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Volume 68 
Part 12 
Pages o3269-o3270  
December 2012  

Received 25 October 2012
Accepted 29 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 17.5
Details
Open access

Diethyl 2,6-dimethyl-4-[5-(4-methylphenyl)-1H-pyrazol-4-yl]-1,4-dihydropyridine-3,5-dicarboxylate

aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India,bKuvempu University, Department of P.G. Studies and Research in Biotechnology and Bioinformatics, Jnanasahyadri-Karnataka, Shankaraghatta 577 451, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C23H27N3O4, the dihydropyridine ring adopts a 1,4B conformation. Intramolecular C-H...O contacts occur. In the crystal, N-H...O and N-H...N hydrogen bonds and C-H...N contacts connect the molecules into strands along the a-axis direction.

Related literature

For background to the biological and pharmaceutical importance of dihydropyridine compounds, see: Stout & Meyers (1982[Stout, D. M. & Meyers, A. I. (1982). Chem. Rev. 82, 223-243.]); Vijesh et al. (2011[Vijesh, A. M., Isloor, A. M., Peethambar, S. K., Shivananda, K. N., Arulmoli, T., Nishitha, A. & Isloor, N. A. (2011). Eur. J. Med. Chem. 46, 5591-5597.]); Boecker & Guengerich (1986[Boecker, R. H. & Guengerich, F. P. (1986). J. Med. Chem. 29, 1596-1603.]); Vo et al. (1995[Vo, D., Matowe, W. C., Ramesh, M., Iqbal, N., Wolowyk, M. W., Howlett, S. E. & Knaus, E. E. (1995). J. Med. Chem. 38, 2851-2859.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Boeyens (1978[Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C23H27N3O4

  • Mr = 409.48

  • Triclinic, [P \overline 1]

  • a = 8.5905 (2) Å

  • b = 10.8253 (3) Å

  • c = 11.3702 (3) Å

  • [alpha] = 91.021 (1)°

  • [beta] = 97.922 (1)°

  • [gamma] = 93.445 (1)°

  • V = 1045.02 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 200 K

  • 0.36 × 0.31 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.986

  • 18073 measured reflections

  • 4983 independent reflections

  • 4313 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.113

  • S = 1.05

  • 4983 reflections

  • 284 parameters

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N11-H11B...N21i 0.890 (17) 2.200 (17) 3.0352 (14) 156.2 (14)
N22-H22...O3ii 0.892 (17) 2.066 (17) 2.9580 (13) 178.6 (15)
C2-H2B...N21iii 0.98 2.52 3.4223 (16) 153
C36-H36...O1 0.95 2.30 3.2428 (17) 173
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and 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: HG5264 ).


Acknowledgements

AMI is thankful to the Board of Research in Nuclear Sciences, Government of India for the Young Scientist award and also thanks the Vision Group on Science & Technology, Government of Karnataka, India for the Best Research Paper award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Boecker, R. H. & Guengerich, F. P. (1986). J. Med. Chem. 29, 1596-1603.  [CrossRef] [ChemPort] [PubMed]
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.  [CrossRef]
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stout, D. M. & Meyers, A. I. (1982). Chem. Rev. 82, 223-243.  [CrossRef] [ChemPort] [ISI]
Vijesh, A. M., Isloor, A. M., Peethambar, S. K., Shivananda, K. N., Arulmoli, T., Nishitha, A. & Isloor, N. A. (2011). Eur. J. Med. Chem. 46, 5591-5597.  [ISI] [CrossRef] [ChemPort] [PubMed]
Vo, D., Matowe, W. C., Ramesh, M., Iqbal, N., Wolowyk, M. W., Howlett, S. E. & Knaus, E. E. (1995). J. Med. Chem. 38, 2851-2859.  [CrossRef] [ChemPort] [PubMed] [ISI]


Acta Cryst (2012). E68, o3269-o3270   [ doi:10.1107/S1600536812044649 ]

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