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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/7/06/32/7063297.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.
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data_7063297
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         'C12 H4 F4 S4'
_chemical_formula_sum            'C12 H4 F4 S4'
_chemical_formula_weight         352.39
_chemical_name_systematic
;
 1,4,8,11-tetrafluorodibenzo[d,g][1,2,3,6]tetrathiocine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 100.540(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4346(4)
_cell_length_b                   29.235(3)
_cell_length_c                   10.3338(11)
_cell_measurement_reflns_used    4516
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.44
_cell_volume                     1317.1(2)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0518
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13123
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.558
_diffrn_reflns_theta_min         2.896
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0410
_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)+(0.0365P)²+0.7257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2357
_reflns_number_total             3042
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj02284j2.cif
_cod_data_source_block           17_gl942f
_cod_depositor_comments
'Adding full bibliography for 7063295--7063298.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063297
_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   0.585
_shelx_estimated_absorpt_t_max   0.929
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.56989(17) 0.59640(3) 0.58386(6) 0.0558(2) Uani 1 1 d . . . . .
S2 S 0.78062(16) 0.55046(2) 0.48020(7) 0.05060(19) Uani 1 1 d . . . . .
S3 S 0.47621(16) 0.53290(2) 0.31439(7) 0.04984(19) Uani 1 1 d . . . . .
S4 S 0.27549(13) 0.64188(2) 0.29570(6) 0.04441(17) Uani 1 1 d . . . . .
F1 F 0.7985(5) 0.50774(6) 0.10393(18) 0.0765(5) Uani 1 1 d . . . . .
F2 F 0.3984(5) 0.68199(6) 0.04468(19) 0.0841(6) Uani 1 1 d . . . . .
F3 F 1.0286(5) 0.65682(8) 0.73551(18) 0.0933(7) Uani 1 1 d . . . . .
F4 F 0.5796(5) 0.73075(6) 0.2611(2) 0.0881(6) Uani 1 1 d . . . . .
C1 C 1.0143(7) 0.71694(12) 0.5838(4) 0.0702(9) Uani 1 1 d . . . . .
H1A H 1.158826 0.732777 0.643869 0.084 Uiso 1 1 calc R U . . .
C2 C 0.9123(7) 0.67457(12) 0.6158(3) 0.0601(8) Uani 1 1 d . . . . .
C3 C 0.6953(5) 0.64953(9) 0.5302(2) 0.0439(6) Uani 1 1 d . . . . .
C4 C 0.5639(5) 0.57002(8) 0.1905(2) 0.0373(5) Uani 1 1 d . . . . .
C5 C 0.7030(6) 0.55175(10) 0.0925(3) 0.0497(6) Uani 1 1 d . . . . .
C6 C 0.9017(7) 0.73547(11) 0.4635(4) 0.0676(9) Uani 1 1 d . . . . .
H6A H 0.969460 0.763869 0.440109 0.081 Uiso 1 1 calc R U . . .
C7 C 0.6876(6) 0.71151(9) 0.3782(3) 0.0531(7) Uani 1 1 d . . . . .
C8 C 0.5784(5) 0.66870(8) 0.4069(2) 0.0393(5) Uani 1 1 d . . . . .
C9 C 0.7431(7) 0.57556(12) -0.0170(3) 0.0608(8) Uani 1 1 d . . . . .
H9A H 0.838514 0.562030 -0.080344 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6402(7) 0.61957(12) -0.0314(3) 0.0615(8) Uani 1 1 d . . . . .
H10A H 0.660895 0.636383 -0.105663 0.074 Uiso 1 1 calc R U . . .
C11 C 0.5059(6) 0.63870(9) 0.0653(3) 0.0504(6) Uani 1 1 d . . . . .
C12 C 0.4682(5) 0.61583(8) 0.1781(2) 0.0373(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
C3 S1 S2 102.24(8) . . ?
S3 S2 S1 107.99(4) . . ?
C4 S3 S2 104.65(8) . . ?
C12 S4 C8 103.25(10) . . ?
C6 C1 C2 119.6(3) . . ?
C6 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
F3 C2 C1 118.4(3) . . ?
F3 C2 C3 118.9(3) . . ?
C1 C2 C3 122.7(3) . . ?
C2 C3 C8 117.7(3) . . ?
C2 C3 S1 118.9(2) . . ?
C8 C3 S1 123.34(19) . . ?
C5 C4 C12 117.9(2) . . ?
C5 C4 S3 118.49(19) . . ?
C12 C4 S3 123.15(17) . . ?
F1 C5 C9 118.0(2) . . ?
F1 C5 C4 118.5(2) . . ?
C9 C5 C4 123.5(3) . . ?
C1 C6 C7 118.7(3) . . ?
C1 C6 H6A 120.6 . . ?
C7 C6 H6A 120.6 . . ?
F4 C7 C6 117.3(3) . . ?
F4 C7 C8 119.2(3) . . ?
C6 C7 C8 123.4(3) . . ?
C7 C8 C3 117.9(2) . . ?
C7 C8 S4 120.5(2) . . ?
C3 C8 S4 121.34(19) . . ?
C5 C9 C10 118.6(3) . . ?
C5 C9 H9A 120.7 . . ?
C10 C9 H9A 120.7 . . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
F2 C11 C10 117.0(2) . . ?
F2 C11 C12 119.4(2) . . ?
C10 C11 C12 123.6(3) . . ?
C11 C12 C4 117.2(2) . . ?
C11 C12 S4 121.12(19) . . ?
C4 C12 S4 121.41(17) . . ?
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 1.772(3) . ?
S1 S2 2.0470(10) . ?
S2 S3 2.0434(10) . ?
S3 C4 1.774(2) . ?
S4 C12 1.779(2) . ?
S4 C8 1.782(2) . ?
F1 C5 1.353(3) . ?
F2 C11 1.355(3) . ?
F3 C2 1.354(4) . ?
F4 C7 1.341(3) . ?
C1 C6 1.364(5) . ?
C1 C2 1.379(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.390(4) . ?
C3 C8 1.402(4) . ?
C4 C5 1.386(3) . ?
C4 C12 1.404(3) . ?
C5 C9 1.368(4) . ?
C6 C7 1.365(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.393(4) . ?
C9 C10 1.364(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.381(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
C6 C1 C2 F3 179.7(3) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
F3 C2 C3 C8 180.0(2) . . . . ?
C1 C2 C3 C8 0.1(4) . . . . ?
F3 C2 C3 S1 2.3(3) . . . . ?
C1 C2 C3 S1 -177.6(2) . . . . ?
S2 S1 C3 C2 -106.7(2) . . . . ?
S2 S1 C3 C8 75.70(19) . . . . ?
S2 S3 C4 C5 108.85(19) . . . . ?
S2 S3 C4 C12 -78.67(19) . . . . ?
C12 C4 C5 F1 179.5(2) . . . . ?
S3 C4 C5 F1 -7.6(3) . . . . ?
C12 C4 C5 C9 -2.1(4) . . . . ?
S3 C4 C5 C9 170.8(2) . . . . ?
C2 C1 C6 C7 0.6(5) . . . . ?
C1 C6 C7 F4 179.5(3) . . . . ?
C1 C6 C7 C8 -0.5(4) . . . . ?
F4 C7 C8 C3 -179.9(2) . . . . ?
C6 C7 C8 C3 0.1(4) . . . . ?
F4 C7 C8 S4 -5.3(3) . . . . ?
C6 C7 C8 S4 174.7(2) . . . . ?
C2 C3 C8 C7 0.1(3) . . . . ?
S1 C3 C8 C7 177.66(18) . . . . ?
C2 C3 C8 S4 -174.41(18) . . . . ?
S1 C3 C8 S4 3.2(3) . . . . ?
C12 S4 C8 C7 82.7(2) . . . . ?
C12 S4 C8 C3 -102.96(19) . . . . ?
F1 C5 C9 C10 178.2(3) . . . . ?
C4 C5 C9 C10 -0.2(4) . . . . ?
C5 C9 C10 C11 1.2(4) . . . . ?
C9 C10 C11 F2 -177.9(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
F2 C11 C12 C4 175.6(2) . . . . ?
C10 C11 C12 C4 -2.4(4) . . . . ?
F2 C11 C12 S4 1.0(4) . . . . ?
C10 C11 C12 S4 -177.0(2) . . . . ?
C5 C4 C12 C11 3.2(3) . . . . ?
S3 C4 C12 C11 -169.28(19) . . . . ?
C5 C4 C12 S4 177.82(18) . . . . ?
S3 C4 C12 S4 5.3(3) . . . . ?
C8 S4 C12 C11 -91.4(2) . . . . ?
C8 S4 C12 C4 94.3(2) . . . . ?
