#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/08/2210871.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210871
loop_
_publ_author_name
'Liu, Ming-Guo'
'Li, Xiao-Yan'
'Lin, Li-Fa'
'Ni, Chun-Lin'
_publ_section_title
;
 Bis[1-(4-nitrobenzyl)pyridinium]
 bis(2,2-dicyanoethylene-1,1-dithiolato-κ²S,S')nickelate(II)
;
_journal_coeditor_code           BH2049
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2919
_journal_page_last               m2921
_journal_paper_doi               10.1107/S1600536806041973
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '(C12 H11 N2 O2)2 [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         '2C12 H11 N2 O2 +, C8 N4 Ni S4 2-'
_chemical_formula_sum            'C32 H22 N8 Ni O4 S4'
_chemical_formula_weight         769.53
_chemical_name_systematic
;
Bis[1-(4-nitrobenzyl)pyridinium]
bis(2,2-dicyanoethylene-1,1-dithiolato-κ²S,S')nickel(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2000
_cell_angle_alpha                90.00
_cell_angle_beta                 100.110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8250(10)
_cell_length_b                   12.0920(10)
_cell_length_c                   14.660(2)
_cell_measurement_reflns_used    607
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.470
_cell_measurement_theta_min      2.697
_cell_volume                     1714.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16784
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.849
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0536
_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/[σ²(Fo²)+(0.03P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                1649
_reflns_number_total             3017
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2049.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210871
_cod_database_fobs_code          2210871
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Ni Ni1 0.0000 0.0000 0.0000 0.0459(2) Uani d SU 1
S S1 -0.10543(12) 0.15741(9) 0.01222(9) 0.0564(4) Uani d U 1
S S2 0.17713(11) 0.11399(9) 0.02447(8) 0.0534(3) Uani d . 1
N N1 -0.1117(4) 0.4509(3) 0.0844(3) 0.0822(14) Uani d . 1
N N2 0.3353(4) 0.3941(3) 0.0902(3) 0.0806(14) Uani d . 1
N N3 0.9123(4) 1.0135(3) 0.2841(3) 0.0523(10) Uani d . 1
N N4 1.0560(5) 0.4937(4) 0.3312(3) 0.0674(12) Uani d . 1
O O1 1.0226(4) 0.4438(3) 0.3963(3) 0.0976(13) Uani d . 1
O O2 1.1361(4) 0.4583(3) 0.2845(3) 0.0926(13) Uani d . 1
C C1 0.0577(4) 0.2150(3) 0.0357(3) 0.0471(11) Uani d . 1
C C2 0.0870(5) 0.3222(3) 0.0622(3) 0.0481(11) Uani d U 1
C C3 -0.0223(5) 0.3942(4) 0.0748(3) 0.0569(13) Uani d . 1
C C4 0.2247(5) 0.3633(4) 0.0781(3) 0.0556(13) Uani d U 1
C C5 0.8601(4) 0.7541(4) 0.3465(3) 0.0605(13) Uani d . 1
H H5 0.8054 0.7860 0.3851 0.073 Uiso calc R 1
C C6 0.9183(5) 0.6513(4) 0.3678(3) 0.0627(13) Uani d . 1
H H6 0.9049 0.6144 0.4212 0.075 Uiso calc R 1
C C7 0.9958(5) 0.6050(4) 0.3094(3) 0.0496(12) Uani d . 1
C C8 1.0183(5) 0.6561(4) 0.2313(3) 0.0625(13) Uani d . 1
H H8 1.0713 0.6227 0.1924 0.075 Uiso calc R 1
C C9 0.9600(5) 0.7601(4) 0.2106(3) 0.0672(14) Uani d . 1
H H9 0.9738 0.7966 0.1571 0.081 Uiso calc R 1
C C10 0.8822(4) 0.8093(3) 0.2690(3) 0.0496(12) Uani d . 1
C C11 0.8193(4) 0.9214(3) 0.2448(3) 0.0612(14) Uani d . 1
H H11A 0.7985 0.9289 0.1779 0.073 Uiso calc R 1
H H11B 0.7329 0.9269 0.2680 0.073 Uiso calc R 1
C C12 0.8938(5) 1.0647(4) 0.3610(4) 0.0692(15) Uani d . 1
H H12 0.8239 1.0414 0.3919 0.083 Uiso calc R 1
C C13 0.9763(6) 1.1508(4) 0.3951(4) 0.0848(17) Uani d . 1
H H13 0.9618 1.1875 0.4483 0.102 Uiso calc R 1
C C14 1.0806(6) 1.1828(4) 0.3505(4) 0.0796(17) Uani d . 1
H H14 1.1378 1.2415 0.3734 0.095 Uiso calc R 1
C C15 1.1007(5) 1.1287(4) 0.2726(4) 0.0751(16) Uani d . 1
H H15 1.1717 1.1494 0.2417 0.090 Uiso calc R 1
C C16 1.0150(6) 1.0440(4) 0.2410(3) 0.0674(14) Uani d . 1
H H16 1.0282 1.0061 0.1880 0.081 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
S1 Ni1 S1 . 3 180.00(8)
S1 Ni1 S2 . . 79.28(4)
S1 Ni1 S2 3 . 100.72(4)
S1 Ni1 S2 . 3 100.72(4)
S1 Ni1 S2 3 3 79.28(4)
S2 Ni1 S2 . 3 180.00(8)
C1 S1 Ni1 . . 86.03(14)
C1 S2 Ni1 . . 85.80(15)
C12 N3 C16 . . 120.1(4)
C12 N3 C11 . . 120.8(4)
C16 N3 C11 . . 119.1(4)
O2 N4 O1 . . 124.0(5)
O2 N4 C7 . . 118.2(5)
O1 N4 C7 . . 117.8(5)
C2 C1 S2 . . 125.8(3)
C2 C1 S1 . . 125.5(3)
S2 C1 S1 . . 108.7(2)
C1 C2 C3 . . 119.4(4)
C1 C2 C4 . . 121.6(4)
C3 C2 C4 . . 119.0(4)
N1 C3 C2 . . 178.9(5)
N2 C4 C2 . . 178.7(5)
C10 C5 C6 . . 120.5(4)
C10 C5 H5 . . 119.8
C6 C5 H5 . . 119.8
C7 C6 C5 . . 118.9(5)
C7 C6 H6 . . 120.6
C5 C6 H6 . . 120.6
C8 C7 C6 . . 122.4(5)
C8 C7 N4 . . 118.7(5)
C6 C7 N4 . . 118.9(5)
C7 C8 C9 . . 118.4(5)
C7 C8 H8 . . 120.8
C9 C8 H8 . . 120.8
C10 C9 C8 . . 120.4(5)
C10 C9 H9 . . 119.8
C8 C9 H9 . . 119.8
C5 C10 C9 . . 119.5(4)
C5 C10 C11 . . 121.1(4)
C9 C10 C11 . . 119.4(5)
N3 C11 C10 . . 112.5(3)
N3 C11 H11A . . 109.1
C10 C11 H11A . . 109.1
N3 C11 H11B . . 109.1
C10 C11 H11B . . 109.1
H11A C11 H11B . . 107.8
N3 C12 C13 . . 120.6(5)
N3 C12 H12 . . 119.7
C13 C12 H12 . . 119.7
C12 C13 C14 . . 119.4(5)
C12 C13 H13 . . 120.3
C14 C13 H13 . . 120.3
C15 C14 C13 . . 119.8(5)
C15 C14 H14 . . 120.1
C13 C14 H14 . . 120.1
C16 C15 C14 . . 118.5(5)
C16 C15 H15 . . 120.7
C14 C15 H15 . . 120.7
N3 C16 C15 . . 121.5(5)
N3 C16 H16 . . 119.2
C15 C16 H16 . . 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 S1 . 2.1894(11)
Ni1 S1 3 2.1894(11)
Ni1 S2 . 2.1996(11)
Ni1 S2 3 2.1996(11)
S1 C1 . 1.725(4)
S2 C1 . 1.721(4)
N1 C3 . 1.142(5)
N2 C4 . 1.133(5)
N3 C12 . 1.325(5)
N3 C16 . 1.334(6)
N3 C11 . 1.491(5)
N4 O2 . 1.210(5)
N4 O1 . 1.221(5)
N4 C7 . 1.482(5)
C1 C2 . 1.370(5)
C2 C3 . 1.419(6)
C2 C4 . 1.421(6)
C5 C10 . 1.367(6)
C5 C6 . 1.381(5)
C5 H5 . 0.9300
C6 C7 . 1.363(6)
C6 H6 . 0.9300
C7 C8 . 1.352(6)
C8 C9 . 1.393(5)
C8 H8 . 0.9300
C9 C10 . 1.378(6)
C9 H9 . 0.9300
C10 C11 . 1.507(5)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 C13 . 1.360(6)
C12 H12 . 0.9300
C13 C14 . 1.365(7)
C13 H13 . 0.9300
C14 C15 . 1.361(7)
C14 H14 . 0.9300
C15 C16 . 1.355(6)
C15 H15 . 0.9300
C16 H16 . 0.9300
