15-Crown-5

15-Crown-5 (systematic name: 1,4,7,10,13-penta­oxacyl­openta­deca­ne), C₁₀H₂₀O₅, which is liquid at room temperature, has been crystallized using in situ methods. It crystallizes with two different conformers in the asymmetric unit, which differ from those identified in conformational searches based on data mining and computational methods. The mol­ecules inter­act through face-to-face C—H...O contacts to form layers which stack along the [001] direction.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.043
• wR factor = 0.084
• Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       1.00 mm

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.730     0.970
            Tmin(prime) and Tmax expected:      0.904     0.970
            RR(prime) =      0.808
            Please check that your absorption correction is appropriate.
CRYSR01_ALERT_1_C  _exptl_crystal_size_rad not in the CIF when expected.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.81
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.37
           From the CIF: _reflns_number_total               2414
           Count of symmetry unique reflns         2414
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

15-crown-5 (I) is a crown ether which is often used as a ligand in coordination chemistry. It crystallizes in space group P4₁ with two molecules in the asymmetric unit. The conformations of the two molecules are different (Figs. 1 and 2). Hill & Feller (2000) studied conformations of I using ab initio methods, identifying 16 low-energy conformers, though none of these appear to match either of those observed here. Raithby et al. (1997) analysed conformers of I in the Cambridge Database (Allen, 2002), and though regions of the uniangular conformers identified in that study resemble the conformations observed here the agreement is not complete. Three CH···O contacts in the range 2.5–2.6 Å are formed between molecules, with a forth intramolecular interaction formed between H84 and O42 (2.51 Å). Hill & Feller (2000) commented that accurate prediction of low-lying conformations in floppy molecules is a challenging task, and the presence of intermolecular interactions, though weak, could well alter computational energy rankings derived for isolated molecules.

Related literature

Hill & Feller (2000) studied conformations of the title compound using ab initio methods. Raithby et al. (1997) analysed conformers of the title compound in the Cambridge Structural Database (Allen, 2002).

For related literature, see: Blessing (1987); Boese & Nussbaumer (1994); Görbitz (1999).

S2. Experimental

15-Crown-5, which is a liquid at room temperature, was obtained from Aldrich and used as received.

A sample of 15-crown-5 was drawn into a glass capillary and mounted on the diffractometer with the low-temperature device set to 220 K. The compound supercooled at first, but solidified into a glassy mass on swabbing with liquid nitrogen. The glass was annealed into a polycrystalline mass by scanning the capillary with an IR laser (OHCD) for 4 h. The power set at half that needed to melt the sample, with the low temperature device set to 230 K. A crystal was subsequently grown over the course of 1 h by Boese's laser-assisted crystal growth method (Boese & Nussbaumer, 1994).

The crystal grown was larger than the beam-size (0.3 mm). This often happens with low-melting compounds, as there is little experimental control over the length of a crystal grown in situ in a capillary. Görbitz (1999) has shown that use of a large crystal does not degrade data quality.

A data set was collected at 220 K, where the unit-cell dimensions were a = 8.8532 (5), c = 30.172 (2) Å. The crystal was then cooled to 120 K at a rate of 360 K h^-1 for the structure determination reported here.

Following data collection a multiscan absorption correction was applied (SADABS, Sheldrick, 2007), though the range of transmission was more extreme than would have been calculated on crystal dimensions. SADABS corrects for all systematic errors that lead to disparities in the intensities of symmetry-equivalent data. These may include absorption by the mount, crystal decay, changes in the volume of the crystal illuminated, etc. Here the glass capillary is an obvious extra source of absorption.

One reflection (011) appears to have been obscured by the beam-stop.

S3. Refinement

Though the space group is P4₁, absolute scattering effects are very slight and data were merged in point group 4/m. The abolute structure has not been established in this study.

H-atoms were placed in calculated positions with a CH bond distance of 0.99 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Siemens, 1993); cell refinement: SAINT; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: XP (Sheldrick, 1997); software used to prepare material for publication: CRYSTALS.

Figures

	Fig. 1. : The molecular structure of the meolecule based on O11 in the crystal structure of (I). Non-H atoms are represented with 50% probability displacement ellipsoids.
	Fig. 2. : The molecular structure of the meolecule based on O12 in the crystal structure of (I). Non-H atoms are represented with 50% probability displacement ellipsoids.

1,4,7,10,13-pentaoxacylopentadecane

Crystal data

C10H20O5	Dx = 1.258 Mg m^−3
Mr = 220.27	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41	Cell parameters from 5144 reflections
Hall symbol: P 4w	θ = 2–21°
a = 8.7954 (1) Å	µ = 0.10 mm^−1
c = 30.0676 (10) Å	T = 120 K
V = 2326.00 (9) Å^3	Cylinder, colourless
Z = 8	1.00 × 0.30 × 0.30 mm
F(000) = 960

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1996 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
Tmin = 0.73, Tmax = 0.97	k = −10→10
24253 measured reflections	l = −37→37
2414 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters not refined
wR(F^2) = 0.084	Method, part 1, Chebychev polynomial, [Watkin, D. (1994). Acta Cryst. A50, 411–437. Prince, E. (2004). Mathematical Techniques in Crystallography and Materials Science, 3rd ed., p. 81. New York: Springer-Verlag] [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 2004) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 158. 236. 145. 57.8 14.6
S = 0.95	(Δ/σ)max = 0.005
2414 reflections	Δρmax = 0.20 e Å^−3
271 parameters	Δρmin = −0.16 e Å^−3
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O11	0.8585 (3)	0.1125 (3)	0.65682 (10)	0.0359
C21	0.7737 (4)	0.2441 (4)	0.64577 (13)	0.0315
C31	0.6206 (4)	0.2220 (4)	0.66747 (13)	0.0313
O41	0.5287 (3)	0.3540 (3)	0.66244 (10)	0.0332
C51	0.3923 (4)	0.3337 (4)	0.63720 (13)	0.0345
C61	0.4052 (4)	0.3894 (4)	0.59059 (14)	0.0356
O71	0.5012 (3)	0.2899 (3)	0.56624 (9)	0.0333
C81	0.5226 (5)	0.3386 (4)	0.52185 (13)	0.0368
C91	0.6388 (5)	0.2377 (4)	0.50020 (13)	0.0373
O101	0.7829 (3)	0.2746 (3)	0.51751 (10)	0.0370
C111	0.8965 (5)	0.1651 (4)	0.50746 (14)	0.0371
C121	1.0431 (4)	0.2156 (4)	0.52836 (15)	0.0387
O131	1.0336 (3)	0.2323 (3)	0.57526 (11)	0.0340
C141	1.0566 (4)	0.0962 (4)	0.59932 (15)	0.0363
C151	1.0171 (4)	0.1225 (4)	0.64738 (14)	0.0349
O12	0.6696 (3)	0.8020 (3)	0.39743 (9)	0.0293
C22	0.7388 (4)	0.7345 (4)	0.43517 (12)	0.0286
C32	0.7435 (4)	0.5657 (4)	0.42843 (12)	0.0293
O42	0.8383 (3)	0.5346 (3)	0.39138 (9)	0.0298
C52	0.8145 (4)	0.3873 (4)	0.37354 (14)	0.0316
C62	0.8974 (4)	0.3728 (4)	0.32991 (14)	0.0341
O72	0.8270 (3)	0.4512 (3)	0.29374 (10)	0.0378
C82	0.8440 (4)	0.6116 (4)	0.29590 (13)	0.0345
C92	0.8089 (5)	0.6733 (5)	0.25020 (14)	0.0427
O102	0.8080 (3)	0.8351 (3)	0.25098 (10)	0.0396
C112	0.6627 (4)	0.8981 (5)	0.25936 (14)	0.0377
C122	0.6797 (4)	1.0472 (4)	0.28319 (13)	0.0332
O132	0.7249 (3)	1.0262 (3)	0.32812 (10)	0.0303
C142	0.6008 (4)	1.0242 (4)	0.35831 (13)	0.0306
C152	0.6532 (4)	0.9617 (4)	0.40185 (13)	0.0302
H21	0.8243	0.3363	0.6577	0.0383*
H22	0.7629	0.2531	0.6132	0.0383*
H31	0.6353	0.2012	0.6996	0.0374*
H32	0.5687	0.1346	0.6534	0.0374*
H51	0.3095	0.3900	0.6524	0.0414*
H52	0.3678	0.2239	0.6369	0.0414*
H61	0.4490	0.4931	0.5904	0.0424*
H62	0.3032	0.3915	0.5767	0.0424*
H81	0.5586	0.4452	0.5217	0.0437*
H82	0.4250	0.3316	0.5056	0.0437*
H91	0.6152	0.1298	0.5067	0.0445*
H92	0.6381	0.2542	0.4677	0.0445*
H111	0.8668	0.0650	0.5197	0.0441*
H112	0.9095	0.1575	0.4749	0.0441*
H121	1.1227	0.1391	0.5216	0.0477*
H122	1.0728	0.3147	0.5153	0.0477*
H141	1.1644	0.0648	0.5969	0.0441*
H142	0.9907	0.0152	0.5870	0.0441*
H151	1.0707	0.0453	0.6656	0.0422*
H152	1.0526	0.2252	0.6559	0.0422*
H23	0.8433	0.7743	0.4389	0.0338*
H24	0.6785	0.7587	0.4623	0.0338*
H33	0.7855	0.5157	0.4555	0.0359*
H34	0.6397	0.5267	0.4229	0.0359*
H53	0.8532	0.3097	0.3947	0.0389*
H54	0.7043	0.3706	0.3687	0.0389*
H63	1.0012	0.4142	0.3340	0.0411*
H64	0.9037	0.2636	0.3222	0.0411*
H83	0.9494	0.6378	0.3046	0.0420*
H84	0.7723	0.6544	0.3181	0.0420*
H93	0.8872	0.6375	0.2291	0.0510*
H94	0.7078	0.6360	0.2407	0.0510*
H113	0.6029	0.8274	0.2781	0.0460*
H114	0.6093	0.9149	0.2309	0.0460*
H123	0.7572	1.1091	0.2678	0.0407*
H124	0.5808	1.1012	0.2827	0.0407*
H143	0.5620	1.1292	0.3627	0.0381*
H144	0.5182	0.9596	0.3463	0.0381*
H153	0.7526	1.0074	0.4100	0.0368*
H154	0.5780	0.9850	0.4254	0.0368*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0300 (14)	0.0283 (13)	0.0495 (17)	0.0026 (11)	0.0000 (12)	0.0089 (12)
C21	0.0331 (19)	0.0276 (18)	0.034 (2)	0.0014 (15)	−0.0017 (16)	0.0081 (16)
C31	0.034 (2)	0.032 (2)	0.0275 (19)	0.0016 (15)	0.0009 (15)	0.0021 (15)
O41	0.0312 (14)	0.0290 (14)	0.0395 (15)	0.0036 (11)	−0.0031 (12)	−0.0071 (11)
C51	0.0281 (19)	0.036 (2)	0.039 (2)	0.0010 (15)	0.0017 (17)	−0.0070 (17)
C61	0.0284 (19)	0.0310 (19)	0.047 (2)	0.0067 (15)	−0.0006 (17)	−0.0013 (17)
O71	0.0343 (14)	0.0338 (13)	0.0317 (15)	0.0054 (11)	−0.0007 (11)	0.0006 (11)
C81	0.040 (2)	0.041 (2)	0.029 (2)	0.0003 (17)	−0.0054 (17)	0.0026 (17)
C91	0.051 (2)	0.034 (2)	0.0268 (19)	−0.0097 (18)	−0.0036 (18)	0.0001 (16)
O101	0.0411 (16)	0.0331 (15)	0.0369 (15)	−0.0011 (12)	0.0060 (12)	−0.0056 (12)
C111	0.049 (2)	0.031 (2)	0.032 (2)	−0.0005 (17)	0.0170 (18)	−0.0028 (16)
C121	0.035 (2)	0.037 (2)	0.044 (2)	0.0009 (17)	0.0172 (18)	−0.0007 (18)
O131	0.0335 (15)	0.0270 (13)	0.0416 (15)	−0.0028 (11)	0.0078 (12)	−0.0040 (12)
C141	0.0276 (19)	0.0260 (19)	0.055 (3)	0.0007 (15)	0.0000 (17)	−0.0028 (18)
C151	0.0246 (18)	0.036 (2)	0.044 (2)	0.0012 (15)	−0.0046 (17)	0.0054 (18)
O12	0.0377 (14)	0.0237 (12)	0.0264 (12)	−0.0021 (10)	−0.0039 (11)	0.0010 (10)
C22	0.0276 (18)	0.035 (2)	0.0231 (18)	−0.0006 (15)	0.0007 (14)	0.0031 (15)
C32	0.0279 (18)	0.0331 (19)	0.0270 (18)	−0.0012 (15)	−0.0004 (15)	0.0068 (15)
O42	0.0324 (14)	0.0278 (13)	0.0291 (14)	−0.0025 (11)	0.0047 (11)	−0.0004 (10)
C52	0.0315 (19)	0.0218 (17)	0.042 (2)	−0.0010 (15)	−0.0030 (16)	0.0050 (15)
C62	0.038 (2)	0.0271 (19)	0.038 (2)	−0.0002 (16)	−0.0059 (17)	−0.0051 (16)
O72	0.0486 (16)	0.0257 (13)	0.0392 (16)	−0.0030 (12)	−0.0123 (13)	−0.0065 (12)
C82	0.045 (2)	0.0305 (19)	0.028 (2)	−0.0049 (16)	−0.0020 (17)	−0.0052 (17)
C92	0.057 (3)	0.040 (2)	0.031 (2)	0.0015 (19)	0.001 (2)	−0.0050 (18)
O102	0.0442 (16)	0.0380 (16)	0.0367 (15)	0.0009 (12)	0.0084 (13)	0.0070 (12)
C112	0.034 (2)	0.045 (2)	0.034 (2)	−0.0028 (17)	−0.0038 (17)	0.0067 (18)
C122	0.033 (2)	0.032 (2)	0.035 (2)	−0.0012 (16)	−0.0039 (16)	0.0074 (16)
O132	0.0247 (12)	0.0374 (14)	0.0289 (13)	0.0004 (10)	−0.0019 (11)	0.0068 (11)
C142	0.0242 (18)	0.0271 (18)	0.040 (2)	−0.0018 (14)	0.0000 (16)	0.0002 (16)
C152	0.0273 (18)	0.0282 (18)	0.035 (2)	−0.0007 (15)	0.0042 (15)	−0.0045 (15)

Geometric parameters (Å, º)

O11—C21	1.416 (4)	O12—C22	1.418 (4)
O11—C151	1.427 (4)	O12—C152	1.419 (4)
C21—C31	1.509 (5)	C22—C32	1.499 (5)
C21—H21	0.992	C22—H23	0.990
C21—H22	0.987	C22—H24	0.995
C31—O41	1.423 (4)	C32—O42	1.418 (4)
C31—H31	0.991	C32—H33	0.995
C31—H32	0.989	C32—H34	0.990
O41—C51	1.430 (4)	O42—C52	1.418 (4)
C51—C61	1.489 (5)	C52—C62	1.507 (5)
C51—H51	0.992	C52—H53	0.992
C51—H52	0.990	C52—H54	0.991
C61—O71	1.420 (4)	C62—O72	1.429 (5)
C61—H61	0.991	C62—H63	0.990
C61—H62	0.990	C62—H64	0.989
O71—C81	1.415 (4)	O72—C82	1.420 (4)
C81—C91	1.502 (6)	C82—C92	1.509 (6)
C81—H81	0.989	C82—H83	0.990
C81—H82	0.989	C82—H84	0.992
C91—O101	1.409 (5)	C92—O102	1.424 (5)
C91—H91	0.991	C92—H93	0.988
C91—H92	0.987	C92—H94	0.990
O101—C111	1.420 (5)	O102—C112	1.416 (5)
C111—C121	1.502 (6)	C112—C122	1.502 (6)
C111—H111	0.989	C112—H113	0.990
C111—H112	0.988	C112—H114	0.988
C121—O131	1.420 (5)	C122—O132	1.420 (4)
C121—H121	0.992	C122—H123	0.988
C121—H122	0.991	C122—H124	0.991
O131—C141	1.413 (5)	O132—C142	1.420 (4)
C141—C151	1.504 (6)	C142—C152	1.493 (5)
C141—H141	0.990	C142—H143	0.992
C141—H142	0.990	C142—H144	0.990
C151—H151	0.992	C152—H153	0.993
C151—H152	0.989	C152—H154	0.990
C21—O11—C151	114.7 (3)	C22—O12—C152	112.5 (3)
O11—C21—C31	105.3 (3)	O12—C22—C32	108.6 (3)
O11—C21—H21	110.3	O12—C22—H23	109.9
C31—C21—H21	110.5	C32—C22—H23	109.9
O11—C21—H22	110.4	O12—C22—H24	109.7
C31—C21—H22	110.7	C32—C22—H24	109.7
H21—C21—H22	109.5	H23—C22—H24	109.1
C21—C31—O41	110.8 (3)	C22—C32—O42	108.3 (3)
C21—C31—H31	109.2	C22—C32—H33	109.7
O41—C31—H31	109.2	O42—C32—H33	109.8
C21—C31—H32	109.1	C22—C32—H34	109.9
O41—C31—H32	109.0	O42—C32—H34	110.1
H31—C31—H32	109.4	H33—C32—H34	109.1
C31—O41—C51	115.5 (3)	C32—O42—C52	112.7 (3)
O41—C51—C61	113.3 (3)	O42—C52—C62	109.6 (3)
O41—C51—H51	108.0	O42—C52—H53	109.6
C61—C51—H51	109.0	C62—C52—H53	109.5
O41—C51—H52	108.1	O42—C52—H54	109.6
C61—C51—H52	109.2	C62—C52—H54	109.4
H51—C51—H52	109.3	H53—C52—H54	109.2
C51—C61—O71	109.1 (3)	C52—C62—O72	114.3 (3)
C51—C61—H61	109.8	C52—C62—H63	107.9
O71—C61—H61	109.4	O72—C62—H63	108.4
C51—C61—H62	109.6	C52—C62—H64	108.2
O71—C61—H62	109.4	O72—C62—H64	108.4
H61—C61—H62	109.4	H63—C62—H64	109.5
C61—O71—C81	112.3 (3)	C62—O72—C82	113.5 (3)
O71—C81—C91	108.7 (3)	O72—C82—C92	107.1 (3)
O71—C81—H81	109.4	O72—C82—H83	110.0
C91—C81—H81	109.9	C92—C82—H83	110.3
O71—C81—H82	109.3	O72—C82—H84	109.9
C91—C81—H82	109.9	C92—C82—H84	110.3
H81—C81—H82	109.6	H83—C82—H84	109.3
C81—C91—O101	108.4 (3)	C82—C92—O102	110.2 (3)
C81—C91—H91	109.8	C82—C92—H93	109.2
O101—C91—H91	109.6	O102—C92—H93	109.4
C81—C91—H92	109.7	C82—C92—H94	109.1
O101—C91—H92	109.7	O102—C92—H94	109.3
H91—C91—H92	109.6	H93—C92—H94	109.6
C91—O101—C111	113.5 (3)	C92—O102—C112	113.5 (3)
O101—C111—C121	108.3 (3)	O102—C112—C122	109.7 (3)
O101—C111—H111	109.8	O102—C112—H113	109.6
C121—C111—H111	109.5	C122—C112—H113	109.2
O101—C111—H112	109.8	O102—C112—H114	109.5
C121—C111—H112	109.6	C122—C112—H114	109.3
H111—C111—H112	109.8	H113—C112—H114	109.6
C111—C121—O131	113.3 (3)	C112—C122—O132	111.6 (3)
C111—C121—H121	108.6	C112—C122—H123	109.0
O131—C121—H121	108.3	O132—C122—H123	109.0
C111—C121—H122	108.8	C112—C122—H124	108.9
O131—C121—H122	108.5	O132—C122—H124	108.8
H121—C121—H122	109.3	H123—C122—H124	109.5
C121—O131—C141	114.4 (3)	C122—O132—C142	113.2 (3)
O131—C141—C151	109.2 (3)	O132—C142—C152	109.1 (3)
O131—C141—H141	109.6	O132—C142—H143	109.7
C151—C141—H141	109.5	C152—C142—H143	109.5
O131—C141—H142	109.5	O132—C142—H144	109.8
C151—C141—H142	109.6	C152—C142—H144	109.5
H141—C141—H142	109.4	H143—C142—H144	109.3
C141—C151—O11	114.0 (3)	C142—C152—O12	108.3 (3)
C141—C151—H151	108.4	C142—C152—H153	109.8
O11—C151—H151	108.2	O12—C152—H153	109.5
C141—C151—H152	108.5	C142—C152—H154	110.1
O11—C151—H152	108.2	O12—C152—H154	109.8
H151—C151—H152	109.4	H153—C152—H154	109.3
C151—O11—C21—C31	−167.9 (3)	C152—O12—C22—C32	177.0 (3)
C31—O41—C51—C61	−100.8 (4)	C32—O42—C52—C62	169.9 (3)
C111—O101—C91—C81	166.4 (3)	C112—O102—C92—C82	−91.7 (4)
C121—O131—C141—C151	−170.2 (3)	C122—O132—C142—C152	165.2 (3)
O71—C81—C91—O101	−73.1 (4)	O72—C82—C92—O102	173.9 (3)
C21—O11—C151—C141	−79.7 (4)	C22—O12—C152—C142	171.9 (3)
C81—O71—C61—C51	−178.1 (3)	C82—O72—C62—C52	73.5 (4)
C91—O101—C111—C121	−178.9 (3)	C92—O102—C112—C122	149.8 (3)
O11—C21—C31—O41	174.4 (3)	O12—C22—C32—O42	64.0 (3)
O101—C111—C121—O131	59.1 (4)	O102—C112—C122—O132	−72.8 (4)
C51—O41—C31—C21	116.9 (3)	C52—O42—C32—C22	−161.6 (3)
C61—O71—C81—C91	173.6 (3)	C62—O72—C82—C92	162.9 (3)
C141—O131—C121—C111	84.8 (4)	C142—O132—C122—C112	−94.9 (3)
O41—C51—C61—O71	71.4 (4)	O42—C52—C62—O72	−74.6 (4)
O131—C141—C151—O11	82.0 (4)	O132—C142—C152—O12	−75.2 (3)