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Volume 69 
Part 5 
Pages o765-o766  
May 2013  

Received 2 April 2013
Accepted 8 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.038
wR = 0.106
Data-to-parameter ratio = 23.8
Details
Open access

A second monoclinic polymorph of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-hydroxyimino-N'-[1-(pyridin-2-yl)ethylidene]acetohydrazide

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

The title compound, C14H16N6O2, is a second monoclinic polymorph of 2-[1-(3,5-dimethyl)pyrazolyl]-2-hydroxyimino-N'-[1-(2-pyridyl)ethylidene] acetohydrazide, with two crystallographically independent molecules per asymmetric unit. The non-planar molecules are chemically equal having similar geometric parameters. The previously reported polymorph [Plutenko et al. (2012[Plutenko, M. O., Lampeka, R. D., Haukka, M. & Nordlander, E. (2012). Acta Cryst. E68, o3381.]). Acta Cryst. E68, o3281] was described in space group Cc (Z = 4). The oxime group and the O atom of the amide group are anti with respect to the C-C bond. In the crystal, molecules are connected by N-H...N hydrogen bonds into zigzag chains extending along the b axis.

Related literature

For uses of oxime ligands, see: Penkova et al. (2009[Penkova, L. V., Maciag, A., Rybak-Akimova, E. V., Haukka, M., Pavlenko, V. A., Iskenderov, T. S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2009). Inorg. Chem. 48, 6960-6971.]); Kanderal et al. (2005[Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.]). For uses of oximes having additional donor functions as versatile ligands, see: Fritsky et al. (1998[Fritsky, I. O., Kozlowski, H., Sadler, P. J., Yefetova, O. P., Swiatek-Kozlowska, J., Kalibabchuk, V. A. & Glowiak, T. (1998). J. Chem. Soc. Dalton Trans. pp. 3269-3274.], 2004[Fritsky, I. O., Swiatek-Kozlowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746-3752.], 2006[Fritsky, I. O., Kozlowski, H., Kanderal, O. M. M., Swiatek-Kozlowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125-4127.]), Kanderal et al. (2005[Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.]), Onindo et al. (1995[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.]); Sliva et al. (1997[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.]). For related structures, see: Duda et al. (1997[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.]); Kanderal et al. (2005[Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.]); Krämer & Fritsky (2000[Krämer, R. & Fritsky, I. O. (2000). Eur. J. Org. Chem. pp. 3505-3510.]); Moroz et al. (2010[Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750-4752.], 2012[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.]); Sliva et al. (1997[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 et al. (2000[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.]); Mokhir et al. (2002[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.]); Penkova et al. (2010[Penkova, L. V., Demeshko, S., Pavlenko, V. A., Dechert, S., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chim. Acta, 363, 3036-3040.]); Strotmeyer et al. (2003[Strotmeyer, K. P., Fritsky, I. O., Ott, R., Pritzkow, H. & Krämer, R. (2003). Supramol. Chem. 15, 529-547.]); Fritsky et al. (2000[Fritsky, I. O., Ott, R. & Krämer, R. (2000). Angew. Chem. Int. Ed. 39, 3255-3258.]). For structure of the first polymorph, see Plutenko et al. (2012[Plutenko, M. O., Lampeka, R. D., Haukka, M. & Nordlander, E. (2012). Acta Cryst. E68, o3381.]). For the synthesis, see: Kozikowski & Adamczyk (1983[Kozikowski, A. P. & Adamczyk, M. (1983). J. Org. Chem. 48, 366-372.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16N6O2

  • Mr = 300.33

  • Monoclinic, P 21 /n

  • a = 19.4734 (4) Å

  • b = 7.7679 (2) Å

  • c = 19.8042 (4) Å

  • [beta] = 97.552 (1)°

  • V = 2969.74 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.39 × 0.33 × 0.28 mm

Data collection
  • Bruker Kappa APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.964, Tmax = 0.974

  • 64574 measured reflections

  • 9973 independent reflections

  • 8213 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.106

  • S = 1.03

  • 9973 reflections

  • 419 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2O...N5i 0.964 (17) 1.664 (17) 2.6193 (10) 170.1 (16)
O4-H4O...N10ii 0.978 (18) 1.670 (18) 2.6341 (10) 167.8 (17)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2008[Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2070 ).


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. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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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.  [CSD] [CrossRef]
Fritsky, I. O., Kozlowski, H., Kanderal, O. M. M., Swiatek-Kozlowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125-4127.  [CSD] [CrossRef]
Fritsky, I. O., Kozlowski, H., Sadler, P. J., Yefetova, O. P., Swiatek-Kozlowska, J., Kalibabchuk, V. A. & Glowiak, T. (1998). J. Chem. Soc. Dalton Trans. pp. 3269-3274.  [CSD] [CrossRef]
Fritsky, I. O., Ott, R. & Krämer, R. (2000). Angew. Chem. Int. Ed. 39, 3255-3258.  [ChemPort]
Fritsky, I. O., Swiatek-Kozlowska, J., Dobosz, A., Sliva, T. Y. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 357, 3746-3752.  [ISI] [CSD] [CrossRef] [ChemPort]
Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.  [CrossRef]
Kozikowski, A. P. & Adamczyk, M. (1983). J. Org. Chem. 48, 366-372.  [CrossRef] [ChemPort]
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.  [ISI] [CSD] [CrossRef] [ChemPort]
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.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750-4752.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
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.  [CrossRef]
Penkova, L. V., Demeshko, S., Pavlenko, V. A., Dechert, S., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chim. Acta, 363, 3036-3040.  [ISI] [CSD] [CrossRef] [ChemPort]
Penkova, L. V., Maciag, A., Rybak-Akimova, E. V., Haukka, M., Pavlenko, V. A., Iskenderov, T. S., Kozlowski, H., Meyer, F. & Fritsky, I. O. (2009). Inorg. Chem. 48, 6960-6971.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Plutenko, M. O., Lampeka, R. D., Haukka, M. & Nordlander, E. (2012). Acta Cryst. E68, o3381.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
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.  [CrossRef] [ChemPort] [ISI]
Strotmeyer, K. P., Fritsky, I. O., Ott, R., Pritzkow, H. & Krämer, R. (2003). Supramol. Chem. 15, 529-547.  [ISI] [CSD] [CrossRef] [ChemPort]
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.


Acta Cryst (2013). E69, o765-o766   [ doi:10.1107/S1600536813009628 ]

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