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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/46/1504623.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_1504623
loop_
_publ_author_name
'Wang, Yongfeng'
'Parkin, Sean R.'
'Gierschner, Johannes'
'Watson, Mark D.'
_publ_section_title
;
 Highly fluorinated benzobisbenzothiophenes.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3307
_journal_page_last               3310
_journal_paper_doi               10.1021/ol8003468
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C38 H36 F6 S2'
_chemical_formula_sum            'C38 H36 F6 S2'
_chemical_formula_weight         670.79
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.3542(3)
_cell_length_b                   4.90030(10)
_cell_length_c                   21.7359(4)
_cell_measurement_reflns_used    8142
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      67.75
_cell_measurement_theta_min      2.90
_cell_volume                     1624.87(5)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker-Nonius, 2004)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1994)'
_computing_publication_material
; 
SHELX97-2 (Sheldrick, 1997) and local procedures 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .992
_diffrn_measured_fraction_theta_max .992
_diffrn_measurement_device_type  'Bruker-Nonius X8 Proteum'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19192
_diffrn_reflns_theta_full        67.75
_diffrn_reflns_theta_max         67.75
_diffrn_reflns_theta_min         2.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.015
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS in APEX2 (Bruker-Nonius, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'very thin needle'
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.696
_refine_diff_density_min         -.386
_refine_diff_density_rms         .083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0907P)²+3.6281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1817
_reflns_number_gt                2621
_reflns_number_total             2919
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol8003468-file001.cif
_cod_data_source_block           x05104_6
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               1504623
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.80441(5) 0.39233(15) 0.45527(3) 0.0255(3) Uani 1 1 d .
F1 F 0.65664(12) 0.0371(4) 0.48263(9) 0.0338(5) Uani 1 1 d .
F2 F 0.81586(13) -0.4177(4) 0.64992(9) 0.0361(5) Uani 1 1 d .
F3 F 0.95306(12) -0.1220(4) 0.64019(9) 0.0345(5) Uani 1 1 d .
C1 C 0.8032(2) 0.1512(6) 0.51309(14) 0.0266(7) Uani 1 1 d .
C2 C 0.7302(2) -0.0022(7) 0.52187(15) 0.0282(7) Uani 1 1 d .
C3 C 0.7303(2) -0.1985(7) 0.56732(15) 0.0297(7) Uani 1 1 d .
C4 C 0.8095(2) -0.2303(7) 0.60575(14) 0.0283(7) Uani 1 1 d .
C5 C 0.8831(2) -0.0726(6) 0.59851(15) 0.0273(7) Uani 1 1 d .
C6 C 0.8837(2) 0.1202(6) 0.55132(14) 0.0252(7) Uani 1 1 d .
C7 C 0.9518(2) 0.3038(6) 0.53070(14) 0.0242(7) Uani 1 1 d .
C8 C 0.9152(2) 0.4611(6) 0.47944(14) 0.0235(6) Uani 1 1 d .
C9 C 0.6556(2) -0.3655(7) 0.57404(16) 0.0327(8) Uani 1 1 d .
C10 C 0.5939(2) -0.5121(7) 0.57729(16) 0.0345(8) Uani 1 1 d .
C11 C 0.5175(2) -0.6858(8) 0.58096(18) 0.0410(9) Uani 1 1 d .
H11A H 0.5369 -0.8599 0.6012 0.049 Uiso 1 1 calc R
H11B H 0.4907 -0.7286 0.5385 0.049 Uiso 1 1 calc R
C12 C 0.4486(3) -0.5565(9) 0.6166(2) 0.0486(10) Uani 1 1 d .
H12A H 0.4745 -0.5138 0.6588 0.073 Uiso 1 1 calc R
H12B H 0.3997 -0.6841 0.6183 0.073 Uiso 1 1 calc R
H12C H 0.4270 -0.3884 0.5957 0.073 Uiso 1 1 calc R
C13 C 1.0405(2) 0.3425(6) 0.55183(13) 0.0235(6) Uani 1 1 d .
C14 C 1.0912(2) 0.1934(6) 0.60500(13) 0.0252(7) Uani 1 1 d .
H14A H 1.1534 0.1820 0.5973 0.030 Uiso 1 1 calc R
H14B H 1.0684 0.0048 0.6064 0.030 Uiso 1 1 calc R
C15 C 1.0862(2) 0.3297(7) 0.66835(14) 0.0286(7) Uani 1 1 d .
H15A H 1.1077 0.5198 0.6669 0.034 Uiso 1 1 calc R
H15B H 1.0243 0.3359 0.6770 0.034 Uiso 1 1 calc R
C16 C 1.1407(2) 0.1770(7) 0.72089(14) 0.0305(7) Uani 1 1 d .
H16A H 1.1325 0.2670 0.7606 0.037 Uiso 1 1 calc R
H16B H 1.1179 -0.0116 0.7227 0.037 Uiso 1 1 calc R
C17 C 1.2380(2) 0.1641(9) 0.71461(15) 0.0379(8) Uani 1 1 d .
H17A H 1.2603 0.3521 0.7104 0.045 Uiso 1 1 calc R
H17B H 1.2467 0.0637 0.6762 0.045 Uiso 1 1 calc R
C18 C 1.2918(3) 0.0260(9) 0.76927(17) 0.0436(9) Uani 1 1 d .
H18A H 1.2859 0.1322 0.8073 0.052 Uiso 1 1 calc R
H18B H 1.2676 -0.1584 0.7749 0.052 Uiso 1 1 calc R
C19 C 1.3874(3) 0.0006(12) 0.7611(2) 0.0630(13) Uani 1 1 d .
H19A H 1.3939 -0.1047 0.7236 0.094 Uiso 1 1 calc R
H19B H 1.4182 -0.0928 0.7971 0.094 Uiso 1 1 calc R
H19C H 1.4126 0.1829 0.7574 0.094 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0727 .0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .3331 .5567 '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
C1 S1 C8 90.19(15) .
C2 C1 C6 121.9(3) .
C2 C1 S1 123.3(2) .
C6 C1 S1 114.8(2) .
F1 C2 C3 119.1(3) .
F1 C2 C1 118.0(3) .
C3 C2 C1 122.9(3) .
C2 C3 C4 115.8(3) .
C2 C3 C9 122.4(3) .
C4 C3 C9 121.8(3) .
F2 C4 C5 118.2(3) .
F2 C4 C3 119.7(3) .
C5 C4 C3 122.0(3) .
F3 C5 C4 114.8(3) .
F3 C5 C6 123.0(3) .
C4 C5 C6 122.2(3) .
C5 C6 C1 115.2(3) .
C5 C6 C7 134.1(3) .
C1 C6 C7 110.8(3) .
C13 C7 C8 117.9(3) .
C13 C7 C6 132.4(3) .
C8 C7 C6 109.7(3) .
C13 C8 C7 125.7(3) 3_766
C13 C8 S1 119.7(2) 3_766
C7 C8 S1 114.5(2) .
C10 C9 C3 176.9(4) .
C9 C10 C11 178.8(4) .
C10 C11 C12 113.3(3) .
C10 C11 H11A 108.9 .
C12 C11 H11A 108.9 .
C10 C11 H11B 108.9 .
C12 C11 H11B 108.9 .
H11A C11 H11B 107.7 .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C8 C13 C7 116.3(3) 3_766
C8 C13 C14 117.9(3) 3_766
C7 C13 C14 125.8(3) .
C13 C14 C15 113.7(2) .
C13 C14 H14A 108.8 .
C15 C14 H14A 108.8 .
C13 C14 H14B 108.8 .
C15 C14 H14B 108.8 .
H14A C14 H14B 107.7 .
C16 C15 C14 112.1(3) .
C16 C15 H15A 109.2 .
C14 C15 H15A 109.2 .
C16 C15 H15B 109.2 .
C14 C15 H15B 109.2 .
H15A C15 H15B 107.9 .
C17 C16 C15 114.4(3) .
C17 C16 H16A 108.7 .
C15 C16 H16A 108.7 .
C17 C16 H16B 108.7 .
C15 C16 H16B 108.7 .
H16A C16 H16B 107.6 .
C16 C17 C18 113.6(3) .
C16 C17 H17A 108.9 .
C18 C17 H17A 108.9 .
C16 C17 H17B 108.9 .
C18 C17 H17B 108.9 .
H17A C17 H17B 107.7 .
C19 C18 C17 113.2(3) .
C19 C18 H18A 108.9 .
C17 C18 H18A 108.9 .
C19 C18 H18B 108.9 .
C17 C18 H18B 108.9 .
H18A C18 H18B 107.7 .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.727(3) .
S1 C8 1.755(3) .
F1 C2 1.349(4) .
F2 C4 1.324(4) .
F3 C5 1.347(4) .
C1 C2 1.382(5) .
C1 C6 1.417(4) .
C2 C3 1.378(5) .
C3 C4 1.404(5) .
C3 C9 1.431(5) .
C4 C5 1.391(5) .
C5 C6 1.396(4) .
C6 C7 1.486(4) .
C7 C13 1.400(4) .
C7 C8 1.418(4) .
C8 C13 1.399(4) 3_766
C9 C10 1.197(5) .
C10 C11 1.459(5) .
C11 C12 1.519(6) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C8 1.399(4) 3_766
C13 C14 1.508(4) .
C14 C15 1.540(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.532(4) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.518(5) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.526(5) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.503(6) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
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_4
C8 S1 C1 C2 -179.0(3) . .
C8 S1 C1 C6 0.7(2) . .
C6 C1 C2 F1 -178.9(3) . .
S1 C1 C2 F1 0.9(4) . .
C6 C1 C2 C3 -1.1(5) . .
S1 C1 C2 C3 178.6(2) . .
F1 C2 C3 C4 179.1(3) . .
C1 C2 C3 C4 1.4(5) . .
F1 C2 C3 C9 0.9(5) . .
C1 C2 C3 C9 -176.8(3) . .
C2 C3 C4 F2 -178.8(3) . .
C9 C3 C4 F2 -0.6(5) . .
C2 C3 C4 C5 0.3(5) . .
C9 C3 C4 C5 178.5(3) . .
F2 C4 C5 F3 -2.8(4) . .
C3 C4 C5 F3 178.1(3) . .
F2 C4 C5 C6 176.8(3) . .
C3 C4 C5 C6 -2.3(5) . .
F3 C5 C6 C1 -177.9(3) . .
C4 C5 C6 C1 2.4(4) . .
F3 C5 C6 C7 3.1(5) . .
C4 C5 C6 C7 -176.5(3) . .
C2 C1 C6 C5 -0.8(4) . .
S1 C1 C6 C5 179.5(2) . .
C2 C1 C6 C7 178.4(3) . .
S1 C1 C6 C7 -1.3(3) . .
C5 C6 C7 C13 1.0(6) . .
C1 C6 C7 C13 -178.0(3) . .
C5 C6 C7 C8 -179.6(3) . .
C1 C6 C7 C8 1.4(3) . .
C13 C7 C8 C13 -1.2(5) . 3_766
C6 C7 C8 C13 179.4(3) . 3_766
C13 C7 C8 S1 178.6(2) . .
C6 C7 C8 S1 -0.9(3) . .
C1 S1 C8 C13 179.9(2) . 3_766
C1 S1 C8 C7 0.1(2) . .
C8 C7 C13 C8 1.1(4) . 3_766
C6 C7 C13 C8 -179.6(3) . 3_766
C8 C7 C13 C14 -179.4(3) . .
C6 C7 C13 C14 -0.1(5) . .
C8 C13 C14 C15 91.7(3) 3_766 .
C7 C13 C14 C15 -87.8(4) . .
C13 C14 C15 C16 -178.4(3) . .
C14 C15 C16 C17 61.4(4) . .
C15 C16 C17 C18 176.6(3) . .
C16 C17 C18 C19 176.9(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102395080
