4-(4-Bromo­phen­yl)-1-(2,6-difluoro­benz­yl)-3-(3,4,5-trimeth­oxy­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Ooi, C.W.; Chandrakantha, B.; Isloor, A.M.; Shetty, P.

doi:10.1107/S1600536811052330

Volume 68
Part 1
Page o89
January 2012

Received 3 December 2011
Accepted 4 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.048
wR = 0.158
Data-to-parameter ratio = 22.7
Details

4-(4-Bromophenyl)-1-(2,6-difluorobenzyl)-3-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^*⁺ Chin Wei Ooi,^a B. Chandrakantha,^b Arun M. Isloor ^c and Prakash Shetty ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Chemistry, Manipal Institute of Technology, Manipal 576 104, India,^cMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₂₄H₂₀BrF₂N₃O₃S, the triazole ring (r.m.s. deviation = 0.0107 Å) makes dihedral angles of 28.18 (14), 63.76 (14) and 77.01 (18)°, respectively, with the trimethoxy-, bromo-, and difluoro-substituted benzene rings. The C atoms of the meta methoxy groups are roughly coplanar with their ring [displacements = -0.289 (4) and 0.083 (7) Å], whereas the C atom of the para group is displaced [1.117 (3) Å]. In the crystal, inversion dimers linked by two pairs of C-HO hydrogen bonds occur. The ring motif of the two hydrogen bonds to their symmetry-generated O-atom acceptors is R₂²(8).

Related literature

For a related structure and background to 1,2,4-triazole derivatives, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₄H₂₀BrF₂N₃O₃S
M_r = 548.40
Monoclinic, C 2/c
a = 17.6694 (18) Å
b = 15.5299 (16) Å
c = 18.0855 (19) Å
= 102.955 (2)°
V = 4836.4 (9) Å³
Z = 8
Mo K radiation
= 1.83 mm^-1
T = 296 K
0.63 × 0.34 × 0.21 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.391, T_max = 0.703
20567 measured reflections
7051 independent reflections
3435 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.158
S = 1.00
7051 reflections
310 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13AO1ⁱ	0.93	2.54	3.284 (3)	137
C14-H14AO2ⁱ	0.93	2.40	3.142 (3)	137
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

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: HB6551 ).

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO thanks the Malaysian Government and USM for the award of the post of research assistant under the Research University Grant (1001/PFIZIK/811151). AMI thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Asik, S. I. J., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2011). Acta Cryst. E67, o3422-o3423.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds