{6,6′-Diethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]di­phenolato}nickel(II) dihydrate

Kargar, H.; Kia, R.; Jamshidvand, A.; Fun, H.-K.

doi:10.1107/S1600536809012641

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m498-m499

doi:10.1107/S1600536809012641

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{6,6′-Diethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) dihydrate

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

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 12 March 2009; accepted 3 April 2009; online 8 April 2009)

In the title complex, [Ni(C₂₆H₂₆N₂O₄)]·2H₂O, the Ni^II ion, lying on a twofold crystallographic rotation axis, has a square-planar geometry, being coordinated by the N₂O₂ unit of the tetradentate Schiff base ligand. The asymmetric unit of the title compound comprises one-half of the complex molecule and one of the water molecules of crystallization. The water H atoms form bifurcated O—H⋯(O,O) hydrogen bonds with the O atoms of the phenolato and ethoxy groups with R₁²(5) and R₁²(6) ring motifs. The dihedral angle between the central benzene ring and the two outer benzene rings are 4.07 (11) and 3.99 (12)°. The dihedral angle between the two O–Ni–N coordination planes is only 0.77 (11)°. In the crystal structure, the molecules are linked together into extended chains along the c axis by intermolecular O—H⋯O and C—H⋯O interactions. An interesting feature of the crystal structure is a short intermolecular C ⋯ C [3.355 (3) Å] contact, which is shorter than the sum of the van der Waals radii. The crystal structure may be further stabilized by intermolecular π–π interactions [centroid–centroid distances in the range 3.5758 (13)–3.6337 (13) Å].

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 bioactivity of Schiff base complexes see, for example: Elmali et al. (2000 ); Blower (1998 ); Granovski et al. (1993 ); Li & Chang, (1991 ); Shahrokhian et al. (2000 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

[Ni(C₂₆H₂₆N₂O₄)]·2H₂O
M_r = 525.23
Orthorhombic, P b c n
a = 12.8706 (4) Å
b = 16.1130 (4) Å
c = 11.8546 (3) Å
V = 2458.45 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 294 K
0.30 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.790, T_max = 0.935
16330 measured reflections
3517 independent reflections
2007 reflections with I > 2σI)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.122
S = 1.01
3517 reflections
161 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1	1.8447 (15)
Ni1—N1	1.8573 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1	0.82	2.50	3.087 (2)	129
O1W—H1W1⋯O2	0.82	2.39	3.145 (3)	152
O1W—H2W1⋯O1ⁱ	0.82	2.47	3.083 (3)	133
O1W—H2W1⋯O2ⁱ	0.82	2.41	3.121 (3)	146
C7—H7A⋯O1Wⁱⁱ	0.93	2.57	3.383 (3)	146
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012641/cs2114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012641/cs2114Isup2.hkl

checkCIF report

Comment top

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 square planar geometry which is coordinated by two imine N atoms and two phenol O atoms of the tetradentate Schiff base ligand and lies across a crystallographic twofold rotation axis. 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 water H atoms form bifurcated O—H(O,O) 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 (Fig. 1). The dihedral angle between the central benzene ring and the two outer benzene rings are 4.07 (11) and 3.99 (12)°. The dihedral angle between the two coordination planes O1—Ni1—N1 and O1A—Ni1—N1A is 0.77 (11)°. In the crystal structure the complex and two water molecules, association of which form the title compound, are linked together into 1-D extended chains by intermolecular O—H···O and C—H···O interactions along the c axis (Fig. 2). The interesting feature of the crystal structure is a short intermolecular C1···C7ⁱⁱⁱ [3.355 (3) Å; (iii) 1 - x, -y, 1 - z ] contact, shorter than the sum of the van der Waals radius of carbon atoms. The crystal structure is further stabilized by intermolecular π-π [Cg1···Cg3ⁱⁱⁱ = 3.5758 (13) Å; Cg2···Cg2ⁱⁱⁱ = 3.6085 (11) Å; Cg2···Cg3ⁱⁱⁱ = 3.6337 (13) Å, Cg1, Cg2 and Cg3 are the centroid of the Ni1/N1/C8/C8A/N1A, C1–C6, and Ni1/O1/C1/C6/C7/N1 rings, respectively].

Related literature top

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 bioactivity of Schiff base complexes see, for example: Elmali et al. (2000); Blower (1998); Granovski et al. (1993); Li & Chang, (1991); Shahrokhian et al. (2000). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A chloroform solution (40 ml) of [N,N'-Bis(3-ethoxy-salicylidene)- 4,5-dimethyl-phenylenediamine (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-red block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.

Computing details top

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

Figures top

	Fig. 1. The title molecular compound, showing 50° probability displacement ellipsoids and the atomic numbering, hydrogen bonds are shown as dashed lines. Symmetry code for suffix A: -x + 1, y, -z + 1/2.
	Fig. 2. A crystal packing excerpt of the title compound viewed down the b-axis, showing 1-D extended chains along the c-axis. Intermolecular interactions are drawn as dashed lines.

{6,6'-Diethoxy-2,2'-[4,5-dimethyl-o- phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) dihydrate top

Crystal data top

[Ni(C₂₆H₂₆N₂O₄)]·2H₂O	F(000) = 1104
M_r = 525.23	D_x = 1.419 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2497 reflections
a = 12.8706 (4) Å	θ = 2.7–22.3°
b = 16.1130 (4) Å	µ = 0.83 mm⁻¹
c = 11.8546 (3) Å	T = 294 K
V = 2458.45 (12) Å³	Block, red
Z = 4	0.30 × 0.16 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3517 independent reflections
Radiation source: fine-focus sealed tube	2007 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ϕ and ω scans	θ_max = 29.8°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
T_min = 0.790, T_max = 0.935	k = −22→22
16330 measured reflections	l = −16→11

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0543P)² + 0.1108P] where P = (F_o² + 2F_c²)/3
3517 reflections	(Δ/σ)_max < 0.001
161 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Ni(C₂₆H₂₆N₂O₄)]·2H₂O	V = 2458.45 (12) Å³
M_r = 525.23	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 12.8706 (4) Å	µ = 0.83 mm⁻¹
b = 16.1130 (4) Å	T = 294 K
c = 11.8546 (3) Å	0.30 × 0.16 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3517 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2007 reflections with I > 2σ(I)
T_min = 0.790, T_max = 0.935	R_int = 0.065
16330 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
3517 reflections	Δρ_min = −0.51 e Å⁻³
161 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	−0.00935 (2)	0.2500	0.04044 (15)
O1	0.44372 (13)	0.07589 (9)	0.33400 (13)	0.0501 (4)
O2	0.38481 (16)	0.21443 (10)	0.42373 (15)	0.0716 (6)
N1	0.44336 (14)	−0.09376 (10)	0.33719 (15)	0.0398 (4)
C1	0.38667 (17)	0.06930 (14)	0.4246 (2)	0.0441 (5)
C2	0.3505 (2)	0.14350 (15)	0.4772 (2)	0.0524 (6)
C3	0.2894 (2)	0.14174 (16)	0.5706 (2)	0.0605 (7)
H3A	0.2659	0.1912	0.6020	0.073*
C4	0.2614 (2)	0.06548 (19)	0.6203 (2)	0.0660 (8)
H4A	0.2193	0.0646	0.6841	0.079*
C5	0.2961 (2)	−0.00668 (16)	0.5746 (2)	0.0566 (7)
H5A	0.2790	−0.0568	0.6088	0.068*
C6	0.35820 (19)	−0.00679 (13)	0.4755 (2)	0.0451 (6)
C7	0.39054 (17)	−0.08387 (14)	0.42982 (19)	0.0441 (5)
H7A	0.3725	−0.1315	0.4695	0.053*
C8	0.46786 (17)	−0.17483 (13)	0.29740 (18)	0.0412 (5)
C9	0.43332 (19)	−0.24982 (14)	0.3410 (2)	0.0498 (6)
H9A	0.3879	−0.2497	0.4020	0.060*
C10	0.4649 (2)	−0.32468 (14)	0.2957 (2)	0.0519 (6)
C11	0.3545 (2)	0.29234 (15)	0.4698 (3)	0.0759 (9)
H11A	0.3783	0.2974	0.5471	0.091*
H11B	0.2794	0.2979	0.4687	0.091*
C12	0.4041 (3)	0.35795 (18)	0.3968 (3)	0.1078 (13)
H12A	0.3824	0.4119	0.4219	0.162*
H12B	0.3832	0.3500	0.3198	0.162*
H12C	0.4783	0.3537	0.4022	0.162*
C13	0.4247 (3)	−0.40558 (15)	0.3438 (2)	0.0791 (10)
H13A	0.3822	−0.3943	0.4086	0.119*
H13B	0.4823	−0.4399	0.3656	0.119*
H13C	0.3841	−0.4338	0.2877	0.119*
O1W	0.38489 (17)	0.20940 (12)	0.15851 (16)	0.0853 (6)
H1W1	0.3725	0.1955	0.2239	0.128*
H2W1	0.4475	0.2018	0.1648	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0477 (2)	0.0286 (2)	0.0450 (3)	0.000	0.00116 (19)	0.000
O1	0.0667 (11)	0.0307 (8)	0.0530 (10)	0.0029 (8)	0.0057 (9)	−0.0006 (7)
O2	0.1017 (15)	0.0353 (9)	0.0778 (13)	0.0146 (9)	0.0068 (11)	−0.0068 (9)
N1	0.0447 (11)	0.0313 (9)	0.0434 (11)	0.0007 (8)	0.0005 (9)	−0.0028 (8)
C1	0.0453 (13)	0.0388 (12)	0.0481 (14)	0.0059 (10)	−0.0064 (11)	−0.0071 (11)
C2	0.0561 (15)	0.0429 (14)	0.0582 (16)	0.0118 (12)	−0.0078 (12)	−0.0123 (12)
C3	0.0610 (17)	0.0553 (16)	0.0651 (18)	0.0144 (13)	−0.0023 (14)	−0.0211 (14)
C4	0.0646 (17)	0.0690 (19)	0.0643 (18)	0.0047 (14)	0.0141 (14)	−0.0177 (15)
C5	0.0582 (16)	0.0584 (16)	0.0533 (17)	−0.0020 (12)	0.0091 (13)	−0.0069 (12)
C6	0.0447 (13)	0.0418 (13)	0.0487 (15)	0.0012 (10)	−0.0008 (10)	−0.0074 (11)
C7	0.0470 (13)	0.0392 (12)	0.0461 (14)	−0.0042 (10)	0.0000 (11)	−0.0020 (10)
C8	0.0496 (13)	0.0312 (11)	0.0429 (13)	0.0000 (9)	−0.0010 (10)	−0.0010 (9)
C9	0.0603 (15)	0.0384 (12)	0.0507 (14)	0.0005 (11)	0.0115 (12)	0.0003 (11)
C10	0.0660 (16)	0.0321 (12)	0.0576 (15)	−0.0057 (10)	0.0056 (12)	0.0027 (10)
C11	0.079 (2)	0.0387 (15)	0.111 (2)	0.0179 (14)	−0.0129 (18)	−0.0251 (16)
C12	0.161 (4)	0.0409 (17)	0.122 (3)	0.016 (2)	−0.011 (3)	−0.0029 (18)
C13	0.111 (3)	0.0372 (15)	0.089 (2)	−0.0093 (15)	0.0313 (19)	0.0036 (14)
O1W	0.1029 (16)	0.0723 (14)	0.0809 (14)	0.0234 (12)	−0.0218 (12)	0.0009 (11)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.8447 (15)	C7—H7A	0.9300
Ni1—O1	1.8447 (15)	C8—C9	1.387 (3)
Ni1—N1	1.8573 (17)	C8—C8ⁱ	1.396 (4)
Ni1—N1ⁱ	1.8573 (17)	C9—C10	1.381 (3)
O1—C1	1.306 (3)	C9—H9A	0.9300
O2—C2	1.380 (3)	C10—C10ⁱ	1.410 (5)
O2—C11	1.423 (3)	C10—C13	1.514 (3)
N1—C7	1.301 (3)	C11—C12	1.508 (4)
N1—C8	1.424 (2)	C11—H11A	0.9700
C1—C6	1.415 (3)	C11—H11B	0.9700
C1—C2	1.427 (3)	C12—H12A	0.9600
C2—C3	1.358 (3)	C12—H12B	0.9600
C3—C4	1.410 (4)	C12—H12C	0.9600
C3—H3A	0.9300	C13—H13A	0.9600
C4—C5	1.358 (3)	C13—H13B	0.9600
C4—H4A	0.9300	C13—H13C	0.9600
C5—C6	1.421 (3)	O1W—H1W1	0.8226
C5—H5A	0.9300	O1W—H2W1	0.8179
C6—C7	1.417 (3)

O1ⁱ—Ni1—O1	83.75 (10)	N1—C7—H7A	117.2
O1ⁱ—Ni1—N1	178.81 (7)	C6—C7—H7A	117.2
O1—Ni1—N1	95.21 (7)	C9—C8—C8ⁱ	119.32 (13)
O1ⁱ—Ni1—N1ⁱ	95.21 (7)	C9—C8—N1	127.2 (2)
O1—Ni1—N1ⁱ	178.81 (7)	C8ⁱ—C8—N1	113.45 (11)
N1—Ni1—N1ⁱ	85.84 (11)	C10—C9—C8	121.4 (2)
C1—O1—Ni1	127.19 (14)	C10—C9—H9A	119.3
C2—O2—C11	117.8 (2)	C8—C9—H9A	119.3
C7—N1—C8	120.49 (18)	C9—C10—C10ⁱ	119.14 (14)
C7—N1—Ni1	125.80 (15)	C9—C10—C13	120.3 (2)
C8—N1—Ni1	113.61 (14)	C10ⁱ—C10—C13	120.54 (14)
O1—C1—C6	124.54 (19)	O2—C11—C12	106.4 (2)
O1—C1—C2	118.4 (2)	O2—C11—H11A	110.5
C6—C1—C2	117.1 (2)	C12—C11—H11A	110.5
C3—C2—O2	125.3 (2)	O2—C11—H11B	110.5
C3—C2—C1	121.8 (2)	C12—C11—H11B	110.5
O2—C2—C1	112.9 (2)	H11A—C11—H11B	108.6
C2—C3—C4	120.5 (2)	C11—C12—H12A	109.5
C2—C3—H3A	119.8	C11—C12—H12B	109.5
C4—C3—H3A	119.8	H12A—C12—H12B	109.5
C5—C4—C3	119.7 (3)	C11—C12—H12C	109.5
C5—C4—H4A	120.2	H12A—C12—H12C	109.5
C3—C4—H4A	120.2	H12B—C12—H12C	109.5
C4—C5—C6	121.1 (2)	C10—C13—H13A	109.5
C4—C5—H5A	119.5	C10—C13—H13B	109.5
C6—C5—H5A	119.5	H13A—C13—H13B	109.5
C1—C6—C7	121.4 (2)	C10—C13—H13C	109.5
C1—C6—C5	119.8 (2)	H13A—C13—H13C	109.5
C7—C6—C5	118.8 (2)	H13B—C13—H13C	109.5
N1—C7—C6	125.7 (2)	H1W1—O1W—H2W1	93.7

O1ⁱ—Ni1—O1—C1	−177.9 (2)	C2—C1—C6—C7	−179.8 (2)
O1—Ni1—N1—C7	−4.77 (19)	O1—C1—C6—C5	179.7 (2)
N1ⁱ—Ni1—N1—C7	175.8 (2)	C2—C1—C6—C5	0.0 (3)
O1—Ni1—N1—C8	178.82 (14)	C4—C5—C6—C1	1.5 (4)
N1ⁱ—Ni1—N1—C8	−0.62 (11)	C4—C5—C6—C7	−178.6 (2)
Ni1—O1—C1—C6	0.5 (3)	C8—N1—C7—C6	−177.5 (2)
Ni1—O1—C1—C2	−179.89 (15)	Ni1—N1—C7—C6	6.3 (3)
C11—O2—C2—C3	0.2 (4)	C1—C6—C7—N1	−3.4 (4)
C11—O2—C2—C1	−179.2 (2)	C5—C6—C7—N1	176.7 (2)
O1—C1—C2—C3	178.9 (2)	C7—N1—C8—C9	6.6 (4)
C6—C1—C2—C3	−1.4 (3)	Ni1—N1—C8—C9	−176.77 (19)
O1—C1—C2—O2	−1.6 (3)	C7—N1—C8—C8ⁱ	−174.9 (2)
C6—C1—C2—O2	178.1 (2)	Ni1—N1—C8—C8ⁱ	1.8 (3)
O2—C2—C3—C4	−178.1 (2)	C8ⁱ—C8—C9—C10	3.0 (4)
C1—C2—C3—C4	1.3 (4)	N1—C8—C9—C10	−178.6 (2)
C2—C3—C4—C5	0.3 (4)	C8—C9—C10—C10ⁱ	1.0 (5)
C3—C4—C5—C6	−1.7 (4)	C8—C9—C10—C13	−179.1 (2)
O1—C1—C6—C7	−0.2 (4)	C2—O2—C11—C12	178.9 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1	0.82	2.50	3.087 (2)	129
O1W—H1W1···O2	0.82	2.39	3.145 (3)	152
O1W—H2W1···O1ⁱ	0.82	2.47	3.083 (3)	133
O1W—H2W1···O2ⁱ	0.82	2.41	3.121 (3)	146
C7—H7A···O1Wⁱⁱ	0.93	2.57	3.383 (3)	146

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₂₆H₂₆N₂O₄)]·2H₂O
M_r	525.23
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	294
a, b, c (Å)	12.8706 (4), 16.1130 (4), 11.8546 (3)
V (Å³)	2458.45 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.30 × 0.16 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.790, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	16330, 3517, 2007
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.700

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.122, 1.01
No. of reflections	3517
No. of parameters	161
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.51

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Ni1—O1

1.8447 (15)

Ni1—N1

1.8573 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1	0.8200	2.5000	3.087 (2)	129.00
O1W—H1W1···O2	0.8200	2.3900	3.145 (3)	152.00
O1W—H2W1···O1ⁱ	0.8200	2.4700	3.083 (3)	133.00
O1W—H2W1···O2ⁱ	0.8200	2.4100	3.121 (3)	146.00
C7—H7A···O1Wⁱⁱ	0.9300	2.5700	3.383 (3)	146.00

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y, z+1/2.

Footnotes

‡Additional correspondence author: zsrkk@yahoo.com.

Acknowledgements

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.

References

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Volume 65| Part 5| May 2009| Pages m498-m499

doi:10.1107/S1600536809012641

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

{6,6′-Di­eth­oxy-2,2′-[4,5-di­methyl-o-phenylenebis(nitrilo­methyl­idyne)]di­phenolato}nickel(II) dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

metal-organic compounds

{6,6′-Diethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) dihydrate