Download citation
Download citation
link to html
In the title complex, 2-methyl-1-(4-nitro­benzyl)pyridinium bis(1,2-di­cyano­ethene-1,2-di­thiol­ato)­nickelate(III), (C13H13N2O2)[Ni(C4N2S2)2], the most prominent general structural feature of the complex is the completely segregated columnar stacks of anions and cations. Within the cation column, there may be stacking interactions between adjacent nitro groups and benzene rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101009064/ta1318sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101009064/ta1318Isup2.hkl
Contains datablock I

CCDC reference: 173342

Comment top

Recently, considerable interest has been focused on low-dimensional molecular solids with novel magnetic properties, such as spin-Peierls transitions (Brown et al., 1998) and room-temperature spin bistability (Fujita & Awaga, 1999). Our aim is to construct quasi-one-dimensional molecule-based magnetic materials formed by platelike maleonitriledithiolene anionic metal complexes [M(mnt)2]- (M is NiIII, PdIII or PtIII). These types of low-dimensional materials are associated with columnar crystallographic packing. Previous work has shown that the geometry of the counter-cations strongly influences the stacking structure of this type of material. Therefore, it is important to select particular counter-cations in order to obtain columnar crystallographic packing. The ground-state conformations of benzylpyridinium derivatives have been extensively investigated by many techniques, and results to date have indicated that the spatial orientation of the benzene and pyridine rings depends on both the electronic and the steric properties of the substituents on the aryl rings (Bulgarevich et al., 1994). The different conformations available to benzylpyridinium derivatives may lead to differences in the geometry of the cations, sufficient to influence the stacking structures of the complexes in the solid state. As a result, the ion-pair complexes consisting of [M(mnt)2]- anions and benzylpyridinium-derived cations present a unique opportunity for the systematic investigation of the fundamental relationship between the stacking structure in the solid and the substituents on the aryl rings. To test this idea, we prepared a series of complexes by systematically varying the substituents on the aryl rings, and found that it is possible to obtain completely separated anions and cations in columnar stacking structures. Herein, we report the crystal structure of the title compound, (I), which has columnar packing. \sch

In the anion of (I), the Ni atom exhibits square-planar coordination geometry involving four S atoms, and the five-membered nickel-containing rings are slightly puckered (Fig. 1), as has been found in other [M(mnt)2]n- structures (Plumlee et al., 1975). The average S—Ni—S bond angle within the five-membered ring is 92.50 (5)° and the average Ni—S bond distance is 2.1477 (13) Å. Other chemically equivalent but crystallographically non-equivalent bond distances within the anion differ by less than three s.u.'s and compare well with those found in [Ni(mnt)2]- complexes (Brunn et al., 1987). The anion is non-planar and the CN groups bend away from the plane of the four S atoms. The CN group with the largest deviation is C1N1, and the deviations from the plane defined by the four S atoms are 0.294 (6) Å for N1 and 0.167 (6) Å for C1. The cation adopts a conformation where the dihedral angle between the benzene ring and the C14/C15/N6 reference plane is 44.5 (4)°, and the pyridine ring is twisted towards the reference plane with a dihedral angle of 72.3 (4)°.

The most prominent general structural features of the complex are the completely segregated stacked columns of [Ni(mnt)2]- anions and 1-(4-nitrobenzyl)-2-methylpyridinium cations, as revealed by the projection along the crystallographic a axis in Fig. 2. Completely segregated stacked columns of [Ni(mnt)2]- anions have been infrequently reported (Hobi et al., 1996). The Ni···Ni distances are alternately 3.847 (1) and 4.281 (1) Å within the [Ni(mnt)2]- column. The nearest Ni···Ni contact between [Ni(mnt)2]- columns is much larger at 10.6 Å, and is larger than the Ni···Ni distance within the [Ni(mnt)2]- column. These results indicate that, compared with intracolumnar interactions, the Ni···Ni magnetic exchange interactions between columns may be neglected. Within the 1-(4-nitrobenzyl)-2-methylbenzylpyridinium cation column, the nitro group of one cation is stacked over the benzene ring of an adjacent cation (Fig. 3). This type of packing structure is often found in nitrobenzene derivatives (Harrowfield et al., 1998). The shorter contacts between adjacent nitro groups and benzene rings are: N5···C9i 3.591 (6), N5···C10i 3.505 (6), N5···C11i 3.636 (6), O1···C9i 3.439 (6), O1···C10i 3.570 (6), O2···C12i 3.611 (6), O2···C13i 3.483 (6) and O2···C14i 3.567 (6) Å [symmetry code: (i) 2 - x, 1 - y, 1 - z].

Experimental top

NiCl2·6H2O, disodium maleonitriledithiolate and 1-(4-nitrobenzyl)-2-methylpyridinium chloride (equivalent molar ratio 1:2:2) were combined in water. The precipitated product was filtered off, washed with water and then dissolved in a little MeCN. Iodine (1 mol equivalent) was added to the solution with stirring at room temperature. Three times the resulting volume of MeOH was then added and the mixture allowed to stand overnight. The microcrystals which formed were filtered off, washed with MeOH and dried in vacuo. Single crystals of (I) suitable for structure analysis were obtained by evaporating an MeCN–n-PrOH (1:1 v/v) mixed solution of (I).

Refinement top

H atoms were placed in geometrically calculated positions (C—H = 0.93 Å) with Ueq(H) = 1.2 Ueq(parent atom).

Structure description top

Recently, considerable interest has been focused on low-dimensional molecular solids with novel magnetic properties, such as spin-Peierls transitions (Brown et al., 1998) and room-temperature spin bistability (Fujita & Awaga, 1999). Our aim is to construct quasi-one-dimensional molecule-based magnetic materials formed by platelike maleonitriledithiolene anionic metal complexes [M(mnt)2]- (M is NiIII, PdIII or PtIII). These types of low-dimensional materials are associated with columnar crystallographic packing. Previous work has shown that the geometry of the counter-cations strongly influences the stacking structure of this type of material. Therefore, it is important to select particular counter-cations in order to obtain columnar crystallographic packing. The ground-state conformations of benzylpyridinium derivatives have been extensively investigated by many techniques, and results to date have indicated that the spatial orientation of the benzene and pyridine rings depends on both the electronic and the steric properties of the substituents on the aryl rings (Bulgarevich et al., 1994). The different conformations available to benzylpyridinium derivatives may lead to differences in the geometry of the cations, sufficient to influence the stacking structures of the complexes in the solid state. As a result, the ion-pair complexes consisting of [M(mnt)2]- anions and benzylpyridinium-derived cations present a unique opportunity for the systematic investigation of the fundamental relationship between the stacking structure in the solid and the substituents on the aryl rings. To test this idea, we prepared a series of complexes by systematically varying the substituents on the aryl rings, and found that it is possible to obtain completely separated anions and cations in columnar stacking structures. Herein, we report the crystal structure of the title compound, (I), which has columnar packing. \sch

In the anion of (I), the Ni atom exhibits square-planar coordination geometry involving four S atoms, and the five-membered nickel-containing rings are slightly puckered (Fig. 1), as has been found in other [M(mnt)2]n- structures (Plumlee et al., 1975). The average S—Ni—S bond angle within the five-membered ring is 92.50 (5)° and the average Ni—S bond distance is 2.1477 (13) Å. Other chemically equivalent but crystallographically non-equivalent bond distances within the anion differ by less than three s.u.'s and compare well with those found in [Ni(mnt)2]- complexes (Brunn et al., 1987). The anion is non-planar and the CN groups bend away from the plane of the four S atoms. The CN group with the largest deviation is C1N1, and the deviations from the plane defined by the four S atoms are 0.294 (6) Å for N1 and 0.167 (6) Å for C1. The cation adopts a conformation where the dihedral angle between the benzene ring and the C14/C15/N6 reference plane is 44.5 (4)°, and the pyridine ring is twisted towards the reference plane with a dihedral angle of 72.3 (4)°.

The most prominent general structural features of the complex are the completely segregated stacked columns of [Ni(mnt)2]- anions and 1-(4-nitrobenzyl)-2-methylpyridinium cations, as revealed by the projection along the crystallographic a axis in Fig. 2. Completely segregated stacked columns of [Ni(mnt)2]- anions have been infrequently reported (Hobi et al., 1996). The Ni···Ni distances are alternately 3.847 (1) and 4.281 (1) Å within the [Ni(mnt)2]- column. The nearest Ni···Ni contact between [Ni(mnt)2]- columns is much larger at 10.6 Å, and is larger than the Ni···Ni distance within the [Ni(mnt)2]- column. These results indicate that, compared with intracolumnar interactions, the Ni···Ni magnetic exchange interactions between columns may be neglected. Within the 1-(4-nitrobenzyl)-2-methylbenzylpyridinium cation column, the nitro group of one cation is stacked over the benzene ring of an adjacent cation (Fig. 3). This type of packing structure is often found in nitrobenzene derivatives (Harrowfield et al., 1998). The shorter contacts between adjacent nitro groups and benzene rings are: N5···C9i 3.591 (6), N5···C10i 3.505 (6), N5···C11i 3.636 (6), O1···C9i 3.439 (6), O1···C10i 3.570 (6), O2···C12i 3.611 (6), O2···C13i 3.483 (6) and O2···C14i 3.567 (6) Å [symmetry code: (i) 2 - x, 1 - y, 1 - z].

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of complex (I) with the atom-numbering scheme and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The packing diagram of (I) showing the completely separated columns of anions and cations.
[Figure 3] Fig. 3. A pair of cations showing the overlapping between the nitro groups and the benzene rings. H atoms have been omitted for clarity.
(I) top
Crystal data top
(C13H13N2O2)[Ni(C4N2S2)2]F(000) = 1156
Mr = 568.32Dx = 1.584 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.2343 (13) ÅCell parameters from 36 reflections
b = 26.691 (4) Åθ = 7.4–14.4°
c = 12.745 (2) ŵ = 1.20 mm1
β = 104.510 (16)°T = 293 K
V = 2382.4 (7) Å3Block, black
Z = 40.40 × 0.30 × 0.30 mm
Data collection top
Bruker P4
diffractometer
2775 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
2θ/ω scansh = 18
Absorption correction: ψ scan
(North et al., 1968)
k = 131
Tmin = 0.646, Tmax = 0.715l = 1515
5502 measured reflections3 standard reflections every 97 reflections
4202 independent reflections intensity decay: 6.6%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0441P)2 + 1.9841P]
where P = (Fo2 + 2Fc2)/3
4202 reflections(Δ/σ)max = 0.001
308 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
(C13H13N2O2)[Ni(C4N2S2)2]V = 2382.4 (7) Å3
Mr = 568.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.2343 (13) ŵ = 1.20 mm1
b = 26.691 (4) ÅT = 293 K
c = 12.745 (2) Å0.40 × 0.30 × 0.30 mm
β = 104.510 (16)°
Data collection top
Bruker P4
diffractometer
2775 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.043
Tmin = 0.646, Tmax = 0.7153 standard reflections every 97 reflections
5502 measured reflections intensity decay: 6.6%
4202 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.41 e Å3
4202 reflectionsΔρmin = 0.55 e Å3
308 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.26470 (8)0.48959 (2)0.07147 (4)0.04639 (18)
S10.3526 (2)0.55562 (5)0.16616 (10)0.0613 (4)
S20.24845 (17)0.52891 (5)0.07804 (9)0.0501 (3)
S30.18266 (17)0.42138 (4)0.01909 (9)0.0501 (3)
S40.2766 (2)0.45348 (5)0.22338 (9)0.0584 (3)
O10.6681 (6)0.43868 (16)0.4447 (4)0.0966 (14)
O20.8831 (7)0.42987 (15)0.3554 (3)0.0876 (12)
N10.4952 (7)0.68572 (18)0.1486 (4)0.0816 (15)
N20.3347 (8)0.65502 (18)0.1792 (4)0.0811 (14)
N30.1068 (9)0.28587 (18)0.0303 (4)0.0927 (17)
N40.1986 (7)0.32979 (18)0.3370 (4)0.0753 (13)
N50.7817 (7)0.45542 (17)0.3965 (4)0.0647 (12)
N61.0602 (6)0.68552 (14)0.4157 (3)0.0523 (10)
C10.4346 (8)0.6482 (2)0.1118 (4)0.0609 (13)
C20.3642 (6)0.60017 (17)0.0715 (4)0.0501 (11)
C30.3156 (6)0.58855 (17)0.0364 (4)0.0473 (11)
C40.3256 (7)0.62569 (19)0.1161 (4)0.0583 (13)
C50.1356 (8)0.3272 (2)0.0513 (4)0.0618 (13)
C60.1759 (6)0.37860 (17)0.0813 (4)0.0477 (11)
C70.2126 (6)0.39294 (17)0.1869 (4)0.0494 (11)
C80.2054 (7)0.35772 (19)0.2707 (4)0.0568 (13)
C90.9462 (7)0.58158 (19)0.3389 (4)0.0613 (13)
H91.03300.59570.30450.074*
C100.9262 (8)0.53067 (19)0.3406 (4)0.0608 (13)
H100.99820.51000.30750.073*
C110.7982 (7)0.51069 (17)0.3920 (4)0.0517 (11)
C120.6876 (8)0.5404 (2)0.4396 (4)0.0693 (15)
H120.59970.52620.47300.083*
C130.7088 (7)0.59123 (19)0.4368 (4)0.0629 (14)
H130.63430.61180.46850.076*
C140.8384 (7)0.61226 (17)0.3879 (4)0.0504 (11)
C150.8572 (7)0.66882 (18)0.3887 (4)0.0625 (13)
H15A0.79230.68180.31790.075*
H15B0.79500.68270.44130.075*
C161.1559 (8)0.67962 (18)0.5235 (4)0.0599 (13)
H161.09440.66430.57090.072*
C171.3343 (8)0.6955 (2)0.5601 (4)0.0687 (15)
H171.39810.69110.63250.082*
C181.4249 (8)0.71874 (19)0.4887 (5)0.0694 (15)
H181.54830.73110.51340.083*
C191.3312 (8)0.72311 (19)0.3829 (5)0.0679 (15)
H191.39290.73750.33460.081*
C201.1436 (9)0.70634 (19)0.3451 (4)0.0645 (14)
C211.0402 (10)0.7121 (2)0.2316 (4)0.100 (2)
H21A0.98900.68030.20330.150*
H21B1.12580.72410.19070.150*
H21C0.93780.73560.22630.150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0474 (3)0.0461 (3)0.0470 (3)0.0024 (3)0.0143 (3)0.0010 (3)
S10.0812 (9)0.0543 (8)0.0478 (7)0.0042 (7)0.0149 (6)0.0017 (6)
S20.0540 (7)0.0480 (7)0.0477 (6)0.0005 (6)0.0118 (5)0.0002 (5)
S30.0558 (7)0.0501 (7)0.0452 (6)0.0025 (6)0.0141 (5)0.0014 (5)
S40.0750 (9)0.0548 (8)0.0477 (6)0.0006 (7)0.0194 (6)0.0014 (5)
O10.095 (3)0.066 (3)0.134 (4)0.012 (2)0.039 (3)0.014 (3)
O20.117 (4)0.053 (2)0.095 (3)0.007 (2)0.029 (3)0.007 (2)
N10.110 (4)0.054 (3)0.074 (3)0.012 (3)0.008 (3)0.005 (2)
N20.116 (4)0.065 (3)0.063 (3)0.004 (3)0.024 (3)0.006 (2)
N30.152 (5)0.053 (3)0.073 (3)0.025 (3)0.029 (3)0.001 (2)
N40.095 (4)0.073 (3)0.061 (3)0.000 (3)0.025 (3)0.019 (2)
N50.070 (3)0.051 (3)0.065 (3)0.004 (2)0.001 (2)0.000 (2)
N60.062 (3)0.040 (2)0.060 (2)0.0028 (19)0.024 (2)0.0011 (18)
C10.068 (4)0.057 (3)0.056 (3)0.000 (3)0.012 (3)0.002 (3)
C20.049 (3)0.045 (3)0.056 (3)0.003 (2)0.013 (2)0.005 (2)
C30.041 (2)0.052 (3)0.049 (3)0.003 (2)0.012 (2)0.001 (2)
C40.068 (4)0.057 (3)0.050 (3)0.002 (3)0.014 (3)0.001 (3)
C50.079 (4)0.056 (3)0.050 (3)0.008 (3)0.016 (3)0.005 (2)
C60.042 (3)0.051 (3)0.051 (3)0.002 (2)0.014 (2)0.004 (2)
C70.051 (3)0.049 (3)0.050 (3)0.002 (2)0.014 (2)0.003 (2)
C80.059 (3)0.056 (3)0.055 (3)0.001 (3)0.014 (2)0.002 (3)
C90.070 (3)0.057 (3)0.064 (3)0.007 (3)0.029 (3)0.003 (2)
C100.078 (4)0.051 (3)0.056 (3)0.002 (3)0.022 (3)0.011 (2)
C110.056 (3)0.041 (3)0.052 (3)0.004 (2)0.001 (2)0.004 (2)
C120.070 (4)0.057 (4)0.088 (4)0.009 (3)0.032 (3)0.008 (3)
C130.063 (3)0.052 (3)0.081 (4)0.001 (3)0.031 (3)0.011 (3)
C140.053 (3)0.044 (3)0.052 (3)0.001 (2)0.008 (2)0.001 (2)
C150.053 (3)0.050 (3)0.082 (4)0.000 (2)0.013 (3)0.003 (3)
C160.065 (3)0.057 (3)0.061 (3)0.005 (3)0.023 (3)0.005 (2)
C170.076 (4)0.073 (4)0.055 (3)0.008 (3)0.013 (3)0.007 (3)
C180.066 (4)0.059 (3)0.085 (4)0.006 (3)0.022 (3)0.011 (3)
C190.067 (4)0.051 (3)0.092 (4)0.007 (3)0.032 (3)0.000 (3)
C200.093 (4)0.047 (3)0.056 (3)0.013 (3)0.025 (3)0.003 (2)
C210.134 (6)0.101 (5)0.060 (4)0.025 (4)0.016 (4)0.018 (3)
Geometric parameters (Å, º) top
Ni1—S12.1407 (14)C9—C141.383 (6)
Ni1—S42.1451 (13)C9—H90.9300
Ni1—S22.1526 (13)C10—C111.369 (7)
Ni1—S32.1577 (13)C10—H100.9300
S1—C21.711 (5)C11—C121.371 (7)
S2—C31.710 (5)C12—C131.368 (7)
S3—C61.725 (4)C12—H120.9300
S4—C71.713 (5)C13—C141.370 (6)
O1—N51.227 (6)C13—H130.9300
O2—N51.213 (5)C14—C151.515 (6)
N1—C11.147 (6)C15—H15A0.9700
N2—C41.135 (6)C15—H15B0.9700
N3—C51.142 (6)C16—C171.327 (7)
N4—C81.137 (6)C16—H160.9300
N5—C111.482 (6)C17—C181.394 (7)
N6—C201.324 (6)C17—H170.9300
N6—C161.384 (6)C18—C191.354 (7)
N6—C151.490 (6)C18—H180.9300
C1—C21.426 (7)C19—C201.395 (7)
C2—C31.367 (6)C19—H190.9300
C3—C41.435 (7)C20—C211.461 (7)
C5—C61.435 (7)C21—H21A0.9600
C6—C71.360 (6)C21—H21B0.9600
C7—C81.433 (6)C21—H21C0.9600
C9—C101.367 (7)
S1—Ni1—S485.53 (5)C10—C11—N5118.5 (5)
S1—Ni1—S292.31 (5)C12—C11—N5119.8 (5)
S4—Ni1—S2177.38 (6)C13—C12—C11118.7 (5)
S1—Ni1—S3177.84 (6)C13—C12—H12120.6
S4—Ni1—S392.70 (5)C11—C12—H12120.6
S2—Ni1—S389.49 (5)C12—C13—C14120.8 (5)
C2—S1—Ni1103.57 (16)C12—C13—H13119.6
C3—S2—Ni1103.34 (16)C14—C13—H13119.6
C6—S3—Ni1102.53 (16)C13—C14—C9119.4 (5)
C7—S4—Ni1103.41 (16)C13—C14—C15118.4 (4)
O2—N5—O1124.4 (5)C9—C14—C15122.2 (4)
O2—N5—C11118.7 (5)N6—C15—C14112.4 (4)
O1—N5—C11116.9 (5)N6—C15—H15A109.1
C20—N6—C16121.5 (5)C14—C15—H15A109.1
C20—N6—C15124.0 (4)N6—C15—H15B109.1
C16—N6—C15114.5 (4)C14—C15—H15B109.1
N1—C1—C2176.8 (6)H15A—C15—H15B107.9
C3—C2—C1123.0 (4)C17—C16—N6120.9 (5)
C3—C2—S1120.4 (4)C17—C16—H16119.5
C1—C2—S1116.5 (3)N6—C16—H16119.5
C2—C3—C4120.7 (4)C16—C17—C18119.2 (5)
C2—C3—S2120.3 (4)C16—C17—H17120.4
C4—C3—S2119.0 (3)C18—C17—H17120.4
N2—C4—C3179.6 (6)C19—C18—C17119.3 (5)
N3—C5—C6178.0 (6)C19—C18—H18120.4
C7—C6—C5120.6 (4)C17—C18—H18120.4
C7—C6—S3120.9 (4)C18—C19—C20121.1 (5)
C5—C6—S3118.5 (3)C18—C19—H19119.4
C6—C7—C8121.2 (4)C20—C19—H19119.4
C6—C7—S4120.4 (4)N6—C20—C19118.0 (5)
C8—C7—S4118.3 (4)N6—C20—C21120.6 (6)
N4—C8—C7179.6 (6)C19—C20—C21121.4 (6)
C10—C9—C14120.5 (5)C20—C21—H21A109.5
C10—C9—H9119.8C20—C21—H21B109.5
C14—C9—H9119.8H21A—C21—H21B109.5
C9—C10—C11118.8 (5)C20—C21—H21C109.5
C9—C10—H10120.6H21A—C21—H21C109.5
C11—C10—H10120.6H21B—C21—H21C109.5
C10—C11—C12121.7 (5)
S4—Ni1—S1—C2179.74 (17)Ni1—S4—C7—C8179.9 (3)
S2—Ni1—S1—C21.23 (17)C6—C7—C8—N480 (70)
S3—Ni1—S1—C2145.3 (15)S4—C7—C8—N4102 (70)
S1—Ni1—S2—C30.56 (16)C14—C9—C10—C110.2 (8)
S4—Ni1—S2—C335.0 (13)C9—C10—C11—C121.3 (8)
S3—Ni1—S2—C3178.24 (16)C9—C10—C11—N5178.1 (4)
S1—Ni1—S3—C634.6 (16)O2—N5—C11—C100.6 (7)
S4—Ni1—S3—C60.27 (16)O1—N5—C11—C10178.8 (5)
S2—Ni1—S3—C6178.83 (16)O2—N5—C11—C12178.8 (5)
S1—Ni1—S4—C7179.58 (17)O1—N5—C11—C120.7 (7)
S2—Ni1—S4—C7145.9 (12)C10—C11—C12—C131.1 (8)
S3—Ni1—S4—C70.82 (17)N5—C11—C12—C13178.3 (5)
N1—C1—C2—C3156 (11)C11—C12—C13—C140.2 (8)
N1—C1—C2—S121 (12)C12—C13—C14—C91.3 (8)
Ni1—S1—C2—C31.9 (4)C12—C13—C14—C15179.3 (5)
Ni1—S1—C2—C1175.2 (3)C10—C9—C14—C131.1 (8)
C1—C2—C3—C42.8 (7)C10—C9—C14—C15179.5 (5)
S1—C2—C3—C4179.8 (4)C20—N6—C15—C14109.5 (5)
C1—C2—C3—S2175.3 (4)C16—N6—C15—C1473.2 (5)
S1—C2—C3—S21.7 (6)C13—C14—C15—N6135.9 (5)
Ni1—S2—C3—C20.5 (4)C9—C14—C15—N644.7 (7)
Ni1—S2—C3—C4178.6 (3)C20—N6—C16—C171.1 (7)
C2—C3—C4—N285 (81)C15—N6—C16—C17176.2 (5)
S2—C3—C4—N293 (81)N6—C16—C17—C180.5 (8)
N3—C5—C6—C729 (19)C16—C17—C18—C192.2 (8)
N3—C5—C6—S3150 (19)C17—C18—C19—C202.3 (8)
Ni1—S3—C6—C71.8 (4)C16—N6—C20—C191.1 (7)
Ni1—S3—C6—C5176.6 (4)C15—N6—C20—C19176.0 (4)
C5—C6—C7—C82.3 (7)C16—N6—C20—C21179.8 (5)
S3—C6—C7—C8179.4 (4)C15—N6—C20—C213.1 (7)
C5—C6—C7—S4175.5 (4)C18—C19—C20—N60.6 (8)
S3—C6—C7—S42.8 (6)C18—C19—C20—C21178.5 (5)
Ni1—S4—C7—C62.2 (4)

Experimental details

Crystal data
Chemical formula(C13H13N2O2)[Ni(C4N2S2)2]
Mr568.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.2343 (13), 26.691 (4), 12.745 (2)
β (°) 104.510 (16)
V3)2382.4 (7)
Z4
Radiation typeMo Kα
µ (mm1)1.20
Crystal size (mm)0.40 × 0.30 × 0.30
Data collection
DiffractometerBruker P4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.646, 0.715
No. of measured, independent and
observed [I > 2σ(I)] reflections
5502, 4202, 2775
Rint0.043
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.124, 1.04
No. of reflections4202
No. of parameters308
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.55

Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXTL (Sheldrick, 1997b), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL.

Selected geometric parameters (Å, º) top
Ni1—S12.1407 (14)S1—C21.711 (5)
Ni1—S42.1451 (13)S2—C31.710 (5)
Ni1—S22.1526 (13)S3—C61.725 (4)
Ni1—S32.1577 (13)S4—C71.713 (5)
S1—Ni1—S485.53 (5)N1—C1—C2176.8 (6)
S1—Ni1—S292.31 (5)N2—C4—C3179.6 (6)
S4—Ni1—S392.70 (5)N3—C5—C6178.0 (6)
S2—Ni1—S389.49 (5)N4—C8—C7179.6 (6)
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds