(S)-2-[(2,4-Dichloro­phen­yl)(hy­droxy)meth­yl]-5,5-dimethyl-1,3,2-dioxa­phosphinane 2-oxide

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

doi:10.1107/S1600536811009585

organic compounds

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Volume 67| Part 4| April 2011| Page o920

doi:10.1107/S1600536811009585

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(S)-2-[(2,4-Dichlorophenyl)(hydroxy)methyl]-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide

Chubei Wang,^a Hao Peng,^a Xiaosong Tan ^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 3 March 2011; accepted 14 March 2011; online 19 March 2011)

In the title molecule, C₁₂H₁₅Cl₂O₄P, the cyclic dioxaphosphinane 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 and biological activity of hydroxydioxaphosphinane derivatives, see: Peng et al. (2007 ); Liu et al. (2006 ). For the synthesis of chiral cyclic hydroxydioxaphosphinanes, see: Zhou et al. (2008 ).

Experimental

Crystal data

C₁₂H₁₅Cl₂O₄P
M_r = 325.11
Monoclinic, P 2₁
a = 7.0263 (9) Å
b = 9.9443 (13) Å
c = 10.6462 (14) Å
β = 93.975 (2)°
V = 742.08 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 298 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
4069 measured reflections
2597 independent reflections
2478 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.105
S = 1.01
2597 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1140 Friedel pairs
Flack parameter: −0.15 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.80 (5)	1.89 (5)	2.686 (3)	173 (4)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009585/cv5059sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009585/cv5059Isup2.hkl

checkCIF report

Comment top

The cyclic alpha-hydroxydioxaphosphinanes exhibit various biological activities (Peng et al., 2007; Liu et al., 2006). The title compound, (I), is a chiral cyclic hydroxydioxaphosphinane derivative. Herewith we present its crystal structure.

In (I) (Fig. 1), the cyclic dioxaphosphinane ring adopts a chair conformation. In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains propagated along b axis (Fig. 2).

Related literature top

For the synthesis and biological activity of hydroxydioxaphosphinane derivatives, see: Peng et al. (2007); Liu et al. (2006). For the synthesis of chiral cyclic hydroxydioxaphosphinanes, see: Zhou et al. (2008).

Experimental top

The title compound was prepared according to the known procedure (Zhou et al., 2008). Diethylaluminum 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, The mixture was stirred at room temperature for 1 h. The aldehyde and cyclic phosphite was added and the mixture was stirred for another 2 h. The reaction was quenched by diluted hydrochloride acid. The pure title compound was afforded by column chromatography on silica gel (acetone/petroleum ether 1:2). Recrystallization from ethyl acetate over a period of one week gave colourless crystals of the title compound.

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).

Figures top

	Fig. 1. Molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Part of the crystal packing, showing the intermolecular O—H···O hydrogen bonds as dashed lines.

(S)-2-[(2,4-Dichlorophenyl)(hydroxy)methyl]-5,5-dimethyl-1,3,2- dioxaphosphinane 2-oxide top

Crystal data top

C₁₂H₁₅Cl₂O₄P	F(000) = 336
M_r = 325.11	D_x = 1.455 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.0263 (9) Å	Cell parameters from 2185 reflections
b = 9.9443 (13) Å	θ = 2.8–28.1°
c = 10.6462 (14) Å	µ = 0.55 mm⁻¹
β = 93.975 (2)°	T = 298 K
V = 742.08 (17) Å³	Block, colourless
Z = 2	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.067
Graphite monochromator	θ_max = 25.5°, θ_min = 1.9°
ϕ and ω scans	h = −8→8
4069 measured reflections	k = −11→12
2597 independent reflections	l = −12→11

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0604P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2597 reflections	Δρ_max = 0.39 e Å⁻³
177 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1140 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.15 (8)

Crystal data top

C₁₂H₁₅Cl₂O₄P	V = 742.08 (17) Å³
M_r = 325.11	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.0263 (9) Å	µ = 0.55 mm⁻¹
b = 9.9443 (13) Å	T = 298 K
c = 10.6462 (14) Å	0.16 × 0.12 × 0.10 mm
β = 93.975 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2478 reflections with I > 2σ(I)
4069 measured reflections	R_int = 0.067
2597 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	Δρ_max = 0.39 e Å⁻³
S = 1.01	Δρ_min = −0.25 e Å⁻³
2597 reflections	Absolute structure: Flack (1983), 1140 Friedel pairs
177 parameters	Absolute structure parameter: −0.15 (8)
1 restraint

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
C1	1.0374 (4)	0.6151 (3)	0.2326 (3)	0.0326 (6)
C2	1.2166 (4)	0.6199 (3)	0.2946 (3)	0.0353 (6)
C3	1.2552 (5)	0.6911 (4)	0.4050 (3)	0.0426 (7)
H3	1.3771	0.6916	0.4451	0.051*
C4	1.1093 (5)	0.7608 (3)	0.4537 (3)	0.0432 (8)
C5	0.9289 (5)	0.7620 (4)	0.3937 (3)	0.0454 (8)
H5	0.8316	0.8117	0.4264	0.054*
C6	0.8951 (4)	0.6891 (3)	0.2856 (3)	0.0395 (7)
H6	0.7728	0.6890	0.2461	0.047*
C8	0.9910 (4)	0.5319 (3)	0.1163 (3)	0.0330 (6)
H8	1.0894	0.4627	0.1112	0.040*
C9	0.7747 (5)	0.4722 (4)	−0.1830 (3)	0.0461 (8)
H9A	0.7300	0.4104	−0.1209	0.055*
H9B	0.7880	0.4222	−0.2601	0.055*
C10	0.6092 (4)	0.6611 (4)	−0.0866 (3)	0.0439 (8)
H10A	0.5200	0.7344	−0.1037	0.053*
H10B	0.5575	0.6030	−0.0242	0.053*
C11	0.6301 (5)	0.5816 (4)	−0.2073 (3)	0.0456 (8)
C12	0.4368 (6)	0.5156 (6)	−0.2449 (5)	0.0766 (14)
H12A	0.4470	0.4632	−0.3199	0.115*
H12B	0.3418	0.5841	−0.2605	0.115*
H12C	0.4008	0.4583	−0.1780	0.115*
C13	0.6874 (6)	0.6734 (5)	−0.3136 (3)	0.0617 (11)
H13A	0.8071	0.7157	−0.2893	0.093*
H13B	0.5913	0.7411	−0.3297	0.093*
H13C	0.6996	0.6211	−0.3884	0.093*
Cl1	1.40915 (11)	0.53739 (10)	0.23277 (9)	0.0563 (3)
Cl2	1.15586 (17)	0.85446 (12)	0.59048 (10)	0.0703 (3)
O1	0.8112 (3)	0.4671 (2)	0.1240 (2)	0.0404 (5)
H1	0.818 (6)	0.390 (5)	0.102 (4)	0.061*
O2	0.9609 (3)	0.5257 (2)	−0.1376 (2)	0.0425 (5)
O3	0.7922 (3)	0.7156 (2)	−0.0361 (2)	0.0390 (5)
O4	1.1503 (3)	0.7162 (2)	−0.0359 (2)	0.0450 (6)
P1	0.98124 (10)	0.63058 (8)	−0.02830 (7)	0.0317 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0314 (14)	0.0335 (17)	0.0328 (14)	−0.0005 (13)	0.0022 (11)	0.0054 (13)
C2	0.0315 (14)	0.0363 (16)	0.0380 (15)	0.0030 (14)	0.0008 (11)	0.0036 (14)
C3	0.0403 (18)	0.0474 (18)	0.0386 (17)	−0.0026 (15)	−0.0067 (13)	0.0031 (15)
C4	0.055 (2)	0.0433 (19)	0.0312 (16)	−0.0031 (16)	0.0021 (14)	−0.0047 (14)
C5	0.0400 (19)	0.051 (2)	0.0456 (19)	0.0057 (16)	0.0073 (15)	−0.0045 (16)
C6	0.0305 (16)	0.0443 (18)	0.0433 (18)	0.0024 (14)	−0.0014 (13)	−0.0034 (15)
C8	0.0277 (13)	0.0318 (15)	0.0397 (16)	0.0010 (13)	0.0031 (12)	0.0010 (13)
C9	0.0453 (18)	0.0470 (19)	0.0452 (19)	−0.0084 (16)	−0.0034 (14)	−0.0094 (16)
C10	0.0304 (15)	0.055 (2)	0.0464 (18)	0.0036 (14)	0.0009 (13)	−0.0034 (16)
C11	0.0402 (18)	0.056 (2)	0.0404 (17)	−0.0018 (16)	−0.0029 (13)	−0.0051 (16)
C12	0.048 (2)	0.099 (4)	0.080 (3)	−0.014 (3)	−0.0139 (19)	−0.019 (3)
C13	0.071 (3)	0.073 (3)	0.040 (2)	−0.001 (2)	−0.0067 (17)	0.0043 (18)
Cl1	0.0313 (4)	0.0680 (6)	0.0690 (6)	0.0119 (4)	−0.0002 (4)	−0.0118 (5)
Cl2	0.0797 (7)	0.0820 (7)	0.0480 (5)	−0.0019 (6)	−0.0050 (5)	−0.0268 (5)
O1	0.0354 (12)	0.0373 (12)	0.0489 (13)	−0.0063 (10)	0.0063 (9)	−0.0050 (11)
O2	0.0359 (11)	0.0502 (14)	0.0411 (12)	0.0067 (11)	0.0015 (9)	−0.0107 (11)
O3	0.0330 (12)	0.0408 (13)	0.0425 (12)	0.0059 (9)	−0.0020 (9)	−0.0058 (10)
O4	0.0364 (12)	0.0445 (13)	0.0544 (14)	−0.0067 (10)	0.0055 (10)	0.0060 (11)
P1	0.0292 (4)	0.0331 (4)	0.0327 (4)	0.0000 (3)	0.0020 (3)	−0.0015 (3)

Geometric parameters (Å, º) top

C1—C2	1.381 (4)	C9—H9B	0.9700
C1—C6	1.393 (4)	C10—O3	1.463 (4)
C1—C8	1.506 (4)	C10—C11	1.524 (5)
C2—C3	1.382 (5)	C10—H10A	0.9700
C2—Cl1	1.750 (3)	C10—H10B	0.9700
C3—C4	1.369 (5)	C11—C13	1.530 (5)
C3—H3	0.9300	C11—C12	1.536 (5)
C4—C5	1.379 (5)	C12—H12A	0.9600
C4—Cl2	1.741 (3)	C12—H12B	0.9600
C5—C6	1.366 (5)	C12—H12C	0.9600
C5—H5	0.9300	C13—H13A	0.9600
C6—H6	0.9300	C13—H13B	0.9600
C8—O1	1.425 (3)	C13—H13C	0.9600
C8—P1	1.822 (3)	O1—H1	0.80 (5)
C8—H8	0.9800	O2—P1	1.561 (2)
C9—O2	1.463 (4)	O3—P1	1.572 (2)
C9—C11	1.499 (5)	O4—P1	1.468 (2)
C9—H9A	0.9700

C2—C1—C6	116.4 (3)	C11—C10—H10A	109.3
C2—C1—C8	123.4 (3)	O3—C10—H10B	109.3
C6—C1—C8	120.2 (2)	C11—C10—H10B	109.3
C1—C2—C3	122.9 (3)	H10A—C10—H10B	108.0
C1—C2—Cl1	120.4 (2)	C9—C11—C10	109.6 (3)
C3—C2—Cl1	116.7 (2)	C9—C11—C13	110.6 (3)
C4—C3—C2	118.2 (3)	C10—C11—C13	111.1 (3)
C4—C3—H3	120.9	C9—C11—C12	108.1 (3)
C2—C3—H3	120.9	C10—C11—C12	107.8 (3)
C3—C4—C5	121.2 (3)	C13—C11—C12	109.6 (3)
C3—C4—Cl2	119.0 (3)	C11—C12—H12A	109.5
C5—C4—Cl2	119.8 (3)	C11—C12—H12B	109.5
C6—C5—C4	119.1 (3)	H12A—C12—H12B	109.5
C6—C5—H5	120.5	C11—C12—H12C	109.5
C4—C5—H5	120.5	H12A—C12—H12C	109.5
C5—C6—C1	122.3 (3)	H12B—C12—H12C	109.5
C5—C6—H6	118.9	C11—C13—H13A	109.5
C1—C6—H6	118.9	C11—C13—H13B	109.5
O1—C8—C1	110.1 (2)	H13A—C13—H13B	109.5
O1—C8—P1	108.08 (19)	C11—C13—H13C	109.5
C1—C8—P1	113.1 (2)	H13A—C13—H13C	109.5
O1—C8—H8	108.5	H13B—C13—H13C	109.5
C1—C8—H8	108.5	C8—O1—H1	110 (3)
P1—C8—H8	108.5	C9—O2—P1	121.52 (19)
O2—C9—C11	111.9 (3)	C10—O3—P1	122.6 (2)
O2—C9—H9A	109.2	O4—P1—O2	112.27 (14)
C11—C9—H9A	109.2	O4—P1—O3	111.68 (14)
O2—C9—H9B	109.2	O2—P1—O3	106.63 (12)
C11—C9—H9B	109.2	O4—P1—C8	112.04 (13)
H9A—C9—H9B	107.9	O2—P1—C8	105.43 (14)
O3—C10—C11	111.6 (2)	O3—P1—C8	108.43 (13)
O3—C10—H10A	109.3

C6—C1—C2—C3	1.5 (5)	O2—C9—C11—C12	−175.9 (3)
C8—C1—C2—C3	−176.6 (3)	O3—C10—C11—C9	56.3 (4)
C6—C1—C2—Cl1	−177.0 (2)	O3—C10—C11—C13	−66.1 (4)
C8—C1—C2—Cl1	5.0 (4)	O3—C10—C11—C12	173.8 (3)
C1—C2—C3—C4	−0.7 (5)	C11—C9—O2—P1	48.4 (4)
Cl1—C2—C3—C4	177.8 (3)	C11—C10—O3—P1	−44.1 (4)
C2—C3—C4—C5	−1.0 (5)	C9—O2—P1—O4	−153.1 (3)
C2—C3—C4—Cl2	−178.4 (2)	C9—O2—P1—O3	−30.4 (3)
C3—C4—C5—C6	1.8 (5)	C9—O2—P1—C8	84.7 (3)
Cl2—C4—C5—C6	179.3 (3)	C10—O3—P1—O4	151.7 (2)
C4—C5—C6—C1	−1.0 (5)	C10—O3—P1—O2	28.8 (3)
C2—C1—C6—C5	−0.6 (5)	C10—O3—P1—C8	−84.3 (3)
C8—C1—C6—C5	177.5 (3)	O1—C8—P1—O4	171.92 (19)
C2—C1—C8—O1	137.8 (3)	C1—C8—P1—O4	49.8 (2)
C6—C1—C8—O1	−40.1 (4)	O1—C8—P1—O2	−65.7 (2)
C2—C1—C8—P1	−101.1 (3)	C1—C8—P1—O2	172.18 (19)
C6—C1—C8—P1	80.9 (3)	O1—C8—P1—O3	48.2 (2)
O2—C9—C11—C10	−58.6 (4)	C1—C8—P1—O3	−73.9 (2)
O2—C9—C11—C13	64.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.80 (5)	1.89 (5)	2.686 (3)	173 (4)

Symmetry code: (i) −x+2, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅Cl₂O₄P
M_r	325.11
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.0263 (9), 9.9443 (13), 10.6462 (14)
β (°)	93.975 (2)
V (Å³)	742.08 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.16 × 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	4069, 2597, 2478
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.105, 1.01
No. of reflections	2597
No. of parameters	177
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.25
Absolute structure	Flack (1983), 1140 Friedel pairs
Absolute structure parameter	−0.15 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.80 (5)	1.89 (5)	2.686 (3)	173 (4)

Symmetry code: (i) −x+2, y−1/2, −z.

Acknowledgements

We gratefully acknowledge 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 Nos. 20772042 and 21002037). This work was supported in part by the PCSIRT (grant No. IRT0953).

References

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doi:10.1107/S1600536811009585

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

(S)-2-[(2,4-Di­chloro­phen­yl)(hy­dr­oxy)meth­yl]-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-[(2,4-Dichlorophenyl)(hydroxy)methyl]-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide