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

In the title complex, [Ni(C(26)H(26)N(2)O(4))]·2H(2)O, the Ni(II) ion, lying on a twofold crystallographic rotation axis, has a square-planar geometry, being coordinated by the N(2)O(2) unit of the tetra-dentate Schiff base ligand. The asymmetric unit of the title compound comprises one-half of the complex mol-ecule and one of the water mol-ecules of crystallization. The water H atoms form bifurcated O-H⋯(O,O) hydrogen bonds with the O atoms of the phenolato and eth-oxy groups with R(1) (2)(5) and R(1) (2)(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 mol-ecules are linked together into extended chains along the c axis by inter-molecular O-H⋯O and C-H⋯O inter-actions. An inter-esting feature of the crystal structure is a short inter-molecular 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 inter-molecular π-π inter-actions [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 = 525.23

Orthorhombic,

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 (; 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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.122

S = 1.01

3517 reflections

161 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.51 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 ▶).

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

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

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

[Ni(C26H26N2O4)]·2H2O	F(000) = 1104
Mr = 525.23	Dx = 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

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

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(Fo2) + (0.0543P)2 + 0.1108P] where P = (Fo2 + 2Fc2)/3
3517 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .