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

Islor, A.M.; Vijesh, A.M.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812045333

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 (C-C) = 0.002 Å
Disorder in main residue
R = 0.040
wR = 0.111
Data-to-parameter ratio = 16.9
Details

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

Arun M. Islor,^a A. M. Vijesh,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^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-HN, O-HO and N-HO hydrogen bonds, as well as C-HO and C-HS 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); Boecker & Guengerich (1986); Gordeev et al. (1996); Buhler & Kiowski (1987); Vo et al. (1995). For puckering analysis of cyclic motifs, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₁H₂₃N₃O₄S·H₂O
M_r = 431.50
Monoclinic, P 2₁ /c
a = 10.5542 (2) Å
b = 14.7260 (2) Å
c = 14.5377 (2) Å
= 110.106 (1)°
V = 2121.77 (6) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.950, T_max = 0.963
20236 measured reflections
5267 independent reflections
4311 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(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
_max = 0.30 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O8-H8AN22ⁱ	0.83 (3)	2.09 (3)	2.8982 (18)	167 (2)
O8-H8BO4ⁱⁱ	0.84 (3)	2.09 (3)	2.8989 (19)	164 (2)
N21-H21O2ⁱⁱⁱ	0.884 (19)	1.985 (19)	2.8505 (15)	165.9 (17)
N31-H31AO8^iv	0.908 (19)	1.965 (19)	2.8561 (18)	166.6 (17)
C23-H23S1A^v	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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

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organic compounds