#------------------------------------------------------------------------------
#$Date: 2022-08-17 01:28:24 +0300 (Wed, 17 Aug 2022) $
#$Revision: 277262 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245319.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_7245319
loop_
_publ_author_name
'Mroweh, Nabil'
'Cauchy, Thomas'
'Vanthuyne, Nicolas'
'Avarvari, Narcis'
_publ_section_title
;
 Chiral diethyl-EDT-TTF and tetraethyl-BEDT-TTF: synthesis, structural
 characterization, radical cation salt and charge transfer complexes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00857B
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H14 S6'
_chemical_formula_sum            'C12 H14 S6'
_chemical_formula_weight         350.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-02 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.154(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1770(3)
_cell_length_b                   10.9534(6)
_cell_length_c                   11.7837(8)
_cell_measurement_reflns_used    1613
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.8900
_cell_measurement_theta_min      3.7320
_cell_volume                     792.68(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, V2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 5.1990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova(Cu)micro-focus sealed X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2914
_diffrn_reflns_point_group_measured_fraction_full 0.730
_diffrn_reflns_point_group_measured_fraction_max 0.698
_diffrn_reflns_theta_full        68.500
_diffrn_reflns_theta_max         73.288
_diffrn_reflns_theta_min         3.773
_exptl_absorpt_coefficient_mu    7.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2231
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0603P)²+0.0096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.381
_reflns_Friedel_fraction_full    0.439
_reflns_Friedel_fraction_max     0.407
_reflns_number_gt                2062
_reflns_number_total             2231
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00857b3.cif
_cod_data_source_block           shelx_CCDC3
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7245319
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2892(13) 0.5906(9) 0.4658(6) 0.095(3) Uani 1 1 d . . . . .
H1 H 0.297404 0.664940 0.428249 0.114 Uiso 1 1 calc R U . . .
C2 C 0.1111(12) 0.5257(10) 0.4541(6) 0.098(3) Uani 1 1 d . . . . .
H2 H -0.011301 0.552821 0.408174 0.117 Uiso 1 1 calc R U . . .
C3 C 0.3655(8) 0.4096(5) 0.6010(4) 0.0524(11) Uani 1 1 d . . . . .
C4 C 0.4399(7) 0.3376(5) 0.6885(4) 0.0476(10) Uani 1 1 d . . . . .
C5 C 0.6446(7) 0.2534(4) 0.8746(4) 0.0424(9) Uani 1 1 d . . . . .
C6 C 0.4552(6) 0.1929(4) 0.8622(4) 0.0434(10) Uani 1 1 d . . . . .
C7 C 0.8298(7) 0.0780(5) 1.0366(4) 0.0506(11) Uani 1 1 d . . . . .
H7 H 0.971359 0.039284 1.031335 0.061 Uiso 1 1 calc R U . . .
C8 C 0.6631(7) 0.0009(5) 0.9641(5) 0.0532(12) Uani 1 1 d . . . . .
H8 H 0.647947 -0.074914 1.006693 0.064 Uiso 1 1 calc R U . . .
C9 C 0.7970(9) 0.0797(7) 1.1632(5) 0.0673(15) Uani 1 1 d . . . . .
H9A H 0.652476 0.111045 1.170860 0.081 Uiso 1 1 calc R U . . .
H9B H 0.802305 -0.003725 1.190945 0.081 Uiso 1 1 calc R U . . .
C10 C 0.7321(9) -0.0367(5) 0.8485(5) 0.0625(14) Uani 1 1 d . . . . .
H10A H 0.743450 0.035998 0.802502 0.075 Uiso 1 1 calc R U . . .
H10B H 0.875536 -0.073547 0.860430 0.075 Uiso 1 1 calc R U . . .
C11 C 0.9581(13) 0.1535(8) 1.2377(6) 0.091(2) Uani 1 1 d . . . . .
H11A H 1.102818 0.133013 1.221701 0.136 Uiso 1 1 calc R U . . .
H11B H 0.942898 0.136188 1.316365 0.136 Uiso 1 1 calc R U . . .
H11C H 0.932120 0.238762 1.223150 0.136 Uiso 1 1 calc R U . . .
C12 C 0.5772(15) -0.1259(8) 0.7826(8) 0.100(3) Uani 1 1 d . . . . .
H12A H 0.578876 -0.202115 0.822957 0.150 Uiso 1 1 calc R U . . .
H12B H 0.622612 -0.139039 0.708190 0.150 Uiso 1 1 calc R U . . .
H12C H 0.432445 -0.092874 0.775187 0.150 Uiso 1 1 calc R U . . .
S1 S 0.5113(3) 0.53398(17) 0.55365(15) 0.0774(5) Uani 1 1 d . . . . .
S2 S 0.1077(2) 0.38849(19) 0.52595(13) 0.0783(5) Uani 1 1 d . . . . .
S3 S 0.70113(18) 0.35101(11) 0.76291(10) 0.0494(3) Uani 1 1 d . . . . .
S4 S 0.28553(18) 0.21632(13) 0.73489(12) 0.0578(3) Uani 1 1 d . . . . .
S5 S 0.8541(2) 0.23660(14) 0.98384(12) 0.0639(4) Uani 1 1 d . . . . .
S6 S 0.39430(17) 0.07517(13) 0.95197(13) 0.0595(4) 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 0.0181 0.0091 '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 0.3331 0.5567 '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 C1 S1 118.0(6) . . ?
C2 C1 H1 121.0 . . ?
S1 C1 H1 121.0 . . ?
C1 C2 S2 118.5(5) . . ?
C1 C2 H2 120.7 . . ?
S2 C2 H2 120.7 . . ?
C4 C3 S2 121.9(4) . . ?
C4 C3 S1 123.8(4) . . ?
S2 C3 S1 114.3(3) . . ?
C3 C4 S4 122.1(4) . . ?
C3 C4 S3 123.7(4) . . ?
S4 C4 S3 114.1(3) . . ?
C6 C5 S5 127.0(3) . . ?
C6 C5 S3 117.4(4) . . ?
S5 C5 S3 115.3(2) . . ?
C5 C6 S6 123.1(4) . . ?
C5 C6 S4 117.1(3) . . ?
S6 C6 S4 118.8(3) . . ?
C8 C7 C9 113.7(4) . . ?
C8 C7 S5 114.0(3) . . ?
C9 C7 S5 109.9(4) . . ?
C8 C7 H7 106.2 . . ?
C9 C7 H7 106.2 . . ?
S5 C7 H7 106.2 . . ?
C7 C8 C10 114.4(4) . . ?
C7 C8 S6 110.4(4) . . ?
C10 C8 S6 112.7(4) . . ?
C7 C8 H8 106.2 . . ?
C10 C8 H8 106.2 . . ?
S6 C8 H8 106.2 . . ?
C11 C9 C7 115.6(5) . . ?
C11 C9 H9A 108.4 . . ?
C7 C9 H9A 108.4 . . ?
C11 C9 H9B 108.4 . . ?
C7 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C12 C10 C8 114.1(6) . . ?
C12 C10 H10A 108.7 . . ?
C8 C10 H10A 108.7 . . ?
C12 C10 H10B 108.7 . . ?
C8 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 S1 C3 93.9(3) . . ?
C2 S2 C3 94.2(4) . . ?
C4 S3 C5 94.4(2) . . ?
C6 S4 C4 94.7(2) . . ?
C5 S5 C7 105.5(2) . . ?
C6 S6 C8 97.1(2) . . ?
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
C1 C2 1.305(13) . ?
C1 S1 1.742(7) . ?
C1 H1 0.9300 . ?
C2 S2 1.727(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.341(7) . ?
C3 S2 1.752(5) . ?
C3 S1 1.756(6) . ?
C4 S4 1.756(5) . ?
C4 S3 1.758(5) . ?
C5 C6 1.339(6) . ?
C5 S5 1.735(5) . ?
C5 S3 1.759(5) . ?
C6 S6 1.734(5) . ?
C6 S4 1.755(5) . ?
C7 C8 1.521(8) . ?
C7 C9 1.527(7) . ?
C7 S5 1.856(5) . ?
C7 H7 0.9800 . ?
C8 C10 1.527(8) . ?
C8 S6 1.841(5) . ?
C8 H8 0.9800 . ?
C9 C11 1.493(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.521(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
