Ethyl trans-12-(pyridin-4-yl)-9,10-ethano­anthracene-11-carboxyl­ate

S Chandrasekar; Prakash Sharma Om; V Srinivasapriyan; M SureshKumar; C R Ramanathan

doi:10.1107/S1600536814006588

. 2014 Apr 2;70(Pt 5):o512. doi: 10.1107/S1600536814006588

Ethyl trans-12-(pyridin-4-yl)-9,10-ethanoanthracene-11-carboxylate

S Chandrasekar ^a, Prakash Sharma Om ^a, V Srinivasapriyan ^b, M SureshKumar ^a,^*, C R Ramanathan ^b

PMCID: PMC4011267 PMID: 24860327

Abstract

In the title compound, C₂₄H₂₁NO₂, the residues at the central ethylene bridge are trans to each other. The dihedral angles between the pyridine and benzene rings are 67.09 (6) and 61.41 (5)°. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of C—H⋯O hydrogen bonds.

Related literature

For the biological activity of ester derivatives, see: Bi et al. (2012 ▶); Bartzatt et al. (2004 ▶); Anadu et al. (2006 ▶). For conformation studies, see: Nardelli (1983 ▶). For a related structure, see: Gnanamani & Ramanathan (2009 ▶).

Experimental

Crystal data

C₂₄H₂₁NO₂
M _r = 355.42
Monoclinic,
a = 10.1733 (19) Å
b = 11.156 (2) Å
c = 16.361 (3) Å
β = 90.877 (3)°
V = 1856.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.40 × 0.38 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.969, T _max = 0.984
18677 measured reflections
3664 independent reflections
3105 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.118
S = 1.05
3664 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, 2R. DOI: 10.1107/S1600536814006588/bt6931sup1.cif

e-70-0o512-sup1.cif^{(28.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006588/bt6931Isup2.hkl

e-70-0o512-Isup2.hkl^{(179.7KB, hkl)}

CCDC reference: 993524

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1ⁱ	0.93	2.55	3.2612 (18)	134

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Symmetry code: (i) Inline graphic .

Acknowledgments

CRR thanks DST–FIST for the single-crystal X-ray facility at the Department of Chemistry, Pondicherry University, Pondicherry.

supplementary crystallographic information

1. Comment

Ester derivatives of many compounds exhibit a variety of pharmacological properties, for example anticancer, antitumor and antimicrobial activities (Anadu et al., 2006; Bi et al., 2012; Bartzatt et al., 2004). In view of their importance, the title compound was synthesized and we report herein on its crystal structure. In the title molecule (Fig. 1) the fused tricyclic rings [DS (C7) = 0.0051 (1) Å and D2 (C7—C6) = 0.2248 (1) Å], [DS (C7) = 0.0135 (8) Å and D2 (C7—C6) = 0.2358 (6) Å] and [DS (C7) = 0.0126 (9) Å and D2 (C7—C6) = 0.2543 (7) Å] adopt a boat conformation which can be defined by the above asymmetry parameters (Nardelli, 1983). The torsion angles H7—C7—C8—H8 = -65.81 (15)° and H8—C8—C9—H9 = 129.38 (12)°, define the ring fusions involving the fused tricyclic ring system of the ethanoanthracene moeity. The C22—O1 distance [1.326 (2) Å] shows a partial double-bond character and so the C23 maintains planarity with C22, O2 and C9. In the crystal, pairs of centrosymmetrically related molecules are linked into dimers by C18—H18···O1 hydrogen bonds (Fig. 2).

2. Experimental

Anthracene (5.34 g, 30 mmol) and 3-(pyridine-4-yl)-acrylic acid ethyl ester (4.4g, 25 mmol) were taken in round bottom flask containing distilled dichloromethane (100 ml). To this mixture anhydrous AlCl₃ (6.6 g, 50 mmol) was added and stirred at 0 °C for 48 h followed by stirring the reaction mixture at room temperature for 10 h. The obtained dark black solution was poured into water, the organic layer was separated and the aqueous layer was extracted with ether. The crude material was purified through column chromatography using hexane and ethyl acetate in the ratio of 9:1 as eluent. Yield: 5.7 g, (65%).