Diaqua­bis(4-methyl­benzoato-κO)bis­(nicotinamide-κN1)nickel(II)

Necefoğlu, H.; Çimen, E.; Tercan, B.; Ermiş, E.; Hökelek, T.

doi:10.1107/S1600536810007385

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m361-m362

doi:10.1107/S1600536810007385

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Diaquabis(4-methylbenzoato-κO)bis(nicotinamide-κN¹)nickel(II)

Hacali Necefoğlu,^a Efdal Çimen,^a Barış Tercan,^b Emel Ermiş ^c and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, ^bDepartment of Physics, Karabük University, 78050 Karabük, Turkey, ^cDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 25 February 2010; accepted 26 February 2010; online 3 March 2010)

The title Ni^II complex, [Ni(C₈H₇O₂)₂(C₆H₆N₂O)₂(H₂O)₂], is centrosymmetric with the Ni atom located on an inversion center. The molecule contains two 4-methylbenzoate (PMB) and two nicotinamide (NA) ligands and two coordinated water molecules, all ligands being monodentate. The four O atoms in the equatorial plane around the Ni atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two N atoms of the NA ligands in the axial positions. The dihedral angle between the carboxylate group and the adjacent benzene ring is 26.15 (10)°, while the pyridine and benzene rings are oriented at a dihedral angle of 87.81 (4)°. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules into a three-dimensional network. The π–π contact between the benzene rings [centroid–centroid distance = 3.896 (1) Å] may further stabilize the crystal structure. A weak C—H⋯π interaction involving the pyridine ring also occurs.

Related literature

For niacin, see: Krishnamachari (1974 ) and for the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972 ). For related structures, see: Hökelek et al. (1996 , 2009a ,b ,c ); Hökelek & Necefoğlu (1998 ).

Experimental

Crystal data

[Ni(C₈H₇O₂)₂(C₆H₆N₂O)₂(H₂O)₂]
M_r = 609.26
Triclinic, $[P \overline 1]$
a = 7.7324 (2) Å
b = 9.7335 (3) Å
c = 9.8198 (3) Å
α = 78.440 (2)°
β = 86.475 (3)°
γ = 71.662 (2)°
V = 687.31 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 99 K
0.33 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.889, T_max = 0.934
12002 measured reflections
3390 independent reflections
3034 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.068
S = 1.05
3390 reflections
204 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1	2.0621 (10)
Ni1—O4	2.0870 (10)
Ni1—N1	2.0859 (12)

Table 2
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the N1/C9–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O2ⁱ	0.86 (2)	2.037 (19)	2.8333 (18)	153.4 (19)
N2—H22⋯O3ⁱⁱ	0.90 (2)	2.05 (2)	2.9192 (19)	161.5 (18)
O4—H41⋯O3ⁱⁱⁱ	0.81 (2)	2.10 (2)	2.8864 (16)	162.9 (19)
O4—H42⋯O2^iv	0.89 (2)	1.75 (2)	2.6240 (16)	165 (2)
C6—H6⋯Cg2^v	0.93	2.65	3.5737 (18)	171
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) -x, -y, -z+1; (v) x, y, z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007385/xu2730sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007385/xu2730Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The title complex, (I), is a crystallographically centrosymmetric mononuclear complex, consisting of two nicotinamide (NA) and two 4-methylbenzoate (PMB) ligands and two coordinated water molecules. The crystal structures of similar complexes of Cu^II, Co^II, Ni^II, Mn^II and Zn^II ions, [Cu(C₇H₅O₂)₂(C₁₀H₁₄N₂O)₂], (II) (Hökelek et al., 1996), [Co(C₆H₆N₂O)₂(C₇H₄NO₄)₂(H₂O)₂], (III) (Hökelek & Necefoğlu, 1998), [Ni(C₇H₄ClO₂)₂(C₆H₆N₂O)₂(H₂O)₂], (IV) (Hökelek et al., 2009a), [Mn(C₇H₄ClO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂], (V) (Hökelek et al., 2009b) and [Zn(C₇H₄BrO₂)₂(C₆H₆N₂O)₂(H₂O)₂], (VI) (Hökelek et al., 2009c) have also been reported. In (II), the two benzoate ions are coordinated to the Cu atom as bidentate ligands, while in the other structures all ligands being monodentate.

The title complex, [Ni(PMB)₂(NA)₂(H₂O)₂], has a centre of symmetry and Ni^II ion is surrounded by two PMB and two NA ligands and two water molecules (Fig. 1). All ligands are monodentate. The four O atoms (O1, O4, and the symmetry-related atoms, O1', O4') in the equatorial plane around the Ni atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two N atoms of the NA ligands (N1, N1') in the axial positions (Fig. 1).

The near equality of the C1—O1 [1.2678 (17) Å] and C1—O2 [1.2654 (17) Å] bonds in the carboxylate group indicates a delocalized bonding arrangement, rather than localized single and double bonds. The average Ni—O bond length is 2.0746 (10) Å (Table 1) and the Ni atom is displaced out of the least-squares plane of the carboxylate group (O1/C1/O2) by 0.5087 (1) Å. The dihedral angle between the planar carboxylate group and the benzene ring A (C2—C7) is 26.15 (10)°, while that between rings A and B (N1/C8—C12) is 87.81 (4)°.

In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds (Table 2) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure. The π–π contact between the benzene rings, Cg1—Cg1ⁱ, [symmetry code (i): 1 - x, -y, 2 - z, where Cg1 is the centroid of ring A (C2—C7)] may further stabilize the structure, with centroid-centroid distance of 3.896 (1) Å. There also exists a weak C—H···π interaction involving the pyridine ring (Table 2).

Related literature top

For niacin, see: Krishnamachari (1974) and for the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek et al. (1996, 2009a,b,c); Hökelek & Necefoğlu (1998).

Experimental top

The title compound was prepared by the reaction of NiSO₄.6(H₂O) (1.32 g, 5 mmol) in H₂O (30 ml) and NA (1.22 g, 10 mmol) in H₂O (15 ml) with sodium 4-methylbenzoate (1.36 g, 10 mmol) in H₂O (300 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving blue single crystals.

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level. Primed atoms are generated by the symmetry operator:(') -x, -y, 1 - z.

Diaquabis(4-methylbenzoato-κO)bis(nicotinamide-κN¹)nickel(II) top

Crystal data top

[Ni(C₈H₇O₂)₂(C₆H₆N₂O)₂(H₂O)₂]	Z = 1
M_r = 609.26	F(000) = 318
Triclinic, P1	D_x = 1.472 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7324 (2) Å	Cell parameters from 6458 reflections
b = 9.7335 (3) Å	θ = 2.8–28.3°
c = 9.8198 (3) Å	µ = 0.76 mm⁻¹
α = 78.440 (2)°	T = 99 K
β = 86.475 (3)°	Prism, blue
γ = 71.662 (2)°	0.33 × 0.28 × 0.25 mm
V = 687.31 (4) Å³

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3390 independent reflections
Radiation source: fine-focus sealed tube	3034 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.889, T_max = 0.934	k = −12→12
12002 measured reflections	l = −12→13

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0238P)² + 0.4565P] where P = (F_o² + 2F_c²)/3
3390 reflections	(Δ/σ)_max < 0.001
204 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Ni(C₈H₇O₂)₂(C₆H₆N₂O)₂(H₂O)₂]	γ = 71.662 (2)°
M_r = 609.26	V = 687.31 (4) Å³
Triclinic, P1	Z = 1
a = 7.7324 (2) Å	Mo Kα radiation
b = 9.7335 (3) Å	µ = 0.76 mm⁻¹
c = 9.8198 (3) Å	T = 99 K
α = 78.440 (2)°	0.33 × 0.28 × 0.25 mm
β = 86.475 (3)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3390 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3034 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.934	R_int = 0.024
12002 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.48 e Å⁻³
3390 reflections	Δρ_min = −0.50 e Å⁻³
204 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.0000	0.0000	0.5000	0.00996 (8)
O1	0.12751 (13)	0.01072 (11)	0.67419 (11)	0.0129 (2)
O2	−0.11125 (14)	0.15789 (11)	0.77116 (11)	0.0149 (2)
O3	0.44171 (14)	0.33247 (11)	0.48634 (12)	0.0177 (2)
O4	0.25984 (15)	−0.07089 (12)	0.41538 (12)	0.0136 (2)
H41	0.342 (3)	−0.137 (2)	0.458 (2)	0.034 (6)*
H42	0.228 (3)	−0.103 (2)	0.345 (2)	0.036 (6)*
N1	−0.00159 (16)	0.21391 (13)	0.41144 (13)	0.0116 (2)
N2	0.33786 (19)	0.55995 (15)	0.35530 (15)	0.0176 (3)
H21	0.252 (3)	0.628 (2)	0.307 (2)	0.022 (5)*
H22	0.425 (3)	0.586 (2)	0.390 (2)	0.024 (5)*
C1	0.05766 (19)	0.09453 (16)	0.75988 (15)	0.0120 (3)
C2	0.18258 (19)	0.12691 (15)	0.85126 (15)	0.0121 (3)
C3	0.3601 (2)	0.12032 (16)	0.81040 (16)	0.0139 (3)
H3	0.4070	0.0851	0.7302	0.017*
C4	0.4678 (2)	0.16598 (16)	0.88863 (16)	0.0153 (3)
H4	0.5855	0.1624	0.8593	0.018*
C5	0.4019 (2)	0.21690 (17)	1.00998 (17)	0.0162 (3)
C6	0.2262 (2)	0.21841 (18)	1.05279 (17)	0.0192 (3)
H6	0.1816	0.2488	1.1356	0.023*
C7	0.1171 (2)	0.17547 (17)	0.97424 (16)	0.0164 (3)
H7	−0.0006	0.1790	1.0037	0.020*
C8	0.5187 (2)	0.26752 (19)	1.09414 (19)	0.0239 (4)
H8A	0.4556	0.3664	1.1063	0.036*
H8B	0.6314	0.2651	1.0463	0.036*
H8C	0.5435	0.2033	1.1834	0.036*
C9	−0.13817 (19)	0.31071 (16)	0.33131 (16)	0.0140 (3)
H9	−0.2385	0.2823	0.3163	0.017*
C10	−0.1356 (2)	0.45107 (17)	0.27015 (17)	0.0169 (3)
H10	−0.2326	0.5157	0.2153	0.020*
C11	0.0139 (2)	0.49377 (16)	0.29208 (16)	0.0156 (3)
H11	0.0188	0.5875	0.2521	0.019*
C12	0.15612 (19)	0.39452 (16)	0.37462 (15)	0.0121 (3)
C13	0.14248 (19)	0.25568 (16)	0.43189 (15)	0.0115 (3)
H13	0.2378	0.1888	0.4869	0.014*
C14	0.32352 (19)	0.42736 (16)	0.40920 (16)	0.0131 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.00972 (13)	0.00810 (13)	0.01255 (14)	−0.00273 (10)	−0.00152 (9)	−0.00267 (10)
O1	0.0132 (5)	0.0108 (5)	0.0144 (5)	−0.0023 (4)	−0.0020 (4)	−0.0036 (4)
O2	0.0120 (5)	0.0152 (5)	0.0175 (6)	−0.0027 (4)	−0.0015 (4)	−0.0050 (4)
O3	0.0162 (5)	0.0107 (5)	0.0257 (6)	−0.0035 (4)	−0.0068 (4)	−0.0016 (5)
O4	0.0114 (5)	0.0124 (5)	0.0163 (6)	−0.0018 (4)	−0.0020 (4)	−0.0038 (5)
N1	0.0122 (6)	0.0100 (6)	0.0128 (6)	−0.0029 (5)	−0.0008 (5)	−0.0035 (5)
N2	0.0172 (7)	0.0113 (6)	0.0254 (8)	−0.0066 (5)	−0.0074 (6)	−0.0003 (6)
C1	0.0134 (7)	0.0098 (7)	0.0124 (7)	−0.0044 (5)	−0.0023 (5)	0.0010 (5)
C2	0.0132 (7)	0.0087 (6)	0.0133 (7)	−0.0021 (5)	−0.0032 (5)	−0.0007 (5)
C3	0.0157 (7)	0.0130 (7)	0.0124 (7)	−0.0033 (6)	−0.0010 (5)	−0.0028 (6)
C4	0.0135 (7)	0.0139 (7)	0.0179 (8)	−0.0040 (6)	−0.0021 (6)	−0.0014 (6)
C5	0.0180 (7)	0.0116 (7)	0.0182 (8)	−0.0024 (6)	−0.0062 (6)	−0.0027 (6)
C6	0.0193 (8)	0.0224 (8)	0.0162 (8)	−0.0028 (6)	−0.0002 (6)	−0.0101 (7)
C7	0.0132 (7)	0.0185 (8)	0.0167 (8)	−0.0030 (6)	−0.0003 (6)	−0.0046 (6)
C8	0.0219 (8)	0.0243 (9)	0.0285 (10)	−0.0062 (7)	−0.0070 (7)	−0.0111 (7)
C9	0.0116 (7)	0.0140 (7)	0.0173 (8)	−0.0039 (6)	−0.0022 (6)	−0.0045 (6)
C10	0.0146 (7)	0.0126 (7)	0.0207 (8)	−0.0008 (6)	−0.0058 (6)	−0.0003 (6)
C11	0.0173 (7)	0.0092 (7)	0.0199 (8)	−0.0040 (6)	−0.0024 (6)	−0.0013 (6)
C12	0.0129 (7)	0.0102 (7)	0.0138 (7)	−0.0028 (5)	−0.0005 (5)	−0.0050 (6)
C13	0.0122 (6)	0.0103 (7)	0.0120 (7)	−0.0025 (5)	−0.0019 (5)	−0.0030 (5)
C14	0.0141 (7)	0.0118 (7)	0.0142 (7)	−0.0032 (6)	0.0000 (5)	−0.0053 (6)

Geometric parameters (Å, º) top

Ni1—O1	2.0621 (10)	C4—C5	1.389 (2)
Ni1—O1ⁱ	2.0621 (10)	C4—H4	0.9300
Ni1—O4ⁱ	2.0870 (10)	C5—C6	1.394 (2)
Ni1—O4	2.0870 (10)	C5—C8	1.509 (2)
Ni1—N1	2.0859 (12)	C6—H6	0.9300
Ni1—N1ⁱ	2.0859 (12)	C7—C2	1.393 (2)
O1—C1	1.2678 (17)	C7—C6	1.383 (2)
O2—C1	1.2654 (17)	C7—H7	0.9300
O3—C14	1.2392 (18)	C8—H8A	0.9600
O4—H41	0.81 (2)	C8—H8B	0.9600
O4—H42	0.88 (2)	C8—H8C	0.9600
N1—C9	1.3421 (19)	C9—C10	1.383 (2)
N1—C13	1.3386 (18)	C9—H9	0.9300
N2—C14	1.3294 (19)	C10—H10	0.9300
N2—H21	0.86 (2)	C11—C10	1.388 (2)
N2—H22	0.89 (2)	C11—H11	0.9300
C1—C2	1.500 (2)	C12—C11	1.388 (2)
C2—C3	1.392 (2)	C12—C13	1.390 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C3	1.389 (2)	C14—C12	1.500 (2)

O1ⁱ—Ni1—O1	180.0	C5—C4—C3	120.87 (14)
O1—Ni1—O4	86.71 (4)	C5—C4—H4	119.6
O1ⁱ—Ni1—O4	93.29 (4)	C4—C5—C6	118.33 (14)
O1—Ni1—O4ⁱ	93.29 (4)	C4—C5—C8	120.73 (14)
O1ⁱ—Ni1—O4ⁱ	86.71 (4)	C6—C5—C8	120.93 (14)
O1—Ni1—N1	89.94 (4)	C5—C6—H6	119.4
O1ⁱ—Ni1—N1	90.06 (4)	C7—C6—C5	121.11 (14)
O1—Ni1—N1ⁱ	90.06 (4)	C7—C6—H6	119.4
O1ⁱ—Ni1—N1ⁱ	89.94 (4)	C2—C7—H7	119.8
O4ⁱ—Ni1—O4	180.0	C6—C7—C2	120.34 (14)
N1—Ni1—O4	86.75 (4)	C6—C7—H7	119.8
N1ⁱ—Ni1—O4	93.25 (4)	C5—C8—H8A	109.5
N1—Ni1—O4ⁱ	93.25 (4)	C5—C8—H8B	109.5
N1ⁱ—Ni1—O4ⁱ	86.75 (4)	C5—C8—H8C	109.5
N1ⁱ—Ni1—N1	180.0	H8A—C8—H8B	109.5
C1—O1—Ni1	125.51 (9)	H8A—C8—H8C	109.5
Ni1—O4—H41	122.0 (15)	H8B—C8—H8C	109.5
Ni1—O4—H42	97.1 (14)	N1—C9—C10	122.60 (14)
H42—O4—H41	108 (2)	N1—C9—H9	118.7
C9—N1—Ni1	123.09 (10)	C10—C9—H9	118.7
C13—N1—Ni1	118.67 (10)	C9—C10—C11	118.88 (14)
C13—N1—C9	118.21 (12)	C9—C10—H10	120.6
C14—N2—H21	122.3 (13)	C11—C10—H10	120.6
C14—N2—H22	117.1 (12)	C10—C11—C12	119.04 (14)
H21—N2—H22	118.3 (18)	C10—C11—H11	120.5
O1—C1—C2	118.42 (13)	C12—C11—H11	120.5
O2—C1—O1	124.67 (14)	C11—C12—C13	118.29 (13)
O2—C1—C2	116.86 (13)	C11—C12—C14	124.54 (13)
C3—C2—C1	121.08 (13)	C13—C12—C14	117.16 (13)
C3—C2—C7	118.83 (14)	N1—C13—C12	122.98 (13)
C7—C2—C1	119.91 (13)	N1—C13—H13	118.5
C2—C3—H3	119.8	C12—C13—H13	118.5
C4—C3—C2	120.46 (14)	O3—C14—N2	122.43 (14)
C4—C3—H3	119.8	O3—C14—C12	119.86 (13)
C3—C4—H4	119.6	N2—C14—C12	117.70 (13)

O4—Ni1—O1—C1	153.43 (11)	O2—C1—C2—C7	23.4 (2)
O4ⁱ—Ni1—O1—C1	−26.57 (11)	C1—C2—C3—C4	172.95 (13)
N1—Ni1—O1—C1	66.68 (11)	C7—C2—C3—C4	−2.1 (2)
N1ⁱ—Ni1—O1—C1	−113.32 (11)	C5—C4—C3—C2	1.0 (2)
O1—Ni1—N1—C9	−144.39 (11)	C3—C4—C5—C6	1.2 (2)
O1ⁱ—Ni1—N1—C9	35.61 (11)	C3—C4—C5—C8	−179.53 (14)
O1—Ni1—N1—C13	37.62 (11)	C4—C5—C6—C7	−2.3 (2)
O1ⁱ—Ni1—N1—C13	−142.38 (11)	C8—C5—C6—C7	178.42 (15)
O4—Ni1—N1—C9	128.90 (12)	C6—C7—C2—C1	−174.10 (14)
O4ⁱ—Ni1—N1—C9	−51.10 (12)	C6—C7—C2—C3	1.0 (2)
O4—Ni1—N1—C13	−49.10 (11)	C2—C7—C6—C5	1.2 (2)
O4ⁱ—Ni1—N1—C13	130.90 (11)	N1—C9—C10—C11	0.1 (2)
Ni1—O1—C1—O2	17.6 (2)	C12—C11—C10—C9	0.0 (2)
Ni1—O1—C1—C2	−159.77 (9)	C13—C12—C11—C10	0.1 (2)
Ni1—N1—C9—C10	−178.28 (11)	C14—C12—C11—C10	−178.64 (14)
C13—N1—C9—C10	−0.3 (2)	C11—C12—C13—N1	−0.3 (2)
Ni1—N1—C13—C12	178.46 (11)	C14—C12—C13—N1	178.56 (13)
C9—N1—C13—C12	0.4 (2)	O3—C14—C12—C11	178.48 (14)
O1—C1—C2—C3	26.1 (2)	O3—C14—C12—C13	−0.3 (2)
O1—C1—C2—C7	−158.94 (14)	N2—C14—C12—C11	−1.1 (2)
O2—C1—C2—C3	−151.54 (14)	N2—C14—C12—C13	−179.83 (13)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the N1/C9–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O2ⁱⁱ	0.86 (2)	2.037 (19)	2.8333 (18)	153.4 (19)
N2—H22···O3ⁱⁱⁱ	0.90 (2)	2.05 (2)	2.9192 (19)	161.5 (18)
O4—H41···O3^iv	0.81 (2)	2.10 (2)	2.8864 (16)	162.9 (19)
O4—H42···O2ⁱ	0.89 (2)	1.75 (2)	2.6240 (16)	165 (2)
C6—H6···Cg2^v	0.93	2.65	3.5737 (18)	171

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

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₇O₂)₂(C₆H₆N₂O)₂(H₂O)₂]
M_r	609.26
Crystal system, space group	Triclinic, P1
Temperature (K)	99
a, b, c (Å)	7.7324 (2), 9.7335 (3), 9.8198 (3)
α, β, γ (°)	78.440 (2), 86.475 (3), 71.662 (2)
V (Å³)	687.31 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.33 × 0.28 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.889, 0.934
No. of measured, independent and observed [I > 2σ(I)] reflections	12002, 3390, 3034
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.068, 1.05
No. of reflections	3390
No. of parameters	204
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.50

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Ni1—O1	2.0621 (10)	Ni1—N1	2.0859 (12)
Ni1—O4	2.0870 (10)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the N1/C9–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O2ⁱ	0.86 (2)	2.037 (19)	2.8333 (18)	153.4 (19)
N2—H22···O3ⁱⁱ	0.90 (2)	2.05 (2)	2.9192 (19)	161.5 (18)
O4—H41···O3ⁱⁱⁱ	0.81 (2)	2.10 (2)	2.8864 (16)	162.9 (19)
O4—H42···O2^iv	0.89 (2)	1.75 (2)	2.6240 (16)	165 (2)
C6—H6···Cg2^v	0.93	2.65	3.5737 (18)	171

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

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 108 T657).

References

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Volume 66| Part 4| April 2010| Pages m361-m362

doi:10.1107/S1600536810007385

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