(5-Benzoyl-2-methyl-4-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl]meth­oxy}-1-benzofuran-7-yl)(phen­yl)methanone

Xiao-qin Zhang; Hai-Liang Zhang; Zhu-Yong Dong; Qiang Qian; Yu-Guang Wang

doi:10.1107/S1600536812023720

. 2012 May 31;68(Pt 6):o1916. doi: 10.1107/S1600536812023720

(5-Benzoyl-2-methyl-4-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}-1-benzofuran-7-yl)(phenyl)methanone

Xiao-qin Zhang ^a, Hai-Liang Zhang ^b, Zhu-Yong Dong ^b, Qiang Qian ^b, Yu-Guang Wang ^a,^*

PMCID: PMC3379472 PMID: 22719670

Abstract

The crystal structure of the title compound, C₃₁H₂₂N₄O₄, features weak C—H⋯O interactions. The dihedral angle between the fused benzene and furan rings is 2.49 (15)°, while that between the triazole and pyridine rings is 10.23(18)°.

Related literature

For bioactive nnitrogen-linked heterocyclic compounds, see: Anderson et al. (2004 ▶); Ha et al. (2009 ▶); Liu et al. (2011 ▶); Tan et al. (2012 ▶); Venkatesan et al. (2010 ▶); Yim et al. (2010 ▶). For the bioactivity of benzofuran analogues substituted by heterocyclic moieties, see: El-Shehry et al. (2010 ▶); Kaldrikyan et al. (2009 ▶); Saberi et al. (2006 ▶). For a related structure, see: Liu et al. (2012 ▶). graphic file with name e-68-o1916-scheme1.jpg

Experimental

Crystal data

C₃₁H₂₂N₄O₄
M _r = 514.53
Triclinic,
a = 10.11 (2) Å
b = 10.87 (3) Å
c = 11.64 (3) Å
α = 94.73 (4)°
β = 92.07 (3)°
γ = 92.05 (4)°
V = 1273 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.38 × 0.22 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.966, T _max = 0.988
9629 measured reflections
4699 independent reflections
2743 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.200
S = 0.85
4699 reflections
353 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023720/ds2193sup1.cif

e-68-o1916-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023720/ds2193Isup2.hkl

e-68-o1916-Isup2.hkl^{(230.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023720/ds2193Isup3.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
C11—H11⋯O3ⁱ	0.93	2.33	3.225 (10)	161
C16—H16⋯O3ⁱ	0.93	2.55	3.473 (10)	171

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful for financial support by the Science and Technology Department of Zhejiang Province Foundation of China (project No. 2010 C32022) and the Zhejiang Province Natural Science Foundation of China (project No. Y4090410.)

supplementary crystallographic information

Experimental

General procedure to synthesize the title compound: Under a positive pressure of nitrogen, to a suspension of the swollen 2-polystyrene supported selanylmethyl-4-(prop-2-ynyloxy)-5,7-dibenzoyl- 2,3-dihydro-benzofuran in DMSO (30 mL) was added the mixed solution of 0.2 g (4.0 mmol) Cu₂SO₄ 5H₂O and 0.8 g(4.5 mmol) ascorbic acid in 10 mL water, 5.0 mmol 4-Azido-pyridine. After stirring for 15 h at 60°C, the resin was collected by filtration, washed with H₂O (30 mL×2), THF (20 mL×1), hot DMF (15 mL×1), H2O (30 mL×1), THF (20 mL×1), THF/H₂O (2:1) (20 mL×2), hot DMF (15 mL×1), THF (20 mL×1), THF/H₂O (2:1) (20 mL×2), THF (20 mL×2). The washed resin was suspended in THF (15 mL), 30% H₂O₂ (20.0 equiv) was added, and the mixture was stirred for 10 h at room temperature. The resin was collected by filtration, washed with H₂O (20 mL×2), THF (10 mL×2), THF/H₂O (2:1) (10 mL×2), THF (10 mL×2) , CH₂Cl₂ (10 mL×2), toluene (10 mL×2). The washed resin was suspended in 15 mL toluene, DBU (0.4 equiv) was added, and the mixture was stirred for 5.0 h at 80°C. The mixture was filtered, and the resin was washed with CH₂Cl₂ (15 mL ×2). The filtrate was washed with 0.25M HCl (30 mL×2), saturated sodium bicarbonate solution(35 mL×2), dried with anhydrous magnesium sulfate, and evaporated to dryness under vacuum to obtain the title compound. Further purification was via flash chromatography with n-hexanes-EtOAc (3:1, V/V) as the eluent for microanalyses. ¹H-NMR(CDCl₃, 400MHz, Bruker Avance spectrometer): δ 8.78-8.76 (d, 2H, J=5.6Hz), 7.85-7.81 (m, 4H), 7.64-7.40 (m, 10H), 6.77 (d, 1H, J=0.8Hz), 5.52 (s, 2H), 2.47 (s, 3H); 13C-NMR(CDCl3): δ 195.6, 192,8, 157.7, 156.2, 152.5, 151.9, 145.4, 143.1, 138.4, 137.9, 133.4, 133.2, 130.3, 130.2, 128.7, 128.6, 128.1, 125.0, 122.1, 120.5, 118.3, 113.9, 101.2, 67.1, 14.3; MS(ESI) m/z 515 (M+H)⁺. The title compound was recrystallized from CHCl₂ at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.