Bis[2-(1-imino­eth­yl)phenolato-κ2N,O]nickel(II)

Wang, N.

doi:10.1107/S1600536811051476

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page m11

doi:10.1107/S1600536811051476

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Bis[2-(1-iminoethyl)phenolato-κ²N,O]nickel(II)

Ning Wang ^a ^*

^aDepartment of Chemical Engineering, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China
^*Correspondence e-mail: wangning7903@yahoo.com.cn

(Received 19 November 2011; accepted 29 November 2011; online 3 December 2011)

There are one and a half independent molecules in the asymmetric unit of the title compound, [Ni(C₈H₈NO)₂], one of which is situated on an inversion center. In both molecules, the Ni^II ion is coordinated by two O and two N atoms from two Schiff base ligands in an approximate square-planar geometry. Intermolecular N—H⋯O hydrogen bonds link three molecules into centrosymmetric trimer. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds and voids of 37 Å³.

Related literature

For general background to the use of Schiff bases in coordination chemistry, see: Haikarainen et al. (2001 ); Miyasaka et al. (2002 ). For nickel complexes with Schiff base ligands, see: Liu et al. (2006 ); Wang (2010 ). For the crystal structure of a similar copper(II) complex, see: Marongiu & Lingafelter (1971 ).

Experimental

Crystal data

[Ni(C₈H₈NO)₂]
M_r = 327.02
Triclinic, $[P \overline 1]$
a = 9.1084 (10) Å
b = 11.3612 (16) Å
c = 11.8249 (18) Å
α = 101.006 (3)°
β = 93.049 (3)°
γ = 109.777 (3)°
V = 1121.1 (3) Å³
Z = 3
Mo Kα radiation
μ = 1.30 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.781, T_max = 0.799
6121 measured reflections
4190 independent reflections
2297 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.146
S = 0.99
4190 reflections
298 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2ⁱ	0.90 (1)	2.16 (2)	3.055 (6)	172 (6)
N1—H1⋯O3	0.90 (1)	2.25 (2)	3.138 (6)	168 (6)
C22—H22⋯O1ⁱⁱ	0.93	2.46	3.332 (6)	157 (6)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051476/cv5207sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051476/cv5207Isup2.hkl

checkCIF report

Comment top

The Schiff bases are a kind of versatile ligands used in coordination chemistry (Haikarainen et al., 2001; Miyasaka et al., 2002). The complexes derived from Schiff bases have proved to be of significant interest in the areas of catalysis, magnetism, medicinal and material chemistry. In the present paper, the title compound (I) - a new Schiff base nickel(II) complex - is reported.

The molecule of (I) is mononuclear nickel(II) complex. The asymmetric unit of (I) contains two crystallographically independent molecules, one of which is situated on inversion center. The Ni atom is coordinated by two O and two N atoms from two Schiff base ligands, forming a square planar geometry. The bond lengths related to the Ni atoms are comparable to those observed in other nickel(II) complexes with Schiff bases (Liu et al., 2006; Wang, 2010), but shorter than the Cu–N and Cu–O bonds observed in a structurally similar copper(II) complex (Marongiu & Lingafelter, 1971).

Intermolecular N—H···O hydrogen bonds link three molecules in (I) into centrosymmetric trimer (Fig. 1). The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds and voids of 37 Å³.

Related literature top

For general background to the use of Schiff bases in coordination chemistry, see: Haikarainen et al. (2001); Miyasaka et al. (2002). For nickel complexes with Schiff base ligands, see: Liu et al. (2006); Wang (2010). For the crystal structure of a similar copper(II) complex, see: Marongiu & Lingafelter (1971).

Experimental top

To a stirred ethanolic solution (30 ml) of 2-acetylphenol (0.136 g, 1 mmol) was added a few drops of 30% ammonia and an ethanolic solution (20 ml) of nickel(II) nitrate hexahydrate (0.291 g, 1 mmol). The final mixture was further stirred at room temperature for 1 h. The clear solution was set aside for a week, yielding red small block-shaped single crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The hydrogen-bonded (dashed lines) trimer in (I), showing the atom-labelling scheme and displacement ellipsoids drawn at the 30% probability level. Unlabeled atoms are related to the labeled ones by the symmetry operation (1 - x, 1 - y, 1 - z).

Bis[2-(1-iminoethyl)phenolato-κ²N,O]nickel(II) top

Crystal data top

[Ni(C₈H₈NO)₂]	Z = 3
M_r = 327.02	F(000) = 510
Triclinic, P1	D_x = 1.453 Mg m⁻³
a = 9.1084 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3612 (16) Å	Cell parameters from 772 reflections
c = 11.8249 (18) Å	θ = 2.3–24.5°
α = 101.006 (3)°	µ = 1.30 mm⁻¹
β = 93.049 (3)°	T = 298 K
γ = 109.777 (3)°	Block, red
V = 1121.1 (3) Å³	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4190 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 25.7°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
T_min = 0.781, T_max = 0.799	k = −13→13
6121 measured reflections	l = −13→14

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) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0585P)²] where P = (F_o² + 2F_c²)/3
4190 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.48 e Å⁻³
3 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Ni(C₈H₈NO)₂]	γ = 109.777 (3)°
M_r = 327.02	V = 1121.1 (3) Å³
Triclinic, P1	Z = 3
a = 9.1084 (10) Å	Mo Kα radiation
b = 11.3612 (16) Å	µ = 1.30 mm⁻¹
c = 11.8249 (18) Å	T = 298 K
α = 101.006 (3)°	0.20 × 0.20 × 0.18 mm
β = 93.049 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4190 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2297 reflections with I > 2σ(I)
T_min = 0.781, T_max = 0.799	R_int = 0.044
6121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	3 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.48 e Å⁻³
4190 reflections	Δρ_min = −0.39 e Å⁻³
298 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	0.0392 (3)
Ni2	0.35993 (9)	0.05065 (7)	0.23238 (6)	0.0385 (3)
O1	0.1878 (5)	−0.0945 (3)	0.2135 (3)	0.0472 (11)
O2	0.5346 (5)	0.1953 (3)	0.2545 (3)	0.0473 (11)
O3	0.4558 (5)	0.4475 (3)	0.3430 (3)	0.0477 (11)
N1	0.2586 (6)	0.1539 (4)	0.3058 (4)	0.0423 (12)
N2	0.4618 (6)	−0.0507 (4)	0.1545 (4)	0.0423 (12)
N3	0.4211 (6)	0.6312 (4)	0.5050 (4)	0.0416 (12)
C1	0.0143 (7)	−0.0061 (6)	0.3199 (5)	0.0451 (15)
C2	0.0540 (7)	−0.1072 (6)	0.2547 (5)	0.0445 (16)
C3	−0.0595 (8)	−0.2330 (6)	0.2351 (6)	0.0571 (18)
H3	−0.0379	−0.3009	0.1913	0.069*
C4	−0.1993 (8)	−0.2566 (7)	0.2789 (6)	0.067 (2)
H4	−0.2708	−0.3403	0.2651	0.080*
C5	−0.2365 (9)	−0.1581 (8)	0.3436 (6)	0.070 (2)
H5	−0.3316	−0.1752	0.3741	0.084*
C6	−0.1317 (8)	−0.0350 (7)	0.3621 (6)	0.0594 (19)
H6	−0.1581	0.0314	0.4039	0.071*
C7	0.1213 (7)	0.1262 (6)	0.3398 (5)	0.0423 (15)
C8	0.0716 (8)	0.2323 (6)	0.4004 (6)	0.065 (2)
H8A	0.1536	0.3133	0.4047	0.098*
H8B	0.0519	0.2216	0.4775	0.098*
H8C	−0.0226	0.2298	0.3579	0.098*
C9	0.7050 (7)	0.1099 (6)	0.1411 (5)	0.0419 (15)
C10	0.6652 (7)	0.2101 (6)	0.2071 (5)	0.0433 (15)
C11	0.7740 (8)	0.3369 (6)	0.2241 (6)	0.0563 (18)
H11	0.7512	0.4047	0.2672	0.068*
C12	0.9132 (9)	0.3605 (7)	0.1774 (6)	0.066 (2)
H12	0.9839	0.4444	0.1908	0.080*
C13	0.9520 (9)	0.2637 (9)	0.1111 (7)	0.075 (2)
H13	1.0458	0.2816	0.0787	0.090*
C14	0.8479 (8)	0.1411 (7)	0.0948 (6)	0.0613 (19)
H14	0.8730	0.0752	0.0508	0.074*
C15	0.5979 (7)	−0.0231 (5)	0.1195 (5)	0.0396 (15)
C16	0.6453 (8)	−0.1295 (6)	0.0558 (5)	0.0563 (18)
H16A	0.5654	−0.2106	0.0551	0.084*
H16B	0.7430	−0.1254	0.0941	0.084*
H16C	0.6577	−0.1204	−0.0226	0.084*
C17	0.3474 (6)	0.6042 (5)	0.3019 (5)	0.0354 (14)
C18	0.3980 (7)	0.4986 (5)	0.2679 (5)	0.0412 (15)
C19	0.3859 (7)	0.4450 (6)	0.1502 (5)	0.0491 (16)
H19	0.4205	0.3770	0.1271	0.059*
C20	0.3235 (8)	0.4911 (6)	0.0672 (6)	0.0562 (18)
H20	0.3155	0.4532	−0.0109	0.067*
C21	0.2730 (8)	0.5925 (6)	0.0987 (6)	0.0567 (18)
H21	0.2314	0.6234	0.0422	0.068*
C22	0.2843 (7)	0.6477 (6)	0.2141 (6)	0.0474 (16)
H22	0.2494	0.7159	0.2348	0.057*
C23	0.3618 (6)	0.6684 (5)	0.4228 (5)	0.0368 (14)
C24	0.3106 (9)	0.7818 (6)	0.4540 (5)	0.066 (2)
H24A	0.3309	0.8143	0.5366	0.099*
H24B	0.2000	0.7559	0.4291	0.099*
H24C	0.3680	0.8477	0.4161	0.099*
H1	0.306 (7)	0.2400 (13)	0.325 (5)	0.080*
H2	0.399 (6)	−0.134 (2)	0.139 (5)	0.080*
H3A	0.434 (8)	0.676 (5)	0.578 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0459 (7)	0.0321 (6)	0.0439 (7)	0.0225 (6)	0.0028 (6)	0.0035 (5)
Ni2	0.0378 (5)	0.0330 (5)	0.0473 (5)	0.0168 (4)	0.0084 (4)	0.0063 (4)
O1	0.038 (2)	0.038 (2)	0.067 (3)	0.018 (2)	0.012 (2)	0.006 (2)
O2	0.045 (3)	0.037 (2)	0.057 (3)	0.016 (2)	0.016 (2)	−0.001 (2)
O3	0.069 (3)	0.041 (2)	0.041 (3)	0.034 (2)	−0.001 (2)	0.003 (2)
N1	0.047 (3)	0.035 (3)	0.044 (3)	0.017 (3)	0.003 (3)	0.004 (3)
N2	0.043 (3)	0.036 (3)	0.049 (3)	0.015 (3)	0.015 (3)	0.006 (3)
N3	0.046 (3)	0.038 (3)	0.044 (3)	0.024 (3)	0.000 (3)	0.003 (3)
C1	0.036 (4)	0.054 (4)	0.050 (4)	0.022 (3)	0.004 (3)	0.014 (3)
C2	0.036 (4)	0.046 (4)	0.058 (4)	0.018 (3)	0.005 (3)	0.023 (3)
C3	0.044 (4)	0.053 (4)	0.076 (5)	0.016 (4)	0.003 (4)	0.020 (4)
C4	0.044 (5)	0.069 (5)	0.079 (6)	0.001 (4)	0.001 (4)	0.033 (4)
C5	0.048 (5)	0.088 (6)	0.078 (6)	0.024 (5)	0.020 (4)	0.025 (5)
C6	0.045 (4)	0.073 (5)	0.067 (5)	0.026 (4)	0.014 (4)	0.021 (4)
C7	0.049 (4)	0.053 (4)	0.032 (4)	0.031 (4)	0.004 (3)	0.005 (3)
C8	0.058 (5)	0.069 (5)	0.077 (5)	0.038 (4)	0.015 (4)	0.004 (4)
C9	0.039 (4)	0.047 (4)	0.042 (4)	0.019 (3)	0.004 (3)	0.008 (3)
C10	0.043 (4)	0.045 (4)	0.039 (4)	0.012 (3)	−0.002 (3)	0.010 (3)
C11	0.047 (4)	0.049 (4)	0.067 (5)	0.012 (4)	0.003 (4)	0.012 (4)
C12	0.054 (5)	0.065 (5)	0.068 (5)	0.001 (4)	0.005 (4)	0.023 (4)
C13	0.044 (5)	0.102 (7)	0.069 (6)	0.010 (5)	0.011 (4)	0.020 (5)
C14	0.042 (4)	0.080 (5)	0.062 (5)	0.024 (4)	0.013 (4)	0.011 (4)
C15	0.045 (4)	0.045 (4)	0.036 (4)	0.024 (3)	0.002 (3)	0.013 (3)
C16	0.066 (5)	0.056 (4)	0.059 (4)	0.038 (4)	0.020 (4)	0.010 (4)
C17	0.028 (3)	0.032 (3)	0.046 (4)	0.012 (3)	0.004 (3)	0.006 (3)
C18	0.036 (4)	0.038 (3)	0.051 (4)	0.015 (3)	0.011 (3)	0.011 (3)
C19	0.056 (4)	0.047 (4)	0.043 (4)	0.021 (3)	0.006 (3)	0.004 (3)
C20	0.058 (4)	0.059 (4)	0.040 (4)	0.010 (4)	−0.001 (4)	0.006 (4)
C21	0.058 (5)	0.059 (5)	0.056 (5)	0.019 (4)	0.001 (4)	0.026 (4)
C22	0.046 (4)	0.045 (4)	0.056 (5)	0.018 (3)	0.006 (3)	0.019 (3)
C23	0.032 (3)	0.030 (3)	0.050 (4)	0.013 (3)	0.010 (3)	0.007 (3)
C24	0.102 (6)	0.063 (4)	0.059 (5)	0.062 (5)	0.017 (4)	0.013 (4)

Geometric parameters (Å, º) top

Ni1—O3ⁱ	1.816 (4)	C8—H8C	0.9600
Ni1—O3	1.816 (4)	C9—C14	1.398 (8)
Ni1—N3	1.853 (5)	C9—C10	1.417 (8)
Ni1—N3ⁱ	1.853 (5)	C9—C15	1.459 (8)
Ni2—O1	1.817 (4)	C10—C11	1.414 (8)
Ni2—O2	1.822 (4)	C11—C12	1.374 (9)
Ni2—N1	1.847 (5)	C11—H11	0.9300
Ni2—N2	1.856 (5)	C12—C13	1.382 (10)
O1—C2	1.310 (7)	C12—H12	0.9300
O2—C10	1.315 (7)	C13—C14	1.364 (9)
O3—C18	1.326 (6)	C13—H13	0.9300
N1—C7	1.289 (7)	C14—H14	0.9300
N1—H1	0.902 (10)	C15—C16	1.501 (7)
N2—C15	1.283 (7)	C16—H16A	0.9600
N2—H2	0.899 (10)	C16—H16B	0.9600
N3—C23	1.294 (7)	C16—H16C	0.9600
N3—H3A	0.897 (10)	C17—C22	1.406 (7)
C1—C6	1.400 (8)	C17—C18	1.422 (7)
C1—C2	1.420 (8)	C17—C23	1.453 (7)
C1—C7	1.454 (8)	C18—C19	1.391 (8)
C2—C3	1.418 (8)	C19—C20	1.378 (8)
C3—C4	1.361 (9)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.375 (8)
C4—C5	1.383 (9)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.371 (8)
C5—C6	1.369 (9)	C21—H21	0.9300
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.502 (7)
C7—C8	1.498 (8)	C24—H24A	0.9600
C8—H8A	0.9600	C24—H24B	0.9600
C8—H8B	0.9600	C24—H24C	0.9600

O3ⁱ—Ni1—O3	180.000 (1)	C10—C9—C15	120.8 (5)
O3ⁱ—Ni1—N3	86.81 (18)	O2—C10—C11	116.8 (6)
O3—Ni1—N3	93.19 (18)	O2—C10—C9	125.4 (5)
O3ⁱ—Ni1—N3ⁱ	93.19 (18)	C11—C10—C9	117.9 (6)
O3—Ni1—N3ⁱ	86.81 (18)	C12—C11—C10	120.3 (7)
N3—Ni1—N3ⁱ	180.000 (2)	C12—C11—H11	119.8
O1—Ni2—O2	178.57 (18)	C10—C11—H11	119.8
O1—Ni2—N1	93.24 (19)	C11—C12—C13	122.3 (7)
O2—Ni2—N1	87.0 (2)	C11—C12—H12	118.9
O1—Ni2—N2	87.43 (19)	C13—C12—H12	118.9
O2—Ni2—N2	92.39 (19)	C14—C13—C12	117.7 (7)
N1—Ni2—N2	178.2 (2)	C14—C13—H13	121.2
C2—O1—Ni2	127.8 (4)	C12—C13—H13	121.2
C10—O2—Ni2	127.8 (4)	C13—C14—C9	123.1 (7)
C18—O3—Ni1	129.2 (4)	C13—C14—H14	118.4
C7—N1—Ni2	131.3 (4)	C9—C14—H14	118.4
C7—N1—H1	108 (4)	N2—C15—C9	120.5 (5)
Ni2—N1—H1	121 (4)	N2—C15—C16	119.1 (5)
C15—N2—Ni2	132.2 (4)	C9—C15—C16	120.4 (5)
C15—N2—H2	118 (4)	C15—C16—H16A	109.5
Ni2—N2—H2	110 (4)	C15—C16—H16B	109.5
C23—N3—Ni1	131.0 (4)	H16A—C16—H16B	109.5
C23—N3—H3A	119 (4)	C15—C16—H16C	109.5
Ni1—N3—H3A	110 (4)	H16A—C16—H16C	109.5
C6—C1—C2	119.1 (6)	H16B—C16—H16C	109.5
C6—C1—C7	120.2 (6)	C22—C17—C18	118.0 (5)
C2—C1—C7	120.6 (5)	C22—C17—C23	119.9 (5)
O1—C2—C3	117.3 (6)	C18—C17—C23	122.1 (5)
O1—C2—C1	125.5 (5)	O3—C18—C19	117.8 (5)
C3—C2—C1	117.2 (6)	O3—C18—C17	123.3 (5)
C4—C3—C2	121.7 (7)	C19—C18—C17	118.9 (5)
C4—C3—H3	119.2	C20—C19—C18	121.1 (6)
C2—C3—H3	119.2	C20—C19—H19	119.5
C3—C4—C5	121.0 (7)	C18—C19—H19	119.5
C3—C4—H4	119.5	C21—C20—C19	120.8 (6)
C5—C4—H4	119.5	C21—C20—H20	119.6
C6—C5—C4	119.2 (7)	C19—C20—H20	119.6
C6—C5—H5	120.4	C22—C21—C20	119.4 (6)
C4—C5—H5	120.4	C22—C21—H21	120.3
C5—C6—C1	121.9 (7)	C20—C21—H21	120.3
C5—C6—H6	119.0	C21—C22—C17	121.9 (6)
C1—C6—H6	119.0	C21—C22—H22	119.1
N1—C7—C1	121.0 (5)	C17—C22—H22	119.1
N1—C7—C8	119.3 (6)	N3—C23—C17	121.1 (5)
C1—C7—C8	119.7 (6)	N3—C23—C24	118.8 (5)
C7—C8—H8A	109.5	C17—C23—C24	120.1 (5)
C7—C8—H8B	109.5	C23—C24—H24A	109.5
H8A—C8—H8B	109.5	C23—C24—H24B	109.5
C7—C8—H8C	109.5	H24A—C24—H24B	109.5
H8A—C8—H8C	109.5	C23—C24—H24C	109.5
H8B—C8—H8C	109.5	H24A—C24—H24C	109.5
C14—C9—C10	118.7 (6)	H24B—C24—H24C	109.5
C14—C9—C15	120.5 (6)

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
N3—H3A···O2ⁱ	0.90 (1)	2.16 (2)	3.055 (6)	172 (6)
N1—H1···O3	0.90 (1)	2.25 (2)	3.138 (6)	168 (6)
C22—H22···O1ⁱⁱ	0.93	2.46	3.332 (6)	157 (6)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₈NO)₂]
M_r	327.02
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.1084 (10), 11.3612 (16), 11.8249 (18)
α, β, γ (°)	101.006 (3), 93.049 (3), 109.777 (3)
V (Å³)	1121.1 (3)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	1.30
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.781, 0.799
No. of measured, independent and observed [I > 2σ(I)] reflections	6121, 4190, 2297
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.146, 0.99
No. of reflections	4190
No. of parameters	298
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)	0.48, −0.39

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2ⁱ	0.897 (10)	2.164 (15)	3.055 (6)	172 (6)
N1—H1···O3	0.902 (10)	2.250 (18)	3.138 (6)	168 (6)
C22—H22···O1ⁱⁱ	0.93	2.46	3.332 (6)	157 (6)

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

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Haikarainen, A., Sipila, J., Pietikainen, P., Pajunen, A. & Mutikainen, I. (2001). Bioorg. Med. Chem. 9, 1633–1638. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liu, H.-Y., Gao, F., Lu, Z.-S. & Wang, H.-Y. (2006). Acta Cryst. E62, m1306–m1308. Web of Science CSD CrossRef IUCr Journals Google Scholar
Marongiu, G. & Lingafelter, E. C. (1971). Acta Cryst. B27, 1195–1201. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Miyasaka, H., Clerac, R., Ishii, T., Chang, H.-C., Kitagawa, S. & Yamashita, M. (2002). J. Chem. Soc. Dalton Trans. pp. 1528–1534. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, N. (2010). Acta Cryst. E66, m1033. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 1| January 2012| Page m11

doi:10.1107/S1600536811051476

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