Phen­yl(2,4,5-triphenyl­cyclo­penta-1,4-dien-1-yl)methanone

David B Cordes; Guoxiong Hua; Alexandra M Z Slawin; J Derek Woollins

doi:10.1107/S1600536811022902

. 2011 Jun 18;67(Pt 7):o1718. doi: 10.1107/S1600536811022902

Phenyl(2,4,5-triphenylcyclopenta-1,4-dien-1-yl)methanone

David B Cordes ^a, Guoxiong Hua ^a, Alexandra M Z Slawin ^a,^*, J Derek Woollins ^a

PMCID: PMC3152139 PMID: 21837110

Abstract

The title compound, C₃₀H₂₂O, does not form face-to-face π–π interactions despite the presence of four phenyl rings within the compound. Instead weak C—H⋯π interactions occur between adjacent molecules, with C⋯C contact distances in the range 3.633 (4)–3.974 (4) Å. The ketone O atom also takes part in a weak C—H⋯O interaction. The three pendant phenyl rings are twisted relative to the central cyclopentadiene ring by 17.82 (17), 29.63 (14) and 61.57 (9)°, while the phenylmethanone is nearly orthogonal, the angle between planes being 87.77 (9)°.

Related literature

For a previous preparation of the title compound, see: Lund (2005 ▶). The crystal studied was obtained by reaction of Woollins’ reagent [2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide] with quinoxaline-2,3-dithiol. For a review of the chemistry of Woollins’ reagent, see: Hua & Woollins (2009 ▶). There are no structurally closely-related compounds in the literature; however, for some of the closest related, see: Evrard et al. (1971 ▶); Wender et al. (2006 ▶).

Experimental

Crystal data

C₃₀H₂₂O
M _r = 398.48
Monoclinic,
a = 25.946 (6) Å
b = 6.1573 (14) Å
c = 26.602 (6) Å
β = 102.236 (7)°
V = 4153.3 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 93 K
0.30 × 0.20 × 0.06 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010 ▶) T _min = 0.978, T _max = 0.996
13266 measured reflections
4252 independent reflections
2479 reflections with I > 2σ(I)
R _int = 0.120

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.225
S = 1.04
4252 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: CrystalClear (Rigaku, 2010 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022902/fj2426sup1.cif

e-67-o1718-sup1.cif^{(27.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022902/fj2426Isup2.hkl

e-67-o1718-Isup2.hkl^{(208.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811022902/fj2426Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C6–C11 and C25–C30 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1ⁱ	0.99	2.64	3.229 (3)	118 (2)
C10—H10⋯Cg1ⁱⁱ	0.95	2.80	3.527 (3)	134 (2)
C20—H20⋯Cg2ⁱⁱⁱ	0.95	2.80	3.605 (3)	143 (2)
C28—H28⋯Cg1^iv	0.95	2.88	3.612 (3)	134 (2)

Open in a new tab

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

Acknowledgments

The authors are grateful to the University of St Andrews and the Engineering and Physical Science Research Council (EPSRC, UK) for financial support.

supplementary crystallographic information

Comment

The previously know title compound (Lund, 2005) has been prepared by the reaction of Woollins' reagent with quinoxaline-2,3-dithiol. In a similar manner to the two somewhat related structures (Evrard et al., 1971 and Wender et al., 2006) no face-to-face π-interactions are observed, adjacent molecules instead interacting via a series of CH···π interactions. The ketone oxygen makes intermolecular CH···O contacts at a distance of 2.64 Å.

Experimental

A mixture of 0.194 g of quinoxaline-2,3-dithiol (1.0 mmol) and Woollins' reagent (0.54 g, 1.0 mmol) in 20 ml of dry toluene was refluxed for 7 h. The red suspension disappeared and a deep red solution formed. Following cooling to room temperature and removal of solvent in vacuuo the residue was purified by silica gel column chromatography (1: 1 hexane/dichloromethane eluent) to give the title compound as a brown solid (0.060 g, 13%). Crystals suitable for X-ray structure determination were obtained from the diffusion of hexane into a dichloromethane solution of the title compound. Selected IR (KBr, cm^-1): 1658(s, C═O), 1596(m), 1490(m), 1443(m), 1243(s), 754(s), 6932(versus). ¹H NMR (CD₂Cl₂, δ), 8.13–8.00 (m, 2H, ArH), 7.93–7.83 (m, 3H, ArH), 7.61–6.92 (m, 15H, ArH), 4.24 (s, 2H, CH₂) p.p.m.. ¹³C NMR (CD₂Cl₂, δ), 168.5 (C═O), 144.0, 135.8, 134.4, 133.4, 132.6, 130.7, 129.8, 129.4, 129.2, 129.0, 128.9, 128.8, 128.5, 128.3, 128.1, 127.9, 127.6, 127.4, 127.2, 127.0, 126.6, 46.0 p.p.m.. MS (CI⁺, m/z), 399 [M+H]⁺. Accurate mass measurement [CI⁺, m/z]: 399.1737 [M+H]⁺, calculated mass for C₃₀H₂₃O: 399.1743.