#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:42:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178820 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/74/4107476.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_4107476
loop_
_publ_author_name
'Sankar Subramanian'
'Sung Kyu Park'
'Sean R. Parkin'
'Vitaly Podzorov'
'Thomas N. Jackson'
'John E. Anthony'
_publ_section_title
;
 Chromophore Fluorination Enhances Crystallization and Stability of
 Soluble Anthradithiophene Semiconductors
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2706
_journal_page_last               2707
_journal_paper_doi               10.1021/ja073235k
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C34 H36 F2 S2 Si2'
_chemical_formula_sum            'C34 H36 F2 S2 Si2'
_chemical_formula_weight         602.93
_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                98.214(4)
_cell_angle_beta                 92.598(5)
_cell_angle_gamma                107.335(4)
_cell_formula_units_Z            1
_cell_length_a                   7.1044(5)
_cell_length_b                   7.1739(5)
_cell_length_c                   16.6481(12)
_cell_measurement_reflns_used    4264
_cell_measurement_temperature    243.0(2)
_cell_measurement_theta_max      67.60
_cell_measurement_theta_min      2.69
_cell_volume                     798.17(10)
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2006)'
_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      243.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10192
_diffrn_reflns_theta_full        67.70
_diffrn_reflns_theta_max         67.70
_diffrn_reflns_theta_min         2.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.500
_exptl_absorpt_correction_T_max  0.9066
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs in APEX2 (Bruker-AXS, 2006)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       flake
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     219
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0560
_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)+(0.0295P)²+1.2610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                2163
_reflns_number_total             2811
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja073235k-file003.cif
_cod_data_source_block           x07047
_cod_database_code               4107476
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
Si1 Si 0.25661(16) 0.86176(16) 0.67565(6) 0.0538(3) Uani 1 1 d . . .
C1 C 0.0652(4) 0.9568(4) 0.92329(17) 0.0333(6) Uani 1 1 d . . .
C2 C -0.1316(4) 0.8682(4) 0.93651(17) 0.0327(6) Uani 1 1 d . B .
C3 C -0.2662(5) 0.7314(4) 0.87473(18) 0.0380(7) Uani 1 1 d U . .
H3 H -0.2232 0.6972 0.8237 0.046 Uiso 1 1 calc R A 1
C4 C -0.4562(4) 0.6501(4) 0.88897(18) 0.0379(6) Uani 0.688(4) 1 d PDU B 1
S5 S -0.6402(3) 0.4776(4) 0.82086(11) 0.0471(5) Uani 0.688(4) 1 d PDU B 1
C6 C -0.8057(7) 0.4876(14) 0.8935(4) 0.0433(12) Uani 0.688(4) 1 d PDU B 1
F1 F -0.9941(6) 0.3736(10) 0.8711(3) 0.0618(12) Uani 0.688(4) 1 d PDU B 1
C7 C -0.7308(15) 0.601(3) 0.9641(9) 0.0433(18) Uani 0.688(4) 1 d PDU B 1
H7 H -0.8048 0.6136 1.0088 0.052 Uiso 0.688(4) 1 calc PR B 1
C8 C -0.5252(4) 0.7007(4) 0.96484(18) 0.0363(6) Uani 0.688(4) 1 d PDU B 1
C4' C -0.4562(4) 0.6501(4) 0.88897(18) 0.0379(6) Uani 0.312(4) 1 d PDU B 2
C5' C -0.616(2) 0.518(4) 0.8349(11) 0.051(3) Uani 0.312(4) 1 d PDU B 2
H5' H -0.6044 0.4682 0.7806 0.062 Uiso 0.312(4) 1 calc PR B 2
F1' F -0.9632(13) 0.353(2) 0.8368(7) 0.071(3) Uani 0.312(4) 1 d PDU B 2
C6' C -0.7833(16) 0.472(4) 0.8698(8) 0.056(3) Uani 0.312(4) 1 d PDU B 2
S7' S -0.7714(8) 0.5881(17) 0.9696(5) 0.0494(13) Uani 0.312(4) 1 d PDU B 2
C8' C -0.5252(4) 0.7007(4) 0.96484(18) 0.0363(6) Uani 0.312(4) 1 d PDU B 2
C9 C -0.3995(4) 0.8280(4) 1.02565(18) 0.0347(6) Uani 1 1 d U . .
H9 H -0.4463 0.8602 1.0761 0.042 Uiso 1 1 calc R B 1
C10 C -0.1993(4) 0.9126(4) 1.01389(17) 0.0318(6) Uani 1 1 d . . .
C11 C 0.1299(5) 0.9186(4) 0.84495(18) 0.0373(7) Uani 1 1 d . . .
C12 C 0.1816(5) 0.8900(5) 0.7787(2) 0.0454(8) Uani 1 1 d . . .
C13 C 0.5242(7) 0.8862(8) 0.6813(3) 0.0764(13) Uani 1 1 d . . .
H13A H 0.5435 0.7727 0.7031 0.092 Uiso 1 1 calc R . .
H13B H 0.5654 0.8798 0.6258 0.092 Uiso 1 1 calc R . .
C14 C 0.6566(8) 1.0719(10) 0.7323(4) 0.112(2) Uani 1 1 d . . .
H14A H 0.6391 1.1858 0.7115 0.169 Uiso 1 1 calc R . .
H14B H 0.7934 1.0740 0.7303 0.169 Uiso 1 1 calc R . .
H14C H 0.6230 1.0764 0.7882 0.169 Uiso 1 1 calc R . .
C15 C 0.1134(9) 0.6104(8) 0.6214(3) 0.0898(16) Uani 1 1 d . . .
H15A H 0.1401 0.6022 0.5639 0.108 Uiso 1 1 calc R . .
H15B H 0.1630 0.5135 0.6441 0.108 Uiso 1 1 calc R . .
C16 C -0.1015(10) 0.5534(10) 0.6251(4) 0.131(3) Uani 1 1 d . . .
H16A H -0.1310 0.5564 0.6815 0.196 Uiso 1 1 calc R . .
H16B H -0.1618 0.4206 0.5951 0.196 Uiso 1 1 calc R . .
H16C H -0.1541 0.6452 0.6011 0.196 Uiso 1 1 calc R . .
C17 C 0.2029(8) 1.0591(7) 0.6280(2) 0.0747(13) Uani 1 1 d . . .
H17A H 0.0594 1.0357 0.6246 0.090 Uiso 1 1 calc R . .
H17B H 0.2648 1.1855 0.6642 0.090 Uiso 1 1 calc R . .
C18 C 0.2703(10) 1.0795(10) 0.5445(3) 0.108(2) Uani 1 1 d . . .
H18A H 0.4138 1.1176 0.5478 0.163 Uiso 1 1 calc R . .
H18B H 0.2255 1.1800 0.5236 0.163 Uiso 1 1 calc R . .
H18C H 0.2152 0.9539 0.5083 0.163 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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
C12 Si1 C17 106.19(17) . .
C12 Si1 C13 108.94(18) . .
C17 Si1 C13 111.7(2) . .
C12 Si1 C15 108.5(2) . .
C17 Si1 C15 112.2(2) . .
C13 Si1 C15 109.2(3) . .
C2 C1 C10 120.8(3) . 2_577
C2 C1 C11 119.7(3) . .
C10 C1 C11 119.5(3) 2_577 .
C1 C2 C3 121.4(3) . .
C1 C2 C10 119.9(3) . .
C3 C2 C10 118.7(3) . .
C4 C3 C2 120.0(3) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C3 C4 C8 121.1(3) . .
C3 C4 S5 126.2(3) . .
C8 C4 S5 112.7(2) . .
C6 S5 C4 88.3(2) . .
C7 C6 F1 128.3(6) . .
C7 C6 S5 116.2(5) . .
F1 C6 S5 115.5(4) . .
C6 C7 C8 112.2(8) . .
C6 C7 H7 123.9 . .
C8 C7 H7 123.9 . .
C9 C8 C4 120.3(3) . .
C9 C8 C7 129.1(6) . .
C4 C8 C7 110.6(6) . .
C6' C5' H5' 123.9 . .
C5' C6' F1' 128.2(10) . .
C5' C6' S7' 115.7(7) . .
F1' C6' S7' 116.0(8) . .
C8 C9 C10 120.3(3) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C9 C10 C1 121.3(3) . 2_577
C9 C10 C2 119.4(3) . .
C1 C10 C2 119.3(3) 2_577 .
C12 C11 C1 178.3(3) . .
C11 C12 Si1 175.9(3) . .
C14 C13 Si1 115.2(3) . .
C14 C13 H13A 108.5 . .
Si1 C13 H13A 108.5 . .
C14 C13 H13B 108.5 . .
Si1 C13 H13B 108.5 . .
H13A C13 H13B 107.5 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 Si1 116.0(4) . .
C16 C15 H15A 108.3 . .
Si1 C15 H15A 108.3 . .
C16 C15 H15B 108.3 . .
Si1 C15 H15B 108.3 . .
H15A C15 H15B 107.4 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 Si1 116.4(3) . .
C18 C17 H17A 108.2 . .
Si1 C17 H17A 108.2 . .
C18 C17 H17B 108.2 . .
Si1 C17 H17B 108.2 . .
H17A C17 H17B 107.3 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C12 1.822(3) .
Si1 C17 1.842(4) .
Si1 C13 1.853(5) .
Si1 C15 1.860(5) .
C1 C2 1.395(4) .
C1 C10 1.406(4) 2_577
C1 C11 1.419(4) .
C2 C3 1.414(4) .
C2 C10 1.422(4) .
C3 C4 1.348(4) .
C3 H3 0.9400 .
C4 C8 1.414(4) .
C4 S5 1.739(3) .
S5 C6 1.733(6) .
C6 C7 1.318(14) .
C6 F1 1.347(5) .
C7 C8 1.421(10) .
C7 H7 0.9400 .
C8 C9 1.351(4) .
C5' C6' 1.317(16) .
C5' H5' 0.9400 .
F1' C6' 1.348(8) .
C6' S7' 1.734(10) .
C9 C10 1.405(4) .
C9 H9 0.9400 .
C10 C1 1.407(4) 2_577
C11 C12 1.187(4) .
C13 C14 1.496(7) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 H14C 0.9700 .
C15 C16 1.465(8) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 H16C 0.9700 .
C17 C18 1.503(6) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 H18C 0.9700 .
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 C3 -177.8(3) 2_577 .
C11 C1 C2 C3 3.8(4) . .
C10 C1 C2 C10 1.1(5) 2_577 .
C11 C1 C2 C10 -177.3(3) . .
C1 C2 C3 C4 -179.2(3) . .
C10 C2 C3 C4 1.9(4) . .
C2 C3 C4 C8 0.7(5) . .
C2 C3 C4 S5 -179.1(3) . .
C3 C4 S5 C6 -177.4(5) . .
C8 C4 S5 C6 2.8(5) . .
C4 S5 C6 C7 -3.2(14) . .
C4 S5 C6 F1 178.7(8) . .
F1 C6 C7 C8 -179.5(11) . .
S5 C6 C7 C8 3(2) . .
C3 C4 C8 C9 -2.0(4) . .
S5 C4 C8 C9 177.9(3) . .
C3 C4 C8 C7 178.2(10) . .
S5 C4 C8 C7 -2.0(11) . .
C6 C7 C8 C9 179.8(10) . .
C6 C7 C8 C4 0(2) . .
C4 C8 C9 C10 0.5(4) . .
C7 C8 C9 C10 -179.7(12) . .
C8 C9 C10 C1 -179.0(3) . 2_577
C8 C9 C10 C2 2.1(4) . .
C1 C2 C10 C9 177.7(3) . .
C3 C2 C10 C9 -3.3(4) . .
C1 C2 C10 C1 -1.1(4) . 2_577
C3 C2 C10 C1 177.8(3) . 2_577
C12 Si1 C13 C14 -54.5(4) . .
C17 Si1 C13 C14 62.5(4) . .
C15 Si1 C13 C14 -172.8(4) . .
C12 Si1 C15 C16 50.3(5) . .
C17 Si1 C15 C16 -66.7(5) . .
C13 Si1 C15 C16 168.9(4) . .
C12 Si1 C17 C18 174.3(4) . .
C13 Si1 C17 C18 55.7(5) . .
C15 Si1 C17 C18 -67.3(5) . .
