Dimethyl (2-hydr­oxy-4-phenyl­but-3-en-2-yl)phospho­nate

Tahir, M.N.; Acar, N.; Yilmaz, H.; Tariq, R.H.

doi:10.1107/S1600536809044067

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2922

https://doi.org/10.1107/S1600536809044067

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Dimethyl (2-hydroxy-4-phenylbut-3-en-2-yl)phosphonate

M. Nawaz Tahir,^a ^* Nurcan Acar,^b Hamza Yilmaz ^b and Riaz H. Tariq ^c

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, Faculty of Science, University of Ankara, Ankara, Turkey, and ^cInstitute of Chemical and Pharmaceutical Sciences, The University of Faisalabad, Faisalabad, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 22 October 2009; accepted 23 October 2009; online 31 October 2009)

In the title compound, C₁₂H₁₇O₄P, the phenylbutenyl group is disordered over two sets of sites with an occupancy ratio of 0.755 (12):0.245 (12). In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds occur, forming R₂²(10) ring motifs. The packing is consolidated by weak C—H⋯π interactions.

Related literature

For related structures, see: Acar et al. (2009 ); Tahir et al. (2007 , 2009a ,b ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₁₇O₄P
M_r = 256.23
Monoclinic, C 2/c
a = 17.1522 (12) Å
b = 8.1571 (13) Å
c = 19.5230 (12) Å
β = 103.771 (10)°
V = 2653.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.25 × 0.14 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (MolEN; Fair, 1990 ) T_min = 0.885, T_max = 0.954
2519 measured reflections
2415 independent reflections
1684 reflections with I > 2σ(I)
R_int = 0.095
3 standard reflections frequency: 120 min intensity decay: 0.6%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.175
S = 1.07
2415 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.90	2.721 (3)	176
C6B—H6B⋯Cg1ⁱⁱ	0.93	2.83	3.568 (17)	137
C6B—H6B⋯Cg2ⁱⁱ	0.93	2.94	3.652 (17)	134
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993 ); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: WinGX (Farrugia, 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809044067/hb5172sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044067/hb5172Isup2.hkl

checkCIF report

Comment top

We have reported the crystal structures which contains α-hydroxy phosphonate such as (II) Dimethyl (1-hydroxy-1,2-diphenylethyl)phosphonate (Tahir et al., 2009a), (III) Dimethyl [hydroxy(2-nitrophenyl)methyl]phosphonate (Tahir et al., 2009b), (IV) (R)-Dimethyl [(2-chlorophenyl)hydroxymethyl]phosphonate (Tahir et al., 2007) and Diethyl (1-hydroxy-1,2-diphenylethyl)phosphonate (Acar et al., 2009). The title compound (I, Fig. 1) is in continuation of synthesizing various α-hydroxy phosphonates.

In the crystal structure of title compound phenylbutan is disordered over two possible sites with occupancy ratio of 0.755 (12):0.245 (12). The benzene rings of disordered moieties A (C1A—C6A) and B (C1B—C6B) are nearly planar to one another as the dihedral angle between A/B is 2.76 (1.35)°. The molecules of title compound are dimerized due to O—H···O type of intermolecular H-bondings (Table 1, Fig. 3) forming R₂²(10) ring motif (Bernstein et al., 1995). The molecules are stabilized due to C–H···π interactions (Table 1).

Related literature top

For related structures, see: Acar et al. (2009); Tahir et al. (2007, 2009a,b). For graph-set theory, see: Bernstein et al. (1995). Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

Experimental top

Benzylacetone (4.45 g, 30 mmol) and dimethylphosphonate (3.30 g, 30 mmol) were dissolved in 50 ml of tetrahydrofuran. The mixture was cooled to 273 K and in it KF (1.74 g, 30 mmol) and γ-Al₂O₃ (1.74 g, 17 mmol) were added and refluxed. The precipitates obtained after 48 h were washed with hot distiled water (50 ml) and dried. The crude material was dissolved in distiled water with few drops of ethyl alcohol and colourless needles of (I) were obtained after 4 days.

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1993); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I) with the atom numbering scheme for atoms of greater occupancy ratio. The displacement ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. View of the title compound with the atom numbering scheme for atoms of smaller occupancy ratio. The displacement ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 3. The partial packing of (I), which shows that molecules form inversion dimers.

Dimethyl (2-hydroxy-4-phenylbut-3-en-2-yl)phosphonate top

Crystal data top

C₁₂H₁₇O₄P	F(000) = 1088
M_r = 256.23	D_x = 1.283 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 17.1522 (12) Å	θ = 9.9–13.9°
b = 8.1571 (13) Å	µ = 0.21 mm⁻¹
c = 19.5230 (12) Å	T = 296 K
β = 103.771 (10)°	Needle, colourless
V = 2653.0 (5) Å³	0.25 × 0.14 × 0.12 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.095
ω/2θ scans	θ_max = 25.5°, θ_min = 2.8°
Absorption correction: ψ scan (MolEN; Fair, 1990)	h = −20→20
T_min = 0.885, T_max = 0.954	k = 0→9
2519 measured reflections	l = −23→0
2415 independent reflections	3 standard reflections every 120 min
1684 reflections with I > 2σ(I)	intensity decay: 0.6%

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)] = 0.061	H-atom parameters constrained
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.114P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2415 reflections	Δρ_max = 0.53 e Å⁻³
177 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints

Crystal data top

C₁₂H₁₇O₄P	V = 2653.0 (5) Å³
M_r = 256.23	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.1522 (12) Å	µ = 0.21 mm⁻¹
b = 8.1571 (13) Å	T = 296 K
c = 19.5230 (12) Å	0.25 × 0.14 × 0.12 mm
β = 103.771 (10)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1684 reflections with I > 2σ(I)
Absorption correction: ψ scan (MolEN; Fair, 1990)	R_int = 0.095
T_min = 0.885, T_max = 0.954	3 standard reflections every 120 min
2519 measured reflections	intensity decay: 0.6%
2415 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.07	Δρ_max = 0.53 e Å⁻³
2415 reflections	Δρ_min = −0.42 e Å⁻³
177 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
P1	0.43961 (4)	0.29251 (9)	0.06739 (4)	0.0399 (3)
O1	0.43699 (13)	0.6068 (3)	0.08493 (11)	0.0548 (8)
O2	0.49603 (12)	0.2946 (3)	0.02130 (12)	0.0528 (8)
O3	0.37510 (12)	0.1526 (2)	0.05085 (11)	0.0500 (7)
O4	0.48115 (13)	0.2636 (3)	0.14713 (12)	0.0597 (8)
C1A	0.2124 (3)	0.4228 (6)	0.1674 (2)	0.0453 (16)	0.755 (12)
C2A	0.23963 (19)	0.4970 (7)	0.2329 (3)	0.058 (2)	0.755 (12)
C3A	0.1939 (3)	0.4884 (9)	0.28271 (18)	0.078 (2)	0.755 (12)
C4A	0.1209 (3)	0.4058 (9)	0.2671 (3)	0.072 (2)	0.755 (12)
C5A	0.0937 (2)	0.3316 (6)	0.2017 (3)	0.062 (2)	0.755 (12)
C6A	0.1395 (3)	0.3401 (6)	0.15183 (15)	0.0524 (17)	0.755 (12)
C7A	0.2601 (3)	0.4283 (6)	0.1139 (2)	0.0451 (16)	0.755 (12)
C8A	0.3344 (4)	0.4814 (7)	0.1215 (3)	0.0414 (19)	0.755 (12)
C9	0.37966 (18)	0.4799 (3)	0.06310 (16)	0.0440 (10)
C10	0.3323 (2)	0.5090 (4)	−0.01138 (18)	0.0584 (11)
C11	0.4001 (2)	−0.0152 (4)	0.0447 (2)	0.0644 (13)
C12	0.5626 (2)	0.3125 (6)	0.1775 (2)	0.0896 (19)
C6B	0.1066 (9)	0.341 (2)	0.1847 (9)	0.061 (3)	0.245 (12)
C7B	0.3065 (12)	0.441 (2)	0.0916 (13)	0.046 (6)	0.245 (12)
C1B	0.1670 (11)	0.380 (2)	0.1509 (5)	0.061 (3)	0.245 (12)
C2B	0.2328 (8)	0.471 (2)	0.1857 (9)	0.061 (3)	0.245 (12)
C3B	0.2381 (8)	0.525 (2)	0.2543 (9)	0.061 (3)	0.245 (12)
C4B	0.1777 (12)	0.486 (3)	0.2880 (7)	0.061 (3)	0.245 (12)
C5B	0.1119 (10)	0.395 (3)	0.2532 (9)	0.061 (3)	0.245 (12)
C8B	0.2981 (10)	0.5086 (19)	0.1470 (10)	0.057 (6)	0.245 (12)
H1	0.45706	0.63143	0.05218	0.0821*
H2A	0.28844	0.55226	0.24331	0.0697*	0.755 (12)
H10C	0.36812	0.51292	−0.04233	0.0875*
H11A	0.35594	−0.08762	0.04446	0.0966*
H11B	0.41720	−0.02795	0.00165	0.0966*
H11C	0.44381	−0.04117	0.08403	0.0966*
H12A	0.59764	0.26187	0.15202	0.1344*
H12B	0.56693	0.42950	0.17485	0.1344*
H12C	0.57762	0.27862	0.22598	0.1344*
H3A	0.21203	0.53806	0.32650	0.0928*	0.755 (12)
H4A	0.09026	0.40008	0.30047	0.0865*	0.755 (12)
H5A	0.04489	0.27630	0.19124	0.0741*	0.755 (12)
H6A	0.12130	0.29050	0.10804	0.0629*	0.755 (12)
H7A	0.23485	0.38956	0.06932	0.0541*	0.755 (12)
H8A	0.36086	0.52242	0.16532	0.0500*	0.755 (12)
H10A	0.29444	0.42147	−0.02555	0.0875*
H10B	0.30398	0.61121	−0.01371	0.0875*
H1B	0.16342	0.34369	0.10503	0.0729*	0.245 (12)
H3B	0.28213	0.58635	0.27758	0.0729*	0.245 (12)
H4B	0.18126	0.52218	0.33391	0.0729*	0.245 (12)
H5B	0.07147	0.36876	0.27580	0.0729*	0.245 (12)
H6B	0.06255	0.27951	0.16136	0.0729*	0.245 (12)
H7B	0.26815	0.36654	0.06805	0.0543*	0.245 (12)
H8B	0.33514	0.58922	0.16626	0.0680*	0.245 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0354 (4)	0.0436 (5)	0.0463 (5)	0.0019 (3)	0.0206 (3)	0.0024 (3)
O1	0.0676 (15)	0.0482 (12)	0.0568 (13)	−0.0064 (11)	0.0312 (12)	−0.0074 (10)
O2	0.0520 (13)	0.0542 (13)	0.0644 (14)	0.0030 (10)	0.0382 (11)	0.0013 (10)
O3	0.0399 (12)	0.0423 (11)	0.0723 (15)	0.0011 (9)	0.0225 (10)	−0.0003 (10)
O4	0.0499 (13)	0.0785 (15)	0.0530 (14)	0.0069 (12)	0.0167 (11)	0.0118 (11)
C1A	0.037 (3)	0.064 (3)	0.036 (2)	0.007 (2)	0.011 (2)	−0.005 (2)
C2A	0.043 (3)	0.093 (4)	0.045 (4)	−0.002 (2)	0.022 (2)	−0.011 (3)
C3A	0.055 (4)	0.140 (5)	0.047 (3)	−0.025 (4)	0.031 (3)	−0.022 (3)
C4A	0.053 (4)	0.121 (5)	0.051 (3)	−0.013 (3)	0.029 (3)	−0.020 (3)
C5A	0.046 (3)	0.096 (4)	0.054 (4)	0.000 (2)	0.033 (2)	−0.008 (3)
C6A	0.035 (3)	0.078 (3)	0.051 (3)	−0.002 (2)	0.024 (2)	−0.007 (2)
C7A	0.040 (3)	0.061 (3)	0.040 (2)	−0.007 (2)	0.021 (2)	−0.011 (2)
C8A	0.038 (4)	0.047 (3)	0.040 (3)	0.002 (2)	0.011 (3)	−0.005 (2)
C9	0.0388 (16)	0.0440 (16)	0.0560 (18)	0.0029 (13)	0.0245 (14)	0.0051 (13)
C10	0.051 (2)	0.0560 (19)	0.069 (2)	0.0017 (15)	0.0160 (17)	0.0091 (16)
C11	0.066 (2)	0.0462 (18)	0.085 (3)	0.0049 (16)	0.026 (2)	−0.0011 (16)
C12	0.065 (3)	0.119 (4)	0.074 (3)	−0.015 (2)	−0.005 (2)	−0.003 (2)
C6B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C7B	0.034 (10)	0.047 (9)	0.058 (13)	0.003 (7)	0.015 (9)	0.002 (7)
C1B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C2B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C3B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C4B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C5B	0.037 (4)	0.112 (7)	0.040 (5)	−0.002 (4)	0.024 (3)	−0.003 (4)
C8B	0.036 (8)	0.056 (9)	0.083 (12)	−0.010 (7)	0.023 (9)	−0.028 (8)

Geometric parameters (Å, º) top

P1—O2	1.470 (2)	C8A—C9	1.525 (7)
P1—O3	1.569 (2)	C9—C10	1.506 (5)
P1—O4	1.568 (2)	C1B—H1B	0.9300
P1—C9	1.833 (3)	C2A—H2A	0.9300
O1—C9	1.422 (4)	C3A—H3A	0.9300
O3—C11	1.448 (4)	C3B—H3B	0.9300
O4—C12	1.438 (4)	C4A—H4A	0.9300
O1—H1	0.8200	C4B—H4B	0.9300
C1A—C2A	1.391 (7)	C5A—H5A	0.9300
C1A—C7A	1.473 (7)	C5B—H5B	0.9300
C1A—C6A	1.389 (7)	C6A—H6A	0.9300
C1B—C2B	1.39 (2)	C6B—H6B	0.9300
C1B—C6B	1.39 (2)	C7A—H7A	0.9300
C2A—C3A	1.389 (6)	C7B—H7B	0.9300
C2B—C8B	1.52 (2)	C8A—H8A	0.9300
C2B—C3B	1.39 (2)	C8B—H8B	0.9300
C3A—C4A	1.390 (8)	C10—H10B	0.9600
C3B—C4B	1.39 (2)	C10—H10A	0.9600
C4A—C5A	1.390 (8)	C10—H10C	0.9600
C4B—C5B	1.39 (3)	C11—H11A	0.9600
C5A—C6A	1.391 (6)	C11—H11B	0.9600
C5B—C6B	1.39 (2)	C11—H11C	0.9600
C7A—C8A	1.321 (9)	C12—H12A	0.9600
C7B—C8B	1.25 (3)	C12—H12B	0.9600
C7B—C9	1.52 (2)	C12—H12C	0.9600

O2—P1—O3	114.66 (13)	C2A—C3A—H3A	120.00
O2—P1—O4	113.56 (13)	C4A—C3A—H3A	120.00
O2—P1—C9	113.97 (14)	C2B—C3B—H3B	120.00
O3—P1—O4	103.09 (12)	C4B—C3B—H3B	120.00
O3—P1—C9	103.70 (12)	C3A—C4A—H4A	120.00
O4—P1—C9	106.75 (14)	C5A—C4A—H4A	120.00
P1—O3—C11	119.8 (2)	C3B—C4B—H4B	120.00
P1—O4—C12	122.3 (2)	C5B—C4B—H4B	120.00
C9—O1—H1	109.00	C4A—C5A—H5A	120.00
C2A—C1A—C7A	121.1 (4)	C6A—C5A—H5A	120.00
C6A—C1A—C7A	118.9 (4)	C4B—C5B—H5B	120.00
C2A—C1A—C6A	120.0 (4)	C6B—C5B—H5B	120.00
C2B—C1B—C6B	120.1 (12)	C5A—C6A—H6A	120.00
C1A—C2A—C3A	120.0 (4)	C1A—C6A—H6A	120.00
C1B—C2B—C3B	120.0 (14)	C1B—C6B—H6B	120.00
C1B—C2B—C8B	118.3 (14)	C5B—C6B—H6B	120.00
C3B—C2B—C8B	121.7 (14)	C1A—C7A—H7A	116.00
C2A—C3A—C4A	120.0 (5)	C8A—C7A—H7A	116.00
C2B—C3B—C4B	119.8 (15)	C9—C7B—H7B	120.00
C3A—C4A—C5A	120.0 (5)	C8B—C7B—H7B	120.00
C3B—C4B—C5B	120.2 (15)	C7A—C8A—H8A	118.00
C4A—C5A—C6A	120.0 (4)	C9—C8A—H8A	118.00
C4B—C5B—C6B	120.0 (16)	C2B—C8B—H8B	117.00
C1A—C6A—C5A	120.0 (4)	C7B—C8B—H8B	117.00
C1B—C6B—C5B	119.9 (15)	C9—C10—H10C	110.00
C1A—C7A—C8A	127.9 (4)	C9—C10—H10B	109.00
C8B—C7B—C9	119.9 (17)	C9—C10—H10A	109.00
C7A—C8A—C9	124.3 (5)	H10B—C10—H10C	109.00
C2B—C8B—C7B	126.1 (17)	H10A—C10—H10B	109.00
C7B—C9—C10	94.8 (9)	H10A—C10—H10C	110.00
O1—C9—C10	110.5 (2)	H11A—C11—H11B	110.00
O1—C9—C7B	127.9 (8)	O3—C11—H11A	109.00
C8A—C9—C10	117.9 (3)	O3—C11—H11B	109.00
P1—C9—O1	104.7 (2)	O3—C11—H11C	109.00
P1—C9—C8A	110.6 (3)	H11A—C11—H11C	109.00
P1—C9—C10	110.1 (2)	H11B—C11—H11C	109.00
P1—C9—C7B	108.2 (7)	H12B—C12—H12C	109.00
O1—C9—C8A	102.1 (3)	O4—C12—H12A	109.00
C2B—C1B—H1B	120.00	O4—C12—H12B	109.00
C6B—C1B—H1B	120.00	O4—C12—H12C	109.00
C1A—C2A—H2A	120.00	H12A—C12—H12B	110.00
C3A—C2A—H2A	120.00	H12A—C12—H12C	109.00

O2—P1—O3—C11	50.8 (3)	C6A—C1A—C2A—C3A	0.0 (8)
O4—P1—O3—C11	−73.1 (2)	C7A—C1A—C2A—C3A	−179.3 (5)
C9—P1—O3—C11	175.7 (2)	C2A—C1A—C6A—C5A	0.1 (7)
O2—P1—O4—C12	28.4 (3)	C7A—C1A—C6A—C5A	179.3 (4)
O3—P1—O4—C12	153.1 (3)	C2A—C1A—C7A—C8A	8.7 (8)
C9—P1—O4—C12	−98.0 (3)	C6A—C1A—C7A—C8A	−170.6 (5)
O2—P1—C9—O1	−60.4 (2)	C1A—C2A—C3A—C4A	−0.1 (9)
O2—P1—C9—C8A	−169.6 (3)	C2A—C3A—C4A—C5A	0.1 (10)
O2—P1—C9—C10	58.4 (3)	C3A—C4A—C5A—C6A	−0.1 (9)
O3—P1—C9—O1	174.29 (18)	C4A—C5A—C6A—C1A	0.0 (8)
O3—P1—C9—C8A	65.1 (3)	C1A—C7A—C8A—C9	179.0 (4)
O3—P1—C9—C10	−67.0 (2)	C7A—C8A—C9—P1	−93.6 (6)
O4—P1—C9—O1	65.8 (2)	C7A—C8A—C9—O1	155.5 (5)
O4—P1—C9—C8A	−43.4 (3)	C7A—C8A—C9—C10	34.2 (7)
O4—P1—C9—C10	−175.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.90	2.721 (3)	176
C6B—H6B···Cg1ⁱⁱ	0.93	2.83	3.568 (17)	137
C6B—H6B···Cg2ⁱⁱ	0.93	2.94	3.652 (17)	134

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇O₄P
M_r	256.23
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	17.1522 (12), 8.1571 (13), 19.5230 (12)
β (°)	103.771 (10)
V (Å³)	2653.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.14 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (MolEN; Fair, 1990)
T_min, T_max	0.885, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	2519, 2415, 1684
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.175, 1.07
No. of reflections	2415
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.42

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1993), MolEN (Fair, 1990), WinGX (Farrugia, 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.90	2.721 (3)	176
C6B—H6B···Cg1ⁱⁱ	0.93	2.83	3.568 (17)	137
C6B—H6B···Cg2ⁱⁱ	0.93	2.94	3.652 (17)	134

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

References

Acar, N., Tahir, M. N., Tariq, R. H. & Yilmaz, H. (2009). Acta Cryst. E65, o1203. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1993). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fair, C. K. (1990). MolEN. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals 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
Tahir, M. N., Acar, N., Yilmaz, H., Danish, M. & Ülkü, D. (2007). Acta Cryst. E63, o3817–o3818. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tahir, M. N., Acar, N., Yilmaz, H. & Tariq, R. H. (2009b). Acta Cryst. E65, o2051. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tahir, M. N., Acar, N., Yilmaz, H., Tariq, M. I. & Ülkü, D. (2009a). Acta Cryst. E65, o562. Web of Science CSD CrossRef IUCr Journals Google Scholar

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