Crystal structure of the supramolecular linear polymer formed by the self-assembly of mono-6-deoxy-6-adamantylamide-β-cyclodextrin

Mono-6-deoxy-6-adamantylamide-β-cyclodextrin–dimethyl­form­amide–15H₂O, C₅₃H₈₅NO₃₅·C₃H₇NO·15H₂O, crystallizes in the orthorhombic space group P2₁2₁2₁. The adamantyl group is inserted into the cyclodextrin cavity of the adjacent molecule, entering by the side of the secondary hydroxy rim, thus forming a supramolecular linear polymer by self-assembly. Adjacent macrocycles are linked into columns by hydrogen bonds involving the nearest glucose residues, and the structure is further stabilized by their involvement in hydrogen bonding with water molecules which reside in channels surrounding the polymer columns, thus acting as bridges between the cyclodextrin units. The centroid of the adamantyl group lies below the plane formed by the seven glycosidic O atoms of the host cyclodextrin, excluding water molecules from the secondary side of β-cyclodextrin (β-CD). Between the adamantyl group and the primary hydroxy rim of the cyclodextrin cavity lies a dimethylformamide molecule, which shields the hydrophobic adamantyl group from the primary hydroxy rim of its carrying β-CD and excludes water molecules from the primary side of the β-CD cavity.

Computing details

Data collection: Collect (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures

(I)

Crystal data

C53H85NO35·C3H7NO·15(H2O)	F(000) = 3520
Mr = 1639.56	Dx = 1.391 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8125 reflections
a = 15.0687 (1) Å	θ = 1.0–74.5°
b = 17.6502 (2) Å	µ = 1.07 mm^−1
c = 29.4386 (3) Å	T = 100 K
V = 7829.65 (13) Å^3	Plate, colourless
Z = 4	0.63 × 0.2 × 0.05 mm

Data collection

Bruker-Nonius kCCD2000 diffractometer	13779 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
ω and phi scans	θmax = 72.4°, θmin = 3.3°
Absorption correction: multi-scan multi-scan from symmetry-related measurements SORTAV (Blessing 1995)	h = −17→18
Tmin = 0.731, Tmax = 0.955	k = −21→20
83976 measured reflections	l = −36→36
15082 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.085	w = 1/[σ^2(Fo^2) + (0.1598P)^2 + 4.5528P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.250	(Δ/σ)max = −0.048
S = 1.05	Δρmax = 1.10 e Å^−3
15082 reflections	Δρmin = −0.54 e Å^−3
914 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0028 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O51	0.2683 (2)	0.32625 (18)	0.31491 (11)	0.0458 (7)
C11	0.2340 (3)	0.3881 (3)	0.29048 (16)	0.0442 (9)
H102	0.1725	0.3754	0.2802	0.053*
C21	0.2301 (3)	0.4584 (3)	0.32045 (16)	0.0455 (9)
H103	0.1894	0.4481	0.3465	0.055*
C31	0.3223 (3)	0.4763 (3)	0.33916 (16)	0.0452 (9)
H104	0.3621	0.489	0.313	0.054*
C41	0.3604 (3)	0.4069 (3)	0.36343 (15)	0.0427 (9)
H105	0.3264	0.3967	0.392	0.051*
C51	0.3573 (3)	0.3370 (2)	0.33218 (15)	0.0430 (9)
H106	0.4001	0.3432	0.3065	0.052*
O41	0.28702 (19)	0.40411 (17)	0.25179 (10)	0.0425 (6)
O21	0.1953 (2)	0.5199 (2)	0.29476 (13)	0.0542 (8)
H108	0.1792	0.5546	0.3125	0.081*
O31	0.3192 (2)	0.54021 (19)	0.36893 (13)	0.0530 (8)
H109	0.288	0.5297	0.3917	0.079*
C61	0.3792 (4)	0.2659 (3)	0.35905 (17)	0.0509 (10)
H11A	0.4349	0.2744	0.3761	0.061*
H11B	0.3314	0.2568	0.3814	0.061*
N61	0.3892 (3)	0.1993 (2)	0.33093 (14)	0.0533 (9)
H1AN	0.4337	0.1992	0.3116	0.064*	0.506 (15)
H1BN	0.4129	0.2052	0.3038	0.064*	0.494 (15)
C112	0.3407 (8)	0.1414 (6)	0.3314 (4)	0.046 (2)*	0.506 (15)
O113	0.2686 (6)	0.1395 (5)	0.3506 (3)	0.064 (3)*	0.506 (15)
C912	0.3635 (9)	0.1280 (7)	0.3436 (5)	0.058 (3)*	0.494 (15)
O913	0.3211 (12)	0.1149 (9)	0.3783 (6)	0.127 (6)*	0.494 (15)
C114	0.3781 (3)	0.0662 (3)	0.30839 (18)	0.0533 (11)
C115	0.3500 (3)	−0.0056 (3)	0.33257 (17)	0.0510 (10)
H11C	0.2852	−0.0044	0.338	0.061*
H11D	0.3802	−0.0087	0.3624	0.061*
C116	0.3734 (4)	−0.0751 (3)	0.30408 (18)	0.0540 (11)
H116	0.3539	−0.1217	0.3205	0.065*
C117	0.3243 (3)	−0.0704 (3)	0.2579 (2)	0.0573 (12)
H11E	0.339	−0.1152	0.2391	0.069*
H11F	0.2594	−0.0697	0.2629	0.069*
C118	0.3535 (4)	0.0023 (3)	0.23346 (18)	0.0577 (12)
H118	0.3227	0.006	0.2035	0.069*
C119	0.3316 (4)	0.0718 (3)	0.26217 (18)	0.0568 (12)
H11G	0.2666	0.0751	0.2667	0.068*
H11H	0.3513	0.1182	0.2462	0.068*
C120	0.4786 (4)	0.0637 (4)	0.3009 (2)	0.0654 (15)
H12A	0.5095	0.0605	0.3305	0.078*
H12B	0.4984	0.1104	0.2853	0.078*
C121	0.5020 (3)	−0.0066 (3)	0.27149 (18)	0.0535 (11)
H121	0.5675	−0.0082	0.2664	0.064*
C122	0.4729 (4)	−0.0787 (3)	0.2963 (2)	0.0608 (13)
H12C	0.4878	−0.1238	0.2777	0.073*
H12D	0.5043	−0.0829	0.3257	0.073*
C123	0.4551 (4)	−0.0014 (3)	0.22592 (18)	0.0570 (12)
H12E	0.47	−0.0462	0.2072	0.068*
H12F	0.4751	0.0445	0.2095	0.068*
O52	0.2516 (2)	0.32133 (19)	0.13800 (10)	0.0453 (7)
C12	0.2666 (3)	0.3875 (3)	0.11143 (16)	0.0478 (10)
H202	0.2396	0.38	0.0807	0.057*
C22	0.2233 (3)	0.4560 (3)	0.13393 (17)	0.0520 (11)
H203	0.1581	0.4462	0.1364	0.062*
C32	0.2605 (3)	0.4664 (3)	0.18144 (17)	0.0481 (10)
H204	0.3254	0.4776	0.1795	0.058*
C42	0.2466 (3)	0.3947 (3)	0.20784 (15)	0.0425 (9)
H205	0.1815	0.3859	0.2118	0.051*
C52	0.2872 (3)	0.3272 (3)	0.18362 (14)	0.0414 (8)
H206	0.353	0.3336	0.1821	0.05*
O42	0.35744 (19)	0.40321 (18)	0.10623 (10)	0.0430 (6)
O22	0.2362 (3)	0.5216 (2)	0.10668 (15)	0.0708 (12)
H208	0.2838	0.5173	0.092	0.106*
O32	0.2162 (3)	0.5280 (2)	0.20268 (15)	0.0625 (10)
H209	0.2377	0.5349	0.2287	0.094*
C62	0.2656 (3)	0.2520 (3)	0.20589 (16)	0.0454 (9)
H21A	0.2889	0.2101	0.187	0.055*
H21B	0.2948	0.2493	0.236	0.055*
O62	0.1706 (2)	0.24318 (19)	0.21138 (12)	0.0489 (7)
H211	0.1579	0.1969	0.2125	0.073*
O53	0.51349 (19)	0.33180 (17)	0.01983 (10)	0.0412 (6)
C13	0.5625 (3)	0.3992 (2)	0.01383 (14)	0.0384 (8)
H302	0.5971	0.3953	−0.0151	0.046*
C23	0.5011 (3)	0.4669 (2)	0.01070 (14)	0.0390 (8)
H303	0.4598	0.4586	−0.0154	0.047*
C33	0.4459 (3)	0.4724 (2)	0.05416 (15)	0.0414 (8)
H304	0.4866	0.482	0.0804	0.05*
C43	0.3969 (3)	0.3985 (2)	0.06213 (14)	0.0394 (8)
H305	0.3495	0.3922	0.0387	0.047*
C53	0.4601 (3)	0.3307 (2)	0.06053 (14)	0.0397 (8)
H306	0.5002	0.3328	0.0876	0.048*
O43	0.62266 (17)	0.41201 (16)	0.05029 (9)	0.0379 (6)
O23	0.5499 (2)	0.53397 (18)	0.00242 (11)	0.0479 (7)
H308	0.5446	0.5463	−0.025	0.072*
O33	0.3846 (2)	0.53305 (18)	0.05095 (12)	0.0478 (7)
H309	0.4116	0.5744	0.054	0.072*
C63	0.4131 (3)	0.2564 (3)	0.06022 (18)	0.0480 (10)
H31A	0.3726	0.2531	0.0866	0.058*
H31B	0.3772	0.2516	0.0322	0.058*
O63	0.4771 (2)	0.19690 (18)	0.06219 (13)	0.0516 (8)
H311	0.455	0.1593	0.0756	0.077*
O54	0.83912 (19)	0.32858 (19)	0.07667 (11)	0.0459 (7)
C14	0.8875 (3)	0.3964 (3)	0.08302 (14)	0.0439 (9)
H402	0.9524	0.3853	0.0813	0.053*
C24	0.8632 (3)	0.4541 (3)	0.04660 (15)	0.0447 (9)
H403	0.8771	0.4316	0.0163	0.054*
C34	0.7647 (3)	0.4696 (3)	0.04860 (14)	0.0396 (8)
H404	0.7502	0.4913	0.0791	0.048*
C44	0.7144 (2)	0.3960 (2)	0.04285 (13)	0.0381 (8)
H405	0.7233	0.3758	0.0115	0.046*
C054	0.7448 (3)	0.3377 (3)	0.07788 (15)	0.0421 (9)
H406	0.7276	0.3562	0.1088	0.051*
O44	0.8675 (2)	0.4273 (2)	0.12617 (10)	0.0520 (8)
O24	0.9153 (2)	0.5212 (2)	0.05201 (12)	0.0520 (8)
H408	0.9695	0.5098	0.0513	0.078*
O34	0.7382 (2)	0.52261 (18)	0.01444 (10)	0.0436 (6)
H409	0.6826	0.5265	0.0144	0.065*
C64	0.7068 (3)	0.2601 (3)	0.07142 (17)	0.0493 (10)
H41A	0.7237	0.2272	0.0973	0.059*
H41B	0.6413	0.2629	0.0702	0.059*
O64	0.7410 (2)	0.2284 (2)	0.02914 (12)	0.0544 (8)
H411	0.6997	0.2069	0.015	0.082*
O55	1.01769 (18)	0.41326 (17)	0.22387 (9)	0.0392 (6)
C15	1.0010 (3)	0.4844 (3)	0.24403 (15)	0.0409 (9)
H502	1.0512	0.4971	0.2649	0.049*
C25	0.9937 (3)	0.5464 (2)	0.20761 (15)	0.0452 (9)
H503	1.0517	0.55	0.1913	0.054*
C35	0.9223 (4)	0.5259 (3)	0.17359 (16)	0.0538 (11)
H504	0.8635	0.5256	0.1893	0.065*
C45	0.9405 (3)	0.4472 (2)	0.15478 (15)	0.0416 (8)
H505	0.9963	0.4481	0.1365	0.05*
C55	0.9494 (3)	0.3894 (3)	0.19298 (13)	0.0397 (8)
H506	0.8919	0.3865	0.2098	0.048*
O45	0.92158 (18)	0.48354 (17)	0.26912 (9)	0.0384 (6)
O25	0.9757 (3)	0.6179 (2)	0.22876 (13)	0.0609 (9)
H508	0.9619	0.6498	0.2088	0.091*
O35	0.9197 (4)	0.5794 (2)	0.13797 (13)	0.0884 (17)
H509	0.8771	0.6093	0.1421	0.133*
C65	0.9737 (3)	0.3115 (3)	0.17651 (16)	0.0454 (9)
H51A	0.9832	0.2779	0.203	0.055*
H51B	0.9237	0.2906	0.1586	0.055*
O65	1.0520 (2)	0.31164 (19)	0.14902 (11)	0.0479 (7)
H511	1.0962	0.3009	0.1652	0.072*
O56	0.87668 (19)	0.41051 (17)	0.38393 (10)	0.0401 (6)
C16	0.8244 (3)	0.4722 (2)	0.39979 (15)	0.0411 (8)
H602	0.8199	0.4695	0.4336	0.049*
C26	0.8665 (3)	0.5468 (2)	0.38637 (14)	0.0406 (9)
H603	0.9264	0.5506	0.4008	0.049*
C36	0.8768 (3)	0.5516 (2)	0.33520 (14)	0.0386 (8)
H604	0.8165	0.5524	0.321	0.046*
C46	0.9270 (3)	0.4828 (2)	0.31779 (13)	0.0371 (8)
H605	0.9906	0.4861	0.3274	0.045*
C56	0.8868 (3)	0.4087 (2)	0.33514 (14)	0.0400 (8)
H606	0.8269	0.4022	0.3211	0.048*
O46	0.73828 (18)	0.46885 (16)	0.38083 (10)	0.0388 (6)
O26	0.8111 (2)	0.60633 (18)	0.40343 (12)	0.0488 (7)
H608	0.8423	0.6447	0.4089	0.059*
O36	0.9227 (2)	0.61926 (18)	0.32270 (12)	0.0484 (7)
H609	0.9699	0.6227	0.3378	0.073*
C66	0.9417 (3)	0.3392 (3)	0.32488 (15)	0.0440 (9)
H61A	0.9129	0.2936	0.3378	0.053*
H61B	0.947	0.3323	0.2916	0.053*
O66	1.0280 (2)	0.34913 (19)	0.34459 (12)	0.0496 (7)
H611	1.0623	0.3152	0.335	0.074*
O57	0.5481 (2)	0.35328 (17)	0.41761 (11)	0.0451 (7)
C17	0.4814 (3)	0.4106 (3)	0.41821 (15)	0.0424 (9)
H702	0.4308	0.3934	0.4376	0.051*
C27	0.5192 (3)	0.4837 (3)	0.43769 (15)	0.0440 (9)
H703	0.5389	0.474	0.4696	0.053*
C37	0.5990 (3)	0.5079 (2)	0.40991 (14)	0.0376 (8)
H704	0.5799	0.5188	0.3781	0.045*
C47	0.6667 (3)	0.4444 (2)	0.40962 (15)	0.0411 (9)
H705	0.689	0.4348	0.4411	0.049*
C57	0.6249 (3)	0.3729 (2)	0.39019 (16)	0.0443 (9)
H706	0.6066	0.3817	0.358	0.053*
O47	0.45047 (19)	0.42487 (17)	0.37399 (10)	0.0415 (6)
O27	0.4523 (2)	0.54120 (19)	0.43818 (11)	0.0481 (7)
H708	0.4135	0.5311	0.4186	0.072*
O37	0.63420 (19)	0.57514 (17)	0.42980 (11)	0.0428 (6)
H709	0.6865	0.5816	0.4208	0.064*
C67	0.6842 (3)	0.3048 (3)	0.3931 (2)	0.0544 (11)
H71A	0.7418	0.3166	0.3785	0.065*
H71B	0.6958	0.2929	0.4254	0.065*
O67	0.6465 (3)	0.2406 (2)	0.37178 (18)	0.0720 (11)
H711	0.6209	0.2137	0.3913	0.108*
O1	0.4799 (6)	0.2402 (5)	0.2506 (3)	0.135 (3)*
C2	0.5620 (7)	0.2319 (6)	0.2470 (4)	0.106 (3)*
H2	0.5962	0.2369	0.274	0.127*
N3	0.6059 (5)	0.2166 (4)	0.2085 (3)	0.0967 (19)*
C4	0.6975 (7)	0.2070 (6)	0.2047 (4)	0.111 (3)*
H4A	0.7241	0.2061	0.2351	0.167*
H4B	0.7227	0.249	0.1872	0.167*
H4C	0.7101	0.159	0.1892	0.167*
C5	0.5515 (8)	0.2073 (6)	0.1658 (4)	0.116 (3)*
H5A	0.4884	0.2123	0.1731	0.173*
H5B	0.5626	0.1572	0.1527	0.173*
H5C	0.5683	0.2465	0.1438	0.173*
O1W	1.0651 (2)	0.21632 (18)	0.07660 (11)	0.0497 (7)*
O2W	0.5909 (2)	0.17237 (19)	−0.01081 (12)	0.0531 (8)*
O3W	0.4408 (3)	0.5997 (2)	−0.06552 (15)	0.0697 (10)*
O4W	0.8893 (3)	0.1560 (2)	0.06826 (14)	0.0628 (9)*
O5W	0.1872 (3)	0.5157 (3)	0.43112 (15)	0.0731 (11)*
O6W	1.0936 (3)	0.4773 (3)	0.04337 (16)	0.0740 (11)*
O7W	0.1047 (3)	0.6291 (3)	0.33936 (16)	0.0737 (11)*
O8W	0.7778 (4)	0.1765 (3)	0.32197 (18)	0.0847 (13)*
O9W	0.1262 (4)	0.2283 (3)	0.3083 (2)	0.0938 (15)*
O10W	0.4601 (5)	0.6714 (4)	0.0674 (2)	0.1091 (18)*
O11W	0.7580 (5)	0.6686 (5)	0.0503 (3)	0.124 (2)*
O12W	1.1140 (6)	0.6976 (5)	0.2472 (3)	0.129 (2)*
O13W	0.1041 (6)	0.6372 (5)	0.1108 (3)	0.138 (3)*
O14W	0.2165 (8)	0.5587 (6)	−0.0058 (4)	0.120 (4)*	0.688 (13)
O15W	0.5938 (7)	0.7309 (6)	0.0209 (4)	0.130 (4)*	0.759 (14)
O16W	0.8239 (10)	0.8036 (8)	0.0154 (5)	0.069 (4)*	0.312 (13)
O17W	0.5535 (13)	0.7879 (10)	−0.0432 (6)	0.070 (6)*	0.241 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O51	0.0414 (15)	0.0461 (15)	0.0498 (17)	−0.0073 (13)	0.0030 (13)	0.0002 (13)
C11	0.036 (2)	0.052 (2)	0.045 (2)	−0.0017 (17)	0.0033 (17)	0.0001 (18)
C21	0.038 (2)	0.050 (2)	0.049 (2)	−0.0024 (17)	0.0031 (18)	−0.0037 (18)
C31	0.036 (2)	0.048 (2)	0.052 (2)	0.0021 (17)	0.0011 (18)	−0.0091 (19)
C41	0.037 (2)	0.050 (2)	0.041 (2)	−0.0041 (17)	0.0040 (16)	−0.0047 (17)
C51	0.043 (2)	0.046 (2)	0.041 (2)	−0.0039 (17)	0.0003 (17)	0.0006 (17)
O41	0.0351 (14)	0.0486 (15)	0.0439 (15)	−0.0018 (12)	0.0048 (12)	−0.0014 (12)
O21	0.0425 (16)	0.0537 (17)	0.066 (2)	0.0065 (14)	−0.0081 (15)	−0.0105 (15)
O31	0.0488 (18)	0.0502 (17)	0.060 (2)	0.0019 (14)	−0.0006 (15)	−0.0123 (15)
C61	0.060 (3)	0.041 (2)	0.052 (2)	−0.0037 (19)	−0.003 (2)	0.0018 (18)
N61	0.065 (3)	0.047 (2)	0.048 (2)	0.0004 (18)	0.0034 (19)	0.0035 (16)
C114	0.051 (3)	0.049 (2)	0.060 (3)	−0.007 (2)	0.007 (2)	−0.005 (2)
C115	0.044 (2)	0.063 (3)	0.047 (2)	−0.001 (2)	0.0052 (19)	0.001 (2)
C116	0.051 (3)	0.055 (3)	0.056 (3)	0.002 (2)	0.007 (2)	0.010 (2)
C117	0.045 (2)	0.060 (3)	0.066 (3)	−0.001 (2)	0.002 (2)	−0.012 (2)
C118	0.056 (3)	0.072 (3)	0.046 (2)	0.011 (2)	−0.003 (2)	0.001 (2)
C119	0.054 (3)	0.062 (3)	0.054 (3)	0.017 (2)	0.013 (2)	0.010 (2)
C120	0.047 (3)	0.075 (3)	0.073 (4)	−0.016 (2)	0.014 (2)	−0.017 (3)
C121	0.040 (2)	0.067 (3)	0.053 (3)	0.002 (2)	0.0044 (19)	−0.002 (2)
C122	0.058 (3)	0.069 (3)	0.055 (3)	0.012 (3)	−0.001 (2)	0.003 (2)
C123	0.053 (3)	0.067 (3)	0.051 (3)	0.009 (2)	0.006 (2)	0.001 (2)
O52	0.0362 (14)	0.0585 (17)	0.0411 (15)	−0.0062 (13)	−0.0021 (12)	0.0036 (13)
C12	0.036 (2)	0.064 (3)	0.043 (2)	−0.0024 (19)	−0.0022 (17)	0.0109 (19)
C22	0.038 (2)	0.064 (3)	0.054 (3)	0.012 (2)	0.0003 (19)	0.016 (2)
C32	0.036 (2)	0.048 (2)	0.060 (3)	0.0082 (17)	0.0108 (19)	0.003 (2)
C42	0.0292 (18)	0.053 (2)	0.045 (2)	0.0030 (16)	−0.0040 (16)	0.0038 (18)
C52	0.0353 (19)	0.050 (2)	0.038 (2)	0.0016 (17)	−0.0030 (16)	0.0002 (17)
O42	0.0314 (13)	0.0554 (16)	0.0422 (15)	0.0019 (12)	0.0008 (12)	0.0025 (13)
O22	0.061 (2)	0.076 (2)	0.075 (2)	0.0320 (19)	0.0270 (19)	0.036 (2)
O32	0.059 (2)	0.0461 (17)	0.082 (3)	0.0147 (16)	0.0246 (19)	0.0099 (17)
C62	0.041 (2)	0.048 (2)	0.047 (2)	0.0001 (17)	−0.0023 (18)	−0.0003 (18)
O62	0.0419 (16)	0.0529 (17)	0.0519 (17)	−0.0046 (13)	0.0065 (13)	−0.0018 (14)
O53	0.0348 (13)	0.0450 (15)	0.0437 (15)	−0.0024 (11)	0.0005 (11)	−0.0006 (12)
C13	0.0331 (18)	0.045 (2)	0.0375 (19)	−0.0010 (16)	−0.0017 (15)	−0.0015 (15)
C23	0.0347 (19)	0.043 (2)	0.039 (2)	0.0000 (16)	−0.0028 (15)	0.0061 (15)
C33	0.0340 (19)	0.045 (2)	0.045 (2)	0.0079 (16)	0.0013 (16)	0.0031 (17)
C43	0.0311 (18)	0.046 (2)	0.041 (2)	0.0029 (16)	−0.0008 (15)	0.0023 (16)
C53	0.0307 (18)	0.048 (2)	0.040 (2)	0.0014 (16)	0.0029 (15)	0.0008 (16)
O43	0.0281 (12)	0.0496 (15)	0.0359 (13)	0.0018 (11)	−0.0034 (11)	−0.0019 (11)
O23	0.0453 (16)	0.0461 (15)	0.0522 (17)	−0.0026 (13)	0.0003 (14)	0.0081 (13)
O33	0.0420 (15)	0.0448 (15)	0.0567 (18)	0.0068 (13)	0.0015 (14)	0.0041 (14)
C63	0.041 (2)	0.043 (2)	0.059 (3)	0.0027 (17)	−0.0013 (19)	0.0016 (19)
O63	0.0419 (16)	0.0460 (16)	0.067 (2)	0.0019 (13)	0.0034 (15)	0.0043 (14)
O54	0.0318 (14)	0.0604 (17)	0.0457 (16)	0.0031 (13)	−0.0025 (12)	−0.0015 (14)
C14	0.0298 (18)	0.064 (3)	0.038 (2)	0.0089 (18)	0.0017 (16)	−0.0072 (18)
C24	0.0333 (19)	0.061 (2)	0.040 (2)	0.0003 (18)	0.0023 (16)	−0.0051 (18)
C34	0.0321 (18)	0.055 (2)	0.0323 (18)	0.0016 (16)	−0.0009 (15)	0.0040 (16)
C44	0.0276 (17)	0.054 (2)	0.0331 (18)	0.0021 (16)	−0.0005 (14)	0.0027 (16)
C054	0.0318 (19)	0.053 (2)	0.041 (2)	0.0093 (17)	0.0017 (16)	0.0065 (17)
O44	0.0347 (15)	0.086 (2)	0.0358 (15)	0.0123 (15)	−0.0038 (12)	−0.0127 (15)
O24	0.0360 (15)	0.070 (2)	0.0500 (17)	−0.0112 (14)	0.0018 (13)	−0.0088 (15)
O34	0.0406 (15)	0.0500 (16)	0.0402 (15)	−0.0020 (13)	−0.0025 (12)	0.0089 (12)
C64	0.041 (2)	0.055 (2)	0.052 (2)	0.0084 (19)	0.0047 (19)	0.007 (2)
O64	0.0466 (17)	0.0586 (19)	0.058 (2)	0.0057 (15)	0.0047 (15)	−0.0029 (15)
O55	0.0313 (13)	0.0492 (15)	0.0371 (14)	0.0037 (11)	−0.0039 (11)	−0.0047 (11)
C15	0.0323 (18)	0.048 (2)	0.042 (2)	−0.0025 (16)	−0.0004 (15)	−0.0023 (17)
C25	0.054 (2)	0.040 (2)	0.041 (2)	0.0012 (17)	0.0067 (19)	−0.0034 (17)
C35	0.065 (3)	0.058 (3)	0.038 (2)	0.018 (2)	−0.008 (2)	0.0009 (19)
C45	0.0362 (19)	0.048 (2)	0.040 (2)	0.0073 (16)	−0.0046 (16)	−0.0028 (16)
C55	0.0326 (18)	0.056 (2)	0.0301 (17)	−0.0035 (17)	−0.0006 (15)	−0.0040 (16)
O45	0.0310 (13)	0.0521 (15)	0.0321 (13)	−0.0003 (11)	0.0015 (10)	−0.0008 (11)
O25	0.082 (3)	0.0423 (17)	0.058 (2)	0.0028 (17)	0.0091 (19)	−0.0028 (14)
O35	0.164 (5)	0.061 (2)	0.0403 (18)	0.051 (3)	−0.007 (2)	0.0031 (16)
C65	0.041 (2)	0.049 (2)	0.047 (2)	−0.0038 (17)	−0.0003 (18)	−0.0065 (18)
O65	0.0417 (15)	0.0608 (18)	0.0412 (16)	0.0073 (14)	0.0034 (13)	−0.0046 (13)
O56	0.0371 (14)	0.0454 (15)	0.0377 (14)	0.0060 (12)	0.0001 (11)	−0.0027 (11)
C16	0.0357 (19)	0.046 (2)	0.041 (2)	0.0029 (16)	0.0024 (16)	−0.0092 (17)
C26	0.0347 (19)	0.049 (2)	0.038 (2)	0.0008 (16)	0.0037 (16)	−0.0077 (16)
C36	0.0346 (19)	0.043 (2)	0.039 (2)	−0.0005 (15)	0.0027 (15)	−0.0047 (15)
C46	0.0355 (18)	0.046 (2)	0.0297 (17)	0.0031 (16)	−0.0012 (14)	−0.0032 (15)
C56	0.038 (2)	0.045 (2)	0.0365 (19)	0.0005 (16)	0.0009 (16)	−0.0041 (16)
O46	0.0328 (13)	0.0463 (14)	0.0372 (14)	0.0011 (11)	0.0017 (11)	−0.0006 (11)
O26	0.0453 (16)	0.0469 (16)	0.0544 (18)	−0.0003 (13)	0.0099 (14)	−0.0123 (13)
O36	0.0457 (16)	0.0442 (15)	0.0554 (18)	−0.0011 (13)	0.0063 (14)	−0.0002 (13)
C66	0.041 (2)	0.047 (2)	0.044 (2)	0.0000 (17)	0.0015 (17)	−0.0019 (17)
O66	0.0443 (16)	0.0526 (17)	0.0519 (17)	0.0078 (13)	−0.0031 (14)	−0.0068 (14)
O57	0.0406 (15)	0.0456 (15)	0.0492 (16)	−0.0004 (12)	0.0102 (13)	0.0002 (12)
C17	0.0353 (19)	0.051 (2)	0.041 (2)	−0.0006 (17)	0.0046 (16)	0.0008 (17)
C27	0.039 (2)	0.049 (2)	0.044 (2)	−0.0006 (17)	0.0041 (17)	−0.0073 (17)
C37	0.0305 (17)	0.044 (2)	0.0383 (19)	0.0018 (15)	0.0013 (15)	−0.0049 (15)
C47	0.0344 (19)	0.047 (2)	0.042 (2)	−0.0001 (16)	0.0027 (16)	−0.0006 (17)
C57	0.041 (2)	0.043 (2)	0.049 (2)	−0.0010 (17)	0.0068 (18)	−0.0034 (17)
O47	0.0348 (14)	0.0501 (15)	0.0395 (14)	−0.0016 (12)	0.0014 (11)	0.0004 (12)
O27	0.0379 (15)	0.0551 (17)	0.0512 (17)	0.0035 (13)	0.0043 (13)	−0.0133 (14)
O37	0.0353 (14)	0.0423 (14)	0.0508 (16)	0.0001 (11)	0.0007 (12)	−0.0089 (12)
C67	0.043 (2)	0.045 (2)	0.075 (3)	0.0035 (19)	0.010 (2)	−0.008 (2)
O67	0.069 (2)	0.0471 (18)	0.100 (3)	−0.0046 (17)	0.022 (2)	−0.011 (2)

Geometric parameters (Å, º)

O51—C11	1.405 (6)	O63—H311	0.84
O51—C51	1.447 (5)	O54—C14	1.414 (6)
C11—O41	1.420 (5)	O54—C054	1.431 (5)
C11—C21	1.524 (6)	C14—O44	1.415 (5)
C11—H102	1	C14—C24	1.523 (7)
C21—O21	1.423 (6)	C14—H402	1
C21—C31	1.527 (6)	C24—O24	1.430 (6)
C21—H103	1	C24—C34	1.511 (6)
C31—O31	1.430 (5)	C24—H403	1
C31—C41	1.530 (6)	C34—O34	1.430 (5)
C31—H104	1	C34—C44	1.513 (6)
C41—O47	1.429 (5)	C34—H404	1
C41—C51	1.539 (6)	C44—C054	1.527 (6)
C41—H105	1	C44—H405	1
C51—C61	1.519 (6)	C054—C64	1.497 (7)
C51—H106	1	C054—H406	1
O41—C42	1.440 (5)	O44—C45	1.430 (5)
O21—H108	0.84	O24—H408	0.84
O31—H109	0.84	O34—H409	0.84
C61—N61	1.447 (6)	C64—O64	1.458 (6)
C61—H11A	0.99	C64—H41A	0.99
C61—H11B	0.99	C64—H41B	0.99
N61—C112	1.256 (11)	O64—H411	0.84
N61—C912	1.368 (14)	O55—C15	1.412 (5)
N61—H1AN	0.88	O55—C55	1.436 (5)
N61—H1BN	0.88	C15—O45	1.406 (5)
C112—O113	1.225 (13)	C15—C25	1.535 (6)
C112—C114	1.594 (11)	C15—H502	1
C912—O913	1.23 (2)	C25—O25	1.433 (5)
C912—C114	1.521 (13)	C25—C35	1.514 (7)
C114—C115	1.514 (7)	C25—H503	1
C114—C120	1.531 (7)	C35—O35	1.411 (6)
C114—C119	1.534 (8)	C35—C45	1.521 (6)
C115—C116	1.527 (7)	C35—H504	1
C115—H11C	0.99	C45—C55	1.524 (6)
C115—H11D	0.99	C45—H505	1
C116—C122	1.518 (8)	C55—C65	1.504 (6)
C116—C117	1.549 (8)	C55—H506	1
C116—H116	1	O45—C46	1.435 (4)
C117—C118	1.536 (8)	O25—H508	0.84
C117—H11E	0.99	O35—H509	0.84
C117—H11F	0.99	C65—O65	1.431 (6)
C118—C119	1.526 (8)	C65—H51A	0.99
C118—C123	1.547 (7)	C65—H51B	0.99
C118—H118	1	O65—H511	0.84
C119—H11G	0.99	O56—C16	1.422 (5)
C119—H11H	0.99	O56—C56	1.445 (5)
C120—C121	1.553 (8)	C16—O46	1.414 (5)
C120—H12A	0.99	C16—C26	1.514 (6)
C120—H12B	0.99	C16—H602	1
C121—C123	1.519 (7)	C26—O26	1.433 (5)
C121—C122	1.531 (8)	C26—C36	1.517 (6)
C121—H121	1	C26—H603	1
C122—H12C	0.99	C36—O36	1.428 (5)
C122—H12D	0.99	C36—C46	1.521 (5)
C123—H12E	0.99	C36—H604	1
C123—H12F	0.99	C46—C56	1.529 (6)
O52—C12	1.424 (6)	C46—H605	1
O52—C52	1.449 (5)	C56—C66	1.511 (6)
C12—O42	1.405 (5)	C56—H606	1
C12—C22	1.525 (7)	O46—C47	1.438 (5)
C12—H202	1	O26—H608	0.84
C22—O22	1.423 (6)	O36—H609	0.84
C22—C32	1.518 (7)	C66—O66	1.434 (5)
C22—H203	1	C66—H61A	0.99
C32—O32	1.419 (5)	C66—H61B	0.99
C32—C42	1.500 (6)	O66—H611	0.84
C32—H204	1	O57—C17	1.425 (5)
C42—C52	1.518 (6)	O57—C57	1.454 (5)
C42—H205	1	C17—O47	1.406 (5)
C52—C62	1.515 (6)	C17—C27	1.522 (6)
C52—H206	1	C17—H702	1
O42—C43	1.430 (5)	C27—O27	1.431 (5)
O22—H208	0.84	C27—C37	1.516 (6)
O32—H209	0.84	C27—H703	1
C62—O62	1.450 (5)	C37—O37	1.426 (5)
C62—H21A	0.99	C37—C47	1.515 (6)
C62—H21B	0.99	C37—H704	1
O62—H211	0.84	C47—C57	1.522 (6)
O53—C13	1.412 (5)	C47—H705	1
O53—C53	1.443 (5)	C57—C67	1.501 (6)
C13—O43	1.423 (5)	C57—H706	1
C13—C23	1.513 (6)	O27—H708	0.84
C13—H302	1	O37—H709	0.84
C23—O23	1.415 (5)	C67—O67	1.413 (6)
C23—C33	1.529 (6)	C67—H71A	0.99
C23—H303	1	C67—H71B	0.99
C33—O33	1.416 (5)	O67—H711	0.84
C33—C43	1.518 (6)	O1—C2	1.250 (13)
C33—H304	1	C2—N3	1.341 (12)
C43—C53	1.529 (6)	C2—H2	0.95
C43—H305	1	N3—C4	1.395 (13)
C53—C63	1.491 (6)	N3—C5	1.511 (13)
C53—H306	1	C4—H4A	0.98
O43—C44	1.427 (5)	C4—H4B	0.98
O23—H308	0.84	C4—H4C	0.98
O33—H309	0.84	C5—H5A	0.98
C63—O63	1.427 (5)	C5—H5B	0.98
C63—H31A	0.99	C5—H5C	0.98
C63—H31B	0.99
C11—O51—C51	114.8 (3)	C33—O33—H309	109.5
O51—C11—O41	111.0 (3)	O63—C63—C53	109.0 (4)
O51—C11—C21	110.5 (4)	O63—C63—H31A	109.9
O41—C11—C21	108.9 (3)	C53—C63—H31A	109.9
O51—C11—H102	108.8	O63—C63—H31B	109.9
O41—C11—H102	108.8	C53—C63—H31B	109.9
C21—C11—H102	108.8	H31A—C63—H31B	108.3
O21—C21—C11	109.1 (4)	C63—O63—H311	109.5
O21—C21—C31	111.7 (4)	C14—O54—C054	114.4 (3)
C11—C21—C31	110.1 (4)	O44—C14—O54	109.6 (4)
O21—C21—H103	108.6	O44—C14—C24	108.9 (4)
C11—C21—H103	108.6	O54—C14—C24	110.4 (3)
C31—C21—H103	108.6	O44—C14—H402	109.3
O31—C31—C21	110.8 (3)	O54—C14—H402	109.3
O31—C31—C41	111.0 (4)	C24—C14—H402	109.3
C21—C31—C41	110.1 (4)	O24—C24—C34	112.7 (4)
O31—C31—H104	108.3	O24—C24—C14	110.1 (4)
C21—C31—H104	108.3	C34—C24—C14	109.3 (3)
C41—C31—H104	108.3	O24—C24—H403	108.3
O47—C41—C31	106.2 (3)	C34—C24—H403	108.3
O47—C41—C51	109.7 (3)	C14—C24—H403	108.3
C31—C41—C51	110.6 (4)	O34—C34—C24	111.5 (3)
O47—C41—H105	110.1	O34—C34—C44	110.1 (3)
C31—C41—H105	110.1	C24—C34—C44	109.4 (4)
C51—C41—H105	110.1	O34—C34—H404	108.6
O51—C51—C61	106.0 (4)	C24—C34—H404	108.6
O51—C51—C41	110.0 (3)	C44—C34—H404	108.6
C61—C51—C41	110.1 (4)	O43—C44—C34	107.4 (3)
O51—C51—H106	110.2	O43—C44—C054	108.7 (3)
C61—C51—H106	110.2	C34—C44—C054	110.6 (3)
C41—C51—H106	110.2	O43—C44—H405	110
C11—O41—C42	117.4 (3)	C34—C44—H405	110
C21—O21—H108	109.5	C054—C44—H405	110
C31—O31—H109	109.5	O54—C054—C64	105.9 (3)
N61—C61—C51	113.4 (4)	O54—C054—C44	110.9 (3)
N61—C61—H11A	108.9	C64—C054—C44	114.6 (4)
C51—C61—H11A	108.9	O54—C054—H406	108.4
N61—C61—H11B	108.9	C64—C054—H406	108.4
C51—C61—H11B	108.9	C44—C054—H406	108.4
H11A—C61—H11B	107.7	C14—O44—C45	117.4 (3)
C112—N61—C61	126.4 (6)	C24—O24—H408	109.5
C912—N61—C61	124.2 (6)	C34—O34—H409	109.5
C112—N61—H1AN	116.8	O64—C64—C054	108.9 (4)
C912—N61—H1AN	113.1	O64—C64—H41A	109.9
C61—N61—H1AN	116.8	C054—C64—H41A	109.9
C112—N61—H1BN	110.1	O64—C64—H41B	109.9
C912—N61—H1BN	118.2	C054—C64—H41B	109.9
C61—N61—H1BN	117.6	H41A—C64—H41B	108.3
O113—C112—N61	123.0 (9)	C64—O64—H411	109.5
O113—C112—C114	119.2 (8)	C15—O55—C55	113.5 (3)
N61—C112—C114	117.8 (8)	O45—C15—O55	111.3 (3)
O913—C912—N61	123.3 (13)	O45—C15—C25	108.3 (3)
O913—C912—C114	120.5 (12)	O55—C15—C25	110.7 (3)
N61—C912—C114	115.6 (9)	O45—C15—H502	108.9
C115—C114—C912	103.8 (6)	O55—C15—H502	108.9
C115—C114—C120	108.7 (5)	C25—C15—H502	108.9
C912—C114—C120	105.2 (6)	O25—C25—C35	111.3 (4)
C115—C114—C119	110.0 (4)	O25—C25—C15	109.7 (4)
C912—C114—C119	119.5 (7)	C35—C25—C15	110.1 (4)
C120—C114—C119	109.1 (5)	O25—C25—H503	108.6
C115—C114—C112	113.4 (5)	C35—C25—H503	108.6
C120—C114—C112	115.8 (5)	C15—C25—H503	108.6
C119—C114—C112	99.3 (6)	O35—C35—C25	110.6 (5)
C114—C115—C116	110.4 (4)	O35—C35—C45	110.2 (4)
C114—C115—H11C	109.6	C25—C35—C45	109.3 (4)
C116—C115—H11C	109.6	O35—C35—H504	108.9
C114—C115—H11D	109.6	C25—C35—H504	108.9
C116—C115—H11D	109.6	C45—C35—H504	108.9
H11C—C115—H11D	108.1	O44—C45—C35	107.5 (4)
C122—C116—C115	110.2 (5)	O44—C45—C55	109.8 (4)
C122—C116—C117	109.9 (4)	C35—C45—C55	111.0 (4)
C115—C116—C117	109.2 (4)	O44—C45—H505	109.5
C122—C116—H116	109.2	C35—C45—H505	109.5
C115—C116—H116	109.2	C55—C45—H505	109.5
C117—C116—H116	109.2	O55—C55—C65	107.4 (3)
C118—C117—C116	108.6 (4)	O55—C55—C45	109.5 (3)
C118—C117—H11E	110	C65—C55—C45	113.3 (3)
C116—C117—H11E	110	O55—C55—H506	108.8
C118—C117—H11F	110	C65—C55—H506	108.8
C116—C117—H11F	110	C45—C55—H506	108.9
H11E—C117—H11F	108.4	C15—O45—C46	118.4 (3)
C119—C118—C117	110.5 (4)	C25—O25—H508	109.5
C119—C118—C123	109.1 (5)	C35—O35—H509	109.5
C117—C118—C123	108.4 (4)	O65—C65—C55	112.4 (4)
C119—C118—H118	109.6	O65—C65—H51A	109.1
C117—C118—H118	109.6	C55—C65—H51A	109.1
C123—C118—H118	109.6	O65—C65—H51B	109.1
C118—C119—C114	109.9 (4)	C55—C65—H51B	109.1
C118—C119—H11G	109.7	H51A—C65—H51B	107.9
C114—C119—H11G	109.7	C65—O65—H511	109.5
C118—C119—H11H	109.7	C16—O56—C56	113.7 (3)
C114—C119—H11H	109.7	O46—C16—O56	110.3 (3)
H11G—C119—H11H	108.2	O46—C16—C26	108.5 (3)
C114—C120—C121	109.1 (4)	O56—C16—C26	110.4 (3)
C114—C120—H12A	109.9	O46—C16—H602	109.2
C121—C120—H12A	109.9	O56—C16—H602	109.2
C114—C120—H12B	109.9	C26—C16—H602	109.2
C121—C120—H12B	109.9	O26—C26—C16	107.6 (3)
H12A—C120—H12B	108.3	O26—C26—C36	111.5 (4)
C123—C121—C122	109.8 (5)	C16—C26—C36	110.6 (3)
C123—C121—C120	109.8 (5)	O26—C26—H603	109
C122—C121—C120	109.5 (4)	C16—C26—H603	109
C123—C121—H121	109.3	C36—C26—H603	109
C122—C121—H121	109.3	O36—C36—C26	110.7 (3)
C120—C121—H121	109.3	O36—C36—C46	109.9 (3)
C116—C122—C121	108.6 (4)	C26—C36—C46	109.9 (3)
C116—C122—H12C	110	O36—C36—H604	108.8
C121—C122—H12C	110	C26—C36—H604	108.8
C116—C122—H12D	110	C46—C36—H604	108.8
C121—C122—H12D	110	O45—C46—C36	107.5 (3)
H12C—C122—H12D	108.4	O45—C46—C56	108.6 (3)
C121—C123—C118	109.6 (4)	C36—C46—C56	111.9 (3)
C121—C123—H12E	109.7	O45—C46—H605	109.6
C118—C123—H12E	109.7	C36—C46—H605	109.6
C121—C123—H12F	109.7	C56—C46—H605	109.6
C118—C123—H12F	109.7	O56—C56—C66	105.9 (3)
H12E—C123—H12F	108.2	O56—C56—C46	110.8 (3)
C12—O52—C52	113.1 (3)	C66—C56—C46	114.2 (3)
O42—C12—O52	112.1 (4)	O56—C56—H606	108.6
O42—C12—C22	107.9 (4)	C66—C56—H606	108.6
O52—C12—C22	110.1 (4)	C46—C56—H606	108.6
O42—C12—H202	108.9	C16—O46—C47	117.9 (3)
O52—C12—H202	108.9	C26—O26—H608	109.5
C22—C12—H202	108.9	C36—O36—H609	109.5
O22—C22—C32	111.7 (5)	O66—C66—C56	108.5 (3)
O22—C22—C12	110.0 (4)	O66—C66—H61A	110
C32—C22—C12	109.8 (4)	C56—C66—H61A	110
O22—C22—H203	108.4	O66—C66—H61B	110
C32—C22—H203	108.4	C56—C66—H61B	110
C12—C22—H203	108.4	H61A—C66—H61B	108.4
O32—C32—C42	110.6 (4)	C66—O66—H611	109.5
O32—C32—C22	109.0 (4)	C17—O57—C57	113.5 (3)
C42—C32—C22	108.9 (4)	O47—C17—O57	110.5 (3)
O32—C32—H204	109.4	O47—C17—C27	108.7 (4)
C42—C32—H204	109.4	O57—C17—C27	110.0 (3)
C22—C32—H204	109.4	O47—C17—H702	109.2
O41—C42—C32	108.0 (4)	O57—C17—H702	109.2
O41—C42—C52	110.0 (3)	C27—C17—H702	109.2
C32—C42—C52	111.3 (4)	O27—C27—C37	111.4 (4)
O41—C42—H205	109.1	O27—C27—C17	110.0 (3)
C32—C42—H205	109.1	C37—C27—C17	109.4 (3)
C52—C42—H205	109.1	O27—C27—H703	108.7
O52—C52—C62	105.0 (3)	C37—C27—H703	108.7
O52—C52—C42	110.0 (3)	C17—C27—H703	108.7
C62—C52—C42	113.5 (4)	O37—C37—C47	111.6 (3)
O52—C52—H206	109.4	O37—C37—C27	108.0 (3)
C62—C52—H206	109.4	C47—C37—C27	109.2 (3)
C42—C52—H206	109.4	O37—C37—H704	109.4
C12—O42—C43	119.5 (3)	C47—C37—H704	109.4
C22—O22—H208	109.5	C27—C37—H704	109.4
C32—O32—H209	109.5	O46—C47—C37	106.6 (3)
O62—C62—C52	110.7 (4)	O46—C47—C57	109.7 (3)
O62—C62—H21A	109.5	C37—C47—C57	109.7 (3)
C52—C62—H21A	109.5	O46—C47—H705	110.2
O62—C62—H21B	109.5	C37—C47—H705	110.2
C52—C62—H21B	109.5	C57—C47—H705	110.2
H21A—C62—H21B	108.1	O57—C57—C67	104.6 (4)
C62—O62—H211	109.5	O57—C57—C47	108.6 (3)
C13—O53—C53	114.0 (3)	C67—C57—C47	113.4 (4)
O53—C13—O43	111.9 (3)	O57—C57—H706	110
O53—C13—C23	110.6 (3)	C67—C57—H706	110
O43—C13—C23	108.1 (3)	C47—C57—H706	110
O53—C13—H302	108.7	C17—O47—C41	118.5 (3)
O43—C13—H302	108.7	C27—O27—H708	109.5
C23—C13—H302	108.7	C37—O37—H709	109.5
O23—C23—C13	110.7 (3)	O67—C67—C57	112.3 (4)
O23—C23—C33	111.9 (4)	O67—C67—H71A	109.2
C13—C23—C33	109.4 (3)	C57—C67—H71A	109.2
O23—C23—H303	108.2	O67—C67—H71B	109.2
C13—C23—H303	108.2	C57—C67—H71B	109.2
C33—C23—H303	108.3	H71A—C67—H71B	107.9
O33—C33—C43	110.1 (3)	C67—O67—H711	109.5
O33—C33—C23	110.3 (3)	O1—C2—N3	125.7 (11)
C43—C33—C23	109.8 (4)	O1—C2—H2	117.2
O33—C33—H304	108.9	N3—C2—H2	117.2
C43—C33—H304	108.9	C2—N3—C4	125.5 (9)
C23—C33—H304	108.9	C2—N3—C5	117.3 (9)
O42—C43—C33	107.0 (3)	C4—N3—C5	117.2 (9)
O42—C43—C53	109.4 (3)	N3—C4—H4A	109.5
C33—C43—C53	111.4 (3)	N3—C4—H4B	109.5
O42—C43—H305	109.7	H4A—C4—H4B	109.5
C33—C43—H305	109.7	N3—C4—H4C	109.5
C53—C43—H305	109.7	H4A—C4—H4C	109.5
O53—C53—C63	105.7 (4)	H4B—C4—H4C	109.5
O53—C53—C43	111.3 (3)	N3—C5—H5A	109.5
C63—C53—C43	113.1 (3)	N3—C5—H5B	109.5
O53—C53—H306	108.9	H5A—C5—H5B	109.5
C63—C53—H306	108.9	N3—C5—H5C	109.5
C43—C53—H306	108.9	H5A—C5—H5C	109.5
C13—O43—C44	118.0 (3)	H5B—C5—H5C	109.5
C23—O23—H308	109.5
C51—O51—C11—O41	60.6 (5)	O33—C33—C43—C53	173.7 (3)
C51—O51—C11—C21	−60.3 (5)	C23—C33—C43—C53	52.1 (4)
O51—C11—C21—O21	179.9 (3)	C13—O53—C53—C63	179.1 (3)
O41—C11—C21—O21	57.8 (4)	C13—O53—C53—C43	56.0 (4)
O51—C11—C21—C31	57.0 (5)	O42—C43—C53—O53	−169.4 (3)
O41—C11—C21—C31	−65.1 (5)	C33—C43—C53—O53	−51.3 (4)
O21—C21—C31—O31	61.1 (5)	O42—C43—C53—C63	71.8 (4)
C11—C21—C31—O31	−177.5 (4)	C33—C43—C53—C63	−170.1 (4)
O21—C21—C31—C41	−175.7 (4)	O53—C13—O43—C44	103.0 (4)
C11—C21—C31—C41	−54.4 (5)	C23—C13—O43—C44	−134.9 (3)
O31—C31—C41—O47	−65.0 (4)	O53—C53—C63—O63	62.4 (5)
C21—C31—C41—O47	171.9 (3)	C43—C53—C63—O63	−175.6 (4)
O31—C31—C41—C51	176.0 (3)	C054—O54—C14—O44	61.0 (4)
C21—C31—C41—C51	53.0 (5)	C054—O54—C14—C24	−58.9 (4)
C11—O51—C51—C61	177.3 (4)	O44—C14—C24—O24	62.3 (4)
C11—O51—C51—C41	58.2 (5)	O54—C14—C24—O24	−177.3 (3)
O47—C41—C51—O51	−170.0 (3)	O44—C14—C24—C34	−61.9 (5)
C31—C41—C51—O51	−53.2 (5)	O54—C14—C24—C34	58.5 (4)
O47—C41—C51—C61	73.5 (5)	O24—C24—C34—O34	58.3 (5)
C31—C41—C51—C61	−169.7 (4)	C14—C24—C34—O34	−179.0 (3)
O51—C11—O41—C42	115.9 (4)	O24—C24—C34—C44	−179.7 (3)
C21—C11—O41—C42	−122.3 (4)	C14—C24—C34—C44	−57.1 (4)
O51—C51—C61—N61	68.7 (5)	C13—O43—C44—C34	118.3 (4)
C41—C51—C61—N61	−172.3 (4)	C13—O43—C44—C054	−122.0 (4)
C51—C61—N61—C112	−115.3 (9)	O34—C34—C44—O43	−63.9 (4)
C51—C61—N61—C912	−144.3 (9)	C24—C34—C44—O43	173.3 (3)
C912—N61—C112—O113	106 (2)	O34—C34—C44—C054	177.6 (3)
C61—N61—C112—O113	13.3 (17)	C24—C34—C44—C054	54.9 (4)
C912—N61—C112—C114	−69.9 (19)	C14—O54—C054—C64	−179.0 (3)
C61—N61—C112—C114	−163.1 (6)	C14—O54—C054—C44	56.1 (5)
C112—N61—C912—O913	−96 (2)	O43—C44—C054—O54	−170.8 (3)
C61—N61—C912—O913	8 (2)	C34—C44—C054—O54	−53.1 (5)
C112—N61—C912—C114	75 (2)	O43—C44—C054—C64	69.4 (4)
C61—N61—C912—C114	178.6 (7)	C34—C44—C054—C64	−172.9 (3)
O913—C912—C114—C115	−12.5 (17)	O54—C14—O44—C45	129.2 (4)
N61—C912—C114—C115	176.3 (9)	C24—C14—O44—C45	−110.0 (4)
O913—C912—C114—C120	−126.7 (15)	O54—C054—C64—O64	−56.4 (4)
N61—C912—C114—C120	62.1 (12)	C44—C054—C64—O64	66.2 (4)
O913—C912—C114—C119	110.4 (15)	C55—O55—C15—O45	60.2 (4)
N61—C912—C114—C119	−60.8 (12)	C55—O55—C15—C25	−60.3 (4)
O913—C912—C114—C112	109 (3)	O45—C15—C25—O25	57.1 (5)
N61—C912—C114—C112	−62.5 (19)	O55—C15—C25—O25	179.3 (4)
O113—C112—C114—C115	−31.7 (13)	O45—C15—C25—C35	−65.7 (4)
N61—C112—C114—C115	144.8 (9)	O55—C15—C25—C35	56.5 (5)
O113—C112—C114—C912	−96 (2)	O25—C25—C35—O35	62.8 (5)
N61—C112—C114—C912	80 (2)	C15—C25—C35—O35	−175.3 (4)
O113—C112—C114—C120	−158.4 (9)	O25—C25—C35—C45	−175.7 (4)
N61—C112—C114—C120	18.1 (13)	C15—C25—C35—C45	−53.9 (5)
O113—C112—C114—C119	85.0 (11)	C14—O44—C45—C35	133.1 (4)
N61—C112—C114—C119	−98.5 (10)	C14—O44—C45—C55	−106.0 (4)
C912—C114—C115—C116	−171.7 (7)	O35—C35—C45—O44	−63.6 (6)
C120—C114—C115—C116	−60.1 (6)	C25—C35—C45—O44	174.7 (4)
C119—C114—C115—C116	59.3 (5)	O35—C35—C45—C55	176.3 (5)
C112—C114—C115—C116	169.5 (6)	C25—C35—C45—C55	54.6 (5)
C114—C115—C116—C122	60.5 (6)	C15—O55—C55—C65	−176.8 (3)
C114—C115—C116—C117	−60.4 (5)	C15—O55—C55—C45	59.8 (4)
C122—C116—C117—C118	−61.4 (6)	O44—C45—C55—O55	−174.9 (3)
C115—C116—C117—C118	59.6 (5)	C35—C45—C55—O55	−56.2 (5)
C116—C117—C118—C119	−59.4 (5)	O44—C45—C55—C65	65.3 (4)
C116—C117—C118—C123	60.1 (5)	C35—C45—C55—C65	−176.1 (4)
C117—C118—C119—C114	58.7 (6)	O55—C15—O45—C46	106.2 (4)
C123—C118—C119—C114	−60.4 (6)	C25—C15—O45—C46	−132.0 (4)
C115—C114—C119—C118	−58.0 (6)	O55—C55—C65—O65	−66.8 (4)
C912—C114—C119—C118	−177.9 (6)	C45—C55—C65—O65	54.2 (5)
C120—C114—C119—C118	61.1 (6)	C56—O56—C16—O46	59.5 (4)
C112—C114—C119—C118	−177.3 (5)	C56—O56—C16—C26	−60.4 (4)
C115—C114—C120—C121	60.0 (6)	O46—C16—C26—O26	59.3 (4)
C912—C114—C120—C121	170.7 (7)	O56—C16—C26—O26	−179.8 (3)
C119—C114—C120—C121	−60.0 (6)	O46—C16—C26—C36	−62.7 (4)
C112—C114—C120—C121	−171.0 (6)	O56—C16—C26—C36	58.3 (4)
C114—C120—C121—C123	59.9 (6)	O26—C26—C36—O36	64.8 (4)
C114—C120—C121—C122	−60.6 (6)	C16—C26—C36—O36	−175.5 (3)
C115—C116—C122—C121	−59.5 (6)	O26—C26—C36—C46	−173.6 (3)
C117—C116—C122—C121	60.9 (6)	C16—C26—C36—C46	−53.9 (4)
C123—C121—C122—C116	−60.8 (6)	C15—O45—C46—C36	122.3 (4)
C120—C121—C122—C116	59.8 (6)	C15—O45—C46—C56	−116.4 (4)
C122—C121—C123—C118	61.0 (6)	O36—C36—C46—O45	−67.8 (4)
C120—C121—C123—C118	−59.4 (6)	C26—C36—C46—O45	170.2 (3)
C119—C118—C123—C121	59.7 (6)	O36—C36—C46—C56	173.1 (3)
C117—C118—C123—C121	−60.7 (6)	C26—C36—C46—C56	51.1 (4)
C52—O52—C12—O42	60.4 (5)	C16—O56—C56—C66	−178.7 (3)
C52—O52—C12—C22	−59.7 (5)	C16—O56—C56—C46	56.9 (4)
O42—C12—C22—O22	59.0 (5)	O45—C46—C56—O56	−170.2 (3)
O52—C12—C22—O22	−178.4 (4)	C36—C46—C56—O56	−51.7 (4)
O42—C12—C22—C32	−64.4 (5)	O45—C46—C56—C66	70.3 (4)
O52—C12—C22—C32	58.3 (5)	C36—C46—C56—C66	−171.2 (3)
O22—C22—C32—O32	60.6 (5)	O56—C16—O46—C47	105.1 (4)
C12—C22—C32—O32	−177.1 (4)	C26—C16—O46—C47	−133.8 (3)
O22—C22—C32—C42	−178.6 (3)	O56—C56—C66—O66	−64.3 (4)
C12—C22—C32—C42	−56.3 (5)	C46—C56—C66—O66	58.0 (5)
C11—O41—C42—C32	128.0 (4)	C57—O57—C17—O47	59.8 (4)
C11—O41—C42—C52	−110.3 (4)	C57—O57—C17—C27	−60.2 (5)
O32—C32—C42—O41	−63.7 (5)	O47—C17—C27—O27	58.8 (4)
C22—C32—C42—O41	176.6 (3)	O57—C17—C27—O27	179.9 (3)
O32—C32—C42—C52	175.4 (4)	O47—C17—C27—C37	−63.8 (4)
C22—C32—C42—C52	55.7 (4)	O57—C17—C27—C37	57.3 (5)
C12—O52—C52—C62	−179.4 (3)	O27—C27—C37—O37	59.8 (4)
C12—O52—C52—C42	58.1 (4)	C17—C27—C37—O37	−178.4 (3)
O41—C42—C52—O52	−175.4 (3)	O27—C27—C37—C47	−178.7 (3)
C32—C42—C52—O52	−55.7 (5)	C17—C27—C37—C47	−56.9 (5)
O41—C42—C52—C62	67.2 (4)	C16—O46—C47—C37	122.2 (4)
C32—C42—C52—C62	−173.0 (4)	C16—O46—C47—C57	−119.1 (4)
O52—C12—O42—C43	114.3 (4)	O37—C37—C47—O46	−63.9 (4)
C22—C12—O42—C43	−124.3 (4)	C27—C37—C47—O46	176.9 (3)
O52—C52—C62—O62	−66.4 (4)	O37—C37—C47—C57	177.3 (3)
C42—C52—C62—O62	53.8 (5)	C27—C37—C47—C57	58.1 (4)
C53—O53—C13—O43	60.3 (4)	C17—O57—C57—C67	−178.2 (4)
C53—O53—C13—C23	−60.3 (4)	C17—O57—C57—C47	60.4 (5)
O53—C13—C23—O23	−177.1 (3)	O46—C47—C57—O57	−175.0 (3)
O43—C13—C23—O23	60.1 (4)	C37—C47—C57—O57	−58.2 (5)
O53—C13—C23—C33	59.2 (4)	O46—C47—C57—C67	69.2 (5)
O43—C13—C23—C33	−63.6 (4)	C37—C47—C57—C67	−174.0 (4)
O23—C23—C33—O33	60.0 (4)	O57—C17—O47—C41	114.6 (4)
C13—C23—C33—O33	−177.0 (3)	C27—C17—O47—C41	−124.6 (4)
O23—C23—C33—C43	−178.5 (3)	C31—C41—O47—C17	132.2 (4)
C13—C23—C33—C43	−55.5 (4)	C51—C41—O47—C17	−108.3 (4)
C12—O42—C43—C33	128.4 (4)	O57—C57—C67—O67	66.3 (5)
C12—O42—C43—C53	−110.8 (4)	C47—C57—C67—O67	−175.6 (4)
O33—C33—C43—O42	−66.7 (4)	O1—C2—N3—C4	−179.6 (10)
C23—C33—C43—O42	171.6 (3)	O1—C2—N3—C5	−1.0 (15)