2-[(Diphenyl­phosphor­yl)(hy­droxy)meth­yl]-5-meth­oxy­phenol

Shao, Y.; Yang, C.; Xia, W.

doi:10.1107/S1600536812020685

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1708

doi:10.1107/S1600536812020685

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2-[(Diphenylphosphoryl)(hydroxy)methyl]-5-methoxyphenol

Yutian Shao,^a Chao Yang ^a ^* and Wujiong Xia ^a

^aState Key Laboratory of Urban Water Resource and Environment (SKLUWRE) & Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin, Heilongjiang 150090, People's Republic of China
^*Correspondence e-mail: xyyang@hit.edu.cn

(Received 28 April 2012; accepted 8 May 2012; online 12 May 2012)

In the title compound, C₂₀H₁₉O₄P, the dihedral angle between the phenyl rings is 73.3 (4)° and the dihedral angles between the benzene ring and the two phenyl rings are 43.0 (3) and 54.3 (1)°. In the crystal, O—H⋯O hydrogen bonds and weak O—H⋯O interactions are observed, which form a supramolecular sheet parallel to (010).

Related literature

For α-hydroxylphosphine oxides, see: Marmor & Seyferth (1969 ); Toyota et al. (1993 ); Kazankova et al. (2003 ); For substrates used in the preparation of α-carboxylphosphine oxides, see: Fischer et al. (1993 ) and for substrates used in the preparation of unsymmetrical phosphine oxides, see: Miller et al. (1957 ).

Experimental

Crystal data

C₂₀H₁₉O₄P
M_r = 354.32
Monoclinic, P 2₁ /n
a = 8.349 (7) Å
b = 17.406 (14) Å
c = 12.639 (10) Å
β = 107.863 (9)°
V = 1748 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.965, T_max = 0.982
8150 measured reflections
3017 independent reflections
2124 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.04
3017 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.81	2.613 (2)	168
O4—H4⋯O3ⁱⁱ	0.82	2.28	3.046 (3)	156
Symmetry codes: (i) -x+1, -y, -z+2; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020685/jj2135sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020685/jj2135Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020685/jj2135Isup3.cml

checkCIF report

Comment top

α-hydroxylphosphine oxides are molecules (Marmor et al., 1969; Toyota, et al., 1993; Kazankova et al.., 2003) that are used as substrates for the preparation of α-carboxylphosphine oxides (Fischer, et al., 1993) and unsymmetrical phosphine oxides (Miller et al., 1957). We present herin, the preparation and crystal structure of the title compound, C₂₀H₁₉O₄P, (I).

In the title compound (I), the dihedral angle between the two mono-substituted benzene rings is 73.3 (4)° (Fig. 1). The dihedral angle between the tri- substituted benzene ring and two mono-substituted benzene rings is 43. 0(3)° and 54.3 (0)°, respectively. O—H···O hydrogen bonds and weak O—H···O intermolecular interactions (Table 1) are observed which form a two-dimensional supramolecular sheet and influence crystal packing (Fig. 2).

Related literature top

For α-hydroxylphosphine oxides, see: Marmor & Seyferth (1969); Toyota et al. (1993); Kazankova et al. (2003); For substrates used in the preparation of α-carboxylphosphine oxides, see: Fischer et al. (1993) and for substrates used in the preparation of unsymmetrical phosphine oxides, see: Miller et al. (1957).

Experimental top

The title compound was obtained from the following procedure. To a flame dried round-bottomed flask, 2-hydroxy-4-methoxy-benzaldehyde (1.0equiv), potassiumtert-butoxide (1.5equiv) and anhydrous DMF were added under N₂ protection. After the addition of chlorodiphenylphosphine (1.5 equiv. in anhydrous DMF) and stirred overnight at room temperature, water was added to quench the reaction. The product was extracted with CH₂Cl₂, dried with Na₂SO₄and concentrated under pressure to give an oil residue, which was purified through a silica gel column to yield the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed aloing the a axis. Dashed lines represent O—H···O hydrogen bonds and weak O—H···O intermolecular interactions. H atoms not involved in hydrogen bonding are omitted for clarity. [symmetry codes: (i) 1 - x, - y, 2 -z; (ii) x - 1/2, 0.5 - y, z - 0.5; (iii) x + 1/2, 0.5 - y, 0.5 + z].

2-[(Diphenylphosphoryl)(hydroxy)methyl]-5-methoxyphenol top

Crystal data top

C₂₀H₁₉O₄P	F(000) = 744
M_r = 354.32	D_x = 1.346 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 255 reflections
a = 8.349 (7) Å	θ = 25.6–3.1°
b = 17.406 (14) Å	µ = 0.18 mm⁻¹
c = 12.639 (10) Å	T = 296 K
β = 107.863 (9)°	Block, colourless
V = 1748 (2) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD APEXII diffractometer	3017 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 10 pixels mm^-1	θ_max = 25.1°, θ_min = 2.1°
ω scans	h = −9→7
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −20→20
T_min = 0.965, T_max = 0.982	l = −15→12
8150 measured reflections

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0511P)² + 0.1885P] where P = (F_o² + 2F_c²)/3
3017 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₀H₁₉O₄P	V = 1748 (2) Å³
M_r = 354.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.349 (7) Å	µ = 0.18 mm⁻¹
b = 17.406 (14) Å	T = 296 K
c = 12.639 (10) Å	0.20 × 0.15 × 0.10 mm
β = 107.863 (9)°

Data collection top

Bruker SMART CCD APEXII diffractometer	3017 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2124 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.982	R_int = 0.043
8150 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
3017 reflections	Δρ_min = −0.25 e Å⁻³
229 parameters

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
P1	0.18172 (8)	0.11354 (3)	0.82003 (5)	0.0358 (2)
O1	0.2141 (2)	0.08777 (9)	0.93707 (13)	0.0448 (5)
O2	0.6011 (2)	0.00424 (8)	0.91075 (14)	0.0510 (5)
H2	0.6570	−0.0200	0.9652	0.077*
O3	0.9492 (2)	0.21531 (10)	1.09662 (15)	0.0536 (5)
O4	0.3359 (2)	0.13072 (10)	0.66335 (14)	0.0510 (5)
H4	0.3793	0.1733	0.6665	0.077*
C1	0.1266 (3)	0.21306 (13)	0.8032 (2)	0.0380 (6)
C2	0.0631 (3)	0.24707 (15)	0.6995 (2)	0.0497 (7)
H2A	0.0431	0.2171	0.6359	0.060*
C3	0.0295 (4)	0.32424 (16)	0.6896 (3)	0.0639 (9)
H3	−0.0112	0.3466	0.6196	0.077*
C4	0.0560 (4)	0.36781 (16)	0.7825 (3)	0.0725 (10)
H4A	0.0307	0.4200	0.7757	0.087*
C5	0.1198 (5)	0.33591 (16)	0.8866 (3)	0.0749 (10)
H5	0.1385	0.3665	0.9495	0.090*
C6	0.1560 (4)	0.25804 (15)	0.8973 (2)	0.0551 (8)
H6	0.1998	0.2362	0.9675	0.066*
C7	0.0125 (3)	0.06133 (13)	0.7244 (2)	0.0389 (6)
C8	−0.1523 (4)	0.07782 (17)	0.7203 (2)	0.0587 (8)
H8	−0.1737	0.1176	0.7632	0.070*
C9	−0.2837 (4)	0.03577 (19)	0.6533 (3)	0.0698 (9)
H9	−0.3933	0.0477	0.6511	0.084*
C10	−0.2562 (4)	−0.02306 (18)	0.5903 (3)	0.0629 (9)
H10	−0.3460	−0.0517	0.5462	0.076*
C11	−0.0960 (4)	−0.03961 (17)	0.5925 (3)	0.0651 (9)
H11	−0.0764	−0.0792	0.5486	0.078*
C12	0.0377 (4)	0.00201 (15)	0.6594 (2)	0.0572 (8)
H12	0.1466	−0.0103	0.6605	0.069*
C13	0.3672 (3)	0.10114 (13)	0.77302 (19)	0.0368 (6)
H13	0.3831	0.0456	0.7680	0.044*
C14	0.5235 (3)	0.13105 (13)	0.85807 (19)	0.0363 (6)
C15	0.6364 (3)	0.07990 (12)	0.92673 (19)	0.0363 (6)
C16	0.7810 (3)	0.10582 (13)	1.0067 (2)	0.0404 (6)
H16	0.8560	0.0710	1.0519	0.048*
C17	0.8119 (3)	0.18334 (14)	1.0182 (2)	0.0412 (6)
C18	0.7035 (3)	0.23562 (14)	0.9503 (2)	0.0465 (7)
H18	0.7269	0.2879	0.9575	0.056*
C19	0.5600 (3)	0.20922 (13)	0.8717 (2)	0.0438 (7)
H19	0.4860	0.2444	0.8268	0.053*
C20	1.0787 (4)	0.16408 (17)	1.1566 (2)	0.0635 (9)
H20A	1.0368	0.1320	1.2040	0.095*
H20B	1.1732	0.1932	1.2009	0.095*
H20C	1.1132	0.1326	1.1051	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0395 (4)	0.0306 (3)	0.0328 (4)	0.0029 (3)	0.0043 (3)	0.0020 (3)
O1	0.0551 (12)	0.0408 (9)	0.0339 (10)	0.0076 (8)	0.0070 (8)	0.0076 (8)
O2	0.0608 (13)	0.0318 (9)	0.0454 (12)	0.0020 (8)	−0.0059 (9)	0.0032 (8)
O3	0.0452 (11)	0.0561 (11)	0.0473 (11)	−0.0069 (9)	−0.0035 (9)	−0.0058 (9)
O4	0.0523 (12)	0.0566 (12)	0.0382 (11)	−0.0021 (9)	0.0052 (9)	−0.0001 (8)
C1	0.0376 (15)	0.0336 (12)	0.0420 (15)	0.0032 (10)	0.0113 (12)	0.0028 (11)
C2	0.0507 (17)	0.0484 (15)	0.0498 (17)	0.0114 (13)	0.0153 (14)	0.0107 (13)
C3	0.061 (2)	0.0520 (18)	0.082 (2)	0.0177 (15)	0.0261 (18)	0.0295 (17)
C4	0.077 (2)	0.0345 (16)	0.111 (3)	0.0128 (15)	0.036 (2)	0.0162 (19)
C5	0.098 (3)	0.0414 (17)	0.084 (3)	0.0054 (17)	0.027 (2)	−0.0193 (16)
C6	0.067 (2)	0.0413 (15)	0.0536 (19)	0.0057 (14)	0.0141 (16)	−0.0002 (13)
C7	0.0437 (16)	0.0392 (13)	0.0317 (14)	−0.0021 (11)	0.0083 (12)	0.0027 (11)
C8	0.0465 (18)	0.0670 (19)	0.064 (2)	−0.0067 (14)	0.0193 (15)	−0.0151 (15)
C9	0.0446 (19)	0.085 (2)	0.076 (2)	−0.0130 (17)	0.0135 (17)	−0.0075 (19)
C10	0.055 (2)	0.073 (2)	0.054 (2)	−0.0242 (16)	0.0065 (16)	−0.0039 (16)
C11	0.072 (2)	0.0586 (18)	0.063 (2)	−0.0190 (17)	0.0185 (18)	−0.0223 (15)
C12	0.0478 (18)	0.0513 (17)	0.070 (2)	−0.0069 (13)	0.0144 (16)	−0.0182 (15)
C13	0.0390 (15)	0.0327 (12)	0.0340 (14)	0.0028 (10)	0.0042 (11)	−0.0002 (10)
C14	0.0371 (14)	0.0358 (13)	0.0336 (14)	0.0011 (10)	0.0074 (11)	0.0002 (10)
C15	0.0399 (15)	0.0327 (13)	0.0337 (14)	0.0010 (11)	0.0073 (12)	−0.0022 (10)
C16	0.0407 (15)	0.0416 (14)	0.0355 (15)	0.0064 (11)	0.0065 (12)	0.0040 (11)
C17	0.0399 (15)	0.0464 (14)	0.0342 (15)	−0.0054 (12)	0.0070 (12)	−0.0039 (11)
C18	0.0501 (17)	0.0331 (13)	0.0487 (17)	−0.0054 (12)	0.0038 (14)	0.0000 (12)
C19	0.0463 (16)	0.0347 (13)	0.0420 (16)	0.0039 (11)	0.0012 (13)	0.0045 (11)
C20	0.0416 (18)	0.080 (2)	0.057 (2)	0.0037 (15)	−0.0022 (15)	−0.0090 (16)

Geometric parameters (Å, º) top

P1—O1	1.489 (2)	C8—C9	1.373 (4)
P1—C1	1.788 (3)	C8—H8	0.9300
P1—C7	1.799 (3)	C9—C10	1.359 (4)
P1—C13	1.833 (3)	C9—H9	0.9300
O2—C15	1.351 (3)	C10—C11	1.360 (4)
O2—H2	0.8200	C10—H10	0.9300
O3—C17	1.382 (3)	C11—C12	1.381 (4)
O3—C20	1.426 (3)	C11—H11	0.9300
O4—C13	1.426 (3)	C12—H12	0.9300
O4—H4	0.8200	C13—C14	1.507 (3)
C1—C6	1.382 (3)	C13—H13	0.9800
C1—C2	1.386 (3)	C14—C15	1.390 (3)
C2—C3	1.370 (4)	C14—C19	1.394 (3)
C2—H2A	0.9300	C15—C16	1.391 (3)
C3—C4	1.358 (4)	C16—C17	1.373 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.375 (4)	C17—C18	1.381 (3)
C4—H4A	0.9300	C18—C19	1.379 (3)
C5—C6	1.386 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20A	0.9600
C7—C12	1.375 (4)	C20—H20B	0.9600
C7—C8	1.391 (4)	C20—H20C	0.9600

O1—P1—C1	111.82 (11)	C11—C10—H10	120.3
O1—P1—C7	112.41 (11)	C10—C11—C12	120.4 (3)
C1—P1—C7	106.81 (12)	C10—C11—H11	119.8
O1—P1—C13	111.88 (11)	C12—C11—H11	119.8
C1—P1—C13	106.70 (11)	C7—C12—C11	121.1 (3)
C7—P1—C13	106.86 (13)	C7—C12—H12	119.4
C15—O2—H2	109.5	C11—C12—H12	119.4
C17—O3—C20	117.1 (2)	O4—C13—C14	115.4 (2)
C13—O4—H4	109.5	O4—C13—P1	110.58 (16)
C6—C1—C2	119.2 (2)	C14—C13—P1	111.17 (17)
C6—C1—P1	118.36 (19)	O4—C13—H13	106.4
C2—C1—P1	122.41 (19)	C14—C13—H13	106.4
C3—C2—C1	120.9 (3)	P1—C13—H13	106.4
C3—C2—H2A	119.6	C15—C14—C19	117.9 (2)
C1—C2—H2A	119.6	C15—C14—C13	119.8 (2)
C4—C3—C2	119.6 (3)	C19—C14—C13	122.3 (2)
C4—C3—H3	120.2	O2—C15—C14	117.1 (2)
C2—C3—H3	120.2	O2—C15—C16	121.7 (2)
C3—C4—C5	120.9 (3)	C14—C15—C16	121.1 (2)
C3—C4—H4A	119.5	C17—C16—C15	119.3 (2)
C5—C4—H4A	119.5	C17—C16—H16	120.4
C4—C5—C6	119.8 (3)	C15—C16—H16	120.4
C4—C5—H5	120.1	C16—C17—C18	121.0 (2)
C6—C5—H5	120.1	C16—C17—O3	124.0 (2)
C1—C6—C5	119.6 (3)	C18—C17—O3	114.9 (2)
C1—C6—H6	120.2	C19—C18—C17	119.1 (2)
C5—C6—H6	120.2	C19—C18—H18	120.4
C12—C7—C8	117.6 (2)	C17—C18—H18	120.4
C12—C7—P1	123.2 (2)	C18—C19—C14	121.5 (2)
C8—C7—P1	119.0 (2)	C18—C19—H19	119.2
C9—C8—C7	120.4 (3)	C14—C19—H19	119.2
C9—C8—H8	119.8	O3—C20—H20A	109.5
C7—C8—H8	119.8	O3—C20—H20B	109.5
C10—C9—C8	121.1 (3)	H20A—C20—H20B	109.5
C10—C9—H9	119.5	O3—C20—H20C	109.5
C8—C9—H9	119.5	H20A—C20—H20C	109.5
C9—C10—C11	119.3 (3)	H20B—C20—H20C	109.5
C9—C10—H10	120.3

O1—P1—C1—C6	14.3 (3)	C10—C11—C12—C7	−0.6 (5)
C7—P1—C1—C6	137.7 (2)	O1—P1—C13—O4	−176.33 (14)
C13—P1—C1—C6	−108.3 (2)	C1—P1—C13—O4	−53.73 (18)
O1—P1—C1—C2	−168.7 (2)	C7—P1—C13—O4	60.24 (18)
C7—P1—C1—C2	−45.3 (2)	O1—P1—C13—C14	−46.77 (19)
C13—P1—C1—C2	68.7 (2)	C1—P1—C13—C14	75.83 (18)
C6—C1—C2—C3	0.0 (4)	C7—P1—C13—C14	−170.20 (15)
P1—C1—C2—C3	−177.0 (2)	O4—C13—C14—C15	−130.8 (2)
C1—C2—C3—C4	−1.1 (4)	P1—C13—C14—C15	102.3 (2)
C2—C3—C4—C5	1.5 (5)	O4—C13—C14—C19	49.7 (3)
C3—C4—C5—C6	−0.7 (5)	P1—C13—C14—C19	−77.3 (3)
C2—C1—C6—C5	0.7 (4)	C19—C14—C15—O2	−178.5 (2)
P1—C1—C6—C5	177.8 (2)	C13—C14—C15—O2	1.9 (3)
C4—C5—C6—C1	−0.4 (5)	C19—C14—C15—C16	0.1 (4)
O1—P1—C7—C12	−100.7 (2)	C13—C14—C15—C16	−179.4 (2)
C1—P1—C7—C12	136.3 (2)	O2—C15—C16—C17	179.0 (2)
C13—P1—C7—C12	22.4 (3)	C14—C15—C16—C17	0.4 (4)
O1—P1—C7—C8	74.9 (2)	C15—C16—C17—C18	−1.3 (4)
C1—P1—C7—C8	−48.0 (2)	C15—C16—C17—O3	178.4 (2)
C13—P1—C7—C8	−161.9 (2)	C20—O3—C17—C16	10.2 (4)
C12—C7—C8—C9	0.0 (4)	C20—O3—C17—C18	−170.1 (2)
P1—C7—C8—C9	−175.9 (2)	C16—C17—C18—C19	1.7 (4)
C7—C8—C9—C10	0.5 (5)	O3—C17—C18—C19	−178.1 (2)
C8—C9—C10—C11	−1.0 (5)	C17—C18—C19—C14	−1.1 (4)
C9—C10—C11—C12	1.1 (5)	C15—C14—C19—C18	0.2 (4)
C8—C7—C12—C11	0.0 (4)	C13—C14—C19—C18	179.7 (2)
P1—C7—C12—C11	175.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.81	2.613 (2)	168
O4—H4···O3ⁱⁱ	0.82	2.28	3.046 (3)	156

Symmetry codes: (i) −x+1, −y, −z+2; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉O₄P
M_r	354.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.349 (7), 17.406 (14), 12.639 (10)
β (°)	107.863 (9)
V (Å³)	1748 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.965, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	8150, 3017, 2124
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.04
No. of reflections	3017
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT (Bruker, 2004, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.81	2.613 (2)	167.5
O4—H4···O3ⁱⁱ	0.82	2.28	3.046 (3)	155.7

Symmetry codes: (i) −x+1, −y, −z+2; (ii) x−1/2, −y+1/2, z−1/2.

Acknowledgements

The work is supported by the National Natural Science Foundation (Nos 21002018 and 21072038), the Fundamental Research Funds for the Central Universities (No. HIT.BRET2.2010001), WZSTP (No. G20100056), ZJSTP (No. 2011-C23116).

References

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