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#$Date: 2024-08-05 22:47:36 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293902 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063298.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_7063298
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         'C23 H14 F8 S2'
_chemical_formula_sum            'C23 H14 F8 S2'
_chemical_formula_weight         506.46
_chemical_name_systematic
'(1,1,2,2,3,3,4,7-octafluoro-2,3-dihydro-1H-indene-5,6-diyl) bis(benzylsulfane)'
_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-2018/3
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                101.990(2)
_cell_angle_beta                 101.874(2)
_cell_angle_gamma                93.494(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0063(5)
_cell_length_b                   9.1070(5)
_cell_length_c                   13.7547(7)
_cell_measurement_reflns_used    4717
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.49
_cell_volume                     1073.59(10)
_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 0.996
_diffrn_measured_fraction_theta_max 0.982
_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  0.0475
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11516
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.197
_diffrn_reflns_theta_min         3.052
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.060
_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     298
_refine_ls_number_reflns         4246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0673P)²+0.5881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3359
_reflns_number_total             4246
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj02284j2.cif
_cod_data_source_block           7_2s1516
_cod_depositor_comments
'Adding full bibliography for 7063295--7063298.cif.'
_cod_database_code               7063298
_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   0.781
_shelx_estimated_absorpt_t_max   0.881
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
S1 S 0.48373(7) 0.60768(7) 0.24713(5) 0.04097(19) Uani 1 1 d . . . . .
S2 S 0.60984(7) 0.38617(8) 0.07540(5) 0.0450(2) Uani 1 1 d . . . . .
F1 F 0.61242(18) 0.56687(16) 0.45391(11) 0.0486(4) Uani 1 1 d . . . . .
F2 F 0.82443(19) 0.18462(17) 0.16638(11) 0.0518(4) Uani 1 1 d . . . . .
F3 F 1.06332(17) 0.2011(2) 0.37149(14) 0.0622(5) Uani 1 1 d . . . . .
F4 F 0.8758(2) 0.02745(16) 0.34018(13) 0.0584(4) Uani 1 1 d . . . . .
F7 F 0.7003(2) 0.3028(2) 0.55425(13) 0.0713(6) Uani 1 1 d . . . . .
F8 F 0.9003(2) 0.46348(19) 0.57972(12) 0.0713(6) Uani 1 1 d . . . . .
F5 F 0.8542(3) 0.0902(2) 0.52115(16) 0.0838(6) Uani 1 1 d . . . . .
C23 C 0.8319(3) 0.6831(3) 0.0323(2) 0.0542(7) Uani 1 1 d . . . . .
H23A H 0.750235 0.667412 -0.026051 0.065 Uiso 1 1 calc R U . . .
C6 C 0.9152(3) 0.2111(3) 0.49720(19) 0.0434(6) Uani 1 1 d . . . . .
C17 C 0.7872(3) 0.4098(3) 0.03159(18) 0.0457(6) Uani 1 1 d . . . . .
H17A H 0.853688 0.333076 0.050883 0.055 Uiso 1 1 calc R U . . .
H17B H 0.762639 0.392143 -0.043722 0.055 Uiso 1 1 calc R U . . .
C12 C 0.4752(4) 0.9921(4) 0.3355(2) 0.0622(8) Uani 1 1 d . . . . .
H12A H 0.497406 0.967160 0.400262 0.075 Uiso 1 1 calc R U . . .
C19 C 0.9929(3) 0.5894(4) 0.1603(2) 0.0571(8) Uani 1 1 d . . . . .
H19A H 1.024021 0.508664 0.190976 0.069 Uiso 1 1 calc R U . . .
C16 C 0.4853(4) 0.9446(3) 0.1626(3) 0.0613(8) Uani 1 1 d . . . . .
H16A H 0.515663 0.886068 0.105714 0.074 Uiso 1 1 calc R U . . .
C22 C 0.9088(4) 0.8254(4) 0.0723(3) 0.0730(10) Uani 1 1 d . . . . .
H22A H 0.880068 0.906681 0.041571 0.088 Uiso 1 1 calc R U . . .
C20 C 1.0686(4) 0.7334(5) 0.2001(2) 0.0742(11) Uani 1 1 d . . . . .
H20A H 1.150631 0.751019 0.258417 0.089 Uiso 1 1 calc R U . . .
C21 C 1.0263(4) 0.8494(5) 0.1562(3) 0.0784(11) Uani 1 1 d . . . . .
H21A H 1.078606 0.947738 0.184083 0.094 Uiso 1 1 calc R U . . .
C13 C 0.3953(4) 1.1154(4) 0.3220(4) 0.0852(13) Uani 1 1 d . . . . .
H13A H 0.364600 1.175957 0.377964 0.102 Uiso 1 1 calc R U . . .
C14 C 0.3614(4) 1.1490(4) 0.2285(5) 0.0895(15) Uani 1 1 d . . . . .
H14A H 0.305925 1.232273 0.218878 0.107 Uiso 1 1 calc R U . . .
C15 C 0.4060(4) 1.0651(5) 0.1507(3) 0.0812(12) Uani 1 1 d . . . . .
H15A H 0.382367 1.089427 0.085684 0.097 Uiso 1 1 calc R U . . .
C10 C 0.6129(4) 0.7762(3) 0.2669(4) 0.0787(11) Uani 1 1 d . . . . .
H10A H 0.679675 0.797299 0.336161 0.094 Uiso 1 1 calc R U . . .
H10B H 0.678219 0.761656 0.216683 0.094 Uiso 1 1 calc R U . . .
F6 F 1.0552(2) 0.2485(3) 0.55552(15) 0.0879(7) Uani 1 1 d . . . . .
C9 C 0.6635(3) 0.4738(2) 0.38123(16) 0.0319(5) Uani 1 1 d . . . . .
C1 C 0.6181(2) 0.4820(2) 0.27975(17) 0.0304(5) Uani 1 1 d . . . . .
C8 C 0.7602(3) 0.3713(2) 0.40949(16) 0.0312(5) Uani 1 1 d . . . . .
C2 C 0.6749(3) 0.3846(2) 0.20506(16) 0.0319(5) Uani 1 1 d . . . . .
C3 C 0.7722(3) 0.2826(2) 0.23590(17) 0.0343(5) Uani 1 1 d . . . . .
C4 C 0.8154(2) 0.2759(2) 0.33708(17) 0.0311(5) Uani 1 1 d . . . . .
C18 C 0.8714(3) 0.5625(3) 0.07540(17) 0.0391(5) Uani 1 1 d . . . . .
C11 C 0.5215(3) 0.9069(3) 0.2548(2) 0.0445(6) Uani 1 1 d . . . . .
C7 C 0.8159(3) 0.3429(3) 0.51362(17) 0.0406(6) Uani 1 1 d . . . . .
C5 C 0.9195(3) 0.1747(3) 0.38273(19) 0.0390(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'
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'
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
C1 S1 C10 99.22(12) . . ?
C2 S2 C17 103.28(11) . . ?
C22 C23 C18 121.3(3) . . ?
F6 C6 F5 107.9(2) . . ?
F6 C6 C7 111.0(2) . . ?
F5 C6 C7 110.4(2) . . ?
F6 C6 C5 110.9(2) . . ?
F5 C6 C5 109.9(2) . . ?
C7 C6 C5 106.78(18) . . ?
C18 C17 S2 112.55(17) . . ?
C11 C12 C13 119.7(3) . . ?
C20 C19 C18 120.3(3) . . ?
C11 C16 C15 121.0(3) . . ?
C21 C22 C23 119.9(3) . . ?
C21 C20 C19 120.4(3) . . ?
C20 C21 C22 120.3(3) . . ?
C14 C13 C12 119.9(3) . . ?
C15 C14 C13 119.9(3) . . ?
C14 C15 C16 121.1(4) . . ?
C11 C10 S1 109.1(2) . . ?
F1 C9 C8 118.77(19) . . ?
F1 C9 C1 120.08(18) . . ?
C8 C9 C1 121.2(2) . . ?
C9 C1 C2 119.02(19) . . ?
C9 C1 S1 119.02(17) . . ?
C2 C1 S1 121.90(16) . . ?
C4 C8 C9 120.04(19) . . ?
C4 C8 C7 111.58(19) . . ?
C9 C8 C7 128.4(2) . . ?
C3 C2 C1 118.47(19) . . ?
C3 C2 S2 121.89(17) . . ?
C1 C2 S2 119.47(16) . . ?
F2 C3 C4 118.35(19) . . ?
F2 C3 C2 120.1(2) . . ?
C4 C3 C2 121.6(2) . . ?
C8 C4 C3 119.74(19) . . ?
C8 C4 C5 112.02(19) . . ?
C3 C4 C5 128.2(2) . . ?
C23 C18 C19 117.7(3) . . ?
C23 C18 C17 120.7(2) . . ?
C19 C18 C17 121.6(3) . . ?
C16 C11 C12 118.5(3) . . ?
C16 C11 C10 120.1(3) . . ?
C12 C11 C10 121.4(3) . . ?
F7 C7 F8 107.7(2) . . ?
F7 C7 C8 112.0(2) . . ?
F8 C7 C8 112.9(2) . . ?
F7 C7 C6 109.8(2) . . ?
F8 C7 C6 109.7(2) . . ?
C8 C7 C6 104.76(19) . . ?
F4 C5 F3 106.00(19) . . ?
F4 C5 C4 112.9(2) . . ?
F3 C5 C4 112.05(19) . . ?
F4 C5 C6 110.94(19) . . ?
F3 C5 C6 110.4(2) . . ?
C4 C5 C6 104.68(18) . . ?
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 C1 1.770(2) . ?
S1 C10 1.806(3) . ?
S2 C2 1.762(2) . ?
S2 C17 1.835(3) . ?
F1 C9 1.347(2) . ?
F2 C3 1.347(3) . ?
F3 C5 1.349(3) . ?
F4 C5 1.345(3) . ?
F7 C7 1.345(3) . ?
F8 C7 1.345(3) . ?
F5 C6 1.332(3) . ?
C23 C22 1.378(4) . ?
C23 C18 1.384(4) . ?
C6 F6 1.329(3) . ?
C6 C7 1.547(3) . ?
C6 C5 1.549(4) . ?
C17 C18 1.486(4) . ?
C12 C11 1.371(4) . ?
C12 C13 1.394(5) . ?
C19 C20 1.387(5) . ?
C19 C18 1.394(4) . ?
C16 C11 1.363(4) . ?
C16 C15 1.365(5) . ?
C22 C21 1.365(5) . ?
C20 C21 1.358(6) . ?
C13 C14 1.362(6) . ?
C14 C15 1.329(6) . ?
C10 C11 1.506(4) . ?
C9 C8 1.376(3) . ?
C9 C1 1.391(3) . ?
C1 C2 1.413(3) . ?
C8 C4 1.375(3) . ?
C8 C7 1.498(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.492(3) . ?
