4-[(E)-2,6-Dichloro­benzyl­ideneamino]-3-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Chantrapromma, S.; Sujith, K.V.; Patil, P.S.; Kalluraya, B.; Muralidharan, A.; Dharmaprakash, S.M.

doi:10.1107/S1600536808021272

Volume 64
Part 8
Pages o1503-o1504
August 2008

Received 7 July 2008
Accepted 9 July 2008
Online 16 July 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.136
Data-to-parameter ratio = 23.6
Details

4-[(E)-2,6-Dichlorobenzylideneamino]-3-{1-[4-(2-methylpropyl)phenyl]ethyl}-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^* Suchada Chantrapromma,^b ⁺ K. V. Sujith,^c P. S. Patil,^d B. Kalluraya,^c A. Muralidharan ^e and S. M. Dharmaprakash ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India,^dDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^eDepartment of Chemistry, Nehru Arts & Science College, Kanhangad, Kerala 671 328, India
Correspondence e-mail: hkfun@usm.my

In the title Schiff base compound, C₂₁H₂₂Cl₂N₄S, the triazole ring makes dihedral angles of 2.15 (11) and 87.48 (11)° with the 2,6-dichlorophenyl and methylpropylphenyl rings, respectively. Weak intramolecular C-HS and C-HCl interactions generate S(6) and S(5) ring motifs, respectively. In the crystal structure, centrosymmetrically related molecules are linked into dimers by N-HS hydrogen bonds. These dimers are arranged into sheets parallel to the ab plane and are stacked along the c axis. C-H [pi] interactions involving the methylpropylphenyl ring and [pi] - [pi] interactions involving the dichlorophenyl ring [centroid-centroid distance = 3.5865 (3) Å] are also observed.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2008a,b). For background to the activities and applications of 1,2,4-triazole derivatives, see: Almasirad et al. (2004); Al-Soud et al. (2003); Amir & Shikha (2004); Holla et al. (2003); Kawashima et al. (1987); Palaska et al. (2002); Walczak et al. (2004); Zitouni et al. (2005).

Experimental

Crystal data

C₂₁H₂₂Cl₂N₄S
M_r = 433.40
Triclinic, $[P \overline 1]$
a = 8.6190 (2) Å
b = 9.4441 (2) Å
c = 14.4244 (4) Å
= 104.669 (2)°
= 95.492 (2)°
= 110.418 (1)°
V = 1042.33 (5) Å³
Z = 2
Mo K radiation
= 0.43 mm^-1
T = 100.0 (1) K
0.29 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.887, T_max = 0.934
19865 measured reflections
6032 independent reflections
4139 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.136
S = 1.00
6032 reflections
256 parameters
H-atom parameters constrained
_max = 0.59 e Å^-3
_min = -0.47 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
N2-H2AS1ⁱ	0.86	2.44	3.2849 (19)	169
C10-H10ACl2	0.93	2.62	2.978 (2)	104
C10-H10AS1	0.93	2.52	3.2066 (19)	131
C15-H15ACg1ⁱⁱ	0.93	2.94	3.793 (3)	154
Symmetry codes: (i) -x+2, -y-1, -z; (ii) -x+1, -y, -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: CI2627 ).

Acknowledgements

KVS, BK and AM are grateful to Kerala State Council for Science Technology and Environment, Thiruvananthapuram, for financial assistance. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
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organic compounds