#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/31/2233153.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_2233153
loop_
_publ_author_name
'Kapoor, Sanjay'
'Kour, Ramandeep'
'Sachar, Renu'
'Kant, Rajni'
'Gupta, Vivek K.'
'Kapoor, Kamini'
_publ_section_title
;
 Bis(O-ethyl
 dithiocarbonato-κ²S,S')bis(pyridine-3-carbonitrile-κN¹)nickel(II)
;
_journal_coeditor_code           GK2438
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m58
_journal_paper_doi               10.1107/S1600536811053475
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ni (C3 H5 O S2)2 (C6 H4 N2)2]'
_chemical_formula_moiety         'C18 H18 N4 Ni O2 S4'
_chemical_formula_sum            'C18 H18 N4 Ni O2 S4'
_chemical_formula_weight         509.31
_chemical_name_systematic
;
Bis(O-ethyl
dithiocarbonato-κ²S,S')bis(pyridine-3-carbonitrile-
κN¹)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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.916(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7302(2)
_cell_length_b                   18.8959(5)
_cell_length_c                   8.7242(2)
_cell_measurement_reflns_used    10361
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.03
_cell_measurement_theta_min      3.64
_cell_volume                     1103.58(5)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'PLATON (Spek, 2009) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Sapphire3'
_diffrn_measurement_method       '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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18847
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.279
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2007)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0253
_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)+(0.0208P)²+0.7659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0604
_reflns_number_gt                1723
_reflns_number_total             1930
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2438.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233153
_cod_database_fobs_code          2233153
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_symmetry_multiplicity
Ni Ni1 0.0000 0.5000 0.5000 0.02943(12) Uani d S 1 2
S S1 0.33453(8) 0.46692(3) 0.60894(6) 0.03356(14) Uani d . 1 1
S S2 0.03241(8) 0.54100(3) 0.23794(7) 0.03737(15) Uani d . 1 1
O O1 0.3099(2) 0.42097(8) 0.89474(17) 0.0404(4) Uani d . 1 1
N N1 0.0499(3) 0.60555(9) 0.5796(2) 0.0340(4) Uani d . 1 1
N N2 -0.3300(4) 0.76898(12) 0.8455(3) 0.0691(7) Uani d . 1 1
C C2 -0.0808(3) 0.63914(11) 0.6579(3) 0.0368(5) Uani d . 1 1
H H2 -0.1910 0.6143 0.6856 0.044 Uiso calc R 1 1
C C3 -0.0591(3) 0.71000(12) 0.6999(3) 0.0401(5) Uani d . 1 1
C C4 0.1050(4) 0.74716(13) 0.6592(3) 0.0484(6) Uani d . 1 1
H H4 0.1222 0.7947 0.6846 0.058 Uiso calc R 1 1
C C5 0.2413(4) 0.71212(13) 0.5805(3) 0.0469(6) Uani d . 1 1
H H5 0.3542 0.7354 0.5532 0.056 Uiso calc R 1 1
C C6 0.2086(3) 0.64182(12) 0.5425(3) 0.0383(5) Uani d . 1 1
H H6 0.3014 0.6186 0.4885 0.046 Uiso calc R 1 1
C C7 -0.2097(4) 0.74323(13) 0.7818(3) 0.0497(6) Uani d . 1 1
C C8 0.2162(3) 0.44638(11) 0.7649(2) 0.0319(5) Uani d . 1 1
C C9 0.5252(3) 0.41173(13) 0.9032(3) 0.0446(6) Uani d . 1 1
H H9A 0.5889 0.4561 0.8807 0.054 Uiso calc R 1 1
H H9B 0.5583 0.3767 0.8285 0.054 Uiso calc R 1 1
C C10 0.5962(4) 0.38776(14) 1.0625(3) 0.0520(6) Uani d . 1 1
H H10A 0.5554 0.4213 1.1357 0.078 Uiso calc R 1 1
H H10B 0.7392 0.3842 1.0732 0.078 Uiso calc R 1 1
H H10C 0.5395 0.3423 1.0810 0.078 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'
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
N1 Ni1 N1 3_566 . 180.00(3)
N1 Ni1 S1 3_566 . 89.73(5)
N1 Ni1 S1 . . 90.27(5)
N1 Ni1 S1 3_566 3_566 90.27(5)
N1 Ni1 S1 . 3_566 89.73(5)
S1 Ni1 S1 . 3_566 180.0
N1 Ni1 S2 3_566 3_566 88.96(5)
N1 Ni1 S2 . 3_566 91.04(5)
S1 Ni1 S2 . 3_566 73.831(18)
S1 Ni1 S2 3_566 3_566 106.169(18)
N1 Ni1 S2 3_566 . 91.04(5)
N1 Ni1 S2 . . 88.96(5)
S1 Ni1 S2 . . 106.169(18)
S1 Ni1 S2 3_566 . 73.831(18)
S2 Ni1 S2 3_566 . 180.0
C8 S1 Ni1 . . 83.10(7)
C8 S2 Ni1 3_566 . 82.80(7)
C8 O1 C9 . . 118.02(17)
C2 N1 C6 . . 117.86(19)
C2 N1 Ni1 . . 121.65(14)
C6 N1 Ni1 . . 120.33(15)
N1 C2 C3 . . 122.5(2)
N1 C2 H2 . . 118.7
C3 C2 H2 . . 118.7
C4 C3 C2 . . 119.0(2)
C4 C3 C7 . . 121.7(2)
C2 C3 C7 . . 119.3(2)
C5 C4 C3 . . 118.4(2)
C5 C4 H4 . . 120.8
C3 C4 H4 . . 120.8
C4 C5 C6 . . 119.1(2)
C4 C5 H5 . . 120.5
C6 C5 H5 . . 120.5
N1 C6 C5 . . 123.1(2)
N1 C6 H6 . . 118.4
C5 C6 H6 . . 118.4
N2 C7 C3 . . 179.3(3)
O1 C8 S2 . 3_566 116.53(15)
O1 C8 S1 . . 123.21(15)
S2 C8 S1 3_566 . 120.26(12)
O1 C9 C10 . . 107.76(19)
O1 C9 H9A . . 110.2
C10 C9 H9A . . 110.2
O1 C9 H9B . . 110.2
C10 C9 H9B . . 110.2
H9A C9 H9B . . 108.5
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
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 N1 . 2.1273(17) y
Ni1 S1 . 2.4335(5) y
Ni1 S2 . 2.4450(6) y
S1 C8 . 1.691(2) ?
S2 C8 3_566 1.688(2) ?
O1 C8 . 1.328(2) ?
O1 C9 . 1.454(3) ?
N1 C2 . 1.329(3) ?
N1 C6 . 1.336(3) ?
N2 C7 . 1.138(3) ?
C2 C3 . 1.392(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.385(3) ?
C3 C7 . 1.442(3) ?
C4 C5 . 1.372(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C9 C10 . 1.493(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 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
_geom_hbond_publ_flag
C9 H9A S2 3_666 0.97 2.85 3.455(2) 121 yes
C10 H10C N2 3_567 0.96 2.65 3.595(4) 169 yes
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_4
_geom_torsion
N1 Ni1 S1 C8 3_566 . -88.58(9)
N1 Ni1 S1 C8 . . 91.42(9)
S2 Ni1 S1 C8 3_566 . 0.42(7)
S2 Ni1 S1 C8 . . -179.58(7)
N1 Ni1 S2 C8 3_566 3_566 90.39(9)
N1 Ni1 S2 C8 . 3_566 -89.61(9)
S1 Ni1 S2 C8 . 3_566 -179.58(7)
S1 Ni1 S2 C8 3_566 3_566 0.42(7)
S1 Ni1 N1 C2 . . -130.63(16)
S1 Ni1 N1 C2 3_566 . 49.37(16)
S2 Ni1 N1 C2 3_566 . -56.80(16)
S2 Ni1 N1 C2 . . 123.20(16)
S1 Ni1 N1 C6 . . 54.10(16)
S1 Ni1 N1 C6 3_566 . -125.90(16)
S2 Ni1 N1 C6 3_566 . 127.93(16)
S2 Ni1 N1 C6 . . -52.07(16)
C6 N1 C2 C3 . . 0.8(3)
Ni1 N1 C2 C3 . . -174.57(16)
N1 C2 C3 C4 . . -0.1(3)
N1 C2 C3 C7 . . 178.6(2)
C2 C3 C4 C5 . . -0.9(4)
C7 C3 C4 C5 . . -179.6(2)
C3 C4 C5 C6 . . 1.2(4)
C2 N1 C6 C5 . . -0.5(3)
Ni1 N1 C6 C5 . . 174.93(18)
C4 C5 C6 N1 . . -0.5(4)
C9 O1 C8 S2 . 3_566 -177.93(16)
C9 O1 C8 S1 . . 1.2(3)
Ni1 S1 C8 O1 . . -179.72(18)
Ni1 S1 C8 S2 . 3_566 -0.67(12)
C8 O1 C9 C10 . . 176.01(19)
