A new route for the synthesis of phosphate esters: 2,2'-[benzene-1,2-diylbis(­oxy)]bis­(5,5-dimethyl-1,3,2-dioxaphosphinane) 2,2'-dioxide

Podand-type ligands are an inter­esting class of acyclic ligands which can form host-guest complexes with many transition metals and can undergo conformational changes. Organic phosphates are components of many biological mol­ecules. A new route for the synthesis of phosphate esters with a retained six-membered ring has been used to prepare 2,2'-[benzene-1,2-diylbis(­oxy)]bis­(5,5-dimethyl-1,3,2-dioxaphosphinane) 2,2'-dioxide, C₆H₄{O[cyclo-P(O)OCH₂CMe₂CH₂O]}₂ or C₁₆H₂₄O₈P₂, (1), 2-[(2'-hy­droxy­biphenyl-2-yl)­oxy]-5,5-di­methyl-1,3,2-dioxaphosphinane 2-oxide, [cyclo-P(O)OCH₂CMe₂CH₂O](2,2'-OC₆H₄-C₆H₄OH), (2), and oxybis(5,5-dimethyl-1,3,2-dioxaphosphinane) 2,2'-dioxide, O[cyclo-P(O)OCH₂CMe₂CH₂O]₂, (3). Compound (1) is novel, whereas the results for compounds (2) and (3) have been reported previously, but we record here our results for compound (3), which we find are more precise and accurate than those currently reported in the literature. In (1), two cyclo-P(O)OCH₂CMe₂CH₂O groups are linked through a catechol group. The conformations about the two catechol O atoms are quite different, viz. one C-C-O-P torsion angle is -169.11 (11)° and indicates a trans arrangement, whereas the other C-C-O-P torsion angle is 92.48 (16)°, showing a gauche conformation. Both six-membered POCCCO rings have good chair-shape conformations. In both the trans and gauche conformations, the catechol O atoms are in the axial sites and the short P=O bonds are equatorially bound.

S1. Introduction

Podand-type ligands are an inter­esting class of acyclic ligands (Fenton, 1987). They have potential donor atoms, such as oxygen, nitro­gen and sulfur, which can form host–guest complexes with many transition metals and can undergo conformational changes due to high flexibility (Oepen et al., 1978; Vögtle et al., 1981; Kumar et al., 2013). These metal complexes can be stabilized by the presence of spheroidal cavities. Such compounds can catalyze reactions and have a high significance in materials science (Neogi & Bharadwaj, 2006). Furthermore, organic phosphates have special importance as they are components of many biological molecules, such as nucleic acids, vitamins and enzymes, which perform essential functions in key life processes (Timosheva et al. 2005).

Inter­estingly, from hydrolysis studies, Kumara Swamy has noted the formation of several phosphate esters of type I while investigating penta- and hexacoordinated cyclic phospho­ranes with six- and higher-membered rings (Kumara Swamy et al., 1998). These reactions are helpful in determining the hydrolytic stability of phospho­rane rings (Kumara Swamy et al., 2000). Compound (2) (literature yield 19%) and other similar compounds were synthesized previously by us through hydrolysis of spiro­phospho­ranes with a saturated 1,3,2-dioxa­phospho­rine ring (see Scheme 1). An alternative route for the synthesis of similar compounds was explored by reacting ClP(O)(OCH₂CMe₂CH₂O) with an equimolar amount of diol in the presence of Et₃N (Kumara Swamy et al., 1998).

In this paper, we use a new method to synthesize 2,2'-[benzene-1,2-diylbis(­oxy)]bis­(5,5-di­methyl-1,3,2-dioxaphosphinane) 2,2'-dioxide, C₆H₄{O[cyclo-P(O)OCH₂CMe₂CH₂O]}₂, (1), 2-[(2'-hy­droxy­biphenyl-2-yl)­oxy]-5,5-di­methyl-1,3,2-dioxaphosphinane 2-oxide, [cyclo-P(O)OCH₂CMe₂CH₂O](2,2'-OC₆H₄–C₆H₄OH), (2), and oxybis(5,5-di­methyl-1,3,2-dioxaphosphinane) 2,2'-dioxide, O[cyclo-P(O)OCH₂CMe₂CH₂O]₂, (3). This involves the use of cyclo-[P(O)(H)OCH₂CMe₂CH₂O] and the corresponding diol in the presence of N-chloro­diiso­propyl­amine (NCDA). Using this novel approach and adjusting the ratios of rea­cta­nts, one or both of the –OH groups of the diol could be reacted with thydrogen phosphite under fewer [less stringent?] air-restriction conditions.

Compounds (1), (2) and (3) are readily isolated in a pure crystalline state by reacting hydrogen phosphite and diol/ClN(ⁱPr)₂, and recrystallizing the product from di­chloro­methane and n-hexane. The side product [H₂(ⁱPr)₂N]⁺.Cl^- is easily removed by washing the precipitate with water. Our new synthetic route leading to compounds (1)–(3) in this study is illustrated in Scheme 2. A range of products can be prepared by reacting 5,5-di­methyl-1,3,2-dioxaphosphinane 2-oxide with either one mole or half a mole of the diol (as in Scheme 2).

The products were characterized by NMR and X-ray methods. The δ phospho­rus NMR values [-13.89 p.p.m. for (1), -14.26 p.p.m. for (2) and -21.13 p.p.m. for (3)] are in the expected range for tetra­coordinated phosphate esters. An inter­esting feature in the ¹H NMR spectra for the OCH₂ groups in all three compounds is illustrated in Fig. 1. A clear AX pattern is observed for compounds (1) and (3), whereas an AB pattern is observed for compound (2). This is due to hydrogen–hydrogen coupling and then ³J coupling to phospho­rus, as shown in Fig. 1. Furthermore, two separate signals are observed for the CH₃ group in 5,5-di­methyl-1,3,2-dioxaphosphinane.

S2. Experimental

Chemicals were procured from Aldrich or from local manufacturers and were purified when required. Solvents were purified according to standard procedures (Perrin et al., 1986). NMR spectra were recorded on a Bruker 400 MHz spectrometer. Chemical shifts (CDCl₃, p.p.m.) are measured against tetra­methyl­silane (¹H and ¹³C) or external 85% H₃PO₄.

S2.1. Synthesis and crystallization

N-Chloro­diiso­propyl­amine was prepared as described in the literature (Antczak et al., 1977). Preparations of [cyclo-P(O)OCH₂CMe₂CH₂O](2,2'-OC₆H₄—C₆H₄OH), (2) (Kumara Swamy et al., 1998), and O[cyclo-P(O)OCH₂CMe₂CH₂O]₂, (3) (Bukowska-Strzyzewska & Dobrowolska, 1978; Cook & White, 1976), have also been described.

S2.1.1. Preparation of 2,2'-[benzene-1,2-diylbis(­oxy)]bis­(5,5-di­methyl-1,3,2-dioxaphosphinane) 2,2'-dioxide, (1)

To an ice-cold mixture of 5,5-di­methyl-1,3,2-dioxaphosphinane 2-oxide (0.38 g, 2.53 mmol) and 1,2-di­hydroxy­benzene (0.14 g, 1.27 mmol) in dry di­ethyl ether (30 ml) was added N-chloro­diisoproyl­amine (0.34 g, 2.53 mmol) dropwise using a syringe over a period of 5 min. The mixture was brought slowly to room temperature and stirred under nitro­gen overnight. The solvent was reduced to 10 ml under vacuum and n-hexane (3 ml) was added to afford (1) and the diiso­propyl­amine hydro­chloride salt. The solid was collected, washed quickly with water (15 ml) and then dried in air. The solid was crystallized from di­chloro­methane and n-hexane (2:1 v/v) to produce a white crystalline solid (yield 0.26 g, 50%; m.p. 420–423 K). ¹H NMR (CDCl₃, 400 MHz): δ 7.36–7.06 (m, 4H, Ar—H), 4.36 (d, 4H, CH₂), 3.91 (dd, 4H, CH₂), 1.26 (s, 6H, CH₃), 0.84 (s, 6H, CH₃). ¹³C NMR (CDCl₃, 400 MHz): δ 141.05, 125.91, 121.36 (aromatic carbons), 78.59 (2C, CMe₂), 32.29 (4C, CH₂), 21.94 (2C, CH₃) 20.11 (2C, CH₃). ³¹P NMR (CDCl₃, 400 MHz): δ -13.89. Analysis calculated for C₁₆H₂₄O₈P₂: C 47.30, H 5.95%; found: C 47.43, H 6.16%.

S2.1.2. Preparation of 2-[(2'-hy­droxy­biphenyl-2-yl)­oxy]-5,5-di­methyl-1,3,2-dioxaphosphinane 2-oxide, (2)

The procedure was essentially the same as that for the preparation of (1) using 5,5-di­methyl-1,3,2-dioxaphosphinane 2-oxide (0.65 g, 4.33 mmol), 2,2'-biphenol (0.81 g, 4.33 mmol) and N-chloro­diisoproyl­amine (0.59 g, 4.33 mmol) [yield: 0.94 g, 65%; m.p. 451–454 K (literature 455 K)]. ¹H NMR (CDCl₃, 400 MHz): δ 6.94–7.66 (m, 8H, Ar—H), 5.35 (br, 1H, OH), 3.45–3.60 (m, 4H, CH₂), 1.11 (s, 3H, CH₃), 0.44 (s, 3H, CH₃). ³¹P NMR (CDCl₃, 400 MHz): δ -14.26 (literature value in DMSO + CDCl₂ is -15.1). Analysis calculated for C₁₇H₁₉O₅P: C 61.08, H 5.73%; found: C 61.19, H 5.95%.

S2.1.3. Preparation of oxybis(5,5-di­methyl-1,3,2-dioxaphosphinane) 2,2'-dioxide, (3)

The procedure was essentially the same as that for the preparation of (1) using 5,5-di­methyl-1,3,2-dioxaphosphinane 2-oxide (0.46 g, 3.06 mmol), H₂O (0.03 g, 1.53 mmol) and N-chloro­diisoproyl­amine (0.41 g, 3.06 mmol) [yield 0.26 g, 58%; m.p. 441 K (literature 461–465 K)]. ¹H NMR (CDCl₃, 400 MHz): 4.41 (d, 4H, CH₂), 3.93 (dd, 4H, CH₂), 1.26 (s, 6H, CH₃), 0.84 (s, 6H, CH₃). ³¹P NMR (CDCl₃, 400 MHz): δ -21.13. Analysis calculated for C₁₀H₂₀O₇P₂: C 38.23, H 6.24%; found: C 38.31, H 6.33%.

S2.2. Refinement

Crystal data, data collection and structure refinement details for compounds (1) and (3) are summarized in Table 1. Intensity data were measured for crystals of three compounds (1)–(3). Compound (1) is novel, where as the results for compounds (2) and (3) have been reported previously [for (2), see Kumara Swamy et al. (1998); for (3), see Cook & White (1976) and Bukowska-Strzyzewska & Dobrowolska (1978)], but we record here our results for compound (3) which we find are more precise and accurate than those currently reported in the literature. In both analyses, all H atoms were located in difference maps. In the refinements, the methyl-group H atoms were refined as rigid groups by rotation about the C—C bond to agree best with the electron density, while the remaining H atoms (coordinates and isotropic displacement parameters) were refined freely.

S3. Results and discussion

X-ray and NMR analyses of compounds (1) and (3) confirm that the six-membered phospho­rinane ring is intact and always adopts the chair conformation. The molecular structure of compound (1) (Fig. 2) confirms that the two cyclo-P(O)OCH₂CMe₂CH₂O groups are linked through a catechol group. The conformations about the two catechol O atoms are quite different, viz. the C2—C1—O1—P1 torsion angle is -169.11 (11)° and indicates a trans arrangement, whereas the C1—C2—O2—P2 angle is 92.48 (16)°, and indicates a gauche conformation. Both six-membered POCCCO rings have good chair shapes; in each, the catechol O atom is in an axial site, and the short P1—O16 and P2—O26 bonds are equatorially bound [the P═O distances are 1.4493 (13) and 1.4473 (13) Å, respectively, whereas the other P—O distances are in the range 1.5509 (13)–1.5894 (12) Å].

In compound (3), the two cyclo-P(O)OCH₂CMe₂CH₂O groups are linked through a central O atom, and are related by a pseudo-twofold symmetry axis (Fig. 3). Both six-membered rings have chair conformations. At both P atoms, the linking O3 atom is in an axial position and a shorter P═O bond is equatorially bonded; the order of P—O bond lengths in both groups is P═ O (as P1—O1 ca 1.44 Å) < P—O_ring (as P1—O11 ca 1.55 Å) < P—O_linking (as P1—O3 ca 1.60 Å).

These dimensions for (1) and (3) are very similar to those for compound (2) (Kumara Swamy et al., 1998). We also note that the angles about the P atoms are very similar, and, following the atom-numbering scheme for compound (1), find that the O16—P1—O1/O11/O15 angles in compound (1) and the corresponding angles in all three compounds are greater than the regular tetra­hedral angle (109.5°), lying in the range 111.97 (9)–115.97 (7)°. The angles corresponding to O11—P1—O15 lie in the narrow range 106.03 (12)–107.24 (6)°. The angles involving a link atom, e.g. O1 in (1), fall into two groups, viz. 100.67 (6)–101.96 (13) and 104.11 (14)–106.92 (8)°, depending on the orientation of the atom beyond the link atom, e.g. C1 is trans to O11 about the O1—P1 bond and, typically, the O1—P1—O11 angle of 100.67 (6)° is in the first group, with the least obtuse angles, and C1 is cis to O15 about the same bond and the O1—P1—O15 angle of 106.28 (7)° is in the second group.

In the phospho­rinane rings we note a consistency in the chair conformations through all the rings in compounds (1) and (3). In each ring, there are three distinct groupings of torsion angles, viz low (absolute) values in the angles about the P atom, medium values about the O—C bonds and higher values about the C—C bonds. In compound (3), the ranges of values in the two phospho­rinane rings are, respectively, -39.6 (3) to -43.6 (3), 49.9 (4) to 54.5 (4), and -55.8 (4) to 57.9 (4)°. The values in the P1-containing ring in compound (1) are very similar, but the second ring in (1) shows more extreme values, viz. 34.44 (14) to -35.32 (14), -49.53 (18) to 51.53 (19) and 59.36 (19) to -60.63 (19)° for the three pairs; here the chair is slightly flatter around the P atoms and deeper at the opposite end.

There are few short inter­molecular contacts in either of compounds (1) and (3). The shortest inter­molecular distances are of C—H···O contacts with a minimum H···O distance of 2.58 Å [2.656 (16) and 2.34 (2) Å in CIF] in compound (1) and 2.64 (3) Å in compound (3).

Computing details

For both compounds, data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPII (Johnson, 1976) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012).

Figures

	Fig. 1. The ^1H NMR spectra of the OCH2 group in the 1,3,2-dioxaphosphorinane ring of compounds (1), (2) and (3).
	Fig. 2. View of a molecule of (1), indicating the atom-numbering scheme. H atoms have been omitted for clarity. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. View of a molecule of (3), indicating the atom-numbering scheme. H atoms have been omitted for clarity. Displacement ellipsoids are drawn at the 50% probability level.

(musa25) 2,2'-[Benzene-1,2-diylbis(oxy)]bis(5,5-dimethyl-1,3,2-dioxaphosphinane) 2,2'-dioxide

Crystal data

C16H24O8P2	Z = 2
Mr = 406.29	F(000) = 428
Triclinic, P1	Dx = 1.389 Mg m^−3
a = 9.5706 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2415 (5) Å	Cell parameters from 6760 reflections
c = 11.6998 (5) Å	θ = 2.9–32.6°
α = 94.507 (4)°	µ = 0.26 mm^−1
β = 110.270 (4)°	T = 293 K
γ = 111.616 (5)°	Polyhedron, colourless
V = 971.75 (8) Å^3	0.28 × 0.22 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur 3/Sapphire3 CCD diffractometer	3522 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3111 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.0050 pixels mm^-1	θmax = 25.3°, θmin = 2.9°
Thin slice φ and ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→12
Tmin = 0.970, Tmax = 1.000	l = −14→14
13183 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: mixed
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.2387P] where P = (Fo^2 + 2Fc^2)/3
3522 reflections	(Δ/σ)max = 0.001
287 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.21 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.63738 (18)	0.36947 (17)	0.56114 (14)	0.0383 (3)
C2	0.7132 (2)	0.50869 (18)	0.54993 (15)	0.0425 (4)
C3	0.7894 (3)	0.5337 (3)	0.46828 (19)	0.0622 (5)
C4	0.7932 (3)	0.4196 (3)	0.3998 (2)	0.0716 (6)
C5	0.7198 (3)	0.2817 (3)	0.41188 (19)	0.0619 (5)
C6	0.6412 (2)	0.2556 (2)	0.49250 (17)	0.0485 (4)
O1	0.55679 (14)	0.35278 (11)	0.64127 (10)	0.0425 (3)
P1	0.48663 (5)	0.21159 (4)	0.68809 (4)	0.04313 (14)
O11	0.41657 (13)	0.26452 (13)	0.77506 (11)	0.0478 (3)
C12	0.5333 (2)	0.3758 (2)	0.88942 (17)	0.0468 (4)
C13	0.6671 (2)	0.33522 (18)	0.96936 (16)	0.0446 (4)
C131	0.7915 (3)	0.4668 (2)	1.07755 (18)	0.0623 (5)
H13A	0.7386	0.4884	1.1279	0.094*
H13B	0.8337	0.5484	1.0444	0.094*
H13C	0.8804	0.4462	1.1282	0.094*
C132	0.5956 (3)	0.2043 (2)	1.0188 (2)	0.0687 (6)
H13D	0.5183	0.1230	0.9496	0.103*
H13E	0.5409	0.2253	1.0678	0.103*
H13F	0.6826	0.1820	1.0702	0.103*
C14	0.7544 (2)	0.3058 (2)	0.89078 (17)	0.0458 (4)
O15	0.63898 (15)	0.19196 (12)	0.77626 (11)	0.0485 (3)
O16	0.36583 (18)	0.08262 (14)	0.59102 (13)	0.0673 (4)
O2	0.70552 (14)	0.62353 (12)	0.61712 (11)	0.0446 (3)
P2	0.84618 (5)	0.71344 (4)	0.75157 (4)	0.04369 (14)
O21	0.78129 (14)	0.82044 (12)	0.78995 (11)	0.0477 (3)
C22	0.7949 (2)	0.94625 (19)	0.73635 (19)	0.0458 (4)
C23	0.96791 (19)	1.02969 (16)	0.74533 (15)	0.0394 (4)
C231	0.9688 (3)	1.1526 (2)	0.67952 (19)	0.0591 (5)
H23A	1.0775	1.2074	0.6848	0.089*
H23B	0.9356	1.2144	0.7193	0.089*
H23C	0.8936	1.1133	0.5930	0.089*
C232	1.0925 (2)	1.0900 (2)	0.88173 (17)	0.0561 (5)
H23D	1.0916	1.0117	0.9220	0.084*
H23E	1.0638	1.1533	0.9245	0.084*
H23F	1.2003	1.1428	0.8844	0.084*
C24	1.0084 (2)	0.92816 (19)	0.67482 (19)	0.0480 (4)
O25	1.00235 (14)	0.80403 (12)	0.72902 (12)	0.0508 (3)
O26	0.87952 (18)	0.62723 (14)	0.84088 (13)	0.0689 (4)
H3	0.842 (3)	0.628 (3)	0.465 (2)	0.076 (7)*
H4	0.845 (3)	0.440 (3)	0.347 (2)	0.084 (7)*
H5	0.717 (3)	0.203 (2)	0.364 (2)	0.067 (6)*
H6	0.593 (2)	0.164 (2)	0.4979 (17)	0.051 (5)*
H121	0.581 (2)	0.464 (2)	0.8678 (16)	0.046 (5)*
H122	0.469 (2)	0.383 (2)	0.9349 (18)	0.056 (5)*
H141	0.828 (2)	0.267 (2)	0.9339 (18)	0.059 (5)*
H142	0.811 (2)	0.390 (2)	0.8635 (17)	0.049 (5)*
H221	0.716 (2)	0.911 (2)	0.6498 (18)	0.047 (5)*
H222	0.765 (2)	0.999 (2)	0.7866 (18)	0.057 (5)*
H241	0.934 (2)	0.894 (2)	0.589 (2)	0.054 (5)*
H242	1.117 (3)	0.975 (2)	0.6787 (18)	0.060 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0345 (8)	0.0408 (8)	0.0341 (8)	0.0151 (7)	0.0087 (6)	0.0084 (6)
C2	0.0423 (9)	0.0417 (9)	0.0376 (8)	0.0172 (7)	0.0099 (7)	0.0116 (7)
C3	0.0714 (13)	0.0601 (13)	0.0551 (11)	0.0210 (11)	0.0305 (10)	0.0247 (10)
C4	0.0831 (16)	0.0895 (17)	0.0542 (12)	0.0355 (13)	0.0411 (12)	0.0211 (12)
C5	0.0695 (13)	0.0698 (14)	0.0483 (11)	0.0337 (11)	0.0233 (10)	0.0043 (10)
C6	0.0489 (10)	0.0442 (10)	0.0460 (9)	0.0194 (8)	0.0136 (8)	0.0054 (8)
O1	0.0457 (6)	0.0333 (6)	0.0473 (6)	0.0137 (5)	0.0208 (5)	0.0086 (5)
P1	0.0428 (2)	0.0308 (2)	0.0453 (3)	0.00669 (18)	0.0167 (2)	0.00380 (18)
O11	0.0353 (6)	0.0501 (7)	0.0505 (7)	0.0114 (5)	0.0171 (5)	0.0072 (5)
C12	0.0457 (10)	0.0431 (10)	0.0519 (10)	0.0189 (8)	0.0212 (8)	0.0048 (8)
C13	0.0453 (9)	0.0389 (9)	0.0446 (9)	0.0141 (7)	0.0168 (8)	0.0086 (7)
C131	0.0599 (12)	0.0614 (12)	0.0488 (10)	0.0190 (10)	0.0128 (9)	0.0007 (9)
C132	0.0756 (14)	0.0655 (13)	0.0651 (13)	0.0229 (11)	0.0328 (11)	0.0297 (11)
C14	0.0432 (9)	0.0422 (9)	0.0525 (10)	0.0206 (8)	0.0170 (8)	0.0130 (8)
O15	0.0583 (7)	0.0366 (6)	0.0542 (7)	0.0240 (6)	0.0230 (6)	0.0081 (5)
O16	0.0688 (9)	0.0416 (7)	0.0580 (8)	−0.0039 (6)	0.0210 (7)	−0.0036 (6)
O2	0.0442 (6)	0.0352 (6)	0.0466 (6)	0.0160 (5)	0.0103 (5)	0.0114 (5)
P2	0.0440 (3)	0.0328 (2)	0.0454 (3)	0.01260 (19)	0.0111 (2)	0.01387 (18)
O21	0.0504 (7)	0.0383 (6)	0.0548 (7)	0.0120 (5)	0.0285 (6)	0.0129 (5)
C22	0.0446 (10)	0.0374 (9)	0.0563 (11)	0.0182 (8)	0.0207 (9)	0.0108 (8)
C23	0.0402 (8)	0.0313 (8)	0.0413 (8)	0.0107 (7)	0.0151 (7)	0.0095 (6)
C231	0.0689 (12)	0.0414 (10)	0.0612 (12)	0.0186 (9)	0.0228 (10)	0.0212 (9)
C232	0.0534 (11)	0.0474 (10)	0.0461 (10)	0.0063 (9)	0.0129 (8)	0.0080 (8)
C24	0.0480 (10)	0.0410 (9)	0.0558 (11)	0.0137 (8)	0.0274 (9)	0.0115 (8)
O25	0.0420 (6)	0.0405 (6)	0.0704 (8)	0.0191 (5)	0.0213 (6)	0.0143 (6)
O26	0.0764 (9)	0.0460 (7)	0.0577 (8)	0.0174 (7)	0.0040 (7)	0.0232 (6)

Geometric parameters (Å, º)

C1—C6	1.382 (2)	C132—H13D	0.9600
C1—C2	1.382 (2)	C132—H13E	0.9600
C1—O1	1.3900 (19)	C132—H13F	0.9600
C2—C3	1.376 (3)	C14—O15	1.468 (2)
C2—O2	1.402 (2)	C14—H141	0.94 (2)
C3—C4	1.383 (3)	C14—H142	0.98 (2)
C3—H3	0.92 (2)	O2—P2	1.5894 (12)
C4—C5	1.370 (3)	P2—O26	1.4473 (13)
C4—H4	0.91 (3)	P2—O21	1.5509 (13)
C5—C6	1.383 (3)	P2—O25	1.5667 (13)
C5—H5	0.93 (2)	O21—C22	1.460 (2)
C6—H6	0.90 (2)	C22—C23	1.518 (2)
O1—P1	1.5830 (12)	C22—H221	0.969 (19)
P1—O16	1.4493 (13)	C22—H222	0.95 (2)
P1—O11	1.5597 (12)	C23—C24	1.515 (2)
P1—O15	1.5611 (13)	C23—C231	1.525 (2)
O11—C12	1.457 (2)	C23—C232	1.528 (2)
C12—C13	1.520 (2)	C231—H23A	0.9600
C12—H121	0.952 (19)	C231—H23B	0.9600
C12—H122	0.96 (2)	C231—H23C	0.9600
C13—C14	1.519 (2)	C232—H23D	0.9600
C13—C132	1.524 (3)	C232—H23E	0.9600
C13—C131	1.530 (2)	C232—H23F	0.9600
C131—H13A	0.9600	C24—O25	1.456 (2)
C131—H13B	0.9600	C24—H241	0.96 (2)
C131—H13C	0.9600	C24—H242	0.95 (2)
C6—C1—C2	120.07 (16)	H13D—C132—H13F	109.5
C6—C1—O1	123.55 (15)	H13E—C132—H13F	109.5
C2—C1—O1	116.36 (14)	O15—C14—C13	111.47 (14)
C3—C2—C1	120.02 (17)	O15—C14—H141	103.7 (12)
C3—C2—O2	119.93 (16)	C13—C14—H141	110.4 (12)
C1—C2—O2	119.98 (15)	O15—C14—H142	106.2 (11)
C2—C3—C4	119.8 (2)	C13—C14—H142	114.2 (11)
C2—C3—H3	117.6 (15)	H141—C14—H142	110.4 (16)
C4—C3—H3	122.5 (15)	C14—O15—P1	117.81 (10)
C5—C4—C3	120.3 (2)	C2—O2—P2	120.58 (10)
C5—C4—H4	121.9 (16)	O26—P2—O21	113.95 (8)
C3—C4—H4	117.8 (16)	O26—P2—O25	111.94 (8)
C4—C5—C6	120.2 (2)	O21—P2—O25	107.24 (6)
C4—C5—H5	121.8 (13)	O26—P2—O2	114.73 (7)
C6—C5—H5	117.9 (14)	O21—P2—O2	101.88 (7)
C1—C6—C5	119.64 (19)	O25—P2—O2	106.26 (7)
C1—C6—H6	121.9 (12)	C22—O21—P2	120.39 (10)
C5—C6—H6	118.4 (12)	O21—C22—C23	111.45 (14)
C1—O1—P1	126.34 (10)	O21—C22—H221	107.1 (11)
O16—P1—O11	113.30 (8)	C23—C22—H221	111.1 (11)
O16—P1—O15	113.22 (8)	O21—C22—H222	101.8 (12)
O11—P1—O15	106.22 (7)	C23—C22—H222	112.7 (12)
O16—P1—O1	115.97 (7)	H221—C22—H222	112.2 (16)
O11—P1—O1	100.67 (6)	C24—C23—C22	107.77 (14)
O15—P1—O1	106.28 (7)	C24—C23—C231	108.23 (14)
C12—O11—P1	117.71 (10)	C22—C23—C231	108.12 (14)
O11—C12—C13	112.49 (14)	C24—C23—C232	111.05 (15)
O11—C12—H121	109.1 (11)	C22—C23—C232	111.39 (15)
C13—C12—H121	110.0 (11)	C231—C23—C232	110.17 (14)
O11—C12—H122	104.9 (12)	C23—C231—H23A	109.5
C13—C12—H122	109.0 (12)	C23—C231—H23B	109.5
H121—C12—H122	111.3 (16)	H23A—C231—H23B	109.5
C14—C13—C12	108.54 (14)	C23—C231—H23C	109.5
C14—C13—C132	111.04 (16)	H23A—C231—H23C	109.5
C12—C13—C132	111.07 (16)	H23B—C231—H23C	109.5
C14—C13—C131	107.97 (15)	C23—C232—H23D	109.5
C12—C13—C131	107.27 (15)	C23—C232—H23E	109.5
C132—C13—C131	110.81 (15)	H23D—C232—H23E	109.5
C13—C131—H13A	109.5	C23—C232—H23F	109.5
C13—C131—H13B	109.5	H23D—C232—H23F	109.5
H13A—C131—H13B	109.5	H23E—C232—H23F	109.5
C13—C131—H13C	109.5	O25—C24—C23	111.35 (14)
H13A—C131—H13C	109.5	O25—C24—H241	108.6 (12)
H13B—C131—H13C	109.5	C23—C24—H241	111.1 (11)
C13—C132—H13D	109.5	O25—C24—H242	106.1 (12)
C13—C132—H13E	109.5	C23—C24—H242	111.4 (13)
H13D—C132—H13E	109.5	H241—C24—H242	108.2 (17)
C13—C132—H13F	109.5	C24—O25—P2	119.42 (11)
C6—C1—C2—C3	1.4 (2)	C131—C13—C14—O15	−173.11 (14)
O1—C1—C2—C3	−177.12 (15)	C13—C14—O15—P1	54.46 (17)
C6—C1—C2—O2	178.32 (14)	O16—P1—O15—C14	−169.25 (12)
O1—C1—C2—O2	−0.2 (2)	O11—P1—O15—C14	−44.30 (13)
C1—C2—C3—C4	−1.5 (3)	O1—P1—O15—C14	62.31 (13)
O2—C2—C3—C4	−178.38 (18)	C3—C2—O2—P2	−90.64 (18)
C2—C3—C4—C5	0.7 (3)	C1—C2—O2—P2	92.48 (16)
C3—C4—C5—C6	0.2 (3)	C2—O2—P2—O26	−53.81 (15)
C2—C1—C6—C5	−0.6 (3)	C2—O2—P2—O21	−177.43 (11)
O1—C1—C6—C5	177.88 (16)	C2—O2—P2—O25	70.43 (13)
C4—C5—C6—C1	−0.2 (3)	O26—P2—O21—C22	158.91 (12)
C6—C1—O1—P1	12.4 (2)	O25—P2—O21—C22	34.44 (14)
C2—C1—O1—P1	−169.11 (11)	O2—P2—O21—C22	−76.96 (13)
C1—O1—P1—O16	−58.42 (15)	P2—O21—C22—C23	−49.53 (18)
C1—O1—P1—O11	178.93 (12)	O21—C22—C23—C24	59.36 (19)
C1—O1—P1—O15	68.38 (13)	O21—C22—C23—C231	176.13 (14)
O16—P1—O11—C12	168.51 (12)	O21—C22—C23—C232	−62.68 (19)
O15—P1—O11—C12	43.60 (13)	C22—C23—C24—O25	−60.63 (19)
O1—P1—O11—C12	−67.00 (13)	C231—C23—C24—O25	−177.34 (15)
P1—O11—C12—C13	−53.54 (18)	C232—C23—C24—O25	61.62 (19)
O11—C12—C13—C14	57.12 (19)	C23—C24—O25—P2	51.53 (19)
O11—C12—C13—C132	−65.2 (2)	O26—P2—O25—C24	−161.00 (13)
O11—C12—C13—C131	173.54 (15)	O21—P2—O25—C24	−35.32 (14)
C12—C13—C14—O15	−57.14 (18)	O2—P2—O25—C24	73.05 (13)
C132—C13—C14—O15	65.23 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O16	0.90 (2)	2.656 (19)	3.224 (2)	122.2 (15)
C14—H142···O26	0.98 (2)	2.34 (2)	3.239 (2)	152.9 (15)
C22—H221···O16^i	0.969 (19)	2.663 (19)	3.540 (2)	150.6 (14)
C231—H23C···O16^i	0.96	2.60	3.489 (2)	154
C22—H222···O15^ii	0.95 (2)	2.66 (2)	3.441 (2)	140.4 (15)
C131—H13C···O26^iii	0.96	2.59	3.471 (3)	152

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

(musa26) 2-[(2'-Hydroxybiphenyl-2-yl)oxy]-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide

Crystal data

C10H20O7P2	Dx = 1.398 Mg m^−3
Mr = 314.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7659 reflections
a = 9.8434 (2) Å	θ = 2.9–32.5°
b = 11.3589 (3) Å	µ = 0.32 mm^−1
c = 26.6986 (8) Å	T = 293 K
V = 2985.18 (13) Å^3	Prism, colourless
Z = 8	0.40 × 0.18 × 0.14 mm
F(000) = 1328

Data collection

Oxford Diffraction Xcalibur 3/Sapphire3 CCD diffractometer	2141 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1920 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 16.0050 pixels mm^-1	θmax = 23.3°, θmin = 3.1°
Thin slice φ and ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→12
Tmin = 0.847, Tmax = 1.000	l = −29→29
33060 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: mixed
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0182P)^2 + 4.2243P] where P = (Fo^2 + 2Fc^2)/3
2141 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.21 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.45899 (9)	0.53260 (8)	0.61971 (3)	0.0490 (3)
O1	0.4212 (3)	0.4270 (2)	0.64655 (11)	0.0842 (9)
O11	0.4325 (2)	0.52680 (18)	0.56282 (8)	0.0515 (6)
C12	0.4428 (4)	0.6361 (4)	0.53372 (15)	0.0594 (10)
C13	0.3530 (3)	0.7315 (3)	0.55525 (12)	0.0478 (8)
C131	0.2040 (3)	0.6951 (3)	0.55180 (14)	0.0636 (10)
H13A	0.1890	0.6265	0.5721	0.095*
H13B	0.1817	0.6776	0.5176	0.095*
H13C	0.1476	0.7583	0.5636	0.095*
C132	0.3768 (5)	0.8453 (4)	0.52559 (17)	0.0938 (16)
H13D	0.3179	0.9059	0.5381	0.141*
H13E	0.3577	0.8316	0.4908	0.141*
H13F	0.4697	0.8695	0.5293	0.141*
C14	0.3931 (4)	0.7527 (3)	0.60888 (15)	0.0558 (9)
O15	0.3881 (2)	0.6456 (2)	0.63904 (8)	0.0544 (6)
P2	0.75239 (9)	0.49307 (8)	0.61789 (3)	0.0476 (2)
O2	0.7449 (3)	0.4006 (2)	0.58107 (9)	0.0713 (7)
O21	0.7854 (2)	0.44840 (18)	0.67142 (8)	0.0536 (6)
C22	0.8171 (4)	0.5358 (4)	0.70966 (14)	0.0593 (10)
C23	0.9300 (3)	0.6177 (3)	0.69381 (11)	0.0457 (8)
C231	1.0617 (4)	0.5494 (4)	0.68676 (15)	0.0763 (12)
H23A	1.0806	0.5044	0.7164	0.115*
H23B	1.1349	0.6034	0.6807	0.115*
H23C	1.0528	0.4971	0.6587	0.115*
C232	0.9474 (5)	0.7134 (4)	0.73355 (14)	0.0826 (13)
H23D	0.8632	0.7550	0.7377	0.124*
H23E	1.0168	0.7675	0.7231	0.124*
H23F	0.9731	0.6779	0.7648	0.124*
C24	0.8875 (4)	0.6773 (3)	0.64565 (13)	0.0540 (9)
O25	0.8577 (2)	0.5910 (2)	0.60644 (8)	0.0545 (6)
O3	0.6157 (2)	0.5672 (2)	0.62471 (10)	0.0640 (7)
H121	0.541 (4)	0.660 (3)	0.5358 (12)	0.066 (11)*
H122	0.412 (4)	0.615 (3)	0.5020 (14)	0.075 (12)*
H141	0.482 (4)	0.780 (3)	0.6115 (13)	0.064 (11)*
H142	0.335 (4)	0.806 (3)	0.6248 (12)	0.065 (11)*
H221	0.846 (3)	0.491 (3)	0.7376 (13)	0.063 (10)*
H222	0.734 (4)	0.577 (4)	0.7158 (14)	0.089 (14)*
H241	0.959 (3)	0.721 (3)	0.6335 (11)	0.052 (9)*
H242	0.808 (4)	0.723 (3)	0.6510 (12)	0.063 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0390 (5)	0.0484 (5)	0.0597 (6)	0.0035 (4)	−0.0082 (4)	0.0031 (4)
O1	0.0702 (18)	0.0701 (17)	0.112 (2)	0.0042 (15)	0.0012 (16)	0.0369 (16)
O11	0.0488 (13)	0.0462 (13)	0.0594 (14)	0.0086 (11)	−0.0104 (11)	−0.0125 (11)
C12	0.059 (3)	0.070 (3)	0.049 (2)	0.019 (2)	0.0053 (19)	−0.0011 (19)
C13	0.0449 (18)	0.0511 (19)	0.0474 (19)	0.0139 (16)	0.0055 (15)	0.0043 (15)
C131	0.050 (2)	0.075 (3)	0.066 (2)	0.0138 (19)	−0.0110 (18)	−0.005 (2)
C132	0.089 (3)	0.080 (3)	0.113 (4)	0.030 (3)	0.034 (3)	0.041 (3)
C14	0.048 (2)	0.046 (2)	0.074 (3)	0.0039 (18)	0.000 (2)	−0.0137 (19)
O15	0.0554 (15)	0.0649 (15)	0.0428 (12)	0.0116 (12)	−0.0045 (11)	−0.0030 (11)
P2	0.0389 (5)	0.0475 (5)	0.0563 (5)	−0.0013 (4)	−0.0077 (4)	0.0025 (4)
O2	0.0698 (17)	0.0644 (16)	0.0797 (17)	−0.0022 (13)	−0.0101 (15)	−0.0171 (14)
O21	0.0502 (14)	0.0472 (13)	0.0634 (14)	−0.0076 (11)	−0.0058 (11)	0.0150 (11)
C22	0.058 (2)	0.071 (3)	0.049 (2)	0.000 (2)	0.0056 (19)	0.015 (2)
C23	0.048 (2)	0.0509 (19)	0.0383 (17)	−0.0042 (16)	0.0008 (15)	0.0003 (14)
C231	0.046 (2)	0.100 (3)	0.083 (3)	0.001 (2)	−0.015 (2)	−0.010 (2)
C232	0.112 (4)	0.079 (3)	0.057 (2)	−0.015 (3)	−0.002 (2)	−0.013 (2)
C24	0.057 (2)	0.051 (2)	0.054 (2)	−0.014 (2)	0.0004 (19)	0.0078 (17)
O25	0.0576 (15)	0.0648 (15)	0.0412 (12)	−0.0149 (12)	−0.0023 (11)	0.0074 (11)
O3	0.0413 (13)	0.0538 (14)	0.0969 (19)	0.0054 (11)	−0.0222 (13)	−0.0075 (13)

Geometric parameters (Å, º)

P1—O1	1.446 (3)	P2—O2	1.440 (2)
P1—O11	1.542 (2)	P2—O25	1.551 (2)
P1—O15	1.549 (2)	P2—O21	1.551 (2)
P1—O3	1.597 (2)	P2—O3	1.597 (2)
O11—C12	1.468 (4)	O21—C22	1.458 (4)
C12—C13	1.512 (5)	C22—C23	1.510 (5)
C12—H121	1.00 (4)	C22—H221	0.95 (3)
C12—H122	0.93 (4)	C22—H222	0.96 (4)
C13—C14	1.505 (5)	C23—C24	1.512 (5)
C13—C131	1.527 (5)	C23—C231	1.523 (5)
C13—C132	1.534 (5)	C23—C232	1.529 (4)
C131—H13A	0.9600	C231—H23A	0.9600
C131—H13B	0.9600	C231—H23B	0.9600
C131—H13C	0.9600	C231—H23C	0.9600
C132—H13D	0.9600	C232—H23D	0.9600
C132—H13E	0.9600	C232—H23E	0.9600
C132—H13F	0.9600	C232—H23F	0.9600
C14—O15	1.460 (4)	C24—O25	1.463 (4)
C14—H141	0.93 (4)	C24—H241	0.92 (3)
C14—H142	0.94 (3)	C24—H242	0.95 (3)
O1—P1—O11	114.16 (16)	O2—P2—O21	113.65 (14)
O1—P1—O15	113.95 (15)	O25—P2—O21	106.03 (12)
O11—P1—O15	106.70 (12)	O2—P2—O3	114.75 (15)
O1—P1—O3	114.26 (15)	O25—P2—O3	101.96 (13)
O11—P1—O3	104.83 (14)	O21—P2—O3	104.11 (14)
O15—P1—O3	101.76 (13)	C22—O21—P2	117.9 (2)
C12—O11—P1	118.3 (2)	O21—C22—C23	112.4 (3)
O11—C12—C13	111.4 (3)	O21—C22—H221	105 (2)
O11—C12—H121	105 (2)	C23—C22—H221	109 (2)
C13—C12—H121	110 (2)	O21—C22—H222	106 (2)
O11—C12—H122	104 (2)	C23—C22—H222	112 (3)
C13—C12—H122	110 (2)	H221—C22—H222	113 (3)
H121—C12—H122	115 (3)	C22—C23—C24	108.1 (3)
C14—C13—C12	108.8 (3)	C22—C23—C231	110.3 (3)
C14—C13—C131	110.7 (3)	C24—C23—C231	111.0 (3)
C12—C13—C131	110.2 (3)	C22—C23—C232	109.1 (3)
C14—C13—C132	108.4 (3)	C24—C23—C232	107.6 (3)
C12—C13—C132	108.6 (3)	C231—C23—C232	110.7 (3)
C131—C13—C132	110.1 (3)	C23—C231—H23A	109.5
C13—C131—H13A	109.5	C23—C231—H23B	109.5
C13—C131—H13B	109.5	H23A—C231—H23B	109.5
H13A—C131—H13B	109.5	C23—C231—H23C	109.5
C13—C131—H13C	109.5	H23A—C231—H23C	109.5
H13A—C131—H13C	109.5	H23B—C231—H23C	109.5
H13B—C131—H13C	109.5	C23—C232—H23D	109.5
C13—C132—H13D	109.5	C23—C232—H23E	109.5
C13—C132—H13E	109.5	H23D—C232—H23E	109.5
H13D—C132—H13E	109.5	C23—C232—H23F	109.5
C13—C132—H13F	109.5	H23D—C232—H23F	109.5
H13D—C132—H13F	109.5	H23E—C232—H23F	109.5
H13E—C132—H13F	109.5	O25—C24—C23	111.4 (3)
O15—C14—C13	112.5 (3)	O25—C24—H241	105.4 (19)
O15—C14—H141	106 (2)	C23—C24—H241	109 (2)
C13—C14—H141	112 (2)	O25—C24—H242	108 (2)
O15—C14—H142	106 (2)	C23—C24—H242	110 (2)
C13—C14—H142	112 (2)	H241—C24—H242	113 (3)
H141—C14—H142	109 (3)	C24—O25—P2	118.3 (2)
C14—O15—P1	119.4 (2)	P1—O3—P2	132.41 (15)
O2—P2—O25	115.03 (15)
O1—P1—O11—C12	168.6 (2)	P2—O21—C22—C23	−53.7 (4)
O15—P1—O11—C12	41.8 (3)	O21—C22—C23—C24	57.8 (4)
O3—P1—O11—C12	−65.6 (3)	O21—C22—C23—C231	−63.7 (4)
P1—O11—C12—C13	−54.3 (4)	O21—C22—C23—C232	174.6 (3)
O11—C12—C13—C14	57.9 (4)	C22—C23—C24—O25	−57.7 (4)
O11—C12—C13—C131	−63.6 (4)	C231—C23—C24—O25	63.4 (4)
O11—C12—C13—C132	175.8 (3)	C232—C23—C24—O25	−175.4 (3)
C12—C13—C14—O15	−55.8 (4)	C23—C24—O25—P2	54.5 (4)
C131—C13—C14—O15	65.4 (4)	O2—P2—O25—C24	−170.1 (2)
C132—C13—C14—O15	−173.8 (3)	O21—P2—O25—C24	−43.6 (3)
C13—C14—O15—P1	49.8 (4)	O3—P2—O25—C24	65.1 (3)
O1—P1—O15—C14	−166.5 (2)	O1—P1—O3—P2	49.1 (3)
O11—P1—O15—C14	−39.6 (3)	O11—P1—O3—P2	−76.6 (2)
O3—P1—O15—C14	70.0 (3)	O15—P1—O3—P2	172.4 (2)
O2—P2—O21—C22	170.2 (2)	O2—P2—O3—P1	32.1 (3)
O25—P2—O21—C22	42.9 (3)	O25—P2—O3—P1	157.1 (2)
O3—P2—O21—C22	−64.2 (3)	O21—P2—O3—P1	−92.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H241···O1^i	0.92 (3)	2.64 (3)	3.405 (5)	141 (2)

Symmetry code: (i) −x+3/2, y+1/2, z.