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Volume 68 
Part 11 
Pages o3240-o3241  
November 2012  

Received 21 October 2012
Accepted 22 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.076
Data-to-parameter ratio = 13.4
Details
Open access

3-[(R)-1-Hydroxybutan-2-yl]-1,2,3-benzotriazin-4(3H)-one

aDepartamento de Ciencias Químico Bilógicas, Universidad de Sonora, Hermosillo, Sonora, 83000 México,bInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México D.F., 04510 México, and cCentro de Graduados e Investigación, Instituto Tecnológico de Tijuana, Tijuana, B.C., 22500 México
Correspondence e-mail: fernando.rocha@guayacan.uson.mx, miguelhake@yahoo.com

The crystal structure of the title compound, C11H13N3O2, is stabilized by O-H...O hydrogen bonds, which link the molecules into chains along [100].

Related literature

For biological and synthetic applications of benzo-1,2,3-triazinones, see: Caliendo et al. (1999[Caliendo, G., Fiorino, F., Grieco, P., Perissutti, E., Santagada, V., Meli, R., Mattace-Raso, G., Zanesco, A. & De Nucci, G. (1999). Eur. J. Med. Chem. 34, 1043-1051.]); Zheng et al. (2005[Zheng, G. Z., Bhatia, P., Daanen, J., Kolasa, T., Patel, M., Latshaw, S., El Kouhen, O. F., Chang, R., Uchic, M. E., Miller, L., Nakane, M., Lehto, S. J., Honore, M. P., Moreland, R. B., Brioni, J. D. & Stewart, A. O. (2005). J. Med. Chem. 48, 7374-7388.]); Vaisburg et al. (2004[Vaisburg, A., Bernstein, N., Frechette, S., Allan, M., Abou-Khalil, E., Leit, S., Moradei, O., Bouchain, G., Wang, J., Hyung Woo, S., Fournel, M., Yan, P. T., Trachy-Bourget, M.-C., Kalita, A., Beaulieu, C., Li, Z., MacLeod, A. R., Bestermanb, J. M. & Delormea, D. (2004). Bioorg. Med. Chem. Lett. 14, 283-287.]); Chollet et al. (2002[Chollet, A. M., Le Diguarher, T., Kucharczyk, N., Oynel, A., Bertrand, M., Tucker, G., Guilbaud, N., Burbridge, M., Pastoureau, P., Fradin, A., Sabatini, M., Fauchére, J.-L. & Casara, P. (2002). Bioorg. Med. Chem. 10, 531-544.]); Le Diguarher et al. (2003[Le Diguarher, T., Chollet, A. M., Bertrand, M., Henning, P., Raimbaud, E., Sabatini, M. N., Guilbaud, N., Pierré, A., Tucker, G. C. & Casara, P. (2003). J. Med. Chem. 46, 3840-3852.]); Clark et al. (1995[Clark, A. S., Deans, B., Stevens, M. F. G., Tisdale, M. J., Wheelhouse, R. T., Denny, B. J. & Hartley, J. A. (1995). J. Med. Chem. 38, 1493-1504.]); Carpino et al. (2004[Carpino, L. A., Xia, J., Zhang, C. & El-Faham, A. (2004). J. Org. Chem. 69, 62-71.]); Janout et al. (2003[Janout, V., Jing, B., Staina, I. V. & Regen, S. L. (2003). J. Am. Chem. Soc. 125, 4436-4437.]); Gierasch et al. (2000[Gierasch, T. M., Chytil, M., Didiuk, M. T., Park, J. Y., Urban, J. J., Nolan, S. P. & Verdine, G. L. (2000). Org. Lett. 2, 3999-4002.]). For structures of benzo-1,2,3-triazinones, see: Hjortås et al. (1973[Hjortås, J. (1973). Acta Cryst. B29, 1916-1922.]); Hunt et al. (1983[Hunt, W. E., Schwalbe, C. H. & Vaughan, K. (1983). Acta Cryst. C39, 738-740.]); Reingruber et al. (2009[Reingruber, R., Vanderheiden, S., Muller, T., Nieger, M., Es-Sayed, M. & Bräse, S. (2009). Tetrahedron Lett. 50, 3439-3442.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, V., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the synthesis, see: Gómez et al. (2005[Gómez, M., Jansat, S., Muller, G., Aullón, G. & Maestro, M. A. (2005). Eur. J. Inorg. Chem. pp. 4341-4351.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13N3O2

  • Mr = 219.24

  • Orthorhombic, P 21 21 21

  • a = 8.9668 (13) Å

  • b = 10.1506 (15) Å

  • c = 12.0238 (17) Å

  • V = 1094.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.32 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 9057 measured reflections

  • 2000 independent reflections

  • 1700 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.076

  • S = 0.93

  • 2000 reflections

  • 149 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.85 (1) 2.03 (1) 2.8712 (19) 171 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZJ2097 ).


Acknowledgements

We gratefully acknowledge support for this project by the Consejo Nacional de Ciencia y Tecnología (CONACyT grant 36435-E) and Consejo del Sistema Nacional de Educación Tecnológica (COSNET) grant 486-02-P. The authors are indebted to Adrián Ochoa Terán and Ignacio Rivero Espejel for their analytical support of this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, V., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Caliendo, G., Fiorino, F., Grieco, P., Perissutti, E., Santagada, V., Meli, R., Mattace-Raso, G., Zanesco, A. & De Nucci, G. (1999). Eur. J. Med. Chem. 34, 1043-1051.  [CrossRef] [ChemPort]
Carpino, L. A., Xia, J., Zhang, C. & El-Faham, A. (2004). J. Org. Chem. 69, 62-71.  [CrossRef] [PubMed] [ChemPort]
Chollet, A. M., Le Diguarher, T., Kucharczyk, N., Oynel, A., Bertrand, M., Tucker, G., Guilbaud, N., Burbridge, M., Pastoureau, P., Fradin, A., Sabatini, M., Fauchére, J.-L. & Casara, P. (2002). Bioorg. Med. Chem. 10, 531-544.  [CrossRef] [PubMed] [ChemPort]
Clark, A. S., Deans, B., Stevens, M. F. G., Tisdale, M. J., Wheelhouse, R. T., Denny, B. J. & Hartley, J. A. (1995). J. Med. Chem. 38, 1493-1504.  [CrossRef] [ChemPort] [PubMed] [ISI]
Gierasch, T. M., Chytil, M., Didiuk, M. T., Park, J. Y., Urban, J. J., Nolan, S. P. & Verdine, G. L. (2000). Org. Lett. 2, 3999-4002.  [CrossRef] [PubMed] [ChemPort]
Gómez, M., Jansat, S., Muller, G., Aullón, G. & Maestro, M. A. (2005). Eur. J. Inorg. Chem. pp. 4341-4351.
Hjortås, J. (1973). Acta Cryst. B29, 1916-1922.  [CrossRef] [details]
Hunt, W. E., Schwalbe, C. H. & Vaughan, K. (1983). Acta Cryst. C39, 738-740.  [CrossRef] [details]
Janout, V., Jing, B., Staina, I. V. & Regen, S. L. (2003). J. Am. Chem. Soc. 125, 4436-4437.  [CrossRef] [PubMed] [ChemPort]
Le Diguarher, T., Chollet, A. M., Bertrand, M., Henning, P., Raimbaud, E., Sabatini, M. N., Guilbaud, N., Pierré, A., Tucker, G. C. & Casara, P. (2003). J. Med. Chem. 46, 3840-3852.  [CrossRef] [PubMed] [ChemPort]
Reingruber, R., Vanderheiden, S., Muller, T., Nieger, M., Es-Sayed, M. & Bräse, S. (2009). Tetrahedron Lett. 50, 3439-3442.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vaisburg, A., Bernstein, N., Frechette, S., Allan, M., Abou-Khalil, E., Leit, S., Moradei, O., Bouchain, G., Wang, J., Hyung Woo, S., Fournel, M., Yan, P. T., Trachy-Bourget, M.-C., Kalita, A., Beaulieu, C., Li, Z., MacLeod, A. R., Bestermanb, J. M. & Delormea, D. (2004). Bioorg. Med. Chem. Lett. 14, 283-287.  [CrossRef] [PubMed] [ChemPort]
Zheng, G. Z., Bhatia, P., Daanen, J., Kolasa, T., Patel, M., Latshaw, S., El Kouhen, O. F., Chang, R., Uchic, M. E., Miller, L., Nakane, M., Lehto, S. J., Honore, M. P., Moreland, R. B., Brioni, J. D. & Stewart, A. O. (2005). J. Med. Chem. 48, 7374-7388.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3240-o3241   [ doi:10.1107/S1600536812043802 ]

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