Ethyl anthracene-9-carboxyl­ate

Edwin Weber; Wilhelm Seichter; Conrad Fischer; L M S Franziska Bendrath; Bakhtiyar T Ibragimov

doi:10.1107/S1600536808017819

. 2008 Jun 19;64(Pt 7):o1288. doi: 10.1107/S1600536808017819

Ethyl anthracene-9-carboxylate

Edwin Weber ^a, Wilhelm Seichter ^a, Conrad Fischer ^a, L M S Franziska Bendrath ^a, Bakhtiyar T Ibragimov ^b,^*

PMCID: PMC2961733 PMID: 21202919

Abstract

In the title compound, C₁₇H₁₄O₂, the COO group and the anthracene fragment form a dihedral angle of 76.00 (19)°. The torsion angle around the O—Csp ³ bond of the ester group is 108.52 (18)°. The crystal structure is stabilized by C—H⋯O interactions and edge-to-face arene interactions with C—H⋯(ring centroid) distances in the range 2.75–2.84 Å.

Related literature

For related crystal structures, see: Bart & Schmidt (1971 ▶); Heller & Schmidt (1971 ▶); Sweeting et al. (1997 ▶). For the preparation of the title compound, see: Larsen & Harpp (1980 ▶).

Experimental

Crystal data

C₁₇H₁₄O₂
M _r = 250.28
Orthorhombic,
a = 8.5431 (6) Å
b = 10.2137 (7) Å
c = 14.5426 (11) Å
V = 1268.94 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 153 (2) K
0.25 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: none
15373 measured reflections
2020 independent reflections
1600 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.085
S = 1.04
2020 reflections
174 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017819/gk2145sup1.cif

e-64-o1288-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017819/gk2145Isup2.hkl

e-64-o1288-Isup2.hkl^{(451.8KB, 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
C5—H5⋯O1ⁱ	0.93	2.53	3.302 (2)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the German Federal Ministry of Economics and Technology (BMWi) under grant No. 16IN0218 ‘ChemoChips’ is gratefully acknowledged. L. M. S. F. Bendrath thanks Dr T. Gruber for supervision of her practical work.

supplementary crystallographic information

Comment

9-Anthracenecarboxylic acid esters are of current interest in materials science (Sweeting et al., 1997). The conformational features of the title compound (Fig. 1) resemble those found in the crystal structure of the analogous methyl 9-anthracenecarboxylate (Bart & Schmidt, 1971). A comparative examination of the crystal structures, however, reveals that a slight modification of the molecular structure has a fundamental influence on the molecular packing mode. According to the presence of a twofold screw axis, helical hydrogen bonded strands (Table 1, Fig. 2) running along the c axis are the basic supramolecular entities of the present crystal structure. Furthermore, the anthracene units of neighbouring strands are arranged in "edge-to-face" herringbone fashion with the closest intermolecular distance of 2.86 Å.

Experimental

9-Anthracenecarbonyl chloride (300 mg) in CH₂Cl₂ (45 ml) was reacted with ethanol (10 ml) and pyridine (2 ml). The resulting solution was heated under reflux for 11 h, then cooled to room temperature and subsequently extracted three times with 2 N aqueous HCl and water (50 ml, each), and finally two times with water (100 ml). After addition of CH₂Cl₂ (200 ml) the organic layer was dried over CaCl₂ and the solvent removed under reduced pressure. Recrystallization of the white powder from acetone yielded colourless crystals suitable for X-ray diffraction analysis. (82%, m.p. 381–382 K). Anal. Calcd. for C₁₇H₁₄O₂: C 81.58; H 5.64; Found: C 81.42; H 5.90%.