(2,5-Diphenyl­pent-4-yn-1-en-3-yl­idene)triphenyl­phospho­rane

Wang, A.; Wang, Q.; Li, X.

doi:10.1107/S1600536807062034

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o68

https://doi.org/10.1107/S1600536807062034

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(2,5-Diphenylpent-4-yn-1-en-3-ylidene)triphenylphosphorane

Aichen Wang,^a Qibao Wang ^a and Xiaoyan Li ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Shanda Nanlu 27, Jinan 250100, People's Republic of China
^*Correspondence e-mail: xli63@sdu.edu.cn

(Received 20 November 2007; accepted 22 November 2007; online 6 December 2007)

The title compound, C₄₅H₂₇P, was obtained as a product of the reaction of triphenylmethylenephosphorane with one molar equivalent of 1,4-diphenylbutadiyne in toluene. The compound was very stable under ambient conditions, but rapidly decomposed in solution when exposed to the air. The P atom is tetracoordinated in an approximately tetrahedral geometry. The length of the C≡C triple bond [1.206 (2) Å] is in the normal range.

Related literature

Related crystal structures of α,β-unsaturated-C,P ylides have been reported, see: Koollenz et al. (1996 ).

Experimental

Crystal data

C₃₅H₂₇P
M_r = 478.54
Triclinic, $[P \overline 1]$
a = 11.439 (2) Å
b = 11.609 (2) Å
c = 11.913 (2) Å
α = 116.00 (3)°
β = 97.24 (3)°
γ = 108.47 (3)°
V = 1281.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 383 (2) K
0.27 × 0.25 × 0.22 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.966, T_max = 0.972
9166 measured reflections
4661 independent reflections
4077 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.133
S = 1.06
4661 reflections
433 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

P1—C19	1.7294 (15)
P1—C13	1.8104 (15)
P1—C7	1.8132 (18)
P1—C1	1.8178 (19)
C20—C21	1.206 (2)
C28—C29	1.343 (2)

C19—P1—C13	108.20 (7)
C19—P1—C7	117.53 (8)
C13—P1—C7	105.18 (7)
C19—P1—C1	111.39 (7)
C13—P1—C1	107.73 (7)
C7—P1—C1	106.29 (8)
C21—C20—C19	179.42 (18)
C20—C21—C22	164.32 (18)

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT and SHELXTL (Sheldrick, 2001 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062034/lw2053sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062034/lw2053Isup2.hkl

checkCIF report

Comment top

In the title molecule (Fig.1) the phosphorane atom is coordinated in a tetragonal pyramid by three C atoms of phenyl groups and one sp₂-C atom. The length of the C—C triple bond is in the range of classic one, and the carbon atoms linked to the C—C triple bond lie in nearly a line.

Related literature top

Related crystal structures of α,β-unsaturated-C,P ylide have been reported, see: Koollenz et al. (1996).

Experimental top

To the solution of triphenylmethylenephosphorane(1.41 g, 5.11 mmol) in 30 ml of toluene was added 1,4-diphenylbutadiyne(1.05 g, 5.20 mmol) at room temperature, a deep red solution formed rapidly. After stirring for at least 24 h the reaction solution was filtrated. The solid residue was dried and extracted with pentane and diethyl ether, respectively. Purple red crystals were obtained suitable for X-ray diffraction analysis. (yield:1.59 g, 65.1%, d.p.: 87 °C)

Structure description top

Related crystal structures of α,β-unsaturated-C,P ylide have been reported, see: Koollenz et al. (1996).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001) and SHELXTL (Sheldrick, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

(2,5-Diphenylpent-4-yn-1-en-3-ylidene)triphenylphosphorane top

Crystal data top

C₃₅H₂₇P	Z = 2
M_r = 478.54	F(000) = 504
Triclinic, P1	D_x = 1.240 Mg m⁻³
a = 11.439 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.609 (2) Å	Cell parameters from 5612 reflections
c = 11.913 (2) Å	θ = 2.2–23.2°
α = 116.00 (3)°	µ = 0.13 mm⁻¹
β = 97.24 (3)°	T = 383 K
γ = 108.47 (3)°	Cubic, purple red
V = 1281.9 (4) Å³	0.27 × 0.25 × 0.22 mm

Data collection top

Bruker SMART diffractometer	4661 independent reflections
Radiation source: fine-focus sealed tube	4077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
T_min = 0.966, T_max = 0.972	k = −13→14
9166 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
4661 reflections	(Δ/σ)_max = 0.002
433 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₃₅H₂₇P	γ = 108.47 (3)°
M_r = 478.54	V = 1281.9 (4) Å³
Triclinic, P1	Z = 2
a = 11.439 (2) Å	Mo Kα radiation
b = 11.609 (2) Å	µ = 0.13 mm⁻¹
c = 11.913 (2) Å	T = 383 K
α = 116.00 (3)°	0.27 × 0.25 × 0.22 mm
β = 97.24 (3)°

Data collection top

Bruker SMART diffractometer	4661 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4077 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.972	R_int = 0.043
9166 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.57 e Å⁻³
4661 reflections	Δρ_min = −0.29 e Å⁻³
433 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	0.68533 (3)	0.36252 (4)	0.11133 (3)	0.01164 (15)
C1	0.56521 (14)	0.24722 (17)	−0.05062 (14)	0.0144 (3)
C2	0.47129 (15)	0.11909 (18)	−0.07668 (15)	0.0164 (3)
C3	0.38692 (16)	0.02065 (19)	−0.20295 (16)	0.0187 (4)
C4	0.39421 (15)	0.04989 (18)	−0.30372 (15)	0.0193 (4)
C5	0.48380 (16)	0.1796 (2)	−0.27692 (16)	0.0206 (4)
C6	0.56947 (15)	0.27875 (19)	−0.15066 (15)	0.0168 (3)
C7	0.76840 (14)	0.52987 (17)	0.12146 (14)	0.0147 (3)
C8	0.74427 (15)	0.64557 (19)	0.19848 (16)	0.0188 (4)
C9	0.80051 (17)	0.7702 (2)	0.19820 (18)	0.0242 (4)
C10	0.88218 (17)	0.7816 (2)	0.12299 (18)	0.0243 (4)
C11	0.90960 (16)	0.6678 (2)	0.04955 (16)	0.0223 (4)
C12	0.85367 (15)	0.54293 (18)	0.04849 (15)	0.0163 (3)
C13	0.80689 (14)	0.29439 (18)	0.11596 (14)	0.0142 (3)
C14	0.92794 (15)	0.38344 (19)	0.21428 (15)	0.0163 (3)
C15	1.01613 (16)	0.3280 (2)	0.22863 (16)	0.0197 (4)
C16	0.98606 (16)	0.1863 (2)	0.14545 (17)	0.0222 (4)
C17	0.86805 (17)	0.0994 (2)	0.04615 (17)	0.0224 (4)
C18	0.77842 (16)	0.15322 (18)	0.03089 (16)	0.0191 (4)
C19	0.61694 (14)	0.36449 (17)	0.23325 (14)	0.0135 (3)
C20	0.68991 (14)	0.36051 (16)	0.33433 (14)	0.0132 (3)
C21	0.75197 (14)	0.35583 (17)	0.42069 (14)	0.0156 (3)
C22	0.80550 (14)	0.30986 (17)	0.49926 (14)	0.0153 (3)
C23	0.90307 (15)	0.26281 (19)	0.47269 (16)	0.0199 (4)
C24	0.94525 (16)	0.2043 (2)	0.53938 (17)	0.0232 (4)
C25	0.89336 (17)	0.1928 (2)	0.63495 (16)	0.0233 (4)
C26	0.80095 (17)	0.24431 (19)	0.66597 (16)	0.0211 (4)
C27	0.75698 (15)	0.30231 (18)	0.59963 (15)	0.0182 (3)
C28	0.48816 (14)	0.36477 (17)	0.22947 (14)	0.0142 (3)
C29	0.42860 (16)	0.4080 (2)	0.16165 (16)	0.0205 (4)
C30	0.41673 (14)	0.30236 (17)	0.30066 (14)	0.0143 (3)
C31	0.34931 (15)	0.36725 (18)	0.37822 (15)	0.0167 (3)
C32	0.27977 (15)	0.30599 (19)	0.44037 (16)	0.0199 (4)
C33	0.27776 (17)	0.1813 (2)	0.42805 (17)	0.0234 (4)
C34	0.34548 (17)	0.1160 (2)	0.35238 (18)	0.0233 (4)
C35	0.41519 (15)	0.17774 (18)	0.29087 (15)	0.0185 (3)
H21	0.3514 (19)	0.457 (2)	0.3947 (19)	0.024 (5)*
H5	0.630 (2)	0.366 (2)	−0.1330 (17)	0.017 (4)*
H1	0.4642 (19)	0.099 (2)	−0.0043 (18)	0.021 (5)*
H14	0.844 (2)	0.003 (3)	−0.013 (2)	0.042 (6)*
H2	0.328 (2)	−0.064 (2)	−0.2167 (19)	0.025 (5)*
H6	0.691 (2)	0.639 (2)	0.2514 (19)	0.023 (5)*
H23	0.229 (2)	0.134 (2)	0.4727 (19)	0.027 (5)*
H11	0.9484 (19)	0.480 (2)	0.2726 (19)	0.021 (5)*
H3	0.338 (2)	−0.017 (2)	−0.390 (2)	0.023 (5)*
H10	0.871 (2)	0.462 (3)	−0.004 (2)	0.030 (5)*
H16	0.9390 (19)	0.268 (2)	0.4059 (19)	0.021 (5)*
H24	0.348 (2)	0.034 (3)	0.343 (2)	0.032 (6)*
H19	0.768 (2)	0.240 (2)	0.735 (2)	0.028 (5)*
H27	0.475 (2)	0.451 (2)	0.1141 (19)	0.025 (5)*
H4	0.487 (2)	0.202 (2)	−0.345 (2)	0.028 (5)*
H15	0.698 (2)	0.092 (2)	−0.0382 (19)	0.021 (5)*
H18	0.921 (2)	0.153 (2)	0.682 (2)	0.029 (5)*
H13	1.050 (2)	0.147 (2)	0.1566 (19)	0.027 (5)*
H12	1.095 (2)	0.388 (2)	0.295 (2)	0.025 (5)*
H22	0.234 (2)	0.355 (2)	0.496 (2)	0.028 (5)*
H25	0.461 (2)	0.133 (3)	0.238 (2)	0.034 (6)*
H7	0.787 (2)	0.853 (3)	0.255 (2)	0.042 (6)*
H20	0.693 (2)	0.338 (2)	0.621 (2)	0.031 (5)*
H17	1.009 (2)	0.167 (2)	0.513 (2)	0.032 (6)*
H8	0.924 (2)	0.870 (3)	0.125 (2)	0.032 (6)*
H9	0.966 (2)	0.670 (3)	0.001 (2)	0.033 (6)*
H26	0.339 (2)	0.390 (2)	0.1535 (18)	0.022 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0118 (2)	0.0110 (3)	0.0152 (2)	0.00594 (17)	0.00547 (16)	0.00793 (17)
C1	0.0143 (7)	0.0151 (9)	0.0155 (7)	0.0084 (6)	0.0046 (6)	0.0077 (6)
C2	0.0179 (7)	0.0137 (9)	0.0211 (8)	0.0078 (6)	0.0067 (6)	0.0106 (6)
C3	0.0175 (7)	0.0137 (9)	0.0246 (8)	0.0072 (7)	0.0055 (6)	0.0092 (7)
C4	0.0178 (8)	0.0172 (9)	0.0186 (8)	0.0085 (7)	0.0038 (6)	0.0054 (7)
C5	0.0194 (8)	0.0279 (11)	0.0186 (8)	0.0114 (7)	0.0076 (6)	0.0136 (7)
C6	0.0149 (7)	0.0145 (9)	0.0229 (8)	0.0053 (7)	0.0066 (6)	0.0115 (7)
C7	0.0128 (7)	0.0152 (9)	0.0180 (7)	0.0061 (6)	0.0030 (6)	0.0101 (6)
C8	0.0160 (7)	0.0181 (10)	0.0266 (8)	0.0090 (7)	0.0082 (7)	0.0131 (7)
C9	0.0214 (8)	0.0144 (10)	0.0413 (10)	0.0104 (7)	0.0079 (7)	0.0161 (8)
C10	0.0196 (8)	0.0217 (11)	0.0393 (10)	0.0057 (7)	0.0050 (7)	0.0248 (8)
C11	0.0189 (8)	0.0272 (11)	0.0235 (8)	0.0068 (7)	0.0059 (7)	0.0173 (7)
C12	0.0159 (7)	0.0156 (9)	0.0182 (7)	0.0049 (6)	0.0052 (6)	0.0105 (6)
C13	0.0157 (7)	0.0175 (9)	0.0184 (7)	0.0108 (7)	0.0101 (6)	0.0125 (6)
C14	0.0171 (7)	0.0167 (9)	0.0202 (7)	0.0086 (7)	0.0095 (6)	0.0113 (7)
C15	0.0170 (8)	0.0278 (10)	0.0238 (8)	0.0128 (7)	0.0096 (7)	0.0175 (7)
C16	0.0237 (8)	0.0287 (11)	0.0337 (9)	0.0196 (8)	0.0181 (7)	0.0231 (8)
C17	0.0291 (9)	0.0138 (10)	0.0349 (9)	0.0138 (7)	0.0185 (7)	0.0153 (7)
C18	0.0179 (8)	0.0154 (9)	0.0238 (8)	0.0075 (7)	0.0086 (7)	0.0089 (7)
C19	0.0144 (7)	0.0145 (9)	0.0164 (7)	0.0076 (6)	0.0072 (6)	0.0100 (6)
C20	0.0139 (7)	0.0100 (8)	0.0165 (7)	0.0055 (6)	0.0075 (6)	0.0064 (6)
C21	0.0157 (7)	0.0170 (9)	0.0169 (7)	0.0083 (6)	0.0076 (6)	0.0092 (6)
C22	0.0144 (7)	0.0110 (8)	0.0164 (7)	0.0031 (6)	0.0014 (6)	0.0061 (6)
C23	0.0180 (8)	0.0241 (10)	0.0217 (8)	0.0095 (7)	0.0077 (6)	0.0140 (7)
C24	0.0187 (8)	0.0281 (11)	0.0282 (9)	0.0135 (8)	0.0066 (7)	0.0162 (7)
C25	0.0245 (8)	0.0242 (11)	0.0233 (8)	0.0100 (8)	0.0018 (7)	0.0152 (7)
C26	0.0253 (8)	0.0200 (10)	0.0176 (8)	0.0069 (7)	0.0070 (6)	0.0110 (7)
C27	0.0186 (7)	0.0171 (9)	0.0195 (7)	0.0082 (7)	0.0078 (6)	0.0087 (6)
C28	0.0147 (7)	0.0127 (8)	0.0172 (7)	0.0077 (6)	0.0062 (6)	0.0074 (6)
C29	0.0180 (8)	0.0257 (10)	0.0266 (8)	0.0133 (7)	0.0099 (6)	0.0165 (7)
C30	0.0108 (7)	0.0135 (8)	0.0167 (7)	0.0054 (6)	0.0034 (6)	0.0063 (6)
C31	0.0157 (7)	0.0153 (9)	0.0205 (7)	0.0088 (7)	0.0061 (6)	0.0086 (6)
C32	0.0185 (8)	0.0191 (9)	0.0244 (8)	0.0095 (7)	0.0109 (7)	0.0107 (7)
C33	0.0237 (8)	0.0243 (10)	0.0286 (9)	0.0098 (7)	0.0144 (7)	0.0171 (7)
C34	0.0268 (9)	0.0169 (10)	0.0340 (9)	0.0115 (8)	0.0148 (7)	0.0161 (8)
C35	0.0193 (8)	0.0151 (9)	0.0224 (8)	0.0092 (7)	0.0091 (6)	0.0086 (6)

Geometric parameters (Å, º) top

P1—C19	1.7294 (15)	C17—C18	1.390 (2)
P1—C13	1.8104 (15)	C17—H14	0.95 (3)
P1—C7	1.8132 (18)	C18—H15	0.95 (2)
P1—C1	1.8178 (19)	C19—C20	1.403 (2)
C1—C6	1.394 (2)	C19—C28	1.4693 (19)
C1—C2	1.401 (2)	C20—C21	1.206 (2)
C2—C3	1.389 (2)	C21—C22	1.427 (2)
C2—H1	0.99 (2)	C22—C23	1.403 (2)
C3—C4	1.388 (2)	C22—C27	1.405 (2)
C3—H2	0.92 (2)	C23—C24	1.382 (2)
C4—C5	1.392 (3)	C23—H16	0.96 (2)
C4—H3	0.95 (2)	C24—C25	1.385 (3)
C5—C6	1.394 (3)	C24—H17	0.98 (2)
C5—H4	0.96 (2)	C25—C26	1.384 (2)
C6—H5	0.94 (2)	C25—H18	0.95 (2)
C7—C8	1.393 (2)	C26—C27	1.383 (2)
C7—C12	1.402 (2)	C26—H19	0.96 (2)
C8—C9	1.387 (3)	C27—H20	0.96 (2)
C8—H6	0.94 (2)	C28—C29	1.343 (2)
C9—C10	1.389 (3)	C28—C30	1.500 (2)
C9—H7	0.98 (2)	C29—H27	1.00 (2)
C10—C11	1.388 (3)	C29—H26	0.96 (2)
C10—H8	0.97 (3)	C30—C35	1.394 (2)
C11—C12	1.381 (3)	C30—C31	1.398 (2)
C11—H9	0.92 (2)	C31—C32	1.392 (2)
C12—H10	0.97 (2)	C31—H21	0.96 (2)
C13—C18	1.393 (2)	C32—C33	1.382 (3)
C13—C14	1.407 (2)	C32—H22	0.99 (2)
C14—C15	1.388 (2)	C33—C34	1.391 (2)
C14—H11	0.95 (2)	C33—H23	1.02 (2)
C15—C16	1.390 (3)	C34—C35	1.390 (2)
C15—H12	0.93 (2)	C34—H24	0.92 (2)
C16—C17	1.388 (3)	C35—H25	0.96 (2)
C16—H13	1.00 (2)

C19—P1—C13	108.20 (7)	C16—C17—C18	120.08 (17)
C19—P1—C7	117.53 (8)	C16—C17—H14	123.3 (15)
C13—P1—C7	105.18 (7)	C18—C17—H14	116.6 (15)
C19—P1—C1	111.39 (7)	C17—C18—C13	119.88 (16)
C13—P1—C1	107.73 (7)	C17—C18—H15	118.6 (12)
C7—P1—C1	106.29 (8)	C13—C18—H15	121.5 (12)
C6—C1—C2	119.66 (15)	C20—C19—C28	121.62 (13)
C6—C1—P1	121.88 (13)	C20—C19—P1	115.92 (10)
C2—C1—P1	118.32 (12)	C28—C19—P1	122.42 (11)
C3—C2—C1	120.33 (15)	C21—C20—C19	179.42 (18)
C3—C2—H1	119.9 (12)	C20—C21—C22	164.32 (18)
C1—C2—H1	119.8 (12)	C23—C22—C27	118.19 (15)
C4—C3—C2	119.99 (17)	C23—C22—C21	120.51 (14)
C4—C3—H2	122.2 (12)	C27—C22—C21	121.19 (14)
C2—C3—H2	117.8 (12)	C24—C23—C22	120.55 (15)
C3—C4—C5	119.77 (16)	C24—C23—H16	119.4 (12)
C3—C4—H3	120.6 (13)	C22—C23—H16	120.1 (12)
C5—C4—H3	119.6 (13)	C23—C24—C25	120.65 (15)
C4—C5—C6	120.66 (16)	C23—C24—H17	117.8 (13)
C4—C5—H4	120.6 (13)	C25—C24—H17	121.4 (13)
C6—C5—H4	118.8 (13)	C26—C25—C24	119.34 (16)
C1—C6—C5	119.49 (16)	C26—C25—H18	118.5 (12)
C1—C6—H5	120.1 (11)	C24—C25—H18	122.1 (12)
C5—C6—H5	120.4 (11)	C27—C26—C25	120.76 (15)
C8—C7—C12	119.35 (16)	C27—C26—H19	120.4 (13)
C8—C7—P1	120.06 (12)	C25—C26—H19	118.8 (13)
C12—C7—P1	120.55 (13)	C26—C27—C22	120.41 (15)
C9—C8—C7	119.84 (15)	C26—C27—H20	121.1 (13)
C9—C8—H6	120.2 (13)	C22—C27—H20	118.5 (13)
C7—C8—H6	119.9 (13)	C29—C28—C19	125.09 (15)
C8—C9—C10	120.66 (16)	C29—C28—C30	118.87 (14)
C8—C9—H7	119.9 (15)	C19—C28—C30	115.91 (13)
C10—C9—H7	119.4 (15)	C28—C29—H27	120.4 (11)
C11—C10—C9	119.51 (18)	C28—C29—H26	118.9 (12)
C11—C10—H8	119.9 (13)	H27—C29—H26	120.5 (16)
C9—C10—H8	120.5 (12)	C35—C30—C31	118.12 (15)
C12—C11—C10	120.36 (16)	C35—C30—C28	120.97 (13)
C12—C11—H9	116.2 (15)	C31—C30—C28	120.91 (15)
C10—C11—H9	123.4 (15)	C32—C31—C30	120.45 (16)
C11—C12—C7	120.22 (16)	C32—C31—H21	116.8 (12)
C11—C12—H10	120.6 (14)	C30—C31—H21	122.6 (12)
C7—C12—H10	119.1 (14)	C33—C32—C31	120.64 (15)
C18—C13—C14	120.01 (15)	C33—C32—H22	120.8 (13)
C18—C13—P1	120.91 (12)	C31—C32—H22	118.5 (13)
C14—C13—P1	118.87 (12)	C32—C33—C34	119.68 (16)
C15—C14—C13	119.37 (16)	C32—C33—H23	122.9 (12)
C15—C14—H11	119.8 (12)	C34—C33—H23	117.5 (12)
C13—C14—H11	120.7 (12)	C35—C34—C33	119.51 (18)
C14—C15—C16	120.36 (16)	C35—C34—H24	118.0 (13)
C14—C15—H12	117.8 (13)	C33—C34—H24	122.4 (14)
C16—C15—H12	121.8 (13)	C34—C35—C30	121.56 (15)
C17—C16—C15	120.25 (15)	C34—C35—H25	119.7 (14)
C17—C16—H13	120.0 (12)	C30—C35—H25	118.7 (14)
C15—C16—H13	119.8 (13)

Experimental details

Crystal data
Chemical formula	C₃₅H₂₇P
M_r	478.54
Crystal system, space group	Triclinic, P1
Temperature (K)	383
a, b, c (Å)	11.439 (2), 11.609 (2), 11.913 (2)
α, β, γ (°)	116.00 (3), 97.24 (3), 108.47 (3)
V (Å³)	1281.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.27 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.966, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	9166, 4661, 4077
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.133, 1.06
No. of reflections	4661
No. of parameters	433
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.29

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001) and SHELXTL (Sheldrick, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2001).

Selected geometric parameters (Å, º) top

P1—C19	1.7294 (15)	P1—C1	1.8178 (19)
P1—C13	1.8104 (15)	C20—C21	1.206 (2)
P1—C7	1.8132 (18)	C28—C29	1.343 (2)

C19—P1—C13	108.20 (7)	C13—P1—C1	107.73 (7)
C19—P1—C7	117.53 (8)	C7—P1—C1	106.29 (8)
C13—P1—C7	105.18 (7)	C21—C20—C19	179.42 (18)
C19—P1—C1	111.39 (7)	C20—C21—C22	164.32 (18)

Acknowledgements

This work was supported by the NSFC (Nos. 20572062 and 20372042) and by the Doctoral Program of the MOE (Nos. 20050422010 and 20050422011).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Koollenz, G., Penn, G., Theuer, R., Fabian, W. M. F., Abd El-Nabi, H. A., Xiong, Z., Peters, K., Peters, E.-M. & von Schnering, H. G. (1996). Tetrahedron, 52, 15, 5427–5440. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar