2-(4-{4-[4-(Oxiran-2-ylmeth-oxy)phen-oxy]phen-yl}phen-oxy-meth-yl)oxirane.

In the title ep-oxy monomer, C(24)H(22)O(5), the dihedral angle in the biphenyl residue is 3.34 (19)°, indicating a nearly coplanar conformation; this residue is not planar with the adjacent benzene ring [dihedral angle = 58.93 (14)°]. Each of the epoxide rings is disordered. Each epoxide ring was resolved over two alternative positions with site-occupancy ratios of 0.638 (10):0.362 (10) and 0.797 (9):0.203 (9).

Related literature

For micro-electronic applications of biphenyl-type ep­oxy compounds, see: Lee & Neville (1990 ▶); Yoda (1997 ▶); Kim & Lee (2002 ▶). For related structures, see: Cho et al. (1999 ▶); Flippen-Anderson & Gilardi (1981 ▶).

Experimental

Crystal data

C24H22O5

M = 390.42

Monoclinic,

a = 21.261 (4) Å

b = 7.3103 (15) Å

c = 6.1322 (12) Å

β = 93.59 (3)°

V = 951.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.35 × 0.15 × 0.08 mm

Data collection

Rigaku Saturn724+ CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.983, T max = 0.992

6607 measured reflections

1965 independent reflections

1728 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.085

wR(F 2) = 0.172

S = 1.18

1965 reflections

318 parameters

264 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005740/tk5057sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005740/tk5057Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005740/tk5057Isup3.cml

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

C24H22O5	F(000) = 412
Mr = 390.42	Dx = 1.363 Mg m−3
Monoclinic, Pc	Melting point: 438 K
Hall symbol: P -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 21.261 (4) Å	Cell parameters from 2903 reflections
b = 7.3103 (15) Å	θ = 1.9–27.4°
c = 6.1322 (12) Å	µ = 0.10 mm−1
β = 93.59 (3)°	T = 173 K
V = 951.2 (3) Å3	Rod, colourless
Z = 2	0.35 × 0.15 × 0.08 mm

Rigaku Saturn724+ CCD diffractometer	1965 independent reflections
Radiation source: fine-focus sealed tube	1728 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 28.5714 pixels mm-1	θmax = 26.5°, θmin = 2.8°
ω scans at fixed χ = 45°	h = −26→26
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −9→8
Tmin = 0.983, Tmax = 0.992	l = −6→7
6607 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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.969P] where P = (Fo2 + 2Fc2)/3
1965 reflections	(Δ/σ)max = 0.001
318 parameters	Δρmax = 0.23 e Å−3
264 restraints	Δρmin = −0.19 e Å−3

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	Occ. (<1)
O2	0.9679 (2)	0.7379 (6)	0.1402 (7)	0.0392 (11)
O3	0.54379 (19)	0.7479 (6)	−0.6168 (6)	0.0332 (10)
O4	0.3068 (2)	0.7607 (6)	−0.2978 (7)	0.0410 (11)
O1	1.0723 (6)	0.8198 (13)	0.6156 (15)	0.061 (2)	0.638 (10)
C1	1.0717 (6)	0.6394 (13)	0.5111 (18)	0.060 (2)	0.638 (10)
H1B	1.1127	0.5836	0.4810	0.072*	0.638 (10)
H1A	1.0386	0.5516	0.5492	0.072*	0.638 (10)
C2	1.0523 (4)	0.7999 (16)	0.3903 (17)	0.055 (2)	0.638 (10)
H2	1.0802	0.8476	0.2777	0.066*	0.638 (10)
O1'	1.0674 (10)	0.770 (3)	0.653 (2)	0.060 (3)	0.362 (10)
C1'	1.0982 (9)	0.767 (3)	0.449 (3)	0.059 (3)	0.362 (10)
H1'B	1.1318	0.6756	0.4321	0.070*	0.362 (10)
H1'A	1.1042	0.8853	0.3743	0.070*	0.362 (10)
C2'	1.0322 (7)	0.700 (2)	0.466 (3)	0.058 (3)	0.362 (10)
H2'	1.0254	0.5642	0.4592	0.070*	0.362 (10)
C3	0.9816 (3)	0.8206 (11)	0.3504 (11)	0.0502 (19)
H3A	0.9591	0.7566	0.4646	0.060*
H3B	0.9692	0.9512	0.3485	0.060*
C4	0.9072 (2)	0.7504 (8)	0.0492 (9)	0.0279 (13)
C5	0.8585 (3)	0.8380 (8)	0.1427 (9)	0.0354 (15)
H5	0.8656	0.8995	0.2784	0.042*
C6	0.7988 (3)	0.8361 (8)	0.0377 (9)	0.0346 (14)
H6	0.7654	0.8960	0.1051	0.041*
C7	0.7856 (3)	0.7487 (8)	−0.1651 (9)	0.0267 (12)
C8	0.8369 (3)	0.6606 (8)	−0.2527 (9)	0.0317 (14)
H8	0.8308	0.5998	−0.3893	0.038*
C9	0.8956 (3)	0.6597 (8)	−0.1472 (9)	0.0300 (13)
H9	0.9289	0.5957	−0.2098	0.036*
C10	0.7221 (3)	0.7498 (7)	−0.2772 (9)	0.0263 (12)
C11	0.6702 (3)	0.8303 (8)	−0.1862 (9)	0.0336 (14)
H11	0.6764	0.8877	−0.0475	0.040*
C12	0.6101 (3)	0.8307 (8)	−0.2881 (10)	0.0343 (14)
H12	0.5760	0.8871	−0.2209	0.041*
C13	0.6008 (3)	0.7464 (8)	−0.4914 (9)	0.0313 (14)
C14	0.6509 (3)	0.6685 (8)	−0.5893 (9)	0.0299 (13)
H14	0.6449	0.6136	−0.7295	0.036*
C15	0.7100 (3)	0.6714 (8)	−0.4809 (9)	0.0315 (13)
H15	0.7441	0.6166	−0.5500	0.038*
C16	0.4871 (3)	0.7515 (8)	−0.5173 (9)	0.0294 (13)
C17	0.4759 (3)	0.6561 (8)	−0.3279 (9)	0.0292 (12)
H17	0.5092	0.5914	−0.2517	0.035*
C18	0.4161 (3)	0.6554 (8)	−0.2499 (10)	0.0370 (14)
H18	0.4082	0.5906	−0.1202	0.044*
C19	0.3672 (3)	0.7514 (8)	−0.3645 (9)	0.0311 (14)
C20	0.3787 (3)	0.8422 (8)	−0.5512 (9)	0.0349 (14)
H20	0.3453	0.9050	−0.6294	0.042*
C21	0.4385 (3)	0.8444 (8)	−0.6291 (9)	0.0299 (13)
H21	0.4460	0.9096	−0.7589	0.036*
C22	0.2927 (3)	0.6724 (9)	−0.1012 (10)	0.0426 (16)
H22B	0.3163	0.7297	0.0254	0.051*
H22A	0.3041	0.5412	−0.1060	0.051*
O5	0.2061 (4)	0.6830 (10)	0.1419 (11)	0.061 (2)	0.797 (9)
C23	0.2222 (4)	0.6948 (12)	−0.0834 (13)	0.056 (2)	0.797 (9)
H23	0.1924	0.6448	−0.2014	0.067*	0.797 (9)
C24	0.2043 (5)	0.8605 (11)	0.0384 (15)	0.063 (2)	0.797 (9)
H24B	0.2380	0.9489	0.0829	0.075*	0.797 (9)
H24A	0.1626	0.9157	0.0004	0.075*	0.797 (9)
O5'	0.1776 (12)	0.714 (4)	−0.023 (4)	0.063 (3)	0.203 (9)
C23'	0.2400 (10)	0.788 (4)	−0.012 (6)	0.059 (3)	0.203 (9)
H23A	0.2427	0.9221	−0.0413	0.071*	0.203 (9)
C24'	0.207 (2)	0.737 (8)	0.193 (4)	0.061 (3)	0.203 (9)
H24C	0.2210	0.6258	0.2739	0.073*	0.203 (9)
H24D	0.1915	0.8373	0.2843	0.073*	0.203 (9)

	U11	U22	U33	U12	U13	U23
O2	0.028 (2)	0.047 (3)	0.042 (3)	0.011 (2)	−0.0011 (18)	−0.008 (2)
O3	0.030 (2)	0.042 (3)	0.028 (2)	−0.0026 (18)	0.0013 (17)	−0.0061 (18)
O4	0.040 (3)	0.042 (3)	0.041 (2)	0.006 (2)	0.001 (2)	0.011 (2)
O1	0.060 (4)	0.069 (5)	0.053 (4)	0.006 (4)	−0.008 (3)	−0.003 (4)
C1	0.057 (4)	0.064 (5)	0.058 (4)	0.004 (4)	−0.005 (4)	−0.005 (4)
C2	0.053 (4)	0.063 (5)	0.048 (4)	0.002 (4)	−0.001 (4)	−0.003 (4)
O1'	0.058 (4)	0.069 (5)	0.052 (5)	0.005 (4)	−0.003 (4)	−0.003 (4)
C1'	0.056 (5)	0.067 (5)	0.052 (5)	0.003 (4)	−0.001 (4)	0.000 (4)
C2'	0.056 (5)	0.064 (5)	0.053 (5)	0.003 (4)	−0.007 (4)	−0.002 (4)
C3	0.039 (4)	0.062 (5)	0.047 (4)	0.015 (3)	−0.012 (3)	−0.011 (4)
C4	0.022 (3)	0.029 (3)	0.032 (3)	0.007 (2)	0.002 (2)	0.005 (2)
C5	0.045 (4)	0.029 (3)	0.032 (3)	−0.003 (3)	0.000 (3)	0.003 (2)
C6	0.045 (4)	0.027 (3)	0.032 (3)	0.009 (3)	0.001 (3)	0.001 (3)
C7	0.031 (3)	0.024 (3)	0.025 (3)	−0.004 (2)	0.005 (2)	0.011 (2)
C8	0.033 (3)	0.032 (3)	0.031 (3)	0.004 (3)	0.007 (3)	−0.006 (2)
C9	0.024 (3)	0.033 (3)	0.035 (3)	0.009 (2)	0.013 (2)	−0.003 (3)
C10	0.031 (3)	0.022 (3)	0.026 (3)	0.003 (2)	0.008 (2)	−0.002 (2)
C11	0.044 (4)	0.026 (3)	0.030 (3)	−0.002 (3)	0.000 (3)	−0.006 (2)
C12	0.037 (4)	0.028 (3)	0.038 (3)	−0.005 (3)	−0.001 (3)	−0.005 (3)
C13	0.036 (3)	0.026 (3)	0.032 (3)	−0.018 (3)	0.004 (3)	0.002 (2)
C14	0.033 (3)	0.035 (3)	0.022 (3)	0.005 (3)	0.002 (2)	−0.006 (2)
C15	0.025 (3)	0.039 (3)	0.032 (3)	−0.003 (3)	0.016 (2)	−0.004 (3)
C16	0.036 (3)	0.020 (3)	0.033 (3)	0.001 (2)	0.003 (2)	−0.011 (2)
C17	0.028 (3)	0.028 (3)	0.031 (3)	0.000 (2)	−0.002 (2)	0.002 (2)
C18	0.045 (4)	0.030 (3)	0.036 (3)	−0.003 (3)	0.001 (3)	−0.004 (3)
C19	0.019 (3)	0.034 (3)	0.040 (3)	0.007 (2)	−0.005 (2)	−0.009 (3)
C20	0.041 (4)	0.033 (3)	0.030 (3)	0.009 (3)	−0.008 (3)	0.007 (3)
C21	0.033 (3)	0.030 (3)	0.027 (3)	0.000 (3)	0.004 (2)	0.007 (2)
C22	0.034 (3)	0.050 (4)	0.044 (4)	0.004 (3)	0.007 (3)	0.017 (3)
O5	0.057 (3)	0.071 (4)	0.058 (3)	0.011 (3)	0.024 (3)	0.009 (3)
C23	0.055 (4)	0.063 (4)	0.053 (4)	0.006 (4)	0.020 (3)	0.001 (4)
C24	0.060 (4)	0.066 (4)	0.064 (4)	0.006 (4)	0.016 (3)	0.002 (4)
O5'	0.061 (5)	0.070 (5)	0.061 (5)	0.005 (5)	0.017 (4)	0.002 (5)
C23'	0.058 (5)	0.064 (5)	0.057 (5)	0.005 (5)	0.015 (5)	0.004 (5)
C24'	0.060 (5)	0.067 (6)	0.058 (5)	0.007 (5)	0.017 (5)	0.002 (5)

O2—C4	1.378 (7)	C11—C12	1.386 (8)
O2—C3	1.437 (7)	C11—H11	0.9500
O3—C16	1.385 (7)	C12—C13	1.393 (8)
O3—C13	1.395 (7)	C12—H12	0.9500
O4—C19	1.374 (7)	C13—C14	1.377 (8)
O4—C22	1.416 (7)	C14—C15	1.385 (8)
O1—C2	1.427 (8)	C14—H14	0.9500
O1—C1	1.466 (9)	C15—H15	0.9500
C1—C2	1.434 (13)	C16—C21	1.382 (8)
C1—H1B	0.9900	C16—C17	1.388 (8)
C1—H1A	0.9900	C17—C18	1.387 (8)
C2—C3	1.517 (8)	C17—H17	0.9500
C2—H2	1.0000	C18—C19	1.405 (8)
O1'—C2'	1.423 (10)	C18—H18	0.9500
O1'—C1'	1.444 (10)	C19—C20	1.359 (9)
C1'—C2'	1.498 (18)	C20—C21	1.386 (8)
C1'—H1'B	0.9900	C20—H20	0.9500
C1'—H1'A	0.9900	C21—H21	0.9500
C2'—C3	1.532 (10)	C22—C23	1.519 (8)
C2'—H2'	1.0000	C22—C23'	1.532 (10)
C3—H3A	0.9900	C22—H22B	0.9900
C3—H3B	0.9900	C22—H22A	0.9900
C4—C5	1.373 (8)	O5—C24	1.444 (8)
C4—C9	1.383 (8)	O5—C23	1.447 (8)
C5—C6	1.387 (8)	C23—C24	1.485 (8)
C5—H5	0.9500	C23—H23	1.0000
C6—C7	1.410 (8)	C24—H24B	0.9900
C6—H6	0.9500	C24—H24A	0.9900
C7—C8	1.404 (8)	O5'—C23'	1.430 (10)
C7—C10	1.476 (7)	O5'—C24'	1.435 (10)
C8—C9	1.369 (8)	C23'—C24'	1.526 (10)
C8—H8	0.9500	C23'—H23A	1.0000
C9—H9	0.9500	C24'—H24C	0.9900
C10—C15	1.383 (8)	C24'—H24D	0.9900
C10—C11	1.398 (8)
C4—O2—C3	117.8 (4)	C13—C12—H12	120.8
C16—O3—C13	120.6 (4)	C14—C13—C12	120.2 (6)
C19—O4—C22	118.8 (5)	C14—C13—O3	115.6 (5)
C2—O1—C1	59.4 (6)	C12—C13—O3	124.0 (6)
C2—C1—O1	59.0 (5)	C13—C14—C15	119.1 (5)
C2—C1—H1B	117.9	C13—C14—H14	120.4
O1—C1—H1B	117.9	C15—C14—H14	120.4
C2—C1—H1A	117.9	C10—C15—C14	123.5 (5)
O1—C1—H1A	117.9	C10—C15—H15	118.3
H1B—C1—H1A	115.0	C14—C15—H15	118.3
O1—C2—C1	61.6 (5)	C21—C16—O3	115.8 (5)
O1—C2—C3	112.2 (9)	C21—C16—C17	120.0 (5)
C1—C2—C3	114.5 (10)	O3—C16—C17	123.9 (5)
O1—C2—H2	118.6	C18—C17—C16	119.9 (5)
C1—C2—H2	118.6	C18—C17—H17	120.0
C3—C2—H2	118.6	C16—C17—H17	120.0
C2'—O1'—C1'	63.0 (9)	C17—C18—C19	119.4 (6)
O1'—C1'—C2'	57.8 (6)	C17—C18—H18	120.3
O1'—C1'—H1'B	118.0	C19—C18—H18	120.3
C2'—C1'—H1'B	118.0	C20—C19—O4	116.6 (5)
O1'—C1'—H1'A	118.0	C20—C19—C18	119.9 (6)
C2'—C1'—H1'A	118.0	O4—C19—C18	123.5 (5)
H1'B—C1'—H1'A	115.2	C19—C20—C21	120.9 (5)
O1'—C2'—C1'	59.2 (6)	C19—C20—H20	119.6
O1'—C2'—C3	118.9 (16)	C21—C20—H20	119.6
C1'—C2'—C3	114.3 (16)	C16—C21—C20	119.8 (5)
O1'—C2'—H2'	117.2	C16—C21—H21	120.1
C1'—C2'—H2'	117.2	C20—C21—H21	120.1
C3—C2'—H2'	117.2	O4—C22—C23	105.8 (5)
O2—C3—C2	104.2 (6)	O4—C22—C23'	104.5 (14)
O2—C3—C2'	105.6 (8)	O4—C22—H22B	110.6
O2—C3—H3A	110.9	C23—C22—H22B	110.6
C2—C3—H3A	110.9	C23'—C22—H22B	80.3
C2'—C3—H3A	75.9	O4—C22—H22A	110.6
O2—C3—H3B	110.9	C23—C22—H22A	110.6
C2—C3—H3B	110.9	C23'—C22—H22A	136.9
C2'—C3—H3B	137.7	H22B—C22—H22A	108.7
H3A—C3—H3B	108.9	C24—O5—C23	61.8 (4)
C5—C4—O2	125.1 (5)	O5—C23—C24	59.0 (4)
C5—C4—C9	119.3 (5)	O5—C23—C22	110.8 (7)
O2—C4—C9	115.6 (5)	C24—C23—C22	114.1 (8)
C4—C5—C6	119.6 (5)	O5—C23—H23	119.5
C4—C5—H5	120.2	C24—C23—H23	119.5
C6—C5—H5	120.2	C22—C23—H23	119.5
C5—C6—C7	122.7 (6)	O5—C24—C23	59.2 (4)
C5—C6—H6	118.7	O5—C24—H24B	117.9
C7—C6—H6	118.7	C23—C24—H24B	117.9
C8—C7—C6	115.4 (6)	O5—C24—H24A	117.9
C8—C7—C10	122.3 (5)	C23—C24—H24A	117.9
C6—C7—C10	122.3 (5)	H24B—C24—H24A	115.0
C9—C8—C7	121.9 (5)	C23'—O5'—C24'	64.3 (6)
C9—C8—H8	119.0	O5'—C23'—C24'	58.0 (6)
C7—C8—H8	119.0	O5'—C23'—C22	118 (2)
C8—C9—C4	121.1 (5)	C24'—C23'—C22	123 (3)
C8—C9—H9	119.4	O5'—C23'—H23A	115.1
C4—C9—H9	119.4	C24'—C23'—H23A	115.1
C15—C10—C11	115.3 (5)	C22—C23'—H23A	115.1
C15—C10—C7	122.1 (5)	O5'—C24'—C23'	57.7 (5)
C11—C10—C7	122.6 (5)	O5'—C24'—H24C	118.0
C12—C11—C10	123.3 (5)	C23'—C24'—H24C	118.0
C12—C11—H11	118.3	O5'—C24'—H24D	118.0
C10—C11—H11	118.3	C23'—C24'—H24D	118.0
C11—C12—C13	118.5 (6)	H24C—C24'—H24D	115.2
C11—C12—H12	120.8
C1—O1—C2—C3	106.7 (11)	C16—O3—C13—C14	154.0 (5)
O1—C1—C2—C3	−103.1 (10)	C16—O3—C13—C12	−31.6 (8)
C1'—O1'—C2'—C3	−103 (2)	C12—C13—C14—C15	1.5 (9)
O1'—C1'—C2'—C3	110.3 (19)	O3—C13—C14—C15	176.2 (5)
C4—O2—C3—C2	−174.2 (6)	C11—C10—C15—C14	−0.9 (8)
C4—O2—C3—C2'	146.9 (9)	C7—C10—C15—C14	179.3 (5)
O1—C2—C3—O2	−161.3 (8)	C13—C14—C15—C10	−0.3 (9)
C1—C2—C3—O2	−93.5 (9)	C13—O3—C16—C21	147.4 (5)
O1—C2—C3—C2'	−64.0 (15)	C13—O3—C16—C17	−38.3 (8)
C1—C2—C3—C2'	3.8 (13)	C21—C16—C17—C18	−0.5 (8)
O1'—C2'—C3—O2	163.7 (14)	O3—C16—C17—C18	−174.6 (5)
C1'—C2'—C3—O2	96.8 (14)	C16—C17—C18—C19	0.1 (8)
O1'—C2'—C3—C2	70.6 (16)	C22—O4—C19—C20	−178.4 (6)
C1'—C2'—C3—C2	3.7 (11)	C22—O4—C19—C18	1.3 (9)
C3—O2—C4—C5	0.8 (9)	C17—C18—C19—C20	0.7 (9)
C3—O2—C4—C9	−176.4 (6)	C17—C18—C19—O4	−178.9 (5)
O2—C4—C5—C6	−177.9 (5)	O4—C19—C20—C21	178.5 (5)
C9—C4—C5—C6	−0.8 (9)	C18—C19—C20—C21	−1.2 (9)
C4—C5—C6—C7	−0.7 (9)	O3—C16—C21—C20	174.6 (5)
C5—C6—C7—C8	1.0 (8)	C17—C16—C21—C20	0.1 (8)
C5—C6—C7—C10	−179.1 (5)	C19—C20—C21—C16	0.8 (9)
C6—C7—C8—C9	0.2 (8)	C19—O4—C22—C23	−175.6 (5)
C10—C7—C8—C9	−179.7 (5)	C19—O4—C22—C23'	149.6 (13)
C7—C8—C9—C4	−1.7 (9)	C24—O5—C23—C22	106.3 (8)
C5—C4—C9—C8	2.0 (9)	O4—C22—C23—O5	−155.6 (6)
O2—C4—C9—C8	179.4 (5)	C23'—C22—C23—O5	−63 (3)
C8—C7—C10—C15	−3.2 (8)	O4—C22—C23—C24	−91.2 (7)
C6—C7—C10—C15	176.9 (6)	C23'—C22—C23—C24	1 (2)
C8—C7—C10—C11	177.1 (6)	C22—C23—C24—O5	−100.7 (8)
C6—C7—C10—C11	−2.8 (8)	C24'—O5'—C23'—C22	113 (4)
C15—C10—C11—C12	1.0 (8)	O4—C22—C23'—O5'	107 (2)
C7—C10—C11—C12	−179.2 (5)	C23—C22—C23'—O5'	10.7 (14)
C10—C11—C12—C13	0.1 (9)	O4—C22—C23'—C24'	176 (2)
C11—C12—C13—C14	−1.4 (9)	C23—C22—C23'—C24'	79 (2)
C11—C12—C13—O3	−175.6 (5)	C22—C23'—C24'—O5'	−105 (3)