4-({(E)-[2-(But-3-en-1-yl)-1-(prop-2-en-1-yl)-4-sulfanyl-1H-imidazol-5-yl]methyl­idene}amino)-3-phenyl-1H-1,2,4-triazole-5(4H)-thione

Sampath Natarajan; Rita Mathews

doi:10.1107/S1600536811039833

. 2011 Oct 5;67(Pt 11):o2828. doi: 10.1107/S1600536811039833

4-({(E)-[2-(But-3-en-1-yl)-1-(prop-2-en-1-yl)-4-sulfanyl-1H-imidazol-5-yl]methylidene}amino)-3-phenyl-1H-1,2,4-triazole-5(4H)-thione

Sampath Natarajan ^a,^*, Rita Mathews ^a

PMCID: PMC3247567 PMID: 22219872

Abstract

In the title compound, C₁₉H₂₀N₆S₂, the dihedral angle between the phenyl and triazole rings is 24.1 (2)° while the dihedral angles between the imidazole ring and the triazole and phenyl rings are 39.9 (2) and 55.3 (2)°, respectively. The crystal structure is stabilized by intermolecular N—H⋯N hydrogen bonds which form chains along [10 Inline graphic ].

Related literature

For biological applications of Schiff base compounds, see: Liang (2003 ▶); Bacci et al. (2005 ▶). For the biological activity of triazoles and their derivatives, see: Amir et al. (2008 ▶); Sztanke et al. (2008 ▶); Padmavathi et al. (2008 ▶); Thenmozhi et al. (2010 ▶). Pharmacological compounds having triazole moieties appear to be very effective aromatese inhibitors for the prevention of breast cancer, see: Ünver et al. (2010 ▶).

Experimental

Crystal data

C₁₉H₂₀N₆S₂
M _r = 396.53
Monoclinic,
a = 13.384 (3) Å
b = 13.892 (3) Å
c = 11.349 (2) Å
β = 101.953 (3)°
V = 2064.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.28 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
7754 measured reflections
3788 independent reflections
3391 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.139
S = 1.07
3788 reflections
244 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039833/kj2187sup1.cif

e-67-o2828-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039833/kj2187Isup2.hkl

e-67-o2828-Isup2.hkl^{(181.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039833/kj2187Isup3.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
N3—H3⋯N16ⁱ	0.86	2.05	2.907 (5)	172

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Synthesis and structural investigation of Schiff base compounds have been given attention due to their interesting structural features and potential biological applications (Liang, 2003; Bacci et al., 2005). The biological importance of imidazoles and triazoles has stimulated much work on these heterocycles. Triazole compounds and their derivatives have many applications in medicine and were reported to exhibit various pharmacological activities such as antimicrobial, analgesic, anti-inflammatory, anticancer and antioxidant properties (Amir et al., 2008; Sztanke et al., 2008; Padmavathi et al., 2008; Thenmozhi et al., 2010). The 1,2,4-triazole group interacts strongly with heme iron and aromatic substituents on the triazoles are very effective for interacting with the active site of aromatase. Furthermore, it was reported that pharmacological compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatese inhibitors for preventing breast cancer (Ünver et al., 2010). In view of these important applications of imidazolines, here we report the crystal structure of the title compound (Fig. 1).

The title compound contains imidazole and 1,2,4-triazole rings connected by an imine group. A phenyl ring is substituted at position 5 of the triazole ring and the dihedral angle between these rings is 24.1 (2)°. The imidazole and triazole groups are substituted on the imine group (N12—C13) in the E-configuration [N1—N12—C13—C14 = -174.4 (3)°]. The triazole ring is not co-planar with the imidazole ring and this may be due to the substitution of the phenyl ring on the triazole ring. The dihedral angles between the imidazole ring and the triazole and phenyl rings are 39.9 (2)° and 55.3 (2)°, respectively. The imidazole ring is substituted by bulky groups (3-butene, 2-propene) as well as an imine and a thiol group, which gives strain on the ring. The 3-butene and imine substituents show an extended zigzag confirmation with respect to the imidazole ring.

The packing diagram of the title compound viewed down the a axis is shown in Fig. 2. The crystal packing displays intermolecular N—H···N hydrogen bonds (Table 1), which join the molecules into chains in the [1 0 -1] direction.

Experimental

The title compound was synthesized by refluxing 4-amino-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (0.01 mmol) and 2-(but-3-en-1-yl)-1-(prop-2-en-1-yl)-4-sulfanyl-1H-imidazole-5- carbaldehyde (0.01 mmol) in ethanol (50 ml) with a few drops of H₂SO₄ for 3 h on a water bath. The reaction progress was monitored by TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as a colorless solid in 74% yield. The resulting Schiff base compound was seperated out and crystallized in ethanol.