#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:28:29 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284274 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246631.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_7246631
loop_
_publ_author_name
'Beau, Maxime'
'Jeannin, Olivier'
'Fourmigué, Marc'
'Auban-Senzier, Pascale'
'Pasquier, Claude'
'Alemany, Pere'
'Canadell, Enric'
'Jeon, Ie-Rang'
_publ_section_title
;
 Chalcogen bonding and variable charge transfer degree in two polymorphs
 of 1 : 1 conducting salts with segregated stacks
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              3189
_journal_page_last               3197
_journal_paper_doi               10.1039/D3CE00260H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C10 H10 S6 Se2, C12 H2 F2 N4'
_chemical_formula_sum            'C22 H12 F2 N4 S6 Se2'
_chemical_formula_weight         720.64
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2023-03-29T14:42:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-03-29 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.272(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3862(16)
_cell_length_b                   20.785(2)
_cell_length_c                   7.6276(9)
_cell_measurement_reflns_used    2416
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.9101
_cell_measurement_theta_min      2.8871
_cell_measurement_wavelength     0.71073
_cell_volume                     2556.2(5)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2902
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.42
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.55
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0327P)²+5.5250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.097
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0
_reflns_number_gt                1929
_reflns_number_total             2902
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00260h2.cif
_cod_data_source_block           beta-[EDT-TTF(SeMe)2](F2TCNQ)
_cod_depositor_comments
'Adding full bibliography for 7246630--7246631.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7246631
_shelx_estimated_absorpt_t_min   0.47
_shelx_estimated_absorpt_t_max   0.904
_shelx_shelxl_version_number     2018/3
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'
'-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_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 0.5 0.5672(3) 0.75 0.0406(19) Uani 1 2 d S T P . .
C2 C 0.5420(3) 0.6856(2) 0.7695(7) 0.0323(11) Uani 1 1 d . . . . .
C3 C 0.7098(3) 0.7313(3) 0.7707(11) 0.070(2) Uani 1 1 d . . . . .
H3A H 0.730232 0.698982 0.857466 0.105 Uiso 1 1 calc R U . . .
H3B H 0.748688 0.766154 0.779595 0.105 Uiso 1 1 calc R U . . .
H3C H 0.702823 0.712905 0.653459 0.105 Uiso 1 1 calc R U . . .
C4 C 0.5 0.5012(3) 0.75 0.0444(19) Uani 1 2 d S T P . .
C5 C 0.4584(3) 0.3827(2) 0.7322(7) 0.0363(12) Uani 1 1 d . . . . .
C6 C 0.4605(4) 0.2521(2) 0.6871(9) 0.0585(17) Uani 1 1 d . . . . .
H6A H 0.431949 0.21204 0.701354 0.07 Uiso 1 1 calc R U . . .
H6B H 0.472448 0.252637 0.567072 0.07 Uiso 1 1 calc R U . . .
C7 C 0.4655(3) 0.9433(2) 0.4403(7) 0.0286(11) Uani 1 1 d . . . . .
C8 C 0.5369(3) 0.9420(2) 0.5602(6) 0.0279(10) Uani 1 1 d . . . . .
H8 H 0.56066 0.902565 0.597594 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5761(3) 0.9994(2) 0.6301(6) 0.0262(10) Uani 1 1 d . . . . .
C10 C 0.6486(3) 0.9987(2) 0.7581(6) 0.0293(10) Uani 1 1 d . . . . .
C11 C 0.6859(3) 0.9395(3) 0.8236(7) 0.0382(12) Uani 1 1 d . . . . .
C12 C 0.6910(3) 1.0546(3) 0.8376(8) 0.0420(13) Uani 1 1 d . . . . .
F1 F 0.43234(19) 0.88635(13) 0.3778(4) 0.0463(8) Uani 1 1 d . . . . .
N1 N 0.7164(3) 0.8926(2) 0.8802(7) 0.0590(15) Uani 1 1 d . . . . .
N2 N 0.7274(3) 1.0961(3) 0.9099(8) 0.0705(17) Uani 1 1 d . . . . .
S1 S 0.59060(7) 0.61158(6) 0.7916(2) 0.0434(4) Uani 1 1 d . . . . .
S2 S 0.40931(7) 0.45685(6) 0.7120(3) 0.0539(4) Uani 1 1 d . . . . .
S3 S 0.39125(9) 0.31724(6) 0.7081(3) 0.0547(4) Uani 1 1 d . . . . .
Se1 Se 0.60476(3) 0.76281(2) 0.81377(8) 0.03985(18) 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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
C4 C1 S1 122.24(19) . . ?
C4 C1 S1 122.24(19) . 2_656 ?
S1 C1 S1 115.5(4) . 2_656 ?
C2 C2 S1 117.00(14) 2_656 . ?
C2 C2 Se1 122.32(14) 2_656 . ?
S1 C2 Se1 120.6(2) . . ?
Se1 C3 H3A 109.5 . . ?
Se1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Se1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 S2 122.2(2) . 2_656 ?
C1 C4 S2 122.2(2) . . ?
S2 C4 S2 115.6(4) 2_656 . ?
C5 C5 S2 117.21(15) 2_656 . ?
C5 C5 S3 128.51(16) 2_656 . ?
S2 C5 S3 114.3(3) . . ?
C6 C6 S3 116.1(4) 2_656 . ?
C6 C6 H6A 108.3 2_656 . ?
S3 C6 H6A 108.3 . . ?
C6 C6 H6B 108.3 2_656 . ?
S3 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 F1 117.8(4) . . ?
C8 C7 C9 124.7(4) . 5_676 ?
F1 C7 C9 117.5(4) . 5_676 ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 121.8(4) . . ?
C10 C9 C7 124.1(4) . 5_676 ?
C8 C9 C7 114.1(4) . 5_676 ?
C9 C10 C11 120.8(4) . . ?
C9 C10 C12 125.1(5) . . ?
C11 C10 C12 114.0(4) . . ?
N1 C11 C10 178.3(6) . . ?
N2 C12 C10 175.2(6) . . ?
C2 S1 C1 95.2(2) . . ?
C4 S2 C5 95.0(3) . . ?
C5 S3 C6 101.6(3) . . ?
C2 Se1 C3 98.9(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 C4 1.373(9) . ?
C1 S1 1.728(4) . ?
C1 S1 1.728(4) 2_656 ?
C2 C2 1.355(9) 2_656 ?
C2 S1 1.728(4) . ?
C2 Se1 1.903(4) . ?
C3 Se1 1.924(6) . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
C4 S2 1.728(4) 2_656 ?
C4 S2 1.728(4) . ?
C5 C5 1.340(9) 2_656 ?
C5 S2 1.733(5) . ?
C5 S3 1.739(5) . ?
C6 C6 1.468(12) 2_656 ?
C6 S3 1.792(6) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.350(6) . ?
C7 F1 1.353(5) . ?
C7 C9 1.428(6) 5_676 ?
C8 C9 1.414(6) . ?
C8 H8 0.93 . ?
C9 C10 1.398(6) . ?
C10 C11 1.424(7) . ?
C10 C12 1.431(7) . ?
C11 N1 1.145(6) . ?
C12 N2 1.135(7) . ?
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
S1 C1 C4 S2 -1.08(10) . . . 2_656 ?
S1 C1 C4 S2 178.92(10) 2_656 . . 2_656 ?
S1 C1 C4 S2 178.92(10) . . . . ?
S1 C1 C4 S2 -1.08(10) 2_656 . . . ?
F1 C7 C8 C9 179.1(4) . . . . ?
C9 C7 C8 C9 1.4(8) 5_676 . . . ?
C7 C8 C9 C10 178.1(5) . . . . ?
C7 C8 C9 C7 -1.2(7) . . . 5_676 ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C7 C9 C10 C11 179.2(4) 5_676 . . . ?
C8 C9 C10 C12 -178.7(5) . . . . ?
C7 C9 C10 C12 0.6(8) 5_676 . . . ?
C2 C2 S1 C1 -0.2(6) 2_656 . . . ?
Se1 C2 S1 C1 175.9(3) . . . . ?
C4 C1 S1 C2 -179.95(19) . . . . ?
S1 C1 S1 C2 0.05(19) 2_656 . . . ?
C1 C4 S2 C5 179.90(19) . . . . ?
S2 C4 S2 C5 -0.10(19) 2_656 . . . ?
C5 C5 S2 C4 0.4(7) 2_656 . . . ?
S3 C5 S2 C4 178.8(3) . . . . ?
C5 C5 S3 C6 -13.9(8) 2_656 . . . ?
S2 C5 S3 C6 167.8(3) . . . . ?
C6 C6 S3 C5 44.6(7) 2_656 . . . ?
