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

Rocha-Alonzo, F.; Morales-Morales, D.; Hernández-Ortega, S.; Reyes-Martínez, R.; Parra-Hake, M.

doi:10.1107/S1600536812043802

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 (C-C) = 0.002 Å
R = 0.034
wR = 0.076
Data-to-parameter ratio = 13.4
Details

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

Fernando Rocha-Alonzo,^a ^* David Morales-Morales,^b Simón Hernández-Ortega,^b Reyna Reyes-Martínez ^b and Miguel Parra-Hake ^c ^*

^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-HO 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); Zheng et al. (2005); Vaisburg et al. (2004); Chollet et al. (2002); Le Diguarher et al. (2003); Clark et al. (1995); Carpino et al. (2004); Janout et al. (2003); Gierasch et al. (2000). For structures of benzo-1,2,3-triazinones, see: Hjortås et al. (1973); Hunt et al. (1983); Reingruber et al. (2009). For bond-length data, see: Allen et al. (1987). For the synthesis, see: Gómez et al. (2005).

Experimental

Crystal data

C₁₁H₁₃N₃O₂
M_r = 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 radiation
= 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(I)
R_int = 0.044

Refinement

R[F² > 2(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
_max = 0.11 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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

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Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
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organic compounds