Aqua-[2-(2-pyridylmethyl-imino-meth-yl)phenolato]nickel(II) nitrate monohydrate.

In the title compound, [Ni(C(13)H(11)N(2)O)(H(2)O)]NO(3)·H(2)O, the Ni(II) ion is coordinated by one O atom and two N atoms of the Schiff base ligand and the O atom from a water mol-ecule, forming a slightly distorted square-planar geometry. A one-dimensional double-chain structure is formed along [001] by O⋯H-O hydrogen bonds and the Ni⋯O [2.617 (3) Å] inter-actions.

Related literature

For background to Schiff bases in coordination chemistry, see: Boskovic et al. (2003 ▶); Koizumi et al. (2005 ▶); Oshiob et al. (2005 ▶). For Ni—O and Ni—N bond distances in related structures, see: Wang et al. (2007 ▶).

Experimental

Crystal data

[Ni(C13n class="Species">H11N2O)(H2O)]NO3·H2O

M = 367.99

Triclinic,

a = 7.7885 (13) Å

b = 9.0155 (15) Å

c = 11.3285 (19) Å

α = 71.244 (2)°

β = 85.846 (3)°

γ = 86.967 (3)°

V = 750.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.33 mm−1

T = 293 K

0.27 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.716, T max = 0.826

3706 measured reflections

2610 independent reflections

2179 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.04

2610 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT-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: XP.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037027/hg2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037027/hg2552Isup2.hkl

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

[Ni(C13H11N2O)(H2O)]NO3·H2O	Z = 2
Mr = 367.99	F(000) = 380
Triclinic, P1	Dx = 1.628 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7885 (13) Å	Cell parameters from 1525 reflections
b = 9.0155 (15) Å	θ = 2.5–25.8°
c = 11.3285 (19) Å	µ = 1.33 mm−1
α = 71.244 (2)°	T = 293 K
β = 85.846 (3)°	Block, red-brown
γ = 86.967 (3)°	0.27 × 0.21 × 0.15 mm
V = 750.9 (2) Å3

Bruker APEXII CCD area-detector diffractometer	2610 independent reflections
Radiation source: fine-focus sealed tube	2179 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.716, Tmax = 0.826	k = −7→10
3706 measured reflections	l = −13→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.2147P] where P = (Fo2 + 2Fc2)/3
2610 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.26 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
Ni1	0.65546 (5)	0.59075 (4)	0.61677 (3)	0.03862 (14)
O1	0.6180 (3)	0.7356 (2)	0.45717 (19)	0.0534 (5)
O2	0.5125 (3)	0.7279 (2)	0.69276 (19)	0.0502 (5)
H2A	0.4512	0.7909	0.6414	0.060*
H2B	0.5764	0.7774	0.7215	0.060*
O3	1.0146 (3)	0.9237 (3)	0.7257 (3)	0.0827 (8)
O4	0.7495 (3)	0.8666 (3)	0.7775 (2)	0.0646 (6)
O5	0.8974 (3)	0.7562 (3)	0.6573 (3)	0.0743 (7)
O6	0.2993 (3)	0.9471 (2)	0.5530 (2)	0.0651 (6)
H6B	0.2135	0.9322	0.6016	0.078*
H6A	0.3320	1.0375	0.5370	0.078*
N1	0.7643 (3)	0.4328 (3)	0.5523 (2)	0.0427 (6)
N2	0.7069 (3)	0.4333 (3)	0.7799 (2)	0.0455 (6)
N3	0.8871 (4)	0.8476 (3)	0.7206 (2)	0.0550 (7)
C1	0.7858 (4)	0.2991 (3)	0.7729 (3)	0.0437 (7)
C2	0.8364 (4)	0.1813 (4)	0.8778 (3)	0.0586 (9)
H2	0.8902	0.0897	0.8707	0.070*
C3	0.8059 (5)	0.2014 (4)	0.9927 (3)	0.0642 (9)
H3	0.8397	0.1239	1.0646	0.077*
C4	0.7247 (5)	0.3378 (4)	1.0002 (3)	0.0626 (9)
H4	0.7027	0.3534	1.0771	0.075*
C5	0.6771 (4)	0.4494 (4)	0.8938 (3)	0.0583 (8)
H5	0.6215	0.5407	0.8999	0.070*
C6	0.8153 (4)	0.2851 (3)	0.6448 (3)	0.0511 (8)
H6C	0.9361	0.2608	0.6296	0.061*
H6D	0.7483	0.2008	0.6381	0.061*
C7	0.7468 (4)	0.5799 (3)	0.3335 (3)	0.0461 (7)
C8	0.6592 (4)	0.7162 (3)	0.3475 (3)	0.0452 (7)
C9	0.6142 (4)	0.8354 (4)	0.2387 (3)	0.0588 (9)
H9	0.5550	0.9250	0.2453	0.071*
C10	0.6560 (5)	0.8222 (4)	0.1225 (3)	0.0629 (9)
H10	0.6235	0.9025	0.0519	0.075*
C11	0.7465 (5)	0.6902 (4)	0.1084 (3)	0.0643 (9)
H11	0.7764	0.6833	0.0293	0.077*
C12	0.7902 (4)	0.5718 (4)	0.2126 (3)	0.0575 (8)
H12	0.8500	0.4836	0.2037	0.069*
C13	0.7934 (4)	0.4472 (3)	0.4359 (3)	0.0457 (7)
H13	0.8501	0.3636	0.4169	0.055*

	U11	U22	U33	U12	U13	U23
Ni1	0.0453 (2)	0.0280 (2)	0.0426 (2)	0.00371 (14)	0.00055 (15)	−0.01290 (15)
O1	0.0696 (14)	0.0374 (11)	0.0513 (13)	0.0101 (10)	−0.0023 (11)	−0.0135 (10)
O2	0.0555 (12)	0.0402 (11)	0.0564 (13)	0.0045 (9)	−0.0031 (10)	−0.0186 (10)
O3	0.0580 (16)	0.108 (2)	0.097 (2)	−0.0215 (15)	−0.0002 (14)	−0.0517 (18)
O4	0.0579 (14)	0.0783 (17)	0.0680 (15)	−0.0067 (12)	0.0113 (12)	−0.0402 (14)
O5	0.0684 (16)	0.0642 (15)	0.104 (2)	0.0061 (12)	0.0087 (14)	−0.0506 (16)
O6	0.0666 (15)	0.0451 (13)	0.0814 (17)	0.0045 (11)	0.0029 (13)	−0.0196 (12)
N1	0.0493 (14)	0.0332 (12)	0.0459 (14)	0.0027 (10)	−0.0025 (11)	−0.0138 (11)
N2	0.0533 (15)	0.0344 (13)	0.0489 (15)	−0.0009 (11)	−0.0015 (11)	−0.0140 (11)
N3	0.0629 (18)	0.0470 (16)	0.0534 (17)	0.0057 (13)	−0.0081 (14)	−0.0137 (13)
C1	0.0502 (17)	0.0327 (15)	0.0477 (17)	−0.0004 (12)	−0.0062 (14)	−0.0115 (13)
C2	0.077 (2)	0.0391 (17)	0.059 (2)	0.0045 (16)	−0.0157 (17)	−0.0128 (16)
C3	0.089 (3)	0.0478 (19)	0.052 (2)	−0.0025 (18)	−0.0216 (18)	−0.0066 (16)
C4	0.086 (3)	0.056 (2)	0.0450 (19)	−0.0036 (18)	−0.0088 (17)	−0.0147 (17)
C5	0.075 (2)	0.0503 (19)	0.051 (2)	0.0010 (16)	0.0011 (17)	−0.0200 (16)
C6	0.065 (2)	0.0321 (15)	0.0563 (19)	0.0097 (14)	−0.0091 (16)	−0.0153 (14)
C7	0.0525 (18)	0.0422 (17)	0.0462 (17)	−0.0014 (14)	−0.0051 (14)	−0.0174 (14)
C8	0.0491 (17)	0.0373 (16)	0.0490 (18)	−0.0039 (13)	−0.0041 (14)	−0.0126 (14)
C9	0.071 (2)	0.0417 (18)	0.060 (2)	−0.0040 (16)	−0.0066 (17)	−0.0100 (16)
C10	0.082 (2)	0.054 (2)	0.046 (2)	−0.0157 (18)	−0.0108 (17)	−0.0043 (16)
C11	0.082 (3)	0.067 (2)	0.047 (2)	−0.0143 (19)	−0.0020 (17)	−0.0204 (18)
C12	0.064 (2)	0.060 (2)	0.054 (2)	−0.0020 (16)	−0.0017 (16)	−0.0248 (17)
C13	0.0476 (17)	0.0392 (16)	0.0542 (19)	0.0031 (13)	−0.0008 (14)	−0.0215 (14)

Ni1—O1	1.891 (2)	C3—C4	1.377 (5)
Ni1—N1	1.931 (2)	C3—H3	0.9300
Ni1—O2	1.9777 (19)	C4—C5	1.359 (4)
Ni1—N2	1.987 (2)	C4—H4	0.9300
O1—C8	1.324 (3)	C5—H5	0.9300
O2—H2A	0.8290	C6—H6C	0.9700
O2—H2B	0.8324	C6—H6D	0.9700
O3—N3	1.251 (3)	C7—C12	1.411 (4)
O4—N3	1.243 (3)	C7—C8	1.422 (4)
O5—N3	1.251 (3)	C7—C13	1.425 (4)
O6—H6B	0.8225	C8—C9	1.402 (4)
O6—H6A	0.8261	C9—C10	1.374 (5)
N1—C13	1.287 (4)	C9—H9	0.9300
N1—C6	1.462 (4)	C10—C11	1.399 (5)
N2—C5	1.347 (4)	C10—H10	0.9300
N2—C1	1.350 (4)	C11—C12	1.363 (5)
C1—C2	1.381 (4)	C11—H11	0.9300
C1—C6	1.497 (4)	C12—H12	0.9300
C2—C3	1.374 (5)	C13—H13	0.9300
C2—H2	0.9300
O1—Ni1—N1	94.39 (9)	C3—C4—H4	120.3
O1—Ni1—O2	89.12 (8)	N2—C5—C4	122.8 (3)
N1—Ni1—O2	170.48 (9)	N2—C5—H5	118.6
O1—Ni1—N2	176.56 (9)	C4—C5—H5	118.6
N1—Ni1—N2	82.56 (10)	N1—C6—C1	109.4 (2)
O2—Ni1—N2	94.14 (9)	N1—C6—H6C	109.8
C8—O1—Ni1	127.20 (18)	C1—C6—H6C	109.8
Ni1—O2—H2A	111.9	N1—C6—H6D	109.8
Ni1—O2—H2B	109.2	C1—C6—H6D	109.8
H2A—O2—H2B	109.2	H6C—C6—H6D	108.2
H6B—O6—H6A	110.5	C12—C7—C8	119.4 (3)
C13—N1—C6	118.2 (2)	C12—C7—C13	116.9 (3)
C13—N1—Ni1	125.4 (2)	C8—C7—C13	123.6 (3)
C6—N1—Ni1	116.37 (18)	O1—C8—C9	118.8 (3)
C5—N2—C1	117.8 (3)	O1—C8—C7	123.5 (3)
C5—N2—Ni1	127.0 (2)	C9—C8—C7	117.7 (3)
C1—N2—Ni1	115.2 (2)	C10—C9—C8	121.2 (3)
O4—N3—O5	120.7 (3)	C10—C9—H9	119.4
O4—N3—O3	118.9 (3)	C8—C9—H9	119.4
O5—N3—O3	120.4 (3)	C9—C10—C11	121.2 (3)
N2—C1—C2	122.1 (3)	C9—C10—H10	119.4
N2—C1—C6	116.1 (2)	C11—C10—H10	119.4
C2—C1—C6	121.8 (3)	C12—C11—C10	118.8 (3)
C3—C2—C1	119.0 (3)	C12—C11—H11	120.6
C3—C2—H2	120.5	C10—C11—H11	120.6
C1—C2—H2	120.5	C11—C12—C7	121.6 (3)
C2—C3—C4	119.1 (3)	C11—C12—H12	119.2
C2—C3—H3	120.5	C7—C12—H12	119.2
C4—C3—H3	120.5	N1—C13—C7	125.9 (3)
C5—C4—C3	119.3 (3)	N1—C13—H13	117.1
C5—C4—H4	120.3	C7—C13—H13	117.1

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1i	0.83	2.12	2.930 (3)	165
O6—H6B···O3ii	0.82	2.00	2.819 (3)	172
O2—H2B···O5	0.83	2.57	3.009 (3)	114
O2—H2B···N3	0.83	2.53	3.234 (4)	143
O2—H2B···O4	0.83	1.85	2.677 (3)	170
O2—H2A···O6	0.83	1.86	2.681 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O1i	0.83	2.12	2.930 (3)	165
O6—H6B⋯O3ii	0.82	2.00	2.819 (3)	172
O2—H2B⋯O5	0.83	2.57	3.009 (3)	114
O2—H2B⋯N3	0.83	2.53	3.234 (4)	143
O2—H2B⋯O4	0.83	1.85	2.677 (3)	170
O2—H2A⋯O6	0.83	1.86	2.681 (3)	168

Symmetry codes: (i) ; (ii) .