4-[(E)-2-Furylmethyl­eneamino]-3-phenyl-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Jebas, S.R.; Sujith, K.V.; Patil, P.S.; Kalluraya, B.; Dharmaprakash, S.M.

doi:10.1107/S1600536808021806

Volume 64
Part 8
Pages o1528-o1529
August 2008

Received 11 July 2008
Accepted 13 July 2008
Online 19 July 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.126
Data-to-parameter ratio = 20.6
Details

4-[(E)-2-Furylmethyleneamino]-3-phenyl-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ⁺ K. V. Sujith,^b P. S. Patil,^c B. Kalluraya ^b and S. M. Dharmaprakash ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

In the title molecule, C₁₃H₁₀N₄OS, the triazole ring makes dihedral angles of 16.14 (9) and 58.51 (11)°, respectively, with the phenyl and furan rings. Intramolecular C-HN hydrogen bonds generate S(5) and S(6) ring motifs. In the crystal structure, centrosymmetrically related molecules are linked via N-HS hydrogen bonds to form dimeric pairs, which are interlinked via C-HO and C-H [pi] interactions.

Related literature

For the biological activities of triazole derivatives, see: Clemons et al. (2004); Glerman et al. (1997); Holla et al. (2003); Johnston (2002); Kane et al. (1990); Kkgzel et al. (2004); Modzelewska & Kalabun (1999); Rollas et al. (1993); Shujuan et al. (2004); For bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₃H₁₀N₄OS
M_r = 270.31
Orthorhombic, P b c n
a = 27.4006 (6) Å
b = 11.4940 (3) Å
c = 7.7886 (2) Å
V = 2452.96 (10) Å³
Z = 8
Mo K radiation
= 0.26 mm^-1
T = 100.0 (1) K
0.40 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.829, T_max = 0.974
40042 measured reflections
3627 independent reflections
2573 reflections with I > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.125
S = 1.05
3627 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3-C8 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1N1S1ⁱ	0.85 (2)	2.42 (2)	3.265 (2)	169 (2)
C4-H4AN2	0.93	2.55	2.859 (2)	100
C6-H6AO1ⁱⁱ	0.93	2.59	3.347 (2)	139
C8-H8AN4	0.93	2.29	2.942 (2)	126
C5-H5ACg1ⁱⁱⁱ	0.93	2.92	3.522 (2)	123
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2631 ).

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a postdoctoral research fellowship.

References

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organic compounds