3-(Di­phenyl­amino)­isobenzo­furan-1(3H)-one

Rodolfo Moreno-Fuquen; Juan C Castillo; Rodrigo Abonia; Javier Ellena; Juan C Tenorio

doi:10.1107/S1600536814006266

. 2014 Mar 29;70(Pt 4):o490. doi: 10.1107/S1600536814006266

3-(Diphenylamino)isobenzofuran-1(3H)-one

Rodolfo Moreno-Fuquen ^a,^*, Juan C Castillo ^a, Rodrigo Abonia ^a, Javier Ellena ^b, Juan C Tenorio ^b

PMCID: PMC3998613 PMID: 24826181

Abstract

In the title isobenzofuranone derivative, C₂₀H₁₅NO₂, the planar fused-ring system (r.m.s. deviation for the 10 fitted atoms = 0.031 Å) forms dihedral angles of 63.58 (6) and 63.17 (8)° with the N-bound phenyl rings; the dihedral angle between the planes of these phenyl rings is 85.92 (7)°. In the crystal, molecules are linked by weak C—H⋯O interactions, involving both O atoms, forming helical supramolecular chains along [001].

Related literature

For biological and pharmacological properties of isobenzofuranones, see: Anderson et al. (2005 ▶); Malpani et al. (2013 ▶); Shode et al. (2002 ▶); Yoganathan et al. (2003 ▶). For the synthesis of diverse amino derivatives, see: Abonia et al. (2010 ▶, 2013 ▶); Moreno-Fuquen et al. (2013 ▶). For similar structures, see: Mendenhall et al. (2003 ▶); Reynolds & Scaringe (1982 ▶).

Experimental

Crystal data

C₂₀H₁₅NO₂
M _r = 301.33
Orthorhombic,
a = 19.1440 (13) Å
b = 8.9363 (6) Å
c = 9.1111 (3) Å
V = 1558.70 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.56 × 0.37 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer
3011 measured reflections
1684 independent reflections
1366 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.106
S = 1.09
1684 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814006266/tk5299sup1.cif

e-70-0o490-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006266/tk5299Isup2.hkl

e-70-0o490-Isup2.hkl^{(83KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814006266/tk5299Isup3.cml

CCDC reference: 992870

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.70	3.413 (3)	135
C1—H1⋯O1ⁱ	1.03 (3)	2.36 (3)	3.307 (3)	153 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

RMF and RA are grateful to the Universidad del Valle, Colombia, for partial financial support. JCC acknowledges his doctoral fellowship granted by COLCIENCIAS.

supplementary crystallographic information

1. Introduction

2. Experimental

2.1. Synthesis and crystallization

Reagents and solvents for the synthesis were obtained from the Aldrich Chemical Co., and were used without additional purification. A 5 mL pyrex test tube was charged with a mixture of diphenylamine (102 mg, 0.60 mmol) and 2-formylbenzoic acid (90 mg, 0.60 mmol) without solvent. The mixture was heated in an oil bath at 120 °C for 1 h until the starting materials were not longer detected by thin-layer chromatography. The solid formed was removed and washed with cold ethanol (1 mL). White crystals of (I) were grown by slow evaporation, under ambient conditions, from its solution in ethanol [92% yield, M.p.: 396 (1) K].

2.2. Refinement

All H-atoms, except H1, were positioned at geometrically idealized positions, C—H = 0.93 Å, and they were refined using a riding model approximation with U_iso(H) = 1.2U_eq(parent atom). Atom H1 was found from the Fourier difference map and its coordinates were freely refined. In the absence of significant anomalous scattering, Friedel pairs were merged.

3. Results and discussion

Isobenzofuranones are an important class of synthetic and naturally occurring products exhibiting diverse biological and pharmacological properties. Some of them appear forming part of the structure of natural products such as fuscinarin (anti-HIV properties) (Yoganathan et al., 2003), typhaphthalide (phenolic compound isolated from Typha capensis) (Shode et al., 2002), noscapine (antitussive and anti-tumor properties) (Anderson et al., 2005), and synthetic compounds like some spirolactones (inhibitors of the influenza virus type B) (Malpani et al., 2013). Continuing with our current studies on the use of imines and imminium ions for the synthesis of diverse amino-derivatives of synthetic and biological interest (Abonia et al., 2010; Abonia et al., 2013; Moreno-Fuquen et al., 2013), 3-diphenylaminoisobenzofuran-1(3H)-one, (I), was obtained from the reaction of 2-formylbenzoic acid and diphenylamine through an imminium ion intermediate. The molecular structure of (I) is shown in Fig. 1. Taking the plane of the phthalide lactone C1—C8(=O1)—O2 (Mendenhall et al., 2003) as a point of reference, the title compound represents the first structure reported with ligands from C1. The bond lengths reported in the phthalide lactone (Reynolds & Scaringe, 1982) are very similar to those presented in (I). In the present molecule, rings A (C9—C14), B (C1—C8—O2) and C (C15—C20) are planar and show dihedral angles between them: A/B = 63.58 (6)°, C/B= 63.17 (8)° and A/C= 85.92 (7)°. In the crystal, the molecules are linked by weak C—H···O interactions, forming eight-membered {···HC₃H···OCO} synthons, leading to a chain along [001], Table 1 and Fig. 2.