Crystal structures of 2,2'-bipyridin-1-ium 1,1,3,3-tetracyano-2-ethoxyprop-2-en-1-ide and bis(2,2'-bipyridin-1-ium) 1,1,3,3-tetracyano-2-(dicyanomethylene)propane-1,3-diide
Setifi, Zouaoui; Valkonen, Arto; Fernandes, Manuel A.; Nummelin, Sami; Boughzala, Habib; Setifi, Fatima; Glidewell, Christopher; Acta Crystallographica Section E 71 (2015) 509–515; doi:10.1107/S2056989015007306

data_2240668
_publ_section_title
;
 Crystal structures of 2,2'-bipyridin-1-ium
 1,1,3,3-tetracyano-2-ethoxyprop-2-en-1-ide and bis(2,2'-bipyridin-1-ium)
 1,1,3,3-tetracyano-2-(dicyanomethylene)propane-1,3-diide
;
_journal_coeditor_code           HB7404
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              509
_journal_page_last               515
_journal_paper_doi               10.1107/S2056989015007306
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '2C10 H9 N2 +, C10 N6 2-'
_chemical_formula_moiety         '2(C10 H9 N2 +), C10 N6 2-'
_chemical_formula_sum            'C30 H18 N10'
_chemical_formula_weight         518.54
_chemical_name_systematic
;
Bis(2,2'-bipyridin-1-ium)
1,1,3,3-tetracyano-2-(dicyanomethylene)propane-1,3-diide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 116.721(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4195(8)
_cell_length_b                   16.1801(8)
_cell_length_c                   12.9058(9)
_cell_measurement_reflns_used    5568
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.294
_cell_measurement_theta_min      1.699
_cell_volume                     2503.0(3)
_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)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f  & \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  0.0855
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14513
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.398
_diffrn_reflns_theta_min         1.699
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0713P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1831
_reflns_number_gt                2137
_reflns_number_total             4607
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb7404sup1.cif
_cod_data_source_block           II
_cod_database_code               2240668
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.992
_shelx_hkl_checksum              84949
_shelx_res_checksum              4970
_shelxl_version_number           2.014
_cod_database_fobs_code 2240668