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

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

doi:10.1107/S160053681202048X

. 2012 May 16;68(Pt 6):o1734. doi: 10.1107/S160053681202048X

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

K Mahesh Kumar ^a, N M Mahabaleshwaraiah ^a, O Kotresh ^a, S Jeyaseelan ^b, H C Devarajegowda ^b,^*

PMCID: PMC3379323 PMID: 22719521

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.

Related literature

For a related structure and background to coumarins, see: Mahabaleshwaraiah et al. (2012 ▶). For further synthetic details, see: Kulkarni & Patil (1981 ▶).

Experimental

Crystal data

C₁₉H₁₇NO₆
M _r = 355.34
Monoclinic,
a = 8.3141 (1) Å
b = 17.3978 (3) Å
c = 11.5729 (2) Å
β = 94.309 (1)°
V = 1669.25 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.770, T _max = 1.000
14973 measured reflections
2939 independent reflections
2374 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.103
S = 1.06
2939 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.12 e Å⁻³

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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202048X/hb6754sup1.cif

e-68-o1734-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202048X/hb6754Isup2.hkl

e-68-o1734-Isup2.hkl^{(141.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681202048X/hb6754Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O2ⁱ	0.86	1.99	2.8428 (16)	170
C15—H15⋯O5	0.93	2.30	2.8764 (19)	120
C19—H19A⋯O5ⁱⁱ	0.97	2.53	3.476 (2)	165

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities, X-ray data collection, GCMS, IR, CHNS and NMR data. KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

supplementary crystallographic information

Comment

As part of our ongoing studies of coumarin derivatives with possible biological activity (Mahabaleshwaraiah et al., 2012), we now describe the structure of the title compound (Fig. 1).

The 2H-chromene (O1/C10–C18) and benzene (C20–C25) rings are almost coplanar; the dihedral angle between them is 5.34 (6)°. In the crystal, (Fig. 2), the molecules are connected by C19—H19A···O5 and N7—H7···O2 interaction hydrogen bonds.(Table 1) Furthermore, 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.

Experimental

The 4-bromomethyl coumarin required for the target molecule was synthesized according to an already reported (Kulkarni et al.1981) procedure involving Pechmann cyclization of phenols with 4-bromoethylacetoacetate. A mixture of 1.56 g (0.005 mol) of 7-carbonylamino-4-bromomethyl coumarin, 0.620 g (0.005 mol) of p-methoxy phenol and 0.70 g (0.005 mol) of powdered anhydrous K₂CO₃ in 30 ml of dry acetone were stirred at room temperature for 24 h. After completion of the reaction, the s eparated solid was filtered, washed with excess of dilute (10%) hydrochloric acid (50 ml) and then with an excess of cold water, dried and crystallized twice from ethanol & 1,4-dioxane mixture to yield colourless plates. Yield= 78%, M. P.475 K.