#------------------------------------------------------------------------------
#$Date: 2018-09-10 23:06:09 +0300 (Mon, 10 Sep 2018) $
#$Revision: 210798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/28/7102805.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_7102805
loop_
_publ_author_name
'Chas, Marcos'
'Lemarié, Margareth'
'Gulea, Mihaela'
'Avarvari, Narcis'
_publ_section_title
;
 Chemo- and enantioselective sulfoxidation of
 bis(ethylenedithio)-tetrathiafulvalene (BEDT-TTF) into chiral
 BEDT-TTF-sulfoxide
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   2
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              220
_journal_page_last               222
_journal_paper_doi               10.1039/b714245e
_journal_year                    2008
_chemical_formula_sum            'C22 H8 F4 N4 O2 S8'
_chemical_formula_weight         692.80
_chemical_name_common            (BEDT-TTF-bis(sulfoxide))(TCNQF4)
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.44(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.776(4)
_cell_length_b                   9.890(3)
_cell_length_c                   10.644(5)
_cell_measurement_reflns_used    113
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.4
_cell_measurement_theta_min      4.4
_cell_volume                     2641.2(1)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  area_detector
_diffrn_measurement_method       CCD
_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  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16031
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.76995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.52(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5001
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0459P)²+0.3008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                3398
_reflns_number_total             5001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b714245e.txt
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7102805
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.55918(5) 0.26381(18) 0.80226(16) 0.0741(5) Uani 1 1 d . . .
S2 S 0.53314(5) 0.53360(15) 0.57204(13) 0.0576(4) Uani 1 1 d . . .
S3 S 0.44425(5) 0.28340(12) 0.75442(12) 0.0440(3) Uani 1 1 d . . .
S4 S 0.42368(4) 0.51200(12) 0.56831(12) 0.0406(3) Uani 1 1 d . . .
S5 S 0.32070(4) 0.28579(12) 0.73420(12) 0.0454(3) Uani 1 1 d . . .
S6 S 0.29888(5) 0.51234(13) 0.54538(12) 0.0415(3) Uani 1 1 d . . .
S7 S 0.21525(5) 0.27480(15) 0.75724(14) 0.0571(4) Uani 1 1 d . . .
S8 S 0.18654(5) 0.54224(15) 0.52345(12) 0.0543(4) Uani 1 1 d . . .
O1A O 0.3175(2) 0.1522(5) 0.6695(6) 0.0478(16) Uani 0.50 1 d P . .
O1B O 0.3470(2) 0.2914(6) 0.8686(6) 0.0433(15) Uiso 0.50 1 d P . .
O2A O 0.4464(3) 0.2864(7) 0.8882(7) 0.0603(18) Uiso 0.50 1 d P . .
O2B O 0.4320(3) 0.1538(8) 0.6858(7) 0.072(2) Uiso 0.50 1 d P . .
C1 C 0.5982(2) 0.3245(8) 0.7088(8) 0.093(2) Uani 1 1 d . . .
H1A H 0.6351 0.2997 0.7564 0.112 Uiso 1 1 calc R . .
H1B H 0.5869 0.2779 0.6233 0.112 Uiso 1 1 calc R . .
C2 C 0.59621(19) 0.4741(8) 0.6820(7) 0.090(2) Uani 1 1 d . . .
H2A H 0.6231 0.4963 0.6435 0.108 Uiso 1 1 calc R . .
H2B H 0.6052 0.5218 0.7667 0.108 Uiso 1 1 calc R . .
C3 C 0.49852(17) 0.3488(5) 0.7228(5) 0.0478(13) Uani 1 1 d . . .
C4 C 0.48861(17) 0.4528(5) 0.6341(5) 0.0439(12) Uani 1 1 d . . .
C5 C 0.39815(16) 0.4009(4) 0.6575(4) 0.0343(10) Uani 1 1 d . . .
C6 C 0.34676(17) 0.4012(4) 0.6487(4) 0.0347(10) Uani 1 1 d . . .
C7 C 0.25695(16) 0.3544(5) 0.6860(4) 0.0376(11) Uani 1 1 d . . .
C8 C 0.24667(17) 0.4568(5) 0.5983(4) 0.0373(11) Uani 1 1 d . . .
C9 C 0.1524(2) 0.3396(6) 0.6532(6) 0.0739(18) Uani 1 1 d . . .
H9A H 0.1420 0.2951 0.5666 0.089 Uiso 1 1 calc R . .
H9B H 0.1259 0.3176 0.6931 0.089 Uiso 1 1 calc R . .
C10 C 0.1523(2) 0.4865(6) 0.6327(6) 0.0697(17) Uani 1 1 d . . .
H10A H 0.1686 0.5297 0.7193 0.084 Uiso 1 1 calc R . .
H10B H 0.1156 0.5171 0.5961 0.084 Uiso 1 1 calc R . .
F1 F 0.85302(10) 0.2313(3) 0.8680(3) 0.0636(8) Uani 1 1 d . . .
F2 F 0.95228(10) 0.2360(3) 0.8753(3) 0.0649(8) Uani 1 1 d . . .
F3 F 0.79928(11) 0.4704(3) 0.4572(3) 0.0573(8) Uani 1 1 d . . .
F4 F 0.89748(10) 0.4777(3) 0.4655(3) 0.0551(8) Uani 1 1 d . . .
N1 N 0.73540(18) 0.2494(5) 0.8384(5) 0.0667(13) Uani 1 1 d . . .
N2 N 0.6905(2) 0.4777(5) 0.4924(5) 0.0853(17) Uani 1 1 d . . .
N3 N 1.06601(18) 0.2736(5) 0.8622(5) 0.0754(15) Uani 1 1 d . . .
N4 N 1.0142(2) 0.4806(6) 0.5069(6) 0.0864(17) Uani 1 1 d . . .
C11 C 0.82163(16) 0.3550(4) 0.6663(4) 0.0363(10) Uani 1 1 d . . .
C12 C 0.86437(19) 0.2931(5) 0.7704(4) 0.0405(11) Uani 1 1 d . . .
C13 C 0.91493(16) 0.2956(5) 0.7746(4) 0.0394(11) Uani 1 1 d . . .
C14 C 0.93045(16) 0.3609(4) 0.6730(4) 0.0358(10) Uani 1 1 d . . .
C15 C 0.88748(17) 0.4186(4) 0.5667(4) 0.0354(10) Uani 1 1 d . . .
C16 C 0.83681(18) 0.4153(4) 0.5626(4) 0.0376(11) Uani 1 1 d . . .
C17 C 0.76970(17) 0.3583(4) 0.6654(4) 0.0389(11) Uani 1 1 d . . .
C18 C 0.75318(18) 0.2950(5) 0.7655(5) 0.0473(12) Uani 1 1 d . . .
C19 C 0.7266(2) 0.4257(5) 0.5666(5) 0.0523(13) Uani 1 1 d . . .
C20 C 0.98280(17) 0.3665(5) 0.6782(4) 0.0394(11) Uani 1 1 d . . .
C21 C 1.0275(2) 0.3128(5) 0.7844(6) 0.0521(13) Uani 1 1 d . . .
C22 C 0.99866(18) 0.4309(6) 0.5808(5) 0.0537(14) 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 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
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
C3 S1 C1 101.2(3) . . ?
C4 S2 C2 102.5(3) . . ?
O2A S3 O2B 116.7(4) . . ?
O2A S3 C3 116.8(3) . . ?
O2B S3 C3 106.8(3) . . ?
O2A S3 C5 110.8(3) . . ?
O2B S3 C5 107.5(3) . . ?
C3 S3 C5 96.0(2) . . ?
C4 S4 C5 95.5(2) . . ?
O1B S5 O1A 116.9(3) . . ?
O1B S5 C7 112.9(3) . . ?
O1A S5 C7 108.7(3) . . ?
O1B S5 C6 111.6(3) . . ?
O1A S5 C6 108.0(3) . . ?
C7 S5 C6 96.9(2) . . ?
C6 S6 C8 95.3(2) . . ?
C7 S7 C9 100.2(2) . . ?
C8 S8 C10 98.8(2) . . ?
C2 C1 S1 116.7(5) . . ?
C1 C2 S2 114.3(5) . . ?
C4 C3 S3 116.5(3) . . ?
C4 C3 S1 128.2(4) . . ?
S3 C3 S1 115.2(3) . . ?
C3 C4 S4 117.5(3) . . ?
C3 C4 S2 128.0(3) . . ?
S4 C4 S2 114.4(3) . . ?
C6 C5 S4 123.2(3) . . ?
C6 C5 S3 122.5(3) . . ?
S4 C5 S3 114.3(2) . . ?
C5 C6 S5 123.1(3) . . ?
C5 C6 S6 123.4(3) . . ?
S5 C6 S6 113.4(2) . . ?
C8 C7 S5 116.3(3) . . ?
C8 C7 S7 129.7(3) . . ?
S5 C7 S7 114.1(3) . . ?
C7 C8 S8 128.1(3) . . ?
C7 C8 S6 117.7(3) . . ?
S8 C8 S6 114.2(3) . . ?
C10 C9 S7 113.6(4) . . ?
C9 C10 S8 115.0(4) . . ?
C17 C11 C12 123.2(4) . . ?
C17 C11 C16 122.5(4) . . ?
C12 C11 C16 114.3(4) . . ?
F1 C12 C13 119.1(4) . . ?
F1 C12 C11 117.7(4) . . ?
C13 C12 C11 123.1(4) . . ?
F2 C13 C12 119.3(4) . . ?
F2 C13 C14 118.3(4) . . ?
C12 C13 C14 122.5(4) . . ?
C20 C14 C15 122.9(4) . . ?
C20 C14 C13 122.8(4) . . ?
C15 C14 C13 114.4(4) . . ?
F4 C15 C16 118.1(4) . . ?
F4 C15 C14 119.0(4) . . ?
C16 C15 C14 122.9(4) . . ?
F3 C16 C15 118.2(4) . . ?
F3 C16 C11 119.0(4) . . ?
C15 C16 C11 122.7(4) . . ?
C11 C17 C19 124.5(4) . . ?
C11 C17 C18 123.6(4) . . ?
C19 C17 C18 111.9(4) . . ?
N1 C18 C17 173.5(5) . . ?
N2 C19 C17 175.9(6) . . ?
C14 C20 C22 123.5(4) . . ?
C14 C20 C21 125.0(4) . . ?
C22 C20 C21 111.5(4) . . ?
N3 C21 C20 173.6(6) . . ?
N4 C22 C20 176.1(6) . . ?
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 C3 1.761(5) . ?
S1 C1 1.780(7) . ?
S2 C4 1.745(5) . ?
S2 C2 1.785(5) . ?
S3 O2A 1.406(7) . ?
S3 O2B 1.455(8) . ?
S3 C3 1.728(5) . ?
S3 C5 1.746(4) . ?
S4 C4 1.734(4) . ?
S4 C5 1.740(4) . ?
S5 O1B 1.357(6) . ?
S5 O1A 1.479(5) . ?
S5 C7 1.739(4) . ?
S5 C6 1.750(4) . ?
S6 C6 1.754(4) . ?
S6 C8 1.768(5) . ?
S7 C7 1.741(4) . ?
S7 C9 1.780(5) . ?
S8 C8 1.745(4) . ?
S8 C10 1.801(6) . ?
C1 C2 1.504(9) . ?
C3 C4 1.358(6) . ?
C5 C6 1.346(5) . ?
C7 C8 1.339(6) . ?
C9 C10 1.469(8) . ?
F1 C12 1.329(5) . ?
F2 C13 1.322(5) . ?
F3 C16 1.334(5) . ?
F4 C15 1.332(5) . ?
N1 C18 1.136(6) . ?
N2 C19 1.137(6) . ?
N3 C21 1.141(6) . ?
N4 C22 1.123(6) . ?
C11 C17 1.388(6) . ?
C11 C12 1.423(6) . ?
C11 C16 1.432(6) . ?
C12 C13 1.339(6) . ?
C13 C14 1.440(6) . ?
C14 C20 1.384(6) . ?
C14 C15 1.421(6) . ?
C15 C16 1.343(5) . ?
C17 C19 1.425(7) . ?
C17 C18 1.433(7) . ?
C20 C22 1.404(7) . ?
C20 C21 1.431(7) . ?
