Experimental. Crystal data. C 37 H 24 N 2 O 3 M r = Orthorhombic, P a = (1) Å b = (2) Å c = 26.

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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN ,3-Bis(naphthalen-2-ylmethyl)-1H- anthra[1,2-d]imidazole-2,6,11(3h)- trione Zahra Afrakssou, a Youssef Kandri Rodi, a Frédéric Capet, b El Mokhtar Essassi c and Seik Weng Ng d,e * a Laboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, b Unité de Catalyse et de Chimie du Solide, Ecole Nationale Supérieure de Chimie de Lille, Lille, France, c Laboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, d Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia, and e Chemistry Department, Faculty of Science, King Abdulaziz University, PO Box Jeddah, Saudi Arabia Correspondence seikweng@um.edu.my Received 17 July 2011; accepted 19 July 2011 Key indicators: single-crystal X-ray study; T = 293 K; mean (C C) = Å; R factor = 0.044; wr factor = 0.138; data-to-parameter ratio = The title compound, C 37 H 24 N 2 O 3,isa1H-anthra[2,1-d]imidazole-2,6,11(3H)-trione derivative having naphthylmethyl substitutents attached to the imidazole N atoms. The anthraquinone part of the molecule is somewhat folded along the the line connecting the carbonyl bonds. The dihedral angle between the two benzene rings is 7.8 (1). The two naphthyl systems of the substituents of the imidazole ring are positioned on the same side of the five-membered ring; these are approximately coplanar, the dihedral angle between the napthyl systems being 4.3 (2). Related literature For the structure of 1,3-dibenzyl-1H-anthra[1,2-d]imidazole- 2,6,11(3H)-trione, see: Afrakssou et al. (2011). Experimental Crystal data C 37 H 24 N 2 O 3 M r = Orthorhombic, P a = (1) Å b = (2) Å c = (4) Å Data collection Bruker X8 APEXII diffractometer measured reflections 3781 independent reflections Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections V = (7) Å 3 Z =4 Mo K radiation = 0.09 mm 1 T = 293 K mm 3453 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.33 e Å 3 min = 0.15 e Å 3 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). We thank Université Sidi Mohammed Ben Abdallah, Université Mohammed V-Agdal and the University of Malaya for supporting this study. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6819). References Afrakssou, Z., Kandri Rodi, Y., Capet, F., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o1253 o1254. Barbour, L. J. (2001). J. Supramol. Chem. 1, Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, Westrip, S. P. (2010). J. Appl. Cryst. 43, o2138 Afrakssou et al. doi: /s Acta Cryst. (2011). E67, o2138

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3 Acta Cryst. (2011). E67, o2138 [ doi: /s ] 1,3-Bis(naphthalen-2-ylmethyl)-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione Z. Afrakssou, Y. K. Rodi, F. Capet, E. M. Essassi and S. W. Ng Comment The two nitrogen-bound H atoms of 1H-anthra [2,1-d]imidazole-2,6,11(3H)-trione can be replaced by a alkyl substitutent when the compound is reacted with an alkyl halide in a reaction catalyzed by tetra-n-butylammonium bromide; the di-benzyl substituted derivative is synthesized in such a synthesis in high yield. The study (Afrakssou et al., 2011) is now extended to the title naphthylmethyl analog (Scheme I, Fig. 1). In the compound, C 37 H 24 N 2 O 3, the anthraquinone part of the molecule is somewhat folded along the the line connecting the carbonyl bonds (dihedral angle between the two phenyl rings is 7.8 (1) ). The two naphthyl rings of the substituents of the imidazole ring are positioned on the same side of the five-membered ring; these are approximately coplanar (dihedral angle between napthyl rings is 4.3 (2) ). Experimental To a solution of 1H-anthra [2,1-d]imidazole-2,6,11(3H)-trione (0.40 g, 1.51 mmol), potassium carbonate (0.83 g, 6.05 mmol) and tetra-n-butylammonium bromide (0.04 g, 0.15 mmol) in DMF (15 ml)) was added 2-(bromomethyl)naphthalene (0.83 g, 3.78 mmol). Stirring was continued at room temperature for 24 h. The mixture was filtered and the solvent removed. The residue was extracted with water. The organic compound was chromatographed on a column of silica gel with ethyl acetate-hexane (1/1) as eluent. Orange crystals were isolated when the solvent was allowed to evaporate. Refinement Carbon-bound H-atoms were placed in calculated positions (C H Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C) Friedel pairs were merged. In the absence of heavy atoms, some 2920 Friedel pairs were merged. Figures Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C 37 H 24 N 2 O 3 at the 50% probability level; hydrogen atoms are drawn as arbitrary radius. 1,3-Bis(naphthalen-2-ylmethyl)-1H-anthra[1,2-d]imidazole- 2,6,11(3H)-trione Crystal data C 37 H 24 N 2 O 3 F(000) = 1136 sup-1

4 M r = D x = Mg m 3 Orthorhombic, P Mo Kα radiation, λ = Å Hall symbol: P 2ac 2ab Cell parameters from 9907 reflections a = (1) Å θ = b = (2) Å µ = 0.09 mm 1 c = (4) Å T = 293 K V = (7) Å 3 Prism, orange Z = mm Data collection Bruker X8 APEXII diffractometer Radiation source: fine-focus sealed tube R int = reflections with I > 2σ(I) graphite θ max = 28.3, θ min = 1.6 φ and ω scans h = measured reflections k = independent reflections l = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained S = 1.10 w = 1/[σ 2 (F 2 o ) + (0.0817P) P] where P = (F 2 o + 2F 2 c )/ reflections (Δ/σ) max = parameters Δρ max = 0.33 e Å 3 0 restraints Δρ min = 0.15 e Å 3 Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq O (3) (16) (10) (6) O (2) (15) (8) (5) O (3) (14) (9) (5) N (3) (15) (7) (4) N (2) (14) (7) (4) C (3) (17) (8) (4) C (3) (19) (9) (5) H * C (3) (2) (9) (5) H * C (3) (18) (8) (4) sup-2

5 C (3) (19) (9) (5) C (3) (18) (8) (5) C (4) (19) (9) (6) H * C (4) (2) (10) (7) H * C (4) (2) (11) (7) H * C (3) (2) (10) (6) H * C (3) (17) (8) (5) C (3) (18) (8) (4) C (3) (17) (8) (4) C (3) (16) (7) (4) C (3) (18) (9) (5) C (3) (19) (10) (6) H16A * H16B * C (3) (17) (10) (5) C (3) (18) (10) (5) H * C (3) (2) (10) (6) C (4) (3) (12) (7) H * C (5) (3) (13) (10) H * C (5) (4) (16) (13) H * C (5) (3) (16) (12) H * C (3) (2) (13) (7) C (4) (3) (14) (9) H * C (4) (2) (13) (8) H * C (3) (19) (9) (5) H27A * H27B * C (3) (2) (10) (5) C (4) (2) (12) (7) H * C (4) (3) (12) (8) C (8) (4) (19) (16) H * C (9) (5) (2) (2) H * C (9) (5) (17) (2) H * C (7) (5) (15) (15) sup-3

6 H * C (5) (3) (13) (9) C (5) (3) (14) (10) H * C (4) (3) (12) (7) H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (11) (10) (16) (9) (11) (11) O (8) (9) (13) (7) (8) (9) O (12) (8) (15) (9) (11) (9) N (10) (9) (10) (8) (8) (7) N (9) (9) (9) (7) (7) (7) C (10) (10) (9) (9) (8) (8) C (9) (12) (11) (9) (9) (10) C (10) (12) (11) (9) (9) (10) C (10) (10) (10) (9) (8) (8) C (12) (11) (12) (10) (10) (9) C (12) (10) (10) (10) (9) (8) C (15) (11) (12) (11) (11) (9) C (19) (11) (14) (12) (14) (10) C (16) (13) (16) (13) (14) (12) C (13) (12) (14) (11) (11) (11) C (11) (10) (11) (9) (9) (8) C (10) (10) (10) (8) (8) (8) C (9) (10) (9) (8) (7) (7) C (9) (10) (8) (8) (7) (7) C (12) (10) (11) (10) (10) (9) C (14) (11) (14) (11) (11) (10) C (11) (10) (13) (9) (10) (9) C (12) (11) (13) (10) (10) (9) C (12) (13) (13) (11) (10) (11) C (18) (17) (16) (16) (14) (13) C (2) (3) (16) (2) (17) (17) C (3) (3) (2) (3) (2) (2) C (2) (3) (3) (2) (2) (2) C (13) (16) (18) (13) (13) (14) C (18) (17) (2) (15) (17) (17) C (16) (13) (2) (13) (15) (13) C (10) (11) (12) (9) (9) (10) C (11) (13) (12) (10) (10) (10) C (14) (16) (16) (13) (13) (12) C (17) (18) (16) (16) (14) (14) C (4) (4) (3) (3) (3) (3) C (5) (4) (3) (4) (3) (3) C (5) (5) (2) (5) (3) (3) sup-4

7 C (4) (4) (2) (3) (2) (2) C (2) (2) (17) (19) (15) (17) C (2) (2) (17) (2) (17) (18) C (18) (17) (15) (16) (14) (13) Geometric parameters (Å, ) O1 C (3) C18 H O2 C (3) C19 C (4) O3 C (3) C19 C (4) N1 C (3) C20 C (5) N1 C (3) C20 H N1 C (3) C21 C (6) N2 C (3) C21 H N2 C (3) C22 C (6) N2 C (3) C22 H C1 C (3) C23 C (5) C1 C (3) C23 H C2 C (3) C24 C (5) C2 H C25 C (5) C3 C (3) C25 H C3 H C26 H C4 C (3) C27 C (3) C4 C (3) C27 H27A C5 C (4) C27 H27B C6 C (3) C28 C (4) C6 C (3) C28 C (4) C7 C (4) C29 C (4) C7 H C29 H C8 C (4) C30 C (5) C8 H C30 C (6) C9 C (4) C31 C (7) C9 H C31 H C10 C (3) C32 C (9) C10 H C32 H C11 C (3) C33 C (8) C12 C (3) C33 H C13 C (3) C34 C (5) C16 C (4) C34 H C16 H16A C35 C (6) C16 H16B C36 C (5) C17 C (3) C36 H C17 C (3) C37 H C18 C (4) C15 N1 C (19) C19 C18 H C15 N1 C (2) C20 C19 C (2) C1 N1 C (2) C20 C19 C (3) C14 N2 C (18) C18 C19 C (3) C14 N2 C (19) C21 C20 C (3) sup-5

8 C15 N2 C (19) C21 C20 H C2 C1 N (2) C19 C20 H C2 C1 C (19) C20 C21 C (4) N1 C1 C (19) C20 C21 H C1 C2 C (2) C22 C21 H C1 C2 H C23 C22 C (3) C3 C2 H C23 C22 H C2 C3 C (2) C21 C22 H C2 C3 H C22 C23 C (4) C4 C3 H C22 C23 H C3 C4 C (2) C24 C23 H C3 C4 C (2) C25 C24 C (3) C13 C4 C (2) C25 C24 C (3) O1 C5 C (2) C23 C24 C (3) O1 C5 C (2) C26 C25 C (3) C6 C5 C (2) C26 C25 H C11 C6 C (2) C24 C25 H C11 C6 C (2) C25 C26 C (3) C7 C6 C (2) C25 C26 H C8 C7 C (3) C17 C26 H C8 C7 H N2 C27 C (19) C6 C7 H N2 C27 H27A C9 C8 C (2) C28 C27 H27A C9 C8 H N2 C27 H27B C7 C8 H C28 C27 H27B C8 C9 C (3) H27A C27 H27B C8 C9 H C29 C28 C (3) C10 C9 H C29 C28 C (3) C11 C10 C (3) C37 C28 C (2) C11 C10 H C28 C29 C (3) C9 C10 H C28 C29 H C6 C11 C (2) C30 C29 H C6 C11 C (2) C35 C30 C (4) C10 C11 C (2) C35 C30 C (3) O2 C12 C (2) C31 C30 C (4) O2 C12 C (2) C32 C31 C (6) C13 C12 C (2) C32 C31 H C14 C13 C (19) C30 C31 H C14 C13 C (19) C31 C32 C (5) C4 C13 C (18) C31 C32 H N2 C14 C (19) C33 C32 H N2 C14 C (17) C34 C33 C (4) C13 C14 C (19) C34 C33 H O3 C15 N (2) C32 C33 H O3 C15 N (2) C33 C34 C (5) N1 C15 N (19) C33 C34 H N1 C16 C (19) C35 C34 H N1 C16 H16A C30 C35 C (3) C17 C16 H16A C30 C35 C (4) sup-6

9 N1 C16 H16B C36 C35 C (4) C17 C16 H16B C37 C36 C (3) H16A C16 H16B C37 C36 H C18 C17 C (3) C35 C36 H C18 C17 C (2) C36 C37 C (3) C26 C17 C (2) C36 C37 H C17 C18 C (2) C28 C37 H C17 C18 H C15 N1 C1 C (2) C1 N1 C15 N2 0.3 (3) C16 N1 C1 C (4) C16 N1 C15 N (19) C15 N1 C1 C (3) C14 N2 C15 O (3) C16 N1 C1 C (2) C27 N2 C15 O (4) N1 C1 C2 C (2) C14 N2 C15 N1 0.5 (2) C14 C1 C2 C3 1.5 (3) C27 N2 C15 N (19) C1 C2 C3 C4 1.8 (3) C15 N1 C16 C (3) C2 C3 C4 C (3) C1 N1 C16 C (3) C2 C3 C4 C (2) N1 C16 C17 C (4) C3 C4 C5 O1 6.7 (4) N1 C16 C17 C (2) C13 C4 C5 O (2) C26 C17 C18 C (4) C3 C4 C5 C (2) C16 C17 C18 C (2) C13 C4 C5 C6 7.3 (3) C17 C18 C19 C (3) O1 C5 C6 C (2) C17 C18 C19 C (4) C4 C5 C6 C (3) C18 C19 C20 C (3) O1 C5 C6 C7 7.5 (4) C24 C19 C20 C (5) C4 C5 C6 C (2) C19 C20 C21 C (5) C11 C6 C7 C8 1.7 (4) C20 C21 C22 C (6) C5 C6 C7 C (2) C21 C22 C23 C (6) C6 C7 C8 C9 0.7 (4) C22 C23 C24 C (4) C7 C8 C9 C (4) C22 C23 C24 C (5) C8 C9 C10 C (4) C20 C19 C24 C (3) C7 C6 C11 C (3) C18 C19 C24 C (4) C5 C6 C11 C (2) C20 C19 C24 C (4) C7 C6 C11 C (2) C18 C19 C24 C (3) C5 C6 C11 C (3) C23 C24 C25 C (3) C9 C10 C11 C6 1.3 (4) C19 C24 C25 C (5) C9 C10 C11 C (2) C24 C25 C26 C (5) C6 C11 C12 O (2) C18 C17 C26 C (4) C10 C11 C12 O (3) C16 C17 C26 C (3) C6 C11 C12 C (3) C14 N2 C27 C (3) C10 C11 C12 C (2) C15 N2 C27 C (2) C3 C4 C13 C (3) N2 C27 C28 C (3) C5 C4 C13 C (19) N2 C27 C28 C (3) C3 C4 C13 C (2) C37 C28 C29 C (4) C5 C4 C13 C (3) C27 C28 C29 C (3) O2 C12 C13 C (3) C28 C29 C30 C (5) C11 C12 C13 C (19) C28 C29 C30 C (4) O2 C12 C13 C (2) C35 C30 C31 C (7) C11 C12 C13 C (3) C29 C30 C31 C (5) C15 N2 C14 C (2) C30 C31 C32 C (9) sup-7

10 C27 N2 C14 C (4) C31 C32 C33 C (10) C15 N2 C14 C1 1.1 (2) C32 C33 C34 C (9) C27 N2 C14 C (2) C31 C30 C35 C (4) C4 C13 C14 N (2) C29 C30 C35 C (5) C12 C13 C14 N2 8.3 (4) C31 C30 C35 C (6) C4 C13 C14 C1 3.2 (3) C29 C30 C35 C (4) C12 C13 C14 C (19) C33 C34 C35 C (7) C2 C1 C14 N (2) C33 C34 C35 C (5) N1 C1 C14 N2 1.3 (2) C30 C35 C36 C (6) C2 C1 C14 C (3) C34 C35 C36 C (4) N1 C1 C14 C (18) C35 C36 C37 C (6) C1 N1 C15 O (2) C29 C28 C37 C (5) C16 N1 C15 O (4) C27 C28 C37 C (3) sup-8

11 Fig. 1 sup-9