3-(4-Methoxy­phen­yl)isochroman-1-one

Muhammad Tahir Hussain; M Nawaz Tahir; Ahmad Adnan; Asif Hanif Ch; Nasim Hassan Rama

doi:10.1107/S1600536808032625

. 2008 Oct 15;64(Pt 11):o2111. doi: 10.1107/S1600536808032625

3-(4-Methoxyphenyl)isochroman-1-one

Muhammad Tahir Hussain ^a, M Nawaz Tahir ^b,^*, Ahmad Adnan ^c, Asif Hanif Ch ^c, Nasim Hassan Rama ^d

PMCID: PMC2959622 PMID: 21580975

Abstract

In the molecule of the title compound, C₁₆H₁₄O₃, the aromatic rings are oriented at a dihedral angle of 72.02 (6)°. The heterocyclic ring adopts a twisted conformation. In the crystal structure, there are C—H⋯π contacts between the heterocyclic and phenyl rings, and between the methyl group and methoxyphenyl ring.

Related literature

For related structures, see: Schmalle et al. (1982 ▶); Schnebel et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C₁₆H₁₄O₃
M _r = 254.27
Monoclinic,
a = 11.8933 (7) Å
b = 14.6874 (9) Å
c = 7.4521 (4) Å
β = 101.040 (2)°
V = 1277.66 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 (2) K
0.24 × 0.16 × 0.12 mm

Data collection

Bruker KappaAPEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.980, T _max = 0.996
12426 measured reflections
3302 independent reflections
2275 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.117
S = 1.01
3302 reflections
175 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032625/hk2543sup1.cif

e-64-o2111-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032625/hk2543Isup2.hkl

e-64-o2111-Isup2.hkl^{(158.7KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cg2ⁱ	0.97	2.94	3.8398 (16)	154
C16—H16B⋯Cg3ⁱⁱ	0.96	2.89	3.7804 (17)	154

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

Acknowledgments

The authors acknowledge the Higher Education Commision, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

supplementary crystallographic information

Comment

The title compound was prepared in order to evalute its potential as antibacterial and antifungal agents. The CCDC search (Allen, 2002) showed that the crystal structures of rac-exo-tricarbonyl-(h6-3-phenylisochromanone)-chromium (Schnebel et al., 2003) and 3,4-dihydro-8-hydroxy-3-(4-hydroxyphenyl)-isocoumarin (Schmalle et al., 1982) have been reported, which have close resemblance as far as isochromane and attached phenyl ring is considered.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2–C7) and C (C10–C15) are, of course, planar, and they are oriented at a dihedral angle of 72.02 (6)°. Ring B (O2/C1/C2/C7–C9) is not planar, having total puckering amplitude, Q_T, of 0.483 (2) Å and twisted conformation [φ = 41.63 (3)° and θ = 116.64 (3)°] (Cremer & Pople, 1975).

In the crystal structure, there are C—H···π contacts (Table 1) between the heterocyclic and phenyl rings and the methyl group and methoxyphenyl ring, in which they may be effective in the stabilization of the structure.

Experimental

As shown in Fig. 3, a mixture of homophthalic acid, (1), (1.98 g, 11.0 mmol) and 4-methoxybenzoyl chloride, (2), (7.85 g, 46 mmol) was heated under reflux at 473 K. After concentration, the residue was chromatographed on silica gel column using petroleum ether (333–353 K) to give 3-(4-methoxyphenyl)isocoumarin, (3). 2-[2'-Oxoethyl-2'-(4'-methoxyphenyl)]benzoic acid, (4), was obtained by refluxing a solution of (3) (4 g, 15.9 mmol) in ethanol (200 ml) and potassium hydroxide (5%, 200 ml) for 4 h. NaBH₄ (1.6 g) was added to a solution of (4) (4.81 g, 17.8 mmol) in sodium hydroxide (1%, 180 ml) and the resulting solution was stirred overnight at room temperature. After being acidified with HCl, the whole mixture was extracted with dichloromethane (2 × 15 ml). Usual work-up gave crude racemic hydroxy-acid, (5), which was dissolved in acetic anhydride (5 ml) and heated under reflux for 2 h to get the title compound (6). The crude compound was purified by column chromatography on silica gel with petroleum ether and recrystallized in ethanol.