#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/46/1504622.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_1504622
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         'C42 H50 F8 S2'
_chemical_formula_sum            'C42 H50 F8 S2'
_chemical_formula_weight         770.96
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.796(1)
_cell_angle_beta                 92.501(1)
_cell_angle_gamma                99.176(1)
_cell_formula_units_Z            1
_cell_length_a                   4.6141(1)
_cell_length_b                   10.8580(2)
_cell_length_c                   19.0229(4)
_cell_measurement_reflns_used    7006
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      68.02
_cell_measurement_theta_min      2.34
_cell_volume                     934.31(3)
_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 .971
_diffrn_measured_fraction_theta_max .971
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13523
_diffrn_reflns_theta_full        68.05
_diffrn_reflns_theta_max         68.05
_diffrn_reflns_theta_min         4.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.898
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS in APEX2 (Bruker-AXS, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin needle'
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         .435
_refine_diff_density_min         -.364
_refine_diff_density_rms         .065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0435
_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)+(0.0731P)²+0.3647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                2909
_reflns_number_total             3319
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol8003468-file001.cif
_cod_data_source_block           x05019_0m_1e
_cod_database_code               1504622
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.6674(2) -0.00359(11) 0.06781(6) 0.0283(3) Uani 1 1 d .
F2 F 0.2804(3) 0.01259(11) 0.17236(7) 0.0339(3) Uani 1 1 d .
F3 F 0.1596(3) 0.23913(12) 0.22229(6) 0.0311(3) Uani 1 1 d .
F4 F 0.3902(2) 0.44567(10) 0.17260(6) 0.0259(3) Uani 1 1 d .
C1 C 1.1720(4) 0.43781(18) -0.05028(9) 0.0187(4) Uani 1 1 d .
C2 C 0.9926(4) 0.37560(17) -0.00277(9) 0.0182(4) Uani 1 1 d .
S3 S 0.95755(9) 0.21260(4) -0.00382(2) 0.01966(16) Uani 1 1 d .
C4 C 0.7219(4) 0.21591(18) 0.06414(10) 0.0207(4) Uani 1 1 d .
C5 C 0.5984(4) 0.10767(18) 0.09225(10) 0.0229(4) Uani 1 1 d .
C6 C 0.4082(4) 0.11527(19) 0.14511(10) 0.0240(4) Uani 1 1 d .
C7 C 0.3458(4) 0.23171(19) 0.17049(10) 0.0236(4) Uani 1 1 d .
C8 C 0.4706(4) 0.33998(18) 0.14315(10) 0.0220(4) Uani 1 1 d .
C9 C 0.6616(4) 0.33582(17) 0.08817(9) 0.0187(4) Uani 1 1 d .
C10 C 0.8217(4) 0.43204(18) 0.04734(9) 0.0184(4) Uani 1 1 d .
C11 C 1.3281(4) 0.35984(18) -0.10081(10) 0.0192(4) Uani 1 1 d .
H11A H 1.3709 0.2857 -0.0785 0.023 Uiso 1 1 calc R
H11B H 1.5180 0.4098 -0.1106 0.023 Uiso 1 1 calc R
C12 C 1.1458(4) 0.31539(18) -0.17112(10) 0.0205(4) Uani 1 1 d .
H12A H 0.9519 0.2693 -0.1610 0.025 Uiso 1 1 calc R
H12B H 1.1117 0.3896 -0.1946 0.025 Uiso 1 1 calc R
C13 C 1.2953(4) 0.23087(19) -0.22130(10) 0.0228(4) Uani 1 1 d .
H13A H 1.3720 0.1682 -0.1945 0.027 Uiso 1 1 calc R
H13B H 1.4648 0.2823 -0.2403 0.027 Uiso 1 1 calc R
C14 C 1.0905(4) 0.16218(18) -0.28304(9) 0.0205(4) Uani 1 1 d .
H14A H 0.9125 0.1168 -0.2641 0.025 Uiso 1 1 calc R
H14B H 1.0275 0.2248 -0.3123 0.025 Uiso 1 1 calc R
C15 C 1.2315(4) 0.06888(19) -0.33004(10) 0.0233(4) Uani 1 1 d .
H15A H 1.3792 0.1159 -0.3578 0.028 Uiso 1 1 calc R
H15B H 1.3358 0.0191 -0.2996 0.028 Uiso 1 1 calc R
C16 C 1.0101(4) -0.02048(18) -0.38078(10) 0.0225(4) Uani 1 1 d .
H16A H 0.8660 -0.0693 -0.3529 0.027 Uiso 1 1 calc R
H16B H 0.9012 0.0295 -0.4101 0.027 Uiso 1 1 calc R
C17 C 1.1501(4) -0.11125(18) -0.42949(10) 0.0231(4) Uani 1 1 d .
H17A H 1.2717 -0.1565 -0.4003 0.028 Uiso 1 1 calc R
H17B H 1.2824 -0.0627 -0.4601 0.028 Uiso 1 1 calc R
C18 C 0.9268(4) -0.20688(18) -0.47620(10) 0.0231(4) Uani 1 1 d .
H18A H 0.7974 -0.2567 -0.4455 0.028 Uiso 1 1 calc R
H18B H 0.8021 -0.1615 -0.5045 0.028 Uiso 1 1 calc R
C19 C 1.0647(4) -0.29612(18) -0.52625(10) 0.0229(4) Uani 1 1 d .
H19A H 1.1913 -0.3409 -0.4981 0.027 Uiso 1 1 calc R
H19B H 1.1917 -0.2466 -0.5575 0.027 Uiso 1 1 calc R
C20 C 0.8393(4) -0.39227(18) -0.57194(10) 0.0225(4) Uani 1 1 d .
H20A H 0.7132 -0.4421 -0.5406 0.027 Uiso 1 1 calc R
H20B H 0.7117 -0.3473 -0.5997 0.027 Uiso 1 1 calc R
C21 C 0.9747(4) -0.48145(19) -0.62262(10) 0.0254(4) Uani 1 1 d .
H21A H 1.1026 -0.4319 -0.6537 0.031 Uiso 1 1 calc R
H21B H 1.0998 -0.5276 -0.5950 0.031 Uiso 1 1 calc R
C22 C 0.7456(5) -0.5754(2) -0.66830(12) 0.0336(5) Uani 1 1 d .
H22A H 0.6230 -0.6269 -0.6379 0.050 Uiso 1 1 calc R
H22B H 0.8444 -0.6294 -0.7003 0.050 Uiso 1 1 calc R
H22C H 0.6218 -0.5303 -0.6961 0.050 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
_geom_angle_site_symmetry_3
C2 C1 C10 115.97(17) . 2_765
C2 C1 C11 117.71(16) . .
C10 C1 C11 126.27(17) 2_765 .
C1 C2 C10 126.08(18) . .
C1 C2 S3 119.97(14) . .
C10 C2 S3 113.93(14) . .
C4 S3 C2 90.37(9) . .
C5 C4 C9 122.72(18) . .
C5 C4 S3 122.15(15) . .
C9 C4 S3 115.12(14) . .
F1 C5 C6 120.27(17) . .
F1 C5 C4 119.96(17) . .
C6 C5 C4 119.77(18) . .
F2 C6 C5 121.36(18) . .
F2 C6 C7 119.53(17) . .
C5 C6 C7 119.11(18) . .
F3 C7 C8 119.57(18) . .
F3 C7 C6 119.10(17) . .
C8 C7 C6 121.34(18) . .
F4 C8 C7 114.87(17) . .
F4 C8 C9 123.86(17) . .
C7 C8 C9 121.26(18) . .
C8 C9 C4 115.78(17) . .
C8 C9 C10 134.05(17) . .
C4 C9 C10 110.17(15) . .
C1 C10 C2 117.95(17) 2_765 .
C1 C10 C9 131.67(17) 2_765 .
C2 C10 C9 110.38(16) . .
C1 C11 C12 112.28(14) . .
C1 C11 H11A 109.1 . .
C12 C11 H11A 109.1 . .
C1 C11 H11B 109.1 . .
C12 C11 H11B 109.1 . .
H11A C11 H11B 107.9 . .
C13 C12 C11 112.74(14) . .
C13 C12 H12A 109.0 . .
C11 C12 H12A 109.0 . .
C13 C12 H12B 109.0 . .
C11 C12 H12B 109.0 . .
H12A C12 H12B 107.8 . .
C12 C13 C14 113.17(14) . .
C12 C13 H13A 108.9 . .
C14 C13 H13A 108.9 . .
C12 C13 H13B 108.9 . .
C14 C13 H13B 108.9 . .
H13A C13 H13B 107.8 . .
C15 C14 C13 113.40(14) . .
C15 C14 H14A 108.9 . .
C13 C14 H14A 108.9 . .
C15 C14 H14B 108.9 . .
C13 C14 H14B 108.9 . .
H14A C14 H14B 107.7 . .
C16 C15 C14 113.25(15) . .
C16 C15 H15A 108.9 . .
C14 C15 H15A 108.9 . .
C16 C15 H15B 108.9 . .
C14 C15 H15B 108.9 . .
H15A C15 H15B 107.7 . .
C17 C16 C15 113.58(15) . .
C17 C16 H16A 108.8 . .
C15 C16 H16A 108.8 . .
C17 C16 H16B 108.8 . .
C15 C16 H16B 108.8 . .
H16A C16 H16B 107.7 . .
C16 C17 C18 113.46(15) . .
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 113.87(15) . .
C19 C18 H18A 108.8 . .
C17 C18 H18A 108.8 . .
C19 C18 H18B 108.8 . .
C17 C18 H18B 108.8 . .
H18A C18 H18B 107.7 . .
C18 C19 C20 113.36(15) . .
C18 C19 H19A 108.9 . .
C20 C19 H19A 108.9 . .
C18 C19 H19B 108.9 . .
C20 C19 H19B 108.9 . .
H19A C19 H19B 107.7 . .
C21 C20 C19 113.82(16) . .
C21 C20 H20A 108.8 . .
C19 C20 H20A 108.8 . .
C21 C20 H20B 108.8 . .
C19 C20 H20B 108.8 . .
H20A C20 H20B 107.7 . .
C22 C21 C20 112.85(17) . .
C22 C21 H21A 109.0 . .
C20 C21 H21A 109.0 . .
C22 C21 H21B 109.0 . .
C20 C21 H21B 109.0 . .
H21A C21 H21B 107.8 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.341(2) .
F2 C6 1.339(2) .
F3 C7 1.340(2) .
F4 C8 1.339(2) .
C1 C2 1.403(3) .
C1 C10 1.404(3) 2_765
C1 C11 1.500(3) .
C2 C10 1.417(3) .
C2 S3 1.7493(19) .
S3 C4 1.7265(19) .
C4 C5 1.390(3) .
C4 C9 1.410(3) .
C5 C6 1.368(3) .
C6 C7 1.385(3) .
C7 C8 1.385(3) .
C8 C9 1.399(3) .
C9 C10 1.486(3) .
C10 C1 1.404(3) 2_765
C11 C12 1.540(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.520(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.526(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.525(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.525(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.523(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.524(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.521(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.523(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.521(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.520(3) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 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
C10 C1 C2 C10 -0.4(3) 2_765 .
C11 C1 C2 C10 -178.12(15) . .
C10 C1 C2 S3 177.76(11) 2_765 .
C11 C1 C2 S3 0.1(2) . .
C1 C2 S3 C4 -179.89(14) . .
C10 C2 S3 C4 -1.50(13) . .
C2 S3 C4 C5 180.00(15) . .
C2 S3 C4 C9 0.79(14) . .
C9 C4 C5 F1 -179.11(15) . .
S3 C4 C5 F1 1.7(2) . .
C9 C4 C5 C6 0.5(3) . .
S3 C4 C5 C6 -178.66(14) . .
F1 C5 C6 F2 -1.9(3) . .
C4 C5 C6 F2 178.54(16) . .
F1 C5 C6 C7 178.57(16) . .
C4 C5 C6 C7 -1.0(3) . .
F2 C6 C7 F3 0.4(3) . .
C5 C6 C7 F3 -179.98(16) . .
F2 C6 C7 C8 -179.19(16) . .
C5 C6 C7 C8 0.4(3) . .
F3 C7 C8 F4 0.3(2) . .
C6 C7 C8 F4 179.88(16) . .
F3 C7 C8 C9 -178.79(15) . .
C6 C7 C8 C9 0.8(3) . .
F4 C8 C9 C4 179.72(15) . .
C7 C8 C9 C4 -1.3(3) . .
F4 C8 C9 C10 -0.5(3) . .
C7 C8 C9 C10 178.44(17) . .
C5 C4 C9 C8 0.7(2) . .
S3 C4 C9 C8 179.89(12) . .
C5 C4 C9 C10 -179.14(15) . .
S3 C4 C9 C10 0.07(18) . .
C1 C2 C10 C1 0.4(3) . 2_765
S3 C2 C10 C1 -177.84(12) . 2_765
C1 C2 C10 C9 -179.93(15) . .
S3 C2 C10 C9 1.79(17) . .
C8 C9 C10 C1 -1.4(3) . 2_765
C4 C9 C10 C1 178.40(16) . 2_765
C8 C9 C10 C2 179.06(18) . .
C4 C9 C10 C2 -1.16(19) . .
C2 C1 C11 C12 90.72(19) . .
C10 C1 C11 C12 -86.7(2) 2_765 .
C1 C11 C12 C13 -177.12(16) . .
C11 C12 C13 C14 166.65(16) . .
C12 C13 C14 C15 -175.08(16) . .
C13 C14 C15 C16 166.70(16) . .
C14 C15 C16 C17 178.19(16) . .
C15 C16 C17 C18 175.60(16) . .
C16 C17 C18 C19 178.69(16) . .
C17 C18 C19 C20 179.25(16) . .
C18 C19 C20 C21 179.57(16) . .
C19 C20 C21 C22 -179.24(17) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102395079
