Trimethyl-3-meth­oxy-4-oxo-5-triphenyl­phospho­ranyl­idene­cyclo­pent-1-ene-1,2,3-tricarboxyl­ate

Krawczyk, K.K.; Wojtasiewicz, K.; Maurin, J.K.; Gronowska, E.; Czarnocki, Z.

doi:10.1107/S1600536810037815

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2792

https://doi.org/10.1107/S1600536810037815

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Trimethyl-3-methoxy-4-oxo-5-triphenylphosphoranylidenecyclopent-1-ene-1,2,3-tricarboxylate

Krzysztof K. Krawczyk,^a Krystyna Wojtasiewicz,^a Jan K. Maurin,^b,^c Ewa Gronowska ^a and Zbigniew Czarnocki ^a ^*

^aFaculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland, ^bNational Medicines Institute, Chełmska 30/34, 00-725 Warsaw, Poland, and ^cInstitute of Atomic Energy, 05-400 Otwock-Świerk, Poland
^*Correspondence e-mail: czarnoz@chem.uw.edu.pl

(Received 16 August 2010; accepted 21 September 2010; online 9 October 2010)

The title compound, C₃₀H₂₇O₈P (2), was formed as one of two products {(1) [Krawczyk et al. (2010 ). Acta Cryst. E66 (cv2752)] and (2)} in the reaction of dimethyl acetylenedicarboxylate with triphenylphosphine. The molecule of (2) consists of a five-membered carbocyclic ring. The P atom is a part of a triphenylphosphoranylidene substituent. In contrast to (1), the five-membered ring of (2) is planar, the r.m.s. deviation being only 0.009 (2) Å.

Related literature

For a detailed study of adduct formation from triarylphosphines and acetylenedicarboxylate, see: Waite et al. (1971 ). For related structures, see: Spek (1987 ); Thomas & Hamor (1993 ); Krawczyk et al. (2010).

Experimental

Crystal data

C₃₀H₂₇O₈P
M_r = 546.49
Monoclinic, P 2₁ /n
a = 10.9220 (1) Å
b = 15.1215 (1) Å
c = 16.7423 (1) Å
β = 92.145 (1)°
V = 2763.17 (4) Å³
Z = 4
Cu Kα radiation
μ = 1.31 mm⁻¹
T = 293 K
0.37 × 0.18 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby CCD
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.717, T_max = 0.926
24587 measured reflections
5014 independent reflections
3667 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.129
S = 1.01
5014 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-NT (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks paper, I. DOI: https://doi.org/10.1107/S1600536810037815/cv2753sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810037815/cv2753Isup2.hkl

checkCIF report

Comment top

Trimethyl-3-methoxy-4-oxo-5-triphenylphosphoranylidenecyclopent-1-ene-1,2,3- tricarboxylate (2) is one of two 1:2 adducts formed as the minor compound in the reaction of triphenylphosphine and acetylenedicarboxylate, described already in 1971 (Waite et al.). By using dry toluene instead of diethyl ether, and by reducing the temperature of the reaction to -78%C we menaged to raise the yield of the reaction from 21% to 28%. Crystal structure of the other compound - tetramethyl 1,1,2-triphenyl-2H-1λ⁵-phosphole-2,3,4,5-tetracarboxylate was also published recently (Krawczyk et al., 2010). In the present comunication we report on the crystal structure of compound (2).

In molecule (2) (Fig. 1), one of the acetyl groups at C4 is almost co-planar with the five-membered ring with a dihedral angle of 8.60 (3)° whereas all other acetyl and methoxy groups at C3 and C5 atoms are perpendicular to it with the dihedral angles of 86.31 (14), 84.95 (12) and 89.09 (9)°, respectively. The phenyl rings bonded to the phosphorous atom in (2) have similar conformations to that observed at room temperature for the parent triphenylphosphine in both polymorphic structures (Spek, 1987; Thomas & Hamor, 1993) assuring the lowest repulsion of the neighboring fragments.

Related literature top

For a detailed study of adduct formation from triarylphosphines and acetylenedicarboxylate, see: Waite et al. (1971). For related structures, see: Spek (1987); Thomas & Hamor (1993); Krawczyk et al. (2010).

Experimental top

A mixture of acetylenedicarboxylate (0.5 g, 3,52 mmol) in 3 ml of dry toluene was placed in a two-neck round bottom flask, and cooled to -78°C (solid CO₂/acetone bath) with stirring. The solution of triphenylphosphine (0.47 g, 1.80 mmol) in 3 ml of dry toluene was then added dropwise under argon during 20 min. The reaction was then left to reach slowly room temperature overnight. After evaporation of the solvent under reduced pressure, the remaining oil was dissolved in ethyl acetate and purified by column chromatography (Merck silica gel, 230 - 400 mesh, ethyl acetate, and then ethyl acetate/methanol 19:1 as eluent). Both products could be easily recrystallized from ethyl acetate/diethyl ether. The 2H-phosphole 1 (0.61 g, 63%) had Rf = 0.46 (ethyl acetate) and a melting point of 253–255°C (Waite, et al.1971). The second eluted product - (2) (0.27 g, 28%) - showed a green fluorescence in UV light (λ = 365 nm), had Rf = 0.18 (ethyl acetate) and melted at 243–244°C [(Waite et al., 1971), m.p. 222–224°C]. The single-crystal of (2) was obtained by slow evaporation of its ethyl acetate/diethyl ether solution.

Structure description top

For a detailed study of adduct formation from triarylphosphines and acetylenedicarboxylate, see: Waite et al. (1971). For related structures, see: Spek (1987); Thomas & Hamor (1993); Krawczyk et al. (2010).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-NT (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (2) showing the atomi labelling and 30% probability displacement ellipsoids.

Trimethyl-3-methoxy-4-oxo-5-triphenylphosphoranylidenecyclopent-1-ene- 1,2,3-tricarboxylate top

Crystal data top

C₃₀H₂₇O₈P	F(000) = 1144
M_r = 546.49	D_x = 1.314 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 10.9220 (1) Å	Cell parameters from 8837 reflections
b = 15.1215 (1) Å	θ = 2.6–70.3°
c = 16.7423 (1) Å	µ = 1.31 mm⁻¹
β = 92.145 (1)°	T = 293 K
V = 2763.17 (4) Å³	Parallelepiped, colourless
Z = 4	0.37 × 0.18 × 0.07 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Ruby CCD	5014 independent reflections
Radiation source: fine-focus sealed tube	3667 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ο and φ scans	θ_max = 70.4°, θ_min = 3.9°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −12→13
T_min = 0.717, T_max = 0.926	k = −17→18
24587 measured reflections	l = −20→19

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) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0824P)²] where P = (F_o² + 2F_c²)/3
5014 reflections	(Δ/σ)_max < 0.001
352 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₀H₂₇O₈P	V = 2763.17 (4) Å³
M_r = 546.49	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 10.9220 (1) Å	µ = 1.31 mm⁻¹
b = 15.1215 (1) Å	T = 293 K
c = 16.7423 (1) Å	0.37 × 0.18 × 0.07 mm
β = 92.145 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Ruby CCD	5014 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	3667 reflections with I > 2σ(I)
T_min = 0.717, T_max = 0.926	R_int = 0.043
24587 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
5014 reflections	Δρ_min = −0.21 e Å⁻³
352 parameters

Special details top

Experimental. Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897)

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

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	0.98130 (5)	0.33555 (3)	0.23236 (3)	0.03465 (16)
O1	0.78889 (16)	0.31389 (11)	0.08918 (8)	0.0499 (4)
O2	0.4783 (2)	0.40415 (17)	0.08401 (15)	0.0969 (8)
O3	0.6135 (2)	0.47924 (12)	0.15999 (11)	0.0676 (5)
O4	0.55002 (18)	0.25150 (12)	0.14528 (10)	0.0587 (5)
O5	0.40520 (18)	0.34126 (14)	0.28230 (12)	0.0676 (5)
O6	0.52975 (17)	0.33087 (15)	0.39062 (10)	0.0690 (6)
O7	0.78341 (18)	0.41525 (11)	0.41526 (9)	0.0579 (5)
O8	0.78057 (17)	0.26709 (11)	0.41634 (8)	0.0519 (4)
C1	0.8225 (2)	0.33213 (13)	0.23123 (11)	0.0344 (4)
C2	0.7528 (2)	0.32327 (12)	0.15769 (12)	0.0373 (5)
C3	0.6140 (2)	0.32578 (14)	0.17661 (12)	0.0396 (5)
C4	0.6183 (2)	0.33365 (13)	0.26716 (12)	0.0392 (5)
C5	0.7364 (2)	0.33655 (12)	0.29464 (11)	0.0342 (4)
C6	0.5565 (2)	0.40552 (18)	0.13463 (14)	0.0541 (6)
C7	0.5738 (4)	0.5607 (2)	0.1224 (2)	0.0985 (13)
H7A	0.6202	0.6091	0.1450	0.148*
H7B	0.4883	0.5698	0.1311	0.148*
H7C	0.5865	0.5575	0.0660	0.148*
C8	0.5827 (4)	0.17164 (18)	0.18298 (19)	0.0814 (10)
H8A	0.5359	0.1242	0.1590	0.122*
H8B	0.5661	0.1754	0.2388	0.122*
H8C	0.6684	0.1607	0.1769	0.122*
C9	0.5071 (2)	0.33579 (15)	0.31160 (13)	0.0440 (5)
C10	0.7700 (2)	0.34554 (14)	0.38231 (11)	0.0390 (5)
C11	1.0463 (2)	0.22934 (14)	0.20702 (12)	0.0419 (5)
C12	0.9720 (3)	0.16379 (15)	0.17490 (15)	0.0522 (6)
H12	0.8905	0.1758	0.1611	0.063*
C13	1.0193 (3)	0.07979 (18)	0.16328 (18)	0.0683 (8)
H13	0.9692	0.0355	0.1416	0.082*
C14	1.1395 (3)	0.06166 (18)	0.18364 (19)	0.0720 (8)
H14	1.1704	0.0049	0.1770	0.086*
C15	1.2136 (3)	0.1272 (2)	0.2137 (2)	0.0718 (8)
H15	1.2955	0.1150	0.2264	0.086*
C16	1.1685 (2)	0.21181 (17)	0.22555 (16)	0.0558 (6)
H16	1.2197	0.2562	0.2457	0.067*
C17	0.4260 (3)	0.3308 (3)	0.4409 (2)	0.0909 (11)
H17A	0.4539	0.3273	0.4959	0.136*
H17B	0.3749	0.2807	0.4280	0.136*
H17C	0.3800	0.3842	0.4325	0.136*
C18	0.7974 (3)	0.2668 (2)	0.50317 (14)	0.0760 (9)
H18A	0.8041	0.2070	0.5219	0.114*
H18B	0.7284	0.2948	0.5265	0.114*
H18C	0.8708	0.2986	0.5182	0.114*
C21	1.0310 (2)	0.42131 (14)	0.16544 (11)	0.0427 (5)
C22	1.1493 (3)	0.42166 (18)	0.13731 (15)	0.0590 (7)
H22	1.2028	0.3754	0.1499	0.071*
C23	1.1869 (3)	0.4911 (2)	0.09070 (18)	0.0762 (9)
H23	1.2657	0.4911	0.0714	0.091*
C24	1.1094 (3)	0.5600 (2)	0.07247 (17)	0.0731 (9)
H24	1.1357	0.6063	0.0408	0.088*
C25	0.9937 (3)	0.56107 (18)	0.10071 (17)	0.0685 (8)
H25	0.9417	0.6083	0.0887	0.082*
C26	0.9535 (3)	0.49155 (16)	0.14749 (14)	0.0554 (6)
H26	0.8746	0.4923	0.1667	0.066*
C31	1.04400 (19)	0.36215 (14)	0.33050 (11)	0.0362 (5)
C32	1.0687 (2)	0.44928 (14)	0.35069 (13)	0.0446 (5)
H32	1.0548	0.4936	0.3129	0.053*
C33	1.1136 (2)	0.47116 (18)	0.42599 (14)	0.0542 (6)
H33	1.1294	0.5299	0.4392	0.065*
C34	1.1349 (2)	0.40574 (19)	0.48145 (14)	0.0566 (7)
H34	1.1658	0.4204	0.5323	0.068*
C35	1.1113 (3)	0.31865 (19)	0.46293 (14)	0.0583 (7)
H35	1.1263	0.2749	0.5011	0.070*
C36	1.0653 (2)	0.29617 (16)	0.38761 (13)	0.0469 (5)
H36	1.0486	0.2374	0.3751	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0370 (3)	0.0358 (3)	0.0312 (3)	−0.0019 (2)	0.0013 (2)	−0.00179 (19)
O1	0.0546 (11)	0.0653 (10)	0.0298 (7)	−0.0056 (8)	0.0028 (7)	−0.0040 (6)
O2	0.0973 (19)	0.1003 (17)	0.0891 (15)	−0.0024 (14)	−0.0496 (15)	0.0148 (13)
O3	0.0841 (15)	0.0491 (10)	0.0682 (11)	0.0071 (9)	−0.0154 (10)	0.0070 (8)
O4	0.0622 (12)	0.0619 (10)	0.0516 (9)	−0.0204 (9)	−0.0027 (8)	−0.0095 (7)
O5	0.0404 (11)	0.0935 (14)	0.0688 (11)	−0.0029 (10)	−0.0008 (9)	−0.0047 (10)
O6	0.0470 (11)	0.1185 (16)	0.0423 (9)	0.0043 (11)	0.0120 (8)	0.0006 (9)
O7	0.0722 (13)	0.0582 (10)	0.0432 (8)	−0.0052 (9)	−0.0007 (8)	−0.0150 (7)
O8	0.0619 (12)	0.0585 (9)	0.0349 (7)	0.0014 (8)	−0.0024 (7)	0.0075 (7)
C1	0.0373 (12)	0.0367 (10)	0.0291 (9)	−0.0007 (9)	−0.0006 (8)	−0.0021 (7)
C2	0.0421 (12)	0.0354 (10)	0.0342 (10)	−0.0051 (9)	−0.0023 (9)	−0.0002 (8)
C3	0.0385 (12)	0.0473 (11)	0.0327 (10)	−0.0073 (10)	−0.0048 (9)	−0.0029 (8)
C4	0.0399 (13)	0.0415 (11)	0.0360 (10)	−0.0016 (10)	0.0006 (9)	−0.0009 (8)
C5	0.0375 (12)	0.0326 (9)	0.0323 (9)	−0.0016 (9)	−0.0009 (9)	−0.0021 (7)
C6	0.0502 (16)	0.0706 (17)	0.0405 (12)	0.0056 (13)	−0.0100 (11)	0.0057 (11)
C7	0.145 (4)	0.0617 (18)	0.088 (2)	0.022 (2)	−0.009 (2)	0.0175 (16)
C8	0.120 (3)	0.0521 (16)	0.0733 (18)	−0.0230 (17)	0.0140 (19)	−0.0109 (13)
C9	0.0382 (13)	0.0468 (12)	0.0469 (12)	−0.0011 (10)	0.0004 (10)	−0.0039 (9)
C10	0.0378 (12)	0.0474 (12)	0.0316 (10)	0.0003 (10)	0.0005 (9)	−0.0027 (9)
C11	0.0453 (14)	0.0412 (11)	0.0398 (10)	0.0030 (10)	0.0077 (10)	−0.0050 (8)
C12	0.0517 (15)	0.0456 (12)	0.0594 (14)	0.0004 (11)	0.0013 (12)	−0.0117 (10)
C13	0.073 (2)	0.0461 (14)	0.0859 (19)	−0.0030 (14)	0.0050 (16)	−0.0171 (13)
C14	0.076 (2)	0.0473 (14)	0.094 (2)	0.0142 (14)	0.0189 (17)	−0.0128 (13)
C15	0.0529 (17)	0.0661 (17)	0.097 (2)	0.0155 (15)	0.0097 (15)	−0.0092 (15)
C16	0.0432 (15)	0.0530 (14)	0.0713 (16)	0.0022 (12)	0.0050 (12)	−0.0120 (12)
C17	0.070 (2)	0.136 (3)	0.0689 (19)	0.002 (2)	0.0368 (17)	0.0042 (19)
C18	0.094 (3)	0.098 (2)	0.0358 (12)	0.0006 (19)	−0.0035 (14)	0.0162 (13)
C21	0.0521 (15)	0.0436 (11)	0.0325 (10)	−0.0067 (10)	0.0022 (10)	0.0006 (8)
C22	0.0573 (17)	0.0634 (15)	0.0572 (14)	−0.0048 (13)	0.0148 (12)	0.0041 (12)
C23	0.077 (2)	0.084 (2)	0.0702 (18)	−0.0189 (18)	0.0276 (16)	0.0059 (15)
C24	0.095 (3)	0.0680 (18)	0.0565 (15)	−0.0271 (17)	0.0095 (16)	0.0160 (13)
C25	0.086 (2)	0.0552 (15)	0.0634 (16)	−0.0090 (15)	−0.0081 (16)	0.0184 (12)
C26	0.0581 (17)	0.0534 (14)	0.0544 (14)	−0.0054 (12)	−0.0013 (12)	0.0105 (11)
C31	0.0326 (11)	0.0422 (10)	0.0337 (9)	−0.0007 (9)	0.0004 (9)	−0.0013 (8)
C32	0.0487 (14)	0.0420 (11)	0.0429 (11)	−0.0054 (10)	0.0002 (10)	−0.0030 (9)
C33	0.0557 (16)	0.0598 (14)	0.0472 (13)	−0.0084 (12)	0.0027 (11)	−0.0156 (11)
C34	0.0478 (15)	0.0851 (18)	0.0366 (11)	−0.0052 (13)	−0.0011 (11)	−0.0119 (11)
C35	0.0570 (17)	0.0771 (18)	0.0405 (12)	0.0070 (14)	−0.0010 (11)	0.0122 (11)
C36	0.0513 (15)	0.0487 (12)	0.0405 (11)	−0.0028 (11)	−0.0022 (10)	0.0032 (9)

Geometric parameters (Å, º) top

P1—C1	1.734 (2)	C13—H13	0.9300
P1—C31	1.802 (2)	C14—C15	1.363 (4)
P1—C21	1.810 (2)	C14—H14	0.9300
P1—C11	1.813 (2)	C15—C16	1.389 (4)
O1—C2	1.235 (2)	C15—H15	0.9300
O2—C6	1.181 (3)	C16—H16	0.9300
O3—C6	1.338 (3)	C17—H17A	0.9600
O3—C7	1.443 (3)	C17—H17B	0.9600
O4—C8	1.403 (4)	C17—H17C	0.9600
O4—C3	1.413 (3)	C18—H18A	0.9600
O5—C9	1.202 (3)	C18—H18B	0.9600
O6—C9	1.339 (3)	C18—H18C	0.9600
O6—C17	1.437 (3)	C21—C26	1.384 (4)
O7—C10	1.196 (3)	C21—C22	1.393 (4)
O8—C10	1.319 (3)	C22—C23	1.380 (4)
O8—C18	1.458 (3)	C22—H22	0.9300
C1—C2	1.430 (3)	C23—C24	1.370 (5)
C1—C5	1.446 (3)	C23—H23	0.9300
C2—C3	1.561 (3)	C24—C25	1.366 (5)
C3—C4	1.520 (3)	C24—H24	0.9300
C3—C6	1.519 (3)	C25—C26	1.392 (4)
C4—C5	1.355 (3)	C25—H25	0.9300
C4—C9	1.448 (3)	C26—H26	0.9300
C5—C10	1.506 (3)	C31—C32	1.384 (3)
C7—H7A	0.9600	C31—C36	1.395 (3)
C7—H7B	0.9600	C32—C33	1.376 (3)
C7—H7C	0.9600	C32—H32	0.9300
C8—H8A	0.9600	C33—C34	1.371 (4)
C8—H8B	0.9600	C33—H33	0.9300
C8—H8C	0.9600	C34—C35	1.375 (4)
C11—C12	1.378 (3)	C34—H34	0.9300
C11—C16	1.384 (3)	C35—C36	1.382 (3)
C12—C13	1.388 (4)	C35—H35	0.9300
C12—H12	0.9300	C36—H36	0.9300
C13—C14	1.372 (4)

C1—P1—C31	111.24 (9)	C15—C14—C13	119.7 (3)
C1—P1—C21	109.71 (10)	C15—C14—H14	120.1
C31—P1—C21	106.98 (10)	C13—C14—H14	120.1
C1—P1—C11	111.81 (10)	C14—C15—C16	120.9 (3)
C31—P1—C11	105.80 (10)	C14—C15—H15	119.6
C21—P1—C11	111.15 (10)	C16—C15—H15	119.6
C6—O3—C7	116.4 (2)	C11—C16—C15	119.3 (2)
C8—O4—C3	113.8 (2)	C11—C16—H16	120.4
C9—O6—C17	117.3 (2)	C15—C16—H16	120.4
C10—O8—C18	116.02 (19)	O6—C17—H17A	109.5
C2—C1—C5	107.24 (18)	O6—C17—H17B	109.5
C2—C1—P1	120.83 (15)	H17A—C17—H17B	109.5
C5—C1—P1	131.93 (15)	O6—C17—H17C	109.5
O1—C2—C1	129.2 (2)	H17A—C17—H17C	109.5
O1—C2—C3	122.51 (19)	H17B—C17—H17C	109.5
C1—C2—C3	108.26 (16)	O8—C18—H18A	109.5
O4—C3—C4	115.39 (17)	O8—C18—H18B	109.5
O4—C3—C6	105.61 (18)	H18A—C18—H18B	109.5
C4—C3—C6	113.33 (18)	O8—C18—H18C	109.5
O4—C3—C2	112.08 (17)	H18A—C18—H18C	109.5
C4—C3—C2	102.15 (17)	H18B—C18—H18C	109.5
C6—C3—C2	108.24 (18)	C26—C21—C22	119.4 (2)
C5—C4—C9	129.16 (19)	C26—C21—P1	119.29 (18)
C5—C4—C3	109.55 (18)	C22—C21—P1	121.04 (19)
C9—C4—C3	121.3 (2)	C23—C22—C21	119.6 (3)
C4—C5—C1	112.75 (17)	C23—C22—H22	120.2
C4—C5—C10	121.88 (18)	C21—C22—H22	120.2
C1—C5—C10	125.35 (19)	C24—C23—C22	120.7 (3)
O2—C6—O3	123.9 (3)	C24—C23—H23	119.6
O2—C6—C3	126.4 (3)	C22—C23—H23	119.6
O3—C6—C3	109.6 (2)	C25—C24—C23	120.2 (3)
O3—C7—H7A	109.5	C25—C24—H24	119.9
O3—C7—H7B	109.5	C23—C24—H24	119.9
H7A—C7—H7B	109.5	C24—C25—C26	120.1 (3)
O3—C7—H7C	109.5	C24—C25—H25	120.0
H7A—C7—H7C	109.5	C26—C25—H25	120.0
H7B—C7—H7C	109.5	C21—C26—C25	119.9 (3)
O4—C8—H8A	109.5	C21—C26—H26	120.1
O4—C8—H8B	109.5	C25—C26—H26	120.1
H8A—C8—H8B	109.5	C32—C31—C36	119.16 (19)
O4—C8—H8C	109.5	C32—C31—P1	119.95 (16)
H8A—C8—H8C	109.5	C36—C31—P1	120.87 (16)
H8B—C8—H8C	109.5	C33—C32—C31	120.8 (2)
O5—C9—O6	122.8 (2)	C33—C32—H32	119.6
O5—C9—C4	125.0 (2)	C31—C32—H32	119.6
O6—C9—C4	112.2 (2)	C34—C33—C32	119.5 (2)
O7—C10—O8	125.88 (19)	C34—C33—H33	120.2
O7—C10—C5	123.38 (19)	C32—C33—H33	120.2
O8—C10—C5	110.73 (17)	C33—C34—C35	120.8 (2)
C12—C11—C16	119.9 (2)	C33—C34—H34	119.6
C12—C11—P1	119.90 (19)	C35—C34—H34	119.6
C16—C11—P1	120.01 (17)	C34—C35—C36	120.0 (2)
C11—C12—C13	119.8 (3)	C34—C35—H35	120.0
C11—C12—H12	120.1	C36—C35—H35	120.0
C13—C12—H12	120.1	C35—C36—C31	119.7 (2)
C14—C13—C12	120.4 (3)	C35—C36—H36	120.2
C14—C13—H13	119.8	C31—C36—H36	120.2
C12—C13—H13	119.8

C31—P1—C1—C2	172.06 (15)	C18—O8—C10—C5	−172.4 (2)
C21—P1—C1—C2	53.89 (18)	C4—C5—C10—O7	−89.4 (3)
C11—P1—C1—C2	−69.89 (18)	C1—C5—C10—O7	89.1 (3)
C31—P1—C1—C5	−8.1 (2)	C4—C5—C10—O8	89.8 (2)
C21—P1—C1—C5	−126.25 (19)	C1—C5—C10—O8	−91.7 (2)
C11—P1—C1—C5	110.0 (2)	C1—P1—C11—C12	12.7 (2)
C5—C1—C2—O1	−177.0 (2)	C31—P1—C11—C12	133.97 (19)
P1—C1—C2—O1	2.9 (3)	C21—P1—C11—C12	−110.25 (19)
C5—C1—C2—C3	2.1 (2)	C1—P1—C11—C16	−162.32 (18)
P1—C1—C2—C3	−177.97 (14)	C31—P1—C11—C16	−41.1 (2)
C8—O4—C3—C4	−48.1 (3)	C21—P1—C11—C16	74.7 (2)
C8—O4—C3—C6	−174.1 (2)	C16—C11—C12—C13	1.7 (4)
C8—O4—C3—C2	68.3 (3)	P1—C11—C12—C13	−173.3 (2)
O1—C2—C3—O4	53.3 (3)	C11—C12—C13—C14	0.1 (4)
C1—C2—C3—O4	−125.94 (18)	C12—C13—C14—C15	−1.6 (5)
O1—C2—C3—C4	177.36 (18)	C13—C14—C15—C16	1.3 (5)
C1—C2—C3—C4	−1.8 (2)	C12—C11—C16—C15	−2.0 (4)
O1—C2—C3—C6	−62.8 (2)	P1—C11—C16—C15	173.1 (2)
C1—C2—C3—C6	118.00 (19)	C14—C15—C16—C11	0.4 (4)
O4—C3—C4—C5	122.7 (2)	C1—P1—C21—C26	24.4 (2)
C6—C3—C4—C5	−115.4 (2)	C31—P1—C21—C26	−96.3 (2)
C2—C3—C4—C5	0.8 (2)	C11—P1—C21—C26	148.61 (18)
O4—C3—C4—C9	−56.5 (3)	C1—P1—C21—C22	−161.12 (19)
C6—C3—C4—C9	65.5 (3)	C31—P1—C21—C22	78.1 (2)
C2—C3—C4—C9	−178.30 (18)	C11—P1—C21—C22	−36.9 (2)
C9—C4—C5—C1	179.5 (2)	C26—C21—C22—C23	−1.3 (4)
C3—C4—C5—C1	0.5 (2)	P1—C21—C22—C23	−175.7 (2)
C9—C4—C5—C10	−1.8 (3)	C21—C22—C23—C24	0.6 (5)
C3—C4—C5—C10	179.16 (17)	C22—C23—C24—C25	0.3 (5)
C2—C1—C5—C4	−1.7 (2)	C23—C24—C25—C26	−0.7 (5)
P1—C1—C5—C4	178.44 (16)	C22—C21—C26—C25	0.9 (4)
C2—C1—C5—C10	179.66 (18)	P1—C21—C26—C25	175.5 (2)
P1—C1—C5—C10	−0.2 (3)	C24—C25—C26—C21	0.0 (4)
C7—O3—C6—O2	0.6 (4)	C1—P1—C31—C32	−92.5 (2)
C7—O3—C6—C3	176.8 (3)	C21—P1—C31—C32	27.3 (2)
O4—C3—C6—O2	−2.9 (4)	C11—P1—C31—C32	145.84 (19)
C4—C3—C6—O2	−130.1 (3)	C1—P1—C31—C36	85.8 (2)
C2—C3—C6—O2	117.3 (3)	C21—P1—C31—C36	−154.43 (19)
O4—C3—C6—O3	−178.97 (19)	C11—P1—C31—C36	−35.8 (2)
C4—C3—C6—O3	53.8 (3)	C36—C31—C32—C33	0.0 (4)
C2—C3—C6—O3	−58.8 (2)	P1—C31—C32—C33	178.32 (18)
C17—O6—C9—O5	1.1 (4)	C31—C32—C33—C34	0.5 (4)
C17—O6—C9—C4	−178.9 (3)	C32—C33—C34—C35	−0.4 (4)
C5—C4—C9—O5	172.6 (2)	C33—C34—C35—C36	−0.1 (4)
C3—C4—C9—O5	−8.4 (3)	C34—C35—C36—C31	0.5 (4)
C5—C4—C9—O6	−7.4 (3)	C32—C31—C36—C35	−0.5 (4)
C3—C4—C9—O6	171.55 (19)	P1—C31—C36—C35	−178.79 (19)
C18—O8—C10—O7	6.8 (4)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₇O₈P
M_r	546.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.9220 (1), 15.1215 (1), 16.7423 (1)
β (°)	92.145 (1)
V (Å³)	2763.17 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.37 × 0.18 × 0.07

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Ruby CCD
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.717, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	24587, 5014, 3667
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.129, 1.01
No. of reflections	5014
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-NT (Sheldrick, 2008).

Acknowledgements

The authors thank the Polish Ministry of Science and Higher Education for financial support (grant No. N204 030636).

References

Krawczyk, K. K., Wojtasiewicz, K., Maurin, J. K., Gronowska, E. & Czarnocki, Z. (2010). Acta Cryst. E66, o2791. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (1987). Acta Cryst. C43, 1233–1235. CSD CrossRef CAS IUCr Journals Google Scholar
Thomas, J. A. & Hamor, T. A. (1993). Acta Cryst. C49, 355–357. CSD CrossRef CAS IUCr Journals Google Scholar
Waite, N. E., Tebby, J. C., Ward, R. S., Shaw, M. A. & Williams, D. H. (1971). J. Chem. Soc. C, pp. 1620–1622. Google Scholar

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