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

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

doi:10.1107/S1600536812044649

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 (C-C) = 0.002 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 17.5
Details

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

Arun M. Islor,^a Shridhar Malladi,^a Sandeep Telkar,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^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-HO contacts occur. In the crystal, N-HO and N-HN hydrogen bonds and C-HN 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); Vijesh et al. (2011); Boecker & Guengerich (1986); Vo et al. (1995). For puckering analysis, see: Cremer & Pople (1975); Boeyens (1978). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₃H₂₇N₃O₄
M_r = 409.48
Triclinic, $[P \overline 1]$
a = 8.5905 (2) Å
b = 10.8253 (3) Å
c = 11.3702 (3) Å
= 91.021 (1)°
= 97.922 (1)°
= 93.445 (1)°
V = 1045.02 (5) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.969, T_max = 0.986
18073 measured reflections
4983 independent reflections
4313 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(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
_max = 0.33 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N11-H11BN21ⁱ	0.890 (17)	2.200 (17)	3.0352 (14)	156.2 (14)
N22-H22O3ⁱⁱ	0.892 (17)	2.066 (17)	2.9580 (13)	178.6 (15)
C2-H2BN21ⁱⁱⁱ	0.98	2.52	3.4223 (16)	153
C36-H36O1	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); 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, 2012) 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: 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

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organic compounds