2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hy­droxy­imino-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide

Plutenko, M.O.; Lampeka, R.D.; Haukka, M.; Nordlander, E.

doi:10.1107/S1600536812045412

Volume 68
Part 12
Page o3381
December 2012

Received 25 September 2012
Accepted 2 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.081
Data-to-parameter ratio = 21.5
Details

2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hydroxyimino-N'-[1-(pyridin-2-yl)ethylidene]acetohydrazide

Maxym O. Plutenko,^a ^* Rostislav D. Lampeka,^a Matti Haukka ^b and Ebbe Nordlander ^c

^aDepartment of Chemistry, National Taras Shevchenko University, Volodymyrska Street 64, 01601 Kyiv, Ukraine,^bDepartment of Chemistry, University of Jyvaskyla, PO Box 35, FI-40014 Jyvaskyla, Finland, and ^cInorganic Chemistry, Center for Chemistry and Chemical Engineering, Lund University, Box 124, SE-221 00 Lund, Sweden
Correspondence e-mail: plutenkom@gmail.com

In the title compound, C₁₄H₁₆N₆O₂, the dihedral angles formed by the mean plane of the acetohydrazide group [maximum deviation 0.0629 (12) Å] with the pyrazole and pyridine rings are 81.62 (6) and 38.38 (4)° respectively. In the crystal, molecules are connected by N-HO and O-HN hydrogen bonds into supramolecular chains extending parallel to the c-axis direction.

Related literature

For uses of polynuclear complexes, see: Swiatek-Kozlowska et al. (2000); Wörl et al. (2005). For the use of oximes having additional donor functions as versatile ligands, see: Krämer & Fritsky (2000); Sachse et al. (2008); Kanderal et al. (2005). For related structures, see: Moroz et al. (2012); Mokhir et al. (2002); Sliva et al. (1997). For the synthesis, see: Kozikowski & Adamczyk (1983).

Experimental

Crystal data

C₁₄H₁₆N₆O₂
M_r = 300.33
Monoclinic, C c
a = 24.5792 (6) Å
b = 7.5795 (2) Å
c = 8.3072 (2) Å
= 107.335 (1)°
V = 1477.32 (6) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.36 × 0.28 × 0.21 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) T_min = 0.966, T_max = 0.980
8846 measured reflections
4395 independent reflections
4096 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.081
S = 1.03
4395 reflections
204 parameters
3 restraints
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2ON6ⁱ	0.88	1.79	2.6686 (13)	175
N3-H3NO1ⁱ	0.86	2.17	3.0196 (13)	174
Symmetry code: (i) $[x, -y+1, z-{\script{1\over 2}}]$ .

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, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5011 ).

Acknowledgements

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.

References

Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.
Kozikowski, A. P. & Adamczyk, M. (1983). J. Org. Chem. 48, 366-372.
Krämer, R. & Fritsky, I. O. (2000). Eur. J. Org. Chem. pp. 3505-3510.
Mokhir, A. A., Gumienna-Kontecka, E., Swiatek-Kozlowska, J., Petkova, E. G., Fritsky, I. O., Jerzykiewicz, L., Kapshuk, A. A. & Sliva, T. Y. (2002). Inorg. Chim. Acta, 329, 113-121.
Moroz, Y. S., Demeshko, S., Haukka, M., Mokhir, A., Mitra, U., Stocker, M., Müller, P., Meyer, F. & Fritsky, I. O. (2012). Inorg. Chem. 51, 7445-7447.
Sachse, A., Penkova, L., Noel, G., Dechert, S., Varzatskii, O. A., Fritsky, I. O. & Meyer, F. (2008). Synthesis, 5, 800-806.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sliva, T. Yu., Kowalik-Jankowska, T., Amirkhanov, V. M., Glowiak, T., Onindo, C. O., Fritsky, I. O. & Kozlowski, H. (1997). J. Inorg. Biochem. 65, 287-294.
Swiatek-Kozlowska, J., Fritsky, I. O., Dobosz, A., Karaczyn, A., Dudarenko, N. M., Sliva, T. Yu., Gumienna-Kontecka, E. & Jerzykiewicz, L. (2000). J. Chem. Soc. Dalton Trans. pp. 4064-4068.
Wörl, S., Pritzkow, H., Fritsky, I. O. & Krämer, R. (2005). Dalton Trans. pp. 27-29.

organic compounds