9-(Pent-4-en­yl)anthracene

Natarajan Arumugam; Abdulrahman I Almansour; Usama Karama; Mohd Mustaqim Rosli; Ibrahim Abdul Razak

doi:10.1107/S1600536811030571

. 2011 Aug 6;67(Pt 9):o2251. doi: 10.1107/S1600536811030571

9-(Pent-4-enyl)anthracene

Natarajan Arumugam ^a,^‡, Abdulrahman I Almansour ^a, Usama Karama ^a, Mohd Mustaqim Rosli ^b, Ibrahim Abdul Razak ^b,^*,^§

PMCID: PMC3200868 PMID: 22064836

Abstract

In the title compound, C₁₉H₁₈, the anthracene system is almost planar, with a maximum deviation of −0.039 (1) Å. The structure is stabilized by C—H⋯π interactions. The pentene moiety is not planar and is twisted away from the attached anthracene system with a maximum torsion angle of 91.2 (1)°.

Related literature

For background to anthracene, see: de Silva et al. (1997 ▶); Klarner et al. (1998 ▶); Han et al. (2009 ▶).

Experimental

Crystal data

C₁₉H₁₈
M _r = 246.33
Monoclinic,
a = 11.1555 (2) Å
b = 7.2678 (1) Å
c = 19.7129 (3) Å
β = 119.096 (1)°
V = 1396.55 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.73 × 0.38 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.953, T _max = 0.983
20185 measured reflections
5271 independent reflections
3948 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.151
S = 1.05
5271 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.23 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) I, global. DOI: 10.1107/S1600536811030571/ng5202sup1.cif

e-67-o2251-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030571/ng5202Isup2.hkl

e-67-o2251-Isup2.hkl^{(258.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811030571/ng5202Isup3.cml

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

Table 1. C—H⋯π interactions (Å, °).

Cg1 and Cg2 are the centroids of the C1–C6 and C1/C6–C8/C13/C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cg2ⁱ	0.95	2.63	3.5729 (9)	175
C7—H7A⋯Cg1ⁱ	0.95	2.74	3.6851 (9)	177
C17—H17A⋯Cg2ⁱⁱ	0.99	2.58	3.4643 (9)	149
C18—H18A⋯Cg1ⁱⁱ	0.95	2.90	3.6553 (11)	138

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

Acknowledgments

NA, AIM and UK gratefully acknowledge the Deanship of Scientific Research, College of Science, King Saud University (KSU) for funding the synthesis work under Research Grant RGP-VPP-026.

supplementary crystallographic information

Comment

Anthracene is an attractive material in its photochemical and electrochemical properties as well as used as a potential medium for photoconductive (de Silva et al., 1997) and electroluminescence (Klarner et al., 1998) devices. Furthermore, anthracene derivatives exhibited anticancer activity has also been reported recently (Han et al., 2009). As part of an ongoing study on such compounds, in this paper, we present the crystal structure of the title compound, which was synthesized as an intermediate.

All parameters in (I) within normal ranges. The anthracene is planar with maximum deviation of -0.039 (1)Å from atom C11. In the crystal, C—H···π (Table 1) interactions contribute in stabilizing the crystal structure involving Cg1 = C1—C6 and Cg2 = C1/C6–8/C13—C14.

Experimental

A solution of anthrone (1 g, 5.1 mmol) in anhydrous THF (20 ml) was slowly added to pent-4-enylmagnesium bromide (0.47 g, 6.5 mmol). The mixture was stirred for 8 h at room temperature. The reaction mixture was subsequently acidified with 10% HCl, the organic layer was separated, and the aqueous layer was extracted with ether (2 X 10 ml). The combined organic layer was washed with water, dried over MgSO₄ and the solvent was evaporated under reduced pressure and the crude product was added 5 ml benzene, 1.2 g P₂O₅ and stirred for 6 h at room temperature. The P₂O₅ was filtered off and the benzene was removed under vacuum. The crude product was purified by column chromatography (hexane-dichloromethene 1:1). The product was recrystallized from EtOAc to yield title compound as colourless crystals.