Ethyl 3-{[(3-methyl­anilino)(1H-1,2,4-triazol-1-yl)methyl­idene]amino}-1-benzofuran-2-carboxyl­ate

Hai-Tao Gao; Li Li; Jun-Kai Ma

doi:10.1107/S1600536810042868

. 2010 Oct 30;66(Pt 11):o2966. doi: 10.1107/S1600536810042868

Ethyl 3-{[(3-methylanilino)(1H-1,2,4-triazol-1-yl)methylidene]amino}-1-benzofuran-2-carboxylate

Hai-Tao Gao ^a, Li Li ^b, Jun-Kai Ma ^a,^*

PMCID: PMC3008986 PMID: 21589133

Abstract

The crystal structure of the title compound, C₂₁H₁₉N₅O₃, is stabilized by intermolecular N—H⋯N and C—H⋯O hydrogen bonds. The molecule contains a planar [maximum deviations = −0.026 (1) and 0.027 (2) Å] benzofuran ring system, which forms dihedral angles of 78.75 (8) and 39.78 (7)° with the benzene and triazole rings, respectively.

Related literature

For the synthesis of heterocyclic compounds, see: Hu et al. (2007 ▶); Hu & Ding (2008 ▶). For related structures, see: Hu et al. (2010 ▶); Chen et al. (2008 ▶); Ma et al. (2009 ▶); Yang et al. (2009 ▶).

Experimental

Crystal data

C₂₁H₁₉N₅O₃
M _r = 389.41
Monoclinic,
a = 10.967 (1) Å
b = 9.9606 (9) Å
c = 17.4807 (15) Å
β = 91.439 (1)°
V = 1909.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.972, T _max = 0.991
14116 measured reflections
4713 independent reflections
3715 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.135
S = 1.07
4713 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042868/jh2221sup1.cif

e-66-o2966-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042868/jh2221Isup2.hkl

e-66-o2966-Isup2.hkl^{(230.9KB, hkl)}

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
C10—H10⋯O2ⁱ	0.93	2.43	3.271 (2)	150
N1—H1⋯N5ⁱⁱ	0.862 (17)	2.250 (17)	3.0755 (19)	160.3 (15)

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

Acknowledgments

We gratefully acknowledge financial support of this work by the Science Research Project of Hubei Medical University (Nos. 2008CXG01 and 2009QDJ22).

supplementary crystallographic information

Comment

As a part of our ongoing investigations on the preparation of derivatives of heterocyclic compounds (Hu et al., 2007, 2008, 2010; Chen et al., 2008; Ma et al., 2009; Yang et al., 2009), we have synthesized and structurally characterized characterized the title compound. Here we wish to report an x-ray crystal structure of it(Fig. 1). In the molecule, the mean plane of the benzofuran system make dihedral angle of 78.75 (8)°, 39.78 (7)°, with the phenyl(C2—C7) ring and the triazole ring, respectively. The crystal structure is mainly stabilized by weak intermolecular N—H···N and C—H···O hydrogen bonding interactions (Table. 1). There are no π-π interactions.

Experimental

The title compound was obtained in excellent yield via aza-WIttig reaction. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.