Multiple N—H···NC, C—H···NC and nitrile···π interactions in 4,4'-bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2-ethoxypropenide): structure determination and DFT calculations of anion···π cation interaction energies
Setifi, Fatima; Geiger, David K.; Abdul Razak, Ibrahim; Setifi, Zouaoui; Acta Crystallographica Section C 71 (2015) –; doi:10.1107/S2053229615012437

data_2020025
_publ_section_title
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 Multiple N---H&#x00B7;&#x00B7;&#x00B7;NC, C---H&#x00B7;&#x00B7;&#x00B7;NC
 and nitrile&#x00B7;&#x00B7;&#x00B7;\p interactions in
 4,4'-bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2-ethoxypropenide):
 structure determination and DFT calculations of
 anion&#x00B7;&#x00B7;&#x00B7;\p cation interaction energies
;
_journal_coeditor_code           LY3016
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615012437
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C10 H10 N2 2+, 2C9 H5 N4 O -'
_chemical_formula_moiety         'C10 H10 N2 2+, 2(C9 H5 N4 O -)'
_chemical_formula_sum            'C28 H20 N10 O2'
_chemical_formula_weight         528.54
_chemical_name_systematic
;
4,4'-Bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2-ethoxypropenide)
;
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 117.882(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.847(3)
_cell_length_b                   7.3242(5)
_cell_length_c                   22.995(2)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    294.(2)
_cell_measurement_theta_max      24.52
_cell_measurement_theta_min      2.57
_cell_volume                     5336.5(8)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae <i>et al.</i>, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      294.(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            43525
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5675
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+2.1115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1183
_reflns_number_gt                4345
_reflns_number_total             5675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ly3016sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        5336.5(7)
_cod_database_code               2020025
_shelx_hkl_checksum              1878
_shelx_res_checksum              60931
_cod_database_fobs_code 2020025