(2-{[2-(4-Chlorophenoxy)-1-oxido-ethyl-idene-κO]hydrazono-methyl}-phenol-ato-κN,O)(1H-imidazole-κN)nickel(II).

In the title complex, [Ni(C(15)H(11)ClN(2)O(3))(C(3)H(4)N(2))], the Ni(II) ion is coordinated by a phenolate O, hydrazine N and carbonyl O atom from the hydrazone ligand and by an N atom from the imidazole mol-ecule, forming a distorted square-planar geometry. Inter-molecular N-H⋯N hydrogen bonds link neighboring molecules into extended chains parallel to [100].

Related literature

For general background, see: Liu & Gao (1998 ▶); Ma et al. (1989 ▶); Sur et al. (1993 ▶); Sun et al. (2005 ▶). For related structures, see: Chen & Liu (2006 ▶).

Experimental

Crystal data

[Ni(C15H11ClN2O3)(C3H4N2)]

M = 429.50

Orthorhombic,

a = 18.745 (5) Å

b = 6.6054 (14) Å

c = 29.230 (8) Å

V = 3619.2 (16) Å3

Z = 8

Mo Kα radiation

μ = 1.25 mm−1

T = 293 (2) K

0.65 × 0.21 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ▶) T min = 0.498, T max = 0.835

29384 measured reflections

4146 independent reflections

2947 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 0.96

4146 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.30 e Å−3

Data collection: TEXRAY (Molecular Structure Corporation, 1999 ▶); cell refinement: TEXRAY; data reduction: TEXSAN (Mol­ec­ular Structure Corporation, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEX (McArdle, 1995 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028171/bv2105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028171/bv2105Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C15H11ClN2O3)(C3H4N2)]	F(000) = 1760
Mr = 429.50	Dx = 1.576 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2947 reflections
a = 18.745 (5) Å	θ = 3.0–27.5°
b = 6.6054 (14) Å	µ = 1.25 mm−1
c = 29.230 (8) Å	T = 293 K
V = 3619.2 (16) Å3	Prism, red
Z = 8	0.65 × 0.21 × 0.15 mm

Rigaku R-AXIS RAPID diffractometer	4146 independent reflections
Radiation source: fine-focus sealed tube	2947 reflections with I > 2σ(I)
graphite	Rint = 0.058
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −24→24
Tmin = 0.498, Tmax = 0.835	k = −8→8
29384 measured reflections	l = −37→37

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0475P)2] where P = (Fo2 + 2Fc2)/3
4146 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni1	0.160819 (13)	0.65045 (4)	0.262178 (8)	0.03514 (10)
O1	0.11416 (8)	0.6681 (2)	0.31655 (5)	0.0519 (4)
O2	0.20944 (7)	0.63914 (19)	0.20727 (4)	0.0397 (3)
O3	0.30335 (9)	0.7513 (2)	0.14068 (5)	0.0524 (4)
N1	0.25009 (9)	0.6404 (2)	0.28711 (5)	0.0344 (3)
N2	0.30584 (9)	0.6336 (2)	0.25500 (6)	0.0381 (4)
N3	0.07133 (9)	0.6479 (2)	0.23119 (6)	0.0403 (4)
N4	−0.04380 (10)	0.6469 (3)	0.21963 (6)	0.0489 (4)
H4A	−0.0889	0.6519	0.2250	0.059*
Cl1	0.44937 (4)	0.82246 (10)	−0.03563 (2)	0.0718 (2)
C1	0.14251 (12)	0.6600 (3)	0.35761 (7)	0.0433 (5)
C2	0.21615 (12)	0.6403 (3)	0.36618 (7)	0.0393 (4)
C3	0.24043 (14)	0.6287 (3)	0.41153 (7)	0.0508 (6)
H3A	0.2890	0.6143	0.4171	0.061*
C4	0.19446 (16)	0.6382 (3)	0.44779 (8)	0.0580 (6)
H4B	0.2114	0.6285	0.4776	0.070*
C5	0.12234 (16)	0.6625 (4)	0.43930 (8)	0.0589 (6)
H5A	0.0908	0.6713	0.4638	0.071*
C6	0.09647 (14)	0.6737 (4)	0.39544 (8)	0.0575 (6)
H6A	0.0478	0.6906	0.3907	0.069*
C7	0.26712 (11)	0.6330 (3)	0.32997 (7)	0.0396 (4)
H7A	0.3151	0.6224	0.3376	0.048*
C8	0.27699 (11)	0.6312 (3)	0.21432 (7)	0.0376 (4)
C9	0.32487 (11)	0.6078 (3)	0.17375 (7)	0.0430 (5)
H9A	0.3741	0.6312	0.1825	0.052*
H9B	0.3210	0.4719	0.1614	0.052*
C10	0.33961 (11)	0.7564 (3)	0.10033 (7)	0.0432 (5)
C11	0.32289 (16)	0.9148 (4)	0.07150 (9)	0.0694 (8)
H11A	0.2890	1.0099	0.0804	0.083*
C12	0.35588 (16)	0.9335 (4)	0.02962 (9)	0.0709 (8)
H12A	0.3440	1.0399	0.0102	0.085*
C13	0.40604 (13)	0.7950 (3)	0.01670 (7)	0.0505 (5)
C14	0.42323 (14)	0.6372 (3)	0.04485 (7)	0.0533 (6)
H14A	0.4573	0.5431	0.0357	0.064*
C15	0.39005 (13)	0.6170 (3)	0.08685 (7)	0.0481 (5)
H15A	0.4018	0.5094	0.1060	0.058*
C16	0.05887 (13)	0.6245 (4)	0.18536 (8)	0.0545 (6)
H16A	0.0938	0.6107	0.1630	0.065*
C17	−0.01198 (13)	0.6245 (4)	0.17777 (8)	0.0619 (7)
H17A	−0.0348	0.6117	0.1497	0.074*
C18	0.00820 (11)	0.6595 (3)	0.25023 (8)	0.0418 (5)
H18A	0.0008	0.6748	0.2815	0.050*

	U11	U22	U33	U12	U13	U23
Ni1	0.02247 (14)	0.04455 (16)	0.03838 (15)	−0.00093 (10)	0.00212 (10)	0.00103 (11)
O1	0.0303 (8)	0.0837 (11)	0.0416 (8)	0.0012 (8)	0.0047 (6)	0.0011 (7)
O2	0.0259 (7)	0.0523 (8)	0.0408 (7)	−0.0004 (6)	0.0013 (6)	0.0006 (6)
O3	0.0488 (10)	0.0576 (9)	0.0507 (8)	0.0156 (8)	0.0168 (7)	0.0097 (7)
N1	0.0259 (8)	0.0354 (8)	0.0419 (9)	0.0007 (7)	0.0018 (7)	0.0000 (7)
N2	0.0249 (8)	0.0471 (9)	0.0422 (9)	0.0004 (7)	0.0043 (7)	0.0010 (7)
N3	0.0268 (9)	0.0488 (9)	0.0453 (9)	−0.0028 (7)	0.0023 (7)	−0.0002 (8)
N4	0.0238 (9)	0.0643 (11)	0.0585 (11)	0.0004 (8)	−0.0006 (8)	0.0004 (9)
Cl1	0.0848 (5)	0.0815 (4)	0.0491 (3)	0.0023 (4)	0.0225 (3)	0.0045 (3)
C1	0.0442 (13)	0.0457 (11)	0.0400 (10)	−0.0037 (10)	0.0040 (9)	0.0005 (9)
C2	0.0423 (12)	0.0345 (9)	0.0413 (10)	0.0001 (9)	0.0003 (9)	0.0005 (8)
C3	0.0533 (15)	0.0526 (13)	0.0467 (12)	0.0052 (11)	−0.0053 (11)	−0.0010 (10)
C4	0.0749 (19)	0.0589 (14)	0.0401 (11)	0.0025 (14)	0.0010 (12)	0.0006 (10)
C5	0.0646 (18)	0.0688 (15)	0.0433 (12)	−0.0019 (13)	0.0152 (12)	−0.0017 (11)
C6	0.0441 (14)	0.0787 (16)	0.0497 (12)	−0.0033 (12)	0.0116 (11)	0.0007 (12)
C7	0.0305 (11)	0.0434 (10)	0.0448 (11)	0.0030 (9)	−0.0038 (9)	0.0021 (9)
C8	0.0282 (10)	0.0399 (10)	0.0448 (11)	0.0005 (8)	0.0034 (9)	0.0026 (9)
C9	0.0302 (11)	0.0569 (12)	0.0418 (11)	0.0031 (9)	0.0044 (9)	0.0037 (10)
C10	0.0353 (12)	0.0492 (11)	0.0450 (11)	−0.0007 (9)	0.0067 (9)	0.0012 (10)
C11	0.0705 (19)	0.0652 (15)	0.0725 (17)	0.0248 (14)	0.0267 (15)	0.0204 (14)
C12	0.076 (2)	0.0674 (15)	0.0692 (16)	0.0195 (15)	0.0218 (15)	0.0269 (14)
C13	0.0502 (14)	0.0613 (13)	0.0400 (10)	−0.0037 (11)	0.0074 (10)	0.0007 (10)
C14	0.0522 (14)	0.0614 (14)	0.0463 (12)	0.0104 (12)	0.0085 (11)	−0.0039 (10)
C15	0.0456 (13)	0.0551 (13)	0.0436 (11)	0.0105 (11)	0.0018 (10)	0.0046 (10)
C16	0.0335 (12)	0.0849 (17)	0.0452 (11)	−0.0035 (12)	0.0035 (10)	−0.0045 (11)
C17	0.0363 (13)	0.100 (2)	0.0490 (13)	−0.0063 (13)	−0.0056 (10)	−0.0039 (13)
C18	0.0267 (10)	0.0506 (11)	0.0480 (11)	0.0006 (9)	0.0016 (9)	−0.0035 (10)

Ni1—O1	1.8178 (14)	C4—C5	1.384 (4)
Ni1—N1	1.8264 (17)	C4—H4B	0.9300
Ni1—O2	1.8473 (14)	C5—C6	1.373 (3)
Ni1—N3	1.9064 (18)	C5—H5A	0.9300
O1—C1	1.314 (3)	C6—H6A	0.9300
O2—C8	1.284 (2)	C7—H7A	0.9300
O3—C10	1.362 (2)	C8—C9	1.495 (3)
O3—C9	1.413 (2)	C9—H9A	0.9700
N1—C7	1.294 (3)	C9—H9B	0.9700
N1—N2	1.405 (2)	C10—C15	1.377 (3)
N2—C8	1.307 (3)	C10—C11	1.380 (3)
N3—C18	1.310 (3)	C11—C12	1.377 (3)
N3—C16	1.368 (3)	C11—H11A	0.9300
N4—C18	1.326 (3)	C12—C13	1.365 (4)
N4—C17	1.369 (3)	C12—H12A	0.9300
N4—H4A	0.8600	C13—C14	1.367 (3)
Cl1—C13	1.741 (2)	C14—C15	1.383 (3)
C1—C6	1.406 (3)	C14—H14A	0.9300
C1—C2	1.409 (3)	C15—H15A	0.9300
C2—C3	1.404 (3)	C16—C17	1.347 (3)
C2—C7	1.427 (3)	C16—H16A	0.9300
C3—C4	1.367 (3)	C17—H17A	0.9300
C3—H3A	0.9300	C18—H18A	0.9300
O1—Ni1—N1	95.41 (7)	N1—C7—H7A	118.3
O1—Ni1—O2	178.45 (7)	C2—C7—H7A	118.3
N1—Ni1—O2	83.87 (7)	O2—C8—N2	123.63 (19)
O1—Ni1—N3	89.58 (7)	O2—C8—C9	117.97 (18)
N1—Ni1—N3	174.52 (7)	N2—C8—C9	118.34 (18)
O2—Ni1—N3	91.20 (7)	O3—C9—C8	107.58 (16)
C1—O1—Ni1	126.98 (15)	O3—C9—H9A	110.2
C8—O2—Ni1	110.41 (13)	C8—C9—H9A	110.2
C10—O3—C9	117.83 (16)	O3—C9—H9B	110.2
C7—N1—N2	117.51 (17)	C8—C9—H9B	110.2
C7—N1—Ni1	127.87 (14)	H9A—C9—H9B	108.5
N2—N1—Ni1	114.59 (12)	O3—C10—C15	125.01 (19)
C8—N2—N1	107.48 (16)	O3—C10—C11	115.7 (2)
C18—N3—C16	105.56 (19)	C15—C10—C11	119.2 (2)
C18—N3—Ni1	126.33 (15)	C12—C11—C10	120.6 (2)
C16—N3—Ni1	128.04 (15)	C12—C11—H11A	119.7
C18—N4—C17	106.83 (19)	C10—C11—H11A	119.7
C18—N4—H4A	126.6	C13—C12—C11	119.7 (2)
C17—N4—H4A	126.6	C13—C12—H12A	120.1
O1—C1—C6	117.9 (2)	C11—C12—H12A	120.1
O1—C1—C2	124.22 (19)	C12—C13—C14	120.5 (2)
C6—C1—C2	117.9 (2)	C12—C13—Cl1	119.65 (18)
C3—C2—C1	119.4 (2)	C14—C13—Cl1	119.89 (19)
C3—C2—C7	118.8 (2)	C13—C14—C15	120.1 (2)
C1—C2—C7	121.83 (19)	C13—C14—H14A	119.9
C4—C3—C2	121.7 (2)	C15—C14—H14A	119.9
C4—C3—H3A	119.2	C10—C15—C14	119.9 (2)
C2—C3—H3A	119.2	C10—C15—H15A	120.1
C3—C4—C5	118.8 (2)	C14—C15—H15A	120.1
C3—C4—H4B	120.6	C17—C16—N3	109.2 (2)
C5—C4—H4B	120.6	C17—C16—H16A	125.4
C6—C5—C4	121.3 (2)	N3—C16—H16A	125.4
C6—C5—H5A	119.4	C16—C17—N4	106.4 (2)
C4—C5—H5A	119.4	C16—C17—H17A	126.8
C5—C6—C1	121.0 (2)	N4—C17—H17A	126.8
C5—C6—H6A	119.5	N3—C18—N4	112.0 (2)
C1—C6—H6A	119.5	N3—C18—H18A	124.0
N1—C7—C2	123.49 (19)	N4—C18—H18A	124.0
N1—Ni1—O1—C1	−3.95 (18)	C2—C1—C6—C5	−1.8 (3)
O2—Ni1—O1—C1	−66 (2)	N2—N1—C7—C2	179.46 (15)
N3—Ni1—O1—C1	173.78 (18)	Ni1—N1—C7—C2	−2.8 (3)
O1—Ni1—O2—C8	62 (2)	C3—C2—C7—N1	179.26 (18)
N1—Ni1—O2—C8	−0.19 (13)	C1—C2—C7—N1	−1.2 (3)
N3—Ni1—O2—C8	−177.80 (13)	Ni1—O2—C8—N2	−0.8 (2)
O1—Ni1—N1—C7	4.62 (17)	Ni1—O2—C8—C9	176.13 (13)
O2—Ni1—N1—C7	−176.76 (16)	N1—N2—C8—O2	1.6 (3)
N3—Ni1—N1—C7	−150.9 (7)	N1—N2—C8—C9	−175.36 (16)
O1—Ni1—N1—N2	−177.59 (11)	C10—O3—C9—C8	−179.55 (18)
O2—Ni1—N1—N2	1.03 (11)	O2—C8—C9—O3	48.3 (2)
N3—Ni1—N1—N2	26.9 (8)	N2—C8—C9—O3	−134.64 (19)
C7—N1—N2—C8	176.44 (17)	C9—O3—C10—C15	8.3 (3)
Ni1—N1—N2—C8	−1.59 (17)	C9—O3—C10—C11	−172.1 (2)
O1—Ni1—N3—C18	0.86 (18)	O3—C10—C11—C12	−179.4 (3)
N1—Ni1—N3—C18	156.5 (6)	C15—C10—C11—C12	0.3 (4)
O2—Ni1—N3—C18	−177.80 (17)	C10—C11—C12—C13	−0.6 (5)
O1—Ni1—N3—C16	−175.8 (2)	C11—C12—C13—C14	0.6 (4)
N1—Ni1—N3—C16	−20.2 (8)	C11—C12—C13—Cl1	−178.4 (2)
O2—Ni1—N3—C16	5.55 (19)	C12—C13—C14—C15	−0.3 (4)
Ni1—O1—C1—C6	−179.05 (14)	Cl1—C13—C14—C15	178.68 (19)
Ni1—O1—C1—C2	1.5 (3)	O3—C10—C15—C14	179.7 (2)
O1—C1—C2—C3	−178.61 (18)	C11—C10—C15—C14	0.0 (4)
C6—C1—C2—C3	2.0 (3)	C13—C14—C15—C10	0.0 (4)
O1—C1—C2—C7	1.8 (3)	C18—N3—C16—C17	0.6 (3)
C6—C1—C2—C7	−177.61 (18)	Ni1—N3—C16—C17	177.80 (16)
C1—C2—C3—C4	−0.7 (3)	N3—C16—C17—N4	−0.4 (3)
C7—C2—C3—C4	178.91 (19)	C18—N4—C17—C16	0.1 (3)
C2—C3—C4—C5	−0.9 (3)	C16—N3—C18—N4	−0.6 (2)
C3—C4—C5—C6	1.1 (4)	Ni1—N3—C18—N4	−177.83 (13)
C4—C5—C6—C1	0.3 (4)	C17—N4—C18—N3	0.3 (2)
O1—C1—C6—C5	178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N2i	0.86	2.06	2.916 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N2i	0.86	2.06	2.916 (3)	172

Symmetry code: (i) .