Diaqua­bis(1,3-propane­diamine)nickel(II) squarate tetrahydrate

Temel, E.; Erer, H.; Yeşilel, O.Z.; Büyükgüngör, O.

doi:10.1107/S160053680902087X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m735-m736

doi:10.1107/S160053680902087X

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Diaquabis(1,3-propanediamine)nickel(II) squarate tetrahydrate

Ersin Temel,^a Hakan Erer,^b Okan Zafer Yeşilel ^b and Orhan Büyükgüngör ^a ^*

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, TR-55139, Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts and Sciences, Eskişehir Osmangazi University, TR-26480, Eskişehir, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 28 May 2009; accepted 2 June 2009; online 6 June 2009)

The asymmetric unit of the title compound, [Ni(C₃H₁₀N₂)₂(H₂O)₂](C₄O₄)·4H₂O, contains one-half of the diaquabis(1,3-propanediamine)nickel(II) cation, one-half of the centrosymmetric squarate anion and two uncoordinated water molecules. In the cation, the Ni^II atom is located on a crystallographic inversion centre and has a slightly distorted octahedral coordination geometry. The six-membered chelate ring adopts a chair conformation. O—H⋯O hydrogen bonds link the cation and anion through the water molecule, while N—H⋯O hydrogen bonds link the cation and anion and cation and water molecules. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules into a three-dimensional network structure.

Related literature

For general background, see: Bertolasi et al. (2001 ); Gollogly & Hawkins (1972 ); Lam & Mak (2000 ); Liebeskind et al. (1993 ); Mathew et al. (2002 ); Reetz et al. (1994 ); Seitz & Imming (1992 ); Zaman et al. (2001 ). For related structures, see: Ghosh et al. (1997 ); Mukherjee et al. (1990 ); Pariya et al. (1995 ). For ring-puckering parameters, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Ni(C₃H₁₀N₂)₂(H₂O)₂](C₄O₄)·4H₂O
M_r = 427.09
Monoclinic, P 2₁ /c
a = 8.0429 (4) Å
b = 9.1752 (5) Å
c = 14.6510 (8) Å
β = 117.570 (4)°
V = 958.40 (9) Å³
Z = 2
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 296 K
0.75 × 0.45 × 0.05 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.638, T_max = 0.949
7288 measured reflections
2204 independent reflections
2003 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.054
S = 1.06
2204 reflections
139 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

O1—Ni1	2.1429 (9)
N1—Ni1	2.1090 (10)
N2—Ni1	2.0997 (10)

N1—Ni1—O1	88.86 (4)
N2—Ni1—O1	91.46 (4)
N2—Ni1—N1	91.94 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O5ⁱ	0.90	2.35	3.1715 (16)	152
N2—H2A⋯O2ⁱⁱ	0.90	2.33	3.2174 (14)	170
O1—H1F⋯O2ⁱⁱⁱ	0.77 (2)	2.08 (2)	2.8345 (15)	165 (2)
O4—H4A⋯O2ⁱⁱⁱ	0.80 (2)	2.10 (2)	2.8765 (16)	165 (2)
O4—H4B⋯O2^iv	0.82 (3)	2.07 (3)	2.8965 (16)	178 (2)
O5—H5B⋯O4^v	0.77 (2)	2.10 (3)	2.8730 (19)	177 (2)
N1—H1A⋯O4	0.90	2.38	3.2442 (17)	160
N2—H2B⋯O3	0.90	2.04	2.9333 (14)	174
O1—H1E⋯O5	0.80 (2)	1.93 (2)	2.7311 (16)	175.8 (19)
O5—H5A⋯O3	0.80 (2)	1.94 (2)	2.7296 (16)	166 (2)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+2, -z+1; (iii) x, y-1, z; (iv) -x+1, -y+1, -z+1; (v) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S160053680902087X/hk2703sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902087X/hk2703Isup2.hkl

checkCIF report

Comment top

The conformation of six-membered rings arranged by the bidentate coordination of pen (1,3-propanediamine) to transition metals has long been of theoretical interest (Gollogly & Hawkins, 1972). Despite this interest, only a limited number of such complexes have been structurally described. Because of their ability to undergo solid-state phase transitions, some nickel(II) complexes of bis(N-substituted-pen) have been studied in recent times (Mukherjee et al., 1990; Pariya et al., 1995; Ghosh et al., 1997).

Squaric acid (H₂C₄O₄) has been of much interest because of its cyclic structure and possible aromaticity. Recently, considerable progress has been made in the crystal engineering of multidimensional arrays and networks containing metal ions as nodes. Squaric acid is a useful tool for constructing crystalline architectures, due to its rigid, planar four membered ring skeleton, and its proton donating and accepting capabilities for hydrogen bonding (Bertolasi et al., 2001; Reetz et al., 1994; Lam & Mak, 2000; Zaman et al., 2001; Mathew et al., 2002). In addition, squaric acid has been studied for potetial application in xerographic photoreceptors, organic solar cells and optical recording (Liebeskind et al., 1993; Seitz & Imming, 1992).

The asymmetric unit of the title compound contains one centrosymmetric cation, where Ni^II is located on a crystallographic inversion centre, one centrosymmetric anion and two uncoordinated water molecules (Fig.1 ), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. In cation, the Ni^II is hexacoordinated by two O atoms of two water molecules in a trans order and by four N atoms of two pen ligands at the equatorial positions (Table 1). It is suggested that the trans geometry is preferred, when the amine ligand is more bulky. Thus, the coordination environment of Ni^II is a slightly distorted octahedral. Intramolecular O-H···O hydrogen bonds (Table 2) link the cation and anion through the water molecule, while intramolecular N-H···O hydrogen bonds (Table 2) link the cation and anion and cation and water molecule. The six-membered chelate ring (Ni1/N1/N2/C1-C3) is not planar, having total puckering amplitude, Q_T, of 0.765 (3) Å and chair conformation [ϕ = 166.25 (3) and θ = 40.42 (3) °] (Cremer & Pople, 1975).

In the crystal structure, intermolecular O-H···O and N-H···O hydrogen bonds (Table 2) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Bertolasi et al. (2001); Gollogly & Hawkins (1972); Lam & Mak (2000); Liebeskind et al. (1993); Mathew et al. (2002); Reetz et al. (1994); Seitz & Imming (1992); Zaman et al. (2001). For related structures, see: Ghosh et al. (1997); Mukherjee et al. (1990); Pariya et al. (1995). For ring-puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, a solution of squaric acid (0.57 g, 5 mmol) in water (25 ml) was neutralized with sodium hydroxide (0.40 g, 10 mmol) and added dropwise with stirring to a solution of Ni(CH₃COO)₂.4(H₂O) (1.24 g, 5 mmol) in water (25 ml) at 323 K. The solution immediately became suspension and was stirred for 2 h. Then, 1,3-propandiamine (0.74 g, 10 mmol) in methanol (10 ml) was added dropwise to the obtained suspension. The clear solution was stirred for 2 h, and then cooled to room temperature. The crystals formed were filtered and washed with water (10 ml) and methanol (1:1), then dried in air. Anal. Calcd. : C 28.12, H 7.55, N 13.12%; Found C 28.06, H 7.61, N 13.18%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability [symmetry code: (i) 1 - x, 1 - y, 1 - z.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity [symmetry code: (i) 1 - x, 1 - y, 1 - z].

Diaquabis(1,3-propanediamine)nickel(II) squarate tetrahydrate top

Crystal data top

[Ni(C₃H₁₀N₂)₂(H₂O)₂](C₄O₄)·4H₂O	F(000) = 456.0
M_r = 427.09	D_x = 1.480 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2204 reflections
a = 8.0429 (4) Å	θ = 2.2–28.0°
b = 9.1752 (5) Å	µ = 1.06 mm⁻¹
c = 14.6510 (8) Å	T = 296 K
β = 117.570 (4)°	Plate, violet
V = 958.40 (9) Å³	0.75 × 0.45 × 0.05 mm
Z = 2

Data collection top

Stoe IPDS II diffractometer	2204 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2003 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.020
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
w–scan rotation method	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
T_min = 0.638, T_max = 0.949	l = −19→17
7288 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0282P)² + 0.2118P] where P = (F_o² + 2F_c²)/3
2204 reflections	(Δ/σ)_max < 0.001
139 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

[Ni(C₃H₁₀N₂)₂(H₂O)₂](C₄O₄)·4H₂O	V = 958.40 (9) Å³
M_r = 427.09	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0429 (4) Å	µ = 1.06 mm⁻¹
b = 9.1752 (5) Å	T = 296 K
c = 14.6510 (8) Å	0.75 × 0.45 × 0.05 mm
β = 117.570 (4)°

Data collection top

Stoe IPDS II diffractometer	2204 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2003 reflections with I > 2σ(I)
T_min = 0.638, T_max = 0.949	R_int = 0.020
7288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.29 e Å⁻³
2204 reflections	Δρ_min = −0.17 e Å⁻³
139 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

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.5000	0.5000	0.02232 (7)
O1	0.64732 (15)	0.39000 (12)	0.43015 (8)	0.0383 (2)
H1E	0.713 (3)	0.432 (2)	0.4113 (14)	0.051 (5)*
H1F	0.692 (3)	0.315 (3)	0.4515 (15)	0.063 (6)*
O2	0.73874 (13)	1.09844 (11)	0.49933 (8)	0.0414 (2)
O3	0.86500 (14)	0.77497 (10)	0.46843 (9)	0.0434 (2)
O4	0.34274 (18)	0.07964 (14)	0.36302 (9)	0.0489 (3)
H4A	0.455 (3)	0.082 (2)	0.3910 (16)	0.067 (6)*
H4B	0.317 (3)	0.029 (3)	0.401 (2)	0.075 (7)*
O5	0.85562 (18)	0.53525 (13)	0.35580 (11)	0.0462 (3)
H5A	0.871 (3)	0.611 (3)	0.3859 (17)	0.066 (6)*
H5B	0.803 (3)	0.550 (3)	0.2975 (19)	0.072 (8)*
N1	0.24635 (14)	0.41813 (12)	0.38210 (8)	0.0317 (2)
H1A	0.2548	0.3203	0.3845	0.038*
H1B	0.1547	0.4421	0.3983	0.038*
N2	0.47942 (14)	0.69084 (11)	0.41632 (8)	0.0294 (2)
H2A	0.4236	0.7588	0.4372	0.035*
H2B	0.5970	0.7221	0.4355	0.035*
C1	0.1833 (2)	0.46195 (17)	0.27461 (10)	0.0423 (3)
H1C	0.0568	0.4263	0.2326	0.051*
H1D	0.2640	0.4173	0.2497	0.051*
C2	0.1860 (2)	0.62587 (16)	0.26262 (11)	0.0438 (3)
H2C	0.1144	0.6502	0.1902	0.053*
H2D	0.1242	0.6710	0.2987	0.053*
C3	0.3806 (2)	0.68931 (16)	0.30294 (10)	0.0406 (3)
H3A	0.4520	0.6320	0.2776	0.049*
H3B	0.3718	0.7880	0.2774	0.049*
C4	0.88219 (16)	1.04411 (13)	0.49952 (9)	0.0269 (2)
C5	0.93844 (16)	0.89777 (13)	0.48539 (9)	0.0271 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02176 (11)	0.02133 (11)	0.02386 (11)	0.00055 (7)	0.01055 (8)	0.00121 (7)
O1	0.0460 (6)	0.0308 (5)	0.0522 (6)	0.0070 (4)	0.0346 (5)	0.0041 (4)
O2	0.0319 (5)	0.0362 (5)	0.0643 (7)	0.0049 (4)	0.0291 (5)	0.0006 (5)
O3	0.0453 (5)	0.0286 (5)	0.0636 (7)	−0.0116 (4)	0.0314 (5)	−0.0089 (4)
O4	0.0416 (6)	0.0539 (7)	0.0491 (6)	−0.0045 (5)	0.0191 (5)	0.0039 (5)
O5	0.0530 (7)	0.0407 (6)	0.0538 (7)	−0.0009 (5)	0.0321 (6)	−0.0024 (5)
N1	0.0279 (5)	0.0315 (5)	0.0311 (5)	−0.0026 (4)	0.0097 (4)	−0.0008 (4)
N2	0.0309 (5)	0.0258 (5)	0.0317 (5)	0.0005 (4)	0.0147 (4)	0.0031 (4)
C1	0.0455 (8)	0.0434 (7)	0.0282 (6)	−0.0033 (6)	0.0089 (6)	−0.0053 (5)
C2	0.0453 (8)	0.0452 (8)	0.0278 (6)	0.0055 (6)	0.0058 (6)	0.0062 (6)
C3	0.0517 (8)	0.0407 (7)	0.0322 (6)	0.0026 (6)	0.0219 (6)	0.0086 (5)
C4	0.0251 (5)	0.0269 (5)	0.0296 (6)	0.0008 (4)	0.0134 (4)	0.0015 (4)
C5	0.0269 (5)	0.0263 (5)	0.0290 (6)	−0.0021 (4)	0.0138 (4)	−0.0006 (4)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	2.1429 (9)	C1—N1	1.4695 (17)
Ni1—N1ⁱ	2.1090 (10)	C1—C2	1.516 (2)
Ni1—N2ⁱ	2.0997 (10)	C1—H1C	0.9700
O1—Ni1	2.1429 (9)	C1—H1D	0.9700
O1—H1E	0.80 (2)	C2—C3	1.511 (2)
O1—H1F	0.77 (2)	C2—H2C	0.9700
O4—H4A	0.80 (2)	C2—H2D	0.9700
O4—H4B	0.82 (3)	C3—N2	1.4728 (16)
O5—H5A	0.80 (2)	C3—H3A	0.9700
O5—H5B	0.77 (2)	C3—H3B	0.9700
N1—Ni1	2.1090 (10)	C4—O2	1.2557 (15)
N1—H1A	0.9000	C4—C5ⁱⁱ	1.4557 (16)
N1—H1B	0.9000	C4—C5	1.4619 (17)
N2—Ni1	2.0997 (10)	C5—O3	1.2427 (15)
N2—H2A	0.9000	C5—C4ⁱⁱ	1.4557 (16)
N2—H2B	0.9000

O1—Ni1—O1ⁱ	180.00 (5)	C3—N2—Ni1	120.41 (8)
N1ⁱ—Ni1—N1	180.0	C3—N2—H2A	107.2
N1ⁱ—Ni1—O1	91.14 (4)	C3—N2—H2B	107.2
N1—Ni1—O1	88.86 (4)	H2A—N2—H2B	106.9
N1ⁱ—Ni1—O1ⁱ	88.86 (4)	N1—C1—C2	112.30 (11)
N1—Ni1—O1ⁱ	91.14 (4)	N1—C1—H1C	109.1
N2ⁱ—Ni1—O1	88.54 (4)	C2—C1—H1C	109.1
N2—Ni1—O1	91.46 (4)	N1—C1—H1D	109.1
N2ⁱ—Ni1—O1ⁱ	91.46 (4)	C2—C1—H1D	109.1
N2—Ni1—O1ⁱ	88.54 (4)	H1C—C1—H1D	107.9
N2ⁱ—Ni1—N2	180.0	C3—C2—C1	113.88 (12)
N2ⁱ—Ni1—N1ⁱ	91.94 (4)	C3—C2—H2C	108.8
N2—Ni1—N1ⁱ	88.06 (4)	C1—C2—H2C	108.8
N2ⁱ—Ni1—N1	88.06 (4)	C3—C2—H2D	108.8
N2—Ni1—N1	91.94 (4)	C1—C2—H2D	108.8
Ni1—O1—H1E	122.4 (14)	H2C—C2—H2D	107.7
Ni1—O1—H1F	118.8 (15)	N2—C3—C2	111.42 (11)
H1E—O1—H1F	108.4 (19)	N2—C3—H3A	109.3
H4A—O4—H4B	104 (2)	C2—C3—H3A	109.3
H5A—O5—H5B	109 (2)	N2—C3—H3B	109.3
Ni1—N1—H1A	107.3	C2—C3—H3B	109.3
Ni1—N1—H1B	107.3	H3A—C3—H3B	108.0
C1—N1—Ni1	120.23 (9)	O2—C4—C5ⁱⁱ	134.42 (12)
C1—N1—H1A	107.3	O2—C4—C5	135.11 (12)
C1—N1—H1B	107.3	C5ⁱⁱ—C4—C5	90.46 (9)
H1A—N1—H1B	106.9	O3—C5—C4ⁱⁱ	135.11 (12)
Ni1—N2—H2A	107.2	O3—C5—C4	135.35 (12)
Ni1—N2—H2B	107.2	C4ⁱⁱ—C5—C4	89.54 (9)

C1—N1—Ni1—O1	−63.90 (10)	N1—C1—C2—C3	72.93 (17)
C1—N1—Ni1—O1ⁱ	116.10 (10)	C1—C2—C3—N2	−73.63 (16)
C1—N1—Ni1—N2ⁱ	−152.47 (10)	C2—C3—N2—Ni1	52.35 (14)
C1—N1—Ni1—N2	27.53 (10)	O2—C4—C5—O3	−0.2 (3)
C3—N2—Ni1—O1	60.31 (10)	C5ⁱⁱ—C4—C5—O3	179.50 (19)
C3—N2—Ni1—O1ⁱ	−119.69 (10)	O2—C4—C5—C4ⁱⁱ	−179.72 (18)
C2—C1—N1—Ni1	−50.38 (16)	C5ⁱⁱ—C4—C5—C4ⁱⁱ	0.0

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O5ⁱⁱⁱ	0.90	2.35	3.1715 (16)	152
N2—H2A···O2^iv	0.90	2.33	3.2174 (14)	170
O1—H1F···O2^v	0.77 (2)	2.08 (2)	2.8345 (15)	165 (2)
O4—H4A···O2^v	0.80 (2)	2.10 (2)	2.8765 (16)	165 (2)
O4—H4B···O2ⁱ	0.82 (3)	2.07 (3)	2.8965 (16)	178 (2)
O5—H5B···O4^vi	0.77 (2)	2.10 (3)	2.8730 (19)	177 (2)
N1—H1A···O4	0.90	2.38	3.2442 (17)	160
N2—H2B···O3	0.90	2.04	2.9333 (14)	174
O1—H1E···O5	0.80 (2)	1.93 (2)	2.7311 (16)	175.8 (19)
O5—H5A···O3	0.80 (2)	1.94 (2)	2.7296 (16)	166 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+1, −y+2, −z+1; (v) x, y−1, z; (vi) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₃H₁₀N₂)₂(H₂O)₂](C₄O₄)·4H₂O
M_r	427.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.0429 (4), 9.1752 (5), 14.6510 (8)
β (°)	117.570 (4)
V (Å³)	958.40 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.75 × 0.45 × 0.05

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.638, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	7288, 2204, 2003
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.054, 1.06
No. of reflections	2204
No. of parameters	139
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.17

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

O1—Ni1	2.1429 (9)	N2—Ni1	2.0997 (10)
N1—Ni1	2.1090 (10)

N1—Ni1—O1	88.86 (4)	N2—Ni1—N1	91.94 (4)
N2—Ni1—O1	91.46 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O5ⁱ	0.90	2.35	3.1715 (16)	151.9
N2—H2A···O2ⁱⁱ	0.90	2.33	3.2174 (14)	170.4
O1—H1F···O2ⁱⁱⁱ	0.77 (2)	2.08 (2)	2.8345 (15)	165 (2)
O4—H4A···O2ⁱⁱⁱ	0.80 (2)	2.10 (2)	2.8765 (16)	165 (2)
O4—H4B···O2^iv	0.82 (3)	2.07 (3)	2.8965 (16)	178 (2)
O5—H5B···O4^v	0.77 (2)	2.10 (3)	2.8730 (19)	177 (2)
N1—H1A···O4	0.90	2.38	3.2442 (17)	160.2
N2—H2B···O3	0.90	2.04	2.9333 (14)	173.5
O1—H1E···O5	0.80 (2)	1.93 (2)	2.7311 (16)	175.8 (19)
O5—H5A···O3	0.80 (2)	1.94 (2)	2.7296 (16)	166 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences of Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Grant of Ondokuz Mayıs University).

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