#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:09:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180378 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/47/7204769.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_7204769
loop_
_publ_author_name
'Smith, Caroline E.'
'Smith, Philip S.'
'Thomas, Rhodri Ll.'
'Robins, Edward G.'
'Collings, Jonathan C.'
'Dai, Chaoyang'
'Scott, Andrew J.'
'Borwick, Simon'
'Batsanov, Andrei S.'
'Watt, Stephen W.'
'Clark, Stewart J.'
'Viney, Christopher'
'Howard, Judith A. K.'
'Clegg, William'
'Marder, Todd B.'
_publ_section_title
;
 Arene-perfluoroarene interactions in crystal engineering: structural
 preferences in polyfluorinated tolansArene?perfluoroarene interactions
 in crystal engineering. Part 9. Presented in part at the 16th
 International Symposium on Fluorine Chemistry, University of Durham,
 2000. Abstract 1P-102. For part 8 see ref. 1.Electronic supplementary
 information (ESI) available: spectroscopic characterisation for 4b?k;
 plots of energy as a function of inter-ring torsion angle in
 1,2,3,4,5-pentafluorotolan and as a function of C(Ph)?C(Ph)?O?C(Me)
 torsion angle in PhOMe. See
 http://www.rsc.org/suppdata/jm/b3/b314094f/
;
_journal_issue                   3
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              413
_journal_paper_doi               10.1039/b314094f
_journal_volume                  14
_journal_year                    2004
_chemical_formula_moiety         'C14 H10,C14 F10'
_chemical_formula_sum            'C28 H10 F10'
_chemical_formula_weight         536.36
_chemical_name_systematic
;
Tolan Perfluorotolan 1:1 molecular complex
;
_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
_cell_angle_alpha                85.554(6)
_cell_angle_beta                 86.479(6)
_cell_angle_gamma                84.095(6)
_cell_formula_units_Z            1
_cell_length_a                   6.0939(13)
_cell_length_b                   7.5286(15)
_cell_length_c                   12.491(3)
_cell_measurement_reflns_used    2140
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.72
_cell_volume                     567.5(2)
_computing_cell_refinement       'local programs'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS-96 (Sheldrick, 1990)'
_diffrn_ambient_temperature      160(2)
_diffrn_measurement_device       'Siemens SMART CCD area detector'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3470
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.947
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_restrained_S_obs      1.128
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1017P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1782
_refine_ls_wR_factor_ref         0.1640
_reflns_number_gt                1486
_reflns_number_total             2403
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b314094f.txt
_cod_data_source_block           1:2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204769
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0497(18) 0.0335(14) 0.0394(15) -0.0018(12) -0.0031(13) -0.0135(12)
C2 0.0371(16) 0.0335(14) 0.0471(17) -0.0064(12) 0.0088(13) -0.0061(11)
C3 0.0275(14) 0.0279(13) 0.0504(17) -0.0007(11) 0.0015(12) -0.0031(10)
C4 0.0287(14) 0.0248(12) 0.0402(15) -0.0001(10) 0.0031(11) -0.0062(10)
C5 0.0301(14) 0.0307(13) 0.0436(15) -0.0020(11) 0.0070(12) -0.0022(10)
C6 0.0313(15) 0.0376(14) 0.0494(17) -0.0003(12) -0.0065(13) -0.0068(11)
C7 0.0295(14) 0.0284(12) 0.0443(14) -0.0012(11) 0.0027(12) -0.0047(10)
C8 0.0361(15) 0.0319(13) 0.0287(13) -0.0001(10) -0.0034(11) -0.0142(11)
F1 0.0536(11) 0.0515(10) 0.0336(9) -0.0039(7) -0.0076(7) -0.0146(8)
C9 0.0307(14) 0.0259(12) 0.0314(13) -0.0049(10) 0.0080(11) -0.0072(10)
F2 0.0418(10) 0.0406(9) 0.0414(9) -0.0117(7) 0.0107(7) -0.0018(7)
C10 0.0211(13) 0.0240(12) 0.0383(14) -0.0003(10) -0.0023(11) -0.0047(9)
F3 0.0213(8) 0.0401(8) 0.0468(9) -0.0025(7) -0.0027(6) 0.0020(6)
C11 0.0238(13) 0.0228(11) 0.0337(13) -0.0018(10) -0.0011(10) -0.0070(9)
C12 0.0231(13) 0.0262(12) 0.0365(14) -0.0034(10) 0.0042(11) -0.0049(9)
F4 0.0245(8) 0.0424(9) 0.0477(9) -0.0093(7) 0.0032(7) 0.0041(6)
C13 0.0249(13) 0.0282(12) 0.0397(14) 0.0026(10) -0.0077(11) -0.0078(10)
F5 0.0264(9) 0.0497(9) 0.0527(10) 0.0039(7) -0.0144(7) -0.0047(7)
C14 0.0216(12) 0.0254(11) 0.0372(13) -0.0020(10) 0.0005(11) -0.0031(9)
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
C1 C 0.3279(5) 0.9286(3) 0.1353(2) 0.0402(7) Uani 1 d . .
H1 H 0.2960 0.9177 0.0627 0.048 Uiso 1 calc R .
C2 C 0.5366(5) 0.8708(3) 0.1707(2) 0.0393(7) Uani 1 d . .
H2 H 0.6472 0.8193 0.1224 0.047 Uiso 1 calc R .
C3 C 0.5840(4) 0.8875(3) 0.2755(2) 0.0355(6) Uani 1 d . .
H3 H 0.7267 0.8461 0.2993 0.043 Uiso 1 calc R .
C4 C 0.4238(4) 0.9649(3) 0.3473(2) 0.0313(6) Uani 1 d . .
C5 C 0.2134(4) 1.0201(3) 0.3110(2) 0.0353(6) Uani 1 d . .
H5 H 0.1014 1.0704 0.3591 0.042 Uiso 1 calc R .
C6 C 0.1673(5) 1.0020(4) 0.2060(2) 0.0392(6) Uani 1 d . .
H6 H 0.0239 1.0403 0.1821 0.047 Uiso 1 calc R .
C7 C 0.4765(4) 0.9885(3) 0.4557(2) 0.0342(6) Uani 1 d . .
C8 C 0.6660(4) 0.5801(3) 0.86430(19) 0.0315(6) Uani 1 d . .
F1 F 0.7093(3) 0.6015(2) 0.96579(11) 0.0454(5) Uani 1 d . .
C9 C 0.4622(4) 0.6444(3) 0.82617(19) 0.0293(6) Uani 1 d . .
F2 F 0.3088(3) 0.72689(19) 0.89172(12) 0.0415(4) Uani 1 d . .
C10 C 0.4189(4) 0.6235(3) 0.72202(19) 0.0277(6) Uani 1 d . .
F3 F 0.2210(2) 0.68838(18) 0.68623(11) 0.0364(4) Uani 1 d . .
C11 C 0.5742(4) 0.5375(3) 0.65203(19) 0.0265(5) Uani 1 d . .
C12 C 0.7783(4) 0.4753(3) 0.69252(19) 0.0286(6) Uani 1 d . .
F4 F 0.9336(2) 0.39162(19) 0.62882(12) 0.0386(4) Uani 1 d . .
C13 C 0.8231(4) 0.4948(3) 0.7974(2) 0.0306(6) Uani 1 d . .
F5 F 1.0196(2) 0.4297(2) 0.83496(12) 0.0428(4) Uani 1 d . .
C14 C 0.5232(4) 0.5116(3) 0.54435(19) 0.0281(5) Uani 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'
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
_geom_angle_publ_flag
C6 C1 C2 119.6(3) . . ?
C3 C2 C1 120.4(3) . . ?
C2 C3 C4 120.5(2) . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 C7 120.3(2) . . ?
C5 C4 C7 121.1(2) . . ?
C6 C5 C4 120.5(2) . . ?
C5 C6 C1 120.4(3) . . ?
C7 C7 C4 178.2(4) 2_676 . ?
F1 C8 C13 120.2(2) . . ?
F1 C8 C9 120.0(2) . . ?
C13 C8 C9 119.8(2) . . ?
F2 C9 C10 120.5(2) . . ?
F2 C9 C8 119.7(2) . . ?
C10 C9 C8 119.9(2) . . ?
F3 C10 C9 119.0(2) . . ?
F3 C10 C11 119.1(2) . . ?
C9 C10 C11 121.9(2) . . ?
C10 C11 C12 116.9(2) . . ?
C10 C11 C14 121.1(2) . . ?
C12 C11 C14 122.0(2) . . ?
F4 C12 C13 118.9(2) . . ?
F4 C12 C11 119.4(2) . . ?
C13 C12 C11 121.6(2) . . ?
F5 C13 C8 119.8(2) . . ?
F5 C13 C12 120.3(2) . . ?
C8 C13 C12 119.9(2) . . ?
C14 C14 C11 178.6(3) 2_666 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.379(4) . ?
C1 C2 1.389(4) . ?
C2 C3 1.376(4) . ?
C3 C4 1.397(4) . ?
C4 C5 1.398(3) . ?
C4 C7 1.439(4) . ?
C5 C6 1.379(4) . ?
C7 C7 1.189(5) 2_676 ?
C8 F1 1.336(3) . ?
C8 C13 1.374(4) . ?
C8 C9 1.384(4) . ?
C9 F2 1.340(3) . ?
C9 C10 1.367(3) . ?
C10 F3 1.343(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.394(3) . ?
C11 C14 1.431(3) . ?
C12 F4 1.337(3) . ?
C12 C13 1.377(3) . ?
C13 F5 1.344(3) . ?
C14 C14 1.190(5) 2_666 ?
