N-[(4-Amino-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-3-yl)meth­yl]-4-methyl­benzamide

Fun, H.-K.; Yeap, C.S.; Mange, Y.; Isloor, A.M.; Hegde, C.

doi:10.1107/S1600536810035014

Volume 66
Part 10
Pages o2501-o2502
October 2010

Received 30 August 2010
Accepted 31 August 2010
Online 4 September 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 19.8
Details

N-[(4-Amino-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-methylbenzamide

Hoong-Kun Fun,^a ^*⁺ Chin Sing Yeap,^a ⁺⁺ Yatin Mange,^b Arun M. Isloor ^b and Chitrakar Hegde ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^cDepartment of Chemistry, NITTE Meenakshi Institute of Technology, Yelahanka, Bangalore, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₁H₁₃N₅OS, the dihedral angle between the triazole ring and the benzene ring is 84.21 (7)°. The amino group adopts a pyramidal configuration. An intramolecular N-HO hydrogen bond stabilizes the molecular structure and generates an S(8) ring. In the crystal, molecules are linked by intermolecular N-HO, N-HS, N-HN and C-HS hydrogen bonds into layers lying parallel to the bc plane. The crystal structure is further stabilized by aromatic [pi] - [pi] stacking interactions [centroid-centroid distance = 3.3330 (7) Å].

Related literature

For applications of 1,2,4-triazole derivatives, see: Demirbas et al. (2002, 2004); Tozkoparan et al. (2000); Turan-Zitouni et al. (1999); Kritsanida et al. (2002); Holla et al. (2002); Foroumadi et al. (2003); Isloor et al. (2009); Shujuan et al. (2004); Verreck et al. (2003); Clemons et al. (2004). For related structures, see: Fun et al. (2009a,b). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₁H₁₃N₅OS
M_r = 263.32
Monoclinic, P 2₁ /c
a = 14.8148 (1) Å
b = 8.6702 (1) Å
c = 9.8534 (1) Å
= 104.923 (1)°
V = 1222.96 (2) Å³
Z = 4
Mo K radiation
= 0.26 mm^-1
T = 100 K
0.30 × 0.27 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.926, T_max = 0.972
15018 measured reflections
3555 independent reflections
3142 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.093
S = 1.07
3555 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O1ⁱ	0.841 (18)	2.187 (17)	2.9824 (14)	157.7 (17)
N3-H1N3S1ⁱⁱ	0.851 (19)	2.524 (19)	3.2168 (11)	139.2 (15)
N3-H1N3N5ⁱⁱ	0.851 (19)	2.276 (18)	2.9738 (15)	139.3 (16)
N5-H1N5O1	0.843 (19)	2.169 (18)	2.9587 (15)	155.9 (16)
N5-H2N5S1ⁱⁱⁱ	0.880 (18)	2.666 (18)	3.5381 (12)	171.2 (14)
C8-H8AS1^iv	0.97	2.87	3.4456 (12)	119
Symmetry codes: (i) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5629 ).

Acknowledgements

HKF thanks Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160. CSY thanks USM for the award of a USM Fellowship. AMI is thankful to the Head of the Department of Chemistry and the Director of the National Institute of Technology-Karnataka, Surathkal, India, for providing the research facilities and encouragement.

References

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organic compounds