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

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

doi:10.1107/S160053681004300X

Volume 66
Part 11
Pages o2990-o2991
November 2010

Received 9 October 2010
Accepted 22 October 2010
Online 31 October 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.054
wR = 0.182
Data-to-parameter ratio = 13.2
Details

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

Hong-Mei Wang,^a Shou-Heng Deng,^b Xiao-Hua Zeng,^a ^* Ping Chen ^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, Shiyan 442000, People's Republic of China
Correspondence e-mail: zengken@126.com

In the title compound, C₂₁H₂₁N₅O₂, the triazolopyrimidine ring system is essentially planar [maximum displacement = 0.021 (4) Å] and forms dihedral angles of 41.17 (9) and 67.99 (8)° with the phenyl and benzene rings, respectively. The n-butyl side chains is disordered over two positions with an ccupancy ratio of 0.77:0.23. An intramolecular C-HO hydrogen-bonding interaction stabilizes the molecular conformation. In the crystal, molecules are linked by intermolecular C-HO and C-HN hydrogen bonds into a three-dimensional network. In addition, [pi] - [pi] stacking interactions involving the triazole and pyrimidine rings of adjacent molecules are observed, with centroid-centroid distances of 3.545 (1) Å.

Related literature

For the synthesis and 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); Zeng et al. (2010). For related structures, see: Ferguson et al. (1998); Li et al. (2004); Zhao, Xie et al. (2005); Zhao, Hu et al. (2005); Zhao, Wang & Ding (2005); Chen & Shi (2006); Maldonado et al. (2006); Xiao et al. (2007); Wang et al. (2006, 2008); Zeng et al. (2006, 2009).

Experimental

Crystal data

C₂₁H₂₁N₅O₂
M_r = 375.43
Monoclinic, P 2₁ /n
a = 11.0954 (10) Å
b = 16.4478 (15) Å
c = 11.3484 (11) Å
= 107.643 (1)°
V = 1973.6 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.983, T_max = 0.985
20458 measured reflections
3876 independent reflections
2663 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.182
S = 1.08
3876 reflections
293 parameters
11 restraints
H-atom parameters constrained
_max = 0.56 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12AO2	0.97	2.50	3.048 (5)	116
C2-H2O1ⁱ	0.93	2.53	3.230 (3)	133
C3-H3N2ⁱⁱ	0.93	2.61	3.535 (2)	174
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: 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: RZ2502 ).

Acknowledgements

The authors 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 of China (grant No. B200624004, B20092412), Shiyan Municipal Science and Technology Bureau (grant No. 20061835) and Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

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organic compounds