#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/53/1505397.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_1505397
loop_
_publ_author_name
'Ie, Yutaka'
'Nitani, Masashi'
'Ishikawa, Motomi'
'Nakayama, Ken-ichi'
'Tada, Hirokazu'
'Kaneda, Takahiro'
'Aso, Yoshio'
_publ_section_title
;
 Electronegative oligothiophenes for n-type semiconductors:
 difluoromethylene-bridged bithiophene and its oligomers.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2115
_journal_page_last               2118
_journal_paper_doi               10.1021/ol070584a
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C29 H6 F28 S4'
_chemical_formula_weight         1014.58
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 95.9290(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   53.0849(14)
_cell_length_b                   6.5227(2)
_cell_length_c                   9.6315(5)
_cell_measurement_temperature    93(2)
_cell_volume                     3317.1(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_max       63
_diffrn_reflns_limit_h_min       -63
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18235
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    4.394
_exptl_absorpt_correction_T_max  0.9574
_exptl_absorpt_correction_T_min  0.4314
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.2252
_reflns_number_gt                1782
_reflns_number_total             3018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070584asi20070309_032535.cif
_cod_data_source_block           DFH-4T
_cod_database_code               1505397
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.92362(3) -0.2235(2) -0.14080(14) 0.0634(5) Uani 1 1 d . . .
S2 S 0.97163(3) -0.1348(2) 0.09271(14) 0.0613(5) Uani 1 1 d . . .
F3 F 0.90016(6) -0.4455(5) -0.4001(3) 0.0664(9) Uani 1 1 d . . .
F4 F 0.87270(6) -0.5017(5) -0.1941(3) 0.0714(9) Uani 1 1 d . . .
F5 F 0.85482(6) -0.1653(5) -0.1134(3) 0.0735(10) Uani 1 1 d . . .
F6 F 0.85050(6) -0.4982(5) -0.3973(3) 0.0723(10) Uani 1 1 d . . .
F7 F 1.01327(6) 0.5053(4) 0.1721(3) 0.0728(9) Uani 1 1 d . . .
F8 F 0.87685(6) -0.1873(5) -0.4834(3) 0.0669(9) Uani 1 1 d . . .
F9 F 0.84256(7) -0.0585(6) -0.3233(4) 0.0835(11) Uani 1 1 d . . .
C10 C 0.98283(10) 0.2332(8) 0.1605(5) 0.0566(14) Uani 1 1 d . . .
C11 C 0.88587(11) -0.2811(8) -0.3622(5) 0.0602(14) Uani 1 1 d . . .
C12 C 0.98945(9) 0.0334(8) 0.1944(5) 0.0528(13) Uani 1 1 d . . .
F10 F 0.82046(7) -0.5063(7) -0.1777(4) 0.0915(12) Uani 1 1 d . . .
C14 C 0.84463(11) -0.2256(10) -0.2412(6) 0.0681(16) Uani 1 1 d . . .
C15 C 0.93427(10) 0.0215(8) -0.1044(5) 0.0550(13) Uani 1 1 d . . .
C16 C 0.86324(11) -0.3763(9) -0.2993(6) 0.0647(15) Uani 1 1 d . . .
F11 F 0.80568(7) -0.3248(7) -0.3586(4) 0.1037(14) Uani 1 1 d . . .
C18 C 0.95469(10) 0.0618(8) 0.0066(5) 0.0542(13) Uani 1 1 d . . .
C19 C 0.90203(10) -0.1376(8) -0.2742(5) 0.0548(13) Uani 1 1 d . . .
C20 C 1.0000 0.3735(13) 0.2500 0.064(2) Uani 1 2 d S . .
C21 C 0.92122(11) 0.1626(9) -0.1892(6) 0.0679(16) Uani 1 1 d . . .
H1 H 0.9241 0.3061 -0.1830 0.081 Uiso 1 1 calc R . .
C22 C 0.96297(11) 0.2523(9) 0.0547(6) 0.0609(14) Uani 1 1 d . . .
H2 H 0.9561 0.3791 0.0204 0.073 Uiso 1 1 calc R . .
C23 C 0.90289(11) 0.0706(9) -0.2871(5) 0.0625(15) Uani 1 1 d . . .
H3 H 0.8923 0.1458 -0.3545 0.075 Uiso 1 1 calc R . .
C24 C 0.81813(12) -0.3144(13) -0.2277(7) 0.082(2) Uani 1 1 d . A .
F12 F 0.81042(7) -0.2230(7) -0.0011(4) 0.1067(14) Uani 1 1 d . A .
C28 C 0.80169(16) -0.1931(19) -0.1362(10) 0.113(3) Uani 1 1 d . . .
C30 C 0.7725(7) -0.208(5) -0.176(4) 0.160(15) Uani 0.630(8) 1 d P A 1
F21 F 0.7846(2) 0.0327(17) -0.2726(10) 0.087(4) Uani 0.370(8) 1 d P A 2
F22 F 0.8140(2) 0.1053(19) -0.1078(13) 0.072(3) Uani 0.370(8) 1 d P A 2
F23 F 0.7758(2) 0.046(2) -0.0553(9) 0.084(4) Uani 0.370(8) 1 d P A 2
F24 F 0.76438(15) -0.167(2) -0.2940(10) 0.190(6) Uani 0.630(8) 1 d P A 1
F25 F 0.76200(16) -0.119(2) -0.0763(10) 0.170(5) Uani 0.630(8) 1 d P A 1
F26 F 0.7705(3) -0.414(3) -0.1541(18) 0.165(7) Uani 0.630(8) 1 d P A 1
F28 F 0.8053(2) 0.026(2) -0.1764(16) 0.111(4) Uani 0.630(8) 1 d P A 1
F27 F 0.7773(3) -0.323(5) -0.126(2) 0.092(6) Uani 0.370(8) 1 d P A 2
C31 C 0.7939(5) -0.005(5) -0.136(3) 0.084(8) Uani 0.370(8) 1 d P A 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
_geom_angle_site_symmetry_3
C15 S1 C19 91.7(3) . .
C12 S2 C18 91.7(3) . .
C12 C10 C22 114.3(5) . .
C12 C10 C20 108.4(5) . .
C22 C10 C20 137.3(5) . .
F8 C11 F3 106.0(4) . .
F8 C11 C19 109.8(4) . .
F3 C11 C19 109.9(4) . .
F8 C11 C16 107.5(4) . .
F3 C11 C16 105.3(5) . .
C19 C11 C16 117.6(5) . .
C10 C12 C12 109.2(3) . 2_755
C10 C12 S2 111.2(4) . .
C12 C12 S2 139.55(18) 2_755 .
F9 C14 F5 107.5(5) . .
F9 C14 C24 109.6(5) . .
F5 C14 C24 108.4(5) . .
F9 C14 C16 108.7(5) . .
F5 C14 C16 107.8(5) . .
C24 C14 C16 114.6(6) . .
C21 C15 C18 127.2(5) . .
C21 C15 S1 111.6(4) . .
C18 C15 S1 121.2(4) . .
F4 C16 F6 106.6(5) . .
F4 C16 C11 107.1(4) . .
F6 C16 C11 108.4(4) . .
F4 C16 C14 108.4(5) . .
F6 C16 C14 109.5(5) . .
C11 C16 C14 116.3(5) . .
C22 C18 C15 126.3(5) . .
C22 C18 S2 112.0(4) . .
C15 C18 S2 121.7(4) . .
C23 C19 C11 127.0(5) . .
C23 C19 S1 111.4(4) . .
C11 C19 S1 121.6(4) . .
F7 C20 F7 103.0(6) . 2_755
F7 C20 C10 112.4(2) . .
F7 C20 C10 112.2(2) 2_755 .
F7 C20 C10 112.2(2) . 2_755
F7 C20 C10 112.4(2) 2_755 2_755
C10 C20 C10 104.8(6) . 2_755
C15 C21 C23 112.5(5) . .
C15 C21 H1 123.8 . .
C23 C21 H1 123.8 . .
C18 C22 C10 110.8(5) . .
C18 C22 H2 124.6 . .
C10 C22 H2 124.6 . .
C19 C23 C21 112.9(5) . .
C19 C23 H3 123.6 . .
C21 C23 H3 123.6 . .
F10 C24 F11 107.7(6) . .
F10 C24 C28 108.2(8) . .
F11 C24 C28 108.0(6) . .
F10 C24 C14 109.3(5) . .
F11 C24 C14 107.5(6) . .
C28 C24 C14 115.9(7) . .
C31 C28 F12 102.3(13) . .
C31 C28 F28 31.2(13) . .
F12 C28 F28 110.3(9) . .
C31 C28 C24 134.0(18) . .
F12 C28 C24 108.8(7) . .
F28 C28 C24 104.5(10) . .
C31 C28 F27 104.4(18) . .
F12 C28 F27 93.6(11) . .
F28 C28 F27 131.6(13) . .
C24 C28 F27 106.5(10) . .
C31 C28 C30 75.7(19) . .
F12 C28 C30 117.5(14) . .
F28 C28 C30 98.4(15) . .
C24 C28 C30 116.0(14) . .
F27 C28 C30 34.1(13) . .
F24 C30 F25 117(3) . .
F24 C30 F26 110(4) . .
F25 C30 F26 106(2) . .
F24 C30 C28 118(2) . .
F25 C30 C28 106(3) . .
F26 C30 C28 97(2) . .
F22 C31 C28 106(2) . .
F22 C31 F23 112(2) . .
C28 C31 F23 119(3) . .
F22 C31 F21 108(2) . .
C28 C31 F21 104(2) . .
F23 C31 F21 107.5(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C15 1.719(5) .
S1 C19 1.725(5) .
S2 C12 1.693(5) .
S2 C18 1.728(5) .
F3 C11 1.384(6) .
F4 C16 1.357(6) .
F5 C14 1.351(6) .
F6 C16 1.360(6) .
F7 C20 1.381(5) .
F8 C11 1.360(5) .
F9 C14 1.344(7) .
C10 C12 1.381(7) .
C10 C22 1.394(7) .
C10 C20 1.500(7) .
C11 C19 1.476(7) .
C11 C16 1.532(8) .
C12 C12 1.468(9) 2_755
F10 C24 1.343(8) .
C14 C24 1.539(9) .
C14 C16 1.539(8) .
C15 C21 1.370(7) .
C15 C18 1.466(7) .
F11 C24 1.363(7) .
C18 C22 1.382(7) .
C19 C23 1.364(7) .
C20 F7 1.381(5) 2_755
C20 C10 1.500(7) 2_755
C21 C23 1.417(7) .
C21 H1 0.9500 .
C22 H2 0.9500 .
C23 H3 0.9500 .
C24 C28 1.524(11) .
F12 C28 1.350(9) .
C28 C31 1.30(3) .
C28 F28 1.499(17) .
C28 F27 1.56(3) .
C28 C30 1.56(4) .
C30 F24 1.20(3) .
C30 F25 1.30(3) .
C30 F26 1.36(4) .
F21 C31 1.38(3) .
F22 C31 1.29(4) .
F23 C31 1.34(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_4
C22 C10 C12 C12 179.6(6) 2_755
C20 C10 C12 C12 0.5(7) 2_755
C22 C10 C12 S2 1.4(6) .
C20 C10 C12 S2 -177.6(3) .
C18 S2 C12 C10 -1.2(4) .
C18 S2 C12 C12 -178.5(8) 2_755
C19 S1 C15 C21 1.6(5) .
C19 S1 C15 C18 -179.1(5) .
F8 C11 C16 F4 168.5(4) .
F3 C11 C16 F4 55.8(5) .
C19 C11 C16 F4 -67.0(6) .
F8 C11 C16 F6 53.8(6) .
F3 C11 C16 F6 -58.9(5) .
C19 C11 C16 F6 178.3(4) .
F8 C11 C16 C14 -70.1(6) .
F3 C11 C16 C14 177.2(4) .
C19 C11 C16 C14 54.4(6) .
F9 C14 C16 F4 157.1(4) .
F5 C14 C16 F4 40.8(6) .
C24 C14 C16 F4 -80.0(6) .
F9 C14 C16 F6 -87.0(6) .
F5 C14 C16 F6 156.7(4) .
C24 C14 C16 F6 36.0(7) .
F9 C14 C16 C11 36.3(6) .
F5 C14 C16 C11 -80.0(6) .
C24 C14 C16 C11 159.3(5) .
C21 C15 C18 C22 6.4(9) .
S1 C15 C18 C22 -172.8(5) .
C21 C15 C18 S2 -173.1(5) .
S1 C15 C18 S2 7.7(7) .
C12 S2 C18 C22 0.8(4) .
C12 S2 C18 C15 -179.7(5) .
F8 C11 C19 C23 17.3(8) .
F3 C11 C19 C23 133.6(6) .
C16 C11 C19 C23 -106.0(7) .
F8 C11 C19 S1 -160.5(4) .
F3 C11 C19 S1 -44.2(6) .
C16 C11 C19 S1 76.1(6) .
C15 S1 C19 C23 -1.1(4) .
C15 S1 C19 C11 177.0(5) .
C12 C10 C20 F7 121.9(5) .
C22 C10 C20 F7 -56.8(8) .
C12 C10 C20 F7 -122.5(5) 2_755
C22 C10 C20 F7 58.8(8) 2_755
C12 C10 C20 C10 -0.2(3) 2_755
C22 C10 C20 C10 -179.0(8) 2_755
C18 C15 C21 C23 179.1(5) .
S1 C15 C21 C23 -1.6(7) .
C15 C18 C22 C10 -179.6(5) .
S2 C18 C22 C10 -0.1(6) .
C12 C10 C22 C18 -0.8(7) .
C20 C10 C22 C18 177.9(5) .
C11 C19 C23 C21 -177.6(6) .
S1 C19 C23 C21 0.4(7) .
C15 C21 C23 C19 0.8(8) .
F9 C14 C24 F10 164.1(5) .
F5 C14 C24 F10 -78.8(6) .
C16 C14 C24 F10 41.6(7) .
F9 C14 C24 F11 47.6(7) .
F5 C14 C24 F11 164.6(5) .
C16 C14 C24 F11 -75.0(7) .
F9 C14 C24 C28 -73.3(8) .
F5 C14 C24 C28 43.7(9) .
C16 C14 C24 C28 164.2(7) .
F10 C24 C28 C31 178.7(18) .
F11 C24 C28 C31 -65(2) .
C14 C24 C28 C31 56(2) .
F10 C24 C28 F12 48.8(9) .
F11 C24 C28 F12 165.1(7) .
C14 C24 C28 F12 -74.3(11) .
F10 C24 C28 F28 166.7(8) .
F11 C24 C28 F28 -77.0(9) .
C14 C24 C28 F28 43.6(10) .
F10 C24 C28 F27 -51.0(12) .
F11 C24 C28 F27 65.3(14) .
C14 C24 C28 F27 -174.1(11) .
F10 C24 C28 C30 -86.3(15) .
F11 C24 C28 C30 30.0(17) .
C14 C24 C28 C30 150.6(14) .
C31 C28 C30 F24 78(3) .
F12 C28 C30 F24 175(2) .
F28 C28 C30 F24 56(3) .
C24 C28 C30 F24 -54(3) .
F27 C28 C30 F24 -135(5) .
C31 C28 C30 F25 -56(2) .
F12 C28 C30 F25 40(3) .
F28 C28 C30 F25 -78(2) .
C24 C28 C30 F25 171.6(17) .
F27 C28 C30 F25 91(3) .
C31 C28 C30 F26 -165(2) .
F12 C28 C30 F26 -69(2) .
F28 C28 C30 F26 173.2(18) .
C24 C28 C30 F26 62(2) .
F27 C28 C30 F26 -18.6(15) .
F12 C28 C31 F22 67(2) .
F28 C28 C31 F22 -42(2) .
C24 C28 C31 F22 -65(2) .
F27 C28 C31 F22 163.6(15) .
C30 C28 C31 F22 -178(2) .
F12 C28 C31 F23 -60(2) .
F28 C28 C31 F23 -169(4) .
C24 C28 C31 F23 168.3(11) .
F27 C28 C31 F23 37(2) .
C30 C28 C31 F23 56(2) .
F12 C28 C31 F21 -179.5(15) .
F28 C28 C31 F21 71(3) .
C24 C28 C31 F21 49(3) .
F27 C28 C31 F21 -82(2) .
C30 C28 C31 F21 -64(2) .
