Abstract
The title compound, C17H19NO4, was synthesized by the reaction of 7-(di-ethyl-amino)-2-oxo-2H-chromene-3-carb-oxy-lic acid with allyl bromide and purified by flash column chromatography on silica gel. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from acetone. The aromatic core of the mol-ecule is not planar with the di-ethyl-amino group and with the carboxyl group that are rotated out of the 2-oxo-2H-chromene plane by 6.7 (2)° and 11.4 (2)°. The NC2 unit of the di-ethyl-amino group is planar with an angle sum close to 360°. Inter-molecular Car-H⋯Ocarbon-yl inter-actions lead to the formation of chains parallel to the b axis. X-ray powder diffraction analysis proves that the title compound was obtained as a pure phase.
Highlights
Coumarins or 2H-1-benzopyran-2-ones are fluorophores with a wide range of biological and chemical applications (Bardajee et al, 2006a)
(N1,C7,C14,C16) of the diethylamino group is nearly planar with a maximum deviation of the N atom from the mean plane of 0.0873 A ; planarity is obvious from the sum of the C— N—C angles of 358.9
This unit is rotated from the 2-oxo-2Hchromene plane by 11.4 (2) (Fig. 3), which points to conjugation between the ring system and the diethylamino group
Summary
Coumarins or 2H-1-benzopyran-2-ones are fluorophores with a wide range of biological and chemical applications (Bardajee et al, 2006a). (coumarin-4-yl)methyl esters are often used as a photocleavable protecting group that could be useful for proton detection in biological processes (Geissler et al, 2005) Another emerging field of application is photoelectricity such as in organic light-emitting diodes (OLEDs) or laser dyes (Bardajee et al, 2006a; Jones et al, 1985; Jones & Rahman, 1992, 1994; Cui et al, 2018). (N1,C7,C14,C16) of the diethylamino group is nearly planar with a maximum deviation of the N atom from the mean plane of 0.0873 A ; planarity is obvious from the sum of the C— N—C angles of 358.9 This unit is rotated from the 2-oxo-2Hchromene plane by 11.4 (2) (Fig. 3), which points to conjugation between the ring system and the diethylamino group. The latter feature is reflected by the C7—N1 bond length of 1.3597 (12)
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