Verticine ethanol hydrate (2/1/1)

The two symmetry-independent mol­ecules of the title compound, cevane-3β,6α,20-triol ethanol hydrate (2/1/1), 2C₂₇H₄₅NO₃·C₂H₆O·H₂O, have the same stereochemical assignments. The six-membered rings A, B, E and F are in the chair conformation, while ring D is in a boat conformation. The ring fusions are A/B trans, B/C trans, C/D cis, D/E trans and E/F trans. The verticine mol­ecules are bridged by water and ethanol mol­ecules via hydrogen bonds to form two-dimensional layers, and the crystal structure is built up by stacking of these layers.

S1. Comment

`Beimu', Bulbs Fritillaria, derived from the dried bulbs of numerous species of the genus Fritillaria (Liliaceae), is most commonly used in mainland China, Hong Kong and other Chinese communities worldwide, and has been for centuries (Xu & Xu, 1991). The main biologically active members of the various Fritillaria species are steroidal alkaloids, including verticine, verticinone and imperialine, among which verticine is one of the major active alkaloids (Li et al., 1988, 1990, 1992, 1993; Ji et al., 1993). The structure of verticine has been characterized previously by NMR and MS spectrometric analyses (Ito et al., 1961, 1963; Shô et al., 1968). In the present study, the single-crystal X-ray crystallographic analysis of verticine ethanol hydrate (2/1/1), (I), is reported.

All bond distances in the molecule of (I) are within the normal range (Allen et al., 1987). As illustrated in Fig. 1, the two independent verticine molecules in the asymmetric unit have the same stereochemical assignments. The six-membered rings A, B, E and F are in the chair conformation, whereas ring D is in a boat conformation, and the ring fusions are A/B trans, B/C trans, C/D cis, D/E trans and E/F trans. While our analysis establishes the relative stereochemistry, it does not allow us to establish the absolute configuration. The configuration shown in Fig. 1 and the scheme is chosen to be in accord with that established previously for other verticine salt derivatives, such as the chloride (Kettmann et al., 1982, 1990) and perchlorate (Codding, 1983).

In the crystal structure of (I), pairs of verticine molecules are parallel and arranged in a head-to-tail manner, interlinked by intermolecular hydrogen bonds (Fig. 2). Hydrogen bonding (see Table 1 for full details of all hydrogen-bond parameters) involving the independent water molecule and three hydroxy groups from three neighbouring verticine molecules gives rise to a nearly coplanar square ring; such rings are further connected with two other adjacent rings by hydrogen bonds to generate an infinite chain extending in the b direction, as shown in Fig. 3. In addition, verticine molecules are bridged by the ethanol hydroxy group to form a one-dimensional ribbon running parallel to the b direction. The packing of the molecules in the crystal structure is characterized by a two-dimensional network approximately parallel to the (101) plane (Fig. 2). The crystal structure is built up by a stacking of these layers such that the interlayer interactions are mainly of the van der Waals type.

S2. Experimental

The dried and ground bulbs of Fritillaria cirrhosa were extracted with 50% aqueous acetone. After removal of the acetone under reduced pressure, the aqueous extracts were passed through a Diaion HP-20 column, eluting first with water, followed by 50% aqueous methanol and finally methanol. The combined methanol fractions were alkalinized with 13% ammonia and extracted with chloroform. A crude alkaloid extract was obtained after removal of the chloroform solvent and it was separated by silica-gel column chromatography with a gradient elution of petroleum ether–EtOAc–Et₂NH (120:1:1—6:1:1). The fractions containing verticine were combined and further purified by silica-gel column chromatography, eluting with chloroform–EtOH (60:1). The solvents of the collected fractions containing verticine were removed under reduced pressure. Compound (I) was obtained by crystallization from a ethanol–water (50:1) solution.

S3. Refinement

All H atoms except those of the water molecule were treated as riding atoms (C—H 0.96–0.98 Å and O—H 0.82 Å). The H atoms of the water molecule were visible in difference maps and were allowed to refine with a fixed isotropic vibration parameter subject to a DFIX restraint that the O—H distance be 0.86 (2) Å. A complete Friedel data set was collected, but initial refinement led to an indeterminate Flack value of 0.7 (10) for this all-light-atom structure. For the final refinement, the Friedel reflection data were merged.

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SHELXTL/PC (Siemens, 1990); software used to prepare material for publication: SHELXTL93.

Figures

	Fig. 1. A perspective view of (I) with 35% displacement ellipsoids, showing the molecular conformation and the atomic labelling. H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. A perspective view of the crystal structure of (I), showing the packing of the two-dimensional layers corresponding to the (101) plane. Hydrogen bonds are indicated by broken lines.
	Fig. 3. The mode of hydrogen bonding and molecular packing indicated by the water and hydroxy O-atoms involved in the hydrogen-bonding network in the crystal structure of (I). Hydrogen bonds are indicated by broken lines [symmetry codes: (i) −x, y + 1/2, 1 − z; (ii) 1 − x, y − 1/2, −z; (iv) x, y − 1, z; (v) x, 1 + y, z; (vi) −x, y − 1/2, 1 − z]. Check.

cevane-3β,6α,20-triol ethanol hydrate

Crystal data

2C27H45NO3·C2H6O·H2O	F(000) = 1024
Mr = 927.36	Dx = 1.156 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 16.146 (3) Å	Cell parameters from 25 reflections
b = 8.660 (2) Å	θ = 5–12.5°
c = 19.096 (4) Å	µ = 0.08 mm^−1
β = 93.74 (3)°	T = 293 K
V = 2664.4 (10) Å^3	Plate, colourless
Z = 2	0.32 × 0.22 × 0.10 mm

Data collection

Siemens P4 diffractometer	5425 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 26.8°, θmin = 1.6°
ω scan (Sparks, 1976)	h = 0→19
Absorption correction: empirical (using intensity measurements) (Kopfmann & Huber, 1968)	k = −10→10
Tmin = 0.967, Tmax = 1.000	l = −24→24
9866 measured reflections	3 standard reflections every 97 reflections
5611 independent reflections	intensity decay: 98%

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.5886P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.002
5611 reflections	Δρmax = 0.28 e Å^−3
616 parameters	Δρmin = −0.18 e Å^−3
3 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (2)

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 on F² for ALL reflections except for 18 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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
O1	−0.08529 (15)	0.5542 (3)	0.43564 (12)	0.0557 (6)
H1	−0.1236	0.6143	0.4261	0.084*
O2	−0.00076 (13)	−0.0142 (3)	0.43946 (10)	0.0457 (5)
H2	0.0304	0.0098	0.4733	0.068*
O3	0.26677 (13)	−0.2083 (3)	0.06246 (10)	0.0468 (5)
H3	0.3080	−0.2488	0.0475	0.070*
N1	0.18369 (15)	0.0446 (3)	−0.02186 (12)	0.0406 (5)
C1	−0.05740 (19)	0.3798 (4)	0.25645 (14)	0.0412 (6)
H1A	−0.0406	0.4268	0.2135	0.049*
H1B	−0.1115	0.3331	0.2463	0.049*
C2	−0.0651 (2)	0.5066 (4)	0.31189 (15)	0.0459 (7)
H2A	−0.0136	0.5643	0.3172	0.055*
H2B	−0.1090	0.5776	0.2964	0.055*
C3	−0.08432 (19)	0.4372 (4)	0.38234 (14)	0.0421 (6)
H3A	−0.1395	0.3900	0.3772	0.050*
C4	−0.02275 (18)	0.3144 (3)	0.40632 (14)	0.0383 (6)
H4A	−0.0386	0.2702	0.4502	0.046*
H4B	0.0319	0.3601	0.4145	0.046*
C5	−0.01976 (17)	0.1871 (3)	0.35083 (13)	0.0340 (5)
H5	−0.0770	0.1504	0.3426	0.041*
C6	0.03096 (18)	0.0467 (3)	0.37639 (14)	0.0386 (6)
H6	0.0891	0.0770	0.3859	0.046*
C7	0.0256 (2)	−0.0820 (4)	0.32202 (15)	0.0462 (7)
H7A	−0.0306	−0.1220	0.3175	0.055*
H7B	0.0624	−0.1657	0.3374	0.055*
C8	0.04986 (19)	−0.0228 (3)	0.25107 (14)	0.0392 (6)
H8	0.1081	0.0095	0.2565	0.047*
C9	−0.00130 (18)	0.1173 (3)	0.22675 (14)	0.0374 (6)
H9	−0.0595	0.0847	0.2231	0.045*
C10	0.00532 (17)	0.2521 (3)	0.27904 (14)	0.0352 (6)
C11	0.0250 (2)	0.1393 (4)	0.15172 (15)	0.0456 (7)
H11A	0.0769	0.1955	0.1517	0.055*
H11B	−0.0172	0.1954	0.1235	0.055*
C12	0.03500 (18)	−0.0264 (4)	0.12320 (14)	0.0403 (6)
H12	−0.0149	−0.0536	0.0939	0.048*
C13	0.11074 (17)	−0.0460 (3)	0.08006 (14)	0.0375 (6)
H13	0.1603	−0.0197	0.1101	0.045*
C14	0.0411 (2)	−0.1342 (4)	0.18922 (15)	0.0445 (7)
H14	−0.0114	−0.1905	0.1913	0.053*
C15	0.1123 (2)	−0.2519 (4)	0.18780 (17)	0.0525 (8)
H15A	0.1647	−0.1995	0.1986	0.063*
H15B	0.1057	−0.3293	0.2237	0.063*
C16	0.1144 (2)	−0.3299 (4)	0.11775 (17)	0.0539 (8)
H16A	0.0649	−0.3926	0.1098	0.065*
H16B	0.1621	−0.3982	0.1185	0.065*
C17	0.11931 (18)	−0.2135 (3)	0.05611 (15)	0.0391 (6)
H17	0.0710	−0.2344	0.0238	0.047*
C18	0.10838 (19)	0.0585 (4)	0.01600 (15)	0.0455 (7)
H18A	0.0607	0.0319	−0.0152	0.055*
H18B	0.1020	0.1648	0.0307	0.055*
C19	0.1782 (2)	0.1541 (4)	−0.08067 (16)	0.0520 (8)
H19A	0.1675	0.2566	−0.0629	0.062*
H19B	0.1318	0.1257	−0.1128	0.062*
C20	0.19603 (18)	−0.2330 (4)	0.01312 (15)	0.0405 (6)
C21	0.19541 (19)	−0.1137 (4)	−0.04672 (15)	0.0408 (6)
H21	0.1485	−0.1384	−0.0800	0.049*
C22	0.2745 (2)	−0.1205 (4)	−0.08675 (17)	0.0537 (8)
H22A	0.3222	−0.1011	−0.0543	0.064*
H22B	0.2804	−0.2234	−0.1058	0.064*
C23	0.2739 (2)	−0.0031 (5)	−0.14645 (16)	0.0552 (9)
H23A	0.3271	−0.0047	−0.1672	0.066*
H23B	0.2315	−0.0314	−0.1825	0.066*
C24	0.2568 (2)	0.1584 (4)	−0.12045 (15)	0.0500 (8)
H24	0.2461	0.2248	−0.1616	0.060*
C25	0.09345 (19)	0.3199 (4)	0.28425 (16)	0.0458 (7)
H25A	0.1328	0.2396	0.2965	0.069*
H25B	0.0972	0.3988	0.3196	0.069*
H25C	0.1055	0.3637	0.2399	0.069*
C26	0.1989 (2)	−0.3966 (4)	−0.01728 (18)	0.0537 (8)
H26A	0.2520	−0.4141	−0.0357	0.081*
H26B	0.1561	−0.4078	−0.0542	0.081*
H26C	0.1903	−0.4705	0.0190	0.081*
C27	0.3297 (2)	0.2260 (5)	−0.07682 (18)	0.0597 (9)
H27A	0.3375	0.1703	−0.0334	0.090*
H27B	0.3190	0.3327	−0.0672	0.090*
H27C	0.3790	0.2179	−0.1022	0.090*
O1'	0.42974 (15)	0.6533 (3)	0.03954 (10)	0.0490 (5)
H1'	0.4474	0.6101	0.0053	0.074*
O2'	0.34850 (15)	0.1007 (3)	0.11070 (11)	0.0581 (6)
H2'	0.3121	0.0352	0.1047	0.087*
O3'	0.23827 (12)	0.1921 (3)	0.59692 (12)	0.0458 (5)
H3'	0.2337	0.2836	0.5862	0.069*
N1'	0.36238 (14)	0.4218 (3)	0.60350 (12)	0.0364 (5)
C1'	0.4515 (2)	0.5645 (4)	0.23238 (14)	0.0458 (7)
H1'1	0.5054	0.5146	0.2363	0.055*
H1'2	0.4484	0.6333	0.2722	0.055*
C2'	0.4442 (2)	0.6601 (4)	0.16454 (14)	0.0474 (7)
H2'1	0.3931	0.7192	0.1627	0.057*
H2'2	0.4902	0.7322	0.1643	0.057*
C3'	0.44475 (19)	0.5567 (4)	0.10085 (14)	0.0423 (6)
H3'1	0.5000	0.5104	0.0994	0.051*
C4'	0.38079 (19)	0.4276 (4)	0.10177 (15)	0.0445 (7)
H4'1	0.3874	0.3591	0.0623	0.053*
H4'2	0.3255	0.4715	0.0967	0.053*
C5'	0.39028 (18)	0.3346 (4)	0.17033 (14)	0.0388 (6)
H5'	0.4469	0.2933	0.1733	0.047*
C6'	0.3319 (2)	0.1945 (4)	0.17040 (15)	0.0457 (7)
H6'	0.2742	0.2303	0.1656	0.055*
C7'	0.3455 (2)	0.1006 (4)	0.23814 (15)	0.0479 (7)
H7'1	0.3033	0.0210	0.2391	0.057*
H7'2	0.3992	0.0503	0.2390	0.057*
C8'	0.34156 (18)	0.2024 (4)	0.30268 (14)	0.0407 (6)
H8'	0.2853	0.2452	0.3024	0.049*
C9'	0.40176 (17)	0.3378 (4)	0.30001 (13)	0.0375 (6)
H9'	0.4573	0.2940	0.2963	0.045*
C10'	0.38386 (17)	0.4413 (4)	0.23530 (13)	0.0377 (6)
C11'	0.3995 (2)	0.4068 (4)	0.37388 (14)	0.0439 (7)
H11C	0.3493	0.4665	0.3785	0.053*
H11D	0.4474	0.4723	0.3849	0.053*
C12'	0.40133 (18)	0.2629 (4)	0.42150 (14)	0.0398 (6)
H12'	0.4596	0.2364	0.4334	0.048*
C13'	0.35877 (17)	0.2846 (3)	0.49023 (14)	0.0365 (6)
H13'	0.3014	0.3175	0.4786	0.044*
C14'	0.36180 (18)	0.1296 (4)	0.37568 (15)	0.0415 (6)
H14'	0.4036	0.0488	0.3712	0.050*
C15'	0.2873 (2)	0.0592 (4)	0.40836 (16)	0.0503 (8)
H15C	0.2675	−0.0285	0.3804	0.060*
H15D	0.2429	0.1349	0.4078	0.060*
C16'	0.3078 (2)	0.0061 (4)	0.48405 (16)	0.0532 (8)
H16C	0.3407	−0.0876	0.4836	0.064*
H16D	0.2567	−0.0180	0.5056	0.064*
C17'	0.35638 (19)	0.1301 (4)	0.52895 (15)	0.0415 (6)
H17'	0.4139	0.0938	0.5356	0.050*
C18'	0.40108 (18)	0.4078 (4)	0.53664 (14)	0.0397 (6)
H18C	0.4592	0.3817	0.5455	0.048*
H18D	0.3979	0.5063	0.5124	0.048*
C19'	0.39490 (19)	0.5599 (4)	0.64080 (15)	0.0451 (7)
H19C	0.3818	0.6503	0.6122	0.054*
H19D	0.4549	0.5521	0.6471	0.054*
C20'	0.32439 (18)	0.1506 (3)	0.60287 (14)	0.0395 (6)
C21'	0.37384 (18)	0.2780 (4)	0.64331 (15)	0.0399 (6)
H21'	0.4328	0.2505	0.6455	0.048*
C22'	0.3469 (2)	0.2950 (4)	0.71872 (15)	0.0477 (7)
H22C	0.2868	0.2989	0.7175	0.057*
H22D	0.3649	0.2046	0.7456	0.057*
C23'	0.3817 (2)	0.4379 (4)	0.75560 (16)	0.0548 (8)
H23C	0.4416	0.4290	0.7625	0.066*
H23D	0.3593	0.4469	0.8013	0.066*
C24'	0.3596 (2)	0.5815 (4)	0.71237 (15)	0.0467 (7)
H24'	0.3878	0.6698	0.7354	0.056*
C25'	0.2994 (2)	0.5209 (4)	0.23720 (17)	0.0489 (7)
H25D	0.2989	0.5850	0.2782	0.073*
H25E	0.2566	0.4443	0.2386	0.073*
H25F	0.2896	0.5834	0.1960	0.073*
C26'	0.3290 (2)	−0.0032 (4)	0.64205 (17)	0.0531 (8)
H26D	0.3007	0.0057	0.6845	0.080*
H26E	0.3860	−0.0297	0.6533	0.080*
H26F	0.3031	−0.0823	0.6130	0.080*
C27'	0.2669 (2)	0.6145 (5)	0.70731 (19)	0.0591 (9)
H27D	0.2381	0.5309	0.6834	0.089*
H27E	0.2564	0.7086	0.6817	0.089*
H27F	0.2478	0.6247	0.7536	0.089*
O4	0.16490 (17)	0.4504 (4)	0.53190 (17)	0.0782 (9)
H4	0.1152	0.4561	0.5379	0.117*
C29	0.1944 (2)	0.5962 (5)	0.5125 (2)	0.0627 (9)
H29A	0.2546	0.5958	0.5166	0.075*
H29B	0.1755	0.6738	0.5444	0.075*
C30	0.1652 (3)	0.6376 (7)	0.4392 (2)	0.0948 (17)
H30A	0.1838	0.5609	0.4075	0.142*
H30B	0.1874	0.7365	0.4275	0.142*
H30C	0.1057	0.6421	0.4354	0.142*
O1W	0.5073 (2)	0.4808 (4)	−0.05736 (17)	0.0790 (9)
H51	0.517 (3)	0.384 (3)	−0.051 (2)	0.080*
H52	0.546 (2)	0.525 (5)	−0.079 (2)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0643 (15)	0.0566 (14)	0.0451 (12)	0.0214 (11)	−0.0056 (10)	−0.0135 (11)
O2	0.0541 (13)	0.0494 (12)	0.0333 (10)	−0.0031 (10)	0.0012 (8)	0.0087 (9)
O3	0.0398 (11)	0.0605 (14)	0.0396 (10)	0.0092 (10)	−0.0023 (8)	−0.0083 (10)
N1	0.0461 (14)	0.0422 (13)	0.0344 (12)	0.0044 (10)	0.0096 (10)	0.0024 (10)
C1	0.0476 (16)	0.0420 (16)	0.0339 (14)	0.0091 (12)	0.0026 (11)	0.0045 (12)
C2	0.0525 (18)	0.0402 (16)	0.0450 (16)	0.0110 (13)	0.0026 (13)	0.0012 (13)
C3	0.0451 (16)	0.0443 (16)	0.0365 (14)	0.0067 (13)	0.0009 (11)	−0.0054 (13)
C4	0.0409 (15)	0.0386 (15)	0.0352 (13)	0.0019 (12)	0.0007 (11)	−0.0014 (12)
C5	0.0340 (14)	0.0349 (14)	0.0331 (13)	−0.0015 (11)	0.0018 (10)	0.0013 (11)
C6	0.0414 (15)	0.0397 (15)	0.0349 (14)	−0.0012 (12)	0.0034 (10)	0.0059 (12)
C7	0.0611 (19)	0.0356 (15)	0.0428 (16)	0.0038 (13)	0.0095 (13)	0.0067 (13)
C8	0.0455 (16)	0.0362 (14)	0.0363 (14)	0.0019 (12)	0.0071 (11)	0.0030 (12)
C9	0.0372 (14)	0.0401 (15)	0.0352 (13)	0.0015 (11)	0.0058 (10)	0.0015 (12)
C10	0.0367 (14)	0.0346 (13)	0.0342 (13)	−0.0006 (11)	0.0017 (10)	0.0014 (11)
C11	0.0563 (18)	0.0453 (17)	0.0363 (15)	0.0111 (14)	0.0116 (12)	0.0064 (13)
C12	0.0416 (15)	0.0426 (16)	0.0370 (14)	0.0032 (12)	0.0060 (11)	0.0016 (12)
C13	0.0379 (14)	0.0403 (15)	0.0346 (14)	0.0033 (11)	0.0037 (10)	0.0003 (12)
C14	0.0528 (18)	0.0408 (16)	0.0408 (15)	−0.0017 (13)	0.0104 (12)	−0.0008 (13)
C15	0.071 (2)	0.0408 (17)	0.0463 (17)	0.0088 (15)	0.0070 (15)	0.0052 (14)
C16	0.068 (2)	0.0448 (18)	0.0499 (18)	0.0086 (15)	0.0110 (15)	0.0042 (15)
C17	0.0383 (15)	0.0414 (16)	0.0374 (14)	0.0020 (12)	0.0020 (11)	0.0004 (12)
C18	0.0504 (18)	0.0472 (17)	0.0399 (15)	0.0110 (13)	0.0113 (12)	0.0044 (13)
C19	0.060 (2)	0.056 (2)	0.0411 (16)	0.0092 (16)	0.0097 (13)	0.0104 (15)
C20	0.0415 (16)	0.0434 (15)	0.0363 (14)	0.0027 (12)	0.0000 (11)	−0.0054 (12)
C21	0.0428 (16)	0.0464 (16)	0.0332 (14)	−0.0003 (12)	0.0019 (11)	−0.0051 (12)
C22	0.061 (2)	0.055 (2)	0.0475 (18)	0.0047 (15)	0.0167 (14)	−0.0078 (15)
C23	0.062 (2)	0.070 (2)	0.0340 (15)	−0.0071 (17)	0.0126 (13)	−0.0082 (16)
C24	0.0537 (19)	0.063 (2)	0.0343 (15)	0.0003 (15)	0.0096 (12)	0.0073 (15)
C25	0.0436 (17)	0.0424 (16)	0.0519 (17)	−0.0057 (13)	0.0078 (12)	0.0023 (14)
C26	0.064 (2)	0.0475 (18)	0.0498 (18)	0.0049 (16)	0.0055 (15)	−0.0092 (15)
C27	0.066 (2)	0.066 (2)	0.0474 (18)	−0.0138 (18)	0.0090 (15)	−0.0011 (17)
O1'	0.0599 (14)	0.0543 (13)	0.0334 (10)	0.0054 (11)	0.0082 (9)	0.0036 (10)
O2'	0.0685 (16)	0.0625 (16)	0.0441 (12)	−0.0166 (12)	0.0097 (10)	−0.0188 (11)
O3'	0.0411 (11)	0.0457 (12)	0.0511 (12)	−0.0054 (9)	0.0075 (8)	0.0078 (10)
N1'	0.0390 (12)	0.0375 (12)	0.0330 (11)	−0.0038 (10)	0.0037 (9)	0.0056 (10)
C1'	0.0534 (18)	0.0513 (18)	0.0326 (14)	−0.0137 (14)	0.0013 (11)	−0.0030 (13)
C2'	0.0582 (19)	0.0492 (18)	0.0345 (14)	−0.0125 (15)	0.0013 (12)	−0.0010 (13)
C3'	0.0473 (16)	0.0481 (17)	0.0314 (13)	−0.0008 (13)	0.0021 (11)	0.0012 (12)
C4'	0.0484 (17)	0.0508 (17)	0.0339 (14)	−0.0050 (14)	−0.0001 (11)	−0.0045 (13)
C5'	0.0402 (15)	0.0444 (16)	0.0317 (13)	−0.0049 (12)	0.0019 (10)	−0.0011 (12)
C6'	0.0479 (17)	0.0518 (18)	0.0375 (15)	−0.0083 (14)	0.0039 (11)	−0.0106 (14)
C7'	0.0542 (18)	0.0455 (17)	0.0439 (16)	−0.0110 (14)	0.0032 (13)	−0.0039 (14)
C8'	0.0374 (15)	0.0463 (16)	0.0381 (14)	−0.0051 (12)	0.0012 (11)	0.0006 (13)
C9'	0.0359 (14)	0.0456 (16)	0.0309 (13)	−0.0036 (12)	0.0014 (10)	−0.0017 (12)
C10'	0.0405 (15)	0.0431 (15)	0.0292 (12)	−0.0033 (12)	0.0008 (10)	−0.0027 (12)
C11'	0.0505 (18)	0.0476 (17)	0.0335 (14)	−0.0090 (13)	0.0031 (11)	0.0016 (13)
C12'	0.0346 (15)	0.0497 (16)	0.0355 (14)	−0.0029 (12)	0.0050 (10)	0.0038 (13)
C13'	0.0340 (14)	0.0406 (15)	0.0350 (13)	−0.0006 (11)	0.0044 (10)	0.0041 (12)
C14'	0.0430 (16)	0.0427 (16)	0.0390 (14)	−0.0013 (12)	0.0031 (11)	0.0013 (13)
C15'	0.0555 (19)	0.0526 (19)	0.0430 (16)	−0.0160 (15)	0.0037 (13)	0.0010 (15)
C16'	0.072 (2)	0.0454 (18)	0.0435 (17)	−0.0110 (16)	0.0119 (14)	0.0027 (14)
C17'	0.0454 (16)	0.0394 (15)	0.0405 (14)	0.0001 (12)	0.0073 (11)	0.0043 (12)
C18'	0.0387 (15)	0.0436 (16)	0.0375 (14)	−0.0034 (12)	0.0082 (11)	0.0058 (12)
C19'	0.0455 (17)	0.0477 (17)	0.0424 (16)	−0.0089 (13)	0.0046 (12)	0.0043 (14)
C20'	0.0407 (15)	0.0394 (15)	0.0385 (14)	0.0008 (12)	0.0034 (11)	0.0087 (12)
C21'	0.0387 (15)	0.0425 (16)	0.0384 (14)	0.0036 (12)	0.0026 (11)	0.0105 (12)
C22'	0.061 (2)	0.0454 (17)	0.0367 (15)	0.0017 (14)	0.0049 (13)	0.0097 (13)
C23'	0.071 (2)	0.056 (2)	0.0374 (15)	−0.0014 (17)	0.0003 (14)	0.0057 (15)
C24'	0.0536 (18)	0.0491 (18)	0.0375 (15)	−0.0047 (14)	0.0040 (12)	0.0013 (14)
C25'	0.0479 (18)	0.0544 (19)	0.0445 (16)	0.0079 (14)	0.0048 (12)	0.0031 (14)
C26'	0.073 (2)	0.0407 (17)	0.0458 (17)	0.0002 (16)	0.0060 (15)	0.0123 (14)
C27'	0.065 (2)	0.057 (2)	0.0571 (19)	0.0111 (17)	0.0165 (16)	0.0029 (17)
O4	0.0513 (15)	0.077 (2)	0.107 (2)	0.0146 (14)	0.0093 (14)	0.0310 (18)
C29	0.055 (2)	0.060 (2)	0.072 (2)	0.0101 (17)	−0.0051 (16)	0.0003 (19)
C30	0.109 (4)	0.101 (4)	0.072 (3)	−0.035 (3)	−0.017 (2)	0.021 (3)
O1W	0.094 (2)	0.0712 (19)	0.0759 (19)	−0.0042 (17)	0.0376 (16)	−0.0100 (17)

Geometric parameters (Å, º)

O1—C3	1.437 (3)	O3'—H3'	0.8200
O1—H1	0.8200	N1'—C18'	1.463 (3)
O2—C6	1.439 (3)	N1'—C21'	1.464 (4)
O2—H2	0.8200	N1'—C19'	1.471 (4)
O3—C20	1.448 (3)	C1'—C10'	1.531 (4)
O3—H3	0.8200	C1'—C2'	1.535 (4)
N1—C18	1.460 (4)	C1'—H1'1	0.9700
N1—C21	1.467 (4)	C1'—H1'2	0.9700
N1—C19	1.468 (4)	C2'—C3'	1.510 (4)
C1—C2	1.536 (4)	C2'—H2'1	0.9700
C1—C10	1.542 (4)	C2'—H2'2	0.9700
C1—H1A	0.9700	C3'—C4'	1.523 (4)
C1—H1B	0.9700	C3'—H3'1	0.9800
C2—C3	1.523 (4)	C4'—C5'	1.536 (4)
C2—H2A	0.9700	C4'—H4'1	0.9700
C2—H2B	0.9700	C4'—H4'2	0.9700
C3—C4	1.507 (4)	C5'—C6'	1.536 (4)
C3—H3A	0.9800	C5'—C10'	1.556 (4)
C4—C5	1.532 (4)	C5'—H5'	0.9800
C4—H4A	0.9700	C6'—C7'	1.532 (4)
C4—H4B	0.9700	C6'—H6'	0.9800
C5—C6	1.528 (4)	C7'—C8'	1.520 (4)
C5—C10	1.560 (4)	C7'—H7'1	0.9700
C5—H5	0.9800	C7'—H7'2	0.9700
C6—C7	1.522 (4)	C8'—C9'	1.526 (4)
C6—H6	0.9800	C8'—C14'	1.545 (4)
C7—C8	1.523 (4)	C8'—H8'	0.9800
C7—H7A	0.9700	C9'—C11'	1.535 (4)
C7—H7B	0.9700	C9'—C10'	1.539 (4)
C8—C9	1.523 (4)	C9'—H9'	0.9800
C8—C14	1.525 (4)	C10'—C25'	1.531 (4)
C8—H8	0.9800	C11'—C12'	1.542 (4)
C9—C11	1.532 (4)	C11'—H11C	0.9700
C9—C10	1.535 (4)	C11'—H11D	0.9700
C9—H9	0.9800	C12'—C13'	1.532 (4)
C10—C25	1.537 (4)	C12'—C14'	1.560 (4)
C11—C12	1.547 (4)	C12'—H12'	0.9800
C11—H11A	0.9700	C13'—C18'	1.520 (4)
C11—H11B	0.9700	C13'—C17'	1.531 (4)
C12—C13	1.528 (4)	C13'—H13'	0.9800
C12—C14	1.567 (4)	C14'—C15'	1.519 (4)
C12—H12	0.9800	C14'—H14'	0.9800
C13—C18	1.520 (4)	C15'—C16'	1.533 (4)
C13—C17	1.530 (4)	C15'—H15C	0.9700
C13—H13	0.9800	C15'—H15D	0.9700
C14—C15	1.537 (5)	C16'—C17'	1.554 (4)
C14—H14	0.9800	C16'—H16C	0.9700
C15—C16	1.501 (5)	C16'—H16D	0.9700
C15—H15A	0.9700	C17'—C20'	1.545 (4)
C15—H15B	0.9700	C17'—H17'	0.9800
C16—C17	1.556 (4)	C18'—H18C	0.9700
C16—H16A	0.9700	C18'—H18D	0.9700
C16—H16B	0.9700	C19'—C24'	1.526 (4)
C17—C20	1.539 (4)	C19'—H19C	0.9700
C17—H17	0.9800	C19'—H19D	0.9700
C18—H18A	0.9700	C20'—C26'	1.527 (4)
C18—H18B	0.9700	C20'—C21'	1.540 (4)
C19—C24	1.522 (4)	C21'—C22'	1.538 (4)
C19—H19A	0.9700	C21'—H21'	0.9800
C19—H19B	0.9700	C22'—C23'	1.514 (5)
C20—C26	1.533 (4)	C22'—H22C	0.9700
C20—C21	1.540 (4)	C22'—H22D	0.9700
C21—C22	1.532 (4)	C23'—C24'	1.522 (5)
C21—H21	0.9800	C23'—H23C	0.9700
C22—C23	1.527 (5)	C23'—H23D	0.9700
C22—H22A	0.9700	C24'—C27'	1.521 (5)
C22—H22B	0.9700	C24'—H24'	0.9800
C23—C24	1.515 (5)	C25'—H25D	0.9600
C23—H23A	0.9700	C25'—H25E	0.9600
C23—H23B	0.9700	C25'—H25F	0.9600
C24—C27	1.515 (5)	C26'—H26D	0.9600
C24—H24	0.9800	C26'—H26E	0.9600
C25—H25A	0.9600	C26'—H26F	0.9600
C25—H25B	0.9600	C27'—H27D	0.9600
C25—H25C	0.9600	C27'—H27E	0.9600
C26—H26A	0.9600	C27'—H27F	0.9600
C26—H26B	0.9600	O4—C29	1.408 (5)
C26—H26C	0.9600	O4—H4	0.8200
C27—H27A	0.9600	C29—C30	1.491 (5)
C27—H27B	0.9600	C29—H29A	0.9700
C27—H27C	0.9600	C29—H29B	0.9700
O1'—C3'	1.446 (3)	C30—H30A	0.9600
O1'—H1'	0.8200	C30—H30B	0.9600
O2'—C6'	1.439 (4)	C30—H30C	0.9600
O2'—H2'	0.8200	O1W—H51	0.86 (2)
O3'—C20'	1.434 (4)	O1W—H52	0.86 (2)
C3—O1—H1	109.5	C10'—C1'—H1'1	109.0
C6—O2—H2	109.5	C2'—C1'—H1'1	109.0
C20—O3—H3	109.5	C10'—C1'—H1'2	109.0
C18—N1—C21	111.5 (2)	C2'—C1'—H1'2	109.0
C18—N1—C19	108.4 (2)	H1'1—C1'—H1'2	107.8
C21—N1—C19	111.0 (2)	C3'—C2'—C1'	110.8 (3)
C2—C1—C10	113.6 (2)	C3'—C2'—H2'1	109.5
C2—C1—H1A	108.8	C1'—C2'—H2'1	109.5
C10—C1—H1A	108.8	C3'—C2'—H2'2	109.5
C2—C1—H1B	108.8	C1'—C2'—H2'2	109.5
C10—C1—H1B	108.8	H2'1—C2'—H2'2	108.1
H1A—C1—H1B	107.7	O1'—C3'—C2'	107.4 (2)
C3—C2—C1	110.9 (3)	O1'—C3'—C4'	110.9 (2)
C3—C2—H2A	109.5	C2'—C3'—C4'	112.7 (2)
C1—C2—H2A	109.5	O1'—C3'—H3'1	108.6
C3—C2—H2B	109.5	C2'—C3'—H3'1	108.6
C1—C2—H2B	109.5	C4'—C3'—H3'1	108.6
H2A—C2—H2B	108.0	C3'—C4'—C5'	111.4 (2)
O1—C3—C4	108.7 (2)	C3'—C4'—H4'1	109.4
O1—C3—C2	111.1 (3)	C5'—C4'—H4'1	109.4
C4—C3—C2	112.2 (2)	C3'—C4'—H4'2	109.4
O1—C3—H3A	108.2	C5'—C4'—H4'2	109.4
C4—C3—H3A	108.2	H4'1—C4'—H4'2	108.0
C2—C3—H3A	108.2	C4'—C5'—C6'	112.8 (2)
C3—C4—C5	110.3 (2)	C4'—C5'—C10'	111.1 (2)
C3—C4—H4A	109.6	C6'—C5'—C10'	113.3 (2)
C5—C4—H4A	109.6	C4'—C5'—H5'	106.3
C3—C4—H4B	109.6	C6'—C5'—H5'	106.3
C5—C4—H4B	109.6	C10'—C5'—H5'	106.3
H4A—C4—H4B	108.1	O2'—C6'—C7'	110.2 (3)
C6—C5—C4	113.1 (2)	O2'—C6'—C5'	107.4 (2)
C6—C5—C10	113.8 (2)	C7'—C6'—C5'	111.5 (2)
C4—C5—C10	111.7 (2)	O2'—C6'—H6'	109.2
C6—C5—H5	105.8	C7'—C6'—H6'	109.2
C4—C5—H5	105.8	C5'—C6'—H6'	109.2
C10—C5—H5	105.8	C8'—C7'—C6'	111.4 (3)
O2—C6—C7	107.1 (2)	C8'—C7'—H7'1	109.3
O2—C6—C5	110.3 (2)	C6'—C7'—H7'1	109.3
C7—C6—C5	111.1 (2)	C8'—C7'—H7'2	109.3
O2—C6—H6	109.4	C6'—C7'—H7'2	109.3
C7—C6—H6	109.4	H7'1—C7'—H7'2	108.0
C5—C6—H6	109.4	C7'—C8'—C9'	111.0 (2)
C6—C7—C8	110.7 (2)	C7'—C8'—C14'	118.5 (3)
C6—C7—H7A	109.5	C9'—C8'—C14'	104.2 (2)
C8—C7—H7A	109.5	C7'—C8'—H8'	107.5
C6—C7—H7B	109.5	C9'—C8'—H8'	107.5
C8—C7—H7B	109.5	C14'—C8'—H8'	107.5
H7A—C7—H7B	108.1	C8'—C9'—C11'	102.4 (2)
C9—C8—C7	111.9 (2)	C8'—C9'—C10'	112.8 (2)
C9—C8—C14	104.3 (2)	C11'—C9'—C10'	119.8 (2)
C7—C8—C14	117.4 (3)	C8'—C9'—H9'	107.0
C9—C8—H8	107.6	C11'—C9'—H9'	107.0
C7—C8—H8	107.6	C10'—C9'—H9'	107.0
C14—C8—H8	107.6	C1'—C10'—C25'	109.0 (3)
C8—C9—C11	101.9 (2)	C1'—C10'—C9'	109.8 (2)
C8—C9—C10	113.2 (2)	C25'—C10'—C9'	111.4 (2)
C11—C9—C10	120.1 (2)	C1'—C10'—C5'	107.4 (2)
C8—C9—H9	106.9	C25'—C10'—C5'	113.1 (2)
C11—C9—H9	106.9	C9'—C10'—C5'	106.0 (2)
C10—C9—H9	106.9	C9'—C11'—C12'	103.1 (2)
C9—C10—C25	111.0 (2)	C9'—C11'—H11C	111.1
C9—C10—C1	110.3 (2)	C12'—C11'—H11C	111.1
C25—C10—C1	109.4 (2)	C9'—C11'—H11D	111.1
C9—C10—C5	106.6 (2)	C12'—C11'—H11D	111.1
C25—C10—C5	111.9 (2)	H11C—C11'—H11D	109.1
C1—C10—C5	107.5 (2)	C13'—C12'—C11'	114.4 (2)
C9—C11—C12	104.8 (2)	C13'—C12'—C14'	112.4 (2)
C9—C11—H11A	110.8	C11'—C12'—C14'	106.0 (2)
C12—C11—H11A	110.8	C13'—C12'—H12'	107.9
C9—C11—H11B	110.8	C11'—C12'—H12'	107.9
C12—C11—H11B	110.8	C14'—C12'—H12'	107.9
H11A—C11—H11B	108.9	C18'—C13'—C17'	110.9 (2)
C13—C12—C11	113.5 (2)	C18'—C13'—C12'	112.1 (2)
C13—C12—C14	110.9 (2)	C17'—C13'—C12'	109.5 (2)
C11—C12—C14	105.8 (2)	C18'—C13'—H13'	108.1
C13—C12—H12	108.8	C17'—C13'—H13'	108.1
C11—C12—H12	108.8	C12'—C13'—H13'	108.1
C14—C12—H12	108.8	C15'—C14'—C8'	114.1 (2)
C18—C13—C12	112.9 (2)	C15'—C14'—C12'	111.9 (2)
C18—C13—C17	108.8 (2)	C8'—C14'—C12'	105.0 (2)
C12—C13—C17	111.0 (2)	C15'—C14'—H14'	108.6
C18—C13—H13	108.0	C8'—C14'—H14'	108.6
C12—C13—H13	108.0	C12'—C14'—H14'	108.6
C17—C13—H13	108.0	C14'—C15'—C16'	112.3 (3)
C8—C14—C15	113.7 (3)	C14'—C15'—H15C	109.2
C8—C14—C12	104.1 (2)	C16'—C15'—H15C	109.2
C15—C14—C12	112.8 (2)	C14'—C15'—H15D	109.2
C8—C14—H14	108.7	C16'—C15'—H15D	109.2
C15—C14—H14	108.7	H15C—C15'—H15D	107.9
C12—C14—H14	108.7	C15'—C16'—C17'	112.5 (3)
C16—C15—C14	112.0 (3)	C15'—C16'—H16C	109.1
C16—C15—H15A	109.2	C17'—C16'—H16C	109.1
C14—C15—H15A	109.2	C15'—C16'—H16D	109.1
C16—C15—H15B	109.2	C17'—C16'—H16D	109.1
C14—C15—H15B	109.2	H16C—C16'—H16D	107.8
H15A—C15—H15B	107.9	C13'—C17'—C20'	111.2 (2)
C15—C16—C17	112.8 (3)	C13'—C17'—C16'	111.4 (2)
C15—C16—H16A	109.0	C20'—C17'—C16'	113.4 (3)
C17—C16—H16A	109.0	C13'—C17'—H17'	106.8
C15—C16—H16B	109.0	C20'—C17'—H17'	106.8
C17—C16—H16B	109.0	C16'—C17'—H17'	106.8
H16A—C16—H16B	107.8	N1'—C18'—C13'	111.4 (2)
C13—C17—C20	110.8 (2)	N1'—C18'—H18C	109.3
C13—C17—C16	112.2 (2)	C13'—C18'—H18C	109.3
C20—C17—C16	114.5 (3)	N1'—C18'—H18D	109.3
C13—C17—H17	106.2	C13'—C18'—H18D	109.3
C20—C17—H17	106.2	H18C—C18'—H18D	108.0
C16—C17—H17	106.2	N1'—C19'—C24'	113.0 (2)
N1—C18—C13	111.8 (2)	N1'—C19'—H19C	109.0
N1—C18—H18A	109.3	C24'—C19'—H19C	109.0
C13—C18—H18A	109.3	N1'—C19'—H19D	109.0
N1—C18—H18B	109.3	C24'—C19'—H19D	109.0
C13—C18—H18B	109.3	H19C—C19'—H19D	107.8
H18A—C18—H18B	107.9	O3'—C20'—C26'	105.9 (2)
N1—C19—C24	112.8 (3)	O3'—C20'—C21'	109.2 (2)
N1—C19—H19A	109.0	C26'—C20'—C21'	111.9 (2)
C24—C19—H19A	109.0	O3'—C20'—C17'	109.7 (2)
N1—C19—H19B	109.0	C26'—C20'—C17'	109.8 (3)
C24—C19—H19B	109.0	C21'—C20'—C17'	110.3 (2)
H19A—C19—H19B	107.8	N1'—C21'—C22'	111.7 (2)
O3—C20—C26	109.9 (3)	N1'—C21'—C20'	107.8 (2)
O3—C20—C17	105.3 (2)	C22'—C21'—C20'	111.7 (2)
C26—C20—C17	110.4 (3)	N1'—C21'—H21'	108.5
O3—C20—C21	110.5 (2)	C22'—C21'—H21'	108.5
C26—C20—C21	109.7 (2)	C20'—C21'—H21'	108.5
C17—C20—C21	110.8 (2)	C23'—C22'—C21'	113.2 (3)
N1—C21—C22	109.1 (2)	C23'—C22'—H22C	108.9
N1—C21—C20	112.4 (2)	C21'—C22'—H22C	108.9
C22—C21—C20	112.3 (3)	C23'—C22'—H22D	108.9
N1—C21—H21	107.6	C21'—C22'—H22D	108.9
C22—C21—H21	107.6	H22C—C22'—H22D	107.7
C20—C21—H21	107.6	C22'—C23'—C24'	110.4 (2)
C23—C22—C21	112.4 (3)	C22'—C23'—H23C	109.6
C23—C22—H22A	109.1	C24'—C23'—H23C	109.6
C21—C22—H22A	109.1	C22'—C23'—H23D	109.6
C23—C22—H22B	109.1	C24'—C23'—H23D	109.6
C21—C22—H22B	109.1	H23C—C23'—H23D	108.1
H22A—C22—H22B	107.9	C27'—C24'—C23'	112.5 (3)
C24—C23—C22	111.3 (2)	C27'—C24'—C19'	112.9 (3)
C24—C23—H23A	109.4	C23'—C24'—C19'	107.3 (3)
C22—C23—H23A	109.4	C27'—C24'—H24'	108.0
C24—C23—H23B	109.4	C23'—C24'—H24'	108.0
C22—C23—H23B	109.4	C19'—C24'—H24'	108.0
H23A—C23—H23B	108.0	C10'—C25'—H25D	109.5
C27—C24—C23	112.7 (3)	C10'—C25'—H25E	109.5
C27—C24—C19	112.2 (3)	H25D—C25'—H25E	109.5
C23—C24—C19	108.4 (3)	C10'—C25'—H25F	109.5
C27—C24—H24	107.8	H25D—C25'—H25F	109.5
C23—C24—H24	107.8	H25E—C25'—H25F	109.5
C19—C24—H24	107.8	C20'—C26'—H26D	109.5
C10—C25—H25A	109.5	C20'—C26'—H26E	109.5
C10—C25—H25B	109.5	H26D—C26'—H26E	109.5
H25A—C25—H25B	109.5	C20'—C26'—H26F	109.5
C10—C25—H25C	109.5	H26D—C26'—H26F	109.5
H25A—C25—H25C	109.5	H26E—C26'—H26F	109.5
H25B—C25—H25C	109.5	C24'—C27'—H27D	109.5
C20—C26—H26A	109.5	C24'—C27'—H27E	109.5
C20—C26—H26B	109.5	H27D—C27'—H27E	109.5
H26A—C26—H26B	109.5	C24'—C27'—H27F	109.5
C20—C26—H26C	109.5	H27D—C27'—H27F	109.5
H26A—C26—H26C	109.5	H27E—C27'—H27F	109.5
H26B—C26—H26C	109.5	C29—O4—H4	109.5
C24—C27—H27A	109.5	O4—C29—C30	111.8 (4)
C24—C27—H27B	109.5	O4—C29—H29A	109.3
H27A—C27—H27B	109.5	C30—C29—H29A	109.3
C24—C27—H27C	109.5	O4—C29—H29B	109.3
H27A—C27—H27C	109.5	C30—C29—H29B	109.3
H27B—C27—H27C	109.5	H29A—C29—H29B	107.9
C3'—O1'—H1'	109.5	C29—C30—H30A	109.5
C6'—O2'—H2'	109.5	C29—C30—H30B	109.5
C20'—O3'—H3'	109.5	H30A—C30—H30B	109.5
C18'—N1'—C21'	109.6 (2)	C29—C30—H30C	109.5
C18'—N1'—C19'	109.3 (2)	H30A—C30—H30C	109.5
C21'—N1'—C19'	114.3 (2)	H30B—C30—H30C	109.5
C10'—C1'—C2'	113.0 (2)	H51—O1W—H52	111 (5)
C10—C1—C2—C3	−53.8 (3)	C10'—C1'—C2'—C3'	−56.0 (4)
C1—C2—C3—O1	175.6 (2)	C1'—C2'—C3'—O1'	174.7 (2)
C1—C2—C3—C4	53.7 (3)	C1'—C2'—C3'—C4'	52.2 (4)
O1—C3—C4—C5	−180.0 (2)	O1'—C3'—C4'—C5'	−174.0 (2)
C2—C3—C4—C5	−56.7 (3)	C2'—C3'—C4'—C5'	−53.5 (3)
C3—C4—C5—C6	−170.9 (2)	C3'—C4'—C5'—C6'	−174.9 (3)
C3—C4—C5—C10	59.1 (3)	C3'—C4'—C5'—C10'	56.6 (3)
C4—C5—C6—O2	56.2 (3)	C4'—C5'—C6'—O2'	56.8 (3)
C10—C5—C6—O2	−174.9 (2)	C10'—C5'—C6'—O2'	−175.9 (2)
C4—C5—C6—C7	174.9 (2)	C4'—C5'—C6'—C7'	177.6 (3)
C10—C5—C6—C7	−56.3 (3)	C10'—C5'—C6'—C7'	−55.0 (3)
O2—C6—C7—C8	174.3 (3)	O2'—C6'—C7'—C8'	171.2 (2)
C5—C6—C7—C8	53.8 (3)	C5'—C6'—C7'—C8'	52.0 (3)
C6—C7—C8—C9	−54.6 (3)	C6'—C7'—C8'—C9'	−54.0 (3)
C6—C7—C8—C14	−175.2 (3)	C6'—C7'—C8'—C14'	−174.5 (2)
C7—C8—C9—C11	−172.1 (3)	C7'—C8'—C9'—C11'	−170.3 (2)
C14—C8—C9—C11	−44.3 (3)	C14'—C8'—C9'—C11'	−41.7 (3)
C7—C8—C9—C10	57.5 (3)	C7'—C8'—C9'—C10'	59.5 (3)
C14—C8—C9—C10	−174.7 (2)	C14'—C8'—C9'—C10'	−171.8 (2)
C8—C9—C10—C25	66.8 (3)	C2'—C1'—C10'—C25'	−64.8 (3)
C11—C9—C10—C25	−53.7 (3)	C2'—C1'—C10'—C9'	172.9 (2)
C8—C9—C10—C1	−171.8 (2)	C2'—C1'—C10'—C5'	58.1 (3)
C11—C9—C10—C1	67.7 (3)	C8'—C9'—C10'—C1'	−174.4 (2)
C8—C9—C10—C5	−55.3 (3)	C11'—C9'—C10'—C1'	64.9 (3)
C11—C9—C10—C5	−175.9 (3)	C8'—C9'—C10'—C25'	64.7 (3)
C2—C1—C10—C9	170.5 (2)	C11'—C9'—C10'—C25'	−55.9 (3)
C2—C1—C10—C25	−67.2 (3)	C8'—C9'—C10'—C5'	−58.7 (3)
C2—C1—C10—C5	54.6 (3)	C11'—C9'—C10'—C5'	−179.3 (2)
C6—C5—C10—C9	55.3 (3)	C4'—C5'—C10'—C1'	−57.9 (3)
C4—C5—C10—C9	−175.2 (2)	C6'—C5'—C10'—C1'	173.9 (3)
C6—C5—C10—C25	−66.3 (3)	C4'—C5'—C10'—C25'	62.5 (3)
C4—C5—C10—C25	63.3 (3)	C6'—C5'—C10'—C25'	−65.8 (3)
C6—C5—C10—C1	173.6 (2)	C4'—C5'—C10'—C9'	−175.2 (2)
C4—C5—C10—C1	−56.9 (3)	C6'—C5'—C10'—C9'	56.5 (3)
C8—C9—C11—C12	37.4 (3)	C8'—C9'—C11'—C12'	42.4 (3)
C10—C9—C11—C12	163.4 (2)	C10'—C9'—C11'—C12'	168.2 (2)
C9—C11—C12—C13	−138.9 (2)	C9'—C11'—C12'—C13'	−151.6 (2)
C9—C11—C12—C14	−17.1 (3)	C9'—C11'—C12'—C14'	−27.1 (3)
C11—C12—C13—C18	−60.0 (3)	C11'—C12'—C13'—C18'	−62.6 (3)
C14—C12—C13—C18	−179.0 (2)	C14'—C12'—C13'—C18'	176.4 (2)
C11—C12—C13—C17	177.5 (2)	C11'—C12'—C13'—C17'	173.9 (2)
C14—C12—C13—C17	58.6 (3)	C14'—C12'—C13'—C17'	52.9 (3)
C9—C8—C14—C15	156.6 (3)	C7'—C8'—C14'—C15'	−88.7 (3)
C7—C8—C14—C15	−78.9 (4)	C9'—C8'—C14'—C15'	147.4 (3)
C9—C8—C14—C12	33.4 (3)	C7'—C8'—C14'—C12'	148.5 (3)
C7—C8—C14—C12	157.9 (3)	C9'—C8'—C14'—C12'	24.5 (3)
C13—C12—C14—C8	113.7 (3)	C13'—C12'—C14'—C15'	3.3 (4)
C11—C12—C14—C8	−9.8 (3)	C11'—C12'—C14'—C15'	−122.5 (3)
C13—C12—C14—C15	−10.0 (4)	C13'—C12'—C14'—C8'	127.5 (2)
C11—C12—C14—C15	−133.5 (3)	C11'—C12'—C14'—C8'	1.7 (3)
C8—C14—C15—C16	−164.6 (3)	C8'—C14'—C15'—C16'	−173.1 (3)
C12—C14—C15—C16	−46.3 (4)	C12'—C14'—C15'—C16'	−54.1 (4)
C14—C15—C16—C17	55.3 (4)	C14'—C15'—C16'—C17'	47.2 (4)
C18—C13—C17—C20	55.7 (3)	C18'—C13'—C17'—C20'	48.4 (3)
C12—C13—C17—C20	−179.6 (2)	C12'—C13'—C17'—C20'	172.6 (2)
C18—C13—C17—C16	−174.9 (2)	C18'—C13'—C17'—C16'	176.0 (3)
C12—C13—C17—C16	−50.2 (3)	C12'—C13'—C17'—C16'	−59.8 (3)
C15—C16—C17—C13	−6.6 (4)	C15'—C16'—C17'—C13'	9.7 (4)
C15—C16—C17—C20	120.8 (3)	C15'—C16'—C17'—C20'	136.1 (3)
C21—N1—C18—C13	60.2 (3)	C21'—N1'—C18'—C13'	64.3 (3)
C19—N1—C18—C13	−177.3 (3)	C19'—N1'—C18'—C13'	−169.7 (2)
C12—C13—C18—N1	176.5 (3)	C17'—C13'—C18'—N1'	−54.5 (3)
C17—C13—C18—N1	−59.9 (3)	C12'—C13'—C18'—N1'	−177.1 (2)
C18—N1—C19—C24	175.4 (3)	C18'—N1'—C19'—C24'	−178.4 (3)
C21—N1—C19—C24	−61.8 (4)	C21'—N1'—C19'—C24'	−55.2 (3)
C13—C17—C20—O3	67.4 (3)	C13'—C17'—C20'—O3'	68.3 (3)
C16—C17—C20—O3	−60.7 (3)	C16'—C17'—C20'—O3'	−58.2 (3)
C13—C17—C20—C26	−173.9 (2)	C13'—C17'—C20'—C26'	−175.7 (2)
C16—C17—C20—C26	57.9 (3)	C16'—C17'—C20'—C26'	57.8 (3)
C13—C17—C20—C21	−52.1 (3)	C13'—C17'—C20'—C21'	−52.0 (3)
C16—C17—C20—C21	179.8 (2)	C16'—C17'—C20'—C21'	−178.5 (2)
C18—N1—C21—C22	179.3 (2)	C18'—N1'—C21'—C22'	170.8 (2)
C19—N1—C21—C22	58.3 (3)	C19'—N1'—C21'—C22'	47.7 (3)
C18—N1—C21—C20	−55.5 (3)	C18'—N1'—C21'—C20'	−66.2 (3)
C19—N1—C21—C20	−176.5 (2)	C19'—N1'—C21'—C20'	170.8 (2)
O3—C20—C21—N1	−64.7 (3)	O3'—C20'—C21'—N1'	−60.4 (3)
C26—C20—C21—N1	173.8 (3)	C26'—C20'—C21'—N1'	−177.3 (2)
C17—C20—C21—N1	51.6 (3)	C17'—C20'—C21'—N1'	60.2 (3)
O3—C20—C21—C22	58.7 (3)	O3'—C20'—C21'—C22'	62.7 (3)
C26—C20—C21—C22	−62.7 (3)	C26'—C20'—C21'—C22'	−54.2 (3)
C17—C20—C21—C22	175.1 (2)	C17'—C20'—C21'—C22'	−176.8 (2)
N1—C21—C22—C23	−55.1 (3)	N1'—C21'—C22'—C23'	−48.2 (4)
C20—C21—C22—C23	179.6 (3)	C20'—C21'—C22'—C23'	−169.0 (3)
C21—C22—C23—C24	53.5 (4)	C21'—C22'—C23'—C24'	54.8 (4)
C22—C23—C24—C27	72.4 (3)	C22'—C23'—C24'—C27'	66.6 (4)
C22—C23—C24—C19	−52.5 (4)	C22'—C23'—C24'—C19'	−58.2 (4)
N1—C19—C24—C27	−67.7 (4)	N1'—C19'—C24'—C27'	−65.7 (4)
N1—C19—C24—C23	57.4 (4)	N1'—C19'—C24'—C23'	58.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3′^i	0.82	1.99	2.777 (3)	160
O2—H2···O1^ii	0.82	1.94	2.746 (3)	168
O3—H3···O1′^iii	0.82	2.16	2.950 (3)	163
O1′—H1′···O1W	0.82	1.94	2.743 (4)	165
O2′—H2′···O3	0.82	2.36	3.097 (3)	151
O3′—H3′···O4	0.82	2.06	2.785 (4)	147
O4—H4···O2^i	0.82	1.94	2.758 (3)	174
O1W—H51···O1′^iv	0.86 (2)	2.18 (2)	3.025 (4)	167 (4)
O1W—H52···O2′^v	0.86 (2)	1.96 (2)	2.802 (4)	166 (5)

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z+1; (iii) x, y−1, z; (iv) −x+1, y−1/2, −z; (v) −x+1, y+1/2, −z.