#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512771.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_4512771
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, C12 H8 N2'
_chemical_formula_sum            'C24 H10 F8 N2'
_chemical_formula_weight         478.34
_chemical_name_systematic
;
Cocrystal between 4H,4'H-octafluorobiphenyl and 1,2-bis(4'-pyridyl)ethyne
;
_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                 123.553(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.527(3)
_cell_length_b                   23.296(7)
_cell_length_c                   7.5729(18)
_cell_measurement_reflns_used    1941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.83
_cell_volume                     1988.8(9)
_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 0.999
_diffrn_measured_fraction_theta_max 1.000
_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  0.0530
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10839
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.163
_diffrn_reflns_theta_min         1.748
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       cut
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0582
_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)+(0.0914P)²+5.3594P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.1975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1568
_reflns_number_total             2219
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5014076_si_005.cif
_cod_data_source_block           eb396
_cod_depositor_comments
'Adding full bibliography for 4512766--4512773.cif.'
_cod_database_code               4512771
#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   0.943
_shelx_estimated_absorpt_t_max   0.993
_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 0.32511(17) 0.47533(8) -0.0923(3) 0.0253(5) Uani 1 1 d . . .
N1 N 0.5000 0.33342(16) 0.2500 0.0260(8) Uani 1 2 d S T P
C1 C 0.5000 0.47266(18) 0.2500 0.0224(9) Uani 1 2 d S T P
H1 H 0.5000 0.4319 0.2500 0.027 Uiso 1 2 calc R U P
F2 F 0.32447(16) 0.59031(7) -0.0936(3) 0.0236(4) Uani 1 1 d . . .
N2 N 0.5000 -0.08139(16) 0.2500 0.0259(9) Uani 1 2 d S T P
C2 C 0.4118(3) 0.50322(13) 0.0804(5) 0.0204(7) Uani 1 1 d . . .
F3 F 0.31459(15) 0.66096(7) 0.2134(3) 0.0232(5) Uani 1 1 d . . .
C3 C 0.4115(3) 0.56289(13) 0.0800(5) 0.0194(6) Uani 1 1 d . . .
F4 F 0.31551(16) 0.77598(7) 0.2147(3) 0.0233(5) Uani 1 1 d . . .
C4 C 0.5000 0.59355(16) 0.2500 0.0163(8) Uani 1 2 d S T P
C5 C 0.5000 0.65766(17) 0.2500 0.0169(8) Uani 1 2 d S T P
C6 C 0.4065(3) 0.68871(13) 0.2303(5) 0.0186(6) Uani 1 1 d . . .
C7 C 0.4074(3) 0.74815(13) 0.2312(5) 0.0184(6) Uani 1 1 d . . .
C8 C 0.5000 0.77894(17) 0.2500 0.0202(9) Uani 1 2 d S T P
H8 H 0.5000 0.8197 0.2500 0.024 Uiso 1 2 calc R U P
C9 C 0.4068(3) 0.30340(14) 0.2179(5) 0.0241(7) Uani 1 1 d . . .
H9 H 0.3397 0.3240 0.1932 0.029 Uiso 1 1 calc R U .
C10 C 0.4032(3) 0.24379(13) 0.2189(5) 0.0220(7) Uani 1 1 d . . .
H10 H 0.3360 0.2243 0.1988 0.026 Uiso 1 1 calc R U .
C11 C 0.5000 0.21326(18) 0.2500 0.0198(9) Uani 1 2 d S T P
C12 C 0.5000 0.15123(19) 0.2500 0.0216(9) Uani 1 2 d S T P
C13 C 0.5000 0.10060(19) 0.2500 0.0220(9) Uani 1 2 d S T P
C14 C 0.5000 0.03868(18) 0.2500 0.0204(9) Uani 1 2 d S T P
C15 C 0.4057(3) 0.00791(13) 0.0838(5) 0.0223(7) Uani 1 1 d . . .
H15 H 0.3399 0.0273 -0.0319 0.027 Uiso 1 1 calc R U .
C16 C 0.4101(3) -0.05137(14) 0.0912(5) 0.0250(7) Uani 1 1 d . . .
H16 H 0.3458 -0.0720 -0.0226 0.030 Uiso 1 1 calc R U .
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
C9 N1 C9 117.1(4) . 2_655
C2 C1 C2 117.5(4) . 2_655
C16 N2 C16 117.1(4) . 2_655
F1 C2 C1 119.9(3) . .
F1 C2 C3 118.7(3) . .
C1 C2 C3 121.4(3) . .
F2 C3 C4 120.4(3) . .
F2 C3 C2 118.5(3) . .
C4 C3 C2 121.1(3) . .
C3 C4 C3 117.5(4) . 2_655
C3 C4 C5 121.23(19) . .
C3 C4 C5 121.23(19) 2_655 .
C6 C5 C6 117.3(4) . 2_655
C6 C5 C4 121.32(18) . .
C6 C5 C4 121.33(18) 2_655 .
F3 C6 C7 119.1(3) . .
F3 C6 C5 119.9(3) . .
C7 C6 C5 120.9(3) . .
F4 C7 C8 119.9(3) . .
F4 C7 C6 118.4(3) . .
C8 C7 C6 121.7(3) . .
C7 C8 C7 117.4(4) 2_655 .
N1 C9 C10 123.6(3) . .
C9 C10 C11 118.6(3) . .
C10 C11 C10 118.5(4) 2_655 .
C10 C11 C12 120.7(2) 2_655 .
C10 C11 C12 120.7(2) . .
C13 C12 C11 180.0 . .
C12 C13 C14 180.0 . .
C15 C14 C15 118.2(4) 2_655 .
C15 C14 C13 120.9(2) 2_655 .
C15 C14 C13 120.9(2) . .
C16 C15 C14 118.6(3) . .
N2 C16 C15 123.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.347(3) .
N1 C9 1.341(4) .
N1 C9 1.341(4) 2_655
C1 C2 1.373(4) .
C1 C2 1.373(4) 2_655
F2 C3 1.346(3) .
N2 C16 1.341(4) .
N2 C16 1.341(4) 2_655
C2 C3 1.390(4) .
F3 C6 1.343(3) .
C3 C4 1.377(4) .
F4 C7 1.346(3) .
C4 C3 1.377(4) 2_655
C4 C5 1.494(5) .
C5 C6 1.391(4) .
C5 C6 1.391(4) 2_655
C6 C7 1.385(4) .
C7 C8 1.380(4) .
C8 C7 1.380(4) 2_655
C9 C10 1.390(4) .
C10 C11 1.391(4) .
C11 C10 1.391(4) 2_655
C11 C12 1.445(6) .
C12 C13 1.179(6) .
C13 C14 1.443(6) .
C14 C15 1.397(4) 2_655
C14 C15 1.397(4) .
C15 C16 1.382(4) .
