(S)-2-[1-(4-Bromo­phen­yl)-1-hy­droxy­ethyl]-5,5-dimethyl-1,3,2-dioxaphos­phinane 2-oxide

Wang, C.; Peng, H.; He, H.

doi:10.1107/S1600536811020587

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1739

doi:10.1107/S1600536811020587

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(S)-2-[1-(4-Bromophenyl)-1-hydroxyethyl]-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide

Chubei Wang,^a Hao Peng ^a and Hongwu He ^a ^*

^aKey Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
^*Correspondence e-mail: he1208@mail.ccnu.edu.cn

(Received 5 March 2011; accepted 29 May 2011; online 18 June 2011)

In the crystal structure of the title molecule, C₁₃H₁₈BrO₄P, the phosphonate ring adopts a chair conformation. Molecules 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 interactions 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_r = 349.15
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.105
S = 0.93
3627 reflections
176 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.45 e Å⁻³
Absolute structure: Flack (1983 ), with 1517 Friedel pairs
Flack parameter: −0.011 (10)

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020587/qk2003sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811020587/qk2003Isup3.cml

checkCIF report

Comment top

Acyclic and cyclic α-hydroxyphosphonates can be used as very viable intermediates and they are also an attractive class of biologically active compounds (Peng et al., 2007; Liu et al., 2006). In our research work aimed at searching for novel agrochemicals, we attempted to synthesize hydroxyphosphonates according to published literature procedures. Here we report the synthesis and crystal structure of the chiral title compound (I) (Fig. 1). The bond lengths and angles show normal values (Allen et al., 1987). In the crystal structure, the cyclic phosphonate ring adopts a chair conformation.

Related literature top

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 top

Hydroxyphosphonate (I) was prepared according to a literature procedure (Zhou et al., 2008). Diethylaluminium chloride (1 mmol) was added to a solution of (S,E)-2-(adamantan-1-yl)-4-(tert-butyl)-6(((1-hydroxy-3-methylbutan-2-yl)imino)methyl)-phenol (1 mmol) in dichloromethane (10 ml). The mixture was stirred at room temperature for 1 h. The ketone (11 mmol) and the cyclic phosphate (10 mmol) were added and the mixture was stirred for 2 h. The reaction was quenched by diluted hydrochloric acid (15:1, v/v). The pure hydroxyphosphonate was afforded by column chromatography on silica gel (acetone/petroleum ether = 1:2), 71% yield, [α]_D = -64.8 ° (c = 0.56, chloroform). Then recrystallization from acetic ester over a period of one week gave colourless crystals of (I).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Spek, 2009) and SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the labeling scheme and 50% probability thermal ellipsoids.
	Fig. 2. Part of the crystal packing, showing the intermolecular hydrogen bonds as dashed lines.

(S)-2-[1-(4-Bromophenyl)-1-hydroxyethyl]-5,5-dimethyl-1,3,2- dioxaphosphinane 2-oxide top

Crystal data top

C₁₃H₁₈BrO₄P	F(000) = 712
M_r = 349.15	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0423P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max = 0.001
3627 reflections	Δρ_max = 0.46 e Å⁻³
176 parameters	Δρ_min = −0.45 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 1517 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.011 (10)

Crystal data top

C₁₃H₁₈BrO₄P	V = 1497.7 (4) Å³
M_r = 349.15	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.0662 (17) Å	µ = 2.86 mm⁻¹
b = 11.3149 (18) Å	T = 298 K
c = 11.9609 (19) Å	0.20 × 0.12 × 0.10 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2691 reflections with I > 2σ(I)
10072 measured reflections	R_int = 0.114
3627 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.105	Δρ_max = 0.46 e Å⁻³
S = 0.93	Δρ_min = −0.45 e Å⁻³
3627 reflections	Absolute structure: Flack (1983), with 1517 Friedel pairs
176 parameters	Absolute structure parameter: −0.011 (10)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₈BrO₄P
M_r	349.15
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	11.0662 (17), 11.3149 (18), 11.9609 (19)
V (Å³)	1497.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.86
Crystal size (mm)	0.20 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10072, 3627, 2691
R_int	0.114
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.105, 0.93
No. of reflections	3627
No. of parameters	176
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.45
Absolute structure	Flack (1983), with 1517 Friedel pairs
Absolute structure parameter	−0.011 (10)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.01	2.780 (3)	156.2
C9—H9B···O1	0.97	2.58	3.163 (4)	118.8
C11—H11A···O2ⁱ	0.97	2.57	3.517 (4)	164.6

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors gratefully acknowledge the financial support of this work by the National Basic Research Program of China (grant No. 2010CB126100) and the National Natural Science Foundation of China (grant No. 20772042,21002037). This work was supported in part by the PCSIRT (grant No. IRT0953).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, H., Zhou, Y. G., Yu, Z. K., Xiao, W. J., Liu, S. H. & He, H. W. (2006). Tetrahedron Lett. 62, 11207–11217. CrossRef CAS Google Scholar
Peng, H., Wang, T., Xie, P., Chen, T., He, H. W. & Wan, J. (2007). J. Agric. Food Chem. 55, 1871–1880. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, X., Liu, X. H., Yang, X., Shang, D. J., Xin, J. G. & Feng, X. M. (2008). Angew. Chem. Int. Ed. 47, 392–394. CrossRef CAS Google Scholar

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Volume 67| Part 7| July 2011| Page o1739

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(S)-2-[1-(4-Bromo­phen­yl)-1-hy­dr­oxy­ethyl]-5,5-di­methyl-1,3,2-dioxaphos­phinane 2-oxide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(S)-2-[1-(4-Bromophenyl)-1-hydroxyethyl]-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide