2-(4-Nitro­phen­yl)-5-phenyl­furan

Zhi Guan; Yan-hong He; Gangqiang Wang

doi:10.1107/S160053680905288X

. 2009 Dec 12;66(Pt 1):o128. doi: 10.1107/S160053680905288X

2-(4-Nitrophenyl)-5-phenylfuran

Zhi Guan ^a, Yan-hong He ^a,^*, Gangqiang Wang ^a

PMCID: PMC2980011 PMID: 21580018

Abstract

The molecular skeleton of the title molecule, C₁₆H₁₁NO₃, is nearly planar with the two aromatic rings forming a dihedral angle of 2.73 (7)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules into ribbons extended along [101]. The crystal packing exhibits also π–π interactions, as indicated by the short centroid–centroid distances between the aromatic rings [3.681 (3) Å] and between the aromatic and furan rings [3.811 (3) Å] of neighbouring molecules.

Related literature

For details of the synthesis, see: Wang et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₁NO₃
M _r = 265.26
Monoclinic,
a = 7.3213 (15) Å
b = 16.290 (3) Å
c = 10.904 (2) Å
β = 100.81 (3)°
V = 1277.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.24 × 0.22 × 0.19 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.977, T _max = 0.982
10136 measured reflections
2924 independent reflections
1168 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.174
S = 1.00
2924 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905288X/cv2666sup1.cif

e-66-0o128-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905288X/cv2666Isup2.hkl

e-66-0o128-Isup2.hkl^{(143.5KB, 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
C3—H3⋯O3ⁱ	0.95	2.51	3.373 (3)	152
C12—H12⋯O2ⁱⁱ	0.95	2.61	3.435 (3)	146

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

Acknowledgments

This work was funded in 2007 as a selected project in scientific and technological activities for returned scholars by the State Personnel Ministry.

supplementary crystallographic information

Comment

The title compound, (I), has been obtained as a by-product in our ongoing research of highly substituted furan derivatives (Wang et al., 2009).

In (I) (Fig. 1), two aromatic rings form a dihedral angle of 2.73 (7) °. Weak intermolecular C—H···O hydrogen bonds (Table 1) and π-π stacking interactions with centroid-centroid separations of 3.681 (3) and 3.811 (3) Å consolidate the crystal packing.

Experimental

A solution of ethyl 2-benzoyl-4-(4-nitrophenyl)-4-oxobutanoate (0.353 g, 0.7 mmol) in ionic liquid [bmim]HSO₄(1.6 g, 6.7 mmol) was stirred at 150 °C for 4 h in oil bath. After cooling to r.t., the reaction mixture was extracted with diethyl ether thoroughly. The combined extracts were washed with water, brine,dried (Na₂SO₄),and filtered. The solvents were removed and the residue was purified by flash chromatography (petroleum ether / dichloromethane 2:1) to get Ethyl 5-(4-nitrophenyl)-2-phenylfuran-3-carboxylate (240 mg, 71%) and the title compound (50 mg,14%) as yellow crystals.