Diaqua­bis(N,N-diethyl­nicotinamide-κN1)bis­(4-formyl­benzoato-κO)nickel(II)

Sertçelik, M.; Tercan, B.; Şahin, E.; Necefoğlu, H.; Hökelek, T.

doi:10.1107/S1600536809006345

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages m326-m327

doi:10.1107/S1600536809006345

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Diaquabis(N,N-diethylnicotinamide-κN¹)bis(4-formylbenzoato-κO)nickel(II)

Mustafa Sertçelik,^a Barış Tercan,^b Ertan Şahin,^c Hacali Necefoğlu ^a and Tuncer Hökelek ^d ^*

^aKafkas University, Department of Chemistry, 63100 Kars, Turkey, ^bKarabük University, Department of Physics, 78050 Karabük, Turkey, ^cAtatürk University, Department of Chemistry, 22240 Erzurum, Turkey, and ^dHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 9 February 2009; accepted 20 February 2009; online 25 February 2009)

In the title centrosymmetric mononuclear Ni^II compound, [Ni(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂], the central Ni^II atom is coordinated by two O atoms from two 4-formylbenzoate (FOB) ligands, two O atoms from two water molecules and two N atoms from two diethylnicotinamide (DENA) ligands. The coordination geometry is slightly distorted octahedral, with four O atoms in the equatorial plane and two N atoms in axial positions. Intramolecular O—H⋯O hydrogen bonds are observed. In the crystal structure, molecules are linked into chains along the a axis by intermolecular O—H⋯O hydrogen bonds. The structure is further stabilized by π–π interactions between the pyridine rings of DENA units, with a centroid–centroid distance of 3.668 (2) Å.

Related literature

For general background, see: Antolini et al. (1982 ); Bigoli et al. (1972 ); Nadzhafov et al. (1981 ); Shnulin et al. (1981 ). For related structures, see: Hökelek et al. (1995 , 1997 , 2007 , 2008 ); Hökelek & Necefouglu (1996 , 1997 ); Hökelek & Necefoğlu (2007 ); Sertçelik et al. (2009 ).

Experimental

Crystal data

[Ni(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r = 749.43
Triclinic, $[P \overline 1]$
a = 7.2909 (2) Å
b = 8.6883 (3) Å
c = 15.9037 (4) Å
α = 85.034 (5)°
β = 78.576 (4)°
γ = 67.594 (3)°
V = 912.85 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 294 K
0.35 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.870, T_max = 0.918
19676 measured reflections
3740 independent reflections
2797 reflections with I > 2σ(I)
R_int = 0.098

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.122
S = 1.04
3740 reflections
242 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Selected bond lengths (Å)

O5—Ni1	2.084 (2)
Ni1—O1	2.069 (2)
Ni1—N1	2.100 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4ⁱ	0.84 (2)	1.97 (2)	2.796 (4)	170 (3)
O5—H52⋯O2	0.85 (3)	1.81 (3)	2.646 (4)	168 (4)
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006345/ci2769sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006345/ci2769Isup2.hkl

checkCIF report

Comment top

The nicotinic acid derivative N,N-diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972). 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). The structure determination of the title compound, a nickel complex with two formylbenzoate (FOB), two diethylnicotinamide (DENA) ligands and two water molecules, was undertaken in order to determine the properties of the ligands and also to compare the results obtained with those reported previously.

The title compound is a monomeric complex, with the Ni^II atom on a centre of symmetry (Fig. 1). All ligands are monodentate. The four O atoms (O1, O5, and the symmetry-related atoms, O1', O5') lie in the equatorial plane around the Ni1 atom forming a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two N atoms of the DENA ligands (N1, N1') in the axial positions (Table 1 and Fig. 1). An intramolecular O—H···O hydrogen bond (Table 2) results in the formation of a six-membered ring Ni1/O1/O2/O5/C1/H52 ring.

The near equality of the C1—O1 [1.263 (4) Å] and C1—O2 [1.249 (4) Å] bonds in the carboxylate group indicates a delocalized bonding arrangement, rather than localized single and double bonds, and may be compared with the corresponding distances: 1.262 (3) and 1.249 (3) Å in [Mn(DENA)₂(C₈H₅O₃)₂(H₂O)₂] (Sertçelik et al., 2009), 1.256 (6) and 1.245 (6) Å in [Mn(DENA)₂(C₇H₄ClO₂)₂(H₂O)₂] (Hökelek et al., 2008), 1.265 (6) and 1.275 (6) Å in [Mn(C₉H₁₀NO₂)₂(H₂O)₄].2H₂O (Hökelek & Necefoğlu, 2007), 1.260 (4) and 1.252 (4) Å in [Zn(DENA)₂(C₇H₄FO₂)₂(H₂O)₂] (Hökelek et al., 2007), 1.259 (9) and 1.273 (9) Å in Cu₂(DENA)₂(C₆H₅COO)₄ (Hökelek et al., 1995), 1.279 (4) and 1.246 (4) Å in [Zn₂(DENA)₂(C₇H₅O₃)₄].2H₂O (Hökelek & Necefoğlu, 1996), 1.251 (6) and 1.254 (7) Å in [Co(DENA)₂(C₇H₅O₃)₂(H₂O)₂] (Hökelek & Necefoğlu, 1997), 1.278 (3) and 1.246 (3) Å in [Cu(DENA)₂(C₇H₄NO₄)₂(H₂O)₂] (Hökelek et al., 1997). The average Ni—O bond length in the title complex is 2.077 (3) Å and the Ni1 atom is displaced out of the least-squares plane of the carboxylate group (O1/C1/O2) by 0.732 (1) Å. The dihedral angle between the planar carboxylate group and the C2-C7 benzene ring is 4.3 (3)°.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into infinite chains (Fig. 2) along the a axis, which may be effective in the stabilization of the structure. A π-π contact is also observed between the pyridine rings (N1/C9—C13, centroid Cg1) of DENA units, with a Cg1···Cg1ⁱ [symmetry code: (i) 1-x, -1-y, -z] distance of 3.668 (2) Å.

Related literature top

For general backgroud, see: Antolini et al. (1982); Bigoli et al. (1972); Nadzhafov et al. (1981); Shnulin et al. (1981). For related structures, see: Hökelek et al. (1995, 1997, 2007, 2008); Hökelek & Necefouglu (1996, 1997); Hökelek & Necefoğlu (2007); Sertçelik et al. (2009).

Experimental top

The title compound was prepared by the reaction of Ni(SO₄)H₂O (1.73 g, 10 mmol) in H₂O (50 ml) and DENA (3.56 g, 20 mmol) in H₂O (15 ml) with sodium 4-formylbenzoate (3.44 g, 20 mmol) in H₂O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving green single crystals.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. Primed atoms are generated by the symmetry operator (-x, -y, -z).
	Fig. 2. A partial packing diagram of the title compound viewed down the a axis, showing hydrogen bonds (dotted lines) linking the molecules into chains. H atoms not involved in hydrogen bonding have been omitted.

Diaquabis(N,N-diethylnicotinamide-κN¹)bis(4- formylbenzoato-κO)nickel(II) top

Crystal data top

[Ni(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	Z = 1
M_r = 749.43	F(000) = 394
Triclinic, P1	D_x = 1.363 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2909 (2) Å	Cell parameters from 4227 reflections
b = 8.6883 (3) Å	θ = 2.5–26.4°
c = 15.9037 (4) Å	µ = 0.59 mm⁻¹
α = 85.034 (5)°	T = 294 K
β = 78.576 (4)°	Prism, green
γ = 67.594 (3)°	0.35 × 0.20 × 0.15 mm
V = 912.85 (5) Å³

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3740 independent reflections
Radiation source: fine-focus sealed tube	2797 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
ω scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→9
T_min = 0.870, T_max = 0.918	k = −10→10
19676 measured reflections	l = −19→19

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0235P)² + 0.8051P] where P = (F_o² + 2F_c²)/3
3740 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.50 e Å⁻³
3 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Ni(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	γ = 67.594 (3)°
M_r = 749.43	V = 912.85 (5) Å³
Triclinic, P1	Z = 1
a = 7.2909 (2) Å	Mo Kα radiation
b = 8.6883 (3) Å	µ = 0.59 mm⁻¹
c = 15.9037 (4) Å	T = 294 K
α = 85.034 (5)°	0.35 × 0.20 × 0.15 mm
β = 78.576 (4)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3740 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2797 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.918	R_int = 0.098
19676 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	3 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.50 e Å⁻³
3740 reflections	Δρ_min = −0.31 e Å⁻³
242 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
O5	−0.2711 (4)	−0.0197 (4)	0.06069 (16)	0.0494 (6)
H52	−0.284 (6)	0.028 (4)	0.1070 (13)	0.069 (14)*
H51	−0.260 (6)	−0.1180 (19)	0.074 (2)	0.072 (15)*
Ni1	0.0000	0.0000	0.0000	0.03948 (19)
O1	0.0244 (3)	0.1122 (3)	0.10462 (14)	0.0465 (6)
O2	−0.2567 (4)	0.1272 (3)	0.19683 (16)	0.0569 (7)
N1	0.1775 (4)	−0.2306 (3)	0.04762 (17)	0.0427 (7)
O4	0.7320 (4)	−0.3311 (3)	0.12366 (16)	0.0579 (7)
C1	−0.0812 (5)	0.1254 (4)	0.1788 (2)	0.0430 (8)
C12	0.4355 (5)	−0.3815 (4)	0.1297 (2)	0.0423 (8)
C13	0.3191 (5)	−0.2372 (4)	0.0918 (2)	0.0433 (8)
H13	0.3401	−0.1398	0.0974	0.052*
C7	0.2092 (5)	0.1420 (4)	0.2370 (2)	0.0467 (8)
H7	0.2787	0.1384	0.1810	0.056*
C9	0.1550 (5)	−0.3738 (4)	0.0380 (2)	0.0467 (8)
H9	0.0593	−0.3722	0.0067	0.056*
C2	0.0178 (5)	0.1355 (4)	0.2521 (2)	0.0420 (8)
N2	0.6115 (5)	−0.4182 (4)	0.2506 (2)	0.0617 (9)
C3	−0.0823 (5)	0.1368 (4)	0.3360 (2)	0.0502 (9)
H3	−0.2093	0.1304	0.3472	0.060*
C11	0.4075 (5)	−0.5277 (4)	0.1196 (2)	0.0477 (9)
H11	0.4824	−0.6269	0.1445	0.057*
O3	0.4414 (5)	0.1916 (5)	0.4558 (2)	0.0974 (11)
C14	0.6023 (5)	−0.3740 (4)	0.1690 (2)	0.0474 (9)
C4	0.0071 (6)	0.1476 (5)	0.4030 (2)	0.0559 (10)
H4	−0.0606	0.1483	0.4591	0.067*
C6	0.2976 (5)	0.1538 (5)	0.3041 (2)	0.0523 (9)
H6	0.4251	0.1592	0.2932	0.063*
C10	0.2674 (5)	−0.5233 (4)	0.0723 (2)	0.0505 (9)
H10	0.2483	−0.6202	0.0635	0.061*
C5	0.1956 (6)	0.1575 (5)	0.3878 (2)	0.0533 (9)
C17	0.7912 (7)	−0.4225 (6)	0.2841 (3)	0.0746 (13)
H17A	0.8047	−0.4912	0.3356	0.090*
H17B	0.9119	−0.4723	0.2417	0.090*
C15	0.4604 (7)	−0.4666 (6)	0.3106 (3)	0.0740 (13)
H15A	0.3689	−0.4823	0.2785	0.089*
H15B	0.5285	−0.5725	0.3373	0.089*
C16	0.3433 (9)	−0.3450 (9)	0.3777 (4)	0.137 (3)
H16A	0.2414	−0.3797	0.4119	0.206*
H16B	0.2804	−0.2383	0.3518	0.206*
H16C	0.4309	−0.3367	0.4134	0.206*
C8	0.2863 (7)	0.1717 (6)	0.4606 (3)	0.0767 (13)
H8	0.2159	0.1645	0.5154	0.092*
C18	0.7725 (8)	−0.2525 (6)	0.3038 (3)	0.0961 (17)
H18A	0.8938	−0.2582	0.3212	0.144*
H18B	0.6600	−0.2068	0.3494	0.144*
H18C	0.7518	−0.1827	0.2537	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0454 (14)	0.0569 (17)	0.0485 (16)	−0.0216 (13)	−0.0106 (12)	0.0032 (14)
Ni1	0.0359 (3)	0.0445 (4)	0.0398 (4)	−0.0152 (3)	−0.0123 (3)	0.0044 (3)
O1	0.0473 (14)	0.0542 (15)	0.0420 (14)	−0.0207 (12)	−0.0141 (11)	0.0019 (11)
O2	0.0440 (14)	0.0733 (18)	0.0544 (15)	−0.0224 (13)	−0.0070 (12)	−0.0074 (13)
N1	0.0374 (15)	0.0452 (17)	0.0475 (17)	−0.0160 (13)	−0.0122 (12)	0.0030 (13)
O4	0.0500 (15)	0.0703 (18)	0.0611 (16)	−0.0315 (14)	−0.0132 (13)	0.0098 (14)
C1	0.0424 (19)	0.0387 (19)	0.046 (2)	−0.0103 (15)	−0.0139 (16)	0.0022 (15)
C12	0.0368 (18)	0.050 (2)	0.0411 (19)	−0.0174 (16)	−0.0105 (15)	0.0058 (16)
C13	0.0418 (18)	0.0436 (19)	0.047 (2)	−0.0158 (16)	−0.0144 (16)	0.0009 (16)
C7	0.048 (2)	0.053 (2)	0.0386 (19)	−0.0192 (17)	−0.0045 (15)	−0.0002 (16)
C9	0.046 (2)	0.054 (2)	0.046 (2)	−0.0236 (18)	−0.0159 (16)	0.0037 (17)
C2	0.0421 (19)	0.0426 (19)	0.0410 (19)	−0.0144 (16)	−0.0106 (15)	0.0013 (15)
N2	0.061 (2)	0.080 (2)	0.057 (2)	−0.0371 (18)	−0.0232 (16)	0.0143 (18)
C3	0.044 (2)	0.057 (2)	0.048 (2)	−0.0182 (18)	−0.0081 (16)	0.0019 (18)
C11	0.0444 (19)	0.046 (2)	0.051 (2)	−0.0137 (17)	−0.0145 (16)	0.0106 (17)
O3	0.101 (3)	0.155 (3)	0.069 (2)	−0.076 (3)	−0.0352 (19)	0.005 (2)
C14	0.044 (2)	0.050 (2)	0.050 (2)	−0.0176 (17)	−0.0140 (17)	0.0077 (17)
C4	0.062 (2)	0.066 (3)	0.038 (2)	−0.024 (2)	−0.0041 (17)	−0.0028 (18)
C6	0.051 (2)	0.061 (2)	0.051 (2)	−0.0257 (19)	−0.0137 (17)	−0.0005 (18)
C10	0.054 (2)	0.046 (2)	0.057 (2)	−0.0224 (18)	−0.0179 (18)	0.0045 (17)
C5	0.058 (2)	0.062 (2)	0.044 (2)	−0.025 (2)	−0.0139 (18)	0.0018 (18)
C17	0.081 (3)	0.078 (3)	0.076 (3)	−0.033 (3)	−0.038 (2)	0.014 (2)
C15	0.081 (3)	0.092 (3)	0.057 (3)	−0.040 (3)	−0.019 (2)	0.009 (2)
C16	0.102 (5)	0.176 (7)	0.131 (5)	−0.059 (5)	0.026 (4)	−0.069 (5)
C8	0.081 (3)	0.106 (4)	0.054 (3)	−0.042 (3)	−0.024 (2)	−0.003 (2)
C18	0.128 (5)	0.085 (4)	0.094 (4)	−0.046 (3)	−0.049 (3)	−0.002 (3)

Geometric parameters (Å, º) top

O5—Ni1	2.084 (2)	N2—C17	1.496 (5)
O5—H52	0.85 (3)	C3—C4	1.380 (5)
O5—H51	0.84 (2)	C3—H3	0.93
Ni1—O1	2.069 (2)	C11—C10	1.371 (5)
Ni1—O1ⁱ	2.069 (2)	C11—H11	0.93
Ni1—O5ⁱ	2.084 (2)	O3—C8	1.194 (5)
Ni1—N1	2.100 (3)	C4—C5	1.382 (5)
Ni1—N1ⁱ	2.100 (3)	C4—H4	0.93
O1—C1	1.263 (4)	C6—C5	1.386 (5)
O2—C1	1.249 (4)	C6—H6	0.93
N1—C9	1.340 (4)	C10—H10	0.93
N1—C13	1.341 (4)	C5—C8	1.478 (5)
O4—C14	1.227 (4)	C17—C18	1.486 (6)
C1—C2	1.511 (4)	C17—H17A	0.97
C12—C13	1.384 (4)	C17—H17B	0.97
C12—C11	1.389 (5)	C15—C16	1.459 (6)
C12—C14	1.498 (4)	C15—H15A	0.97
C13—H13	0.93	C15—H15B	0.97
C7—C6	1.380 (4)	C16—H16A	0.96
C7—C2	1.391 (4)	C16—H16B	0.96
C7—H7	0.93	C16—H16C	0.96
C9—C10	1.379 (5)	C8—H8	0.93
C9—H9	0.93	C18—H18A	0.96
C2—C3	1.388 (5)	C18—H18B	0.96
N2—C14	1.328 (4)	C18—H18C	0.96
N2—C15	1.473 (5)

Ni1—O5—H52	98 (3)	C10—C11—C12	118.8 (3)
Ni1—O5—H51	113 (3)	C10—C11—H11	120.6
H52—O5—H51	106 (2)	C12—C11—H11	120.6
O1—Ni1—O1ⁱ	180.00 (6)	O4—C14—N2	121.3 (3)
O1—Ni1—O5	92.91 (10)	O4—C14—C12	118.6 (3)
O1ⁱ—Ni1—O5	87.09 (10)	N2—C14—C12	120.1 (3)
O1—Ni1—O5ⁱ	87.09 (10)	C3—C4—C5	121.0 (3)
O1ⁱ—Ni1—O5ⁱ	92.91 (10)	C3—C4—H4	119.5
O5—Ni1—O5ⁱ	180.00 (19)	C5—C4—H4	119.5
O1—Ni1—N1	88.53 (10)	C7—C6—C5	119.8 (3)
O1ⁱ—Ni1—N1	91.47 (10)	C7—C6—H6	120.1
O5—Ni1—N1	93.76 (10)	C5—C6—H6	120.1
O5ⁱ—Ni1—N1	86.24 (10)	C11—C10—C9	119.3 (3)
O1—Ni1—N1ⁱ	91.47 (10)	C11—C10—H10	120.3
O1ⁱ—Ni1—N1ⁱ	88.53 (10)	C9—C10—H10	120.3
O5—Ni1—N1ⁱ	86.24 (10)	C4—C5—C6	119.4 (3)
O5ⁱ—Ni1—N1ⁱ	93.76 (10)	C4—C5—C8	119.8 (4)
N1—Ni1—N1ⁱ	180.0 (2)	C6—C5—C8	120.8 (4)
C1—O1—Ni1	126.8 (2)	C18—C17—N2	111.3 (4)
C9—N1—C13	117.2 (3)	C18—C17—H17A	109.4
C9—N1—Ni1	123.6 (2)	N2—C17—H17A	109.4
C13—N1—Ni1	119.3 (2)	C18—C17—H17B	109.4
O2—C1—O1	125.9 (3)	N2—C17—H17B	109.4
O2—C1—C2	117.7 (3)	H17A—C17—H17B	108.0
O1—C1—C2	116.3 (3)	C16—C15—N2	113.6 (4)
C13—C12—C11	118.2 (3)	C16—C15—H15A	108.8
C13—C12—C14	117.4 (3)	N2—C15—H15A	108.8
C11—C12—C14	123.8 (3)	C16—C15—H15B	108.8
N1—C13—C12	123.4 (3)	N2—C15—H15B	108.8
N1—C13—H13	118.3	H15A—C15—H15B	107.7
C12—C13—H13	118.3	C15—C16—H16A	109.5
C6—C7—C2	120.9 (3)	C15—C16—H16B	109.5
C6—C7—H7	119.6	H16A—C16—H16B	109.5
C2—C7—H7	119.6	C15—C16—H16C	109.5
N1—C9—C10	123.0 (3)	H16A—C16—H16C	109.5
N1—C9—H9	118.5	H16B—C16—H16C	109.5
C10—C9—H9	118.5	O3—C8—C5	126.2 (4)
C3—C2—C7	119.0 (3)	O3—C8—H8	116.9
C3—C2—C1	119.8 (3)	C5—C8—H8	116.9
C7—C2—C1	121.2 (3)	C17—C18—H18A	109.5
C14—N2—C15	125.2 (3)	C17—C18—H18B	109.5
C14—N2—C17	117.6 (3)	H18A—C18—H18B	109.5
C15—N2—C17	117.1 (3)	C17—C18—H18C	109.5
C4—C3—C2	119.9 (3)	H18A—C18—H18C	109.5
C4—C3—H3	120.1	H18B—C18—H18C	109.5
C2—C3—H3	120.1

O5—Ni1—O1—C1	10.8 (3)	C7—C2—C3—C4	1.2 (5)
O5ⁱ—Ni1—O1—C1	−169.2 (3)	C1—C2—C3—C4	−179.4 (3)
N1—Ni1—O1—C1	−82.9 (3)	C13—C12—C11—C10	0.4 (5)
N1ⁱ—Ni1—O1—C1	97.1 (3)	C14—C12—C11—C10	−171.1 (3)
O1—Ni1—N1—C9	146.8 (3)	C15—N2—C14—O4	178.1 (4)
O1ⁱ—Ni1—N1—C9	−33.2 (3)	C17—N2—C14—O4	−3.2 (6)
O5—Ni1—N1—C9	54.0 (3)	C15—N2—C14—C12	−4.0 (6)
O5ⁱ—Ni1—N1—C9	−126.0 (3)	C17—N2—C14—C12	174.7 (3)
O1—Ni1—N1—C13	−31.7 (2)	C13—C12—C14—O4	−57.3 (5)
O1ⁱ—Ni1—N1—C13	148.3 (2)	C11—C12—C14—O4	114.3 (4)
O5—Ni1—N1—C13	−124.5 (3)	C13—C12—C14—N2	124.7 (4)
O5ⁱ—Ni1—N1—C13	55.5 (3)	C11—C12—C14—N2	−63.7 (5)
Ni1—O1—C1—O2	−26.2 (5)	C2—C3—C4—C5	0.1 (6)
Ni1—O1—C1—C2	152.2 (2)	C2—C7—C6—C5	0.7 (5)
C9—N1—C13—C12	−2.3 (5)	C12—C11—C10—C9	−1.6 (5)
Ni1—N1—C13—C12	176.3 (2)	N1—C9—C10—C11	0.8 (6)
C11—C12—C13—N1	1.6 (5)	C3—C4—C5—C6	−1.0 (6)
C14—C12—C13—N1	173.7 (3)	C3—C4—C5—C8	179.0 (4)
C13—N1—C9—C10	1.1 (5)	C7—C6—C5—C4	0.7 (6)
Ni1—N1—C9—C10	−177.5 (3)	C7—C6—C5—C8	−179.4 (4)
C6—C7—C2—C3	−1.6 (5)	C14—N2—C17—C18	78.7 (5)
C6—C7—C2—C1	179.0 (3)	C15—N2—C17—C18	−102.4 (5)
O2—C1—C2—C3	3.7 (5)	C14—N2—C15—C16	−110.3 (5)
O1—C1—C2—C3	−174.9 (3)	C17—N2—C15—C16	71.0 (6)
O2—C1—C2—C7	−177.0 (3)	C4—C5—C8—O3	−175.0 (5)
O1—C1—C2—C7	4.5 (5)	C6—C5—C8—O3	5.1 (7)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ⁱⁱ	0.84 (2)	1.97 (2)	2.796 (4)	170 (3)
O5—H52···O2	0.85 (3)	1.81 (3)	2.646 (4)	168 (4)

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r	749.43
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.2909 (2), 8.6883 (3), 15.9037 (4)
α, β, γ (°)	85.034 (5), 78.576 (4), 67.594 (3)
V (Å³)	912.85 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.35 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.870, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	19676, 3740, 2797
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.122, 1.04
No. of reflections	3740
No. of parameters	242
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.31

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

O5—Ni1	2.084 (2)	Ni1—N1	2.100 (3)
Ni1—O1	2.069 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ⁱ	0.84 (2)	1.97 (2)	2.796 (4)	170 (3)
O5—H52···O2	0.85 (3)	1.81 (3)	2.646 (4)	168 (4)

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors are indebted to the Department of Chemistry, Atatürk University, Erzurum, Turkey, for the use of the X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund.

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