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Volume 69 
Part 10 
Page o1534  
October 2013  

Received 15 July 2013
Accepted 29 August 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.160
Data-to-parameter ratio = 20.7
Details
Open access

4-Hydroxy-6-methylpyridin-2(1H)-one

aCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500, Tijuana, B.C., Mexico
Correspondence e-mail: dchavez@tectijuana.mx

In the crystal structure of the title compound, C6H7NO2, N-H...O and O-H...O hydrogen bonds link the molecules, forming a zigzag array along [001] and a layer structure parallel to the ab plane.

Related literature

For the potential of related compounds in anti-HIV treatment, see: De Clercq (2005[De Clercq, E. (2005). J. Med. Chem. 48, 1297-1313.]); Dollé et al. (1995[Dollé, V., Fan, E., Nguyen, C. H., Aubertin, A.-M., Kirn, A., Andreola, M. L., Jamieson, G., Tarrago-Litvak, L. & Bisagni, E. (1995). J. Med. Chem. 38, 4679-4686.]); Medina-Franco et al. (2007[Medina-Franco, J. L., Martinez-Mayorga, K., Juárez-Gordiano, C. & Castillo, R. (2007). ChemMedChem, 2, 1141-1147.]).

[Scheme 1]

Experimental

Crystal data
  • C6H7NO2

  • Mr = 125.13

  • Monoclinic, P 21 /n

  • a = 4.7082 (5) Å

  • b = 12.2988 (8) Å

  • c = 10.0418 (7) Å

  • [beta] = 91.303 (7)°

  • V = 581.32 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.65 × 0.20 × 0.18 mm

Data collection
  • Bruker P4 diffractometer

  • Absorption correction: [psi] scan (XSCANS; Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.216, Tmax = 0.259

  • 2445 measured reflections

  • 1701 independent reflections

  • 1269 reflections with I > 2[sigma](I)

  • Rint = 0.026

  • 3 standard reflections every 97 reflections intensity decay: 9.4%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.160

  • S = 1.06

  • 1701 reflections

  • 82 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 1.98 2.835 (2) 175
O2-H2B...O1ii 0.82 1.79 2.609 (2) 180
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: XSCANS (Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2437 ).


Acknowledgements

We gratefully acknowledge support for this project by the Dirección General de Educación Superior Tecnológica (DGEST grants 2535.09P and 3604.10-P).

References

De Clercq, E. (2005). J. Med. Chem. 48, 1297-1313.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Dollé, V., Fan, E., Nguyen, C. H., Aubertin, A.-M., Kirn, A., Andreola, M. L., Jamieson, G., Tarrago-Litvak, L. & Bisagni, E. (1995). J. Med. Chem. 38, 4679-4686.  [ChemPort] [PubMed] [Web of Science]
Medina-Franco, J. L., Martinez-Mayorga, K., Juárez-Gordiano, C. & Castillo, R. (2007). ChemMedChem, 2, 1141-1147.  [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.


Acta Cryst (2013). E69, o1534  [ doi:10.1107/S1600536813024240 ]

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