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

Cordes, D.B.; Hua, G.; Slawin, A.M.Z.; Woollins, J.D.

doi:10.1107/S1600536811024202

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1790

doi:10.1107/S1600536811024202

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

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

^aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: amzs@st-and.ac.uk

(Received 3 June 2011; accepted 20 June 2011; online 25 June 2011)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.090
wR(F²) = 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

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)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024202/fj2429sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811024202/fj2429Isup3.cml

checkCIF report

Comment top

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.

Related literature top

For related material [on what subject?], see: Ovchinnikov et al. (1995); Chauvin (1990); Ovchinnikov et al. (1979). For related structures of dioxaphospholane oxides, see: Hoppe et al. (1985); Ananikov et al. (2010); Han et al. (2008).

Experimental top

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..

Computing details top

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

Figures top

Fig. 1. The structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

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

Crystal data top

C₂₀H₁₇O₃P	F(000) = 704
M_r = 336.31	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4362 reflections
a = 16.744 (12) Å	θ = 2.1–28.5°
b = 6.098 (4) Å	µ = 0.18 mm⁻¹
c = 17.300 (13) Å	T = 93 K
β = 111.810 (15)°	Needle, colorless
V = 1640 (2) Å³	0.20 × 0.01 × 0.01 mm
Z = 4

Data collection top

Rigaku Mercury CCD diffractometer	3462 independent reflections
Radiation source: rotating anode	2034 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.109
Detector resolution: 14.7059 pixels mm^-1	θ_max = 28.6°, θ_min = 1.3°
ω and ϕ scans	h = −18→21
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −8→7
T_min = 0.435, T_max = 1.000	l = −22→19
10244 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.090	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.256	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1305P)²] where P = (F_o² + 2F_c²)/3
3462 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₂₀H₁₇O₃P	V = 1640 (2) Å³
M_r = 336.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.744 (12) Å	µ = 0.18 mm⁻¹
b = 6.098 (4) Å	T = 93 K
c = 17.300 (13) Å	0.20 × 0.01 × 0.01 mm
β = 111.810 (15)°

Data collection top

Rigaku Mercury CCD diffractometer	3462 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	2034 reflections with I > 2σ(I)
T_min = 0.435, T_max = 1.000	R_int = 0.109
10244 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.090	0 restraints
wR(F²) = 0.256	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
3462 reflections	Δρ_min = −0.53 e Å⁻³
217 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.10931 (6)	0.10326 (17)	0.61793 (7)	0.0392 (4)
O1	0.18993 (16)	0.1930 (4)	0.69493 (17)	0.0423 (7)
O2	0.11788 (15)	0.2675 (4)	0.54921 (16)	0.0392 (7)
O3	0.11527 (17)	−0.1319 (4)	0.6046 (2)	0.0498 (8)
C1	0.2142 (2)	0.4112 (6)	0.6780 (2)	0.0356 (9)
H1	0.1770	0.5201	0.6920	0.043*
C2	0.1911 (2)	0.4166 (6)	0.5822 (2)	0.0364 (9)
H2	0.1701	0.5677	0.5623	0.044*
C3	0.0125 (2)	0.1775 (6)	0.6301 (2)	0.0372 (9)
C4	−0.0305 (3)	0.0204 (6)	0.6596 (3)	0.0419 (10)
H4	−0.0079	−0.1240	0.6713	0.050*
C5	−0.1057 (3)	0.0729 (7)	0.6720 (3)	0.0441 (10)
H5	−0.1338	−0.0340	0.6928	0.053*
C6	−0.1395 (2)	0.2845 (7)	0.6535 (3)	0.0431 (10)
H6	−0.1914	0.3209	0.6609	0.052*
C7	−0.0975 (2)	0.4423 (7)	0.6243 (3)	0.0410 (9)
H7	−0.1204	0.5864	0.6124	0.049*
C8	−0.0221 (2)	0.3888 (6)	0.6125 (3)	0.0385 (9)
H8	0.0062	0.4967	0.5923	0.046*
C9	0.3069 (2)	0.4558 (6)	0.7331 (2)	0.0362 (9)
C10	0.3694 (2)	0.2941 (7)	0.7478 (2)	0.0406 (9)
H10	0.3546	0.1538	0.7227	0.049*
C11	0.4540 (3)	0.3391 (7)	0.7996 (3)	0.0425 (10)
H11	0.4967	0.2283	0.8100	0.051*
C12	0.4766 (3)	0.5434 (7)	0.8360 (3)	0.0479 (11)
H12	0.5343	0.5725	0.8714	0.057*
C13	0.4146 (3)	0.7049 (7)	0.8205 (3)	0.0499 (11)
H13	0.4298	0.8455	0.8452	0.060*
C14	0.3300 (3)	0.6616 (6)	0.7686 (3)	0.0434 (10)
H14	0.2878	0.7737	0.7575	0.052*
C15	0.2596 (2)	0.3581 (6)	0.5482 (2)	0.0356 (9)
C16	0.2620 (2)	0.1556 (7)	0.5115 (3)	0.0405 (9)
H16	0.2230	0.0430	0.5121	0.049*
C17	0.3218 (3)	0.1181 (7)	0.4740 (3)	0.0475 (11)
H17	0.3228	−0.0195	0.4487	0.057*
C18	0.3789 (3)	0.2794 (8)	0.4737 (3)	0.0513 (11)
H18	0.4190	0.2531	0.4477	0.062*
C19	0.3784 (3)	0.4806 (7)	0.5111 (3)	0.0494 (11)
H19	0.4186	0.5910	0.5117	0.059*
C20	0.3185 (2)	0.5192 (6)	0.5477 (3)	0.0416 (10)
H20	0.3177	0.6575	0.5727	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0441 (7)	0.0296 (6)	0.0438 (7)	0.0021 (4)	0.0162 (5)	0.0008 (4)
O1	0.0442 (15)	0.0345 (15)	0.0459 (18)	−0.0013 (12)	0.0140 (13)	0.0093 (12)
O2	0.0440 (16)	0.0365 (15)	0.0369 (16)	−0.0033 (12)	0.0148 (12)	0.0003 (12)
O3	0.0563 (18)	0.0260 (15)	0.070 (2)	0.0028 (12)	0.0273 (16)	−0.0024 (13)
C1	0.050 (2)	0.0274 (19)	0.033 (2)	0.0038 (16)	0.0199 (18)	0.0019 (15)
C2	0.037 (2)	0.033 (2)	0.039 (2)	0.0013 (16)	0.0141 (17)	0.0017 (17)
C3	0.048 (2)	0.028 (2)	0.029 (2)	−0.0025 (17)	0.0077 (17)	−0.0065 (15)
C4	0.046 (2)	0.037 (2)	0.038 (2)	−0.0028 (18)	0.0108 (18)	0.0037 (17)
C5	0.053 (2)	0.043 (2)	0.037 (2)	−0.0083 (19)	0.0184 (19)	0.0030 (18)
C6	0.037 (2)	0.052 (3)	0.041 (3)	−0.0032 (18)	0.0157 (18)	−0.0034 (19)
C7	0.044 (2)	0.037 (2)	0.038 (2)	−0.0005 (18)	0.0103 (18)	−0.0017 (17)
C8	0.040 (2)	0.038 (2)	0.036 (2)	−0.0002 (17)	0.0114 (17)	0.0007 (17)
C9	0.045 (2)	0.036 (2)	0.029 (2)	0.0000 (17)	0.0162 (17)	−0.0018 (16)
C10	0.050 (2)	0.040 (2)	0.035 (2)	−0.0019 (18)	0.0189 (19)	−0.0010 (17)
C11	0.046 (2)	0.049 (3)	0.032 (2)	−0.0002 (19)	0.0150 (18)	0.0041 (18)
C12	0.050 (2)	0.054 (3)	0.036 (3)	−0.013 (2)	0.0117 (19)	−0.004 (2)
C13	0.063 (3)	0.042 (3)	0.048 (3)	−0.015 (2)	0.023 (2)	−0.010 (2)
C14	0.054 (3)	0.036 (2)	0.043 (3)	−0.0036 (18)	0.022 (2)	−0.0031 (18)
C15	0.044 (2)	0.034 (2)	0.029 (2)	0.0040 (17)	0.0139 (17)	0.0012 (15)
C16	0.042 (2)	0.041 (2)	0.037 (2)	0.0006 (17)	0.0127 (18)	−0.0045 (17)
C17	0.054 (3)	0.050 (3)	0.038 (3)	0.013 (2)	0.017 (2)	−0.0046 (19)
C18	0.052 (3)	0.066 (3)	0.040 (3)	0.008 (2)	0.021 (2)	0.004 (2)
C19	0.048 (2)	0.055 (3)	0.046 (3)	−0.002 (2)	0.018 (2)	0.009 (2)
C20	0.048 (2)	0.036 (2)	0.042 (3)	−0.0039 (18)	0.0185 (19)	0.0004 (17)

Geometric parameters (Å, º) top

P1—O3	1.462 (3)	C9—C14	1.388 (5)
P1—O1	1.600 (3)	C9—C10	1.392 (5)
P1—O2	1.601 (3)	C10—C11	1.393 (6)
P1—C3	1.769 (4)	C10—H10	0.9500
O1—C1	1.452 (4)	C11—C12	1.384 (6)
O2—C2	1.461 (4)	C11—H11	0.9500
C1—C9	1.514 (5)	C12—C13	1.383 (6)
C1—C2	1.556 (5)	C12—H12	0.9500
C1—H1	1.0000	C13—C14	1.392 (6)
C2—C15	1.515 (5)	C13—H13	0.9500
C2—H2	1.0000	C14—H14	0.9500
C3—C8	1.399 (5)	C15—C20	1.394 (5)
C3—C4	1.404 (5)	C15—C16	1.395 (5)
C4—C5	1.391 (6)	C16—C17	1.399 (6)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.398 (6)	C17—C18	1.374 (6)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.394 (6)	C18—C19	1.389 (6)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.390 (6)	C19—C20	1.390 (6)
C7—H7	0.9500	C19—H19	0.9500
C8—H8	0.9500	C20—H20	0.9500

O3—P1—O1	112.38 (16)	C3—C8—H8	119.7
O3—P1—O2	117.82 (17)	C14—C9—C10	119.5 (4)
O1—P1—O2	97.11 (15)	C14—C9—C1	119.5 (3)
O3—P1—C3	112.89 (17)	C10—C9—C1	120.9 (3)
O1—P1—C3	109.87 (17)	C9—C10—C11	119.7 (4)
O2—P1—C3	105.51 (16)	C9—C10—H10	120.2
C1—O1—P1	111.0 (2)	C11—C10—H10	120.2
C2—O2—P1	113.1 (2)	C12—C11—C10	120.6 (4)
O1—C1—C9	109.6 (3)	C12—C11—H11	119.7
O1—C1—C2	104.9 (3)	C10—C11—H11	119.7
C9—C1—C2	117.3 (3)	C13—C12—C11	119.7 (4)
O1—C1—H1	108.3	C13—C12—H12	120.2
C9—C1—H1	108.3	C11—C12—H12	120.2
C2—C1—H1	108.3	C12—C13—C14	120.0 (4)
O2—C2—C15	110.4 (3)	C12—C13—H13	120.0
O2—C2—C1	104.1 (3)	C14—C13—H13	120.0
C15—C2—C1	119.0 (3)	C9—C14—C13	120.4 (4)
O2—C2—H2	107.6	C9—C14—H14	119.8
C15—C2—H2	107.6	C13—C14—H14	119.8
C1—C2—H2	107.6	C20—C15—C16	118.8 (4)
C8—C3—C4	118.8 (4)	C20—C15—C2	118.4 (3)
C8—C3—P1	122.2 (3)	C16—C15—C2	122.6 (3)
C4—C3—P1	119.0 (3)	C15—C16—C17	120.1 (4)
C5—C4—C3	121.0 (4)	C15—C16—H16	120.0
C5—C4—H4	119.5	C17—C16—H16	120.0
C3—C4—H4	119.5	C18—C17—C16	120.3 (4)
C4—C5—C6	119.4 (4)	C18—C17—H17	119.8
C4—C5—H5	120.3	C16—C17—H17	119.8
C6—C5—H5	120.3	C17—C18—C19	120.3 (4)
C7—C6—C5	120.3 (4)	C17—C18—H18	119.8
C7—C6—H6	119.9	C19—C18—H18	119.8
C5—C6—H6	119.9	C18—C19—C20	119.5 (4)
C8—C7—C6	120.0 (4)	C18—C19—H19	120.2
C8—C7—H7	120.0	C20—C19—H19	120.2
C6—C7—H7	120.0	C19—C20—C15	120.9 (4)
C7—C8—C3	120.6 (4)	C19—C20—H20	119.5
C7—C8—H8	119.7	C15—C20—H20	119.5

O3—P1—O1—C1	143.1 (2)	C4—C3—C8—C7	0.2 (6)
O2—P1—O1—C1	19.0 (2)	P1—C3—C8—C7	−178.8 (3)
C3—P1—O1—C1	−90.3 (3)	O1—C1—C9—C14	−139.9 (4)
O3—P1—O2—C2	−118.9 (3)	C2—C1—C9—C14	100.8 (4)
O1—P1—O2—C2	1.1 (2)	O1—C1—C9—C10	41.0 (5)
C3—P1—O2—C2	114.1 (2)	C2—C1—C9—C10	−78.4 (4)
P1—O1—C1—C9	−158.1 (2)	C14—C9—C10—C11	1.6 (6)
P1—O1—C1—C2	−31.4 (3)	C1—C9—C10—C11	−179.3 (3)
P1—O2—C2—C15	110.0 (3)	C9—C10—C11—C12	−0.5 (6)
P1—O2—C2—C1	−18.8 (3)	C10—C11—C12—C13	−0.3 (6)
O1—C1—C2—O2	30.1 (3)	C11—C12—C13—C14	0.1 (6)
C9—C1—C2—O2	152.0 (3)	C10—C9—C14—C13	−1.8 (6)
O1—C1—C2—C15	−93.2 (4)	C1—C9—C14—C13	179.1 (4)
C9—C1—C2—C15	28.6 (5)	C12—C13—C14—C9	1.0 (6)
O3—P1—C3—C8	−155.4 (3)	O2—C2—C15—C20	157.7 (3)
O1—P1—C3—C8	78.3 (4)	C1—C2—C15—C20	−82.1 (4)
O2—P1—C3—C8	−25.4 (4)	O2—C2—C15—C16	−17.2 (5)
O3—P1—C3—C4	25.5 (4)	C1—C2—C15—C16	103.0 (4)
O1—P1—C3—C4	−100.8 (3)	C20—C15—C16—C17	−1.0 (6)
O2—P1—C3—C4	155.5 (3)	C2—C15—C16—C17	173.9 (4)
C8—C3—C4—C5	−0.6 (6)	C15—C16—C17—C18	0.6 (6)
P1—C3—C4—C5	178.5 (3)	C16—C17—C18—C19	0.5 (7)
C3—C4—C5—C6	1.0 (6)	C17—C18—C19—C20	−1.2 (6)
C4—C5—C6—C7	−1.1 (6)	C18—C19—C20—C15	0.7 (6)
C5—C6—C7—C8	0.7 (6)	C16—C15—C20—C19	0.4 (6)
C6—C7—C8—C3	−0.3 (6)	C2—C15—C20—C19	−174.8 (4)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇O₃P
M_r	336.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	16.744 (12), 6.098 (4), 17.300 (13)
β (°)	111.810 (15)
V (Å³)	1640 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.20 × 0.01 × 0.01

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2010)
T_min, T_max	0.435, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10244, 3462, 2034
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.090, 0.256, 1.01
No. of reflections	3462
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.53

Computer programs: CrystalClear (Rigaku, 2010), SIR2004 (Burla et al., 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+3/2.

Acknowledgements

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

References

Ananikov, V. P., Khemchyan, L. L., Beletskaya, I. P. & Starikova, Z. A. (2010). Adv. Synth. Catal. 352, 2979–2992. CrossRef CAS Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Chauvin, R. (1990). Tetrahedron Asymmetry, 1, 737–742. CrossRef CAS Google Scholar
Han, L.-B., Ono, Y. & Shimada, S. (2008). J. Am. Chem. Soc. 130, 2752–2753. Web of Science CrossRef PubMed CAS Google Scholar
Hoppe, I., Schollkopf, U., Nieger, M. & Egert, E. (1985). Angew. Chem. Int. Ed. Engl. 24, 1067–1068. CrossRef Google Scholar
Ovchinnikov, V. V., Galkin, V. I., Yarkova, E. G., Cherkasov, R. A. & Pudovik, A. N. (1979). Dokl. Akad. Nauk SSSR, 245, 1390–1393. CAS Google Scholar
Ovchinnikov, V. V., Karataeva, F. Kh. & Cherkasov, R. A. (1995). Zh. Obshch. Khim. 65, 412–25. CAS Google Scholar
Rigaku (2010). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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