Tetra-methyl 1,1,2-triphenyl-2H-1λ-phosphole-2,3,4,5-tetra-carboxyl-ate.

The title compound, C(30)H(27)O(8)P (1), was formed as one of two products {(1) and (2) [Krawczyk et al. (2010 ▶). Acta Cryst. E66 (cv2753)]} in the reaction of dimethyl acetyl-enedicarboxyl-ate with triphenyl-phosphine. The mol-ecule of (1) consists of a five-membered ring, in which the P atom is incorporated. One of the phenyl groups of the triphenyl-phosphine migrated to a vicinal C atom during the reaction. The five-membered ring of (1) is corrugated [r.m.s. deviation = 0.0719 (8) Å], whereas that in compound (2) is planar, the r.m.s. deviation being only 0.009 (2) Å.

Related literature

For general background to derivatives of dimethyl­enesuccinic anhydride (fulgides), see: Hadjoudis & Mavridis (2004 ▶); Gordaliza et al. (1996 ▶); Datta et al. (2001 ▶); Stobbe (1893 ▶); Maercker (1965 ▶); Shaw et al. (1967 ▶). 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

Triclinic,

a = 10.445 (6) Å

b = 10.897 (4) Å

c = 13.778 (4) Å

α = 73.93 (3)°

β = 72.54 (4)°

γ = 69.24 (4)°

V = 1373.0 (10) Å3

Z = 2

Cu Kα radiation

μ = 1.32 mm−1

T = 293 K

0.20 × 0.12 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby CCD

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.714, T max = 0.885

20877 measured reflections

5207 independent reflections

4503 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.128

S = 1.10

5207 reflections

352 parameters

H-atom parameters not refined

Δρmax = 0.33 e Å−3

Δρmin = −0.24 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/S1600536810037827/cv2752sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037827/cv2752Isup2.hkl

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

C30H27O8P	F(000) = 572
Mr = 546.49	Dx = 1.322 Mg m−3
Triclinic, P1	Melting point: 527 K
a = 10.445 (6) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.897 (4) Å	Cell parameters from 13436 reflections
c = 13.778 (4) Å	θ = 3.4–70.3°
α = 73.93 (3)°	µ = 1.32 mm−1
β = 72.54 (4)°	T = 293 K
γ = 69.24 (4)°	Parallelepiped, colourless
V = 1373.0 (10) Å3	0.20 × 0.12 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with Ruby CCD	5207 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4503 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 10.4922 pixels mm-1	θmax = 70.9°, θmin = 3.4°
ο and φ scans	h = −12→12
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	k = −13→13
Tmin = 0.714, Tmax = 0.885	l = −16→16
20877 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters not refined
S = 1.10	w = 1/[σ2(Fo2) + (0.0892P)2 + 0.105P] where P = (Fo2 + 2Fc2)/3
5207 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.24 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	0.87807 (4)	0.28700 (3)	0.28773 (3)	0.03454 (13)
O1	0.74905 (14)	0.07868 (13)	0.47544 (10)	0.0626 (4)
O2	0.56979 (14)	0.26500 (16)	0.47158 (9)	0.0707 (4)
O3	0.38795 (12)	0.44323 (14)	0.23622 (10)	0.0600 (3)
O4	0.45565 (13)	0.23001 (13)	0.31754 (11)	0.0608 (3)
O5	0.52801 (15)	0.67511 (12)	0.19216 (10)	0.0620 (4)
O6	0.58094 (12)	0.56597 (11)	0.06301 (8)	0.0463 (3)
O7	0.85225 (13)	0.62633 (11)	0.08444 (10)	0.0549 (3)
O8	1.01365 (12)	0.49540 (11)	0.17693 (9)	0.0489 (3)
C1	0.72232 (15)	0.22390 (14)	0.31095 (11)	0.0364 (3)
C2	0.61807 (15)	0.34781 (15)	0.26462 (11)	0.0383 (3)
C3	0.67344 (15)	0.44912 (14)	0.20778 (11)	0.0368 (3)
C4	0.81626 (15)	0.43265 (14)	0.20266 (11)	0.0381 (3)
C5	0.68130 (17)	0.17803 (17)	0.42808 (12)	0.0458 (4)
C6	0.5292 (3)	0.2358 (4)	0.58405 (17)	0.1184 (13)
H6A	0.4466	0.3048	0.6076	0.178*
H6B	0.6044	0.2319	0.6123	0.178*
H6C	0.5097	0.1513	0.6065	0.178*
C7	0.47704 (16)	0.34920 (17)	0.26968 (12)	0.0439 (4)
C8	0.3211 (2)	0.2186 (3)	0.3245 (2)	0.0829 (7)
H8A	0.3171	0.1304	0.3599	0.124*
H8B	0.3063	0.2346	0.2560	0.124*
H8C	0.2495	0.2833	0.3621	0.124*
C9	0.58512 (16)	0.57734 (15)	0.15500 (12)	0.0413 (3)
C10	0.4878 (2)	0.6777 (2)	0.00915 (16)	0.0659 (5)
H10A	0.4926	0.6597	−0.0564	0.099*
H10B	0.5155	0.7566	−0.0021	0.099*
H10C	0.3934	0.6914	0.0500	0.099*
C11	0.89050 (16)	0.52834 (14)	0.14811 (11)	0.0398 (3)
C12	1.1076 (2)	0.5725 (2)	0.11739 (17)	0.0631 (5)
H12A	1.1909	0.5410	0.1442	0.095*
H12B	1.0622	0.6650	0.1219	0.095*
H12C	1.1326	0.5632	0.0463	0.095*
C13	0.76060 (16)	0.11180 (15)	0.24985 (12)	0.0417 (3)
C14	0.79602 (19)	0.14481 (18)	0.14288 (14)	0.0520 (4)
H14	0.7991	0.2313	0.1112	0.062*
C15	0.8269 (2)	0.0515 (2)	0.08212 (17)	0.0666 (5)
H15	0.8517	0.0751	0.0103	0.080*
C16	0.8210 (3)	−0.0755 (2)	0.1277 (2)	0.0758 (6)
H16	0.8411	−0.1382	0.0870	0.091*
C17	0.7855 (3)	−0.1097 (2)	0.2332 (2)	0.0795 (7)
H17	0.7814	−0.1961	0.2641	0.095*
C18	0.7554 (2)	−0.01671 (18)	0.29509 (17)	0.0617 (5)
H18	0.7319	−0.0413	0.3669	0.074*
C19	1.03797 (15)	0.16713 (15)	0.24022 (12)	0.0386 (3)
C20	1.07591 (19)	0.03839 (16)	0.29863 (14)	0.0514 (4)
H20	1.0197	0.0152	0.3630	0.062*
C21	1.1982 (2)	−0.05435 (18)	0.25964 (19)	0.0651 (5)
H21	1.2241	−0.1404	0.2981	0.078*
C22	1.2813 (2)	−0.0205 (2)	0.16489 (19)	0.0674 (5)
H22	1.3643	−0.0830	0.1401	0.081*
C23	1.24248 (19)	0.1049 (2)	0.10654 (15)	0.0586 (5)
H23	1.2988	0.1268	0.0418	0.070*
C24	1.11999 (17)	0.19945 (16)	0.14305 (12)	0.0452 (4)
H24	1.0931	0.2840	0.1026	0.054*
C25	0.88459 (16)	0.32367 (15)	0.40546 (12)	0.0422 (3)
C26	0.97926 (18)	0.24694 (18)	0.46578 (13)	0.0492 (4)
H26	1.0461	0.1693	0.4469	0.059*
C27	0.9748 (2)	0.2854 (2)	0.55454 (15)	0.0661 (5)
H27	1.0402	0.2343	0.5944	0.079*
C28	0.8755 (3)	0.3978 (3)	0.58435 (17)	0.0789 (6)
H28	0.8729	0.4227	0.6444	0.095*
C29	0.7807 (3)	0.4726 (3)	0.5259 (2)	0.0965 (9)
H29	0.7122	0.5484	0.5467	0.116*
C30	0.7848 (3)	0.4378 (2)	0.43626 (18)	0.0789 (7)
H30	0.7203	0.4910	0.3961	0.095*

	U11	U22	U33	U12	U13	U23
P1	0.0331 (2)	0.0310 (2)	0.0361 (2)	−0.00411 (15)	−0.01189 (14)	−0.00373 (14)
O1	0.0660 (8)	0.0580 (8)	0.0472 (7)	−0.0097 (7)	−0.0169 (6)	0.0087 (6)
O2	0.0576 (8)	0.0871 (10)	0.0400 (6)	0.0074 (7)	−0.0074 (6)	−0.0113 (6)
O3	0.0386 (6)	0.0697 (8)	0.0637 (8)	−0.0056 (6)	−0.0192 (5)	−0.0055 (6)
O4	0.0423 (6)	0.0612 (8)	0.0795 (9)	−0.0201 (6)	−0.0157 (6)	−0.0060 (6)
O5	0.0722 (8)	0.0435 (6)	0.0633 (7)	0.0130 (6)	−0.0303 (6)	−0.0223 (6)
O6	0.0543 (6)	0.0410 (6)	0.0410 (6)	−0.0028 (5)	−0.0215 (5)	−0.0068 (4)
O7	0.0622 (7)	0.0400 (6)	0.0618 (7)	−0.0175 (6)	−0.0285 (6)	0.0100 (5)
O8	0.0456 (6)	0.0440 (6)	0.0573 (7)	−0.0155 (5)	−0.0196 (5)	0.0015 (5)
C1	0.0332 (7)	0.0361 (7)	0.0372 (7)	−0.0083 (6)	−0.0099 (5)	−0.0031 (6)
C2	0.0346 (7)	0.0391 (7)	0.0380 (7)	−0.0039 (6)	−0.0117 (6)	−0.0077 (6)
C3	0.0379 (7)	0.0347 (7)	0.0356 (7)	−0.0014 (6)	−0.0139 (6)	−0.0093 (6)
C4	0.0395 (7)	0.0309 (7)	0.0404 (7)	−0.0051 (6)	−0.0144 (6)	−0.0026 (5)
C5	0.0428 (8)	0.0503 (9)	0.0406 (8)	−0.0146 (7)	−0.0097 (6)	−0.0017 (7)
C6	0.0901 (19)	0.162 (3)	0.0423 (11)	0.0193 (19)	−0.0018 (11)	−0.0134 (15)
C7	0.0366 (7)	0.0540 (9)	0.0395 (7)	−0.0072 (7)	−0.0096 (6)	−0.0133 (7)
C8	0.0564 (12)	0.0940 (17)	0.1114 (19)	−0.0385 (12)	−0.0180 (12)	−0.0192 (15)
C9	0.0412 (8)	0.0369 (7)	0.0422 (8)	−0.0004 (6)	−0.0156 (6)	−0.0099 (6)
C10	0.0837 (14)	0.0527 (10)	0.0630 (11)	−0.0071 (10)	−0.0465 (11)	0.0017 (9)
C11	0.0455 (8)	0.0315 (7)	0.0417 (7)	−0.0076 (6)	−0.0149 (6)	−0.0054 (6)
C12	0.0531 (10)	0.0639 (11)	0.0758 (13)	−0.0278 (9)	−0.0145 (9)	−0.0047 (10)
C13	0.0370 (7)	0.0365 (7)	0.0516 (8)	−0.0076 (6)	−0.0147 (6)	−0.0077 (6)
C14	0.0590 (10)	0.0472 (9)	0.0503 (9)	−0.0108 (8)	−0.0158 (8)	−0.0129 (7)
C15	0.0774 (13)	0.0631 (12)	0.0621 (11)	−0.0089 (10)	−0.0212 (10)	−0.0260 (9)
C16	0.0861 (15)	0.0580 (12)	0.0943 (17)	−0.0055 (11)	−0.0352 (13)	−0.0363 (12)
C17	0.0990 (17)	0.0417 (10)	0.1046 (19)	−0.0212 (11)	−0.0300 (14)	−0.0160 (11)
C18	0.0737 (12)	0.0437 (9)	0.0665 (11)	−0.0186 (9)	−0.0187 (10)	−0.0042 (8)
C19	0.0345 (7)	0.0354 (7)	0.0441 (7)	−0.0036 (6)	−0.0146 (6)	−0.0075 (6)
C20	0.0491 (9)	0.0397 (8)	0.0572 (10)	−0.0055 (7)	−0.0166 (8)	−0.0014 (7)
C21	0.0596 (11)	0.0380 (9)	0.0876 (14)	0.0051 (8)	−0.0289 (11)	−0.0087 (9)
C22	0.0480 (10)	0.0590 (11)	0.0890 (15)	0.0070 (9)	−0.0155 (10)	−0.0343 (11)
C23	0.0475 (9)	0.0654 (11)	0.0585 (10)	−0.0068 (8)	−0.0037 (8)	−0.0272 (9)
C24	0.0459 (8)	0.0445 (8)	0.0433 (8)	−0.0083 (7)	−0.0120 (7)	−0.0099 (7)
C25	0.0444 (8)	0.0421 (8)	0.0414 (7)	−0.0109 (7)	−0.0132 (6)	−0.0085 (6)
C26	0.0490 (9)	0.0516 (9)	0.0455 (8)	−0.0133 (8)	−0.0167 (7)	−0.0026 (7)
C27	0.0751 (13)	0.0788 (14)	0.0506 (10)	−0.0234 (11)	−0.0307 (9)	−0.0029 (9)
C28	0.1066 (18)	0.0837 (15)	0.0560 (11)	−0.0224 (14)	−0.0288 (12)	−0.0244 (11)
C29	0.116 (2)	0.0873 (17)	0.0825 (16)	0.0170 (16)	−0.0434 (15)	−0.0498 (14)
C30	0.0877 (15)	0.0693 (13)	0.0761 (14)	0.0194 (12)	−0.0430 (12)	−0.0377 (11)

P1—C4	1.7342 (17)	C12—H12C	0.9600
P1—C19	1.7872 (19)	C13—C18	1.379 (2)
P1—C25	1.8001 (16)	C13—C14	1.383 (2)
P1—C1	1.8921 (17)	C14—C15	1.384 (3)
O1—C5	1.201 (2)	C14—H14	0.9300
O2—C5	1.314 (2)	C15—C16	1.367 (3)
O2—C6	1.453 (3)	C15—H15	0.9300
O3—C7	1.204 (2)	C16—C17	1.365 (4)
O4—C7	1.347 (2)	C16—H16	0.9300
O4—C8	1.426 (2)	C17—C18	1.395 (3)
O5—C9	1.192 (2)	C17—H17	0.9300
O6—C9	1.3220 (19)	C18—H18	0.9300
O6—C10	1.440 (2)	C19—C24	1.384 (2)
O7—C11	1.2078 (19)	C19—C20	1.395 (2)
O8—C11	1.357 (2)	C20—C21	1.384 (3)
O8—C12	1.436 (2)	C20—H20	0.9300
C1—C2	1.521 (2)	C21—C22	1.369 (3)
C1—C5	1.526 (2)	C21—H21	0.9300
C1—C13	1.543 (2)	C22—C23	1.369 (3)
C2—C3	1.367 (2)	C22—H22	0.9300
C2—C7	1.448 (2)	C23—C24	1.385 (3)
C3—C4	1.420 (2)	C23—H23	0.9300
C3—C9	1.503 (2)	C24—H24	0.9300
C4—C11	1.429 (2)	C25—C26	1.375 (2)
C6—H6A	0.9600	C25—C30	1.386 (3)
C6—H6B	0.9600	C26—C27	1.382 (3)
C6—H6C	0.9600	C26—H26	0.9300
C8—H8A	0.9600	C27—C28	1.366 (3)
C8—H8B	0.9600	C27—H27	0.9300
C8—H8C	0.9600	C28—C29	1.355 (4)
C10—H10A	0.9600	C28—H28	0.9300
C10—H10B	0.9600	C29—C30	1.374 (3)
C10—H10C	0.9600	C29—H29	0.9300
C12—H12A	0.9600	C30—H30	0.9300
C12—H12B	0.9600
C4—P1—C19	118.31 (8)	O8—C12—H12C	109.5
C4—P1—C25	111.01 (8)	H12A—C12—H12C	109.5
C19—P1—C25	110.45 (8)	H12B—C12—H12C	109.5
C4—P1—C1	95.25 (8)	C18—C13—C14	118.39 (16)
C19—P1—C1	110.67 (8)	C18—C13—C1	124.08 (16)
C25—P1—C1	110.13 (8)	C14—C13—C1	117.46 (14)
C5—O2—C6	116.29 (17)	C13—C14—C15	121.17 (18)
C7—O4—C8	116.36 (17)	C13—C14—H14	119.4
C9—O6—C10	115.99 (13)	C15—C14—H14	119.4
C11—O8—C12	116.43 (14)	C16—C15—C14	120.0 (2)
C2—C1—C5	115.65 (13)	C16—C15—H15	120.0
C2—C1—C13	109.52 (12)	C14—C15—H15	120.0
C5—C1—C13	113.31 (13)	C17—C16—C15	119.67 (19)
C2—C1—P1	101.49 (10)	C17—C16—H16	120.2
C5—C1—P1	105.46 (10)	C15—C16—H16	120.2
C13—C1—P1	110.62 (10)	C16—C17—C18	120.8 (2)
C3—C2—C7	123.29 (14)	C16—C17—H17	119.6
C3—C2—C1	114.70 (13)	C18—C17—H17	119.6
C7—C2—C1	121.52 (14)	C13—C18—C17	120.0 (2)
C2—C3—C4	118.33 (14)	C13—C18—H18	120.0
C2—C3—C9	121.37 (14)	C17—C18—H18	120.0
C4—C3—C9	120.26 (14)	C24—C19—C20	119.92 (15)
C3—C4—C11	125.85 (14)	C24—C19—P1	120.09 (12)
C3—C4—P1	108.19 (12)	C20—C19—P1	119.89 (13)
C11—C4—P1	125.44 (12)	C21—C20—C19	119.24 (18)
O1—C5—O2	124.05 (16)	C21—C20—H20	120.4
O1—C5—C1	123.65 (15)	C19—C20—H20	120.4
O2—C5—C1	112.10 (14)	C22—C21—C20	120.56 (18)
O2—C6—H6A	109.5	C22—C21—H21	119.7
O2—C6—H6B	109.5	C20—C21—H21	119.7
H6A—C6—H6B	109.5	C23—C22—C21	120.22 (17)
O2—C6—H6C	109.5	C23—C22—H22	119.9
H6A—C6—H6C	109.5	C21—C22—H22	119.9
H6B—C6—H6C	109.5	C22—C23—C24	120.53 (18)
O3—C7—O4	122.88 (15)	C22—C23—H23	119.7
O3—C7—C2	125.66 (17)	C24—C23—H23	119.7
O4—C7—C2	111.46 (14)	C23—C24—C19	119.47 (16)
O4—C8—H8A	109.5	C23—C24—H24	120.3
O4—C8—H8B	109.5	C19—C24—H24	120.3
H8A—C8—H8B	109.5	C26—C25—C30	118.85 (16)
O4—C8—H8C	109.5	C26—C25—P1	124.91 (13)
H8A—C8—H8C	109.5	C30—C25—P1	116.24 (13)
H8B—C8—H8C	109.5	C25—C26—C27	119.85 (18)
O5—C9—O6	125.55 (14)	C25—C26—H26	120.1
O5—C9—C3	123.73 (14)	C27—C26—H26	120.1
O6—C9—C3	110.72 (12)	C28—C27—C26	120.73 (19)
O6—C10—H10A	109.5	C28—C27—H27	119.6
O6—C10—H10B	109.5	C26—C27—H27	119.6
H10A—C10—H10B	109.5	C29—C28—C27	119.59 (19)
O6—C10—H10C	109.5	C29—C28—H28	120.2
H10A—C10—H10C	109.5	C27—C28—H28	120.2
H10B—C10—H10C	109.5	C28—C29—C30	120.7 (2)
O7—C11—O8	122.87 (14)	C28—C29—H29	119.6
O7—C11—C4	126.20 (15)	C30—C29—H29	119.6
O8—C11—C4	110.93 (13)	C29—C30—C25	120.2 (2)
O8—C12—H12A	109.5	C29—C30—H30	119.9
O8—C12—H12B	109.5	C25—C30—H30	119.9
H12A—C12—H12B	109.5
C4—P1—C1—C2	−12.94 (10)	C12—O8—C11—O7	−8.6 (2)
C19—P1—C1—C2	−135.88 (10)	C12—O8—C11—C4	171.39 (14)
C25—P1—C1—C2	101.72 (11)	C3—C4—C11—O7	−13.6 (3)
C4—P1—C1—C5	−133.91 (11)	P1—C4—C11—O7	175.67 (13)
C19—P1—C1—C5	103.16 (11)	C3—C4—C11—O8	166.45 (13)
C25—P1—C1—C5	−19.25 (12)	P1—C4—C11—O8	−4.29 (19)
C4—P1—C1—C13	103.22 (11)	C2—C1—C13—C18	−129.20 (17)
C19—P1—C1—C13	−19.72 (12)	C5—C1—C13—C18	1.6 (2)
C25—P1—C1—C13	−142.12 (11)	P1—C1—C13—C18	119.74 (16)
C5—C1—C2—C3	124.77 (14)	C2—C1—C13—C14	47.76 (18)
C13—C1—C2—C3	−105.73 (14)	C5—C1—C13—C14	178.51 (14)
P1—C1—C2—C3	11.24 (14)	P1—C1—C13—C14	−63.30 (17)
C5—C1—C2—C7	−63.05 (18)	C18—C13—C14—C15	−0.6 (3)
C13—C1—C2—C7	66.44 (17)	C1—C13—C14—C15	−177.72 (17)
P1—C1—C2—C7	−176.59 (11)	C13—C14—C15—C16	0.8 (3)
C7—C2—C3—C4	−175.57 (13)	C14—C15—C16—C17	−0.5 (4)
C1—C2—C3—C4	−3.56 (19)	C15—C16—C17—C18	−0.1 (4)
C7—C2—C3—C9	6.7 (2)	C14—C13—C18—C17	0.0 (3)
C1—C2—C3—C9	178.76 (12)	C1—C13—C18—C17	176.93 (18)
C2—C3—C4—C11	−179.26 (14)	C16—C17—C18—C13	0.4 (4)
C9—C3—C4—C11	−1.5 (2)	C4—P1—C19—C24	9.56 (15)
C2—C3—C4—P1	−7.20 (16)	C25—P1—C19—C24	−119.90 (13)
C9—C3—C4—P1	170.51 (10)	C1—P1—C19—C24	117.88 (13)
C19—P1—C4—C3	128.76 (11)	C4—P1—C19—C20	−166.72 (12)
C25—P1—C4—C3	−102.04 (12)	C25—P1—C19—C20	63.82 (15)
C1—P1—C4—C3	11.88 (11)	C1—P1—C19—C20	−58.40 (15)
C19—P1—C4—C11	−59.14 (15)	C24—C19—C20—C21	2.1 (3)
C25—P1—C4—C11	70.06 (15)	P1—C19—C20—C21	178.33 (14)
C1—P1—C4—C11	−176.01 (13)	C19—C20—C21—C22	0.0 (3)
C6—O2—C5—O1	0.0 (3)	C20—C21—C22—C23	−1.5 (3)
C6—O2—C5—C1	−175.0 (2)	C21—C22—C23—C24	0.9 (3)
C2—C1—C5—O1	176.41 (15)	C22—C23—C24—C19	1.2 (3)
C13—C1—C5—O1	48.8 (2)	C20—C19—C24—C23	−2.7 (2)
P1—C1—C5—O1	−72.36 (19)	P1—C19—C24—C23	−178.96 (13)
C2—C1—C5—O2	−8.5 (2)	C4—P1—C25—C26	−149.65 (14)
C13—C1—C5—O2	−136.16 (15)	C19—P1—C25—C26	−16.38 (17)
P1—C1—C5—O2	102.70 (15)	C1—P1—C25—C26	106.15 (16)
C8—O4—C7—O3	1.7 (3)	C4—P1—C25—C30	30.89 (19)
C8—O4—C7—C2	−178.33 (17)	C19—P1—C25—C30	164.16 (17)
C3—C2—C7—O3	−9.5 (2)	C1—P1—C25—C30	−73.31 (19)
C1—C2—C7—O3	179.04 (15)	C30—C25—C26—C27	−0.9 (3)
C3—C2—C7—O4	170.58 (14)	P1—C25—C26—C27	179.64 (15)
C1—C2—C7—O4	−0.9 (2)	C25—C26—C27—C28	1.3 (3)
C10—O6—C9—O5	−6.5 (3)	C26—C27—C28—C29	−0.3 (4)
C10—O6—C9—C3	173.85 (15)	C27—C28—C29—C30	−0.9 (5)
C2—C3—C9—O5	94.9 (2)	C28—C29—C30—C25	1.3 (5)
C4—C3—C9—O5	−82.8 (2)	C26—C25—C30—C29	−0.4 (4)
C2—C3—C9—O6	−85.44 (17)	P1—C25—C30—C29	179.1 (2)
C4—C3—C9—O6	96.92 (17)