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

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

doi:10.1107/S160053680901602X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1203

doi:10.1107/S160053680901602X

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

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

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

(Received 26 April 2009; accepted 28 April 2009; online 7 May 2009)

In the title compound, C₁₈H₂₃O₄P, the dihedral angle between the aromatic ring planes is 69.94 (14)°. Both ethyl side chains are disordered over two sets of sites, with occupancy ratios of 80:20 and 70:30. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds occur, leading to R₂¹(8) loops, and C—H⋯O and weak C—H⋯π interactions are also seen.

Related literature

For related structures, see: Acar et al. (2009 ); Tahir et al. (2007 , 2009a ,b ). For the synthesis, see: Texier-Boullet & Lequitte (1986 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₂₃O₄P
M_r = 334.33
Monoclinic, C 2/c
a = 23.8545 (11) Å
b = 10.6663 (5) Å
c = 18.4994 (14) Å
β = 129.451 (2)°
V = 3634.6 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.953, T_max = 0.968
18572 measured reflections
4354 independent reflections
2742 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.198
S = 1.05
4354 reflections
217 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.86 (4)	1.87 (4)	2.718 (3)	170 (5)
C10—H10⋯O4ⁱ	0.93	2.54	3.409 (4)	155
C16A—H16B⋯CgAⁱⁱ	0.97	2.94	3.657 (8)	133
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ . CgA is the centroid of the C9–C14 ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901602X/hb2959sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901602X/hb2959Isup2.hkl

checkCIF report

Comment top

We have reported the preparation and crystal structures of the phosphonate compounds (Acar et al., 2009; Tahir et al., 2007, 2009a, 2009b). In continuation to the study of phosphonate compounds, we, herein report the preparation and crystal structure of the title compound (I), (Fig. 1).

The crystal structures of (II) Dimethyl (1-hydroxy-1,2-diphenylethyl)phosphonate (Acar et al., 2009) has been reported which differs from (I) due to dimethylphosphonate instead of diethylphosphonate. In the title compound ethyl moieties of diethylphosphonate are disordered over two sites with occupancy ratios of 80:20 and 70:30, respectively. The disorder in diethyl moieties is also present in the reported structure (Tahir et al., 2009a). The present compound is basically dimerized forming ring motifs R₂²(10) (Bernstein et al., 1995) due to O—H···O type of intermolecular H-bonding (Fig. 2). The title molecule is also stabilized due to intermolecular H-bonding of C—H···O type and C—H···CgA interaction (Table 1), Where CgA is the centroid of the aromatic ring A (C9–C14). Ring motifs of R₂¹(8) are also present which are formed due to the intermolecular H-bondings (Fig. 2). The dihedral angle between the ring A and the benzene ring B (C1–C6) is 69.94 (14)°.

Related literature top

For related structures, see: Acar et al. (2009); Tahir et al. (2007, 2009a,b). For the synthesis, see: Texier-Boullet & Lequitte (1986). For graph-set notation, see: Bernstein et al. (1995). CgA is the centroid of the C9–C14 ring.

Experimental top

The title compound was prepared according to method described by Texier-Boullet & Lequitte (1986). In a solution mixture of 2-phenylacetophenone (3.92 g, 20 mmol) and diethylphosphonate (2.76 g, 20 mmol), a mixture of KF (5 g, 86.20 mmol) and commercial Al₂O₃ (5 g, 49 mmol) was slowly added at 273 K. The reaction mixture remained at room temperature for two days. The product was extracted twice with CH₃Cl₂. The extracted product was recrystallized in a mixture of distalled water and ethyl alcohol to yield colourless prisms of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) showing 30% displacement ellipoids (H-atoms are shown by small spheres of arbitrary radius). The ethyl moieties of smaller occupancy factor are not shown for clarity.
	Fig. 2. Detail of (I) showing the formation of dimers through hydrogen bonding forming R₂²(10) motifs.

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

Crystal data top

C₁₈H₂₃O₄P	F(000) = 1424
M_r = 334.33	D_x = 1.220 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4354 reflections
a = 23.8545 (11) Å	θ = 2.2–27.9°
b = 10.6663 (5) Å	µ = 0.17 mm⁻¹
c = 18.4994 (14) Å	T = 296 K
β = 129.451 (2)°	Prism, colourless
V = 3634.6 (4) Å³	0.30 × 0.25 × 0.22 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	4354 independent reflections
Radiation source: fine-focus sealed tube	2742 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 7.50 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ω scans	h = −27→31
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→14
T_min = 0.953, T_max = 0.968	l = −23→24
18572 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0851P)² + 3.8003P] where P = (F_o² + 2F_c²)/3
4354 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.73 e Å⁻³
8 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₈H₂₃O₄P	V = 3634.6 (4) Å³
M_r = 334.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.8545 (11) Å	µ = 0.17 mm⁻¹
b = 10.6663 (5) Å	T = 296 K
c = 18.4994 (14) Å	0.30 × 0.25 × 0.22 mm
β = 129.451 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4354 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2742 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.968	R_int = 0.031
18572 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	8 restraints
wR(F²) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.73 e Å⁻³
4354 reflections	Δρ_min = −0.63 e Å⁻³
217 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

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	Occ. (<1)
P1	0.23098 (5)	0.51952 (7)	0.48295 (5)	0.0564 (3)
O1	0.24033 (11)	0.65326 (19)	0.37591 (14)	0.0534 (7)
O2	0.17697 (15)	0.4238 (2)	0.47220 (16)	0.0809 (10)
O3	0.29721 (15)	0.4365 (2)	0.51385 (17)	0.0789 (9)
O4	0.25082 (14)	0.62304 (19)	0.54704 (14)	0.0684 (8)
C1	0.17620 (15)	0.4629 (3)	0.30222 (18)	0.0499 (9)
C2	0.1240 (2)	0.3727 (3)	0.2725 (2)	0.0713 (12)
C3	0.1151 (2)	0.2728 (4)	0.2178 (3)	0.0802 (14)
C4	0.1576 (2)	0.2619 (3)	0.1929 (2)	0.0781 (14)
C5	0.2088 (2)	0.3494 (4)	0.2220 (3)	0.0832 (16)
C6	0.21863 (19)	0.4501 (3)	0.2765 (2)	0.0656 (12)
C7	0.18743 (15)	0.5724 (3)	0.36315 (18)	0.0473 (8)
C8	0.11690 (18)	0.6435 (3)	0.3225 (2)	0.0603 (11)
C9	0.08167 (17)	0.7045 (3)	0.2292 (2)	0.0604 (11)
C10	0.1049 (2)	0.8214 (3)	0.2239 (2)	0.0742 (11)
C11	0.0723 (2)	0.8779 (4)	0.1386 (3)	0.0914 (14)
C12	0.0159 (3)	0.8215 (4)	0.0578 (3)	0.1001 (16)
C13	−0.0075 (2)	0.7068 (5)	0.0618 (3)	0.0986 (18)
C14	0.02499 (19)	0.6485 (4)	0.1464 (3)	0.0802 (14)
C15A	0.1966 (3)	0.3662 (6)	0.5570 (4)	0.1000 (17)	0.800
C16A	0.1312 (3)	0.3721 (6)	0.5486 (4)	0.1000 (17)	0.800
C17A	0.3652 (4)	0.4948 (10)	0.5515 (7)	0.130 (3)	0.700
C18A	0.4280 (4)	0.4270 (8)	0.6305 (6)	0.130 (3)	0.700
C17B	0.3660 (8)	0.434 (2)	0.6034 (12)	0.130 (3)	0.300
C15B	0.1434 (12)	0.424 (2)	0.5136 (14)	0.1000 (17)	0.200
C16B	0.1959 (13)	0.347 (2)	0.5989 (15)	0.1000 (17)	0.200
C18B	0.3938 (11)	0.497 (3)	0.5609 (19)	0.130 (3)	0.300
H1	0.241 (2)	0.719 (4)	0.403 (3)	0.0799*
H6	0.25426	0.50943	0.29577	0.0793*
H8A	0.08260	0.58537	0.31588	0.0722*
H8B	0.12741	0.70761	0.36680	0.0722*
H2	0.09468	0.37888	0.28914	0.0847*
H3	0.07968	0.21271	0.19812	0.0963*
H4	0.15139	0.19501	0.15622	0.0936*
H5	0.23811	0.34205	0.20531	0.0991*
H14	0.00846	0.57023	0.14766	0.0964*
H15A	0.23620	0.41156	0.61197	0.1200*	0.800
H15B	0.21144	0.27982	0.56195	0.1200*	0.800
H16A	0.11604	0.45783	0.54114	0.1500*	0.800
H16B	0.14165	0.33803	0.60407	0.1500*	0.800
H16C	0.09302	0.32440	0.49513	0.1500*	0.800
H17A	0.36568	0.57932	0.57130	0.1557*	0.700
H17B	0.36904	0.50098	0.50248	0.1557*	0.700
H18A	0.44289	0.46306	0.68793	0.1947*	0.700
H18B	0.46708	0.43278	0.62840	0.1947*	0.700
H18C	0.41540	0.34059	0.62738	0.1947*	0.700
H10	0.14295	0.86168	0.27863	0.0893*
H11	0.08898	0.95540	0.13628	0.1095*
H12	−0.00657	0.86058	0.00042	0.1191*
H13	−0.04578	0.66759	0.00674	0.1182*
H15C	0.09576	0.38470	0.47291	0.1200*	0.200
H15D	0.13903	0.50761	0.52946	0.1200*	0.200
H16D	0.17588	0.26456	0.59053	0.1500*	0.200
H16E	0.20506	0.38620	0.65210	0.1500*	0.200
H16F	0.24055	0.33917	0.60908	0.1500*	0.200
H17C	0.38530	0.35052	0.62670	0.1557*	0.300
H17D	0.36927	0.48414	0.64973	0.1557*	0.300
H18D	0.39393	0.43929	0.52126	0.1947*	0.300
H18E	0.44239	0.52619	0.60936	0.1947*	0.300
H18F	0.36325	0.56736	0.52431	0.1947*	0.300

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0822 (6)	0.0449 (4)	0.0468 (4)	−0.0038 (4)	0.0432 (4)	−0.0023 (3)
O1	0.0690 (13)	0.0474 (11)	0.0556 (11)	−0.0050 (10)	0.0452 (10)	−0.0051 (9)
O2	0.122 (2)	0.0731 (15)	0.0634 (14)	−0.0310 (14)	0.0663 (15)	−0.0082 (12)
O3	0.0938 (18)	0.0634 (14)	0.0675 (14)	0.0183 (13)	0.0456 (13)	0.0055 (12)
O4	0.1092 (18)	0.0490 (12)	0.0520 (12)	−0.0039 (12)	0.0535 (12)	−0.0053 (9)
C1	0.0603 (16)	0.0497 (16)	0.0407 (13)	0.0008 (13)	0.0326 (13)	−0.0008 (11)
C2	0.078 (2)	0.074 (2)	0.069 (2)	−0.0178 (18)	0.0501 (18)	−0.0185 (17)
C3	0.089 (3)	0.071 (2)	0.068 (2)	−0.025 (2)	0.044 (2)	−0.0217 (18)
C4	0.097 (3)	0.066 (2)	0.058 (2)	0.000 (2)	0.043 (2)	−0.0160 (16)
C5	0.097 (3)	0.090 (3)	0.082 (2)	−0.004 (2)	0.066 (2)	−0.025 (2)
C6	0.077 (2)	0.069 (2)	0.068 (2)	−0.0109 (17)	0.0541 (18)	−0.0174 (16)
C7	0.0609 (16)	0.0482 (15)	0.0432 (13)	−0.0041 (13)	0.0379 (13)	−0.0029 (11)
C8	0.0692 (19)	0.071 (2)	0.0582 (17)	0.0050 (16)	0.0487 (16)	0.0000 (15)
C9	0.0586 (18)	0.071 (2)	0.0551 (17)	0.0118 (15)	0.0378 (15)	0.0033 (15)
C10	0.079 (2)	0.066 (2)	0.0573 (19)	0.0130 (18)	0.0338 (17)	0.0025 (16)
C11	0.101 (3)	0.071 (2)	0.071 (2)	0.013 (2)	0.040 (2)	0.0162 (19)
C12	0.102 (3)	0.099 (3)	0.060 (2)	0.015 (3)	0.033 (2)	0.018 (2)
C13	0.076 (3)	0.118 (4)	0.057 (2)	−0.003 (3)	0.0213 (19)	0.003 (2)
C14	0.066 (2)	0.095 (3)	0.067 (2)	−0.007 (2)	0.0364 (18)	0.004 (2)
C15A	0.125 (3)	0.104 (3)	0.091 (3)	−0.004 (3)	0.078 (3)	0.017 (2)
C16A	0.125 (3)	0.104 (3)	0.091 (3)	−0.004 (3)	0.078 (3)	0.017 (2)
C17A	0.084 (4)	0.133 (4)	0.136 (5)	0.020 (4)	0.053 (4)	0.032 (3)
C18A	0.084 (4)	0.133 (4)	0.136 (5)	0.020 (4)	0.053 (4)	0.032 (3)
C17B	0.084 (4)	0.133 (4)	0.136 (5)	0.020 (4)	0.053 (4)	0.032 (3)
C15B	0.125 (3)	0.104 (3)	0.091 (3)	−0.004 (3)	0.078 (3)	0.017 (2)
C16B	0.125 (3)	0.104 (3)	0.091 (3)	−0.004 (3)	0.078 (3)	0.017 (2)
C18B	0.084 (4)	0.133 (4)	0.136 (5)	0.020 (4)	0.053 (4)	0.032 (3)

Geometric parameters (Å, º) top

P1—O2	1.554 (4)	C4—H4	0.9300
P1—O3	1.568 (4)	C5—H5	0.9300
P1—O4	1.461 (2)	C6—H6	0.9300
P1—C7	1.839 (3)	C8—H8A	0.9700
O1—C7	1.419 (5)	C8—H8B	0.9700
O2—C15A	1.458 (7)	C10—H10	0.9300
O2—C15B	1.42 (3)	C11—H11	0.9300
O3—C17A	1.438 (12)	C12—H12	0.9300
O3—C17B	1.408 (19)	C13—H13	0.9300
O1—H1	0.86 (4)	C14—H14	0.9300
C1—C2	1.382 (6)	C15A—H15A	0.9700
C1—C7	1.524 (4)	C15A—H15B	0.9700
C1—C6	1.372 (6)	C15B—H15C	0.9700
C2—C3	1.390 (6)	C15B—H15D	0.9600
C3—C4	1.359 (8)	C16A—H16A	0.9600
C4—C5	1.348 (7)	C16A—H16C	0.9600
C5—C6	1.387 (6)	C16A—H16B	0.9600
C7—C8	1.537 (6)	C16B—H16E	0.9600
C8—C9	1.505 (4)	C16B—H16D	0.9700
C9—C14	1.378 (5)	C16B—H16F	0.9600
C9—C10	1.393 (5)	C17A—H17A	0.9700
C10—C11	1.378 (5)	C17A—H17B	0.9700
C11—C12	1.360 (6)	C17B—H17C	0.9700
C12—C13	1.366 (8)	C17B—H17D	0.9700
C13—C14	1.377 (6)	C18A—H18A	0.9600
C15A—C16A	1.468 (12)	C18A—H18B	0.9600
C15B—C16B	1.49 (3)	C18A—H18C	0.9600
C17A—C18A	1.456 (14)	C18B—H18D	0.9600
C17B—C18B	1.47 (4)	C18B—H18E	0.9600
C2—H2	0.9300	C18B—H18F	0.9600
C3—H3	0.9300

O2—P1—O3	103.70 (16)	C11—C10—H10	120.00
O2—P1—O4	114.51 (19)	C10—C11—H11	120.00
O2—P1—C7	105.05 (15)	C12—C11—H11	120.00
O3—P1—O4	113.52 (16)	C11—C12—H12	120.00
O3—P1—C7	106.21 (17)	C13—C12—H12	120.00
O4—P1—C7	112.93 (13)	C12—C13—H13	120.00
P1—O2—C15A	117.8 (3)	C14—C13—H13	120.00
P1—O2—C15B	129.6 (9)	C9—C14—H14	120.00
P1—O3—C17A	119.8 (5)	C13—C14—H14	120.00
P1—O3—C17B	126.2 (9)	O2—C15A—H15A	111.00
C7—O1—H1	106 (4)	O2—C15A—H15B	111.00
C2—C1—C6	118.0 (3)	C16A—C15A—H15A	111.00
C2—C1—C7	121.2 (4)	C16A—C15A—H15B	111.00
C6—C1—C7	120.7 (3)	H15A—C15A—H15B	109.00
C1—C2—C3	120.4 (5)	O2—C15B—H15D	112.00
C2—C3—C4	120.7 (4)	C16B—C15B—H15C	111.00
C3—C4—C5	119.2 (4)	O2—C15B—H15C	111.00
C4—C5—C6	121.2 (5)	H15C—C15B—H15D	110.00
C1—C6—C5	120.5 (4)	C16B—C15B—H15D	112.00
P1—C7—O1	102.96 (19)	C15A—C16A—H16B	110.00
P1—C7—C8	110.2 (3)	C15A—C16A—H16A	110.00
O1—C7—C1	108.0 (3)	C15A—C16A—H16C	110.00
P1—C7—C1	110.8 (2)	H16A—C16A—H16B	109.00
C1—C7—C8	113.1 (3)	H16A—C16A—H16C	109.00
O1—C7—C8	111.3 (3)	H16B—C16A—H16C	109.00
C7—C8—C9	114.5 (4)	C15B—C16B—H16E	110.00
C8—C9—C10	120.7 (3)	C15B—C16B—H16F	110.00
C8—C9—C14	121.7 (3)	C15B—C16B—H16D	110.00
C10—C9—C14	117.6 (3)	H16D—C16B—H16E	109.00
C9—C10—C11	120.8 (3)	H16D—C16B—H16F	109.00
C10—C11—C12	120.6 (4)	H16E—C16B—H16F	110.00
C11—C12—C13	119.3 (4)	O3—C17A—H17A	109.00
C12—C13—C14	120.8 (4)	O3—C17A—H17B	109.00
C9—C14—C13	120.9 (4)	C18A—C17A—H17A	109.00
O2—C15A—C16A	106.0 (5)	C18A—C17A—H17B	109.00
O2—C15B—C16B	101 (2)	H17A—C17A—H17B	108.00
O3—C17A—C18A	113.3 (8)	O3—C17B—H17C	114.00
O3—C17B—C18B	87.0 (15)	C18B—C17B—H17D	114.00
C1—C2—H2	120.00	O3—C17B—H17D	114.00
C3—C2—H2	120.00	C18B—C17B—H17C	114.00
C2—C3—H3	120.00	H17C—C17B—H17D	111.00
C4—C3—H3	120.00	C17A—C18A—H18B	110.00
C3—C4—H4	120.00	C17A—C18A—H18C	109.00
C5—C4—H4	120.00	C17A—C18A—H18A	109.00
C4—C5—H5	119.00	H18A—C18A—H18C	109.00
C6—C5—H5	119.00	H18B—C18A—H18C	110.00
C1—C6—H6	120.00	H18A—C18A—H18B	109.00
C5—C6—H6	120.00	C17B—C18B—H18D	110.00
C7—C8—H8A	109.00	C17B—C18B—H18E	110.00
C7—C8—H8B	109.00	C17B—C18B—H18F	110.00
C9—C8—H8A	109.00	H18D—C18B—H18E	109.00
C9—C8—H8B	109.00	H18D—C18B—H18F	109.00
H8A—C8—H8B	108.00	H18E—C18B—H18F	109.00
C9—C10—H10	120.00

O3—P1—O2—C15A	69.5 (4)	C2—C1—C7—O1	−175.6 (3)
O4—P1—O2—C15A	−54.7 (4)	C2—C1—C7—C8	−52.0 (4)
C7—P1—O2—C15A	−179.2 (4)	C6—C1—C7—P1	−106.6 (3)
O2—P1—O3—C17A	−165.6 (5)	C6—C1—C7—O1	5.5 (4)
O4—P1—O3—C17A	−40.8 (5)	C6—C1—C7—C8	129.1 (3)
C7—P1—O3—C17A	83.9 (5)	C1—C2—C3—C4	0.2 (6)
O2—P1—C7—O1	−176.6 (2)	C2—C3—C4—C5	0.0 (6)
O2—P1—C7—C1	−61.4 (3)	C3—C4—C5—C6	−0.2 (6)
O2—P1—C7—C8	64.6 (3)	C4—C5—C6—C1	0.0 (6)
O3—P1—C7—O1	−67.1 (2)	P1—C7—C8—C9	172.9 (2)
O3—P1—C7—C1	48.1 (3)	O1—C7—C8—C9	59.3 (3)
O3—P1—C7—C8	174.1 (2)	C1—C7—C8—C9	−62.4 (4)
O4—P1—C7—O1	57.9 (3)	C7—C8—C9—C10	−83.0 (5)
O4—P1—C7—C1	173.1 (3)	C7—C8—C9—C14	98.0 (5)
O4—P1—C7—C8	−60.9 (3)	C8—C9—C10—C11	−179.4 (5)
P1—O2—C15A—C16A	134.5 (4)	C14—C9—C10—C11	−0.4 (7)
P1—O3—C17A—C18A	139.4 (7)	C8—C9—C14—C13	178.7 (5)
C6—C1—C2—C3	−0.3 (5)	C10—C9—C14—C13	−0.3 (8)
C7—C1—C2—C3	−179.3 (3)	C9—C10—C11—C12	1.1 (8)
C2—C1—C6—C5	0.2 (5)	C10—C11—C12—C13	−1.1 (10)
C7—C1—C6—C5	179.2 (3)	C11—C12—C13—C14	0.4 (10)
C2—C1—C7—P1	72.4 (4)	C12—C13—C14—C9	0.3 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.86 (4)	1.87 (4)	2.718 (3)	170 (5)
C10—H10···O4ⁱ	0.93	2.54	3.409 (4)	155
C16A—H16B···CgAⁱⁱ	0.97	2.94	3.657 (8)	133

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃O₄P
M_r	334.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	23.8545 (11), 10.6663 (5), 18.4994 (14)
β (°)	129.451 (2)
V (Å³)	3634.6 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.30 × 0.25 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.953, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	18572, 4354, 2742
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.198, 1.05
No. of reflections	4354
No. of parameters	217
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.63

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.86 (4)	1.87 (4)	2.718 (3)	170 (5)
C10—H10···O4ⁱ	0.93	2.54	3.409 (4)	155
C16A—H16B···CgAⁱⁱ	0.97	2.94	3.657 (8)	133

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer and for technical support, respectively.

References

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