Ethyl 2-amino-4-(4-bromophenyl)-6-methoxy-4H-benzo[h]chromene-3-carboxylate

Ahmed M El-Agrody,Ahmed M Fouda,Seik Weng Ng,Mohamed A Al-Omar,Abd El-Galil E Amr,Edward R T Tiekink

doi:10.1107/s160053681300490x

Abstract

In the title compound, C23H20BrNO4, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å) with the bromobenzene ring almost perpendicular [dihedral angle = 83.27 (16)°] and the ester group coplanar [C—C—C—O = 3.4 (5)°]; the methoxy substituent is also coplanar [C—O—C—C = 174.5 (3)°]. In addition to an intramolecular N—H⋯O(ester carbonyl) hydrogen bond, the ester carbonyl O atom also forms an intermolecular N—H⋯O hydrogen bond with the second amine H atom, generating a zigzag supramolecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N—H⋯Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C—H⋯π interactions.

Highlights

In the title compound, C23H20BrNO4, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms
The chains are linked into layers in the bc plane by N—H Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C—H interactions
The authors are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University

Summary

Structure Reports

Experimental a Chemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO. C23H20BrNO4, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. In addition to an intramolecular N—H O(ester carbonyl) hydrogen bond, the ester carbonyl O atom forms an intermolecular N—H O hydrogen bond with the second amine H atom, generating a zigzag supramolecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N—H Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C—H interactions

Agilent SuperNova Dual diffractometer with an Atlas detector

Mo K radiation

Special details