3-(2-Hydr­oxy-5-methyl­anilino)isobenzo­furan-1(3H)-one

Mustafa Odabaşoğlu; Orhan Büyükgüngör

doi:10.1107/S1600536808008441

. 2008 Apr 2;64(Pt 5):o780. doi: 10.1107/S1600536808008441

3-(2-Hydroxy-5-methylanilino)isobenzofuran-1(3H)-one¹

Mustafa Odabaşoğlu ^a, Orhan Büyükgüngör ^b,^*

PMCID: PMC2961204 PMID: 21202273

Abstract

In the molecule of the title compound, C₁₅H₁₃NO₃, the phthalide ring system is virtually planar, with a dihedral angle of 1.98 (3)° between the fused five- and six-membered rings. The substituted aromatic ring is oriented at a dihedral angle of 57.50 (3)° with respect to the phthalide ring system. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules, forming a three-dimensional network.

Related literature

For a related structure, see: Odabaşoğlu & Büyükgüngör (2006 ▶). For ring-motif details, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C₁₅H₁₃NO₃
M _r = 255.26
Orthorhombic,
a = 8.7198 (5) Å
b = 15.5950 (14) Å
c = 9.3992 (6) Å
V = 1278.15 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.64 × 0.42 × 0.28 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.957, T _max = 0.982
4658 measured reflections
1418 independent reflections
1196 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.066
S = 0.99
1418 reflections
175 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.08 e Å⁻³
Δρ_min = −0.09 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008441/hk2444sup1.cif

e-64-0o780-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008441/hk2444Isup2.hkl

e-64-0o780-Isup2.hkl^{(68.6KB, hkl)}

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
O3—H3A⋯O1ⁱ	0.82	1.95	2.767 (2)	173
N1—H1⋯O2ⁱⁱ	0.86	2.78	3.5593 (19)	152

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

The present work is part of a structural study of compounds of 3-substituted phthalides, and we report here the crystal structure of the title compound, (I).

The molecule of (I), (Fig. 1), is built up from a phthalimide unit connected to 2-hydroxy-5-methylphnyl group through an amino group. Rings A (C2-C7), B (C1/C2/C7/C8/O2) and C (C9-C14) are, of course, planar. The dihedral angles between them are A/B = 1.98 (3)°, A/C = 58.27 (3)° and B/C = 56.39 (3)°. So, rings A and B are also nearly coplanar. Ring C is oriented with respect to the coplanar ring system at a dihedral angle of 57.50 (3)°.

In the crystal structure, intermolecular O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules by C(4) chains (Fig. 2) (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network (Fig. 3), in which they may be effective in the stabilization of the structure.

Experimental

The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006), using phthalaldehydic acid and 2-aminophenol as starting materials (yield; 80%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol-DMF (1:1) solution at room temperature.