Tris(4-tert-butyl-phen-yl)phosphine oxide.

In the title compound, C(30)H(39)OP, the P=O bond length is 1.4866 (12) Å and the P-C bond lengths range from 1.804 (2) to 1.808 (13) Å. The molecle is located on a crystallographic mirror plane. The methyl groups of one tert-butyl group are disordered over two sites in a 0.776 (4):0.224 (4) ratio.

Related literature

For applications of phosphine ligands in palladium-catalysed syntheses, see: Buchwald et al. (2006 ▶); Surry & Buchwald (2008 ▶); Xu et al. (2009 ▶). For related structures, see: Baures & Silverton (1990 ▶); Shawkataly et al. (2009 ▶). For the synthesis, see: Issleib & Brack (1954 ▶).

Experimental

Crystal data

C30H39OP

M = 446.58

Orthorhombic,

a = 11.7986 (10) Å

b = 20.9246 (18) Å

c = 10.5204 (9) Å

V = 2597.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 294 K

0.45 × 0.43 × 0.42 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.946, T max = 0.949

17327 measured reflections

2485 independent reflections

2143 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.03

2485 reflections

161 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052155/si2225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052155/si2225Isup2.hkl

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

C30H39OP	Dx = 1.142 Mg m−3
Mr = 446.58	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 5668 reflections
a = 11.7986 (10) Å	θ = 2.6–28.1°
b = 20.9246 (18) Å	µ = 0.13 mm−1
c = 10.5204 (9) Å	T = 294 K
V = 2597.3 (4) Å3	Block, colourless
Z = 4	0.45 × 0.43 × 0.42 mm
F(000) = 968

Bruker SMART APEX CCD area-detector diffractometer	2485 independent reflections
Radiation source: fine-focus sealed tube	2143 reflections with I > 2σ(I)
graphite	Rint = 0.027
phi and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.946, Tmax = 0.949	k = −25→25
17327 measured reflections	l = −12→12

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0575P)2 + 1.3437P] where P = (Fo2 + 2Fc2)/3
2485 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.38 e Å−3
18 restraints	Δρmin = −0.30 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.77025 (14)	0.31883 (8)	0.30317 (15)	0.0298 (4)
C2	0.66436 (14)	0.33374 (8)	0.35431 (16)	0.0340 (4)
H2	0.6014	0.3093	0.3328	0.041*
C3	0.65284 (15)	0.38473 (8)	0.43698 (17)	0.0370 (4)
H3	0.5814	0.3944	0.4689	0.044*
C4	0.74507 (15)	0.42213 (8)	0.47393 (16)	0.0342 (4)
C5	0.84902 (15)	0.40734 (9)	0.42064 (17)	0.0400 (4)
H5	0.9119	0.4319	0.4419	0.048*
C6	0.86199 (14)	0.35678 (9)	0.33627 (17)	0.0381 (4)
H6	0.9329	0.3483	0.3016	0.046*
C7	0.72901 (17)	0.47686 (9)	0.56942 (18)	0.0422 (4)
C8	0.8417 (2)	0.50323 (12)	0.6179 (2)	0.0656 (7)
H8A	0.8839	0.4696	0.6579	0.098*
H8B	0.8276	0.5366	0.6784	0.098*
H8C	0.8844	0.5201	0.5478	0.098*
C9	0.6599 (2)	0.45282 (11)	0.6836 (2)	0.0654 (7)
H9A	0.5866	0.4390	0.6553	0.098*
H9B	0.6513	0.4868	0.7443	0.098*
H9C	0.6988	0.4176	0.7228	0.098*
C10	0.6641 (2)	0.53167 (10)	0.5049 (2)	0.0592 (6)
H10A	0.7100	0.5498	0.4387	0.089*
H10B	0.6467	0.5640	0.5667	0.089*
H10C	0.5950	0.5155	0.4691	0.089*
C11	0.6881 (2)	0.2500	0.0829 (2)	0.0299 (5)
C12	0.64869 (17)	0.30649 (9)	0.03060 (18)	0.0432 (5)
H12	0.6743	0.3453	0.0627	0.052*
C13	0.57171 (17)	0.30618 (9)	−0.06884 (18)	0.0453 (5)
H13	0.5472	0.3450	−0.1021	0.054*
C14	0.5301 (2)	0.2500	−0.1204 (2)	0.0342 (5)
C15	0.4417 (2)	0.2500	−0.2271 (2)	0.0433 (6)
C16	0.3243 (4)	0.2500	−0.1637 (5)	0.0934 (17)	0.776 (4)
H16A	0.3112	0.2906	−0.1240	0.140*	0.776 (4)
H16B	0.2671	0.2500	−0.2269	0.140*	0.776 (4)
C17	0.4487 (4)	0.3089 (2)	−0.3094 (4)	0.1069 (16)	0.776 (4)
H17A	0.3956	0.3054	−0.3782	0.160*	0.776 (4)
H17B	0.5240	0.3129	−0.3429	0.160*	0.776 (4)
H17C	0.4309	0.3460	−0.2594	0.160*	0.776 (4)
C18	0.5182 (14)	0.2500	−0.3521 (17)	0.0934 (17)	0.224 (4)
H18A	0.4698	0.2500	−0.4229	0.140*	0.224 (4)
H18B	0.5516	0.2086	−0.3543	0.140*	0.224 (4)
C19	0.3708 (5)	0.3102 (7)	−0.2313 (5)	0.1069 (16)	0.224 (4)
H19A	0.3178	0.3074	−0.3003	0.160*	0.224 (4)
H19B	0.4193	0.3465	−0.2436	0.160*	0.224 (4)
H19C	0.3303	0.3148	−0.1526	0.160*	0.224 (4)
O1	0.91419 (9)	0.2500 (7)	0.15255 (12)	0.0397 (4)
P1	0.79669 (5)	0.2500 (7)	0.20357 (5)	0.02885 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0308 (8)	0.0304 (8)	0.0281 (8)	−0.0013 (7)	−0.0028 (6)	0.0019 (7)
C2	0.0283 (8)	0.0345 (9)	0.0393 (9)	−0.0042 (7)	−0.0036 (7)	−0.0025 (7)
C3	0.0323 (9)	0.0385 (9)	0.0401 (9)	0.0005 (7)	0.0026 (7)	−0.0037 (8)
C4	0.0393 (9)	0.0304 (9)	0.0327 (9)	−0.0023 (7)	−0.0031 (7)	0.0006 (7)
C5	0.0341 (9)	0.0405 (10)	0.0455 (10)	−0.0099 (8)	−0.0034 (8)	−0.0057 (8)
C6	0.0299 (9)	0.0429 (10)	0.0414 (9)	−0.0036 (7)	0.0022 (7)	−0.0047 (8)
C7	0.0487 (11)	0.0362 (9)	0.0418 (10)	−0.0038 (8)	0.0006 (8)	−0.0080 (8)
C8	0.0646 (15)	0.0595 (14)	0.0728 (15)	−0.0078 (12)	−0.0120 (12)	−0.0304 (12)
C9	0.0945 (19)	0.0592 (14)	0.0425 (11)	−0.0148 (13)	0.0137 (12)	−0.0147 (10)
C10	0.0685 (14)	0.0424 (12)	0.0665 (14)	0.0090 (10)	0.0018 (12)	−0.0086 (11)
C11	0.0328 (12)	0.0310 (12)	0.0260 (11)	0.000	0.0004 (9)	0.000
C12	0.0580 (12)	0.0298 (9)	0.0418 (10)	−0.0022 (8)	−0.0149 (9)	−0.0015 (7)
C13	0.0597 (12)	0.0328 (10)	0.0434 (10)	0.0061 (9)	−0.0153 (9)	0.0027 (8)
C14	0.0334 (13)	0.0424 (13)	0.0270 (11)	0.000	0.0005 (10)	0.000
C15	0.0486 (16)	0.0461 (15)	0.0352 (14)	0.000	−0.0122 (12)	0.000
C16	0.055 (3)	0.157 (5)	0.068 (3)	0.000	−0.026 (2)	0.000
C17	0.121 (3)	0.117 (3)	0.083 (3)	−0.045 (3)	−0.065 (2)	0.053 (2)
C18	0.055 (3)	0.157 (5)	0.068 (3)	0.000	−0.026 (2)	0.000
C19	0.121 (3)	0.117 (3)	0.083 (3)	−0.045 (3)	−0.065 (2)	0.053 (2)
O1	0.0300 (9)	0.0473 (10)	0.0419 (10)	0.000	0.0059 (7)	0.000
P1	0.0270 (3)	0.0314 (3)	0.0282 (3)	0.000	0.0000 (2)	0.000

C1—C6	1.387 (2)	C11—P1	1.804 (2)
C1—C2	1.396 (2)	C12—C13	1.385 (3)
C1—P1	1.808 (13)	C12—H12	0.9300
C2—C3	1.383 (2)	C13—C14	1.384 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.396 (2)	C14—C13i	1.384 (2)
C3—H3	0.9300	C14—C15	1.533 (3)
C4—C5	1.384 (3)	C15—C17i	1.509 (4)
C4—C7	1.535 (2)	C15—C17	1.509 (4)
C5—C6	1.389 (2)	C15—C19i	1.512 (13)
C5—H5	0.9300	C15—C19	1.512 (13)
C6—H6	0.9300	C15—C16	1.537 (6)
C7—C8	1.527 (3)	C15—C18	1.596 (19)
C7—C9	1.537 (3)	C16—H16A	0.9600
C7—C10	1.537 (3)	C16—H16B	0.9471
C8—H8A	0.9600	C17—H17A	0.9600
C8—H8B	0.9600	C17—H17B	0.9600
C8—H8C	0.9600	C17—H17C	0.9600
C9—H9A	0.9600	C18—H18A	0.9378
C9—H9B	0.9600	C18—H18B	0.9517
C9—H9C	0.9600	C19—H19A	0.9600
C10—H10A	0.9600	C19—H19B	0.9600
C10—H10B	0.9600	C19—H19C	0.9600
C10—H10C	0.9600	O1—P1	1.4866 (12)
C11—C12i	1.384 (2)	P1—C1i	1.808 (13)
C11—C12	1.384 (2)
C6—C1—C2	118.28 (15)	C14—C13—H13	118.9
C6—C1—P1	117.83 (17)	C12—C13—H13	118.9
C2—C1—P1	123.78 (18)	C13—C14—C13i	116.2 (2)
C3—C2—C1	120.19 (15)	C13—C14—C15	121.88 (11)
C3—C2—H2	119.9	C13i—C14—C15	121.88 (11)
C1—C2—H2	119.9	C17i—C15—C17	109.6 (4)
C2—C3—C4	122.08 (16)	C17i—C15—C19i	48.2 (3)
C2—C3—H3	119.0	C17—C15—C19i	133.9 (3)
C4—C3—H3	119.0	C17i—C15—C19	133.9 (3)
C5—C4—C3	116.92 (16)	C17—C15—C19	48.2 (3)
C5—C4—C7	122.78 (16)	C19i—C15—C19	112.7 (7)
C3—C4—C7	120.30 (16)	C17i—C15—C14	112.50 (18)
C4—C5—C6	121.79 (16)	C17—C15—C14	112.50 (18)
C4—C5—H5	119.1	C19i—C15—C14	113.5 (2)
C6—C5—H5	119.1	C19—C15—C14	113.5 (2)
C1—C6—C5	120.69 (16)	C17i—C15—C16	107.4 (3)
C1—C6—H6	119.7	C17—C15—C16	107.4 (3)
C5—C6—H6	119.7	C19i—C15—C16	60.9 (4)
C8—C7—C4	112.37 (16)	C19—C15—C16	60.9 (4)
C8—C7—C9	108.61 (18)	C14—C15—C16	107.2 (2)
C4—C7—C9	109.45 (15)	C17i—C15—C18	59.7 (3)
C8—C7—C10	108.16 (17)	C17—C15—C18	59.7 (3)
C4—C7—C10	109.22 (15)	C19i—C15—C18	106.8 (4)
C9—C7—C10	108.98 (19)	C19—C15—C18	106.8 (4)
C7—C8—H8A	109.5	C14—C15—C18	102.6 (6)
C7—C8—H8B	109.5	C16—C15—C18	150.1 (6)
H8A—C8—H8B	109.5	C15—C16—H16A	109.5
C7—C8—H8C	109.5	C15—C16—H16B	109.7
H8A—C8—H8C	109.5	H16A—C16—H16B	101.0
H8B—C8—H8C	109.5	C15—C17—H17A	109.5
C7—C9—H9A	109.5	C15—C17—H17B	109.5
C7—C9—H9B	109.5	C15—C17—H17C	109.5
H9A—C9—H9B	109.5	C15—C18—H18A	108.1
C7—C9—H9C	109.5	C15—C18—H18B	104.7
H9A—C9—H9C	109.5	H18A—C18—H18B	103.5
H9B—C9—H9C	109.5	C15—C19—H16A	90.7
C7—C10—H10A	109.5	C15—C19—H19A	109.5
C7—C10—H10B	109.5	C15—C19—H19B	109.5
H10A—C10—H10B	109.5	H19A—C19—H19B	109.5
C7—C10—H10C	109.5	C15—C19—H19C	109.5
H10A—C10—H10C	109.5	H19A—C19—H19C	109.5
H10B—C10—H10C	109.5	H19B—C19—H19C	109.5
C12i—C11—C12	117.3 (2)	O1—P1—C1	111.72 (19)
C12i—C11—P1	121.2 (5)	O1—P1—C11	114.10 (9)
C12—C11—P1	121.2 (5)	C1—P1—C11	106.6 (5)
C11—C12—C13	121.07 (17)	O1—P1—C1i	111.72 (16)
C11—C12—H12	119.5	C1—P1—C1i	105.59 (10)
C13—C12—H12	119.5	C11—P1—C1i	106.6 (5)
C14—C13—C12	122.14 (17)
C6—C1—C2—C3	−0.8 (2)	C13—C14—C15—C17	28.3 (4)
P1—C1—C2—C3	175.4 (4)	C13i—C14—C15—C17	−152.7 (3)
C1—C2—C3—C4	−1.1 (3)	C13—C14—C15—C19i	−154.7 (4)
C2—C3—C4—C5	2.1 (3)	C13i—C14—C15—C19i	24.3 (5)
C2—C3—C4—C7	−177.92 (16)	C13—C14—C15—C19	−24.3 (5)
C3—C4—C5—C6	−1.4 (3)	C13i—C14—C15—C19	154.7 (4)
C7—C4—C5—C6	178.71 (16)	C13—C14—C15—C16	−89.5 (2)
C2—C1—C6—C5	1.5 (3)	C13i—C14—C15—C16	89.5 (2)
P1—C1—C6—C5	−174.9 (3)	C13—C14—C15—C18	90.5 (2)
C4—C5—C6—C1	−0.5 (3)	C13i—C14—C15—C18	−90.5 (2)
C5—C4—C7—C8	−11.6 (3)	C6—C1—P1—O1	−9.6 (3)
C3—C4—C7—C8	168.51 (18)	C2—C1—P1—O1	174.21 (16)
C5—C4—C7—C9	−132.3 (2)	C6—C1—P1—C11	−134.9 (3)
C3—C4—C7—C9	47.8 (2)	C2—C1—P1—C11	48.9 (6)
C5—C4—C7—C10	108.5 (2)	C6—C1—P1—C1i	112.0 (2)
C3—C4—C7—C10	−71.5 (2)	C2—C1—P1—C1i	−64.1 (2)
C12i—C11—C12—C13	0.9 (4)	C12i—C11—P1—O1	86.9 (3)
P1—C11—C12—C13	174.97 (17)	C12—C11—P1—O1	−86.9 (3)
C11—C12—C13—C14	0.3 (3)	C12i—C11—P1—C1	−149.3 (4)
C12—C13—C14—C13i	−1.4 (4)	C12—C11—P1—C1	36.9 (4)
C12—C13—C14—C15	177.7 (2)	C12i—C11—P1—C1i	−36.9 (4)
C13—C14—C15—C17i	152.7 (3)	C12—C11—P1—C1i	149.3 (4)
C13i—C14—C15—C17i	−28.3 (4)