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

Moroz, Y.S.; Konovalova, I.S.; Iskenderov, T.S.; Pavlova, S.V.; Shishkin, O.V.

doi:10.1107/S1600536809033352

Volume 65
Part 9
Page o2242
September 2009

Received 3 August 2009
Accepted 21 August 2009
Online 26 August 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.046
wR = 0.097
Data-to-parameter ratio = 6.2
Details

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

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

^aNational Taras Shevchenko University, Department of Chemistry, Volodymyrska Str. 64, 01033 Kyiv, Ukraine, and ^bSCT `Institute for Syngle Crystals', National Acadamy of Science of Ukraine, Lenina Ave. 60, 61001 Kharkiv, Ukraine
Correspondence e-mail: ysmoroz@yahoo.com

The title compound, C₁₀H₁₂N₄O₂, features an intramolecular N-HN 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-HO 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, C c
a = 4.4498 (11) Å
b = 22.833 (7) Å
c = 10.955 (3) Å
= 97.47 (2)°
V = 1103.7 (5) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.986, T_max = 0.995
3899 measured reflections
958 independent reflections
793 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.097
S = 1.10
958 reflections
155 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.13 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2OAO1ⁱ	0.84 (5)	1.88 (5)	2.709 (4)	170 (5)
N3-H3NAN4	0.87 (4)	2.30 (4)	2.640 (4)	104 (3)
Symmetry code: (i) $[x+1, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: TK2523 ).

Acknowledgements

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

References

Bürgi, H.-D. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2., Weinhiem: VCH.
Duda, A. M., Karaczyn, A., Kozlowski, H., Fritsky, I. O., Glowiak, T., Prisyazhnaya, E. V., Sliva, T. Yu. & Swiatek-Kozlowska, J. (1997). J. Chem. Soc. Dalton Trans. pp. 3853-3859.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kovbasyuk, L., Pritzkow, H., Krämer, R. & Fritsky, I. O. (2004). Chem. Commun. pp. 880-881.
Krämer, R., Fritsky, I. O., Pritzkow, H. & Kovbasyuk, L. A. (2002). J. Chem. Soc. Dalton Trans. pp. 1307-1314.
Mokhir, A. A., Gumienna-Kontecka, E., Swiatek-Kozlowska, J., Petkova, E. G., Fritsky, I. O., Jerzykiewicz, L., Kapshuk, A. A. & Sliva, T. Yu. (2002). Inorg. Chim. Acta, 329, 113-121.
Moroz, Yu. S., Kulon, K., Haukka, M., Gumienna-Kontecka, E., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2008a). Inorg. Chem. 47, 5656-5665.
Moroz, Y. S., Sliva, T. Yu., Kulon, K., Kozlowski, H. & Fritsky, I. O. (2008b). Acta Cryst. E64, m353-m354.
Onindo, C. O., Sliva, T. Yu., Kowalik-Jankowska, T., Fritsky, I. O., Buglyo, P., Pettit, L. D., Kozlowski, H. & Kiss, T. (1995). J. Chem. Soc. Dalton Trans. pp. 3911-3915.
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sliva, T. Yu., Duda, A. M., Glowiak, T., Fritsky, I. O., Amirkhanov, V. M., Mokhir, A. A. & Kozlowski, H. (1997a). J. Chem. Soc. Dalton Trans. pp. 273-276.
Sliva, T. Yu., Kowalik-Jankowska, T., Amirkhanov, V. M., Glowiak, T., Onindo, C. O., Fritsky, I. O. & Kozlowski, H. (1997b). J. Inorg. Biochem. 65, 287-294.

organic compounds