#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504857.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_1504857
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 H8 F10 O2 S2'
_chemical_formula_sum            'C24 H8 F10 O2 S2'
_chemical_formula_weight         582.42
_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                98.625(3)
_cell_angle_beta                 93.623(3)
_cell_angle_gamma                105.298(3)
_cell_formula_units_Z            1
_cell_length_a                   7.1780(5)
_cell_length_b                   7.9513(4)
_cell_length_c                   9.4507(5)
_cell_measurement_reflns_used    3300
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      69.26
_cell_measurement_theta_min      4.76
_cell_volume                     511.40(5)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0737
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3507
_diffrn_reflns_theta_full        69.55
_diffrn_reflns_theta_max         69.55
_diffrn_reflns_theta_min         4.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.459
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Twinabs (BrukerAXS, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'twinned blade'
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3507
_refine_ls_number_restraints     118
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0770
_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)+(0.1435P)²+1.8803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2498
_refine_ls_wR_factor_ref         0.2629
_reflns_number_gt                3147
_reflns_number_total             3507
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol801569m_si_001.cif
_cod_data_source_block           x07101b_1g
_cod_database_code               1504857
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 0.5456(6) 0.6865(5) 0.5400(4) 0.0198(8) Uani 1 1 d . . .
C2 C 0.5816(6) 0.5820(6) 0.6359(4) 0.0202(8) Uani 0.959(5) 1 d PDU A 1
S3 S 0.68244(18) 0.65741(13) 0.81191(11) 0.0200(4) Uani 0.959(5) 1 d PDU A 1
C4 C 0.6629(6) 0.4375(6) 0.8388(5) 0.0183(9) Uani 0.959(5) 1 d PDU A 1
C5 C 0.5833(10) 0.3155(8) 0.7138(6) 0.0256(11) Uani 0.959(5) 1 d PDU A 1
H5 H 0.5627 0.1914 0.7071 0.031 Uiso 0.959(5) 1 calc PR A 1
C6 C 0.5369(6) 0.3957(5) 0.5990(4) 0.0203(8) Uani 0.959(5) 1 d PDU . 1
C2' C 0.5816(6) 0.5820(6) 0.6359(4) 0.0202(8) Uani 0.041(5) 1 d PDU A 2
C3' C 0.687(18) 0.650(3) 0.772(6) 0.021(3) Uiso 0.041(5) 1 d PDU A 2
H3' H 0.7249 0.7723 0.8134 0.025 Uiso 0.041(5) 1 calc PR A 2
C4' C 0.728(11) 0.517(4) 0.838(5) 0.020(4) Uiso 0.041(5) 1 d PDU A 2
S5' S 0.586(7) 0.306(3) 0.748(3) 0.028(4) Uiso 0.041(5) 1 d PDU A 2
C6' C 0.5369(6) 0.3957(5) 0.5990(4) 0.0203(8) Uani 0.041(5) 1 d PDU . 2
C7 C 0.7279(6) 0.4043(5) 0.9795(4) 0.0194(9) Uani 1 1 d . . .
C8 C 0.7979(6) 0.5397(5) 1.0984(4) 0.0207(9) Uani 1 1 d . A .
C9 C 0.8529(6) 0.5071(5) 1.2321(4) 0.0225(9) Uani 1 1 d . . .
C10 C 0.8443(7) 0.3390(6) 1.2522(5) 0.0234(9) Uani 1 1 d . A .
C11 C 0.7801(7) 0.2032(5) 1.1365(5) 0.0236(9) Uani 1 1 d . . .
C12 C 0.7242(7) 0.2364(5) 1.0048(5) 0.0226(9) Uani 1 1 d . A .
F1 F 0.8121(4) 0.7068(3) 1.0883(3) 0.0277(6) Uani 1 1 d . . .
F2 F 0.9185(4) 0.6422(3) 1.3410(3) 0.0284(6) Uani 1 1 d . A .
F3 F 0.9007(4) 0.3088(4) 1.3796(3) 0.0304(7) Uani 1 1 d . . .
F4 F 0.7738(5) 0.0390(4) 1.1544(3) 0.0371(8) Uani 1 1 d . A .
F5 F 0.6652(4) 0.0963(3) 0.8990(3) 0.0348(7) Uani 1 1 d . . .
O1 O 0.5856(4) 0.8660(4) 0.5818(3) 0.0240(7) Uani 1 1 d . A .
C13 C 0.7696(7) 0.9593(6) 0.5450(5) 0.0287(10) Uani 1 1 d . . .
H13A H 0.8727 0.9232 0.5949 0.043 Uiso 1 1 calc R A .
H13B H 0.7894 1.0869 0.5742 0.043 Uiso 1 1 calc R . .
H13C H 0.7731 0.9319 0.4408 0.043 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 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'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_3
O1 C1 C2 120.5(4) . .
O1 C1 C6' 121.2(4) . 2_666
C2 C1 C6' 118.2(4) . 2_666
O1 C1 C6 121.2(4) . 2_666
C2 C1 C6 118.2(4) . 2_666
C1 C2 C6 122.5(4) . .
C1 C2 S3 125.4(3) . .
C6 C2 S3 112.1(3) . .
C2 S3 C4 90.8(2) . .
C5 C4 C7 128.5(4) . .
C5 C4 S3 111.4(4) . .
C7 C4 S3 120.1(3) . .
C4 C5 C6 112.7(5) . .
C4 C5 H5 123.6 . .
C6 C5 H5 123.6 . .
C1 C6 C5 127.8(4) 2_666 .
C1 C6 C2 119.2(4) 2_666 .
C5 C6 C2 112.9(4) . .
C4' C3' H3' 124.1 . .
C3' C4' C7 153(6) . .
C3' C4' S5' 110.3(13) . .
C7 C4' S5' 81.9(18) . .
C12 C7 C8 114.9(4) . .
C12 C7 C4 122.6(4) . .
C8 C7 C4 122.5(4) . .
C12 C7 C4' 139.7(17) . .
C8 C7 C4' 103.1(11) . .
F1 C8 C9 116.5(4) . .
F1 C8 C7 121.1(4) . .
C9 C8 C7 122.3(4) . .
F2 C9 C10 120.1(4) . .
F2 C9 C8 119.3(4) . .
C10 C9 C8 120.5(4) . .
F3 C10 C9 120.3(4) . .
F3 C10 C11 121.1(4) . .
C9 C10 C11 118.6(4) . .
F4 C11 C12 120.4(4) . .
F4 C11 C10 119.1(4) . .
C12 C11 C10 120.5(4) . .
F5 C12 C11 116.2(4) . .
F5 C12 C7 120.8(4) . .
C11 C12 C7 123.1(4) . .
C1 O1 C13 112.6(3) . .
O1 C13 H13A 109.5 . .
O1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
O1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.370(5) .
C1 C2 1.374(6) .
C1 C6' 1.394(6) 2_666
C1 C6 1.394(6) 2_666
C2 C6 1.414(6) .
C2 S3 1.724(4) .
S3 C4 1.775(4) .
C4 C5 1.393(7) .
C4 C7 1.466(6) .
C5 C6 1.403(7) .
C5 H5 0.9500 .
C6 C1 1.394(6) 2_666
C3' C4' 1.396(12) .
C3' H3' 0.9500 .
C4' S5' 1.777(11) .
C7 C12 1.385(6) .
C7 C8 1.398(6) .
C8 F1 1.323(5) .
C8 C9 1.382(6) .
C9 F2 1.332(5) .
C9 C10 1.364(6) .
C10 F3 1.323(5) .
C10 C11 1.375(6) .
C11 F4 1.331(5) .
C11 C12 1.368(6) .
C12 F5 1.335(5) .
O1 C13 1.426(5) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 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
O1 C1 C2 C6 177.9(4) . .
C6' C1 C2 C6 -0.4(7) 2_666 .
C6 C1 C2 C6 -0.4(7) 2_666 .
O1 C1 C2 S3 -1.7(6) . .
C6' C1 C2 S3 180.0(3) 2_666 .
C6 C1 C2 S3 180.0(3) 2_666 .
C1 C2 S3 C4 178.9(4) . .
C6 C2 S3 C4 -0.7(3) . .
C2 S3 C4 C5 0.7(4) . .
C2 S3 C4 C7 -179.5(4) . .
C7 C4 C5 C6 179.7(4) . .
S3 C4 C5 C6 -0.6(7) . .
C4 C5 C6 C1 -179.5(4) . 2_666
C4 C5 C6 C2 0.1(7) . .
C1 C2 C6 C1 0.4(7) . 2_666
S3 C2 C6 C1 -179.9(3) . 2_666
C1 C2 C6 C5 -179.2(5) . .
S3 C2 C6 C5 0.5(5) . .
C5 C4 C7 C12 2.7(8) . .
S3 C4 C7 C12 -177.0(3) . .
C5 C4 C7 C8 -177.2(5) . .
S3 C4 C7 C8 3.1(6) . .
C5 C4 C7 C4' 147(7) . .
S3 C4 C7 C4' -33(7) . .
C3' C4' C7 C12 152(8) . .
S5' C4' C7 C12 32(6) . .
C3' C4' C7 C8 -47(9) . .
S5' C4' C7 C8 -167(2) . .
C3' C4' C7 C4 102(14) . .
S5' C4' C7 C4 -17(5) . .
C12 C7 C8 F1 178.9(4) . .
C4 C7 C8 F1 -1.2(6) . .
C4' C7 C8 F1 12(3) . .
C12 C7 C8 C9 -2.1(6) . .
C4 C7 C8 C9 177.8(4) . .
C4' C7 C8 C9 -169(3) . .
F1 C8 C9 F2 -1.0(6) . .
C7 C8 C9 F2 -180.0(4) . .
F1 C8 C9 C10 -179.6(4) . .
C7 C8 C9 C10 1.4(7) . .
F2 C9 C10 F3 0.1(7) . .
C8 C9 C10 F3 178.7(4) . .
F2 C9 C10 C11 -178.5(4) . .
C8 C9 C10 C11 0.1(7) . .
F3 C10 C11 F4 0.4(7) . .
C9 C10 C11 F4 179.0(4) . .
F3 C10 C11 C12 -179.3(4) . .
C9 C10 C11 C12 -0.7(7) . .
F4 C11 C12 F5 -0.1(7) . .
C10 C11 C12 F5 179.6(4) . .
F4 C11 C12 C7 -179.9(4) . .
C10 C11 C12 C7 -0.2(7) . .
C8 C7 C12 F5 -178.2(4) . .
C4 C7 C12 F5 1.9(7) . .
C4' C7 C12 F5 -19(4) . .
C8 C7 C12 C11 1.5(7) . .
C4 C7 C12 C11 -178.4(4) . .
C4' C7 C12 C11 161(4) . .
C2 C1 O1 C13 96.7(5) . .
C6' C1 O1 C13 -85.0(5) 2_666 .
C6 C1 O1 C13 -85.0(5) 2_666 .
