Crystal and Molecular Structure of N-[2-(6-Methoxy-2-oxo-2H-Chromen-4-yl-Benzofuran-3-yl]- Benzamide

Abstract

The crystal structure of the potential active N-[2-(6-Methoxy-2-oxo-2H-chromen-4-yl)-benzofuran-3-yl]-benzamide (C 25 H 17 NO 5 ) (I) has been determined from single crystal X-ray diffraction data. The title compound crystallizes in the monoclinic space group P 21/n, with a = 12.0551(11), b = 9.7853(8), c = 16.6517(16) Å, β = 90.092(4)˚, V = 1964.28(3) Å 3 , D calc = 1.391 Mg/m 3 , Z = 4. In the structure, intermolecular H-bonds lead to the formation of a centrosymmetric dimer of the molecule. There is an intramolecular C7-H7…N1 hydrogen bond forming a closed seven membered ring. There are also intramolecular π-π interactions presented between the 3,6-Dihydro-2H-pyran ring of the chromen moiety [Cg2…Cg2 distance = 3.5812(13) Å]. The packing structure is stabilized by these C-H…N, N-H…O hydrogen bonds, C-H… π and π…π interactions.

Newer chalcone scaffolds with reactive functional groups: Process, spectral and single crystal XRD studies

“…1 H NMR spectra were recorded in CDCl3 or DMSO-d6 at room temperature using a Bruker AVANCE III 500 MHz (AV500) multi-nuclei solution NMR spectrometer, TMS was used as internal reference, integration, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, quin = quintet, m = multiplet, br = broad, app = apparent), coupling constants (J, Hz), and assignment. 13 C and DEPT-135 NMR spectra were measured on a Bruker AVANCE III 125 MHz (AV125) instrument with complete proton decoupling. Chemical shifts in ppm from the residual solvent were reported as an internal standard.…”

“…Spectral analysis by 1 H NMR and 13 C NMR revealed the structure of all these compounds (Ch1-5). The chalcones appeared to be geometrically pure and configured trans (JHa-Hb = 16 Hz) according to 1 H NMR spectra.…”

“…The methoxy proton in Ch2 chalcone was observed at δ 3.986 ppm. In the 13 C NMR spectrum, carbonyl carbon was observed at δ 198 ppm and aromatic carbons were observed in the range of δ 150 to120 ppm. R1 = 0.0657, wR2 = 0.1257 Largest diff.…”

“…In recent years, chalcone and its derivatives have exhibited numerous other properties, such as optical, photochemical, and nonlinear optic properties (Figure 1), and have been used as fluorescent dyes in light-emitting diodes, fluorescent sensors, and as fluorescent probes [12][13][14][15][16]. Due to its π-conjugated system, the optical characteristics of chalcone and its derivatives have received substantial attention due to their nonlinear optical and fluorescence nature due to the delocalization of the electronic charge and overlapping π-orbitals [17].…”