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

Islor, A.M.; Malladi, S.; Sundershan, S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812042614

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 (C-C) = 0.002 Å
R = 0.040
wR = 0.114
Data-to-parameter ratio = 17.9
Details

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

Arun M. Islor,^a Shridhar Malladi,^a S. Sundershan,^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,^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-HO, N-HN and O-HO hydrogen bonds connect the entities into a three-dimensional network. Intramolecular C-HO contacts are also observed.

Related literature

For the pharmaceutical properties of 1,4-dihydropyridine-derived drugs, see: Janis & Triggle (1983); Boecker & Guengerich (1986); Gordeev et al. (1996); Buhler & Kiowski (1987); Vo et al. (1995). For the conformational analysis of puckering factors of five- and six-membered rings, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₀H₂₁N₃O₂·H₂O
M_r = 353.41
Monoclinic, P 2₁ /c
a = 10.3516 (2) Å
b = 12.4352 (3) Å
c = 15.4101 (3) Å
= 112.798 (1)°
V = 1828.68 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.965, T_max = 0.984
17882 measured reflections
4559 independent reflections
3849 reflections with I > 2(I)
R_int = 0.015

Refinement

R[F² > 2(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
_max = 0.30 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO3ⁱ	0.938 (19)	1.855 (19)	2.7822 (14)	169.1 (16)
N3-H3N1ⁱⁱ	0.878 (17)	2.075 (17)	2.9454 (13)	171.1 (15)
O3-H3BO2ⁱⁱⁱ	0.86 (2)	1.92 (2)	2.7838 (13)	175.8 (17)
O3-H3CO1^iv	0.87 (2)	1.88 (2)	2.7372 (14)	169.8 (18)
C6-H6O2	0.95	2.44	3.282 (2)	148
C10-H10O2	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); 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: ORTEPIII (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: 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

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