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Volume 68 
Part 12 
Pages o3302-o3303  
December 2012  

Received 16 October 2012
Accepted 2 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.040
wR = 0.111
Data-to-parameter ratio = 16.9
Details
Open access

Dimethyl 2,6-dimethyl-4-{3-[4-(methylsulfanyl)phenyl]-1H-pyrazol-4-yl}-1,4-dihydropyridine-3,5-dicarboxylate monohydrate

aNational Institute of Technology-Karnataka, Department of Chemistry, Organic Chemistry Laboratory, Surathkal, Mangalore 575 025, India,bGITAM University, Department of Engineering Chemistry, GIT, Rushikonda, Visakhapatnam, A.P. 530 045, 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, C21H23N3O4S·H2O, the methylsulfanyl group is disordered over two sets of sites with site-occupancy factors of 0.631 (11) and 0.369 (11). The dihydropyridine ring adopts an E4 conformation. In the crystal, classical O-H...N, O-H...O and N-H...O hydrogen bonds, as well as C-H...O and C-H...S contacts, connect the molecules into a three-dimensional network.

Related literature

For general information about the pharmacological importance of 1,4-dihydropyridine-based 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 puckering analysis of cyclic motifs, 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
  • C21H23N3O4S·H2O

  • Mr = 431.50

  • Monoclinic, P 21 /c

  • a = 10.5542 (2) Å

  • b = 14.7260 (2) Å

  • c = 14.5377 (2) Å

  • [beta] = 110.106 (1)°

  • V = 2121.77 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 200 K

  • 0.27 × 0.23 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.963

  • 20236 measured reflections

  • 5267 independent reflections

  • 4311 reflections with I > 2[sigma](I)

  • Rint = 0.019

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

  • wR(F2) = 0.111

  • S = 1.03

  • 5267 reflections

  • 312 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O8-H8A...N22i 0.83 (3) 2.09 (3) 2.8982 (18) 167 (2)
O8-H8B...O4ii 0.84 (3) 2.09 (3) 2.8989 (19) 164 (2)
N21-H21...O2iii 0.884 (19) 1.985 (19) 2.8505 (15) 165.9 (17)
N31-H31A...O8iv 0.908 (19) 1.965 (19) 2.8561 (18) 166.6 (17)
C23-H23...S1Av 0.95 2.79 3.637 (3) 149
Symmetry codes: (i) [-x+2, 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{3\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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, 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: RN2110 ).


Acknowledgements

AMI thanks the Board for Research in Nuclear Sciences, 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, Wisconsin, 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, o3302-o3303   [ doi:10.1107/S1600536812045333 ]

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