Methyl N-{4-[(4-methoxyphenoxy)methyl]-2-oxo-2H-chromen-7-yl}carbamate

K Mahesh Kumar,O Kotresh,H C Devarajegowda,S Jeyaseelan,N M Mahabaleshwaraiah

doi:10.1107/s160053681202048x

Abstract

In the title compound, C19H17NO6, the dihedral angle between the 2H-chromene ring system and benzene ring is 5.34 (6)°. A short intramolecular C—H⋯O contact occurs. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating C(8) chains propagating in [010]. The chains are linked by C—H⋯O interactions and the packing also exhibits π–π stacking interactions between benzene and pyran rings, with a centroid–centroid distance of 3.676 (9) Å.

Highlights

In the title compound, C19H17NO6, the dihedral angle between the 2H-chromene ring system and benzene ring is 5.34 (6)
As part of our ongoing studies of coumarin derivatives with possible biological activity (Mahabaleshwaraiah et al, 2012), we describe the structure of the title compound (Fig. 1)
In the crystal, (Fig. 2), the molecules are connected by C19—H19A···O5 and N7—H7···O2 interaction hydrogen bonds.(Table 1) the crystal structure features π-π stacking interactions between pyranCg2 and benzeneCg3 rings, with a centroid Cg2 (O3/C12–C16) -centroid Cg3 (C13/C14/C17–C20) distance of 3.676 (9) Å

Summary

Bruker SMART CCD diffractometer

Refinement a Department of Chemistry, Karnatak Science College, Dharwad 580 001, Karnataka, India, and bDepartment of Physics, Yuvaraja’s College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India. R factor = 0.035; wR factor = 0.103; data-to-parameter ratio = 12.3. C19H17NO6, the dihedral angle between the 2H-chromene ring system and benzene ring is 5.34 (6). A short intramolecular C—H O contact occurs. Molecules are linked by N—H O hydrogen bonds, generating C(8) chains propagating in [010]. The chains are linked by C—H O interactions and the packing exhibits – stacking interactions between benzene and pyran rings, with a centroid–centroid distance of 3.676 (9) Å. Symmetry codes: (i) x þ 12; y 12; z þ 12; (ii) x þ 1; y; z. Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97

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Crystal data

Graphite monochromator ω and φ scans

Findings

Special details