The Power of Nonconventional Phenyl C–H···N Hydrogen Bonds: Supportive Crystal-Packing Force and Dominant Supramolecular Engineering Force
Bosch, Eric; Bowling, Nathan P.; Darko, Jeffery; Crystal Growth & Design 15 (2015) 1634–; doi:10.1021/cg5014076

data_4512771
_publ_section_title
;
 The Power of Nonconventional Phenyl C--H&#x00B7;&#x00B7;&#x00B7;N
 Hydrogen Bonds: Supportive Crystal-Packing Force and Dominant
 Supramolecular Engineering Force
;
_journal_issue                   4
_journal_name_full               'Crystal Growth &amp; 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'
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_computing_molecular_graphics    'XSeed (Barbour, 2003)'
_computing_publication_material  'XSeed (Barbour, 2003)'
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_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/[\s^2^(Fo^2^)+(0.0914P)^2^+5.3594P]
 where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-2
_shelx_res_checksum              65493
_shelx_hkl_checksum              33957