2-Phenyl-ethyl 1-thio-β-d-galactopyran-oside hemihydrate.

The title compound, C(14)H(20)O(5)S·0.5H(2)O, crystallizes with two organic mol-ecules and a solvent water mol-ecule in the asymmetric unit. In both mol-ecules, the hexa-pyranosyl rings adopt a slightly distorted chair conformation ((5)C(2)) with four substituents in equatorial positions and one substituent in an axial position. The main difference between the organic mol-ecules is the dihedral angle between the phenyl ring and the best plane defined by the O-C(1)-C(2)-C(3) atoms (r.m.s deviations = 0.003 and 0.043 Å) of the hexa-pyranosyl rings [47.4 (4) and 86.5 (4)°]. In the asymmetric unit, mol-ecules are linked by two strong O-H⋯O hydrogen bonds. In the crystal, the components are linked by a total of 10 distinct O-H⋯O hydrogen bonds, resulting in the formation of a two-dimensional network parallel to the ab plane.

Related literature

For synthetic methods see: Helferich & Türk (1956 ▶). For pharmacological properties of the title compound, see: De Bruyne et al. (1977 ▶); Choi et al. (2003 ▶). Gutiérrez et al. (2011 ▶). For puckering parameters see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H20O5S·0.5H2O

M = 309.37

Orthorhombic,

a = 4.8358 (4) Å

b = 14.8218 (16) Å

c = 41.390 (3) Å

V = 2966.6 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.20 × 0.09 × 0.08 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 200; ▶ Blessing, 1995 ▶) T min = 0.954, T max = 0.981

14206 measured reflections

5217 independent reflections

2395 reflections with I > 2σ(I)

R int = 0.169

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.117

S = 0.68

5217 reflections

377 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 2269 Friedel pairs

Flack parameter: −0.25 (16)

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶)’.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031667/om2454sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031667/om2454Isup2.hkl

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

C14H20O5S·0.5H2O	F(000) = 1320
Mr = 309.37	Dx = 1.385 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3425 reflections
a = 4.8358 (4) Å	θ = 2.8–25.6°
b = 14.8218 (16) Å	µ = 0.24 mm−1
c = 41.390 (3) Å	T = 173 K
V = 2966.6 (5) Å3	Needle, colourless
Z = 8	0.20 × 0.09 × 0.08 mm

Stoe IPDS II two-circle diffractometer	5217 independent reflections
Radiation source: fine-focus sealed tube	2395 reflections with I > 2σ(I)
graphite	Rint = 0.169
ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (MULABS; Spek, 200; Blessing, 1995)	h = −4→5
Tmin = 0.954, Tmax = 0.981	k = −17→17
14206 measured reflections	l = −49→47

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0007P)2] where P = (Fo2 + 2Fc2)/3
S = 0.68	(Δ/σ)max = 0.001
5217 reflections	Δρmax = 0.28 e Å−3
377 parameters	Δρmin = −0.30 e Å−3
0 restraints	Absolute structure: Flack (1983), 2269 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.25 (16)

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
S1	0.3816 (4)	0.92470 (10)	0.85163 (4)	0.0217 (4)
O1	0.2305 (9)	0.7771 (2)	0.82113 (11)	0.0186 (11)
C2	0.1463 (14)	0.8684 (3)	0.82448 (14)	0.0171 (14)
H2	−0.0432	0.8697	0.8341	0.020*
C3	0.1355 (15)	0.9128 (3)	0.79134 (14)	0.0192 (15)
H3	0.3253	0.9114	0.7818	0.023*
C4	−0.0578 (14)	0.8611 (4)	0.76924 (14)	0.0150 (14)
H4	−0.2469	0.8656	0.7789	0.018*
C5	0.0165 (15)	0.7603 (4)	0.76836 (16)	0.0206 (17)
H5	−0.1313	0.7263	0.7566	0.025*
C6	0.0370 (14)	0.7259 (4)	0.80286 (15)	0.0176 (15)
H6	−0.1488	0.7321	0.8132	0.021*
C7	0.1644 (18)	0.9413 (4)	0.88681 (16)	0.0298 (18)
H7A	0.2706	0.9759	0.9031	0.036*
H7B	0.0036	0.9785	0.8804	0.036*
C8	0.0570 (17)	0.8546 (4)	0.90277 (18)	0.0335 (19)
H8A	−0.0909	0.8706	0.9183	0.040*
H8B	−0.0258	0.8156	0.8859	0.040*
C11	0.2787 (17)	0.8018 (4)	0.92039 (17)	0.0302 (19)
C12	0.3759 (19)	0.8276 (4)	0.95047 (17)	0.036 (2)
H12	0.3035	0.8805	0.9603	0.043*
C13	0.5745 (19)	0.7786 (5)	0.96658 (19)	0.040 (2)
H13	0.6369	0.7982	0.9872	0.049*
C14	0.684 (2)	0.7011 (4)	0.9531 (2)	0.044 (2)
H14	0.8212	0.6671	0.9641	0.053*
C15	0.588 (2)	0.6744 (5)	0.9230 (2)	0.050 (3)
H15	0.6588	0.6205	0.9137	0.060*
C16	0.395 (2)	0.7234 (4)	0.90633 (19)	0.042 (2)
H16	0.3392	0.7048	0.8854	0.050*
O31	0.0486 (12)	1.0048 (3)	0.79387 (11)	0.0352 (14)
H31	−0.0953	1.0262	0.7855	0.053*
O41	−0.0739 (10)	0.8992 (3)	0.73781 (10)	0.0234 (11)
H41	0.0863	0.9052	0.7303	0.035*
O51	0.2726 (10)	0.7497 (2)	0.75186 (12)	0.0239 (12)
H51	0.3191	0.6951	0.7521	0.036*
C61	0.1245 (16)	0.6275 (4)	0.80496 (16)	0.0254 (16)
H61B	0.0055	0.5902	0.7908	0.030*
H61C	0.3182	0.6210	0.7976	0.030*
O61	0.0999 (11)	0.5973 (3)	0.83768 (11)	0.0276 (11)
H61	0.2498	0.5739	0.8436	0.041*
S1A	0.1800 (4)	0.92289 (11)	0.58806 (4)	0.0207 (4)
O1A	0.4361 (10)	0.7963 (2)	0.62109 (10)	0.0185 (11)
C2A	0.4278 (15)	0.8930 (4)	0.61866 (14)	0.0174 (15)
H2A	0.6142	0.9150	0.6118	0.021*
C3A	0.3507 (14)	0.9383 (3)	0.65050 (15)	0.0162 (14)
H3A	0.1519	0.9264	0.6556	0.019*
C4A	0.5327 (14)	0.9033 (4)	0.67780 (14)	0.0166 (15)
H4A	0.7246	0.9268	0.6747	0.020*
C5A	0.5420 (14)	0.8010 (4)	0.67805 (16)	0.0170 (15)
H5A	0.6784	0.7805	0.6947	0.020*
C6A	0.6377 (15)	0.7696 (3)	0.64495 (15)	0.0171 (14)
H6A	0.8174	0.7998	0.6398	0.021*
C7A	0.3763 (16)	0.8986 (4)	0.55177 (15)	0.0246 (16)
H7A1	0.5560	0.9305	0.5526	0.030*
H7A2	0.4135	0.8330	0.5504	0.030*
C8A	0.2146 (16)	0.9289 (5)	0.52203 (15)	0.0298 (18)
H8A1	0.0333	0.8979	0.5216	0.036*
H8A2	0.1805	0.9946	0.5233	0.036*
C11A	0.3715 (16)	0.9077 (4)	0.49135 (15)	0.0265 (16)
C12A	0.5655 (18)	0.9652 (5)	0.47895 (18)	0.0323 (19)
H12A	0.6040	1.0207	0.4896	0.039*
C13A	0.7059 (17)	0.9425 (5)	0.45085 (19)	0.042 (2)
H13A	0.8432	0.9822	0.4426	0.050*
C14A	0.650 (2)	0.8640 (6)	0.43483 (19)	0.046 (2)
H14A	0.7484	0.8492	0.4157	0.055*
C15A	0.4537 (19)	0.8077 (5)	0.44622 (19)	0.039 (2)
H15A	0.4146	0.7536	0.4348	0.047*
C16A	0.3062 (18)	0.8271 (4)	0.47450 (17)	0.034 (2)
H16A	0.1666	0.7874	0.4822	0.041*
O31A	0.3948 (11)	1.0327 (2)	0.64734 (11)	0.0213 (10)
H31A	0.2432	1.0585	0.6437	0.032*
O41A	0.4250 (10)	0.9385 (3)	0.70761 (10)	0.0241 (11)
H41A	0.5551	0.9456	0.7208	0.036*
O51A	0.2770 (10)	0.7663 (3)	0.68599 (11)	0.0261 (12)
H51A	0.2409	0.7220	0.6740	0.039*
C61A	0.6753 (15)	0.6677 (4)	0.64172 (16)	0.0196 (15)
H61D	0.5043	0.6362	0.6484	0.023*
H61E	0.7153	0.6517	0.6190	0.023*
O61A	0.8991 (13)	0.6415 (3)	0.66183 (13)	0.0420 (15)
H61A	0.8688	0.5898	0.6693	0.063*
O1W	−0.4231 (11)	1.0767 (3)	0.76658 (13)	0.0445 (14)
H1WA	−0.5761	1.0770	0.7762	0.067*
H1WB	−0.4623	1.0412	0.7514	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.0215 (10)	0.0253 (7)	0.0184 (9)	0.0002 (8)	−0.0020 (8)	−0.0018 (7)
O1	0.016 (3)	0.018 (2)	0.022 (3)	0.0012 (18)	−0.004 (2)	0.0002 (19)
C2	0.016 (4)	0.020 (3)	0.015 (4)	0.003 (3)	−0.001 (3)	0.002 (3)
C3	0.029 (4)	0.015 (3)	0.014 (3)	0.003 (3)	−0.005 (3)	−0.004 (2)
C4	0.012 (4)	0.024 (3)	0.009 (4)	0.004 (3)	0.003 (3)	0.006 (2)
C5	0.020 (4)	0.025 (3)	0.017 (4)	−0.003 (3)	0.003 (3)	−0.003 (3)
C6	0.019 (4)	0.017 (3)	0.017 (4)	−0.002 (3)	−0.001 (3)	−0.003 (3)
C7	0.038 (5)	0.035 (4)	0.017 (4)	0.004 (4)	0.000 (4)	0.000 (3)
C8	0.033 (5)	0.039 (4)	0.028 (5)	0.007 (4)	0.003 (4)	0.003 (3)
C11	0.041 (5)	0.024 (3)	0.025 (5)	−0.010 (3)	0.002 (4)	0.007 (3)
C12	0.044 (6)	0.038 (4)	0.024 (4)	0.011 (4)	0.011 (4)	0.002 (3)
C13	0.051 (6)	0.040 (4)	0.030 (5)	−0.010 (4)	0.004 (5)	0.008 (4)
C14	0.063 (7)	0.028 (4)	0.041 (5)	0.004 (4)	−0.013 (5)	0.007 (3)
C15	0.066 (7)	0.033 (4)	0.053 (6)	0.011 (5)	−0.001 (6)	−0.004 (4)
C16	0.062 (6)	0.034 (4)	0.029 (5)	−0.005 (4)	−0.013 (5)	−0.004 (3)
O31	0.055 (4)	0.021 (2)	0.029 (3)	0.020 (2)	−0.018 (3)	0.001 (2)
O41	0.021 (3)	0.029 (2)	0.021 (3)	0.000 (2)	−0.005 (2)	0.0035 (19)
O51	0.034 (3)	0.013 (2)	0.024 (3)	0.0057 (19)	0.002 (3)	0.0008 (19)
C61	0.019 (4)	0.024 (3)	0.033 (4)	−0.009 (3)	0.002 (4)	0.001 (3)
O61	0.023 (3)	0.028 (2)	0.032 (3)	0.001 (2)	0.002 (2)	0.0133 (19)
S1A	0.0180 (9)	0.0286 (8)	0.0154 (9)	0.0032 (7)	−0.0022 (7)	−0.0005 (7)
O1A	0.020 (3)	0.0161 (19)	0.020 (3)	0.0050 (19)	−0.006 (2)	0.0004 (17)
C2A	0.017 (4)	0.021 (3)	0.014 (4)	0.002 (3)	−0.003 (3)	0.004 (2)
C3A	0.015 (4)	0.015 (3)	0.019 (3)	−0.003 (3)	0.000 (3)	−0.002 (3)
C4A	0.020 (4)	0.021 (3)	0.008 (3)	−0.005 (3)	−0.007 (3)	−0.002 (3)
C5A	0.014 (4)	0.019 (3)	0.018 (4)	−0.002 (3)	−0.002 (3)	0.002 (3)
C6A	0.015 (4)	0.018 (3)	0.019 (4)	0.003 (3)	−0.003 (3)	0.002 (3)
C7A	0.029 (4)	0.033 (3)	0.012 (4)	0.004 (3)	0.003 (4)	0.007 (3)
C8A	0.043 (5)	0.031 (3)	0.016 (4)	0.014 (4)	−0.003 (3)	−0.003 (3)
C11A	0.026 (4)	0.035 (4)	0.018 (4)	0.007 (4)	−0.006 (3)	0.001 (3)
C12A	0.034 (5)	0.035 (4)	0.028 (4)	0.002 (4)	−0.004 (4)	0.002 (3)
C13A	0.025 (5)	0.067 (5)	0.032 (5)	−0.001 (4)	0.004 (4)	0.016 (4)
C14A	0.042 (6)	0.074 (5)	0.022 (5)	0.023 (5)	0.000 (4)	0.000 (4)
C15A	0.044 (6)	0.042 (4)	0.032 (5)	0.013 (4)	0.005 (5)	−0.011 (4)
C16A	0.051 (6)	0.031 (4)	0.022 (4)	0.007 (4)	0.002 (4)	0.005 (3)
O31A	0.022 (3)	0.0197 (19)	0.023 (3)	−0.002 (2)	−0.008 (3)	0.002 (2)
O41A	0.032 (3)	0.027 (2)	0.014 (2)	−0.005 (2)	−0.003 (2)	−0.0025 (19)
O51A	0.029 (3)	0.028 (2)	0.021 (3)	−0.012 (2)	0.003 (2)	−0.001 (2)
C61A	0.020 (4)	0.021 (3)	0.018 (4)	0.001 (3)	0.003 (3)	0.000 (3)
O61A	0.050 (4)	0.019 (2)	0.057 (4)	0.005 (3)	−0.021 (3)	0.007 (2)
O1W	0.026 (3)	0.049 (3)	0.058 (4)	−0.015 (3)	0.005 (3)	−0.002 (3)

S1—C2	1.804 (7)	S1A—C7A	1.813 (7)
S1—C7	1.812 (7)	O1A—C2A	1.437 (6)
O1—C2	1.420 (7)	O1A—C6A	1.443 (8)
O1—C6	1.422 (7)	C2A—C3A	1.526 (8)
C2—C3	1.522 (8)	C2A—H2A	1.0000
C2—H2	1.0000	C3A—O31A	1.421 (6)
C3—O31	1.432 (7)	C3A—C4A	1.523 (8)
C3—C4	1.516 (9)	C3A—H3A	1.0000
C3—H3	1.0000	C4A—O41A	1.437 (7)
C4—O41	1.420 (7)	C4A—C5A	1.517 (8)
C4—C5	1.537 (8)	C4A—H4A	1.0000
C4—H4	1.0000	C5A—O51A	1.419 (8)
C5—O51	1.423 (8)	C5A—C6A	1.519 (9)
C5—C6	1.519 (9)	C5A—H5A	1.0000
C5—H5	1.0000	C6A—C61A	1.527 (7)
C6—C61	1.521 (8)	C6A—H6A	1.0000
C6—H6	1.0000	C7A—C8A	1.525 (9)
C7—C8	1.535 (9)	C7A—H7A1	0.9900
C7—H7A	0.9900	C7A—H7A2	0.9900
C7—H7B	0.9900	C8A—C11A	1.512 (9)
C8—C11	1.515 (10)	C8A—H8A1	0.9900
C8—H8A	0.9900	C8A—H8A2	0.9900
C8—H8B	0.9900	C11A—C12A	1.368 (11)
C11—C12	1.385 (10)	C11A—C16A	1.419 (9)
C11—C16	1.416 (10)	C12A—C13A	1.388 (10)
C12—C13	1.376 (11)	C12A—H12A	0.9500
C12—H12	0.9500	C13A—C14A	1.366 (11)
C13—C14	1.383 (10)	C13A—H13A	0.9500
C13—H13	0.9500	C14A—C15A	1.348 (12)
C14—C15	1.386 (11)	C14A—H14A	0.9500
C14—H14	0.9500	C15A—C16A	1.400 (10)
C15—C16	1.371 (12)	C15A—H15A	0.9500
C15—H15	0.9500	C16A—H16A	0.9500
C16—H16	0.9500	O31A—H31A	0.8400
O31—H31	0.8395	O41A—H41A	0.8400
O41—H41	0.8400	O51A—H51A	0.8400
O51—H51	0.8400	C61A—O61A	1.420 (8)
C61—O61	1.431 (8)	C61A—H61D	0.9900
C61—H61B	0.9900	C61A—H61E	0.9900
C61—H61C	0.9900	O61A—H61A	0.8400
O61—H61	0.8400	O1W—H1WA	0.8394
S1A—C2A	1.799 (7)	O1W—H1WB	0.8399
C2—S1—C7	101.4 (4)	C2A—O1A—C6A	109.8 (4)
C2—O1—C6	111.8 (5)	O1A—C2A—C3A	112.7 (5)
O1—C2—C3	109.5 (5)	O1A—C2A—S1A	108.3 (4)
O1—C2—S1	108.7 (4)	C3A—C2A—S1A	109.7 (4)
C3—C2—S1	112.5 (4)	O1A—C2A—H2A	108.7
O1—C2—H2	108.7	C3A—C2A—H2A	108.7
C3—C2—H2	108.7	S1A—C2A—H2A	108.7
S1—C2—H2	108.7	O31A—C3A—C4A	108.5 (5)
O31—C3—C4	110.2 (5)	O31A—C3A—C2A	108.5 (5)
O31—C3—C2	110.9 (5)	C4A—C3A—C2A	110.4 (5)
C4—C3—C2	110.2 (5)	O31A—C3A—H3A	109.8
O31—C3—H3	108.5	C4A—C3A—H3A	109.8
C4—C3—H3	108.5	C2A—C3A—H3A	109.8
C2—C3—H3	108.5	O41A—C4A—C5A	111.6 (5)
O41—C4—C3	112.7 (5)	O41A—C4A—C3A	107.7 (5)
O41—C4—C5	112.2 (5)	C5A—C4A—C3A	111.3 (5)
C3—C4—C5	111.2 (5)	O41A—C4A—H4A	108.7
O41—C4—H4	106.8	C5A—C4A—H4A	108.7
C3—C4—H4	106.8	C3A—C4A—H4A	108.7
C5—C4—H4	106.8	O51A—C5A—C4A	109.7 (5)
O51—C5—C6	110.9 (6)	O51A—C5A—C6A	111.9 (5)
O51—C5—C4	108.8 (5)	C4A—C5A—C6A	108.0 (5)
C6—C5—C4	108.6 (5)	O51A—C5A—H5A	109.1
O51—C5—H5	109.5	C4A—C5A—H5A	109.1
C6—C5—H5	109.5	C6A—C5A—H5A	109.1
C4—C5—H5	109.5	O1A—C6A—C5A	109.1 (5)
O1—C6—C5	111.3 (5)	O1A—C6A—C61A	106.9 (5)
O1—C6—C61	107.4 (5)	C5A—C6A—C61A	114.7 (5)
C5—C6—C61	113.2 (5)	O1A—C6A—H6A	108.6
O1—C6—H6	108.3	C5A—C6A—H6A	108.6
C5—C6—H6	108.3	C61A—C6A—H6A	108.6
C61—C6—H6	108.3	C8A—C7A—S1A	110.0 (5)
C8—C7—S1	115.4 (5)	C8A—C7A—H7A1	109.7
C8—C7—H7A	108.4	S1A—C7A—H7A1	109.7
S1—C7—H7A	108.4	C8A—C7A—H7A2	109.7
C8—C7—H7B	108.4	S1A—C7A—H7A2	109.7
S1—C7—H7B	108.4	H7A1—C7A—H7A2	108.2
H7A—C7—H7B	107.5	C11A—C8A—C7A	111.1 (6)
C11—C8—C7	113.6 (7)	C11A—C8A—H8A1	109.4
C11—C8—H8A	108.8	C7A—C8A—H8A1	109.4
C7—C8—H8A	108.8	C11A—C8A—H8A2	109.4
C11—C8—H8B	108.8	C7A—C8A—H8A2	109.4
C7—C8—H8B	108.8	H8A1—C8A—H8A2	108.0
H8A—C8—H8B	107.7	C12A—C11A—C16A	119.6 (7)
C12—C11—C16	117.5 (7)	C12A—C11A—C8A	122.0 (6)
C12—C11—C8	122.0 (6)	C16A—C11A—C8A	118.4 (7)
C16—C11—C8	120.5 (7)	C11A—C12A—C13A	119.9 (7)
C13—C12—C11	121.8 (7)	C11A—C12A—H12A	120.1
C13—C12—H12	119.1	C13A—C12A—H12A	120.1
C11—C12—H12	119.1	C14A—C13A—C12A	121.1 (8)
C12—C13—C14	120.7 (8)	C14A—C13A—H13A	119.5
C12—C13—H13	119.7	C12A—C13A—H13A	119.5
C14—C13—H13	119.7	C15A—C14A—C13A	119.8 (8)
C13—C14—C15	118.2 (8)	C15A—C14A—H14A	120.1
C13—C14—H14	120.9	C13A—C14A—H14A	120.1
C15—C14—H14	120.9	C14A—C15A—C16A	121.6 (7)
C16—C15—C14	121.9 (8)	C14A—C15A—H15A	119.2
C16—C15—H15	119.0	C16A—C15A—H15A	119.2
C14—C15—H15	119.0	C15A—C16A—C11A	118.0 (8)
C15—C16—C11	119.9 (7)	C15A—C16A—H16A	121.0
C15—C16—H16	120.0	C11A—C16A—H16A	121.0
C11—C16—H16	120.0	C3A—O31A—H31A	109.5
C3—O31—H31	125.0	C4A—O41A—H41A	109.5
C4—O41—H41	109.5	C5A—O51A—H51A	109.5
C5—O51—H51	109.5	O61A—C61A—C6A	108.1 (5)
O61—C61—C6	109.3 (5)	O61A—C61A—H61D	110.1
O61—C61—H61B	109.8	C6A—C61A—H61D	110.1
C6—C61—H61B	109.8	O61A—C61A—H61E	110.1
O61—C61—H61C	109.8	C6A—C61A—H61E	110.1
C6—C61—H61C	109.8	H61D—C61A—H61E	108.4
H61B—C61—H61C	108.3	C61A—O61A—H61A	109.5
C61—O61—H61	109.5	H1WA—O1W—H1WB	99.1
C2A—S1A—C7A	100.7 (3)
C6—O1—C2—C3	−63.2 (7)	C6A—O1A—C2A—C3A	−59.8 (7)
C6—O1—C2—S1	173.6 (4)	C6A—O1A—C2A—S1A	178.7 (4)
C7—S1—C2—O1	−109.5 (4)	C7A—S1A—C2A—O1A	−76.8 (5)
C7—S1—C2—C3	129.0 (5)	C7A—S1A—C2A—C3A	159.8 (4)
O1—C2—C3—O31	179.5 (5)	O1A—C2A—C3A—O31A	169.9 (5)
S1—C2—C3—O31	−59.5 (6)	S1A—C2A—C3A—O31A	−69.4 (6)
O1—C2—C3—C4	57.2 (7)	O1A—C2A—C3A—C4A	51.1 (7)
S1—C2—C3—C4	178.2 (4)	S1A—C2A—C3A—C4A	171.8 (4)
O31—C3—C4—O41	57.8 (7)	O31A—C3A—C4A—O41A	69.2 (6)
C2—C3—C4—O41	−179.5 (5)	C2A—C3A—C4A—O41A	−171.9 (5)
O31—C3—C4—C5	−175.2 (5)	O31A—C3A—C4A—C5A	−168.2 (5)
C2—C3—C4—C5	−52.5 (7)	C2A—C3A—C4A—C5A	−49.3 (7)
O41—C4—C5—O51	57.6 (7)	O41A—C4A—C5A—O51A	53.7 (7)
C3—C4—C5—O51	−69.6 (6)	C3A—C4A—C5A—O51A	−66.6 (7)
O41—C4—C5—C6	178.4 (6)	O41A—C4A—C5A—C6A	175.9 (5)
C3—C4—C5—C6	51.3 (7)	C3A—C4A—C5A—C6A	55.6 (7)
C2—O1—C6—C5	63.8 (7)	C2A—O1A—C6A—C5A	66.0 (6)
C2—O1—C6—C61	−171.8 (5)	C2A—O1A—C6A—C61A	−169.4 (5)
O51—C5—C6—O1	63.5 (6)	O51A—C5A—C6A—O1A	57.2 (6)
C4—C5—C6—O1	−56.0 (7)	C4A—C5A—C6A—O1A	−63.6 (6)
O51—C5—C6—C61	−57.5 (7)	O51A—C5A—C6A—C61A	−62.7 (7)
C4—C5—C6—C61	−177.1 (5)	C4A—C5A—C6A—C61A	176.5 (6)
C2—S1—C7—C8	61.9 (6)	C2A—S1A—C7A—C8A	−174.0 (5)
S1—C7—C8—C11	71.3 (7)	S1A—C7A—C8A—C11A	−178.9 (5)
C7—C8—C11—C12	77.3 (9)	C7A—C8A—C11A—C12A	−86.0 (8)
C7—C8—C11—C16	−102.6 (8)	C7A—C8A—C11A—C16A	96.4 (8)
C16—C11—C12—C13	−1.1 (12)	C16A—C11A—C12A—C13A	−3.0 (11)
C8—C11—C12—C13	179.0 (8)	C8A—C11A—C12A—C13A	179.5 (7)
C11—C12—C13—C14	−0.1 (13)	C11A—C12A—C13A—C14A	1.4 (12)
C12—C13—C14—C15	0.0 (13)	C12A—C13A—C14A—C15A	0.5 (12)
C13—C14—C15—C16	1.4 (14)	C13A—C14A—C15A—C16A	−0.7 (13)
C14—C15—C16—C11	−2.7 (14)	C14A—C15A—C16A—C11A	−0.9 (12)
C12—C11—C16—C15	2.5 (12)	C12A—C11A—C16A—C15A	2.7 (11)
C8—C11—C16—C15	−177.7 (8)	C8A—C11A—C16A—C15A	−179.6 (7)
O1—C6—C61—O61	65.0 (7)	O1A—C6A—C61A—O61A	172.2 (5)
C5—C6—C61—O61	−171.8 (6)	C5A—C6A—C61A—O61A	−66.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O31—H31···O1W	0.84	1.92	2.759 (7)	179.
O41—H41···O41A	0.84	1.95	2.779 (7)	169.
O51—H51···O1Wi	0.84	1.98	2.773 (6)	156.
O61—H61···O31Aii	0.84	1.86	2.697 (7)	172.
O31A—H31A···O61iii	0.84	1.92	2.650 (7)	145.
O41A—H41A···O41iv	0.84	2.05	2.788 (7)	147.
O51A—H51A···O61Av	0.84	2.10	2.785 (7)	138.
O61A—H61A···O31ii	0.84	2.02	2.744 (6)	145.
O1W—H1WA···O31v	0.84	2.23	2.989 (8)	150.
O1W—H1WB···O41Av	0.84	2.43	3.270 (6)	180.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O31—H31⋯O1W	0.84	1.92	2.759 (7)	179
O41—H41⋯O41A	0.84	1.95	2.779 (7)	169
O51—H51⋯O1Wi	0.84	1.98	2.773 (6)	156
O61—H61⋯O31Aii	0.84	1.86	2.697 (7)	172
O31A—H31A⋯O61iii	0.84	1.92	2.650 (7)	145
O41A—H41A⋯O41iv	0.84	2.05	2.788 (7)	147
O51A—H51A⋯O61Av	0.84	2.10	2.785 (7)	138
O61A—H61A⋯O31ii	0.84	2.02	2.744 (6)	145
O1W—H1WA⋯O31v	0.84	2.23	2.989 (8)	150
O1W—H1WB⋯O41Av	0.84	2.43	3.270 (6)	180

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