{2,2'-[o-Phenyl-enebis(nitrilo-methanylyl-idene)]diphenolato-κO,N,N',O'}nickel(II) monohydrate.

The Ni(II) atom in the title monohydrate, [Ni(C(20)H(14)N(2)O(2))]·H(2)O, is coordinated within a cis-N(2)O(2) square-planar donor set provided by the tetra-dentate Schiff base ligand. Overall, the mol-ecule has a curved shape with the dihedral angle formed between the planes of the outer benzene rings being 13.92 (18)°. The water mol-ecule was found to be disordered over two positions [ratio 0.80 (1):0.20 (1)] and the major component is linked to the complex via an O-H⋯O hydrogen bond.

Related literature

For background to the catalytic potential of transition metal Schiff base complexes, see: Gupta & Sutar (2008) ▶. For the structure of the unsolvated form of the title complex. see: Radha et al. (1985 ▶); Wang et al. (2003 ▶). For our recent work in this area, see: Ghaemi et al. (2011 ▶).

Experimental

Crystal data

[Ni(C20H14N2O2)]·H2O

M = 391.06

Trigonal,

a = 31.5519 (13) Å

c = 9.0255 (6) Å

V = 7781.3 (6) Å3

Z = 18

Mo Kα radiation

μ = 1.14 mm−1

T = 294 K

0.30 × 0.15 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.732, T max = 1.0

13452 measured reflections

3897 independent reflections

2850 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.04

3897 reflections

251 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039730/hb6421sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039730/hb6421Isup2.hkl

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

[Ni(C20H14N2O2)]·H2O	Dx = 1.502 Mg m−3
Mr = 391.06	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 4020 reflections
Hall symbol: -R 3	θ = 2.2–29.2°
a = 31.5519 (13) Å	µ = 1.14 mm−1
c = 9.0255 (6) Å	T = 294 K
V = 7781.3 (6) Å3	Block, dark-brown
Z = 18	0.30 × 0.15 × 0.15 mm
F(000) = 3636

Agilent SuperNova Dual diffractometer with an Atlas detector	3897 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2850 reflections with I > 2σ(I)
Mirror	Rint = 0.036
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω scans	h = −40→39
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −30→40
Tmin = 0.732, Tmax = 1.0	l = −11→11
13452 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0632P)2 + 2.9091P] where P = (Fo2 + 2Fc2)/3
3897 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.52 e Å−3
3 restraints	Δρmin = −0.43 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)
Ni	0.517165 (12)	0.069858 (12)	0.75915 (3)	0.04310 (14)
O1	0.46763 (7)	0.05129 (7)	0.9031 (2)	0.0534 (5)
O2	0.53199 (8)	0.13507 (8)	0.7881 (2)	0.0663 (6)
O1W	0.49982 (18)	0.12723 (16)	1.1173 (4)	0.0839 (16)	0.799 (10)
O1W'	0.5396 (7)	0.1609 (5)	1.128 (2)	0.081 (6)	0.201 (10)
H1	0.4901 (17)	0.1108 (15)	1.040 (3)	0.122*
H2	0.5295 (9)	0.149 (2)	1.109 (7)	0.122*
N1	0.50665 (8)	0.00460 (8)	0.7325 (2)	0.0433 (5)
N2	0.56480 (8)	0.08656 (8)	0.6025 (2)	0.0461 (5)
C1	0.43849 (9)	0.00727 (10)	0.9530 (3)	0.0442 (6)
C2	0.40283 (10)	0.00071 (12)	1.0577 (3)	0.0518 (7)
H2A	0.4003	0.0276	1.0871	0.062*
C3	0.37181 (10)	−0.04400 (12)	1.1177 (3)	0.0558 (7)
H3	0.3485	−0.0471	1.1865	0.067*
C4	0.37476 (11)	−0.08475 (12)	1.0770 (3)	0.0594 (8)
H4	0.3539	−0.1151	1.1191	0.071*
C5	0.40858 (10)	−0.07978 (12)	0.9743 (3)	0.0559 (7)
H5	0.4104	−0.1072	0.9465	0.067*
C6	0.44089 (10)	−0.03438 (10)	0.9090 (3)	0.0454 (6)
C7	0.47473 (10)	−0.03337 (10)	0.8036 (3)	0.0457 (6)
H7	0.4738	−0.0628	0.7842	0.055*
C8	0.53948 (9)	0.00265 (10)	0.6283 (3)	0.0440 (6)
C9	0.54204 (11)	−0.03870 (11)	0.5953 (3)	0.0523 (7)
H9	0.5209	−0.0685	0.6403	0.063*
C10	0.57666 (12)	−0.03518 (13)	0.4942 (3)	0.0616 (8)
H10	0.5784	−0.0630	0.4704	0.074*
C11	0.60844 (11)	0.00867 (13)	0.4287 (3)	0.0598 (8)
H11	0.6317	0.0105	0.3617	0.072*
C12	0.60606 (10)	0.04971 (12)	0.4617 (3)	0.0547 (7)
H12	0.6279	0.0795	0.4183	0.066*
C13	0.57083 (9)	0.04682 (11)	0.5604 (3)	0.0446 (6)
C14	0.58649 (11)	0.12823 (12)	0.5356 (3)	0.0573 (7)
H14	0.6062	0.1312	0.4551	0.069*
C15	0.58292 (11)	0.16991 (11)	0.5738 (3)	0.0585 (7)
C16	0.60823 (15)	0.21219 (14)	0.4862 (4)	0.0843 (11)
H16	0.6253	0.2110	0.4038	0.101*
C17	0.60896 (16)	0.25426 (14)	0.5161 (5)	0.0889 (11)
H17	0.6255	0.2813	0.4543	0.107*
C18	0.58475 (14)	0.25664 (13)	0.6400 (5)	0.0827 (11)
H18	0.5858	0.2858	0.6635	0.099*
C19	0.55925 (13)	0.21665 (13)	0.7291 (5)	0.0774 (10)
H19	0.5428	0.2191	0.8112	0.093*
C20	0.55721 (11)	0.17190 (11)	0.6999 (3)	0.0571 (7)

	U11	U22	U33	U12	U13	U23
Ni	0.0432 (2)	0.0485 (2)	0.0423 (2)	0.02653 (17)	0.00544 (14)	0.00408 (14)
O1	0.0591 (12)	0.0557 (12)	0.0528 (10)	0.0342 (10)	0.0125 (9)	0.0075 (9)
O2	0.0752 (15)	0.0579 (13)	0.0735 (13)	0.0390 (12)	0.0244 (11)	0.0102 (11)
O1W	0.104 (4)	0.077 (3)	0.073 (2)	0.047 (3)	0.0052 (19)	−0.0180 (17)
O1W'	0.085 (12)	0.046 (9)	0.123 (11)	0.041 (9)	0.002 (8)	−0.005 (7)
N1	0.0423 (12)	0.0541 (13)	0.0354 (10)	0.0255 (11)	−0.0041 (9)	−0.0004 (9)
N2	0.0407 (12)	0.0571 (14)	0.0417 (10)	0.0252 (11)	−0.0020 (9)	0.0009 (10)
C1	0.0427 (14)	0.0569 (16)	0.0363 (12)	0.0274 (13)	−0.0026 (11)	0.0060 (11)
C2	0.0486 (16)	0.0707 (19)	0.0419 (13)	0.0341 (15)	0.0008 (12)	0.0025 (13)
C3	0.0446 (15)	0.080 (2)	0.0409 (13)	0.0293 (16)	0.0013 (12)	0.0049 (14)
C4	0.0476 (16)	0.0648 (19)	0.0514 (15)	0.0172 (15)	0.0003 (13)	0.0110 (14)
C5	0.0515 (17)	0.0613 (18)	0.0531 (15)	0.0270 (15)	−0.0010 (13)	0.0019 (14)
C6	0.0429 (14)	0.0567 (16)	0.0391 (12)	0.0267 (13)	−0.0028 (11)	0.0027 (12)
C7	0.0473 (15)	0.0508 (15)	0.0419 (12)	0.0266 (13)	−0.0053 (12)	−0.0019 (12)
C8	0.0400 (14)	0.0608 (17)	0.0354 (12)	0.0284 (13)	−0.0068 (10)	−0.0063 (12)
C9	0.0538 (16)	0.0594 (18)	0.0474 (14)	0.0311 (15)	−0.0048 (13)	−0.0087 (13)
C10	0.066 (2)	0.076 (2)	0.0523 (16)	0.0428 (18)	−0.0050 (15)	−0.0175 (16)
C11	0.0526 (17)	0.084 (2)	0.0502 (15)	0.0399 (17)	0.0007 (13)	−0.0127 (15)
C12	0.0471 (16)	0.0686 (19)	0.0464 (14)	0.0274 (15)	0.0010 (12)	−0.0033 (14)
C13	0.0387 (14)	0.0627 (17)	0.0344 (11)	0.0269 (13)	−0.0063 (11)	−0.0053 (12)
C14	0.0477 (16)	0.066 (2)	0.0518 (15)	0.0237 (15)	0.0072 (13)	0.0060 (14)
C15	0.0519 (17)	0.0570 (18)	0.0622 (17)	0.0239 (15)	0.0021 (14)	0.0096 (14)
C16	0.088 (3)	0.072 (2)	0.085 (2)	0.034 (2)	0.020 (2)	0.021 (2)
C17	0.091 (3)	0.060 (2)	0.103 (3)	0.029 (2)	0.015 (2)	0.022 (2)
C18	0.079 (2)	0.054 (2)	0.115 (3)	0.0332 (19)	0.005 (2)	0.010 (2)
C19	0.068 (2)	0.059 (2)	0.108 (3)	0.0333 (18)	0.014 (2)	0.007 (2)
C20	0.0512 (17)	0.0544 (18)	0.0683 (18)	0.0283 (15)	0.0026 (14)	0.0082 (15)

Ni—O1	1.8865 (18)	C6—C7	1.419 (4)
Ni—O2	1.886 (2)	C7—H7	0.9300
Ni—N1	1.930 (2)	C8—C9	1.379 (4)
Ni—N2	1.935 (2)	C8—C13	1.385 (4)
O1—C1	1.304 (3)	C9—C10	1.385 (4)
O2—C20	1.301 (3)	C9—H9	0.9300
O1W—O1W'	1.175 (15)	C10—C11	1.372 (5)
O1W—H1	0.829 (10)	C10—H10	0.9300
O1W—H2	0.841 (10)	C11—C12	1.367 (4)
O1W'—H2	0.39 (4)	C11—H11	0.9300
N1—C7	1.286 (3)	C12—C13	1.391 (4)
N1—C8	1.423 (3)	C12—H12	0.9300
N2—C14	1.289 (4)	C14—C15	1.417 (4)
N2—C13	1.411 (3)	C14—H14	0.9300
C1—C2	1.403 (4)	C15—C16	1.406 (5)
C1—C6	1.410 (4)	C15—C20	1.417 (4)
C2—C3	1.364 (4)	C16—C17	1.343 (5)
C2—H2A	0.9300	C16—H16	0.9300
C3—C4	1.384 (4)	C17—C18	1.378 (6)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.362 (4)	C18—C19	1.368 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.407 (4)	C19—C20	1.406 (4)
C5—H5	0.9300	C19—H19	0.9300
O2—Ni—O1	87.61 (9)	C9—C8—C13	120.4 (2)
O2—Ni—N1	176.06 (9)	C9—C8—N1	124.8 (3)
O1—Ni—N1	94.63 (9)	C13—C8—N1	114.7 (2)
O2—Ni—N2	93.96 (9)	C8—C9—C10	118.9 (3)
O1—Ni—N2	176.40 (9)	C8—C9—H9	120.6
N1—Ni—N2	83.98 (9)	C10—C9—H9	120.6
C1—O1—Ni	127.01 (17)	C11—C10—C9	121.0 (3)
C20—O2—Ni	126.63 (19)	C11—C10—H10	119.5
O1W'—O1W—H1	122 (4)	C9—C10—H10	119.5
O1W'—O1W—H2	12 (4)	C12—C11—C10	120.2 (3)
H1—O1W—H2	110.1 (18)	C12—C11—H11	119.9
O1W—O1W'—H2	27 (8)	C10—C11—H11	119.9
C7—N1—C8	122.5 (2)	C11—C12—C13	119.9 (3)
C7—N1—Ni	124.63 (18)	C11—C12—H12	120.1
C8—N1—Ni	112.83 (17)	C13—C12—H12	120.1
C14—N2—C13	122.8 (2)	C8—C13—C12	119.6 (3)
C14—N2—Ni	124.3 (2)	C8—C13—N2	115.4 (2)
C13—N2—Ni	112.72 (17)	C12—C13—N2	124.9 (3)
O1—C1—C2	118.4 (3)	N2—C14—C15	125.8 (3)
O1—C1—C6	123.9 (2)	N2—C14—H14	117.1
C2—C1—C6	117.7 (3)	C15—C14—H14	117.1
C3—C2—C1	121.8 (3)	C16—C15—C20	118.4 (3)
C3—C2—H2A	119.1	C16—C15—C14	118.2 (3)
C1—C2—H2A	119.1	C20—C15—C14	123.3 (3)
C2—C3—C4	120.6 (3)	C17—C16—C15	123.1 (4)
C2—C3—H3	119.7	C17—C16—H16	118.5
C4—C3—H3	119.7	C15—C16—H16	118.5
C5—C4—C3	119.1 (3)	C16—C17—C18	118.7 (4)
C5—C4—H4	120.5	C16—C17—H17	120.6
C3—C4—H4	120.5	C18—C17—H17	120.6
C4—C5—C6	122.0 (3)	C19—C18—C17	120.9 (4)
C4—C5—H5	119.0	C19—C18—H18	119.5
C6—C5—H5	119.0	C17—C18—H18	119.5
C5—C6—C1	118.8 (2)	C18—C19—C20	121.8 (4)
C5—C6—C7	117.3 (3)	C18—C19—H19	119.1
C1—C6—C7	123.9 (3)	C20—C19—H19	119.1
N1—C7—C6	125.8 (3)	O2—C20—C19	118.9 (3)
N1—C7—H7	117.1	O2—C20—C15	124.1 (3)
C6—C7—H7	117.1	C19—C20—C15	117.1 (3)
O2—Ni—O1—C1	−178.2 (2)	Ni—N1—C8—C9	175.7 (2)
N1—Ni—O1—C1	−1.4 (2)	C7—N1—C8—C13	179.0 (2)
N2—Ni—O1—C1	65.8 (15)	Ni—N1—C8—C13	−3.1 (3)
O1—Ni—O2—C20	−162.7 (3)	C13—C8—C9—C10	0.4 (4)
N1—Ni—O2—C20	72.5 (13)	N1—C8—C9—C10	−178.3 (2)
N2—Ni—O2—C20	14.1 (3)	C8—C9—C10—C11	0.8 (4)
O2—Ni—N1—C7	123.7 (12)	C9—C10—C11—C12	−0.6 (4)
O1—Ni—N1—C7	−0.9 (2)	C10—C11—C12—C13	−0.9 (4)
N2—Ni—N1—C7	−177.6 (2)	C9—C8—C13—C12	−1.9 (4)
O2—Ni—N1—C8	−54.1 (13)	N1—C8—C13—C12	177.0 (2)
O1—Ni—N1—C8	−178.72 (16)	C9—C8—C13—N2	179.9 (2)
N2—Ni—N1—C8	4.61 (16)	N1—C8—C13—N2	−1.2 (3)
O2—Ni—N2—C14	−13.2 (2)	C11—C12—C13—C8	2.2 (4)
O1—Ni—N2—C14	102.7 (14)	C11—C12—C13—N2	−179.8 (2)
N1—Ni—N2—C14	170.2 (2)	C14—N2—C13—C8	−170.6 (2)
O2—Ni—N2—C13	171.37 (17)	Ni—N2—C13—C8	5.0 (3)
O1—Ni—N2—C13	−72.8 (14)	C14—N2—C13—C12	11.3 (4)
N1—Ni—N2—C13	−5.26 (16)	Ni—N2—C13—C12	−173.1 (2)
Ni—O1—C1—C2	−178.18 (17)	C13—N2—C14—C15	−178.6 (3)
Ni—O1—C1—C6	2.5 (4)	Ni—N2—C14—C15	6.4 (4)
O1—C1—C2—C3	−178.4 (2)	N2—C14—C15—C16	−178.5 (3)
C6—C1—C2—C3	1.0 (4)	N2—C14—C15—C20	4.8 (5)
C1—C2—C3—C4	0.3 (4)	C20—C15—C16—C17	−0.4 (6)
C2—C3—C4—C5	−1.0 (4)	C14—C15—C16—C17	−177.2 (4)
C3—C4—C5—C6	0.5 (4)	C15—C16—C17—C18	1.5 (6)
C4—C5—C6—C1	0.8 (4)	C16—C17—C18—C19	−1.8 (7)
C4—C5—C6—C7	179.8 (3)	C17—C18—C19—C20	1.0 (6)
O1—C1—C6—C5	177.8 (2)	Ni—O2—C20—C19	171.7 (2)
C2—C1—C6—C5	−1.5 (4)	Ni—O2—C20—C15	−7.9 (4)
O1—C1—C6—C7	−1.1 (4)	C18—C19—C20—O2	−179.4 (3)
C2—C1—C6—C7	179.5 (2)	C18—C19—C20—C15	0.2 (5)
C8—N1—C7—C6	179.9 (2)	C16—C15—C20—O2	179.1 (3)
Ni—N1—C7—C6	2.3 (4)	C14—C15—C20—O2	−4.2 (5)
C5—C6—C7—N1	179.6 (2)	C16—C15—C20—C19	−0.5 (5)
C1—C6—C7—N1	−1.5 (4)	C14—C15—C20—C19	176.2 (3)
C7—N1—C8—C9	−2.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1···O1	0.83 (1)	2.06 (2)	2.842 (4)	158 (5)

Table 1

Selected bond lengths (Å)

Ni—O1	1.8865 (18)
Ni—O2	1.886 (2)
Ni—N1	1.930 (2)
Ni—N2	1.935 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1⋯O1	0.83 (1)	2.06 (2)	2.842 (4)	158 (5)