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Volume 69 
Part 6 
Page o944  
June 2013  

Received 7 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 = 0.044
wR = 0.129
Data-to-parameter ratio = 13.5
Details
Open access

1,3-Bis(prop-2-yn-1-yl)-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,cUSR 3290 Miniaturisation pour l'Analyse, la Synthèse et la Protéomique, 59655 Villeneuve d'Ascq Cedex, Université Lille 1, France, and dLaboratoire 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

In the title compound, C21H12N2O3, the fused-ring system is roughly planar, the largest deviation from the mean plane being 0.084 (2) Å. The two prop-2-yn-1-yl groups are almost perpendicular to the fused ring plane, making C-C-N-C torsion angles of -103.4 (2) and -105.3 (2)°, and point in opposite directions with respect to the plane. In the crystal, molecules are linked by weak C-H...O hydrogen bonds, forming a three-dimensional network.

Related literature

For background to the pharmacological activity and potential applications of anthraquinones, see: Alves et al. (2004[Alves, D. S., Perez-Fons, L., Estepa, A. & Micol, V. (2004). Biochem. Pharmacol. 68, 549-561.]); Ellis et al. (2003[Ellis, L. T., Perkins, D. F., Turner, P. & Hambley, T. W. (2003). Dalton Trans. pp. 2728-2736.]); Boseggia et al. (2004[Boseggia, E., Gatos, M., Lucatello, L., Mancin, F., Moro, S., Palumbo, M., Sissi, C., Tecilla, P., Tonellato, U. & Zagotto, G. (2004). J. Am. Chem. Soc. 126, 4543-4549.]); Mariappan & Basa (2011[Mariappan, K. & Basa, P. N. (2011). Inorg. Chim. Acta, 366, 344-349.]); Kadarkaraisamy et al. (2008[Kadarkaraisamy, M., Caple, G., Gorden, A. R. & Sykes, A. G. (2008). Inorg. Chem. 47, 11644-11655.]). 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., Kandri Rodi, Y., Capet, F., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o1253-o1254.]); Guimarães et al. (2009[Guimarães, T. T., Da Silva Júnior, E. N., Carvalho, C. E. M., De Simone, C. A. & Pinto, A. V. (2009). Acta Cryst. E65, o1063.]).

[Scheme 1]

Experimental

Crystal data
  • C21H12N2O3

  • Mr = 340.33

  • Monoclinic, P 21 /c

  • a = 16.6972 (5) Å

  • b = 4.5602 (1) Å

  • c = 21.2500 (5) Å

  • [beta] = 96.352 (2)°

  • V = 1608.10 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.46 × 0.14 × 0.05 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 20426 measured reflections

  • 3177 independent reflections

  • 2301 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.129

  • S = 1.02

  • 3177 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18...O2i 0.93 2.31 3.165 (3) 152
C21-H21...O1ii 0.93 2.38 3.275 (3) 161
C2-H2...O3iii 0.93 2.62 3.333 (3) 134
Symmetry codes: (i) [-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 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: IM2432 ).


References

Afrakssou, Z., Kandri Rodi, Y., Capet, F., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o1253-o1254.  [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]
Alves, D. S., Perez-Fons, L., Estepa, A. & Micol, V. (2004). Biochem. Pharmacol. 68, 549-561.  [ISI] [CrossRef] [PubMed] [ChemPort]
Boseggia, E., Gatos, M., Lucatello, L., Mancin, F., Moro, S., Palumbo, M., Sissi, C., Tecilla, P., Tonellato, U. & Zagotto, G. (2004). J. Am. Chem. Soc. 126, 4543-4549.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Ellis, L. T., Perkins, D. F., Turner, P. & Hambley, T. W. (2003). Dalton Trans. pp. 2728-2736.  [CSD] [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Guimarães, T. T., Da Silva Júnior, E. N., Carvalho, C. E. M., De Simone, C. A. & Pinto, A. V. (2009). Acta Cryst. E65, o1063.  [CSD] [CrossRef] [details]
Kadarkaraisamy, M., Caple, G., Gorden, A. R. & Sykes, A. G. (2008). Inorg. Chem. 47, 11644-11655.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Mariappan, K. & Basa, P. N. (2011). Inorg. Chim. Acta, 366, 344-349.  [ISI] [CSD] [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]


Acta Cryst (2013). E69, o944  [ doi:10.1107/S1600536813013688 ]

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