trans-Bis(2-benzoyl­benzoato-κO1)bis­(ethanol-κO)bis­(1H-imidazole-κN3)nickel(II)

Heren, Z.; Paşaoğlu, H.; Yıldırım, M.H.; Hıra, D.

doi:10.1107/S160053680902621X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages m907-m908

doi:10.1107/S160053680902621X

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trans-Bis(2-benzoylbenzoato-κO¹)bis(ethanol-κO)bis(1H-imidazole-κN³)nickel(II)

Zerrin Heren,^a Hümeyra Paşaoğlu,^b M. Hakkı Yıldırım ^b ^* and Derya Hıra ^a

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

(Received 30 June 2009; accepted 6 July 2009; online 11 July 2009)

In the title centrosymmetric mononuclear nickel(II) complex, [Ni(C₁₄H₉O₃)₂(C₃H₄N₂)₂(CH₃CH₂OH)₂], the central Ni^II ion lies on an inversion centre and is octahedrally coordinated. The equatorial plane is formed by two O atoms from two symmetry-related 2-benzoylbenzoate ligands and two N atoms from two symmetry-related imidazole ligands, whereas the axial positions are occupied by two O atoms from two ethanol ligands. Intramolecular O---H...O hydrogen bonds stabilize this arrangement. The molecules are linked into chains running along the b axis by N—H⋯O hydrogen bonds.

Related literature

For crystal structures with 2-benzoylbenzoate ligands, see: Diop et al. (2006 , 2007 ); Foreman et al. (2001 ); Jones et al. (1996 ); Martin & Valente (1998 ); Prout et al. (1996 ); Song et al. (2005 ); Yıldırım et al. (2009 ). For the crystal structure of 2-benzoylbenzoic acid, see: Lalancette et al. (1990 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

[Ni(C₁₄H₉O₃)₂(C₃H₄N₂)₂(C₂H₆O)₂]
M_r = 737.43
Monoclinic, P 2₁ /c
a = 12.8914 (8) Å
b = 8.3908 (5) Å
c = 16.4590 (11) Å
β = 90.832 (5)°
V = 1780.17 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 296 K
0.43 × 0.25 × 0.14 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.809, T_max = 0.921
15078 measured reflections
3889 independent reflections
2704 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.150
S = 1.11
3889 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.78 (5)	1.86 (5)	2.627 (4)	170 (6)
N2—H2⋯O3ⁱ	0.86	2.02	2.837 (5)	159
Symmetry code: (i) x, y-1, z.

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 datablocks global, I. DOI: 10.1107/S160053680902621X/ci2845sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902621X/ci2845Isup2.hkl

checkCIF report

Comment top

We have previously reported the crystal structure of [Cu(2-byba)₂(bim)₂] (bim = benzimidazole, 2-byba = 2-benzoylbenzoate) (Yıldırım et al., 2009). As an extension of this study, we now report the structure of a new nickel(II) complex with the 2-byba ligand.

In the title complex, the Ni^II ion lies on a centre of symmetry and has a octahedral coordination geometry formed by 2-byba, imidazole (im), ethanol ligands and their symmetry-related equivalents. All ligands are monodentate with the 2-byba coordinates through a carboxylate O atom, im coordinates through the aromatic N atom and ethanol coordinates through the O atom. Intramolecular O—H···O hydrogen bonds are observed.

The molecular packing is mainly stabilized by strong intermolecular N—H···O hydrogen bonds (Table 2 and Fig. 2). Atom N2 in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H2, to atom O3 in the molecule at (x, y - 1, z) forming C(8) chains with R₂²(16) rings (Bernstein et al., 1995). These chains run parallel to the [010] (Fig. 2).

Related literature top

For crystal structures with 2-benzoylbenzoate ligands, see: Diop et al. (2006, 2007); Foreman et al. (2001); Jones et al. (1996); Martin et al. (1998); Prout et al. (1996); Song et al. (2005); Yıldırım et al., 2009). For the crystal structure of 2-benzoylbenzoic acid, see: Lalancette et al. (1990). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A solution of 2-benzoylbenzoate (0.45 g, 2 mmol) in ethanol (10 ml) was added to a solution of nickel acetate tetrahydrate (0.25 g, 1 mmol) in ethanol (10 ml) and the solution was stirred for 15 min at 333 K. To this solution, a solution of imidazole (0.23 g, 2 mmol) in ethanol (10 ml) was added and the resultant solution was left to evaporate slowly at room temperature. After one week, single crystals of the title complex were isolated.

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 complex, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability. Symmetry code: (i) 1 -x, 1 -y, 1 -z.
	Fig. 2. Part of the crystal structure of the title compound showing the chain of R₂²(16) rings along [010] generated by N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity.Symmetry code: (ii) x, y - 1, z

trans-Bis(2-benzoylbenzoato-κO¹)bis(ethanol- κO)bis(1H-imidazole-κN³)nickel(II) top

Crystal data top

[Ni(C₁₄H₉O₃)₂(C₃H₄N₂)₂(C₂H₆O)₂]	F(000) = 772
M_r = 737.43	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15078 reflections
a = 12.8914 (8) Å	θ = 1.6–27.6°
b = 8.3908 (5) Å	µ = 0.60 mm⁻¹
c = 16.4590 (11) Å	T = 296 K
β = 90.832 (5)°	Prism, green
V = 1780.17 (19) Å³	0.43 × 0.25 × 0.14 mm
Z = 2

Data collection top

Stoe IPDSII diffractometer	3889 independent reflections
Radiation source: fine-focus sealed tube	2704 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.0°, θ_min = 1.6°
ω scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
T_min = 0.809, T_max = 0.921	l = −20→20
15078 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0435P)² + 2.752P] where P = (F_o² + 2F_c²)/3
3889 reflections	(Δ/σ)_max = 0.004
235 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Ni(C₁₄H₉O₃)₂(C₃H₄N₂)₂(C₂H₆O)₂]	V = 1780.17 (19) Å³
M_r = 737.43	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8914 (8) Å	µ = 0.60 mm⁻¹
b = 8.3908 (5) Å	T = 296 K
c = 16.4590 (11) Å	0.43 × 0.25 × 0.14 mm
β = 90.832 (5)°

Data collection top

Stoe IPDSII diffractometer	3889 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2704 reflections with I > 2σ(I)
T_min = 0.809, T_max = 0.921	R_int = 0.046
15078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.31 e Å⁻³
3889 reflections	Δρ_min = −0.26 e Å⁻³
235 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
C1	0.3658 (4)	0.5474 (6)	0.3388 (3)	0.0630 (13)
H1A	0.3057	0.4882	0.3568	0.076*
H1B	0.4138	0.4723	0.3151	0.076*
C2	0.3320 (5)	0.6663 (8)	0.2749 (3)	0.0848 (18)
H2A	0.2993	0.6112	0.2303	0.127*
H2B	0.3915	0.7231	0.2558	0.127*
H2C	0.2838	0.7402	0.2979	0.127*
C3	0.5546 (4)	0.1822 (5)	0.4290 (3)	0.0525 (11)
H3	0.6248	0.2074	0.4330	0.063*
C4	0.4127 (4)	0.0507 (6)	0.4036 (3)	0.0623 (13)
H4	0.3661	−0.0284	0.3879	0.075*
C5	0.3897 (4)	0.1970 (6)	0.4334 (3)	0.0563 (11)
H5	0.3230	0.2356	0.4416	0.068*
C6	0.6557 (3)	0.6330 (5)	0.3827 (2)	0.0448 (9)
C7	0.7620 (3)	0.6345 (5)	0.3466 (2)	0.0452 (9)
C8	0.7755 (4)	0.7083 (5)	0.2710 (3)	0.0548 (11)
H8	0.7192	0.7560	0.2448	0.066*
C9	0.8715 (4)	0.7106 (6)	0.2352 (3)	0.0660 (13)
H9	0.8800	0.7617	0.1856	0.079*
C10	0.9537 (4)	0.6380 (7)	0.2724 (3)	0.0724 (15)
H10	1.0181	0.6391	0.2477	0.087*
C11	0.9426 (4)	0.5622 (6)	0.3471 (3)	0.0658 (13)
H11	0.9991	0.5124	0.3720	0.079*
C12	0.8466 (3)	0.5616 (5)	0.3841 (2)	0.0454 (9)
C13	0.8422 (3)	0.4876 (6)	0.4681 (2)	0.0481 (9)
C14	0.8461 (3)	0.3113 (5)	0.4742 (3)	0.0463 (10)
C15	0.8481 (4)	0.2143 (6)	0.4068 (3)	0.0616 (12)
H15	0.8446	0.2587	0.3551	0.074*
C16	0.8554 (5)	0.0506 (6)	0.4159 (4)	0.0829 (17)
H16	0.8574	−0.0150	0.3704	0.100*
C17	0.8597 (4)	−0.0149 (7)	0.4934 (4)	0.0815 (16)
H17	0.8650	−0.1249	0.4993	0.098*
C18	0.8564 (5)	0.0769 (7)	0.5591 (4)	0.0770 (16)
H18	0.8585	0.0306	0.6104	0.092*
C19	0.8498 (4)	0.2423 (6)	0.5516 (3)	0.0613 (12)
H19	0.8479	0.3062	0.5978	0.074*
N1	0.4796 (3)	0.2796 (4)	0.44961 (19)	0.0431 (8)
N2	0.5184 (3)	0.0434 (4)	0.4016 (2)	0.0601 (10)
H2	0.5548	−0.0362	0.3857	0.072*
Ni1	0.5000	0.5000	0.5000	0.0385 (2)
O1	0.4142 (2)	0.6220 (4)	0.40705 (17)	0.0489 (7)
O2	0.6371 (2)	0.5278 (3)	0.43480 (16)	0.0462 (7)
O3	0.5923 (2)	0.7370 (4)	0.35828 (19)	0.0566 (8)
O4	0.8429 (3)	0.5724 (4)	0.52801 (18)	0.0585 (8)
H1	0.465 (4)	0.665 (7)	0.395 (3)	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.080 (3)	0.056 (3)	0.052 (3)	−0.004 (2)	−0.011 (2)	−0.007 (2)
C2	0.106 (5)	0.099 (5)	0.049 (3)	0.009 (4)	−0.017 (3)	0.005 (3)
C3	0.062 (3)	0.041 (2)	0.054 (2)	−0.002 (2)	0.007 (2)	−0.003 (2)
C4	0.071 (3)	0.046 (3)	0.070 (3)	−0.008 (2)	−0.009 (2)	−0.009 (2)
C5	0.058 (3)	0.050 (3)	0.061 (3)	−0.001 (2)	−0.003 (2)	−0.007 (2)
C6	0.053 (2)	0.036 (2)	0.045 (2)	0.0040 (19)	0.0011 (18)	−0.0035 (18)
C7	0.055 (2)	0.040 (2)	0.041 (2)	−0.0023 (19)	0.0071 (18)	−0.0004 (17)
C8	0.067 (3)	0.051 (3)	0.047 (2)	−0.001 (2)	0.006 (2)	0.004 (2)
C9	0.075 (3)	0.070 (3)	0.054 (3)	−0.010 (3)	0.017 (2)	0.008 (2)
C10	0.067 (3)	0.083 (4)	0.068 (3)	−0.010 (3)	0.025 (3)	0.001 (3)
C11	0.056 (3)	0.069 (3)	0.073 (3)	0.005 (2)	0.014 (2)	0.004 (3)
C12	0.047 (2)	0.042 (2)	0.047 (2)	−0.0058 (18)	0.0040 (18)	−0.0009 (18)
C13	0.044 (2)	0.049 (2)	0.051 (2)	−0.001 (2)	0.0021 (16)	−0.002 (2)
C14	0.042 (2)	0.041 (2)	0.056 (2)	−0.0002 (18)	0.0046 (18)	0.0022 (19)
C15	0.071 (3)	0.052 (3)	0.062 (3)	−0.003 (2)	0.007 (2)	−0.006 (2)
C16	0.096 (4)	0.045 (3)	0.108 (5)	0.001 (3)	0.017 (4)	−0.020 (3)
C17	0.081 (4)	0.044 (3)	0.120 (5)	0.000 (3)	0.016 (3)	0.015 (3)
C18	0.090 (4)	0.059 (3)	0.082 (4)	−0.001 (3)	0.005 (3)	0.022 (3)
C19	0.071 (3)	0.051 (3)	0.062 (3)	−0.004 (2)	0.002 (2)	0.006 (2)
N1	0.0491 (19)	0.0369 (18)	0.0434 (17)	−0.0001 (16)	0.0029 (15)	−0.0017 (14)
N2	0.078 (3)	0.042 (2)	0.061 (2)	0.0093 (19)	0.0084 (19)	−0.0090 (17)
Ni1	0.0424 (4)	0.0347 (4)	0.0384 (3)	0.0010 (4)	0.0027 (3)	−0.0022 (3)
O1	0.0534 (18)	0.0486 (19)	0.0446 (15)	0.0003 (14)	−0.0038 (13)	−0.0035 (13)
O2	0.0521 (16)	0.0393 (17)	0.0474 (14)	0.0011 (13)	0.0080 (12)	0.0042 (12)
O3	0.0580 (19)	0.0476 (18)	0.0644 (18)	0.0100 (15)	0.0056 (15)	0.0074 (15)
O4	0.078 (2)	0.0487 (18)	0.0485 (17)	0.0015 (16)	−0.0019 (15)	−0.0077 (14)

Geometric parameters (Å, º) top

C1—O1	1.423 (5)	C10—H10	0.93
C1—C2	1.509 (7)	C11—C12	1.387 (6)
C1—H1A	0.97	C11—H11	0.93
C1—H1B	0.97	C12—C13	1.517 (6)
C2—H2A	0.96	C13—O4	1.216 (5)
C2—H2B	0.96	C13—C14	1.483 (6)
C2—H2C	0.96	C14—C15	1.377 (6)
C3—N1	1.315 (5)	C14—C19	1.400 (6)
C3—N2	1.331 (5)	C15—C16	1.384 (7)
C3—H3	0.93	C15—H15	0.93
C4—C5	1.356 (6)	C16—C17	1.389 (8)
C4—N2	1.365 (6)	C16—H16	0.93
C4—H4	0.93	C17—C18	1.329 (8)
C5—N1	1.373 (5)	C17—H17	0.93
C5—H5	0.93	C18—C19	1.396 (7)
C6—O2	1.257 (5)	C18—H18	0.93
C6—O3	1.257 (5)	C19—H19	0.93
C6—C7	1.502 (6)	N1—Ni1	2.042 (3)
C7—C12	1.388 (6)	N2—H2	0.8600
C7—C8	1.403 (6)	Ni1—N1ⁱ	2.042 (3)
C8—C9	1.378 (6)	Ni1—O2ⁱ	2.094 (3)
C8—H8	0.93	Ni1—O2	2.094 (3)
C9—C10	1.361 (7)	Ni1—O1ⁱ	2.136 (3)
C9—H9	0.93	Ni1—O1	2.136 (3)
C10—C11	1.394 (7)	O1—H1	0.78 (5)

O1—C1—C2	112.2 (4)	C14—C13—C12	117.9 (4)
O1—C1—H1A	109.2	C15—C14—C19	119.2 (4)
C2—C1—H1A	109.2	C15—C14—C13	122.4 (4)
O1—C1—H1B	109.2	C19—C14—C13	118.4 (4)
C2—C1—H1B	109.2	C14—C15—C16	120.1 (5)
H1A—C1—H1B	107.9	C14—C15—H15	119.9
C1—C2—H2A	109.5	C16—C15—H15	119.9
C1—C2—H2B	109.5	C15—C16—C17	119.6 (6)
H2A—C2—H2B	109.5	C15—C16—H16	120.2
C1—C2—H2C	109.5	C17—C16—H16	120.2
H2A—C2—H2C	109.5	C18—C17—C16	121.1 (6)
H2B—C2—H2C	109.5	C18—C17—H17	119.5
N1—C3—N2	112.0 (4)	C16—C17—H17	119.5
N1—C3—H3	124.0	C17—C18—C19	120.5 (6)
N2—C3—H3	124.0	C17—C18—H18	119.8
C5—C4—N2	105.8 (4)	C19—C18—H18	119.8
C5—C4—H4	127.1	C18—C19—C14	119.5 (5)
N2—C4—H4	127.1	C18—C19—H19	120.2
C4—C5—N1	109.8 (4)	C14—C19—H19	120.2
C4—C5—H5	125.1	C3—N1—C5	105.0 (4)
N1—C5—H5	125.1	C3—N1—Ni1	125.2 (3)
O2—C6—O3	125.1 (4)	C5—N1—Ni1	129.8 (3)
O2—C6—C7	117.4 (4)	C3—N2—C4	107.4 (4)
O3—C6—C7	117.4 (4)	C3—N2—H2	126.3
C12—C7—C8	118.9 (4)	C4—N2—H2	126.3
C12—C7—C6	122.4 (4)	N1ⁱ—Ni1—N1	180.0
C8—C7—C6	118.7 (4)	N1ⁱ—Ni1—O2ⁱ	89.87 (12)
C9—C8—C7	120.6 (5)	N1—Ni1—O2ⁱ	90.13 (12)
C9—C8—H8	119.7	N1ⁱ—Ni1—O2	90.13 (12)
C7—C8—H8	119.7	N1—Ni1—O2	89.87 (12)
C10—C9—C8	120.0 (5)	O2ⁱ—Ni1—O2	180.0
C10—C9—H9	120.0	N1ⁱ—Ni1—O1ⁱ	94.64 (12)
C8—C9—H9	120.0	N1—Ni1—O1ⁱ	85.36 (12)
C9—C10—C11	120.7 (5)	O2ⁱ—Ni1—O1ⁱ	90.65 (11)
C9—C10—H10	119.6	O2—Ni1—O1ⁱ	89.35 (11)
C11—C10—H10	119.6	N1ⁱ—Ni1—O1	85.36 (12)
C12—C11—C10	119.6 (5)	N1—Ni1—O1	94.64 (12)
C12—C11—H11	120.2	O2ⁱ—Ni1—O1	89.35 (11)
C10—C11—H11	120.2	O2—Ni1—O1	90.65 (11)
C11—C12—C7	120.2 (4)	O1ⁱ—Ni1—O1	180.0
C11—C12—C13	116.6 (4)	C1—O1—Ni1	124.9 (3)
C7—C12—C13	123.1 (4)	C1—O1—H1	112 (4)
O4—C13—C14	121.9 (4)	Ni1—O1—H1	88 (4)
O4—C13—C12	120.0 (4)	C6—O2—Ni1	126.8 (3)

N2—C4—C5—N1	0.0 (5)	C17—C18—C19—C14	0.4 (8)
O2—C6—C7—C12	−20.1 (6)	C15—C14—C19—C18	0.6 (7)
O3—C6—C7—C12	160.0 (4)	C13—C14—C19—C18	−178.3 (4)
O2—C6—C7—C8	158.0 (4)	N2—C3—N1—C5	−0.6 (5)
O3—C6—C7—C8	−21.9 (6)	N2—C3—N1—Ni1	176.6 (3)
C12—C7—C8—C9	−1.1 (7)	C4—C5—N1—C3	0.3 (5)
C6—C7—C8—C9	−179.2 (4)	C4—C5—N1—Ni1	−176.7 (3)
C7—C8—C9—C10	1.4 (8)	N1—C3—N2—C4	0.7 (5)
C8—C9—C10—C11	−0.7 (8)	C5—C4—N2—C3	−0.4 (5)
C9—C10—C11—C12	−0.4 (8)	C3—N1—Ni1—O2ⁱ	−147.8 (3)
C10—C11—C12—C7	0.7 (7)	C5—N1—Ni1—O2ⁱ	28.7 (4)
C10—C11—C12—C13	−175.6 (5)	C3—N1—Ni1—O2	32.2 (3)
C8—C7—C12—C11	0.0 (6)	C5—N1—Ni1—O2	−151.3 (4)
C6—C7—C12—C11	178.1 (4)	C3—N1—Ni1—O1ⁱ	−57.2 (3)
C8—C7—C12—C13	176.1 (4)	C5—N1—Ni1—O1ⁱ	119.3 (4)
C6—C7—C12—C13	−5.9 (6)	C3—N1—Ni1—O1	122.8 (3)
C11—C12—C13—O4	100.0 (5)	C5—N1—Ni1—O1	−60.7 (4)
C7—C12—C13—O4	−76.2 (5)	C2—C1—O1—Ni1	−167.2 (3)
C11—C12—C13—C14	−74.9 (5)	N1ⁱ—Ni1—O1—C1	−179.8 (4)
C7—C12—C13—C14	108.9 (5)	N1—Ni1—O1—C1	0.2 (4)
O4—C13—C14—C15	−178.2 (4)	O2ⁱ—Ni1—O1—C1	−89.8 (3)
C12—C13—C14—C15	−3.4 (6)	O2—Ni1—O1—C1	90.2 (3)
O4—C13—C14—C19	0.6 (6)	O3—C6—O2—Ni1	−3.1 (6)
C12—C13—C14—C19	175.4 (4)	C7—C6—O2—Ni1	177.0 (2)
C19—C14—C15—C16	−1.0 (7)	N1ⁱ—Ni1—O2—C6	−61.3 (3)
C13—C14—C15—C16	177.8 (5)	N1—Ni1—O2—C6	118.7 (3)
C14—C15—C16—C17	0.6 (9)	O1ⁱ—Ni1—O2—C6	−155.9 (3)
C15—C16—C17—C18	0.4 (9)	O1—Ni1—O2—C6	24.1 (3)
C16—C17—C18—C19	−0.8 (9)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.78 (5)	1.86 (5)	2.627 (4)	170 (6)
N2—H2···O3ⁱⁱ	0.86	2.02	2.837 (5)	159

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₉O₃)₂(C₃H₄N₂)₂(C₂H₆O)₂]
M_r	737.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.8914 (8), 8.3908 (5), 16.4590 (11)
β (°)	90.832 (5)
V (Å³)	1780.17 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.43 × 0.25 × 0.14

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.809, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	15078, 3889, 2704
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.150, 1.11
No. of reflections	3889
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.26

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).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.78 (5)	1.86 (5)	2.627 (4)	170 (6)
N2—H2···O3ⁱ	0.86	2.02	2.837 (5)	159

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors thank Professor Dr Orhan Büyükgüngör for his help with the data collection and acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Diop, C. A. K., Touré, A., Diop, L., Tinant, B. & Mahieu, B. (2007). Acta Cryst. E63, m91–m93. Web of Science CSD CrossRef IUCr Journals Google Scholar
Diop, C. A. K., Touré, A., Diop, L. & Welter, R. (2006). Acta Cryst. E62, m3338–m3340. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Foreman, M. R. J., Plater, M. J. & Skakle, M. S. (2001). J. Chem. Soc. Dalton Trans. pp. 1897–1903. Web of Science CSD CrossRef Google Scholar
Jones, P. B., Pollastri, M. P. & Porter, N. A. (1996). J. Org. Chem. 61, 9455–9461. CrossRef CAS Web of Science Google Scholar
Lalancette, R. A., Vanderhoff, P. A. & Thompson, H. W. (1990). Acta Cryst. C46, 1682–1686. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Martin, S. B. & Valente, J. (1998). J. Chem. Crystallogr. 28, 203–207. Web of Science CSD CrossRef CAS Google Scholar
Prout, K., Vaughan-Lee, D., Moloney, M. G. & Prottey, S. C. (1996). Acta Cryst. C52, 351–354. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, Y., Yan, B. & Chen, Z. (2005). J. Coord. Chem. 58, 1417–1421. Web of Science CSD CrossRef CAS Google Scholar
Stoe & Cie (2002). X-RED32 and X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Yıldırım, M. H., Heren, Z., Paşaoğlu, H., Hıra, D. & Büyükgüngör, O. (2009). Acta Cryst. E65, m638–m639. Web of Science CSD CrossRef IUCr Journals Google Scholar

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