Bis[2-(hy-droxy-imino-meth-yl)phenolato]nickel(II): a second monoclinic polymorph.

The title compound, [Ni(C(7)H(6)NO(2))(2)], (I), is a second monoclinic polymorph of the compound, (II), reported by Srivastava et al. [Acta Cryst. (1967), 22, 922] and Mereiter [Private communication (2002) CCDC refcode NISALO01]. The bond lengths and angles are similar in both structures. The mol-ecule in both structures lies on a crystallographic inversion center and both have an inter-nal hydrogen bond. The title compound crystallizes in the space group P2(1)/c (Z = 2), whereas compound (II) is in the space group P2(1)/n (Z = 2) with a similar cell volume but different cell parameters. In both polymorphs, mol-ecules are arranged in the layers but in contrast to the previously published compound (II) where the dihedral angle between the layers is 86.3°, in the title polymorph the same dihedral angle is 29.4°. The structure of (I) is stabilized by strong intra-molecular O-H⋯O hydrogen bonding between the O-H group and the phenolate O atom.

Related literature

For the original monoclinic polymorph, see: Srivastava et al. (1967 ▶); Mereiter (2002 ▶). For background to direct synthesis, see: Nesterov et al. (2004 ▶, 2006 ▶); Kovbasyuk et al. (1998 ▶); Vassilyeva et al. (1997 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Ni(C7H6NO2)2]

M = 330.97

Monoclinic,

a = 4.9912 (2) Å

b = 7.4717 (3) Å

c = 17.4152 (7) Å

β = 90.653 (3)°

V = 649.42 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.51 mm−1

T = 296 K

0.53 × 0.36 × 0.11 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 2002 ▶) T min = 0.501, T max = 0.851

4678 measured reflections

1342 independent reflections

1096 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.072

S = 1.06

1342 reflections

121 parameters

All H-atom parameters refined

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 I, global. DOI: 10.1107/S1600536811001383/br2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001383/br2156Isup2.hkl

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

[Ni(C7H6NO2)2]	F(000) = 340
Mr = 330.97	Dx = 1.693 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1800 reflections
a = 4.9912 (2) Å	θ = 2.3–26.1°
b = 7.4717 (3) Å	µ = 1.51 mm−1
c = 17.4152 (7) Å	T = 296 K
β = 90.653 (3)°	Prizm, green
V = 649.42 (5) Å3	0.53 × 0.36 × 0.11 mm
Z = 2

Bruker SMART APEXII diffractometer	1342 independent reflections
Radiation source: fine-focus sealed tube	1096 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: numerical (SADABS; Sheldrick, 2002)	h = −6→6
Tmin = 0.501, Tmax = 0.851	k = −9→8
4678 measured reflections	l = −19→21

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.030P)2 + 0.3216P] where P = (Fo2 + 2Fc2)/3
1342 reflections	(Δ/σ)max = 0.005
121 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. Numerical absorption corrections based on indexed crystal faces were applied using the Crystal Faces plugin in Bruker APEX2 software (Bruker, 2007)

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
C1	0.0820 (4)	0.3351 (3)	0.41130 (12)	0.0363 (5)
C2	0.0261 (5)	0.4911 (3)	0.36993 (13)	0.0383 (5)
C3	−0.1766 (5)	0.4888 (4)	0.31268 (15)	0.0471 (6)
C4	−0.3212 (6)	0.3375 (4)	0.29774 (16)	0.0540 (7)
C5	−0.2652 (6)	0.1845 (4)	0.33888 (16)	0.0530 (7)
C6	−0.0674 (5)	0.1815 (4)	0.39413 (15)	0.0482 (6)
C7	0.1642 (5)	0.6566 (3)	0.38506 (14)	0.0415 (6)
H3	−0.208 (5)	0.586 (3)	0.2867 (14)	0.040 (7)*
H4	−0.455 (6)	0.342 (4)	0.2600 (17)	0.071 (9)*
H5	−0.369 (6)	0.088 (4)	0.3311 (16)	0.064 (9)*
H6	−0.029 (5)	0.081 (4)	0.4202 (15)	0.048 (7)*
H7	0.106 (5)	0.757 (3)	0.3582 (13)	0.037 (6)*
H2	0.578 (7)	0.828 (5)	0.4672 (18)	0.074 (11)*
N1	0.3534 (4)	0.6733 (3)	0.43480 (11)	0.0386 (4)
Ni1	0.5000	0.5000	0.5000	0.03283 (15)
O1	0.2671 (3)	0.3269 (2)	0.46661 (9)	0.0413 (4)
O2	0.4542 (4)	0.8474 (3)	0.43860 (12)	0.0586 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0337 (11)	0.0407 (13)	0.0346 (12)	−0.0023 (10)	0.0046 (9)	−0.0038 (10)
C2	0.0372 (11)	0.0425 (12)	0.0355 (12)	0.0022 (11)	0.0022 (9)	−0.0003 (11)
C3	0.0458 (14)	0.0516 (16)	0.0436 (14)	0.0049 (14)	−0.0054 (11)	0.0030 (13)
C4	0.0467 (15)	0.069 (2)	0.0457 (15)	−0.0028 (15)	−0.0113 (12)	−0.0060 (15)
C5	0.0522 (16)	0.0531 (17)	0.0536 (16)	−0.0145 (14)	−0.0064 (13)	−0.0100 (14)
C6	0.0537 (16)	0.0421 (15)	0.0488 (15)	−0.0064 (13)	−0.0030 (12)	−0.0010 (12)
C7	0.0470 (14)	0.0384 (13)	0.0391 (13)	0.0027 (11)	−0.0033 (11)	0.0092 (11)
N1	0.0450 (11)	0.0306 (10)	0.0401 (10)	−0.0052 (9)	−0.0023 (9)	0.0034 (9)
Ni1	0.0366 (2)	0.0295 (2)	0.0324 (2)	−0.00221 (19)	−0.00104 (15)	0.00314 (18)
O1	0.0474 (10)	0.0329 (9)	0.0434 (9)	−0.0062 (7)	−0.0100 (7)	0.0056 (7)
O2	0.0717 (14)	0.0338 (10)	0.0698 (13)	−0.0151 (9)	−0.0272 (11)	0.0166 (9)

C1—O1	1.328 (3)	C5—C6	1.371 (4)
C1—C2	1.397 (3)	C5—H5	0.90 (3)
C1—C6	1.399 (3)	C6—H6	0.90 (3)
C2—C3	1.412 (3)	C7—N1	1.280 (3)
C2—C7	1.439 (3)	C7—H7	0.93 (2)
C3—C4	1.365 (4)	N1—O2	1.396 (3)
C3—H3	0.87 (2)	N1—Ni1	1.8661 (19)
C4—C5	1.376 (4)	Ni1—O1	1.8292 (16)
C4—H4	0.93 (3)	O2—H2	0.80 (3)
O1—C1—C2	123.1 (2)	C5—C6—C1	121.0 (3)
O1—C1—C6	118.8 (2)	C5—C6—H6	121.2 (17)
C2—C1—C6	118.1 (2)	C1—C6—H6	117.8 (18)
C1—C2—C3	119.4 (2)	N1—C7—C2	123.8 (2)
C1—C2—C7	122.0 (2)	N1—C7—H7	119.1 (15)
C3—C2—C7	118.5 (2)	C2—C7—H7	117.1 (15)
C4—C3—C2	121.2 (3)	C7—N1—O2	112.7 (2)
C4—C3—H3	120.3 (17)	C7—N1—Ni1	128.70 (18)
C2—C3—H3	118.6 (17)	O2—N1—Ni1	118.62 (15)
C3—C4—C5	119.0 (3)	O1i—Ni1—O1	180.0
C3—C4—H4	118 (2)	O1i—Ni1—N1	86.92 (8)
C5—C4—H4	123 (2)	O1—Ni1—N1	93.08 (8)
C6—C5—C4	121.3 (3)	N1i—Ni1—N1	180.00 (9)
C6—C5—H5	120.1 (19)	C1—O1—Ni1	129.22 (15)
C4—C5—H5	118.5 (19)	N1—O2—H2	98 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.80 (3)	1.80 (3)	2.511 (2)	146 (4)

N1—Ni1	1.8661 (19)
Ni1—O1	1.8292 (16)

O1—Ni1—N1

93.08 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.80 (3)	1.80 (3)	2.511 (2)	146 (4)

Symmetry code: (i) .