(4-Methoxy­phen­yl)diphenyl­phosphine

Flower, K.R.; Miles, P.J.; Pritchard, R.G.

doi:10.1107/S1600536807007271

organic compounds

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ISSN: 2056-9890

Volume 63| Part 3| March 2007| Pages o1339-o1340

https://doi.org/10.1107/S1600536807007271

(4-Methoxyphenyl)diphenylphosphine

Kevin R. Flower,^a ^* Philip J. Miles ^a and Robin G. Pritchard ^a

^aSchool of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, England
^*Correspondence e-mail: kevin.r.flower@manchester.ac.uk

(Received 12 February 2007; accepted 12 February 2007; online 16 February 2007)

The crystal structure of the title compound, C₁₉H₁₇OP, is stabilized by C—H⋯O and C—H⋯π interactions.

Comment

Triphenylphosphine, PPh₃, and its derivatives, such as compound (I), have been widely used in many areas of chemistry, especially as ligands in transition-metal-based homogeneous catalysis. Compound (I) was made as part of a larger synthetic investigation into complexes containing substituted phosphines. The structure of (I) has not previously been reported, although the structure of its corresponding oxide has been described (Whitaker et al., 1995 ).

The molecular structure of (I) (Fig. 1) has a slightly distorted pyramidal geometry; the mean C—P—C angle (103.03°) angle is comparable with values of 102.99 and 102.8° for triphenylphosphine (Daly, 1964 ; Dunne & Orpen, 1991 ), as is the mean C—P bond length [1.831 (2) Å compared to 1.828 and 1.831 Å, respectively].

The extended structure exhibits a zigzag pattern where the molecules pack so that the methoxy groups of near neighbours pack are as far apart as possible. There is a clear intermolecular hydrogen bond [C10—H10 = 0.96 (2), H10⋯Oⁱ = 2.694 (1), C10⋯Oⁱ = 3.354 (3) Å and C10—H10⋯Oⁱ 126.5 (5)°; symmetry code: (i) 1 + x, y, z] which links molecules into chains along the a direction. A C—H⋯Cπ interaction [C2—H2 = 0.98 (2), H2⋯C11ⁱⁱ = 2.874 (1) Å, C2⋯C11ⁱⁱ = 3.354 (5) Å and C2—H2⋯C11ⁱⁱ = 165.41 (9)°; symmetry code: (ii) $[3 \over 2]$ + x, −½ + y, z] is also present. A graphical representation of the extended structure is given in Fig. 2.

Figure 1
The structure of (I)

, with displacement ellipsoids drawn at the 30% probability level.

Figure 2
View normal to (100) of the extended structure of (I)

, showing the zigzag packing.

Experimental

Compound (I) was prepared according to a reported method (McEwan et al., 1975 ). Crystals suitable for the diffraction study were obtained by slow cooling of a hot saturated ethanol solution.

Crystal data

C₁₉H₁₇OP
M_r = 292.3
Orthorhombic, P b c a
a = 10.8879 (4) Å
b = 11.8128 (4) Å
c = 23.9654 (14) Å
V = 3082.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 (2) K
0.2 × 0.2 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
33037 measured reflections
3193 independent reflections
2498 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.104
S = 1.05
3193 reflections
258 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

All H atoms were refined isotropically [C—H = 0.94 (2)–1.00 (3) Å].

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807007271/sg2134sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807007271/sg2134Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(4-Methoxyphenyl)diphenylphosphine top

Crystal data top

C₁₉H₁₇OP	F(000) = 1232
M_r = 292.3	D_x = 1.26 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3722 reflections
a = 10.8879 (4) Å	θ = 2–27°
b = 11.8128 (4) Å	µ = 0.17 mm⁻¹
c = 23.9654 (14) Å	T = 293 K
V = 3082.3 (2) Å³	Prism, colourless
Z = 8	0.2 × 0.2 × 0.15 mm

Data collection top

Nonius KappaCCD diffractometer	2498 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	R_int = 0.065
Graphite monochromator	θ_max = 26.5°, θ_min = 3.1°
Detector resolution: 9 pixels mm^-1	h = 0→13
CCD rotation images, thick slices scans	k = 0→14
33037 measured reflections	l = 0→30
3193 independent 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.041P)² + 1.4742P] where P = (F_o² + 2F_c²)/3
3193 reflections	(Δ/σ)_max = 0.002
258 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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
C1	0.88214 (16)	0.57892 (14)	0.64240 (7)	0.0337 (4)
C2	0.99900 (18)	0.62695 (16)	0.64880 (8)	0.0424 (4)
C3	1.09525 (17)	0.56660 (17)	0.67109 (9)	0.0437 (5)
C4	1.07743 (16)	0.45571 (16)	0.68899 (8)	0.0375 (4)
C5	0.96335 (17)	0.40543 (16)	0.68238 (8)	0.0379 (4)
C6	0.86713 (16)	0.46720 (15)	0.65923 (8)	0.0366 (4)
C7	1.1591 (2)	0.2977 (2)	0.73846 (11)	0.0539 (5)
C8	0.62513 (15)	0.57439 (14)	0.61868 (8)	0.0349 (4)
C9	0.55593 (17)	0.56854 (16)	0.66757 (9)	0.0416 (4)
C10	0.45233 (18)	0.50101 (18)	0.67087 (9)	0.0475 (5)
C11	0.41621 (18)	0.43818 (18)	0.62500 (10)	0.0482 (5)
C12	0.4850 (2)	0.44130 (18)	0.57668 (10)	0.0510 (5)
C13	0.58858 (18)	0.50932 (17)	0.57329 (9)	0.0437 (4)
C14	0.79069 (16)	0.69045 (14)	0.54461 (8)	0.0362 (4)
C15	0.8692 (2)	0.6235 (2)	0.51312 (9)	0.0504 (5)
C16	0.8938 (2)	0.6493 (2)	0.45795 (9)	0.0592 (6)
C17	0.8404 (2)	0.7429 (2)	0.43347 (9)	0.0573 (6)
C18	0.7608 (2)	0.8086 (2)	0.46334 (10)	0.0603 (6)
C19	0.7362 (2)	0.78278 (17)	0.51891 (9)	0.0490 (5)
O1	1.17739 (12)	0.40407 (12)	0.71215 (6)	0.0501 (4)
P1	0.75715 (4)	0.67060 (4)	0.61893 (2)	0.03547 (14)
H2	1.0096 (19)	0.7059 (18)	0.6368 (9)	0.052 (6)*
H3	1.178 (2)	0.5994 (18)	0.6762 (9)	0.054 (6)*
H5	0.9490 (18)	0.3257 (18)	0.6934 (9)	0.046 (5)*
H6	0.7889 (19)	0.4305 (16)	0.6562 (8)	0.042 (5)*
H7A	1.132 (2)	0.2382 (19)	0.7117 (10)	0.056 (6)*
H7B	1.095 (2)	0.303 (2)	0.7666 (11)	0.074 (8)*
H7C	1.240 (2)	0.2778 (19)	0.7527 (10)	0.063 (6)*
H9	0.5791 (18)	0.6119 (18)	0.7006 (9)	0.050 (6)*
H10	0.402 (2)	0.4981 (19)	0.7037 (10)	0.058 (6)*
H11	0.342 (2)	0.3925 (18)	0.6269 (9)	0.058 (6)*
H12	0.463 (2)	0.3969 (18)	0.5438 (10)	0.058 (6)*
H13	0.633 (2)	0.5124 (18)	0.5387 (10)	0.056 (6)*
H15	0.909 (2)	0.560 (2)	0.5290 (11)	0.072 (7)*
H16	0.950 (2)	0.599 (2)	0.4375 (12)	0.080 (8)*
H17	0.861 (2)	0.762 (2)	0.3941 (11)	0.069 (7)*
H18	0.719 (2)	0.873 (2)	0.4464 (12)	0.089 (9)*
H19	0.682 (2)	0.829 (2)	0.5403 (11)	0.074 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0361 (9)	0.0355 (9)	0.0295 (9)	−0.0016 (7)	0.0002 (7)	−0.0015 (7)
C2	0.0430 (10)	0.0386 (10)	0.0456 (11)	−0.0083 (8)	−0.0001 (9)	0.0042 (9)
C3	0.0345 (9)	0.0487 (11)	0.0478 (12)	−0.0089 (8)	−0.0030 (8)	0.0036 (9)
C4	0.0330 (9)	0.0484 (10)	0.0310 (9)	0.0007 (8)	−0.0006 (7)	0.0026 (8)
C5	0.0375 (9)	0.0394 (10)	0.0369 (10)	−0.0027 (8)	0.0004 (8)	0.0060 (8)
C6	0.0324 (9)	0.0381 (9)	0.0394 (10)	−0.0041 (8)	−0.0014 (8)	0.0019 (8)
C7	0.0493 (12)	0.0561 (13)	0.0562 (15)	0.0059 (10)	−0.0108 (11)	0.0140 (11)
C8	0.0329 (8)	0.0353 (9)	0.0365 (9)	0.0064 (7)	−0.0008 (7)	0.0039 (8)
C9	0.0417 (10)	0.0447 (10)	0.0383 (11)	0.0049 (8)	0.0006 (8)	0.0029 (8)
C10	0.0395 (10)	0.0541 (12)	0.0488 (12)	0.0041 (9)	0.0060 (9)	0.0129 (10)
C11	0.0362 (10)	0.0496 (11)	0.0589 (14)	−0.0026 (9)	−0.0049 (9)	0.0137 (10)
C12	0.0509 (12)	0.0514 (12)	0.0507 (13)	−0.0054 (10)	−0.0109 (10)	−0.0003 (10)
C13	0.0445 (10)	0.0477 (11)	0.0389 (11)	−0.0005 (9)	0.0001 (9)	0.0009 (9)
C14	0.0361 (9)	0.0362 (9)	0.0364 (10)	−0.0032 (7)	−0.0016 (7)	0.0019 (7)
C15	0.0529 (12)	0.0579 (13)	0.0403 (12)	0.0119 (10)	0.0049 (9)	0.0061 (10)
C16	0.0555 (13)	0.0841 (17)	0.0381 (12)	0.0065 (12)	0.0068 (10)	0.0028 (12)
C17	0.0648 (14)	0.0713 (15)	0.0358 (12)	−0.0179 (12)	−0.0029 (10)	0.0124 (11)
C18	0.0805 (16)	0.0524 (12)	0.0480 (13)	0.0008 (12)	−0.0137 (12)	0.0142 (10)
C19	0.0590 (12)	0.0426 (11)	0.0453 (12)	0.0068 (10)	−0.0047 (10)	0.0031 (9)
O1	0.0346 (7)	0.0616 (9)	0.0541 (9)	−0.0001 (6)	−0.0068 (6)	0.0148 (7)
P1	0.0389 (3)	0.0329 (2)	0.0346 (3)	0.00217 (18)	0.0016 (2)	−0.00096 (18)

Geometric parameters (Å, º) top

C1—C6	1.390 (2)	C9—H9	0.98 (2)
C1—C2	1.402 (2)	C10—C11	1.384 (3)
C1—P1	1.8279 (18)	C10—H10	0.96 (2)
C2—C3	1.375 (3)	C11—C12	1.380 (3)
C2—H2	0.98 (2)	C11—H11	0.97 (2)
C3—C4	1.392 (3)	C12—C13	1.387 (3)
C3—H3	0.99 (2)	C12—H12	0.98 (2)
C4—O1	1.366 (2)	C13—H13	0.96 (2)
C4—C5	1.386 (3)	C14—C19	1.386 (3)
C5—C6	1.392 (3)	C14—C15	1.388 (3)
C5—H5	0.99 (2)	C14—P1	1.8331 (19)
C6—H6	0.96 (2)	C15—C16	1.383 (3)
C7—O1	1.420 (3)	C15—H15	0.94 (2)
C7—H7A	1.00 (2)	C16—C17	1.380 (3)
C7—H7B	0.98 (3)	C16—H16	0.98 (3)
C7—H7C	0.97 (2)	C17—C18	1.366 (3)
C8—C13	1.390 (3)	C17—H17	1.00 (3)
C8—C9	1.395 (3)	C18—C19	1.392 (3)
C8—P1	1.8325 (18)	C18—H18	0.97 (3)
C9—C10	1.384 (3)	C19—H19	0.95 (3)

C6—C1—C2	117.35 (16)	C9—C10—H10	122.2 (14)
C6—C1—P1	124.37 (13)	C12—C11—C10	119.9 (2)
C2—C1—P1	118.02 (13)	C12—C11—H11	120.3 (14)
C3—C2—C1	121.63 (17)	C10—C11—H11	119.8 (14)
C3—C2—H2	121.1 (13)	C11—C12—C13	120.4 (2)
C1—C2—H2	117.3 (13)	C11—C12—H12	121.8 (13)
C2—C3—C4	120.08 (17)	C13—C12—H12	117.8 (13)
C2—C3—H3	122.6 (13)	C12—C13—C8	120.49 (19)
C4—C3—H3	117.3 (12)	C12—C13—H13	118.9 (13)
O1—C4—C5	124.71 (17)	C8—C13—H13	120.6 (13)
O1—C4—C3	115.75 (16)	C19—C14—C15	118.05 (19)
C5—C4—C3	119.54 (17)	C19—C14—P1	116.57 (15)
C4—C5—C6	119.70 (17)	C15—C14—P1	125.33 (14)
C4—C5—H5	121.2 (12)	C16—C15—C14	120.9 (2)
C6—C5—H5	119.1 (12)	C16—C15—H15	118.2 (16)
C1—C6—C5	121.67 (17)	C14—C15—H15	120.9 (16)
C1—C6—H6	120.8 (11)	C17—C16—C15	120.1 (2)
C5—C6—H6	117.5 (11)	C17—C16—H16	122.2 (16)
O1—C7—H7A	112.3 (13)	C15—C16—H16	117.7 (16)
O1—C7—H7B	110.5 (15)	C18—C17—C16	120.0 (2)
H7A—C7—H7B	106 (2)	C18—C17—H17	121.1 (14)
O1—C7—H7C	104.2 (14)	C16—C17—H17	118.9 (14)
H7A—C7—H7C	108.7 (19)	C17—C18—C19	119.9 (2)
H7B—C7—H7C	115 (2)	C17—C18—H18	121.4 (17)
C13—C8—C9	118.38 (17)	C19—C18—H18	118.7 (17)
C13—C8—P1	124.76 (14)	C14—C19—C18	121.0 (2)
C9—C8—P1	116.85 (14)	C14—C19—H19	118.4 (16)
C10—C9—C8	121.1 (2)	C18—C19—H19	120.6 (16)
C10—C9—H9	117.8 (12)	C4—O1—C7	117.65 (15)
C8—C9—H9	121.1 (13)	C1—P1—C8	102.56 (8)
C11—C10—C9	119.7 (2)	C1—P1—C14	103.10 (8)
C11—C10—H10	118.1 (14)	C8—P1—C14	103.44 (8)

C6—C1—C2—C3	−0.3 (3)	C14—C15—C16—C17	0.3 (4)
P1—C1—C2—C3	173.97 (16)	C15—C16—C17—C18	−1.6 (4)
C1—C2—C3—C4	−1.3 (3)	C16—C17—C18—C19	1.7 (4)
C2—C3—C4—O1	−177.96 (18)	C15—C14—C19—C18	−0.9 (3)
C2—C3—C4—C5	2.3 (3)	P1—C14—C19—C18	176.67 (17)
O1—C4—C5—C6	178.64 (18)	C17—C18—C19—C14	−0.4 (3)
C3—C4—C5—C6	−1.6 (3)	C5—C4—O1—C7	−9.4 (3)
C2—C1—C6—C5	1.0 (3)	C3—C4—O1—C7	170.80 (19)
P1—C1—C6—C5	−172.91 (15)	C6—C1—P1—C8	−4.60 (18)
C4—C5—C6—C1	0.0 (3)	C2—C1—P1—C8	−178.47 (14)
C13—C8—C9—C10	−0.9 (3)	C6—C1—P1—C14	−111.83 (16)
P1—C8—C9—C10	177.97 (14)	C2—C1—P1—C14	74.29 (16)
C8—C9—C10—C11	−0.1 (3)	C13—C8—P1—C1	−90.17 (17)
C9—C10—C11—C12	1.4 (3)	C9—C8—P1—C1	91.05 (15)
C10—C11—C12—C13	−1.7 (3)	C13—C8—P1—C14	16.80 (17)
C11—C12—C13—C8	0.6 (3)	C9—C8—P1—C14	−161.97 (14)
C9—C8—C13—C12	0.6 (3)	C19—C14—P1—C1	−160.33 (15)
P1—C8—C13—C12	−178.14 (15)	C15—C14—P1—C1	17.01 (19)
C19—C14—C15—C16	1.0 (3)	C19—C14—P1—C8	93.10 (16)
P1—C14—C15—C16	−176.35 (18)	C15—C14—P1—C8	−89.55 (18)

Acknowledgements

PJM thanks the EPSRC for a studentship.

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