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Volume 69 
Part 3 
Page o389  
March 2013  

Received 27 December 2012
Accepted 11 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.048
wR = 0.146
Data-to-parameter ratio = 14.6
Details
Open access

Diethyl 2,6-dimethyl-4-[4-(3-phenylacryloyloxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate hemihydrate

aDepartment of Physics, Presidency College, Chennai 600 005, India, and bAsthagiri Herbal Research Foundation, Perungudi, Chennai 600 096, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title ester derivative, C28H29NO6·0.5H2O, the 1,4-dihydropyridine ring has a flattened boat conformation. The mean plane is almost perpendicular to the attached benzene ring, making a dihedral angle of 86.87 (9)°. The terminal phenyl ring is inclined to the central benzene ring by 67.56 (12)°. In the crystal, molecules are bridged via O-H...O hydrogen bonds involving the partially occupied water molecule, and this arrangement is strengthened by a pair of N-H...O hydrogen bonds and C-H...O interactions. The ethyl atoms of one of the ethyl ester groups are disordered over two sites with an occupancy ratio of 0.716 (5):0.284 (5).

Related literature

For the biological activity of ester derivatives, see: Bi et al. (2012[Bi, Y., Xu, J., Sun, F., Wu, X., Ye, W., Sun, Y. & Huang, W. (2012). Molecules, 17, 8832-8841.]); Bartzatt et al. (2004[Bartzatt, R., Cirillo, S. L. & Cirillo, J. D. (2004). Physiol. Chem. Phys. Med. NMR, 36, 85-94.]); Anadu et al. (2006[Anadu, N. O., Davisson, V. J. & Cushman, M. (2006). J. Med. Chem. 49, 3897-3905.]).

[Scheme 1]

Experimental

Crystal data
  • C28H29NO6·0.5H2O

  • Mr = 484.53

  • Monoclinic, C 2/c

  • a = 25.4905 (11) Å

  • b = 8.6166 (4) Å

  • c = 23.2902 (10) Å

  • [beta] = 92.235 (2)°

  • V = 5111.6 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.983

  • 24059 measured reflections

  • 5036 independent reflections

  • 3271 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.146

  • S = 1.09

  • 5036 reflections

  • 344 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.87 (2) 2.31 (2) 3.148 (2) 163 (2)
O1W-H1W...O5 1.04 1.81 2.615 (6) 132
C14-H14...O1Wii 0.93 2.50 3.140 (6) 126
Symmetry codes: (i) [-x, y, -z+{\script{1\over 2}}]; (ii) [-x, y-1, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: 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: SU2546 ).


Acknowledgements

SA thanks the UGC, India, for financial support

References

Anadu, N. O., Davisson, V. J. & Cushman, M. (2006). J. Med. Chem. 49, 3897-3905.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bartzatt, R., Cirillo, S. L. & Cirillo, J. D. (2004). Physiol. Chem. Phys. Med. NMR, 36, 85-94.  [PubMed] [ChemPort]
Bi, Y., Xu, J., Sun, F., Wu, X., Ye, W., Sun, Y. & Huang, W. (2012). Molecules, 17, 8832-8841.  [CrossRef] [ChemPort] [PubMed]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [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]


Acta Cryst (2013). E69, o389  [ doi:10.1107/S1600536813004108 ]

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