6-Chloro-4-(4-methyl­phen­oxy­meth­yl)-2H-chromen-2-one

Ramakrishna Gowda; KV Arjuna Gowda; Mahantesha Basanagouda; Manohar V Kulkarni

doi:10.1107/S1600536811019258

. 2011 Jun 18;67(Pt 7):o1650. doi: 10.1107/S1600536811019258

6-Chloro-4-(4-methylphenoxymethyl)-2H-chromen-2-one

Ramakrishna Gowda ^a,^*, KV Arjuna Gowda ^b, Mahantesha Basanagouda ^c, Manohar V Kulkarni ^c

PMCID: PMC3151822 PMID: 21837053

Abstract

In the title compound, C₁₇H₁₃ClO₃, the coumarin and phenoxy moieties are essentially co-planar, making a dihedral angle of 1.99 (7)°. The phenoxy moiety is oriented antiperiplanar with respect to the coumarin ring as indicated by the C—C—O—C angle of −179.97 (16)°. In the crystal, the sheet-like packing is stabilized by intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds.

Related literature

For the structure of 7-methyl-4-tolyloxymethylcoumarin, see: Vasudevan et al. (1990 ▶).

Experimental

Crystal data

C₁₇H₁₃ClO₃
M _r = 300.72
Monoclinic,
a = 15.3068 (5) Å
b = 6.9353 (2) Å
c = 14.9566 (5) Å
β = 116.923 (2)°
V = 1415.66 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.932, T _max = 0.967
16899 measured reflections
3818 independent reflections
2448 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.170
S = 1.08
3818 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811019258/vm2090sup1.cif

e-67-o1650-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019258/vm2090Isup2.hkl

e-67-o1650-Isup2.hkl^{(183.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811019258/vm2090Isup3.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
C10—H10B⋯O2ⁱ	0.97	2.47	3.303 (5)	143
C4—H4⋯O2ⁱ	0.93	2.69	3.553 (4)	154
C1—H1⋯Cl1ⁱⁱ	0.93	2.88	3.693 (4)	146

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

Acknowledgments

RG thanks the MVJ College of Engineering, Bangalore-67 (VTU Research Center), for providing research facilities. The authors also thank the SAIF, IIT-Madras, Chennai, for the data collection

supplementary crystallographic information

Comment

The first report on X-ray diffraction studies on 4-aryloxymethylcoumarins has revealed that in solid state the molecules exist as head-tail dimers as observed in the case of 7-methyl-4-tolyloxymethylcoumarin (Vasudevan et al., 1990). In the light of these observations a chloro substituted 4-aryloxymethylcoumarin has been subjected to X-ray diffraction studies. A significant bond deviation is observed at C5—C7 (1.449 (2) Å) due to the bridging of α-pyrone and benzene ring at C5 and the substituent present at C7. This is also reflected at C8—C9 and C7—C10 due to the presence of O2 at C9 and a phenoxy group at C10, respectively. Significant bond angle deviations are observed at C6—C5—C4 (117.91 (17)°) and C6—C5—C7 (117.61 (18)°). Another significant bond angle deviation is observed at C15—C14—C13 (117.46 (18)°) due to presence of the electron donating methyl group on C14. The molecules are oriented as parallel layers along the c axis as shown in Fig 2. The sheet-like packing is stabilized by intermolecular C—H···O and C—H···Cl hydrogen bonds (Table 1, Fig. 3).

Experimental

A mixture of 4-methyl-phenol (10 mmol) and anhydrous potassium carbonate (10 mmol) was stirred for 30 minutes in dry acetone (30 ml). To this, 6-chloro-4-bromomethylcoumarin (10 mmol) was added and the stirring was continued for 24 h. Then, the resulting reaction mixture was poured to crushed ice. The separated solid was filtered and washed with 1:1 HCl (30 ml) and with water. Then product 6-chloro-4-[(4-methyl)phenoxymethyl]coumarin was recrystallized from ethyl acetate.