#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/05/4110563.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_4110563
loop_
_publ_author_name
'Myung-Han Yoon'
'Antonio Facchetti'
'Charlotte E. Stern'
'Tobin J. Marks'
_publ_section_title
;
 Fluorocarbon-Modified Organic Semiconductors: Molecular Architecture,
 Electronic, and Crystal Structure Tuning of Arene- versus
 Fluoroarene-Thiophene Oligomer Thin-Film Properties
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5792
_journal_page_last               5801
_journal_paper_doi               10.1021/ja060016a
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C16 H2 F10 S'
_chemical_formula_weight         416.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.2771(16)
_cell_length_b                   12.8839(15)
_cell_length_c                   29.459(5)
_cell_measurement_temperature    153(2)
_cell_volume                     2762.0(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            23871
_diffrn_reflns_theta_full        28.88
_diffrn_reflns_theta_max         28.88
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.8769
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0388
_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)+(0.0563P)²+0.7125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                2454
_reflns_number_total             3481
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja060016asi20060102_112208.cif
_cod_data_source_block           s56n
_cod_database_code               4110563
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
S1 S 0.14097(6) 0.90042(3) 0.179977(16) 0.02567(13) Uani 1 1 d .
F1 F 0.21367(17) 0.98729(9) 0.26170(4) 0.0352(3) Uani 1 1 d .
F2 F 0.22210(17) 1.01242(9) 0.35099(4) 0.0378(3) Uani 1 1 d .
F3 F 0.12330(17) 0.85555(10) 0.40777(4) 0.0392(3) Uani 1 1 d .
F4 F 0.00583(17) 0.67143(9) 0.37181(4) 0.0414(3) Uani 1 1 d .
F5 F -0.01096(17) 0.64484(8) 0.28293(4) 0.0373(3) Uani 1 1 d .
F6 F -0.07458(16) 0.72810(9) 0.05730(4) 0.0362(3) Uani 1 1 d .
F7 F -0.02651(18) 0.78885(10) -0.02782(4) 0.0433(3) Uani 1 1 d .
F8 F 0.19233(17) 0.95436(10) -0.04784(4) 0.0422(3) Uani 1 1 d .
F9 F 0.35749(17) 1.06076(9) 0.02102(4) 0.0411(3) Uani 1 1 d .
F10 F 0.31602(15) 1.00011(9) 0.10690(4) 0.0352(3) Uani 1 1 d .
C1 C 0.1587(2) 0.90698(14) 0.28774(7) 0.0272(4) Uani 1 1 d .
C2 C 0.1660(3) 0.92141(15) 0.33390(7) 0.0293(4) Uani 1 1 d .
C3 C 0.1155(3) 0.84218(16) 0.36260(6) 0.0302(4) Uani 1 1 d .
C4 C 0.0564(3) 0.74957(15) 0.34438(7) 0.0304(4) Uani 1 1 d .
C5 C 0.0494(3) 0.73702(14) 0.29788(7) 0.0283(4) Uani 1 1 d .
C6 C 0.1004(2) 0.81503(14) 0.26717(6) 0.0252(4) Uani 1 1 d .
C7 C 0.0945(2) 0.80023(14) 0.21773(6) 0.0258(4) Uani 1 1 d .
C8 C 0.0536(3) 0.71084(15) 0.19404(7) 0.0326(4) Uani 1 1 d .
H8 H 0.0248 0.6469 0.2084 0.039 Uiso 1 1 calc R
C9 C 0.0585(3) 0.72299(15) 0.14677(7) 0.0329(4) Uani 1 1 d .
H9 H 0.0324 0.6683 0.1261 0.039 Uiso 1 1 calc R
C10 C 0.1047(2) 0.82165(14) 0.13319(6) 0.0258(4) Uani 1 1 d .
C11 C 0.1235(2) 0.85920(14) 0.08634(6) 0.0257(4) Uani 1 1 d .
C12 C 0.0379(3) 0.80944(14) 0.04983(7) 0.0298(4) Uani 1 1 d .
C13 C 0.0608(3) 0.83968(16) 0.00550(7) 0.0325(4) Uani 1 1 d .
C14 C 0.1709(3) 0.92367(16) -0.00468(7) 0.0333(5) Uani 1 1 d .
C15 C 0.2549(3) 0.97704(15) 0.03015(7) 0.0314(4) Uani 1 1 d .
C16 C 0.2300(3) 0.94522(14) 0.07424(6) 0.0285(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C10 S1 C7 92.55(9)
F1 C1 C2 116.60(16)
F1 C1 C6 119.61(17)
C2 C1 C6 123.78(17)
F2 C2 C1 120.14(17)
F2 C2 C3 120.00(18)
C1 C2 C3 119.85(18)
F3 C3 C2 120.17(19)
F3 C3 C4 120.70(18)
C2 C3 C4 119.14(18)
F4 C4 C3 120.05(17)
F4 C4 C5 119.96(18)
C3 C4 C5 119.98(18)
F5 C5 C4 116.22(17)
F5 C5 C6 120.64(17)
C4 C5 C6 123.14(18)
C1 C6 C5 114.10(17)
C1 C6 C7 123.29(17)
C5 C6 C7 122.60(17)
C8 C7 C6 128.04(18)
C8 C7 S1 109.79(15)
C6 C7 S1 122.17(14)
C7 C8 C9 113.83(18)
C7 C8 H8 123.1
C9 C8 H8 123.1
C10 C9 C8 113.50(17)
C10 C9 H9 123.3
C8 C9 H9 123.3
C9 C10 C11 126.94(17)
C9 C10 S1 110.34(14)
C11 C10 S1 122.73(14)
C12 C11 C16 114.45(17)
C12 C11 C10 122.02(17)
C16 C11 C10 123.52(17)
F6 C12 C13 116.72(17)
F6 C12 C11 120.08(17)
C13 C12 C11 123.19(18)
F7 C13 C12 120.02(19)
F7 C13 C14 119.96(19)
C12 C13 C14 120.01(18)
F8 C14 C15 120.48(19)
F8 C14 C13 120.36(19)
C15 C14 C13 119.15(18)
F9 C15 C16 120.23(18)
F9 C15 C14 119.99(18)
C16 C15 C14 119.77(18)
F10 C16 C15 117.19(17)
F10 C16 C11 119.41(16)
C15 C16 C11 123.40(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.7319(19)
S1 C7 1.7372(19)
F1 C1 1.349(2)
F2 C2 1.340(2)
F3 C3 1.343(2)
F4 C4 1.342(2)
F5 C5 1.341(2)
F6 C12 1.348(2)
F7 C13 1.340(2)
F8 C14 1.340(2)
F9 C15 1.339(2)
F10 C16 1.348(2)
C1 C2 1.374(3)
C1 C6 1.397(3)
C2 C3 1.375(3)
C3 C4 1.377(3)
C4 C5 1.380(3)
C5 C6 1.402(3)
C6 C7 1.469(3)
C7 C8 1.379(3)
C8 C9 1.402(3)
C8 H8 0.9500
C9 C10 1.374(3)
C9 H9 0.9500
C10 C11 1.469(3)
C11 C12 1.399(3)
C11 C16 1.399(3)
C12 C13 1.373(3)
C13 C14 1.379(3)
C14 C15 1.378(3)
C15 C16 1.374(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28558791
