2-(2-Fluoro-4-hy­droxy­benz­yl)isoindoline-1,3-dione

Hilal Vesek; Canan Kazak; Ayşen Alaman Ağar; Sümeyye Gümüş; Muhittin Aygün

doi:10.1107/S1600536812029923

. 2012 Jul 18;68(Pt 8):o2478. doi: 10.1107/S1600536812029923

2-(2-Fluoro-4-hydroxybenzyl)isoindoline-1,3-dione

Hilal Vesek ^a,^*, Canan Kazak ^a, Ayşen Alaman Ağar ^b, Sümeyye Gümüş ^b, Muhittin Aygün ^c

PMCID: PMC3414933 PMID: 22904920

Abstract

In the title compound, C₁₅H₁₀FNO₃, the dihedral angle between the isoindoline-1,3-dione and 3-fluoro-4-methylphenol groups is 86.88 (8)°. The isoindoline-1,3-dione fragment is almost planar, with an r.m.s. deviation of 0.0154 Å within the group. Intermolecular C—H⋯O hydrogen bonds generate C(6) chains running parallel to the [010] direction.

Related literature

For background to indoline-1,3-dione and its derivatives, see: Raza et al. (2010 ▶). For discussion of the broad spectrum of properties of these compounds, see: Bhattacharya & Chakrabarti (1998 ▶). For discussion of their anti-inflammatory properties, see: Sridhar & Ramesh (2001 ▶). For discussion of their anxiogenic activities, see: Medvedev et al. (1996 ▶). For related structures, see: Asad et al. (2012 ▶); Fu et al. (2010 ▶). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₀FNO₃
M _r = 271.24
Monoclinic,
a = 12.4362 (7) Å
b = 13.8189 (8) Å
c = 7.2376 (4) Å
β = 105.784 (6)°
V = 1196.92 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.49 × 0.36 × 0.16 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶) and Clark & Reid (1995 ▶)] T _min = 0.977, T _max = 0.995
6558 measured reflections
2475 independent reflections
1455 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.141
S = 1.04
2475 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, global. DOI: 10.1107/S1600536812029923/mw2073sup1.cif

e-68-o2478-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029923/mw2073Isup2.hkl

e-68-o2478-Isup2.hkl^{(119.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812029923/mw2073Isup3.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
O1—H1⋯F1ⁱ	0.82	2.52	3.267 (2)	152
C2—H6⋯O2ⁱⁱ	0.93	2.51	3.303 (3)	144
C12—H12⋯O2ⁱⁱⁱ	0.93	2.51	3.403 (3)	161
C15—H15⋯O3^iv	0.93	2.47	3.346 (3)	157

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences of Dokuz Eylul University, Turkey, for the use of the Agilent Xcalibur Eos diffractometer (purchased under University Research grant No. 2010.KB.FEN.13).

supplementary crystallographic information

Comment

Indoline-2,3-dione and its derivatives are well known for their broad spectrum properties including anticonvulsant (Bhattacharya & Chakrabarti, 1998), anti-inflammatory (Sridhar & Ramesh, 2001) and anxiogenic (Medvedev et al., 1996) activities. On the other hand, dithiocarbamates also show a large range of biological activities for example fungicidal (Ozkirimli et al., 2005) and antitumor activities (Cao et al., 2005; Gaspari et al., 2006).

As an extension of the work on the structural characterization of indoline-2,3-dione derivatives, the crystal structure of the title compound is reported here. The isoindoline-1,3-dione fragment is almost planar with an r.m.s. deviation of 0.0154 Å within the group. This unit makes a dihedral angle of 86.88 (8)° with the benzene ring.

The F1—C4 bond length of 1.349 (3) Å agrees with the corresponding distance in 9-(7-fluoro-4-oxo-4H-chromen-3-yl)-3,3,6,6-tetramethyl-2,3,4,5,6, 7,8,9-octahydro-1H-xanthene-1,8-dione [1.349 (2) Å (Asad et al., 2012)]. The C═O bond lengths are 1.205 (3) Å for C8═O2 and C11═O3 which are similar to the corresponding values found in 2-(2-oxothiolan-3-yl)isoindoline-1,3-dione [1.202 (5) Å and 1.207 (5) Å (Raza et al., 2010)].

The molecules are linked into sheets by a combination of C—H···O and O—H···F interactions (Table 1). C(6) chains along [010] are created by pairwise C12—H12···O2 and C15—H15···O3 hydrogen bond interactions. The combination of the C(6) chains generates chain edge-fused R₂²(10) rings running along [010]. C(6) chains along [001] are formed by O1—H1···F1 hydrogen bond interactions (Fig.2).

Experimental

The compound 2-(2-fluoro-4-hydroxybenzyl)-1H-isoindole-1,3(2H)-dione was prepared by combining solutions of 2-hydroxy-1H-isoindole-1,3(2H)-dione (0.011 g 0.067 mmol) in 20 ml of ethanol and 1-(2,4-difluorophenyl)methanamine (0.009 g, 0.067 mmol) in 20 ml of ethanol and refluxing the resulting mixture for 1 h with stirring. Crystals of 2-(2-fluoro-4-hydroxybenzyl)-1H-isoindole-1,3(2H)-dione suitable for X-ray analysis were obtained from ethyl alcohol by slow evaporation (yield 72%; m.p. 155–158°C).