Aqua-{6,6'-dimeth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}nickel(II).

The title complex, [Ni(C(18)H(18)N(2)O(4))(H(2)O)], lies on a mirror plane with the Ni(II) ion coordinated by two N and two O atoms of a tetra-dentate Schiff base ligand and one water O atom in a distorted square-pyramidal enviroment. The -CH(2)-CH(2)- group of the ligand is disordered equally over two sites about the mirror plane. The dihedral angle between the mean planes of the two symmetry-related chelate rings is 37.16 (6)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link complex mol-ecules into one-dimensional chains along [100] and these chains are linked, in turn, by very weak inter-molecular C-H⋯O hydrogen bonds into a two-dimensional network.

Related literature

For background to Schiff base complexes, see: Akine et al. (2005 ▶); Gamovski et al. (1993 ▶); Garg & Kumar (2003 ▶); Tarafder et al. (2002 ▶); Yang et al. (2000 ▶). For a related crystal structure, see: Wang et al. (2007 ▶).

Experimental

Crystal data

[Ni(C18H18N2O4)(H2O)]

M = 403.07

Orthorhombic,

a = 9.2712 (11) Å

b = 24.763 (3) Å

c = 7.5185 (10) Å

V = 1726.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.16 mm−1

T = 298 K

0.48 × 0.42 × 0.26 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.607, T max = 0.753

7520 measured reflections

1550 independent reflections

1368 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.19

1550 reflections

131 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034278/lh2877sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034278/lh2877Isup2.hkl

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

[Ni(C18H18N2O4)(H2O)]	F(000) = 840
Mr = 403.07	Dx = 1.551 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 3742 reflections
a = 9.2712 (11) Å	θ = 2.5–27.9°
b = 24.763 (3) Å	µ = 1.16 mm−1
c = 7.5185 (10) Å	T = 298 K
V = 1726.1 (4) Å3	Block, green
Z = 4	0.48 × 0.42 × 0.26 mm

Bruker SMART 1000 CCD area-detector diffractometer	1550 independent reflections
Radiation source: fine-focus sealed tube	1368 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.607, Tmax = 0.753	k = −29→27
7520 measured reflections	l = −5→8

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0321P)2 + 0.8008P] where P = (Fo2 + 2Fc2)/3
1550 reflections	(Δ/σ)max = 0.001
131 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.53 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	Occ. (<1)
Ni1	0.42518 (4)	0.7500	0.52345 (5)	0.03327 (16)
N1	0.5687 (2)	0.69791 (9)	0.4405 (3)	0.0577 (6)
O1	0.28010 (18)	0.69435 (6)	0.5505 (2)	0.0442 (4)
O2	0.04869 (19)	0.63591 (7)	0.5874 (3)	0.0602 (5)
O3	0.5119 (2)	0.7500	0.8191 (3)	0.0477 (6)
H3	0.5568	0.7224	0.8569	0.057*
C1	0.5493 (3)	0.64757 (11)	0.4103 (4)	0.0545 (7)
H1	0.6273	0.6282	0.3657	0.065*
C2	0.4180 (3)	0.61846 (10)	0.4391 (3)	0.0451 (6)
C3	0.2919 (3)	0.64343 (9)	0.5057 (3)	0.0402 (6)
C4	0.1686 (3)	0.60950 (10)	0.5265 (3)	0.0460 (6)
C5	0.1735 (3)	0.55512 (11)	0.4884 (4)	0.0587 (8)
H5	0.0919	0.5339	0.5055	0.070*
C6	0.2999 (4)	0.53165 (11)	0.4244 (4)	0.0675 (9)
H6	0.3025	0.4950	0.3984	0.081*
C7	0.4188 (3)	0.56250 (11)	0.4003 (4)	0.0592 (7)
H7	0.5028	0.5466	0.3574	0.071*
C8	−0.0821 (3)	0.60639 (13)	0.5993 (4)	0.0647 (8)
H8A	−0.1042	0.5908	0.4855	0.097*
H8B	−0.1587	0.6302	0.6344	0.097*
H8C	−0.0719	0.5782	0.6859	0.097*
C9	0.7178 (7)	0.7189 (3)	0.4502 (9)	0.0473 (14)	0.50
H9A	0.7867	0.6957	0.3901	0.057*	0.50
H9B	0.7479	0.7246	0.5723	0.057*	0.50
C10	0.6943 (7)	0.7720 (3)	0.3518 (9)	0.0544 (17)	0.50
H10A	0.7810	0.7939	0.3574	0.065*	0.50
H10B	0.6726	0.7650	0.2278	0.065*	0.50

	U11	U22	U33	U12	U13	U23
Ni1	0.0290 (2)	0.0330 (2)	0.0378 (3)	0.000	0.00299 (18)	0.000
N1	0.0405 (12)	0.0549 (14)	0.0778 (16)	−0.0030 (10)	0.0128 (12)	−0.0225 (12)
O1	0.0373 (9)	0.0355 (9)	0.0597 (11)	−0.0010 (7)	0.0046 (8)	−0.0087 (8)
O2	0.0454 (11)	0.0488 (11)	0.0864 (14)	−0.0098 (9)	0.0128 (10)	−0.0104 (10)
O3	0.0477 (14)	0.0425 (13)	0.0530 (15)	0.000	−0.0102 (12)	0.000
C1	0.0427 (15)	0.0547 (17)	0.0660 (18)	0.0056 (13)	0.0070 (13)	−0.0214 (14)
C2	0.0498 (15)	0.0426 (14)	0.0428 (14)	0.0031 (12)	0.0001 (12)	−0.0074 (11)
C3	0.0437 (14)	0.0385 (13)	0.0386 (13)	0.0008 (11)	−0.0034 (11)	−0.0022 (10)
C4	0.0468 (15)	0.0422 (14)	0.0492 (15)	−0.0034 (11)	0.0006 (12)	−0.0051 (11)
C5	0.0609 (18)	0.0424 (15)	0.073 (2)	−0.0111 (13)	0.0024 (15)	−0.0039 (13)
C6	0.081 (2)	0.0335 (14)	0.088 (2)	0.0001 (15)	0.0074 (19)	−0.0114 (14)
C7	0.0620 (18)	0.0454 (15)	0.0703 (19)	0.0081 (14)	0.0064 (15)	−0.0127 (14)
C8	0.0517 (17)	0.075 (2)	0.0676 (19)	−0.0234 (15)	0.0137 (15)	−0.0146 (16)
C9	0.035 (3)	0.051 (3)	0.056 (4)	0.005 (2)	0.000 (3)	−0.012 (3)
C10	0.036 (3)	0.062 (4)	0.065 (4)	−0.001 (3)	0.011 (3)	0.010 (3)

Ni1—O1	1.9364 (16)	C5—C6	1.393 (4)
Ni1—O1i	1.9364 (16)	C5—H5	0.9300
Ni1—N1i	1.956 (2)	C6—C7	1.353 (4)
Ni1—N1	1.956 (2)	C6—H6	0.9300
Ni1—O3	2.363 (2)	C7—H7	0.9300
N1—C1	1.280 (3)	C8—H8A	0.9600
N1—C9	1.479 (7)	C8—H8B	0.9600
N1—C10i	1.535 (7)	C8—H8C	0.9600
O1—C3	1.310 (3)	C9—C10i	0.803 (7)
O2—C4	1.369 (3)	C9—C10	1.525 (7)
O2—C8	1.419 (3)	C9—C9i	1.541 (13)
O3—H3	0.8501	C9—H9A	0.9700
C1—C2	1.431 (4)	C9—H9B	0.9700
C1—H1	0.9300	C10—C9i	0.803 (7)
C2—C3	1.414 (3)	C10—C10i	1.092 (13)
C2—C7	1.416 (4)	C10—N1i	1.535 (7)
C3—C4	1.428 (3)	C10—H10A	0.9700
C4—C5	1.377 (4)	C10—H10B	0.9700
O1—Ni1—O1i	90.74 (10)	C6—C7—H7	119.3
O1—Ni1—N1i	167.34 (9)	C2—C7—H7	119.3
O1i—Ni1—N1i	92.11 (8)	O2—C8—H8A	109.5
O1—Ni1—N1	92.11 (8)	O2—C8—H8B	109.5
O1i—Ni1—N1	167.34 (9)	H8A—C8—H8B	109.5
N1i—Ni1—N1	82.55 (14)	O2—C8—H8C	109.5
O1—Ni1—O3	97.90 (7)	H8A—C8—H8C	109.5
O1i—Ni1—O3	97.90 (7)	H8B—C8—H8C	109.5
N1i—Ni1—O3	93.93 (9)	C10i—C9—N1	78.4 (8)
N1—Ni1—O3	93.93 (9)	C10i—C9—C10	43.4 (8)
C1—N1—C9	118.9 (3)	N1—C9—C10	98.4 (5)
C1—N1—C10i	120.1 (3)	C10i—C9—C9i	73.8 (8)
C9—N1—C10i	30.8 (3)	N1—C9—C9i	110.6 (3)
C1—N1—Ni1	127.10 (19)	C10—C9—C9i	30.4 (3)
C9—N1—Ni1	112.9 (3)	C10i—C9—H9A	85.1
C10i—N1—Ni1	109.6 (3)	N1—C9—H9A	112.6
C3—O1—Ni1	126.86 (15)	C10—C9—H9A	112.2
C4—O2—C8	118.0 (2)	C9i—C9—H9A	126.2
Ni1—O3—H3	118.8	C10i—C9—H9B	155.4
N1—C1—C2	125.7 (2)	N1—C9—H9B	111.5
N1—C1—H1	117.2	C10—C9—H9B	112.0
C2—C1—H1	117.2	C9i—C9—H9B	81.6
C3—C2—C7	120.3 (2)	H9A—C9—H9B	109.8
C3—C2—C1	122.4 (2)	C9i—C10—C10i	106.2 (8)
C7—C2—C1	117.2 (2)	C9i—C10—C9	75.9 (9)
O1—C3—C2	125.5 (2)	C10i—C10—C9	30.4 (3)
O1—C3—C4	118.1 (2)	C9i—C10—N1i	70.7 (8)
C2—C3—C4	116.3 (2)	C10i—C10—N1i	119.0 (3)
O2—C4—C5	124.3 (2)	C9—C10—N1i	108.4 (5)
O2—C4—C3	113.9 (2)	C9i—C10—H10A	65.1
C5—C4—C3	121.7 (3)	C10i—C10—H10A	124.0
C4—C5—C6	120.5 (3)	C9—C10—H10A	110.1
C4—C5—H5	119.8	N1i—C10—H10A	109.8
C6—C5—H5	119.8	C9i—C10—H10B	172.9
C7—C6—C5	119.7 (3)	C10i—C10—H10B	79.6
C7—C6—H6	120.1	C9—C10—H10B	109.9
C5—C6—H6	120.1	N1i—C10—H10B	110.4
C6—C7—C2	121.4 (3)	H10A—C10—H10B	108.4
O1—Ni1—N1—C1	4.5 (3)	C8—O2—C4—C5	−5.1 (4)
O1i—Ni1—N1—C1	−98.3 (4)	C8—O2—C4—C3	175.3 (2)
N1i—Ni1—N1—C1	−163.9 (2)	O1—C3—C4—O2	2.0 (3)
O3—Ni1—N1—C1	102.6 (3)	C2—C3—C4—O2	−178.5 (2)
O1—Ni1—N1—C9	−162.9 (3)	O1—C3—C4—C5	−177.7 (2)
O1i—Ni1—N1—C9	94.2 (5)	C2—C3—C4—C5	1.8 (4)
N1i—Ni1—N1—C9	28.6 (4)	O2—C4—C5—C6	179.1 (3)
O3—Ni1—N1—C9	−64.8 (3)	C3—C4—C5—C6	−1.3 (4)
O1—Ni1—N1—C10i	164.1 (3)	C4—C5—C6—C7	0.3 (5)
O1i—Ni1—N1—C10i	61.3 (5)	C5—C6—C7—C2	0.1 (5)
N1i—Ni1—N1—C10i	−4.3 (3)	C3—C2—C7—C6	0.5 (5)
O3—Ni1—N1—C10i	−97.8 (3)	C1—C2—C7—C6	179.6 (3)
O1i—Ni1—O1—C3	162.41 (15)	C1—N1—C9—C10i	101.3 (8)
N1i—Ni1—O1—C3	59.4 (4)	Ni1—N1—C9—C10i	−90.2 (8)
N1—Ni1—O1—C3	−5.2 (2)	C1—N1—C9—C10	140.0 (4)
O3—Ni1—O1—C3	−99.51 (19)	C10i—N1—C9—C10	38.8 (7)
C9—N1—C1—C2	163.8 (4)	Ni1—N1—C9—C10	−51.4 (4)
C10i—N1—C1—C2	−160.6 (4)	C1—N1—C9—C9i	168.8 (2)
Ni1—N1—C1—C2	−2.9 (5)	C10i—N1—C9—C9i	67.6 (8)
N1—C1—C2—C3	0.2 (5)	Ni1—N1—C9—C9i	−22.6 (3)
N1—C1—C2—C7	−178.9 (3)	C10i—C9—C10—C9i	180.000 (4)
Ni1—O1—C3—C2	4.5 (3)	N1—C9—C10—C9i	116.8 (6)
Ni1—O1—C3—C4	−176.08 (17)	N1—C9—C10—C10i	−63.2 (6)
C7—C2—C3—O1	178.0 (3)	C9i—C9—C10—C10i	180.000 (10)
C1—C2—C3—O1	−1.0 (4)	C10i—C9—C10—N1i	116.3 (6)
C7—C2—C3—C4	−1.4 (4)	N1—C9—C10—N1i	53.1 (4)
C1—C2—C3—C4	179.5 (2)	C9i—C9—C10—N1i	−63.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ii	0.85	2.29	3.007 (3)	142
O3—H3···O2ii	0.85	2.18	2.9313 (19)	147
C10—H10B···O1iii	0.97	2.53	3.236 (7)	130
C9—H9B···O3ii	0.97	2.66	3.322 (7)	126

Ni1—O1	1.9364 (16)
Ni1—N1	1.956 (2)
Ni1—O3	2.363 (2)

O1—Ni1—O1i	90.74 (10)
O1—Ni1—N1i	167.34 (9)
O1—Ni1—N1	92.11 (8)
N1i—Ni1—N1	82.55 (14)
O1—Ni1—O3	97.90 (7)
N1—Ni1—O3	93.93 (9)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ii	0.85	2.29	3.007 (3)	142
O3—H3⋯O2ii	0.85	2.18	2.9313 (19)	147
C10—H10B⋯O1iii	0.97	2.53	3.236 (7)	130
C9—H9B⋯O3ii	0.97	2.66	3.322 (7)	126

Symmetry codes: (ii) ; (iii) .