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Volume 68 
Part 11 
Pages o3235-o3236  
November 2012  

Received 2 October 2012
Accepted 24 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.111
Data-to-parameter ratio = 19.7
Details
Open access

2-Ethyl-3-hydroxy-1-isopropyl-4-pyridone

aDepartment of Chemistry, University of Free State, Bloemfontein, 9301, PO Box 339, South Africa
Correspondence e-mail: schuttem@ufs.ac.za

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-H...O 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-H...O hydrogen bonds. This results in the formation of a three-dimensional network structure.

Related literature

For background on this type of ligand system, see: Fassihi et al. (2009[Fassihi, A., Abedi, D., Saghaie, L., Sabet, R., Fazeli, H., Bostaki, G., Deilami, O. & Sadinpour, H. (2009). Eur. J. Med. Chem. 44, 2145-2157.]); Weinberg (1994[Weinberg, G. A. (1994). Antimicrob. Agents Chemother. 38, 997-1003.]); Galanello, 2007[Galanello, R. (2007). Ther. Clin. Risk Manage. 3, 795-805.]); Scott et al. (2008[Scott, L. E., Page, B. D. G., Patrick, B. O. & Orvig, C. (2008). Dalton Trans. pp. 6364-6367.]). For similar structures, see: Xiao et al. (1992[Xiao, G., van der Helm, D., Hider, R. C. & Dobbin, P. S. (1992). J. Chem. Soc. Dalton Trans. pp. 3265-3271.]); Burgess et al. (1993[Burgess, J., Fawcett, J., Patel, M. S. & Russell, D. R. (1993). J. Chem. Res. (S). pp. 50-51.]); Hider et al. (1990[Hider, R. C., Taylor, P. D., Walkinshaw, M., Wang, J. L. & van der Helm, D. (1990). J. Chem. Res. (S), pp. 316-317.]); Dobbin et al. (1993[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.]); Brown et al. (1995[Brown, S. D., Burgess, J., Fawcett, J., Parsons, S. A., Russell, D. R. & Waltham, E. (1995). Acta Cryst. C51, 1335-1338.]).

[Scheme 1]

Experimental

Crystal data
  • C10H15NO2

  • Mr = 181.23

  • Orthorhombic, P b c a

  • a = 11.7408 (2) Å

  • b = 13.3554 (2) Å

  • c = 37.5523 (8) Å

  • V = 5888.32 (18) Å3

  • Z = 24

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.43 × 0.32 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.986

  • 66795 measured reflections

  • 7343 independent reflections

  • 5939 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.111

  • S = 1.01

  • 7343 reflections

  • 373 parameters

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2A-H2A...O1Ci 0.89 (2) 1.85 (2) 2.6503 (13) 149.9 (17)
O2B-H2B...O1Bii 0.882 (19) 1.859 (18) 2.6480 (13) 147.8 (17)
O2C-H2C...O1Aiii 0.869 (18) 1.796 (18) 2.5868 (12) 150.3 (17)
C5B-H5B...O1Cii 0.95 2.43 3.3237 (16) 156
C6C-H6C...O2Civ 1.00 2.59 3.4623 (15) 146
C9B-H9B1...O1Bv 0.99 2.44 3.3548 (16) 153
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+1; (iii) x-1, y, z; (iv) [x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (v) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2508 ).


Acknowledgements

The University of the Free State, the Chemistry Department, the NRF and Sasol Ltd and Inkaba yeAfrica are greatly acknowledged for funding.

References

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.  [CrossRef] [details]
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.  [CrossRef] [ChemPort] [PubMed] [ISI]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Fassihi, A., Abedi, D., Saghaie, L., Sabet, R., Fazeli, H., Bostaki, G., Deilami, O. & Sadinpour, H. (2009). Eur. J. Med. Chem. 44, 2145-2157.  [ISI] [CrossRef] [PubMed] [ChemPort]
Galanello, R. (2007). Ther. Clin. Risk Manage. 3, 795-805.  [ChemPort]
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.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Weinberg, G. A. (1994). Antimicrob. Agents Chemother. 38, 997-1003.  [CrossRef] [ChemPort] [PubMed]
Xiao, G., van der Helm, D., Hider, R. C. & Dobbin, P. S. (1992). J. Chem. Soc. Dalton Trans. pp. 3265-3271.  [CrossRef]


Acta Cryst (2012). E68, o3235-o3236   [ doi:10.1107/S1600536812044091 ]

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