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

Nl-Mohammed, N.; Alias, Y.; Abdullah, Z.; Khaledi, H.

doi:10.1107/S1600536811022082

Volume 67
Part 7
Page o1666
July 2011

Received 22 May 2011
Accepted 7 June 2011
Online 18 June 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.107
Data-to-parameter ratio = 14.2
Details

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

Nassir N. Al-Mohammed,^a ⁺ Yatimah Alias,^a Zanariah Abdullah ^a and Hamid Khaledi ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: khaledi@siswa.um.edu.my

The title butterfly-shaped molecule, C₁₁H₆N₂O₂, is folded slightly along the O=CC=O line, the dihedral angle between the two parts being 6.42 (3)°. In the crystal, adjacent molecules are linked through C-HO hydrogen bonds into infinite layers parallel to the ac plane. The layers are further connected into a three-dimensional netweork via [pi] - [pi] 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, P 2₁ /c
a = 7.6518 (7) Å
b = 7.2469 (6) Å
c = 15.5197 (13) Å
= 99.947 (1)°
V = 847.66 (13) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.107
S = 1.04
1925 reflections
136 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O1ⁱ	0.95	2.46	3.2828 (17)	146
C6-H6O1ⁱⁱ	0.95	2.57	3.5190 (19)	179
C8-H8O2ⁱⁱⁱ	0.95	2.55	3.2233 (17)	128
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x-1, y, z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: GK2380 ).

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem, 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Du, M.-H. & Hitchcock, P. B. (1992). Acta Cryst. C48, 2058-2060.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References