#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504854.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_1504854
loop_
_publ_author_name
'Wang, Yongfeng'
'Parkin, Sean R.'
'Watson, Mark D.'
_publ_section_title
;
 Benzodichalcogenophenes with perfluoroarene termini.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4421
_journal_page_last               4424
_journal_paper_doi               10.1021/ol801569m
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C24 H4 F14 S2'
_chemical_formula_sum            'C24 H4 F14 S2'
_chemical_formula_weight         622.39
_chemical_name_systematic
; 
 ? 
;
_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                88.429(3)
_cell_angle_beta                 77.042(3)
_cell_angle_gamma                76.840(3)
_cell_formula_units_Z            1
_cell_length_a                   6.3778(5)
_cell_length_b                   7.8235(6)
_cell_length_c                   10.9923(8)
_cell_measurement_reflns_used    5550
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      69.36
_cell_measurement_theta_min      5.81
_cell_volume                     520.31(7)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
; 
SHELX97-2 (Sheldrick, 2008) and local procedures 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0971
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7596
_diffrn_reflns_theta_full        69.49
_diffrn_reflns_theta_max         69.49
_diffrn_reflns_theta_min         4.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.666
_exptl_absorpt_correction_T_max  0.8672
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs in APEX2 (BrukerAXS, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.103
_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     219
_refine_ls_number_reflns         1915
_refine_ls_number_restraints     184
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0829P)²+0.5493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                1763
_reflns_number_total             1915
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol801569m_si_001.cif
_cod_data_source_block           x07067_1b
_cod_database_code               1504854
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4015(4) 0.6631(3) 0.5662(2) 0.0229(5) Uani 1 1 d . . .
H1 H 0.3368 0.7719 0.6103 0.028 Uiso 1 1 calc R A 1
C2 C 0.6082(4) 0.6344(3) 0.4853(2) 0.0224(5) Uani 0.884(2) 1 d PDU B 1
S3 S 0.76569(11) 0.78849(9) 0.45480(6) 0.0201(3) Uani 0.884(2) 1 d PDU B 1
C4 C 0.9761(10) 0.6374(8) 0.3533(7) 0.0197(12) Uani 0.884(2) 1 d PDU B 1
C5 C 0.9182(5) 0.4839(4) 0.3457(3) 0.0214(6) Uani 0.884(2) 1 d PDU B 1
H5 H 1.0120 0.3886 0.2942 0.026 Uiso 0.884(2) 1 calc PR B 1
C6 C 0.7058(4) 0.4729(3) 0.4201(2) 0.0220(5) Uani 0.884(2) 1 d PDU . 1
C2' C 0.6082(4) 0.6344(3) 0.4853(2) 0.0224(5) Uani 0.116(2) 1 d PDU B 2
C3' C 0.800(3) 0.714(2) 0.4358(18) 0.0201(3) Uani 0.116(2) 1 d PDU B 2
H3' H 0.8078 0.8215 0.4714 0.024 Uiso 0.116(2) 1 calc PR B 2
C4' C 0.964(9) 0.635(5) 0.341(7) 0.0197(12) Uani 0.116(2) 1 d PDU B 2
S5' S 0.9449(10) 0.4160(8) 0.3088(5) 0.0214(6) Uani 0.116(2) 1 d PDU B 2
C6' C 0.7058(4) 0.4729(3) 0.4201(2) 0.0220(5) Uani 0.116(2) 1 d PDU . 2
C7 C 1.1786(4) 0.6879(3) 0.2874(2) 0.0203(5) Uani 1 1 d . . .
C8 C 1.2132(4) 0.8555(3) 0.2964(2) 0.0224(5) Uani 1 1 d . B .
C9 C 1.4021(4) 0.9042(3) 0.2353(2) 0.0221(5) Uani 1 1 d . . .
C10 C 1.5717(4) 0.7887(3) 0.1582(2) 0.0231(6) Uani 1 1 d . B .
C11 C 1.5403(4) 0.6221(4) 0.1469(3) 0.0280(6) Uani 1 1 d . . .
C12 C 1.3514(4) 0.5736(3) 0.2091(3) 0.0264(6) Uani 1 1 d . B .
F1 F 1.0563(3) 0.9810(2) 0.36548(16) 0.0345(4) Uani 1 1 d . . .
F2 F 1.4150(3) 1.0691(2) 0.25027(15) 0.0318(4) Uani 1 1 d . B .
F3 F 1.6933(3) 0.4998(2) 0.0734(2) 0.0483(6) Uani 1 1 d . B .
F4 F 1.3404(3) 0.4089(2) 0.19093(19) 0.0419(5) Uani 1 1 d . . .
C13 C 1.7718(4) 0.8465(4) 0.0859(3) 0.0295(6) Uani 1 1 d DU . .
F5 F 1.8345(12) 0.9515(9) 0.1584(7) 0.0345(13) Uani 0.66(3) 1 d PDU B 1
F6 F 1.7297(15) 0.942(2) -0.0115(9) 0.051(2) Uani 0.66(3) 1 d PDU B 1
F7 F 1.9442(18) 0.7168(12) 0.0485(14) 0.039(2) Uani 0.66(3) 1 d PDU B 1
F5' F 1.952(3) 0.716(3) 0.073(2) 0.034(3) Uani 0.34(3) 1 d PDU B 2
F6' F 1.820(3) 0.984(3) 0.129(3) 0.064(4) Uani 0.34(3) 1 d PDU B 2
F7' F 1.753(3) 0.872(4) -0.0326(13) 0.054(3) Uani 0.34(3) 1 d PDU B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C6' C1 C2 117.2(2) 2_666
C6 C1 C2 117.2(2) 2_666
C6' C1 H1 121.4 2_666
C6 C1 H1 121.4 2_666
C2 C1 H1 121.4 .
C1 C2 C6 121.7(2) .
C1 C2 S3 124.0(2) .
C6 C2 S3 114.24(18) .
C2 S3 C4 90.34(13) .
C5 C4 C7 128.2(4) .
C5 C4 S3 111.1(2) .
C7 C4 S3 120.6(3) .
C4 C5 C6 115.9(3) .
C4 C5 H5 122.0 .
C6 C5 H5 122.0 .
C1 C6 C2 121.1(2) 2_666
C1 C6 C5 130.6(2) 2_666
C2 C6 C5 108.4(2) .
C4' C3' H3' 119.9 .
C3' C4' C7 127(2) .
C3' C4' S5' 112.3(10) .
C7 C4' S5' 118.3(16) .
C12 C7 C8 113.9(2) .
C12 C7 C4 123.2(3) .
C8 C7 C4 122.9(3) .
C12 C7 C4' 120.6(7) .
C8 C7 C4' 124.9(11) .
F1 C8 C9 116.3(2) .
F1 C8 C7 120.3(2) .
C9 C8 C7 123.4(2) .
F2 C9 C8 117.9(2) .
F2 C9 C10 120.4(2) .
C8 C9 C10 121.7(2) .
C9 C10 C11 116.0(2) .
C9 C10 C13 121.2(2) .
C11 C10 C13 122.8(3) .
F3 C11 C12 116.8(2) .
F3 C11 C10 121.0(2) .
C12 C11 C10 122.1(3) .
F4 C12 C11 116.6(2) .
F4 C12 C7 120.5(2) .
C11 C12 C7 122.9(2) .
F6' C13 F7 113.6(12) .
F6' C13 F6 87.4(11) .
F7 C13 F6 109.5(6) .
F6' C13 F5' 107.2(14) .
F6 C13 F5' 120.4(11) .
F6' C13 F7' 109.6(8) .
F7 C13 F7' 89.9(10) .
F5' C13 F7' 101.8(11) .
F7 C13 F5 105.8(6) .
F6 C13 F5 105.6(5) .
F5' C13 F5 96.8(12) .
F7' C13 F5 127.3(10) .
F6' C13 C10 117.5(8) .
F7 C13 C10 113.8(6) .
F6 C13 C10 112.0(4) .
F5' C13 C10 110.8(13) .
F7' C13 C10 108.8(8) .
F5 C13 C10 109.6(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6' 1.378(4) 2_666
C1 C6 1.378(4) 2_666
C1 C2 1.389(4) .
C1 H1 0.9500 .
C2 C6 1.410(4) .
C2 S3 1.719(2) .
S3 C4 1.767(4) .
C4 C5 1.344(5) .
C4 C7 1.464(4) .
C5 C6 1.437(4) .
C5 H5 0.9500 .
C6 C1 1.378(4) 2_666
C3' C4' 1.349(11) .
C3' H3' 0.9500 .
C4' C7 1.51(2) .
C4' S5' 1.793(12) .
C7 C12 1.387(4) .
C7 C8 1.389(4) .
C8 F1 1.339(3) .
C8 C9 1.371(4) .
C9 F2 1.328(3) .
C9 C10 1.375(4) .
C10 C11 1.376(4) .
C10 C13 1.501(4) .
C11 F3 1.336(3) .
C11 C12 1.374(4) .
C12 F4 1.330(3) .
C13 F6' 1.310(10) .
C13 F7 1.311(7) .
C13 F6 1.330(6) .
C13 F5' 1.335(11) .
C13 F7' 1.339(10) .
C13 F5 1.341(6) .
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
C6' C1 C2 C6 -0.3(4) 2_666 .
C6 C1 C2 C6 -0.3(4) 2_666 .
C6' C1 C2 S3 179.28(18) 2_666 .
C6 C1 C2 S3 179.28(18) 2_666 .
C1 C2 S3 C4 179.2(4) . .
C6 C2 S3 C4 -1.1(4) . .
C2 S3 C4 C5 1.1(6) . .
C2 S3 C4 C7 179.3(7) . .
C7 C4 C5 C6 -178.9(7) . .
S3 C4 C5 C6 -0.7(8) . .
C1 C2 C6 C1 0.3(4) . 2_666
S3 C2 C6 C1 -179.31(18) . 2_666
C1 C2 C6 C5 -179.4(2) . .
S3 C2 C6 C5 0.9(3) . .
C4 C5 C6 C1 -179.8(5) . 2_666
C4 C5 C6 C2 -0.1(6) . .
C5 C4 C7 C12 -3.7(12) . .
S3 C4 C7 C12 178.3(4) . .
C5 C4 C7 C8 175.3(7) . .
S3 C4 C7 C8 -2.6(9) . .
C5 C4 C7 C4' 66(17) . .
S3 C4 C7 C4' -112(19) . .
C3' C4' C7 C12 165(6) . .
S5' C4' C7 C12 4(8) . .
C3' C4' C7 C8 -24(11) . .
S5' C4' C7 C8 175(3) . .
C3' C4' C7 C4 51(11) . .
S5' C4' C7 C4 -110(24) . .
C12 C7 C8 F1 177.7(2) . .
C4 C7 C8 F1 -1.5(6) . .
C4' C7 C8 F1 6(5) . .
C12 C7 C8 C9 -1.0(4) . .
C4 C7 C8 C9 179.9(5) . .
C4' C7 C8 C9 -172(5) . .
F1 C8 C9 F2 0.6(3) . .
C7 C8 C9 F2 179.3(2) . .
F1 C8 C9 C10 -177.7(2) . .
C7 C8 C9 C10 1.0(4) . .
F2 C9 C10 C11 -178.6(2) . .
C8 C9 C10 C11 -0.3(4) . .
F2 C9 C10 C13 -2.0(4) . .
C8 C9 C10 C13 176.3(2) . .
C9 C10 C11 F3 179.3(2) . .
C13 C10 C11 F3 2.8(4) . .
C9 C10 C11 C12 -0.3(4) . .
C13 C10 C11 C12 -176.8(2) . .
F3 C11 C12 F4 0.5(4) . .
C10 C11 C12 F4 -179.8(2) . .
F3 C11 C12 C7 -179.4(2) . .
C10 C11 C12 C7 0.2(5) . .
C8 C7 C12 F4 -179.6(2) . .
C4 C7 C12 F4 -0.4(6) . .
C4' C7 C12 F4 -8(4) . .
C8 C7 C12 C11 0.4(4) . .
C4 C7 C12 C11 179.5(5) . .
C4' C7 C12 C11 172(4) . .
C9 C10 C13 F6' 23.8(17) . .
C11 C10 C13 F6' -159.9(17) . .
C9 C10 C13 F7 160.1(7) . .
C11 C10 C13 F7 -23.6(8) . .
C9 C10 C13 F6 -75.1(8) . .
C11 C10 C13 F6 101.2(8) . .
C9 C10 C13 F5' 147.4(11) . .
C11 C10 C13 F5' -36.2(11) . .
C9 C10 C13 F7' -101.4(13) . .
C11 C10 C13 F7' 74.9(13) . .
C9 C10 C13 F5 41.8(4) . .
C11 C10 C13 F5 -141.8(4) . .
