[Journal logo]

Volume 69 
Part 9 
Page o1489  
September 2013  

Received 19 August 2013
Accepted 22 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.097
Data-to-parameter ratio = 16.8
Details
Open access

1-[2-(3-Methoxyphenyl)ethyl]pyrrolidine-2,5-dione

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C13H15NO3, the pyrrolidine ring makes a dihedral angle of 4.69 (9)° with the 3-methoxy-phenyl ring. In the crystal, hydrogen-bonded chains running along [101] are generated by connecting neighbouring molecules via C-H...O hydrogen bonds. Parallel chains are linked by further C-H...O hydrogen bonds, forming a three-dimensional structure.

Related literature

For the bioactivity of pyrrolidine-2,5-dione derivatives, see: Obniska et al. (2012[Obniska, J., Rzepka, S. & Kamin' ski, K. (2012). Bioorg. Med. Chem. 20, 4872-4880.]); Ha et al. (2011[Ha, Y. M., Kim, J., Parkl, Y. J., Park, D., Choi, Y. J., Kim, J. M., Chung, K. W., Han, Y. K., Park, J. Y., Lee, J. Y., Moon, H. R. & Chung, H. Y. (2011). Med. Chem. Commun. 2, 542-549.]); Kaminski et al. (2011[Kaminski, K., Rzepka, S. & Obniska, J. (2011). Bioorg. Med. Chem. Lett. 21, 5800-5803.]). For related structures, see: Khorasani & Fernandes (2012[Khorasani, S. & Fernandes, M. A. (2012). Acta Cryst. E68, o1503.]); Mayes et al. (2008[Mayes, B. A., McGarry, P., Moussa, A. & Watkin, D. J. (2008). Acta Cryst. E64, o1355.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15NO3

  • Mr = 233.26

  • Monoclinic, C c

  • a = 12.8719 (9) Å

  • b = 12.5878 (8) Å

  • c = 7.4523 (5) Å

  • [beta] = 90.831 (3)°

  • V = 1207.36 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.40 × 0.35 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]) Tmin = 0.964, Tmax = 0.982

  • 5692 measured reflections

  • 2615 independent reflections

  • 2328 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.097

  • S = 1.02

  • 2615 reflections

  • 156 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1B...O3i 0.96 2.54 3.418 (3) 151
C8-H8B...O1ii 0.97 2.54 3.469 (2) 161
C12-H12A...O2iii 0.97 2.57 3.456 (3) 152
Symmetry codes: (i) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+1]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); data reduction: SAINT; 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: SHELXL97 and 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: SU2640 ).


Acknowledgements

We are grateful to Dr C. R. Ramanathan, Department of Chemistry, Pondicherry University for support of this research. The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. ZF and DV acknowledge the UGC (SAP-CAS) for departmental facilities. ZF also thanks the UGC for a meritorious fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ha, Y. M., Kim, J., Parkl, Y. J., Park, D., Choi, Y. J., Kim, J. M., Chung, K. W., Han, Y. K., Park, J. Y., Lee, J. Y., Moon, H. R. & Chung, H. Y. (2011). Med. Chem. Commun. 2, 542-549.  [CrossRef] [ChemPort]
Kaminski, K., Rzepka, S. & Obniska, J. (2011). Bioorg. Med. Chem. Lett. 21, 5800-5803.  [ChemPort] [PubMed]
Khorasani, S. & Fernandes, M. A. (2012). Acta Cryst. E68, o1503.  [CSD] [CrossRef] [details]
Mayes, B. A., McGarry, P., Moussa, A. & Watkin, D. J. (2008). Acta Cryst. E64, o1355.  [CSD] [CrossRef] [details]
Obniska, J., Rzepka, S. & Kamin' ski, K. (2012). Bioorg. Med. Chem. 20, 4872-4880.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1489  [ doi:10.1107/S1600536813023751 ]

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.