2-Bromo-5,7-dimethoxy-4-phenylquinoline

Veshal Gopal,Chao-Wei Leu,Mohan Bhadbhade,Daniel Shiu Hin Chan,David Stc Black,Naresh Kumar

doi:10.1107/s160053680900587x

Veshal Gopal, Chao-Wei Leu + Show 4 more

Open Access

https://doi.org/10.1107/s160053680900587x

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Abstract

The title compound, C17H14BrNO2, was synthesized by the treatment of 5,7-dimethoxy-4-phenylquinolin-2-one with phosphoryl bromide in a Vilsmeier-type reaction. There are two independent molecules (A and B) in the asymmetric unit which differ by 11.2° in the orientation of the 4-phenyl ring with respect to the planar quinoline ring system [dihedral angles = 55.15 (8) and 66.34 (8)° in molecules A and B, respectively]. In the crystal structure, the independent molecules are linked via C—H⋯N and C—H⋯O hydrogen bonds, forming centrosymmetric tetrameric units which are cross-linked through C—H⋯π and C—Br⋯π interactions with Br⋯centroid distances of 3.4289 (8) and 3.5967 (8) Å.

Highlights

The title compound, C17H14BrNO2, was synthesized by the treatment of 5,7-dimethoxy-4-phenylquinolin-2-one with phosphoryl bromide in a Vilsmeier-type reaction
The independent molecules are linked via C—H N and C—H O hydrogen bonds, forming centrosymmetric tetrameric units which are cross-linked through C—H and C—Br interactions with Br centroid distances of 3.4289 (8) and 3.5967 (8) Å
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1

Summary

Mo K radiation

R factor = 0.029; wR factor = 0.100; data-to-parameter ratio = 10.2. The title compound, C17H14BrNO2, was synthesized by the treatment of 5,7-dimethoxy-4-phenylquinolin-2-one with phosphoryl bromide in a Vilsmeier-type reaction. There are two independent molecules (A and B) in the asymmetric unit which differ by 11.2 in the orientation of the 4-phenyl ring with respect to the planar quinoline ring system [dihedral angles = 55.15 (8) and 66.34 (8) in molecules A and B, respectively]. The independent molecules are linked via C—H N and C—H O hydrogen bonds, forming centrosymmetric tetrameric units which are cross-linked through C—H and C—Br interactions with Br centroid distances of 3.4289 (8) and 3.5967 (8) Å

Bruker Kappa APEXII CCD areadetector diffractometer

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