Crystal structures of 4-chloropyridine-2-carbonitrile and 6-chloropyridine-2-carbonitrile exhibit different intermolecular π-stacking, C—H···N~nitrile~ and C—H···N~pyridine~ interactions
Montgomery, Matthew J.; O'Connor, Thomas J.; Tanski, Joseph M.; Acta Crystallographica Section E 71 (2015) 852–856; doi:10.1107/S2056989015011767

data_2240876
_publ_section_title
;
 Crystal structures of 4-chloropyridine-2-carbonitrile and
 6-chloropyridine-2-carbonitrile exhibit different intermolecular
 \p-stacking, C---H&#x00B7;&#x00B7;&#x00B7;N~nitrile~ and
 C---H&#x00B7;&#x00B7;&#x00B7;N~pyridine~ interactions
;
_journal_coeditor_code           RZ5161
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              852
_journal_page_last               856
_journal_paper_doi               10.1107/S2056989015011767
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C6 H3 Cl N2'
_chemical_formula_moiety         'C6 H3 Cl N2'
_chemical_formula_sum            'C6 H3 Cl N2'
_chemical_formula_weight         138.55
_chemical_name_systematic
;
4-Chloropyridine-2-carbonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 96.806(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.813(5)
_cell_length_b                   14.047(19)
_cell_length_c                   11.356(15)
_cell_measurement_reflns_used    3637
_cell_measurement_temperature    125.(2)
_cell_measurement_theta_max      30.2826
_cell_measurement_theta_min      2.9003
_cell_volume                     604.0(14)
_computing_cell_refinement
;
APEX2 (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL2014 (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov <i>et al.</i>,
2009) and Mercury
(Macrae <i>et al.</i>,  2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      125.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \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  0.0625
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12191
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.370
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0646P)^2^+0.4268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1348
_reflns_number_gt                1498
_reflns_number_total             1852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rz5161sup1.cif
_cod_data_source_block           I
_cod_database_code               2240876
_cod_database_fobs_code          2240876
_shelx_hkl_checksum              180
_shelx_res_checksum              40192