metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Bis(pyridine-κN){N2,N2′-[1,1′-(pyridine-2,6-di­yl)di­ethyl­­idyne]benzene­sulfono­hydrazonato-κ5O,N,N′,N′′,O′}nickel(II)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bDepartment of Molecular Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: khaledi@perdana.um.edu.my

(Received 14 December 2009; accepted 28 December 2009; online 9 January 2010)

In the crystal structure of the title compound, [Ni(C21H19N5O4S2)(C5H5N)2], the metal center is seven-coordinate, with an approximate penta­gonal-bipyramidal configuration. The Ni atom is chelated by a dianionic penta­dentate Schiff base via the pyridine N atom, the two azomethine N atoms and the two sulfonyl O atoms. The latter coordinate to Ni at different distances, viz. 2.3337 (12) and 2.7988 (12) Å. Two apically coordinated pyridine mol­ecules complete the seven-coordin­ate geometry. The dihedral angle between the two pyridine ring planes is 68.25 (6)°.

Related literature

For the structure of the ligand and its zinc(II) complex, see: Yusnita et al. (2009a[Yusnita, J., Puvaneswary, S., Abdulla, M. A., Robinson, W. T. & Ali, H. M. (2009a). J. Chem. Crystallogr. 39, 615-618.]). For the structure of copper(II) complex of a similar ligand, see: Yusnita et al. (2009b[Yusnita, J., Puvaneswary, S., Ali, H. M., Robinson, W. T. & Kwai-Lin, T. (2009b). Polyhedron, 28, 3050-3054.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C21H19N5O4S2)(C5H5N)2]

  • Mr = 686.44

  • Monoclinic, P 21 /n

  • a = 11.6029 (2) Å

  • b = 15.8298 (3) Å

  • c = 16.4156 (3) Å

  • β = 91.823 (2)°

  • V = 3013.55 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.83 mm−1

  • T = 100 K

  • 0.30 × 0.22 × 0.19 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.788, Tmax = 0.858

  • 22997 measured reflections

  • 5308 independent reflections

  • 4815 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.024

  • wR(F2) = 0.065

  • S = 1.05

  • 5308 reflections

  • 406 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supporting information


Related literature top

For the structure of the ligand and its zinc(II) complex, see: Yusnita et al. (2009a). For the structure of copper(II) complex of a similar ligand, see: Yusnita et al. (2009b).

Experimental top

2,6-Diacetylpyridinebis(benzenesulfonylhydrazide) (1.413 g, 3 mmol) was dissolved in ethanol (50 ml) and three droplets of triethylamine were added, followed by addition of an ethanolic solution of stoichiometric amount of hydrated nickel (II) acetate. The mixture was refluxed for 5 h. The resulting dark brown solids were filtered and dried over silica gel. Brown crystals of the title compound were grown by slow evaporation of a pyridine solution.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å), and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C).

Structure description top

For the structure of the ligand and its zinc(II) complex, see: Yusnita et al. (2009a). For the structure of copper(II) complex of a similar ligand, see: Yusnita et al. (2009b).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the title compound at the 40% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Bis(pyridine-κN){N2,N2'-[1,1'-(pyridine-2,6- diyl)diethylidyne]benzenesulfonohydrazonato- κ5O,N,N',N'',O'}nickel(II) top
Crystal data top
[Ni(C21H19N5O4S2)(C5H5N)2]F(000) = 1428
Mr = 686.44Dx = 1.515 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9879 reflections
a = 11.6029 (2) Åθ = 2.5–28.3°
b = 15.8298 (3) ŵ = 0.83 mm1
c = 16.4156 (3) ÅT = 100 K
β = 91.823 (2)°Block, brown
V = 3013.55 (9) Å30.30 × 0.22 × 0.19 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
5308 independent reflections
Radiation source: fine-focus sealed tube4815 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.788, Tmax = 0.858k = 1818
22997 measured reflectionsl = 1919
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)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0291P)2 + 2.4638P]
where P = (Fo2 + 2Fc2)/3
5308 reflections(Δ/σ)max = 0.001
406 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Ni(C21H19N5O4S2)(C5H5N)2]V = 3013.55 (9) Å3
Mr = 686.44Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.6029 (2) ŵ = 0.83 mm1
b = 15.8298 (3) ÅT = 100 K
c = 16.4156 (3) Å0.30 × 0.22 × 0.19 mm
β = 91.823 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
5308 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4815 reflections with I > 2σ(I)
Tmin = 0.788, Tmax = 0.858Rint = 0.020
22997 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.065H-atom parameters constrained
S = 1.05Δρmax = 0.34 e Å3
5308 reflectionsΔρmin = 0.36 e Å3
406 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
Ni0.410517 (18)0.141485 (13)0.215880 (12)0.01157 (7)
S10.59292 (4)0.00687 (3)0.18463 (3)0.01400 (10)
S20.27045 (4)0.12194 (3)0.40344 (2)0.01272 (10)
O10.60699 (11)0.09339 (8)0.16025 (8)0.0207 (3)
O20.49868 (10)0.01082 (7)0.23919 (7)0.0157 (3)
O30.33543 (10)0.06141 (7)0.35665 (7)0.0166 (3)
O40.17478 (10)0.08872 (8)0.44772 (7)0.0174 (3)
N10.38858 (12)0.24587 (9)0.14898 (8)0.0127 (3)
N20.28461 (12)0.21687 (9)0.28339 (8)0.0125 (3)
N30.22201 (12)0.19994 (9)0.35170 (8)0.0137 (3)
N40.52548 (12)0.12310 (9)0.12007 (9)0.0134 (3)
N50.58722 (12)0.05107 (9)0.10487 (9)0.0156 (3)
N60.53749 (12)0.19065 (9)0.29575 (9)0.0143 (3)
N70.27701 (12)0.07348 (9)0.15452 (9)0.0140 (3)
C10.25986 (14)0.28945 (11)0.24972 (10)0.0131 (3)
C20.17637 (15)0.35009 (11)0.28509 (11)0.0169 (4)
H2A0.10360.32090.29480.025*
H2B0.16230.39680.24690.025*
H2C0.20840.37230.33670.025*
C30.32043 (14)0.30847 (11)0.17453 (10)0.0131 (3)
C40.31328 (15)0.38448 (11)0.13167 (11)0.0166 (4)
H40.26530.42900.14940.020*
C50.37776 (15)0.39357 (11)0.06257 (11)0.0182 (4)
H50.37420.44500.03280.022*
C60.44751 (15)0.32834 (11)0.03648 (10)0.0163 (4)
H60.49130.33420.01110.020*
C70.45153 (14)0.25424 (11)0.08200 (10)0.0139 (3)
C80.52355 (14)0.18075 (11)0.06381 (10)0.0145 (4)
C90.58566 (16)0.17241 (12)0.01367 (11)0.0209 (4)
H9A0.58510.22680.04210.031*
H9B0.54730.12970.04830.031*
H9C0.66550.15510.00170.031*
C100.72211 (15)0.02117 (11)0.24006 (11)0.0169 (4)
C110.78134 (15)0.09477 (12)0.22277 (11)0.0208 (4)
H110.75560.13040.17930.025*
C120.87894 (17)0.11586 (14)0.26986 (12)0.0275 (5)
H120.91970.16650.25900.033*
C130.91686 (16)0.06321 (15)0.33268 (12)0.0305 (5)
H130.98410.07750.36420.037*
C140.85730 (17)0.00988 (14)0.34959 (12)0.0288 (5)
H140.88340.04550.39300.035*
C150.75943 (16)0.03152 (13)0.30345 (11)0.0227 (4)
H150.71830.08180.31500.027*
C160.36809 (14)0.16219 (11)0.48003 (10)0.0140 (3)
C170.41986 (15)0.10464 (12)0.53378 (11)0.0192 (4)
H170.40480.04590.52800.023*
C180.49334 (17)0.13345 (13)0.59570 (11)0.0233 (4)
H180.52880.09450.63280.028*
C190.51522 (16)0.21932 (13)0.60359 (11)0.0236 (4)
H190.56560.23920.64610.028*
C200.46384 (17)0.27609 (12)0.54965 (12)0.0235 (4)
H200.47920.33480.55530.028*
C210.39001 (15)0.24778 (11)0.48730 (11)0.0188 (4)
H210.35500.28670.45010.023*
C220.57825 (16)0.26962 (12)0.28800 (12)0.0211 (4)
H220.54900.30330.24420.025*
C230.66049 (17)0.30403 (13)0.34058 (13)0.0277 (5)
H230.68670.36030.33310.033*
C240.70418 (17)0.25566 (13)0.40424 (12)0.0267 (4)
H240.76160.27760.44090.032*
C250.66268 (15)0.17464 (12)0.41350 (11)0.0205 (4)
H250.69060.14000.45710.025*
C260.57989 (15)0.14469 (11)0.35850 (10)0.0161 (4)
H260.55160.08890.36540.019*
C270.28759 (15)0.04331 (11)0.07836 (11)0.0170 (4)
H270.35660.05480.05080.020*
C280.20283 (16)0.00357 (11)0.03843 (11)0.0197 (4)
H280.21300.02250.01580.024*
C290.10303 (16)0.02267 (12)0.07827 (11)0.0203 (4)
H290.04440.05610.05260.024*
C300.09044 (16)0.00798 (12)0.15641 (12)0.0205 (4)
H300.02270.00390.18540.025*
C310.17797 (15)0.05617 (11)0.19157 (11)0.0178 (4)
H310.16770.07820.24470.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.01215 (12)0.01122 (12)0.01132 (12)0.00032 (8)0.00009 (8)0.00054 (8)
S10.0129 (2)0.0136 (2)0.0155 (2)0.00219 (16)0.00011 (16)0.00047 (16)
S20.0127 (2)0.0124 (2)0.0131 (2)0.00030 (16)0.00112 (16)0.00026 (16)
O10.0209 (7)0.0145 (6)0.0266 (7)0.0039 (5)0.0017 (5)0.0031 (5)
O20.0139 (6)0.0156 (6)0.0177 (6)0.0009 (5)0.0019 (5)0.0016 (5)
O30.0159 (6)0.0149 (6)0.0191 (6)0.0006 (5)0.0013 (5)0.0028 (5)
O40.0165 (6)0.0180 (6)0.0180 (6)0.0024 (5)0.0031 (5)0.0015 (5)
N10.0128 (7)0.0137 (7)0.0113 (7)0.0001 (6)0.0011 (6)0.0001 (6)
N20.0125 (7)0.0146 (7)0.0104 (7)0.0016 (6)0.0004 (5)0.0016 (6)
N30.0140 (7)0.0162 (7)0.0110 (7)0.0011 (6)0.0018 (6)0.0008 (6)
N40.0117 (7)0.0145 (7)0.0140 (7)0.0014 (6)0.0000 (6)0.0017 (6)
N50.0153 (7)0.0167 (8)0.0149 (7)0.0040 (6)0.0022 (6)0.0016 (6)
N60.0126 (7)0.0154 (7)0.0150 (7)0.0002 (6)0.0025 (6)0.0004 (6)
N70.0150 (7)0.0122 (7)0.0147 (7)0.0027 (6)0.0009 (6)0.0003 (6)
C10.0129 (8)0.0146 (8)0.0116 (8)0.0003 (7)0.0024 (6)0.0024 (7)
C20.0184 (9)0.0177 (9)0.0146 (9)0.0042 (7)0.0006 (7)0.0011 (7)
C30.0117 (8)0.0134 (8)0.0140 (8)0.0004 (7)0.0029 (7)0.0022 (7)
C40.0180 (9)0.0134 (9)0.0181 (9)0.0013 (7)0.0025 (7)0.0001 (7)
C50.0211 (9)0.0150 (9)0.0183 (9)0.0024 (7)0.0037 (7)0.0042 (7)
C60.0171 (9)0.0177 (9)0.0138 (9)0.0024 (7)0.0005 (7)0.0029 (7)
C70.0121 (8)0.0169 (9)0.0126 (8)0.0023 (7)0.0018 (7)0.0004 (7)
C80.0133 (8)0.0167 (9)0.0136 (9)0.0022 (7)0.0002 (7)0.0007 (7)
C90.0228 (10)0.0223 (10)0.0179 (9)0.0012 (8)0.0058 (8)0.0013 (8)
C100.0131 (8)0.0220 (9)0.0156 (9)0.0043 (7)0.0018 (7)0.0046 (7)
C110.0159 (9)0.0259 (10)0.0207 (10)0.0005 (8)0.0034 (7)0.0033 (8)
C120.0169 (9)0.0357 (12)0.0301 (11)0.0047 (8)0.0054 (8)0.0115 (9)
C130.0138 (9)0.0548 (14)0.0226 (10)0.0055 (9)0.0012 (8)0.0169 (10)
C140.0240 (10)0.0454 (13)0.0168 (10)0.0133 (10)0.0029 (8)0.0057 (9)
C150.0223 (10)0.0274 (10)0.0184 (10)0.0060 (8)0.0023 (8)0.0016 (8)
C160.0124 (8)0.0177 (9)0.0120 (8)0.0006 (7)0.0021 (6)0.0001 (7)
C170.0200 (9)0.0176 (9)0.0201 (10)0.0009 (7)0.0014 (7)0.0039 (7)
C180.0224 (10)0.0284 (11)0.0188 (10)0.0011 (8)0.0038 (8)0.0077 (8)
C190.0223 (10)0.0307 (11)0.0173 (9)0.0025 (8)0.0058 (8)0.0014 (8)
C200.0268 (10)0.0180 (9)0.0254 (10)0.0020 (8)0.0055 (8)0.0034 (8)
C210.0202 (9)0.0170 (9)0.0191 (9)0.0018 (7)0.0028 (7)0.0012 (7)
C220.0206 (9)0.0197 (10)0.0228 (10)0.0045 (8)0.0012 (8)0.0045 (8)
C230.0260 (10)0.0245 (10)0.0324 (11)0.0115 (8)0.0042 (9)0.0029 (9)
C240.0200 (10)0.0345 (12)0.0251 (11)0.0067 (9)0.0054 (8)0.0033 (9)
C250.0161 (9)0.0290 (10)0.0164 (9)0.0024 (8)0.0012 (7)0.0020 (8)
C260.0144 (9)0.0183 (9)0.0158 (9)0.0021 (7)0.0038 (7)0.0000 (7)
C270.0188 (9)0.0163 (9)0.0160 (9)0.0020 (7)0.0019 (7)0.0006 (7)
C280.0234 (10)0.0200 (9)0.0156 (9)0.0048 (8)0.0018 (7)0.0053 (7)
C290.0180 (9)0.0174 (9)0.0249 (10)0.0018 (7)0.0062 (8)0.0059 (8)
C300.0152 (9)0.0235 (10)0.0227 (10)0.0003 (8)0.0012 (7)0.0034 (8)
C310.0184 (9)0.0189 (9)0.0163 (9)0.0018 (7)0.0015 (7)0.0036 (7)
Geometric parameters (Å, º) top
Ni—N11.9959 (14)C9—H9C0.9800
Ni—N62.0910 (14)C10—C111.387 (3)
Ni—N42.1145 (14)C10—C151.392 (3)
Ni—N72.1152 (14)C11—C121.391 (3)
Ni—N22.2111 (14)C11—H110.9500
Ni—O22.3337 (12)C12—C131.387 (3)
Ni—O32.7988 (12)C12—H120.9500
S1—O11.4376 (13)C13—C141.380 (3)
S1—O21.4624 (12)C13—H130.9500
S1—N51.5984 (15)C14—C151.388 (3)
S1—C101.7847 (18)C14—H140.9500
S2—O41.4450 (12)C15—H150.9500
S2—O31.4538 (12)C16—C211.383 (3)
S2—N31.5911 (15)C16—C171.391 (2)
S2—C161.7832 (17)C17—C181.383 (3)
N1—C31.343 (2)C17—H170.9500
N1—C71.346 (2)C18—C191.388 (3)
N2—C11.303 (2)C18—H180.9500
N2—N31.3816 (19)C19—C201.383 (3)
N4—C81.298 (2)C19—H190.9500
N4—N51.374 (2)C20—C211.388 (3)
N6—C261.342 (2)C20—H200.9500
N6—C221.344 (2)C21—H210.9500
N7—C311.345 (2)C22—C231.378 (3)
N7—C271.348 (2)C22—H220.9500
C1—C31.471 (2)C23—C241.379 (3)
C1—C21.494 (2)C23—H230.9500
C2—H2A0.9800C24—C251.380 (3)
C2—H2B0.9800C24—H240.9500
C2—H2C0.9800C25—C261.381 (3)
C3—C41.395 (2)C25—H250.9500
C4—C51.386 (3)C26—H260.9500
C4—H40.9500C27—C281.381 (3)
C5—C61.388 (3)C27—H270.9500
C5—H50.9500C28—C291.381 (3)
C6—C71.391 (2)C28—H280.9500
C6—H60.9500C29—C301.384 (3)
C7—C81.469 (2)C29—H290.9500
C8—C91.488 (2)C30—C311.382 (3)
C9—H9A0.9800C30—H300.9500
C9—H9B0.9800C31—H310.9500
N1—Ni—N696.42 (6)N4—C8—C7114.16 (15)
N1—Ni—N477.12 (6)N4—C8—C9123.23 (16)
N6—Ni—N493.96 (5)C7—C8—C9122.58 (15)
N1—Ni—N794.63 (6)C8—C9—H9A109.5
N6—Ni—N7168.17 (6)C8—C9—H9B109.5
N4—Ni—N792.61 (5)H9A—C9—H9B109.5
N1—Ni—N275.77 (5)C8—C9—H9C109.5
N6—Ni—N287.04 (5)H9A—C9—H9C109.5
N4—Ni—N2152.81 (5)H9B—C9—H9C109.5
N7—Ni—N291.59 (5)C11—C10—C15120.81 (17)
N1—Ni—O2150.64 (5)C11—C10—S1121.21 (14)
N6—Ni—O286.02 (5)C15—C10—S1117.93 (14)
N4—Ni—O273.52 (5)C10—C11—C12119.19 (18)
N7—Ni—O286.42 (5)C10—C11—H11120.4
N2—Ni—O2133.58 (5)C12—C11—H11120.4
N1—Ni—O3142.34 (5)C13—C12—C11120.2 (2)
N6—Ni—O383.25 (5)C13—C12—H12119.9
N4—Ni—O3140.54 (5)C11—C12—H12119.9
N7—Ni—O385.42 (5)C14—C13—C12120.28 (18)
N2—Ni—O366.59 (4)C14—C13—H13119.9
O2—Ni—O367.02 (4)C12—C13—H13119.9
O1—S1—O2116.53 (7)C13—C14—C15120.23 (19)
O1—S1—N5108.70 (8)C13—C14—H14119.9
O2—S1—N5112.31 (7)C15—C14—H14119.9
O1—S1—C10106.14 (8)C14—C15—C10119.33 (19)
O2—S1—C10105.81 (8)C14—C15—H15120.3
N5—S1—C10106.69 (8)C10—C15—H15120.3
O4—S2—O3116.46 (7)C21—C16—C17120.82 (16)
O4—S2—N3106.68 (7)C21—C16—S2121.46 (13)
O3—S2—N3114.18 (7)C17—C16—S2117.71 (14)
O4—S2—C16104.86 (7)C18—C17—C16119.59 (17)
O3—S2—C16106.23 (7)C18—C17—H17120.2
N3—S2—C16107.75 (8)C16—C17—H17120.2
S1—O2—Ni113.69 (7)C17—C18—C19119.87 (17)
S2—O3—Ni108.55 (6)C17—C18—H18120.1
C3—N1—C7121.51 (15)C19—C18—H18120.1
C3—N1—Ni120.33 (11)C20—C19—C18120.18 (18)
C7—N1—Ni117.91 (11)C20—C19—H19119.9
C1—N2—N3113.63 (14)C18—C19—H19119.9
C1—N2—Ni113.80 (11)C19—C20—C21120.38 (18)
N3—N2—Ni132.44 (11)C19—C20—H20119.8
N2—N3—S2113.45 (11)C21—C20—H20119.8
C8—N4—N5116.85 (14)C16—C21—C20119.16 (17)
C8—N4—Ni115.81 (11)C16—C21—H21120.4
N5—N4—Ni126.47 (11)C20—C21—H21120.4
N4—N5—S1109.62 (11)N6—C22—C23123.16 (17)
C26—N6—C22117.09 (15)N6—C22—H22118.4
C26—N6—Ni120.89 (12)C23—C22—H22118.4
C22—N6—Ni122.00 (12)C22—C23—C24119.05 (18)
C31—N7—C27116.84 (15)C22—C23—H23120.5
C31—N7—Ni120.77 (12)C24—C23—H23120.5
C27—N7—Ni122.36 (12)C23—C24—C25118.58 (18)
N2—C1—C3115.57 (15)C23—C24—H24120.7
N2—C1—C2122.58 (15)C25—C24—H24120.7
C3—C1—C2121.85 (15)C24—C25—C26118.99 (17)
C1—C2—H2A109.5C24—C25—H25120.5
C1—C2—H2B109.5C26—C25—H25120.5
H2A—C2—H2B109.5N6—C26—C25123.11 (17)
C1—C2—H2C109.5N6—C26—H26118.4
H2A—C2—H2C109.5C25—C26—H26118.4
H2B—C2—H2C109.5N7—C27—C28123.12 (17)
N1—C3—C4120.33 (15)N7—C27—H27118.4
N1—C3—C1114.38 (15)C28—C27—H27118.4
C4—C3—C1125.27 (15)C27—C28—C29119.21 (17)
C5—C4—C3118.51 (16)C27—C28—H28120.4
C5—C4—H4120.7C29—C28—H28120.4
C3—C4—H4120.7C28—C29—C30118.49 (17)
C4—C5—C6120.69 (16)C28—C29—H29120.8
C4—C5—H5119.7C30—C29—H29120.8
C6—C5—H5119.7C31—C30—C29118.88 (17)
C5—C6—C7118.14 (16)C31—C30—H30120.6
C5—C6—H6120.9C29—C30—H30120.6
C7—C6—H6120.9N7—C31—C30123.42 (16)
N1—C7—C6120.81 (16)N7—C31—H31118.3
N1—C7—C8114.53 (15)C30—C31—H31118.3
C6—C7—C8124.65 (15)
O1—S1—O2—Ni145.14 (7)O3—Ni—N7—C3133.11 (13)
N5—S1—O2—Ni18.82 (10)N1—Ni—N7—C2772.98 (14)
C10—S1—O2—Ni97.20 (8)N6—Ni—N7—C27128.0 (3)
N1—Ni—O2—S18.70 (14)N4—Ni—N7—C274.30 (14)
N6—Ni—O2—S187.33 (8)N2—Ni—N7—C27148.83 (13)
N4—Ni—O2—S17.99 (7)O2—Ni—N7—C2777.61 (13)
N7—Ni—O2—S1101.78 (8)O3—Ni—N7—C27144.81 (13)
N2—Ni—O2—S1169.43 (6)N3—N2—C1—C3177.23 (13)
O3—Ni—O2—S1171.68 (8)Ni—N2—C1—C30.80 (18)
O4—S2—O3—Ni145.87 (6)N3—N2—C1—C23.3 (2)
N3—S2—O3—Ni20.78 (9)Ni—N2—C1—C2179.72 (12)
C16—S2—O3—Ni97.82 (7)C7—N1—C3—C40.0 (2)
N1—Ni—O3—S212.32 (11)Ni—N1—C3—C4174.16 (12)
N6—Ni—O3—S279.45 (7)C7—N1—C3—C1178.66 (15)
N4—Ni—O3—S2167.49 (7)Ni—N1—C3—C14.52 (19)
N7—Ni—O3—S2103.97 (7)N2—C1—C3—N13.3 (2)
N2—Ni—O3—S210.24 (6)C2—C1—C3—N1177.22 (15)
O2—Ni—O3—S2167.98 (8)N2—C1—C3—C4175.31 (16)
N6—Ni—N1—C382.17 (13)C2—C1—C3—C44.2 (3)
N4—Ni—N1—C3174.78 (13)N1—C3—C4—C50.0 (3)
N7—Ni—N1—C393.59 (13)C1—C3—C4—C5178.56 (16)
N2—Ni—N1—C33.12 (12)C3—C4—C5—C60.3 (3)
O2—Ni—N1—C3175.48 (10)C4—C5—C6—C70.6 (3)
O3—Ni—N1—C35.10 (17)C3—N1—C7—C60.4 (2)
N6—Ni—N1—C792.18 (12)Ni—N1—C7—C6174.65 (12)
N4—Ni—N1—C70.43 (12)C3—N1—C7—C8178.48 (14)
N7—Ni—N1—C792.05 (12)Ni—N1—C7—C84.20 (19)
N2—Ni—N1—C7177.47 (13)C5—C6—C7—N10.6 (3)
O2—Ni—N1—C71.13 (19)C5—C6—C7—C8178.08 (16)
O3—Ni—N1—C7179.45 (10)N5—N4—C8—C7177.13 (14)
N1—Ni—N2—C11.11 (11)Ni—N4—C8—C77.13 (19)
N6—Ni—N2—C196.28 (12)N5—N4—C8—C91.0 (2)
N4—Ni—N2—C13.37 (19)Ni—N4—C8—C9171.04 (13)
N7—Ni—N2—C195.48 (12)N1—C7—C8—N47.5 (2)
O2—Ni—N2—C1177.94 (10)C6—C7—C8—N4171.34 (16)
O3—Ni—N2—C1179.80 (13)N1—C7—C8—C9170.72 (16)
N1—Ni—N2—N3174.46 (15)C6—C7—C8—C910.5 (3)
N6—Ni—N2—N388.15 (14)O1—S1—C10—C11130.91 (15)
N4—Ni—N2—N3178.94 (12)O2—S1—C10—C11104.67 (15)
N7—Ni—N2—N380.09 (14)N5—S1—C10—C1115.11 (17)
O2—Ni—N2—N36.49 (17)O1—S1—C10—C1551.50 (16)
O3—Ni—N2—N34.23 (13)O2—S1—C10—C1572.92 (15)
C1—N2—N3—S2167.49 (12)N5—S1—C10—C15167.30 (14)
Ni—N2—N3—S216.94 (18)C15—C10—C11—C120.2 (3)
O4—S2—N3—N2155.04 (11)S1—C10—C11—C12177.28 (14)
O3—S2—N3—N224.92 (14)C10—C11—C12—C130.7 (3)
C16—S2—N3—N292.82 (12)C11—C12—C13—C140.8 (3)
N1—Ni—N4—C83.93 (12)C12—C13—C14—C150.5 (3)
N6—Ni—N4—C899.62 (13)C13—C14—C15—C100.0 (3)
N7—Ni—N4—C890.22 (13)C11—C10—C15—C140.1 (3)
N2—Ni—N4—C88.4 (2)S1—C10—C15—C14177.72 (14)
O2—Ni—N4—C8175.71 (13)O4—S2—C16—C21112.94 (15)
O3—Ni—N4—C8176.19 (10)O3—S2—C16—C21123.19 (15)
N1—Ni—N4—N5172.83 (14)N3—S2—C16—C210.43 (17)
N6—Ni—N4—N591.48 (13)O4—S2—C16—C1765.61 (15)
N7—Ni—N4—N578.68 (13)O3—S2—C16—C1758.26 (15)
N2—Ni—N4—N5177.28 (11)N3—S2—C16—C17178.98 (13)
O2—Ni—N4—N56.81 (12)C21—C16—C17—C180.6 (3)
O3—Ni—N4—N57.29 (17)S2—C16—C17—C18177.96 (14)
C8—N4—N5—S1172.91 (12)C16—C17—C18—C190.2 (3)
Ni—N4—N5—S118.29 (16)C17—C18—C19—C200.1 (3)
O1—S1—N5—N4153.45 (11)C18—C19—C20—C210.1 (3)
O2—S1—N5—N423.01 (13)C17—C16—C21—C200.6 (3)
C10—S1—N5—N492.48 (12)S2—C16—C21—C20177.89 (14)
N1—Ni—N6—C26176.50 (13)C19—C20—C21—C160.3 (3)
N4—Ni—N6—C26106.03 (13)C26—N6—C22—C230.4 (3)
N7—Ni—N6—C2617.5 (3)Ni—N6—C22—C23178.89 (15)
N2—Ni—N6—C26101.19 (13)N6—C22—C23—C240.3 (3)
O2—Ni—N6—C2632.88 (13)C22—C23—C24—C250.8 (3)
O3—Ni—N6—C2634.42 (12)C23—C24—C25—C260.5 (3)
N1—Ni—N6—C221.92 (14)C22—N6—C26—C250.7 (2)
N4—Ni—N6—C2275.54 (14)Ni—N6—C26—C25179.16 (13)
N7—Ni—N6—C22160.9 (2)C24—C25—C26—N60.2 (3)
N2—Ni—N6—C2277.23 (14)C31—N7—C27—C280.2 (3)
O2—Ni—N6—C22148.70 (14)Ni—N7—C27—C28177.80 (13)
O3—Ni—N6—C22144.00 (14)N7—C27—C28—C291.6 (3)
N1—Ni—N7—C31109.10 (13)C27—C28—C29—C301.7 (3)
N6—Ni—N7—C3149.9 (3)C28—C29—C30—C310.2 (3)
N4—Ni—N7—C31173.62 (13)C27—N7—C31—C301.8 (3)
N2—Ni—N7—C3133.25 (13)Ni—N7—C31—C30176.19 (14)
O2—Ni—N7—C31100.31 (13)C29—C30—C31—N71.7 (3)

Experimental details

Crystal data
Chemical formula[Ni(C21H19N5O4S2)(C5H5N)2]
Mr686.44
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)11.6029 (2), 15.8298 (3), 16.4156 (3)
β (°) 91.823 (2)
V3)3013.55 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.83
Crystal size (mm)0.30 × 0.22 × 0.19
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.788, 0.858
No. of measured, independent and
observed [I > 2σ(I)] reflections
22997, 5308, 4815
Rint0.020
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.065, 1.05
No. of reflections5308
No. of parameters406
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

The authors thank the University of Malaya for funding this study (UMRG grant No. RG136/09HTM).

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). publCIF. In preparation.  Google Scholar
First citationYusnita, J., Puvaneswary, S., Abdulla, M. A., Robinson, W. T. & Ali, H. M. (2009a). J. Chem. Crystallogr. 39, 615-618.  Web of Science CSD CrossRef CAS Google Scholar
First citationYusnita, J., Puvaneswary, S., Ali, H. M., Robinson, W. T. & Kwai-Lin, T. (2009b). Polyhedron, 28, 3050–3054.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds