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

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

doi:10.1107/S1600536809029808

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2051

doi:10.1107/S1600536809029808

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Dimethyl (1-hydroxy-1,2-diphenylethyl)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 25 July 2009; accepted 27 July 2009; online 31 July 2009)

In the crystal of the title compound, C₁₆H₁₉O₄P, the molecules are dimerized with R₂²(10) ring motifs through the hydroxy and P=O O atoms. The dihedral angle between the aromatic rings is 66.89 (9)°. There are π–π interactions [centroid–centroid distance = 3.9669 (16) Å] between the benzene rings of adjacent benzyl groups. A C—H⋯π interaction between the aromatic rings where C—H is from a benzyl group is also present.

Related literature

For the preparation and crystal structures of α-hydroxy phosphonates, see: Acar et al. (2009a ,b ); Tahir et al. (2007 , 2009a ,b ). For an isomer of the title compouns, see: Acar et al. (2009a). For ring-motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₉O₄P
M_r = 306.28
Monoclinic, P 2₁ /c
a = 8.4767 (5) Å
b = 15.8978 (10) Å
c = 13.3888 (7) Å
β = 119.397 (3)°
V = 1571.97 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.963, T_max = 0.974
16757 measured reflections
3861 independent reflections
2183 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 1.01
3861 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.79 (2)	1.92 (2)	2.684 (2)	164 (3)
C12—H12⋯CgAⁱⁱ	0.93	2.86	3.755 (4)	163
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . CgA is the centroid of the C1–C6 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 for Windows (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/S1600536809029808/at2852sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029808/at2852Isup2.hkl

checkCIF report

Comment top

We have reported preparation and crystal structures containing α-Hydroxy phosphonates (Tahir et al., 2007, 2009a,b) and (Acar et al. 2009a,b). The title compound (I, Fig. 1) is chemically isomer of (II) (Acar et al., 2009a). The crystals of title compound were selected from the sample of Acar et al., 2009a present at low yield.

The difference of (I) with (II) exist due to various reasons. In (I) the dihedral angle between the aromatic rings A (C1–C6) and B (C9–C14) is 66.89 (9)° compared to 72.28 (11)°. The distorted tetrahedral geometry around C7 have range of angles 104.15 (13)° to 113.43 (16)° instead of 104.4 (2)° to 112.8 (2)°. There exist small variations in bond lengths e.g, P1—C7 is 1.835 (2) Å compared to 1.845 (3) Å. In (I) the molecules form dimers only and dimers are not linked to each other as observed in (II). The dimers (Fig. 2) are formed due to intermolecular H-bonding of O—H···O type with ring motif R₂²(10) (Bernstein et al., 1995). There exist C—H···π interaction between the two aromatic rings (Table 1) and π–π interaction at a distance of 3.9669 (16) Å between the centroids of aromatic ring B with CgB···CgBⁱ [symmetry code: (i) 1 - x, 1 - y, -z].

Related literature top

For the preparation and crystal structures of α-hydroxy phosphonates, see: Acar et al. (2009a,b); Tahir et al. (2007, 2009a,b). For an isomer of the title compouns, see: Acar et al. (2009a). For ring-motifs, see: Bernstein et al. (1995).

Experimental top

The preparation is reported in Acar et al., 2009a.

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 for Windows (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 the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form dimers.

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

Crystal data top

C₁₆H₁₉O₄P	F(000) = 648
M_r = 306.28	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3861 reflections
a = 8.4767 (5) Å	θ = 2.8–28.3°
b = 15.8978 (10) Å	µ = 0.19 mm⁻¹
c = 13.3888 (7) Å	T = 296 K
β = 119.397 (3)°	Prismatic, colourless
V = 1571.97 (17) Å³	0.25 × 0.18 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3861 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 2.8°
ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→21
T_min = 0.963, T_max = 0.974	l = −17→17
16757 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0517P)² + 0.2804P] where P = (F_o² + 2F_c²)/3
3861 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₉O₄P	V = 1571.97 (17) Å³
M_r = 306.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4767 (5) Å	µ = 0.19 mm⁻¹
b = 15.8978 (10) Å	T = 296 K
c = 13.3888 (7) Å	0.25 × 0.18 × 0.15 mm
β = 119.397 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3861 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2183 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.974	R_int = 0.043
16757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.27 e Å⁻³
3861 reflections	Δρ_min = −0.28 e Å⁻³
195 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
P1	1.16204 (7)	0.38185 (3)	0.45831 (5)	0.0440 (2)
O1	0.83863 (19)	0.37902 (9)	0.43056 (13)	0.0455 (5)
O2	1.20677 (18)	0.46360 (9)	0.51545 (14)	0.0587 (5)
O3	1.25054 (19)	0.36505 (11)	0.38159 (14)	0.0660 (6)
O4	1.2208 (2)	0.30558 (10)	0.54132 (14)	0.0762 (6)
C1	0.8814 (2)	0.27486 (12)	0.31946 (16)	0.0393 (6)
C2	0.9200 (3)	0.24523 (14)	0.23689 (18)	0.0528 (8)
C3	0.8833 (3)	0.16197 (17)	0.2000 (2)	0.0636 (9)
C4	0.8104 (3)	0.10853 (16)	0.2456 (2)	0.0684 (9)
C5	0.7733 (3)	0.13707 (15)	0.3286 (2)	0.0658 (9)
C6	0.8080 (3)	0.21952 (13)	0.3647 (2)	0.0512 (8)
C7	0.9192 (2)	0.36591 (12)	0.36066 (16)	0.0371 (6)
C8	0.8505 (3)	0.43043 (13)	0.26211 (17)	0.0444 (7)
C9	0.6550 (3)	0.41928 (13)	0.17226 (18)	0.0456 (7)
C10	0.6074 (4)	0.38734 (16)	0.0652 (2)	0.0691 (9)
C11	0.4283 (5)	0.37485 (19)	−0.0165 (2)	0.0922 (11)
C12	0.2939 (4)	0.39384 (18)	0.0079 (3)	0.0883 (11)
C13	0.3378 (3)	0.42615 (17)	0.1120 (3)	0.0762 (10)
C14	0.5166 (3)	0.43991 (14)	0.1941 (2)	0.0565 (8)
C15	1.4435 (3)	0.36510 (19)	0.4291 (3)	0.0795 (11)
C16	1.3067 (5)	0.3068 (2)	0.6594 (3)	0.1003 (15)
H1	0.844 (3)	0.4272 (14)	0.4467 (19)	0.0546*
H2	0.97088	0.28115	0.20561	0.0634*
H3	0.90891	0.14285	0.14384	0.0763*
H4	0.78583	0.05302	0.22077	0.0821*
H5	0.72445	0.10061	0.36055	0.0789*
H6	0.78141	0.23814	0.42066	0.0615*
H8A	0.86629	0.48651	0.29419	0.0533*
H8B	0.92463	0.42629	0.22556	0.0533*
H10	0.69787	0.37396	0.04765	0.0829*
H11	0.39936	0.35349	−0.08820	0.1106*
H12	0.17327	0.38469	−0.04633	0.1061*
H13	0.24629	0.43934	0.12862	0.0914*
H14	0.54368	0.46321	0.26443	0.0678*
H15A	1.48869	0.42133	0.45095	0.1196*
H15B	1.47329	0.34472	0.37294	0.1196*
H15C	1.49759	0.32926	0.49535	0.1196*
H16A	1.42483	0.28223	0.68969	0.1505*
H16B	1.23695	0.27518	0.68516	0.1505*
H16C	1.31802	0.36388	0.68549	0.1505*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0404 (3)	0.0400 (3)	0.0461 (3)	0.0007 (2)	0.0169 (2)	−0.0084 (3)
O1	0.0601 (9)	0.0362 (8)	0.0526 (9)	−0.0011 (7)	0.0373 (8)	−0.0051 (7)
O2	0.0475 (8)	0.0454 (9)	0.0735 (10)	−0.0043 (7)	0.0221 (8)	−0.0213 (8)
O3	0.0412 (8)	0.0905 (13)	0.0680 (10)	−0.0029 (8)	0.0282 (8)	−0.0230 (9)
O4	0.0837 (12)	0.0515 (11)	0.0533 (10)	0.0049 (8)	0.0027 (9)	0.0020 (8)
C1	0.0361 (10)	0.0373 (11)	0.0383 (11)	0.0022 (8)	0.0134 (9)	−0.0029 (9)
C2	0.0604 (13)	0.0521 (14)	0.0467 (12)	0.0047 (10)	0.0268 (11)	−0.0044 (11)
C3	0.0687 (16)	0.0608 (17)	0.0498 (14)	0.0114 (12)	0.0203 (12)	−0.0182 (13)
C4	0.0593 (14)	0.0453 (15)	0.0803 (19)	−0.0029 (11)	0.0185 (14)	−0.0198 (14)
C5	0.0632 (15)	0.0430 (14)	0.0912 (19)	−0.0100 (11)	0.0380 (15)	−0.0106 (14)
C6	0.0529 (12)	0.0425 (13)	0.0643 (14)	−0.0049 (10)	0.0334 (11)	−0.0079 (11)
C7	0.0403 (10)	0.0355 (11)	0.0379 (10)	−0.0005 (8)	0.0211 (9)	−0.0020 (9)
C8	0.0472 (12)	0.0397 (12)	0.0494 (12)	−0.0004 (9)	0.0261 (10)	0.0038 (10)
C9	0.0516 (12)	0.0355 (12)	0.0430 (12)	0.0005 (9)	0.0181 (10)	0.0072 (10)
C10	0.0815 (18)	0.0677 (17)	0.0464 (14)	0.0126 (14)	0.0223 (13)	0.0061 (13)
C11	0.108 (2)	0.074 (2)	0.0480 (16)	0.0089 (18)	0.0023 (17)	−0.0025 (15)
C12	0.0672 (18)	0.0561 (18)	0.084 (2)	−0.0079 (14)	−0.0073 (16)	0.0017 (16)
C13	0.0484 (14)	0.0614 (18)	0.096 (2)	0.0007 (12)	0.0179 (14)	0.0064 (16)
C14	0.0518 (13)	0.0459 (14)	0.0631 (15)	0.0036 (10)	0.0215 (12)	0.0023 (12)
C15	0.0484 (14)	0.101 (2)	0.093 (2)	−0.0057 (14)	0.0377 (14)	−0.0070 (17)
C16	0.121 (3)	0.102 (3)	0.0607 (18)	0.000 (2)	0.0312 (19)	0.0099 (18)

Geometric parameters (Å, º) top

P1—O2	1.4606 (16)	C12—C13	1.355 (5)
P1—O3	1.5639 (19)	C13—C14	1.385 (4)
P1—O4	1.5524 (17)	C2—H2	0.9300
P1—C7	1.835 (2)	C3—H3	0.9300
O1—C7	1.419 (3)	C4—H4	0.9300
O3—C15	1.435 (4)	C5—H5	0.9300
O4—C16	1.378 (4)	C6—H6	0.9300
O1—H1	0.79 (2)	C8—H8A	0.9700
C1—C6	1.378 (3)	C8—H8B	0.9700
C1—C7	1.526 (3)	C10—H10	0.9300
C1—C2	1.381 (3)	C11—H11	0.9300
C2—C3	1.394 (3)	C12—H12	0.9300
C3—C4	1.359 (4)	C13—H13	0.9300
C4—C5	1.372 (4)	C14—H14	0.9300
C5—C6	1.378 (3)	C15—H15A	0.9600
C7—C8	1.542 (3)	C15—H15B	0.9600
C8—C9	1.506 (3)	C15—H15C	0.9600
C9—C14	1.381 (4)	C16—H16A	0.9600
C9—C10	1.381 (3)	C16—H16B	0.9600
C10—C11	1.382 (5)	C16—H16C	0.9600
C11—C12	1.364 (6)

O1···O2	3.059 (2)	C5···H16A^v	2.9000
O1···O4	3.056 (3)	C6···H16A^v	2.9300
O1···C14	3.151 (3)	C8···H2	2.8300
O1···C15ⁱ	3.347 (4)	C13···H5^vii	2.8800
O1···O2ⁱⁱ	2.684 (2)	C14···H15Bⁱ	3.0000
O2···O1ⁱⁱ	2.684 (2)	H1···O2	2.80 (3)
O2···O1	3.059 (2)	H1···H8A	2.3400
O3···C2	3.147 (3)	H1···H14	2.5800
O4···C6	3.404 (3)	H1···O2ⁱⁱ	1.92 (2)
O4···C12ⁱⁱⁱ	3.303 (3)	H2···O3	2.7300
O4···O1	3.056 (3)	H2···C8	2.8300
O1···H6	2.2800	H2···H8B	2.3800
O1···H14	2.7400	H2···H16B^viii	2.5600
O1···H15Bⁱ	2.8500	H3···O1^viii	2.6400
O1···H3^iv	2.6400	H5···C13^ix	2.8800
O2···H1	2.80 (3)	H5···H13^ix	2.5700
O2···H1ⁱⁱ	1.92 (2)	H6···O1	2.2800
O2···H16C	2.5500	H8A···H1	2.3400
O2···H14ⁱⁱ	2.9000	H8A···H14	2.5900
O3···H8B	2.7000	H8B···O3	2.7000
O3···H2	2.7300	H8B···C2	2.8800
O4···H15C	2.7300	H8B···H2	2.3800
C1···C10	3.524 (3)	H8B···H10	2.3600
C2···O3	3.147 (3)	H10···C2	3.0800
C2···C9	3.398 (3)	H10···H8B	2.3600
C2···C10	3.381 (4)	H12···C4^v	2.9700
C5···C16^v	3.574 (5)	H12···C5^v	2.9700
C6···O4	3.404 (3)	H13···H5^vii	2.5700
C9···C2	3.398 (3)	H14···O1	2.7400
C10···C2	3.381 (4)	H14···H1	2.5800
C10···C1	3.524 (3)	H14···H8A	2.5900
C12···O4^v	3.303 (3)	H14···O2ⁱⁱ	2.9000
C14···O1	3.151 (3)	H15B···O1^vi	2.8500
C15···O1^vi	3.347 (4)	H15B···C14^vi	3.0000
C16···C5ⁱⁱⁱ	3.574 (5)	H15C···O4	2.7300
C2···H10	3.0800	H15C···C3ⁱⁱⁱ	3.0700
C2···H8B	2.8800	H16A···C5ⁱⁱⁱ	2.9000
C3···H15C^v	3.0700	H16A···C6ⁱⁱⁱ	2.9300
C4···H12ⁱⁱⁱ	2.9700	H16B···H2^iv	2.5600
C5···H12ⁱⁱⁱ	2.9700	H16C···O2	2.5500

O2—P1—O3	114.27 (10)	C4—C3—H3	120.00
O2—P1—O4	114.23 (9)	C3—C4—H4	120.00
O2—P1—C7	114.08 (10)	C5—C4—H4	120.00
O3—P1—O4	104.36 (10)	C4—C5—H5	120.00
O3—P1—C7	103.91 (9)	C6—C5—H5	120.00
O4—P1—C7	104.81 (10)	C1—C6—H6	119.00
P1—O3—C15	121.25 (18)	C5—C6—H6	119.00
P1—O4—C16	127.83 (17)	C7—C8—H8A	109.00
C7—O1—H1	109.9 (19)	C7—C8—H8B	109.00
C2—C1—C6	118.02 (19)	C9—C8—H8A	109.00
C6—C1—C7	120.45 (18)	C9—C8—H8B	109.00
C2—C1—C7	121.52 (18)	H8A—C8—H8B	108.00
C1—C2—C3	120.6 (2)	C9—C10—H10	119.00
C2—C3—C4	120.4 (2)	C11—C10—H10	119.00
C3—C4—C5	119.5 (2)	C10—C11—H11	120.00
C4—C5—C6	120.3 (2)	C12—C11—H11	120.00
C1—C6—C5	121.2 (2)	C11—C12—H12	120.00
P1—C7—C1	110.58 (13)	C13—C12—H12	120.00
P1—C7—C8	109.76 (15)	C12—C13—H13	119.00
O1—C7—C1	107.11 (15)	C14—C13—H13	119.00
O1—C7—C8	111.40 (17)	C9—C14—H14	120.00
C1—C7—C8	113.43 (16)	C13—C14—H14	120.00
P1—C7—O1	104.15 (13)	O3—C15—H15A	109.00
C7—C8—C9	114.24 (19)	O3—C15—H15B	109.00
C8—C9—C10	121.2 (3)	O3—C15—H15C	109.00
C10—C9—C14	117.5 (2)	H15A—C15—H15B	110.00
C8—C9—C14	121.3 (2)	H15A—C15—H15C	109.00
C9—C10—C11	121.5 (3)	H15B—C15—H15C	109.00
C10—C11—C12	120.0 (3)	O4—C16—H16A	109.00
C11—C12—C13	119.4 (3)	O4—C16—H16B	109.00
C12—C13—C14	121.2 (3)	O4—C16—H16C	109.00
C9—C14—C13	120.5 (2)	H16A—C16—H16B	110.00
C1—C2—H2	120.00	H16A—C16—H16C	109.00
C3—C2—H2	120.00	H16B—C16—H16C	109.00
C2—C3—H3	120.00

O2—P1—O3—C15	59.8 (2)	C2—C1—C7—C8	47.6 (3)
O4—P1—O3—C15	−65.7 (2)	C6—C1—C7—P1	103.4 (2)
C7—P1—O3—C15	−175.28 (19)	C6—C1—C7—O1	−9.5 (3)
O2—P1—O4—C16	0.5 (3)	C6—C1—C7—C8	−132.8 (2)
O3—P1—O4—C16	126.0 (3)	C1—C2—C3—C4	−0.6 (4)
C7—P1—O4—C16	−125.1 (3)	C2—C3—C4—C5	−0.1 (4)
O2—P1—C7—O1	−56.34 (15)	C3—C4—C5—C6	0.6 (4)
O2—P1—C7—C1	−171.09 (13)	C4—C5—C6—C1	−0.5 (4)
O2—P1—C7—C8	63.03 (17)	P1—C7—C8—C9	176.07 (16)
O3—P1—C7—O1	178.59 (12)	O1—C7—C8—C9	−69.1 (2)
O3—P1—C7—C1	63.84 (15)	C1—C7—C8—C9	51.8 (3)
O3—P1—C7—C8	−62.04 (16)	C7—C8—C9—C10	−106.8 (2)
O4—P1—C7—O1	69.34 (14)	C7—C8—C9—C14	72.6 (3)
O4—P1—C7—C1	−45.42 (15)	C8—C9—C10—C11	178.2 (2)
O4—P1—C7—C8	−171.30 (14)	C14—C9—C10—C11	−1.2 (4)
C6—C1—C2—C3	0.8 (3)	C8—C9—C14—C13	−177.5 (2)
C7—C1—C2—C3	−179.6 (2)	C10—C9—C14—C13	2.0 (3)
C2—C1—C6—C5	−0.2 (3)	C9—C10—C11—C12	−0.3 (4)
C7—C1—C6—C5	−179.9 (2)	C10—C11—C12—C13	1.0 (4)
C2—C1—C7—P1	−76.2 (2)	C11—C12—C13—C14	−0.2 (4)
C2—C1—C7—O1	170.90 (19)	C12—C13—C14—C9	−1.3 (4)

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x+1, −y+1/2, z+1/2; (iv) x, −y+1/2, z+1/2; (v) x−1, −y+1/2, z−1/2; (vi) x+1, y, z; (vii) −x+1, y+1/2, −z+1/2; (viii) x, −y+1/2, z−1/2; (ix) −x+1, 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···O2ⁱⁱ	0.79 (2)	1.92 (2)	2.684 (2)	164 (3)
C6—H6···O1	0.93	2.28	2.655 (3)	103.00
C16—H16C···O2	0.96	2.55	3.007 (4)	110.00
C12—H12···CgA^v	0.93	2.86	3.755 (4)	163.00

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

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)	8.4767 (5), 15.8978 (10), 13.3888 (7)
β (°)	119.397 (3)
V (Å³)	1571.97 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.25 × 0.18 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.963, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	16757, 3861, 2183
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.01
No. of reflections	3861
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (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···O2ⁱ	0.79 (2)	1.92 (2)	2.684 (2)	164 (3)
C6—H6···O1	0.93	2.28	2.655 (3)	103.00
C16—H16C···O2	0.96	2.55	3.007 (4)	110.00
C12—H12···CgAⁱⁱ	0.93	2.86	3.755 (4)	163.00

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