N′-(2-Hy­droxy­benzyl­idene)-2-(hy­droxy­imino)­propano­hydrazide

Maxym O Plutenko; Rostyslav D Lampeka; Yurii S Moroz; Matti Haukka; Svetlana V Pavlova

doi:10.1107/S1600536811045818

. 2011 Nov 12;67(Pt 12):o3282–o3283. doi: 10.1107/S1600536811045818

N′-(2-Hydroxybenzylidene)-2-(hydroxyimino)propanohydrazide

Maxym O Plutenko ^a,^*, Rostyslav D Lampeka ^a, Yurii S Moroz ^a, Matti Haukka ^b, Svetlana V Pavlova ^a

PMCID: PMC3238939 PMID: 22199788

Abstract

The molecule of the title compound, C₁₀H₁₁N₃O₃, adopts an all-trans conformation and is approxomately planar, the largest deviation from the least-squares plane through all non-H atoms being 0.261 (1) Å. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal, the molecules are packed into layers lying parallel to the ab plane by π-stacking interactions between the benzene ring of one molecule and the C—N bond of the oxime group of another molecule; the shortest intermolecular C⋯C separation within the layer is 3.412 (1) Å. The layers are connected by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the preparation and characterization of 3d metal complexes with related oxime derivatives, see: Kanderal et al. (2005 ▶); Moroz et al. (2010 ▶). For the crystal structures of similar oxime derivatives, see: Świątek-Kozłowska et al. (2000 ▶); Mokhir et al. (2002 ▶); Sachse et al. (2008 ▶). For 2-hydroxyiminopropanamide and amide derivatives of 2-hydroxyiminopropanoic acid, see: Onindo et al. (1995 ▶); Duda et al. (1997 ▶); Sliva et al. (1997 ▶). For the synthesis of 2-(hydroxyimino)propanehydrazide, see: Fritsky et al. (1998 ▶). For related structures, see: Krämer & Fritsky (2000 ▶); Wörl et al. (2005 ▶).

Experimental

Crystal data

C₁₀H₁₁N₃O₃
M _r = 221.22
Monoclinic,
a = 11.2296 (4) Å
b = 8.1905 (4) Å
c = 11.1000 (5) Å
β = 102.223 (2)°
V = 997.79 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.61 × 0.47 × 0.34 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T _min = 0.935, T _max = 0.964
16456 measured reflections
2465 independent reflections
2383 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.086
S = 1.07
2465 reflections
148 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045818/yk2025sup1.cif

e-67-o3282-sup1.cif^{(14.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045818/yk2025Isup2.hkl

e-67-o3282-Isup2.hkl^{(121.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811045818/yk2025Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811045818/yk2025Isup4.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.85	2.5808 (10)	144
O3—H3⋯O2ⁱ	0.84	1.82	2.6518 (9)	171
N2—H2⋯O1ⁱⁱ	0.88	2.32	3.1535 (9)	157

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The financial support from the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041) and the Swedish Institute (Visby Program) is gratefully acknowledged.

supplementary crystallographic information

Comment

Polynucleative oxime ligands attract considerable interest because of their ability to act as efficient chelating agents with respect to 3 d-metal ions and their tendency to form polynuclear metal complexes (Kanderal et al. 2005; Moroz et al. 2010). In the present work we present the synthesis and structure of the title compound (1) (Fig. 1), which comprises several donor groups: oxime, hydrazone, azomethine, and phenolic.

In the structure 1 the N'-(2-hydroxybenzylidene)-2-(hydroxyimino)propanehydrazide molecules are connected by extensive system of hydrogen bonds. The bond lengths N—O and C—N in the oxime group are 1.3838 (9) and 1.2854 (9) Å respectively, which is typical for protonated moieties of this type (Świątek-Kozłowska et al., 2000; Mokhir et al., 2002; Sachse et al., 2008). The oxime group is in a trans position with respect to the amide group, in accordance with the structures of 2-hydroxyiminopropanamide and other amide derivatives of 2-hydroxyiminopropanoic acid (Onindo et al., 1995; Duda et al., 1997; Sliva et al., 1997).

Bond lengths N—N', N—C and C—O of the hydrazone group are 1.3643 (9), 1.3544 (9) and 1.2353 (9) Å, respectively, and are typical for the protonated hydrazone groups (Moroz et al., 2010). The oxime and the hydrazide groups are situated in trans-position around the C(8)—C(9) bond. The CH₃C(NOH)C(O)NH fragment is almost planar (deviations of the non-hydrogen atoms from the moiety's mean plane are less than 0.2 Å).

The C—C (1.3814 (11) – 1.4115 (9) Å) bond lengths in the benzene ring have their typical values (Krämer et al., 2000; Wörl et al., 2005). The angles C—C'-C'', C—N—C' and N—C—C' are near 120°.

There are three hydrogen bonds in structure of 1 (Table 2). The O1—H1···N1 is an intramolecular hydrogen bond, where the phenolic oxygen atom acts as donor and the azomethine nitrogen atom acts as receptor. The O3—H3···O2 and N2—H2···O1 hydrogen bonds are intermolecular, the oximic oxygen and the hydrazone nitrogen atoms act as donors and the hydrazone oxygen and the phenolic oxygen atoms act as acceptors.

In the crystal packing, molecules of 1 form layers parallel to ab plane. The molecules in the layer are connected by π-stacking between the benzene ring of one molecule and C—N bond of the oxime group of another molecule. The distance between two planes formed by neighboring molecules is 3.3493 (7) Å. The layers are connected by extensive system of hydrogen bonds.

Experimental

A mixture of 2-(hydroxyimino)propanehydrazide synthesized according to (Fritsky et al., 1998) (0.117 g, 0.1 mmol) and salicylic aldehyde (0.122 g, 0.1 mmol) in 10 ml of methanol was heated to reflux for 2 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Yellowish needle crystals of 1 were obtained by slow evaporation of the methanolic solution. Yield: 2 g (90%).