(E)-3-Allyl­sulfanyl-N-(4-methoxy­benzyl­idene)-5-(3,4,5-trimethoxy­phen­yl)-4H-1,2,4-triazol-4-amine

Qian-Zhu Li; Bao-An Song; Song Yang; Yu-Guo Zheng; Qing-Qing Guo

doi:10.1107/S1600536809002645

. 2009 Feb 6;65(Pt 3):o469. doi: 10.1107/S1600536809002645

(E)-3-Allylsulfanyl-N-(4-methoxybenzylidene)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-amine

Qian-Zhu Li ^a,^b, Bao-An Song ^a,^*, Song Yang ^a, Yu-Guo Zheng ^a, Qing-Qing Guo ^a

PMCID: PMC2968670 PMID: 21582140

Abstract

The title compound, C₂₂H₂₄N₄O₄S, adopts a trans configuration with respect to the C=N double bond. A weak intramolecular C—H⋯N hydrogen bond is observed between the N atom of the C=N double bond and its neighboring phenyl H atom. The crystal structure is stabilized by intermolecular C—H⋯N hydrogen bonds and C—H⋯π interactions.

Related literature

For background on the biological activity of triazole compounds, see: Bekircan & Gumrukcuoglu (2005 ▶); Ewiss et al. (1986 ▶); Ikizler et al. (1998 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₂H₂₄N₄O₄S
M _r = 440.51
Monoclinic,
a = 7.9414 (12) Å
b = 15.043 (2) Å
c = 19.047 (3) Å
β = 100.385 (6)°
V = 2238.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 (2) K
0.36 × 0.30 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.936, T _max = 0.956
23323 measured reflections
3929 independent reflections
3354 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.103
S = 1.07
3929 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002645/zl2154sup1.cif

e-65-0o469-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002645/zl2154Isup2.hkl

e-65-0o469-Isup2.hkl^{(188.7KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C1–C6 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N4	0.93	2.38	2.960 (2)	120
C12—H12⋯N2ⁱ	0.93	2.59	3.359 (2)	141
C19—H19A⋯N1ⁱⁱ	0.96	2.60	3.477 (3)	152
C9—H9A⋯Cg1ⁱⁱⁱ	0.97	2.79	3.616 (2)	143
C11—H11A⋯Cg2^iv	0.93	2.83	3.703 (2)	158
C15—H15⋯Cg1^v	0.93	2.70	3.514 (2)	147
C22—H22C⋯Cg2^vi	0.96	2.94	3.747 (2)	143

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

Acknowledgments

The authors acknowledge the National Key Project for International Cooperation in Science and Technology (grant No. 2005DFA30650) and the National Natural Science Foundation of China (No. 20872021) for supporting this work.

supplementary crystallographic information

Comment

Triazole derivatives are of great interest in medicinal chemistry in relation to antibacterial bioactivities (Bekircan & Gumrukcuoglu, 2005; Ewiss et al., 1986; Ikizler et al., 1998). However, to date, only a few reports have been dedicated to the synthesis and antimicrobial activity evaluation of triazole derivatives with a 3,4,5-trimethoxyphenyl substituent. Herein, we want to report on the synthesis and structure such a compound, (E)-4-(4-methoxybenzylideneamino)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol.

The molecule of the title compound (Fig. 1), exists in an E configuration with respect to the C12=N4 double bond [1.278 (2) Å] with a N3–N4–C12–C13 torsion angle of 179.08 (13)°. The whole molecule is not planar as the dihedral angles between the triazole ring and the two phenyl rings are 25.3 (2)° and 113.8 (2)°, respectively. There is one weak intramolecular C–H···N hydrogen bond between C1 and N4 (Table 1).

In the crystal structure (Fig. 3), two neighboring molecules are linked by weak C12—H12···N2 intermolecular interactions into a centrosymmetric R₂²(12) ring motif (Bernstein et al., 1995) with two parallel trizole rings with a centroid-centroid separation of 3.650 (1) Å between them (Fig. 2). Moreover, an intermolecular C-H···N hydrogen bond (C19—H19A···N1) is also observed. The molecular packing is further stabilized by C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids of the C1–C6 and C13–C18 rings, respectively).

Experimental

A mixture of 3-bromoprop-1-ene (5 mmol) and methanol (3 mL) was added dropwise to a stirred solution of (E)-4-(4-methoxybenzylideneamino)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol (5 mmol) and sodium hydroxide (5 mmol) in water (15 mL). The resulting mixture was stirred at room temperature for 4 hours. After allowing the resulting solution to stand in air at room temperature for 2 days, colorless block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent. The crystals were isolated, washed with ethanol and dried.