Received 2 October 2012
The title compound, C10H15NO2, crystallized with three molecules in the asymmetric unit. These three molecules are quite similar except for slight differences in the torsion angles of the substituents on the ring. The isopropyl C-C-N-C torsion angles (towards the carbon next to the ethyl bound carbon), for example, are -150.63 (11), -126.77 (13) and -138.76 (11)° for molecules A, B and C, respectively, and the C-C-C-N torsion angles involving the ethyl C atoms are 102.90 (13), 87.81 (14) and 86.47 (13)°. The main difference between the three molecules lies in the way they are arranged in the solid-state structure. All three molecules form dimers that are connected through strong O-HO hydrogen bonds with R22(10) graph-set motifs. The symmetry of the dimers formed does however differ between molecules. Molecules B connect with each other to form inversion dimers. Molecules A and C, on the other hand, form dimers with local twofold symmetry, but the two molecules are crystallographically distinct. The B and C molecules are linked to themselves and to each other via C-HO hydrogen bonds. This results in the formation of a three-dimensional network structure.
For background on this type of ligand system, see: Fassihi et al. (2009); Weinberg (1994); Galanello, 2007); Scott et al. (2008). For similar structures, see: Xiao et al. (1992); Burgess et al. (1993); Hider et al. (1990); Dobbin et al. (1993); Brown et al. (1995).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2508 ).
The University of the Free State, the Chemistry Department, the NRF and Sasol Ltd and Inkaba yeAfrica are greatly acknowledged for funding.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brown, S. D., Burgess, J., Fawcett, J., Parsons, S. A., Russell, D. R. & Waltham, E. (1995). Acta Cryst. C51, 1335-1338.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burgess, J., Fawcett, J., Patel, M. S. & Russell, D. R. (1993). J. Chem. Res. (S). pp. 50-51.
Dobbin, P. S., Hider, R. C., Hall, A. D., Taylor, P. D., Sarpong, P., Porter, J. B., Xiao, G., Xiao, G. & van der Helm, D. (1993). J. Med. Chem. 36, 2448-2458.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Fassihi, A., Abedi, D., Saghaie, L., Sabet, R., Fazeli, H., Bostaki, G., Deilami, O. & Sadinpour, H. (2009). Eur. J. Med. Chem. 44, 2145-2157.
Galanello, R. (2007). Ther. Clin. Risk Manage. 3, 795-805.
Hider, R. C., Taylor, P. D., Walkinshaw, M., Wang, J. L. & van der Helm, D. (1990). J. Chem. Res. (S), pp. 316-317.
Scott, L. E., Page, B. D. G., Patrick, B. O. & Orvig, C. (2008). Dalton Trans. pp. 6364-6367.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Weinberg, G. A. (1994). Antimicrob. Agents Chemother. 38, 997-1003.
Xiao, G., van der Helm, D., Hider, R. C. & Dobbin, P. S. (1992). J. Chem. Soc. Dalton Trans. pp. 3265-3271.