8 C9 1.333(2) .
C9 C10 1.487(2) .
C10 C11 1.488(2) .
C11 C12 1.3361(19) .
C13 C14 1.357(2) .
C13 C21 1.407(2) .
C13 C23 1.512(2) .
C14 H14 0.9300 .
C14 C15 1.411(2) .
C15 H15 0.9300 .
C15 C16 1.365(3) .
C16 H16 0.9300 .
C16 C22 1.418(2) .
C17 H17 0.9300 .
C17 C18 1.363(3) .
C17 C22 1.421(2) .
C18 H18 0.9300 .
C18 C19 1.417(2) .
C19 H19 0.9300 .
C19 C20 1.367(2) .
C20 C21 1.405(2) .
C20 C24 1.515(2) .
C21 C22 1.4079(19) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C23 C24 1.546(3) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
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
S1 C2 C3 S2 0.72(18) . .
C1 S1 C2 C3 -0.79(14) . .
C1 S2 C3 C2 -0.23(14) . .
C2 S1 C1 S2 0.60(9) . .
C2 S1 C1 C1 -179.84(16) . 2_776
C3 S2 C1 S1 -0.31(9) . .
C3 S2 C1 C1 -179.88(16) . 2_776
Cl1 C5 C6 Cl2 0.85(17) . .
Cl1 C5 C6 C4 -177.42(9) . 2_676
O1 C4 C5 Cl1 -3.99(18) . .
O1 C4 C5 C6 175.65(13) . .
C4 C5 C6 Cl2 -178.76(9) . .
C4 C5 C6 C4 3.0(2) . 2_676
C6 C4 C5 Cl1 177.52(9) 2_676 .
C6 C4 C5 C6 -2.8(2) 2_676 .
Cl3 C8 C9 Cl4 0.7(2) . .
Cl3 C8 C9 C10 -177.04(11) . .
Cl4 C9 C10 O3 2.1(2) . .
Cl4 C9 C10 C11 -177.61(11) . .
Cl5 C11 C12 Cl6 -0.19(18) . .
Cl5 C11 C12 C7 178.71(10) . .
O2 C7 C8 Cl3 -3.71(19) . .
O2 C7 C8 C9 177.80(15) . .
O2 C7 C12 Cl6 0.57(18) . .
O2 C7 C12 C11 -178.40(14) . .
O3 C10 C11 Cl5 0.5(2) . .
O3 C10 C11 C12 179.47(15) . .
C7 C8 C9 Cl4 179.07(11) . .
C7 C8 C9 C10 1.3(2) . .
C8 C7 C12 Cl6 -179.32(10) . .
C8 C7 C12 C11 1.71(19) . .
C8 C9 C10 O3 179.93(16) . .
C8 C9 C10 C11 0.3(2) . .
C9 C10 C11 Cl5 -179.81(11) . .
C9 C10 C11 C12 -0.9(2) . .
C10 C11 C12 Cl6 -179.06(10) . .
C10 C11 C12 C7 -0.2(2) . .
C12 C7 C8 Cl3 176.19(10) . .
C12 C7 C8 C9 -2.3(2) . .
C13 C14 C15 C16 0.3(3) . .
C13 C21 C22 C16 -0.1(2) . .
C13 C21 C22 C17 -179.11(13) . .
C13 C23 C24 C20 2.16(17) . .
C14 C13 C21 C20 -179.64(14) . .
C14 C13 C21 C22 0.4(2) . .
C14 C13 C23 C24 178.20(17) . .
C14 C15 C16 C22 -0.1(3) . .
C15 C16 C22 C17 178.83(16) . .
C15 C16 C22 C21 0.0(2) . .
C17 C18 C19 C20 0.2(2) . .
C18 C17 C22 C16 -179.51(16) . .
C18 C17 C22 C21 -0.7(2) . .
C18 C19 C20 C21 0.0(2) . .
C18 C19 C20 C24 177.43(16) . .
C19 C20 C21 C13 179.44(13) . .
C19 C20 C21 C22 -0.6(2) . .
C19 C20 C24 C23 -179.83(16) . .
C20 C21 C22 C16 179.86(13) . .
C20 C21 C22 C17 0.9(2) . .
C21 C13 C14 C15 -0.4(2) . .
C21 C13 C23 C24 -1.41(17) . .
C21 C20 C24 C23 -2.20(17) . .
C22 C17 C18 C19 0.2(2) . .
C23 C13 C14 C15 179.99(17) . .
C23 C13 C21 C20 0.03(17) . .
C23 C13 C21 C22 -179.96(13) . .
C24 C20 C21 C13 1.41(17) . .
C24 C20 C21 C22 -178.59(13) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168344066
