Imidazo[1,2-b]isoquinoline-5,10-dione

Nassir N Al-Mohammed; Yatimah Alias; Zanariah Abdullah; Hamid Khaledi

doi:10.1107/S1600536811022082

. 2011 Jun 18;67(Pt 7):o1666. doi: 10.1107/S1600536811022082

Imidazo[1,2-b]isoquinoline-5,10-dione

Nassir N Al-Mohammed ^a,^‡, Yatimah Alias ^a, Zanariah Abdullah ^a, Hamid Khaledi ^a,^*

PMCID: PMC3151919 PMID: 21837065

Abstract

The title butterfly-shaped molecule, C₁₁H₆N₂O₂, is folded slightly along the O=C⋯C=O line, the dihedral angle between the two parts being 6.42 (3)°. In the crystal, adjacent molecules are linked through C—H⋯O hydrogen bonds into infinite layers parallel to the ac plane. The layers are further connected into a three-dimensional netweork via π–π interactions formed between pairs of antiparallel arranged molecules, with a centroid–centroid distance between the central six-membered ring and the benzene ring of 3.4349 (9) Å.

Related literature

For the structure of isoquinolinedione-pyrrole fused system in 1,3-dinitropyrrolo[1,2-b]isoquinoline-5,10-dione, see: Du & Hitchcock (1992 ▶).

Experimental

Crystal data

C₁₁H₆N₂O₂
M _r = 198.18
Monoclinic,
a = 7.6518 (7) Å
b = 7.2469 (6) Å
c = 15.5197 (13) Å
β = 99.947 (1)°
V = 847.66 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.21 × 0.17 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.977, T _max = 0.990
4894 measured reflections
1925 independent reflections
1583 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.107
S = 1.04
1925 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536811022082/gk2380sup1.cif

e-67-o1666-sup1.cif^{(13.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022082/gk2380Isup2.hkl

e-67-o1666-Isup2.hkl^{(94.8KB, 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
C2—H2⋯O1ⁱ	0.95	2.46	3.2828 (17)	146
C6—H6⋯O1ⁱⁱ	0.95	2.57	3.5190 (19)	179
C8—H8⋯O2ⁱⁱⁱ	0.95	2.55	3.2233 (17)	128

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

Acknowledgments

The authors thank the University of Malaya for funding this study (FRGS grant No. FP001/2010 A).

supplementary crystallographic information

Comment

This work reports the first crystal structure of an isoquinolinedione-fused imidazole. The structure of an isoquinolinedione-pyrrole fused system has been reported previously (Du & Hitchcock, 1992). The present molecule (Fig. 1) is almost planar (r.m.s deviation = 0.0718 Å) but slighly bent along the O=C···.C=O line with the corresponding dihedral angle of 6.42 (3)°. In the crystal, intermolecular C—H···O interactions (Table 1) connect the molecules into a two-dimensional array in the ac plane (Fig. 2). The isoquinoline rings of pairs of the molecule related by symmetry –x + 1, -y + 1, -z, are placed above each other in an anti-parallel manner with the centriods of the six-membered heterocyclic ring and the benzene ring at a distance of 3.4349 (9) Å.

Experimental

A solution of phthaloyl chloride (5.58 g, 27.5 mmol) in dry pyridine (20 ml) was added dropwise to a mixture of imidazole (1.7 g, 25 mmol) and bis (triphenylphosphine)palladium (II) chloride (0.87 g) in dry pyridine (15 ml) at 273 K. The mixture was refluxed for 4 h, then cooled to room temperature and poured into ice water (150 ml). The aqueous solution was extracted with chloroform and the chloroform solution was washed with 2 % aqueous HCl solution and distilled water (3 x15 ml). It was dried over magnesium sulfate and evaporated under vacuum. The amorphous residue was re-crystallized from acetonitrile to give yellow crystals of the title compound (m.p. = 232-234° C).