1,3-Diallyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Afrakssou, Z.; Rodi, Y.K.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810024748

Volume 66
Part 7
Page o1851
July 2010

Received 22 June 2010
Accepted 24 June 2010
Online 26 June 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.049
wR = 0.153
Data-to-parameter ratio = 20.4
Details

1,3-Diallyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Zahra Afrakssou,^a Youssef Kandri Rodi,^a Hafid Zouihri,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès, Morocco,^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco,^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the title compound, C₂₁H₁₆N₂O₃, the fused-ring system (r.m.s. deviation = 0.067 Å) is slightly buckled at the carbonyl C atom of the anthracenyl ring system [deviation = 0.177 (1) Å] that is closer to an allyl substituent. The two allyl units lie on the same side of the fused-ring plane but are oriented in opposite directions, with N-C-C-C torsion angles of 126.9 (2) and 116.7 (2)°. In the crystal, the molecules are linked into chains propagating along the b axis by C-HO hydrogen bonds.

Related literature

For a related structure, see: Guimarães et al. (2009).

Experimental

Crystal data

C₂₁H₁₆N₂O₃
M_r = 344.36
Monoclinic, P 2₁ /c
a = 7.8539 (2) Å
b = 11.5822 (3) Å
c = 18.1455 (4) Å
= 93.537 (1)°
V = 1647.47 (7) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.40 × 0.35 × 0.20 mm

Data collection

Bruker X8 APEXII area-detector diffractometer
22612 measured reflections
4806 independent reflections 4805 in Refinement?
3053 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.153
S = 1.02
4805 reflections
236 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13O3ⁱ	0.93	2.49	3.406 (2)	168
C16-H16BO3ⁱ	0.97	2.42	3.362 (2)	165
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5112 ).

Acknowledgements

The authors thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Guimarães, T. T., Da Silva Júnior, E. N., Carvalho, C. E. M., De Simone, C. A. & Pinto, A. V. (2009). Acta Cryst. E65, o1063.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.

organic compounds

1,3-Diallyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References