Dimethyl (2-hydr-oxy-4-phenyl-but-3-en-2-yl)phospho-nate.

In the title compound, C(12)H(17)O(4)P, the phenyl-butenyl group is disordered over two sets of sites with an occupancy ratio of 0.755 (12):0.245 (12). In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds occur, forming R(2) (2)(10) ring motifs. The packing is consolidated by weak C-H⋯π inter-actions.

Related literature

For related structures, see: Acar et al. (2009 ▶); Tahir et al. (2007 ▶, 2009a ▶,b ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H17O4P

M = 256.23

Monoclinic,

a = 17.1522 (12) Å

b = 8.1571 (13) Å

c = 19.5230 (12) Å

β = 103.771 (10)°

V = 2653.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.25 × 0.14 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (MolEN; Fair, 1990 ▶) T min = 0.885, T max = 0.954

2519 measured reflections

2415 independent reflections

1684 reflections with I > 2σ(I)

R int = 0.095

3 standard reflections frequency: 120 min intensity decay: 0.6%

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.175

S = 1.07

2415 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993 ▶); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ▶); program(s) used to solve structure: WinGX (Farrugia, 1999 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044067/hb5172sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044067/hb5172Isup2.hkl

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

C12H17O4P	F(000) = 1088
Mr = 256.23	Dx = 1.283 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 17.1522 (12) Å	θ = 9.9–13.9°
b = 8.1571 (13) Å	µ = 0.21 mm−1
c = 19.5230 (12) Å	T = 296 K
β = 103.771 (10)°	Needle, colourless
V = 2653.0 (5) Å3	0.25 × 0.14 × 0.12 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	Rint = 0.095
ω/2θ scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: ψ scan (MolEN; Fair, 1990)	h = −20→20
Tmin = 0.885, Tmax = 0.954	k = 0→9
2519 measured reflections	l = −23→0
2415 independent reflections	3 standard reflections every 120 min
1684 reflections with I > 2σ(I)	intensity decay: 0.6%

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)] = 0.061	H-atom parameters constrained
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.114P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2415 reflections	Δρmax = 0.53 e Å−3
177 parameters	Δρmin = −0.42 e Å−3
0 restraints

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.43961 (4)	0.29251 (9)	0.06739 (4)	0.0399 (3)
O1	0.43699 (13)	0.6068 (3)	0.08493 (11)	0.0548 (8)
O2	0.49603 (12)	0.2946 (3)	0.02130 (12)	0.0528 (8)
O3	0.37510 (12)	0.1526 (2)	0.05085 (11)	0.0500 (7)
O4	0.48115 (13)	0.2636 (3)	0.14713 (12)	0.0597 (8)
C1A	0.2124 (3)	0.4228 (6)	0.1674 (2)	0.0453 (16)	0.755 (12)
C2A	0.23963 (19)	0.4970 (7)	0.2329 (3)	0.058 (2)	0.755 (12)
C3A	0.1939 (3)	0.4884 (9)	0.28271 (18)	0.078 (2)	0.755 (12)
C4A	0.1209 (3)	0.4058 (9)	0.2671 (3)	0.072 (2)	0.755 (12)
C5A	0.0937 (2)	0.3316 (6)	0.2017 (3)	0.062 (2)	0.755 (12)
C6A	0.1395 (3)	0.3401 (6)	0.15183 (15)	0.0524 (17)	0.755 (12)
C7A	0.2601 (3)	0.4283 (6)	0.1139 (2)	0.0451 (16)	0.755 (12)
C8A	0.3344 (4)	0.4814 (7)	0.1215 (3)	0.0414 (19)	0.755 (12)
C9	0.37966 (18)	0.4799 (3)	0.06310 (16)	0.0440 (10)
C10	0.3323 (2)	0.5090 (4)	−0.01138 (18)	0.0584 (11)
C11	0.4001 (2)	−0.0152 (4)	0.0447 (2)	0.0644 (13)
C12	0.5626 (2)	0.3125 (6)	0.1775 (2)	0.0896 (19)
C6B	0.1066 (9)	0.341 (2)	0.1847 (9)	0.061 (3)	0.245 (12)
C7B	0.3065 (12)	0.441 (2)	0.0916 (13)	0.046 (6)	0.245 (12)
C1B	0.1670 (11)	0.380 (2)	0.1509 (5)	0.061 (3)	0.245 (12)
C2B	0.2328 (8)	0.471 (2)	0.1857 (9)	0.061 (3)	0.245 (12)
C3B	0.2381 (8)	0.525 (2)	0.2543 (9)	0.061 (3)	0.245 (12)
C4B	0.1777 (12)	0.486 (3)	0.2880 (7)	0.061 (3)	0.245 (12)
C5B	0.1119 (10)	0.395 (3)	0.2532 (9)	0.061 (3)	0.245 (12)
C8B	0.2981 (10)	0.5086 (19)	0.1470 (10)	0.057 (6)	0.245 (12)
H1	0.45706	0.63143	0.05218	0.0821*
H2A	0.28844	0.55226	0.24331	0.0697*	0.755 (12)
H10C	0.36812	0.51292	−0.04233	0.0875*
H11A	0.35594	−0.08762	0.04446	0.0966*
H11B	0.41720	−0.02795	0.00165	0.0966*
H11C	0.44381	−0.04117	0.08403	0.0966*
H12A	0.59764	0.26187	0.15202	0.1344*
H12B	0.56693	0.42950	0.17485	0.1344*
H12C	0.57762	0.27862	0.22598	0.1344*
H3A	0.21203	0.53806	0.32650	0.0928*	0.755 (12)
H4A	0.09026	0.40008	0.30047	0.0865*	0.755 (12)
H5A	0.04489	0.27630	0.19124	0.0741*	0.755 (12)
H6A	0.12130	0.29050	0.10804	0.0629*	0.755 (12)
H7A	0.23485	0.38956	0.06932	0.0541*	0.755 (12)
H8A	0.36086	0.52242	0.16532	0.0500*	0.755 (12)
H10A	0.29444	0.42147	−0.02555	0.0875*
H10B	0.30398	0.61121	−0.01371	0.0875*
H1B	0.16342	0.34369	0.10503	0.0729*	0.245 (12)
H3B	0.28213	0.58635	0.27758	0.0729*	0.245 (12)
H4B	0.18126	0.52218	0.33391	0.0729*	0.245 (12)
H5B	0.07147	0.36876	0.27580	0.0729*	0.245 (12)
H6B	0.06255	0.27951	0.16136	0.0729*	0.245 (12)
H7B	0.26815	0.36654	0.06805	0.0543*	0.245 (12)
H8B	0.33514	0.58922	0.16626	0.0680*	0.245 (12)

	U11	U22	U33	U12	U13	U23
P1	0.0354 (4)	0.0436 (5)	0.0463 (5)	0.0019 (3)	0.0206 (3)	0.0024 (3)
O1	0.0676 (15)	0.0482 (12)	0.0568 (13)	−0.0064 (11)	0.0312 (12)	−0.0074 (10)
O2	0.0520 (13)	0.0542 (13)	0.0644 (14)	0.0030 (10)	0.0382 (11)	0.0013 (10)
O3	0.0399 (12)	0.0423 (11)	0.0723 (15)	0.0011 (9)	0.0225 (10)	−0.0003 (10)
O4	0.0499 (13)	0.0785 (15)	0.0530 (14)	0.0069 (12)	0.0167 (11)	0.0118 (11)
C1A	0.037 (3)	0.064 (3)	0.036 (2)	0.007 (2)	0.011 (2)	−0.005 (2)
C2A	0.043 (3)	0.093 (4)	0.045 (4)	−0.002 (2)	0.022 (2)	−0.011 (3)
C3A	0.055 (4)	0.140 (5)	0.047 (3)	−0.025 (4)	0.031 (3)	−0.022 (3)
C4A	0.053 (4)	0.121 (5)	0.051 (3)	−0.013 (3)	0.029 (3)	−0.020 (3)
C5A	0.046 (3)	0.096 (4)	0.054 (4)	0.000 (2)	0.033 (2)	−0.008 (3)
C6A	0.035 (3)	0.078 (3)	0.051 (3)	−0.002 (2)	0.024 (2)	−0.007 (2)
C7A	0.040 (3)	0.061 (3)	0.040 (2)	−0.007 (2)	0.021 (2)	−0.011 (2)
C8A	0.038 (4)	0.047 (3)	0.040 (3)	0.002 (2)	0.011 (3)	−0.005 (2)
C9	0.0388 (16)	0.0440 (16)	0.0560 (18)	0.0029 (13)	0.0245 (14)	0.0051 (13)
C10	0.051 (2)	0.0560 (19)	0.069 (2)	0.0017 (15)	0.0160 (17)	0.0091 (16)
C11	0.066 (2)	0.0462 (18)	0.085 (3)	0.0049 (16)	0.026 (2)	−0.0011 (16)
C12	0.065 (3)	0.119 (4)	0.074 (3)	−0.015 (2)	−0.005 (2)	−0.003 (2)
C6B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C7B	0.034 (10)	0.047 (9)	0.058 (13)	0.003 (7)	0.015 (9)	0.002 (7)
C1B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C2B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C3B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C4B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C5B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C8B	0.036 (8)	0.056 (9)	0.083 (12)	−0.010 (7)	0.023 (9)	−0.028 (8)

P1—O2	1.470 (2)	C8A—C9	1.525 (7)
P1—O3	1.569 (2)	C9—C10	1.506 (5)
P1—O4	1.568 (2)	C1B—H1B	0.9300
P1—C9	1.833 (3)	C2A—H2A	0.9300
O1—C9	1.422 (4)	C3A—H3A	0.9300
O3—C11	1.448 (4)	C3B—H3B	0.9300
O4—C12	1.438 (4)	C4A—H4A	0.9300
O1—H1	0.8200	C4B—H4B	0.9300
C1A—C2A	1.391 (7)	C5A—H5A	0.9300
C1A—C7A	1.473 (7)	C5B—H5B	0.9300
C1A—C6A	1.389 (7)	C6A—H6A	0.9300
C1B—C2B	1.39 (2)	C6B—H6B	0.9300
C1B—C6B	1.39 (2)	C7A—H7A	0.9300
C2A—C3A	1.389 (6)	C7B—H7B	0.9300
C2B—C8B	1.52 (2)	C8A—H8A	0.9300
C2B—C3B	1.39 (2)	C8B—H8B	0.9300
C3A—C4A	1.390 (8)	C10—H10B	0.9600
C3B—C4B	1.39 (2)	C10—H10A	0.9600
C4A—C5A	1.390 (8)	C10—H10C	0.9600
C4B—C5B	1.39 (3)	C11—H11A	0.9600
C5A—C6A	1.391 (6)	C11—H11B	0.9600
C5B—C6B	1.39 (2)	C11—H11C	0.9600
C7A—C8A	1.321 (9)	C12—H12A	0.9600
C7B—C8B	1.25 (3)	C12—H12B	0.9600
C7B—C9	1.52 (2)	C12—H12C	0.9600
O2—P1—O3	114.66 (13)	C2A—C3A—H3A	120.00
O2—P1—O4	113.56 (13)	C4A—C3A—H3A	120.00
O2—P1—C9	113.97 (14)	C2B—C3B—H3B	120.00
O3—P1—O4	103.09 (12)	C4B—C3B—H3B	120.00
O3—P1—C9	103.70 (12)	C3A—C4A—H4A	120.00
O4—P1—C9	106.75 (14)	C5A—C4A—H4A	120.00
P1—O3—C11	119.8 (2)	C3B—C4B—H4B	120.00
P1—O4—C12	122.3 (2)	C5B—C4B—H4B	120.00
C9—O1—H1	109.00	C4A—C5A—H5A	120.00
C2A—C1A—C7A	121.1 (4)	C6A—C5A—H5A	120.00
C6A—C1A—C7A	118.9 (4)	C4B—C5B—H5B	120.00
C2A—C1A—C6A	120.0 (4)	C6B—C5B—H5B	120.00
C2B—C1B—C6B	120.1 (12)	C5A—C6A—H6A	120.00
C1A—C2A—C3A	120.0 (4)	C1A—C6A—H6A	120.00
C1B—C2B—C3B	120.0 (14)	C1B—C6B—H6B	120.00
C1B—C2B—C8B	118.3 (14)	C5B—C6B—H6B	120.00
C3B—C2B—C8B	121.7 (14)	C1A—C7A—H7A	116.00
C2A—C3A—C4A	120.0 (5)	C8A—C7A—H7A	116.00
C2B—C3B—C4B	119.8 (15)	C9—C7B—H7B	120.00
C3A—C4A—C5A	120.0 (5)	C8B—C7B—H7B	120.00
C3B—C4B—C5B	120.2 (15)	C7A—C8A—H8A	118.00
C4A—C5A—C6A	120.0 (4)	C9—C8A—H8A	118.00
C4B—C5B—C6B	120.0 (16)	C2B—C8B—H8B	117.00
C1A—C6A—C5A	120.0 (4)	C7B—C8B—H8B	117.00
C1B—C6B—C5B	119.9 (15)	C9—C10—H10C	110.00
C1A—C7A—C8A	127.9 (4)	C9—C10—H10B	109.00
C8B—C7B—C9	119.9 (17)	C9—C10—H10A	109.00
C7A—C8A—C9	124.3 (5)	H10B—C10—H10C	109.00
C2B—C8B—C7B	126.1 (17)	H10A—C10—H10B	109.00
C7B—C9—C10	94.8 (9)	H10A—C10—H10C	110.00
O1—C9—C10	110.5 (2)	H11A—C11—H11B	110.00
O1—C9—C7B	127.9 (8)	O3—C11—H11A	109.00
C8A—C9—C10	117.9 (3)	O3—C11—H11B	109.00
P1—C9—O1	104.7 (2)	O3—C11—H11C	109.00
P1—C9—C8A	110.6 (3)	H11A—C11—H11C	109.00
P1—C9—C10	110.1 (2)	H11B—C11—H11C	109.00
P1—C9—C7B	108.2 (7)	H12B—C12—H12C	109.00
O1—C9—C8A	102.1 (3)	O4—C12—H12A	109.00
C2B—C1B—H1B	120.00	O4—C12—H12B	109.00
C6B—C1B—H1B	120.00	O4—C12—H12C	109.00
C1A—C2A—H2A	120.00	H12A—C12—H12B	110.00
C3A—C2A—H2A	120.00	H12A—C12—H12C	109.00
O2—P1—O3—C11	50.8 (3)	C6A—C1A—C2A—C3A	0.0 (8)
O4—P1—O3—C11	−73.1 (2)	C7A—C1A—C2A—C3A	−179.3 (5)
C9—P1—O3—C11	175.7 (2)	C2A—C1A—C6A—C5A	0.1 (7)
O2—P1—O4—C12	28.4 (3)	C7A—C1A—C6A—C5A	179.3 (4)
O3—P1—O4—C12	153.1 (3)	C2A—C1A—C7A—C8A	8.7 (8)
C9—P1—O4—C12	−98.0 (3)	C6A—C1A—C7A—C8A	−170.6 (5)
O2—P1—C9—O1	−60.4 (2)	C1A—C2A—C3A—C4A	−0.1 (9)
O2—P1—C9—C8A	−169.6 (3)	C2A—C3A—C4A—C5A	0.1 (10)
O2—P1—C9—C10	58.4 (3)	C3A—C4A—C5A—C6A	−0.1 (9)
O3—P1—C9—O1	174.29 (18)	C4A—C5A—C6A—C1A	0.0 (8)
O3—P1—C9—C8A	65.1 (3)	C1A—C7A—C8A—C9	179.0 (4)
O3—P1—C9—C10	−67.0 (2)	C7A—C8A—C9—P1	−93.6 (6)
O4—P1—C9—O1	65.8 (2)	C7A—C8A—C9—O1	155.5 (5)
O4—P1—C9—C8A	−43.4 (3)	C7A—C8A—C9—C10	34.2 (7)
O4—P1—C9—C10	−175.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.90	2.721 (3)	176
C6B—H6B···Cg1ii	0.93	2.83	3.568 (17)	137
C6B—H6B···Cg2ii	0.93	2.94	3.652 (17)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.90	2.721 (3)	176
C6B—H6B⋯Cg1ii	0.93	2.83	3.568 (17)	137
C6B—H6B⋯Cg2ii	0.93	2.94	3.652 (17)	134

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.