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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page m421
doi:10.1107/S1600536812010458

Tri­ethyl­ammonium (indane-1,2,3-trione 1,2-dioximato-κ2N1,O2)(indane-1,2,3-trione 2-oximato 1-oxime-κ2N1,O2)nickel(II)

Baoyun Zhong,a Shengli Lib and Guifang Chenb*

aThe Third Middle School in Liaocheng, Shandong 252059, People's Republic of China, and bDepartment of Chemistry and Biology, Dongchang College Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: lidacheng62@163.com

(Received 11 February 2012; accepted 9 March 2012; online 14 March 2012)

In the title compound, (C6H16N)[Ni(C9H4N2O3)(C9H5N2O3)], the NiIIion is four-coordinated by two N atoms and two O atoms from two indane-1,2,3-trione-1,2-dioxime ligands. The two organic ligands are linked by an intra­molecular O—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by N—H⋯O hydrogen-bonds.

Related literature

For the use of oximes, see: Chaudhuri (2003[Chaudhuri, P. (2003). Coord. Chem. Rev. 243, 143-190.]). For theoretical research on their magnetic properties, see: Pavlishchuk et al. (2003[Pavlishchuk, V. V., Kolotilov, S. V., Addison, A. W., Prushan, M. J., Schollmeyer, D., Thompson, L. K., Weyhermuller, T. & Goreshnik, E. A. (2003). Dalton Trans. pp. 1587-1595.]). For a related structure, see: Chen et al. (2010[Chen, Z. L., Jia, M. M., Zhang, Z. & Liang, F. P. (2010). Cryst. Growth Des. 10, 4806-4814.]). For the properties of related complexes, see: Davidson et al. (2007[Davidson, M. G., Johnson, A. L., Jones, M. D., Lunn, M. D. & Mahon, M. F. (2007). Polyhedron, 26, 975-980.]).

[Scheme 1]

Experimental

Crystal data

  • (C6H16N)[Ni(C9H4N2O3)(C9H5N2O3)]

  • Mr = 538.20

  • Triclinic, [P \overline 1]

  • a = 9.710 (5) Å

  • b = 10.470 (5) Å

  • c = 12.156 (6) Å

  • α = 80.785 (6)°

  • β = 87.639 (6)°

  • γ = 72.217 (6)°

  • V = 1161.6 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.89 mm−1

  • T = 298 K

  • 0.45 × 0.35 × 0.33 mm
Data collection

  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.691, Tmax = 0.758

  • 6186 measured reflections

  • 4073 independent reflections

  • 2650 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.075

  • S = 1.00

  • 4073 reflections

  • 332 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Selected bond lengths (Å)

Ni1—O2 1.849 (2)
Ni1—N3 1.872 (3)
Ni1—O5 1.875 (2)
Ni1—N1 1.883 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N5—H5⋯O5i 0.91 1.94 2.815 (3) 160
N5—H5⋯O2i 0.91 2.21 2.903 (3) 132
O4—H4⋯O1 1.18 (3) 1.19 (3) 2.363 (3) 177 (3)
O4—H4⋯N1 1.18 (3) 1.96 (3) 2.904 (3) 134 (2)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812010458/vm2155sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010458/vm2155Isup2.hkl

checkCIF report


Comment top

There is currently a renewed interest in the coordination chemistry of oximes (Davidson et al., 2007; Pavlishchuk et al., 2003). The planar aromatic polyoxime ligand indane-1,2,3-trione-1,2-dioxime abbreviated as H2Itdo, was used for the synthesis of the title compound. The complex (Fig.1) consists of two indane-1,2,3-trione-1,2-dioxime ligands, Ni2+and one [HNEt3]+. The Ni center is four-coordinated by two N atoms and two O atoms from two indane-1,2,3-trione-1,2-dioxime ligands (Table 1). The sum of four angles around the Ni atom is 360.04 (1)° showing that the coordination is planar. There exists one deprotonated and one protonated oxime ligand with a strong intramolecular hydrogen bond between the OH group and the negatively charged oxygen of the other ligand (Table 2). The molecules are linked by weak C17—H17···O3ii interactions (C17···O3 = 3.402 (5) Å, symmetry code: (ii) x+1, y, z+1) to give a 1D chain.

Related literature top

For the use of oximes, see: Chaudhuri (2003). For theoretical research on their magnetic properties, see: Pavlishchuk et al. (2003). For a related structure, see: Chen et al. (2010). For the properties of related complexes, see: Davidson et al. (2007).

Experimental top

A solution of Ni(NO3)2 (0.0727 g, 0.25 mmol) in MeOH (10 ml) was added to a solution of indane-1,2,3-trione-1,2-dioxime (0.1056 g, 0.5 mmol) and 0.5 mmol NEt3 in MeOH (10 ml).The resulting black solution was stirred for about 6 h and was then allowed to slowly concentrate by solvent evaporation at room temperature. Green block crystals suitable for X-ray diffraction were obtained within one month (yield 30.6%, m.p. 310-320K).

Refinement top

All H atoms were placed in geometrically idealized positions (C—H 0.96 (methyl), C—H 0.97 (CH2), C—H 0.93 (phenyl) and N—H 0.91 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2Ueq or 1.5Ueq(C), Uiso(H) = 1.2Ueq(O).

Structure description top

There is currently a renewed interest in the coordination chemistry of oximes (Davidson et al., 2007; Pavlishchuk et al., 2003). The planar aromatic polyoxime ligand indane-1,2,3-trione-1,2-dioxime abbreviated as H2Itdo, was used for the synthesis of the title compound. The complex (Fig.1) consists of two indane-1,2,3-trione-1,2-dioxime ligands, Ni2+and one [HNEt3]+. The Ni center is four-coordinated by two N atoms and two O atoms from two indane-1,2,3-trione-1,2-dioxime ligands (Table 1). The sum of four angles around the Ni atom is 360.04 (1)° showing that the coordination is planar. There exists one deprotonated and one protonated oxime ligand with a strong intramolecular hydrogen bond between the OH group and the negatively charged oxygen of the other ligand (Table 2). The molecules are linked by weak C17—H17···O3ii interactions (C17···O3 = 3.402 (5) Å, symmetry code: (ii) x+1, y, z+1) to give a 1D chain.

For the use of oximes, see: Chaudhuri (2003). For theoretical research on their magnetic properties, see: Pavlishchuk et al. (2003). For a related structure, see: Chen et al. (2010). For the properties of related complexes, see: Davidson et al. (2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bond is shown as dashed line.
Triethylammonium (indane-1,2,3-trione 1,2-dioximato-κ2N1,O2)(indane-1,2,3-trione 2-oximato 1-oxime-κ2N1,O2)nickel(II) top
Crystal data top
(C6H16N)[Ni(C9H4N2O3)(C9H5N2O3)]Z = 2
Mr = 538.20F(000) = 560
Triclinic, P1Dx = 1.539 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.710 (5) ÅCell parameters from 1572 reflections
b = 10.470 (5) Åθ = 2.8–21.3°
c = 12.156 (6) ŵ = 0.89 mm−1
α = 80.785 (6)°T = 298 K
β = 87.639 (6)°Block, green
γ = 72.217 (6)°0.45 × 0.35 × 0.33 mm
V = 1161.6 (10) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer		4073 independent reflections
Radiation source: fine-focus sealed tube2650 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
phi and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −7→11
Tmin = 0.691, Tmax = 0.758k = −9→12
6186 measured reflectionsl = −14→13
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.015P)2]
where P = (Fo2 + 2Fc2)/3
4073 reflections(Δ/σ)max < 0.001
332 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
(C6H16N)[Ni(C9H4N2O3)(C9H5N2O3)]γ = 72.217 (6)°
Mr = 538.20V = 1161.6 (10) Å3
Triclinic, P1Z = 2
a = 9.710 (5) ÅMo Kα radiation
b = 10.470 (5) ŵ = 0.89 mm−1
c = 12.156 (6) ÅT = 298 K
α = 80.785 (6)°0.45 × 0.35 × 0.33 mm
β = 87.639 (6)°
Data collection top
Siemens SMART CCD area-detector
diffractometer		4073 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2650 reflections with I > 2σ(I)
Tmin = 0.691, Tmax = 0.758Rint = 0.027
6186 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.34 e Å−3
4073 reflectionsΔρmin = −0.27 e Å−3
332 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.36828 (5)0.15590 (4)0.77300 (3)0.04715 (15)
N10.4326 (3)0.0088 (2)0.69308 (19)0.0420 (7)
N20.1501 (3)0.2012 (3)0.6025 (2)0.0552 (8)
N30.5272 (3)0.1035 (2)0.8702 (2)0.0448 (7)
N40.3108 (3)0.3589 (3)0.9226 (2)0.0561 (8)
N5−0.0031 (3)0.5196 (2)0.24499 (19)0.0427 (7)
H5−0.08780.58730.22930.051*
O10.5575 (2)−0.09090 (19)0.71801 (18)0.0532 (6)
O20.2013 (2)0.23611 (19)0.68845 (17)0.0577 (6)
O30.0705 (3)0.0957 (2)0.41575 (18)0.0704 (8)
O40.6413 (2)−0.0075 (2)0.86314 (18)0.0608 (7)
H40.603 (3)−0.051 (3)0.791 (3)0.078 (11)*
O50.2738 (2)0.3093 (2)0.83908 (17)0.0599 (7)
O60.4210 (2)0.4371 (2)1.11162 (18)0.0663 (7)
C10.3587 (3)−0.0071 (3)0.6126 (2)0.0413 (8)
C20.2244 (4)0.0886 (3)0.5700 (2)0.0459 (9)
C30.1763 (4)0.0403 (3)0.4754 (3)0.0530 (9)
C40.2861 (4)−0.0905 (3)0.4650 (3)0.0503 (9)
C50.3935 (4)−0.1196 (3)0.5465 (2)0.0458 (8)
C60.5076 (4)−0.2386 (3)0.5533 (3)0.0591 (10)
H60.5798−0.26000.60710.071*
C70.5104 (4)−0.3236 (3)0.4778 (3)0.0702 (11)
H70.5856−0.40450.48180.084*
C80.4065 (5)−0.2942 (4)0.3965 (3)0.0729 (12)
H80.4136−0.35350.34570.087*
C90.2915 (4)−0.1767 (4)0.3900 (3)0.0660 (11)
H90.2195−0.15650.33610.079*
C100.5401 (3)0.1702 (3)0.9481 (2)0.0417 (8)
C110.4322 (3)0.2923 (3)0.9718 (3)0.0444 (8)
C120.4829 (4)0.3399 (3)1.0668 (3)0.0472 (9)
C130.6247 (3)0.2408 (3)1.0977 (2)0.0418 (8)
C140.6586 (3)0.1395 (3)1.0295 (2)0.0413 (8)
C150.7877 (3)0.0347 (3)1.0470 (2)0.0508 (9)
H150.8124−0.03351.00270.061*
C160.8782 (4)0.0341 (3)1.1312 (3)0.0564 (9)
H160.9649−0.03571.14340.068*
C170.8443 (4)0.1341 (3)1.1983 (3)0.0579 (10)
H170.90800.13171.25420.069*
C180.7154 (4)0.2375 (3)1.1818 (3)0.0528 (9)
H180.69040.30431.22740.063*
C190.0059 (4)0.4224 (3)0.1653 (2)0.0528 (9)
H19A−0.08050.39380.17280.063*
H19B0.00690.46970.09000.063*
C200.1351 (4)0.2988 (3)0.1811 (3)0.0665 (11)
H20A0.22160.32560.17450.100*
H20B0.13450.24370.12530.100*
H20C0.13220.24770.25370.100*
C21−0.0122 (4)0.4581 (3)0.3641 (2)0.0540 (10)
H21A0.07380.38140.38280.065*
H21B−0.01330.52470.41150.065*
C22−0.1422 (4)0.4113 (3)0.3886 (3)0.0682 (11)
H22A−0.22660.48130.35760.102*
H22B−0.15280.39150.46780.102*
H22C−0.13080.33090.35630.102*
C230.1134 (4)0.5863 (3)0.2317 (3)0.0610 (10)
H23A0.20650.51750.24610.073*
H23B0.10030.64700.28640.073*
C240.1133 (4)0.6654 (3)0.1169 (3)0.0888 (14)
H24A0.15530.60390.06530.133*
H24B0.16870.72710.11770.133*
H24C0.01570.71580.09430.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0395 (3)0.0407 (3)0.0519 (3)0.00054 (19)−0.0017 (2)−0.00464 (19)
N10.0343 (17)0.0376 (15)0.0459 (16)−0.0028 (13)0.0006 (13)0.0007 (12)
N20.053 (2)0.0496 (18)0.0560 (18)−0.0058 (15)−0.0135 (15)−0.0033 (15)
N30.0405 (18)0.0402 (16)0.0472 (16)−0.0037 (13)0.0045 (13)−0.0059 (13)
N40.048 (2)0.0550 (18)0.0605 (19)−0.0047 (15)−0.0020 (15)−0.0174 (15)
N50.0418 (18)0.0368 (15)0.0408 (15)0.0009 (13)−0.0014 (13)−0.0056 (12)
O10.0382 (15)0.0431 (13)0.0675 (15)0.0068 (11)−0.0067 (12)−0.0138 (12)
O20.0469 (16)0.0497 (14)0.0663 (15)0.0053 (11)−0.0157 (12)−0.0144 (12)
O30.076 (2)0.0643 (16)0.0637 (16)−0.0127 (14)−0.0219 (14)−0.0005 (13)
O40.0473 (16)0.0564 (15)0.0625 (15)0.0146 (12)−0.0102 (12)−0.0191 (12)
O50.0477 (16)0.0546 (14)0.0645 (15)0.0094 (11)−0.0120 (12)−0.0185 (12)
O60.0517 (17)0.0601 (16)0.0826 (17)−0.0024 (13)0.0047 (13)−0.0284 (13)
C10.041 (2)0.0376 (19)0.0425 (19)−0.0127 (16)0.0075 (16)0.0012 (15)
C20.045 (2)0.0396 (19)0.046 (2)−0.0074 (17)0.0006 (17)0.0005 (16)
C30.065 (3)0.049 (2)0.044 (2)−0.021 (2)−0.0001 (19)0.0026 (17)
C40.057 (3)0.045 (2)0.051 (2)−0.0197 (19)0.0041 (19)−0.0045 (17)
C50.050 (2)0.040 (2)0.046 (2)−0.0150 (17)0.0103 (17)−0.0019 (16)
C60.061 (3)0.050 (2)0.063 (2)−0.0125 (19)0.0074 (19)−0.0091 (19)
C70.075 (3)0.053 (2)0.081 (3)−0.014 (2)0.018 (2)−0.023 (2)
C80.101 (4)0.059 (3)0.066 (3)−0.032 (3)0.019 (2)−0.025 (2)
C90.082 (3)0.059 (2)0.061 (2)−0.026 (2)−0.001 (2)−0.010 (2)
C100.039 (2)0.0417 (19)0.0413 (19)−0.0121 (16)0.0048 (16)0.0023 (15)
C110.030 (2)0.0423 (19)0.054 (2)−0.0033 (16)0.0000 (16)−0.0046 (16)
C120.041 (2)0.049 (2)0.050 (2)−0.0132 (18)0.0045 (17)−0.0035 (17)
C130.037 (2)0.0432 (19)0.047 (2)−0.0165 (16)0.0085 (16)−0.0050 (16)
C140.037 (2)0.0403 (19)0.0421 (19)−0.0099 (16)0.0031 (16)0.0019 (15)
C150.046 (2)0.050 (2)0.053 (2)−0.0090 (17)−0.0026 (18)−0.0075 (17)
C160.043 (2)0.052 (2)0.066 (2)−0.0035 (17)−0.0082 (19)−0.0031 (19)
C170.049 (3)0.064 (2)0.062 (2)−0.022 (2)−0.0099 (19)−0.0009 (19)
C180.048 (2)0.058 (2)0.057 (2)−0.0200 (19)0.0050 (19)−0.0147 (18)
C190.060 (2)0.048 (2)0.043 (2)−0.0036 (18)−0.0016 (17)−0.0101 (16)
C200.063 (3)0.050 (2)0.083 (3)−0.0069 (19)0.021 (2)−0.0266 (19)
C210.069 (3)0.050 (2)0.0364 (19)−0.0085 (19)−0.0028 (18)−0.0075 (16)
C220.064 (3)0.060 (2)0.073 (2)−0.013 (2)0.020 (2)−0.0048 (19)
C230.052 (3)0.053 (2)0.082 (3)−0.0187 (19)0.014 (2)−0.020 (2)
C240.076 (3)0.060 (2)0.111 (3)−0.012 (2)0.038 (3)0.014 (2)
Geometric parameters (Å, º) top
Ni1—O21.849 (2)C9—H90.9300
Ni1—N31.872 (3)C10—C111.446 (4)
Ni1—O51.875 (2)C10—C141.473 (4)
Ni1—N11.883 (2)C11—C121.485 (4)
N1—C11.298 (3)C12—C131.469 (4)
N1—O11.345 (3)C13—C181.366 (4)
N2—C21.294 (4)C13—C141.402 (4)
N2—O21.322 (3)C14—C151.388 (4)
N3—C101.295 (3)C15—C161.374 (4)
N3—O41.350 (3)C15—H150.9300
N4—C111.287 (3)C16—C171.383 (4)
N4—O51.320 (3)C16—H160.9300
N5—C231.491 (4)C17—C181.379 (4)
N5—C191.496 (3)C17—H170.9300
N5—C211.499 (3)C18—H180.9300
N5—H50.9100C19—C201.495 (4)
O1—H41.19 (3)C19—H19A0.9700
O3—C31.217 (4)C19—H19B0.9700
O4—H41.18 (3)C20—H20A0.9600
O6—C121.213 (3)C20—H20B0.9600
C1—C21.436 (4)C20—H20C0.9600
C1—C51.477 (4)C21—C221.490 (4)
C2—C31.473 (4)C21—H21A0.9700
C3—C41.477 (4)C21—H21B0.9700
C4—C91.371 (4)C22—H22A0.9600
C4—C51.399 (4)C22—H22B0.9600
C5—C61.385 (4)C22—H22C0.9600
C6—C71.372 (4)C23—C241.505 (4)
C6—H60.9300C23—H23A0.9700
C7—C81.373 (5)C23—H23B0.9700
C7—H70.9300C24—H24A0.9600
C8—C91.380 (4)C24—H24B0.9600
C8—H80.9300C24—H24C0.9600
O2—Ni1—N3169.62 (10)O6—C12—C13126.9 (3)
O2—Ni1—O576.52 (9)O6—C12—C11128.3 (3)
N3—Ni1—O593.23 (10)C13—C12—C11104.8 (3)
O2—Ni1—N193.68 (10)C18—C13—C14121.3 (3)
N3—Ni1—N196.61 (11)C18—C13—C12128.1 (3)
O5—Ni1—N1170.02 (11)C14—C13—C12110.6 (3)
C1—N1—O1114.7 (2)C15—C14—C13119.3 (3)
C1—N1—Ni1123.1 (2)C15—C14—C10132.2 (3)
O1—N1—Ni1122.17 (19)C13—C14—C10108.5 (3)
C2—N2—O2117.2 (3)C16—C15—C14118.5 (3)
C10—N3—O4113.8 (2)C16—C15—H15120.7
C10—N3—Ni1123.9 (2)C14—C15—H15120.7
O4—N3—Ni1122.29 (19)C15—C16—C17122.0 (3)
C11—N4—O5117.1 (3)C15—C16—H16119.0
C23—N5—C19114.3 (2)C17—C16—H16119.0
C23—N5—C21110.4 (2)C18—C17—C16119.5 (3)
C19—N5—C21112.9 (2)C18—C17—H17120.2
C23—N5—H5106.2C16—C17—H17120.2
C19—N5—H5106.2C13—C18—C17119.3 (3)
C21—N5—H5106.2C13—C18—H18120.3
N1—O1—H4101.0 (14)C17—C18—H18120.3
N2—O2—Ni1132.04 (17)C20—C19—N5114.8 (2)
N3—O4—H4101.0 (15)C20—C19—H19A108.6
N4—O5—Ni1131.86 (18)N5—C19—H19A108.6
N1—C1—C2124.2 (3)C20—C19—H19B108.6
N1—C1—C5128.6 (3)N5—C19—H19B108.6
C2—C1—C5107.2 (3)H19A—C19—H19B107.6
N2—C2—C1129.7 (3)C19—C20—H20A109.5
N2—C2—C3121.4 (3)C19—C20—H20B109.5
C1—C2—C3108.9 (3)H20A—C20—H20B109.5
O3—C3—C2128.3 (3)C19—C20—H20C109.5
O3—C3—C4126.1 (3)H20A—C20—H20C109.5
C2—C3—C4105.6 (3)H20B—C20—H20C109.5
C9—C4—C5121.5 (3)C22—C21—N5113.8 (3)
C9—C4—C3128.8 (3)C22—C21—H21A108.8
C5—C4—C3109.7 (3)N5—C21—H21A108.8
C6—C5—C4119.8 (3)C22—C21—H21B108.8
C6—C5—C1131.6 (3)N5—C21—H21B108.8
C4—C5—C1108.6 (3)H21A—C21—H21B107.7
C7—C6—C5117.6 (3)C21—C22—H22A109.5
C7—C6—H6121.2C21—C22—H22B109.5
C5—C6—H6121.2H22A—C22—H22B109.5
C6—C7—C8122.6 (4)C21—C22—H22C109.5
C6—C7—H7118.7H22A—C22—H22C109.5
C8—C7—H7118.7H22B—C22—H22C109.5
C7—C8—C9120.1 (3)N5—C23—C24112.1 (3)
C7—C8—H8120.0N5—C23—H23A109.2
C9—C8—H8120.0C24—C23—H23A109.2
C4—C9—C8118.3 (3)N5—C23—H23B109.2
C4—C9—H9120.9C24—C23—H23B109.2
C8—C9—H9120.9H23A—C23—H23B107.9
N3—C10—C11124.0 (3)C23—C24—H24A109.5
N3—C10—C14129.0 (3)C23—C24—H24B109.5
C11—C10—C14107.0 (3)H24A—C24—H24B109.5
N4—C11—C10129.9 (3)C23—C24—H24C109.5
N4—C11—C12121.1 (3)H24A—C24—H24C109.5
C10—C11—C12109.1 (3)H24B—C24—H24C109.5
O2—Ni1—N1—C1−2.3 (2)C4—C5—C6—C70.3 (5)
N3—Ni1—N1—C1179.0 (2)C1—C5—C6—C7−179.3 (3)
O5—Ni1—N1—C18.5 (7)C5—C6—C7—C80.8 (5)
O2—Ni1—N1—O1−180.0 (2)C6—C7—C8—C9−1.6 (6)
N3—Ni1—N1—O11.3 (2)C5—C4—C9—C80.0 (5)
O5—Ni1—N1—O1−169.2 (5)C3—C4—C9—C8179.7 (3)
O2—Ni1—N3—C108.2 (7)C7—C8—C9—C41.2 (5)
O5—Ni1—N3—C10−0.6 (3)O4—N3—C10—C11180.0 (2)
N1—Ni1—N3—C10−179.0 (2)Ni1—N3—C10—C111.3 (4)
O2—Ni1—N3—O4−170.4 (5)O4—N3—C10—C14−1.6 (4)
O5—Ni1—N3—O4−179.2 (2)Ni1—N3—C10—C14179.8 (2)
N1—Ni1—N3—O42.5 (2)O5—N4—C11—C102.0 (5)
C2—N2—O2—Ni12.3 (4)O5—N4—C11—C12−179.8 (3)
N3—Ni1—O2—N2172.0 (5)N3—C10—C11—N4−2.2 (5)
O5—Ni1—O2—N2−179.0 (3)C14—C10—C11—N4179.1 (3)
N1—Ni1—O2—N2−0.9 (3)N3—C10—C11—C12179.5 (3)
C11—N4—O5—Ni1−1.4 (4)C14—C10—C11—C120.8 (3)
O2—Ni1—O5—N4−177.7 (3)N4—C11—C12—O63.0 (5)
N3—Ni1—O5—N40.7 (3)C10—C11—C12—O6−178.5 (3)
N1—Ni1—O5—N4171.3 (5)N4—C11—C12—C13−178.5 (3)
O1—N1—C1—C2−178.1 (3)C10—C11—C12—C130.0 (3)
Ni1—N1—C1—C24.1 (4)O6—C12—C13—C18−0.2 (6)
O1—N1—C1—C50.5 (4)C11—C12—C13—C18−178.7 (3)
Ni1—N1—C1—C5−177.4 (2)O6—C12—C13—C14177.7 (3)
O2—N2—C2—C1−0.8 (5)C11—C12—C13—C14−0.9 (3)
O2—N2—C2—C3179.7 (3)C18—C13—C14—C15−0.8 (4)
N1—C1—C2—N2−2.6 (5)C12—C13—C14—C15−178.9 (3)
C5—C1—C2—N2178.6 (3)C18—C13—C14—C10179.4 (3)
N1—C1—C2—C3177.0 (3)C12—C13—C14—C101.4 (3)
C5—C1—C2—C3−1.9 (3)N3—C10—C14—C150.3 (5)
N2—C2—C3—O32.3 (6)C11—C10—C14—C15179.0 (3)
C1—C2—C3—O3−177.4 (3)N3—C10—C14—C13−179.9 (3)
N2—C2—C3—C4−179.0 (3)C11—C10—C14—C13−1.3 (3)
C1—C2—C3—C41.4 (3)C13—C14—C15—C160.1 (4)
O3—C3—C4—C9−1.3 (6)C10—C14—C15—C16179.8 (3)
C2—C3—C4—C9179.9 (3)C14—C15—C16—C170.0 (5)
O3—C3—C4—C5178.4 (3)C15—C16—C17—C180.6 (5)
C2—C3—C4—C5−0.3 (4)C14—C13—C18—C171.5 (5)
C9—C4—C5—C6−0.7 (5)C12—C13—C18—C17179.2 (3)
C3—C4—C5—C6179.5 (3)C16—C17—C18—C13−1.4 (5)
C9—C4—C5—C1179.0 (3)C23—N5—C19—C2066.2 (3)
C3—C4—C5—C1−0.8 (4)C21—N5—C19—C20−61.0 (4)
N1—C1—C5—C62.6 (6)C23—N5—C21—C22169.6 (3)
C2—C1—C5—C6−178.7 (3)C19—N5—C21—C22−61.1 (3)
N1—C1—C5—C4−177.1 (3)C19—N5—C23—C2459.2 (3)
C2—C1—C5—C41.7 (3)C21—N5—C23—C24−172.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O5i0.911.942.815 (3)160
N5—H5···O2i0.912.212.903 (3)132
O4—H4···O11.18 (3)1.19 (3)2.363 (3)177 (3)
O4—H4···N11.18 (3)1.96 (3)2.904 (3)134 (2)
Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula(C6H16N)[Ni(C9H4N2O3)(C9H5N2O3)]
Mr538.20
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.710 (5), 10.470 (5), 12.156 (6)
α, β, γ (°)80.785 (6), 87.639 (6), 72.217 (6)
V (Å3)1161.6 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.89
Crystal size (mm)0.45 × 0.35 × 0.33
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.691, 0.758
No. of measured, independent and
observed [I > 2σ(I)] reflections		6186, 4073, 2650
Rint0.027
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.075, 1.00
No. of reflections4073
No. of parameters332
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.34, −0.27

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ni1—O21.849 (2)Ni1—O51.875 (2)
Ni1—N31.872 (3)Ni1—N11.883 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O5i0.911.942.815 (3)160.3
N5—H5···O2i0.912.212.903 (3)132.3
O4—H4···O11.18 (3)1.19 (3)2.363 (3)177 (3)
O4—H4···N11.18 (3)1.96 (3)2.904 (3)134 (2)
Symmetry code: (i) −x, −y+1, −z+1.
 

References

First citationChaudhuri, P. (2003). Coord. Chem. Rev. 243, 143–190.  Web of Science CrossRef CAS Google Scholar
 First citationChen, Z. L., Jia, M. M., Zhang, Z. & Liang, F. P. (2010). Cryst. Growth Des. 10, 4806-4814.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDavidson, M. G., Johnson, A. L., Jones, M. D., Lunn, M. D. & Mahon, M. F. (2007). Polyhedron, 26, 975–980.  Web of Science CSD CrossRef CAS Google Scholar
 First citationPavlishchuk, V. V., Kolotilov, S. V., Addison, A. W., Prushan, M. J., Schollmeyer, D., Thompson, L. K., Weyhermuller, T. & Goreshnik, E. A. (2003). Dalton Trans. pp. 1587–1595.  Web of Science CSD CrossRef 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 citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page m421
doi:10.1107/S1600536812010458
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