#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/87/2208729.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_2208729
loop_
_publ_author_name
'Chun-Lin Ni'
'Ming-Guo Liu'
_publ_section_title
;
 1-(2-Chlorobenzyl)-2-methylpyridinium
 bis(maleonitriledithiolato)nickelate(III)
;
_journal_coeditor_code           SJ2027
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m936
_journal_page_last               m938
_journal_paper_doi               10.1107/S1600536806010993
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '(C13 H13 Cl N)][Ni (C4 N2 S2)2]'
_chemical_formula_moiety         'C13 H13 Cl N +, C8 N4 Ni S4 -'
_chemical_formula_sum            'C21 H13 Cl N5 Ni S4'
_chemical_formula_weight         557.76
_chemical_name_systematic
;
1-(2-Chlorobenzyl)-2-methylpyridinium) bis(maleonitriledithiolate)
nickel(III)
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.7000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.99500(10)
_cell_length_b                   26.658(5)
_cell_length_c                   13.013(3)
_cell_measurement_reflns_used    977
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.36
_cell_measurement_theta_min      2.80
_cell_volume                     2357.5(7)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11580
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.310
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+1.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1571
_reflns_number_gt                3364
_reflns_number_total             4141
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2027.cif
_cod_data_source_block           I
_cod_original_cell_volume        2357.5(8)
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               2208729
_cod_database_fobs_code          2208729
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 0.20130(9) 0.02370(2) 0.43111(4) 0.0423(2) Uani d . 1
Cl Cl1 0.9482(2) 0.09158(7) 0.96539(17) 0.0928(6) Uani d . 1
S S1 0.22787(19) 0.09234(4) 0.51987(10) 0.0484(3) Uani d . 1
S S2 0.0970(2) 0.06190(5) 0.28295(10) 0.0524(3) Uani d . 1
S S3 0.1927(2) -0.04437(5) 0.34274(10) 0.0551(4) Uani d . 1
S S4 0.29778(19) -0.01483(5) 0.57829(9) 0.0497(3) Uani d . 1
N N1 0.1630(9) 0.22900(19) 0.4812(4) 0.0834(16) Uani d . 1
N N2 -0.0250(10) 0.1887(2) 0.1728(5) 0.0919(18) Uani d . 1
N N3 0.2877(9) -0.1796(2) 0.3737(5) 0.0926(18) Uani d . 1
N N4 0.4247(8) -0.14105(19) 0.6896(4) 0.0789(15) Uani d . 1
N N5 0.4045(7) 0.18378(15) 0.8720(4) 0.0572(11) Uani d . 1
C C1 0.1552(8) 0.1887(2) 0.4560(4) 0.0560(13) Uani d . 1
C C2 0.1496(7) 0.13708(17) 0.4233(4) 0.0456(11) Uani d . 1
C C3 0.0919(7) 0.12355(17) 0.3205(4) 0.0454(11) Uani d . 1
C C4 0.0269(9) 0.1604(2) 0.2386(5) 0.0615(14) Uani d . 1
C C5 0.2754(9) -0.1398(2) 0.4032(5) 0.0631(14) Uani d . 1
C C6 0.2638(7) -0.08920(17) 0.4381(4) 0.0480(12) Uani d . 1
C C7 0.3114(7) -0.07622(17) 0.5423(4) 0.0445(11) Uani d . 1
C C8 0.3749(8) -0.11265(19) 0.6244(4) 0.0533(12) Uani d . 1
C C9 0.3743(8) 0.07761(19) 0.8421(5) 0.0641(15) Uani d . 1
H H9 0.2657 0.0984 0.8193 0.077 Uiso calc R 1
C C10 0.3505(10) 0.0264(2) 0.8351(5) 0.0683(16) Uani d . 1
H H10 0.2265 0.0125 0.8089 0.082 Uiso calc R 1
C C11 0.5123(11) -0.0038(2) 0.8672(4) 0.0687(17) Uani d . 1
H H11 0.4974 -0.0385 0.8620 0.082 Uiso calc R 1
C C12 0.6932(10) 0.0159(2) 0.9064(4) 0.0640(15) Uani d . 1
H H12 0.8019 -0.0051 0.9268 0.077 Uiso calc R 1
C C13 0.7152(8) 0.0667(2) 0.9157(4) 0.0580(13) Uani d . 1
C C14 0.5577(8) 0.09867(19) 0.8825(4) 0.0556(13) Uani d . 1
C C15 0.5910(8) 0.1552(2) 0.8865(5) 0.0684(16) Uani d . 1
H H15A 0.6770 0.1640 0.9541 0.082 Uiso calc R 1
H H15B 0.6565 0.1646 0.8315 0.082 Uiso calc R 1
C C16 0.3278(10) 0.2031(2) 0.7753(5) 0.0743(17) Uani d . 1
H H16 0.3917 0.1985 0.7209 0.089 Uiso calc R 1
C C17 0.1596(11) 0.2289(2) 0.7579(6) 0.086(2) Uani d . 1
H H17 0.1058 0.2421 0.6913 0.103 Uiso calc R 1
C C18 0.0658(10) 0.2358(2) 0.8385(6) 0.0775(18) Uani d . 1
H H18 -0.0521 0.2535 0.8258 0.093 Uiso calc R 1
C C19 0.1436(9) 0.2172(2) 0.9357(6) 0.0702(16) Uani d . 1
H H19 0.0814 0.2225 0.9906 0.084 Uiso calc R 1
C C20 0.3197(9) 0.18967(18) 0.9533(4) 0.0608(14) Uani d . 1
C C21 0.4088(11) 0.1680(3) 1.0561(5) 0.087(2) Uani d . 1
H H21A 0.4083 0.1321 1.0506 0.130 Uiso calc R 1
H H21B 0.3350 0.1780 1.1062 0.130 Uiso calc R 1
H H21C 0.5418 0.1797 1.0793 0.130 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
S1 Ni1 S2 92.66(5) y
S3 Ni1 S2 87.68(5) y
S4 Ni1 S3 92.10(5) ?
S4 Ni1 S1 87.64(5) y
S3 Ni1 S1 176.66(6) y
S4 Ni1 S2 178.59(6) y
C2 S1 Ni1 103.01(17) y
C3 S2 Ni1 102.94(17) y
C6 S3 Ni1 103.66(17) y
C7 S4 Ni1 103.94(17) y
C20 N5 C16 122.7(5) ?
C20 N5 C15 120.1(5) ?
C16 N5 C15 117.2(5) ?
N1 C1 C2 178.7(6) ?
C3 C2 C1 122.0(4) ?
C3 C2 S1 120.4(4) ?
C1 C2 S1 117.6(4) ?
C2 C3 C4 121.2(5) ?
C2 C3 S2 121.0(4) ?
C4 C3 S2 117.8(4) ?
N2 C4 C3 178.8(7) ?
N3 C5 C6 178.2(7) ?
C7 C6 C5 122.4(5) ?
C7 C6 S3 120.4(4) ?
C5 C6 S3 117.2(4) ?
C6 C7 C8 121.9(5) ?
C6 C7 S4 119.9(4) ?
C8 C7 S4 118.1(4) ?
N4 C8 C7 179.4(6) ?
C10 C9 C14 120.9(6) ?
C10 C9 H9 119.5 ?
C14 C9 H9 119.5 ?
C11 C10 C9 119.0(6) ?
C11 C10 H10 120.5 ?
C9 C10 H10 120.5 ?
C12 C11 C10 121.1(5) ?
C12 C11 H11 119.4 ?
C10 C11 H11 119.4 ?
C11 C12 C13 119.6(6) ?
C11 C12 H12 120.2 ?
C13 C12 H12 120.2 ?
C12 C13 C14 121.4(6) ?
C12 C13 Cl1 119.3(5) ?
C14 C13 Cl1 119.3(4) y
C13 C14 C9 117.9(5) ?
C13 C14 C15 119.8(5) ?
C9 C14 C15 122.3(5) y
N5 C15 C14 112.4(4) y
N5 C15 H15A 109.1 ?
C14 C15 H15A 109.1 ?
N5 C15 H15B 109.1 ?
C14 C15 H15B 109.1 ?
H15A C15 H15B 107.9 ?
C17 C16 N5 119.6(6) ?
C17 C16 H16 120.2 ?
N5 C16 H16 120.2 ?
C16 C17 C18 120.1(7) ?
C16 C17 H17 120.0 ?
C18 C17 H17 120.0 ?
C19 C18 C17 120.4(6) ?
C19 C18 H18 119.8 ?
C17 C18 H18 119.8 ?
C18 C19 C20 119.2(6) ?
C18 C19 H19 120.4 ?
C20 C19 H19 120.4 ?
N5 C20 C19 117.9(5) ?
N5 C20 C21 120.4(6) y
C19 C20 C21 121.6(6) ?
C20 C21 H21A 109.5 ?
C20 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C20 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 S1 2.1484(13) y
Ni1 S2 2.1496(14) y
Ni1 S3 2.1416(14) y
Ni1 S4 2.1369(14) y
S1 C2 1.725(5) y
S2 C3 1.717(5) y
S3 C6 1.710(5) y
S4 C7 1.711(5) y
N1 C1 1.122(7) y
N2 C4 1.135(7) y
N3 C5 1.140(7) y
N4 C8 1.129(7) y
N5 C20 1.338(7) ?
N5 C16 1.348(8) ?
N5 C15 1.485(7) y
C14 C15 1.523(7) y
C1 C2 1.438(7) y
C2 C3 1.352(7) y
C3 C4 1.441(7) y
C5 C6 1.431(7) y
C6 C7 1.363(7) y
C7 C8 1.434(7) y
Cl1 C13 1.737(6) y
C9 C10 1.376(7) ?
C9 C14 1.385(8) ?
C9 H9 0.9300 ?
C10 C11 1.372(8) ?
C10 H10 0.9300 ?
C11 C12 1.353(8) ?
C11 H11 0.9300 ?
C12 C13 1.365(7) ?
C12 H12 0.9300 ?
C13 C14 1.379(7) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C17 1.334(9) ?
C16 H16 0.9300 ?
C17 C18 1.374(9) ?
C17 H17 0.9300 ?
C18 C19 1.349(9) ?
C18 H18 0.9300 ?
C19 C20 1.405(8) ?
C19 H19 0.9300 ?
C20 C21 1.455(8) ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
