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#$Revision: 293902 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063296.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_7063296
loop_
_publ_author_name
'Buravlev, Alexander A.'
'Makarov, Alexander Yu.'
'Salnikov, Georgy E.'
'Genaev, Alexander M.'
'Bagryanskaya, Irina Yu.'
'Nikulshin, Pavel V.'
'Platonov, Vyacheslav E.'
'Zibarev, Andrey V.'
_publ_section_title
;
 Synthesis, structural peculiarities, and photosensitivity of fluorinated
 dibenzo-1,2,5,6-tetrathiocines
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12807
_journal_page_last               12816
_journal_paper_doi               10.1039/D4NJ02284J
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C18 F16 S4'
_chemical_formula_sum            'C18 F16 S4'
_chemical_formula_weight         648.42
_chemical_name_systematic
;
 perfluorodiindeno[5,6-c:5',6'-g][1,2,5,6]tetrathiocine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-12 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.983(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0085(7)
_cell_length_b                   11.8439(4)
_cell_length_c                   10.6197(4)
_cell_measurement_reflns_used    5407
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.55
_cell_volume                     2012.32(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12137
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.043
_diffrn_reflns_theta_min         2.139
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0343P)²+4.6389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1746
_reflns_number_total             1989
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj02284j2.cif
_cod_data_source_block           2_gl81252
_cod_depositor_comments
'Adding full bibliography for 7063295--7063298.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7063296
_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.
;
_shelx_estimated_absorpt_t_min   0.787
_shelx_estimated_absorpt_t_max   0.885
loop_
_space_group_symop_operation_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
S1 S 0.48314(3) 0.54440(5) 0.34195(5) 0.02615(16) Uani 1 1 d . . . . .
S2 S 0.45043(3) 0.28572(5) 0.18733(6) 0.02672(16) Uani 1 1 d . . . . .
F1 F 0.06457(11) 0.48538(16) 0.33962(19) 0.0575(5) Uani 1 1 d . . . . .
F2 F 0.04607(11) 0.37916(17) 0.5023(2) 0.0676(6) Uani 1 1 d . . . . .
F3 F 0.18723(11) 0.44302(16) 0.60940(14) 0.0497(4) Uani 1 1 d . . . . .
F4 F 0.27930(9) 0.22451(12) 0.19732(14) 0.0352(3) Uani 1 1 d . . . . .
F5 F 0.14383(10) 0.22326(13) 0.42075(18) 0.0494(4) Uani 1 1 d . . . . .
F6 F 0.10438(9) 0.29771(14) 0.24222(15) 0.0442(4) Uani 1 1 d . . . . .
F7 F 0.15727(9) 0.59237(13) 0.50081(15) 0.0434(4) Uani 1 1 d . . . . .
F8 F 0.33939(8) 0.60054(12) 0.47891(13) 0.0341(3) Uani 1 1 d . . . . .
C1 C 0.10317(15) 0.4157(2) 0.4243(3) 0.0375(6) Uani 1 1 d . . . . .
C2 C 0.17447(15) 0.4823(2) 0.4897(2) 0.0304(5) Uani 1 1 d . . . . .
C3 C 0.24869(14) 0.45594(19) 0.4114(2) 0.0245(5) Uani 1 1 d . . . . .
C4 C 0.32543(14) 0.50681(19) 0.4097(2) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.38955(13) 0.46449(19) 0.3378(2) 0.0226(5) Uani 1 1 d . . . . .
C6 C 0.37518(13) 0.36338(19) 0.2693(2) 0.0227(5) Uani 1 1 d . . . . .
C7 C 0.29495(14) 0.31708(19) 0.2671(2) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.23262(13) 0.3616(2) 0.3370(2) 0.0252(5) Uani 1 1 d . . . . .
C9 C 0.14511(14) 0.3196(2) 0.3513(2) 0.0303(5) 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'
F F 0.0171 0.0103 '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
C5 S1 S1 103.13(8) . 2_655 ?
C6 S2 S2 101.95(8) . 2_655 ?
F2 C1 F1 107.8(2) . . ?
F2 C1 C2 113.7(2) . . ?
F1 C1 C2 107.6(2) . . ?
F2 C1 C9 113.2(2) . . ?
F1 C1 C9 108.2(2) . . ?
C2 C1 C9 106.09(19) . . ?
F7 C2 F3 106.0(2) . . ?
F7 C2 C3 114.8(2) . . ?
F3 C2 C3 110.38(19) . . ?
F7 C2 C1 112.9(2) . . ?
F3 C2 C1 109.4(2) . . ?
C3 C2 C1 103.4(2) . . ?
C4 C3 C8 119.7(2) . . ?
C4 C3 C2 129.9(2) . . ?
C8 C3 C2 110.3(2) . . ?
F8 C4 C3 119.17(19) . . ?
F8 C4 C5 118.98(19) . . ?
C3 C4 C5 121.8(2) . . ?
C4 C5 C6 118.42(19) . . ?
C4 C5 S1 115.62(17) . . ?
C6 C5 S1 125.96(16) . . ?
C7 C6 C5 118.29(19) . . ?
C7 C6 S2 115.44(17) . . ?
C5 C6 S2 126.26(16) . . ?
F4 C7 C8 119.2(2) . . ?
F4 C7 C6 118.95(19) . . ?
C8 C7 C6 121.8(2) . . ?
C7 C8 C3 119.6(2) . . ?
C7 C8 C9 128.9(2) . . ?
C3 C8 C9 111.4(2) . . ?
F6 C9 F5 107.0(2) . . ?
F6 C9 C8 114.01(19) . . ?
F5 C9 C8 111.42(19) . . ?
F6 C9 C1 111.8(2) . . ?
F5 C9 C1 109.4(2) . . ?
C8 C9 C1 103.3(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
S1 C5 1.771(2) . ?
S1 S1 2.0441(11) 2_655 ?
S2 C6 1.769(2) . ?
S2 S2 2.0358(11) 2_655 ?
F1 C1 1.354(3) . ?
F2 C1 1.327(3) . ?
F3 C2 1.362(3) . ?
F4 C7 1.342(3) . ?
F5 C9 1.359(3) . ?
F6 C9 1.335(3) . ?
F7 C2 1.338(3) . ?
F8 C4 1.346(3) . ?
C1 C2 1.534(4) . ?
C1 C9 1.544(4) . ?
C2 C3 1.506(3) . ?
C3 C4 1.369(3) . ?
C3 C8 1.387(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.416(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.370(3) . ?
C8 C9 1.499(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
F2 C1 C2 F7 -87.1(3) . . . . ?
F1 C1 C2 F7 32.1(3) . . . . ?
C9 C1 C2 F7 147.8(2) . . . . ?
F2 C1 C2 F3 30.6(3) . . . . ?
F1 C1 C2 F3 149.9(2) . . . . ?
C9 C1 C2 F3 -94.5(2) . . . . ?
F2 C1 C2 C3 148.2(2) . . . . ?
F1 C1 C2 C3 -92.5(2) . . . . ?
C9 C1 C2 C3 23.1(2) . . . . ?
F7 C2 C3 C4 43.0(3) . . . . ?
F3 C2 C3 C4 -76.7(3) . . . . ?
C1 C2 C3 C4 166.4(2) . . . . ?
F7 C2 C3 C8 -140.2(2) . . . . ?
F3 C2 C3 C8 100.1(2) . . . . ?
C1 C2 C3 C8 -16.8(3) . . . . ?
C8 C3 C4 F8 177.73(19) . . . . ?
C2 C3 C4 F8 -5.8(4) . . . . ?
C8 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 C5 174.5(2) . . . . ?
F8 C4 C5 C6 177.52(19) . . . . ?
C3 C4 C5 C6 -2.7(3) . . . . ?
F8 C4 C5 S1 -2.2(3) . . . . ?
C3 C4 C5 S1 177.54(18) . . . . ?
S1 S1 C5 C4 -137.67(16) 2_655 . . . ?
S1 S1 C5 C6 42.6(2) 2_655 . . . ?
C4 C5 C6 C7 6.2(3) . . . . ?
S1 C5 C6 C7 -174.02(17) . . . . ?
C4 C5 C6 S2 -172.11(17) . . . . ?
S1 C5 C6 S2 7.6(3) . . . . ?
S2 S2 C6 C7 -134.38(16) 2_655 . . . ?
S2 S2 C6 C5 44.0(2) 2_655 . . . ?
C5 C6 C7 F4 176.58(19) . . . . ?
S2 C6 C7 F4 -4.9(3) . . . . ?
C5 C6 C7 C8 -5.3(3) . . . . ?
S2 C6 C7 C8 173.21(18) . . . . ?
F4 C7 C8 C3 178.7(2) . . . . ?
C6 C7 C8 C3 0.6(3) . . . . ?
F4 C7 C8 C9 1.7(4) . . . . ?
C6 C7 C8 C9 -176.4(2) . . . . ?
C4 C3 C8 C7 3.1(3) . . . . ?
C2 C3 C8 C7 -174.0(2) . . . . ?
C4 C3 C8 C9 -179.3(2) . . . . ?
C2 C3 C8 C9 3.5(3) . . . . ?
C7 C8 C9 F6 -50.0(3) . . . . ?
C3 C8 C9 F6 132.8(2) . . . . ?
C7 C8 C9 F5 71.2(3) . . . . ?
C3 C8 C9 F5 -106.0(2) . . . . ?
C7 C8 C9 C1 -171.5(2) . . . . ?
C3 C8 C9 C1 11.3(3) . . . . ?
F2 C1 C9 F6 90.4(3) . . . . ?
F1 C1 C9 F6 -29.0(3) . . . . ?
C2 C1 C9 F6 -144.2(2) . . . . ?
F2 C1 C9 F5 -27.9(3) . . . . ?
F1 C1 C9 F5 -147.2(2) . . . . ?
C2 C1 C9 F5 97.6(2) . . . . ?
F2 C1 C9 C8 -146.6(2) . . . . ?
F1 C1 C9 C8 94.0(2) . . . . ?
C2 C1 C9 C8 -21.2(2) . . . . ?
