#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012230.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_2012230
loop_
_publ_author_name
'Ren, Xiao-Ming'
'Li, Hai-Fang'
'Wu, Pei-Heng'
'Meng, Qing-Jin'
_publ_section_title
;
 2-Methyl-1-(4-nitrobenzyl)pyridinium
 bis(maleonitriledithiolato)nickelate(III)
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1022
_journal_page_last               1024
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          '(C13 H13 N2 O2) [Ni (C4 N2 S2)2]'
_chemical_formula_moiety         'C13 H13 N2 O2 + , C8 N4 Ni S4 -'
_chemical_formula_sum            'C21 H13 N6 Ni O2 S4'
_chemical_formula_weight         568.32
_chemical_name_systematic
;
 ?
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.510(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2343(13)
_cell_length_b                   26.691(4)
_cell_length_c                   12.745(2)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.41
_cell_measurement_theta_min      7.40
_cell_volume                     2382.4(7)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'SHELXTL (Sheldrick, 1997b)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       2\q/\w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0432
_diffrn_reflns_av_sigmaI/netI    .0628
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5502
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        6.57
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_T_max  .7153
_exptl_absorpt_correction_T_min  .6460
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .30
_refine_diff_density_max         .411
_refine_diff_density_min         -.549
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          .0917
_refine_ls_R_factor_gt           .0479
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0441P)^2^+1.9841P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1241
_reflns_number_gt                2775
_reflns_number_total             4202
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ta1318.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2012230
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 .26470(8) .48959(2) .07147(4) .04639(18) Uani d . 1 Ni
S1 .3526(2) .55562(5) .16616(10) .0613(4) Uani d . 1 S
S2 .24845(17) .52891(5) -.07804(9) .0501(3) Uani d . 1 S
S3 .18266(17) .42138(4) -.01909(9) .0501(3) Uani d . 1 S
S4 .2766(2) .45348(5) .22338(9) .0584(3) Uani d . 1 S
O1 .6681(6) .43868(16) .4447(4) .0966(14) Uani d . 1 O
O2 .8831(7) .42987(15) .3554(3) .0876(12) Uani d . 1 O
N1 .4952(7) .68572(18) .1486(4) .0816(15) Uani d . 1 N
N2 .3347(8) .65502(18) -.1792(4) .0811(14) Uani d . 1 N
N3 .1068(9) .28587(18) .0303(4) .0927(17) Uani d . 1 N
N4 .1986(7) .32979(18) .3370(4) .0753(13) Uani d . 1 N
N5 .7817(7) .45542(17) .3965(4) .0647(12) Uani d . 1 N
N6 1.0602(6) .68552(14) .4157(3) .0523(10) Uani d . 1 N
C1 .4346(8) .6482(2) .1118(4) .0609(13) Uani d . 1 C
C2 .3642(6) .60017(17) .0715(4) .0501(11) Uani d . 1 C
C3 .3156(6) .58855(17) -.0364(4) .0473(11) Uani d . 1 C
C4 .3256(7) .62569(19) -.1161(4) .0583(13) Uani d . 1 C
C5 .1356(8) .3272(2) .0513(4) .0618(13) Uani d . 1 C
C6 .1759(6) .37860(17) .0813(4) .0477(11) Uani d . 1 C
C7 .2126(6) .39294(17) .1869(4) .0494(11) Uani d . 1 C
C8 .2054(7) .35772(19) .2707(4) .0568(13) Uani d . 1 C
C9 .9462(7) .58158(19) .3389(4) .0613(13) Uani d . 1 C
H9 1.0330 .5957 .3045 .074 Uiso calc R 1 H
C10 .9262(8) .53067(19) .3406(4) .0608(13) Uani d . 1 C
H10 .9982 .5100 .3075 .073 Uiso calc R 1 H
C11 .7982(7) .51069(17) .3920(4) .0517(11) Uani d . 1 C
C12 .6876(8) .5404(2) .4396(4) .0693(15) Uani d . 1 C
H12 .5997 .5262 .4730 .083 Uiso calc R 1 H
C13 .7088(7) .59123(19) .4368(4) .0629(14) Uani d . 1 C
H13 .6343 .6118 .4685 .076 Uiso calc R 1 H
C14 .8384(7) .61226(17) .3879(4) .0504(11) Uani d . 1 C
C15 .8572(7) .66882(18) .3887(4) .0625(13) Uani d . 1 C
H15A .7923 .6818 .3179 .075 Uiso calc R 1 H
H15B .7950 .6827 .4413 .075 Uiso calc R 1 H
C16 1.1559(8) .67962(18) .5235(4) .0599(13) Uani d . 1 C
H16 1.0944 .6643 .5709 .072 Uiso calc R 1 H
C17 1.3343(8) .6955(2) .5601(4) .0687(15) Uani d . 1 C
H17 1.3981 .6911 .6325 .082 Uiso calc R 1 H
C18 1.4249(8) .71874(19) .4887(5) .0694(15) Uani d . 1 C
H18 1.5483 .7311 .5134 .083 Uiso calc R 1 H
C19 1.3312(8) .72311(19) .3829(5) .0679(15) Uani d . 1 C
H19 1.3929 .7375 .3346 .081 Uiso calc R 1 H
C20 1.1436(9) .70634(19) .3451(4) .0645(14) Uani d . 1 C
C21 1.0402(10) .7121(2) .2316(4) .100(2) Uani d . 1 C
H21A .9890 .6803 .2033 .150 Uiso calc R 1 H
H21B 1.1258 .7241 .1907 .150 Uiso calc R 1 H
H21C .9378 .7356 .2263 .150 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Ni1 .0474(3) .0461(3) .0470(3) .0024(3) .0143(3) .0010(3)
S1 .0812(9) .0543(8) .0478(7) -.0042(7) .0149(6) -.0017(6)
S2 .0540(7) .0480(7) .0477(6) .0005(6) .0118(5) .0002(5)
S3 .0558(7) .0501(7) .0452(6) -.0025(6) .0141(5) .0014(5)
S4 .0750(9) .0548(8) .0477(6) -.0006(7) .0194(6) -.0014(5)
O1 .095(3) .066(3) .134(4) -.012(2) .039(3) .014(3)
O2 .117(4) .053(2) .095(3) .007(2) .029(3) -.007(2)
N1 .110(4) .054(3) .074(3) -.012(3) .008(3) -.005(2)
N2 .116(4) .065(3) .063(3) -.004(3) .024(3) .006(2)
N3 .152(5) .053(3) .073(3) -.025(3) .029(3) -.001(2)
N4 .095(4) .073(3) .061(3) .000(3) .025(3) .019(2)
N5 .070(3) .051(3) .065(3) -.004(2) .001(2) .000(2)
N6 .062(3) .040(2) .060(2) .0028(19) .024(2) -.0011(18)
C1 .068(4) .057(3) .056(3) .000(3) .012(3) .002(3)
C2 .049(3) .045(3) .056(3) -.003(2) .013(2) -.005(2)
C3 .041(2) .052(3) .049(3) .003(2) .012(2) -.001(2)
C4 .068(4) .057(3) .050(3) .002(3) .014(3) .001(3)
C5 .079(4) .056(3) .050(3) -.008(3) .016(3) .005(2)
C6 .042(3) .051(3) .051(3) -.002(2) .014(2) .004(2)
C7 .051(3) .049(3) .050(3) .002(2) .014(2) .003(2)
C8 .059(3) .056(3) .055(3) .001(3) .014(2) .002(3)
C9 .070(3) .057(3) .064(3) -.007(3) .029(3) -.003(2)
C10 .078(4) .051(3) .056(3) .002(3) .022(3) -.011(2)
C11 .056(3) .041(3) .052(3) -.004(2) .001(2) -.004(2)
C12 .070(4) .057(4) .088(4) -.009(3) .032(3) -.008(3)
C13 .063(3) .052(3) .081(4) -.001(3) .031(3) -.011(3)
C14 .053(3) .044(3) .052(3) .001(2) .008(2) -.001(2)
C15 .053(3) .050(3) .082(4) .000(2) .013(3) -.003(3)
C16 .065(3) .057(3) .061(3) .005(3) .023(3) .005(2)
C17 .076(4) .073(4) .055(3) .008(3) .013(3) -.007(3)
C18 .066(4) .059(3) .085(4) -.006(3) .022(3) -.011(3)
C19 .067(4) .051(3) .092(4) -.007(3) .032(3) .000(3)
C20 .093(4) .047(3) .056(3) .013(3) .025(3) .003(2)
C21 .134(6) .101(5) .060(4) .025(4) .016(4) .018(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni .3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
_geom_angle_publ_flag
S1 Ni1 S4 85.53(5) yes
S1 Ni1 S2 92.31(5) yes
S4 Ni1 S2 177.38(6) ?
S1 Ni1 S3 177.84(6) ?
S4 Ni1 S3 92.70(5) yes
S2 Ni1 S3 89.49(5) yes
C2 S1 Ni1 103.57(16) ?
C3 S2 Ni1 103.34(16) ?
C6 S3 Ni1 102.53(16) ?
C7 S4 Ni1 103.41(16) ?
O2 N5 O1 124.4(5) ?
O2 N5 C11 118.7(5) ?
O1 N5 C11 116.9(5) ?
C20 N6 C16 121.5(5) ?
C20 N6 C15 124.0(4) ?
C16 N6 C15 114.5(4) ?
N1 C1 C2 176.8(6) yes
C3 C2 C1 123.0(4) ?
C3 C2 S1 120.4(4) ?
C1 C2 S1 116.5(3) ?
C2 C3 C4 120.7(4) ?
C2 C3 S2 120.3(4) ?
C4 C3 S2 119.0(3) ?
N2 C4 C3 179.6(6) yes
N3 C5 C6 178.0(6) yes
C7 C6 C5 120.6(4) ?
C7 C6 S3 120.9(4) ?
C5 C6 S3 118.5(3) ?
C6 C7 C8 121.2(4) ?
C6 C7 S4 120.4(4) ?
C8 C7 S4 118.3(4) ?
N4 C8 C7 179.6(6) yes
C10 C9 C14 120.5(5) ?
C10 C9 H9 119.8 ?
C14 C9 H9 119.8 ?
C9 C10 C11 118.8(5) ?
C9 C10 H10 120.6 ?
C11 C10 H10 120.6 ?
C10 C11 C12 121.7(5) ?
C10 C11 N5 118.5(5) ?
C12 C11 N5 119.8(5) ?
C13 C12 C11 118.7(5) ?
C13 C12 H12 120.6 ?
C11 C12 H12 120.6 ?
C12 C13 C14 120.8(5) ?
C12 C13 H13 119.6 ?
C14 C13 H13 119.6 ?
C13 C14 C9 119.4(5) ?
C13 C14 C15 118.4(4) ?
C9 C14 C15 122.2(4) ?
N6 C15 C14 112.4(4) ?
N6 C15 H15A 109.1 ?
C14 C15 H15A 109.1 ?
N6 C15 H15B 109.1 ?
C14 C15 H15B 109.1 ?
H15A C15 H15B 107.9 ?
C17 C16 N6 120.9(5) ?
C17 C16 H16 119.5 ?
N6 C16 H16 119.5 ?
C16 C17 C18 119.2(5) ?
C16 C17 H17 120.4 ?
C18 C17 H17 120.4 ?
C19 C18 C17 119.3(5) ?
C19 C18 H18 120.4 ?
C17 C18 H18 120.4 ?
C18 C19 C20 121.1(5) ?
C18 C19 H19 119.4 ?
C20 C19 H19 119.4 ?
N6 C20 C19 118.0(5) ?
N6 C20 C21 120.6(6) ?
C19 C20 C21 121.4(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 2.1407(14) yes
Ni1 S4 2.1451(13) yes
Ni1 S2 2.1526(13) yes
Ni1 S3 2.1577(13) yes
S1 C2 1.711(5) yes
S2 C3 1.710(5) yes
S3 C6 1.725(4) yes
S4 C7 1.713(5) yes
O1 N5 1.227(6) ?
O2 N5 1.213(5) ?
N1 C1 1.147(6) ?
N2 C4 1.135(6) ?
N3 C5 1.142(6) ?
N4 C8 1.137(6) ?
N5 C11 1.482(6) ?
N6 C20 1.324(6) ?
N6 C16 1.384(6) ?
N6 C15 1.490(6) ?
C1 C2 1.426(7) ?
C2 C3 1.367(6) ?
C3 C4 1.435(7) ?
C5 C6 1.435(7) ?
C6 C7 1.360(6) ?
C7 C8 1.433(6) ?
C9 C10 1.367(7) ?
C9 C14 1.383(6) ?
C9 H9 .9300 ?
C10 C11 1.369(7) ?
C10 H10 .9300 ?
C11 C12 1.371(7) ?
C12 C13 1.368(7) ?
C12 H12 .9300 ?
C13 C14 1.370(6) ?
C13 H13 .9300 ?
C14 C15 1.515(6) ?
C15 H15A .9700 ?
C15 H15B .9700 ?
C16 C17 1.327(7) ?
C16 H16 .9300 ?
C17 C18 1.394(7) ?
C17 H17 .9300 ?
C18 C19 1.354(7) ?
C18 H18 .9300 ?
C19 C20 1.395(7) ?
C19 H19 .9300 ?
C20 C21 1.461(7) ?
C21 H21A .9600 ?
C21 H21B .9600 ?
C21 H21C .9600 ?
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
S4 Ni1 S1 C2 -179.74(17)
S2 Ni1 S1 C2 -1.23(17)
S3 Ni1 S1 C2 145.3(15)
S1 Ni1 S2 C3 .56(16)
S4 Ni1 S2 C3 35.0(13)
S3 Ni1 S2 C3 -178.24(16)
S1 Ni1 S3 C6 34.6(16)
S4 Ni1 S3 C6 -.27(16)
S2 Ni1 S3 C6 -178.83(16)
S1 Ni1 S4 C7 -179.58(17)
S2 Ni1 S4 C7 145.9(12)
S3 Ni1 S4 C7 -.82(17)
N1 C1 C2 C3 -156(11)
N1 C1 C2 S1 21(12)
Ni1 S1 C2 C3 1.9(4)
Ni1 S1 C2 C1 -175.2(3)
C1 C2 C3 C4 -2.8(7)
S1 C2 C3 C4 -179.8(4)
C1 C2 C3 S2 175.3(4)
S1 C2 C3 S2 -1.7(6)
Ni1 S2 C3 C2 .5(4)
Ni1 S2 C3 C4 178.6(3)
C2 C3 C4 N2 9E1(8)
S2 C3 C4 N2 -9E1(8)
N3 C5 C6 C7 -29(19)
N3 C5 C6 S3 150(19)
Ni1 S3 C6 C7 1.8(4)
Ni1 S3 C6 C5 -176.6(4)
C5 C6 C7 C8 -2.3(7)
S3 C6 C7 C8 179.4(4)
C5 C6 C7 S4 175.5(4)
S3 C6 C7 S4 -2.8(6)
Ni1 S4 C7 C6 2.2(4)
Ni1 S4 C7 C8 -179.9(3)
C6 C7 C8 N4 -8E1(7)
S4 C7 C8 N4 10E1(7)
C14 C9 C10 C11 -.2(8)
C9 C10 C11 C12 1.3(8)
C9 C10 C11 N5 -178.1(4)
O2 N5 C11 C10 .6(7)
O1 N5 C11 C10 178.8(5)
O2 N5 C11 C12 -178.8(5)
O1 N5 C11 C12 -.7(7)
C10 C11 C12 C13 -1.1(8)
N5 C11 C12 C13 178.3(5)
C11 C12 C13 C14 -.2(8)
C12 C13 C14 C9 1.3(8)
C12 C13 C14 C15 -179.3(5)
C10 C9 C14 C13 -1.1(8)
C10 C9 C14 C15 179.5(5)
C20 N6 C15 C14 109.5(5)
C16 N6 C15 C14 -73.2(5)
C13 C14 C15 N6 135.9(5)
C9 C14 C15 N6 -44.7(7)
C20 N6 C16 C17 1.1(7)
C15 N6 C16 C17 -176.2(5)
N6 C16 C17 C18 .5(8)
C16 C17 C18 C19 -2.2(8)
C17 C18 C19 C20 2.3(8)
C16 N6 C20 C19 -1.1(7)
C15 N6 C20 C19 176.0(4)
C16 N6 C20 C21 179.8(5)
C15 N6 C20 C21 -3.1(7)
C18 C19 C20 N6 -.6(8)
C18 C19 C20 C21 178.5(5)