Tuberostemoamide hemihydrate.

In the crystal structure of the title compound {systematic name: (1'S,2R,2'R,3'S,6'R)-3'-ethyl-4-methyl-5H-5'-oxa-10'-aza-spiro-[furan-2,4'-tricyclo-[8.3.0.0(2,6)]trideca-ne]-5,11'-dione hemihydrate}, C(17)H(23)NO(4)·0.5H(2)O, the asymmetric unit contains two mol-ecules of tuberostemoamide with similar conformations and one water mol-ecule. The tuberostemoamide mol-ecule is composed of one seven-membered ring (A) and three five-membered rings (B, C and D). Ring A exists in a chair conformation, both rings B and C exist in envelope conformations, and ring D is almost planar with a mean deviation of 0.0143 (4) Å in one molecule and 0.0095 (3) Å in the other.. The dihedral angles between the planes of rings C and D are 75.1 (3)° in one mol-ecule and 74.5 (3)° for the other. The solvent water mol-ecule links the tuberostemoamide mol-ecules through O-H⋯O(ketone) hydrogen bonds. Weak C-H⋯O inter-actions are also present, involving both the water mol-ecule and a heterocyclic ether O-atom acceptor.

Related literature

For general background, see: Pilli & Ferreira de Oliveira (2000 ▶); Jiang et al. (2006 ▶). For the biological activity of Stemona alkaloids, see: Xu et al. (2010 ▶); Lin et al. (2008 ▶); Hu et al. (2009 ▶).

Experimental

Crystal data

C17H23NO4·0.5H2O

M = 314.37

Orthorhombic,

a = 8.6412 (2) Å

b = 10.7998 (2) Å

c = 36.1685 (7) Å

V = 3375.36 (12) Å3

Z = 8

Cu Kα radiation

μ = 0.73 mm−1

T = 298 K

0.42 × 0.30 × 0.27 mm

Data collection

Oxford Diffraction Gemini S Ultra CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.822, T max = 1.000

8573 measured reflections

4837 independent reflections

4514 reflections with I > 2I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.142

S = 1.06

4837 reflections

412 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1743 Friedel pairs

Flack parameter: −0.1 (2)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1998 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043340/zs2152sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043340/zs2152Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H23NO4·0.5H2O	F(000) = 1352
Mr = 314.37	Dx = 1.237 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4774 reflections
a = 8.6412 (2) Å	θ = 3.7–62.5°
b = 10.7998 (2) Å	µ = 0.73 mm−1
c = 36.1685 (7) Å	T = 298 K
V = 3375.36 (12) Å3	Block, colorless
Z = 8	0.42 × 0.30 × 0.27 mm

Oxford Diffraction Gemini S Ultra CCD diffractometer	4837 independent reflections
Radiation source: fine-focus sealed tube	4514 reflections with I > 2˘I)
graphite	Rint = 0.021
ω scans	θmax = 62.6°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.822, Tmax = 1.000	k = −12→10
8573 measured reflections	l = −19→41

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0913P)2 + 0.4948P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4837 reflections	Δρmax = 0.51 e Å−3
412 parameters	Δρmin = −0.24 e Å−3
2 restraints	Absolute structure: Flack (1983), 1743 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.1 (2)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1'	0.3987 (3)	0.6908 (2)	0.08626 (7)	0.0818 (7)
O2'	0.9749 (2)	0.7450 (2)	0.18688 (6)	0.0688 (6)
O3'	1.0512 (3)	0.9441 (2)	0.20168 (6)	0.0792 (7)
O4'	1.2437 (4)	1.0530 (3)	0.22680 (11)	0.1210 (12)
C1'	0.4852 (4)	0.7634 (3)	0.18058 (9)	0.0663 (8)
H1'A	0.4397	0.8047	0.2018	0.080*
H1'B	0.5442	0.6924	0.1890	0.080*
C2'	0.3601 (4)	0.7249 (4)	0.15240 (10)	0.0828 (10)
H2'A	0.3262	0.6405	0.1567	0.099*
H2'B	0.2713	0.7797	0.1537	0.099*
C3'	0.4403 (3)	0.7360 (3)	0.11593 (9)	0.0614 (7)
N4'	0.5691 (3)	0.8034 (2)	0.12056 (6)	0.0530 (5)
C5'	0.6762 (4)	0.8299 (3)	0.09050 (7)	0.0583 (7)
H5'A	0.7141	0.9140	0.0931	0.070*
H5'B	0.6214	0.8244	0.0672	0.070*
C6'	0.8127 (4)	0.7416 (3)	0.08984 (7)	0.0617 (7)
H6'A	0.7732	0.6575	0.0902	0.074*
H6'B	0.8673	0.7527	0.0666	0.074*
C7'	0.9266 (3)	0.7555 (3)	0.12079 (8)	0.0612 (7)
H7'A	0.9796	0.8341	0.1181	0.073*
H7'B	1.0035	0.6904	0.1188	0.073*
C8'	0.8538 (3)	0.7500 (3)	0.15902 (7)	0.0513 (6)
H8'A	0.7900	0.6752	0.1609	0.062*
C9'	0.7566 (3)	0.8615 (2)	0.16928 (7)	0.0477 (6)
H9'A	0.8006	0.9338	0.1567	0.057*
C9A'	0.5859 (3)	0.8521 (2)	0.15822 (7)	0.0514 (6)
H9AB	0.5397	0.9349	0.1592	0.062*
C10'	0.7858 (4)	0.8767 (3)	0.21083 (7)	0.0547 (6)
H10B	0.7249	0.8140	0.2239	0.066*
C11'	0.9562 (4)	0.8396 (3)	0.21282 (8)	0.0596 (7)
C12'	1.0220 (4)	0.8032 (3)	0.24871 (9)	0.0681 (8)
H12B	0.9854	0.7383	0.2632	0.082*
C13'	1.1403 (4)	0.8751 (4)	0.25765 (9)	0.0762 (9)
C14'	1.1569 (4)	0.9670 (4)	0.22847 (11)	0.0810 (10)
C15'	1.2413 (6)	0.8803 (6)	0.29114 (12)	0.1187 (17)
H15D	1.2159	0.8129	0.3073	0.178*
H15E	1.2251	0.9574	0.3038	0.178*
H15F	1.3478	0.8739	0.2838	0.178*
C16'	0.7445 (6)	1.0033 (4)	0.22668 (10)	0.0858 (11)
H16C	0.8230	1.0618	0.2188	0.103*
H16D	0.6473	1.0294	0.2158	0.103*
C17'	0.7300 (10)	1.0123 (6)	0.26649 (16)	0.157 (3)
H17D	0.7049	1.0960	0.2732	0.236*
H17E	0.8260	0.9891	0.2779	0.236*
H17F	0.6493	0.9579	0.2748	0.236*
O1	−0.0168 (3)	0.5873 (2)	0.01640 (7)	0.0779 (6)
O2	−0.5911 (2)	0.31108 (18)	−0.03973 (5)	0.0528 (4)
O3	−0.6774 (2)	0.36455 (16)	−0.09836 (5)	0.0564 (5)
O4	−0.8917 (3)	0.3499 (2)	−0.13237 (6)	0.0742 (6)
C1	−0.1041 (3)	0.3420 (3)	−0.04581 (9)	0.0591 (7)
H1A	−0.1618	0.2844	−0.0305	0.071*
H1B	−0.0599	0.2974	−0.0665	0.071*
C2	0.0210 (3)	0.4071 (3)	−0.02354 (9)	0.0595 (7)
H2A	0.0564	0.3556	−0.0033	0.071*
H2B	0.1087	0.4283	−0.0390	0.071*
C3	−0.0582 (3)	0.5213 (3)	−0.00945 (8)	0.0545 (6)
N4	−0.1863 (2)	0.5401 (2)	−0.02972 (6)	0.0515 (5)
C5	−0.2939 (3)	0.6411 (3)	−0.02211 (9)	0.0610 (7)
H5A	−0.3387	0.6697	−0.0452	0.073*
H5B	−0.2378	0.7097	−0.0111	0.073*
C6	−0.4218 (3)	0.6016 (3)	0.00366 (9)	0.0610 (7)
H6A	−0.4763	0.6751	0.0120	0.073*
H6B	−0.3755	0.5633	0.0252	0.073*
C7	−0.5400 (3)	0.5116 (3)	−0.01270 (8)	0.0544 (7)
H7A	−0.6114	0.4867	0.0066	0.065*
H7B	−0.5992	0.5543	−0.0316	0.065*
C8	−0.4694 (3)	0.3976 (2)	−0.02940 (7)	0.0437 (5)
H8A	−0.4020	0.3583	−0.0111	0.052*
C9	−0.3777 (3)	0.4177 (2)	−0.06508 (7)	0.0457 (6)
H9A	−0.4245	0.4879	−0.0781	0.055*
C9A	−0.2073 (3)	0.4480 (2)	−0.05906 (7)	0.0493 (6)
H9AA	−0.1645	0.4812	−0.0821	0.059*
C10	−0.4123 (3)	0.3013 (3)	−0.08746 (7)	0.0529 (6)
H10A	−0.3504	0.2334	−0.0772	0.063*
C11	−0.5799 (3)	0.2795 (2)	−0.07690 (7)	0.0500 (6)
C12	−0.6566 (3)	0.1570 (2)	−0.08304 (8)	0.0576 (7)
H12A	−0.6192	0.0819	−0.0742	0.069*
C13	−0.7846 (3)	0.1697 (2)	−0.10266 (7)	0.0536 (6)
C14	−0.7969 (3)	0.3011 (2)	−0.11322 (7)	0.0523 (6)
C15	−0.9043 (4)	0.0787 (3)	−0.11504 (10)	0.0691 (8)
H15A	−0.8783	−0.0022	−0.1059	0.104*
H15B	−0.9079	0.0770	−0.1416	0.104*
H15C	−1.0036	0.1028	−0.1056	0.104*
C16	−0.3768 (5)	0.3105 (4)	−0.12896 (9)	0.0858 (11)
H16A	−0.4557	0.3617	−0.1404	0.103*
H16B	−0.2787	0.3530	−0.1319	0.103*
C17	−0.3690 (9)	0.1966 (7)	−0.14874 (13)	0.158 (3)
H17A	−0.3458	0.2129	−0.1742	0.238*
H17B	−0.4666	0.1546	−0.1470	0.238*
H17C	−0.2892	0.1455	−0.1383	0.238*
O1W	0.1914 (4)	0.5014 (3)	0.06972 (10)	0.1025 (9)
H1WA	0.128 (6)	0.529 (6)	0.0552 (14)	0.154*
H1WB	0.256 (6)	0.553 (5)	0.0765 (16)	0.154*

	U11	U22	U33	U12	U13	U23
O1'	0.0742 (14)	0.0875 (15)	0.0837 (14)	−0.0204 (13)	−0.0242 (12)	−0.0017 (13)
O2'	0.0611 (12)	0.0800 (13)	0.0653 (11)	0.0199 (11)	−0.0105 (10)	−0.0137 (10)
O3'	0.0698 (14)	0.0857 (15)	0.0821 (14)	−0.0206 (13)	−0.0149 (12)	0.0174 (13)
O4'	0.091 (2)	0.112 (2)	0.160 (3)	−0.042 (2)	−0.032 (2)	0.014 (2)
C1'	0.0494 (15)	0.082 (2)	0.0676 (16)	−0.0068 (16)	0.0064 (14)	0.0036 (15)
C2'	0.0488 (17)	0.102 (3)	0.098 (2)	−0.0145 (18)	0.0042 (17)	0.005 (2)
C3'	0.0522 (15)	0.0579 (16)	0.0743 (18)	−0.0020 (14)	−0.0125 (15)	0.0050 (14)
N4'	0.0514 (12)	0.0490 (11)	0.0584 (12)	−0.0085 (10)	−0.0059 (10)	0.0023 (10)
C5'	0.0723 (18)	0.0559 (15)	0.0468 (13)	−0.0160 (15)	−0.0060 (13)	0.0078 (11)
C6'	0.0733 (19)	0.0614 (16)	0.0504 (13)	−0.0130 (16)	0.0116 (14)	−0.0043 (12)
C7'	0.0525 (15)	0.0713 (17)	0.0600 (15)	−0.0030 (14)	0.0116 (14)	−0.0109 (14)
C8'	0.0498 (14)	0.0514 (13)	0.0527 (13)	0.0004 (12)	−0.0008 (12)	−0.0050 (11)
C9'	0.0488 (14)	0.0443 (13)	0.0499 (12)	−0.0011 (11)	0.0021 (11)	−0.0011 (10)
C9A'	0.0452 (14)	0.0500 (14)	0.0590 (13)	0.0032 (12)	−0.0023 (11)	−0.0015 (12)
C10'	0.0597 (16)	0.0550 (15)	0.0495 (13)	−0.0005 (14)	0.0021 (12)	−0.0034 (12)
C11'	0.0627 (17)	0.0599 (17)	0.0562 (14)	−0.0039 (15)	−0.0038 (13)	−0.0001 (13)
C12'	0.078 (2)	0.0655 (18)	0.0606 (15)	−0.0022 (17)	−0.0118 (15)	0.0012 (14)
C13'	0.077 (2)	0.081 (2)	0.0708 (18)	−0.0006 (19)	−0.0223 (17)	−0.0044 (17)
C14'	0.063 (2)	0.083 (2)	0.097 (3)	−0.0072 (19)	−0.0125 (18)	−0.006 (2)
C15'	0.115 (4)	0.149 (4)	0.092 (3)	−0.008 (3)	−0.049 (3)	−0.011 (3)
C16'	0.113 (3)	0.071 (2)	0.073 (2)	0.017 (2)	0.002 (2)	−0.0231 (16)
C17'	0.199 (7)	0.147 (5)	0.126 (4)	0.035 (5)	0.007 (5)	−0.050 (4)
O1	0.0652 (13)	0.0750 (14)	0.0937 (15)	−0.0013 (12)	−0.0213 (12)	−0.0129 (12)
O2	0.0478 (10)	0.0594 (10)	0.0513 (9)	−0.0123 (9)	0.0013 (8)	−0.0019 (8)
O3	0.0622 (11)	0.0405 (9)	0.0666 (10)	−0.0009 (9)	−0.0147 (9)	0.0045 (8)
O4	0.0718 (13)	0.0615 (12)	0.0894 (14)	−0.0005 (11)	−0.0272 (12)	0.0171 (11)
C1	0.0472 (14)	0.0535 (15)	0.0766 (17)	0.0057 (13)	0.0086 (14)	−0.0014 (13)
C2	0.0387 (13)	0.0603 (16)	0.0796 (17)	0.0042 (12)	0.0029 (13)	0.0114 (14)
C3	0.0432 (13)	0.0489 (14)	0.0715 (16)	−0.0047 (12)	−0.0008 (13)	0.0056 (13)
N4	0.0423 (11)	0.0430 (11)	0.0694 (13)	0.0004 (10)	−0.0003 (10)	0.0047 (10)
C5	0.0508 (14)	0.0412 (13)	0.0910 (19)	0.0048 (12)	−0.0096 (15)	−0.0014 (13)
C6	0.0551 (16)	0.0517 (15)	0.0762 (17)	0.0089 (13)	−0.0022 (14)	−0.0142 (14)
C7	0.0451 (14)	0.0561 (15)	0.0621 (15)	0.0054 (12)	0.0043 (12)	−0.0048 (12)
C8	0.0390 (12)	0.0449 (12)	0.0471 (12)	−0.0019 (11)	−0.0027 (10)	0.0023 (10)
C9	0.0458 (12)	0.0465 (13)	0.0449 (12)	0.0005 (11)	0.0003 (11)	0.0059 (10)
C9A	0.0465 (13)	0.0511 (14)	0.0504 (13)	−0.0016 (12)	0.0086 (11)	0.0050 (11)
C10	0.0575 (15)	0.0511 (13)	0.0501 (13)	0.0047 (13)	0.0009 (12)	−0.0020 (11)
C11	0.0543 (15)	0.0437 (13)	0.0520 (13)	0.0039 (12)	−0.0072 (12)	0.0008 (11)
C12	0.0657 (17)	0.0416 (13)	0.0656 (15)	0.0039 (13)	−0.0101 (14)	0.0035 (12)
C13	0.0589 (15)	0.0397 (13)	0.0621 (14)	0.0011 (12)	−0.0061 (13)	−0.0011 (11)
C14	0.0556 (15)	0.0461 (13)	0.0553 (13)	0.0025 (13)	−0.0057 (13)	0.0019 (11)
C15	0.0646 (18)	0.0528 (16)	0.090 (2)	−0.0069 (15)	−0.0156 (17)	−0.0028 (15)
C16	0.102 (3)	0.097 (3)	0.0583 (17)	0.010 (2)	0.0197 (19)	−0.0043 (17)
C17	0.192 (6)	0.202 (6)	0.081 (3)	0.027 (6)	0.009 (4)	−0.047 (4)
O1W	0.104 (2)	0.0833 (18)	0.120 (2)	−0.0337 (17)	−0.0342 (18)	0.0232 (15)

O1'—C3'	1.233 (4)	O2—C11	1.390 (3)
O2'—C11'	1.396 (4)	O2—C8	1.455 (3)
O2'—C8'	1.454 (3)	O3—C14	1.351 (3)
O3'—C14'	1.354 (4)	O3—C11	1.468 (3)
O3'—C11'	1.453 (4)	O4—C14	1.195 (3)
O4'—C14'	1.195 (5)	C1—C2	1.521 (4)
C1'—C9A'	1.525 (4)	C1—C9A	1.528 (4)
C1'—C2'	1.542 (5)	C1—H1A	0.9700
C1'—H1'A	0.9700	C1—H1B	0.9700
C1'—H1'B	0.9700	C2—C3	1.499 (4)
C2'—C3'	1.495 (5)	C2—H2A	0.9700
C2'—H2'A	0.9700	C2—H2B	0.9700
C2'—H2'B	0.9700	C3—N4	1.343 (4)
C3'—N4'	1.340 (4)	N4—C5	1.460 (3)
N4'—C5'	1.456 (4)	N4—C9A	1.466 (3)
N4'—C9A'	1.467 (3)	C5—C6	1.507 (4)
C5'—C6'	1.517 (4)	C5—H5A	0.9700
C5'—H5'A	0.9700	C5—H5B	0.9700
C5'—H5'B	0.9700	C6—C7	1.529 (4)
C6'—C7'	1.498 (4)	C6—H6A	0.9700
C6'—H6'A	0.9700	C6—H6B	0.9700
C6'—H6'B	0.9700	C7—C8	1.501 (4)
C7'—C8'	1.520 (4)	C7—H7A	0.9700
C7'—H7'A	0.9700	C7—H7B	0.9700
C7'—H7'B	0.9700	C8—C9	1.530 (3)
C8'—C9'	1.515 (4)	C8—H8A	0.9800
C8'—H8'A	0.9800	C9—C10	1.524 (4)
C9'—C9A'	1.532 (4)	C9—C9A	1.524 (4)
C9'—C10'	1.533 (3)	C9—H9A	0.9800
C9'—H9'A	0.9800	C9A—H9AA	0.9800
C9A'—H9AB	0.9800	C10—C11	1.517 (4)
C10'—C16'	1.525 (4)	C10—C16	1.535 (4)
C10'—C11'	1.528 (4)	C10—H10A	0.9800
C10'—H10B	0.9800	C11—C12	1.496 (4)
C11'—C12'	1.470 (4)	C12—C13	1.321 (4)
C12'—C13'	1.324 (5)	C12—H12A	0.9300
C12'—H12B	0.9300	C13—C14	1.473 (4)
C13'—C14'	1.456 (5)	C13—C15	1.496 (4)
C13'—C15'	1.494 (5)	C15—H15A	0.9600
C15'—H15D	0.9600	C15—H15B	0.9600
C15'—H15E	0.9600	C15—H15C	0.9600
C15'—H15F	0.9600	C16—C17	1.425 (7)
C16'—C17'	1.449 (6)	C16—H16A	0.9700
C16'—H16C	0.9700	C16—H16B	0.9700
C16'—H16D	0.9700	C17—H17A	0.9600
C17'—H17D	0.9600	C17—H17B	0.9600
C17'—H17E	0.9600	C17—H17C	0.9600
C17'—H17F	0.9600	O1W—H1WA	0.81 (2)
O1—C3	1.229 (4)	O1W—H1WB	0.82 (2)
C11'—O2'—C8'	110.8 (2)	C14—O3—C11	109.35 (19)
C14'—O3'—C11'	108.9 (3)	C2—C1—C9A	103.5 (2)
C9A'—C1'—C2'	102.6 (3)	C2—C1—H1A	111.1
C9A'—C1'—H1'A	111.2	C9A—C1—H1A	111.1
C2'—C1'—H1'A	111.2	C2—C1—H1B	111.1
C9A'—C1'—H1'B	111.2	C9A—C1—H1B	111.1
C2'—C1'—H1'B	111.2	H1A—C1—H1B	109.0
H1'A—C1'—H1'B	109.2	C3—C2—C1	103.6 (2)
C3'—C2'—C1'	103.7 (2)	C3—C2—H2A	111.0
C3'—C2'—H2'A	111.0	C1—C2—H2A	111.0
C1'—C2'—H2'A	111.0	C3—C2—H2B	111.0
C3'—C2'—H2'B	111.0	C1—C2—H2B	111.0
C1'—C2'—H2'B	111.0	H2A—C2—H2B	109.0
H2'A—C2'—H2'B	109.0	O1—C3—N4	124.6 (3)
O1'—C3'—N4'	124.5 (3)	O1—C3—C2	127.0 (3)
O1'—C3'—C2'	126.9 (3)	N4—C3—C2	108.4 (2)
N4'—C3'—C2'	108.6 (3)	C3—N4—C5	122.3 (2)
C3'—N4'—C5'	122.8 (2)	C3—N4—C9A	113.2 (2)
C3'—N4'—C9A'	113.1 (2)	C5—N4—C9A	124.4 (2)
C5'—N4'—C9A'	124.0 (2)	N4—C5—C6	111.9 (2)
N4'—C5'—C6'	112.5 (2)	N4—C5—H5A	109.2
N4'—C5'—H5'A	109.1	C6—C5—H5A	109.2
C6'—C5'—H5'A	109.1	N4—C5—H5B	109.2
N4'—C5'—H5'B	109.1	C6—C5—H5B	109.2
C6'—C5'—H5'B	109.1	H5A—C5—H5B	107.9
H5'A—C5'—H5'B	107.8	C5—C6—C7	115.5 (2)
C7'—C6'—C5'	115.9 (2)	C5—C6—H6A	108.4
C7'—C6'—H6'A	108.3	C7—C6—H6A	108.4
C5'—C6'—H6'A	108.3	C5—C6—H6B	108.4
C7'—C6'—H6'B	108.3	C7—C6—H6B	108.4
C5'—C6'—H6'B	108.3	H6A—C6—H6B	107.5
H6'A—C6'—H6'B	107.4	C8—C7—C6	113.9 (2)
C6'—C7'—C8'	113.8 (2)	C8—C7—H7A	108.8
C6'—C7'—H7'A	108.8	C6—C7—H7A	108.8
C8'—C7'—H7'A	108.8	C8—C7—H7B	108.8
C6'—C7'—H7'B	108.8	C6—C7—H7B	108.8
C8'—C7'—H7'B	108.8	H7A—C7—H7B	107.7
H7'A—C7'—H7'B	107.7	O2—C8—C7	109.7 (2)
O2'—C8'—C9'	105.0 (2)	O2—C8—C9	104.40 (18)
O2'—C8'—C7'	109.5 (2)	C7—C8—C9	115.7 (2)
C9'—C8'—C7'	114.9 (2)	O2—C8—H8A	108.9
O2'—C8'—H8'A	109.1	C7—C8—H8A	108.9
C9'—C8'—H8'A	109.1	C9—C8—H8A	108.9
C7'—C8'—H8'A	109.1	C10—C9—C9A	116.2 (2)
C8'—C9'—C9A'	114.6 (2)	C10—C9—C8	103.3 (2)
C8'—C9'—C10'	103.5 (2)	C9A—C9—C8	114.2 (2)
C9A'—C9'—C10'	114.9 (2)	C10—C9—H9A	107.5
C8'—C9'—H9'A	107.8	C9A—C9—H9A	107.5
C9A'—C9'—H9'A	107.8	C8—C9—H9A	107.5
C10'—C9'—H9'A	107.8	N4—C9A—C9	111.6 (2)
N4'—C9A'—C1'	102.2 (2)	N4—C9A—C1	102.1 (2)
N4'—C9A'—C9'	111.2 (2)	C9—C9A—C1	116.6 (2)
C1'—C9A'—C9'	116.9 (2)	N4—C9A—H9AA	108.7
N4'—C9A'—H9AB	108.7	C9—C9A—H9AA	108.7
C1'—C9A'—H9AB	108.7	C1—C9A—H9AA	108.7
C9'—C9A'—H9AB	108.7	C11—C10—C9	100.5 (2)
C16'—C10'—C11'	116.3 (3)	C11—C10—C16	116.5 (3)
C16'—C10'—C9'	115.2 (3)	C9—C10—C16	115.3 (3)
C11'—C10'—C9'	100.2 (2)	C11—C10—H10A	108.0
C16'—C10'—H10B	108.2	C9—C10—H10A	108.0
C11'—C10'—H10B	108.2	C16—C10—H10A	108.0
C9'—C10'—H10B	108.2	O2—C11—O3	108.5 (2)
O2'—C11'—O3'	108.5 (2)	O2—C11—C12	109.3 (2)
O2'—C11'—C12'	110.7 (3)	O3—C11—C12	102.7 (2)
O3'—C11'—C12'	103.6 (2)	O2—C11—C10	105.8 (2)
O2'—C11'—C10'	105.7 (2)	O3—C11—C10	108.5 (2)
O3'—C11'—C10'	109.1 (2)	C12—C11—C10	121.6 (2)
C12'—C11'—C10'	119.0 (3)	C13—C12—C11	111.0 (2)
C13'—C12'—C11'	110.9 (3)	C13—C12—H12A	124.5
C13'—C12'—H12B	124.5	C11—C12—H12A	124.5
C11'—C12'—H12B	124.5	C12—C13—C14	107.5 (2)
C12'—C13'—C14'	107.4 (3)	C12—C13—C15	132.2 (3)
C12'—C13'—C15'	132.1 (4)	C14—C13—C15	120.4 (2)
C14'—C13'—C15'	120.3 (4)	O4—C14—O3	122.0 (2)
O4'—C14'—O3'	121.9 (4)	O4—C14—C13	128.7 (3)
O4'—C14'—C13'	128.9 (4)	O3—C14—C13	109.3 (2)
O3'—C14'—C13'	109.1 (3)	C13—C15—H15A	109.5
C13'—C15'—H15D	109.5	C13—C15—H15B	109.5
C13'—C15'—H15E	109.5	H15A—C15—H15B	109.5
H15D—C15'—H15E	109.5	C13—C15—H15C	109.5
C13'—C15'—H15F	109.5	H15A—C15—H15C	109.5
H15D—C15'—H15F	109.5	H15B—C15—H15C	109.5
H15E—C15'—H15F	109.5	C17—C16—C10	116.4 (4)
C17'—C16'—C10'	117.0 (4)	C17—C16—H16A	108.2
C17'—C16'—H16C	108.0	C10—C16—H16A	108.2
C10'—C16'—H16C	108.0	C17—C16—H16B	108.2
C17'—C16'—H16D	108.0	C10—C16—H16B	108.2
C10'—C16'—H16D	108.0	H16A—C16—H16B	107.3
H16C—C16'—H16D	107.3	C16—C17—H17A	109.5
C16'—C17'—H17D	109.5	C16—C17—H17B	109.5
C16'—C17'—H17E	109.5	H17A—C17—H17B	109.5
H17D—C17'—H17E	109.5	C16—C17—H17C	109.5
C16'—C17'—H17F	109.5	H17A—C17—H17C	109.5
H17D—C17'—H17F	109.5	H17B—C17—H17C	109.5
H17E—C17'—H17F	109.5	H1WA—O1W—H1WB	113 (6)
C11—O2—C8	110.84 (19)
C9A'—C1'—C2'—C3'	28.3 (4)	C9A—C1—C2—C3	28.4 (3)
C1'—C2'—C3'—O1'	163.4 (3)	C1—C2—C3—O1	161.7 (3)
C1'—C2'—C3'—N4'	−15.8 (4)	C1—C2—C3—N4	−17.6 (3)
O1'—C3'—N4'—C5'	−0.5 (5)	O1—C3—N4—C5	−2.0 (4)
C2'—C3'—N4'—C5'	178.8 (3)	C2—C3—N4—C5	177.3 (2)
O1'—C3'—N4'—C9A'	176.5 (3)	O1—C3—N4—C9A	179.5 (3)
C2'—C3'—N4'—C9A'	−4.2 (3)	C2—C3—N4—C9A	−1.3 (3)
C3'—N4'—C5'—C6'	−97.1 (3)	C3—N4—C5—C6	−91.8 (3)
C9A'—N4'—C5'—C6'	86.2 (3)	C9A—N4—C5—C6	86.6 (3)
N4'—C5'—C6'—C7'	−69.8 (3)	N4—C5—C6—C7	−70.3 (3)
C5'—C6'—C7'—C8'	53.7 (4)	C5—C6—C7—C8	53.6 (3)
C11'—O2'—C8'—C9'	1.6 (3)	C11—O2—C8—C7	124.5 (2)
C11'—O2'—C8'—C7'	125.5 (3)	C11—O2—C8—C9	0.0 (3)
C6'—C7'—C8'—O2'	171.3 (3)	C6—C7—C8—O2	172.6 (2)
C6'—C7'—C8'—C9'	−70.9 (3)	C6—C7—C8—C9	−69.7 (3)
O2'—C8'—C9'—C9A'	−150.5 (2)	O2—C8—C9—C10	−23.5 (2)
C7'—C8'—C9'—C9A'	89.2 (3)	C7—C8—C9—C10	−144.1 (2)
O2'—C8'—C9'—C10'	−24.5 (3)	O2—C8—C9—C9A	−150.7 (2)
C7'—C8'—C9'—C10'	−144.9 (2)	C7—C8—C9—C9A	88.7 (3)
C3'—N4'—C9A'—C1'	22.5 (3)	C3—N4—C9A—C9	144.6 (2)
C5'—N4'—C9A'—C1'	−160.5 (2)	C5—N4—C9A—C9	−33.9 (3)
C3'—N4'—C9A'—C9'	147.9 (2)	C3—N4—C9A—C1	19.3 (3)
C5'—N4'—C9A'—C9'	−35.1 (3)	C5—N4—C9A—C1	−159.2 (2)
C2'—C1'—C9A'—N4'	−30.1 (3)	C10—C9—C9A—N4	−164.9 (2)
C2'—C1'—C9A'—C9'	−151.7 (3)	C8—C9—C9A—N4	−44.8 (3)
C8'—C9'—C9A'—N4'	−44.1 (3)	C10—C9—C9A—C1	−48.2 (3)
C10'—C9'—C9A'—N4'	−163.9 (2)	C8—C9—C9A—C1	72.0 (3)
C8'—C9'—C9A'—C1'	72.6 (3)	C2—C1—C9A—N4	−28.6 (3)
C10'—C9'—C9A'—C1'	−47.2 (3)	C2—C1—C9A—C9	−150.5 (2)
C8'—C9'—C10'—C16'	161.7 (3)	C9A—C9—C10—C11	162.2 (2)
C9A'—C9'—C10'—C16'	−72.5 (4)	C8—C9—C10—C11	36.3 (2)
C8'—C9'—C10'—C11'	36.2 (3)	C9A—C9—C10—C16	−71.6 (3)
C9A'—C9'—C10'—C11'	161.9 (2)	C8—C9—C10—C16	162.5 (3)
C8'—O2'—C11'—O3'	−94.7 (3)	C8—O2—C11—O3	−92.3 (2)
C8'—O2'—C11'—C12'	152.3 (3)	C8—O2—C11—C12	156.4 (2)
C8'—O2'—C11'—C10'	22.2 (3)	C8—O2—C11—C10	24.0 (3)
C14'—O3'—C11'—O2'	−118.9 (3)	C14—O3—C11—O2	−113.1 (2)
C14'—O3'—C11'—C12'	−1.3 (4)	C14—O3—C11—C12	2.5 (3)
C14'—O3'—C11'—C10'	126.3 (3)	C14—O3—C11—C10	132.4 (2)
C16'—C10'—C11'—O2'	−160.9 (3)	C9—C10—C11—O2	−37.4 (2)
C9'—C10'—C11'—O2'	−36.0 (3)	C16—C10—C11—O2	−162.7 (3)
C16'—C10'—C11'—O3'	−44.4 (3)	C9—C10—C11—O3	78.8 (2)
C9'—C10'—C11'—O3'	80.5 (3)	C16—C10—C11—O3	−46.4 (3)
C16'—C10'—C11'—C12'	74.0 (4)	C9—C10—C11—C12	−162.6 (2)
C9'—C10'—C11'—C12'	−161.1 (3)	C16—C10—C11—C12	72.2 (4)
O2'—C11'—C12'—C13'	115.6 (3)	O2—C11—C12—C13	111.1 (3)
O3'—C11'—C12'—C13'	−0.4 (4)	O3—C11—C12—C13	−4.0 (3)
C10'—C11'—C12'—C13'	−121.7 (3)	C10—C11—C12—C13	−125.3 (3)
C11'—C12'—C13'—C14'	1.9 (4)	C11—C12—C13—C14	3.8 (3)
C11'—C12'—C13'—C15'	177.3 (4)	C11—C12—C13—C15	−177.6 (3)
C11'—O3'—C14'—O4'	−175.9 (4)	C11—O3—C14—O4	−179.0 (3)
C11'—O3'—C14'—C13'	2.5 (4)	C11—O3—C14—C13	−0.5 (3)
C12'—C13'—C14'—O4'	175.5 (5)	C12—C13—C14—O4	176.3 (3)
C15'—C13'—C14'—O4'	−0.6 (7)	C15—C13—C14—O4	−2.5 (5)
C12'—C13'—C14'—O3'	−2.7 (4)	C12—C13—C14—O3	−2.1 (3)
C15'—C13'—C14'—O3'	−178.8 (4)	C15—C13—C14—O3	179.1 (2)
C11'—C10'—C16'—C17'	−79.4 (6)	C11—C10—C16—C17	−78.4 (5)
C9'—C10'—C16'—C17'	163.8 (5)	C9—C10—C16—C17	164.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1	0.81	1.98	2.796 (3)	175.
O1W—H1WB···O1'	0.83	1.97	2.784 (3)	171.
C5'—H5'A···O3i	0.97	2.58	3.545 (4)	178.
C10—H10A···O1Wii	0.98	2.58	3.450 (4)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1	0.81	1.98	2.796 (3)	175
O1W—H1WB⋯O1′	0.83	1.97	2.784 (3)	171
C5′—H5′A⋯O3i	0.97	2.58	3.545 (4)	178
C10—H10A⋯O1Wii	0.98	2.58	3.450 (4)	149

Symmetry codes: (i) ; (ii) .