(2-{[2-(4-Chlorophenoxy)-1-oxido­ethyl­idene-κO1]hydrazono­methyl}­phenol­ato-κ2N1,O)(1H-imidazole-κN3)nickel(II)

Chen, X.-H.

doi:10.1107/S1600536808028171

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1253

doi:10.1107/S1600536808028171

Open

access

(2-{[2-(4-Chlorophenoxy)-1-oxidoethylidene-κO¹]hydrazonomethyl}phenolato-κ²N¹,O)(1H-imidazole-κN³)nickel(II)

Xiao-Hua Chen ^a ^*

^aCollege of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian 350007, People's Republic of China
^*Correspondence e-mail: xiaohuachen03@163.com

(Received 3 July 2008; accepted 3 September 2008; online 6 September 2008)

In the title complex, [Ni(C₁₅H₁₁ClN₂O₃)(C₃H₄N₂)], 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 molecule, forming a distorted square-planar geometry. Intermolecular 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_r = 429.50
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.087
S = 0.96
4146 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Hydrazones are of interest owing to their capacity for chelating to transition (Sur et al., 1993; Sun et al., 2005), lanthanide (Ma et al., 1989) and main group (Liu & Gao 1998) metals. Here we report the crystal structure of the title complex, (I) (Fig. 1). The Ni(II) ion exists in a square-planar N₂O₂ coordination geometry defined by the phenolate O1, hydrazine N1, and carbonyl O2 atom of the hydrazone ligand, and N3 atom from the 1H-imidazole molecule. The hydrazone ligand in the title complex is distorted, the dihedral angle between the two phenyl rings being 50.56 (9)°. The corresponding dihedral angle is about 87° in the complex [Co(C₁₅H₁₂N₂O₃)(C₅H₇O₂)(C₃H₇NO)] (Chen & Liu, 2006) with the ligand of salicylaldehyde phenoxyacylhydrazone. In the title complex, an extended one-dimensional chain structure is formed via intermolecular hydrogen bonds between the 1H-imidazole N—H groups and the uncoordinated N-atom of the hydrazone ligand (Fig. 2). The N4···N2(A) distance and the N4—H···N2(A) angle are 2.916 (3) Å and 171.92°, respectively [Symmetry code: (A) x - 1/2, y, -z + 1/2].

Related literature top

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 top

The hydrazone ligand was prepared by the reaction of salicylaldehyde and 4-chloro-phenoxyacetylhydrazine in a molar ratio of 1:1 under reflux in ethanol for 2 h. The yellow product obtained on cooling was recrystallized from methanol. Salicylaldehyde 4-chloro-phenoxyacetylhydrazone (1 mmol), [Ni(OAc)₂].4H₂O (1 mmol), imidazole (1 mmol), N,N-dimethylformamide (5 ml), and methanol (10 ml) were stirred for 2 h. The solution was filtered and allowed to stand at room temperature for one week, and red crystals of complex (I) were obtained.

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation,1999); cell refinement: TEXRAY (Molecular Structure Corporation,1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Extended chain structure of (I).

(2-{[2-(4-Chlorophenoxy)-1-oxidoethylidene-κO¹]hydrazonomethyl}phenolato- κ²N¹,O)(1H-imidazole-κN³)nickel(II) top

Crystal data top

[Ni(C₁₅H₁₁ClN₂O₃)(C₃H₄N₂)]	F(000) = 1760
M_r = 429.50	D_x = 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

Data collection top

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

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0475P)²] where P = (F_o² + 2F_c²)/3
4146 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Ni(C₁₅H₁₁ClN₂O₃)(C₃H₄N₂)]	V = 3619.2 (16) Å³
M_r = 429.50	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.745 (5) Å	µ = 1.25 mm⁻¹
b = 6.6054 (14) Å	T = 293 K
c = 29.230 (8) Å	0.65 × 0.21 × 0.15 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	4146 independent reflections
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	2947 reflections with I > 2σ(I)
T_min = 0.498, T_max = 0.835	R_int = 0.058
29384 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 0.96	Δρ_max = 0.40 e Å⁻³
4146 reflections	Δρ_min = −0.30 e Å⁻³
244 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	0.160819 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₁₁ClN₂O₃)(C₃H₄N₂)]
M_r	429.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	18.745 (5), 6.6054 (14), 29.230 (8)
V (Å³)	3619.2 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.25
Crystal size (mm)	0.65 × 0.21 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (TEXRAY; Molecular Structure Corporation, 1999)
T_min, T_max	0.498, 0.835
No. of measured, independent and observed [I > 2σ(I)] reflections	29384, 4146, 2947
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.087, 0.96
No. of reflections	4146
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30

Computer programs: TEXRAY (Molecular Structure Corporation,1999), TEXSAN (Molecular Structure Corporation,1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEX (McArdle,1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N2ⁱ	0.86	2.06	2.916 (3)	171.9

Symmetry code: (i) x−1/2, y, −z+1/2.

References

Chen, X.-H. & Liu, S.-X. (2006). Acta Cryst. E62, m2869–m2871. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Liu, S.-X. & Gao, S. (1998). Polyhedron, 17, 81–84. CSD CrossRef Web of Science Google Scholar
Ma, Y.-X., Ma, Z.-Q., Zhao, G., Ma, Y. & Yang, M. (1989). Polyhedron, 8, 2105–2108. CAS Google Scholar
McArdle, P. (1995). J. Appl. Cryst. 28, 65. CrossRef IUCr Journals Google Scholar
Molecular Structure Corporation (1999). TEXRAY and TEXSAN. MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, M.-M., Li, W.-P. & Liu, S.-X. (2005). Acta Cryst. E61, m1818–m1820. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sur, H., Roychowdhuri, S. & Seth, S. (1993). Acta Cryst. C49, 870–873. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1253

doi:10.1107/S1600536808028171

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)