6-(3-Pyrid­yl)-3-(3,4,5-trimethoxy­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Du, H.; Du, H.; An, Y.; Li, S.

doi:10.1107/S1600536808019855

Volume 64
Part 8
Page o1402
August 2008

Received 26 June 2008
Accepted 30 June 2008
Online 5 July 2008

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.109
Data-to-parameter ratio = 15.2
Details

6-(3-Pyridyl)-3-(3,4,5-trimethoxyphenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Haitang Du,^a ^* Haijun Du,^b Ying An ^c and Shengnan Li ^c

^aDepartment of Biology and Environment Technology, Guiyang College, Guiyang 550005, People's Republic of China,^bSchool of Chemistry and Environment Science, Guizhou University for Nationalities, Guiyang 550025, People's Republic of China, and ^cDepartment of Chemistry, College of Science, Tianjin University, Tianjin 300072, People's Republic of China
Correspondence e-mail: haitangdu@gz139.com.cn

In the molecule of the title compound, C₁₇H₁₅N₅O₃S, the planar central heterocylic ring system is oriented with respect to the benzene and pyridine rings at dihedral angles of 6.61 (3) and 19.22 (3)°, respectively. An intramolecular C-HN hydrogen bond results in the formation of a six-membered ring, adopting a flattened boat conformation. In the crystal structure, intermolecular C-HN hydrogen bonds link the molecules.

Related literature

For general background, see: Karabasanagouda et al. (2007); Mathew et al. (2007). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₇H₁₅N₅O₃S
M_r = 369.40
Monoclinic, P 2₁ /c
a = 7.4682 (15) Å
b = 14.128 (3) Å
c = 15.550 (3) Å
= 90.46 (3)°
V = 1640.6 (6) Å³
Z = 4
Mo K radiation
= 0.23 mm^-1
T = 113 (2) K
0.20 × 0.06 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.956, T_max = 0.991
18716 measured reflections
3620 independent reflections
3121 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.108
S = 1.17
3620 reflections
238 parameters
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2N4	0.95	2.40	3.0869 (19)	129
C9-H9AN1ⁱ	0.98	2.60	3.576 (2)	171
C8-H8CN5ⁱⁱ	0.98	2.63	3.573 (2)	161
C14-H14N2ⁱⁱⁱ	0.95	2.57	3.410 (2)	148
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2481 ).

Acknowledgements

The authors thank Guiyang College (grant No. 2008012) for financial support.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Karabasanagouda, T., Adhikari, A. V. & Shetty, S. N. (2007). Eur. J. Med. Chem. 42, 521-529.
Mathew, V., Keshavayya, J., Vaidya, V. P. & Giles, D. (2007). Eur. J. Med. Chem. 42, 823-840.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds