catena-Poly[[di­aqua­bis­(4-formyl­benzo­ato-κO1)nickel(II)]-μ-pyrazine-κ2N:N′]

Çelik, F.; Dilek, N.; Çaylak Delibaş, N.; Necefoğlu, H.; Hökelek, T.

doi:10.1107/S160053681400155X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Pages m65-m66

doi:10.1107/S160053681400155X

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catena-Poly[[diaquabis(4-formylbenzoato-κO¹)nickel(II)]-μ-pyrazine-κ²N:N′]

Fatih Çelik,^a Nefise Dilek,^b Nagihan Çaylak Delibaş,^c Hacali Necefoğlu ^a and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, ^bAksaray University, Department of Physics, 68100, Aksaray, Turkey, ^cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 16 January 2014; accepted 22 January 2014; online 25 January 2014)

In the title polymeric compound, [Ni(C₈H₅O₃)₂(C₄H₄N₂)(H₂O)₂]_n, the Ni^II atom is located on a twofold rotation axis and has a slightly distorted octahedral coordination sphere. In the equatorial plane, it is coordinated by two carboxylate O atoms of two symmetry-related monodentate formylbenzoate anions and by two N atoms of the bridging pyrazine ligand, which is bisected by the twofold rotation axis. The axial positions are occupied by two O atoms of the coordinating water molecules. In the formylbenzoate anion, the carboxylate group is twisted away from the attached benzene ring by 7.0 (6)°, while the benzene and pyrazine rings are oriented at a dihedral angle of 66.2 (3)°. The pyrazine ligands bridge the Ni^II cations, forming polymeric chains running along the b-axis direction. Intramolecular O—H⋯O hydrogen bonds link the water ligands to the carboxylate O atoms. In the crystal, water–water O—H⋯O hydrogen bonds link adjacent chains into layers parallel to the bc plane. Pyrazine–formyl C—H⋯O hydrogen bonds link the layers, forming a three-dimensional network. There are also weak C—H⋯π interactions present. The title compound is isotypic with the copper(II) complex [Çelik et al. (2014a). Acta Cryst. E70, m4–m5].

CCDC reference: 982792

Related literature

For the structural functions and coordination relationships of the arylcarboxylate ion in transition-metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981 ); Shnulin et al. (1981 ). For applications of transition-metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982 ). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes, see: Chen & Chen (2002 ); Amiraslanov et al. (1979 ); Hauptmann et al. (2000 ). For the isotypic copper(II) complex, see: Çelik et al. (2014a ). For other related structures involving 4-formylbenzoate, see: Çelik et al. (2014b ); Hökelek et al. (2009 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

[Ni(C₈H₅O₃)₂(C₄H₄N₂)(H₂O)₂]
M_r = 473.07
Monoclinic, C 2/c
a = 22.1032 (5) Å
b = 6.9925 (2) Å
c = 12.3366 (3) Å
β = 94.160 (3)°
V = 1901.68 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 296 K
0.48 × 0.23 × 0.14 mm

Data collection

Bruker SMART BREEZE CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.743, T_max = 0.860
9913 measured reflections
1717 independent reflections
1554 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.209
S = 1.16
1717 reflections
150 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.49 e Å⁻³
Δρ_min = −1.05 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H42⋯O1	0.82 (5)	1.81 (6)	2.579 (6)	155 (8)
O4—H41⋯O3ⁱ	0.82 (2)	2.65 (5)	3.395 (8)	152 (8)
C9—H9⋯O3ⁱⁱ	0.93	2.45	3.311 (8)	154
C7—H7⋯Cg1ⁱⁱⁱ	0.93	2.62	3.395 (6)	141
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); 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, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 982792

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681400155X/su2690sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400155X/su2690Isup2.hkl

checkCIF report

Comment top

The structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, as a result they may find applications in biological systems (Antolini et al., 1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes (Chen & Chen, 2002; Amiraslanov et al., 1979; Hauptmann et al., 2000). The title compound, which is isotructural with the copper(II) complex (Çelik et al., 2014a) was synthesized and its crystal structure is reported on herein.

The asymmetric unit of the title compound contains half a Ni^II ion, one formylbenzoate (FB) anion, one water molecule and half of a pyrazine molecule. Atoms Ni1, and N1 and N2 of the pyrazine ligand, are located on a two-fold rotation axis (Fig. 1). The pyrazine ligands bridge adjacent Ni^II ions forming polymeric chains running along the b-axis direction (Fig. 2). The distances between the symmetry related Ni^II ions [Ni1···Ni1ⁱ; symmetry code: (i) x, y + 1, z] is 6.992 (3) Å.

In the equatorial plane of the Ni^II, coordination sphere is composed of two carboxylate O atoms (O2 and O2ⁱⁱ; symmetry code: (ii) - x, y, - z + 1/2) of two symmetry related monodentate formylbenzoate anions and two N atoms (N1 and N2) of the bridging pyrazine ligand, which is bisected by the two-fold rotation axis. The axial positions are occupied by two O atoms (O4 and O4ⁱⁱ) of the coordinated water molecules.

The near equality of the C1—O1 [1.250 (7) Å] and C1—O2 [1.260 (6) Å] bonds in the carboxylate group indicate delocalized bonding arrangement, rather than localized single and double bonds. The Ni—N bond lengths are 2.108 (6) and 2.112 (6) Å, while the Ni—O bond lengths are 2.047 (4) Å (for benzoate oxygen) and 2.107 (4) Å (for water oxygen) close to standard values (Allen et al., 1987). The Ni1 atom is displaced out of the mean-plane of the carboxylate group (O1/C1/O2) by 0.0658 (8) Å. The dihedral angle between the planar carboxylate group and the adjacent benzene ring (C2—C7) is 7.0 (6)°, while the benzene and pyrazine rings are oriented at a dihedral angle of 66.2 (3) °. Strong intramolecular O—H···O hydrogen bonds (Table 1) link the water molecules to the carboxylate oxygens.

In the crystal, O-H_water···O_water hydrogen bonds link adjacent chains into layers parallel to the bc plane (Table 1). C—H_pyrazine···O_formyl hydrogen bonds (Table 1) link the layers to form a three-dimensional network. There are also weak C—H···π interactions present (Table 1).

Related literature top

For the structural functions and coordination relationships of the arylcarboxylate ion in transition-metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981); Shnulin et al. (1981). For applications of transition-metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes, see: Chen & Chen (2002); Amiraslanov et al. (1979); Hauptmann et al. (2000). For the isotypic copper(II) complex, see: Çelik et al. (2014a). For other related structures involving 4-formylbenzoate, see: Çelik et al. (2014b); Hökelek et al. (2009). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of NiSO₄.6H₂O (1.31 g, 5 mmol) in H₂O (70 ml) and pyrazine (0.40 g, 5 mmol) in H₂O (30 ml) with sodium 4-formylbenzoate (1.72 g, 10 mmol) in H₂O (100 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving blue prismatic crystals.

Structure description top

For the structural functions and coordination relationships of the arylcarboxylate ion in transition-metal complexes of benzoic acid derivatives, see: Nadzhafov et al. (1981); Shnulin et al. (1981). For applications of transition-metal complexes with biochemical molecules in biological systems, see: Antolini et al. (1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry, as bifunctional organic ligands, due to the varieties of their coordination modes, see: Chen & Chen (2002); Amiraslanov et al. (1979); Hauptmann et al. (2000). For the isotypic copper(II) complex, see: Çelik et al. (2014a). For other related structures involving 4-formylbenzoate, see: Çelik et al. (2014b); Hökelek et al. (2009). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the coordination geometry around the Ni^II atom of the title molecule, with the atom-labelling. Displacement ellipsoids are drawn at the 50% probability level. The two-fold rotation axis bisects atoms Ni1, N1 and N2.
	Fig. 2. A partial view along the c axis of the crystal packing of the title compound. Hydrogen atoms have been omitted for clarity.

catena-Poly[[diaquabis(4-formylbenzoato-κO¹)nickel(II)]-µ-pyrazine-κ²N:N'] top

Crystal data top

[Ni(C₈H₅O₃)₂(C₄H₄N₂)(H₂O)₂]	F(000) = 976
M_r = 473.07	D_x = 1.652 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5837 reflections
a = 22.1032 (5) Å	θ = 3.1–28.3°
b = 6.9925 (2) Å	µ = 1.08 mm⁻¹
c = 12.3366 (3) Å	T = 296 K
β = 94.160 (3)°	Prism, blue
V = 1901.68 (8) Å³	0.48 × 0.23 × 0.14 mm
Z = 4

Data collection top

Bruker SMART BREEZE CCD diffractometer	1717 independent reflections
Radiation source: fine-focus sealed tube	1554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
φ and ω scans	θ_max = 25.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −26→26
T_min = 0.743, T_max = 0.860	k = −8→8
9913 measured reflections	l = −14→12

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.209	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.1238P)² + 9.9995P] where P = (F_o² + 2F_c²)/3
1717 reflections	(Δ/σ)_max < 0.001
150 parameters	Δρ_max = 2.49 e Å⁻³
2 restraints	Δρ_min = −1.05 e Å⁻³

Crystal data top

[Ni(C₈H₅O₃)₂(C₄H₄N₂)(H₂O)₂]	V = 1901.68 (8) Å³
M_r = 473.07	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.1032 (5) Å	µ = 1.08 mm⁻¹
b = 6.9925 (2) Å	T = 296 K
c = 12.3366 (3) Å	0.48 × 0.23 × 0.14 mm
β = 94.160 (3)°

Data collection top

Bruker SMART BREEZE CCD diffractometer	1717 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	1554 reflections with I > 2σ(I)
T_min = 0.743, T_max = 0.860	R_int = 0.070
9913 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	2 restraints
wR(F²) = 0.209	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 2.49 e Å⁻³
1717 reflections	Δρ_min = −1.05 e Å⁻³
150 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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	0.00000	0.44790 (12)	0.25000	0.0222 (3)
O1	0.13672 (19)	0.3246 (7)	0.3338 (3)	0.0435 (14)
O2	0.08397 (17)	0.4511 (5)	0.1900 (3)	0.0294 (11)
O3	0.3999 (2)	0.3724 (9)	0.0460 (4)	0.0614 (19)
O4	0.0372 (2)	0.4332 (6)	0.4119 (3)	0.0342 (12)
N1	0.00000	0.1464 (8)	0.25000	0.0242 (17)
N2	0.00000	0.7500 (8)	0.25000	0.0260 (19)
C1	0.1321 (2)	0.3907 (7)	0.2394 (5)	0.0277 (16)
C2	0.1890 (2)	0.3983 (7)	0.1787 (5)	0.0284 (16)
C3	0.1889 (3)	0.4908 (8)	0.0787 (5)	0.0300 (17)
C4	0.2420 (3)	0.5042 (9)	0.0271 (5)	0.0320 (17)
C5	0.2955 (3)	0.4294 (8)	0.0736 (5)	0.0339 (17)
C6	0.2958 (3)	0.3342 (8)	0.1733 (5)	0.0338 (17)
C7	0.2424 (2)	0.3196 (8)	0.2243 (5)	0.0290 (17)
C8	0.3520 (3)	0.4471 (10)	0.0178 (6)	0.045 (2)
C9	0.0252 (3)	0.0463 (7)	0.1723 (5)	0.0290 (17)
C10	0.0250 (2)	0.8494 (7)	0.1733 (4)	0.0280 (17)
H3	0.15320	0.54320	0.04700	0.0360*
H4	0.24170	0.56450	−0.04010	0.0380*
H6	0.33140	0.28130	0.20480	0.0410*
H7	0.24240	0.25590	0.29040	0.0350*
H8	0.35070	0.52240	−0.04450	0.0540*
H9	0.04310	0.11080	0.11700	0.0350*
H10	0.04300	0.78400	0.11840	0.0340*
H41	0.040 (4)	0.545 (5)	0.430 (7)	0.06 (3)*
H42	0.0721 (18)	0.396 (13)	0.407 (7)	0.07 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0321 (6)	0.0093 (5)	0.0253 (6)	0.0000	0.0022 (4)	0.0000
O1	0.046 (2)	0.049 (3)	0.036 (2)	0.008 (2)	0.0059 (18)	0.012 (2)
O2	0.032 (2)	0.0188 (19)	0.038 (2)	0.0020 (14)	0.0065 (16)	0.0009 (16)
O3	0.045 (3)	0.085 (4)	0.055 (3)	0.001 (3)	0.010 (2)	−0.006 (3)
O4	0.047 (2)	0.031 (2)	0.024 (2)	0.0063 (19)	−0.0012 (17)	−0.0034 (17)
N1	0.036 (3)	0.011 (3)	0.026 (3)	0.0000	0.005 (2)	0.0000
N2	0.034 (3)	0.006 (3)	0.038 (4)	0.0000	0.003 (3)	0.0000
C1	0.039 (3)	0.012 (2)	0.032 (3)	−0.002 (2)	0.002 (2)	0.000 (2)
C2	0.040 (3)	0.013 (2)	0.032 (3)	−0.002 (2)	0.002 (2)	−0.004 (2)
C3	0.036 (3)	0.022 (3)	0.031 (3)	0.000 (2)	−0.004 (2)	−0.002 (2)
C4	0.047 (3)	0.023 (3)	0.026 (3)	−0.006 (2)	0.003 (2)	0.000 (2)
C5	0.040 (3)	0.026 (3)	0.036 (3)	−0.005 (2)	0.004 (2)	−0.007 (2)
C6	0.036 (3)	0.027 (3)	0.038 (3)	0.005 (2)	0.001 (2)	−0.002 (2)
C7	0.039 (3)	0.021 (3)	0.027 (3)	0.005 (2)	0.003 (2)	0.002 (2)
C8	0.050 (4)	0.044 (4)	0.043 (4)	−0.007 (3)	0.008 (3)	−0.002 (3)
C9	0.045 (3)	0.017 (3)	0.026 (3)	−0.002 (2)	0.009 (2)	0.002 (2)
C10	0.041 (3)	0.016 (3)	0.028 (3)	0.000 (2)	0.010 (2)	−0.004 (2)

Geometric parameters (Å, º) top

Ni1—O2	2.048 (4)	C2—C3	1.393 (8)
Ni1—O4	2.107 (4)	C2—C7	1.384 (7)
Ni1—N1	2.108 (6)	C3—C4	1.378 (9)
Ni1—N2	2.112 (6)	C4—C5	1.379 (9)
Ni1—O2ⁱ	2.048 (4)	C5—C6	1.398 (9)
Ni1—O4ⁱ	2.107 (4)	C5—C8	1.474 (9)
O1—C1	1.250 (7)	C6—C7	1.381 (8)
O2—C1	1.260 (6)	C9—C10ⁱⁱ	1.377 (7)
O3—C8	1.209 (8)	C3—H3	0.9300
O4—H42	0.82 (5)	C4—H4	0.9300
O4—H41	0.81 (4)	C6—H6	0.9300
N1—C9ⁱ	1.340 (7)	C7—H7	0.9300
N1—C9	1.340 (7)	C8—H8	0.9300
N2—C10	1.327 (6)	C9—H9	0.9300
N2—C10ⁱ	1.327 (6)	C10—H10	0.9300
C1—C2	1.511 (7)

O2—Ni1—O4	92.38 (16)	C3—C2—C7	119.4 (5)
O2—Ni1—N1	90.63 (10)	C1—C2—C7	120.0 (5)
O2—Ni1—N2	89.37 (10)	C1—C2—C3	120.5 (5)
O2—Ni1—O2ⁱ	178.75 (15)	C2—C3—C4	119.6 (6)
O2—Ni1—O4ⁱ	87.68 (16)	C3—C4—C5	121.0 (6)
O4—Ni1—N1	87.20 (12)	C4—C5—C6	119.7 (6)
O4—Ni1—N2	92.80 (12)	C4—C5—C8	120.2 (6)
O2ⁱ—Ni1—O4	87.68 (16)	C6—C5—C8	120.0 (6)
O4—Ni1—O4ⁱ	174.41 (17)	C5—C6—C7	119.1 (6)
N1—Ni1—N2	180.00 (1)	C2—C7—C6	121.2 (6)
O2ⁱ—Ni1—N1	90.63 (10)	O3—C8—C5	125.7 (7)
O4ⁱ—Ni1—N1	87.20 (12)	N1—C9—C10ⁱⁱ	120.9 (5)
O2ⁱ—Ni1—N2	89.37 (10)	N2—C10—C9ⁱⁱⁱ	122.2 (5)
O4ⁱ—Ni1—N2	92.80 (12)	C2—C3—H3	120.00
O2ⁱ—Ni1—O4ⁱ	92.38 (16)	C4—C3—H3	120.00
Ni1—O2—C1	125.3 (4)	C3—C4—H4	119.00
Ni1—O4—H41	103 (6)	C5—C4—H4	120.00
Ni1—O4—H42	105 (6)	C5—C6—H6	120.00
H41—O4—H42	106 (9)	C7—C6—H6	120.00
C9—N1—C9ⁱ	117.0 (5)	C2—C7—H7	120.00
Ni1—N1—C9	121.5 (3)	C6—C7—H7	119.00
Ni1—N1—C9ⁱ	121.5 (3)	O3—C8—H8	117.00
Ni1—N2—C10	121.6 (3)	C5—C8—H8	117.00
Ni1—N2—C10ⁱ	121.6 (3)	N1—C9—H9	120.00
C10—N2—C10ⁱ	116.8 (5)	C10ⁱⁱ—C9—H9	120.00
O1—C1—O2	125.7 (5)	N2—C10—H10	119.00
O2—C1—C2	116.9 (5)	C9ⁱⁱⁱ—C10—H10	119.00
O1—C1—C2	117.4 (4)

O4—Ni1—O2—C1	22.0 (4)	Ni1—N1—C9—C10ⁱⁱ	179.9 (4)
N1—Ni1—O2—C1	−65.3 (4)	Ni1—N2—C10—C9ⁱⁱⁱ	179.9 (4)
N2—Ni1—O2—C1	114.7 (4)	O1—C1—C2—C3	−172.2 (5)
O4ⁱ—Ni1—O2—C1	−152.5 (4)	O1—C1—C2—C7	5.2 (8)
O2—Ni1—N1—C9	−35.6 (3)	O2—C1—C2—C3	8.0 (7)
O2—Ni1—N1—C9ⁱ	144.4 (3)	O2—C1—C2—C7	−174.5 (5)
O4—Ni1—N1—C9	−128.0 (3)	C1—C2—C3—C4	176.9 (5)
O4—Ni1—N1—C9ⁱ	52.0 (3)	C7—C2—C3—C4	−0.6 (8)
O2ⁱ—Ni1—N1—C9	144.4 (3)	C1—C2—C7—C6	−176.3 (5)
O4ⁱ—Ni1—N1—C9	52.0 (3)	C3—C2—C7—C6	1.2 (8)
O2—Ni1—N2—C10	35.5 (3)	C2—C3—C4—C5	−0.8 (9)
O2—Ni1—N2—C10ⁱ	−144.5 (3)	C3—C4—C5—C6	1.6 (9)
O4—Ni1—N2—C10	127.9 (3)	C3—C4—C5—C8	−179.3 (6)
O4—Ni1—N2—C10ⁱ	−52.1 (3)	C4—C5—C6—C7	−1.0 (9)
O2ⁱ—Ni1—N2—C10	−144.5 (3)	C8—C5—C6—C7	179.9 (6)
O4ⁱ—Ni1—N2—C10	−52.1 (3)	C4—C5—C8—O3	−172.9 (7)
Ni1—O2—C1—O1	−2.3 (8)	C6—C5—C8—O3	6.3 (10)
Ni1—O2—C1—C2	177.5 (3)	C5—C6—C7—C2	−0.4 (9)

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H42···O1	0.82 (5)	1.81 (6)	2.579 (6)	155 (8)
O4—H41···O3^iv	0.82 (2)	2.65 (5)	3.395 (8)	152 (8)
C9—H9···O3^v	0.93	2.45	3.311 (8)	154
C7—H7···Cg1^vi	0.93	2.62	3.395 (6)	141

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H42···O1	0.82 (5)	1.81 (6)	2.579 (6)	155 (8)
O4—H41···O3ⁱ	0.82 (2)	2.65 (5)	3.395 (8)	152 (8)
C9—H9···O3ⁱⁱ	0.93	2.45	3.311 (8)	154
C7—H7···Cg1ⁱⁱⁱ	0.93	2.62	3.395 (6)	141

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

Acknowledgements

The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization). This work is supported financially by Kafkas University Research Fund (grant No. 2012-FEF-12).

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Volume 70| Part 2| February 2014| Pages m65-m66

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