2-Hydroxy­imino-N′-[1-(2-pyrid­yl)ethyl­idene]propanohydrazide

Yurii S Moroz; Irina S Konovalova; Turganbay S Iskenderov; Svetlana V Pavlova; Oleg V Shishkin

doi:10.1107/S1600536809033352

. 2009 Aug 26;65(Pt 9):o2242. doi: 10.1107/S1600536809033352

2-Hydroxyimino-N′-[1-(2-pyridyl)ethylidene]propanohydrazide

Yurii S Moroz ^a,^*, Irina S Konovalova ^b, Turganbay S Iskenderov ^a, Svetlana V Pavlova ^a, Oleg V Shishkin ^b

PMCID: PMC2969988 PMID: 21577640

Abstract

The title compound, C₁₀H₁₂N₄O₂, features an intramolecular N—H⋯N hydrogen bond formed between the imine NH and oxime N atoms. The oxime group and the amide C=O bond are anti to each other. In the crystal, molecules are connected by O—H⋯O hydrogen bonds into supramolecular zigzag chains along the c axis.

Related literature

For oxime and pyridine derivatives, see: Sliva et al. (1997b ▶); Mokhir et al. (2002 ▶); Krämer et al. (2002 ▶); Kovbasyuk et al. (2004 ▶). For 2-hydroxyiminopropanamide and amide derivatives of 2-hydroxyiminopropanoic acid, see: Onindo et al. (1995 ▶); Duda et al. (1997 ▶); Sliva et al. (1997a ▶). For the preparation and characterization of 3d-metal complexes with 2-hydroxyimino-N′-[1-(2-pyridyl)ethylidene]propanohydrazone, see: Moroz et al. (2008a ▶,b ▶). For typical bond lengths, see: Bürgi & Dunitz (1994 ▶).

Experimental

Crystal data

C₁₀H₁₂N₄O₂
M _r = 220.24
Monoclinic,
a = 4.4498 (11) Å
b = 22.833 (7) Å
c = 10.955 (3) Å
β = 97.47 (2)°
V = 1103.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.15 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction KM-4/Xcalibur diffractometer with a Sapphire3 detector
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2006 ▶) T _min = 0.986, T _max = 0.995
3899 measured reflections
958 independent reflections
793 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.097
S = 1.10
958 reflections
155 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033352/tk2523sup1.cif

e-65-o2242-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033352/tk2523Isup2.hkl

e-65-o2242-Isup2.hkl^{(47.5KB, hkl)}

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
O2—H2OA⋯O1ⁱ	0.84 (5)	1.88 (5)	2.709 (4)	170 (5)
N3—H3NA⋯N4	0.87 (4)	2.30 (4)	2.640 (4)	104 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Ministry of Education and Science of Ukraine for financial support (grant No. F28/241–2009).

supplementary crystallographic information

Comment

As a part of our on-going work, we would like to report the structure of the title compound (I), Fig. 1, which comprises several groups capable of forming hydrogen bonding interactions: oxime, hydrazone, azomethine, and pyridine. Molecule (I) has been shown previously to form mono- and tetra-nuclear grid-like complexes with 3d-metals (Moroz et al., 2008a,b).

The C—N and N—O bond lengths in the oxime group, i.e. 1.285 (5) and 1.388 (4) Å, respectively, adopt typical values (Sliva et al., 1997b; Mokhir et al., 2002). The oxime group is in an anti- position with respect to the amide group, an observation consistent 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., 1997a). This conformation is stabilised by an N3—H···N4 intramolecular interaction, Table 1. The CH₃C(=NOH)C(O)NH fragment deviates from planarity as seen in a twist between the oxime and amide groups about the C8—C9 bond; the O1-C8-C9-N4 torsion angle is -164.0 (4)°. The flattened geometry of molecule results in the appearance of short intramolecular contacts H10···O2 is 2.34 Å and H7C···H3N 2.28 Å. The C—N bond distance in the azomethine group is 1.277 (4) Å, and the N2—C6—C1 angle is 115.7 (3)°. The pyridine-N atom is situated in an anti- position with respect to the azomethine group. Finally, the C—N and C—C bond lengths within the pyridine ring are normal for 2-substituted pyridine derivatives (Krämer et al., 2002; Kovbasyuk et al., 2004).

In the crystal packing molecules are united by O2—H···O1 hydrogen bonds, Table 1, where oximic-oxygen atom acts as donor and the hydrazone-oxygen atom acts as an acceptor (Fig. 2). This interaction probably results in the elongation of the C8—O1 bond to 1.233 (4) Å as compared with its mean value 1.210 Å (Bürgi & Dunitz, 1994). Due to the presence of the O2—H···O1 hydrogen bonds, zig-zag supramolecular chains are formed along the c axis.

Experimental

Compound (I) was prepared according to the reported procedure (Moroz et al., 2008b).