(3S,7R)-7,14,16-Trihy-droxy-3-methyl-3,4,5,6,7,8,9,10,11,12-deca-hydro-1H-2-benzoxacyclo-tetra-decin-1-one.

The asymmetric unit of the title compound, C(18)H(26)O(5), which is known as α-zearalanol, contains two mol-ecules having the same conformation, with a r.m.s. deviation of less than 0.03 Å for all non-H atoms. In each independent mol-ecule, an intra-molecular O-H⋯O hydrogen bond stabilizes the mol-ecular conformation. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules, forming infinite chains along [110] and [1-10].

Related literature

For the chemical preparation of α-zearalanol, see: Urry et al. (1966 ▶). For its natural occurrence as a metabolite, see: Baldwin et al. (1983 ▶) and for its use as an animal growth promoter, see: Wang & Wang (2007 ▶). For the crystal structures of related derivatives, see: Panneerselvam et al. (1996 ▶); Gelo-Pujić et al. (1994 ▶); Zhao et al. (2008 ▶); Köppen et al. (2012 ▶); Drzymala et al. (2012 ▶).

Experimental

Crystal data

C18H26O5

M = 322.39

Triclinic,

a = 5.0734 (11) Å

b = 11.618 (2) Å

c = 14.718 (3) Å

α = 87.388 (13)°

β = 86.595 (15)°

γ = 89.780 (15)°

V = 865.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.43 × 0.22 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.186, T max = 0.350

19642 measured reflections

4264 independent reflections

3421 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.147

S = 0.95

4264 reflections

431 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812041141/fj2595sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041141/fj2595Isup2.hkl

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

C18H26O5	Z = 2
Mr = 322.39	F(000) = 348
Triclinic, P1	Dx = 1.238 Mg m−3
a = 5.0734 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.618 (2) Å	Cell parameters from 6563 reflections
c = 14.718 (3) Å	θ = 2.3–26.4°
α = 87.388 (13)°	µ = 0.09 mm−1
β = 86.595 (15)°	T = 296 K
γ = 89.780 (15)°	Block, colourless
V = 865.0 (3) Å3	0.43 × 0.22 × 0.10 mm

Bruker APEXII CCD diffractometer	4264 independent reflections
Radiation source: fine-focus sealed tube	3421 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
φ and ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.186, Tmax = 0.350	k = −15→15
19642 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0803P)2] where P = (Fo2 + 2Fc2)/3
4264 reflections	(Δ/σ)max < 0.001
431 parameters	Δρmax = 0.24 e Å−3
7 restraints	Δρmin = −0.16 e Å−3

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	−0.1448 (4)	0.89233 (14)	0.65863 (11)	0.0465 (4)
O2	0.0413 (4)	0.99572 (16)	0.76207 (12)	0.0555 (5)
O3	−0.3004 (5)	0.45828 (17)	0.45181 (16)	0.0618 (6)
O4	0.2440 (5)	1.34395 (16)	0.41989 (13)	0.0570 (5)
O5	0.3693 (4)	1.15285 (17)	0.70652 (13)	0.0578 (5)
H5A	0.3015	1.1038	0.7423	0.087*
C1	−0.0231 (5)	0.9872 (2)	0.68358 (16)	0.0409 (5)
C2	−0.4309 (7)	0.8317 (3)	0.7915 (2)	0.0683 (8)
H2A	−0.3901	0.9000	0.8222	0.102*
H2B	−0.4694	0.7698	0.8356	0.102*
H2C	−0.5817	0.8459	0.7561	0.102*
C3	−0.1985 (5)	0.7995 (2)	0.72962 (16)	0.0435 (6)
H3B	−0.0429	0.7882	0.7654	0.052*
C4	−0.2456 (5)	0.6918 (2)	0.67829 (18)	0.0469 (6)
H4B	−0.3192	0.6329	0.7211	0.056*
H4C	−0.3763	0.7093	0.6341	0.056*
C5	−0.0035 (6)	0.6437 (2)	0.6292 (2)	0.0526 (7)
H5B	0.1227	0.6215	0.6738	0.063*
H5C	0.0767	0.7042	0.5893	0.063*
C6	−0.0549 (7)	0.5390 (2)	0.5722 (2)	0.0580 (7)
H6A	0.1135	0.5081	0.5500	0.070*
H6B	−0.1424	0.4797	0.6115	0.070*
C7	−0.2229 (6)	0.5653 (2)	0.49103 (19)	0.0493 (6)
H7A	−0.3846	0.6033	0.5140	0.059*
C8	−0.0915 (6)	0.6456 (2)	0.41628 (19)	0.0535 (7)
H8A	0.0351	0.6937	0.4435	0.064*
H8B	0.0053	0.5991	0.3725	0.064*
C9	−0.2828 (6)	0.7229 (2)	0.36581 (18)	0.0563 (7)
H9A	−0.1933	0.7532	0.3097	0.068*
H9B	−0.4294	0.6763	0.3493	0.068*
C10	−0.3925 (6)	0.8235 (2)	0.41891 (19)	0.0482 (6)
H10A	−0.4831	0.7935	0.4749	0.058*
H10B	−0.5218	0.8637	0.3833	0.058*
C11	−0.1827 (5)	0.9100 (2)	0.44291 (17)	0.0444 (6)
H11A	−0.0530	0.8701	0.4787	0.053*
H11B	−0.0925	0.9408	0.3871	0.053*
C12	−0.2995 (5)	1.0093 (2)	0.49636 (17)	0.0411 (5)
H12A	−0.4017	0.9785	0.5497	0.049*
H12B	−0.4182	1.0532	0.4587	0.049*
C13	−0.0089 (5)	1.1798 (2)	0.46580 (17)	0.0438 (6)
H13A	−0.0918	1.1891	0.4113	0.053*
C14	0.1884 (5)	1.2568 (2)	0.48410 (17)	0.0437 (6)
C15	0.3129 (6)	1.2462 (2)	0.56527 (18)	0.0457 (6)
H15A	0.4448	1.2977	0.5775	0.055*
C16	0.2384 (5)	1.1575 (2)	0.62849 (16)	0.0415 (5)
C17	0.0383 (5)	1.07732 (19)	0.61033 (16)	0.0372 (5)
C18	−0.0857 (5)	1.08946 (19)	0.52648 (16)	0.0377 (5)
O1'	0.5442 (4)	0.37345 (14)	0.94217 (11)	0.0462 (4)
O2'	0.3680 (4)	0.48975 (16)	0.83705 (12)	0.0549 (5)
O3'	0.6823 (5)	−0.08133 (17)	1.15210 (15)	0.0602 (5)
O4'	0.1425 (4)	0.79967 (16)	1.17536 (14)	0.0567 (5)
O5'	0.0323 (4)	0.63890 (17)	0.89001 (13)	0.0608 (5)
H5'A	0.1034	0.5941	0.8547	0.091*
C1'	0.4249 (5)	0.4708 (2)	0.91655 (17)	0.0414 (5)
C2'	0.8444 (7)	0.3297 (3)	0.8122 (3)	0.0726 (9)
H2'A	0.8052	0.4014	0.7807	0.109*
H2'B	0.8904	0.2729	0.7686	0.109*
H2'C	0.9897	0.3403	0.8498	0.109*
C3'	0.6061 (5)	0.2899 (2)	0.87071 (17)	0.0436 (6)
H3'B	0.4548	0.2832	0.8329	0.052*
C4'	0.6511 (6)	0.1755 (2)	0.92215 (19)	0.0484 (6)
H4'B	0.7733	0.1878	0.9690	0.058*
H4'C	0.7338	0.1224	0.8801	0.058*
C5'	0.4010 (6)	0.1196 (2)	0.96673 (18)	0.0497 (6)
H5'B	0.2853	0.1009	0.9194	0.060*
H5'C	0.3099	0.1750	1.0047	0.060*
C6'	0.4513 (6)	0.0096 (2)	1.02532 (19)	0.0548 (7)
H6'A	0.2827	−0.0263	1.0432	0.066*
H6'B	0.5524	−0.0437	0.9882	0.066*
C7'	0.5984 (6)	0.0283 (2)	1.11146 (18)	0.0472 (6)
H7'A	0.7575	0.0733	1.0933	0.057*
C8'	0.4374 (6)	0.0953 (2)	1.18242 (19)	0.0511 (6)
H8'A	0.3308	0.0415	1.2210	0.061*
H8'B	0.3183	0.1471	1.1514	0.061*
C9'	0.6079 (7)	0.1660 (2)	1.24287 (19)	0.0594 (8)
H9'A	0.4982	0.1905	1.2947	0.071*
H9'B	0.7455	0.1166	1.2660	0.071*
C10'	0.7366 (6)	0.2724 (2)	1.1937 (2)	0.0537 (7)
H10C	0.8532	0.3073	1.2345	0.064*
H10D	0.8440	0.2479	1.1414	0.064*
C11'	0.5409 (6)	0.3635 (2)	1.16147 (18)	0.0491 (6)
H11C	0.4388	0.3909	1.2140	0.059*
H11D	0.4194	0.3281	1.1227	0.059*
C12'	0.6742 (5)	0.4672 (2)	1.10867 (18)	0.0440 (6)
H12C	0.7903	0.5050	1.1480	0.053*
H12D	0.7810	0.4401	1.0571	0.053*
C13'	0.3928 (6)	0.6373 (2)	1.13423 (18)	0.0456 (6)
H13B	0.4704	0.6401	1.1898	0.055*
C14'	0.1995 (5)	0.7179 (2)	1.11290 (17)	0.0444 (6)
C15'	0.0797 (6)	0.7162 (2)	1.03129 (18)	0.0450 (6)
H15B	−0.0523	0.7690	1.0180	0.054*
C16'	0.1590 (5)	0.6347 (2)	0.96934 (16)	0.0417 (6)
C17'	0.3551 (5)	0.55111 (19)	0.98913 (16)	0.0376 (5)
C18'	0.4720 (5)	0.55347 (19)	1.07492 (16)	0.0389 (5)
H4A	0.388 (4)	1.371 (3)	0.431 (2)	0.073 (11)*
H3'A	0.543 (5)	−0.113 (4)	1.169 (3)	0.108 (17)*
H3A	−0.175 (5)	0.418 (3)	0.436 (3)	0.087 (14)*
H4'A	−0.005 (5)	0.823 (4)	1.163 (4)	0.13 (2)*

	U11	U22	U33	U12	U13	U23
O1	0.0625 (12)	0.0364 (9)	0.0408 (9)	−0.0108 (8)	−0.0077 (8)	0.0041 (7)
O2	0.0760 (13)	0.0506 (10)	0.0408 (9)	−0.0087 (10)	−0.0120 (9)	−0.0022 (8)
O3	0.0717 (16)	0.0379 (11)	0.0762 (14)	−0.0139 (11)	−0.0031 (12)	−0.0090 (9)
O4	0.0772 (15)	0.0375 (10)	0.0557 (11)	−0.0172 (10)	−0.0011 (11)	0.0022 (8)
O5	0.0702 (13)	0.0535 (11)	0.0519 (11)	−0.0147 (10)	−0.0194 (10)	−0.0050 (9)
C1	0.0458 (14)	0.0372 (12)	0.0393 (13)	0.0009 (10)	0.0025 (10)	−0.0048 (9)
C2	0.066 (2)	0.0638 (19)	0.072 (2)	−0.0032 (16)	0.0199 (16)	−0.0031 (15)
C3	0.0473 (14)	0.0422 (13)	0.0400 (12)	−0.0025 (11)	−0.0010 (10)	0.0090 (10)
C4	0.0490 (15)	0.0413 (14)	0.0494 (14)	−0.0106 (11)	−0.0020 (11)	0.0078 (11)
C5	0.0513 (16)	0.0489 (15)	0.0584 (16)	−0.0009 (13)	−0.0098 (13)	−0.0034 (12)
C6	0.072 (2)	0.0400 (14)	0.0628 (17)	−0.0007 (13)	−0.0070 (15)	−0.0040 (12)
C7	0.0560 (16)	0.0319 (12)	0.0593 (16)	−0.0116 (11)	0.0059 (13)	−0.0059 (11)
C8	0.0623 (18)	0.0402 (14)	0.0568 (16)	−0.0132 (13)	0.0130 (14)	−0.0098 (12)
C9	0.078 (2)	0.0482 (15)	0.0433 (13)	−0.0210 (14)	−0.0054 (13)	−0.0057 (11)
C10	0.0565 (16)	0.0425 (13)	0.0466 (13)	−0.0088 (12)	−0.0128 (12)	0.0004 (10)
C11	0.0509 (15)	0.0368 (12)	0.0456 (13)	−0.0098 (11)	−0.0031 (11)	−0.0029 (10)
C12	0.0397 (13)	0.0377 (12)	0.0462 (13)	−0.0041 (10)	−0.0068 (10)	0.0001 (10)
C13	0.0559 (16)	0.0344 (12)	0.0420 (13)	−0.0015 (11)	−0.0082 (11)	−0.0033 (10)
C14	0.0554 (15)	0.0291 (11)	0.0461 (13)	−0.0034 (11)	0.0019 (11)	−0.0035 (10)
C15	0.0515 (14)	0.0356 (12)	0.0506 (14)	−0.0083 (11)	−0.0005 (11)	−0.0105 (10)
C16	0.0462 (14)	0.0379 (13)	0.0413 (13)	−0.0012 (11)	−0.0031 (11)	−0.0091 (10)
C17	0.0438 (13)	0.0297 (11)	0.0384 (11)	−0.0005 (10)	−0.0001 (10)	−0.0067 (9)
C18	0.0377 (12)	0.0324 (11)	0.0432 (12)	0.0003 (10)	−0.0024 (10)	−0.0050 (9)
O1'	0.0606 (11)	0.0368 (9)	0.0418 (9)	0.0061 (8)	−0.0066 (8)	−0.0057 (7)
O2'	0.0787 (14)	0.0458 (10)	0.0406 (10)	0.0043 (9)	−0.0097 (9)	0.0003 (8)
O3'	0.0700 (15)	0.0376 (10)	0.0724 (13)	0.0094 (10)	−0.0038 (11)	0.0034 (9)
O4'	0.0712 (14)	0.0415 (11)	0.0567 (11)	0.0081 (10)	0.0065 (10)	−0.0081 (8)
O5'	0.0785 (14)	0.0532 (11)	0.0521 (11)	0.0131 (10)	−0.0191 (10)	0.0004 (9)
C1'	0.0474 (14)	0.0343 (12)	0.0420 (13)	−0.0040 (10)	−0.0006 (11)	0.0016 (9)
C2'	0.070 (2)	0.0622 (19)	0.082 (2)	−0.0024 (17)	0.0238 (18)	−0.0024 (16)
C3'	0.0473 (14)	0.0415 (13)	0.0417 (12)	−0.0006 (11)	0.0031 (10)	−0.0074 (10)
C4'	0.0502 (15)	0.0445 (14)	0.0504 (14)	0.0071 (12)	0.0012 (11)	−0.0080 (11)
C5'	0.0538 (16)	0.0470 (15)	0.0486 (14)	−0.0032 (12)	−0.0060 (12)	−0.0012 (11)
C6'	0.0695 (19)	0.0388 (14)	0.0564 (16)	−0.0056 (13)	−0.0047 (14)	−0.0040 (12)
C7'	0.0563 (16)	0.0320 (12)	0.0528 (14)	0.0023 (11)	0.0000 (12)	−0.0001 (10)
C8'	0.0619 (17)	0.0403 (13)	0.0499 (14)	0.0036 (12)	0.0029 (12)	0.0013 (11)
C9'	0.093 (2)	0.0404 (14)	0.0452 (14)	0.0140 (15)	−0.0131 (15)	0.0002 (11)
C10'	0.0653 (18)	0.0387 (13)	0.0596 (17)	0.0054 (12)	−0.0225 (14)	−0.0040 (12)
C11'	0.0591 (16)	0.0382 (13)	0.0500 (14)	0.0053 (12)	−0.0073 (12)	0.0019 (11)
C12'	0.0495 (15)	0.0388 (13)	0.0452 (13)	0.0012 (11)	−0.0107 (11)	−0.0059 (10)
C13'	0.0550 (16)	0.0367 (13)	0.0452 (13)	−0.0047 (11)	−0.0045 (11)	−0.0019 (10)
C14'	0.0549 (15)	0.0313 (12)	0.0452 (13)	−0.0010 (11)	0.0090 (11)	0.0015 (10)
C15'	0.0498 (15)	0.0321 (12)	0.0521 (14)	0.0041 (11)	0.0010 (11)	0.0045 (10)
C16'	0.0492 (15)	0.0344 (12)	0.0406 (12)	−0.0055 (11)	−0.0030 (10)	0.0074 (10)
C17'	0.0413 (13)	0.0309 (11)	0.0402 (12)	−0.0052 (10)	−0.0010 (10)	0.0017 (9)
C18'	0.0409 (13)	0.0298 (12)	0.0456 (13)	−0.0046 (10)	−0.0033 (10)	0.0024 (10)

O1—C1	1.341 (3)	O1'—C1'	1.331 (3)
O1—C3	1.482 (3)	O1'—C3'	1.483 (3)
O2—C1	1.227 (3)	O2'—C1'	1.232 (3)
O3—C7	1.460 (3)	O3'—C7'	1.456 (3)
O3—H3A	0.818 (10)	O3'—H3'A	0.821 (10)
O4—C14	1.372 (3)	O4'—C14'	1.370 (3)
O4—H4A	0.826 (10)	O4'—H4'A	0.821 (10)
O5—C16	1.359 (3)	O5'—C16'	1.365 (3)
O5—H5A	0.8200	O5'—H5'A	0.8200
C1—C17	1.489 (3)	C1'—C17'	1.476 (3)
C2—C3	1.503 (4)	C2'—C3'	1.504 (4)
C2—H2A	0.9600	C2'—H2'A	0.9600
C2—H2B	0.9600	C2'—H2'B	0.9600
C2—H2C	0.9600	C2'—H2'C	0.9600
C3—C4	1.517 (4)	C3'—C4'	1.523 (4)
C3—H3B	0.9800	C3'—H3'B	0.9800
C4—C5	1.507 (4)	C4'—C5'	1.527 (4)
C4—H4B	0.9700	C4'—H4'B	0.9700
C4—H4C	0.9700	C4'—H4'C	0.9700
C5—C6	1.540 (4)	C5'—C6'	1.538 (4)
C5—H5B	0.9700	C5'—H5'B	0.9700
C5—H5C	0.9700	C5'—H5'C	0.9700
C6—C7	1.527 (4)	C6'—C7'	1.533 (4)
C6—H6A	0.9700	C6'—H6'A	0.9700
C6—H6B	0.9700	C6'—H6'B	0.9700
C7—C8	1.532 (4)	C7'—C8'	1.527 (4)
C7—H7A	0.9800	C7'—H7'A	0.9800
C8—C9	1.523 (5)	C8'—C9'	1.542 (4)
C8—H8A	0.9700	C8'—H8'A	0.9700
C8—H8B	0.9700	C8'—H8'B	0.9700
C9—C10	1.520 (4)	C9'—C10'	1.532 (4)
C9—H9A	0.9700	C9'—H9'A	0.9700
C9—H9B	0.9700	C9'—H9'B	0.9700
C10—C11	1.534 (3)	C10'—C11'	1.528 (4)
C10—H10A	0.9700	C10'—H10C	0.9700
C10—H10B	0.9700	C10'—H10D	0.9700
C11—C12	1.524 (3)	C11'—C12'	1.540 (4)
C11—H11A	0.9700	C11'—H11C	0.9700
C11—H11B	0.9700	C11'—H11D	0.9700
C12—C18	1.531 (3)	C12'—C18'	1.520 (3)
C12—H12A	0.9700	C12'—H12C	0.9700
C12—H12B	0.9700	C12'—H12D	0.9700
C13—C18	1.388 (3)	C13'—C18'	1.381 (3)
C13—C14	1.391 (4)	C13'—C14'	1.392 (4)
C13—H13A	0.9300	C13'—H13B	0.9300
C14—C15	1.385 (4)	C14'—C15'	1.379 (4)
C15—C16	1.394 (3)	C15'—C16'	1.387 (4)
C15—H15A	0.9300	C15'—H15B	0.9300
C16—C17	1.425 (3)	C16'—C17'	1.421 (3)
C17—C18	1.419 (3)	C17'—C18'	1.428 (3)
C1—O1—C3	117.26 (18)	C1'—O1'—C3'	116.96 (18)
C7—O3—H3A	113 (3)	C7'—O3'—H3'A	103 (3)
C14—O4—H4A	106 (3)	C14'—O4'—H4'A	104 (4)
C16—O5—H5A	109.5	C16'—O5'—H5'A	109.5
O2—C1—O1	120.9 (2)	O2'—C1'—O1'	121.1 (2)
O2—C1—C17	122.7 (2)	O2'—C1'—C17'	122.5 (2)
O1—C1—C17	116.3 (2)	O1'—C1'—C17'	116.3 (2)
C3—C2—H2A	109.5	C3'—C2'—H2'A	109.5
C3—C2—H2B	109.5	C3'—C2'—H2'B	109.5
H2A—C2—H2B	109.5	H2'A—C2'—H2'B	109.5
C3—C2—H2C	109.5	C3'—C2'—H2'C	109.5
H2A—C2—H2C	109.5	H2'A—C2'—H2'C	109.5
H2B—C2—H2C	109.5	H2'B—C2'—H2'C	109.5
O1—C3—C2	109.9 (2)	O1'—C3'—C2'	109.8 (2)
O1—C3—C4	105.53 (19)	O1'—C3'—C4'	105.24 (19)
C2—C3—C4	113.1 (2)	C2'—C3'—C4'	112.8 (2)
O1—C3—H3B	109.4	O1'—C3'—H3'B	109.6
C2—C3—H3B	109.4	C2'—C3'—H3'B	109.6
C4—C3—H3B	109.4	C4'—C3'—H3'B	109.6
C5—C4—C3	114.9 (2)	C3'—C4'—C5'	114.6 (2)
C5—C4—H4B	108.5	C3'—C4'—H4'B	108.6
C3—C4—H4B	108.5	C5'—C4'—H4'B	108.6
C5—C4—H4C	108.5	C3'—C4'—H4'C	108.6
C3—C4—H4C	108.5	C5'—C4'—H4'C	108.6
H4B—C4—H4C	107.5	H4'B—C4'—H4'C	107.6
C4—C5—C6	114.8 (2)	C4'—C5'—C6'	114.1 (2)
C4—C5—H5B	108.6	C4'—C5'—H5'B	108.7
C6—C5—H5B	108.6	C6'—C5'—H5'B	108.7
C4—C5—H5C	108.6	C4'—C5'—H5'C	108.7
C6—C5—H5C	108.6	C6'—C5'—H5'C	108.7
H5B—C5—H5C	107.5	H5'B—C5'—H5'C	107.6
C7—C6—C5	114.4 (2)	C7'—C6'—C5'	114.9 (2)
C7—C6—H6A	108.7	C7'—C6'—H6'A	108.5
C5—C6—H6A	108.7	C5'—C6'—H6'A	108.5
C7—C6—H6B	108.7	C7'—C6'—H6'B	108.5
C5—C6—H6B	108.7	C5'—C6'—H6'B	108.5
H6A—C6—H6B	107.6	H6'A—C6'—H6'B	107.5
O3—C7—C6	110.1 (2)	O3'—C7'—C8'	109.8 (2)
O3—C7—C8	109.6 (2)	O3'—C7'—C6'	110.6 (2)
C6—C7—C8	114.5 (2)	C8'—C7'—C6'	113.3 (2)
O3—C7—H7A	107.5	O3'—C7'—H7'A	107.6
C6—C7—H7A	107.5	C8'—C7'—H7'A	107.6
C8—C7—H7A	107.5	C6'—C7'—H7'A	107.6
C9—C8—C7	114.4 (2)	C7'—C8'—C9'	113.6 (3)
C9—C8—H8A	108.7	C7'—C8'—H8'A	108.8
C7—C8—H8A	108.7	C9'—C8'—H8'A	108.8
C9—C8—H8B	108.7	C7'—C8'—H8'B	108.8
C7—C8—H8B	108.7	C9'—C8'—H8'B	108.8
H8A—C8—H8B	107.6	H8'A—C8'—H8'B	107.7
C10—C9—C8	114.9 (2)	C10'—C9'—C8'	114.1 (2)
C10—C9—H9A	108.5	C10'—C9'—H9'A	108.7
C8—C9—H9A	108.5	C8'—C9'—H9'A	108.7
C10—C9—H9B	108.5	C10'—C9'—H9'B	108.7
C8—C9—H9B	108.5	C8'—C9'—H9'B	108.7
H9A—C9—H9B	107.5	H9'A—C9'—H9'B	107.6
C9—C10—C11	114.1 (2)	C11'—C10'—C9'	114.4 (3)
C9—C10—H10A	108.7	C11'—C10'—H10C	108.7
C11—C10—H10A	108.7	C9'—C10'—H10C	108.7
C9—C10—H10B	108.7	C11'—C10'—H10D	108.7
C11—C10—H10B	108.7	C9'—C10'—H10D	108.7
H10A—C10—H10B	107.6	H10C—C10'—H10D	107.6
C12—C11—C10	112.7 (2)	C10'—C11'—C12'	113.4 (2)
C12—C11—H11A	109.1	C10'—C11'—H11C	108.9
C10—C11—H11A	109.1	C12'—C11'—H11C	108.9
C12—C11—H11B	109.1	C10'—C11'—H11D	108.9
C10—C11—H11B	109.1	C12'—C11'—H11D	108.9
H11A—C11—H11B	107.8	H11C—C11'—H11D	107.7
C11—C12—C18	112.0 (2)	C18'—C12'—C11'	111.6 (2)
C11—C12—H12A	109.2	C18'—C12'—H12C	109.3
C18—C12—H12A	109.2	C11'—C12'—H12C	109.3
C11—C12—H12B	109.2	C18'—C12'—H12D	109.3
C18—C12—H12B	109.2	C11'—C12'—H12D	109.3
H12A—C12—H12B	107.9	H12C—C12'—H12D	108.0
C18—C13—C14	122.0 (2)	C18'—C13'—C14'	121.6 (2)
C18—C13—H13A	119.0	C18'—C13'—H13B	119.2
C14—C13—H13A	119.0	C14'—C13'—H13B	119.2
O4—C14—C15	122.8 (2)	O4'—C14'—C15'	122.5 (2)
O4—C14—C13	116.8 (2)	O4'—C14'—C13'	116.7 (2)
C15—C14—C13	120.4 (2)	C15'—C14'—C13'	120.8 (2)
C14—C15—C16	119.3 (2)	C14'—C15'—C16'	119.0 (2)
C14—C15—H15A	120.4	C14'—C15'—H15B	120.5
C16—C15—H15A	120.4	C16'—C15'—H15B	120.5
O5—C16—C15	115.8 (2)	O5'—C16'—C15'	115.6 (2)
O5—C16—C17	123.2 (2)	O5'—C16'—C17'	122.9 (2)
C15—C16—C17	121.0 (2)	C15'—C16'—C17'	121.5 (2)
C18—C17—C16	118.8 (2)	C16'—C17'—C18'	118.2 (2)
C18—C17—C1	125.7 (2)	C16'—C17'—C1'	116.0 (2)
C16—C17—C1	115.6 (2)	C18'—C17'—C1'	125.8 (2)
C13—C18—C17	118.6 (2)	C13'—C18'—C17'	118.8 (2)
C13—C18—C12	116.4 (2)	C13'—C18'—C12'	116.2 (2)
C17—C18—C12	125.0 (2)	C17'—C18'—C12'	124.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2	0.82	1.83	2.549 (3)	146
O5′—H5′A···O2′	0.82	1.82	2.540 (3)	146
O4—H4A···O3i	0.83 (2)	1.93 (3)	2.745 (3)	171 (3)
O4′—H4′A···O3′ii	0.82 (3)	1.94 (3)	2.740 (3)	163 (4)
O3—H3A···O4iii	0.82 (3)	2.29 (3)	3.080 (3)	162 (3)
O3′—H3′A···O4′iii	0.82 (3)	2.27 (3)	3.067 (3)	165 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2	0.82	1.83	2.549 (3)	146
O5′—H5′A⋯O2′	0.82	1.82	2.540 (3)	146
O4—H4A⋯O3i	0.83 (2)	1.93 (3)	2.745 (3)	171 (3)
O4′—H4′A⋯O3′ii	0.82 (3)	1.94 (3)	2.740 (3)	163 (4)
O3—H3A⋯O4iii	0.82 (3)	2.29 (3)	3.080 (3)	162 (3)
O3′—H3′A⋯O4′iii	0.82 (3)	2.27 (3)	3.067 (3)	165 (4)

Symmetry codes: (i) ; (ii) ; (iii) .