2-(4-Bromo­phen­yl)-2-oxoethyl anthracene-9-carboxyl­ate

Hoong-Kun Fun; Safra Izuani Jama Asik; B Garudachari; Arun M Isloor; M N Satyanarayan

doi:10.1107/S1600536812022684

. 2012 May 26;68(Pt 6):o1876. doi: 10.1107/S1600536812022684

2-(4-Bromophenyl)-2-oxoethyl anthracene-9-carboxylate

Hoong-Kun Fun ^a,^*,^‡, Safra Izuani Jama Asik ^a, B Garudachari ^b, Arun M Isloor ^b, M N Satyanarayan ^c

PMCID: PMC3379439 PMID: 22719637

Abstract

In the title compound, C₂₃H₁₅BrO₃, the anthracene ring system is essentially planar [maximum deviation = 0.29 (2) Å] and makes a dihedral angle of 5.74 (8)° with the mean plane of the bromo-substituted benzene ring. An intramolecular C—H⋯O hydrogen bond generates an S(9) ring motif. In the crystal, molecules are linked by C—H⋯O interactions, forming a two-dimensional network parallel to the ac plane. π–π stacking interactions are observed between benzene rings [centroid–centroid distances = 3.5949 (14) and 3.5960 (13) Å].

Related literature

For background to the applications of anthracene, see: Bae et al. (2010 ▶); Reddy et al. (2011 ▶); Rather & Reid (1919 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). graphic file with name e-68-o1876-scheme1.jpg

Experimental

Crystal data

C₂₃H₁₅BrO₃
M _r = 419.26
Monoclinic,
a = 10.1906 (8) Å
b = 15.0591 (12) Å
c = 13.7938 (8) Å
β = 122.376 (4)°
V = 1787.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.32 mm⁻¹
T = 100 K
0.29 × 0.19 × 0.18 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.550, T _max = 0.677
23513 measured reflections
6409 independent reflections
4600 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.141
S = 1.01
6409 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 1.67 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022684/rz2758sup1.cif

e-68-o1876-sup1.cif^{(27.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022684/rz2758Isup2.hkl

e-68-o1876-Isup2.hkl^{(313.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022684/rz2758Isup3.cml

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
C12—H12A⋯O3	0.93	2.50	3.401 (3)	164
C20—H20A⋯O1ⁱ	0.93	2.47	3.394 (3)	176
C22—H22A⋯O3ⁱⁱ	0.93	2.31	3.199 (3)	159

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

HKF and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Research University grants (Nos.1001/PFIZIK/811160 and 1001/PFIZIK/ 811151). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award. SMN thanks Department of Information Technology, New Delhi, India, for financial support.

supplementary crystallographic information

Comment

Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings. It is used in the production of the dyes and organic semiconductor (Bae et al., 2010) as high energy photons, electrons and alpha particle detectors and also used in blue light emitter in OLEDs (Reddy et al., 2011) and identification of organic acids (Rather & Reid, 1919). Keeping this in view, the title compound (I) was synthesized to study its crystal structure.

In the title compound of (I), (Fig. 1), the anthracene (C1–C14) is essentially planar with maximum deviation of 0.029 (2) Å at atom C7 and makes a dihedral angle of 5.74 (8)° with the mean plane of bromo-substituted benzene (C18–C23) ring. The intramolecular C12—H12A···O3 interaction generates a S(9) ring motif (Bernstein et al., 1995).

In the crystal structure of (Fig, 2), the molecules are linked by C20—H20A···O1 and C22—H22A···O3 interactions to form a two-dimensional network parallel to ac plane. π–π stacking interactions are observed between benzene rings with Cg2···Cg3 and Cg2···Cg4 distances of 3.5949 (14) and 3.5960 (13) Å, respectively. [Cg2 , Cg3 and Cg4 are the centroids of (C1/C6–C8/C13–C14), (C8–C13) and (C18–C23) rings, respectively.]

Experimental

A mixture of anthracene-9-carboxylic acid (1.0 g, 0.0044 mol), potassium carbonate (0.589 g, 0.0043 mol) and 2-bromo-1-(4-bromophenyl)ethanone (0.746 g, 0.0053 mol) in dimethylformamide (10 ml) was stirred at room temperature for 1 h. On cooling, colourless needle-shaped crystals of 2-(4-bromophenyl)-2-oxoethyl anthracene-9-carboxylate separated. They were collected by filtration and recrystallized from ethanol. Yield: 1.60 g, 85.1 %, M.p. 421–423 K.