Dimethyl (1-hydr­oxy-1,2-diphenyl­ethyl)phospho­nate

Acar, N.; Tahir, M.N.; Yılmaz, H.; Chishti, M.S.A.; Malik, M.A.

doi:10.1107/S1600536809004036

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o481

doi:10.1107/S1600536809004036

Open

access

Dimethyl (1-hydroxy-1,2-diphenylethyl)phosphonate

Nurcan Acar,^a M. Nawaz Tahir,^b ^* Hamza Yılmaz,^a Muhammad Saeed Ahmad Chishti ^b and Muhammad Ali Malik ^b

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

(Received 30 January 2009; accepted 3 February 2009; online 6 February 2009)

In the molecule of the title compound, C₁₆H₁₉O₄P, the coordination around the P atom is distorted tetrahedral. The aromatic rings are oriented at a dihedral angle of 72.28 (11)°. Intramolecular C—H⋯O hydrogen bonding result in the formation of five- and six-membered rings. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules. There is also a weak C—H⋯π interaction.

Related literature

For related structures, see: Hudson et al. (1993 ); Tahir et al. (2007 ); Wroblewski et al. (2000 ).

Experimental

Crystal data

C₁₆H₁₉O₄P
M_r = 306.28
Monoclinic, P 2₁ /c
a = 6.0671 (12) Å
b = 17.0962 (11) Å
c = 15.0502 (12) Å
β = 95.0021 (11)°
V = 1555.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.28 × 0.12 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.968, T_max = 0.982
2800 measured reflections
2794 independent reflections
1655 reflections with I > 2σ(I)
R_int = 0.059
3 standard reflections frequency: 120 min intensity decay: −1.3%

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.159
S = 1.01
2794 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.8200	1.9000	2.710 (3)	172.00
C2—H2⋯O4	0.9300	2.5200	2.956 (4)	109.00
C6—H6⋯O1	0.9300	2.3000	2.671 (4)	103.00
C14—H14⋯O1ⁱⁱ	0.9300	2.5700	3.432 (5)	154.00
C16—H16A⋯O3ⁱⁱ	0.9600	2.4700	3.336 (5)	149.00
C15—H15B⋯CgA	0.9600	2.7200	3.608 (5)	154.00
Symmetry codes: (i) -x+2, -y, -z; (ii) x-1, y, z. CgA is centroid of the C1–C6 ring.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004036/hk2619sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004036/hk2619Isup2.hkl

checkCIF report

Comment top

The crystal structure of (R)-dimethyl [(2-chlorophenyl)hydroxymethyl]- phosphonate (Tahir et al., 2007), which is a member of α-hydroxy phosphonates, has been reported, previously. In continuation to the study of such organic compounds, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1) the coordination around the P atom is a distorted tetrahedral. The crystal structure of dimethyl α-chloromethyl-α -hydroxybenzylphosphonate, (II) (Hudson et al., 1993) and C₂₄H₂₆NO₄P, (III) (Wroblewski et al., 2000) have also been reported, in which both of them have similar coordinations around the C-atom having α-hydroxy group. In (I), the benzene rings A (C1-C6) and B (C9-C14) are oriented at a dihedral angle of 72.28 (11)°. The intramolecular C-H···O hydrogen bonds (Table 1) result in the formations of five- and six-membered rings C (O1/C1/C6/C7/H6) and D (P1/O4/C1/C2/C7/H2), respectively, having planar and boat conformations.

In the crystal structure, intermolecular O-H···O and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. There is also a weak C—H···π interaction (Table 1).

Related literature top

For related structures, see: Hudson et al. (1993); Tahir et al. (2007); Wroblewski et al. (2000). CgA is centroid of the C1–C6 ring.

Experimental top

For the preparation of the title compound, 2-phenylacetophenone (1.96 g, 10 mmol) was disolved in dimethylphosphonate (1.10 g, 10 mmol) at room temperature. Then, KF (2.5 g) and ψ-Al₂O₃ (2.5 g) were added partwise and the mixture was kept at room temperature for 72 h. The product was extracted twice with 50 ml portions of a dichloromethane/methanol mixture (1:1). After the evaporation of the solvent on a rotary evaporator, the residue was crystallized from a mixture of diethyl ether/acetone (3:1) (m.p. 414 K).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Dimethyl (1-hydroxy-1,2-diphenylethyl)phosphonate top

Crystal data top

C₁₆H₁₉O₄P	F(000) = 648
M_r = 306.28	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 83–86 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.0671 (12) Å	Cell parameters from 15 reflections
b = 17.0962 (11) Å	θ = 10.0–11.3°
c = 15.0502 (12) Å	µ = 0.19 mm⁻¹
β = 95.0021 (11)°	T = 296 K
V = 1555.1 (3) Å³	Needle, colorless
Z = 4	0.28 × 0.12 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.059
ω/2θ scans	θ_max = 25.2°, θ_min = 2.4°
Absorption correction: ψ scan (North et al., 1968)	h = 0→7
T_min = 0.968, T_max = 0.982	k = 0→20
2800 measured reflections	l = −18→17
2794 independent reflections	3 standard reflections every 120 min
1655 reflections with I > 2σ(I)	intensity decay: −1.3%

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)] = 0.064	H-atom parameters constrained
wR(F²) = 0.159	w = 1/[σ²(F_o²) + (0.088P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2794 reflections	Δρ_max = 0.40 e Å⁻³
191 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints

Crystal data top

C₁₆H₁₉O₄P	V = 1555.1 (3) Å³
M_r = 306.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0671 (12) Å	µ = 0.19 mm⁻¹
b = 17.0962 (11) Å	T = 296 K
c = 15.0502 (12) Å	0.28 × 0.12 × 0.10 mm
β = 95.0021 (11)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1655 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.059
T_min = 0.968, T_max = 0.982	3 standard reflections every 120 min
2800 measured reflections	intensity decay: −1.3%
2794 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.01	Δρ_max = 0.40 e Å⁻³
2794 reflections	Δρ_min = −0.35 e Å⁻³
191 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
P1	0.79483 (14)	0.12098 (5)	−0.05193 (6)	0.0416 (3)
O1	1.0479 (3)	0.10996 (12)	0.09544 (16)	0.0460 (8)
O2	0.8463 (4)	0.04357 (13)	−0.08487 (15)	0.0576 (9)
O3	0.9546 (5)	0.18125 (15)	−0.08944 (18)	0.0659 (10)
O4	0.5517 (4)	0.14911 (15)	−0.07722 (15)	0.0582 (9)
C1	0.7793 (5)	0.21108 (17)	0.1007 (2)	0.0368 (10)
C2	0.5716 (5)	0.24481 (19)	0.0869 (2)	0.0444 (11)
C3	0.5409 (6)	0.3227 (2)	0.1076 (2)	0.0533 (12)
C4	0.7133 (7)	0.3671 (2)	0.1449 (3)	0.0567 (14)
C5	0.9175 (7)	0.3333 (2)	0.1623 (3)	0.0555 (14)
C6	0.9516 (6)	0.25648 (18)	0.1401 (2)	0.0470 (11)
C7	0.8226 (5)	0.12778 (17)	0.0709 (2)	0.0387 (10)
C8	0.6654 (5)	0.06725 (18)	0.1090 (2)	0.0435 (11)
C9	0.6703 (6)	0.06607 (17)	0.2091 (2)	0.0411 (10)
C10	0.8471 (6)	0.03455 (19)	0.2618 (2)	0.0522 (12)
C11	0.8457 (7)	0.0313 (2)	0.3538 (2)	0.0573 (14)
C12	0.6657 (8)	0.0583 (2)	0.3943 (3)	0.0628 (14)
C13	0.4908 (8)	0.0895 (2)	0.3432 (3)	0.0635 (16)
C14	0.4917 (6)	0.0931 (2)	0.2520 (3)	0.0537 (12)
C15	0.9185 (9)	0.2641 (2)	−0.0979 (3)	0.0863 (19)
C16	0.4445 (7)	0.1432 (3)	−0.1647 (3)	0.0733 (16)
H1	1.06744	0.06272	0.09092	0.0552*
H2	0.45212	0.21495	0.06361	0.0534*
H3	0.40178	0.34518	0.09602	0.0636*
H4	0.69192	0.41953	0.15824	0.0679*
H5	1.03397	0.36254	0.18933	0.0666*
H6	1.09151	0.23458	0.15143	0.0565*
H8A	0.51529	0.07819	0.08461	0.0520*
H8B	0.70402	0.01557	0.08879	0.0520*
H10	0.96854	0.01529	0.23501	0.0623*
H11	0.96685	0.01083	0.38820	0.0688*
H12	0.66330	0.05520	0.45591	0.0750*
H13	0.36975	0.10860	0.37031	0.0764*
H14	0.37005	0.11401	0.21825	0.0644*
H15A	1.04258	0.28789	−0.12280	0.1294*
H15B	0.90211	0.28613	−0.04020	0.1294*
H15C	0.78662	0.27362	−0.13644	0.1294*
H16A	0.29675	0.16336	−0.16523	0.1095*
H16B	0.43893	0.08928	−0.18277	0.1095*
H16C	0.52532	0.17277	−0.20525	0.1095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0398 (5)	0.0398 (5)	0.0458 (5)	0.0101 (4)	0.0066 (4)	−0.0001 (4)
O1	0.0323 (13)	0.0371 (12)	0.0669 (15)	0.0059 (10)	−0.0053 (11)	−0.0040 (11)
O2	0.0693 (17)	0.0495 (15)	0.0533 (14)	0.0195 (13)	0.0007 (12)	−0.0048 (11)
O3	0.0681 (18)	0.0571 (17)	0.0766 (17)	0.0082 (13)	0.0295 (14)	0.0097 (13)
O4	0.0503 (15)	0.0781 (17)	0.0450 (14)	0.0233 (13)	−0.0034 (11)	−0.0082 (12)
C1	0.0363 (18)	0.0357 (17)	0.0389 (17)	0.0016 (14)	0.0064 (14)	0.0009 (13)
C2	0.0339 (19)	0.047 (2)	0.053 (2)	0.0006 (15)	0.0075 (14)	−0.0066 (15)
C3	0.051 (2)	0.051 (2)	0.060 (2)	0.0171 (19)	0.0163 (18)	−0.0002 (17)
C4	0.071 (3)	0.0351 (19)	0.067 (2)	0.0015 (19)	0.024 (2)	−0.0090 (17)
C5	0.057 (3)	0.041 (2)	0.069 (2)	−0.0050 (18)	0.0085 (19)	−0.0118 (17)
C6	0.0391 (19)	0.042 (2)	0.059 (2)	−0.0002 (15)	0.0000 (16)	0.0002 (16)
C7	0.0306 (18)	0.0371 (17)	0.0476 (18)	0.0025 (14)	−0.0013 (14)	−0.0015 (14)
C8	0.0370 (19)	0.0395 (18)	0.053 (2)	−0.0038 (14)	−0.0009 (15)	0.0002 (15)
C9	0.0426 (19)	0.0294 (16)	0.0501 (19)	−0.0046 (14)	−0.0022 (16)	−0.0009 (14)
C10	0.054 (2)	0.048 (2)	0.054 (2)	0.0105 (17)	0.0010 (17)	0.0012 (16)
C11	0.063 (3)	0.053 (2)	0.054 (2)	0.0051 (19)	−0.0051 (19)	0.0080 (18)
C12	0.085 (3)	0.059 (2)	0.045 (2)	−0.010 (2)	0.009 (2)	−0.0025 (18)
C13	0.062 (3)	0.068 (2)	0.063 (3)	0.000 (2)	0.019 (2)	−0.004 (2)
C14	0.041 (2)	0.055 (2)	0.065 (2)	−0.0028 (16)	0.0034 (18)	0.0010 (17)
C15	0.131 (4)	0.050 (3)	0.082 (3)	−0.005 (3)	0.032 (3)	0.010 (2)
C16	0.061 (3)	0.098 (3)	0.059 (2)	0.012 (2)	−0.006 (2)	−0.001 (2)

Geometric parameters (Å, º) top

P1—O2	1.457 (2)	C12—C13	1.364 (6)
P1—O3	1.554 (3)	C13—C14	1.374 (6)
P1—O4	1.567 (3)	C2—H2	0.9300
P1—C7	1.845 (3)	C3—H3	0.9300
O1—C7	1.418 (4)	C4—H4	0.9300
O3—C15	1.437 (4)	C5—H5	0.9300
O4—C16	1.420 (5)	C6—H6	0.9300
O1—H1	0.8200	C8—H8A	0.9700
C1—C6	1.392 (5)	C8—H8B	0.9700
C1—C7	1.523 (4)	C10—H10	0.9300
C1—C2	1.385 (4)	C11—H11	0.9300
C2—C3	1.384 (5)	C12—H12	0.9300
C3—C4	1.372 (5)	C13—H13	0.9300
C4—C5	1.371 (6)	C14—H14	0.9300
C5—C6	1.375 (5)	C15—H15A	0.9600
C7—C8	1.551 (4)	C15—H15B	0.9600
C8—C9	1.504 (4)	C15—H15C	0.9600
C9—C14	1.388 (5)	C16—H16A	0.9600
C9—C10	1.386 (5)	C16—H16B	0.9600
C10—C11	1.387 (4)	C16—H16C	0.9600
C11—C12	1.376 (6)

O1···O2	3.094 (3)	C9···H16B^vi	2.7600
O1···O3	3.045 (4)	C10···H16B^vi	2.9200
O1···C10	3.154 (4)	C10···H1	3.0400
O1···O2ⁱ	2.710 (3)	C11···H5^vii	3.0600
O2···O1ⁱ	2.710 (3)	C12···H15Cⁱⁱⁱ	3.0100
O2···O1	3.094 (3)	C13···H15Cⁱⁱⁱ	2.9500
O3···C16ⁱⁱ	3.336 (5)	C16···H15C	3.0500
O3···O1	3.045 (4)	H1···O2	2.8800
O4···C2	2.956 (4)	H1···C10	3.0400
O1···H14ⁱⁱ	2.5700	H1···H8B	2.3500
O1···H6	2.3000	H1···H10	2.4400
O1···H10	2.7300	H1···O2ⁱ	1.9000
O1···H8Aⁱⁱ	2.9100	H2···O4	2.5200
O2···H16B	2.8700	H2···C8	2.8900
O2···H8Bⁱ	2.9100	H2···H8A	2.3900
O2···H10ⁱ	2.8000	H5···C11^viii	3.0600
O2···H1ⁱ	1.9000	H6···O1	2.3000
O2···H8B	2.8600	H8A···O1^v	2.9100
O2···H1	2.8800	H8A···O4	2.7500
O3···H16Aⁱⁱ	2.4700	H8A···C2	2.8700
O4···H2	2.5200	H8A···H2	2.3900
O4···H8A	2.7500	H8A···H14	2.3500
O4···H15C	2.7500	H8B···O2	2.8600
C1···C15	3.303 (5)	H8B···H1	2.3500
C2···O4	2.956 (4)	H8B···O2ⁱ	2.9100
C2···C9	3.590 (4)	H8B···H16B^vi	2.4900
C3···C16ⁱⁱⁱ	3.574 (5)	H10···O1	2.7300
C4···C16ⁱⁱⁱ	3.423 (6)	H10···H1	2.4400
C6···C15	3.572 (5)	H10···O2ⁱ	2.8000
C9···C2	3.590 (4)	H14···O1^v	2.5700
C10···O1	3.154 (4)	H14···H8A	2.3500
C11···C15ⁱⁱⁱ	3.592 (5)	H15B···C1	2.6400
C12···C15ⁱⁱⁱ	3.399 (5)	H15B···C2	2.9700
C15···C1	3.303 (5)	H15B···C6	2.7500
C15···C11^iv	3.592 (5)	H15C···O4	2.7500
C15···C12^iv	3.399 (5)	H15C···C16	3.0500
C15···C6	3.572 (5)	H15C···H16C	2.5000
C16···O3^v	3.336 (5)	H15C···C12^iv	3.0100
C16···C3^iv	3.574 (5)	H15C···C13^iv	2.9500
C16···C4^iv	3.423 (6)	H16A···O3^v	2.4700
C1···H15B	2.6400	H16B···O2	2.8700
C2···H8A	2.8700	H16B···C8^vi	2.9900
C2···H15B	2.9700	H16B···C9^vi	2.7600
C3···H16Cⁱⁱⁱ	2.8300	H16B···C10^vi	2.9200
C4···H16Cⁱⁱⁱ	2.7000	H16B···H8B^vi	2.4900
C6···H15B	2.7500	H16C···H15C	2.5000
C8···H16B^vi	2.9900	H16C···C3^iv	2.8300
C8···H2	2.8900	H16C···C4^iv	2.7000

O2—P1—O3	108.65 (15)	C4—C3—H3	120.00
O2—P1—O4	114.93 (14)	C3—C4—H4	120.00
O2—P1—C7	113.24 (14)	C5—C4—H4	120.00
O3—P1—O4	108.19 (15)	C4—C5—H5	120.00
O3—P1—C7	108.47 (14)	C6—C5—H5	120.00
O4—P1—C7	103.05 (13)	C1—C6—H6	120.00
P1—O3—C15	126.2 (3)	C5—C6—H6	120.00
P1—O4—C16	123.3 (2)	C7—C8—H8A	109.00
C7—O1—H1	109.00	C7—C8—H8B	109.00
C2—C1—C6	118.1 (3)	C9—C8—H8A	109.00
C6—C1—C7	120.3 (3)	C9—C8—H8B	109.00
C2—C1—C7	121.6 (3)	H8A—C8—H8B	108.00
C1—C2—C3	120.4 (3)	C9—C10—H10	119.00
C2—C3—C4	120.8 (3)	C11—C10—H10	120.00
C3—C4—C5	119.3 (3)	C10—C11—H11	120.00
C4—C5—C6	120.6 (4)	C12—C11—H11	120.00
C1—C6—C5	120.8 (3)	C11—C12—H12	120.00
P1—C7—C1	110.6 (2)	C13—C12—H12	120.00
P1—C7—C8	108.9 (2)	C12—C13—H13	120.00
O1—C7—C1	108.2 (2)	C14—C13—H13	120.00
O1—C7—C8	111.7 (2)	C9—C14—H14	119.00
C1—C7—C8	112.8 (2)	C13—C14—H14	119.00
P1—C7—O1	104.4 (2)	O3—C15—H15A	109.00
C7—C8—C9	114.9 (3)	O3—C15—H15B	109.00
C8—C9—C10	121.7 (3)	O3—C15—H15C	109.00
C10—C9—C14	117.4 (3)	H15A—C15—H15B	109.00
C8—C9—C14	120.9 (3)	H15A—C15—H15C	109.00
C9—C10—C11	121.0 (3)	H15B—C15—H15C	109.00
C10—C11—C12	120.2 (4)	O4—C16—H16A	110.00
C11—C12—C13	119.3 (4)	O4—C16—H16B	109.00
C12—C13—C14	120.7 (4)	O4—C16—H16C	110.00
C9—C14—C13	121.4 (4)	H16A—C16—H16B	109.00
C1—C2—H2	120.00	H16A—C16—H16C	110.00
C3—C2—H2	120.00	H16B—C16—H16C	109.00
C2—C3—H3	120.00

O2—P1—O3—C15	158.6 (3)	C2—C1—C7—C8	−55.0 (4)
O4—P1—O3—C15	33.2 (3)	C6—C1—C7—P1	−110.6 (3)
C7—P1—O3—C15	−77.9 (3)	C6—C1—C7—O1	3.2 (4)
O2—P1—O4—C16	−47.0 (3)	C6—C1—C7—C8	127.3 (3)
O3—P1—O4—C16	74.6 (3)	C1—C2—C3—C4	−2.3 (5)
C7—P1—O4—C16	−170.7 (3)	C2—C3—C4—C5	−0.5 (6)
O2—P1—C7—O1	60.7 (2)	C3—C4—C5—C6	2.1 (6)
O2—P1—C7—C1	176.8 (2)	C4—C5—C6—C1	−0.9 (6)
O2—P1—C7—C8	−58.8 (2)	P1—C7—C8—C9	180.0 (2)
O3—P1—C7—O1	−60.0 (2)	O1—C7—C8—C9	65.2 (3)
O3—P1—C7—C1	56.1 (2)	C1—C7—C8—C9	−56.9 (3)
O3—P1—C7—C8	−179.5 (2)	C7—C8—C9—C10	−73.5 (4)
O4—P1—C7—O1	−174.51 (18)	C7—C8—C9—C14	109.9 (3)
O4—P1—C7—C1	−58.4 (2)	C8—C9—C10—C11	−177.6 (3)
O4—P1—C7—C8	66.0 (2)	C14—C9—C10—C11	−0.8 (5)
C6—C1—C2—C3	3.4 (4)	C8—C9—C14—C13	177.4 (3)
C7—C1—C2—C3	−174.4 (3)	C10—C9—C14—C13	0.6 (5)
C2—C1—C6—C5	−1.8 (5)	C9—C10—C11—C12	1.1 (5)
C7—C1—C6—C5	176.0 (3)	C10—C11—C12—C13	−1.2 (5)
C2—C1—C7—P1	67.1 (3)	C11—C12—C13—C14	1.0 (6)
C2—C1—C7—O1	−179.1 (3)	C12—C13—C14—C9	−0.7 (6)

Symmetry codes: (i) −x+2, −y, −z; (ii) x+1, y, z; (iii) x, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2; (v) x−1, y, z; (vi) −x+1, −y, −z; (vii) −x+2, y−1/2, −z+1/2; (viii) −x+2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.8200	1.9000	2.710 (3)	172.00
C2—H2···O4	0.9300	2.5200	2.956 (4)	109.00
C6—H6···O1	0.9300	2.3000	2.671 (4)	103.00
C14—H14···O1^v	0.9300	2.5700	3.432 (5)	154.00
C16—H16A···O3^v	0.9600	2.4700	3.336 (5)	149.00
C15—H15B···CgA	0.9600	2.7200	3.608 (5)	154.00

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉O₄P
M_r	306.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.0671 (12), 17.0962 (11), 15.0502 (12)
β (°)	95.0021 (11)
V (Å³)	1555.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.28 × 0.12 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.968, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	2800, 2794, 1655
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.159, 1.01
No. of reflections	2794
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.35

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.8200	1.9000	2.710 (3)	172.00
C2—H2···O4	0.9300	2.5200	2.956 (4)	109.00
C6—H6···O1	0.9300	2.3000	2.671 (4)	103.00
C14—H14···O1ⁱⁱ	0.9300	2.5700	3.432 (5)	154.00
C16—H16A···O3ⁱⁱ	0.9600	2.4700	3.336 (5)	149.00
C15—H15B···CgA	0.9600	2.7200	3.608 (5)	154.00

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

References

Enraf–Nonius (1994). CAD-4 EXPRESS. 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
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Hudson, H. R., McPartlin, M., Matthews, R. W., Powell, H. R., Yusuf, R. O., Jaszay, Z. M., Keglevich, G., Petnehazy, I. & Toke, L. (1993). Phosphorus Sulfur Silicon Relat. Elem. 79, 239–243. CrossRef CAS Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. 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
Wroblewski, A. E., Maniukiewicz, W. & Karolczak, W. (2000). J. Chem. Soc. Perkin Trans. 1, pp. 1433–1435. Web of Science CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o481

doi:10.1107/S1600536809004036

Open

access