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Volume 68 
Part 11 
Pages o3156-o3157  
November 2012  

Received 10 October 2012
Accepted 11 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.114
Data-to-parameter ratio = 17.9
Details
Open access

1-[5-Acetyl-2,6-dimethyl-4-(5-phenyl-1H-pyrazol-3-yl)-1,4-dihydropyridin-3-yl]ethanone monohydrate

aNational Institute of Technology-Karnataka, Department of Chemistry, Organic Chemistry Laboratory, Surathkal, Mangalore 575 025, India,bUAS Hebbal, Veterinary College, Department of Microbiology, Bangalore 24, 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, C20H21N3O2·H2O, the aza-substitued six-membered ring adopts a L4B conformation. In the crystal, classical N-H...O, N-H...N and O-H...O hydrogen bonds connect the entities into a three-dimensional network. Intramolecular C-H...O contacts are also observed.

Related literature

For the pharmaceutical properties of 1,4-dihydropyridine-derived drugs, see: Janis & Triggle (1983[Janis, R. A. & Triggle, D. J. (1983). J. Med. Chem. 26, 775-785.]); Boecker & Guengerich (1986[Boecker, R. H. & Guengerich, F. P. (1986). J. Med. Chem. 29, 1596-1603.]); Gordeev et al. (1996[Gordeev, M. F., Patel, D. V. & Gordon, E. M. (1996). J. Org. Chem. 61, 924-928.]); Buhler & Kiowski (1987[Buhler, F. R. & Kiowski, W. (1987). J. Hypertens. 5, S3-S10.]); 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 the conformational analysis of puckering factors of five- and six-membered rings, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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
  • C20H21N3O2·H2O

  • Mr = 353.41

  • Monoclinic, P 21 /c

  • a = 10.3516 (2) Å

  • b = 12.4352 (3) Å

  • c = 15.4101 (3) Å

  • [beta] = 112.798 (1)°

  • V = 1828.68 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 200 K

  • 0.41 × 0.34 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.984

  • 17882 measured reflections

  • 4559 independent reflections

  • 3849 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.114

  • S = 1.04

  • 4559 reflections

  • 255 parameters

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

  • [Delta][rho]max = 0.30 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
N2-H2A...O3i 0.938 (19) 1.855 (19) 2.7822 (14) 169.1 (16)
N3-H3...N1ii 0.878 (17) 2.075 (17) 2.9454 (13) 171.1 (15)
O3-H3B...O2iii 0.86 (2) 1.92 (2) 2.7838 (13) 175.8 (17)
O3-H3C...O1iv 0.87 (2) 1.88 (2) 2.7372 (14) 169.8 (18)
C6-H6...O2 0.95 2.44 3.282 (2) 148
C10-H10...O2 1.00 2.33 2.7624 (13) 105
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, 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: ORTEPIII (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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: HG5260 ).


Acknowledgements

AMI is thankful to the Director of the National Institute of Technology for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, and the Government of India for a Young Scientist 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]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Buhler, F. R. & Kiowski, W. (1987). J. Hypertens. 5, S3-S10.  [CrossRef] [ChemPort]
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. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gordeev, M. F., Patel, D. V. & Gordon, E. M. (1996). J. Org. Chem. 61, 924-928.  [CrossRef] [ChemPort]
Janis, R. A. & Triggle, D. J. (1983). J. Med. Chem. 26, 775-785.  [CrossRef] [ChemPort] [PubMed] [ISI]
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]
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, o3156-o3157   [ doi:10.1107/S1600536812042614 ]

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