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_2016754
_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 H7 N6 +, Cl -, 2H2 O'
_chemical_formula_moiety         'C16 H7 N6 +, Cl -, 2(H2 O)'
_chemical_formula_sum            'C16 H11 Cl N6 O2'
_chemical_formula_weight         354.76
_chemical_name_systematic
;
6,7-dicyanodipyrido[f,h]quinoxalin-1-ium chloride dihydrate
;
_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                 100.452(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9417(4)
_cell_length_b                   12.0846(4)
_cell_length_c                   9.6350(3)
_cell_measurement_reflns_used    3363
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.25
_cell_volume                     1596.37(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1\% \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  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10352
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0452P)^2^+1.1734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                2381
_reflns_number_total             3123
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3158.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016754
_cod_database_fobs_code          2016754