Diethyl (1-hydr-oxy-1,2-diphenyl-ethyl)phospho-nate.

In the title compound, C(18)H(23)O(4)P, the dihedral angle between the aromatic ring planes is 69.94 (14)°. Both ethyl side chains are disordered over two sets of sites, with occupancy ratios of 80:20 and 70:30. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds occur, leading to R(2) (1)(8) loops, and C-H⋯O and weak C-H⋯π inter-actions are also seen.

Related literature

For related structures, see: Acar et al. (2009 ▶); Tahir et al. (2007 ▶, 2009a ▶,b ▶). For the synthesis, see: Texier-Boullet & Lequitte (1986 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H23O4P

M = 334.33

Monoclinic,

a = 23.8545 (11) Å

b = 10.6663 (5) Å

c = 18.4994 (14) Å

β = 129.451 (2)°

V = 3634.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.17 mm−1

T = 296 K

0.30 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.953, T max = 0.968

18572 measured reflections

4354 independent reflections

2742 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.198

S = 1.05

4354 reflections

217 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901602X/hb2959sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901602X/hb2959Isup2.hkl

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

C18H23O4P	F(000) = 1424
Mr = 334.33	Dx = 1.220 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4354 reflections
a = 23.8545 (11) Å	θ = 2.2–27.9°
b = 10.6663 (5) Å	µ = 0.17 mm−1
c = 18.4994 (14) Å	T = 296 K
β = 129.451 (2)°	Prism, colourless
V = 3634.6 (4) Å3	0.30 × 0.25 × 0.22 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	4354 independent reflections
Radiation source: fine-focus sealed tube	2742 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 7.50 pixels mm-1	θmax = 27.9°, θmin = 2.2°
ω scans	h = −27→31
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→14
Tmin = 0.953, Tmax = 0.968	l = −23→24
18572 measured reflections

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0851P)2 + 3.8003P] where P = (Fo2 + 2Fc2)/3
4354 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.73 e Å−3
8 restraints	Δρmin = −0.63 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
P1	0.23098 (5)	0.51952 (7)	0.48295 (5)	0.0564 (3)
O1	0.24033 (11)	0.65326 (19)	0.37591 (14)	0.0534 (7)
O2	0.17697 (15)	0.4238 (2)	0.47220 (16)	0.0809 (10)
O3	0.29721 (15)	0.4365 (2)	0.51385 (17)	0.0789 (9)
O4	0.25082 (14)	0.62304 (19)	0.54704 (14)	0.0684 (8)
C1	0.17620 (15)	0.4629 (3)	0.30222 (18)	0.0499 (9)
C2	0.1240 (2)	0.3727 (3)	0.2725 (2)	0.0713 (12)
C3	0.1151 (2)	0.2728 (4)	0.2178 (3)	0.0802 (14)
C4	0.1576 (2)	0.2619 (3)	0.1929 (2)	0.0781 (14)
C5	0.2088 (2)	0.3494 (4)	0.2220 (3)	0.0832 (16)
C6	0.21863 (19)	0.4501 (3)	0.2765 (2)	0.0656 (12)
C7	0.18743 (15)	0.5724 (3)	0.36315 (18)	0.0473 (8)
C8	0.11690 (18)	0.6435 (3)	0.3225 (2)	0.0603 (11)
C9	0.08167 (17)	0.7045 (3)	0.2292 (2)	0.0604 (11)
C10	0.1049 (2)	0.8214 (3)	0.2239 (2)	0.0742 (11)
C11	0.0723 (2)	0.8779 (4)	0.1386 (3)	0.0914 (14)
C12	0.0159 (3)	0.8215 (4)	0.0578 (3)	0.1001 (16)
C13	−0.0075 (2)	0.7068 (5)	0.0618 (3)	0.0986 (18)
C14	0.02499 (19)	0.6485 (4)	0.1464 (3)	0.0802 (14)
C15A	0.1966 (3)	0.3662 (6)	0.5570 (4)	0.1000 (17)	0.800
C16A	0.1312 (3)	0.3721 (6)	0.5486 (4)	0.1000 (17)	0.800
C17A	0.3652 (4)	0.4948 (10)	0.5515 (7)	0.130 (3)	0.700
C18A	0.4280 (4)	0.4270 (8)	0.6305 (6)	0.130 (3)	0.700
C17B	0.3660 (8)	0.434 (2)	0.6034 (12)	0.130 (3)	0.300
C15B	0.1434 (12)	0.424 (2)	0.5136 (14)	0.1000 (17)	0.200
C16B	0.1959 (13)	0.347 (2)	0.5989 (15)	0.1000 (17)	0.200
C18B	0.3938 (11)	0.497 (3)	0.5609 (19)	0.130 (3)	0.300
H1	0.241 (2)	0.719 (4)	0.403 (3)	0.0799*
H6	0.25426	0.50943	0.29577	0.0793*
H8A	0.08260	0.58537	0.31588	0.0722*
H8B	0.12741	0.70761	0.36680	0.0722*
H2	0.09468	0.37888	0.28914	0.0847*
H3	0.07968	0.21271	0.19812	0.0963*
H4	0.15139	0.19501	0.15622	0.0936*
H5	0.23811	0.34205	0.20531	0.0991*
H14	0.00846	0.57023	0.14766	0.0964*
H15A	0.23620	0.41156	0.61197	0.1200*	0.800
H15B	0.21144	0.27982	0.56195	0.1200*	0.800
H16A	0.11604	0.45783	0.54114	0.1500*	0.800
H16B	0.14165	0.33803	0.60407	0.1500*	0.800
H16C	0.09302	0.32440	0.49513	0.1500*	0.800
H17A	0.36568	0.57932	0.57130	0.1557*	0.700
H17B	0.36904	0.50098	0.50248	0.1557*	0.700
H18A	0.44289	0.46306	0.68793	0.1947*	0.700
H18B	0.46708	0.43278	0.62840	0.1947*	0.700
H18C	0.41540	0.34059	0.62738	0.1947*	0.700
H10	0.14295	0.86168	0.27863	0.0893*
H11	0.08898	0.95540	0.13628	0.1095*
H12	−0.00657	0.86058	0.00042	0.1191*
H13	−0.04578	0.66759	0.00674	0.1182*
H15C	0.09576	0.38470	0.47291	0.1200*	0.200
H15D	0.13903	0.50761	0.52946	0.1200*	0.200
H16D	0.17588	0.26456	0.59053	0.1500*	0.200
H16E	0.20506	0.38620	0.65210	0.1500*	0.200
H16F	0.24055	0.33917	0.60908	0.1500*	0.200
H17C	0.38530	0.35052	0.62670	0.1557*	0.300
H17D	0.36927	0.48414	0.64973	0.1557*	0.300
H18D	0.39393	0.43929	0.52126	0.1947*	0.300
H18E	0.44239	0.52619	0.60936	0.1947*	0.300
H18F	0.36325	0.56736	0.52431	0.1947*	0.300

	U11	U22	U33	U12	U13	U23
P1	0.0822 (6)	0.0449 (4)	0.0468 (4)	−0.0038 (4)	0.0432 (4)	−0.0023 (3)
O1	0.0690 (13)	0.0474 (11)	0.0556 (11)	−0.0050 (10)	0.0452 (10)	−0.0051 (9)
O2	0.122 (2)	0.0731 (15)	0.0634 (14)	−0.0310 (14)	0.0663 (15)	−0.0082 (12)
O3	0.0938 (18)	0.0634 (14)	0.0675 (14)	0.0183 (13)	0.0456 (13)	0.0055 (12)
O4	0.1092 (18)	0.0490 (12)	0.0520 (12)	−0.0039 (12)	0.0535 (12)	−0.0053 (9)
C1	0.0603 (16)	0.0497 (16)	0.0407 (13)	0.0008 (13)	0.0326 (13)	−0.0008 (11)
C2	0.078 (2)	0.074 (2)	0.069 (2)	−0.0178 (18)	0.0501 (18)	−0.0185 (17)
C3	0.089 (3)	0.071 (2)	0.068 (2)	−0.025 (2)	0.044 (2)	−0.0217 (18)
C4	0.097 (3)	0.066 (2)	0.058 (2)	0.000 (2)	0.043 (2)	−0.0160 (16)
C5	0.097 (3)	0.090 (3)	0.082 (2)	−0.004 (2)	0.066 (2)	−0.025 (2)
C6	0.077 (2)	0.069 (2)	0.068 (2)	−0.0109 (17)	0.0541 (18)	−0.0174 (16)
C7	0.0609 (16)	0.0482 (15)	0.0432 (13)	−0.0041 (13)	0.0379 (13)	−0.0029 (11)
C8	0.0692 (19)	0.071 (2)	0.0582 (17)	0.0050 (16)	0.0487 (16)	0.0000 (15)
C9	0.0586 (18)	0.071 (2)	0.0551 (17)	0.0118 (15)	0.0378 (15)	0.0033 (15)
C10	0.079 (2)	0.066 (2)	0.0573 (19)	0.0130 (18)	0.0338 (17)	0.0025 (16)
C11	0.101 (3)	0.071 (2)	0.071 (2)	0.013 (2)	0.040 (2)	0.0162 (19)
C12	0.102 (3)	0.099 (3)	0.060 (2)	0.015 (3)	0.033 (2)	0.018 (2)
C13	0.076 (3)	0.118 (4)	0.057 (2)	−0.003 (3)	0.0213 (19)	0.003 (2)
C14	0.066 (2)	0.095 (3)	0.067 (2)	−0.007 (2)	0.0364 (18)	0.004 (2)
C15A	0.125 (3)	0.104 (3)	0.091 (3)	−0.004 (3)	0.078 (3)	0.017 (2)
C16A	0.125 (3)	0.104 (3)	0.091 (3)	−0.004 (3)	0.078 (3)	0.017 (2)
C17A	0.084 (4)	0.133 (4)	0.136 (5)	0.020 (4)	0.053 (4)	0.032 (3)
C18A	0.084 (4)	0.133 (4)	0.136 (5)	0.020 (4)	0.053 (4)	0.032 (3)
C17B	0.084 (4)	0.133 (4)	0.136 (5)	0.020 (4)	0.053 (4)	0.032 (3)
C15B	0.125 (3)	0.104 (3)	0.091 (3)	−0.004 (3)	0.078 (3)	0.017 (2)
C16B	0.125 (3)	0.104 (3)	0.091 (3)	−0.004 (3)	0.078 (3)	0.017 (2)
C18B	0.084 (4)	0.133 (4)	0.136 (5)	0.020 (4)	0.053 (4)	0.032 (3)

P1—O2	1.554 (4)	C4—H4	0.9300
P1—O3	1.568 (4)	C5—H5	0.9300
P1—O4	1.461 (2)	C6—H6	0.9300
P1—C7	1.839 (3)	C8—H8A	0.9700
O1—C7	1.419 (5)	C8—H8B	0.9700
O2—C15A	1.458 (7)	C10—H10	0.9300
O2—C15B	1.42 (3)	C11—H11	0.9300
O3—C17A	1.438 (12)	C12—H12	0.9300
O3—C17B	1.408 (19)	C13—H13	0.9300
O1—H1	0.86 (4)	C14—H14	0.9300
C1—C2	1.382 (6)	C15A—H15A	0.9700
C1—C7	1.524 (4)	C15A—H15B	0.9700
C1—C6	1.372 (6)	C15B—H15C	0.9700
C2—C3	1.390 (6)	C15B—H15D	0.9600
C3—C4	1.359 (8)	C16A—H16A	0.9600
C4—C5	1.348 (7)	C16A—H16C	0.9600
C5—C6	1.387 (6)	C16A—H16B	0.9600
C7—C8	1.537 (6)	C16B—H16E	0.9600
C8—C9	1.505 (4)	C16B—H16D	0.9700
C9—C14	1.378 (5)	C16B—H16F	0.9600
C9—C10	1.393 (5)	C17A—H17A	0.9700
C10—C11	1.378 (5)	C17A—H17B	0.9700
C11—C12	1.360 (6)	C17B—H17C	0.9700
C12—C13	1.366 (8)	C17B—H17D	0.9700
C13—C14	1.377 (6)	C18A—H18A	0.9600
C15A—C16A	1.468 (12)	C18A—H18B	0.9600
C15B—C16B	1.49 (3)	C18A—H18C	0.9600
C17A—C18A	1.456 (14)	C18B—H18D	0.9600
C17B—C18B	1.47 (4)	C18B—H18E	0.9600
C2—H2	0.9300	C18B—H18F	0.9600
C3—H3	0.9300
O2—P1—O3	103.70 (16)	C11—C10—H10	120.00
O2—P1—O4	114.51 (19)	C10—C11—H11	120.00
O2—P1—C7	105.05 (15)	C12—C11—H11	120.00
O3—P1—O4	113.52 (16)	C11—C12—H12	120.00
O3—P1—C7	106.21 (17)	C13—C12—H12	120.00
O4—P1—C7	112.93 (13)	C12—C13—H13	120.00
P1—O2—C15A	117.8 (3)	C14—C13—H13	120.00
P1—O2—C15B	129.6 (9)	C9—C14—H14	120.00
P1—O3—C17A	119.8 (5)	C13—C14—H14	120.00
P1—O3—C17B	126.2 (9)	O2—C15A—H15A	111.00
C7—O1—H1	106 (4)	O2—C15A—H15B	111.00
C2—C1—C6	118.0 (3)	C16A—C15A—H15A	111.00
C2—C1—C7	121.2 (4)	C16A—C15A—H15B	111.00
C6—C1—C7	120.7 (3)	H15A—C15A—H15B	109.00
C1—C2—C3	120.4 (5)	O2—C15B—H15D	112.00
C2—C3—C4	120.7 (4)	C16B—C15B—H15C	111.00
C3—C4—C5	119.2 (4)	O2—C15B—H15C	111.00
C4—C5—C6	121.2 (5)	H15C—C15B—H15D	110.00
C1—C6—C5	120.5 (4)	C16B—C15B—H15D	112.00
P1—C7—O1	102.96 (19)	C15A—C16A—H16B	110.00
P1—C7—C8	110.2 (3)	C15A—C16A—H16A	110.00
O1—C7—C1	108.0 (3)	C15A—C16A—H16C	110.00
P1—C7—C1	110.8 (2)	H16A—C16A—H16B	109.00
C1—C7—C8	113.1 (3)	H16A—C16A—H16C	109.00
O1—C7—C8	111.3 (3)	H16B—C16A—H16C	109.00
C7—C8—C9	114.5 (4)	C15B—C16B—H16E	110.00
C8—C9—C10	120.7 (3)	C15B—C16B—H16F	110.00
C8—C9—C14	121.7 (3)	C15B—C16B—H16D	110.00
C10—C9—C14	117.6 (3)	H16D—C16B—H16E	109.00
C9—C10—C11	120.8 (3)	H16D—C16B—H16F	109.00
C10—C11—C12	120.6 (4)	H16E—C16B—H16F	110.00
C11—C12—C13	119.3 (4)	O3—C17A—H17A	109.00
C12—C13—C14	120.8 (4)	O3—C17A—H17B	109.00
C9—C14—C13	120.9 (4)	C18A—C17A—H17A	109.00
O2—C15A—C16A	106.0 (5)	C18A—C17A—H17B	109.00
O2—C15B—C16B	101 (2)	H17A—C17A—H17B	108.00
O3—C17A—C18A	113.3 (8)	O3—C17B—H17C	114.00
O3—C17B—C18B	87.0 (15)	C18B—C17B—H17D	114.00
C1—C2—H2	120.00	O3—C17B—H17D	114.00
C3—C2—H2	120.00	C18B—C17B—H17C	114.00
C2—C3—H3	120.00	H17C—C17B—H17D	111.00
C4—C3—H3	120.00	C17A—C18A—H18B	110.00
C3—C4—H4	120.00	C17A—C18A—H18C	109.00
C5—C4—H4	120.00	C17A—C18A—H18A	109.00
C4—C5—H5	119.00	H18A—C18A—H18C	109.00
C6—C5—H5	119.00	H18B—C18A—H18C	110.00
C1—C6—H6	120.00	H18A—C18A—H18B	109.00
C5—C6—H6	120.00	C17B—C18B—H18D	110.00
C7—C8—H8A	109.00	C17B—C18B—H18E	110.00
C7—C8—H8B	109.00	C17B—C18B—H18F	110.00
C9—C8—H8A	109.00	H18D—C18B—H18E	109.00
C9—C8—H8B	109.00	H18D—C18B—H18F	109.00
H8A—C8—H8B	108.00	H18E—C18B—H18F	109.00
C9—C10—H10	120.00
O3—P1—O2—C15A	69.5 (4)	C2—C1—C7—O1	−175.6 (3)
O4—P1—O2—C15A	−54.7 (4)	C2—C1—C7—C8	−52.0 (4)
C7—P1—O2—C15A	−179.2 (4)	C6—C1—C7—P1	−106.6 (3)
O2—P1—O3—C17A	−165.6 (5)	C6—C1—C7—O1	5.5 (4)
O4—P1—O3—C17A	−40.8 (5)	C6—C1—C7—C8	129.1 (3)
C7—P1—O3—C17A	83.9 (5)	C1—C2—C3—C4	0.2 (6)
O2—P1—C7—O1	−176.6 (2)	C2—C3—C4—C5	0.0 (6)
O2—P1—C7—C1	−61.4 (3)	C3—C4—C5—C6	−0.2 (6)
O2—P1—C7—C8	64.6 (3)	C4—C5—C6—C1	0.0 (6)
O3—P1—C7—O1	−67.1 (2)	P1—C7—C8—C9	172.9 (2)
O3—P1—C7—C1	48.1 (3)	O1—C7—C8—C9	59.3 (3)
O3—P1—C7—C8	174.1 (2)	C1—C7—C8—C9	−62.4 (4)
O4—P1—C7—O1	57.9 (3)	C7—C8—C9—C10	−83.0 (5)
O4—P1—C7—C1	173.1 (3)	C7—C8—C9—C14	98.0 (5)
O4—P1—C7—C8	−60.9 (3)	C8—C9—C10—C11	−179.4 (5)
P1—O2—C15A—C16A	134.5 (4)	C14—C9—C10—C11	−0.4 (7)
P1—O3—C17A—C18A	139.4 (7)	C8—C9—C14—C13	178.7 (5)
C6—C1—C2—C3	−0.3 (5)	C10—C9—C14—C13	−0.3 (8)
C7—C1—C2—C3	−179.3 (3)	C9—C10—C11—C12	1.1 (8)
C2—C1—C6—C5	0.2 (5)	C10—C11—C12—C13	−1.1 (10)
C7—C1—C6—C5	179.2 (3)	C11—C12—C13—C14	0.4 (10)
C2—C1—C7—P1	72.4 (4)	C12—C13—C14—C9	0.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.86 (4)	1.87 (4)	2.718 (3)	170 (5)
C10—H10···O4i	0.93	2.54	3.409 (4)	155
C16A—H16B···CgAii	0.97	2.94	3.657 (8)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.86 (4)	1.87 (4)	2.718 (3)	170 (5)
C10—H10⋯O4i	0.93	2.54	3.409 (4)	155
C16A—H16B⋯CgAii	0.97	2.94	3.657 (8)	133

Symmetry codes: (i) ; (ii) . CgA is the centroid of the C9–C14 ring.