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_4512768
_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_sum            'C13 H5 F4 N'
_chemical_formula_weight         251.18
_chemical_name_systematic
;
3-[(2,3,4,5-tetrafluorophenyl)ethynyl]pyridine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                63.113(3)
_cell_angle_beta                 74.909(3)
_cell_angle_gamma                77.066(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9023(11)
_cell_length_b                   9.8718(19)
_cell_length_c                   10.399(2)
_cell_measurement_reflns_used    2153
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      3.49
_cell_volume                     517.80(17)
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0158
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6464
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.217
_diffrn_reflns_theta_min         2.234
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       irregular
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0528P)^2^+0.2005P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2026
_reflns_number_total             2316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5014076_si_003.cif
_cod_data_source_block           eb357
_cod_depositor_comments
'Adding full bibliography for 4512766--4512773.cif.'
_cod_original_cell_volume        517.78(17)
_cod_database_code               4512768
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.971
_shelxl_version_number           2013-2
_shelx_res_checksum              68174
_shelx_hkl_checksum              25624