6-Isopropyl-5-meth­oxy-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

Zeng, X.-H.; Wang, H.-M.; Deng, S.-H.; Chen, L.-L.

doi:10.1107/S1600536810041978

Volume 66
Part 11
Pages o2947-o2948
November 2010

Received 9 October 2010
Accepted 16 October 2010
Online 30 October 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.065
wR = 0.185
Data-to-parameter ratio = 11.3
Details

6-Isopropyl-5-methoxy-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

Xiao-Hua Zeng,^a Hong-Mei Wang,^a Shou-Heng Deng ^b ^* and Li-Li Chen ^a

^aInstitute of Medicinal Chemistry, Hubei Medical University, Shiyan 442000, People's Republic of China, and ^bCenter of Oncology, People's Hospital affiliated with Hubei Medical University, Shi Yan 442000, People's Republic of China
Correspondence e-mail: zken710@yahoo.com.cn

In the title compound, C₁₄H₁₅N₅O₂, the whole molecule apart from the terminal C atoms of the isopropyl group is located on a crystallographic mirror plane. An intramolecular C-HN hydrogen-bonding interaction may stabilize the molecular conformation. The crystal packing features weak slipped [pi] - [pi] interactions between the pyrimidine and the phenyl rings of symmetry-related molecules [centroid-centroid distance = 3.746 (1)Å, slippage of 1.574 Å].

Related literature

Fpr the biological activity of 8-azaguanine derivatives, see: Roblin et al. (1945); Ding et al. (2004); Mitchell et al. (1950); Levine et al. (1963); Montgomery et al. (1962); Yamamoto et al. (1967); Bariana (1971); Holland et al. (1975). For related structures, see: Chen & Shi (2006); Ferguson et al. (1998); Li et al. (2004); Maldonado et al. (2006); Wang et al. (2006); Xiao & Shi (2007); Zeng et al. (2006, 2009); Zhao, Hu et al. (2005); Zhao, Wang & Ding (2005); Zhao, Xie et al. (2005).

Experimental

Crystal data

C₁₄H₁₅N₅O₂
M_r = 285.31
Orthorhombic, P n m a
a = 14.921 (2) Å
b = 6.7989 (11) Å
c = 13.839 (2) Å
V = 1404.0 (4) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) T_min = 0.985, T_max = 0.991
7422 measured reflections
1418 independent reflections
1045 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.185
S = 1.07
1418 reflections
125 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2N4	0.93	2.37	3.021 (4)	127

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1999) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2610 ).

Acknowledgements

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (2003CB114400), the National Natural Science Foundation of China (20372023, 20102001), the Educational Commission of Hubei Province (grant Nos. B200624004, B20092412), the Shiyan Municipal Science and Technology Bureau (grant No. 20061835) and Hubei Medical University (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

References

Bariana, D. S. (1971). J. Med. Chem. 14, 535-543.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Chen, X.-B. & Shi, D.-Q. (2006). Acta Cryst. E62, o4780-o4782.
Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366-8371.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Ferguson, G., Low, J. N., Nogueras, M., Cobo, J., Lopez, M. D., Quijano, M. L. & Sanchez, A. (1998). Acta Cryst. C54, IUC9800031.
Holland, A., Jackson, D., Chaplen, P., Lunt, E., Marshall, S., Pain, C. L. & Wooldridge, K. R. H. (1975). Eur. J. Med. Chem. 10, 447-449.
Levine, R. J., Hall, T. C. & Harris, C. A. (1963). Cancer (N. Y.), 16, 269-272.
Li, M., Wen, L. R., Fu, W. J., Hu, F. Z. & Yang, H. Z. (2004). Chin. J. Struct. Chem. 23, 11-14.
Maldonado, C. R., Quirós, M. & Salas, J. M. (2006). Acta Cryst. C62, o489-o491.
Mitchell, J. H., Skipper, H. E. & Bennett, L. L. (1950). Cancer Res. 10, 647-649.
Montgomery, J. A., Schabel, F. M. & Skipper, H. E. (1962). Cancer Res. 22, 504-509.
Roblin, R. O., Lampen, J. O., English, J. P., Cole, Q. P. & Vaughan, J. R. (1945). J. Am. Chem. Soc. 67, 290-294.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, H.-M., Zeng, X.-H., Hu, Z.-Q., Li, G.-H. & Tian, J.-H. (2006). Acta Cryst. E62, o5038-o5040.
Xiao, L.-X. & Shi, D.-Q. (2007). Acta Cryst. E63, o2843.
Yamamoto, I., Inoki, R., Tamari, Y. & Iwatsubo, K. (1967). Jpn J. Pharmacol. 17, 140-142.
Zeng, X.-H., Liu, X.-L., Deng, S.-H., Chen, P. & Wang, H.-M. (2009). Acta Cryst. E65, o2583-o2584.
Zeng, X.-H., Wang, H.-M., Ding, M.-W. & He, H.-W. (2006). Acta Cryst. E62, o1888-o1890.
Zhao, J.-F., Hu, Y.-G., Ding, M.-W. & He, H.-W. (2005). Acta Cryst. E61, o2791-o2792.
Zhao, J. F., Wang, C. G. & Ding, M. W. (2005). Chin. J. Struct. Chem. 24, 439-444.
Zhao, J. F., Xie, C., Ding, M. W. & He, H. W. (2005). Chem. Lett. 34, 1020-1022.

organic compounds