#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/34/2203454.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_2203454
loop_
_publ_author_name
'Tian, Zheng-Fang'
'Li, Yi-Zhi'
'Meng, Qing-Jin'
'Liu, San-Hui'
'Ji, Xing-Xiang'
_publ_section_title
;
 Bis[1-(3-cyanobenzyl)-3-methylpyrazinium]
 bis(1,2-dicyanoethene-1,2-dithiolato)nickel(II)
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m396
_journal_page_last               m398
_journal_paper_doi               10.1107/S1600536804005616
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '(C13 H12 N3)2 [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         '2C13 H12 N3 1+, C8 N4 Ni S4 2-'
_chemical_formula_sum            'C34 H24 N10 Ni S4'
_chemical_formula_weight         759.58
_chemical_name_systematic
;
Bis[1-(3-cyanobenzyl)-3-methylpyrazinium]
bis(1,2-dicyanoethene-1,2-dithiolato)nickel(II)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.831(2)
_cell_length_b                   14.220(2)
_cell_length_c                   14.256(2)
_cell_measurement_reflns_used    951
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.72
_cell_volume                     1743.6(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker; 2000)'
_computing_data_reduction        'SAINT (Bruker; 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker; 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9111
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0549
_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)+(0.06P)²+1.99P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                2473
_reflns_number_total             3401
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6177.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2203454
_cod_database_fobs_code          2203454
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_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_type_symbol
Ni1 1.0000 0.5000 0.0000 0.0490(2) Uani d S 1 Ni
S1 0.91760(11) 0.40198(7) 0.09433(7) 0.0511(2) Uani d . 1 S
S2 0.80570(11) 0.59381(6) -0.00389(7) 0.0506(2) Uani d . 1 S
N1 0.6118(5) 0.3725(3) 0.2293(3) 0.0774(11) Uani d . 1 N
N2 0.4732(4) 0.6331(3) 0.1062(3) 0.0764(11) Uani d . 1 N
C1 0.6733(5) 0.4110(3) 0.1795(3) 0.0534(9) Uani d . 1 C
C2 0.7534(4) 0.4587(3) 0.1159(2) 0.0453(8) Uani d . 1 C
C3 0.7065(4) 0.5399(2) 0.0733(2) 0.0439(8) Uani d . 1 C
C4 0.5756(4) 0.5899(3) 0.0923(3) 0.0524(9) Uani d . 1 C
N3 1.1059(3) 0.6681(2) 0.19793(19) 0.0442(6) Uani d . 1 N
N4 0.9137(4) 0.8148(2) 0.1328(3) 0.0594(8) Uani d . 1 N
N5 1.1716(5) 0.4414(3) 0.6131(3) 0.0867(13) Uani d . 1 N
C5 1.1320(4) 0.7208(3) 0.1274(3) 0.0514(9) Uani d . 1 C
H5 1.2158 0.7084 0.0999 0.062 Uiso calc R 1 H
C6 1.0335(5) 0.7942(3) 0.0953(3) 0.0650(11) Uani d . 1 C
H6 1.0516 0.8311 0.0450 0.078 Uiso calc R 1 H
C7 0.8901(4) 0.7623(3) 0.2038(3) 0.0484(8) Uani d . 1 C
C8 0.9829(4) 0.6871(2) 0.2367(2) 0.0452(8) Uani d . 1 C
H8 0.9617 0.6491 0.2853 0.054 Uiso calc R 1 H
C9 1.2055(5) 0.5843(2) 0.2328(3) 0.0535(9) Uani d . 1 C
H9A 1.1422 0.5279 0.2222 0.064 Uiso calc R 1 H
H9B 1.2851 0.5785 0.1962 0.064 Uiso calc R 1 H
C10 1.2809(4) 0.5925(2) 0.3374(2) 0.0427(7) Uani d . 1 C
C11 1.2251(4) 0.5379(2) 0.4025(3) 0.0478(8) Uani d . 1 C
H11 1.1439 0.4961 0.3804 0.057 Uiso calc R 1 H
C12 1.2895(4) 0.5451(3) 0.5007(3) 0.0504(9) Uani d . 1 C
C13 1.4094(5) 0.6081(3) 0.5330(3) 0.0603(10) Uani d . 1 C
H13 1.4516 0.6141 0.5987 0.072 Uiso calc R 1 H
C14 1.4657(5) 0.6612(3) 0.4697(3) 0.0631(11) Uani d . 1 C
H14 1.5471 0.7029 0.4918 0.076 Uiso calc R 1 H
C15 1.4023(5) 0.6533(3) 0.3725(3) 0.0556(9) Uani d . 1 C
H15 1.4421 0.6898 0.3296 0.067 Uiso calc R 1 H
C16 0.7533(5) 0.7843(3) 0.2477(3) 0.0682(12) Uani d . 1 C
H16A 0.6588 0.7816 0.1986 0.102 Uiso calc R 1 H
H16B 0.7654 0.8462 0.2753 0.102 Uiso calc R 1 H
H16C 0.7488 0.7391 0.2970 0.102 Uiso calc R 1 H
C17 1.2269(5) 0.4865(3) 0.5653(3) 0.0649(11) Uani d . 1 C
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'
Ni Ni 0.3393 1.1124 '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'
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 . 3_765 180.0 y
S2 Ni1 S1 . . 92.09(4) y
S2 Ni1 S1 3_765 . 87.91(4) n
S2 Ni1 S1 . 3_765 87.91(4) y
S2 Ni1 S1 3_765 3_765 92.09(4) ?
S1 Ni1 S1 . 3_765 180.0 y
C2 S1 Ni1 . . 102.72(12) ?
C3 S2 Ni1 . . 102.90(13) ?
N1 C1 C2 . . 179.0(5) ?
C3 C2 C1 . . 123.4(3) ?
C3 C2 S1 . . 120.5(2) ?
C1 C2 S1 . . 116.0(3) ?
C2 C3 C4 . . 121.7(3) ?
C2 C3 S2 . . 121.7(3) ?
C4 C3 S2 . . 116.5(3) ?
N2 C4 C3 . . 177.2(4) ?
C5 N3 C8 . . 119.6(3) ?
C5 N3 C9 . . 121.0(3) ?
C8 N3 C9 . . 119.3(3) ?
C7 N4 C6 . . 117.9(3) ?
N3 C5 C6 . . 118.8(3) ?
N3 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
N4 C6 C5 . . 122.6(4) ?
N4 C6 H6 . . 118.7 ?
C5 C6 H6 . . 118.7 ?
N4 C7 C8 . . 121.5(3) ?
N4 C7 C16 . . 118.9(3) ?
C8 C7 C16 . . 119.6(3) ?
N3 C8 C7 . . 119.5(3) ?
N3 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C10 C9 N3 . . 111.4(3) ?
C10 C9 H9A . . 109.3 ?
N3 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
N3 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
C15 C10 C11 . . 118.3(3) ?
C15 C10 C9 . . 123.0(3) ?
C11 C10 C9 . . 118.7(3) ?
C10 C11 C12 . . 120.6(3) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.3(3) ?
C13 C12 C17 . . 122.5(4) ?
C11 C12 C17 . . 118.3(4) ?
C14 C13 C12 . . 120.5(4) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 119.9(4) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C10 . . 121.5(3) ?
C14 C15 H15 . . 119.3 ?
C10 C15 H15 . . 119.3 ?
C7 C16 H16A . . 109.5 ?
C7 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C7 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N5 C17 C12 . . 176.9(5) ?
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 . 2.1642(10) y
Ni1 S2 3_765 2.1642(10) ?
Ni1 S1 . 2.1735(9) y
Ni1 S1 3_765 2.1735(9) ?
S1 C2 . 1.746(4) ?
S2 C3 . 1.732(3) ?
N1 C1 . 1.129(5) ?
N2 C4 . 1.147(5) ?
C1 C2 . 1.440(5) ?
C2 C3 . 1.327(5) ?
C3 C4 . 1.434(5) ?
N3 C5 . 1.316(4) ?
N3 C8 . 1.353(4) ?
N3 C9 . 1.497(4) ?
N4 C7 . 1.311(5) ?
N4 C6 . 1.322(5) ?
N5 C17 . 1.125(5) ?
C5 C6 . 1.369(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.365(5) ?
C7 C16 . 1.514(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.494(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C15 . 1.380(5) ?
C10 C11 . 1.382(5) ?
C11 C12 . 1.390(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.384(5) ?
C12 C17 . 1.441(5) ?
C13 C14 . 1.355(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.376(5) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 N2 1_655 0.93 2.50 3.338(5) 151
C8 H8 N5 3_766 0.93 2.43 3.333(5) 163
C9 H9B N2 1_655 0.97 2.44 3.356(5) 157
