(Z)-2-(4-Nitro­benzyl­idene)-1-benzofuran-3(2H)-one

J Satyanarayana Reddy; N Ravikumar; J Venkata Prasad; G Gopi Krishna; K Anand Solomon

doi:10.1107/S1600536811041869

. 2011 Oct 12;67(Pt 11):o2961. doi: 10.1107/S1600536811041869

(Z)-2-(4-Nitrobenzylidene)-1-benzofuran-3(2H)-one

J Satyanarayana Reddy ^a, N Ravikumar ^a, J Venkata Prasad ^a, G Gopi Krishna ^a, K Anand Solomon ^a,^*

PMCID: PMC3247368 PMID: 22219986

Abstract

In the crystal structure of the title compound, C₁₅H₉NO₄, weak C—H⋯O interactions generate rings with R ² ₂(8) motifs. The supramolecular aggregation is completed by the presence of C—H⋯O and van der Waals interactions.

Related literature

For the synthesis and biological activity of substituted aurones, see: Varma & Varma (1992 ▶); Beney et al. (2001 ▶); Sim et al. (2008 ▶). For the assignment of conformations and the orientation of the substituents, see: Nardelli (1983 ▶, 1995 ▶); Klyne & Prelog (1960 ▶). For hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For the diverse theraputic properties of aurones, see: Villemin et al. (1998 ▶). Several multifunctionalized aurones have been reported to exhibit anti-malarial (Souard et al. 2010 ▶) and anti-histamine (Wang et al. 2007 ▶) properties.

Experimental

Crystal data

C₁₅H₉NO₄
M _r = 267.23
Triclinic,
a = 6.6916 (2) Å
b = 7.4708 (2) Å
c = 12.6414 (3) Å
α = 100.459 (1)°
β = 93.019 (2)°
γ = 102.043 (1)°
V = 605.09 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 303 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) ▶ T _min = 0.932, T _max = 0.955
12519 measured reflections
2116 independent reflections
1869 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.105
S = 1.03
2116 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041869/zj2025sup1.cif

e-67-o2961-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041869/zj2025Isup2.hkl

e-67-o2961-Isup2.hkl^{(104KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811041869/zj2025Isup3.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
C15—H15⋯O1	0.93	2.32	2.9547 (16)	125
C9—H9⋯O2ⁱ	0.93	2.50	3.2951 (14)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Managing Trustee and the Founder Trustee of the Sankar Foundation for their financial support and encouragement. We also acknowledge, The Head, SAIF, IIT-Chennai, for the data collection.

supplementary crystallographic information

Comment

Aurones belong flavonoids family, which are structurally isomers of flavones. They form essential structural scaffolds in many natural and synthetic molecules possessing diverse therapeutic properties (Villemin et al. 1998) Several multifunctionalized aurones were reported to exhibit anti-malarial (Souard et al. 2010) and anti-histamine (Wang et al. 2007) properties.

The title compound (Fig.1),C₁₅H₉NO₄,crystallized in triclinic space group P-1 with two molecules in the assymetric unit (Fig.2).The crystal structure of (I) is stabilized by C—H···O interactions.The range of H···O distances (Table 1) found in (I) agrees with those found for C—H···O hydrogen bonds (Desiraju & Steiner,1999). The coumaranone moiety at C10 is in co-planar conformation [C7—C8—C9—C10=179.55 (13)°].The translational related molecules interact with each other via weak C—H···O [C9—H9···O2: H9···O2 = 2.50 Å, θ = 143°] hydrogen bonds along the c axis, and form a one dimensional chain (Fig. 3).

Experimental

3-coumaranone was allowed to react with 4-nitrobenzaldehyde in ethanolic solution of potassium hydroxide for 30 minutes to yield the title compound (Fig.4). The pure product was obtained by recrystallization in methanol.