#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/84/2208494.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_2208494
loop_
_publ_author_name
'Ni, Chun-Lin'
'Liu, Ming-Guo'
_publ_section_title
;
 Bis[1-(4-bromobenzyl)-3-methylpyrazinium]
 bis(1,2-dicyanoethene-1,2-dithiolato-κ³S,S')nickelate(II)
;
_journal_coeditor_code           BH2003
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m767
_journal_page_last               m769
_journal_paper_doi               10.1107/S1600536806008373
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '(C12 H12 Br N2)2 [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         '2C12 H12 Br N2 + , C8 N4 Ni S4 2-'
_chemical_formula_sum            'C32 H24 Br2 N8 Ni S4'
_chemical_formula_weight         867.36
_chemical_name_systematic
;
Bis[1-(4-bromobenzyl)-3-methylpyrazinium]
bis(1,2-dicyanoethene-1,2-dithiolato-κ³S,S')nickelate(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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.692(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.182(2)
_cell_length_b                   15.944(4)
_cell_length_c                   15.384(4)
_cell_measurement_reflns_used    908
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.61
_cell_measurement_theta_min      2.88
_cell_volume                     1755.7(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0969
_diffrn_reflns_av_sigmaI/netI    0.0733
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8550
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.103
_exptl_absorpt_correction_T_max  0.628
_exptl_absorpt_correction_T_min  0.480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.816
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0649P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2162
_reflns_number_total             3085
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2003.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2208494
_cod_database_fobs_code          2208494
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 0.5000 0.0000 0.0406(2) Uani d S 1
S S1 0.14451(15) 0.41032(6) -0.07610(7) 0.0509(3) Uani d . 1
S S2 0.25519(15) 0.50956(6) 0.08510(7) 0.0550(3) Uani d . 1
N N1 0.0389(8) 0.2542(3) -0.2512(3) 0.0980(16) Uani d . 1
N N2 0.4563(8) 0.6344(3) 0.2724(3) 0.1075(18) Uani d . 1
Br Br1 0.14550(7) 0.08035(4) -0.02801(4) 0.0853(2) Uani d . 1
C C2 0.0105(7) 0.3100(3) -0.2089(3) 0.0610(12) Uani d . 1
C C1 -0.0283(6) 0.3780(2) -0.1533(2) 0.0477(10) Uani d . 1
C C4 0.3445(8) 0.6136(3) 0.2216(3) 0.0674(13) Uani d . 1
C C3 0.2009(6) 0.5865(2) 0.1574(3) 0.0511(10) Uani d . 1
C C5 0.7388(6) 0.3799(3) 0.1473(3) 0.0570(11) Uani d . 1
H H5 0.6296 0.3769 0.1105 0.068 Uiso calc R 1
C C6 0.7544(7) 0.4357(3) 0.2145(3) 0.0631(12) Uani d . 1
H H6 0.6533 0.4706 0.2221 0.076 Uiso calc R 1
C C7 1.0480(7) 0.3937(3) 0.2553(3) 0.0544(11) Uani d . 1
C C8 1.0379(6) 0.3373(2) 0.1877(3) 0.0542(10) Uani d . 1
H H8 1.1409 0.3041 0.1785 0.065 Uiso calc R 1
C C9 0.8800(6) 0.2701(3) 0.0595(3) 0.0618(12) Uani d . 1
H H9A 0.9106 0.3009 0.0082 0.074 Uiso calc R 1
H H9B 0.9766 0.2283 0.0720 0.074 Uiso calc R 1
C C10 0.6972(6) 0.2261(2) 0.0392(2) 0.0461(9) Uani d . 1
C C11 0.5613(7) 0.2574(3) -0.0204(3) 0.0667(13) Uani d . 1
H H11 0.5804 0.3086 -0.0474 0.080 Uiso calc R 1
C C12 0.3980(6) 0.2143(3) -0.0407(3) 0.0679(13) Uani d . 1
H H12 0.3069 0.2359 -0.0810 0.081 Uiso calc R 1
C C13 0.3713(6) 0.1396(3) -0.0011(3) 0.0534(10) Uani d . 1
C C14 0.5055(6) 0.1064(2) 0.0579(3) 0.0537(10) Uani d . 1
H H14 0.4857 0.0550 0.0843 0.064 Uiso calc R 1
C C15 0.6691(6) 0.1495(2) 0.0777(2) 0.0502(10) Uani d . 1
H H15 0.7609 0.1271 0.1170 0.060 Uiso calc R 1
C C16 1.2231(8) 0.4018(3) 0.3144(3) 0.0795(15) Uani d . 1
H H16A 1.2568 0.4599 0.3203 0.119 Uiso calc R 1
H H16B 1.3220 0.3715 0.2901 0.119 Uiso calc R 1
H H16C 1.2027 0.3792 0.3706 0.119 Uiso calc R 1
N N3 0.8821(5) 0.32974(19) 0.13510(19) 0.0473(8) Uani d . 1
N N4 0.9049(6) 0.4432(2) 0.2696(2) 0.0621(10) 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'
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'
Br Br -0.2901 2.4595 '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_565 . 180.00(5)
S1 Ni1 S2 3_565 3_565 87.36(4)
S1 Ni1 S2 . 3_565 92.64(4)
S1 Ni1 S2 3_565 . 92.64(4)
S1 Ni1 S2 . . 87.36(4)
S2 Ni1 S2 3_565 . 180.00(5)
C1 S1 Ni1 . . 102.68(15)
C3 S2 Ni1 . . 102.43(15)
N1 C2 C1 . . 177.7(5)
C3 C1 C2 3_565 . 120.8(4)
C3 C1 S1 3_565 . 120.7(3)
C2 C1 S1 . . 118.4(3)
N2 C4 C3 . . 179.4(7)
C1 C3 C4 3_565 . 120.5(4)
C1 C3 S2 3_565 . 121.3(3)
C4 C3 S2 . . 118.1(4)
N3 C5 C6 . . 118.9(4)
N3 C5 H5 . . 120.5
C6 C5 H5 . . 120.5
N4 C6 C5 . . 123.9(5)
N4 C6 H6 . . 118.0
C5 C6 H6 . . 118.0
N4 C7 C8 . . 121.4(4)
N4 C7 C16 . . 118.2(4)
C8 C7 C16 . . 120.4(4)
N3 C8 C7 . . 120.6(4)
N3 C8 H8 . . 119.7
C7 C8 H8 . . 119.7
C10 C9 N3 . . 114.3(3)
C10 C9 H9A . . 108.7
N3 C9 H9A . . 108.7
C10 C9 H9B . . 108.7
N3 C9 H9B . . 108.7
H9A C9 H9B . . 107.6
C15 C10 C11 . . 119.1(4)
C15 C10 C9 . . 118.8(4)
C11 C10 C9 . . 122.0(4)
C12 C11 C10 . . 121.0(4)
C12 C11 H11 . . 119.5
C10 C11 H11 . . 119.5
C13 C12 C11 . . 119.1(4)
C13 C12 H12 . . 120.4
C11 C12 H12 . . 120.4
C12 C13 C14 . . 121.1(4)
C12 C13 Br1 . . 119.2(3)
C14 C13 Br1 . . 119.6(3)
C13 C14 C15 . . 119.6(4)
C13 C14 H14 . . 120.2
C15 C14 H14 . . 120.2
C14 C15 C10 . . 120.1(4)
C14 C15 H15 . . 120.0
C10 C15 H15 . . 120.0
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
C5 N3 C8 . . 118.8(4)
C5 N3 C9 . . 122.1(4)
C8 N3 C9 . . 118.8(4)
C6 N4 C7 . . 116.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ni1 S1 3_565 2.1659(10)
Ni1 S1 . 2.1659(10)
Ni1 S2 3_565 2.1687(11)
Ni1 S2 . 2.1687(11)
S1 C1 . 1.724(4)
S2 C3 . 1.722(4)
N1 C2 . 1.131(5)
N2 C4 . 1.124(6)
Br1 C13 . 1.893(4)
C2 C1 . 1.423(6)
C1 C3 3_565 1.360(6)
C4 C3 . 1.435(6)
C3 C1 3_565 1.360(6)
C5 N3 . 1.328(5)
C5 C6 . 1.362(6)
C5 H5 . 0.9300
C6 N4 . 1.324(6)
C6 H6 . 0.9300
C7 N4 . 1.328(6)
C7 C8 . 1.373(6)
C7 C16 . 1.495(6)
C8 N3 . 1.332(5)
C8 H8 . 0.9300
C9 C10 . 1.498(5)
C9 N3 . 1.502(5)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C15 . 1.378(5)
C10 C11 . 1.378(6)
C11 C12 . 1.373(6)
C11 H11 . 0.9300
C12 C13 . 1.359(6)
C12 H12 . 0.9300
C13 C14 . 1.374(6)
C14 C15 . 1.374(5)
C14 H14 . 0.9300
C15 H15 . 0.9300
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
