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Volume 69 
Part 3 
Page o372  
March 2013  

Received 20 November 2012
Accepted 30 January 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.162
Data-to-parameter ratio = 19.8
Details
Open access

[4-(4-Methoxyphenyl)-1-methyl-3-nitropyrrolidin-3-yl]methanol

aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, Tamilnadu, India
Correspondence e-mail: guqmc@yahoo.com

In the title compound, C13H18N2O4, the dihedral angle between the benzene and pyrrolidine (all atoms) rings is 70.6 (1)°. The pyrrolidine ring adopts a half-chair conformation. In the crystal, molecules form chains along the c-axis direction linked by O-H...N hydrogen bonds, which are then connected by C-H...O interactions, forming a sheet parallel to the bc plane.

Related literature

For information on the pyrrolidine ring in biologically active natural compounds, see: Gu et al. (2004[Gu, Y. G., Zhang, X., Clark, R. F., Djuric, S. & Ma, Z. (2004). Tetrahedron Lett. 45, 3051-3053.]). For the use of pyrrolidine-containing molecules in the treatment of diseases, see, for example: Horri et al. (1986[Horri, S., Fukase, H., Matsuo, T., Kameda, Y., Asano, N. & Matsui, K. (1986). J. Med. Chem. 29, 1038-1046.]) for diabetes and Karpas et al. (1988[Karpas, A., Fleet, G. W. J., Dwek, R. A., Petursson, S., Mamgoong, S. K., Ramsden, N. G., Jacob, G. S. & Rademacher, T. W. (1988). Proc. Natl Acad. Sci. USA, 85, 9229-9233.]) for viral infections. For bond lengths in a related structure, see: Jayabharathi et al. (2009[Jayabharathi, J., Thanikachalam, V. & Saravanan, K. (2009). J. Photochem. Photobiol. A, 208, 13-20.]).

[Scheme 1]

Experimental

Crystal data
  • C13H18N2O4

  • Mr = 266.29

  • Monoclinic, P 21 /c

  • a = 11.6827 (10) Å

  • b = 11.1912 (11) Å

  • c = 11.1789 (11) Å

  • [beta] = 109.118 (2)°

  • V = 1381.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.22 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • 12464 measured reflections

  • 3407 independent reflections

  • 2282 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.162

  • S = 1.01

  • 3407 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 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
O2-H2...N1i 0.82 2.01 2.8237 (16) 170
C1-H1A...O2ii 0.96 2.51 3.390 (2) 153
C3-H3...O3iii 0.93 2.51 3.429 (2) 171
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. 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: 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: NK2193 ).


Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data collection and computer facilities.

References

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gu, Y. G., Zhang, X., Clark, R. F., Djuric, S. & Ma, Z. (2004). Tetrahedron Lett. 45, 3051-3053.  [ISI] [CrossRef] [ChemPort]
Horri, S., Fukase, H., Matsuo, T., Kameda, Y., Asano, N. & Matsui, K. (1986). J. Med. Chem. 29, 1038-1046.  [PubMed] [ISI]
Jayabharathi, J., Thanikachalam, V. & Saravanan, K. (2009). J. Photochem. Photobiol. A, 208, 13-20.  [CrossRef] [ChemPort]
Karpas, A., Fleet, G. W. J., Dwek, R. A., Petursson, S., Mamgoong, S. K., Ramsden, N. G., Jacob, G. S. & Rademacher, T. W. (1988). Proc. Natl Acad. Sci. USA, 85, 9229-9233.  [CrossRef] [ChemPort] [PubMed]
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, o372  [ doi:10.1107/S1600536813003073 ]

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