(S)-2-[1-(4-Bromo-phen-yl)-1-hy-droxy-ethyl]-5,5-dimethyl-1,3,2-dioxaphos-phinane 2-oxide.

In the crystal structure of the title mol-ecule, C(13)H(18)BrO(4)P, the phospho-nate ring adopts a chair conformation. Mol-ecules are linked by an O-H⋯O hydrogen bond [O⋯O = 2.780 (3) Å] to form chains parallel to the c axis. Two C-H⋯O inter-actions help to stabilize the crystal structure.

Related literature

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

Experimental

Crystal data

C13H18BrO4P

M = 349.15

Orthorhombic,

a = 11.0662 (17) Å

b = 11.3149 (18) Å

c = 11.9609 (19) Å

V = 1497.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.86 mm−1

T = 298 K

0.20 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

10072 measured reflections

3627 independent reflections

2691 reflections with I > 2σ(I)

R int = 0.114

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.105

S = 0.93

3627 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.45 e Å−3

Absolute structure: Flack (1983 ▶), with 1517 Friedel pairs

Flack parameter: −0.011 (10)

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 and SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020587/qk2003sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020587/qk2003Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020587/qk2003Isup3.cml

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

C13H18BrO4P	F(000) = 712
Mr = 349.15	Dx = 1.549 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3882 reflections
a = 11.0662 (17) Å	θ = 2.5–26.7°
b = 11.3149 (18) Å	µ = 2.86 mm−1
c = 11.9609 (19) Å	T = 298 K
V = 1497.7 (4) Å3	Block, colourless
Z = 4	0.20 × 0.12 × 0.10 mm

Bruker SMART APEX CCD area-detector diffractometer	2691 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.114
graphite	θmax = 28.3°, θmin = 2.5°
φ and ω scans	h = −14→14
10072 measured reflections	k = −14→14
3627 independent reflections	l = −15→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0423P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max = 0.001
3627 reflections	Δρmax = 0.46 e Å−3
176 parameters	Δρmin = −0.45 e Å−3
0 restraints	Absolute structure: Flack (1983), with 1517 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.011 (10)

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
Br1	−0.07457 (4)	0.16872 (4)	0.69930 (5)	0.0869 (2)
C1	0.0650 (3)	0.2689 (3)	0.7001 (3)	0.0535 (8)
C2	0.0982 (3)	0.3216 (3)	0.7973 (3)	0.0533 (8)
H2	0.0520	0.3113	0.8615	0.064*
C3	0.2007 (3)	0.3905 (3)	0.8000 (3)	0.0429 (7)
H3	0.2244	0.4250	0.8671	0.052*
C4	0.2690 (2)	0.4094 (2)	0.7050 (3)	0.0373 (6)
C5	0.2317 (3)	0.3561 (3)	0.6058 (3)	0.0498 (8)
H5	0.2762	0.3679	0.5408	0.060*
C6	0.1288 (3)	0.2857 (3)	0.6026 (3)	0.0542 (9)
H6	0.1037	0.2507	0.5362	0.065*
C7	0.3824 (3)	0.4854 (2)	0.7128 (3)	0.0364 (6)
C8	0.4129 (4)	0.5472 (3)	0.6033 (3)	0.0557 (9)
H8A	0.3464	0.5965	0.5813	0.084*
H8B	0.4277	0.4892	0.5464	0.084*
H8C	0.4838	0.5949	0.6133	0.084*
C9	0.5250 (3)	0.4228 (4)	0.9724 (3)	0.0608 (10)
H9A	0.5186	0.3769	1.0406	0.073*
H9B	0.4712	0.4902	0.9791	0.073*
C10	0.6530 (3)	0.4663 (4)	0.9596 (3)	0.0598 (10)
C11	0.6616 (3)	0.5380 (3)	0.8524 (3)	0.0544 (9)
H11A	0.6113	0.6079	0.8592	0.065*
H11B	0.7444	0.5638	0.8419	0.065*
C12	0.6801 (5)	0.5486 (6)	1.0566 (4)	0.1081 (19)
H12A	0.6297	0.6174	1.0514	0.162*
H12B	0.7635	0.5720	1.0540	0.162*
H12C	0.6644	0.5085	1.1258	0.162*
C13	0.7422 (4)	0.3633 (4)	0.9547 (5)	0.0885 (15)
H13A	0.7281	0.3112	1.0167	0.133*
H13B	0.8233	0.3932	0.9585	0.133*
H13C	0.7314	0.3208	0.8860	0.133*
O1	0.36447 (19)	0.56809 (16)	0.80211 (19)	0.0426 (5)
H1	0.3995	0.6301	0.7874	0.064*
O2	0.5245 (2)	0.28766 (19)	0.6800 (2)	0.0596 (6)
O3	0.48668 (19)	0.34977 (18)	0.8773 (2)	0.0497 (5)
O4	0.6236 (2)	0.4709 (2)	0.7554 (2)	0.0520 (6)
P1	0.50921 (6)	0.38934 (6)	0.75398 (7)	0.03831 (18)

	U11	U22	U33	U12	U13	U23
Br1	0.0855 (3)	0.0813 (3)	0.0938 (3)	−0.0491 (2)	−0.0168 (3)	0.0076 (2)
C1	0.0510 (16)	0.0373 (14)	0.072 (2)	−0.0124 (14)	−0.013 (2)	0.0034 (18)
C2	0.0555 (18)	0.0470 (16)	0.057 (2)	−0.0092 (15)	0.0010 (18)	0.0093 (18)
C3	0.0469 (15)	0.0378 (14)	0.0441 (16)	−0.0061 (13)	−0.0027 (15)	−0.0018 (16)
C4	0.0366 (13)	0.0287 (12)	0.0464 (16)	0.0067 (11)	−0.0042 (14)	−0.0006 (13)
C5	0.0528 (17)	0.0502 (19)	0.0464 (18)	0.0022 (17)	−0.0007 (15)	−0.0032 (16)
C6	0.0547 (18)	0.0492 (18)	0.059 (2)	−0.0037 (18)	−0.0127 (18)	−0.0109 (17)
C7	0.0373 (13)	0.0317 (12)	0.0400 (15)	0.0021 (11)	−0.0015 (13)	−0.0030 (12)
C8	0.064 (2)	0.0477 (17)	0.055 (2)	−0.0051 (19)	0.0061 (18)	0.0061 (16)
C9	0.0599 (19)	0.077 (2)	0.0454 (19)	0.006 (2)	−0.0014 (17)	0.0083 (18)
C10	0.0461 (17)	0.067 (2)	0.067 (2)	0.0070 (18)	−0.0158 (18)	−0.002 (2)
C11	0.0437 (16)	0.0476 (19)	0.072 (2)	−0.0055 (15)	−0.0129 (17)	−0.0052 (18)
C12	0.104 (4)	0.146 (5)	0.074 (3)	−0.010 (4)	−0.031 (3)	−0.029 (4)
C13	0.063 (2)	0.079 (3)	0.124 (4)	0.015 (2)	−0.022 (3)	0.020 (3)
O1	0.0476 (11)	0.0263 (9)	0.0540 (13)	−0.0040 (8)	0.0070 (11)	−0.0088 (10)
O2	0.0618 (13)	0.0404 (11)	0.0768 (17)	0.0148 (12)	−0.0035 (13)	−0.0178 (11)
O3	0.0441 (10)	0.0430 (11)	0.0619 (13)	−0.0006 (11)	−0.0005 (11)	0.0105 (10)
O4	0.0416 (10)	0.0596 (13)	0.0548 (13)	−0.0138 (11)	0.0053 (11)	−0.0026 (12)
P1	0.0339 (3)	0.0299 (3)	0.0511 (4)	0.0027 (3)	0.0014 (3)	−0.0047 (3)

Br1—C1	1.915 (3)	C9—C10	1.508 (5)
C1—C2	1.357 (5)	C9—H9A	0.9700
C1—C6	1.377 (5)	C9—H9B	0.9700
C2—C3	1.377 (4)	C10—C12	1.518 (7)
C2—H2	0.9300	C10—C11	1.520 (5)
C3—C4	1.382 (5)	C10—C13	1.528 (5)
C3—H3	0.9300	C11—O4	1.449 (4)
C4—C5	1.393 (5)	C11—H11A	0.9700
C4—C7	1.524 (4)	C11—H11B	0.9700
C5—C6	1.391 (5)	C12—H12A	0.9600
C5—H5	0.9300	C12—H12B	0.9600
C6—H6	0.9300	C12—H12C	0.9600
C7—O1	1.434 (4)	C13—H13A	0.9600
C7—C8	1.522 (5)	C13—H13B	0.9600
C7—P1	1.842 (3)	C13—H13C	0.9600
C8—H8A	0.9600	O1—H1	0.8200
C8—H8B	0.9600	O2—P1	1.461 (2)
C8—H8C	0.9600	O3—P1	1.562 (2)
C9—O3	1.469 (4)	O4—P1	1.566 (2)
C2—C1—C6	121.7 (3)	H9A—C9—H9B	107.9
C2—C1—Br1	118.9 (3)	C9—C10—C12	107.9 (4)
C6—C1—Br1	119.4 (3)	C9—C10—C11	108.6 (3)
C1—C2—C3	119.5 (3)	C12—C10—C11	107.8 (4)
C1—C2—H2	120.3	C9—C10—C13	111.3 (3)
C3—C2—H2	120.3	C12—C10—C13	111.7 (4)
C2—C3—C4	121.3 (3)	C11—C10—C13	109.6 (3)
C2—C3—H3	119.4	O4—C11—C10	112.2 (3)
C4—C3—H3	119.4	O4—C11—H11A	109.2
C3—C4—C5	118.1 (3)	C10—C11—H11A	109.2
C3—C4—C7	119.2 (3)	O4—C11—H11B	109.2
C5—C4—C7	122.7 (3)	C10—C11—H11B	109.2
C6—C5—C4	120.9 (3)	H11A—C11—H11B	107.9
C6—C5—H5	119.5	C10—C12—H12A	109.5
C4—C5—H5	119.5	C10—C12—H12B	109.5
C1—C6—C5	118.4 (3)	H12A—C12—H12B	109.5
C1—C6—H6	120.8	C10—C12—H12C	109.5
C5—C6—H6	120.8	H12A—C12—H12C	109.5
O1—C7—C8	111.8 (2)	H12B—C12—H12C	109.5
O1—C7—C4	107.5 (2)	C10—C13—H13A	109.5
C8—C7—C4	112.9 (3)	C10—C13—H13B	109.5
O1—C7—P1	106.92 (19)	H13A—C13—H13B	109.5
C8—C7—P1	109.4 (2)	C10—C13—H13C	109.5
C4—C7—P1	108.11 (18)	H13A—C13—H13C	109.5
C7—C8—H8A	109.5	H13B—C13—H13C	109.5
C7—C8—H8B	109.5	C7—O1—H1	109.5
H8A—C8—H8B	109.5	C9—O3—P1	121.6 (2)
C7—C8—H8C	109.5	C11—O4—P1	123.5 (2)
H8A—C8—H8C	109.5	O2—P1—O3	111.41 (14)
H8B—C8—H8C	109.5	O2—P1—O4	112.12 (14)
O3—C9—C10	112.1 (3)	O3—P1—O4	106.72 (12)
O3—C9—H9A	109.2	O2—P1—C7	112.97 (13)
C10—C9—H9A	109.2	O3—P1—C7	107.47 (13)
O3—C9—H9B	109.2	O4—P1—C7	105.74 (13)
C10—C9—H9B	109.2
C6—C1—C2—C3	−2.4 (5)	C12—C10—C11—O4	−173.3 (4)
Br1—C1—C2—C3	177.7 (2)	C13—C10—C11—O4	65.0 (4)
C1—C2—C3—C4	1.6 (5)	C10—C9—O3—P1	−47.2 (4)
C2—C3—C4—C5	−0.3 (4)	C10—C11—O4—P1	43.1 (4)
C2—C3—C4—C7	−179.4 (3)	C9—O3—P1—O2	150.2 (2)
C3—C4—C5—C6	−0.2 (4)	C9—O3—P1—O4	27.5 (3)
C7—C4—C5—C6	178.8 (3)	C9—O3—P1—C7	−85.6 (2)
C2—C1—C6—C5	1.8 (5)	C11—O4—P1—O2	−148.2 (2)
Br1—C1—C6—C5	−178.3 (2)	C11—O4—P1—O3	−25.9 (3)
C4—C5—C6—C1	−0.5 (5)	C11—O4—P1—C7	88.3 (3)
C3—C4—C7—O1	−28.2 (3)	O1—C7—P1—O2	169.99 (19)
C5—C4—C7—O1	152.7 (3)	C8—C7—P1—O2	−68.8 (2)
C3—C4—C7—C8	−152.0 (3)	C4—C7—P1—O2	54.6 (2)
C5—C4—C7—C8	29.0 (4)	O1—C7—P1—O3	46.7 (2)
C3—C4—C7—P1	86.8 (3)	C8—C7—P1—O3	167.9 (2)
C5—C4—C7—P1	−92.2 (3)	C4—C7—P1—O3	−68.8 (2)
O3—C9—C10—C12	175.4 (4)	O1—C7—P1—O4	−67.0 (2)
O3—C9—C10—C11	58.9 (4)	C8—C7—P1—O4	54.2 (2)
O3—C9—C10—C13	−61.8 (4)	C4—C7—P1—O4	177.5 (2)
C9—C10—C11—O4	−56.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	2.01	2.780 (3)	156.
C9—H9B···O1	0.97	2.58	3.163 (4)	119.
C11—H11A···O2i	0.97	2.57	3.517 (4)	165.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	2.01	2.780 (3)	156
C9—H9B⋯O1	0.97	2.58	3.163 (4)	119
C11—H11A⋯O2i	0.97	2.57	3.517 (4)	165

Symmetry code: (i) .