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#$Date: 2022-08-17 01:28:24 +0300 (Wed, 17 Aug 2022) $
#$Revision: 277262 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245317.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_7245317
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_formula_sum            'C15 H12 Cl0 F2 N2 O0 S4'
_chemical_formula_weight         386.51
_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
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2022-06-17 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.828(8)
_cell_angle_beta                 101.369(7)
_cell_angle_gamma                108.957(8)
_cell_formula_units_Z            2
_cell_length_a                   7.0619(6)
_cell_length_b                   10.1071(10)
_cell_length_c                   12.5228(11)
_cell_measurement_reflns_used    1656
_cell_measurement_temperature    294.5(5)
_cell_measurement_theta_max      71.0520
_cell_measurement_theta_min      5.4740
_cell_volume                     820.47(14)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5580
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.009
_diffrn_reflns_theta_min         3.637
_exptl_absorpt_coefficient_mu    5.504
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       plates
_exptl_crystal_F_000             396
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.080
_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     210
_refine_ls_number_reflns         3112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0678
_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)+(0.0749P)²+0.8926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2282
_reflns_number_total             3112
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00857b3.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7245317
_shelx_shelxl_version_number     2016/4
_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, -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
S2 S 1.07971(18) 0.04496(14) 0.67797(11) 0.0573(3) Uani 1 1 d . . . . .
S1 S 0.76752(18) 0.09526(13) 0.51325(10) 0.0532(3) Uani 1 1 d . . . . .
S3 S 0.6111(2) 0.23490(18) 0.67347(11) 0.0694(4) Uani 1 1 d . . . . .
S4 S 0.9810(2) 0.17718(18) 0.86828(12) 0.0735(4) Uani 1 1 d . . . . .
F1 F 0.2942(5) 0.3941(4) 0.5829(2) 0.0741(9) Uani 1 1 d . . . . .
F2 F 0.1773(6) 0.5435(4) 0.7172(2) 0.0757(10) Uani 1 1 d . . . . .
C13 C -0.0661(7) 0.5837(4) 0.5749(4) 0.0457(10) Uani 1 1 d . . . . .
C12 C -0.1282(7) 0.6656(5) 0.6471(4) 0.0490(10) Uani 1 1 d . . . . .
C14 C 0.0900(7) 0.5248(5) 0.6095(4) 0.0504(10) Uani 1 1 d . . . . .
N1 N -0.4357(8) 0.7503(6) 0.5955(4) 0.0733(13) Uani 1 1 d . . . . .
C15 C 0.1494(7) 0.4474(5) 0.5394(4) 0.0508(11) Uani 1 1 d . . . . .
C3 C 0.9690(7) 0.0316(5) 0.5411(4) 0.0500(10) Uani 1 1 d . . . . .
N2 N 0.0567(9) 0.7578(6) 0.8498(4) 0.0787(14) Uani 1 1 d . . . . .
C2 C 0.7888(7) 0.1569(5) 0.6502(4) 0.0517(11) Uani 1 1 d . . . . .
C10 C -0.2999(8) 0.7109(5) 0.6146(4) 0.0550(11) Uani 1 1 d . . . . .
C11 C -0.0223(8) 0.7131(5) 0.7590(4) 0.0567(12) Uani 1 1 d . . . . .
C1 C 0.9360(7) 0.1365(5) 0.7259(4) 0.0556(11) Uani 1 1 d . . . . .
C5 C 0.7089(9) 0.1398(6) 0.8759(5) 0.0671(14) Uani 1 1 d . . . . .
H5 H 0.710463 0.155123 0.954268 0.081 Uiso 1 1 calc R U . . .
C7 C 0.5704(9) -0.0155(6) 0.8334(5) 0.0670(14) Uani 1 1 d . . . . .
H7A H 0.429335 -0.025957 0.834574 0.080 Uiso 1 1 calc R U . . .
H7B H 0.574892 -0.037909 0.757623 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6234(9) 0.2435(6) 0.8232(5) 0.0676(14) Uani 1 1 d . . . . .
H4 H 0.480162 0.214538 0.829936 0.081 Uiso 1 1 calc R U . . .
C9 C 0.6334(13) -0.1194(8) 0.9002(6) 0.097(2) Uani 1 1 d . . . . .
H9A H 0.769367 -0.114438 0.895253 0.146 Uiso 1 1 calc R U . . .
H9B H 0.538464 -0.213252 0.872233 0.146 Uiso 1 1 calc R U . . .
H9C H 0.632336 -0.096665 0.975730 0.146 Uiso 1 1 calc R U . . .
C6 C 0.7284(13) 0.3956(7) 0.8855(7) 0.101(2) Uani 1 1 d . . . . .
H6A H 0.767384 0.390993 0.963529 0.121 Uiso 1 1 calc R U . . .
H6B H 0.853398 0.440754 0.861326 0.121 Uiso 1 1 calc R U . . .
C8 C 0.6036(17) 0.4792(10) 0.8697(11) 0.168(6) Uani 1 1 d . . . . .
H8A H 0.581933 0.496723 0.794642 0.253 Uiso 1 1 calc R U . . .
H8B H 0.669939 0.567458 0.917666 0.253 Uiso 1 1 calc R U . . .
H8C H 0.473427 0.430678 0.886021 0.253 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
F F 0.0727 0.0534 '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 S2 C1 96.0(2) . . ?
C3 S1 C2 95.3(2) . . ?
C2 S3 C4 105.7(2) . . ?
C1 S4 C5 97.3(2) . . ?
C15 C13 C12 123.8(4) 2_566 . ?
C15 C13 C14 112.5(4) 2_566 . ?
C12 C13 C14 123.6(4) . . ?
C13 C12 C11 122.9(4) . . ?
C13 C12 C10 123.4(4) . . ?
C11 C12 C10 113.7(4) . . ?
F2 C14 C15 118.5(4) . . ?
F2 C14 C13 118.3(4) . . ?
C15 C14 C13 123.1(4) . . ?
F1 C15 C14 117.3(4) . . ?
F1 C15 C13 118.3(4) . 2_566 ?
C14 C15 C13 124.3(4) . 2_566 ?
C3 C3 S2 122.3(5) 2_756 . ?
C3 C3 S1 122.5(5) 2_756 . ?
S2 C3 S1 115.1(3) . . ?
C1 C2 S3 127.2(4) . . ?
C1 C2 S1 116.9(4) . . ?
S3 C2 S1 115.9(3) . . ?
N1 C10 C12 175.6(5) . . ?
N2 C11 C12 175.5(6) . . ?
C2 C1 S2 116.5(4) . . ?
C2 C1 S4 126.5(4) . . ?
S2 C1 S4 116.7(3) . . ?
C4 C5 C7 112.9(5) . . ?
C4 C5 S4 111.5(4) . . ?
C7 C5 S4 113.3(4) . . ?
C4 C5 H5 106.2 . . ?
C7 C5 H5 106.2 . . ?
S4 C5 H5 106.2 . . ?
C9 C7 C5 113.2(5) . . ?
C9 C7 H7A 108.9 . . ?
C5 C7 H7A 108.9 . . ?
C9 C7 H7B 108.9 . . ?
C5 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C5 C4 C6 112.8(5) . . ?
C5 C4 S3 113.4(4) . . ?
C6 C4 S3 112.8(5) . . ?
C5 C4 H4 105.6 . . ?
C6 C4 H4 105.6 . . ?
S3 C4 H4 105.6 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C6 C4 113.6(7) . . ?
C8 C6 H6A 108.8 . . ?
C4 C6 H6A 108.8 . . ?
C8 C6 H6B 108.8 . . ?
C4 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
S2 C3 1.715(5) . ?
S2 C1 1.738(5) . ?
S1 C3 1.729(5) . ?
S1 C2 1.746(5) . ?
S3 C2 1.743(5) . ?
S3 C4 1.855(6) . ?
S4 C1 1.744(5) . ?
S4 C5 1.857(6) . ?
F1 C15 1.346(5) . ?
F2 C14 1.340(5) . ?
C13 C15 1.408(6) 2_566 ?
C13 C12 1.409(6) . ?
C13 C14 1.425(6) . ?
C12 C11 1.420(7) . ?
C12 C10 1.427(7) . ?
C14 C15 1.352(7) . ?
N1 C10 1.143(7) . ?
C15 C13 1.408(6) 2_566 ?
C3 C3 1.388(10) 2_756 ?
N2 C11 1.151(7) . ?
C2 C1 1.341(7) . ?
C5 C4 1.498(8) . ?
C5 C7 1.546(8) . ?
C5 H5 0.9800 . ?
C7 C9 1.508(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C4 C6 1.547(8) . ?
C4 H4 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 C8 1.403(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
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
C15 C13 C12 C11 -170.4(5) 2_566 . . . ?
C14 C13 C12 C11 8.6(8) . . . . ?
C15 C13 C12 C10 8.3(8) 2_566 . . . ?
C14 C13 C12 C10 -172.6(5) . . . . ?
C15 C13 C14 F2 -178.1(4) 2_566 . . . ?
C12 C13 C14 F2 2.7(7) . . . . ?
C15 C13 C14 C15 -0.2(8) 2_566 . . . ?
C12 C13 C14 C15 -179.4(5) . . . . ?
F2 C14 C15 F1 -0.2(7) . . . . ?
C13 C14 C15 F1 -178.0(4) . . . . ?
F2 C14 C15 C13 178.1(5) . . . 2_566 ?
C13 C14 C15 C13 0.3(9) . . . 2_566 ?
C1 S2 C3 C3 178.0(6) . . . 2_756 ?
C1 S2 C3 S1 -4.7(3) . . . . ?
C2 S1 C3 C3 -179.0(6) . . . 2_756 ?
C2 S1 C3 S2 3.7(3) . . . . ?
C4 S3 C2 C1 -13.6(6) . . . . ?
C4 S3 C2 S1 164.8(3) . . . . ?
C3 S1 C2 C1 -0.8(4) . . . . ?
C3 S1 C2 S3 -179.3(3) . . . . ?
S3 C2 C1 S2 175.9(3) . . . . ?
S1 C2 C1 S2 -2.4(6) . . . . ?
S3 C2 C1 S4 2.6(8) . . . . ?
S1 C2 C1 S4 -175.8(3) . . . . ?
C3 S2 C1 C2 4.3(5) . . . . ?
C3 S2 C1 S4 178.3(3) . . . . ?
C5 S4 C1 C2 33.6(5) . . . . ?
C5 S4 C1 S2 -139.7(3) . . . . ?
C1 S4 C5 C4 -67.1(4) . . . . ?
C1 S4 C5 C7 61.5(5) . . . . ?
C4 C5 C7 C9 -169.3(6) . . . . ?
S4 C5 C7 C9 62.9(6) . . . . ?
C7 C5 C4 C6 165.1(6) . . . . ?
S4 C5 C4 C6 -66.1(6) . . . . ?
C7 C5 C4 S3 -65.1(6) . . . . ?
S4 C5 C4 S3 63.7(5) . . . . ?
C2 S3 C4 C5 -21.8(5) . . . . ?
C2 S3 C4 C6 108.1(5) . . . . ?
C5 C4 C6 C8 -154.4(9) . . . . ?
S3 C4 C6 C8 75.5(10) . . . . ?
