Diethyl [hydr-oxy(phen-yl)meth-yl]phospho-nate.

Mol-ecules of the title compound, C(11)H(17)O(4)P, are linked into chiral helical chains along the crystallographic b axis via O-H⋯O hydrogen bonds between the hydr-oxy group and an O atom of the phospho-nate group. One ethyl group is disordered over two positions; the site occupancy factors are ca 0.7 and 0.3.

Related literature

For related literature, see: Fang et al. (2006a ▶,b ▶,c ▶, 2007 ▶); Kaboudin (2000 ▶); Maier & Diel (1994 ▶); Stowasser et al. (1992 ▶).

Experimental

Crystal data

C11H17O4P

M = 244.22

Monoclinic,

a = 9.2361 (6) Å

b = 8.0719 (5) Å

c = 17.4599 (13) Å

β = 95.096 (5)°

V = 1296.54 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 (2) K

0.30 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.940, T max = 0.959

10679 measured reflections

2345 independent reflections

1723 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.174

S = 1.07

2345 reflections

168 parameters

48 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018424/rk2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018424/rk2099Isup2.hkl

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

C11H17O4P	Z = 4
Mr = 244.22	F000 = 520
Monoclinic, P21/n	Dx = 1.251 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 9.2361 (6) Å	θ = 2.3–25.2º
b = 8.0719 (5) Å	µ = 0.21 mm−1
c = 17.4599 (13) Å	T = 296 (2) K
β = 95.096 (5)º	Prism, colourless
V = 1296.54 (15) Å3	0.30 × 0.30 × 0.20 mm

Rigaku Mercury diffractometer	2345 independent reflections
Radiation source: Fine–focus sealed tube	1723 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.030
Detector resolution: 7.31 pixels mm-1	θmax = 25.2º
T = 296(2) K	θmin = 2.3º
ω scans	h = −11→11
Absorption correction: multi-scan(Jacobson, 1998)	k = −9→8
Tmin = 0.940, Tmax = 0.959	l = −17→20
10679 measured reflections

Refinement on F2	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.1001P)2 + 0.236P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2345 reflections	Δρmax = 0.38 e Å−3
168 parameters	Δρmin = −0.34 e Å−3
48 restraints	Extinction correction: none
Primary atom site location: Direct

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.0039 (3)	0.8100 (3)	0.27207 (16)	0.0699 (7)
C2	−0.1128 (4)	0.9141 (5)	0.2543 (2)	0.0945 (10)
H2	−0.1080	0.9916	0.2152	0.113*
C3	−0.2344 (5)	0.9061 (6)	0.2925 (3)	0.1194 (14)
H3	−0.3115	0.9773	0.2789	0.143*
C4	−0.2447 (5)	0.7966 (7)	0.3498 (3)	0.1225 (15)
H4	−0.3278	0.7927	0.3761	0.147*
C5	−0.1305 (5)	0.6901 (6)	0.3689 (2)	0.1170 (14)
H5	−0.1370	0.6138	0.4084	0.140*
C6	−0.0049 (4)	0.6957 (4)	0.3296 (2)	0.0888 (10)
H6	0.0716	0.6229	0.3423	0.107*
C7	0.1365 (3)	0.8216 (3)	0.22835 (17)	0.0700 (7)
H7	0.1517	0.9376	0.2146	0.084*
C8	−0.0806 (5)	0.7118 (5)	0.0237 (2)	0.1202 (15)
H8A	−0.0072	0.6701	−0.0078	0.144*
H8B	−0.1403	0.6191	0.0370	0.144*
C9	−0.1684 (5)	0.8298 (5)	−0.0188 (2)	0.1294 (16)
H9A	−0.2427	0.8689	0.0118	0.194*
H9B	−0.2128	0.7791	−0.0648	0.194*
H9C	−0.1093	0.9213	−0.0322	0.194*
C10	0.3970 (12)	0.693 (3)	0.1245 (10)	0.128 (2)	0.273 (7)
H10A	0.3922	0.6073	0.1630	0.153*	0.273 (7)
H10B	0.4512	0.7864	0.1477	0.153*	0.273 (7)
C11	0.4683 (18)	0.629 (2)	0.0560 (10)	0.131 (2)	0.273 (7)
H11A	0.4753	0.7168	0.0194	0.197*	0.273 (7)
H11B	0.4110	0.5404	0.0325	0.197*	0.273 (7)
H11C	0.5638	0.5889	0.0725	0.197*	0.273 (7)
C10'	0.3723 (5)	0.6344 (7)	0.0883 (5)	0.122 (2)	0.727 (7)
H10C	0.3621	0.5770	0.0394	0.147*	0.727 (7)
H10D	0.3777	0.5529	0.1293	0.147*	0.727 (7)
C11'	0.5025 (6)	0.7386 (9)	0.0942 (5)	0.136 (2)	0.727 (7)
H11D	0.4976	0.8149	0.0518	0.204*	0.727 (7)
H11E	0.5872	0.6700	0.0928	0.204*	0.727 (7)
H11F	0.5081	0.7992	0.1416	0.204*	0.727 (7)
O1	0.2648 (2)	0.7606 (3)	0.26977 (14)	0.0876 (7)
H1	0.3101	0.8380	0.2908	0.131*
O2	0.1031 (2)	0.5201 (2)	0.15362 (11)	0.0787 (6)
O3	−0.0104 (2)	0.7844 (3)	0.09335 (11)	0.0889 (7)
O4	0.2499 (3)	0.7456 (3)	0.09497 (16)	0.1077 (8)
P1	0.11894 (8)	0.69802 (9)	0.14126 (4)	0.0710 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0760 (17)	0.0661 (16)	0.0641 (15)	0.0012 (13)	−0.0139 (13)	−0.0117 (12)
C2	0.097 (2)	0.101 (2)	0.084 (2)	0.0294 (19)	0.0000 (18)	−0.0047 (17)
C3	0.100 (3)	0.146 (4)	0.111 (3)	0.030 (3)	0.002 (2)	−0.027 (3)
C4	0.107 (3)	0.144 (4)	0.119 (3)	−0.012 (3)	0.027 (3)	−0.048 (3)
C5	0.143 (4)	0.119 (3)	0.091 (3)	−0.029 (3)	0.022 (3)	−0.005 (2)
C6	0.102 (2)	0.080 (2)	0.082 (2)	−0.0091 (17)	−0.0077 (19)	0.0029 (16)
C7	0.0726 (16)	0.0543 (14)	0.0788 (17)	0.0010 (12)	−0.0172 (14)	0.0031 (12)
C8	0.125 (3)	0.118 (3)	0.108 (3)	0.018 (2)	−0.044 (3)	−0.014 (2)
C9	0.148 (4)	0.129 (3)	0.100 (3)	0.009 (3)	−0.050 (3)	−0.001 (2)
C10	0.093 (3)	0.113 (5)	0.179 (6)	0.013 (4)	0.031 (4)	0.015 (4)
C11	0.098 (4)	0.117 (5)	0.181 (6)	0.016 (4)	0.031 (4)	0.012 (4)
C10'	0.091 (3)	0.107 (4)	0.173 (6)	0.014 (2)	0.038 (3)	0.016 (3)
C11'	0.101 (3)	0.121 (4)	0.188 (6)	0.007 (3)	0.023 (3)	0.012 (4)
O1	0.0732 (12)	0.0743 (12)	0.1085 (16)	0.0046 (10)	−0.0301 (12)	−0.0079 (12)
O2	0.0826 (13)	0.0656 (12)	0.0845 (13)	0.0092 (9)	−0.0106 (10)	−0.0046 (9)
O3	0.1065 (16)	0.0916 (15)	0.0645 (11)	0.0306 (11)	−0.0157 (11)	−0.0027 (9)
O4	0.1062 (16)	0.0990 (16)	0.1221 (19)	0.0288 (14)	0.0325 (15)	0.0324 (15)
P1	0.0741 (5)	0.0677 (5)	0.0694 (5)	0.0125 (3)	−0.0035 (4)	0.0054 (3)

C1—C6	1.371 (4)	C9—H9B	0.9600
C1—C2	1.380 (4)	C9—H9C	0.9600
C1—C7	1.503 (4)	C10—O4	1.471 (8)
C2—C3	1.358 (5)	C10—C11	1.509 (10)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.344 (7)	C10—H10B	0.9700
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.378 (7)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C5—C6	1.401 (5)	C10'—O4	1.456 (5)
C5—H5	0.9300	C10'—C11'	1.464 (7)
C6—H6	0.9300	C10'—H10C	0.9700
C7—O1	1.420 (3)	C10'—H10D	0.9700
C7—P1	1.814 (3)	C11'—H11D	0.9600
C7—H7	0.9800	C11'—H11E	0.9600
C8—C9	1.418 (5)	C11'—H11F	0.9600
C8—O3	1.450 (4)	O1—H1	0.82
C8—H8A	0.9700	O2—P1	1.462 (2)
C8—H8B	0.9700	O3—P1	1.561 (2)
C9—H9A	0.9600	O4—P1	1.562 (3)
C6—C1—C2	118.6 (3)	H9A—C9—H9B	109.5
C6—C1—C7	121.2 (3)	C8—C9—H9C	109.5
C2—C1—C7	120.2 (3)	H9A—C9—H9C	109.5
C3—C2—C1	121.6 (4)	H9B—C9—H9C	109.5
C3—C2—H2	119.2	O4—C10—C11	105.9 (11)
C1—C2—H2	119.2	O4—C10—H10A	110.5
C4—C3—C2	120.9 (4)	C11—C10—H10A	110.5
C4—C3—H3	119.6	O4—C10—H10B	110.5
C2—C3—H3	119.6	C11—C10—H10B	110.5
C3—C4—C5	119.1 (4)	H10A—C10—H10B	108.7
C3—C4—H4	120.4	O4—C10'—C11'	106.2 (5)
C5—C4—H4	120.4	O4—C10'—H10C	110.5
C4—C5—C6	120.7 (4)	C11'—C10'—H10C	110.5
C4—C5—H5	119.6	O4—C10'—H10D	110.5
C6—C5—H5	119.6	C11'—C10'—H10D	110.5
C1—C6—C5	119.1 (4)	H10C—C10'—H10D	108.7
C1—C6—H6	120.5	C10'—C11'—H11D	109.5
C5—C6—H6	120.5	C10'—C11'—H11E	109.5
O1—C7—C1	113.6 (2)	H11D—C11'—H11E	109.5
O1—C7—P1	104.17 (19)	C10'—C11'—H11F	109.5
C1—C7—P1	112.03 (18)	H11D—C11'—H11F	109.5
O1—C7—H7	109.0	H11E—C11'—H11F	109.5
C1—C7—H7	109.0	C7—O1—H1	109.5
P1—C7—H7	109.0	C8—O3—P1	122.2 (2)
C9—C8—O3	111.1 (3)	C10'—O4—P1	122.1 (3)
C9—C8—H8A	109.4	C10—O4—P1	118.8 (8)
O3—C8—H8A	109.4	O2—P1—O3	115.86 (12)
C9—C8—H8B	109.4	O2—P1—O4	114.24 (13)
O3—C8—H8B	109.4	O3—P1—O4	101.79 (14)
H8A—C8—H8B	108.0	O2—P1—C7	114.79 (12)
C8—C9—H9A	109.5	O3—P1—C7	102.18 (12)
C8—C9—H9B	109.5	O4—P1—C7	106.42 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.90	2.716 (3)	174

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	2.716 (3)	174

Symmetry code: (i) .