N-(2-Chloro­phen­yl)-2-({5-[4-(methyl­sulfan­yl)benz­yl]-4-phenyl-4H-1,2,4-triazol-3-yl}sulfan­yl)acetamide

Hoong-Kun Fun; Chin Sing Yeap; K Manjunath; D Jagadeesh Prasad; Boja Poojary

doi:10.1107/S1600536811027565

. 2011 Jul 16;67(Pt 8):o2063. doi: 10.1107/S1600536811027565

N-(2-Chlorophenyl)-2-({5-[4-(methylsulfanyl)benzyl]-4-phenyl-4H-1,2,4-triazol-3-yl}sulfanyl)acetamide

Hoong-Kun Fun ^a,^*,^‡, Chin Sing Yeap ^a,^§, K Manjunath ^b, D Jagadeesh Prasad ^b, Boja Poojary ^b

PMCID: PMC3213509 PMID: 22091088

Abstract

In the title molecule, C₂₄H₂₁ClN₄OS₂, the central 1,2,4-triazole ring forms dihedral angles of 89.05 (9), 86.66 (9) and 82.70 (10)° with the chloro-substituted benzene ring, the methylsulfanyl-substituted benzene ring and the phenyl ring, respectively. In the crystal, molecules are linked into sheets parallel to (100) by intermolecular N—H⋯N and weak C—H⋯O hydrogen bonds.

Related literature

For general background to and applications of 1,2,4-triazole derivatives, see: Holla et al. (2002 ▶, 2003 ▶); Rudnicka et al. (1986 ▶); Burch & Smith (1966 ▶); Kalyoncuoglu et al. (1992 ▶); Mhasalkar et al. (1970 ▶); Mir et al. (1970 ▶).

Experimental

Crystal data

C₂₄H₂₁ClN₄OS₂
M _r = 481.02
Monoclinic,
a = 14.2542 (7) Å
b = 16.3273 (9) Å
c = 10.1584 (6) Å
β = 96.372 (1)°
V = 2349.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 297 K
0.52 × 0.27 × 0.22 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.832, T _max = 0.924
29877 measured reflections
7900 independent reflections
5235 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.159
S = 1.05
7900 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.45 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027565/lh5283sup1.cif

e-67-o2063-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027565/lh5283Isup2.hkl

e-67-o2063-Isup2.hkl^{(386.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811027565/lh5283Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N3ⁱ	0.94	2.04	2.9787 (19)	174
C8—H8A⋯O1ⁱⁱ	0.97	2.52	3.147 (2)	123
C11—H11B⋯O1ⁱⁱⁱ	0.97	2.47	3.416 (2)	165

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

HKF and CSY thank Universiti Sains Malaysia for the Research University Grant 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

1,2,4-Triazole compounds show a broad spectrum of biological activities, possibly due to the presence of the N–C–S group (Holla et al., 2002). Among the 1,2,4-triazoles, the mercapto-thione-substituted 1,2,4-triazole ring systems have been well studied and so far, a variety of biological activities have been reported for a large number of their derivatives, such as antibacterial (Burch & Smith, 1966), antifungal (Kalyoncuoglu et al., 1992), antitubercular (Mir et al., 1970), antimycobacterial (Rudnicka et al., 1986), anticancer (Holla et al., 2003) and hypoglycemic properties (Mhasalkar et al., 1970). In view of the above findings, and in continuation of our earlier work on the synthesis and biological activity of triazoles and their derivatives, we have synthesized a series of 1,2,4-triazole derivatives via joining a 1,2,4-triazole and acylamide group together in the same molecule and have studied their biological activities. As part of this research we have determined the crystal structure of th title compound.

The molecular structure of the title compound (I) is shown in Fig. 1. The central 1,2,4-triazole ring forms dihedral angles of 89.05 (9), 86.66 (9) and 82.70 (10)° with the three benzene rings (C1–C6, C18–C23 and C12–C17). In the crystal, molecules are linked into double sheets parallel to (1 0 0) by intermolecular N1—H1N1···N3ⁱ, C8—H8A···O1ⁱⁱ and C11—H11B···O1ⁱⁱⁱ hydrogen bonds (Table 1, Fig. 2).

Experimental

A equimolar mixture of 5-[4-(methylthiobenzyl]-4-phenyl-4H-[1,2,4]-triazole-3-thione (0.01 mol), 2-Chloro-N-(2-chlorophenyl)acetamide (0.01 mol) and dry potassium carbonate (0.01 mol) were refluxed for 6 h in 20 ml of absolute alcohol and excess of solvent was removed by distillation under reduced pressure. After cooling to room temperature, the reaction mixture was poured into 50 ml of water. The product which precipitated was filtered off, washed with methanol and dried. The crude product was re-crystallized from ethanol.