2-[(4-Chloro-phen-yl)(hy-droxy)meth-yl]-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one.

In the title compound, C(12)H(16)ClO(4)P, the phospho-nate ring adopts a chair conformation. In the crystal, intermolecular O-H⋯O hydrogen bonds link the molecules into chains propagating along the b axis.

Related literature

For the synthesis of hy­droxy­phospho­nates, see: Zhou et al. (2008 ▶). For the synthesis and biological activity of hy­droxy­phospho­nate derivatives, see: Peng et al. (2007 ▶); Liu et al. (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H16ClO4P

M = 290.67

Monoclinic,

a = 12.8965 (11) Å

b = 9.4449 (8) Å

c = 11.6425 (10) Å

β = 98.630 (1)°

V = 1402.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 298 K

0.23 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

10123 measured reflections

3463 independent reflections

3141 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.154

S = 1.15

3463 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008944/wn2424sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008944/wn2424Isup2.hkl

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

C12H16ClO4P	F(000) = 608
Mr = 290.67	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8965 (11) Å	Cell parameters from 4935 reflections
b = 9.4449 (8) Å	θ = 2.7–28.2°
c = 11.6425 (10) Å	µ = 0.39 mm−1
β = 98.630 (1)°	T = 298 K
V = 1402.1 (2) Å3	Block, colourless
Z = 4	0.23 × 0.16 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	3141 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
graphite	θmax = 28.3°, θmin = 2.7°
φ and ω scans	h = −13→17
10123 measured reflections	k = −9→12
3463 independent reflections	l = −15→15

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.7742P] where P = (Fo2 + 2Fc2)/3
3463 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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. 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
C1	0.2944 (2)	0.3005 (3)	0.5354 (2)	0.0543 (6)
H1A	0.2923	0.3256	0.6150	0.081*
H1B	0.3596	0.3312	0.5135	0.081*
H1C	0.2883	0.1996	0.5267	0.081*
C2	0.2096 (3)	0.5330 (3)	0.4720 (3)	0.0635 (8)
H2A	0.1547	0.5765	0.4188	0.095*
H2B	0.2764	0.5659	0.4561	0.095*
H2C	0.2014	0.5577	0.5501	0.095*
C3	0.2035 (2)	0.3720 (2)	0.4576 (2)	0.0407 (5)
C4	0.2059 (2)	0.3377 (2)	0.3303 (2)	0.0430 (5)
H4A	0.1519	0.3917	0.2823	0.052*
H4B	0.2733	0.3655	0.3099	0.052*
C5	0.09896 (19)	0.3251 (2)	0.4897 (2)	0.0429 (5)
H5A	0.0971	0.3465	0.5708	0.052*
H5B	0.0428	0.3773	0.4434	0.052*
C6	0.12155 (17)	−0.0698 (2)	0.36460 (19)	0.0359 (4)
H6	0.0632	−0.1171	0.3939	0.043*
C7	0.21964 (16)	−0.09498 (19)	0.44979 (18)	0.0330 (4)
C8	0.31652 (19)	−0.1076 (3)	0.4118 (2)	0.0432 (5)
H8	0.3212	−0.0978	0.3333	0.052*
C9	0.4058 (2)	−0.1346 (3)	0.4902 (3)	0.0550 (6)
H9	0.4705	−0.1435	0.4647	0.066*
C10	0.3983 (2)	−0.1482 (3)	0.6055 (3)	0.0554 (7)
C11	0.3035 (2)	−0.1347 (3)	0.6457 (2)	0.0509 (6)
H11	0.2996	−0.1430	0.7245	0.061*
C12	0.21483 (19)	−0.1088 (2)	0.5673 (2)	0.0422 (5)
H12	0.1505	−0.1004	0.5936	0.051*
Cl1	0.51070 (8)	−0.18286 (16)	0.70446 (9)	0.1062 (4)
O1	0.18909 (13)	0.18663 (16)	0.30702 (13)	0.0403 (4)
O2	0.08252 (12)	0.17262 (17)	0.46986 (13)	0.0402 (4)
O3	−0.00798 (14)	0.1404 (2)	0.26116 (16)	0.0537 (5)
O4	0.12788 (16)	−0.12340 (19)	0.25263 (15)	0.0526 (5)
H4	0.0926	−0.1957	0.2418	0.079*
P1	0.08858 (4)	0.11632 (6)	0.34372 (5)	0.03362 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0489 (14)	0.0561 (16)	0.0541 (14)	−0.0019 (12)	−0.0045 (11)	0.0008 (12)
C2	0.088 (2)	0.0332 (12)	0.0674 (17)	−0.0063 (13)	0.0042 (16)	−0.0104 (12)
C3	0.0505 (13)	0.0286 (10)	0.0416 (11)	−0.0025 (9)	0.0024 (10)	−0.0031 (8)
C4	0.0560 (14)	0.0298 (10)	0.0439 (12)	−0.0069 (10)	0.0099 (10)	0.0024 (9)
C5	0.0511 (13)	0.0373 (11)	0.0411 (11)	0.0065 (10)	0.0093 (10)	−0.0078 (9)
C6	0.0345 (10)	0.0291 (9)	0.0438 (11)	−0.0071 (8)	0.0048 (8)	−0.0022 (8)
C7	0.0356 (10)	0.0188 (8)	0.0442 (11)	−0.0014 (7)	0.0045 (8)	0.0004 (7)
C8	0.0402 (12)	0.0439 (12)	0.0463 (12)	−0.0019 (10)	0.0096 (10)	0.0011 (10)
C9	0.0366 (12)	0.0619 (17)	0.0668 (16)	0.0031 (11)	0.0087 (11)	0.0032 (13)
C10	0.0442 (14)	0.0571 (16)	0.0606 (16)	0.0052 (12)	−0.0060 (11)	0.0079 (13)
C11	0.0615 (16)	0.0483 (14)	0.0421 (12)	0.0045 (12)	0.0049 (11)	0.0084 (10)
C12	0.0419 (12)	0.0384 (12)	0.0476 (12)	0.0039 (9)	0.0114 (10)	0.0043 (9)
Cl1	0.0629 (6)	0.1541 (11)	0.0912 (7)	0.0175 (6)	−0.0221 (5)	0.0266 (7)
O1	0.0520 (9)	0.0310 (8)	0.0412 (8)	−0.0050 (7)	0.0175 (7)	−0.0022 (6)
O2	0.0435 (9)	0.0373 (8)	0.0423 (8)	0.0009 (7)	0.0150 (7)	−0.0016 (6)
O3	0.0485 (10)	0.0528 (10)	0.0546 (10)	0.0105 (8)	−0.0089 (8)	0.0022 (8)
O4	0.0622 (12)	0.0444 (10)	0.0503 (10)	−0.0086 (8)	0.0054 (8)	−0.0130 (8)
P1	0.0342 (3)	0.0304 (3)	0.0358 (3)	0.0021 (2)	0.0039 (2)	0.0004 (2)

C1—C3	1.528 (3)	C6—P1	1.816 (2)
C1—H1A	0.9600	C6—H6	0.9800
C1—H1B	0.9600	C7—C12	1.385 (3)
C1—H1C	0.9600	C7—C8	1.392 (3)
C2—C3	1.530 (3)	C8—C9	1.382 (3)
C2—H2A	0.9600	C8—H8	0.9300
C2—H2B	0.9600	C9—C10	1.367 (4)
C2—H2C	0.9600	C9—H9	0.9300
C3—C5	1.518 (3)	C10—C11	1.379 (4)
C3—C4	1.522 (3)	C10—Cl1	1.742 (3)
C4—O1	1.463 (3)	C11—C12	1.373 (3)
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	C12—H12	0.9300
C5—O2	1.469 (3)	O1—P1	1.5716 (16)
C5—H5A	0.9700	O2—P1	1.5748 (16)
C5—H5B	0.9700	O3—P1	1.4721 (18)
C6—O4	1.412 (3)	O4—H4	0.8200
C6—C7	1.505 (3)
C3—C1—H1A	109.5	C7—C6—P1	113.47 (14)
C3—C1—H1B	109.5	O4—C6—H6	108.2
H1A—C1—H1B	109.5	C7—C6—H6	108.2
C3—C1—H1C	109.5	P1—C6—H6	108.2
H1A—C1—H1C	109.5	C12—C7—C8	118.8 (2)
H1B—C1—H1C	109.5	C12—C7—C6	120.54 (19)
C3—C2—H2A	109.5	C8—C7—C6	120.7 (2)
C3—C2—H2B	109.5	C9—C8—C7	120.4 (2)
H2A—C2—H2B	109.5	C9—C8—H8	119.8
C3—C2—H2C	109.5	C7—C8—H8	119.8
H2A—C2—H2C	109.5	C10—C9—C8	119.4 (2)
H2B—C2—H2C	109.5	C10—C9—H9	120.3
C5—C3—C4	109.08 (19)	C8—C9—H9	120.3
C5—C3—C1	110.8 (2)	C9—C10—C11	121.5 (2)
C4—C3—C1	110.9 (2)	C9—C10—Cl1	119.5 (2)
C5—C3—C2	107.2 (2)	C11—C10—Cl1	119.0 (2)
C4—C3—C2	108.0 (2)	C12—C11—C10	118.9 (2)
C1—C3—C2	110.6 (2)	C12—C11—H11	120.6
O1—C4—C3	111.34 (17)	C10—C11—H11	120.6
O1—C4—H4A	109.4	C11—C12—C7	121.1 (2)
C3—C4—H4A	109.4	C11—C12—H12	119.4
O1—C4—H4B	109.4	C7—C12—H12	119.4
C3—C4—H4B	109.4	C4—O1—P1	117.87 (14)
H4A—C4—H4B	108.0	C5—O2—P1	116.83 (14)
O2—C5—C3	111.10 (17)	C6—O4—H4	109.5
O2—C5—H5A	109.4	O3—P1—O1	114.12 (11)
C3—C5—H5A	109.4	O3—P1—O2	113.65 (10)
O2—C5—H5B	109.4	O1—P1—O2	105.62 (9)
C3—C5—H5B	109.4	O3—P1—C6	113.27 (10)
H5A—C5—H5B	108.0	O1—P1—C6	105.02 (9)
O4—C6—C7	113.10 (18)	O2—P1—C6	104.20 (9)
O4—C6—P1	105.57 (15)
C5—C3—C4—O1	−57.7 (3)	C10—C11—C12—C7	−0.6 (4)
C1—C3—C4—O1	64.7 (3)	C8—C7—C12—C11	−0.1 (3)
C2—C3—C4—O1	−173.9 (2)	C6—C7—C12—C11	178.7 (2)
C4—C3—C5—O2	58.9 (2)	C3—C4—O1—P1	54.0 (2)
C1—C3—C5—O2	−63.5 (2)	C3—C5—O2—P1	−56.2 (2)
C2—C3—C5—O2	175.7 (2)	C4—O1—P1—O3	80.51 (18)
O4—C6—C7—C12	−151.46 (19)	C4—O1—P1—O2	−45.05 (18)
P1—C6—C7—C12	88.3 (2)	C4—O1—P1—C6	−154.86 (16)
O4—C6—C7—C8	27.3 (3)	C5—O2—P1—O3	−79.99 (18)
P1—C6—C7—C8	−92.9 (2)	C5—O2—P1—O1	45.86 (17)
C12—C7—C8—C9	0.5 (3)	C5—O2—P1—C6	156.25 (16)
C6—C7—C8—C9	−178.2 (2)	O4—C6—P1—O3	56.16 (18)
C7—C8—C9—C10	−0.3 (4)	C7—C6—P1—O3	−179.45 (15)
C8—C9—C10—C11	−0.4 (5)	O4—C6—P1—O1	−69.01 (15)
C8—C9—C10—Cl1	179.8 (2)	C7—C6—P1—O1	55.38 (17)
C9—C10—C11—C12	0.8 (4)	O4—C6—P1—O2	−179.83 (14)
Cl1—C10—C11—C12	−179.3 (2)	C7—C6—P1—O2	−55.44 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	1.89	2.705 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	1.89	2.705 (3)	172

Symmetry code: (i) .