{6,6'-Dieth-oxy-2,2'-[ethyl-enebis(nitrilo-methyl-idyne)]diphenolato}nickel(II) monohydrate.

In the title compound, [Ni(C(20)H(22)N(2)O(4))]·H(2)O, the Ni(II) ion and the water mol-ecule are located on a twofold rotation axis. The Ni ion is coordinated by two N [Ni-N = 1.8462 (18) Å] and two O [Ni-O = 1.8645 (14) Å] atoms in a distorted square-planar geometry. The water mol-ecule and the Ni complex mol-ecule are paired via O-H⋯O hydrogen bonds.

Related literature

For details of the synthesis, see Mohanta et al. (2002 ▶). For a related crystal structure, see Yu (2006 ▶). For general background, see: Ghosh et al. (2006 ▶); Samanta et al. (2007 ▶); Singh et al. (2007 ▶); Yu et al. (2007 ▶).

Experimental

Crystal data

[Ni(C20H22N2O4)]·H2O

M = 431.12

Orthorhombic,

a = 12.8401 (8) Å

b = 19.6133 (12) Å

c = 7.5853 (5) Å

V = 1910.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.05 mm−1

T = 273 (2) K

0.15 × 0.13 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.858, T max = 0.893

8741 measured reflections

1676 independent reflections

1381 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.072

S = 1.04

1676 reflections

129 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 1998 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039822/cv2487sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039822/cv2487Isup2.hkl

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

[Ni(C20H22N2O4)]·H2O	F000 = 904
Mr = 431.12	Dx = 1.499 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -p 2n 2ab	Cell parameters from 2990 reflections
a = 12.8401 (8) Å	θ = 3.2–26.5º
b = 19.6133 (12) Å	µ = 1.05 mm−1
c = 7.5853 (5) Å	T = 273 (2) K
V = 1910.3 (2) Å3	Block, red-brown
Z = 4	0.15 × 0.13 × 0.11 mm

Bruker APEXII CCD area-detector diffractometer	1676 independent reflections
Radiation source: fine-focus sealed tube	1381 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −15→14
Tmin = 0.858, Tmax = 0.893	k = −16→23
8741 measured reflections	l = −8→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0307P)2 + 0.9816P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1676 reflections	Δρmax = 0.33 e Å−3
129 parameters	Δρmin = −0.41 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Ni1	0.5000	0.023585 (17)	0.2500	0.03740 (14)
O1	0.41162 (10)	0.09308 (7)	0.17417 (19)	0.0406 (3)
O2	0.32670 (11)	0.20336 (7)	0.03750 (19)	0.0454 (4)
O3	0.5000	0.23474 (14)	0.2500	0.1240 (15)
H3A	0.4599	0.2100	0.1962	0.149*
N1	0.58936 (15)	−0.04538 (8)	0.3175 (2)	0.0457 (5)
C1	0.54450 (19)	−0.11475 (10)	0.3139 (3)	0.0565 (6)
H1A	0.5201	−0.1274	0.4305	0.068*
H1B	0.5969	−0.1474	0.2773	0.068*
C2	0.6841 (2)	−0.03851 (12)	0.3700 (3)	0.0546 (6)
H2	0.7227	−0.0782	0.3842	0.066*
C3	0.31834 (15)	0.08654 (10)	0.1050 (3)	0.0398 (5)
C4	0.26463 (18)	0.02419 (11)	0.0914 (3)	0.0495 (6)
C5	0.1623 (2)	0.02214 (15)	0.0224 (4)	0.0684 (8)
H5	0.1269	−0.0192	0.0171	0.082*
C6	0.1152 (2)	0.07964 (15)	−0.0361 (4)	0.0709 (8)
H6	0.0474	0.0777	−0.0789	0.085*
C7	0.16808 (17)	0.14183 (13)	−0.0323 (3)	0.0550 (6)
H7	0.1361	0.1811	−0.0748	0.066*
C8	0.26779 (16)	0.14498 (11)	0.0345 (3)	0.0427 (5)
C9	0.28968 (19)	0.26143 (11)	−0.0578 (3)	0.0535 (6)
H9A	0.2273	0.2793	−0.0024	0.064*
H9B	0.2727	0.2486	−0.1780	0.064*
C10	0.3732 (2)	0.31410 (12)	−0.0576 (4)	0.0677 (7)
H10A	0.3886	0.3270	0.0616	0.102*
H10B	0.3500	0.3534	−0.1223	0.102*
H10C	0.4347	0.2959	−0.1120	0.102*

	U11	U22	U33	U12	U13	U23
Ni1	0.0425 (2)	0.0303 (2)	0.0394 (2)	0.000	0.01083 (17)	0.000
O1	0.0376 (8)	0.0359 (7)	0.0481 (8)	−0.0025 (6)	0.0007 (7)	−0.0011 (6)
O2	0.0452 (8)	0.0416 (8)	0.0493 (9)	0.0033 (7)	−0.0080 (7)	0.0010 (7)
O3	0.132 (3)	0.0510 (17)	0.189 (4)	0.000	−0.113 (3)	0.000
N1	0.0557 (12)	0.0352 (9)	0.0464 (10)	0.0072 (9)	0.0186 (9)	0.0028 (8)
C1	0.0755 (17)	0.0324 (11)	0.0617 (16)	0.0066 (11)	0.0279 (12)	0.0043 (10)
C2	0.0599 (16)	0.0458 (14)	0.0581 (15)	0.0219 (12)	0.0157 (12)	0.0051 (11)
C3	0.0369 (11)	0.0475 (12)	0.0350 (11)	−0.0042 (9)	0.0075 (9)	−0.0053 (9)
C4	0.0469 (13)	0.0523 (13)	0.0492 (13)	−0.0144 (11)	0.0076 (11)	−0.0052 (11)
C5	0.0511 (15)	0.0715 (18)	0.082 (2)	−0.0239 (13)	0.0014 (14)	−0.0063 (15)
C6	0.0411 (14)	0.092 (2)	0.0792 (19)	−0.0118 (14)	−0.0080 (13)	−0.0123 (17)
C7	0.0427 (13)	0.0687 (16)	0.0538 (14)	0.0038 (12)	−0.0028 (11)	−0.0060 (12)
C8	0.0392 (12)	0.0522 (13)	0.0367 (11)	−0.0006 (10)	0.0034 (9)	−0.0073 (10)
C9	0.0616 (15)	0.0533 (14)	0.0455 (13)	0.0159 (12)	−0.0076 (11)	−0.0005 (11)
C10	0.0848 (19)	0.0510 (14)	0.0673 (17)	0.0039 (14)	−0.0112 (15)	0.0131 (13)

Ni1—N1i	1.8462 (18)	C3—C8	1.422 (3)
Ni1—N1	1.8462 (18)	C4—C5	1.415 (3)
Ni1—O1i	1.8645 (14)	C4—C2i	1.426 (3)
Ni1—O1	1.8645 (14)	C5—C6	1.354 (4)
O1—C3	1.314 (2)	C5—H5	0.9300
O2—C8	1.372 (2)	C6—C7	1.396 (3)
O2—C9	1.431 (2)	C6—H6	0.9300
O3—H3A	0.8168	C7—C8	1.378 (3)
N1—C2	1.287 (3)	C7—H7	0.9300
N1—C1	1.478 (3)	C9—C10	1.489 (3)
C1—C1i	1.498 (5)	C9—H9A	0.9700
C1—H1A	0.9700	C9—H9B	0.9700
C1—H1B	0.9700	C10—H10A	0.9600
C2—C4i	1.426 (3)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.408 (3)
N1i—Ni1—N1	85.77 (12)	C5—C4—C2i	118.7 (2)
N1i—Ni1—O1i	178.06 (7)	C6—C5—C4	120.8 (2)
N1—Ni1—O1i	94.12 (7)	C6—C5—H5	119.6
N1i—Ni1—O1	94.12 (7)	C4—C5—H5	119.6
N1—Ni1—O1	178.06 (7)	C5—C6—C7	120.2 (2)
O1i—Ni1—O1	86.06 (8)	C5—C6—H6	119.9
C3—O1—Ni1	127.35 (13)	C7—C6—H6	119.9
C8—O2—C9	118.21 (16)	C8—C7—C6	119.9 (2)
C2—N1—C1	118.07 (19)	C8—C7—H7	120.1
C2—N1—Ni1	126.62 (16)	C6—C7—H7	120.1
C1—N1—Ni1	115.29 (16)	O2—C8—C7	123.7 (2)
N1—C1—C1i	108.01 (14)	O2—C8—C3	114.51 (17)
N1—C1—H1A	110.1	C7—C8—C3	121.8 (2)
C1i—C1—H1A	110.1	O2—C9—C10	108.22 (18)
N1—C1—H1B	110.1	O2—C9—H9A	110.1
C1i—C1—H1B	110.1	C10—C9—H9A	110.1
H1A—C1—H1B	108.4	O2—C9—H9B	110.1
N1—C2—C4i	126.2 (2)	C10—C9—H9B	110.1
N1—C2—H2	116.9	H9A—C9—H9B	108.4
C4i—C2—H2	116.9	C9—C10—H10A	109.5
O1—C3—C4	124.1 (2)	C9—C10—H10B	109.5
O1—C3—C8	119.19 (18)	H10A—C10—H10B	109.5
C4—C3—C8	116.69 (19)	C9—C10—H10C	109.5
C3—C4—C5	120.4 (2)	H10A—C10—H10C	109.5
C3—C4—C2i	120.5 (2)	H10B—C10—H10C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.82	2.38	3.056 (3)	140
O3—H3A···O2	0.82	2.10	2.8158 (15)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	2.10	2.8158 (15)	147