[Journal logo]

Volume 69 
Part 10 
Page o1530  
October 2013  

Received 2 July 2013
Accepted 2 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.009 Å
R = 0.048
wR = 0.106
Data-to-parameter ratio = 8.8
Details
Open access

2-Dichloromethyl-N-ethyl-5-(1-phenylsilolan-1-yl)cyclopent-3-enecarboxamide

aChemical Science and Technology Department, Kunming University, Kunming 650091, People's Republic of China
Correspondence e-mail: blackcrossing630@vip.sina.com

In the title compound, C19H25Cl2NOSi, the NH group and the carbonyl O atom of the amide fragment are involved in an intermolecular N-H...O hydrogen bond forming chains of molecules. The plane of the benzene ring forms a dihedral angle of 50.5 (2)° with respect to the silolane ring and an angle of 49.74 (2)° with the cyclopentyl moiety.

Related literature

For biological activity of silicon-containing compounds, see: Tacke & Wannagat (1975[Tacke, R. & Wannagat, U. (1975). Monatsh. Chem. 106, 1005-1018.], 1979[Tacke, R. & Wannagat, U. (1979). Top. Curr. Chem. 84, 1-75.]); Voronkov (1979[Voronkov, M. G. (1979). Top. Curr. Chem. 84, 77-135.]). For synthetic methods, see: Matthews et al. (2001[Matthews, J. L., McArthur, D. R., Muir, K. W. & White, D. N. J. (2001). Acta Cryst. C57, 120-122.], 2002[Matthews, J. L., McArthur, D. R. & Muir, K. W. (2002). Tetrahedron Lett. 43, 5401-5404.]); Benkeser et al. (1962[Benkeser, R. A., Grossman, R. F. & Stanton, G. M. (1962). J. Am. Chem. Soc. 84, 4727-4730.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H25Cl2NOSi

  • Mr = 382.39

  • Orthorhombic, F d d 2

  • a = 42.892 (9) Å

  • b = 13.335 (3) Å

  • c = 14.234 (3) Å

  • V = 8141 (3) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 295 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.927, Tmax = 0.963

  • 3814 measured reflections

  • 1925 independent reflections

  • 1375 reflections with I > 2[sigma](I)

  • Rint = 0.045

  • 3 standard reflections every 200 reflections intensity decay: 1%

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

  • wR(F2) = 0.106

  • S = 1.03

  • 1925 reflections

  • 219 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.10 2.945 (5) 170
Symmetry code: (i) [-x+{\script{7\over 4}}, y-{\script{1\over 4}}, z+{\script{1\over 4}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2436 ).


Acknowledgements

This work was supported by Yunnan Provincial Department of Science and Technology: Study on neuro-activities of gastrodin and helicid derivatives (grant No. 2013FZ102), Synthesis and Sturcture-Activity Relationship of Pulverolide and Its Analogues (grant No. 2013FZ101).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Benkeser, R. A., Grossman, R. F. & Stanton, G. M. (1962). J. Am. Chem. Soc. 84, 4727-4730.  [CrossRef] [ChemPort] [Web of Science]
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Matthews, J. L., McArthur, D. R. & Muir, K. W. (2002). Tetrahedron Lett. 43, 5401-5404.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Matthews, J. L., McArthur, D. R., Muir, K. W. & White, D. N. J. (2001). Acta Cryst. C57, 120-122.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tacke, R. & Wannagat, U. (1975). Monatsh. Chem. 106, 1005-1018.  [CrossRef] [ChemPort]
Tacke, R. & Wannagat, U. (1979). Top. Curr. Chem. 84, 1-75.  [CrossRef] [ChemPort] [PubMed]
Voronkov, M. G. (1979). Top. Curr. Chem. 84, 77-135.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1530  [ doi:10.1107/S160053681302446X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.