#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/81/2228107.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228107
loop_
_publ_author_name
'Li, Kai-Hui'
'Lei, Qing-Duo'
'Mei, Chong-Zhen'
_publ_section_title
;
 4-Cyano-1-(4-nitrobenzyl)pyridinium
 bis(2-thioxo-1,3-dithiole-4,5-dithiolato-κ²S⁴,S⁵)nickelate(III)
;
_journal_coeditor_code           XU5018
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1311
_journal_paper_doi               10.1107/S1600536810037426
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '(C13 H10 N3 O2) [Ni (C3 S5)2]'
_chemical_formula_moiety         'C13 H10 N3 O2, C6 Ni S10'
_chemical_formula_sum            'C19 H10 N3 Ni O2 S10'
_chemical_formula_weight         691.61
_chemical_name_systematic
;
4-Cyano-1-(4-nitrobenzyl)pyridinium
bis(2-thioxo-1,3-dithiole-4,5-dithiolato-
κ²S⁴,S⁵)nickelate(III)
;
_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                 106.181(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4896(17)
_cell_length_b                   25.789(5)
_cell_length_c                   12.043(3)
_cell_measurement_reflns_used    947
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.313
_cell_measurement_theta_min      2.366
_cell_volume                     2532.2(9)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12415
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.617
_exptl_absorpt_correction_T_max  0.7935
_exptl_absorpt_correction_T_min  0.7380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                3343
_reflns_number_total             4423
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5018.cif
_cod_data_source_block           I
_cod_original_cell_volume        2532.3(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228107
_cod_database_fobs_code          2228107
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.12504(5) 0.535201(17) 0.42287(3) 0.04673(14) Uani d . 1 . .
O O1 0.2608(4) 0.40743(10) -0.0690(2) 0.0797(9) Uani d . 1 . .
O O2 0.5120(4) 0.39512(10) 0.0279(2) 0.0754(8) Uani d . 1 . .
N N1 0.5275(4) 0.80533(13) -0.0531(3) 0.0746(10) Uani d . 1 . .
N N2 0.4084(3) 0.64870(9) 0.1936(2) 0.0424(6) Uani d . 1 . .
N N3 0.3834(4) 0.41930(11) 0.0065(2) 0.0552(8) Uani d . 1 . .
S S1 0.08507(13) 0.76215(4) 0.75005(9) 0.0690(3) Uani d . 1 . .
S S2 -0.05329(12) 0.69214(4) 0.55265(9) 0.0660(3) Uani d . 1 . .
S S3 0.27096(11) 0.67162(4) 0.69657(8) 0.0602(3) Uani d . 1 . .
S S4 -0.05363(11) 0.59682(4) 0.40526(8) 0.0620(3) Uani d . 1 . .
S S5 0.29798(11) 0.57297(4) 0.56561(8) 0.0578(3) Uani d . 1 . .
S S6 -0.04453(10) 0.49687(4) 0.27893(8) 0.0581(3) Uani d . 1 . .
S S7 0.30541(10) 0.47438(4) 0.44187(8) 0.0559(3) Uani d . 1 . .
S S8 -0.01230(12) 0.39818(4) 0.15167(8) 0.0661(3) Uani d . 1 . .
S S9 0.31466(11) 0.37927(4) 0.29563(8) 0.0596(3) Uani d . 1 . .
S S10 0.16951(15) 0.30728(4) 0.10160(11) 0.0842(4) Uani d . 1 . .
C C1 0.0997(4) 0.71136(13) 0.6712(3) 0.0553(9) Uani d . 1 . .
C C2 0.0396(4) 0.63686(13) 0.5171(3) 0.0514(9) Uani d . 1 . .
C C3 0.1933(4) 0.62697(13) 0.5861(3) 0.0499(9) Uani d . 1 . .
C C4 0.0626(4) 0.44299(13) 0.2605(3) 0.0510(9) Uani d . 1 . .
C C5 0.2162(4) 0.43352(13) 0.3297(3) 0.0487(8) Uani d . 1 . .
C C6 0.1579(4) 0.35837(14) 0.1780(3) 0.0602(10) Uani d . 1 . .
C C8 0.4722(4) 0.72766(12) 0.0638(3) 0.0442(8) Uani d . 1 . .
C C9 0.5968(4) 0.70593(12) 0.1495(3) 0.0480(8) Uani d . 1 . .
H H9 0.7035 0.7184 0.1643 0.058 Uiso calc R 1 . .
C C10 0.5612(4) 0.66582(12) 0.2124(3) 0.0472(8) Uani d . 1 . .
H H10 0.6451 0.6503 0.2693 0.057 Uiso calc R 1 . .
C C11 0.2853(4) 0.66928(12) 0.1100(3) 0.0458(8) Uani d . 1 . .
H H11 0.1793 0.6565 0.0976 0.055 Uiso calc R 1 . .
C C12 0.3145(4) 0.70877(12) 0.0432(3) 0.0484(8) Uani d . 1 . .
H H12 0.2295 0.7228 -0.0153 0.058 Uiso calc R 1 . .
C C13 0.3706(4) 0.60448(12) 0.2623(3) 0.0511(9) Uani d . 1 . .
H H13A 0.2637 0.6097 0.2749 0.061 Uiso calc R 1 . .
H H13B 0.4516 0.6031 0.3372 0.061 Uiso calc R 1 . .
C C14 0.5122(4) 0.52460(13) 0.2208(3) 0.0485(9) Uani d . 1 . .
H H14 0.6052 0.5348 0.2781 0.058 Uiso calc R 1 . .
C C15 0.3716(4) 0.55425(11) 0.1992(2) 0.0404(7) Uani d . 1 . .
C C16 0.2328(4) 0.53870(12) 0.1150(3) 0.0476(8) Uani d . 1 . .
H H16 0.1371 0.5581 0.1013 0.057 Uiso calc R 1 . .
C C17 0.2358(4) 0.49449(12) 0.0513(3) 0.0474(8) Uani d . 1 . .
H H17 0.1435 0.4841 -0.0064 0.057 Uiso calc R 1 . .
C C18 0.3785(4) 0.46620(12) 0.0752(2) 0.0415(8) Uani d . 1 . .
C C19 0.5162(4) 0.48020(13) 0.1588(3) 0.0484(8) Uani d . 1 . .
H H19 0.6109 0.4602 0.1735 0.058 Uiso calc R 1 . .
C C20 0.5035(4) 0.77070(14) -0.0025(3) 0.0538(9) Uani d . 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
_geom_angle_publ_flag
S5 Ni1 S7 . . 86.47(4) ?
S5 Ni1 S6 . . 178.98(4) ?
S7 Ni1 S6 . . 92.69(4) ?
S5 Ni1 S4 . . 92.83(4) ?
S7 Ni1 S4 . . 179.28(4) ?
S6 Ni1 S4 . . 88.01(4) ?
C10 N2 C11 . . 121.1(3) ?
C10 N2 C13 . . 120.6(3) ?
C11 N2 C13 . . 118.3(3) ?
O1 N3 O2 . . 124.0(3) ?
O1 N3 C18 . . 118.4(3) ?
O2 N3 C18 . . 117.7(3) ?
C1 S2 C2 . . 98.72(17) ?
C1 S3 C3 . . 97.80(16) ?
C2 S4 Ni1 . . 102.02(12) ?
C3 S5 Ni1 . . 102.58(11) ?
C4 S6 Ni1 . . 102.50(11) ?
C5 S7 Ni1 . . 102.63(12) ?
C6 S8 C4 . . 98.39(16) ?
C5 S9 C6 . . 97.64(17) ?
S1 C1 S2 . . 123.4(2) ?
S1 C1 S3 . . 124.3(2) ?
S2 C1 S3 . . 112.3(2) ?
C3 C2 S4 . . 121.6(3) ?
C3 C2 S2 . . 115.2(3) ?
S4 C2 S2 . . 123.19(19) ?
C2 C3 S5 . . 120.9(3) ?
C2 C3 S3 . . 115.9(3) ?
S5 C3 S3 . . 123.24(19) ?
C5 C4 S6 . . 121.4(3) ?
C5 C4 S8 . . 115.6(3) ?
S6 C4 S8 . . 123.02(19) ?
C4 C5 S7 . . 120.7(3) ?
C4 C5 S9 . . 116.3(3) ?
S7 C5 S9 . . 123.06(19) ?
S10 C6 S8 . . 123.9(2) ?
S10 C6 S9 . . 124.0(2) ?
S8 C6 S9 . . 112.1(2) ?
C9 C8 C12 . . 119.7(3) ?
C9 C8 C20 . . 120.7(3) ?
C12 C8 C20 . . 119.6(3) ?
C10 C9 C8 . . 118.9(3) ?
C10 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
N2 C10 C9 . . 120.9(3) ?
N2 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
N2 C11 C12 . . 120.4(3) ?
N2 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 C8 . . 119.0(3) ?
C11 C12 H12 . . 120.5 ?
C8 C12 H12 . . 120.5 ?
N2 C13 C15 . . 110.2(2) ?
N2 C13 H13A . . 109.6 ?
C15 C13 H13A . . 109.6 ?
N2 C13 H13B . . 109.6 ?
C15 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
C19 C14 C15 . . 120.7(3) ?
C19 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C14 C15 C16 . . 119.5(3) ?
C14 C15 C13 . . 120.6(3) ?
C16 C15 C13 . . 119.8(3) ?
C17 C16 C15 . . 120.3(3) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C18 C17 C16 . . 118.3(3) ?
C18 C17 H17 . . 120.9 ?
C16 C17 H17 . . 120.9 ?
C19 C18 C17 . . 122.6(3) ?
C19 C18 N3 . . 118.7(3) ?
C17 C18 N3 . . 118.6(3) ?
C18 C19 C14 . . 118.5(3) ?
C18 C19 H19 . . 120.8 ?
C14 C19 H19 . . 120.8 ?
N1 C20 C8 . . 178.6(4) ?
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 S5 . 2.1570(10) ?
Ni1 S7 . 2.1591(10) ?
Ni1 S6 . 2.1596(10) ?
Ni1 S4 . 2.1661(10) ?
O1 N3 . 1.215(3) ?
O2 N3 . 1.220(4) ?
N1 C20 . 1.132(4) ?
N2 C10 . 1.328(4) ?
N2 C11 . 1.343(4) ?
N2 C13 . 1.495(4) ?
N3 C18 . 1.473(4) ?
S1 C1 . 1.643(4) ?
S2 C1 . 1.714(4) ?
S2 C2 . 1.740(4) ?
S3 C1 . 1.735(4) ?
S3 C3 . 1.744(3) ?
S4 C2 . 1.707(4) ?
S5 C3 . 1.707(4) ?
S6 C4 . 1.709(4) ?
S7 C5 . 1.714(3) ?
S8 C6 . 1.728(4) ?
S8 C4 . 1.730(3) ?
S9 C5 . 1.736(4) ?
S9 C6 . 1.738(4) ?
S10 C6 . 1.626(4) ?
C2 C3 . 1.362(4) ?
C4 C5 . 1.360(4) ?
C8 C9 . 1.375(4) ?
C8 C12 . 1.380(4) ?
C8 C20 . 1.434(5) ?
C9 C10 . 1.365(4) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.362(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C15 . 1.503(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C19 . 1.373(4) ?
C14 C15 . 1.379(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.383(4) ?
C16 C17 . 1.378(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.375(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.362(4) ?
C19 H19 . 0.9300 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S5 Ni1 S4 C2 . . . . -3.08(12) ?
S6 Ni1 S4 C2 . . . . 177.50(12) ?
S7 Ni1 S5 C3 . . . . -177.63(12) ?
S4 Ni1 S5 C3 . . . . 2.52(12) ?
S7 Ni1 S6 C4 . . . . -2.01(12) ?
S4 Ni1 S6 C4 . . . . 177.84(12) ?
S5 Ni1 S7 C5 . . . . -176.49(12) ?
S6 Ni1 S7 C5 . . . . 2.94(12) ?
C2 S2 C1 S1 . . . . -177.9(2) ?
C2 S2 C1 S3 . . . . 2.8(2) ?
C3 S3 C1 S1 . . . . 177.6(2) ?
C3 S3 C1 S2 . . . . -3.1(2) ?
Ni1 S4 C2 C3 . . . . 3.3(3) ?
Ni1 S4 C2 S2 . . . . -175.84(18) ?
C1 S2 C2 C3 . . . . -1.3(3) ?
C1 S2 C2 S4 . . . . 177.9(2) ?
S4 C2 C3 S5 . . . . -1.5(4) ?
S2 C2 C3 S5 . . . . 177.70(18) ?
S4 C2 C3 S3 . . . . -179.97(18) ?
S2 C2 C3 S3 . . . . -0.7(4) ?
Ni1 S5 C3 C2 . . . . -1.2(3) ?
Ni1 S5 C3 S3 . . . . 177.12(18) ?
C1 S3 C3 C2 . . . . 2.4(3) ?
C1 S3 C3 S5 . . . . -176.0(2) ?
Ni1 S6 C4 C5 . . . . 0.3(3) ?
Ni1 S6 C4 S8 . . . . -177.69(18) ?
C6 S8 C4 C5 . . . . -1.7(3) ?
C6 S8 C4 S6 . . . . 176.4(2) ?
S6 C4 C5 S7 . . . . 2.4(4) ?
S8 C4 C5 S7 . . . . -179.46(18) ?
S6 C4 C5 S9 . . . . -176.42(18) ?
S8 C4 C5 S9 . . . . 1.7(4) ?
Ni1 S7 C5 C4 . . . . -3.7(3) ?
Ni1 S7 C5 S9 . . . . 175.08(17) ?
C6 S9 C5 C4 . . . . -0.8(3) ?
C6 S9 C5 S7 . . . . -179.6(2) ?
C4 S8 C6 S10 . . . . -179.0(2) ?
C4 S8 C6 S9 . . . . 1.1(2) ?
C5 S9 C6 S10 . . . . 179.7(2) ?
C5 S9 C6 S8 . . . . -0.4(2) ?
C12 C8 C9 C10 . . . . 0.2(5) ?
C20 C8 C9 C10 . . . . 178.5(3) ?
C11 N2 C10 C9 . . . . 2.0(5) ?
C13 N2 C10 C9 . . . . 179.5(3) ?
C8 C9 C10 N2 . . . . -1.7(5) ?
C10 N2 C11 C12 . . . . -0.7(5) ?
C13 N2 C11 C12 . . . . -178.4(3) ?
N2 C11 C12 C8 . . . . -0.8(5) ?
C9 C8 C12 C11 . . . . 1.0(5) ?
C20 C8 C12 C11 . . . . -177.3(3) ?
C10 N2 C13 C15 . . . . -93.8(3) ?
C11 N2 C13 C15 . . . . 83.8(4) ?
C19 C14 C15 C16 . . . . 0.7(5) ?
C19 C14 C15 C13 . . . . -176.3(3) ?
N2 C13 C15 C14 . . . . 93.1(3) ?
N2 C13 C15 C16 . . . . -84.0(4) ?
C14 C15 C16 C17 . . . . -1.4(5) ?
C13 C15 C16 C17 . . . . 175.7(3) ?
C15 C16 C17 C18 . . . . 1.1(5) ?
C16 C17 C18 C19 . . . . -0.1(5) ?
C16 C17 C18 N3 . . . . -179.2(3) ?
O1 N3 C18 C19 . . . . -179.0(3) ?
O2 N3 C18 C19 . . . . -0.1(4) ?
O1 N3 C18 C17 . . . . 0.1(4) ?
O2 N3 C18 C17 . . . . 179.0(3) ?
C17 C18 C19 C14 . . . . -0.5(5) ?
N3 C18 C19 C14 . . . . 178.5(3) ?
C15 C14 C19 C18 . . . . 0.2(5) ?
