Trimethyl-3-meth-oxy-4-oxo-5-triphenyl-phospho-ranyl-idene-cyclo-pent-1-ene-1,2,3-tricarboxyl-ate.

The title compound, C(30)H(27)O(8)P (2), was formed as one of two products {(1) [Krawczyk et al. (2010 ▶). Acta Cryst. E66 (cv2752)] and (2)} in the reaction of dimethyl acetyl-enedicarboxyl-ate with triphenyl-phosphine. The mol-ecule 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 = 546.49

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.01

5014 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037815/cv2753Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H27O8P	F(000) = 1144
Mr = 546.49	Dx = 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

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

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(Fo2) + (0.0824P)2] where P = (Fo2 + 2Fc2)/3
5014 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)