{6,6′-Dieth­oxy-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato}nickel(II) monohydrate

Hadi Kargar; Arezoo Jamshidvand; Hoong-Kun Fun; Reza Kia

doi:10.1107/S1600536809008721

. 2009 Mar 14;65(Pt 4):m403–m404. doi: 10.1107/S1600536809008721

{6,6′-Diethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)]diphenolato}nickel(II) monohydrate

Hadi Kargar ^a, Arezoo Jamshidvand ^a, Hoong-Kun Fun ^b,^*, Reza Kia ^b,^‡

PMCID: PMC2968910 PMID: 21582349

Abstract

In the title complex, [Ni(C₂₃H₂₈N₂O₄)]·H₂O, the Ni^II ion is coordinated by the N₂O₂ unit of the tetradentate Schiff base ligand in a slightly distorted planar geometry. The asymmetric unit of the title compound comprises one complex molecule and a water molecule of crystallization. The H atoms of the water molecule make bifurcated intermolecular hydrogen bonds with the O atoms of the phenolate and ethoxy groups with R ₁ ²(5) and R ₁ ²(6) ring motifs, which may, in part, influence the molecular configuration. The dihedral angle between the two benzene rings is 31.43 (5)°. The crystal structure is further stabilized by intermolecular C—H⋯O and C—H⋯π interactions, which link neighbouring molecules into one-dimensional extended chains along the a axis. An interesting feature of the crystal structure is the short intermolecular C⋯C [3.3044 (14) Å] contact which is shorter than the sum of the van der Waals radii.

Related literature

For bond-length data, see Allen et al. (1987 ▶). For related structures see, for example: Clark et al. (1968 ▶, 1969 ▶, 1970 ▶). For the applications and bioactivities of Schiff base complexes with transition metals, see, for example: Elmali et al. (2000 ▶); Blower (1998 ▶); Granovski et al., (1993 ▶); Li & Chang (1991 ▶); Shahrokhian et al. (2000 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Ni(C₂₃H₂₈N₂O₄)]·H₂O
M _r = 473.20
Triclinic,
a = 9.3797 (1) Å
b = 10.7570 (1) Å
c = 12.8002 (1) Å
α = 65.811 (1)°
β = 68.87°
γ = 78.336 (1)°
V = 1096.64 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 100 K
0.36 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.733, T _max = 0.879
29688 measured reflections
9211 independent reflections
8270 reflections with I > 2σI)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.073
S = 1.04
9211 reflections
290 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008721/at2741sup1.cif

e-65-0m403-sup1.cif^{(24.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008721/at2741Isup2.hkl

e-65-0m403-Isup2.hkl^{(450.5KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Ni1—O1	1.8523 (6)
Ni1—O2	1.8605 (6)
Ni1—N2	1.8748 (7)
Ni1—N1	1.8766 (8)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O1	0.80 (2)	2.499 (19)	3.0368 (12)	125.8 (16)
O1W—H2W1⋯O3	0.80 (2)	2.20 (2)	2.9805 (12)	164.7 (18)
O1W—H1W1⋯O2	0.77 (2)	2.15 (2)	2.8597 (10)	152 (2)
O1W—H1W1⋯O4	0.77 (2)	2.53 (2)	3.1658 (12)	140 (2)
C8—H8B⋯O1ⁱ	0.99	2.42	3.3216 (13)	151
C11—H11A⋯O1Wⁱⁱ	0.95	2.51	3.4242 (13)	161
C5—-H5A⋯Cg1ⁱ	0.95	2.88	3.3506 (12)	111
C10—-H10B⋯Cg1ⁱⁱ	0.99	2.73	3.4406 (11)	129
C22—-H22B⋯Cg2ⁱⁱⁱ	0.99	2.87	3.8068 (11)	158

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C12–C17 and C1–C6 benzene rings, respectively.

Acknowledgments

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK and AJ thank PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Schiff base complexes are some of the most important stereochemical models in transition metal coordination chemistry, with their ease of preparation and structural variations (Granovski et al., 1993). Metal derivatives of Schiff bases have been studied extensively, and copper(II) and Ni(II) complexes play a major role in both synthetic and structural research (Elmali et al., 2000; Blower, 1998; Granovski et al., 1993; Li & Chang, 1991; Shahrokhian et al., 2000). Tetradentate Schiff base metal complexes may form trans or cis planar or tetrahedral structures (Elmali et al., 2000).

The Ni^II ion of the title compound (Fig. 1), shows a sligthly distorted planar geometry which is coordinated by two imine N atoms and two phenol O atoms of the tetradentate Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with the related structures (Clark et al., 1968, 1969, 1970). The asymmetric unit of the title compound comprises one molecule of complex and a water molecule of crystallization. The hydrogen atoms of the water molecule make bifurcated intermolecular hydrogen bonds with the oxygen atoms of the phenolato- and ethoxy groups with R²₁(5) and R²₁(6) ring motifs (Bernstein et al., 1995), which may, in part, influence the molecular configuration. The dihedral angle between the two benzene rings is 31.43 (5)°. The crystal structure is further stabilized by intermolecular C—H···O and C—H···π interactions which link neighbouring molecules into 1-D extended chains along the a axis. The interesting feature of the crystal structure is a short intermolecular C7···C17ⁱ [3.3044 (14) Å] contact which is shorter than the sum of the van der Waals radius of a carbon atom. The crystal structure is further stabilized by intermolecular C—H···O and C—H···π interactions (Table 2, Cg1 and Cg2 are the centroids of the C12–C17 and C1–C6 benzene rings) which link neighbouring molecules into 1-D extended chains along the b-axis (Fig. 2).

Experimental

A chloroform solution (40 ml) of [N,N'-Bis(3-ethoxy-salicylidene)-2, 2-dimethyl-1,3-propanediamin (1 mmol) was added to a ethanol solution (20 mL) of NiCl₂.6H₂O (1.05 mmol, 237 mg). The mixture was refluxed for 30 min and then filtered. After keeping the filtrate in air, deep-green block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.