#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512769.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_4512769
loop_
_publ_author_name
'Bosch, Eric'
'Bowling, Nathan P.'
'Darko, Jeffery'
_publ_section_title
;
 The Power of Nonconventional Phenyl C--H···N
 Hydrogen Bonds: Supportive Crystal-Packing Force and Dominant
 Supramolecular Engineering Force
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1634
_journal_paper_doi               10.1021/cg5014076
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C12 H2 F8, C10 H8 N2'
_chemical_formula_sum            'C22 H10 F8 N2'
_chemical_formula_weight         454.32
_chemical_name_systematic
;
Cocrystal between 4H,4'H-octafluorobiphenyl and 4,4'-bipyridine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 121.774(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8283(19)
_cell_length_b                   20.692(4)
_cell_length_c                   7.4577(10)
_cell_measurement_reflns_used    3284
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.90
_cell_volume                     1814.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'XSeed (Barbour, 2003)'
_computing_publication_material  'XSeed (Barbour, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and 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  0.0431
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11239
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.131
_diffrn_reflns_theta_min         1.968
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_description       cut
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0659P)²+1.2579P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1395
_reflns_number_total             1993
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5014076_si_004.cif
_cod_data_source_block           eb394n
_cod_depositor_comments
'Adding full bibliography for 4512766--4512773.cif.'
_cod_database_code               4512769
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1 F 0.17884(13) 0.29691(5) 0.2807(2) 0.0628(5) Uani 1 1 d . . .
N1 N 0.0000 0.79925(10) 0.2500 0.0558(8) Uani 1 2 d S T P
C1 C 0.0895(2) 0.76546(9) 0.2818(4) 0.0509(6) Uani 1 1 d . . .
H1 H 0.1543 0.7886 0.3043 0.061 Uiso 1 1 calc R U .
F2 F 0.17724(11) 0.16765(5) 0.27448(19) 0.0476(4) Uani 1 1 d . . .
N2 N 0.0000 0.45624(12) 0.2500 0.0669(10) Uani 1 2 d S T P
C2 C 0.0942(2) 0.69830(9) 0.2842(3) 0.0432(6) Uani 1 1 d . . .
H2 H 0.1606 0.6765 0.3089 0.052 Uiso 1 1 calc R U .
F3 F 0.17289(12) 0.08857(6) 0.5792(2) 0.0528(4) Uani 1 1 d . . .
C3 C 0.0000 0.66370(11) 0.2500 0.0394(7) Uani 1 2 d S T P
F4 F 0.17380(14) -0.04063(6) 0.5771(3) 0.0700(5) Uani 1 1 d . . .
C4 C 0.0000 0.59155(11) 0.2500 0.0425(8) Uani 1 2 d S T P
C5 C 0.0926(2) 0.55733(9) 0.4040(4) 0.0492(6) Uani 1 1 d . . .
H5 H 0.1579 0.5791 0.5122 0.059 Uiso 1 1 calc R U .
C6 C 0.0877(3) 0.48988(10) 0.3964(5) 0.0603(8) Uani 1 1 d . . .
H6 H 0.1515 0.4666 0.5031 0.072 Uiso 1 1 calc R U .
C7 C 0.0000 0.30002(12) 0.2500 0.0565(10) Uani 1 2 d S T P
H7 H 0.0000 0.3459 0.2500 0.068 Uiso 1 2 calc R U P
C8 C 0.0888(2) 0.26572(8) 0.2652(4) 0.0501(7) Uani 1 1 d . . .
C9 C 0.0891(2) 0.19895(8) 0.2637(3) 0.0424(6) Uani 1 1 d . . .
C10 C 0.0000 0.16421(11) 0.2500 0.0394(7) Uani 1 2 d S T P
C11 C 0.0000 0.09221(11) 0.2500 0.0415(8) Uani 1 2 d S T P
C12 C 0.0873(2) 0.05743(9) 0.4134(4) 0.0469(6) Uani 1 1 d . . .
C13 C 0.0870(2) -0.00955(9) 0.4119(4) 0.0550(7) Uani 1 1 d . . .
C14 C 0.0000 -0.04369(12) 0.2500 0.0593(11) Uani 1 2 d S T P
H14 H 0.0000 -0.0896 0.2500 0.071 Uiso 1 2 calc R U P
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'
N N 0.0061 0.0033 '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
C1 N1 C1 116.6(2) . 2
N1 C1 C2 124.0(2) . .
C6 N2 C6 116.6(3) . 2
C3 C2 C1 118.8(2) . .
C2 C3 C2 117.8(2) . 2
C2 C3 C4 121.08(12) . .
C2 C3 C4 121.08(12) 2 .
C5 C4 C5 118.4(3) . 2
C5 C4 C3 120.80(13) . .
C5 C4 C3 120.80(13) 2 .
C4 C5 C6 118.3(2) . .
N2 C6 C5 124.2(3) . .
C8 C7 C8 117.6(2) 2 .
F1 C8 C7 120.31(16) . .
F1 C8 C9 118.1(2) . .
C7 C8 C9 121.6(2) . .
F2 C9 C8 119.19(17) . .
F2 C9 C10 119.89(15) . .
C8 C9 C10 120.92(19) . .
C9 C10 C9 117.4(2) . 2
C9 C10 C11 121.31(11) . .
C9 C10 C11 121.31(11) 2 .
C12 C11 C12 117.2(2) . 2
C12 C11 C10 121.38(12) . .
C12 C11 C10 121.38(12) 2 .
F3 C12 C11 119.94(16) . .
F3 C12 C13 119.0(2) . .
C11 C12 C13 121.1(2) . .
F4 C13 C14 120.42(17) . .
F4 C13 C12 118.2(2) . .
C14 C13 C12 121.4(2) . .
C13 C14 C13 117.9(3) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C8 1.352(2) .
N1 C1 1.330(3) .
N1 C1 1.330(3) 2
C1 C2 1.391(3) .
F2 C9 1.344(2) .
N2 C6 1.324(3) .
N2 C6 1.324(3) 2
C2 C3 1.387(2) .
F3 C12 1.343(3) .
C3 C2 1.387(2) 2
C3 C4 1.493(3) .
F4 C13 1.347(3) .
C4 C5 1.383(3) .
C4 C5 1.383(3) 2
C5 C6 1.397(3) .
C7 C8 1.371(3) 2
C7 C8 1.371(3) .
C8 C9 1.382(3) .
C9 C10 1.383(2) .
C10 C9 1.383(2) 2
C10 C11 1.490(3) .
C11 C12 1.382(3) .
C11 C12 1.382(3) 2
C12 C13 1.386(3) .
C13 C14 1.369(3) .
C14 C13 1.369(3) 2
