#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/39/7203967.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_7203967
loop_
_publ_author_name
'John, Derek E.'
'Moore, Adrian J.'
'Bryce, Martin R.'
'Batsanov, Andrei S.'
'Leech, Michael A.'
'Howard, Judith A. K.'
_publ_section_title
;
 New bi(tetrathiafulvalenyl) derivatives and their radical cations:
 synthetic and X-ray structural studies
;
_journal_issue                   6
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1273
_journal_paper_doi               10.1039/b000790k
_journal_volume                  10
_journal_year                    2000
_chemical_formula_sum            'C18 H18 S14'
_chemical_formula_weight         683.16
_chemical_melting_point          433.6(5)
_chemical_name_systematic
; 
 4-bis[4',5,5'-tris(methylsulfanyl)tetrathiafulvalenyl] 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.20(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.374(1)
_cell_length_b                   12.684(2)
_cell_length_c                   26.295(3)
_cell_measurement_reflns_used    371
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      15.7
_cell_volume                     2776.6(6)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measurement_device       'SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21201
_diffrn_reflns_theta_max         26.16
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0.14
_diffrn_standards_number         'not measured'
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  0.6938
_exptl_absorpt_correction_T_min  0.4647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS (G.M.Sheldrick,1997), R(int)=0.050 before correction'
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.187
_refine_ls_goodness_of_fit_obs   1.203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         21168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.199
_refine_ls_restrained_S_obs      1.203
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_obs          0.0420
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²+10.3475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1194
_refine_ls_wR_factor_obs         0.1145
_reflns_number_observed          19392
_reflns_number_total             21201
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b000790k.txt
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to
'/home/adriana/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '160-161 deg.C' was changed to
'433.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+10.3475P] where P=(Fo^2^+2Fc^2^)/3'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+10.3475P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

data name '_exptl_absorp_process_details' was replaced with
'_exptl_absorpt_process_details' as specified in the replacement file
'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               7203967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
S1 S 0.07372(7) 0.53391(5) 0.16303(3) 0.0308(2) Uani 1 d . .
S2 S 0.31402(7) 0.37867(4) 0.13466(2) 0.02396(13) Uani 1 d . .
S3 S -0.08302(8) 0.36809(5) 0.23130(3) 0.0352(2) Uani 1 d . .
S4 S 0.14828(7) 0.20338(4) 0.20756(2) 0.02326(13) Uani 1 d . .
S5A S -0.31517(13) 0.20529(8) 0.26862(4) 0.0279(2) Uani 0.6121(11) d P 1
S5B S -0.2461(2) 0.23034(13) 0.30158(7) 0.0279(2) Uani 0.3879(11) d P 2
S6 S -0.02445(10) 0.03286(5) 0.26116(3) 0.0520(2) Uani 1 d . .
S7 S 0.44643(9) 0.53314(5) 0.06139(3) 0.0427(2) Uani 1 d . .
S11 S 0.28771(7) 0.78610(4) 0.14228(2) 0.02350(13) Uani 1 d . .
S12 S 0.07805(7) 0.85353(4) 0.05037(2) 0.02311(13) Uani 1 d . .
S13 S 0.46816(7) 1.01991(4) 0.14333(2) 0.02414(13) Uani 1 d . .
S14 S 0.25810(7) 1.07714(4) 0.05032(2) 0.02486(13) Uani 1 d . .
S15 S 0.72838(7) 1.17238(5) 0.12212(2) 0.02893(14) Uani 1 d . .
S16 S 0.48861(8) 1.24097(5) 0.01730(2) 0.03109(15) Uani 1 d . .
S17 S -0.02572(7) 0.63149(5) 0.02212(2) 0.02998(14) Uani 1 d . .
C1 C 0.1491(3) 0.4043(2) 0.16903(8) 0.0198(5) Uani 1 d . .
C2 C 0.2103(3) 0.5765(2) 0.12122(8) 0.0207(5) Uani 1 d . .
C3 C 0.3180(3) 0.5062(2) 0.10781(9) 0.0241(5) Uani 1 d . .
C4 C 0.0802(3) 0.3338(2) 0.19800(8) 0.0194(5) Uani 1 d . .
C5 C -0.1172(3) 0.2379(2) 0.25112(11) 0.0420(7) Uani 1 d . .
C6 C -0.0119(3) 0.1639(2) 0.24106(9) 0.0278(5) Uani 1 d . .
C7 C 0.6367(3) 0.4890(2) 0.09281(14) 0.0558(9) Uani 1 d . .
H71 H 0.7227(4) 0.5096(12) 0.0723(3) 0.053(5) Uiso 1 d R .
H72 H 0.6353(8) 0.4120(3) 0.0962(6) 0.053(5) Uiso 1 d R .
H73 H 0.6560(10) 0.5211(10) 0.1268(3) 0.053(5) Uiso 1 d R .
C8A C -0.2848(6) 0.2612(4) 0.3320(2) 0.0442(12) Uani 0.6121(11) d P 1
H81A H -0.3865(10) 0.2598(22) 0.3475(5) 0.066 Uiso 0.6121(11) d PR 1
H82A H -0.2484(34) 0.3345(8) 0.3298(2) 0.066 Uiso 0.6121(11) d PR 1
H83A H -0.2037(26) 0.2206(14) 0.3535(4) 0.066 Uiso 0.6121(11) d PR 1
C8B C -0.4192(9) 0.2158(5) 0.2537(3) 0.035(2) Uiso 0.3879(11) d P 2
H81B H -0.5169(9) 0.2097(5) 0.2710(3) 0.053 Uiso 0.3879(11) d PR 2
H82B H -0.4066(9) 0.1524(5) 0.2333(3) 0.053 Uiso 0.3879(11) d PR 2
H83B H -0.4274(9) 0.2778(5) 0.2313(3) 0.053 Uiso 0.3879(11) d PR 2
C9 C 0.1083(3) -0.0347(2) 0.22336(9) 0.0375(6) Uani 1 d . .
H91 H 0.1106(15) -0.1098(3) 0.2322(4) 0.044(4) Uiso 1 d R .
H92 H 0.2169(5) -0.0055(8) 0.2298(4) 0.044(4) Uiso 1 d R .
H93 H 0.0692(11) -0.0262(10) 0.18711(10) 0.044(4) Uiso 1 d R .
C11 C 0.2358(2) 0.8870(2) 0.09720(8) 0.0198(5) Uani 1 d . .
C12 C 0.1914(3) 0.6860(2) 0.10307(8) 0.0195(5) Uani 1 d . .
C13 C 0.0959(3) 0.7168(2) 0.06169(8) 0.0208(5) Uani 1 d . .
C14 C 0.3097(3) 0.9812(2) 0.09791(8) 0.0189(5) Uani 1 d .. .
C15 C 0.5409(3) 1.1159(2) 0.10266(8) 0.0206(5) Uani 1 d . .
C16 C 0.4454(3) 1.1414(2) 0.06008(8) 0.0211(5) Uani 1 d . .
C17 C 0.0327(3) 0.6658(2) -0.04008(9) 0.0334(6) Uani 1 d . .
H171 H -0.0244(15) 0.7300(7) -0.0523(3) 0.053(5) Uiso 1 d R .
H172 H 0.0045(18) 0.6081(6) -0.0642(2) 0.053(5) Uiso 1 d R .
H173 H 0.1488(4) 0.6783(13) -0.03754(15) 0.053(5) Uiso 1 d R .
C18 C 0.8562(3) 1.0706(2) 0.10101(11) 0.0391(7) Uani 1 d . .
H181 H 0.9690(3) 1.0886(6) 0.1112(5) 0.045(4) Uiso 1 d R .
H182 H 0.8380(14) 1.0650(8) 0.06362(12) 0.045(4) Uiso 1 d R .
H183 H 0.8314(13) 1.0028(3) 0.1163(5) 0.045(4) Uiso 1 d R .
C19 C 0.4048(3) 1.1873(2) -0.04313(9) 0.0329(6) Uani 1 d . .
H191 H 0.4388(16) 1.2300(8) -0.07140(9) 0.053(5) Uiso 1 d R .
H192 H 0.2863(3) 1.1870(12) -0.0455(3) 0.053(5) Uiso 1 d R .
H193 H 0.4429(16) 1.1143(5) -0.0465(3) 0.053(5) Uiso 1 d 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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C2 S1 C1 95.27(10) . . ?
C1 S2 C3 94.92(10) . . ?
C4 S3 C5 94.31(11) . . ?
C6 S4 C4 94.97(10) . . ?
C8A S5A C5 95.9(2) . . ?
C5 S5B C8B 89.5(2) . . ?
C6 S6 C9 103.08(11) . . ?
C3 S7 C7 101.52(13) . . ?
C11 S11 C12 93.73(10) . . ?
C11 S12 C13 94.36(10) . . ?
C14 S13 C15 93.74(10) . . ?
C16 S14 C14 94.00(10) . . ?
C15 S15 C18 99.22(11) . . ?
C16 S16 C19 101.88(11) . . ?
C13 S17 C17 101.08(11) . . ?
C4 C1 S2 125.2(2) . . ?
C4 C1 S1 120.0(2) . . ?
S2 C1 S1 114.82(11) . . ?
C3 C2 C12 126.4(2) . . ?
C3 C2 S1 117.5(2) . . ?
C12 C2 S1 116.04(15) . . ?
C2 C3 S7 122.4(2) . . ?
C2 C3 S2 117.5(2) . . ?
S7 C3 S2 119.89(12) . . ?
C1 C4 S3 121.5(2) . . ?
C1 C4 S4 123.7(2) . . ?
S3 C4 S4 114.82(12) . . ?
C6 C5 S3 117.9(2) . . ?
C6 C5 S5B 124.8(2) . . ?
S3 C5 S5B 113.35(15) . . ?
C6 C5 S5A 122.1(2) . . ?
S3 C5 S5A 118.01(14) . . ?
C5 C6 S6 123.1(2) . . ?
C5 C6 S4 117.1(2) . . ?
S6 C6 S4 119.76(14) . . ?
C14 C11 S12 122.3(2) . . ?
C14 C11 S11 123.7(2) . . ?
S12 C11 S11 114.00(12) . . ?
C13 C12 C2 125.0(2) . . ?
C13 C12 S11 117.3(2) . . ?
C2 C12 S11 117.4(2) . . ?
C12 C13 S17 124.2(2) . . ?
C12 C13 S12 117.2(2) . . ?
S17 C13 S12 118.33(13) . . ?
C11 C14 S13 124.8(2) . . ?
C11 C14 S14 121.7(2) . . ?
S13 C14 S14 113.47(12) . . ?
C16 C15 S15 125.4(2) . . ?
C16 C15 S13 117.1(2) . . ?
S15 C15 S13 117.42(13) . . ?
C15 C16 S16 124.2(2) . . ?
C15 C16 S14 116.8(2) . . ?
S16 C16 S14 118.80(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.755(2) . ?
S1 C1 1.762(2) . ?
S2 C1 1.760(2) . ?
S2 C3 1.766(2) . ?
S3 C4 1.756(2) . ?
S3 C5 1.765(2) . ?
S4 C6 1.756(2) . ?
S4 C4 1.758(2) . ?
S5A C8A 1.804(4) . ?
S5A C5 1.815(3) . ?
S5B C5 1.801(3) . ?
S5B C8B 1.823(7) . ?
S6 C6 1.750(2) . ?
S6 C9 1.788(3) . ?
S7 C3 1.746(2) . ?
S7 C7 1.803(3) . ?
S11 C11 1.767(2) . ?
S11 C12 1.773(2) . ?
S12 C11 1.758(2) . ?
S12 C13 1.764(2) . ?
S13 C14 1.757(2) . ?
S13 C15 1.771(2) . ?
S14 C16 1.761(2) . ?
S14 C14 1.765(2) . ?
S15 C15 1.751(2) . ?
S15 C18 1.802(3) . ?
S16 C16 1.755(2) . ?
S16 C19 1.800(2) . ?
S17 C13 1.749(2) . ?
S17 C17 1.810(2) . ?
C1 C4 1.345(3) . ?
C2 C3 1.342(3) . ?
C2 C12 1.472(3) . ?
C5 C6 1.334(3) . ?
C11 C14 1.345(3) . ?
C12 C13 1.337(3) . ?
C15 C16 1.343(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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S7 C7 C3 C2 -81.1(3) . . . . ?
C7 C3 C2 C12 43.8(4) . . . . ?
C3 C2 C12 C13 89.9(3) . . . . ?
C2 C12 C13 S17 0.8(3) . . . . ?
C12 C13 S17 C17 -128.1(2) . . . . ?
C8A S5A C5 C6 116.4(3) . . . . ?
S5A C5 C6 S6 -19.5(4) . . . . ?
C5 C6 S6 C9 164.9(3) . . . . ?
C8B S5B C5 C6 -110.7(4) . . . . ?
C18 S15 C15 C16 -100.2(2) . . . . ?
S15 C15 C16 S16 -2.8(3) . . . . ?
C15 C16 S16 C19 145.8(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15494551
