Hydrogen-bonding <i>versus</i> π–π stacking interactions in dipyrido[<i>f</i>,<i>h</i>]quinoxaline-6,7-dicarbonitrile and 6,7-dicyanodipyrido[<i>f</i>,<i>h</i>]quinoxalin-1-ium chloride dihydrate
Kozlov, Leonid; Goldberg, Israel; Acta Crystallographica Section C 64 (2008) o498–o501; doi:10.1107/S0108270108025377

data_2016753
_publ_section_title
;
 Hydrogen-bonding <i>versus</i> \p--\p stacking interactions in
 dipyrido[<i>f</i>,<i>h</i>]quinoxaline-6,7-dicarbonitrile and
 6,7-dicyanodipyrido[<i>f</i>,<i>h</i>]quinoxalin-1-ium chloride
 dihydrate
;
_journal_coeditor_code           FA3158
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o498
_journal_page_last               o501
_journal_paper_doi               10.1107/S0108270108025377
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C16 H6 N6'
_chemical_formula_moiety         'C16 H6 N6'
_chemical_formula_sum            'C16 H6 N6'
_chemical_formula_weight         282.27
_chemical_name_systematic
;
dipyrido[f,h]quinoxaline-6,7-dicarbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.224(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.0150(14)
_cell_length_b                   6.9620(6)
_cell_length_c                   24.5189(16)
_cell_measurement_reflns_used    4063
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.41
_cell_volume                     2484.5(4)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae <i>et al.</i>,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare <i>et al.</i>,  1999)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '0.5\% \f and \w'
_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  0.0840
_diffrn_reflns_av_sigmaI/netI    0.0794
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13248
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0808
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+2.1196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1686
_reflns_number_gt                2660
_reflns_number_total             4340
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3158.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016753
_cod_database_fobs_code          2016753