(2-Hydro­xy-5-methyl­phenyl)­di­phenyl­phosphine oxide

Pairs of individual mol­ecules of the title compound, C₁₉H₁₇O₂P, (I), containing tetrahedrally coordinated P atoms are connected across crystallographic inversion centres via complementary O-H...O=P hydrogen bonds.

S1. Comment

NO COMMENT TEXT

S2. Experimental

Yellow crystals of the title compound were obtained when recrystallization of the ReN(O–P)₂ complex of the (2-hydroxy-5-methylphenyl)diphenylphosphine anion (O–P) was attempted from dimethyl sulfoxide. The phosphine oxide probably resulted from oxygen bstraction from the sulfoxide.

S3. Refinement

H atoms were constrained to the parent sites using a riding model; SHELXL96 defaults, C—H 0.93–0.96 Å and O—H 0.82 Å. The isotropic displacement parameters, U_iso, were adjusted to a value 50% (methyl and hydroxyl) or 20% (phenyl) higher than that of the parent site. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 1995).

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRC-2 and NRC-2A (Ahmed et al., 1973); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: NRCVAX (Gabe et al., 1989) and SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson (1976) in NRCVAX; software used to prepare material for publication: NRCVAX and SHELXL93.

(2-Hydroxy-4-methylphenyl)bis(4-methylphenyl)phosphine Oxide

Crystal data

C19H17O2P	F(000) = 648
Mr = 308.30	Dx = 1.294 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 10.730 (2) Å	Cell parameters from 25 reflections
b = 9.659 (2) Å	θ = 20.0–22.0°
c = 15.287 (3) Å	µ = 1.57 mm^−1
β = 92.49 (2)°	T = 293 K
V = 1582.9 (5) Å^3	Block, pale yellow
Z = 4	0.62 × 0.25 × 0.18 mm

Data collection

Nonius CAD-4 diffractometer	2666 reflections with I > 2σ(I)
Radiation source: normal-focus xray tube	Rint = 0.020
Graphite monochromator	θmax = 69.8°, θmin = 4.9°
ω/2θ scans	h = −13→13
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al, 1989)	k = −11→11
Tmin = 0.539, Tmax = 0.777	l = −18→18
11236 measured reflections	5 standard reflections every 60 min
2994 independent reflections	intensity decay: variation 2.2

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0567P)^2 + 0.5028P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.006
2994 reflections	Δρmax = 0.49 e Å^−3
201 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (5)

Special details

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. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R-factor_obs 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 (Ų)

	x	y	z	Uiso*/Ueq
P	0.04832 (4)	0.13921 (4)	0.17572 (2)	0.03090 (15)
O	−0.02811 (11)	0.01072 (12)	0.16342 (8)	0.0407 (3)
O12	0.04141 (11)	0.14137 (12)	−0.01796 (7)	0.0391 (3)
H12	0.0337	0.0841	−0.0574	0.059*
C11	0.18021 (14)	0.14814 (15)	0.10681 (10)	0.0318 (3)
C12	0.16058 (15)	0.13984 (15)	0.01550 (10)	0.0329 (3)
C13	0.26247 (17)	0.13383 (18)	−0.03723 (11)	0.0405 (4)
H13	0.2501	0.1255	−0.0976	0.049*
C14	0.38247 (17)	0.14015 (19)	−0.00036 (13)	0.0453 (4)
H14	0.4497	0.1374	−0.0367	0.054*
C15	0.40485 (16)	0.15059 (18)	0.08977 (12)	0.0421 (4)
C16	0.30269 (15)	0.15332 (17)	0.14187 (11)	0.0368 (4)
H16	0.3159	0.1588	0.2023	0.044*
C17	0.53511 (19)	0.1592 (3)	0.13058 (16)	0.0663 (6)
H17A	0.5325	0.2020	0.1872	0.099*
H17B	0.5865	0.2135	0.0938	0.099*
H17C	0.5693	0.0677	0.1368	0.099*
C21	−0.03979 (15)	0.29671 (17)	0.16077 (10)	0.0341 (3)
C22	−0.15694 (16)	0.3044 (2)	0.19589 (11)	0.0442 (4)
H22	−0.1904	0.2268	0.2222	0.053*
C23	−0.22406 (18)	0.4266 (2)	0.19193 (13)	0.0541 (5)
H23	−0.3017	0.4318	0.2165	0.065*
C24	−0.1756 (2)	0.5405 (2)	0.15157 (13)	0.0581 (6)
H24	−0.2215	0.6222	0.1480	0.070*
C25	−0.0602 (2)	0.5349 (2)	0.11656 (13)	0.0573 (5)
H25	−0.0278	0.6126	0.0897	0.069*
C26	0.00814 (18)	0.41336 (19)	0.12135 (12)	0.0461 (4)
H26	0.0867	0.4099	0.0980	0.055*
C31	0.11215 (15)	0.15011 (16)	0.28655 (10)	0.0333 (3)
C32	0.11305 (18)	0.03265 (19)	0.33851 (12)	0.0452 (4)
H32	0.0776	−0.0490	0.3169	0.054*
C33	0.1668 (2)	0.0366 (2)	0.42276 (13)	0.0571 (5)
H33	0.1663	−0.0421	0.4578	0.069*
C34	0.2206 (2)	0.1567 (2)	0.45453 (12)	0.0551 (5)
H34	0.2580	0.1584	0.5106	0.066*
C35	0.21952 (19)	0.2746 (2)	0.40371 (12)	0.0512 (5)
H35	0.2556	0.3557	0.4255	0.061*
C36	0.16483 (18)	0.27192 (19)	0.32043 (11)	0.0439 (4)
H36	0.1630	0.3520	0.2866	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.0346 (2)	0.0296 (2)	0.0283 (2)	−0.00252 (15)	−0.00077 (15)	−0.00013 (14)
O	0.0463 (7)	0.0375 (6)	0.0382 (6)	−0.0120 (5)	−0.0003 (5)	−0.0027 (5)
O12	0.0409 (6)	0.0397 (6)	0.0360 (6)	−0.0003 (5)	−0.0059 (5)	−0.0035 (5)
C11	0.0358 (8)	0.0275 (8)	0.0319 (8)	0.0003 (6)	−0.0001 (6)	−0.0015 (6)
C12	0.0388 (8)	0.0260 (7)	0.0337 (8)	0.0004 (6)	−0.0017 (6)	0.0001 (6)
C13	0.0494 (10)	0.0396 (9)	0.0327 (8)	0.0017 (7)	0.0044 (7)	−0.0015 (7)
C14	0.0424 (9)	0.0458 (10)	0.0486 (10)	0.0015 (8)	0.0112 (8)	−0.0034 (8)
C15	0.0356 (9)	0.0419 (10)	0.0487 (10)	0.0015 (7)	−0.0002 (7)	−0.0053 (8)
C16	0.0380 (8)	0.0358 (9)	0.0363 (8)	0.0008 (7)	−0.0022 (7)	−0.0034 (7)
C17	0.0362 (10)	0.0914 (18)	0.0709 (14)	0.0025 (10)	−0.0019 (9)	−0.0192 (13)
C21	0.0373 (8)	0.0371 (8)	0.0276 (7)	0.0016 (7)	−0.0020 (6)	−0.0002 (6)
C22	0.0410 (9)	0.0523 (11)	0.0394 (9)	0.0015 (8)	0.0042 (7)	0.0019 (8)
C23	0.0469 (10)	0.0684 (13)	0.0470 (10)	0.0174 (10)	0.0029 (8)	−0.0064 (10)
C24	0.0778 (14)	0.0516 (12)	0.0443 (11)	0.0282 (11)	−0.0028 (10)	−0.0055 (9)
C25	0.0847 (15)	0.0372 (10)	0.0504 (11)	0.0091 (10)	0.0079 (10)	0.0063 (8)
C26	0.0523 (10)	0.0397 (9)	0.0470 (10)	0.0033 (8)	0.0094 (8)	0.0062 (8)
C31	0.0369 (8)	0.0333 (8)	0.0297 (7)	0.0005 (6)	0.0010 (6)	0.0004 (6)
C32	0.0557 (11)	0.0377 (9)	0.0415 (9)	−0.0037 (8)	−0.0043 (8)	0.0065 (7)
C33	0.0775 (14)	0.0512 (12)	0.0416 (10)	0.0014 (10)	−0.0090 (10)	0.0141 (9)
C34	0.0673 (13)	0.0640 (13)	0.0330 (9)	0.0082 (10)	−0.0100 (9)	−0.0012 (9)
C35	0.0654 (12)	0.0463 (11)	0.0407 (10)	−0.0027 (9)	−0.0100 (9)	−0.0102 (8)
C36	0.0605 (11)	0.0349 (9)	0.0358 (9)	−0.0041 (8)	−0.0038 (8)	−0.0003 (7)

Geometric parameters (Å, º)

P—O	1.4950 (12)	C22—C23	1.383 (3)
P—C21	1.8004 (17)	C22—H22	0.9300
P—C11	1.8027 (17)	C23—C24	1.375 (3)
P—C31	1.8027 (16)	C23—H23	0.9300
O12—C12	1.3565 (19)	C24—C25	1.371 (3)
O12—H12	0.8200	C24—H24	0.9300
C11—C16	1.398 (2)	C25—C26	1.384 (3)
C11—C12	1.405 (2)	C25—H25	0.9300
C12—C13	1.387 (2)	C26—H26	0.9300
C13—C14	1.384 (3)	C31—C32	1.385 (2)
C13—H13	0.9300	C31—C36	1.395 (2)
C14—C15	1.392 (3)	C32—C33	1.389 (3)
C14—H14	0.9300	C32—H32	0.9300
C15—C16	1.383 (2)	C33—C34	1.376 (3)
C15—C17	1.508 (3)	C33—H33	0.9300
C16—H16	0.9300	C34—C35	1.378 (3)
C17—H17A	0.9600	C34—H34	0.9300
C17—H17B	0.9600	C35—C36	1.379 (2)
C17—H17C	0.9600	C35—H35	0.9300
C21—C26	1.387 (2)	C36—H36	0.9300
C21—C22	1.390 (2)
O—P—C21	113.79 (7)	C23—C22—C21	120.44 (18)
O—P—C11	113.98 (7)	C23—C22—H22	119.78
C21—P—C11	107.85 (7)	C21—C22—H22	119.78
O—P—C31	110.53 (7)	C24—C23—C22	119.77 (18)
C21—P—C31	104.24 (7)	C24—C23—H23	120.12
C11—P—C31	105.70 (7)	C22—C23—H23	120.12
C12—O12—H12	109.47	C25—C24—C23	120.61 (18)
C16—C11—C12	118.73 (15)	C25—C24—H24	119.70
C16—C11—P	121.75 (12)	C23—C24—H24	119.70
C12—C11—P	119.36 (12)	C24—C25—C26	119.87 (19)
O12—C12—C13	122.35 (15)	C24—C25—H25	120.07
O12—C12—C11	118.18 (14)	C26—C25—H25	120.07
C13—C12—C11	119.45 (15)	C25—C26—C21	120.44 (18)
C14—C13—C12	120.27 (16)	C25—C26—H26	119.78
C14—C13—H13	119.86	C21—C26—H26	119.78
C12—C13—H13	119.86	C32—C31—C36	119.04 (15)
C13—C14—C15	121.58 (16)	C32—C31—P	118.95 (13)
C13—C14—H14	119.21	C36—C31—P	121.96 (12)
C15—C14—H14	119.21	C31—C32—C33	120.12 (17)
C16—C15—C14	117.67 (16)	C31—C32—H32	119.94
C16—C15—C17	120.29 (17)	C33—C32—H32	119.94
C14—C15—C17	122.04 (17)	C34—C33—C32	120.12 (18)
C15—C16—C11	122.27 (16)	C34—C33—H33	119.94
C15—C16—H16	118.87	C32—C33—H33	119.94
C11—C16—H16	118.87	C33—C34—C35	120.30 (17)
C15—C17—H17A	109.47	C33—C34—H34	119.85
C15—C17—H17B	109.47	C35—C34—H34	119.85
H17A—C17—H17B	109.5	C34—C35—C36	119.90 (18)
C15—C17—H17C	109.47	C34—C35—H35	120.05
H17A—C17—H17C	109.5	C36—C35—H35	120.05
H17B—C17—H17C	109.5	C35—C36—C31	120.51 (17)
C26—C21—C22	118.87 (16)	C35—C36—H36	119.75
C26—C21—P	122.62 (13)	C31—C36—H36	119.75
C22—C21—P	118.34 (13)
O—P—C11—C16	−118.04 (13)	C31—P—C21—C22	−78.52 (14)
C21—P—C11—C16	114.58 (13)	C26—C21—C22—C23	−0.4 (3)
C31—P—C11—C16	3.54 (15)	P—C21—C22—C23	175.05 (14)
O—P—C11—C12	57.36 (14)	C21—C22—C23—C24	1.2 (3)
C21—P—C11—C12	−70.02 (13)	C22—C23—C24—C25	−1.2 (3)
C31—P—C11—C12	178.95 (12)	C23—C24—C25—C26	0.4 (3)
C16—C11—C12—O12	−176.99 (14)	C24—C25—C26—C21	0.5 (3)
P—C11—C12—O12	7.47 (19)	C22—C21—C26—C25	−0.5 (3)
C16—C11—C12—C13	1.4 (2)	P—C21—C26—C25	−175.69 (15)
P—C11—C12—C13	−174.09 (12)	O—P—C31—C32	16.00 (16)
O12—C12—C13—C14	176.44 (15)	C21—P—C31—C32	138.64 (14)
C11—C12—C13—C14	−1.9 (2)	C11—P—C31—C32	−107.79 (15)
C12—C13—C14—C15	0.9 (3)	O—P—C31—C36	−166.44 (14)
C13—C14—C15—C16	0.5 (3)	C21—P—C31—C36	−43.79 (16)
C13—C14—C15—C17	−179.28 (19)	C11—P—C31—C36	69.77 (16)
C14—C15—C16—C11	−1.0 (3)	C36—C31—C32—C33	−0.6 (3)
C17—C15—C16—C11	178.80 (18)	P—C31—C32—C33	177.07 (16)
C12—C11—C16—C15	0.0 (2)	C31—C32—C33—C34	−0.8 (3)
P—C11—C16—C15	175.46 (13)	C32—C33—C34—C35	1.3 (3)
O—P—C21—C26	−142.81 (14)	C33—C34—C35—C36	−0.4 (3)
C11—P—C21—C26	−15.32 (16)	C34—C35—C36—C31	−1.0 (3)
C31—P—C21—C26	96.71 (15)	C32—C31—C36—C35	1.5 (3)
O—P—C21—C22	41.97 (15)	P—C31—C36—C35	−176.10 (15)
C11—P—C21—C22	169.46 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O^i	0.82	1.86	2.664 (2)	166

Symmetry code: (i) −x, −y, −z.