2-(3-Oxo-1,3-dihydro­isobenzofuran-1-ylamino)benzoic acid

Mustafa Odabaşoğlu; Orhan Büyükgüngör

doi:10.1107/S160053680800754X

. 2008 Mar 29;64(Pt 4):o752–o753. doi: 10.1107/S160053680800754X

2-(3-Oxo-1,3-dihydroisobenzofuran-1-ylamino)benzoic acid¹

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

PMCID: PMC2960995 PMID: 21202142

Abstract

In the molecule of the title compound, C₁₅H₁₁NO₄, the essentially planar phthalide group is oriented at a dihedral angle of 56.78 (5)° with respect to the substituted aromatic ring. An intramolecular N—H⋯O hydrogen bond results in the formation of a non-planar six-membered ring, which adopts a nearly flattened-boat conformation. In the crystal structure, intermolecular C—H⋯O, O—H⋯O and N—H⋯O hydrogen bonds link the molecules, generating centrosymmetric R ₂ ²(8) and R ₂ ²(11) ring motifs and forming a three-dimensional network.

Related literature

For general background, see: Aoki et al. (1973 ▶, 1974 ▶); Lacova (1973 ▶, 1974 ▶); Elderfield (1951 ▶); Bellasio (1974 ▶, 1975 ▶); Roy & Sarkar (2005 ▶); Kubota & Tatsuno (1971 ▶); Tsi & Tan (1997 ▶). For related structures, see: Büyükgüngör & Odabaşoğlu (2006 ▶); Odabaşoğlu & Büyükgüngör (2006 ▶; 2007 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For ring motif details, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C₁₅H₁₁NO₄
M _r = 269.25
Monoclinic,
a = 7.8135 (6) Å
b = 22.6205 (10) Å
c = 7.0902 (5) Å
β = 101.061 (5)°
V = 1229.88 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.55 × 0.36 × 0.18 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.958, T _max = 0.982
12715 measured reflections
2536 independent reflections
1958 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.093
S = 1.07
2536 reflections
225 parameters
All H-atom parameters refined
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 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/S160053680800754X/hk2434sup1.cif

e-64-0o752-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800754X/hk2434Isup2.hkl

e-64-0o752-Isup2.hkl^{(122.1KB, 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
N1—H1⋯O3	0.86 (2)	2.074 (19)	2.7004 (18)	129.3 (16)
N1—H1⋯O1ⁱ	0.86 (2)	2.58 (2)	3.281 (2)	138.9 (15)
O4—H4A⋯O3ⁱⁱ	0.97 (3)	1.67 (3)	2.6329 (17)	174 (2)
C4—H4⋯O2ⁱⁱⁱ	0.93 (2)	2.58 (2)	3.464 (2)	158.9 (17)
C8—H8⋯O1^iv	0.983 (18)	2.580 (17)	3.403 (2)	141.4 (12)

Open in a new tab

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

Acknowledgments

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

supplementary crystallographic information

Comment

Phthalides are known to show diverse biological activities as hormones, pheromones and antibiotics (Aoki et al., 1973, 1974; Lacova, 1973, 1974; Elderfield, 1951; Bellasio, 1974, 1975; Roy & Sarkar, 2005; Kubota & Tatsuno, 1971; Tsi & Tan, 1997). As part of our ongoing research on 3-substituted phthalides (Büyükgüngör & Odabaşoğlu, 2006; Odabaşoğlu & Büyükgüngör, 2006; 2007), the title compound, (I), has been synthesized and its crystal structure is reported here.

In the molecule of (I), (Fig. 1), 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 = 3.08 (3)°, A/C = 57.11 (4)° and B/C = 56.56 (5)°. 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 56.78 (5)°. The intramolecular N-H···O hydrogen bond (Table 1) results in the formation of a non-planar six-membered ring D (N1/H1/O3/C9/C10/C15), having total puckering amplitude, Q_T, of 1.408 (3) Å, in which it adopts a nearly flattened-boat [φ = -42.43 (2)° and θ = 97.94 (3)°] conformation (Cremer & Pople, 1975).

In the crystal structure, intermolecular C-H···O, O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules, generating centrosymmetric R₂²(8) and R₂²(11) (Fig. 2) ring motifs (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network, 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 antranilic acid as starting materials (yield; 70%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol-DMF (1:1) solution at room temperature.