Ethyl 1-aminonaphtho[2,1-b]furan-2-carboxylate

In the title compound, C15H13NO3, there is intramolecular N—H⋯O hydrogen bond between the amino group and the ester carbonyl O atom and the dihedral angle between the aromatic ring and the ester group is 2.05 (15)°. In the crystal, molecules are connected by N—H⋯O hydrogen bonds into chains parallel to [010]. In addition there are short C—H⋯O interactions and π–π stacking interactions with a distance of 3.555 (2) Å between the centroids of the furan and benzene rings.

In the title compound, C 15 H 13 NO 3 , there is intramolecular N-HÁ Á ÁO hydrogen bond between the amino group and the ester carbonyl O atom and the dihedral angle between the aromatic ring and the ester group is 2.05 (15) . In the crystal, molecules are connected by N-HÁ Á ÁO hydrogen bonds into chains parallel to [010]. In addition there are short C-HÁ Á ÁO interactions andstacking interactions with a distance of 3.555 (2) Å between the centroids of the furan and benzene rings.
The title compound was synthesized as an intermediate in the synthesis of aza heterocyclic derivative of naphtho[2,1b]furan. The synthesis of the title compound was reported by Veena et al. (2011).
The ORTEP drawing of the title molecule is shown in Fig. 1. The naphthofuran system is basically planar and its geometry is similar to ethyl naphtho[2,1-b]furan-2-carboxylate (Shruthi et al., 2012). The dihedral angle between aromatic ring and the ester group is 2.05 (15)°.
The molecules are connected by N-H···O interactions into chains along the b axis (Fig. 2). There are π-π stacking interactions between molecules related by unit translation along the a axis with the distance of 3.555 (2) Å between centroids of the furan and benzene rings.

Experimental
Ethyl 3-aminonaphtho[2,1-b]furan-2-carboxylate was synthesized as per the procedure reported in the literature (Veena et al., 2011). The final product was obtained by recrystallization using aqueous ethanol as a solvent. Slow evaporation method yielded crystals.

Refinement
In the absence of significant anomalous dispersion effects Friedel pairs have been merged. All the hydrogen atoms of the compound are fixed geometrically (N-H = 0.86 and C-H= 0.93-0.97 Å) and allowed to ride on their parent atoms.

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.