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Volume 69 
Part 6 
Pages o945-o946  
June 2013  

Received 13 May 2013
Accepted 17 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.148
Data-to-parameter ratio = 17.9
Details
Open access

1-(Prop-2-en-1-yl)-3-{[3-(pyridin-4-yl)-4,5-dihydroisoxazol-5-yl]methyl}-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed, Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco,bUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181 Ecole Nationale Supérieure de Chimie de Lille, France,cLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014, Avenue Ibn Batouta, Rabat , Morocco,dUSR 3290 Miniaturisation pour l'Analyse, la Synthèse et la Protéomique, 59655 Villeneuve d'Ascq Cedex, Université Lille 1, France, and eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: afrassou@yahoo.fr

The fused five- and three six-membered rings of the anthra[1,2-d]imidazoletrione part of the title compound, C27H20N4O4, show two different substituents at the imidazole N atoms, viz. an allyl group and a [3-(pyridin-4-yl)-4,5-dihydroisoxazol-5-yl]methyl group. The fused-ring system is approximately planar [r.m.s. deviation = 0.232 (2) Å], but is slightly buckled along the common edge of the two pairs of adjacent rings, with a dihedral angle between them of 11.17 (6)°. The isoxazole ring makes dihedral angles of 27.2 (2) and 12.7 (2)° with the imidazole and pyridine rings, respectively. Weak C-H...O and C-H...N hydrogen bonds ensure the cohesion of the crystal structure, forming a three-dimensional network.

Related literature

For the use of anthraquinone as an organic redox mediator, see: Campos-Martin et al. (2006[Campos-Martin, J. M., Blanco-Brieva, G. & Fierro, J. L. G. (2006). Angew. Chem. Int. Ed. 45, 6962-6984.]); Harish et al. (2009[Harish, S., Sridharan, D., Kumar, S. S., Joseph, J. & Phani, K. L. N. (2009). Electrochim. Acta, 54, 3618-3622.]); Jürmann et al. (2007[Jürmann, G., Schiffrin, D. J. & Tammeveski, K. (2007). Electrochim. Acta, 53, 390-399.]); Manisankar & Gomathi (2005[Manisankar, P. & Gomathi, A. (2005). J. Mol. Catal. A Chem. 232, 45-52.]). For the biological activity of anthraquinone derivatives, see: Henderson et al. (1998[Henderson, P. T., Armitage, B. & Schuster, G. B. (1998). Biochemistry, 37, 2991-3000.]); Barasch et al. (1999[Barasch, D., Zipori, O., Ringel, I., Ginsbury, I., Samuni, A. & Katzhendler, J. (1999). Eur. J. Med. Chem. 34, 597-615.]); Dou et al. (2009[Dou, Y., Haswell, S., Greenman, J. & Wadhawan, J. (2009). Electrochem. Commun. 11, 1976-1981.]). For background to pH sensor applications, see: Wong et al. (2004[Wong, E. L. S., Erohkin, P. & Gooding, J. J. (2004). Electrochem. Commun. 6, 648-654.]); Lafitte et al. (2008[Lafitte, V. G. H., Wang, W., Yashina, A. S. & Lawrence, N. S. (2008). Electrochem. Commun. 10, 1831-1834.]); Wildgoose et al. (2003[Wildgoose, G. G., Pandurangappa, M., Lawrence, N. S., Jiang, L., Jones, T. G. J. & Compton, R. G. (2003). Talanta, 60, 887-893.]). For similar compounds, see: Afrakssou et al. (2010[Afrakssou, Z., Rodi, Y. K., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1851.], 2011[Afrakssou, Z., Haoudi, A., Capet, F., Rolando, C. & El Ammari, L. (2011). Acta Cryst. E67, o1363-o1364.]).

[Scheme 1]

Experimental

Crystal data
  • C27H20N4O4

  • Mr = 464.47

  • Triclinic, [P \overline 1]

  • a = 8.0930 (2) Å

  • b = 12.1191 (3) Å

  • c = 12.2743 (2) Å

  • [alpha] = 87.109 (1)°

  • [beta] = 73.612 (1)°

  • [gamma] = 72.283 (1)°

  • V = 1099.35 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.14 × 0.10 × 0.08 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 36799 measured reflections

  • 5659 independent reflections

  • 3900 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.148

  • S = 1.02

  • 5659 reflections

  • 316 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...N3i 0.93 2.58 3.471 (2) 160
C3-H3...O4i 0.93 2.67 3.470 (2) 145
C19-H19A...O3ii 0.97 2.56 3.3356 (19) 137
C21-H21A...O3ii 0.97 2.45 3.350 (2) 154
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+3, -y, -z+2.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2433 ).


References

Afrakssou, Z., Haoudi, A., Capet, F., Rolando, C. & El Ammari, L. (2011). Acta Cryst. E67, o1363-o1364.  [CSD] [CrossRef] [ChemPort] [details]
Afrakssou, Z., Rodi, Y. K., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1851.  [CSD] [CrossRef] [details]
Barasch, D., Zipori, O., Ringel, I., Ginsbury, I., Samuni, A. & Katzhendler, J. (1999). Eur. J. Med. Chem. 34, 597-615.  [ISI] [PubMed] [ChemPort]
Bruker (2009). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Campos-Martin, J. M., Blanco-Brieva, G. & Fierro, J. L. G. (2006). Angew. Chem. Int. Ed. 45, 6962-6984.  [ChemPort]
Dou, Y., Haswell, S., Greenman, J. & Wadhawan, J. (2009). Electrochem. Commun. 11, 1976-1981.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Harish, S., Sridharan, D., Kumar, S. S., Joseph, J. & Phani, K. L. N. (2009). Electrochim. Acta, 54, 3618-3622.  [ISI] [CrossRef] [ChemPort]
Henderson, P. T., Armitage, B. & Schuster, G. B. (1998). Biochemistry, 37, 2991-3000.  [ISI] [CrossRef] [ChemPort] [PubMed]
Jürmann, G., Schiffrin, D. J. & Tammeveski, K. (2007). Electrochim. Acta, 53, 390-399.
Lafitte, V. G. H., Wang, W., Yashina, A. S. & Lawrence, N. S. (2008). Electrochem. Commun. 10, 1831-1834.  [ISI] [CrossRef] [ChemPort]
Manisankar, P. & Gomathi, A. (2005). J. Mol. Catal. A Chem. 232, 45-52.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Wildgoose, G. G., Pandurangappa, M., Lawrence, N. S., Jiang, L., Jones, T. G. J. & Compton, R. G. (2003). Talanta, 60, 887-893.  [ISI] [CrossRef] [PubMed] [ChemPort]
Wong, E. L. S., Erohkin, P. & Gooding, J. J. (2004). Electrochem. Commun. 6, 648-654.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o945-o946   [ doi:10.1107/S160053681301369X ]

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