Bis[2-(hy­droxy­imino­meth­yl)phenolato]nickel(II): a second monoclinic polymorph

Rusanova, J.A.; Buvaylo, E.A.; Rusanov, E.B.

doi:10.1107/S1600536811001383

metal-organic compounds

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Volume 67| Part 2| February 2011| Pages m222-m223

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Bis[2-(hydroxyiminomethyl)phenolato]nickel(II): a second monoclinic polymorph

Julia A. Rusanova,^a ^* Elena A. Buvaylo ^a and Eduard B. Rusanov ^b

^aNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01033 Kyiv, Ukraine, and ^bInst. of Organic Chemistry, Acad. Sci. Ukraine, Murmanska Str. 5, Kiev 02094, Ukraine
^*Correspondence e-mail: rusanova_j@yahoo.com

(Received 21 December 2010; accepted 10 January 2011; online 15 January 2011)

The title compound, [Ni(C₇H₆NO₂)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 molecule in both structures lies on a crystallographic inversion center and both have an internal hydrogen bond. The title compound crystallizes in the space group P2₁/c (Z = 2), whereas compound (II) is in the space group P2₁/n (Z = 2) with a similar cell volume but different cell parameters. In both polymorphs, molecules 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 intramolecular 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_r = 330.97
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.072
S = 1.06
1342 reflections
121 parameters
All H-atom parameters refined
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001383/br2156sup1.cif

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

checkCIF report

Comment top

The cell dimensions of the title modification after transformation from P2₁/c to P2₁/n setting, are: a=18.062, b=7.472, c=4.991, β =105.39, whereas the cell dimensions of the reported compound (II) monoclinic P2₁/n modification are: a = 13. 830, b = 4.880, c = 10.200 Å; β = 110.43° ( Srivastava et al., 1967). The asymmetric unit of the title compound contains half molecule (Fig. 1), lying across a crystallographic inversion centre. The bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with the structure of the compound (II).

Related literature top

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 top

The title compound was prepared by direct synthesis: manganese powder (0.06 g, 1 mmol), Ni(OAc)₂ (0.25 g, 1 mmol), salicylic aldehyde (0.21 ml, 2 mmol), NH₂OH^.HCl (0.14 g, 2 mmol), dimethylformamide (20 ml) were heated to 323–333 K and stirred magnetically for 40 min, until total dissolution of the manganese powder was observed. The transparent brown solution was allowed to stand at room temperature and brown-green crystals of the title compound suitable for X-ray analysis precipitated within few days. They were collected by filter-suction, washed with dry PrⁱOH and finally dried in vacuo at room temperature (yield; 0.12 g)

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code: 1-x;1-y;1-z].
	Fig. 2. The crystal packing of the title compound (a) and compound (II) (NISALO) (b). Hydrogen atoms are omited for clarity.

Bis[2-(hydroxyiminomethyl)phenolato]nickel(II) top

Crystal data top

[Ni(C₇H₆NO₂)₂]	F(000) = 340
M_r = 330.97	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.030P)² + 0.3216P] where P = (F_o² + 2F_c²)/3
1342 reflections	(Δ/σ)_max = 0.005
121 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Ni(C₇H₆NO₂)₂]	V = 649.42 (5) Å³
M_r = 330.97	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9912 (2) Å	µ = 1.51 mm⁻¹
b = 7.4717 (3) Å	T = 296 K
c = 17.4152 (7) Å	0.53 × 0.36 × 0.11 mm
β = 90.653 (3)°

Data collection top

Bruker SMART APEXII diffractometer	1342 independent reflections
Absorption correction: numerical (SADABS; Sheldrick, 2002)	1096 reflections with I > 2σ(I)
T_min = 0.501, T_max = 0.851	R_int = 0.028
4678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.072	All H-atom parameters refined
S = 1.06	Δρ_max = 0.28 e Å⁻³
1342 reflections	Δρ_min = −0.26 e Å⁻³
121 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₆NO₂)₂]
M_r	330.97
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	4.9912 (2), 7.4717 (3), 17.4152 (7)
β (°)	90.653 (3)
V (Å³)	649.42 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.53 × 0.36 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Numerical (SADABS; Sheldrick, 2002)
T_min, T_max	0.501, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections	4678, 1342, 1096
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.072, 1.06
No. of reflections	1342
No. of parameters	121
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

N1—Ni1	1.8661 (19)	Ni1—O1	1.8292 (16)

O1—Ni1—N1	93.08 (8)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

The authors gratefully acknowledge the Ukrainian State Fund for Fundamental Researchers (SFFR) for financial support of the Research Program (Chemistry).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kovbasyuk, L. A., Vassilyeva, O. Yu., Kokozay, V. N., Linert, W., Reedijk, J., Skelton, B. W. & Oliver, A. G. (1998). J. Chem. Soc. Dalton Trans. pp. 2735–2738. Web of Science CSD CrossRef Google Scholar
Mereiter, K. (2002). Private communication (refcode NISALO01). CCDC, Cambrige, England. Google Scholar
Nesterov, D. S., Kokozay, V. N., Dyakonenko, V. V., Shishkin, O. V., Jezierska, J., Ozarowski, F., Kirillov, A. M., Kopylovich, M. N. & Pombeiro, A. J. L. (2006). Chem. Commun. pp. 4605–4607. Web of Science CSD CrossRef Google Scholar
Nesterov, D. S., Makhankova, V. G., Vassilyeva, O. Yu., Kokozay, V. N., Kovbasyuk, L. A., Skelton, B. W. & Jezierska, J. (2004). Inorg. Chem. 43, 7868–7876. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany. Google Scholar
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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m222-m223

doi:10.1107/S1600536811001383

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[2-(hy­dr­oxy­imino­meth­yl)phenolato]nickel(II): a second monoclinic polymorph

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[2-(hydroxyiminomethyl)phenolato]nickel(II): a second monoclinic polymorph