Single-crystal structure analysis of a novel aryl phosphinate diglycidyl ether

Cho, C.-S.; Liau, W.-B.; Chen, L.-W.

doi:10.1107/S010876819900018X

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Single-crystal structure analysis of a novel aryl phosphinate diglycidyl ether

C.-S. Cho, W.-B. Liau and L.-W. Chen

The crystal structure of 10-[2,5-bis(2,3-epoxy-1-propoxy)phenyl]-9-oxa-10-phosphaphenanthren-10-one has been studied by single-crystal X-ray diffraction. The unit cell of C₂₄H₂₁O₆P, M_r = 436.4, is triclinic, P1, with a = 8.507 (3), b = 10.613 (4), c = 12.457 (3) Å, α = 80.05 (3), β = 71.38 (2), γ = 76.69 (3)°, V = 1031.1 (6) Å³, Z = 2, D_x = 1.406 Mg m⁻³ and μ(Mo Kα) = 0.17 mm⁻¹. The final R (wR) is 0.063 (0.057) {w = 1/[σ²(F) + 0.0004F²]} for 3619 unique reflections measured at 295 K. The aryl phosphinate group bonded to the central phenyl ring comes close to one of the two glycidyl ether groups, the epoxide ring of which is ordered. The epoxide ring far from the aryl phosphinate group is disordered. The NMR chemical shifts of the protons of the glycidyl ether group close to the aryl phosphinate group are reduced by the `ring-current effect'.

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Supporting information

	Crystallographic Information File (CIF) Contains datablocks global, I
	Structure factor file (SHELXL table format) Supplementary material

CCDC reference: 134779

Comment top

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Experimental top

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Computing details top

Data collection: CAD-4 EXPRESS; cell refinement: CAD-4 EXPRESS; data reduction: NRCVAX DATRD2; program(s) used to solve structure: NRCVAX SOLVER; program(s) used to refine structure: NRCVAX LSTSQ; molecular graphics: NRCVAX ORTEP; software used to prepare material for publication: NRCVAX TABLES.

Figures top

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Crystal data top

C₂₄H₂₁O₆P	F(000) = 456.37
M_r = 436.40	? #Insert any comments here.
Triclinic, P1	D_x = 1.406 Mg m⁻³
a = 8.507 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.613 (4) Å	Cell parameters from 25 reflections
c = 12.457 (3) Å	θ = 7.4–10.9°
α = 80.05 (3)°	µ = 0.17 mm⁻¹
β = 71.38 (2)°	T = 295 K
γ = 76.69 (3)°	Block, colorless
V = 1031.1 (6) Å³	0.50 × 0.38 × 0.20 mm
Z = 2

Data collection top

Enraf-Nonius CAD4 diffractometer	2634 reflections with I_net > 2.0σ(I_net)
Radiation source: xray tube	R_int = 0.010
Graphite monochromator	θ_max = 24.9°, θ_min = 0.0°
θ/2θ scan b/P/b	h = −9→10
Absorption correction: empirical (using intensity measurements) ?	k = 0→12
T_min = 0.918, T_max = 0.953	l = −14→14
3632 measured reflections	3 standard reflections every 60 min
3619 independent reflections	intensity decay: 0.0%

Refinement top

Refinement on F	1/(σ²(F) + 0.0004F²)
Least-squares matrix: block diagonal per atom	(Δ/σ)_max = 0.010
R[F² > 2σ(F²)] = 0.063	Δρ_max = 4.30 e Å⁻³
wR(F²) = 0.057	Δρ_min = −2.50 e Å⁻³
3619 reflections	Extinction correction: Larson
299 parameters	Extinction coefficient: 624 (213)

Crystal data top

C₂₄H₂₁O₆P	γ = 76.69 (3)°
M_r = 436.40	V = 1031.1 (6) Å³
Triclinic, P1	Z = 2
a = 8.507 (3) Å	Mo Kα radiation
b = 10.613 (4) Å	µ = 0.17 mm⁻¹
c = 12.457 (3) Å	T = 295 K
α = 80.05 (3)°	0.50 × 0.38 × 0.20 mm
β = 71.38 (2)°

Data collection top

Enraf-Nonius CAD4 diffractometer	2634 reflections with I_net > 2.0σ(I_net)
Absorption correction: empirical (using intensity measurements) ?	R_int = 0.010
T_min = 0.918, T_max = 0.953	3 standard reflections every 60 min
3632 measured reflections	intensity decay: 0.0%
3619 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	299 parameters
wR(F²) = 0.057	Δρ_max = 4.30 e Å⁻³
3619 reflections	Δρ_min = −2.50 e Å⁻³

Special details top

Experimental. ? #Insert any special details here.

Refinement. ? #Insert any special details here.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P	0.91830 (7)	0.72952 (5)	0.42866 (4)	0.0383 (3)
O1	0.9139 (2)	0.88184 (13)	0.41924 (11)	0.0509 (10)
O2	1.01965 (18)	0.65441 (14)	0.50183 (12)	0.0500 (9)
O3	0.62925 (19)	0.88473 (16)	0.34941 (13)	0.0628 (10)
O4	0.4335 (2)	0.50935 (19)	0.70245 (17)	0.0863 (13)
O5	0.6501 (3)	1.0762 (2)	0.13093 (17)	0.0982 (17)
O6	0.3526 (3)	0.3511 (2)	0.93426 (15)	0.0861 (14)
C1	0.9910 (2)	0.69429 (19)	0.28446 (17)	0.0388 (11)
C2	0.9979 (3)	0.5676 (2)	0.26422 (19)	0.0539 (15)
C3	1.0522 (4)	0.5342 (2)	0.1545 (2)	0.0658 (18)
C4	1.0977 (3)	0.6271 (2)	0.0647 (2)	0.0621 (17)
C5	1.0911 (3)	0.7526 (2)	0.08321 (18)	0.0512 (14)
C6	1.0400 (2)	0.78933 (19)	0.19331 (17)	0.0390 (11)
C7	1.0431 (2)	0.92132 (19)	0.21477 (17)	0.0387 (11)
C8	1.1068 (3)	1.0145 (2)	0.12615 (18)	0.0537 (14)
C9	1.1138 (3)	1.1359 (2)	0.1470 (2)	0.0637 (16)
C10	1.0608 (3)	1.1689 (2)	0.2571 (2)	0.0555 (14)
C11	0.9971 (3)	1.0809 (2)	0.34569 (18)	0.0453 (12)
C12	0.9875 (2)	0.96034 (19)	0.32373 (17)	0.0379 (11)
C13	0.7009 (3)	0.7147 (2)	0.48413 (17)	0.0417 (12)
C14	0.5772 (3)	0.7927 (2)	0.43766 (18)	0.0481 (12)
C15	0.4131 (3)	0.7708 (3)	0.4793 (2)	0.0609 (16)
C16	0.3723 (3)	0.6749 (3)	0.5663 (2)	0.0655 (16)
C17	0.4916 (3)	0.5992 (2)	0.6148 (2)	0.0573 (14)
C18	0.6568 (3)	0.6177 (2)	0.57315 (19)	0.0492 (13)
C19	0.5078 (3)	0.9919 (3)	0.3251 (2)	0.0695 (16)
C20	0.5989 (4)	1.0917 (3)	0.2456 (2)	0.0769 (19)
C21	0.5268 (4)	1.1872 (3)	0.1737 (3)	0.097 (2)
C22	0.5480 (4)	0.4195 (3)	0.7485 (3)	0.084 (2)
C23	0.4298 (5)	0.3256 (4)	0.8195 (3)	0.061 (3)
C24	0.4840 (6)	0.2380 (6)	0.9056 (4)	0.092 (4)
C23'	0.4999 (8)	0.3175 (7)	0.8488 (6)	0.072 (4)
C24'	0.3475 (8)	0.2776 (6)	0.8532 (5)	0.063 (4)
H2	0.964	0.503	0.328	0.0657*
H3	1.060	0.445	0.141	0.0764*
H4	1.135	0.604	−0.013	0.0735*
H5	1.121	0.817	0.019	0.0623*
H8	1.146	0.992	0.049	0.0621*
H9	1.158	1.199	0.084	0.0698*
H10	1.069	1.254	0.272	0.0634*
H11	0.959	1.103	0.424	0.0565*
H15	0.328	0.825	0.446	0.0693*
H16	0.257	0.659	0.595	0.0729*
H18	0.743	0.563	0.605	0.0587*
H19a	0.459	0.990	0.274	0.0935*
H19b	0.434	1.029	0.395	0.0708*
H20	0.684	1.119	0.274	0.0865*
H21a	0.547	1.273	0.143	0.0988*
H21b	0.414	1.188	0.176	0.0988*
H22a	0.634	0.378	0.687	0.0848*
H22b	0.589	0.467	0.792	0.0848*
H23	0.366	0.295	0.781	0.0685*
H24a	0.464	0.150	0.926	0.0914*
H24b	0.599	0.232	0.913	0.0914*
H23'	0.591	0.247	0.867	0.0807*
H24'a	0.331	0.190	0.869	0.0736*
H24'b	0.293	0.318	0.793	0.0736*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0412 (3)	0.0364 (3)	0.0391 (3)	−0.0121 (2)	−0.0130 (2)	−0.0002 (2)
O1	0.0743 (10)	0.0405 (8)	0.0379 (8)	−0.0217 (7)	−0.0088 (7)	−0.0040 (6)
O2	0.0481 (8)	0.0549 (9)	0.0510 (9)	−0.0146 (7)	−0.0224 (7)	0.0055 (7)
O3	0.0507 (9)	0.0657 (11)	0.0572 (10)	0.0032 (8)	−0.0131 (8)	0.0085 (8)
O4	0.0670 (12)	0.0783 (13)	0.0946 (14)	−0.0305 (10)	0.0007 (11)	0.0164 (11)
O5	0.1186 (17)	0.0961 (16)	0.0604 (12)	−0.0238 (13)	0.0043 (12)	−0.0105 (11)
O6	0.0883 (14)	0.0970 (15)	0.0603 (12)	−0.0291 (11)	0.0048 (10)	−0.0101 (10)
C1	0.0392 (11)	0.0353 (11)	0.0444 (11)	−0.0073 (9)	−0.0152 (9)	−0.0050 (9)
C2	0.0719 (16)	0.0387 (12)	0.0527 (13)	−0.0134 (11)	−0.0194 (12)	−0.0028 (10)
C3	0.099 (2)	0.0427 (14)	0.0630 (16)	−0.0160 (13)	−0.0282 (15)	−0.0115 (12)
C4	0.0859 (18)	0.0595 (15)	0.0453 (13)	−0.0144 (13)	−0.0198 (13)	−0.0151 (11)
C5	0.0646 (14)	0.0485 (13)	0.0425 (12)	−0.0173 (11)	−0.0144 (11)	−0.0037 (10)
C6	0.0377 (10)	0.0398 (11)	0.0400 (11)	−0.0080 (9)	−0.0113 (9)	−0.0043 (9)
C7	0.0376 (10)	0.0350 (11)	0.0431 (11)	−0.0076 (8)	−0.0113 (9)	−0.0032 (9)
C8	0.0629 (14)	0.0487 (13)	0.0433 (13)	−0.0169 (11)	−0.0035 (11)	−0.0022 (10)
C9	0.0806 (17)	0.0437 (13)	0.0584 (15)	−0.0246 (12)	−0.0047 (13)	0.0039 (11)
C10	0.0649 (15)	0.0352 (12)	0.0643 (15)	−0.0179 (11)	−0.0103 (12)	−0.0046 (11)
C11	0.0493 (12)	0.0383 (12)	0.0497 (12)	−0.0093 (10)	−0.0133 (10)	−0.0090 (10)
C12	0.0358 (10)	0.0361 (11)	0.0417 (11)	−0.0087 (8)	−0.0118 (9)	−0.0004 (9)
C13	0.0410 (11)	0.0406 (11)	0.0434 (11)	−0.0080 (9)	−0.0104 (9)	−0.0070 (9)
C14	0.0454 (12)	0.0499 (13)	0.0450 (12)	−0.0029 (10)	−0.0104 (10)	−0.0082 (10)
C15	0.0393 (12)	0.0772 (17)	0.0623 (15)	−0.0032 (11)	−0.0135 (11)	−0.0104 (13)
C16	0.0391 (13)	0.0768 (18)	0.0762 (17)	−0.0129 (12)	−0.0038 (12)	−0.0190 (14)
C17	0.0519 (13)	0.0536 (14)	0.0598 (15)	−0.0212 (11)	0.0015 (11)	−0.0077 (11)
C18	0.0477 (12)	0.0452 (13)	0.0519 (13)	−0.0114 (10)	−0.0099 (10)	−0.0025 (10)
C19	0.0677 (16)	0.0687 (17)	0.0514 (14)	0.0185 (13)	−0.0109 (12)	−0.0065 (13)
C20	0.088 (2)	0.0664 (17)	0.0721 (18)	0.0075 (15)	−0.0336 (16)	−0.0075 (14)
C21	0.081 (2)	0.097 (2)	0.095 (2)	0.0012 (18)	−0.0298 (18)	0.0199 (19)
C22	0.094 (2)	0.0631 (18)	0.0715 (18)	−0.0211 (16)	0.0090 (16)	−0.0011 (14)
C23	0.061 (3)	0.067 (3)	0.055 (2)	−0.021 (2)	−0.012 (2)	0.001 (2)
C24	0.071 (3)	0.103 (4)	0.076 (3)	−0.005 (3)	−0.012 (3)	0.024 (3)
C23'	0.054 (4)	0.086 (5)	0.071 (4)	−0.020 (3)	−0.022 (3)	0.025 (4)
C24'	0.061 (4)	0.066 (4)	0.061 (4)	−0.023 (3)	−0.005 (3)	−0.010 (3)

Geometric parameters (Å, º) top

P—O1	1.5932 (16)	C7—C8	1.406 (3)
P—O2	1.4641 (15)	C7—C12	1.390 (3)
P—C1	1.779 (2)	C8—C9	1.376 (3)
P—C13	1.790 (2)	C9—C10	1.381 (4)
O1—C12	1.387 (2)	C10—C11	1.371 (3)
O3—C14	1.370 (3)	C11—C12	1.379 (3)
O3—C19	1.412 (3)	C13—C14	1.396 (3)
O4—C17	1.363 (3)	C13—C18	1.396 (3)
O4—C22	1.389 (4)	C14—C15	1.384 (3)
O5—C20	1.381 (3)	C15—C16	1.369 (4)
O5—C21	1.437 (4)	C16—C17	1.375 (4)
O6—C23	1.415 (4)	C17—C18	1.382 (3)
O6—C24	1.447 (6)	C19—C20	1.494 (4)
O6—C23'	1.380 (7)	C20—C21	1.399 (4)
O6—C24'	1.395 (7)	C22—C23	1.541 (5)
C1—C2	1.395 (3)	C22—C23'	1.520 (7)
C1—C6	1.406 (3)	C23—C24	1.415 (6)
C2—C3	1.376 (3)	C23—C23'	0.776 (8)
C3—C4	1.375 (4)	C23—C24'	0.910 (7)
C4—C5	1.377 (3)	C24—C23'	1.008 (8)
C5—C6	1.395 (3)	C24—C24'	1.455 (8)
C6—C7	1.478 (3)	C23'—C24'	1.436 (9)

O1—P—O2	111.96 (9)	O4—C17—C16	115.3 (2)
O1—P—C1	103.87 (9)	O4—C17—C18	125.2 (2)
O1—P—C13	104.14 (9)	C16—C17—C18	119.5 (2)
O2—P—C1	115.46 (9)	C13—C18—C17	120.0 (2)
O2—P—C13	112.41 (9)	O3—C19—C20	108.1 (2)
C1—P—C13	108.07 (10)	O5—C20—C19	116.8 (3)
P—O1—C12	127.02 (13)	O5—C20—C21	62.3 (2)
C14—O3—C19	118.50 (18)	C19—C20—C21	123.4 (3)
C17—O4—C22	119.2 (2)	O5—C21—C20	58.26 (19)
C20—O5—C21	59.49 (19)	O4—C22—C23	98.6 (3)
C23—O6—C24	59.3 (3)	O4—C22—C23'	124.6 (3)
C23—O6—C23'	32.2 (3)	C23—C22—C23'	29.3 (3)
C23—O6—C24'	37.8 (3)	O6—C23—C22	114.2 (3)
C24—O6—C23'	41.7 (3)	O6—C23—C24	61.5 (3)
C24—O6—C24'	61.5 (4)	O6—C23—C23'	71.4 (6)
C23'—O6—C24'	62.3 (4)	O6—C23—C24'	69.9 (5)
P—C1—C2	117.50 (16)	C22—C23—C24	116.7 (4)
P—C1—C6	122.00 (15)	C22—C23—C23'	73.9 (6)
C2—C1—C6	120.51 (19)	C22—C23—C24'	169.4 (6)
C1—C2—C3	120.4 (2)	C24—C23—C23'	43.7 (6)
C2—C3—C4	119.6 (2)	C24—C23—C24'	73.9 (5)
C3—C4—C5	120.8 (2)	C23'—C23—C24'	116.6 (8)
C4—C5—C6	121.2 (2)	O6—C24—C23	59.2 (3)
C1—C6—C5	117.53 (18)	O6—C24—C23'	65.6 (5)
C1—C6—C7	120.62 (18)	O6—C24—C24'	57.5 (3)
C5—C6—C7	121.81 (18)	C23—C24—C23'	32.1 (4)
C6—C7—C8	121.96 (18)	C23—C24—C24'	37.0 (3)
C6—C7—C12	122.35 (17)	C23'—C24—C24'	68.6 (5)
C8—C7—C12	115.67 (18)	O6—C23'—C22	117.7 (5)
C7—C8—C9	121.7 (2)	O6—C23'—C23	76.4 (6)
C8—C9—C10	120.4 (2)	O6—C23'—C24	72.7 (5)
C9—C10—C11	119.6 (2)	O6—C23'—C24'	59.4 (4)
C10—C11—C12	119.6 (2)	C22—C23'—C23	76.8 (6)
O1—C12—C7	122.51 (17)	C22—C23'—C24	169.2 (8)
O1—C12—C11	114.45 (18)	C22—C23'—C24'	111.3 (5)
C7—C12—C11	123.02 (18)	C23—C23'—C24	104.3 (8)
P—C13—C14	122.03 (16)	C23—C23'—C24'	34.5 (5)
P—C13—C18	118.26 (16)	C24—C23'—C24'	70.6 (6)
C14—C13—C18	119.64 (19)	O6—C24'—C23	72.3 (5)
O3—C14—C13	116.71 (19)	O6—C24'—C24	61.0 (4)
O3—C14—C15	123.9 (2)	O6—C24'—C23'	58.3 (4)
C13—C14—C15	119.4 (2)	C23—C24'—C24	69.2 (5)
C14—C15—C16	120.2 (2)	C23—C24'—C23'	28.9 (4)
C15—C16—C17	121.2 (2)	C24—C24'—C23'	40.8 (4)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁O₆P
M_r	436.40
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.507 (3), 10.613 (4), 12.457 (3)
α, β, γ (°)	80.05 (3), 71.38 (2), 76.69 (3)
V (Å³)	1031.1 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.50 × 0.38 × 0.20

Data collection
Diffractometer	Enraf-Nonius CAD4 diffractometer
Absorption correction	Empirical (using intensity measurements)
T_min, T_max	0.918, 0.953
No. of measured, independent and observed [I_net > 2.0σ(I_net)] reflections	3632, 3619, 2634
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.057, ?
No. of reflections	3619
No. of parameters	299
No. of restraints	?
Δρ_max, Δρ_min (e Å⁻³)	4.30, −2.50

Computer programs: CAD-4 EXPRESS, NRCVAX DATRD2, NRCVAX SOLVER, NRCVAX LSTSQ, NRCVAX ORTEP, NRCVAX TABLES.

Selected geometric parameters (Å, º) top

P—O1	1.5932 (16)	C7—C8	1.406 (3)
P—O2	1.4641 (15)	C7—C12	1.390 (3)
P—C1	1.779 (2)	C8—C9	1.376 (3)
P—C13	1.790 (2)	C9—C10	1.381 (4)
O1—C12	1.387 (2)	C10—C11	1.371 (3)
O3—C14	1.370 (3)	C11—C12	1.379 (3)
O3—C19	1.412 (3)	C13—C14	1.396 (3)
O4—C17	1.363 (3)	C13—C18	1.396 (3)
O4—C22	1.389 (4)	C14—C15	1.384 (3)
O5—C20	1.381 (3)	C15—C16	1.369 (4)
O5—C21	1.437 (4)	C16—C17	1.375 (4)
O6—C23	1.415 (4)	C17—C18	1.382 (3)
O6—C24	1.447 (6)	C19—C20	1.494 (4)
O6—C23'	1.380 (7)	C20—C21	1.399 (4)
O6—C24'	1.395 (7)	C22—C23	1.541 (5)
C1—C2	1.395 (3)	C22—C23'	1.520 (7)
C1—C6	1.406 (3)	C23—C24	1.415 (6)
C2—C3	1.376 (3)	C23—C23'	0.776 (8)
C3—C4	1.375 (4)	C23—C24'	0.910 (7)
C4—C5	1.377 (3)	C24—C23'	1.008 (8)
C5—C6	1.395 (3)	C24—C24'	1.455 (8)
C6—C7	1.478 (3)	C23'—C24'	1.436 (9)

O1—P—O2	111.96 (9)	O4—C17—C16	115.3 (2)
O1—P—C1	103.87 (9)	O4—C17—C18	125.2 (2)
O1—P—C13	104.14 (9)	C16—C17—C18	119.5 (2)
O2—P—C1	115.46 (9)	C13—C18—C17	120.0 (2)
O2—P—C13	112.41 (9)	O3—C19—C20	108.1 (2)
C1—P—C13	108.07 (10)	O5—C20—C19	116.8 (3)
P—O1—C12	127.02 (13)	O5—C20—C21	62.3 (2)
C14—O3—C19	118.50 (18)	C19—C20—C21	123.4 (3)
C17—O4—C22	119.2 (2)	O5—C21—C20	58.26 (19)
C20—O5—C21	59.49 (19)	O4—C22—C23	98.6 (3)
C23—O6—C24	59.3 (3)	O4—C22—C23'	124.6 (3)
C23—O6—C23'	32.2 (3)	C23—C22—C23'	29.3 (3)
C23—O6—C24'	37.8 (3)	O6—C23—C22	114.2 (3)
C24—O6—C23'	41.7 (3)	O6—C23—C24	61.5 (3)
C24—O6—C24'	61.5 (4)	O6—C23—C23'	71.4 (6)
C23'—O6—C24'	62.3 (4)	O6—C23—C24'	69.9 (5)
P—C1—C2	117.50 (16)	C22—C23—C24	116.7 (4)
P—C1—C6	122.00 (15)	C22—C23—C23'	73.9 (6)
C2—C1—C6	120.51 (19)	C22—C23—C24'	169.4 (6)
C1—C2—C3	120.4 (2)	C24—C23—C23'	43.7 (6)
C2—C3—C4	119.6 (2)	C24—C23—C24'	73.9 (5)
C3—C4—C5	120.8 (2)	C23'—C23—C24'	116.6 (8)
C4—C5—C6	121.2 (2)	O6—C24—C23	59.2 (3)
C1—C6—C5	117.53 (18)	O6—C24—C23'	65.6 (5)
C1—C6—C7	120.62 (18)	O6—C24—C24'	57.5 (3)
C5—C6—C7	121.81 (18)	C23—C24—C23'	32.1 (4)
C6—C7—C8	121.96 (18)	C23—C24—C24'	37.0 (3)
C6—C7—C12	122.35 (17)	C23'—C24—C24'	68.6 (5)
C8—C7—C12	115.67 (18)	O6—C23'—C22	117.7 (5)
C7—C8—C9	121.7 (2)	O6—C23'—C23	76.4 (6)
C8—C9—C10	120.4 (2)	O6—C23'—C24	72.7 (5)
C9—C10—C11	119.6 (2)	O6—C23'—C24'	59.4 (4)
C10—C11—C12	119.6 (2)	C22—C23'—C23	76.8 (6)
O1—C12—C7	122.51 (17)	C22—C23'—C24	169.2 (8)
O1—C12—C11	114.45 (18)	C22—C23'—C24'	111.3 (5)
C7—C12—C11	123.02 (18)	C23—C23'—C24	104.3 (8)
P—C13—C14	122.03 (16)	C23—C23'—C24'	34.5 (5)
P—C13—C18	118.26 (16)	C24—C23'—C24'	70.6 (6)
C14—C13—C18	119.64 (19)	O6—C24'—C23	72.3 (5)
O3—C14—C13	116.71 (19)	O6—C24'—C24	61.0 (4)
O3—C14—C15	123.9 (2)	O6—C24'—C23'	58.3 (4)
C13—C14—C15	119.4 (2)	C23—C24'—C24	69.2 (5)
C14—C15—C16	120.2 (2)	C23—C24'—C23'	28.9 (4)
C15—C16—C17	121.2 (2)	C24—C24'—C23'	40.8 (4)

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