Molecular analysis of the β-polymorphic form of trielaidin: crystal structure at low temperature

This work reports on the structure of trielaidin [EEE, 1,2,3-tri(trans-9-octadecenoyl)glycerol], a trans unsaturated triglyceride present in many refined fatty materials (margarines, chocolate products etc.). Firstly, the polymorphism, i.e. the existence of different crystalline forms at various temperature ranges, was defined. Secondly, the crystal growth was examined. By developing a particular growing system, monocrystals of the most stable polymorphic form, i.e. the β-form, were obtained. To reduce thermal vibrations the X-ray data were collected at low temperature (173 K) and the structure was solved using direct methods. The structure was then analyzed in terms of conformation and crystal packing and compared with those of the other known triglycerides.

Computing details

Program(s) used to solve structure: SIR88 (Casearano,1988); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(eeelt)

Crystal data

C57H104O6	Z = 2
Mr = 885.40	F(000) = 988
Triclinic, P1	Dx = 1.051 Mg m^−3
a = 11.6650 (12) Å	Cu Kα radiation, λ = 1.54178 Å
b = 44.933 (5) Å	Cell parameters from 25 reflections
c = 5.432 (6) Å	θ = 15–27°
α = 87.034 (10)°	µ = 0.50 mm^−1
β = 100.17 (9)°	T = 173 K
γ = 89.09 (9)°	Prism, colourless
V = 2798 (3) Å^3	0.30 × 0.15 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.034
Radiation source: fine-focus sealed tube	θmax = 65.0°, θmin = 3.0°
Graphite monochromator	h = −13→13
θ/2θ scans	k = −52→52
10414 measured reflections	l = −3→6
9523 independent reflections	3 standard reflections every 200 reflections
6467 reflections with I > 2σ(I)	intensity decay: 7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.112	H-riding
wR(F^2) = 0.201	Calculated w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.5807P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max = 0.030
9523 reflections	Δρmax = 0.27 e Å^−3
569 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00010 (5)

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.5186 (3)	0.97146 (8)	0.7873 (8)	0.0526 (10)
H1A	0.4993	0.9631	0.9447	0.079*
H1B	0.4586	0.9863	0.7109	0.079*
H1C	0.5943	0.9810	0.8211	0.079*
C2	0.5240 (3)	0.94664 (8)	0.6090 (7)	0.0470 (9)
H2A	0.4459	0.9379	0.5689	0.056*
H2B	0.5436	0.9553	0.4509	0.056*
C3	0.6122 (3)	0.92197 (7)	0.7130 (6)	0.0384 (8)
H3A	0.6902	0.9307	0.7527	0.046*
H3B	0.5926	0.9134	0.8714	0.046*
C4	0.6177 (3)	0.89724 (7)	0.5374 (6)	0.0368 (8)
H4A	0.6373	0.9059	0.3790	0.044*
H4B	0.5396	0.8885	0.4975	0.044*
C5	0.7054 (3)	0.87254 (7)	0.6395 (6)	0.0392 (8)
H5A	0.6862	0.8639	0.7982	0.047*
H5B	0.7837	0.8812	0.6783	0.047*
C6	0.7098 (3)	0.84771 (7)	0.4620 (6)	0.0383 (8)
H6A	0.7266	0.8564	0.3013	0.046*
H6B	0.6322	0.8387	0.4273	0.046*
C7	0.8009 (3)	0.82328 (7)	0.5621 (6)	0.0370 (8)
H7A	0.7845	0.8146	0.7232	0.044*
H7B	0.8787	0.8323	0.5953	0.044*
C8	0.8036 (3)	0.79834 (7)	0.3821 (6)	0.0416 (9)
H8A	0.7261	0.7892	0.3515	0.050*
H8B	0.8183	0.8071	0.2200	0.050*
C9	0.8946 (3)	0.77439 (7)	0.4767 (7)	0.0437 (9)
H9	0.9727	0.7807	0.5167	0.052*
C10	0.8788 (3)	0.74644 (7)	0.5095 (6)	0.0396 (8)
H10	0.8006	0.7402	0.4709	0.047*
C11	0.9687 (3)	0.72258 (7)	0.6010 (7)	0.0393 (8)
H11A	0.9531	0.7134	0.7611	0.047*
H11B	1.0461	0.7317	0.6351	0.047*
C12	0.9724 (3)	0.69814 (7)	0.4170 (6)	0.0353 (8)
H12A	0.8943	0.6894	0.3788	0.042*
H12B	0.9903	0.7072	0.2586	0.042*
C13	1.0619 (3)	0.67329 (7)	0.5141 (6)	0.0375 (8)
H13A	1.1398	0.6821	0.5538	0.045*
H13B	1.0434	0.6641	0.6716	0.045*
C14	1.0665 (3)	0.64903 (6)	0.3300 (6)	0.0312 (7)
H14A	0.9881	0.6406	0.2878	0.037*
H14B	1.0863	0.6582	0.1737	0.037*
C15	1.1530 (3)	0.62411 (7)	0.4258 (6)	0.0331 (7)
H15A	1.1311	0.6143	0.5776	0.040*
H15B	1.2309	0.6326	0.4752	0.040*
C16	1.1607 (3)	0.60061 (7)	0.2350 (6)	0.0323 (7)
H16A	1.0818	0.5931	0.1771	0.039*
H16B	1.1876	0.6102	0.0879	0.039*
C17	1.2414 (3)	0.57460 (7)	0.3356 (5)	0.0309 (7)
H17A	1.3177	0.5823	0.4132	0.037*
H17B	1.2090	0.5634	0.4682	0.037*
C18	1.2597 (3)	0.55391 (6)	0.1406 (6)	0.0283 (7)
O1	1.2486 (2)	0.56063 (5)	−0.0814 (4)	0.0395 (6)
O2	1.29758 (19)	0.52660 (4)	0.2404 (4)	0.0300 (5)
C19	1.3171 (3)	0.50488 (6)	0.0619 (6)	0.0287 (7)
H19	1.3500	0.5151	−0.0771	0.034*
O3	1.4277 (2)	0.46062 (5)	0.0482 (4)	0.0350 (5)
O4	1.4708 (2)	0.42831 (5)	0.3807 (4)	0.0513 (7)
C20	1.4082 (3)	0.48390 (7)	0.2118 (6)	0.0344 (8)
H20A	1.4812	0.4945	0.2668	0.041*
H20B	1.3806	0.4753	0.3618	0.041*
C21	1.4552 (3)	0.43312 (7)	0.1594 (6)	0.0309 (7)
C22	1.4607 (3)	0.41033 (6)	−0.0320 (6)	0.0312 (7)
H22A	1.4884	0.4199	−0.1784	0.037*
H22B	1.3815	0.4030	−0.0903	0.037*
C23	1.5417 (3)	0.38400 (6)	0.0734 (5)	0.0279 (7)
H23A	1.6214	0.3913	0.1269	0.033*
H23B	1.5155	0.3749	0.2233	0.033*
C24	1.5454 (3)	0.36027 (7)	−0.1151 (5)	0.0294 (7)
H24A	1.5669	0.3696	−0.2692	0.035*
H24B	1.4667	0.3520	−0.1606	0.035*
C25	1.6319 (3)	0.33491 (7)	−0.0147 (6)	0.0335 (7)
H25A	1.7105	0.3433	0.0278	0.040*
H25B	1.6113	0.3261	0.1421	0.040*
C26	1.6372 (3)	0.31015 (7)	−0.1936 (6)	0.0329 (7)
H26A	1.5593	0.3013	−0.2328	0.039*
H26B	1.6562	0.3189	−0.3521	0.039*
C27	1.7258 (3)	0.28566 (7)	−0.0917 (7)	0.0397 (8)
H27A	1.7079	0.2771	0.0685	0.048*
H27B	1.8040	0.2944	−0.0561	0.048*
C28	1.7283 (4)	0.26070 (8)	−0.2709 (7)	0.0488 (10)
H28A	1.6515	0.2511	−0.2974	0.059*
H28B	1.7408	0.2695	−0.4348	0.059*
C29	1.8215 (4)	0.23723 (8)	−0.1787 (7)	0.0497 (10)
H29	1.8992	0.2437	−0.1349	0.060*
C30	1.8045 (3)	0.20898 (7)	−0.1542 (7)	0.0447 (9)
H30	1.7268	0.2025	−0.1978	0.054*
C31	1.8971 (3)	0.18557 (7)	−0.0627 (7)	0.0466 (9)
H31A	1.8843	0.1766	0.1002	0.056*
H31B	1.9741	0.1950	−0.0351	0.056*
C32	1.8984 (3)	0.16096 (7)	−0.2469 (6)	0.0389 (8)
H32A	1.9158	0.1698	−0.4064	0.047*
H32B	1.8199	0.1524	−0.2824	0.047*
C33	1.9879 (3)	0.13587 (7)	−0.1490 (7)	0.0399 (8)
H33A	2.0662	0.1446	−0.1125	0.048*
H33B	1.9703	0.1271	0.0106	0.048*
C34	1.9915 (3)	0.11119 (7)	−0.3274 (6)	0.0366 (8)
H34A	1.9129	0.1028	−0.3671	0.044*
H34B	2.0111	0.1199	−0.4856	0.044*
C35	2.0782 (3)	0.08609 (7)	−0.2280 (6)	0.0385 (8)
H35A	2.0578	0.0770	−0.0720	0.046*
H35B	2.1568	0.0945	−0.1854	0.046*
C36	2.0820 (3)	0.06173 (7)	−0.4140 (7)	0.0413 (9)
H36A	2.0031	0.0536	−0.4589	0.050*
H36B	2.1037	0.0708	−0.5689	0.050*
C37	2.1673 (4)	0.03625 (8)	−0.3132 (7)	0.0518 (10)
H37A	2.2457	0.0445	−0.2626	0.062*
H37B	2.1440	0.0268	−0.1617	0.062*
C38	2.1744 (4)	0.01266 (9)	−0.4998 (8)	0.0603 (12)
H38A	2.0987	0.0033	−0.5410	0.090*
H38B	2.2337	−0.0025	−0.4265	0.090*
H38C	2.1954	0.0219	−0.6524	0.090*
O5	1.17331 (19)	0.47234 (5)	0.1618 (4)	0.0379 (6)
C39	1.2063 (3)	0.49027 (6)	−0.0453 (6)	0.0312 (7)
H39A	1.1448	0.5054	−0.1128	0.037*
H39B	1.2187	0.4775	−0.1819	0.037*
C40	1.0685 (3)	0.45911 (7)	0.1152 (6)	0.0348 (8)
O6	1.0062 (2)	0.46229 (6)	−0.0865 (4)	0.0455 (6)
C41	1.0444 (3)	0.44171 (7)	0.3412 (6)	0.0326 (7)
H41A	0.9688	0.4318	0.2981	0.039*
H41B	1.0376	0.4556	0.4738	0.039*
C42	1.1387 (3)	0.41810 (7)	0.4435 (6)	0.0334 (7)
H42A	1.2147	0.4279	0.4824	0.040*
H42B	1.1216	0.4088	0.6016	0.040*
C43	1.1477 (3)	0.39401 (7)	0.2617 (6)	0.0316 (7)
H43A	1.1679	0.4033	0.1064	0.038*
H43B	1.0705	0.3849	0.2169	0.038*
C44	1.2384 (3)	0.36921 (7)	0.3641 (6)	0.0363 (8)
H44A	1.3164	0.3780	0.4016	0.044*
H44B	1.2202	0.3603	0.5228	0.044*
C45	1.2413 (3)	0.34483 (7)	0.1809 (6)	0.0341 (7)
H45A	1.2605	0.3538	0.0233	0.041*
H45B	1.1628	0.3364	0.1412	0.041*
C46	1.3293 (3)	0.31974 (7)	0.2802 (6)	0.0319 (7)
H46A	1.3105	0.3108	0.4382	0.038*
H46B	1.4080	0.3281	0.3185	0.038*
C47	1.3303 (3)	0.29537 (8)	0.0939 (7)	0.0450 (9)
H47A	1.2528	0.2862	0.0638	0.054*
H47B	1.3440	0.3046	−0.0675	0.054*
C48	1.4214 (3)	0.27134 (8)	0.1815 (7)	0.0464 (9)
H48	1.4993	0.2776	0.2280	0.056*
C49	1.4049 (4)	0.24309 (8)	0.2000 (7)	0.0507 (10)
H49	1.3272	0.2368	0.1522	0.061*
C50	1.4960 (4)	0.21911 (8)	0.2894 (7)	0.0512 (10)
H50A	1.4832	0.2105	0.4535	0.061*
H50B	1.5734	0.2283	0.3158	0.061*
C51	1.4976 (3)	0.19397 (7)	0.1125 (6)	0.0397 (8)
H51A	1.5148	0.2022	−0.0491	0.048*
H51B	1.4194	0.1852	0.0796	0.048*
C52	1.5886 (3)	0.16929 (7)	0.2194 (6)	0.0383 (8)
H52A	1.6665	0.1782	0.2542	0.046*
H52B	1.5708	0.1610	0.3804	0.046*
C53	1.5927 (3)	0.14392 (7)	0.0440 (6)	0.0393 (8)
H53A	1.5149	0.1350	0.0081	0.047*
H53B	1.6114	0.1521	−0.1166	0.047*
C54	1.6829 (3)	0.11959 (7)	0.1541 (6)	0.0390 (8)
H54A	1.7603	0.1286	0.1931	0.047*
H54B	1.6633	0.1112	0.3133	0.047*
C55	1.6898 (3)	0.09454 (7)	−0.0182 (7)	0.0390 (8)
H55A	1.7085	0.1029	−0.1782	0.047*
H55B	1.6126	0.0853	−0.0555	0.047*
C56	1.7804 (3)	0.07056 (8)	0.0903 (7)	0.0449 (9)
H56A	1.7610	0.0620	0.2489	0.054*
H56B	1.8573	0.0799	0.1304	0.054*
C57	1.7897 (4)	0.04540 (8)	−0.0837 (7)	0.0523 (10)
H57A	1.7156	0.0351	−0.1152	0.078*
H57B	1.8519	0.0313	−0.0051	0.078*
H57C	1.8076	0.0537	−0.2427	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.059 (3)	0.036 (2)	0.064 (3)	0.0137 (18)	0.011 (2)	−0.0101 (18)
C2	0.065 (3)	0.037 (2)	0.038 (2)	0.0072 (18)	0.0071 (18)	−0.0104 (16)
C3	0.047 (2)	0.0326 (18)	0.0359 (19)	0.0051 (15)	0.0095 (16)	−0.0007 (15)
C4	0.044 (2)	0.0312 (18)	0.0317 (18)	0.0087 (15)	−0.0019 (15)	−0.0058 (14)
C5	0.046 (2)	0.0373 (19)	0.0338 (19)	0.0121 (16)	0.0069 (16)	−0.0035 (15)
C6	0.043 (2)	0.0329 (18)	0.0369 (19)	0.0088 (15)	0.0020 (15)	−0.0029 (15)
C7	0.040 (2)	0.0369 (19)	0.0321 (18)	0.0072 (15)	0.0008 (15)	−0.0053 (15)
C8	0.049 (2)	0.0370 (19)	0.0355 (19)	0.0147 (16)	0.0001 (16)	−0.0045 (15)
C9	0.047 (2)	0.033 (2)	0.050 (2)	0.0081 (16)	0.0034 (18)	−0.0129 (16)
C10	0.051 (2)	0.0312 (18)	0.0367 (19)	0.0139 (16)	0.0089 (16)	−0.0023 (14)
C11	0.051 (2)	0.0244 (17)	0.042 (2)	0.0069 (15)	0.0060 (17)	−0.0029 (14)
C12	0.046 (2)	0.0284 (17)	0.0301 (18)	0.0104 (15)	0.0033 (15)	−0.0024 (13)
C13	0.050 (2)	0.0282 (17)	0.0343 (18)	0.0076 (15)	0.0060 (16)	−0.0063 (14)
C14	0.0433 (19)	0.0254 (16)	0.0226 (16)	0.0032 (14)	−0.0005 (14)	−0.0041 (12)
C15	0.0409 (18)	0.0251 (16)	0.0311 (17)	0.0051 (14)	0.0002 (14)	−0.0047 (13)
C16	0.0387 (18)	0.0304 (17)	0.0255 (17)	0.0105 (14)	0.0004 (14)	−0.0029 (13)
C17	0.045 (2)	0.0282 (16)	0.0212 (16)	0.0057 (14)	0.0092 (14)	−0.0099 (12)
C18	0.0341 (17)	0.0215 (15)	0.0296 (17)	−0.0054 (12)	0.0059 (13)	−0.0031 (12)
O1	0.0605 (16)	0.0302 (12)	0.0288 (13)	0.0060 (11)	0.0109 (11)	−0.0022 (10)
O2	0.0444 (13)	0.0232 (11)	0.0229 (11)	0.0072 (9)	0.0065 (10)	−0.0071 (8)
C19	0.0343 (17)	0.0276 (16)	0.0248 (16)	0.0028 (13)	0.0049 (13)	−0.0098 (13)
O3	0.0515 (14)	0.0252 (11)	0.0274 (12)	0.0117 (10)	0.0063 (10)	0.0011 (9)
O4	0.088 (2)	0.0439 (15)	0.0194 (12)	0.0227 (14)	0.0041 (12)	−0.0014 (10)
C20	0.0419 (19)	0.0337 (18)	0.0300 (17)	0.0053 (15)	0.0102 (15)	−0.0141 (14)
C21	0.0323 (17)	0.0325 (17)	0.0252 (17)	0.0077 (14)	−0.0019 (13)	−0.0018 (13)
C22	0.0416 (19)	0.0214 (15)	0.0292 (17)	0.0081 (13)	0.0023 (14)	−0.0030 (13)
C23	0.0432 (18)	0.0235 (15)	0.0178 (15)	0.0027 (13)	0.0072 (13)	−0.0026 (12)
C24	0.0337 (17)	0.0312 (17)	0.0223 (16)	0.0031 (13)	0.0010 (13)	−0.0060 (13)
C25	0.0350 (18)	0.0257 (16)	0.0382 (19)	0.0089 (13)	0.0027 (15)	−0.0021 (14)
C26	0.0409 (19)	0.0288 (16)	0.0281 (17)	0.0065 (14)	0.0028 (14)	−0.0067 (13)
C27	0.044 (2)	0.0270 (17)	0.046 (2)	0.0106 (15)	0.0025 (16)	−0.0076 (15)
C28	0.071 (3)	0.0303 (19)	0.040 (2)	0.0144 (18)	−0.0038 (19)	−0.0052 (16)
C29	0.055 (2)	0.041 (2)	0.051 (2)	0.0031 (18)	0.0003 (19)	−0.0159 (18)
C30	0.050 (2)	0.0295 (18)	0.051 (2)	0.0010 (16)	−0.0050 (18)	−0.0084 (16)
C31	0.062 (2)	0.0328 (19)	0.047 (2)	0.0063 (17)	0.0121 (19)	−0.0079 (16)
C32	0.0409 (19)	0.0333 (18)	0.040 (2)	0.0149 (15)	0.0031 (16)	−0.0029 (15)
C33	0.043 (2)	0.0302 (18)	0.044 (2)	0.0103 (15)	0.0023 (16)	−0.0006 (15)
C34	0.0402 (19)	0.0265 (17)	0.041 (2)	0.0079 (14)	0.0011 (15)	−0.0064 (14)
C35	0.049 (2)	0.0264 (17)	0.040 (2)	0.0068 (15)	0.0078 (16)	−0.0022 (14)
C36	0.049 (2)	0.0352 (19)	0.041 (2)	0.0066 (16)	0.0123 (17)	−0.0022 (15)
C37	0.068 (3)	0.036 (2)	0.049 (2)	0.0193 (19)	0.005 (2)	−0.0034 (17)
C38	0.084 (3)	0.044 (2)	0.056 (3)	0.004 (2)	0.019 (2)	−0.0151 (19)
O5	0.0384 (13)	0.0385 (13)	0.0338 (13)	−0.0070 (10)	−0.0013 (10)	0.0005 (10)
C39	0.042 (2)	0.0219 (16)	0.0274 (17)	0.0016 (13)	0.0014 (14)	−0.0001 (12)
C40	0.0437 (19)	0.0234 (16)	0.039 (2)	0.0042 (14)	0.0120 (16)	−0.0069 (14)
O6	0.0476 (15)	0.0542 (16)	0.0322 (14)	−0.0046 (12)	0.0009 (12)	0.0002 (11)
C41	0.0313 (17)	0.0355 (18)	0.0327 (18)	0.0019 (14)	0.0099 (14)	−0.0045 (14)
C42	0.0402 (19)	0.0352 (18)	0.0259 (17)	0.0002 (14)	0.0093 (14)	−0.0003 (13)
C43	0.0419 (19)	0.0305 (17)	0.0208 (15)	0.0017 (14)	−0.0006 (13)	−0.0093 (13)
C44	0.0423 (19)	0.0340 (18)	0.0291 (18)	0.0032 (15)	−0.0020 (15)	0.0013 (14)
C45	0.0416 (19)	0.0297 (17)	0.0292 (17)	0.0101 (14)	0.0029 (14)	0.0008 (13)
C46	0.0371 (18)	0.0270 (16)	0.0305 (17)	0.0070 (14)	0.0029 (14)	−0.0040 (13)
C47	0.040 (2)	0.045 (2)	0.050 (2)	0.0094 (16)	0.0059 (17)	−0.0110 (17)
C48	0.048 (2)	0.038 (2)	0.047 (2)	0.0096 (17)	−0.0079 (17)	−0.0098 (17)
C49	0.055 (2)	0.049 (2)	0.048 (2)	0.0059 (19)	0.0093 (19)	−0.0076 (18)
C50	0.075 (3)	0.035 (2)	0.042 (2)	0.0135 (19)	0.004 (2)	−0.0110 (17)
C51	0.050 (2)	0.0266 (17)	0.039 (2)	0.0065 (15)	0.0009 (17)	−0.0012 (15)
C52	0.049 (2)	0.0366 (19)	0.0259 (17)	0.0014 (16)	−0.0036 (15)	−0.0068 (14)
C53	0.058 (2)	0.0313 (18)	0.0271 (17)	0.0023 (16)	0.0006 (16)	−0.0108 (14)
C54	0.048 (2)	0.0342 (18)	0.0344 (19)	0.0025 (15)	0.0046 (16)	−0.0062 (15)
C55	0.043 (2)	0.0338 (18)	0.040 (2)	0.0020 (15)	0.0064 (16)	−0.0059 (15)
C56	0.047 (2)	0.042 (2)	0.044 (2)	0.0138 (17)	0.0041 (17)	−0.0032 (16)
C57	0.063 (3)	0.040 (2)	0.054 (2)	0.0080 (18)	0.012 (2)	−0.0077 (18)

Geometric parameters (Å, º)

C1—C2	1.522 (5)	C29—C30	1.292 (5)
C1—H1A	0.9800	C29—H29	0.9500
C1—H1B	0.9800	C30—C31	1.497 (5)
C1—H1C	0.9800	C30—H30	0.9500
C2—C3	1.517 (5)	C31—C32	1.531 (4)
C2—H2A	0.9900	C31—H31A	0.9900
C2—H2B	0.9900	C31—H31B	0.9900
C3—C4	1.509 (4)	C32—C33	1.533 (4)
C3—H3A	0.9900	C32—H32A	0.9900
C3—H3B	0.9900	C32—H32B	0.9900
C4—C5	1.512 (4)	C33—C34	1.515 (4)
C4—H4A	0.9900	C33—H33A	0.9900
C4—H4B	0.9900	C33—H33B	0.9900
C5—C6	1.518 (4)	C34—C35	1.514 (4)
C5—H5A	0.9900	C34—H34A	0.9900
C5—H5B	0.9900	C34—H34B	0.9900
C6—C7	1.526 (4)	C35—C36	1.533 (4)
C6—H6A	0.9900	C35—H35A	0.9900
C6—H6B	0.9900	C35—H35B	0.9900
C7—C8	1.528 (4)	C36—C37	1.519 (5)
C7—H7A	0.9900	C36—H36A	0.9900
C7—H7B	0.9900	C36—H36B	0.9900
C8—C9	1.504 (5)	C37—C38	1.515 (5)
C8—H8A	0.9900	C37—H37A	0.9900
C8—H8B	0.9900	C37—H37B	0.9900
C9—C10	1.280 (5)	C38—H38A	0.9800
C9—H9	0.9500	C38—H38B	0.9800
C10—C11	1.490 (4)	C38—H38C	0.9800
C10—H10	0.9500	O5—C40	1.358 (4)
C11—C12	1.528 (4)	O5—C39	1.460 (4)
C11—H11A	0.9900	C39—H39A	0.9900
C11—H11B	0.9900	C39—H39B	0.9900
C12—C13	1.524 (4)	C40—O6	1.203 (4)
C12—H12A	0.9900	C40—C41	1.492 (4)
C12—H12B	0.9900	C41—C42	1.526 (4)
C13—C14	1.524 (4)	C41—H41A	0.9900
C13—H13A	0.9900	C41—H41B	0.9900
C13—H13B	0.9900	C42—C43	1.517 (4)
C14—C15	1.504 (4)	C42—H42A	0.9900
C14—H14A	0.9900	C42—H42B	0.9900
C14—H14B	0.9900	C43—C44	1.537 (4)
C15—C16	1.530 (4)	C43—H43A	0.9900
C15—H15A	0.9900	C43—H43B	0.9900
C15—H15B	0.9900	C44—C45	1.521 (4)
C16—C17	1.506 (4)	C44—H44A	0.9900
C16—H16A	0.9900	C44—H44B	0.9900
C16—H16B	0.9900	C45—C46	1.523 (4)
C17—C18	1.486 (4)	C45—H45A	0.9900
C17—H17A	0.9900	C45—H45B	0.9900
C17—H17B	0.9900	C46—C47	1.530 (4)
C18—O1	1.212 (4)	C46—H46A	0.9900
C18—O2	1.350 (4)	C46—H46B	0.9900
O2—C19	1.454 (3)	C47—C48	1.501 (5)
C19—C39	1.497 (4)	C47—H47A	0.9900
C19—C20	1.505 (4)	C47—H47B	0.9900
C19—H19	1.0000	C48—C49	1.288 (5)
O3—C21	1.355 (4)	C48—H48	0.9500
O3—C20	1.448 (3)	C49—C50	1.501 (5)
O4—C21	1.192 (4)	C49—H49	0.9500
C20—H20A	0.9900	C50—C51	1.522 (4)
C20—H20B	0.9900	C50—H50A	0.9900
C21—C22	1.505 (4)	C50—H50B	0.9900
C22—C23	1.524 (4)	C51—C52	1.541 (4)
C22—H22A	0.9900	C51—H51A	0.9900
C22—H22B	0.9900	C51—H51B	0.9900
C23—C24	1.522 (4)	C52—C53	1.529 (4)
C23—H23A	0.9900	C52—H52A	0.9900
C23—H23B	0.9900	C52—H52B	0.9900
C24—C25	1.523 (4)	C53—C54	1.527 (5)
C24—H24A	0.9900	C53—H53A	0.9900
C24—H24B	0.9900	C53—H53B	0.9900
C25—C26	1.522 (4)	C54—C55	1.511 (4)
C25—H25A	0.9900	C54—H54A	0.9900
C25—H25B	0.9900	C54—H54B	0.9900
C26—C27	1.512 (4)	C55—C56	1.518 (5)
C26—H26A	0.9900	C55—H55A	0.9900
C26—H26B	0.9900	C55—H55B	0.9900
C27—C28	1.526 (4)	C56—C57	1.525 (5)
C27—H27A	0.9900	C56—H56A	0.9900
C27—H27B	0.9900	C56—H56B	0.9900
C28—C29	1.504 (5)	C57—H57A	0.9800
C28—H28A	0.9900	C57—H57B	0.9800
C28—H28B	0.9900	C57—H57C	0.9800
C2—C1—H1A	109.5	C30—C29—H29	117.3
C2—C1—H1B	109.5	C28—C29—H29	117.3
H1A—C1—H1B	109.5	C29—C30—C31	125.4 (4)
C2—C1—H1C	109.5	C29—C30—H30	117.3
H1A—C1—H1C	109.5	C31—C30—H30	117.3
H1B—C1—H1C	109.5	C30—C31—C32	112.5 (3)
C3—C2—C1	113.7 (3)	C30—C31—H31A	109.1
C3—C2—H2A	108.8	C32—C31—H31A	109.1
C1—C2—H2A	108.8	C30—C31—H31B	109.1
C3—C2—H2B	108.8	C32—C31—H31B	109.1
C1—C2—H2B	108.8	H31A—C31—H31B	107.8
H2A—C2—H2B	107.7	C31—C32—C33	113.2 (3)
C4—C3—C2	114.0 (3)	C31—C32—H32A	108.9
C4—C3—H3A	108.8	C33—C32—H32A	108.9
C2—C3—H3A	108.8	C31—C32—H32B	108.9
C4—C3—H3B	108.8	C33—C32—H32B	108.9
C2—C3—H3B	108.8	H32A—C32—H32B	107.8
H3A—C3—H3B	107.7	C34—C33—C32	114.4 (3)
C3—C4—C5	114.3 (3)	C34—C33—H33A	108.7
C3—C4—H4A	108.7	C32—C33—H33A	108.6
C5—C4—H4A	108.7	C34—C33—H33B	108.6
C3—C4—H4B	108.7	C32—C33—H33B	108.6
C5—C4—H4B	108.7	H33A—C33—H33B	107.6
H4A—C4—H4B	107.6	C35—C34—C33	114.4 (3)
C4—C5—C6	113.9 (3)	C35—C34—H34A	108.7
C4—C5—H5A	108.8	C33—C34—H34A	108.7
C6—C5—H5A	108.8	C35—C34—H34B	108.7
C4—C5—H5B	108.8	C33—C34—H34B	108.7
C6—C5—H5B	108.8	H34A—C34—H34B	107.6
H5A—C5—H5B	107.7	C34—C35—C36	113.4 (3)
C5—C6—C7	113.8 (3)	C34—C35—H35A	108.9
C5—C6—H6A	108.8	C36—C35—H35A	108.9
C7—C6—H6A	108.8	C34—C35—H35B	108.9
C5—C6—H6B	108.8	C36—C35—H35B	108.9
C7—C6—H6B	108.8	H35A—C35—H35B	107.7
H6A—C6—H6B	107.7	C37—C36—C35	113.5 (3)
C6—C7—C8	113.2 (3)	C37—C36—H36A	108.9
C6—C7—H7A	108.9	C35—C36—H36A	108.9
C8—C7—H7A	108.9	C37—C36—H36B	108.9
C6—C7—H7B	108.9	C35—C36—H36B	108.9
C8—C7—H7B	108.9	H36A—C36—H36B	107.7
H7A—C7—H7B	107.8	C38—C37—C36	113.6 (3)
C9—C8—C7	113.7 (3)	C38—C37—H37A	108.8
C9—C8—H8A	108.8	C36—C37—H37A	108.8
C7—C8—H8A	108.8	C38—C37—H37B	108.8
C9—C8—H8B	108.8	C36—C37—H37B	108.8
C7—C8—H8B	108.8	H37A—C37—H37B	107.7
H8A—C8—H8B	107.7	C37—C38—H38A	109.5
C10—C9—C8	127.4 (4)	C37—C38—H38B	109.5
C10—C9—H9	116.3	H38A—C38—H38B	109.5
C8—C9—H9	116.3	C37—C38—H38C	109.5
C9—C10—C11	127.7 (4)	H38A—C38—H38C	109.5
C9—C10—H10	116.2	H38B—C38—H38C	109.5
C11—C10—H10	116.2	C40—O5—C39	116.5 (3)
C10—C11—C12	113.7 (3)	O5—C39—C19	105.8 (3)
C10—C11—H11A	108.8	O5—C39—H39A	110.6
C12—C11—H11A	108.8	C19—C39—H39A	110.6
C10—C11—H11B	108.8	O5—C39—H39B	110.6
C12—C11—H11B	108.8	C19—C39—H39B	110.6
H11A—C11—H11B	107.7	H39A—C39—H39B	108.7
C13—C12—C11	113.6 (3)	O6—C40—O5	121.3 (3)
C13—C12—H12A	108.8	O6—C40—C41	127.3 (3)
C11—C12—H12A	108.8	O5—C40—C41	111.4 (3)
C13—C12—H12B	108.8	C40—C41—C42	113.1 (3)
C11—C12—H12B	108.8	C40—C41—H41A	109.0
H12A—C12—H12B	107.7	C42—C41—H41A	109.0
C14—C13—C12	113.7 (3)	C40—C41—H41B	109.0
C14—C13—H13A	108.8	C42—C41—H41B	109.0
C12—C13—H13A	108.8	H41A—C41—H41B	107.8
C14—C13—H13B	108.8	C43—C42—C41	112.9 (3)
C12—C13—H13B	108.8	C43—C42—H42A	109.0
H13A—C13—H13B	107.7	C41—C42—H42A	109.0
C15—C14—C13	114.2 (3)	C43—C42—H42B	109.0
C15—C14—H14A	108.7	C41—C42—H42B	109.0
C13—C14—H14A	108.7	H42A—C42—H42B	107.8
C15—C14—H14B	108.7	C42—C43—C44	114.0 (3)
C13—C14—H14B	108.7	C42—C43—H43A	108.8
H14A—C14—H14B	107.6	C44—C43—H43A	108.8
C14—C15—C16	113.7 (3)	C42—C43—H43B	108.8
C14—C15—H15A	108.8	C44—C43—H43B	108.8
C16—C15—H15A	108.8	H43A—C43—H43B	107.7
C14—C15—H15B	108.8	C45—C44—C43	112.4 (3)
C16—C15—H15B	108.8	C45—C44—H44A	109.1
H15A—C15—H15B	107.7	C43—C44—H44A	109.1
C17—C16—C15	113.8 (3)	C45—C44—H44B	109.1
C17—C16—H16A	108.8	C43—C44—H44B	109.1
C15—C16—H16A	108.8	H44A—C44—H44B	107.8
C17—C16—H16B	108.8	C44—C45—C46	113.4 (3)
C15—C16—H16B	108.8	C44—C45—H45A	108.9
H16A—C16—H16B	107.7	C46—C45—H45A	108.9
C18—C17—C16	113.3 (3)	C44—C45—H45B	108.9
C18—C17—H17A	108.9	C46—C45—H45B	108.9
C16—C17—H17A	108.9	H45A—C45—H45B	107.7
C18—C17—H17B	108.9	C45—C46—C47	112.6 (3)
C16—C17—H17B	108.9	C45—C46—H46A	109.1
H17A—C17—H17B	107.7	C47—C46—H46A	109.1
O1—C18—O2	122.8 (3)	C45—C46—H46B	109.1
O1—C18—C17	125.1 (3)	C47—C46—H46B	109.1
O2—C18—C17	112.1 (3)	H46A—C46—H46B	107.8
C18—O2—C19	115.6 (2)	C48—C47—C46	113.4 (3)
O2—C19—C39	111.3 (3)	C48—C47—H47A	108.9
O2—C19—C20	103.4 (2)	C46—C47—H47A	108.9
C39—C19—C20	114.2 (3)	C48—C47—H47B	108.9
O2—C19—H19	109.2	C46—C47—H47B	108.9
C39—C19—H19	109.2	H47A—C47—H47B	107.7
C20—C19—H19	109.2	C49—C48—C47	126.7 (4)
C21—O3—C20	116.3 (2)	C49—C48—H48	116.6
O3—C20—C19	106.4 (3)	C47—C48—H48	116.6
O3—C20—H20A	110.4	C48—C49—C50	126.7 (4)
C19—C20—H20A	110.4	C48—C49—H49	116.7
O3—C20—H20B	110.4	C50—C49—H49	116.7
C19—C20—H20B	110.4	C49—C50—C51	114.7 (3)
H20A—C20—H20B	108.6	C49—C50—H50A	108.6
O4—C21—O3	122.9 (3)	C51—C50—H50A	108.6
O4—C21—C22	125.9 (3)	C49—C50—H50B	108.6
O3—C21—C22	111.2 (3)	C51—C50—H50B	108.6
C21—C22—C23	112.0 (3)	H50A—C50—H50B	107.6
C21—C22—H22A	109.2	C50—C51—C52	112.4 (3)
C23—C22—H22A	109.2	C50—C51—H51A	109.1
C21—C22—H22B	109.2	C52—C51—H51A	109.1
C23—C22—H22B	109.2	C50—C51—H51B	109.1
H22A—C22—H22B	107.9	C52—C51—H51B	109.1
C24—C23—C22	112.7 (3)	H51A—C51—H51B	107.9
C24—C23—H23A	109.0	C53—C52—C51	113.4 (3)
C22—C23—H23A	109.0	C53—C52—H52A	108.9
C24—C23—H23B	109.0	C51—C52—H52A	108.9
C22—C23—H23B	109.0	C53—C52—H52B	108.9
H23A—C23—H23B	107.8	C51—C52—H52B	108.9
C23—C24—C25	112.6 (3)	H52A—C52—H52B	107.7
C23—C24—H24A	109.1	C54—C53—C52	112.6 (3)
C25—C24—H24A	109.1	C54—C53—H53A	109.1
C23—C24—H24B	109.1	C52—C53—H53A	109.1
C25—C24—H24B	109.1	C54—C53—H53B	109.1
H24A—C24—H24B	107.8	C52—C53—H53B	109.1
C26—C25—C24	114.8 (3)	H53A—C53—H53B	107.8
C26—C25—H25A	108.6	C55—C54—C53	113.5 (3)
C24—C25—H25A	108.6	C55—C54—H54A	108.9
C26—C25—H25B	108.6	C53—C54—H54A	108.9
C24—C25—H25B	108.6	C55—C54—H54B	108.9
H25A—C25—H25B	107.5	C53—C54—H54B	108.9
C27—C26—C25	113.7 (3)	H54A—C54—H54B	107.7
C27—C26—H26A	108.8	C54—C55—C56	113.4 (3)
C25—C26—H26A	108.8	C54—C55—H55A	108.9
C27—C26—H26B	108.8	C56—C55—H55A	108.9
C25—C26—H26B	108.8	C54—C55—H55B	108.9
H26A—C26—H26B	107.7	C56—C55—H55B	108.9
C26—C27—C28	113.1 (3)	H55A—C55—H55B	107.7
C26—C27—H27A	109.0	C55—C56—C57	113.9 (3)
C28—C27—H27A	109.0	C55—C56—H56A	108.8
C26—C27—H27B	109.0	C57—C56—H56A	108.8
C28—C27—H27B	109.0	C55—C56—H56B	108.8
H27A—C27—H27B	107.8	C57—C56—H56B	108.8
C29—C28—C27	113.5 (3)	H56A—C56—H56B	107.7
C29—C28—H28A	108.9	C56—C57—H57A	109.5
C27—C28—H28A	108.9	C56—C57—H57B	109.5
C29—C28—H28B	108.9	H57A—C57—H57B	109.5
C27—C28—H28B	108.9	C56—C57—H57C	109.5
H28A—C28—H28B	107.7	H57A—C57—H57C	109.5
C30—C29—C28	125.3 (4)	H57B—C57—H57C	109.5
C1—C2—C3—C4	179.8 (3)	C26—C27—C28—C29	176.2 (3)
C2—C3—C4—C5	−180.0 (3)	C27—C28—C29—C30	125.6 (4)
C3—C4—C5—C6	179.7 (3)	C28—C29—C30—C31	179.9 (4)
C4—C5—C6—C7	178.3 (3)	C29—C30—C31—C32	−125.1 (4)
C5—C6—C7—C8	179.6 (3)	C30—C31—C32—C33	−176.6 (3)
C6—C7—C8—C9	178.9 (3)	C31—C32—C33—C34	−179.8 (3)
C7—C8—C9—C10	122.9 (4)	C32—C33—C34—C35	−178.7 (3)
C8—C9—C10—C11	179.4 (3)	C33—C34—C35—C36	−178.8 (3)
C9—C10—C11—C12	−121.3 (4)	C34—C35—C36—C37	−179.0 (3)
C10—C11—C12—C13	−178.3 (3)	C35—C36—C37—C38	−178.0 (3)
C11—C12—C13—C14	−179.5 (3)	C40—O5—C39—C19	173.8 (2)
C12—C13—C14—C15	−178.9 (3)	O2—C19—C39—O5	−67.5 (3)
C13—C14—C15—C16	−177.4 (3)	C20—C19—C39—O5	49.2 (3)
C14—C15—C16—C17	−176.3 (3)	C39—O5—C40—O6	−0.5 (4)
C15—C16—C17—C18	−172.7 (3)	C39—O5—C40—C41	−179.5 (2)
C16—C17—C18—O1	24.6 (5)	O6—C40—C41—C42	124.4 (4)
C16—C17—C18—O2	−159.0 (3)	O5—C40—C41—C42	−56.6 (4)
O1—C18—O2—C19	−3.9 (4)	C40—C41—C42—C43	−64.1 (4)
C17—C18—O2—C19	179.7 (2)	C41—C42—C43—C44	−177.5 (3)
C18—O2—C19—C39	−83.6 (3)	C42—C43—C44—C45	177.6 (3)
C18—O2—C19—C20	153.3 (3)	C43—C44—C45—C46	−179.1 (3)
C21—O3—C20—C19	−147.3 (3)	C44—C45—C46—C47	179.6 (3)
O2—C19—C20—O3	177.1 (2)	C45—C46—C47—C48	176.5 (3)
C39—C19—C20—O3	55.9 (3)	C46—C47—C48—C49	125.7 (4)
C20—O3—C21—O4	−5.1 (5)	C47—C48—C49—C50	−179.5 (4)
C20—O3—C21—C22	174.0 (3)	C48—C49—C50—C51	−127.6 (4)
O4—C21—C22—C23	−27.4 (5)	C49—C50—C51—C52	−177.3 (3)
O3—C21—C22—C23	153.6 (3)	C50—C51—C52—C53	−179.4 (3)
C21—C22—C23—C24	178.2 (3)	C51—C52—C53—C54	−179.6 (3)
C22—C23—C24—C25	176.5 (3)	C52—C53—C54—C55	−179.0 (3)
C23—C24—C25—C26	178.7 (3)	C53—C54—C55—C56	179.3 (3)
C24—C25—C26—C27	178.6 (3)	C54—C55—C56—C57	−179.0 (3)
C25—C26—C27—C28	178.8 (3)