(Z)-3-(9-Anthr­yl)-1-(4-bromo­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Yi-Hui Lu; Guang-Zhou Wang; Cheng-He Zhou; Yi-Yi Zhang

doi:10.1107/S1600536809018352

. 2009 May 23;65(Pt 6):o1396. doi: 10.1107/S1600536809018352

(Z)-3-(9-Anthryl)-1-(4-bromophenyl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Yi-Hui Lu ^a, Guang-Zhou Wang ^a, Cheng-He Zhou ^a,^*, Yi-Yi Zhang ^a

PMCID: PMC2969633 PMID: 21583241

Abstract

In the title molecule, C₂₆H₁₆BrN₃O₃, the anthracene and benzene mean planes make dihedral angles of 63.79 (2) and 14.67 (2)°, respectively, with the plane of the imidazole ring. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules to form centrosymmetric dimers. Weak π–π stacking interactions, with centroid–centroid distances of 3.779 (2) and 3.826 (2) Å, supply additional stabilization. The crystal packing also exhibits short intermolecular contacts between the nitro groups and Br atoms [Br⋯O = 3.114 (2) Å].

Related literature

For the crystal structure of the chloro analog of the title compound, see: Wang et al. (2009 ▶). For general background on the pharmacological activities of chalcones, see: Corréa et al. (2001 ▶); Jasinski et al. (2009 ▶); Nielsen et al. (1998 ▶); Vogel et al. (2008 ▶). For the synthetic details, see: Erhardt et al. (1985 ▶); Kranz et al. (1980 ▶).

Experimental

Crystal data

C₂₆H₁₆BrN₃O₃
M _r = 498.33
Triclinic,
a = 8.1438 (11) Å
b = 11.0916 (14) Å
c = 12.7979 (17) Å
α = 78.146 (2)°
β = 86.193 (2)°
γ = 70.768 (2)°
V = 1068.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 292 K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.775, T _max = 0.828
6422 measured reflections
4315 independent reflections
3095 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.116
S = 1.02
4315 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018352/lh2825sup1.cif

e-65-o1396-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018352/lh2825Isup2.hkl

e-65-o1396-Isup2.hkl^{(211.4KB, 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
C23—H23⋯O3ⁱ	0.93	2.56	3.303 (4)	137

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant No. 2007BB5369) for financial support.

supplementary crystallographic information

Comment

Chalcones and their derivatives have been reported responsible for a variety of pharmacological activities, including antibacterial, antifungal, anti-leishmanial, antimalarial, analgesic, anti-inflammatory and chemopreventive ones (Corréa et al., 2001; Jasinski et al., 2009; Simon et al., 1998; Vogel et al., 2008). Due to these varied applications, we have synthesized the title compound and report its crystal structure.

In the molecular structure of the title compound (I) (Fig. 1), the dihedral angle between the anthracene unit and imidazole ring is 63.79 (2) ° and that between the imidazole ring and benzene ring is 14.67 (2) °. In the crystal structure, weak intermolecular C—H···O hydrogen bonds link molecules to form centrosymmetric dimers (Fig. 2). Weak π–π staking interactions, with centroid to centroid distances of 3.779 (2) and 3.826 (2)Å supply additional stabilization.

Experimental

Compound (I) was synthesized according to the procedure of Erhardt et al. (1985); Kranz et al. (1980). A crystal suitable for X-ray analysis was grown from a chloroform and acetone solution of (I) by slow evaporation at room temperature.