2-[(E)-(2,4-Dichloro­benzyl­idene)amino]­isoindoline-1,3-dione

Mohammad Asad; Chuan-Wei Oo; Hasnah Osman; Madhukar Hemamalini; Hoong-Kun Fun

doi:10.1107/S1600536811023063

. 2011 Jun 18;67(Pt 7):o1712. doi: 10.1107/S1600536811023063

2-[(E)-(2,4-Dichlorobenzylidene)amino]isoindoline-1,3-dione

Mohammad Asad ^a, Chuan-Wei Oo ^a,^‡, Hasnah Osman ^a, Madhukar Hemamalini ^b, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3151809 PMID: 21837105

Abstract

In the title compound, C₁₅H₈Cl₂N₂O₂, the molecule adopts an E configuration about the central C=N double bond. The isoindoline ring is essentially planar, with a maximum deviation of 0.019 (2) Å. The dihedral angle between the isoindoline ring and the dichloro-substituted benzene ring is 6.54 (9)°. An intramolecular C—H⋯O hydrogen bond occurs. A short Cl⋯Cl contact of 3.4027 (9) Å is present in the crystal structure. The crystal packing is further stabilized by weak C—H⋯π interactions.

Related literature

For the coordination ability and biological activity of Schiff bases, see: Bhunora et al. (2011 ▶); Gupta & Sutar (2008 ▶); Sridhar et al., (2001 ▶); Mladenova et al. (2002 ▶); Bharti et al. (2010 ▶); Tenorio et al. (2005 ▶); Liu et al. (1992 ▶); Hodnett & Dunn (1970 ▶).

Experimental

Crystal data

C₁₅H₈Cl₂N₂O₂
M _r = 319.13
Monoclinic,
a = 8.0387 (8) Å
b = 7.6981 (8) Å
c = 22.2686 (19) Å
β = 101.828 (3)°
V = 1348.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 296 K
0.44 × 0.19 × 0.15 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.815, T _max = 0.930
13900 measured reflections
3902 independent reflections
2795 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.113
S = 1.07
3902 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023063/rz2609sup1.cif

e-67-o1712-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023063/rz2609Isup2.hkl

e-67-o1712-Isup2.hkl^{(191.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023063/rz2609Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1	0.93	2.18	2.857 (2)	129
C2—H2A⋯Cg1ⁱ	0.93	2.81	3.663 (2)	153

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Symmetry code: (i) Inline graphic .

Acknowledgments

MA, CWO and HO thank Universiti Sains Malaysia (USM) for providing the necessary research facilities and RU research funding under grant No. 1001/PKIMIA/811134. MA also thanks USM for the award of a post-doctoral fellowship. HKF and MH thank the Malaysian Government and USM for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Schiff bases have been prepared from the condensation of aldehydes or ketones with amines and their coordination ability with metal ions such as copper (II), cobalt (II), iron (II) and zinc (II) (Bhunora et al., 2011; Gupta & Sutar, 2008) has been studied. Many Schiff bases have been reported to possess antibacterial (Sridhar et al.,, 2001; Mladenova et al., 2002); antifungal (Bharti et al., 2010; Tenorio et al., 2005); and antitumor activities (Liu et al., 1992; Hodnett & Dunn, 1970).

In the title compound (Fig. 1), the molecule adopts an E configuration about the central C7═N1 double bond. The isoindoline ring is essentially planar, with a maximum deviation of 0.019 (2) Å for atom C8. The dihedral angle between the isoindoline ring and the dichloro-substituted phenyl ring is 6.54 (9)°. An intramolecular C—H···O hydrogen bond which generates an S(6) ring motif and a short Cl···Cl contact of 3.4027 (9) Å are present in the crystal structure. The crystal packing (Fig. 2) is further stabilized by a weak C—H···π (Table 1) interactions involving the C1–C6 ring.

Experimental

A mixture of 2-amino-1,3-isoindolinedione (6.15 mmol, 1.0 g) and 2,4-dichloro benzaldehyde (6.15 mmol, 1.08 g) was dissolved in an appropriate amount of ethanol-glacial acetic acid (2:1 v/v). The mixture was refluxed on water-bath for 0.5 hr to give a white colour precipitate. The solution was cooled at room temperature, filtered off, washed with ethanol and dried. The isolated product was recrystallized from chloroform-methanol (1:1 v/v)to get the new Schiff base in 80% yield.