#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/04/8000414.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_8000414
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                96.1080(10)
_cell_angle_beta                 98.5800(10)
_cell_angle_gamma                92.3400(10)
_cell_formula_units_Z            1
_cell_length_a                   7.1814(6)
_cell_length_b                   7.6740(6)
_cell_length_c                   21.6396(17)
_cell_measurement_reflns_used    9624
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.014
_cell_measurement_theta_min      2.674
_cell_volume                     1170.57(16)
_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      100
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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            26132
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.013
_diffrn_reflns_theta_min         1.916
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.8497
_exptl_absorpt_correction_T_min  0.6898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1411 before and 0.0400 after correction. The Ratio of minimum to maximum transmission is 0.8118. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.774
_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         0.690
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0248
_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)+(0.0297P)²+0.7344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6430
_reflns_number_total             6790
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz9b03847_si_003.cif
_cod_data_source_block           (TTF)(Ace)2(CA)3_100K
_cod_database_code               8000414
_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   0.917
_shelx_estimated_absorpt_t_min   0.635
_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 0.93040(4) 0.91404(4) 0.39903(2) 0.01176(6) Uani 1 1 d .
S2 S 0.88332(4) 0.73892(3) 0.51118(2) 0.01225(6) Uani 1 1 d .
C1 C 0.96058(15) 0.92728(14) 0.48109(5) 0.01090(19) Uani 1 1 d .
C2 C 0.82566(16) 0.70200(15) 0.38716(5) 0.0139(2) Uani 1 1 d .
H2 H 0.7844 0.6450 0.3459 0.017 Uiso 1 1 calc R
C3 C 0.80510(16) 0.62213(14) 0.43766(6) 0.0139(2) Uani 1 1 d .
H3 H 0.7500 0.5061 0.4338 0.017 Uiso 1 1 calc R
Cl1 Cl 0.31924(4) 0.63333(3) 0.43657(2) 0.01223(6) Uani 1 1 d .
Cl2 Cl 0.41260(4) 0.93531(3) 0.35266(2) 0.01253(6) Uani 1 1 d .
O1 O 0.40380(12) 0.75605(11) 0.57029(4) 0.01480(16) Uani 1 1 d .
C4 C 0.45137(15) 0.86548(14) 0.53824(5) 0.01025(19) Uani 1 1 d .
C5 C 0.41559(15) 0.83597(13) 0.46839(5) 0.00958(18) Uani 1 1 d .
C6 C 0.45613(15) 0.96220(14) 0.43280(5) 0.00993(19) Uani 1 1 d .
Cl3 Cl 0.18547(4) -0.03373(4) 0.08243(2) 0.01848(6) Uani 1 1 d .
Cl4 Cl 0.23887(5) 0.28958(4) 0.00520(2) 0.02241(7) Uani 1 1 d .
Cl5 Cl 0.55618(4) 0.68589(3) 0.21914(2) 0.01567(6) Uani 1 1 d .
Cl6 Cl 0.49716(4) 0.36266(4) 0.29674(2) 0.01390(6) Uani 1 1 d .
O2 O 0.30929(13) 0.06062(11) 0.21663(4) 0.01546(16) Uani 1 1 d .
O3 O 0.41193(14) 0.59832(11) 0.08598(4) 0.01849(18) Uani 1 1 d .
C7 C 0.33586(15) 0.18128(14) 0.18667(5) 0.01112(19) Uani 1 1 d .
C8 C 0.27705(16) 0.16692(14) 0.11718(5) 0.01199(19) Uani 1 1 d .
C9 C 0.30092(16) 0.30334(15) 0.08470(5) 0.0132(2) Uani 1 1 d .
C10 C 0.39086(16) 0.47581(14) 0.11554(5) 0.0126(2) Uani 1 1 d .
C11 C 0.45443(15) 0.48802(14) 0.18476(5) 0.01168(19) Uani 1 1 d .
C12 C 0.42912(15) 0.35235(14) 0.21747(5) 0.01110(19) Uani 1 1 d .
C13 C 0.82163(16) 0.14224(15) 0.19367(5) 0.0131(2) Uani 1 1 d .
C14 C 0.73057(17) 0.05336(15) 0.13831(6) 0.0159(2) Uani 1 1 d .
H14 H 0.6793 -0.0633 0.1370 0.019 Uiso 1 1 calc R
C15 C 0.71468(17) 0.13990(16) 0.08299(6) 0.0161(2) Uani 1 1 d .
H15 H 0.6519 0.0784 0.0446 0.019 Uiso 1 1 calc R
C16 C 0.78619(17) 0.30866(16) 0.08259(6) 0.0152(2) Uani 1 1 d .
H16 H 0.7719 0.3618 0.0446 0.018 Uiso 1 1 calc R
C17 C 0.96820(16) 0.57689(15) 0.14775(6) 0.0133(2) Uani 1 1 d .
H17 H 0.9650 0.6424 0.1128 0.016 Uiso 1 1 calc R
C18 C 1.05624(16) 0.64950(15) 0.20638(6) 0.0156(2) Uani 1 1 d .
H18 H 1.1124 0.7653 0.2109 0.019 Uiso 1 1 calc R
C19 C 1.06611(16) 0.55777(16) 0.26024(6) 0.0150(2) Uani 1 1 d .
H19 H 1.1270 0.6115 0.3001 0.018 Uiso 1 1 calc R
C20 C 0.98606(15) 0.38998(15) 0.25366(5) 0.01190(19) Uani 1 1 d .
C21 C 0.89575(15) 0.31502(14) 0.19355(5) 0.01165(19) Uani 1 1 d .
C22 C 0.88194(16) 0.40362(15) 0.13950(5) 0.0126(2) Uani 1 1 d .
C23 C 0.86308(18) 0.09182(15) 0.25997(6) 0.0159(2) Uani 1 1 d .
H23A H 0.9377 -0.0138 0.2610 0.019 Uiso 1 1 calc R
H23B H 0.7445 0.0675 0.2765 0.019 Uiso 1 1 calc R
C24 C 0.97819(17) 0.25396(16) 0.29936(6) 0.0158(2) Uani 1 1 d .
H24A H 0.9145 0.2988 0.3349 0.019 Uiso 1 1 calc R
H24B H 1.1068 0.2226 0.3162 0.019 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 94.70(5) . .
C3 S2 C1 94.85(5) . .
S1 C1 S2 115.06(6) . .
C1 C1 S1 122.58(11) 2_776 .
C1 C1 S2 122.36(12) 2_776 .
S1 C2 H2 121.0 . .
C3 C2 S1 117.97(9) . .
C3 C2 H2 121.0 . .
S2 C3 H3 121.3 . .
C2 C3 S2 117.40(9) . .
C2 C3 H3 121.3 . .
O1 C4 C5 121.80(10) . .
O1 C4 C6 121.39(10) . 2_676
C5 C4 C6 116.78(9) . 2_676
C4 C5 Cl1 115.67(8) . .
C6 C5 Cl1 122.53(9) . .
C6 C5 C4 121.80(9) . .
C4 C6 Cl2 115.37(8) 2_676 .
C5 C6 Cl2 123.26(8) . .
C5 C6 C4 121.34(9) . 2_676
O2 C7 C8 121.83(10) . .
O2 C7 C12 121.61(10) . .
C8 C7 C12 116.55(9) . .
C7 C8 Cl3 115.67(8) . .
C9 C8 Cl3 122.90(9) . .
C9 C8 C7 121.40(10) . .
C8 C9 Cl4 122.40(9) . .
C8 C9 C10 122.18(10) . .
C10 C9 Cl4 115.37(8) . .
O3 C10 C9 121.85(11) . .
O3 C10 C11 121.91(11) . .
C11 C10 C9 116.24(9) . .
C10 C11 Cl5 115.56(8) . .
C12 C11 Cl5 122.71(9) . .
C12 C11 C10 121.72(10) . .
C7 C12 Cl6 115.17(8) . .
C11 C12 Cl6 122.96(9) . .
C11 C12 C7 121.87(10) . .
C14 C13 C21 118.93(11) . .
C14 C13 C23 132.43(11) . .
C21 C13 C23 108.63(10) . .
C13 C14 H14 120.8 . .
C13 C14 C15 118.49(11) . .
C15 C14 H14 120.8 . .
C14 C15 H15 118.6 . .
C16 C15 C14 122.88(11) . .
C16 C15 H15 118.6 . .
C15 C16 H16 120.1 . .
C15 C16 C22 119.70(11) . .
C22 C16 H16 120.1 . .
C18 C17 H17 119.9 . .
C18 C17 C22 120.12(11) . .
C22 C17 H17 119.9 . .
C17 C18 H18 118.8 . .
C17 C18 C19 122.48(11) . .
C19 C18 H18 118.8 . .
C18 C19 H19 120.6 . .
C20 C19 C18 118.77(11) . .
C20 C19 H19 120.6 . .
C19 C20 C21 118.89(11) . .
C19 C20 C24 132.67(11) . .
C21 C20 C24 108.39(10) . .
C13 C21 C20 112.74(10) . .
C22 C21 C13 123.70(10) . .
C22 C21 C20 123.55(11) . .
C17 C22 C16 127.52(11) . .
C21 C22 C16 116.29(10) . .
C21 C22 C17 116.18(10) . .
C13 C23 H23A 110.7 . .
C13 C23 H23B 110.7 . .
C13 C23 C24 105.08(9) . .
H23A C23 H23B 108.8 . .
C24 C23 H23A 110.7 . .
C24 C23 H23B 110.7 . .
C20 C24 C23 105.07(9) . .
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 1.7480(11) .
S1 C2 1.7415(12) .
S2 C1 1.7503(11) .
S2 C3 1.7432(12) .
C1 C1 1.361(2) 2_776
C2 H2 0.9500 .
C2 C3 1.3323(17) .
C3 H3 0.9500 .
Cl1 C5 1.7068(11) .
Cl2 C6 1.7043(11) .
O1 C4 1.2140(14) .
C4 C5 1.4862(15) .
C4 C6 1.4867(14) 2_676
C5 C6 1.3486(15) .
C6 C4 1.4866(14) 2_676
Cl3 C8 1.7007(11) .
Cl4 C9 1.7025(12) .
Cl5 C11 1.7029(11) .
Cl6 C12 1.7043(11) .
O2 C7 1.2101(14) .
O3 C10 1.2088(14) .
C7 C8 1.4909(15) .
C7 C12 1.4917(15) .
C8 C9 1.3405(16) .
C9 C10 1.4926(16) .
C10 C11 1.4912(16) .
C11 C12 1.3408(15) .
C13 C14 1.3725(17) .
C13 C21 1.4089(15) .
C13 C23 1.5157(16) .
C14 H14 0.9500 .
C14 C15 1.4217(17) .
C15 H15 0.9500 .
C15 C16 1.3749(17) .
C16 H16 0.9500 .
C16 C22 1.4267(16) .
C17 H17 0.9500 .
C17 C18 1.3789(17) .
C17 C22 1.4258(16) .
C18 H18 0.9500 .
C18 C19 1.4187(17) .
C19 H19 0.9500 .
C19 C20 1.3729(16) .
C20 C21 1.4150(15) .
C20 C24 1.5172(16) .
C21 C22 1.4073(15) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C23 C24 1.5614(17) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
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 0.62(13) . .
C1 S1 C2 C3 -0.95(10) . .
C1 S2 C3 C2 0.07(10) . .
C2 S1 C1 S2 0.96(7) . .
C2 S1 C1 C1 -179.46(14) . 2_776
C3 S2 C1 S1 -0.71(7) . .
C3 S2 C1 C1 179.71(14) . 2_776
Cl1 C5 C6 Cl2 1.10(14) . .
Cl1 C5 C6 C4 -176.97(8) . 2_676
O1 C4 C5 Cl1 -4.49(14) . .
O1 C4 C5 C6 175.16(11) . .
C4 C5 C6 Cl2 -178.53(8) . .
C4 C5 C6 C4 3.39(18) . 2_676
C6 C4 C5 Cl1 177.10(8) 2_676 .
C6 C4 C5 C6 -3.24(17) 2_676 .
Cl3 C8 C9 Cl4 0.82(15) . .
Cl3 C8 C9 C10 -176.70(8) . .
Cl4 C9 C10 O3 2.33(15) . .
Cl4 C9 C10 C11 -177.25(8) . .
Cl5 C11 C12 Cl6 -0.42(15) . .
Cl5 C11 C12 C7 178.64(8) . .
O2 C7 C8 Cl3 -4.29(15) . .
O2 C7 C8 C9 177.56(11) . .
O2 C7 C12 Cl6 0.92(14) . .
O2 C7 C12 C11 -178.20(11) . .
O3 C10 C11 Cl5 0.57(15) . .
O3 C10 C11 C12 179.34(11) . .
C7 C8 C9 Cl4 178.83(8) . .
C7 C8 C9 C10 1.31(17) . .
C8 C7 C12 Cl6 -179.14(8) . .
C8 C7 C12 C11 1.73(16) . .
C8 C9 C10 O3 -179.99(11) . .
C8 C9 C10 C11 0.43(16) . .
C9 C10 C11 Cl5 -179.85(8) . .
C9 C10 C11 C12 -1.08(16) . .
C10 C11 C12 Cl6 -179.10(8) . .
C10 C11 C12 C7 -0.05(17) . .
C12 C7 C8 Cl3 175.78(8) . .
C12 C7 C8 C9 -2.37(16) . .
C13 C14 C15 C16 -0.13(18) . .
C13 C21 C22 C16 0.10(16) . .
C13 C21 C22 C17 -178.84(10) . .
C13 C23 C24 C20 2.88(12) . .
C14 C13 C21 C20 -179.80(10) . .
C14 C13 C21 C22 0.08(17) . .
C14 C13 C23 C24 178.06(12) . .
C14 C15 C16 C22 0.32(18) . .
C15 C16 C22 C17 178.52(11) . .
C15 C16 C22 C21 -0.29(16) . .
C17 C18 C19 C20 0.42(17) . .
C18 C17 C22 C16 -179.74(11) . .
C18 C17 C22 C21 -0.93(16) . .
C18 C19 C20 C21 -0.35(16) . .
C18 C19 C20 C24 176.81(11) . .
C19 C20 C21 C13 179.49(10) . .
C19 C20 C21 C22 -0.39(17) . .
C19 C20 C24 C23 179.80(12) . .
C20 C21 C22 C16 179.97(10) . .
C20 C21 C22 C17 1.02(16) . .
C21 C13 C14 C15 -0.07(17) . .
C21 C13 C23 C24 -2.01(12) . .
C21 C20 C24 C23 -2.82(12) . .
C22 C17 C18 C19 0.25(17) . .
C23 C13 C14 C15 179.85(12) . .
C23 C13 C21 C20 0.26(13) . .
C23 C13 C21 C22 -179.86(10) . .
C24 C20 C21 C13 1.69(13) . .
C24 C20 C21 C22 -178.19(10) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168344066
