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

In the crystal of the title compound, C(16)H(19)O(4)P, the mol-ecules are dimerized with R(2) (2)(10) ring motifs through the hydr-oxy and P=O O atoms. The dihedral angle between the aromatic rings is 66.89 (9)°. There are π-π inter-actions [centroid-centroid distance = 3.9669 (16) Å] between the benzene rings of adjacent benzyl groups. A C-H⋯π inter-action between the aromatic rings where C-H is from a benzyl group is also present.

Related literature

For the preparation and crystal structures of α-hydr­oxy phospho­nates, see: Acar et al. (2009a ▶,b ▶); Tahir et al. (2007 ▶, 2009a ▶,b ▶). For an isomer of the title compouns, see: Acar et al. (2009a ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H19O4P

M = 306.28

Monoclinic,

a = 8.4767 (5) Å

b = 15.8978 (10) Å

c = 13.3888 (7) Å

β = 119.397 (3)°

V = 1571.97 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.963, T max = 0.974

16757 measured reflections

3861 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.126

S = 1.01

3861 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.28 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 for Windows (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/S1600536809029808/at2852sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029808/at2852Isup2.hkl

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

C16H19O4P	F(000) = 648
Mr = 306.28	Dx = 1.294 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3861 reflections
a = 8.4767 (5) Å	θ = 2.8–28.3°
b = 15.8978 (10) Å	µ = 0.19 mm−1
c = 13.3888 (7) Å	T = 296 K
β = 119.397 (3)°	Prismatic, colourless
V = 1571.97 (17) Å3	0.25 × 0.18 × 0.15 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3861 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.8°
ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→21
Tmin = 0.963, Tmax = 0.974	l = −17→17
16757 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2804P] where P = (Fo2 + 2Fc2)/3
3861 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.28 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
P1	1.16204 (7)	0.38185 (3)	0.45831 (5)	0.0440 (2)
O1	0.83863 (19)	0.37902 (9)	0.43056 (13)	0.0455 (5)
O2	1.20677 (18)	0.46360 (9)	0.51545 (14)	0.0587 (5)
O3	1.25054 (19)	0.36505 (11)	0.38159 (14)	0.0660 (6)
O4	1.2208 (2)	0.30558 (10)	0.54132 (14)	0.0762 (6)
C1	0.8814 (2)	0.27486 (12)	0.31946 (16)	0.0393 (6)
C2	0.9200 (3)	0.24523 (14)	0.23689 (18)	0.0528 (8)
C3	0.8833 (3)	0.16197 (17)	0.2000 (2)	0.0636 (9)
C4	0.8104 (3)	0.10853 (16)	0.2456 (2)	0.0684 (9)
C5	0.7733 (3)	0.13707 (15)	0.3286 (2)	0.0658 (9)
C6	0.8080 (3)	0.21952 (13)	0.3647 (2)	0.0512 (8)
C7	0.9192 (2)	0.36591 (12)	0.36066 (16)	0.0371 (6)
C8	0.8505 (3)	0.43043 (13)	0.26211 (17)	0.0444 (7)
C9	0.6550 (3)	0.41928 (13)	0.17226 (18)	0.0456 (7)
C10	0.6074 (4)	0.38734 (16)	0.0652 (2)	0.0691 (9)
C11	0.4283 (5)	0.37485 (19)	−0.0165 (2)	0.0922 (11)
C12	0.2939 (4)	0.39384 (18)	0.0079 (3)	0.0883 (11)
C13	0.3378 (3)	0.42615 (17)	0.1120 (3)	0.0762 (10)
C14	0.5166 (3)	0.43991 (14)	0.1941 (2)	0.0565 (8)
C15	1.4435 (3)	0.36510 (19)	0.4291 (3)	0.0795 (11)
C16	1.3067 (5)	0.3068 (2)	0.6594 (3)	0.1003 (15)
H1	0.844 (3)	0.4272 (14)	0.4467 (19)	0.0546*
H2	0.97088	0.28115	0.20561	0.0634*
H3	0.90891	0.14285	0.14384	0.0763*
H4	0.78583	0.05302	0.22077	0.0821*
H5	0.72445	0.10061	0.36055	0.0789*
H6	0.78141	0.23814	0.42066	0.0615*
H8A	0.86629	0.48651	0.29419	0.0533*
H8B	0.92463	0.42629	0.22556	0.0533*
H10	0.69787	0.37396	0.04765	0.0829*
H11	0.39936	0.35349	−0.08820	0.1106*
H12	0.17327	0.38469	−0.04633	0.1061*
H13	0.24629	0.43934	0.12862	0.0914*
H14	0.54368	0.46321	0.26443	0.0678*
H15A	1.48869	0.42133	0.45095	0.1196*
H15B	1.47329	0.34472	0.37294	0.1196*
H15C	1.49759	0.32926	0.49535	0.1196*
H16A	1.42483	0.28223	0.68969	0.1505*
H16B	1.23695	0.27518	0.68516	0.1505*
H16C	1.31802	0.36388	0.68549	0.1505*

	U11	U22	U33	U12	U13	U23
P1	0.0404 (3)	0.0400 (3)	0.0461 (3)	0.0007 (2)	0.0169 (2)	−0.0084 (3)
O1	0.0601 (9)	0.0362 (8)	0.0526 (9)	−0.0011 (7)	0.0373 (8)	−0.0051 (7)
O2	0.0475 (8)	0.0454 (9)	0.0735 (10)	−0.0043 (7)	0.0221 (8)	−0.0213 (8)
O3	0.0412 (8)	0.0905 (13)	0.0680 (10)	−0.0029 (8)	0.0282 (8)	−0.0230 (9)
O4	0.0837 (12)	0.0515 (11)	0.0533 (10)	0.0049 (8)	0.0027 (9)	0.0020 (8)
C1	0.0361 (10)	0.0373 (11)	0.0383 (11)	0.0022 (8)	0.0134 (9)	−0.0029 (9)
C2	0.0604 (13)	0.0521 (14)	0.0467 (12)	0.0047 (10)	0.0268 (11)	−0.0044 (11)
C3	0.0687 (16)	0.0608 (17)	0.0498 (14)	0.0114 (12)	0.0203 (12)	−0.0182 (13)
C4	0.0593 (14)	0.0453 (15)	0.0803 (19)	−0.0029 (11)	0.0185 (14)	−0.0198 (14)
C5	0.0632 (15)	0.0430 (14)	0.0912 (19)	−0.0100 (11)	0.0380 (15)	−0.0106 (14)
C6	0.0529 (12)	0.0425 (13)	0.0643 (14)	−0.0049 (10)	0.0334 (11)	−0.0079 (11)
C7	0.0403 (10)	0.0355 (11)	0.0379 (10)	−0.0005 (8)	0.0211 (9)	−0.0020 (9)
C8	0.0472 (12)	0.0397 (12)	0.0494 (12)	−0.0004 (9)	0.0261 (10)	0.0038 (10)
C9	0.0516 (12)	0.0355 (12)	0.0430 (12)	0.0005 (9)	0.0181 (10)	0.0072 (10)
C10	0.0815 (18)	0.0677 (17)	0.0464 (14)	0.0126 (14)	0.0223 (13)	0.0061 (13)
C11	0.108 (2)	0.074 (2)	0.0480 (16)	0.0089 (18)	0.0023 (17)	−0.0025 (15)
C12	0.0672 (18)	0.0561 (18)	0.084 (2)	−0.0079 (14)	−0.0073 (16)	0.0017 (16)
C13	0.0484 (14)	0.0614 (18)	0.096 (2)	0.0007 (12)	0.0179 (14)	0.0064 (16)
C14	0.0518 (13)	0.0459 (14)	0.0631 (15)	0.0036 (10)	0.0215 (12)	0.0023 (12)
C15	0.0484 (14)	0.101 (2)	0.093 (2)	−0.0057 (14)	0.0377 (14)	−0.0070 (17)
C16	0.121 (3)	0.102 (3)	0.0607 (18)	0.000 (2)	0.0312 (19)	0.0099 (18)

P1—O2	1.4606 (16)	C12—C13	1.355 (5)
P1—O3	1.5639 (19)	C13—C14	1.385 (4)
P1—O4	1.5524 (17)	C2—H2	0.9300
P1—C7	1.835 (2)	C3—H3	0.9300
O1—C7	1.419 (3)	C4—H4	0.9300
O3—C15	1.435 (4)	C5—H5	0.9300
O4—C16	1.378 (4)	C6—H6	0.9300
O1—H1	0.79 (2)	C8—H8A	0.9700
C1—C6	1.378 (3)	C8—H8B	0.9700
C1—C7	1.526 (3)	C10—H10	0.9300
C1—C2	1.381 (3)	C11—H11	0.9300
C2—C3	1.394 (3)	C12—H12	0.9300
C3—C4	1.359 (4)	C13—H13	0.9300
C4—C5	1.372 (4)	C14—H14	0.9300
C5—C6	1.378 (3)	C15—H15A	0.9600
C7—C8	1.542 (3)	C15—H15B	0.9600
C8—C9	1.506 (3)	C15—H15C	0.9600
C9—C14	1.381 (4)	C16—H16A	0.9600
C9—C10	1.381 (3)	C16—H16B	0.9600
C10—C11	1.382 (5)	C16—H16C	0.9600
C11—C12	1.364 (6)
O1···O2	3.059 (2)	C5···H16Av	2.9000
O1···O4	3.056 (3)	C6···H16Av	2.9300
O1···C14	3.151 (3)	C8···H2	2.8300
O1···C15i	3.347 (4)	C13···H5vii	2.8800
O1···O2ii	2.684 (2)	C14···H15Bi	3.0000
O2···O1ii	2.684 (2)	H1···O2	2.80 (3)
O2···O1	3.059 (2)	H1···H8A	2.3400
O3···C2	3.147 (3)	H1···H14	2.5800
O4···C6	3.404 (3)	H1···O2ii	1.92 (2)
O4···C12iii	3.303 (3)	H2···O3	2.7300
O4···O1	3.056 (3)	H2···C8	2.8300
O1···H6	2.2800	H2···H8B	2.3800
O1···H14	2.7400	H2···H16Bviii	2.5600
O1···H15Bi	2.8500	H3···O1viii	2.6400
O1···H3iv	2.6400	H5···C13ix	2.8800
O2···H1	2.80 (3)	H5···H13ix	2.5700
O2···H1ii	1.92 (2)	H6···O1	2.2800
O2···H16C	2.5500	H8A···H1	2.3400
O2···H14ii	2.9000	H8A···H14	2.5900
O3···H8B	2.7000	H8B···O3	2.7000
O3···H2	2.7300	H8B···C2	2.8800
O4···H15C	2.7300	H8B···H2	2.3800
C1···C10	3.524 (3)	H8B···H10	2.3600
C2···O3	3.147 (3)	H10···C2	3.0800
C2···C9	3.398 (3)	H10···H8B	2.3600
C2···C10	3.381 (4)	H12···C4v	2.9700
C5···C16v	3.574 (5)	H12···C5v	2.9700
C6···O4	3.404 (3)	H13···H5vii	2.5700
C9···C2	3.398 (3)	H14···O1	2.7400
C10···C2	3.381 (4)	H14···H1	2.5800
C10···C1	3.524 (3)	H14···H8A	2.5900
C12···O4v	3.303 (3)	H14···O2ii	2.9000
C14···O1	3.151 (3)	H15B···O1vi	2.8500
C15···O1vi	3.347 (4)	H15B···C14vi	3.0000
C16···C5iii	3.574 (5)	H15C···O4	2.7300
C2···H10	3.0800	H15C···C3iii	3.0700
C2···H8B	2.8800	H16A···C5iii	2.9000
C3···H15Cv	3.0700	H16A···C6iii	2.9300
C4···H12iii	2.9700	H16B···H2iv	2.5600
C5···H12iii	2.9700	H16C···O2	2.5500
O2—P1—O3	114.27 (10)	C4—C3—H3	120.00
O2—P1—O4	114.23 (9)	C3—C4—H4	120.00
O2—P1—C7	114.08 (10)	C5—C4—H4	120.00
O3—P1—O4	104.36 (10)	C4—C5—H5	120.00
O3—P1—C7	103.91 (9)	C6—C5—H5	120.00
O4—P1—C7	104.81 (10)	C1—C6—H6	119.00
P1—O3—C15	121.25 (18)	C5—C6—H6	119.00
P1—O4—C16	127.83 (17)	C7—C8—H8A	109.00
C7—O1—H1	109.9 (19)	C7—C8—H8B	109.00
C2—C1—C6	118.02 (19)	C9—C8—H8A	109.00
C6—C1—C7	120.45 (18)	C9—C8—H8B	109.00
C2—C1—C7	121.52 (18)	H8A—C8—H8B	108.00
C1—C2—C3	120.6 (2)	C9—C10—H10	119.00
C2—C3—C4	120.4 (2)	C11—C10—H10	119.00
C3—C4—C5	119.5 (2)	C10—C11—H11	120.00
C4—C5—C6	120.3 (2)	C12—C11—H11	120.00
C1—C6—C5	121.2 (2)	C11—C12—H12	120.00
P1—C7—C1	110.58 (13)	C13—C12—H12	120.00
P1—C7—C8	109.76 (15)	C12—C13—H13	119.00
O1—C7—C1	107.11 (15)	C14—C13—H13	119.00
O1—C7—C8	111.40 (17)	C9—C14—H14	120.00
C1—C7—C8	113.43 (16)	C13—C14—H14	120.00
P1—C7—O1	104.15 (13)	O3—C15—H15A	109.00
C7—C8—C9	114.24 (19)	O3—C15—H15B	109.00
C8—C9—C10	121.2 (3)	O3—C15—H15C	109.00
C10—C9—C14	117.5 (2)	H15A—C15—H15B	110.00
C8—C9—C14	121.3 (2)	H15A—C15—H15C	109.00
C9—C10—C11	121.5 (3)	H15B—C15—H15C	109.00
C10—C11—C12	120.0 (3)	O4—C16—H16A	109.00
C11—C12—C13	119.4 (3)	O4—C16—H16B	109.00
C12—C13—C14	121.2 (3)	O4—C16—H16C	109.00
C9—C14—C13	120.5 (2)	H16A—C16—H16B	110.00
C1—C2—H2	120.00	H16A—C16—H16C	109.00
C3—C2—H2	120.00	H16B—C16—H16C	109.00
C2—C3—H3	120.00
O2—P1—O3—C15	59.8 (2)	C2—C1—C7—C8	47.6 (3)
O4—P1—O3—C15	−65.7 (2)	C6—C1—C7—P1	103.4 (2)
C7—P1—O3—C15	−175.28 (19)	C6—C1—C7—O1	−9.5 (3)
O2—P1—O4—C16	0.5 (3)	C6—C1—C7—C8	−132.8 (2)
O3—P1—O4—C16	126.0 (3)	C1—C2—C3—C4	−0.6 (4)
C7—P1—O4—C16	−125.1 (3)	C2—C3—C4—C5	−0.1 (4)
O2—P1—C7—O1	−56.34 (15)	C3—C4—C5—C6	0.6 (4)
O2—P1—C7—C1	−171.09 (13)	C4—C5—C6—C1	−0.5 (4)
O2—P1—C7—C8	63.03 (17)	P1—C7—C8—C9	176.07 (16)
O3—P1—C7—O1	178.59 (12)	O1—C7—C8—C9	−69.1 (2)
O3—P1—C7—C1	63.84 (15)	C1—C7—C8—C9	51.8 (3)
O3—P1—C7—C8	−62.04 (16)	C7—C8—C9—C10	−106.8 (2)
O4—P1—C7—O1	69.34 (14)	C7—C8—C9—C14	72.6 (3)
O4—P1—C7—C1	−45.42 (15)	C8—C9—C10—C11	178.2 (2)
O4—P1—C7—C8	−171.30 (14)	C14—C9—C10—C11	−1.2 (4)
C6—C1—C2—C3	0.8 (3)	C8—C9—C14—C13	−177.5 (2)
C7—C1—C2—C3	−179.6 (2)	C10—C9—C14—C13	2.0 (3)
C2—C1—C6—C5	−0.2 (3)	C9—C10—C11—C12	−0.3 (4)
C7—C1—C6—C5	−179.9 (2)	C10—C11—C12—C13	1.0 (4)
C2—C1—C7—P1	−76.2 (2)	C11—C12—C13—C14	−0.2 (4)
C2—C1—C7—O1	170.90 (19)	C12—C13—C14—C9	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ii	0.79 (2)	1.92 (2)	2.684 (2)	164 (3)
C6—H6···O1	0.93	2.28	2.655 (3)	103.00
C16—H16C···O2	0.96	2.55	3.007 (4)	110.00
C12—H12···CgAv	0.93	2.86	3.755 (4)	163.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.79 (2)	1.92 (2)	2.684 (2)	164 (3)
C12—H12⋯CgAii	0.93	2.86	3.755 (4)	163

Symmetry codes: (i) ; (ii) . CgA is the centroid of the C1–C6 ring.