2,4,5-Triphenyl-1,3,2-dioxa­phospho­lan-2-one

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

doi:10.1107/S1600536811024202

. 2011 Jun 25;67(Pt 7):o1790. doi: 10.1107/S1600536811024202

2,4,5-Triphenyl-1,3,2-dioxaphospholan-2-one

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

PMCID: PMC3152137 PMID: 21837163

Abstract

The dioxaphospholane ring in the title compound, C₂₀H₁₇O₃P, adopts an envelope conformation about one of the ring carbons. The benzene rings of the compound do not form face-to-face π–π interactions, instead weak C—H⋯π interactions occur between adjacent molecules. The methine H atoms on the dioxaphospholane ring form weak C—H⋯O hydrogen bonds to the oxide group of an adjacent molecule.

Related literature

For the synthesis of the title compound and isomeric forms, see: Ovchinnikov et al. (1979 ▶, 1995 ▶); Chauvin (1990 ▶). For related structures of dioxaphospholane oxides, see: Hoppe et al. (1985 ▶); Ananikov et al. (2010 ▶); Han et al. (2008 ▶).

Experimental

Crystal data

C₂₀H₁₇O₃P
M _r = 336.31
Monoclinic,
a = 16.744 (12) Å
b = 6.098 (4) Å
c = 17.300 (13) Å
β = 111.810 (15)°
V = 1640 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 93 K
0.20 × 0.01 × 0.01 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010 ▶) T _min = 0.435, T _max = 1.000
10244 measured reflections
3462 independent reflections
2034 reflections with I > 2σ(I)
R _int = 0.109

Refinement

R[F ² > 2σ(F ²)] = 0.090
wR(F ²) = 0.256
S = 1.01
3462 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Data collection: CrystalClear (Rigaku, 2010 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024202/fj2429sup1.cif

e-67-o1790-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024202/fj2429Isup2.hkl

e-67-o1790-Isup2.hkl^{(169.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024202/fj2429Isup3.cml

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

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

Cg1 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O3ⁱ	1.00	2.59	3.248 (5)	123 (3)
C2—H2⋯O3ⁱ	1.00	2.29	3.115 (5)	139 (3)
C12—H12⋯Cg1ⁱⁱ	0.95	2.94	3.838 (5)	158 (3)
C12—H12⋯C18ⁱⁱ	0.95	2.83	3.585 (6)	138 (3)

Open in a new tab

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

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 known title compound (Ovchinnikov et al., 1995) has been prepared by the reaction of Woollins' reagent with 1,2-diphenylethane-1,2-diol. The resulting dioxaphospholane ring in the title compound is similar to the only three structurally known phospholanes, bond lengths about P being very similar (P—O, 1.586–1.604 Å, P═O, 1.461–1.467 Å, P—C, 1.765–1.815 Å; Hoppe et al., 1985, Han et al., 2008 and Ananikov et al., 2010). The dioxaphospholane ring displays an envelope conformation about C1, the torsion angles O2—P1—O1—C1 and P1—O2—C2—C1 being 19.0 (2) and -18.8 (3) °, respectively. The phenyl rings in the title compound do not form face-to-face π–π interactions, instead weak CH···π interactions result at a distance of 2.94 (5) Å. The phospholane oxide oxygen forms weak hydrogen bonds with the H1 and H2 H atoms, at distances of 2.29 (4) and 2.59 (4) Å forming chains along the [0 1 0] direction.

Experimental

A mixture of diphenylethane-1,2-diol (0.214 g, 1.0 mmol) and Woollins' reagent (0.54 g, 1.0 mmol) in 20 ml of dry toluene was stirred at room temperature for 3 h. Then the mixture was heated to 60 °C with stirring for 2 h. The red suspension disappeared and a grayish-green solution formed. Following cooling to room temperature and removal of the solvent in vacuuo the residue was purified by silica gel column chromatography (dichloromethane eluent) to give the title compound as a pale green solid in low yield (0.055 g, 14%). 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): 1439(m), 1269(m), 1133(m), 992(s), 870(m), 840(m), 716(s), 693(s), 510(m). ¹H NMR (CD₂Cl₂, δ), 8.06–7.94 (m, 2H, ArH), 7.71–7.55 (m, 2H, ArH), 7.23–7.05 (m, 11H, ArH), 5.88 (m, J = 9.1 Hz, 2H, CH) p.p.m.. ¹³C NMR (CD₂Cl₂, δ), 134.4, 131.9, 130.9, 130.6, 129.1, 128.4, 128.1, 126.8, 83.9 (COO) p.p.m.. ³¹P NMR (CD₂Cl₂, δ), 34.88 p.p.m..