#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/44/2234421.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_2234421
loop_
_publ_author_name
'Yu, Shan-Shan'
'Zhou, Hong'
'Ren, Xiao-Ming'
_publ_section_title
;
 Bis(4-dimethylamino-1-ethylpyridinium)
 bis(1,2-dicyanoethene-1,2-dithiolato-κ²S,S')nickelate(II)
;
_journal_coeditor_code           TK5062
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m395
_journal_paper_doi               10.1107/S1600536812008161
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '(C9 H15 N2)2 [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         '2(C9 H15 N2 +), C8 N4 Ni S4 2-'
_chemical_formula_sum            'C26 H30 N8 Ni S4'
_chemical_formula_weight         641.55
_chemical_name_systematic
;
Bis(4-dimethylamino-1-ethylpyridinium)
bis(1,2-dicyanoethene-1,2-dithiolato-κ²S,S')nickelate(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.243(3)
_cell_angle_beta                 100.034(3)
_cell_angle_gamma                107.830(2)
_cell_formula_units_Z            1
_cell_length_a                   8.1468(14)
_cell_length_b                   9.3305(16)
_cell_length_c                   11.663(3)
_cell_measurement_temperature    296(2)
_cell_volume                     764.9(3)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5798
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0370
_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)+(0.0910P)²+0.1169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2371
_reflns_number_total             2827
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5062.cif
_cod_data_source_block           I
_cod_original_cell_volume        765.0(3)
_cod_database_code               2234421
_cod_database_fobs_code          2234421
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_symmetry_multiplicity
Ni Ni1 1.0000 0.5000 0.5000 0.04490(19) Uani d S 1 2
S S1 0.82193(11) 0.48140(9) 0.32858(7) 0.0569(2) Uani d . 1 1
S S2 0.98454(10) 0.73406(8) 0.59749(7) 0.0544(2) Uani d . 1 1
N N1 0.6004(5) 0.2159(4) -0.0092(3) 0.0933(10) Uani d . 1 1
N N2 1.1487(5) 1.0752(4) 0.9081(3) 0.1059(12) Uani d . 1 1
N N3 0.4538(3) 0.6143(3) 0.2736(2) 0.0612(6) Uani d . 1 1
C C9 0.6202(4) 0.8572(3) 0.5178(3) 0.0537(6) Uani d . 1 1
C C1 0.6864(5) 0.2485(4) 0.0912(3) 0.0653(8) Uani d . 1 1
C C2 0.7958(4) 0.2948(3) 0.2175(3) 0.0524(6) Uani d . 1 1
C C3 1.1208(4) 0.7989(3) 0.7514(3) 0.0514(6) Uani d . 1 1
C C4 1.1395(4) 0.9529(4) 0.8407(3) 0.0664(8) Uani d . 1 1
C C5 0.1777(5) 0.4619(5) 0.0912(4) 0.0947(12) Uani d . 1 1
H H5A 0.1089 0.4361 0.1461 0.142 Uiso calc R 1 1
H H5B 0.1256 0.3745 0.0089 0.142 Uiso calc R 1 1
H H5C 0.1762 0.5614 0.0844 0.142 Uiso calc R 1 1
C C6 0.3668(5) 0.4828(4) 0.1439(3) 0.0798(10) Uani d . 1 1
H H6A 0.4360 0.5097 0.0884 0.096 Uiso calc R 1 1
H H6B 0.3682 0.3805 0.1468 0.096 Uiso calc R 1 1
C C7 0.4085(4) 0.5897(4) 0.3731(3) 0.0648(8) Uani d . 1 1
H H7 0.3215 0.4893 0.3593 0.078 Uiso calc R 1 1
C C8 0.4840(4) 0.7048(4) 0.4930(3) 0.0634(8) Uani d . 1 1
H H8 0.4462 0.6834 0.5589 0.076 Uiso calc R 1 1
N N4 0.7030(4) 0.9716(3) 0.6353(2) 0.0637(6) Uani d . 1 1
C C10 0.6603(6) 0.9431(5) 0.7439(3) 0.0926(11) Uani d . 1 1
H H10A 0.5331 0.9145 0.7325 0.139 Uiso calc R 1 1
H H10B 0.7268 1.0406 0.8190 0.139 Uiso calc R 1 1
H H10C 0.6925 0.8554 0.7523 0.139 Uiso calc R 1 1
C C11 0.8478(5) 1.1248(4) 0.6603(3) 0.0776(9) Uani d . 1 1
H H11A 0.9461 1.1030 0.6341 0.116 Uiso calc R 1 1
H H11B 0.8891 1.1914 0.7493 0.116 Uiso calc R 1 1
H H11C 0.8042 1.1815 0.6142 0.116 Uiso calc R 1 1
C C12 0.6630(4) 0.8805(3) 0.4110(3) 0.0567(7) Uani d . 1 1
H H12 0.7490 0.9796 0.4213 0.068 Uiso calc R 1 1
C C13 0.5803(4) 0.7602(4) 0.2938(3) 0.0599(7) Uani d . 1 1
H H13 0.6116 0.7786 0.2252 0.072 Uiso calc R 1 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'
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
_geom_angle_publ_flag
S2 Ni1 S2 . 2_766 180.0 ?
S2 Ni1 S1 . 2_766 92.00(3) ?
S2 Ni1 S1 2_766 2_766 88.00(3) ?
S2 Ni1 S1 . . 88.00(3) y
S2 Ni1 S1 2_766 . 92.00(3) ?
S1 Ni1 S1 2_766 . 180.0000(10) ?
C2 S1 Ni1 . . 103.04(10) ?
C3 S2 Ni1 . . 103.41(10) ?
C7 N3 C13 . . 118.5(3) ?
C7 N3 C6 . . 120.5(3) ?
C13 N3 C6 . . 121.0(3) ?
N4 C9 C8 . . 121.9(3) ?
N4 C9 C12 . . 122.3(3) ?
C8 C9 C12 . . 115.8(3) ?
N1 C1 C2 . . 178.1(3) ?
C3 C2 C1 2_766 . 122.2(3) ?
C3 C2 S1 2_766 . 121.3(2) ?
C1 C2 S1 . . 116.5(2) ?
C2 C3 C4 2_766 . 122.6(3) ?
C2 C3 S2 2_766 . 120.3(2) ?
C4 C3 S2 . . 117.2(2) ?
N2 C4 C3 . . 177.2(4) ?
C6 C5 H5A . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C6 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C5 C6 N3 . . 112.0(3) ?
C5 C6 H6A . . 109.2 ?
N3 C6 H6A . . 109.2 ?
C5 C6 H6B . . 109.2 ?
N3 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
N3 C7 C8 . . 122.9(3) ?
N3 C7 H7 . . 118.5 ?
C8 C7 H7 . . 118.5 ?
C7 C8 C9 . . 120.0(3) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C9 N4 C11 . . 121.5(3) ?
C9 N4 C10 . . 121.3(3) ?
C11 N4 C10 . . 117.0(3) ?
N4 C10 H10A . . 109.5 ?
N4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N4 C11 H11A . . 109.5 ?
N4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C9 . . 120.8(3) ?
C13 C12 H12 . . 119.6 ?
C9 C12 H12 . . 119.6 ?
N3 C13 C12 . . 122.0(3) ?
N3 C13 H13 . . 119.0 ?
C12 C13 H13 . . 119.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 S2 . 2.1776(8) y
Ni1 S2 2_766 2.1776(8) ?
Ni1 S1 2_766 2.1794(8) ?
Ni1 S1 . 2.1794(8) y
S1 C2 . 1.738(3) ?
S2 C3 . 1.742(3) ?
N1 C1 . 1.147(4) ?
N2 C4 . 1.136(4) ?
N3 C7 . 1.342(4) ?
N3 C13 . 1.351(4) ?
N3 C6 . 1.493(4) ?
C9 N4 . 1.339(4) ?
C9 C8 . 1.415(4) ?
C9 C12 . 1.412(4) ?
C1 C2 . 1.435(4) ?
C2 C3 2_766 1.354(4) ?
C3 C2 2_766 1.354(4) ?
C3 C4 . 1.431(4) ?
C5 C6 . 1.483(5) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.358(4) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
N4 C11 . 1.452(4) ?
N4 C10 . 1.451(4) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.356(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
