[Journal logo]

Volume 66 
Part 5 
Page o1242  
May 2010  

Received 19 April 2010
Accepted 27 April 2010
Online 30 April 2010

[ng2761sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.117
Data-to-parameter ratio = 12.9
Details
Open access

Ethyl 2-(6-amino-5-cyano-3,4-dimethyl-2H,4H-pyrano[2,3-c]pyrazol-4-yl)acetate

M. Kannan,a Kandhasamy Kumaravel,b Gnanasambandam Vasukib and R. Krishnaa*

aCentre for Bioinformatics, Pondicherry University, Puducherry 605 014, India, and bDepartment of chemistry, Pondicherry university, Puducherry 605 014, India
Correspondence e-mail: krishstrucbio@gmail.com

In he title compound, C13H16N4O3, the pyrazole ring is planar (r.m.s. deviation = 0.054 Å). The pyran ring is not planar; the mean plane makes a dihedral angle of 1.9 (1)° with the pyrazole ring. In the crystal structure, intermolecular N-H...N and N-H...O interactions lead to a linear chain motif.

Related literature

For biological applications of pyrazole and pyranopyrazole derivatives, see: Wamhoff et al. (1993[Wamhoff, H., Kroth, E. & Strauch, K. (1993). Synthesis, 11, 1129.]).; Velaparthi et al. (2008[Velaparthi, S., Brunsteiner, M., Uddin, R., Wan, B., Franzblau, S. G. & Petukhov, P. A. (2008). J. Med. Chem. 51, 1999-2002.]); Magedov et al. (2007[Magedov, I. V., Manpadi, M., Vanslambrouck, S., Steelant, W. F. A., Rozhkova, E., Przhevalskii, N. M., Rogelj, S. & Kornienko, A. (2007). J. Med. Chem. 50, 5183-5192.]); Rovnyak et al. (1982[Rovnyak, G. C., Millonig, R. C., Schwartz, J. & Shu, V. (1982). J. Med. Chem. 25, 1482-1488.]). For the synthesis, see: Vasuki & Kumaravel (2008[Vasuki, G. & Kumaravel, K. (2008). Tetrahedron Lett. 49, 5636-5638.]).

[Scheme 1]

Experimental

Crystal data

  • C13H16N4O3

  • Mr = 276.30

  • Triclinic, [P \overline 1]

  • a = 6.961 (5) Å

  • b = 7.373 (5) Å

  • c = 14.535 (5) Å

  • [alpha] = 86.405 (5)°

  • [beta] = 85.183 (5)°

  • [gamma] = 65.726 (5)°

  • V = 677.3 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.981

  • 12811 measured reflections

  • 2385 independent reflections

  • 2130 reflections with I > 2[sigma](I)

  • Rint = 0.020
Refinement

  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.117

  • S = 1.02

  • 2378 reflections

  • 184 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O2i 0.86 2.55 3.274 (2) 142
N2-H2...N1ii 0.86 2.37 2.956 (2) 126
N3-H3A...N4iii 0.86 2.19 3.012 (2) 160
N3-H3B...O3iv 0.86 2.40 3.192 (2) 154
Symmetry codes: (i) -x, -y+2, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x+1, -y+1, -z+1; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2761 ).

Acknowledgements

The authors acknowledge the Centre of Excellence in Bioinformatics, Pondicherry University, for providing the facilities and GV thanks the Department of Science and Technology, New Delhi, Government of India, (No. SR/S5/GC-22/2007) for financial support.

References

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Magedov, I. V., Manpadi, M., Vanslambrouck, S., Steelant, W. F. A., Rozhkova, E., Przhevalskii, N. M., Rogelj, S. & Kornienko, A. (2007). J. Med. Chem. 50, 5183-5192.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rovnyak, G. C., Millonig, R. C., Schwartz, J. & Shu, V. (1982). J. Med. Chem. 25, 1482-1488.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vasuki, G. & Kumaravel, K. (2008). Tetrahedron Lett. 49, 5636-5638.  [ISI] [CSD] [CrossRef] [ChemPort]
Velaparthi, S., Brunsteiner, M., Uddin, R., Wan, B., Franzblau, S. G. & Petukhov, P. A. (2008). J. Med. Chem. 51, 1999-2002.  [ISI] [CrossRef] [PubMed] [ChemPort]
Wamhoff, H., Kroth, E. & Strauch, K. (1993). Synthesis, 11, 1129.  [CrossRef]

Acta Cryst (2010). E66, o1242  [ doi:10.1107/S1600536810015540 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.