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

Zahra Afrakssou; Youssef Kandri Rodi; Hafid Zouihri; El Mokhtar Essassi; Seik Weng Ng

doi:10.1107/S1600536810024748

. 2010 Jun 26;66(Pt 7):o1851. doi: 10.1107/S1600536810024748

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, Seik Weng Ng ^d,^*

PMCID: PMC3007069 PMID: 21588049

Abstract

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—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₂₁H₁₆N₂O₃
M _r = 344.36
Monoclinic,
a = 7.8539 (2) Å
b = 11.5822 (3) Å
c = 18.1455 (4) Å
β = 93.537 (1)°
V = 1647.47 (7) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.153
S = 1.02
4805 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.22 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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024748/ci5112sup1.cif

e-66-o1851-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024748/ci5112Isup2.hkl

e-66-o1851-Isup2.hkl^{(235.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3ⁱ	0.93	2.49	3.406 (2)	168
C16—H16B⋯O3ⁱ	0.97	2.42	3.362 (2)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

An imidazol-one such as 1H-anthra[2,1-d]imidazole-2,6,11(3H)-trione, in which the five-membered ring is fused with an anthraquinone system, alkyl halides under catalytic conditions to yield di-N,N'-substituted derivatives that serve as starting reagents for the synthesis of other drugs. The anthraquinone system itself is found in a large number of pigments and dyes. The title compound (Scheme I, Fig. 1) is a deep orange material that may be useful as an organic fluorophone.

The title molecule features four rings that are fused together (r.m.s. deviation 0.067 Å). The fused-ring system is slightly buckled at that carbonyl C-atom, C3, of the anthracenyl system [0.177 (1) Å] that is closer to an allyl substituent. The pendant allyl units lie on the same side of the fused-ring plane but are oriented in opposite directions. The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1).

Experimental

To a solution of 1H-anthra[2,1-d]imidazole-2,6,11(3H)-trione (1.00 g, 0.38 mmol), potassium carbonate (1.56 g,11 mmol) and tetra n-butyl ammonium bromide (0.12 g, 0.38 mmol) in DMF (20 ml)) was added allyl bromide (0.77 ml, 11 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.