#------------------------------------------------------------------------------
#$Date: 2014-07-12 05:06:18 +0100 (Sat, 12 Jul 2014) $
#$Revision: 120112 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/12/7051205.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_7051205
loop_
_publ_author_name
'Collings, Jonathan C.'
'Roscoe, Karl P.'
'Thomas, Rhodri Ll.'
'Batsanov, Andrei S.'
'Stimson, Lorna M.'
'Howard, Judith A. K.'
'Marder, Todd B.'
_publ_section_title
;
 Arene-perfluoroarene interactions in crystal engineering. Part 3.
 Single-crystal structures of 1 : 1 complexes of octafluoronaphthalene
 with fused-ring polyaromatic hydrocarbonsFor part 1, see ref. 1. For
 part 2, see ref. 2. Presented at the 16th International Symposium on
 Fluorine Chemistry, University of Durham, UK, 16\^a€“21
 July 2000, Abstract no. 308.Electronic supplementary information (ESI)
 available: experimental data for the re-determination of the crystal
 structure of triphenylene, tables of the average bond lengths in OFN
 and the polyaromatic molecules in both the complexes and pure
 compounds, and a table of distances and angles for intermolecular
 H\^A·\^A·\^A·F contacts in the complexes which
 are below the sum of the van der Waals radii. See
 http://www.rsc.org/suppdata/nj/b1/b105502j/
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1410
_journal_volume                  25
_journal_year                    2001
_chemical_formula_moiety         'C10 F8,C16 H10'
_chemical_formula_sum            'C26 H10 F8'
_chemical_formula_weight         474.34
_chemical_melting_point          522.1(10)
_chemical_name_systematic
; 
perfluoronaphthalene pyrene complex (1:1)  
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.51(1)
_cell_angle_beta                 105.23(1)
_cell_angle_gamma                106.82(1)
_cell_formula_units_Z            1
_cell_length_a                   6.725(1)
_cell_length_b                   8.864(1)
_cell_length_c                   9.488(1)
_cell_measurement_reflns_used    331
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      10.3
_cell_volume                     476.90(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SMART 1K CCD area detector'
_diffrn_measurement_method       '\w 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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2866
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        0.2
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0442
_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/[\s^2^(Fo^2^)+(0.0591P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                1106
_reflns_number_total             1661
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    b105502j.txt
_[local]_cod_data_source_block   3
_[local]_cod_cif_authors_sg_H-M  P-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '248--250\% C' was changed to
'522.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        476.9(1)
_cod_database_code               7051205
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
F1 F 0.3891(2) 0.14979(16) 0.51281(15) 0.0321(4) Uani 1 1 d . . .
F2 F 0.2314(2) 0.02898(16) 0.19297(16) 0.0395(4) Uani 1 1 d . . .
F3 F 0.2519(2) 0.24496(17) 0.04342(14) 0.0362(4) Uani 1 1 d . . .
F4 F 0.4302(2) 0.58963(17) 0.21227(15) 0.0316(4) Uani 1 1 d . . .
C1 C 0.4016(3) 0.2628(3) 0.4434(3) 0.0231(5) Uani 1 1 d . . .
C2 C 0.3216(4) 0.2002(3) 0.2822(3) 0.0270(6) Uani 1 1 d . . .
C3 C 0.3320(4) 0.3123(3) 0.2038(3) 0.0257(5) Uani 1 1 d . . .
C4 C 0.4211(3) 0.4856(3) 0.2916(3) 0.0222(5) Uani 1 1 d . . .
C5 C 0.5057(3) 0.5579(3) 0.4602(3) 0.0198(5) Uani 1 1 d . . .
C6 C 0.7820(4) 0.3044(3) 0.0795(3) 0.0286(6) Uani 1 1 d . . .
H6 H 0.721(4) 0.249(3) -0.031(3) 0.032(7) Uiso 1 1 d . . .
C7 C 0.7809(4) 0.2024(3) 0.1654(3) 0.0267(6) Uani 1 1 d . . .
H7 H 0.719(4) 0.081(3) 0.113(3) 0.033(7) Uiso 1 1 d . . .
C8 C 0.8657(3) 0.2765(3) 0.3327(3) 0.0219(5) Uani 1 1 d . . .
C9 C 0.9554(3) 0.4598(3) 0.4147(3) 0.0200(5) Uani 1 1 d . . .
C10 C 0.9572(3) 0.5639(3) 0.3245(3) 0.0219(5) Uani 1 1 d . . .
C11 C 0.8684(4) 0.4828(3) 0.1574(3) 0.0262(6) Uani 1 1 d . . .
H11 H 0.869(4) 0.552(3) 0.095(3) 0.027(6) Uiso 1 1 d . . .
C12 C 0.8677(4) 0.1760(3) 0.4274(3) 0.0257(5) Uani 1 1 d . . .
H12 H 0.807(4) 0.055(3) 0.373(3) 0.034(7) Uiso 1 1 d . . .
C13 C 0.9503(4) 0.2510(3) 0.5885(3) 0.0254(6) Uani 1 1 d . . .
H13 H 0.950(4) 0.188(3) 0.649(3) 0.040(7) Uiso 1 1 d . . .
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
F1 0.0375(8) 0.0259(7) 0.0435(9) 0.0229(6) 0.0198(7) 0.0141(6)
F2 0.0425(9) 0.0238(8) 0.0399(9) 0.0036(6) 0.0144(7) 0.0078(7)
F3 0.0339(8) 0.0463(9) 0.0215(8) 0.0083(6) 0.0072(6) 0.0155(7)
F4 0.0340(8) 0.0413(8) 0.0322(8) 0.0257(6) 0.0154(6) 0.0188(7)
C1 0.0158(12) 0.0271(13) 0.0330(14) 0.0176(11) 0.0123(10) 0.0093(10)
C2 0.0217(13) 0.0226(12) 0.0334(14) 0.0071(11) 0.0121(11) 0.0076(10)
C3 0.0185(12) 0.0358(14) 0.0203(13) 0.0079(11) 0.0079(10) 0.0106(11)
C4 0.0180(12) 0.0326(13) 0.0255(13) 0.0196(11) 0.0102(10) 0.0130(11)
C5 0.0132(11) 0.0263(13) 0.0260(13) 0.0140(10) 0.0094(10) 0.0110(10)
C6 0.0268(13) 0.0375(14) 0.0232(14) 0.0113(12) 0.0103(11) 0.0159(11)
C7 0.0215(13) 0.0302(14) 0.0282(14) 0.0097(11) 0.0103(10) 0.0114(11)
C8 0.0153(12) 0.0256(13) 0.0288(13) 0.0130(10) 0.0106(10) 0.0098(10)
C9 0.0129(11) 0.0265(12) 0.0251(12) 0.0132(10) 0.0099(9) 0.0088(9)
C10 0.0157(11) 0.0309(13) 0.0270(13) 0.0163(10) 0.0111(10) 0.0126(10)
C11 0.0253(13) 0.0401(14) 0.0277(14) 0.0221(12) 0.0158(11) 0.0187(11)
C12 0.0236(13) 0.0231(13) 0.0341(15) 0.0131(11) 0.0145(11) 0.0099(11)
C13 0.0238(13) 0.0311(14) 0.0346(15) 0.0227(12) 0.0155(11) 0.0153(11)
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
F1 C1 C2 118.5(2) . . ?
F1 C1 C5 119.80(19) . 2_666 ?
C2 C1 C5 121.7(2) . 2_666 ?
F2 C2 C1 120.6(2) . . ?
F2 C2 C3 118.6(2) . . ?
C1 C2 C3 120.8(2) . . ?
F3 C3 C4 121.5(2) . . ?
F3 C3 C2 118.9(2) . . ?
C4 C3 C2 119.5(2) . . ?
F4 C4 C3 117.92(19) . . ?
F4 C4 C5 119.98(19) . . ?
C3 C4 C5 122.1(2) . . ?
C4 C5 C1 124.14(19) . 2_666 ?
C4 C5 C5 118.1(2) . 2_666 ?
C1 C5 C5 117.8(2) 2_666 2_666 ?
C11 C6 C7 120.8(2) . . ?
C11 C6 H6 121.5(14) . . ?
C7 C6 H6 117.7(14) . . ?
C6 C7 C8 121.0(2) . . ?
C6 C7 H7 121.0(14) . . ?
C8 C7 H7 118.0(14) . . ?
C7 C8 C9 118.9(2) . . ?
C7 C8 C12 123.1(2) . . ?
C9 C8 C12 118.0(2) . . ?
C9 C9 C8 120.6(2) 2_766 . ?
C9 C9 C10 119.8(3) 2_766 . ?
C8 C9 C10 119.5(2) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 C13 122.9(2) . 2_766 ?
C9 C10 C13 118.0(2) . 2_766 ?
C6 C11 C10 120.7(2) . . ?
C6 C11 H11 119.5(13) . . ?
C10 C11 H11 119.8(14) . . ?
C13 C12 C8 121.8(2) . . ?
C13 C12 H12 120.7(14) . . ?
C8 C12 H12 117.6(14) . . ?
C12 C13 C10 121.7(2) . 2_766 ?
C12 C13 H13 122.2(16) . . ?
C10 C13 H13 116.0(16) 2_766 . ?
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
F1 C1 1.350(2) . ?
F2 C2 1.346(3) . ?
F3 C3 1.342(2) . ?
F4 C4 1.353(2) . ?
C1 C2 1.350(3) . ?
C1 C5 1.415(3) 2_666 ?
C2 C3 1.405(3) . ?
C3 C4 1.359(3) . ?
C4 C5 1.410(3) . ?
C5 C1 1.415(3) 2_666 ?
C5 C5 1.442(4) 2_666 ?
C6 C11 1.387(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.93(2) . ?
C7 C8 1.399(3) . ?
C7 H7 0.94(2) . ?
C8 C9 1.427(3) . ?
C8 C12 1.443(3) . ?
C9 C9 1.426(4) 2_766 ?
C9 C10 1.435(3) . ?
C10 C11 1.398(3) . ?
C10 C13 1.445(3) 2_766 ?
C11 H11 0.97(2) . ?
C12 C13 1.347(3) . ?
C12 H12 0.94(2) . ?
C13 C10 1.445(3) 2_766 ?
C13 H13 0.92(2) . ?
_journal_paper_doi 10.1039/b105502j