Pseudophomins A and B, a class of cyclic lipodepsipeptides isolated from a Pseudomonas species

The crystal structures of pseudophomins A and B, with primary structures β-hydroxy­decanoyl–L-Leu–D-Glu–D-allo-Thr–D-Ile–D-Leu–D-Ser–L-Leu–D-Ser–L-Ile monohydrate, C₅₅H₉₇N₉O₁₆·H₂O, and β-hydroxy­dodecanoyl–L-Leu–D-Glu–D-allo-Thr–D-Ile–D-Leu–D-Ser–L-Leu–D-Ser–L-Ile monohydrate, C₅₇H₁₀₁N₉O₁₆·H₂O, new cyclic lipodepsipeptides isolated from Pseudomonas fluorescens strain BRG100, have been solved. The absolute configuration of pseudophomin A has been determined from anomalous dispersion and the stereochemistry of the β-hydroxy acid group is R.

S1. Comment

As a result of their general ability to produce potent antifungal and herbicidal metabolites, bacteria of the genus Pseudomonas comprise a large group of potential biocontrol agents (Balkovec, 1994; Dowling & O'Gara, 1994; Faull & Powell, 1995). Microorganisms, such as soil bacteria, can be used for the biological control of weeds and plant pathogens to avoid the continuous use of chemical herbicides and fungicides. However, the successful application of such agents presupposes a good understanding of their chemistry and mechanism of action. Integrated in a program to discover and apply new biological control agents, we investigated the production of antifungal and herbicidal metabolites by the bacterium P. fluorescens strain BRG100. We established that the major metabolites, named pseudophomins A, (I), and B, (II), are a pair of new cyclic depsipeptides active against some plant pathogens. The chemical structure of these compounds was established by a combination of spectroscopic techniques, chemical derivatization and degradation, and X-ray crystallography. We describe here the crystal structure determination of (I) and (II).

X-ray crystallography allowed us to assign the following primary structure to the peptide moiety, i.e. Leu-Glu-allo-Thr-Ile-Leu-Ser-Leu-Ser-Ile, with the terminal carboxy group closing a macrocyclic ring on the hydroxy group of the allo-threonine residue. The N-terminus is, in turn, acylated by 3-hydroxydecanoate in pseudophomin A and by 3-hydroxydodecanoate in pseudophomin B. The configuration of ten acentric centers in the ring and lipid side chain are given in the Abstract in terms of D and L nomenclature. The configurations of all 13 acentric sites are given in R/S nomenclature in the Scheme above.

The few crystal structures of cyclic lipodepsipeptides determined to date include WLIP (Han et al., 1992), tensin (Henriksen et al., 2000), and amphisin (Sørensen et al., 2001). A literature search showed that pseudophomin A is a diastereomer of massetolide A and pseudophomin B is a diastereomer of massetolide C (Gerard et al., 1997). Interestingly, the chemical structure of pseudophomin A is very similar to that of WLIP, except for the D-Ile-4 residue, which in WLIP is replaced with a D-Val residue (Mortishire-Smith et al., 1991; Han et al., 1992). Furthermore, pseudophomin A has the same absolute configuration of each stereogenic center identical to WLIP (Bateman et al., 1990; Baldwin et al., 1990; Abraham & Podell, 1981).

Because (I) and (II) are produced in the same bacteria and possess almost identical sequences of amino acids, we have presumed that they must have the same stereochemistry. Thus, for pseudophomin B, the primary structure is β-hydroxydodecanoyl-L-Leu-D-Glu-D-allo-Thr-D-Ile-D-Leu-D-Ser-L-Leu-D-Ser-L-Ile. The superimposition of all atoms of (II), except the disordered regions, but including the solvent water molecule on the equivalent atoms of (I), using the program PROFIT (Smith, 1983), gave an r.m.s. deviation of 0.225 Å, with the largest deviation being 0.378 Å for C5. When the superposition was limited to the backbone atoms of (II) starting at atom O3' and including the O atoms in the side chains and the solvent water molecule, the r.m.s. deviation was 0.070 Å, with the largest deviation being 0.225 Å for the solvent water molecule. Examination of the ellipsoid plots and coordinates reported for WLIP (Han et al., 1992) indicated that the authors had deposited the mirror-image coordinates of the reported isomer and used these coordinates to draw the diagrams. The coordinates of WLIP were inverted to fit the structure to the reported stereochemistry. The superimposition of the inverted coordinates of the WLIP atoms, including the solvent water molecule, on the backbone atoms of (I) (leaving out the methyl group which is not in WLIP) using PROFIT gave an r.m.s. deviation of 0.042 Å, with the largest deviation being 0.171 Å. When the comparison was limited to the backbone plus side chain O atoms and the water molecule, the r.m.s. deviation was 0.027 Å, with the maximum deviation being 0.150 Å for atom O12B.

The structures of (I) and (II) are shown in the same orientation if Figs. 1 and 2, respectively.. A stereoview of (I) in the same orientation is shown in Fig. 3. Compounds (I), (II) and WLIP are isostructural, with the same space group and very similar cell dimensions. With the remarkable similarities in the structures, it is not suprizing that the hydrogen-bonding schemes are essentially identical for (I), (II) and WLIP. 17 separate hydrogen bonds (both intermolecular and intramolecular) were identified per asymmetric unit in (I) and (II), and are described in Tables 3 and 4, respectively. Only 11 hydrogen bonds per asymmetric unit were identified in WLIP (Han et al., 1992), but these authors limited their list to D···A distances of less than 3 Å. They also included two hydrogen bonds with bond angles of less than 100° that we have not selected.

The crystal structure of (I) showed a solvent accessible void of about 35 ų. In the structures of (I) and (II), there is no evidence of electron density from further solvent water molecules. The void volume is smaller than required for a water molecule (40 ų according to checkCIF). It is likely that the shape of the void is not consistent with the shape required by a water molecule. There was a low-occupancy water molecule reported by Han et al. (1992) in WLIP. The crystallization conditions may have also reduced the ability of a water molecule to fill the void in (I) and (II).

S2. Experimental

Pseudophomins A and B were bioassay-guided isolated from EtOAc extracts obtained from culture supernatants of P. fluorescens strain BRG100, following multiple column chromatography utilizing both normal and reverse-phase silica gel. Pseudophomin A was crystallized twice from dichloromethane–methanol (10:90), whereas pseudophomin B was crystallized from aqueous acetonitrile. The specific optical rotations at 299 K and λ = 589 nm for the two lipodepsipeptides in ethanol were found to be [α]^D = -23 for (I) and [α]^D = -15 for (II).

S3. Refinement

All H atoms were placed in calculated positions on the corresponding atoms (C—H = 0.99 Å on aliphatic C atoms, 0.95 Å on aromatic C atoms, 0.84 Å on sp² N atoms, and 0.85 Å on O atoms). The U_iso value of each H atom was assigned as equal to 1.2 times the U_eq of the attached atom. Methyl groups were staggered relative to the bonds of the attached atom. The H atoms on the solvent water molecules (O99) for (I) and (II) were constrained to make O—H distances 0.85 Å and H···H distances 1.34 Å. U_iso values for the water H atoms were allowed to refine for (I) and were set to 1.2U_eq of the water O atom for (II). For (I), the TWIN and BASF commands were used in the refinement to determine the Flack parameter (Flack, 1983; Flack & Bernardinelli, 1999, 2000), whose value of 0.02 (9) indicated that the correct configuration had been assigned. The refinement of (II) showed two regions of disorder. The last six C atoms of the lipid chain are disordered and L-ILe-9 is also disordered. The lipid region disorder was modeled by three chains having isotropic displacement parameters and riding H atoms. The isoleucine was modeled with two separate isoleucine units modeled with isotropic displacement parameters and riding H atoms. The methyl group of each ethyl unit on the two Ile components were each modeled with two disordered methyl positions. The TWIN and BASF commands were used in the refinement to determine the Flack parameter (Flack, 1983; Flack & Bernardinelli, 1999, 2000), which was found to be 0.10 (17); the s.u. value is too large to give certainty in the determination of the absolute configuration. Since the two molecules have similar specific optical rotations and come from the same biological source, it is probable that (I) and (II) have the same absolute configuration.

Computing details

Data collection: COLLECT (Nonius, 2000) for (I); SMART (Bruker, 1997) for (II). Cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997) for (I); SMART for (II). Data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK for (I); SAINT (Bruker, 1997) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: Xtal3.7 (Hall et al., 2000) for (I); Xtal3.7 (Hall et al., 1997) for (II). For both compounds, software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A general view (Hall et al., 2000) of pseudophomin A with non-H-atom displacement ellipsoids drawn at the 50% probability level. For clarity, the H atoms have been omitted.
	Fig. 2. A general view (Hall et al., 2000) of view of pseudophomin B with non-H-atom displacement ellipsoids drawn at the 50% probability level. For clarity, the H atoms have been omitted. In the disordered parts of the molecule, the segment with the largest population parameter is displayed.
	Fig. 3. A stereoview of pseudophomin A (Hall et al., 2000).

(I) β-hydroxydecanoyl-L-Leu-D-Glu-D-allo-Thr-D-Ile-D-Leu-D-Ser-L-Leu- D-Ser-L-Ile

Crystal data

C55H97N9O16·H2O	F(000) = 2512
Mr = 1158.43	Dx = 1.187 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.541780 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6097 reflections
a = 14.139 (1) Å	θ = 3.0–65.1°
b = 18.739 (1) Å	µ = 0.72 mm^−1
c = 24.473 (2) Å	T = 100 K
V = 6484.1 (8) Å^3	Block, colourless
Z = 4	0.22 × 0.17 × 0.15 mm

Data collection

KappaCCD2000 diffractometer	11039 independent reflections
Radiation source: rotating anode	10778 reflections with I > 2σ(I)
Graded mirror monochromator	Rint = 0.050
Detector resolution: 14 pixels mm^-1	θmax = 65.7°, θmin = 3.0°
Nonius CCD scans	h = −16→16
Absorption correction: multi-scan (Otwinowski & Minor, 1997)	k = −21→22
Tmin = 0.857, Tmax = 0.899	l = −28→28
61093 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 1.1181P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.092	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.30 e Å^−3
11039 reflections	Δρmin = −0.26 e Å^−3
742 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.00210 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (9)

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 > 2σ(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.

The structures were solved using direct methods (SHELX97) (Sheldrick, 1997) and subsequent difference Fourier synthesis and refined by full-matrix least squares (SHELXL97) (Sheldrick, 1997).

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

	x	y	z	Uiso*/Ueq
O7	0.41165 (8)	0.40811 (6)	0.86525 (4)	0.0238 (2)
O12A	0.26879 (11)	0.51057 (8)	1.12311 (5)	0.0464 (4)
O12B	0.37356 (13)	0.59864 (10)	1.11584 (6)	0.0594 (5)
H12B	0.3637	0.6024	1.1496	0.089*
O13	0.17486 (8)	0.41966 (6)	0.90575 (4)	0.0259 (2)
O16	0.17463 (8)	0.15467 (6)	0.90231 (4)	0.0247 (2)
O18	0.12767 (8)	0.27087 (6)	0.82599 (4)	0.0263 (2)
O25	0.16431 (8)	0.37178 (6)	0.71822 (4)	0.0267 (2)
O32	0.04173 (8)	0.53353 (6)	0.74744 (5)	0.0278 (3)
O35	−0.02491 (8)	0.38981 (7)	0.91446 (5)	0.0298 (3)
H35	−0.0548	0.3521	0.9076	0.045*
O36	−0.17833 (8)	0.37711 (7)	0.80273 (5)	0.0361 (3)
O43	−0.19064 (8)	0.19475 (6)	0.76942 (5)	0.0279 (3)
O46	−0.08400 (10)	0.25503 (7)	0.92848 (5)	0.0346 (3)
H46	−0.0627	0.2408	0.9586	0.052*
O47	−0.01327 (9)	0.10162 (7)	0.93939 (5)	0.0318 (3)
O54	0.26471 (10)	0.06041 (7)	0.92450 (6)	0.0422 (3)
O1'	0.45546 (8)	0.27033 (6)	0.96056 (4)	0.0258 (2)
O3'	0.58004 (8)	0.13547 (6)	0.98850 (4)	0.0271 (2)
H3'O	0.5722	0.1055	1.0136	0.041*
O99	0.66330 (9)	0.28934 (7)	0.79984 (6)	0.0373 (3)
H99A	0.6906	0.2512	0.7903	0.069 (9)*
H99B	0.7077	0.3209	0.7999	0.072 (9)*
N1	0.56162 (9)	0.30778 (7)	0.89846 (5)	0.0235 (3)
H1	0.5991	0.2972	0.8709	0.028*
N8	0.40951 (9)	0.42997 (7)	0.95610 (5)	0.0218 (3)
H8	0.4409	0.4296	0.9872	0.026*
N14	0.26671 (9)	0.33026 (7)	0.93716 (5)	0.0218 (3)
H14	0.3175	0.3176	0.9555	0.026*
N19	0.28428 (9)	0.29287 (7)	0.82590 (5)	0.0216 (3)
H19	0.3377	0.2935	0.8443	0.026*
N26	0.24452 (9)	0.43058 (7)	0.78357 (5)	0.0228 (3)
H26A	0.2848	0.4281	0.8109	0.027*
N33	0.05556 (9)	0.45416 (7)	0.81669 (5)	0.0229 (3)
H33	0.0944	0.4291	0.8372	0.028*
N37	−0.03725 (10)	0.34152 (7)	0.76905 (5)	0.0244 (3)
H37	0.0238	0.3504	0.7676	0.029*
N44	−0.05827 (10)	0.20276 (8)	0.82083 (5)	0.0256 (3)
H44	0.0007	0.2175	0.8224	0.031*
N48	0.04222 (9)	0.08131 (7)	0.85434 (5)	0.0251 (3)
H48	0.0327	0.0870	0.8191	0.030*
C2	0.55314 (11)	0.38186 (9)	0.91677 (6)	0.0235 (3)
H2	0.5711	0.3847	0.9562	0.028*
C3	0.61857 (11)	0.43041 (9)	0.88376 (7)	0.0276 (4)
H3A	0.6843	0.4129	0.8875	0.033*
H3B	0.6011	0.4271	0.8447	0.033*
C4	0.61496 (13)	0.50858 (10)	0.90126 (7)	0.0319 (4)
H4	0.5474	0.5242	0.9002	0.038*
C5	0.65141 (17)	0.52014 (12)	0.95920 (9)	0.0470 (5)
H5A	0.6487	0.5711	0.9682	0.071*
H5B	0.7170	0.5035	0.9617	0.071*
H5C	0.6120	0.4933	0.9850	0.071*
C6	0.67003 (14)	0.55450 (11)	0.86077 (9)	0.0429 (5)
H6A	0.6441	0.5478	0.8240	0.064*
H6B	0.7368	0.5404	0.8611	0.064*
H6C	0.6645	0.6048	0.8712	0.064*
C7	0.45124 (11)	0.40735 (8)	0.91015 (6)	0.0214 (3)
C9	0.31213 (11)	0.45512 (9)	0.95456 (6)	0.0218 (3)
H9	0.3100	0.4985	0.9308	0.026*
C10	0.27874 (11)	0.47651 (9)	1.01168 (6)	0.0236 (3)
H10A	0.2119	0.4920	1.0097	0.028*
H10B	0.2820	0.4344	1.0361	0.028*
C11	0.33803 (12)	0.53647 (9)	1.03591 (7)	0.0277 (3)
H11A	0.4058	0.5260	1.0297	0.033*
H11B	0.3229	0.5816	1.0168	0.033*
C12	0.32124 (13)	0.54604 (10)	1.09582 (7)	0.0312 (4)
C13	0.24559 (11)	0.39973 (9)	0.93012 (6)	0.0213 (3)
C15	0.20429 (11)	0.27651 (9)	0.91396 (6)	0.0220 (3)
H15	0.1390	0.2852	0.9281	0.026*
C16	0.23559 (11)	0.20260 (9)	0.93281 (6)	0.0239 (3)
H16	0.3033	0.1942	0.9230	0.029*
C17	0.22100 (15)	0.19265 (11)	0.99370 (7)	0.0370 (4)
H17A	0.2411	0.1445	1.0043	0.055*
H17B	0.1539	0.1989	1.0025	0.055*
H17C	0.2586	0.2280	1.0137	0.055*
C18	0.20117 (11)	0.28034 (8)	0.85143 (6)	0.0222 (3)
C20	0.28334 (11)	0.30540 (9)	0.76704 (6)	0.0231 (3)
H20	0.2514	0.2638	0.7492	0.028*
C21	0.38506 (11)	0.31005 (10)	0.74442 (7)	0.0276 (4)
H21	0.4199	0.3465	0.7664	0.033*
C22	0.38600 (13)	0.33473 (10)	0.68454 (7)	0.0324 (4)
H22A	0.3558	0.3823	0.6825	0.039*
H22B	0.4526	0.3403	0.6728	0.039*
C23	0.43549 (13)	0.23889 (11)	0.75186 (8)	0.0364 (4)
H23A	0.5000	0.2425	0.7375	0.055*
H23B	0.4011	0.2016	0.7320	0.055*
H23C	0.4377	0.2268	0.7908	0.055*
C24	0.33634 (16)	0.28522 (12)	0.64428 (8)	0.0439 (5)
H24A	0.2699	0.2797	0.6550	0.066*
H24B	0.3674	0.2385	0.6445	0.066*
H24C	0.3397	0.3057	0.6075	0.066*
C25	0.22585 (11)	0.37212 (9)	0.75426 (6)	0.0227 (3)
C27	0.19898 (11)	0.49864 (9)	0.77089 (6)	0.0237 (3)
H27	0.2134	0.5105	0.7319	0.028*
C28	0.24115 (12)	0.55767 (9)	0.80683 (7)	0.0260 (3)
H28A	0.2098	0.6033	0.7975	0.031*
H28B	0.2261	0.5469	0.8455	0.031*
C29	0.34836 (12)	0.56774 (9)	0.80164 (8)	0.0316 (4)
H29	0.3800	0.5239	0.8161	0.038*
C30	0.38050 (13)	0.57862 (11)	0.74248 (8)	0.0382 (4)
H30A	0.3602	0.5379	0.7203	0.057*
H30B	0.4496	0.5825	0.7413	0.057*
H30C	0.3523	0.6225	0.7280	0.057*
C31	0.37798 (14)	0.63091 (11)	0.83719 (9)	0.0425 (5)
H31A	0.3577	0.6226	0.8749	0.064*
H31B	0.3484	0.6746	0.8233	0.064*
H31C	0.4469	0.6361	0.8361	0.064*
C32	0.09130 (11)	0.49622 (9)	0.77733 (6)	0.0234 (3)
C34	−0.04583 (11)	0.44907 (9)	0.82614 (6)	0.0235 (3)
H34	−0.0752	0.4933	0.8108	0.028*
C35	−0.06828 (12)	0.44767 (9)	0.88728 (6)	0.0261 (3)
H35A	−0.0466	0.4929	0.9041	0.031*
H35B	−0.1376	0.4446	0.8923	0.031*
C36	−0.09242 (11)	0.38542 (9)	0.79772 (6)	0.0246 (3)
C38	−0.07388 (11)	0.27925 (9)	0.73982 (7)	0.0246 (3)
H38	−0.1267	0.2956	0.7157	0.029*
C39	0.00528 (12)	0.25073 (9)	0.70318 (7)	0.0270 (3)
H39A	0.0606	0.2397	0.7265	0.032*
H39B	0.0244	0.2892	0.6777	0.032*
C40	−0.01852 (13)	0.18423 (9)	0.66949 (7)	0.0295 (4)
H40	−0.0421	0.1464	0.6949	0.035*
C41	−0.09467 (14)	0.19853 (11)	0.62687 (8)	0.0379 (4)
H41A	−0.1523	0.2154	0.6450	0.057*
H41B	−0.1084	0.1544	0.6069	0.057*
H41C	−0.0723	0.2350	0.6012	0.057*
C42	0.07194 (14)	0.15713 (11)	0.64236 (8)	0.0377 (4)
H42A	0.0575	0.1148	0.6204	0.057*
H42B	0.1183	0.1447	0.6705	0.057*
H42C	0.0980	0.1945	0.6187	0.057*
C43	−0.11310 (11)	0.22224 (9)	0.77860 (6)	0.0248 (3)
C45	−0.09596 (12)	0.15722 (9)	0.86412 (7)	0.0268 (3)
H45	−0.1439	0.1247	0.8473	0.032*
C46	−0.14605 (13)	0.20249 (10)	0.90648 (7)	0.0320 (4)
H46A	−0.2012	0.2263	0.8895	0.038*
H46B	−0.1695	0.1715	0.9363	0.038*
C47	−0.01840 (11)	0.11093 (9)	0.88942 (7)	0.0255 (3)
C49	0.12338 (12)	0.03995 (9)	0.87233 (7)	0.0277 (3)
H49	0.1000	0.0024	0.8980	0.033*
C50	0.16721 (14)	0.00199 (11)	0.82259 (8)	0.0395 (4)
H50	0.1140	−0.0223	0.8031	0.047*
C51	0.23832 (18)	−0.05636 (14)	0.83769 (10)	0.0573 (6)
H51A	0.2570	−0.0817	0.8039	0.069*
H51B	0.2958	−0.0333	0.8526	0.069*
C52	0.20988 (16)	0.05409 (15)	0.78259 (9)	0.0544 (6)
H52A	0.2366	0.0279	0.7516	0.082*
H52B	0.2600	0.0814	0.8007	0.082*
H52C	0.1608	0.0868	0.7695	0.082*
C53	0.2038 (2)	−0.11096 (13)	0.87866 (13)	0.0709 (8)
H53A	0.2541	−0.1457	0.8858	0.106*
H53B	0.1483	−0.1356	0.8639	0.106*
H53C	0.1868	−0.0869	0.9128	0.106*
C54	0.19588 (12)	0.08497 (9)	0.90285 (7)	0.0282 (4)
C1'	0.51274 (11)	0.25635 (9)	0.92331 (6)	0.0233 (3)
C2'	0.52773 (12)	0.18058 (9)	0.90328 (7)	0.0267 (3)
H2'A	0.5935	0.1757	0.8899	0.032*
H2'B	0.4848	0.1714	0.8721	0.032*
C3'	0.51000 (12)	0.12489 (9)	0.94725 (6)	0.0255 (3)
H3'	0.4460	0.1331	0.9635	0.031*
C4'	0.51365 (12)	0.04984 (9)	0.92367 (7)	0.0276 (4)
H4'A	0.5788	0.0398	0.9110	0.033*
H4'B	0.4713	0.0473	0.8915	0.033*
C5'	0.48438 (13)	−0.00734 (9)	0.96472 (7)	0.0299 (4)
H5'A	0.5285	−0.0063	0.9961	0.036*
H5'B	0.4203	0.0037	0.9786	0.036*
C6'	0.48419 (15)	−0.08196 (10)	0.94000 (8)	0.0365 (4)
H6'A	0.5498	−0.0952	0.9302	0.044*
H6'B	0.4465	−0.0813	0.9059	0.044*
C7'	0.44387 (16)	−0.13861 (10)	0.97830 (8)	0.0406 (5)
H7'A	0.4825	−0.1399	1.0120	0.049*
H7'B	0.3788	−0.1247	0.9888	0.049*
C8'	0.44126 (19)	−0.21322 (11)	0.95347 (9)	0.0480 (5)
H8'A	0.4060	−0.2110	0.9185	0.058*
H8'B	0.5068	−0.2280	0.9450	0.058*
C9'	0.39618 (19)	−0.27004 (12)	0.98947 (10)	0.0513 (5)
H9'A	0.4072	−0.3175	0.9729	0.062*
H9'B	0.4272	−0.2695	1.0257	0.062*
C10'	0.2904 (2)	−0.25885 (15)	0.99687 (14)	0.0719 (8)
H10'A	0.2650	−0.2962	1.0208	0.108*
H10'B	0.2590	−0.2612	0.9612	0.108*
H10'C	0.2791	−0.2120	1.0134	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0237 (5)	0.0275 (6)	0.0203 (5)	−0.0015 (4)	−0.0011 (4)	0.0009 (4)
O12A	0.0551 (9)	0.0566 (9)	0.0275 (6)	−0.0249 (7)	0.0085 (6)	−0.0087 (6)
O12B	0.0732 (11)	0.0719 (11)	0.0329 (7)	−0.0452 (9)	0.0204 (7)	−0.0265 (7)
O13	0.0227 (5)	0.0312 (6)	0.0238 (5)	0.0006 (5)	−0.0027 (5)	0.0008 (5)
O16	0.0259 (5)	0.0234 (6)	0.0247 (5)	−0.0018 (5)	−0.0034 (5)	−0.0002 (4)
O18	0.0235 (6)	0.0320 (6)	0.0235 (5)	−0.0044 (5)	−0.0023 (4)	0.0014 (5)
O25	0.0261 (6)	0.0321 (6)	0.0218 (5)	−0.0036 (5)	−0.0024 (5)	0.0032 (5)
O32	0.0261 (5)	0.0303 (6)	0.0272 (6)	0.0016 (5)	−0.0045 (5)	0.0058 (5)
O35	0.0286 (6)	0.0330 (6)	0.0279 (6)	−0.0050 (5)	−0.0040 (5)	0.0060 (5)
O36	0.0215 (6)	0.0417 (7)	0.0450 (7)	−0.0041 (5)	0.0026 (5)	−0.0127 (6)
O43	0.0226 (6)	0.0285 (6)	0.0327 (6)	−0.0034 (5)	−0.0022 (4)	−0.0047 (5)
O46	0.0532 (8)	0.0262 (6)	0.0245 (6)	−0.0029 (6)	−0.0007 (5)	0.0013 (5)
O47	0.0331 (6)	0.0409 (7)	0.0215 (6)	−0.0051 (5)	0.0042 (5)	0.0025 (5)
O54	0.0389 (7)	0.0329 (7)	0.0547 (8)	0.0033 (6)	−0.0189 (6)	0.0004 (6)
O1'	0.0259 (6)	0.0272 (6)	0.0243 (5)	0.0012 (5)	0.0009 (5)	0.0016 (5)
O3'	0.0273 (6)	0.0303 (6)	0.0237 (5)	−0.0020 (5)	−0.0047 (5)	0.0013 (5)
O99	0.0293 (7)	0.0371 (8)	0.0454 (7)	−0.0050 (6)	0.0109 (6)	−0.0100 (6)
N1	0.0225 (6)	0.0235 (7)	0.0246 (6)	0.0012 (5)	0.0024 (5)	−0.0006 (5)
N8	0.0209 (6)	0.0241 (7)	0.0204 (6)	0.0002 (5)	−0.0021 (5)	0.0000 (5)
N14	0.0197 (6)	0.0250 (7)	0.0208 (6)	−0.0014 (5)	−0.0018 (5)	0.0002 (5)
N19	0.0197 (6)	0.0257 (7)	0.0193 (6)	0.0005 (5)	−0.0017 (5)	0.0005 (5)
N26	0.0228 (6)	0.0252 (7)	0.0206 (6)	0.0018 (5)	−0.0022 (5)	0.0013 (5)
N33	0.0209 (6)	0.0253 (7)	0.0226 (6)	0.0013 (5)	−0.0023 (5)	0.0035 (5)
N37	0.0215 (6)	0.0257 (7)	0.0261 (7)	−0.0016 (5)	−0.0016 (5)	−0.0015 (5)
N44	0.0204 (6)	0.0310 (8)	0.0253 (7)	−0.0042 (6)	0.0007 (5)	0.0007 (6)
N48	0.0272 (7)	0.0284 (7)	0.0195 (6)	−0.0008 (6)	−0.0018 (5)	−0.0008 (5)
C2	0.0229 (8)	0.0240 (8)	0.0235 (7)	−0.0001 (6)	0.0002 (6)	−0.0004 (6)
C3	0.0215 (8)	0.0298 (9)	0.0314 (8)	−0.0003 (7)	0.0046 (6)	0.0005 (7)
C4	0.0291 (9)	0.0291 (9)	0.0376 (9)	−0.0007 (7)	0.0051 (7)	0.0008 (8)
C5	0.0567 (13)	0.0361 (11)	0.0483 (12)	−0.0133 (10)	−0.0020 (10)	−0.0081 (9)
C6	0.0384 (10)	0.0341 (10)	0.0563 (12)	−0.0037 (9)	0.0118 (9)	0.0061 (9)
C7	0.0220 (7)	0.0191 (7)	0.0231 (7)	−0.0019 (6)	0.0004 (6)	0.0029 (6)
C9	0.0205 (7)	0.0228 (8)	0.0219 (7)	0.0012 (6)	−0.0002 (6)	0.0016 (6)
C10	0.0240 (8)	0.0249 (8)	0.0219 (7)	−0.0003 (6)	0.0002 (6)	−0.0006 (6)
C11	0.0320 (9)	0.0275 (9)	0.0235 (8)	−0.0024 (7)	0.0026 (7)	−0.0033 (7)
C12	0.0322 (9)	0.0334 (9)	0.0280 (8)	−0.0039 (8)	0.0038 (7)	−0.0056 (7)
C13	0.0197 (7)	0.0273 (8)	0.0167 (7)	0.0010 (6)	0.0023 (6)	0.0022 (6)
C15	0.0186 (7)	0.0270 (8)	0.0205 (7)	−0.0037 (6)	0.0006 (6)	−0.0009 (6)
C16	0.0221 (8)	0.0257 (8)	0.0239 (8)	−0.0049 (6)	−0.0029 (6)	0.0016 (6)
C17	0.0496 (11)	0.0372 (10)	0.0241 (8)	−0.0143 (9)	−0.0048 (8)	0.0043 (7)
C18	0.0228 (8)	0.0210 (8)	0.0228 (7)	−0.0005 (6)	−0.0003 (6)	0.0006 (6)
C20	0.0249 (8)	0.0245 (8)	0.0199 (7)	−0.0013 (6)	0.0008 (6)	0.0001 (6)
C21	0.0249 (8)	0.0342 (9)	0.0237 (8)	−0.0002 (7)	0.0036 (6)	−0.0012 (7)
C22	0.0318 (9)	0.0380 (10)	0.0275 (8)	0.0012 (8)	0.0076 (7)	0.0038 (7)
C23	0.0319 (9)	0.0464 (11)	0.0308 (9)	0.0088 (8)	0.0033 (7)	0.0023 (8)
C24	0.0494 (11)	0.0556 (13)	0.0266 (9)	−0.0024 (10)	0.0033 (8)	−0.0007 (9)
C25	0.0217 (7)	0.0284 (8)	0.0179 (7)	−0.0028 (6)	0.0039 (6)	0.0015 (6)
C27	0.0229 (8)	0.0244 (8)	0.0238 (8)	−0.0001 (6)	−0.0016 (6)	0.0044 (6)
C28	0.0268 (8)	0.0221 (8)	0.0289 (8)	−0.0007 (7)	−0.0030 (6)	0.0027 (6)
C29	0.0261 (8)	0.0271 (9)	0.0416 (10)	−0.0040 (7)	−0.0058 (7)	0.0069 (7)
C30	0.0250 (8)	0.0375 (10)	0.0523 (11)	−0.0020 (8)	0.0042 (8)	0.0005 (9)
C31	0.0363 (10)	0.0416 (11)	0.0497 (11)	−0.0124 (9)	−0.0069 (9)	0.0026 (9)
C32	0.0252 (8)	0.0233 (8)	0.0217 (7)	−0.0002 (7)	−0.0022 (6)	−0.0017 (6)
C34	0.0205 (7)	0.0253 (8)	0.0247 (8)	0.0005 (6)	−0.0022 (6)	0.0005 (6)
C35	0.0275 (8)	0.0269 (8)	0.0239 (8)	0.0006 (7)	0.0009 (6)	0.0012 (6)
C36	0.0242 (8)	0.0274 (8)	0.0223 (7)	−0.0018 (7)	−0.0015 (6)	0.0017 (6)
C38	0.0234 (8)	0.0252 (8)	0.0251 (8)	−0.0021 (6)	−0.0031 (6)	−0.0017 (7)
C39	0.0292 (8)	0.0282 (8)	0.0235 (7)	−0.0039 (7)	0.0016 (7)	−0.0003 (7)
C40	0.0369 (9)	0.0264 (9)	0.0251 (8)	−0.0031 (7)	0.0017 (7)	−0.0004 (7)
C41	0.0424 (10)	0.0426 (11)	0.0288 (9)	−0.0043 (9)	−0.0042 (8)	−0.0049 (8)
C42	0.0448 (10)	0.0343 (10)	0.0340 (9)	0.0012 (8)	0.0056 (8)	−0.0068 (8)
C43	0.0234 (8)	0.0265 (8)	0.0243 (8)	0.0017 (7)	0.0018 (6)	−0.0050 (7)
C45	0.0248 (8)	0.0295 (9)	0.0262 (8)	−0.0062 (7)	0.0030 (6)	−0.0014 (7)
C46	0.0359 (9)	0.0276 (9)	0.0324 (9)	−0.0016 (7)	0.0104 (7)	0.0011 (7)
C47	0.0253 (8)	0.0260 (8)	0.0251 (8)	−0.0085 (7)	0.0011 (6)	−0.0012 (6)
C49	0.0307 (8)	0.0255 (8)	0.0269 (8)	0.0000 (7)	−0.0029 (7)	0.0003 (7)
C50	0.0399 (10)	0.0440 (11)	0.0345 (10)	0.0101 (9)	−0.0050 (8)	−0.0107 (8)
C51	0.0588 (14)	0.0596 (15)	0.0536 (13)	0.0248 (12)	−0.0181 (11)	−0.0235 (11)
C52	0.0396 (11)	0.0902 (18)	0.0333 (10)	0.0098 (12)	0.0058 (9)	0.0007 (11)
C53	0.097 (2)	0.0351 (12)	0.0810 (18)	0.0176 (13)	−0.0269 (16)	−0.0088 (12)
C54	0.0301 (9)	0.0261 (9)	0.0285 (8)	0.0004 (7)	−0.0016 (7)	0.0035 (7)
C1'	0.0223 (7)	0.0272 (8)	0.0204 (7)	0.0008 (6)	−0.0042 (6)	0.0014 (6)
C2'	0.0308 (8)	0.0263 (9)	0.0228 (8)	0.0008 (7)	−0.0010 (7)	−0.0015 (7)
C3'	0.0249 (8)	0.0281 (9)	0.0236 (8)	0.0017 (7)	−0.0019 (6)	0.0014 (6)
C4'	0.0305 (8)	0.0270 (9)	0.0253 (8)	0.0008 (7)	−0.0018 (6)	0.0000 (7)
C5'	0.0329 (9)	0.0273 (9)	0.0294 (8)	−0.0023 (7)	−0.0005 (7)	0.0012 (7)
C6'	0.0474 (11)	0.0286 (10)	0.0335 (9)	0.0000 (8)	0.0026 (8)	0.0009 (8)
C7'	0.0546 (12)	0.0318 (10)	0.0356 (10)	−0.0052 (9)	0.0021 (9)	−0.0007 (8)
C8'	0.0672 (14)	0.0309 (10)	0.0460 (11)	−0.0058 (10)	0.0130 (11)	0.0000 (9)
C9'	0.0708 (15)	0.0339 (11)	0.0492 (12)	−0.0077 (10)	0.0083 (11)	0.0011 (9)
C10'	0.0774 (18)	0.0509 (15)	0.0875 (19)	−0.0132 (14)	0.0143 (16)	0.0134 (14)

Geometric parameters (Å, º)

O7—C7	1.2334 (19)	C22—H22B	0.9900
O12A—C12	1.199 (2)	C23—H23A	0.9800
O12B—C12	1.326 (2)	C23—H23B	0.9800
O12B—H12B	0.8400	C23—H23C	0.9800
O13—C13	1.2229 (19)	C24—H24A	0.9800
O16—C54	1.340 (2)	C24—H24B	0.9800
O16—C16	1.4514 (19)	C24—H24C	0.9800
O18—C18	1.224 (2)	C27—C32	1.531 (2)
O25—C25	1.2390 (19)	C27—C28	1.534 (2)
O32—C32	1.231 (2)	C27—H27	1.0000
O35—C35	1.412 (2)	C28—C29	1.533 (2)
O35—H35	0.8400	C28—H28A	0.9900
O36—C36	1.231 (2)	C28—H28B	0.9900
O43—C43	1.232 (2)	C29—C31	1.528 (3)
O46—C46	1.424 (2)	C29—C30	1.531 (3)
O46—H46	0.8400	C29—H29	1.0000
O47—C47	1.238 (2)	C30—H30A	0.9800
O54—C54	1.200 (2)	C30—H30B	0.9800
O1'—C1'	1.247 (2)	C30—H30C	0.9800
O3'—C3'	1.4279 (19)	C31—H31A	0.9800
O3'—H3'O	0.8400	C31—H31B	0.9800
O99—H99A	0.845	C31—H31C	0.9800
O99—H99B	0.863	C34—C36	1.530 (2)
N1—C1'	1.333 (2)	C34—C35	1.530 (2)
N1—C2	1.464 (2)	C34—H34	1.0000
N1—H1	0.8800	C35—H35A	0.9900
N8—C7	1.339 (2)	C35—H35B	0.9900
N8—C9	1.456 (2)	C38—C39	1.530 (2)
N8—H8	0.8800	C38—C43	1.533 (2)
N14—C13	1.347 (2)	C38—H38	1.0000
N14—C15	1.455 (2)	C39—C40	1.532 (2)
N14—H14	0.8800	C39—H39A	0.9900
N19—C18	1.351 (2)	C39—H39B	0.9900
N19—C20	1.4596 (19)	C40—C41	1.523 (3)
N19—H19	0.8800	C40—C42	1.528 (3)
N26—C25	1.336 (2)	C40—H40	1.0000
N26—C27	1.462 (2)	C41—H41A	0.9800
N26—H26A	0.8800	C41—H41B	0.9800
N33—C32	1.343 (2)	C41—H41C	0.9800
N33—C34	1.455 (2)	C42—H42A	0.9800
N33—H33	0.8800	C42—H42B	0.9800
N37—C36	1.333 (2)	C42—H42C	0.9800
N37—C38	1.463 (2)	C45—C46	1.515 (2)
N37—H37	0.8800	C45—C47	1.529 (2)
N44—C43	1.342 (2)	C45—H45	1.0000
N44—C45	1.461 (2)	C46—H46A	0.9900
N44—H44	0.8800	C46—H46B	0.9900
N48—C47	1.334 (2)	C49—C54	1.523 (2)
N48—C49	1.453 (2)	C49—C50	1.540 (2)
N48—H48	0.8800	C49—H49	1.0000
C2—C7	1.526 (2)	C50—C52	1.508 (3)
C2—C3	1.528 (2)	C50—C51	1.531 (3)
C2—H2	1.0000	C50—H50	1.0000
C3—C4	1.527 (2)	C51—C53	1.513 (4)
C3—H3A	0.9900	C51—H51A	0.9900
C3—H3B	0.9900	C51—H51B	0.9900
C4—C5	1.524 (3)	C52—H52A	0.9800
C4—C6	1.526 (3)	C52—H52B	0.9800
C4—H4	1.0000	C52—H52C	0.9800
C5—H5A	0.9800	C53—H53A	0.9800
C5—H5B	0.9800	C53—H53B	0.9800
C5—H5C	0.9800	C53—H53C	0.9800
C6—H6A	0.9800	C1'—C2'	1.517 (2)
C6—H6B	0.9800	C2'—C3'	1.520 (2)
C6—H6C	0.9800	C2'—H2'A	0.9900
C9—C13	1.523 (2)	C2'—H2'B	0.9900
C9—C10	1.529 (2)	C3'—C4'	1.521 (2)
C9—H9	1.0000	C3'—H3'	1.0000
C10—C11	1.522 (2)	C4'—C5'	1.526 (2)
C10—H10A	0.9900	C4'—H4'A	0.9900
C10—H10B	0.9900	C4'—H4'B	0.9900
C11—C12	1.496 (2)	C5'—C6'	1.524 (3)
C11—H11A	0.9900	C5'—H5'A	0.9900
C11—H11B	0.9900	C5'—H5'B	0.9900
C15—C16	1.525 (2)	C6'—C7'	1.527 (3)
C15—C18	1.533 (2)	C6'—H6'A	0.9900
C15—H15	1.0000	C6'—H6'B	0.9900
C16—C17	1.516 (2)	C7'—C8'	1.525 (3)
C16—H16	1.0000	C7'—H7'A	0.9900
C17—H17A	0.9800	C7'—H7'B	0.9900
C17—H17B	0.9800	C8'—C9'	1.522 (3)
C17—H17C	0.9800	C8'—H8'A	0.9900
C20—C25	1.524 (2)	C8'—H8'B	0.9900
C20—C21	1.544 (2)	C9'—C10'	1.521 (4)
C20—H20	1.0000	C9'—H9'A	0.9900
C21—C23	1.523 (3)	C9'—H9'B	0.9900
C21—C22	1.537 (2)	C10'—H10'A	0.9800
C21—H21	1.0000	C10'—H10'B	0.9800
C22—C24	1.524 (3)	C10'—H10'C	0.9800
C22—H22A	0.9900
C12—O12B—H12B	109.5	C29—C30—H30C	109.5
C54—O16—C16	117.71 (13)	H30A—C30—H30C	109.5
C35—O35—H35	109.5	H30B—C30—H30C	109.5
C46—O46—H46	109.5	C29—C31—H31A	109.5
C3'—O3'—H3'O	109.5	C29—C31—H31B	109.5
H99A—O99—H99B	104	H31A—C31—H31B	109.5
C1'—N1—C2	120.24 (13)	C29—C31—H31C	109.5
C1'—N1—H1	119.9	H31A—C31—H31C	109.5
C2—N1—H1	119.9	H31B—C31—H31C	109.5
C7—N8—C9	119.84 (13)	O32—C32—N33	123.04 (15)
C7—N8—H8	120.1	O32—C32—C27	119.22 (14)
C9—N8—H8	120.1	N33—C32—C27	117.72 (14)
C13—N14—C15	119.01 (13)	N33—C34—C36	113.77 (13)
C13—N14—H14	120.5	N33—C34—C35	111.15 (13)
C15—N14—H14	120.5	C36—C34—C35	110.00 (13)
C18—N19—C20	118.44 (13)	N33—C34—H34	107.2
C18—N19—H19	120.8	C36—C34—H34	107.2
C20—N19—H19	120.8	C35—C34—H34	107.2
C25—N26—C27	120.97 (13)	O35—C35—C34	112.56 (13)
C25—N26—H26A	119.5	O35—C35—H35A	109.1
C27—N26—H26A	119.5	C34—C35—H35A	109.1
C32—N33—C34	121.53 (13)	O35—C35—H35B	109.1
C32—N33—H33	119.2	C34—C35—H35B	109.1
C34—N33—H33	119.2	H35A—C35—H35B	107.8
C36—N37—C38	122.84 (13)	O36—C36—N37	123.49 (15)
C36—N37—H37	118.6	O36—C36—C34	118.58 (15)
C38—N37—H37	118.6	N37—C36—C34	117.93 (14)
C43—N44—C45	120.43 (14)	N37—C38—C39	107.82 (13)
C43—N44—H44	119.8	N37—C38—C43	112.40 (13)
C45—N44—H44	119.8	C39—C38—C43	112.58 (14)
C47—N48—C49	122.30 (13)	N37—C38—H38	108.0
C47—N48—H48	118.9	C39—C38—H38	108.0
C49—N48—H48	118.9	C43—C38—H38	108.0
N1—C2—C7	109.97 (13)	C38—C39—C40	116.03 (14)
N1—C2—C3	110.67 (13)	C38—C39—H39A	108.3
C7—C2—C3	109.21 (13)	C40—C39—H39A	108.3
N1—C2—H2	109.0	C38—C39—H39B	108.3
C7—C2—H2	109.0	C40—C39—H39B	108.3
C3—C2—H2	109.0	H39A—C39—H39B	107.4
C4—C3—C2	113.74 (14)	C41—C40—C42	110.65 (15)
C4—C3—H3A	108.8	C41—C40—C39	112.39 (15)
C2—C3—H3A	108.8	C42—C40—C39	108.69 (15)
C4—C3—H3B	108.8	C41—C40—H40	108.3
C2—C3—H3B	108.8	C42—C40—H40	108.3
H3A—C3—H3B	107.7	C39—C40—H40	108.3
C5—C4—C6	110.58 (16)	C40—C41—H41A	109.5
C5—C4—C3	112.70 (16)	C40—C41—H41B	109.5
C6—C4—C3	109.98 (15)	H41A—C41—H41B	109.5
C5—C4—H4	107.8	C40—C41—H41C	109.5
C6—C4—H4	107.8	H41A—C41—H41C	109.5
C3—C4—H4	107.8	H41B—C41—H41C	109.5
C4—C5—H5A	109.5	C40—C42—H42A	109.5
C4—C5—H5B	109.5	C40—C42—H42B	109.5
H5A—C5—H5B	109.5	H42A—C42—H42B	109.5
C4—C5—H5C	109.5	C40—C42—H42C	109.5
H5A—C5—H5C	109.5	H42A—C42—H42C	109.5
H5B—C5—H5C	109.5	H42B—C42—H42C	109.5
C4—C6—H6A	109.5	O43—C43—N44	122.73 (16)
C4—C6—H6B	109.5	O43—C43—C38	120.03 (14)
H6A—C6—H6B	109.5	N44—C43—C38	117.21 (14)
C4—C6—H6C	109.5	N44—C45—C46	109.85 (14)
H6A—C6—H6C	109.5	N44—C45—C47	111.31 (13)
H6B—C6—H6C	109.5	C46—C45—C47	112.07 (14)
O7—C7—N8	123.00 (14)	N44—C45—H45	107.8
O7—C7—C2	121.78 (14)	C46—C45—H45	107.8
N8—C7—C2	115.20 (13)	C47—C45—H45	107.8
N8—C9—C13	111.95 (13)	O46—C46—C45	110.96 (14)
N8—C9—C10	110.69 (12)	O46—C46—H46A	109.4
C13—C9—C10	110.30 (12)	C45—C46—H46A	109.4
N8—C9—H9	107.9	O46—C46—H46B	109.4
C13—C9—H9	107.9	C45—C46—H46B	109.4
C10—C9—H9	107.9	H46A—C46—H46B	108.0
C11—C10—C9	112.31 (13)	O47—C47—N48	122.66 (16)
C11—C10—H10A	109.1	O47—C47—C45	121.48 (15)
C9—C10—H10A	109.1	N48—C47—C45	115.86 (14)
C11—C10—H10B	109.1	N48—C49—C54	112.62 (14)
C9—C10—H10B	109.1	N48—C49—C50	108.95 (14)
H10A—C10—H10B	107.9	C54—C49—C50	111.87 (15)
C12—C11—C10	112.51 (14)	N48—C49—H49	107.7
C12—C11—H11A	109.1	C54—C49—H49	107.7
C10—C11—H11A	109.1	C50—C49—H49	107.7
C12—C11—H11B	109.1	C52—C50—C51	110.87 (19)
C10—C11—H11B	109.1	C52—C50—C49	112.03 (18)
H11A—C11—H11B	107.8	C51—C50—C49	113.79 (16)
O12A—C12—O12B	123.45 (16)	C52—C50—H50	106.5
O12A—C12—C11	125.28 (16)	C51—C50—H50	106.5
O12B—C12—C11	111.26 (15)	C49—C50—H50	106.5
O13—C13—N14	122.60 (15)	C53—C51—C50	115.6 (2)
O13—C13—C9	119.25 (14)	C53—C51—H51A	108.4
N14—C13—C9	118.14 (13)	C50—C51—H51A	108.4
N14—C15—C16	109.55 (12)	C53—C51—H51B	108.4
N14—C15—C18	112.01 (13)	C50—C51—H51B	108.4
C16—C15—C18	110.67 (13)	H51A—C51—H51B	107.5
N14—C15—H15	108.2	C50—C52—H52A	109.5
C16—C15—H15	108.2	C50—C52—H52B	109.5
C18—C15—H15	108.2	H52A—C52—H52B	109.5
O16—C16—C17	110.40 (13)	C50—C52—H52C	109.5
O16—C16—C15	103.54 (12)	H52A—C52—H52C	109.5
C17—C16—C15	111.69 (14)	H52B—C52—H52C	109.5
O16—C16—H16	110.3	C51—C53—H53A	109.5
C17—C16—H16	110.3	C51—C53—H53B	109.5
C15—C16—H16	110.3	H53A—C53—H53B	109.5
C16—C17—H17A	109.5	C51—C53—H53C	109.5
C16—C17—H17B	109.5	H53A—C53—H53C	109.5
H17A—C17—H17B	109.5	H53B—C53—H53C	109.5
C16—C17—H17C	109.5	O54—C54—O16	124.04 (16)
H17A—C17—H17C	109.5	O54—C54—C49	123.37 (16)
H17B—C17—H17C	109.5	O16—C54—C49	112.58 (14)
O18—C18—N19	121.89 (14)	O1'—C1'—N1	121.23 (15)
O18—C18—C15	121.69 (14)	O1'—C1'—C2'	121.56 (15)
N19—C18—C15	116.40 (13)	N1—C1'—C2'	117.19 (14)
N19—C20—C25	109.84 (13)	C1'—C2'—C3'	113.01 (13)
N19—C20—C21	110.77 (13)	C1'—C2'—H2'A	109.0
C25—C20—C21	112.16 (13)	C3'—C2'—H2'A	109.0
N19—C20—H20	108.0	C1'—C2'—H2'B	109.0
C25—C20—H20	108.0	C3'—C2'—H2'B	109.0
C21—C20—H20	108.0	H2'A—C2'—H2'B	107.8
C23—C21—C22	111.93 (14)	O3'—C3'—C2'	106.91 (13)
C23—C21—C20	110.12 (14)	O3'—C3'—C4'	111.90 (13)
C22—C21—C20	111.54 (14)	C2'—C3'—C4'	111.14 (13)
C23—C21—H21	107.7	O3'—C3'—H3'	108.9
C22—C21—H21	107.7	C2'—C3'—H3'	108.9
C20—C21—H21	107.7	C4'—C3'—H3'	108.9
C24—C22—C21	115.41 (16)	C3'—C4'—C5'	112.97 (14)
C24—C22—H22A	108.4	C3'—C4'—H4'A	109.0
C21—C22—H22A	108.4	C5'—C4'—H4'A	109.0
C24—C22—H22B	108.4	C3'—C4'—H4'B	109.0
C21—C22—H22B	108.4	C5'—C4'—H4'B	109.0
H22A—C22—H22B	107.5	H4'A—C4'—H4'B	107.8
C21—C23—H23A	109.5	C6'—C5'—C4'	112.55 (14)
C21—C23—H23B	109.5	C6'—C5'—H5'A	109.1
H23A—C23—H23B	109.5	C4'—C5'—H5'A	109.1
C21—C23—H23C	109.5	C6'—C5'—H5'B	109.1
H23A—C23—H23C	109.5	C4'—C5'—H5'B	109.1
H23B—C23—H23C	109.5	H5'A—C5'—H5'B	107.8
C22—C24—H24A	109.5	C5'—C6'—C7'	113.26 (15)
C22—C24—H24B	109.5	C5'—C6'—H6'A	108.9
H24A—C24—H24B	109.5	C7'—C6'—H6'A	108.9
C22—C24—H24C	109.5	C5'—C6'—H6'B	108.9
H24A—C24—H24C	109.5	C7'—C6'—H6'B	108.9
H24B—C24—H24C	109.5	H6'A—C6'—H6'B	107.7
O25—C25—N26	121.68 (15)	C8'—C7'—C6'	113.69 (16)
O25—C25—C20	121.10 (15)	C8'—C7'—H7'A	108.8
N26—C25—C20	117.22 (13)	C6'—C7'—H7'A	108.8
N26—C27—C32	112.97 (13)	C8'—C7'—H7'B	108.8
N26—C27—C28	109.65 (13)	C6'—C7'—H7'B	108.8
C32—C27—C28	110.41 (13)	H7'A—C7'—H7'B	107.7
N26—C27—H27	107.9	C9'—C8'—C7'	114.89 (18)
C32—C27—H27	107.9	C9'—C8'—H8'A	108.5
C28—C27—H27	107.9	C7'—C8'—H8'A	108.5
C29—C28—C27	115.19 (14)	C9'—C8'—H8'B	108.5
C29—C28—H28A	108.5	C7'—C8'—H8'B	108.5
C27—C28—H28A	108.5	H8'A—C8'—H8'B	107.5
C29—C28—H28B	108.5	C10'—C9'—C8'	112.6 (2)
C27—C28—H28B	108.5	C10'—C9'—H9'A	109.1
H28A—C28—H28B	107.5	C8'—C9'—H9'A	109.1
C31—C29—C30	110.73 (15)	C10'—C9'—H9'B	109.1
C31—C29—C28	108.62 (16)	C8'—C9'—H9'B	109.1
C30—C29—C28	112.84 (15)	H9'A—C9'—H9'B	107.8
C31—C29—H29	108.2	C9'—C10'—H10'A	109.5
C30—C29—H29	108.2	C9'—C10'—H10'B	109.5
C28—C29—H29	108.2	H10'A—C10'—H10'B	109.5
C29—C30—H30A	109.5	C9'—C10'—H10'C	109.5
C29—C30—H30B	109.5	H10'A—C10'—H10'C	109.5
H30A—C30—H30B	109.5	H10'B—C10'—H10'C	109.5
C1'—N1—C2—C7	−61.55 (18)	C28—C27—C32—O32	88.75 (17)
C1'—N1—C2—C3	177.70 (13)	N26—C27—C32—N33	33.5 (2)
N1—C2—C3—C4	−178.96 (14)	C28—C27—C32—N33	−89.72 (17)
C7—C2—C3—C4	59.83 (18)	C32—N33—C34—C36	96.08 (18)
C2—C3—C4—C5	64.9 (2)	C32—N33—C34—C35	−139.09 (15)
C2—C3—C4—C6	−171.18 (15)	N33—C34—C35—O35	−59.20 (18)
C9—N8—C7—O7	1.7 (2)	C36—C34—C35—O35	67.73 (17)
C9—N8—C7—C2	−179.68 (13)	C38—N37—C36—O36	0.9 (3)
N1—C2—C7—O7	−59.58 (19)	C38—N37—C36—C34	−179.54 (14)
C3—C2—C7—O7	62.05 (19)	N33—C34—C36—O36	−179.10 (15)
N1—C2—C7—N8	121.80 (14)	C35—C34—C36—O36	55.5 (2)
C3—C2—C7—N8	−116.57 (15)	N33—C34—C36—N37	1.4 (2)
C7—N8—C9—C13	55.19 (18)	C35—C34—C36—N37	−124.10 (15)
C7—N8—C9—C10	178.69 (14)	C36—N37—C38—C39	169.19 (14)
N8—C9—C10—C11	60.50 (18)	C36—N37—C38—C43	−66.14 (19)
C13—C9—C10—C11	−175.05 (13)	N37—C38—C39—C40	179.06 (13)
C9—C10—C11—C12	−166.52 (14)	C43—C38—C39—C40	54.51 (19)
C10—C11—C12—O12A	1.3 (3)	C38—C39—C40—C41	65.52 (19)
C10—C11—C12—O12B	−179.86 (16)	C38—C39—C40—C42	−171.67 (15)
C15—N14—C13—O13	1.3 (2)	C45—N44—C43—O43	−11.7 (2)
C15—N14—C13—C9	−179.75 (12)	C45—N44—C43—C38	170.56 (14)
N8—C9—C13—O13	−150.21 (14)	N37—C38—C43—O43	133.08 (15)
C10—C9—C13—O13	86.07 (17)	C39—C38—C43—O43	−104.91 (17)
N8—C9—C13—N14	30.85 (18)	N37—C38—C43—N44	−49.13 (19)
C10—C9—C13—N14	−92.87 (16)	C39—C38—C43—N44	72.87 (18)
C13—N14—C15—C16	−173.25 (13)	C43—N44—C45—C46	−85.23 (18)
C13—N14—C15—C18	63.55 (18)	C43—N44—C45—C47	150.04 (15)
C54—O16—C16—C17	−71.66 (18)	N44—C45—C46—O46	−57.21 (18)
C54—O16—C16—C15	168.66 (13)	C47—C45—C46—O46	67.07 (18)
N14—C15—C16—O16	−174.04 (12)	C49—N48—C47—O47	−4.6 (2)
C18—C15—C16—O16	−50.05 (15)	C49—N48—C47—C45	175.75 (14)
N14—C15—C16—C17	67.17 (16)	N44—C45—C47—O47	137.72 (16)
C18—C15—C16—C17	−168.84 (14)	C46—C45—C47—O47	14.3 (2)
C20—N19—C18—O18	8.8 (2)	N44—C45—C47—N48	−42.67 (19)
C20—N19—C18—C15	−172.85 (14)	C46—C45—C47—N48	−166.14 (14)
N14—C15—C18—O18	−141.45 (15)	C47—N48—C49—C54	−65.9 (2)
C16—C15—C18—O18	95.98 (18)	C47—N48—C49—C50	169.41 (16)
N14—C15—C18—N19	40.22 (19)	N48—C49—C50—C52	66.6 (2)
C16—C15—C18—N19	−82.35 (17)	C54—C49—C50—C52	−58.5 (2)
C18—N19—C20—C25	62.02 (18)	N48—C49—C50—C51	−166.61 (18)
C18—N19—C20—C21	−173.54 (14)	C54—C49—C50—C51	68.2 (2)
N19—C20—C21—C23	63.99 (18)	C52—C50—C51—C53	178.8 (2)
C25—C20—C21—C23	−172.90 (14)	C49—C50—C51—C53	51.4 (3)
N19—C20—C21—C22	−171.12 (14)	C16—O16—C54—O54	−4.1 (2)
C25—C20—C21—C22	−48.00 (19)	C16—O16—C54—C49	176.48 (13)
C23—C21—C22—C24	61.5 (2)	N48—C49—C54—O54	174.51 (16)
C20—C21—C22—C24	−62.4 (2)	C50—C49—C54—O54	−62.4 (2)
C27—N26—C25—O25	−5.7 (2)	N48—C49—C54—O16	−6.1 (2)
C27—N26—C25—C20	174.46 (13)	C50—C49—C54—O16	117.03 (16)
N19—C20—C25—O25	−131.43 (14)	C2—N1—C1'—O1'	3.7 (2)
C21—C20—C25—O25	104.94 (17)	C2—N1—C1'—C2'	−177.99 (14)
N19—C20—C25—N26	48.44 (18)	O1'—C1'—C2'—C3'	−29.1 (2)
C21—C20—C25—N26	−75.20 (17)	N1—C1'—C2'—C3'	152.54 (14)
C25—N26—C27—C32	62.35 (19)	C1'—C2'—C3'—O3'	−64.78 (17)
C25—N26—C27—C28	−174.03 (13)	C1'—C2'—C3'—C4'	172.83 (14)
N26—C27—C28—C29	57.82 (18)	O3'—C3'—C4'—C5'	67.61 (18)
C32—C27—C28—C29	−177.07 (14)	C2'—C3'—C4'—C5'	−172.95 (14)
C27—C28—C29—C31	176.68 (14)	C3'—C4'—C5'—C6'	177.53 (15)
C27—C28—C29—C30	53.5 (2)	C4'—C5'—C6'—C7'	−173.09 (16)
C34—N33—C32—O32	1.0 (2)	C5'—C6'—C7'—C8'	178.67 (18)
C34—N33—C32—C27	179.39 (14)	C6'—C7'—C8'—C9'	−176.6 (2)
N26—C27—C32—O32	−148.06 (14)	C7'—C8'—C9'—C10'	68.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12B—H12B···O25^i	0.84	1.79	2.6215 (17)	169
O35—H35···O46	0.84	1.93	2.6824 (17)	148
O46—H46···O1′^ii	0.84	2.01	2.8126 (16)	161
O3′—H3′O···O35^iii	0.84	2.23	2.8402 (16)	129
O3′—H3′O···O13^iii	0.84	2.49	3.0925 (16)	129
O99—H99A···O43^iv	0.85	2.05	2.8215 (17)	152
O99—H99B···O36^iv	0.86	1.93	2.7791 (18)	170
N1—H1···O99	0.88	1.97	2.8304 (18)	166
N8—H8···O47^iii	0.88	2.00	2.8432 (17)	161
N14—H14···O1′	0.88	2.15	2.9516 (18)	152
N19—H19···O7	0.88	2.44	2.9720 (17)	119
N26—H26A···O7	0.88	2.26	3.1237 (17)	166
N33—H33···O13	0.88	2.03	2.8307 (17)	150
N37—H37···O25	0.88	2.36	3.1608 (17)	151
N37—H37···O18	0.88	2.53	3.0220 (18)	116
N44—H44···O18	0.88	2.06	2.9252 (18)	169
N48—H48···O32^v	0.88	2.18	2.9008 (17)	139

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x−1/2, −y+1/2, −z+2; (iii) x+1/2, −y+1/2, −z+2; (iv) x+1, y, z; (v) −x, y−1/2, −z+3/2.

(II) β-hydroxydodecanoyl-L-Leu-D-Glu-D-allo-Thr-D-Ile-D-Leu-D-Ser-L-Leu- D-Ser-L-Ile

Crystal data

C57H101N9O16·H2O	F(000) = 2576
Mr = 1186.48	Dx = 1.194 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: p 2ac 2ab	Cell parameters from 5508 reflections
a = 14.245 (2) Å	θ = 3.0–65.1°
b = 18.870 (3) Å	µ = 0.72 mm^−1
c = 24.558 (4) Å	T = 100 K
V = 6601.7 (18) Å^3	Rod, colourless
Z = 4	0.46 × 0.04 × 0.04 mm

Data collection

Bruker SMART 6000 diffractometer	11751 independent reflections
Radiation source: rotating anode	9543 reflections with I > 2σ(I)
Confocal Max-Flux optics (greens) monochromator	Rint = 0.049
CCD scans	θmax = 71.3°, θmin = 3.0°
Absorption correction: multi-scan (Blessing, 1995)	h = −16→12
Tmin = 0.735, Tmax = 0.975	k = −22→22
30846 measured reflections	l = −30→28

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0655P)^2 + 1.5509P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.134	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.54 e Å^−3
11751 reflections	Δρmin = −0.31 e Å^−3
798 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
79 restraints	Extinction coefficient: 0.00052 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.10 (17)

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 > 2σ(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.

The molecule has two regions of disorder. The lipid chain is disordered from C7' to C12'. This disorder was modeled by three chains with isotropic thermal parameters and riding attached H atoms. The isoleucine attached at C49 is modeled with two separate isoleucine units modeled with isotropic thermal and riding attached H atoms, each isoleucine with two disordered methyl groups (C53, C53A on one isoleucine and C53B, C53C on the other).

The TWIN and BASF commands were used in the refinement to check the Flack Parameter.

The structures were solved using direct methods (SHELX97) (Sheldrick, 1997) and subsequent difference Fourier synthesis and refined by full-matrix least squares (SHELXL97) (Sheldrick, 1997).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O7	0.41800 (13)	0.40710 (10)	0.86422 (7)	0.0291 (4)
O12A	0.2711 (2)	0.51384 (15)	1.11902 (9)	0.0660 (8)
O12B	0.3664 (2)	0.60602 (14)	1.11242 (10)	0.0658 (8)
H12B	0.3522	0.6109	1.1454	0.099*
O13	0.18351 (13)	0.42247 (10)	0.90369 (8)	0.0314 (5)
O16	0.18245 (13)	0.15731 (9)	0.90711 (8)	0.0304 (4)
O18	0.13780 (13)	0.26639 (10)	0.82620 (7)	0.0303 (4)
O25	0.17492 (14)	0.36285 (10)	0.71467 (8)	0.0331 (5)
O32	0.04339 (13)	0.52155 (10)	0.74201 (8)	0.0346 (5)
O35	−0.01294 (14)	0.38268 (11)	0.91159 (8)	0.0363 (5)
H35	−0.0482	0.3470	0.9114	0.054*
O36	−0.16736 (15)	0.36483 (12)	0.80377 (10)	0.0475 (6)
O43	−0.17840 (14)	0.18628 (10)	0.77278 (8)	0.0357 (5)
O46	−0.07219 (16)	0.24991 (11)	0.92860 (8)	0.0417 (5)
H46	−0.0640	0.2437	0.9621	0.063*
O47	−0.00242 (15)	0.09530 (12)	0.94184 (8)	0.0407 (5)
O54	0.27816 (17)	0.06772 (12)	0.92937 (10)	0.0504 (6)
O1'	0.45712 (13)	0.26977 (10)	0.96031 (8)	0.0304 (4)
O3'	0.58564 (14)	0.13792 (10)	0.98978 (8)	0.0342 (5)
H3'O	0.5627	0.1330	1.0211	0.051*
O99	0.67557 (16)	0.27874 (13)	0.80563 (10)	0.0486 (6)
H99A	0.703	0.2447	0.7893	0.058*
H99B	0.720	0.3102	0.8061	0.058*
N1	0.56233 (16)	0.30489 (12)	0.89835 (9)	0.0302 (5)
H1	0.5981	0.2933	0.8705	0.036*
N8	0.41626 (15)	0.43055 (12)	0.95428 (9)	0.0260 (5)
H8	0.4475	0.4309	0.9852	0.031*
N14	0.27332 (16)	0.33331 (11)	0.93598 (9)	0.0259 (5)
H14	0.3237	0.3209	0.9544	0.031*
N19	0.29194 (15)	0.29289 (11)	0.82638 (9)	0.0255 (5)
H19	0.3444	0.2963	0.8451	0.031*
N26	0.24824 (16)	0.42551 (12)	0.77983 (9)	0.0281 (5)
H26	0.2876	0.4248	0.8074	0.034*
N33	0.06138 (16)	0.44679 (12)	0.81302 (9)	0.0276 (5)
H33	0.1014	0.4235	0.8337	0.033*
N37	−0.02709 (17)	0.33135 (12)	0.76936 (10)	0.0317 (5)
H37	0.0332	0.3412	0.7673	0.038*
N44	−0.04605 (17)	0.19468 (13)	0.82272 (9)	0.0317 (5)
H44	0.0125	0.2094	0.8239	0.038*
N48	0.05812 (17)	0.07860 (12)	0.85853 (10)	0.0329 (6)
H48	0.0495	0.0833	0.8232	0.040*
C2	0.55715 (19)	0.37879 (14)	0.91569 (11)	0.0273 (6)
H2	0.5754	0.3821	0.9549	0.033*
C3	0.6233 (2)	0.42399 (17)	0.88212 (13)	0.0369 (7)
H3A	0.6035	0.4220	0.8435	0.044*
H3B	0.6872	0.4036	0.8845	0.044*
C4	0.6274 (2)	0.50161 (17)	0.89989 (13)	0.0440 (8)
H4A	0.5615	0.5195	0.9026	0.053*
C5	0.6725 (3)	0.5089 (2)	0.95559 (17)	0.0690 (12)
H5A	0.6382	0.4797	0.9819	0.103*
H5B	0.6705	0.5586	0.9671	0.103*
H5C	0.7380	0.4930	0.9537	0.103*
C6	0.6780 (3)	0.5457 (2)	0.85788 (17)	0.0619 (11)
H6A	0.6468	0.5404	0.8225	0.093*
H6B	0.7432	0.5296	0.8549	0.093*
H6C	0.6768	0.5956	0.8689	0.093*
C7	0.45698 (19)	0.40586 (14)	0.90890 (11)	0.0277 (6)
C9	0.32010 (19)	0.45684 (14)	0.95234 (11)	0.0282 (6)
H9	0.3191	0.4996	0.9283	0.034*
C10	0.2865 (2)	0.47931 (15)	1.00853 (11)	0.0314 (6)
H10A	0.2888	0.4378	1.0331	0.038*
H10B	0.2203	0.4948	1.0059	0.038*
C11	0.3445 (2)	0.53908 (16)	1.03340 (12)	0.0376 (7)
H11A	0.4120	0.5277	1.0297	0.045*
H11B	0.3324	0.5834	1.0131	0.045*
C12	0.3218 (2)	0.55033 (18)	1.09211 (13)	0.0401 (7)
C13	0.25335 (19)	0.40226 (15)	0.92815 (10)	0.0259 (6)
C15	0.2110 (2)	0.27943 (14)	0.91380 (11)	0.0267 (6)
H15	0.1458	0.2894	0.9268	0.032*
C16	0.2414 (2)	0.20716 (14)	0.93613 (11)	0.0285 (6)
H16	0.3090	0.1983	0.9276	0.034*
C17	0.2245 (3)	0.20080 (18)	0.99670 (12)	0.0423 (8)
H17A	0.2438	0.1536	1.0091	0.063*
H17B	0.1576	0.2077	1.0044	0.063*
H17C	0.2612	0.2369	1.0159	0.063*
C18	0.2104 (2)	0.27934 (14)	0.85172 (11)	0.0266 (6)
C20	0.29244 (19)	0.30193 (15)	0.76732 (11)	0.0273 (6)
H20	0.2634	0.2589	0.7506	0.033*
C21	0.3939 (2)	0.30823 (16)	0.74620 (12)	0.0331 (7)
H21A	0.4257	0.3463	0.7677	0.040*
C22	0.3962 (2)	0.33029 (18)	0.68617 (12)	0.0433 (8)
H22A	0.4623	0.3382	0.6754	0.052*
H22B	0.3627	0.3760	0.6823	0.052*
C23	0.4470 (2)	0.23960 (18)	0.75621 (13)	0.0442 (8)
H23A	0.5114	0.2443	0.7426	0.066*
H23B	0.4155	0.2007	0.7372	0.066*
H23C	0.4485	0.2296	0.7954	0.066*
C24	0.3518 (3)	0.2762 (2)	0.64624 (15)	0.0645 (11)
H24A	0.3555	0.2947	0.6090	0.097*
H24B	0.2859	0.2685	0.6560	0.097*
H24C	0.3860	0.2312	0.6484	0.097*
C25	0.2333 (2)	0.36585 (15)	0.75176 (11)	0.0272 (6)
C27	0.20118 (19)	0.49181 (14)	0.76603 (11)	0.0287 (6)
H27	0.2153	0.5028	0.7270	0.034*
C28	0.2413 (2)	0.55155 (15)	0.80072 (12)	0.0320 (7)
H28A	0.2269	0.5413	0.8394	0.038*
H28B	0.2084	0.5960	0.7910	0.038*
C29	0.3471 (2)	0.56429 (17)	0.79557 (14)	0.0402 (8)
H29A	0.3799	0.5213	0.8099	0.048*
C30	0.3780 (2)	0.57473 (18)	0.73701 (15)	0.0478 (8)
H30A	0.4460	0.5824	0.7359	0.072*
H30B	0.3458	0.6160	0.7216	0.072*
H30C	0.3622	0.5325	0.7157	0.072*
C31	0.3755 (3)	0.62661 (19)	0.83088 (15)	0.0537 (9)
H31A	0.4432	0.6346	0.8275	0.081*
H31B	0.3600	0.6164	0.8690	0.081*
H31C	0.3416	0.6691	0.8190	0.081*
C32	0.0946 (2)	0.48769 (14)	0.77236 (11)	0.0287 (6)
C34	−0.03809 (19)	0.43998 (15)	0.82367 (11)	0.0291 (6)
H34	−0.0700	0.4825	0.8079	0.035*
C35	−0.0579 (2)	0.43934 (16)	0.88470 (12)	0.0346 (7)
H35A	−0.0363	0.4846	0.9008	0.041*
H35B	−0.1265	0.4357	0.8906	0.041*
C36	−0.0820 (2)	0.37418 (15)	0.79773 (12)	0.0318 (7)
C38	−0.0622 (2)	0.26824 (15)	0.74111 (12)	0.0332 (7)
H38	−0.1145	0.2831	0.7165	0.040*
C39	0.0164 (2)	0.23866 (16)	0.70610 (12)	0.0350 (7)
H39A	0.0710	0.2291	0.7299	0.042*
H39B	0.0355	0.2757	0.6798	0.042*
C40	−0.0057 (2)	0.17153 (16)	0.67446 (12)	0.0402 (8)
H40A	−0.0275	0.1347	0.7009	0.048*
C41	−0.0821 (3)	0.1826 (2)	0.63279 (14)	0.0554 (10)
H41A	−0.1391	0.1995	0.6510	0.083*
H41B	−0.0953	0.1377	0.6143	0.083*
H41C	−0.0615	0.2179	0.6060	0.083*
C42	0.0838 (3)	0.14466 (19)	0.64743 (15)	0.0570 (10)
H42A	0.0699	0.1014	0.6269	0.086*
H42B	0.1309	0.1343	0.6754	0.086*
H42C	0.1081	0.1810	0.6226	0.086*
C43	−0.1007 (2)	0.21293 (15)	0.78120 (12)	0.0315 (7)
C45	−0.0833 (2)	0.15004 (15)	0.86650 (11)	0.0315 (6)
H45	−0.1305	0.1169	0.8503	0.038*
C46	−0.1328 (2)	0.19588 (16)	0.90783 (14)	0.0402 (7)
H46A	−0.1883	0.2182	0.8907	0.048*
H46B	−0.1550	0.1659	0.9383	0.048*
C47	−0.0055 (2)	0.10588 (15)	0.89238 (12)	0.0319 (7)
C49	0.1411 (2)	0.04152 (15)	0.87763 (13)	0.0402 (8)
H49	0.1158	0.0105	0.9072	0.048*
C50	0.1880 (4)	−0.0109 (3)	0.8397 (2)	0.0389 (16)*	0.564 (7)
H50	0.2485	−0.0265	0.8566	0.047*	0.564 (7)
C51	0.2091 (4)	0.0265 (3)	0.7883 (2)	0.0401 (16)*	0.564 (7)
H51A	0.1509	0.0490	0.7746	0.048*	0.564 (7)
H51B	0.2299	−0.0085	0.7608	0.048*	0.564 (7)
C52	0.1261 (4)	−0.0748 (3)	0.8324 (3)	0.0527 (19)*	0.564 (7)
H52A	0.1563	−0.1081	0.8072	0.079*	0.564 (7)
H52B	0.0654	−0.0600	0.8174	0.079*	0.564 (7)
H52C	0.1164	−0.0979	0.8676	0.079*	0.564 (7)
C53A	0.2862 (15)	0.0841 (11)	0.7949 (9)	0.027 (6)*	0.1522 (18)
H53D	0.2992	0.1057	0.7594	0.040*	0.1522 (18)
H53E	0.3436	0.0623	0.8091	0.040*	0.1522 (18)
H53F	0.2643	0.1206	0.8203	0.040*	0.1522 (18)
C53	0.2610 (8)	0.0956 (5)	0.7892 (4)	0.035 (3)*	0.411 (5)
H53A	0.279 (4)	0.108 (2)	0.7516 (11)	0.052*	0.411 (5)
H53B	0.318 (3)	0.092 (3)	0.811 (2)	0.052*	0.411 (5)
H53C	0.220 (3)	0.1339 (18)	0.803 (2)	0.052*	0.411 (5)
C50B	0.1888 (6)	0.0191 (5)	0.8248 (2)	0.060 (3)*	0.436 (7)
H50B	0.1382	−0.0051	0.8036	0.072*	0.436 (7)
C51B	0.2662 (7)	−0.0369 (5)	0.8300 (4)	0.081 (3)*	0.436 (7)
H51C	0.3079	−0.0220	0.8602	0.097*	0.436 (7)
H51D	0.2359	−0.0817	0.8414	0.097*	0.436 (7)
C52B	0.2265 (12)	0.0770 (9)	0.7856 (6)	0.110 (5)*	0.436 (7)
H52D	0.1767	0.1114	0.7781	0.165*	0.436 (7)
H52E	0.2468	0.0550	0.7515	0.165*	0.436 (7)
H52F	0.2799	0.1012	0.8026	0.165*	0.436 (7)
C53C	0.3275 (14)	−0.0534 (11)	0.7821 (7)	0.091 (6)*	0.253 (4)
H53J	0.3734	−0.0896	0.7923	0.137*	0.253 (4)
H53K	0.3604	−0.0103	0.7706	0.137*	0.253 (4)
H53L	0.2887	−0.0709	0.7521	0.137*	0.253 (4)
C53B	0.227 (2)	−0.1031 (12)	0.8587 (12)	0.099 (9)*	0.183 (3)
H53G	0.279 (4)	−0.131 (6)	0.872 (8)	0.149*	0.183 (3)
H53H	0.192 (13)	−0.129 (6)	0.831 (3)	0.149*	0.183 (3)
H53I	0.185 (12)	−0.091 (3)	0.889 (6)	0.149*	0.183 (3)
C54	0.2083 (2)	0.08940 (15)	0.90773 (12)	0.0332 (7)
C1'	0.5138 (2)	0.25485 (15)	0.92402 (11)	0.0293 (6)
C2'	0.5279 (2)	0.17942 (15)	0.90517 (12)	0.0340 (7)
H2'A	0.5920	0.1746	0.8900	0.041*
H2'B	0.4827	0.1691	0.8756	0.041*
C3'	0.5151 (2)	0.12539 (15)	0.95024 (11)	0.0304 (6)
H3'A	0.4522	0.1327	0.9674	0.036*
C4'	0.5204 (2)	0.05014 (16)	0.92806 (13)	0.0415 (8)
H4'A	0.4772	0.0457	0.8967	0.050*
H4'B	0.5849	0.0411	0.9147	0.050*
C5'	0.4951 (3)	−0.00552 (17)	0.97037 (16)	0.0521 (9)
H5'A	0.4324	0.0054	0.9855	0.063*
H5'B	0.5411	−0.0034	1.0006	0.063*
C6'	0.4941 (5)	−0.0801 (2)	0.9469 (2)	0.1027 (19)
H6'A	0.5597	−0.0966	0.9430	0.123*
H6'B	0.4660	−0.0784	0.9101	0.123*
C7'	0.4401 (10)	−0.1339 (5)	0.9812 (4)	0.047 (2)*	0.37
H7'A	0.4752	−0.1422	1.0154	0.056*	0.37
H7'B	0.3786	−0.1132	0.9910	0.056*	0.37
C8'	0.4234 (9)	−0.2051 (5)	0.9535 (5)	0.072 (3)*	0.37
H8'A	0.3814	−0.1976	0.9220	0.086*	0.37
H8'B	0.4841	−0.2227	0.9393	0.086*	0.37
C9'	0.3810 (11)	−0.2617 (8)	0.9894 (7)	0.113 (5)*	0.37
H9'A	0.4259	−0.2734	1.0188	0.135*	0.37
H9'B	0.3712	−0.3051	0.9675	0.135*	0.37
C10'	0.2869 (11)	−0.2396 (13)	1.0150 (7)	0.143 (7)*	0.37
H10'A	0.2648	−0.2787	1.0386	0.172*	0.37
H10'B	0.2981	−0.1979	1.0386	0.172*	0.37
C11'	0.2101 (11)	−0.2215 (11)	0.9759 (7)	0.109 (6)*	0.37
H11'A	0.2052	−0.2604	0.9490	0.131*	0.37
H11'B	0.2288	−0.1783	0.9558	0.131*	0.37
C12'	0.1103 (13)	−0.2086 (13)	1.0005 (9)	0.150 (8)*	0.37
H12'A	0.0656	−0.1992	0.9710	0.225*	0.37
H12'B	0.1124	−0.1677	1.0251	0.225*	0.37
H12'C	0.0904	−0.2507	1.0208	0.225*	0.37
C7'A	0.4942 (11)	−0.1370 (8)	0.9781 (6)	0.065 (4)*	0.30
H7'C	0.5273	−0.1293	1.0131	0.078*	0.30
H7'D	0.5202	−0.1791	0.9594	0.078*	0.30
C8'A	0.3888 (10)	−0.1410 (7)	0.9849 (6)	0.059 (3)*	0.30
H8'C	0.3617	−0.0930	0.9805	0.071*	0.30
H8'D	0.3740	−0.1576	1.0222	0.071*	0.30
C9'A	0.3435 (19)	−0.1916 (15)	0.9432 (11)	0.149 (11)*	0.30
H9'C	0.3896	−0.2056	0.9150	0.178*	0.30
H9'D	0.2893	−0.1687	0.9252	0.178*	0.30
C10'A	0.310 (2)	−0.2593 (14)	0.978 (2)	0.33 (3)*	0.30
H10'C	0.2892	−0.2989	0.9542	0.398*	0.30
H10'D	0.3590	−0.2760	1.0034	0.398*	0.30
C11'A	0.2287 (16)	−0.2222 (11)	1.0064 (8)	0.096 (6)*	0.30
H11'C	0.2528	−0.1914	1.0359	0.115*	0.30
H11'D	0.1860	−0.2578	1.0226	0.115*	0.30
C12'A	0.174 (2)	−0.1763 (16)	0.9631 (12)	0.162 (11)*	0.30
H12'D	0.1177	−0.1563	0.9798	0.243*	0.30
H12'E	0.1565	−0.2062	0.9321	0.243*	0.30
H12'F	0.2149	−0.1377	0.9503	0.243*	0.30
C7'B	0.4140 (10)	−0.0977 (6)	0.9184 (6)	0.070 (3)*	0.33
H7'E	0.4206	−0.0801	0.8807	0.084*	0.33
H7'F	0.3602	−0.0726	0.9351	0.084*	0.33
C8'B	0.3911 (13)	−0.1766 (8)	0.9163 (7)	0.104 (5)*	0.33
H8'E	0.4509	−0.2032	0.9152	0.125*	0.33
H8'F	0.3575	−0.1862	0.8818	0.125*	0.33
C9'B	0.3317 (13)	−0.2057 (14)	0.9635 (10)	0.151 (10)*	0.33
H9'E	0.3549	−0.1880	0.9990	0.181*	0.33
H9'F	0.3324	−0.2582	0.9639	0.181*	0.33
C10'B	0.2292 (8)	−0.1762 (7)	0.9508 (5)	0.060 (3)*	0.33
H10'E	0.2291	−0.1238	0.9511	0.072*	0.33
H10'F	0.2077	−0.1926	0.9146	0.072*	0.33
C11'B	0.1645 (10)	−0.2052 (8)	0.9958 (6)	0.074 (4)*	0.33
H11'E	0.1925	−0.1941	1.0317	0.089*	0.33
H11'F	0.1611	−0.2574	0.9924	0.089*	0.33
C12'B	0.0630 (8)	−0.1743 (7)	0.9937 (5)	0.063 (3)*	0.33
H12'G	0.0253	−0.1951	1.0230	0.095*	0.33
H12'H	0.0343	−0.1857	0.9585	0.095*	0.33
H12'I	0.0654	−0.1227	0.9983	0.095*	0.33

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0294 (10)	0.0363 (11)	0.0217 (10)	−0.0022 (8)	−0.0028 (9)	0.0018 (8)
O12A	0.0836 (19)	0.0794 (18)	0.0351 (13)	−0.0375 (16)	0.0123 (14)	−0.0148 (13)
O12B	0.0822 (19)	0.0721 (17)	0.0430 (14)	−0.0398 (15)	0.0214 (14)	−0.0265 (13)
O13	0.0269 (10)	0.0395 (11)	0.0277 (10)	0.0019 (9)	−0.0042 (9)	−0.0009 (9)
O16	0.0321 (10)	0.0265 (10)	0.0326 (10)	−0.0013 (8)	−0.0030 (9)	−0.0012 (8)
O18	0.0284 (11)	0.0361 (11)	0.0265 (10)	−0.0055 (8)	−0.0026 (9)	0.0007 (8)
O25	0.0346 (11)	0.0385 (11)	0.0262 (10)	−0.0053 (9)	−0.0059 (10)	0.0064 (8)
O32	0.0340 (11)	0.0371 (11)	0.0327 (11)	0.0013 (9)	−0.0071 (10)	0.0091 (9)
O35	0.0342 (11)	0.0394 (12)	0.0353 (11)	−0.0071 (9)	−0.0045 (10)	0.0082 (9)
O36	0.0299 (12)	0.0565 (14)	0.0561 (14)	−0.0097 (10)	0.0073 (11)	−0.0150 (12)
O43	0.0289 (11)	0.0369 (11)	0.0412 (12)	−0.0064 (9)	−0.0041 (10)	−0.0063 (9)
O46	0.0650 (15)	0.0365 (11)	0.0237 (10)	−0.0062 (11)	0.0019 (11)	0.0014 (9)
O47	0.0438 (13)	0.0537 (13)	0.0246 (11)	−0.0079 (10)	0.0041 (10)	0.0031 (9)
O54	0.0557 (14)	0.0388 (12)	0.0568 (14)	0.0100 (11)	−0.0193 (13)	0.0018 (11)
O1'	0.0323 (11)	0.0341 (10)	0.0246 (10)	0.0035 (8)	0.0027 (9)	0.0045 (8)
O3'	0.0323 (11)	0.0424 (11)	0.0278 (10)	−0.0016 (9)	−0.0039 (9)	−0.0003 (9)
O99	0.0338 (12)	0.0512 (14)	0.0607 (15)	−0.0083 (10)	0.0152 (12)	−0.0167 (12)
N1	0.0282 (12)	0.0356 (13)	0.0268 (12)	0.0027 (10)	0.0042 (11)	0.0020 (10)
N8	0.0251 (12)	0.0319 (12)	0.0209 (11)	0.0002 (10)	−0.0030 (10)	−0.0012 (10)
N14	0.0259 (12)	0.0291 (12)	0.0226 (11)	−0.0011 (10)	−0.0032 (10)	0.0008 (9)
N19	0.0232 (12)	0.0309 (12)	0.0224 (12)	0.0004 (9)	0.0001 (10)	0.0006 (9)
N26	0.0286 (12)	0.0306 (12)	0.0250 (12)	0.0003 (10)	−0.0029 (10)	0.0016 (10)
N33	0.0261 (12)	0.0301 (12)	0.0268 (12)	0.0018 (10)	−0.0026 (11)	0.0048 (10)
N37	0.0278 (13)	0.0351 (13)	0.0321 (13)	−0.0038 (10)	0.0008 (11)	−0.0018 (11)
N44	0.0273 (12)	0.0411 (13)	0.0266 (13)	−0.0080 (11)	−0.0003 (11)	0.0007 (10)
N48	0.0394 (14)	0.0345 (13)	0.0249 (12)	−0.0055 (11)	0.0001 (12)	−0.0044 (10)
C2	0.0243 (14)	0.0326 (14)	0.0249 (14)	0.0022 (11)	−0.0009 (13)	0.0012 (12)
C3	0.0284 (16)	0.0438 (17)	0.0384 (17)	−0.0012 (13)	0.0054 (14)	0.0038 (14)
C4	0.0421 (18)	0.0403 (17)	0.050 (2)	−0.0037 (14)	0.0077 (17)	0.0067 (15)
C5	0.089 (3)	0.051 (2)	0.067 (3)	−0.027 (2)	−0.013 (2)	0.0015 (19)
C6	0.055 (2)	0.053 (2)	0.077 (3)	−0.0050 (18)	0.019 (2)	0.017 (2)
C7	0.0292 (15)	0.0277 (14)	0.0261 (15)	−0.0059 (11)	−0.0003 (14)	0.0019 (12)
C9	0.0279 (14)	0.0290 (14)	0.0278 (15)	0.0003 (12)	−0.0038 (13)	0.0039 (11)
C10	0.0341 (16)	0.0328 (15)	0.0274 (15)	0.0004 (13)	0.0000 (14)	−0.0014 (12)
C11	0.0422 (18)	0.0355 (16)	0.0352 (17)	−0.0014 (14)	0.0043 (15)	−0.0065 (13)
C12	0.0384 (17)	0.0473 (18)	0.0348 (17)	−0.0057 (15)	0.0055 (16)	−0.0088 (15)
C13	0.0263 (15)	0.0370 (15)	0.0143 (13)	0.0037 (12)	0.0021 (12)	0.0022 (11)
C15	0.0256 (14)	0.0318 (15)	0.0226 (14)	−0.0024 (11)	0.0016 (12)	0.0020 (11)
C16	0.0295 (15)	0.0303 (14)	0.0257 (14)	−0.0049 (12)	−0.0024 (13)	−0.0008 (12)
C17	0.053 (2)	0.0434 (18)	0.0307 (16)	−0.0132 (16)	−0.0042 (16)	0.0055 (14)
C18	0.0306 (15)	0.0255 (14)	0.0238 (14)	0.0021 (11)	−0.0008 (14)	−0.0002 (11)
C20	0.0300 (15)	0.0315 (14)	0.0204 (14)	0.0020 (12)	0.0006 (12)	−0.0008 (11)
C21	0.0288 (16)	0.0426 (17)	0.0280 (15)	−0.0003 (13)	0.0064 (13)	−0.0004 (13)
C22	0.0405 (18)	0.053 (2)	0.0363 (18)	0.0022 (15)	0.0143 (15)	0.0074 (15)
C23	0.0400 (18)	0.056 (2)	0.0366 (17)	0.0089 (16)	0.0062 (15)	0.0014 (15)
C24	0.073 (3)	0.085 (3)	0.036 (2)	0.003 (2)	0.007 (2)	−0.0042 (19)
C25	0.0279 (15)	0.0361 (15)	0.0177 (13)	−0.0027 (12)	0.0034 (13)	0.0041 (11)
C27	0.0306 (16)	0.0283 (14)	0.0271 (15)	0.0004 (12)	−0.0002 (13)	0.0073 (11)
C28	0.0363 (16)	0.0290 (15)	0.0307 (15)	−0.0022 (12)	−0.0019 (14)	0.0067 (12)
C29	0.0323 (16)	0.0361 (16)	0.052 (2)	−0.0062 (13)	−0.0068 (15)	0.0114 (15)
C30	0.0380 (18)	0.0411 (18)	0.064 (2)	−0.0031 (14)	0.0053 (18)	0.0063 (16)
C31	0.049 (2)	0.051 (2)	0.061 (2)	−0.0194 (17)	−0.0032 (19)	0.0041 (18)
C32	0.0328 (15)	0.0275 (14)	0.0257 (15)	0.0014 (12)	−0.0035 (13)	−0.0025 (12)
C34	0.0260 (15)	0.0301 (14)	0.0313 (15)	0.0020 (11)	−0.0013 (13)	0.0032 (12)
C35	0.0331 (16)	0.0362 (16)	0.0345 (16)	−0.0003 (13)	0.0004 (14)	0.0026 (13)
C36	0.0309 (16)	0.0351 (15)	0.0295 (15)	−0.0053 (13)	−0.0010 (14)	0.0039 (13)
C38	0.0337 (16)	0.0367 (16)	0.0292 (15)	−0.0082 (13)	−0.0057 (14)	−0.0017 (12)
C39	0.0382 (17)	0.0371 (16)	0.0298 (15)	−0.0058 (13)	0.0003 (14)	0.0011 (13)
C40	0.054 (2)	0.0374 (17)	0.0296 (16)	−0.0124 (15)	0.0058 (16)	0.0004 (13)
C41	0.068 (2)	0.063 (2)	0.0351 (18)	−0.019 (2)	−0.0015 (18)	−0.0078 (17)
C42	0.077 (3)	0.046 (2)	0.049 (2)	−0.0094 (19)	0.017 (2)	−0.0117 (17)
C43	0.0318 (16)	0.0344 (15)	0.0284 (15)	−0.0010 (13)	0.0010 (14)	−0.0073 (12)
C45	0.0318 (16)	0.0368 (16)	0.0258 (14)	−0.0096 (13)	0.0023 (13)	−0.0003 (12)
C46	0.0426 (18)	0.0350 (16)	0.0430 (18)	−0.0059 (14)	0.0102 (16)	0.0009 (14)
C47	0.0347 (17)	0.0336 (15)	0.0276 (16)	−0.0102 (13)	0.0024 (14)	−0.0015 (12)
C49	0.0382 (18)	0.0341 (16)	0.0484 (19)	−0.0013 (14)	−0.0018 (16)	−0.0010 (14)
C54	0.0429 (18)	0.0308 (16)	0.0259 (15)	0.0030 (13)	0.0017 (15)	0.0034 (12)
C1'	0.0293 (15)	0.0383 (16)	0.0204 (14)	0.0060 (13)	−0.0060 (14)	0.0021 (12)
C2'	0.0390 (17)	0.0361 (16)	0.0269 (15)	0.0045 (13)	−0.0021 (14)	0.0002 (12)
C3'	0.0293 (15)	0.0323 (15)	0.0297 (15)	0.0025 (12)	−0.0060 (13)	−0.0018 (12)
C4'	0.0456 (19)	0.0380 (17)	0.0410 (18)	0.0012 (14)	−0.0079 (16)	−0.0051 (14)
C5'	0.061 (2)	0.0324 (17)	0.063 (2)	−0.0001 (16)	−0.002 (2)	0.0013 (16)
C6'	0.158 (5)	0.034 (2)	0.116 (4)	−0.002 (3)	−0.014 (4)	0.000 (2)

Geometric parameters (Å, º)

O7—C7	1.230 (3)	C39—H39A	0.9900
O12A—C12	1.197 (4)	C39—H39B	0.9900
O12B—C12	1.326 (4)	C40—C41	1.509 (5)
O12B—H12B	0.8400	C40—C42	1.523 (5)
O13—C13	1.223 (3)	C40—H40A	1.0000
O16—C54	1.334 (3)	C41—H41A	0.9800
O16—C16	1.448 (3)	C41—H41B	0.9800
O18—C18	1.233 (3)	C41—H41C	0.9800
O25—C25	1.235 (3)	C42—H42A	0.9800
O32—C32	1.223 (3)	C42—H42B	0.9800
O35—C35	1.410 (4)	C42—H42C	0.9800
O35—H35	0.8400	C45—C46	1.508 (4)
O36—C36	1.238 (3)	C45—C47	1.526 (4)
O43—C43	1.233 (3)	C45—H45	1.0000
O46—C46	1.430 (4)	C46—H46A	0.9900
O46—H46	0.8400	C46—H46B	0.9900
O47—C47	1.232 (3)	C49—C54	1.510 (4)
O54—C54	1.200 (4)	C49—C50	1.513 (2)
O1'—C1'	1.235 (3)	C49—C50B	1.525 (2)
O3'—C3'	1.417 (3)	C49—H49	1.0000
O3'—H3'O	0.8400	C50—C51	1.477 (8)
O99—H99A	0.851	C50—C52	1.505 (8)
O99—H99B	0.872	C50—H50	1.0000
N1—C1'	1.329 (4)	C51—C53A	1.554 (15)
N1—C2	1.460 (4)	C51—H51A	0.9900
N1—H1	0.8800	C51—H51B	0.9900
N8—C7	1.340 (4)	C52—H52A	0.9800
N8—C9	1.458 (4)	C52—H52B	0.9800
N8—H8	0.8800	C52—H52C	0.9800
N14—C13	1.346 (4)	C53A—H53D	0.9800
N14—C15	1.455 (3)	C53A—H53E	0.9800
N14—H14	0.8800	C53A—H53F	0.9800
N19—C18	1.343 (4)	C53—H53A	0.983 (18)
N19—C20	1.460 (3)	C53—H53B	0.977 (18)
N19—H19	0.8800	C53—H53C	0.988 (18)
N26—C25	1.337 (4)	C50B—C51B	1.532 (11)
N26—C27	1.459 (3)	C50B—C52B	1.552 (14)
N26—H26	0.8800	C50B—H50B	1.0000
N33—C32	1.348 (4)	C51B—C53C	1.497 (15)
N33—C34	1.447 (4)	C51B—H51C	0.9900
N33—H33	0.8800	C51B—H51D	0.9900
N37—C36	1.323 (4)	C52B—H52D	0.9800
N37—C38	1.466 (4)	C52B—H52E	0.9800
N37—H37	0.8800	C52B—H52F	0.9800
N44—C43	1.328 (4)	C53C—H53J	0.9800
N44—C45	1.465 (4)	C53C—H53K	0.9800
N44—H44	0.8800	C53C—H53L	0.9800
N48—C47	1.333 (4)	C53B—H53G	0.974 (19)
N48—C49	1.451 (4)	C53B—H53H	0.979 (19)
N48—H48	0.8800	C53B—H53I	0.971 (19)
C2—C3	1.515 (4)	C1'—C2'	1.510 (4)
C2—C7	1.525 (4)	C2'—C3'	1.516 (4)
C2—H2	1.0000	C2'—H2'A	0.9900
C3—C4	1.529 (5)	C2'—H2'B	0.9900
C3—H3A	0.9900	C3'—C4'	1.523 (4)
C3—H3B	0.9900	C3'—H3'A	1.0000
C4—C6	1.508 (5)	C4'—C5'	1.521 (5)
C4—C5	1.517 (5)	C4'—H4'A	0.9900
C4—H4A	1.0000	C4'—H4'B	0.9900
C5—H5A	0.9800	C5'—C6'	1.521 (6)
C5—H5B	0.9800	C5'—H5'A	0.9900
C5—H5C	0.9800	C5'—H5'B	0.9900
C6—H6A	0.9800	C6'—C7'A	1.319 (15)
C6—H6B	0.9800	C6'—C7'B	1.379 (14)
C6—H6C	0.9800	C6'—C7'	1.526 (11)
C9—C10	1.521 (4)	C6'—H6'A	0.9900
C9—C13	1.522 (4)	C6'—H6'B	0.9900
C9—H9	1.0000	C7'—C8'	1.524 (11)
C10—C11	1.525 (4)	C7'—H7'A	0.9900
C10—H10A	0.9900	C7'—H7'B	0.9900
C10—H10B	0.9900	C8'—C9'	1.511 (13)
C11—C12	1.493 (4)	C8'—H8'A	0.9900
C11—H11A	0.9900	C8'—H8'B	0.9900
C11—H11B	0.9900	C9'—C10'	1.539 (15)
C15—C18	1.525 (4)	C9'—H9'A	0.9900
C15—C16	1.532 (4)	C9'—H9'B	0.9900
C15—H15	1.0000	C10'—C11'	1.496 (14)
C16—C17	1.511 (4)	C10'—H10'A	0.9900
C16—H16	1.0000	C10'—H10'B	0.9900
C17—H17A	0.9800	C11'—C12'	1.563 (14)
C17—H17B	0.9800	C11'—H11'A	0.9900
C17—H17C	0.9800	C11'—H11'B	0.9900
C20—C25	1.520 (4)	C12'—H12'A	0.9800
C20—C21	1.540 (4)	C12'—H12'B	0.9800
C20—H20	1.0000	C12'—H12'C	0.9800
C21—C23	1.520 (4)	C7'A—C8'A	1.512 (14)
C21—C22	1.532 (4)	C7'A—H7'C	0.9900
C21—H21A	1.0000	C7'A—H7'D	0.9900
C22—C24	1.550 (5)	C8'A—C9'A	1.543 (19)
C22—H22A	0.9900	C8'A—H8'C	0.9900
C22—H22B	0.9900	C8'A—H8'D	0.9900
C23—H23A	0.9800	C9'A—C10'A	1.60 (2)
C23—H23B	0.9800	C9'A—H9'C	0.9900
C23—H23C	0.9800	C9'A—H9'D	0.9900
C24—H24A	0.9800	C10'A—C11'A	1.53 (2)
C24—H24B	0.9800	C10'A—H10'C	0.9900
C24—H24C	0.9800	C10'A—H10'D	0.9900
C27—C28	1.524 (4)	C11'A—C12'A	1.576 (19)
C27—C32	1.528 (4)	C11'A—H11'C	0.9900
C27—H27	1.0000	C11'A—H11'D	0.9900
C28—C29	1.531 (4)	C12'A—H12'D	0.9800
C28—H28A	0.9900	C12'A—H12'E	0.9800
C28—H28B	0.9900	C12'A—H12'F	0.9800
C29—C31	1.516 (5)	C7'B—C8'B	1.525 (15)
C29—C30	1.517 (5)	C7'B—H7'E	0.9900
C29—H29A	1.0000	C7'B—H7'F	0.9900
C30—H30A	0.9800	C8'B—C9'B	1.538 (19)
C30—H30B	0.9800	C8'B—H8'E	0.9900
C30—H30C	0.9800	C8'B—H8'F	0.9900
C31—H31A	0.9800	C9'B—C10'B	1.59 (2)
C31—H31B	0.9800	C9'B—H9'E	0.9900
C31—H31C	0.9800	C9'B—H9'F	0.9900
C34—C35	1.525 (4)	C10'B—C11'B	1.538 (17)
C34—C36	1.529 (4)	C10'B—H10'E	0.9900
C34—H34	1.0000	C10'B—H10'F	0.9900
C35—H35A	0.9900	C11'B—C12'B	1.561 (17)
C35—H35B	0.9900	C11'B—H11'E	0.9900
C38—C39	1.518 (4)	C11'B—H11'F	0.9900
C38—C43	1.536 (4)	C12'B—H12'G	0.9800
C38—H38	1.0000	C12'B—H12'H	0.9800
C39—C40	1.519 (4)	C12'B—H12'I	0.9800
C12—O12B—H12B	109.5	O46—C46—H46A	109.3
C54—O16—C16	117.3 (2)	C45—C46—H46A	109.3
C35—O35—H35	109.5	O46—C46—H46B	109.3
C46—O46—H46	109.5	C45—C46—H46B	109.3
C3'—O3'—H3'O	109.5	H46A—C46—H46B	108.0
H99A—O99—H99B	101	O47—C47—N48	121.9 (3)
C1'—N1—C2	120.9 (2)	O47—C47—C45	121.7 (3)
C1'—N1—H1	119.5	N48—C47—C45	116.4 (3)
C2—N1—H1	119.5	N48—C49—C54	112.7 (2)
C7—N8—C9	119.9 (2)	N48—C49—C50	118.4 (3)
C7—N8—H8	120.1	C54—C49—C50	114.3 (3)
C9—N8—H8	120.1	N48—C49—C50B	102.8 (4)
C13—N14—C15	119.5 (2)	C54—C49—C50B	107.4 (4)
C13—N14—H14	120.2	N48—C49—H49	102.9
C15—N14—H14	120.2	C54—C49—H49	102.9
C18—N19—C20	119.1 (2)	C50—C49—H49	102.9
C18—N19—H19	120.4	C50B—C49—H49	128.0
C20—N19—H19	120.4	C51—C50—C52	113.5 (5)
C25—N26—C27	121.9 (2)	C51—C50—C49	107.7 (4)
C25—N26—H26	119.0	C52—C50—C49	109.8 (4)
C27—N26—H26	119.0	C51—C50—H50	108.6
C32—N33—C34	121.9 (2)	C52—C50—H50	108.6
C32—N33—H33	119.0	C49—C50—H50	108.6
C34—N33—H33	119.0	C50—C51—C53A	112.8 (9)
C36—N37—C38	123.0 (2)	C50—C51—H51A	109.0
C36—N37—H37	118.5	C53A—C51—H51A	109.0
C38—N37—H37	118.5	C50—C51—H51B	109.0
C43—N44—C45	120.0 (2)	C53A—C51—H51B	109.0
C43—N44—H44	120.0	H51A—C51—H51B	107.8
C45—N44—H44	120.0	C50—C52—H52A	109.5
C47—N48—C49	122.6 (2)	C50—C52—H52B	109.5
C47—N48—H48	118.7	H52A—C52—H52B	109.5
C49—N48—H48	118.7	C50—C52—H52C	109.5
N1—C2—C3	110.3 (2)	H52A—C52—H52C	109.5
N1—C2—C7	109.6 (2)	H52B—C52—H52C	109.5
C3—C2—C7	109.5 (2)	C50—C52—H53H	102 (3)
N1—C2—H2	109.1	C51—C53A—H53D	109.5
C3—C2—H2	109.1	C51—C53A—H53E	109.5
C7—C2—H2	109.1	H53D—C53A—H53E	109.5
C2—C3—C4	114.0 (2)	C51—C53A—H53F	109.5
C2—C3—H3A	108.7	H53D—C53A—H53F	109.5
C4—C3—H3A	108.7	H53E—C53A—H53F	109.5
C2—C3—H3B	108.7	C51—C53A—H53A	96 (3)
C4—C3—H3B	108.7	H53E—C53A—H53A	124.2
H3A—C3—H3B	107.6	H53F—C53A—H53A	106.7
C6—C4—C5	111.4 (3)	C51—C53A—H53B	139 (6)
C6—C4—C3	110.5 (3)	H53D—C53A—H53B	109.7
C5—C4—C3	111.1 (3)	H53A—C53A—H53B	124 (5)
C6—C4—H4A	107.9	H53B—C53A—H53C	103 (5)
C5—C4—H4A	107.9	H53A—C53—H53B	109 (2)
C3—C4—H4A	107.9	H53A—C53—H53C	108 (2)
C4—C5—H5A	109.5	H53B—C53—H53C	110 (2)
C4—C5—H5B	109.5	C49—C50B—C51B	116.2 (7)
H5A—C5—H5B	109.5	C49—C50B—C52B	119.1 (8)
C4—C5—H5C	109.5	C51B—C50B—C52B	106.8 (8)
H5A—C5—H5C	109.5	C49—C50B—H50B	104.4
H5B—C5—H5C	109.5	C51B—C50B—H50B	104.4
C4—C6—H6A	109.5	C52B—C50B—H50B	104.4
C4—C6—H6B	109.5	C53C—C51B—C50B	119.8 (11)
H6A—C6—H6B	109.5	C53C—C51B—H51C	107.4
C4—C6—H6C	109.5	C50B—C51B—H51C	107.4
H6A—C6—H6C	109.5	C53C—C51B—H51D	107.4
H6B—C6—H6C	109.5	C50B—C51B—H51D	107.4
O7—C7—N8	122.7 (3)	H51C—C51B—H51D	106.9
O7—C7—C2	121.8 (3)	C50B—C52B—H53A	160 (3)
N8—C7—C2	115.5 (2)	C50B—C52B—H53B	100 (2)
N8—C9—C10	111.1 (2)	C50B—C52B—H53C	113 (3)
N8—C9—C13	111.7 (2)	C50B—C52B—H52D	109.5
C10—C9—C13	110.3 (2)	H53B—C52B—H52D	126.2
N8—C9—H9	107.9	C50B—C52B—H52E	109.5
C10—C9—H9	107.9	H53B—C52B—H52E	100.9
C13—C9—H9	107.9	H53C—C52B—H52E	137.3
C9—C10—C11	113.5 (2)	H52D—C52B—H52E	109.5
C9—C10—H10A	108.9	C50B—C52B—H52F	109.5
C11—C10—H10A	108.9	H52D—C52B—H52F	109.5
C9—C10—H10B	108.9	H52E—C52B—H52F	109.5
C11—C10—H10B	108.9	C51B—C53C—H53J	109.5
H10A—C10—H10B	107.7	C51B—C53C—H53K	109.5
C12—C11—C10	112.0 (3)	H53J—C53C—H53K	109.5
C12—C11—H11A	109.2	C51B—C53C—H53L	109.5
C10—C11—H11A	109.2	H53J—C53C—H53L	109.5
C12—C11—H11B	109.2	H53K—C53C—H53L	109.5
C10—C11—H11B	109.2	H53G—C53B—H53H	110 (3)
H11A—C11—H11B	107.9	H53G—C53B—H53I	111 (3)
O12A—C12—O12B	122.5 (3)	H53H—C53B—H53I	110 (3)
O12A—C12—C11	125.6 (3)	O54—C54—O16	124.2 (3)
O12B—C12—C11	111.9 (3)	O54—C54—C49	122.6 (3)
O13—C13—N14	122.9 (3)	O16—C54—C49	113.2 (3)
O13—C13—C9	119.3 (2)	O1'—C1'—N1	121.4 (3)
N14—C13—C9	117.8 (2)	O1'—C1'—C2'	121.5 (3)
N14—C15—C18	112.3 (2)	N1—C1'—C2'	117.1 (3)
N14—C15—C16	108.4 (2)	C1'—C2'—C3'	113.2 (2)
C18—C15—C16	111.0 (2)	C1'—C2'—H2'A	108.9
N14—C15—H15	108.4	C3'—C2'—H2'A	108.9
C18—C15—H15	108.4	C1'—C2'—H2'B	108.9
C16—C15—H15	108.4	C3'—C2'—H2'B	108.9
O16—C16—C17	109.9 (2)	H2'A—C2'—H2'B	107.7
O16—C16—C15	103.8 (2)	O3'—C3'—C2'	107.6 (2)
C17—C16—C15	112.2 (2)	O3'—C3'—C4'	111.4 (2)
O16—C16—H16	110.3	C2'—C3'—C4'	111.1 (2)
C17—C16—H16	110.3	O3'—C3'—H3'A	108.9
C15—C16—H16	110.3	C2'—C3'—H3'A	108.9
C16—C17—H17A	109.5	C4'—C3'—H3'A	108.9
C16—C17—H17B	109.5	C5'—C4'—C3'	112.8 (3)
H17A—C17—H17B	109.5	C5'—C4'—H4'A	109.0
C16—C17—H17C	109.5	C3'—C4'—H4'A	109.0
H17A—C17—H17C	109.5	C5'—C4'—H4'B	109.0
H17B—C17—H17C	109.5	C3'—C4'—H4'B	109.0
O18—C18—N19	121.8 (2)	H4'A—C4'—H4'B	107.8
O18—C18—C15	120.9 (2)	C4'—C5'—C6'	112.5 (4)
N19—C18—C15	117.3 (2)	C4'—C5'—H5'A	109.1
N19—C20—C25	109.8 (2)	C6'—C5'—H5'A	109.1
N19—C20—C21	110.4 (2)	C4'—C5'—H5'B	109.1
C25—C20—C21	112.0 (2)	C6'—C5'—H5'B	109.1
N19—C20—H20	108.2	H5'A—C5'—H5'B	107.8
C25—C20—H20	108.2	C7'A—C6'—C5'	122.3 (8)
C21—C20—H20	108.2	C7'B—C6'—C5'	115.0 (7)
C23—C21—C22	112.1 (3)	C5'—C6'—C7'	114.3 (5)
C23—C21—C20	110.3 (3)	C5'—C6'—H6'A	108.7
C22—C21—C20	111.4 (2)	C7'—C6'—H6'A	108.7
C23—C21—H21A	107.6	C7'A—C6'—H6'B	123.8
C22—C21—H21A	107.6	C5'—C6'—H6'B	108.7
C20—C21—H21A	107.6	C7'—C6'—H6'B	108.7
C21—C22—C24	114.9 (3)	H6'A—C6'—H6'B	107.6
C21—C22—H22A	108.5	C8'—C7'—C6'	114.8 (8)
C24—C22—H22A	108.5	C8'—C7'—H7'A	108.6
C21—C22—H22B	108.5	C6'—C7'—H7'A	108.6
C24—C22—H22B	108.5	C8'—C7'—H7'B	108.6
H22A—C22—H22B	107.5	C6'—C7'—H7'B	108.6
C21—C23—H23A	109.5	H7'A—C7'—H7'B	107.5
C21—C23—H23B	109.5	C9'—C8'—C7'	115.3 (10)
H23A—C23—H23B	109.5	C9'—C8'—H8'A	108.5
C21—C23—H23C	109.5	C7'—C8'—H8'A	108.5
H23A—C23—H23C	109.5	C9'—C8'—H8'B	108.5
H23B—C23—H23C	109.5	C7'—C8'—H8'B	108.5
C22—C24—H24A	109.5	H8'A—C8'—H8'B	107.5
C22—C24—H24B	109.5	C8'—C9'—C10'	113.2 (12)
H24A—C24—H24B	109.5	C8'—C9'—H9'A	108.9
C22—C24—H24C	109.5	C10'—C9'—H9'A	108.9
H24A—C24—H24C	109.5	C8'—C9'—H9'B	108.9
H24B—C24—H24C	109.5	C10'—C9'—H9'B	108.9
O25—C25—N26	121.7 (3)	H9'A—C9'—H9'B	107.7
O25—C25—C20	121.5 (3)	C11'—C10'—C9'	115.9 (13)
N26—C25—C20	116.8 (2)	C11'—C10'—H10'A	108.3
N26—C27—C28	109.4 (2)	C9'—C10'—H10'A	108.3
N26—C27—C32	112.9 (2)	C11'—C10'—H10'B	108.3
C28—C27—C32	110.7 (2)	C9'—C10'—H10'B	108.3
N26—C27—H27	107.9	H10'A—C10'—H10'B	107.4
C28—C27—H27	107.9	C10'—C11'—C12'	116.9 (14)
C32—C27—H27	107.9	C10'—C11'—H11'A	108.1
C27—C28—C29	116.1 (3)	C12'—C11'—H11'A	108.1
C27—C28—H28A	108.3	C10'—C11'—H11'B	108.1
C29—C28—H28A	108.3	C12'—C11'—H11'B	108.1
C27—C28—H28B	108.3	H11'A—C11'—H11'B	107.3
C29—C28—H28B	108.3	C11'—C12'—H12'A	109.5
H28A—C28—H28B	107.4	C11'—C12'—H12'B	109.5
C31—C29—C30	111.4 (3)	H12'A—C12'—H12'B	109.5
C31—C29—C28	109.7 (3)	C11'—C12'—H12'C	109.5
C30—C29—C28	112.6 (3)	H12'A—C12'—H12'C	109.5
C31—C29—H29A	107.7	H12'B—C12'—H12'C	109.5
C30—C29—H29A	107.7	C6'—C7'A—C8'A	96.0 (12)
C28—C29—H29A	107.7	C6'—C7'A—H7'C	112.6
C29—C30—H30A	109.5	C8'A—C7'A—H7'C	112.6
C29—C30—H30B	109.5	C6'—C7'A—H7'D	112.6
H30A—C30—H30B	109.5	C8'A—C7'A—H7'D	112.6
C29—C30—H30C	109.5	H7'C—C7'A—H7'D	110.1
H30A—C30—H30C	109.5	C7'A—C8'A—C9'A	111.8 (14)
H30B—C30—H30C	109.5	C7'A—C8'A—H8'C	109.2
C29—C31—H31A	109.5	C9'A—C8'A—H8'C	109.2
C29—C31—H31B	109.5	C7'A—C8'A—H8'D	109.2
H31A—C31—H31B	109.5	C9'A—C8'A—H8'D	109.2
C29—C31—H31C	109.5	H8'C—C8'A—H8'D	107.9
H31A—C31—H31C	109.5	C8'A—C9'A—C10'A	105.4 (19)
H31B—C31—H31C	109.5	C8'A—C9'A—H9'C	110.7
O32—C32—N33	122.8 (3)	C10'A—C9'A—H9'C	110.7
O32—C32—C27	120.3 (3)	C8'A—C9'A—H9'D	110.7
N33—C32—C27	116.9 (2)	C10'A—C9'A—H9'D	110.7
N33—C34—C35	111.1 (2)	H9'C—C9'A—H9'D	108.8
N33—C34—C36	113.4 (2)	C11'A—C10'A—C9'A	95.9 (16)
C35—C34—C36	109.1 (2)	C11'A—C10'A—H10'C	112.6
N33—C34—H34	107.7	C9'A—C10'A—H10'C	112.6
C35—C34—H34	107.7	C11'A—C10'A—H10'D	112.6
C36—C34—H34	107.7	C9'A—C10'A—H10'D	112.6
O35—C35—C34	112.5 (2)	H10'C—C10'A—H10'D	110.1
O35—C35—H35A	109.1	C10'A—C11'A—C12'A	108.3 (18)
C34—C35—H35A	109.1	C10'A—C11'A—H11'C	110.0
O35—C35—H35B	109.1	C12'A—C11'A—H11'C	110.0
C34—C35—H35B	109.1	C10'A—C11'A—H11'D	110.0
H35A—C35—H35B	107.8	C12'A—C11'A—H11'D	110.0
O36—C36—N37	123.8 (3)	H11'C—C11'A—H11'D	108.4
O36—C36—C34	117.9 (3)	C11'A—C12'A—H12'D	109.5
N37—C36—C34	118.3 (2)	C11'A—C12'A—H12'E	109.5
N37—C38—C39	108.4 (2)	H12'D—C12'A—H12'E	109.5
N37—C38—C43	111.7 (2)	C11'A—C12'A—H12'F	109.5
C39—C38—C43	112.1 (2)	H12'D—C12'A—H12'F	109.5
N37—C38—H38	108.1	H12'E—C12'A—H12'F	109.5
C39—C38—H38	108.1	C6'—C7'B—C8'B	115.4 (12)
C43—C38—H38	108.1	C6'—C7'B—H7'E	108.4
C38—C39—C40	116.3 (3)	C8'B—C7'B—H7'E	108.4
C38—C39—H39A	108.2	C6'—C7'B—H7'F	108.4
C40—C39—H39A	108.2	C8'B—C7'B—H7'F	108.4
C38—C39—H39B	108.2	H7'E—C7'B—H7'F	107.5
C40—C39—H39B	108.2	C7'B—C8'B—C9'B	116.2 (15)
H39A—C39—H39B	107.4	C7'B—C8'B—H8'E	108.2
C41—C40—C39	112.4 (3)	C9'B—C8'B—H8'E	108.2
C41—C40—C42	110.7 (3)	C7'B—C8'B—H8'F	108.2
C39—C40—C42	109.1 (3)	C9'B—C8'B—H8'F	108.2
C41—C40—H40A	108.2	H8'E—C8'B—H8'F	107.4
C39—C40—H40A	108.2	C8'B—C9'B—C10'B	103.4 (15)
C42—C40—H40A	108.2	C8'B—C9'B—H9'E	111.1
C40—C41—H41A	109.5	C10'B—C9'B—H9'E	111.1
C40—C41—H41B	109.5	C8'B—C9'B—H9'F	111.1
H41A—C41—H41B	109.5	C10'B—C9'B—H9'F	111.1
C40—C41—H41C	109.5	H9'E—C9'B—H9'F	109.0
H41A—C41—H41C	109.5	C11'B—C10'B—C9'B	106.5 (11)
H41B—C41—H41C	109.5	C11'B—C10'B—H10'E	110.4
C40—C42—H42A	109.5	C9'B—C10'B—H10'E	110.4
C40—C42—H42B	109.5	C11'B—C10'B—H10'F	110.4
H42A—C42—H42B	109.5	C9'B—C10'B—H10'F	110.4
C40—C42—H42C	109.5	H10'E—C10'B—H10'F	108.6
H42A—C42—H42C	109.5	C10'B—C11'B—C12'B	113.5 (12)
H42B—C42—H42C	109.5	C10'B—C11'B—H11'E	108.9
O43—C43—N44	123.3 (3)	C12'B—C11'B—H11'E	108.9
O43—C43—C38	119.4 (3)	C10'B—C11'B—H11'F	108.9
N44—C43—C38	117.3 (2)	C12'B—C11'B—H11'F	108.9
N44—C45—C46	109.5 (2)	H11'E—C11'B—H11'F	107.7
N44—C45—C47	110.9 (2)	C11'B—C12'B—H12'G	109.5
C46—C45—C47	111.9 (2)	C11'B—C12'B—H12'H	109.5
N44—C45—H45	108.2	H12'G—C12'B—H12'H	109.5
C46—C45—H45	108.2	C11'B—C12'B—H12'I	109.5
C47—C45—H45	108.2	H12'G—C12'B—H12'I	109.5
O46—C46—C45	111.6 (2)	H12'H—C12'B—H12'I	109.5
C1'—N1—C2—C3	176.5 (2)	C38—C39—C40—C41	63.7 (4)
C1'—N1—C2—C7	−62.8 (3)	C38—C39—C40—C42	−173.1 (3)
N1—C2—C3—C4	−176.2 (2)	C45—N44—C43—O43	−10.8 (4)
C7—C2—C3—C4	63.0 (3)	C45—N44—C43—C38	171.4 (2)
C2—C3—C4—C6	−168.1 (3)	N37—C38—C43—O43	131.4 (3)
C2—C3—C4—C5	67.8 (4)	C39—C38—C43—O43	−106.7 (3)
C9—N8—C7—O7	3.3 (4)	N37—C38—C43—N44	−50.8 (3)
C9—N8—C7—C2	−179.2 (2)	C39—C38—C43—N44	71.2 (3)
N1—C2—C7—O7	−60.4 (3)	C43—N44—C45—C46	−84.9 (3)
C3—C2—C7—O7	60.8 (3)	C43—N44—C45—C47	151.2 (3)
N1—C2—C7—N8	122.1 (2)	N44—C45—C46—O46	−56.1 (3)
C3—C2—C7—N8	−116.7 (3)	C47—C45—C46—O46	67.2 (3)
C7—N8—C9—C10	177.6 (2)	C49—N48—C47—O47	−7.2 (4)
C7—N8—C9—C13	54.0 (3)	C49—N48—C47—C45	173.7 (2)
N8—C9—C10—C11	61.0 (3)	N44—C45—C47—O47	140.9 (3)
C13—C9—C10—C11	−174.6 (2)	C46—C45—C47—O47	18.4 (4)
C9—C10—C11—C12	−169.1 (3)	N44—C45—C47—N48	−40.1 (3)
C10—C11—C12—O12A	6.4 (5)	C46—C45—C47—N48	−162.6 (2)
C10—C11—C12—O12B	−174.8 (3)	C47—N48—C49—C54	−66.3 (3)
C15—N14—C13—O13	1.3 (4)	C47—N48—C49—C50	156.5 (4)
C15—N14—C13—C9	179.6 (2)	C47—N48—C49—C50B	178.4 (5)
N8—C9—C13—O13	−150.6 (2)	N48—C49—C50—C51	54.6 (5)
C10—C9—C13—O13	85.4 (3)	C54—C49—C50—C51	−82.0 (5)
N8—C9—C13—N14	31.0 (3)	C50B—C49—C50—C51	−2.4 (10)
C10—C9—C13—N14	−93.1 (3)	N48—C49—C50—C52	−69.4 (5)
C13—N14—C15—C18	65.8 (3)	C54—C49—C50—C52	154.0 (4)
C13—N14—C15—C16	−171.2 (2)	C50B—C49—C50—C52	−126.4 (13)
C54—O16—C16—C17	−76.2 (3)	C52—C50—C51—C53A	−170.1 (11)
C54—O16—C16—C15	163.6 (2)	C49—C50—C51—C53A	68.2 (11)
N14—C15—C16—O16	−173.8 (2)	N48—C49—C50B—C51B	−165.6 (7)
C18—C15—C16—O16	−50.1 (3)	C54—C49—C50B—C51B	75.3 (9)
N14—C15—C16—C17	67.6 (3)	C50—C49—C50B—C51B	−34.8 (9)
C18—C15—C16—C17	−168.7 (2)	N48—C49—C50B—C52B	64.6 (10)
C20—N19—C18—O18	8.3 (4)	C54—C49—C50B—C52B	−54.6 (10)
C20—N19—C18—C15	−172.6 (2)	C50—C49—C50B—C52B	−164.6 (18)
N14—C15—C18—O18	−144.3 (2)	C49—C50B—C51B—C53C	−170.0 (12)
C16—C15—C18—O18	94.2 (3)	C52B—C50B—C51B—C53C	−34.4 (16)
N14—C15—C18—N19	36.6 (3)	C16—O16—C54—O54	−2.2 (4)
C16—C15—C18—N19	−84.9 (3)	C16—O16—C54—C49	178.5 (2)
C18—N19—C20—C25	62.7 (3)	N48—C49—C54—O54	175.5 (3)
C18—N19—C20—C21	−173.4 (2)	C50—C49—C54—O54	−45.5 (5)
N19—C20—C21—C23	64.5 (3)	C50B—C49—C54—O54	−72.0 (5)
C25—C20—C21—C23	−172.8 (2)	N48—C49—C54—O16	−5.2 (4)
N19—C20—C21—C22	−170.3 (2)	C50—C49—C54—O16	133.9 (4)
C25—C20—C21—C22	−47.6 (3)	C50B—C49—C54—O16	107.4 (5)
C23—C21—C22—C24	60.4 (4)	C2—N1—C1'—O1'	5.9 (4)
C20—C21—C22—C24	−63.7 (4)	C2—N1—C1'—C2'	−176.6 (2)
C27—N26—C25—O25	−4.1 (4)	O1'—C1'—C2'—C3'	−32.8 (4)
C27—N26—C25—C20	175.2 (2)	N1—C1'—C2'—C3'	149.8 (3)
N19—C20—C25—O25	−133.0 (3)	C1'—C2'—C3'—O3'	−63.4 (3)
C21—C20—C25—O25	104.0 (3)	C1'—C2'—C3'—C4'	174.4 (3)
N19—C20—C25—N26	47.7 (3)	O3'—C3'—C4'—C5'	67.6 (4)
C21—C20—C25—N26	−75.3 (3)	C2'—C3'—C4'—C5'	−172.4 (3)
C25—N26—C27—C28	−173.2 (2)	C3'—C4'—C5'—C6'	176.1 (4)
C25—N26—C27—C32	63.0 (3)	C4'—C5'—C6'—C7'A	165.0 (9)
N26—C27—C28—C29	58.4 (3)	C4'—C5'—C6'—C7'B	−79.9 (8)
C32—C27—C28—C29	−176.6 (2)	C4'—C5'—C6'—C7'	−161.3 (7)
C27—C28—C29—C31	178.1 (3)	C7'A—C6'—C7'—C8'	−77.8 (17)
C27—C28—C29—C30	53.5 (3)	C7'B—C6'—C7'—C8'	59.3 (11)
C34—N33—C32—O32	0.0 (4)	C5'—C6'—C7'—C8'	169.5 (9)
C34—N33—C32—C27	178.7 (2)	C6'—C7'—C8'—C9'	172.6 (11)
N26—C27—C32—O32	−147.0 (2)	C7'—C8'—C9'—C10'	56.9 (17)
C28—C27—C32—O32	90.0 (3)	C8'—C9'—C10'—C11'	60 (2)
N26—C27—C32—N33	34.3 (3)	C9'—C10'—C11'—C12'	172.1 (18)
C28—C27—C32—N33	−88.7 (3)	C7'B—C6'—C7'A—C8'A	−37.3 (11)
C32—N33—C34—C35	−140.1 (3)	C5'—C6'—C7'A—C8'A	87.1 (10)
C32—N33—C34—C36	96.6 (3)	C7'—C6'—C7'A—C8'A	3.5 (12)
N33—C34—C35—O35	−60.1 (3)	C6'—C7'A—C8'A—C9'A	94.9 (17)
C36—C34—C35—O35	65.6 (3)	C7'A—C8'A—C9'A—C10'A	109.1 (19)
C38—N37—C36—O36	0.9 (4)	C8'A—C9'A—C10'A—C11'A	72 (3)
C38—N37—C36—C34	−177.7 (2)	C9'A—C10'A—C11'A—C12'A	44 (3)
N33—C34—C36—O36	−178.5 (3)	C7'A—C6'—C7'B—C8'B	−24.6 (14)
C35—C34—C36—O36	57.1 (3)	C5'—C6'—C7'B—C8'B	−154.2 (10)
N33—C34—C36—N37	0.2 (4)	C7'—C6'—C7'B—C8'B	−44.9 (11)
C35—C34—C36—N37	−124.1 (3)	C6'—C7'B—C8'B—C9'B	87.8 (17)
C36—N37—C38—C39	171.4 (3)	C7'B—C8'B—C9'B—C10'B	74 (2)
C36—N37—C38—C43	−64.5 (3)	C8'B—C9'B—C10'B—C11'B	178.4 (14)
N37—C38—C39—C40	178.5 (2)	C9'B—C10'B—C11'B—C12'B	173.2 (15)
C43—C38—C39—C40	54.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12B—H12B···O25^i	0.84	1.81	2.645 (3)	170
O35—H35···O46	0.84	1.91	2.677 (3)	151
O46—H46···O1′^ii	0.84	1.94	2.785 (3)	179
O3′—H3′O···O35^iii	0.84	2.00	2.827 (3)	170
O3′—H3′O···O13^iii	0.84	2.73	3.176 (3)	115
O99—H99A···O43^iv	0.85	2.06	2.832 (3)	151
O99—H99B···O36^iv	0.87	1.90	2.766 (3)	170
N1—H1···O99	0.88	1.96	2.834 (3)	173
N8—H8···O47^iii	0.88	1.99	2.844 (3)	163
N14—H14···O1′	0.88	2.14	2.941 (3)	152
N19—H19···O7	0.88	2.39	2.955 (3)	123
N26—H26···O7	0.88	2.35	3.204 (3)	165
N33—H33···O13	0.88	2.08	2.863 (3)	148
N37—H37···O25	0.88	2.43	3.231 (3)	151
N37—H37···O18	0.88	2.51	2.995 (3)	115
N44—H44···O18	0.88	2.08	2.949 (3)	167
N48—H48···O32^v	0.88	2.38	3.057 (3)	134

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x−1/2, −y+1/2, −z+2; (iii) x+1/2, −y+1/2, −z+2; (iv) x+1, y, z; (v) −x, y−1/2, −z+3/2.