N,N,N-Trimethyl-N-(methyl 5-de-oxy-2,3-O-iso-propyl-idene-β-d-ribo-furan-osid-5-yl)ammonium 4-methyl-benzene-sulfonate sesquihydrate.

The structure of the title compound, [C12H24NO4][C7H7O3S]·1.5H2O, contains alternating layers parallel to (001) of hydro-phobic and polar character, stabilized by C-H⋯O hydrogen bonding. The furan ring adopts an envelope conformation with the C(OMe) atom as the flap, and the dioxolane ring is twisted about one of the O-C(methine) bonds. A comparison to related compounds is presented. The tosyl-ate-O atoms were disordered over two positions with the major component having a site occupancy factor = 0.566 (12). The structure was refined as a rotary twin with regard to rotation about the c axis with the contribution of the second component being 0.0048 (6). Solvate water mol-ecules are highly disordered and were removed using the SQUEEZE procedure; the unit cell characteristics take into account the presence of the disordered solvent. High-resolution (1)H and (13)C NMR spectroscopic data are also presented.

Related literature

For background to quaternary ammonium compounds, see: Jones (1984 ▶); Śliwa (1996 ▶); Sajomsang et al. (2009 ▶); Obłąk & Gamian (2010 ▶); Binks et al. (2011 ▶); Singh et al. (2009 ▶); Cruz-Guzman et al. (2005 ▶); Rabea et al. (2003 ▶); Belalia et al., 2008 ▶; McDonnell & Russell (1999 ▶); Boethling (1984 ▶); Levinson (1999 ▶); Cross & Singer (1994 ▶). For QAC sugar derivatives, see: Abel et al. (2002 ▶); Blizzard et al. (2002 ▶); Honda et al. (1988 ▶); Thomas et al. (2009 ▶); Maslov et al. (2010 ▶); Dmochowska et al. (2006 ▶, 2009 ▶, 2011 ▶); Pellowska-Januszek et al. (2004 ▶); Skorupa et al. (2004 ▶). For related synthetic methods, see: Gosh & Liu (1996 ▶); Sairam et al. 2003 ▶; Sarabia-Garcia & Lopez-Herrera (1996 ▶); Dibrov et al. (2010 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H24NO4 +·C7H7O3S−·1.5H2O

M = 444.53

Monoclinic,

a = 11.4896 (15) Å

b = 7.9311 (11) Å

c = 13.4853 (17) Å

β = 111.619 (12)°

V = 1142.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 200 K

0.37 × 0.2 × 0.17 mm

Data collection

Kuma KM4CCD (Sapphire2 detector) diffractometer

26053 measured reflections

4481 independent reflections

4325 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.139

S = 1.07

4481 reflections

283 parameters

40 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack & Bernardinelli (1999 ▶)

Flack parameter: 0.08 (12)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and WinGX (Farrugia, 2012 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014797/tk5228sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014797/tk5228Isup2.hkl

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

C12H24NO4+·C7H7O3S−·1.5H2O	F(000) = 478
Mr = 444.53	Dx = 1.292 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3067 reflections
a = 11.4896 (15) Å	θ = 2–30°
b = 7.9311 (11) Å	µ = 0.19 mm−1
c = 13.4853 (17) Å	T = 200 K
β = 111.619 (12)°	Block, colourless
V = 1142.4 (3) Å3	0.37 × 0.2 × 0.17 mm
Z = 2

Kuma KM4CCD (Sapphire2 detector) diffractometer	Rint = 0.038
Graphite monochromator	θmax = 26°, θmin = 2.9°
ω scans, 1 deg frames	h = −14→14
26053 measured reflections	k = −9→9
4481 independent reflections	l = −16→16
4325 reflections with I > 2σ(I)

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0737P)2 + 0.6709P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.007
4481 reflections	Δρmax = 0.40 e Å−3
283 parameters	Δρmin = −0.31 e Å−3
40 restraints	Absolute structure: Flack & Bernardinelli (1999)
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (12)

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.4006 (3)	0.9674 (4)	0.8428 (2)	0.0299 (6)
H1	0.4517	1.0147	0.9144	0.036*
C2	0.4217 (3)	0.7801 (4)	0.8398 (2)	0.0294 (6)
H2	0.3676	0.7123	0.8683	0.035*
C3	0.3957 (3)	0.7445 (4)	0.7215 (2)	0.0284 (6)
H3	0.3089	0.701	0.6836	0.034*
C4	0.4153 (3)	0.9195 (3)	0.6776 (2)	0.0261 (6)
H4	0.4913	0.9144	0.6584	0.031*
O5	0.43649 (19)	1.0397 (3)	0.76273 (15)	0.0295 (5)
O6	0.5509 (2)	0.7393 (3)	0.88856 (15)	0.0322 (5)
C7	0.5743 (3)	0.6006 (4)	0.8296 (2)	0.0314 (6)
O8	0.4872 (2)	0.6252 (3)	0.72143 (15)	0.0392 (5)
C9	0.5476 (4)	0.4340 (4)	0.8700 (3)	0.0447 (8)
H9A	0.5643	0.3425	0.8281	0.067*
H9B	0.4597	0.43	0.8628	0.067*
H9C	0.6015	0.4207	0.9452	0.067*
C10	0.7061 (3)	0.6147 (5)	0.8315 (3)	0.0457 (8)
H10A	0.7229	0.5206	0.7916	0.069*
H10B	0.7656	0.6114	0.9054	0.069*
H10C	0.7154	0.7215	0.7985	0.069*
C11	0.3025 (3)	0.9654 (4)	0.5787 (2)	0.0282 (6)
H11A	0.2815	0.8671	0.53	0.034*
H11B	0.2304	0.9857	0.6005	0.034*
N12	0.3178 (2)	1.1180 (3)	0.51680 (16)	0.0272 (5)
C13	0.4218 (3)	1.0949 (4)	0.4768 (2)	0.0378 (7)
H13A	0.4081	0.9909	0.4347	0.057*
H13B	0.5016	1.0875	0.5374	0.057*
H13C	0.4239	1.1911	0.4319	0.057*
C14	0.1974 (3)	1.1358 (5)	0.4218 (2)	0.0424 (7)
H14A	0.1277	1.1511	0.4463	0.064*
H14B	0.1833	1.034	0.3777	0.064*
H14C	0.2028	1.2339	0.3796	0.064*
C15	0.3408 (4)	1.2769 (4)	0.5807 (3)	0.0407 (8)
H15A	0.2732	1.2939	0.6076	0.061*
H15B	0.3434	1.3725	0.5354	0.061*
H15C	0.4209	1.2686	0.6409	0.061*
O16	0.2726 (2)	0.9863 (3)	0.8220 (2)	0.0411 (6)
C17	0.2344 (4)	1.1544 (6)	0.8338 (3)	0.0527 (9)
H17A	0.144	1.1564	0.8176	0.079*
H17B	0.2545	1.2296	0.7847	0.079*
H17C	0.2787	1.1924	0.9073	0.079*
C18	0.8291 (3)	0.1549 (4)	0.8487 (2)	0.0322 (6)
C19	0.9296 (3)	0.2527 (5)	0.9119 (4)	0.0503 (9)
H19	0.9773	0.3154	0.8802	0.06*
C20	0.9596 (3)	0.2581 (5)	1.0210 (4)	0.0550 (10)
H20	1.028	0.3257	1.0638	0.066*
C21	0.8916 (3)	0.1665 (5)	1.0694 (3)	0.0497 (10)
C22	0.7906 (3)	0.0723 (4)	1.0053 (3)	0.0391 (7)
H22	0.7424	0.0101	1.0368	0.047*
C23	0.7587 (3)	0.0678 (4)	0.8952 (2)	0.0313 (6)
H23	0.6881	0.0044	0.8519	0.038*
C24	0.9289 (5)	0.1691 (8)	1.1889 (3)	0.086 (2)
H24A	1.0139	0.124	1.2227	0.13*
H24B	0.8705	0.0995	1.2089	0.13*
H24C	0.9265	0.2852	1.2129	0.13*
S25	0.78821 (10)	0.14712 (13)	0.70869 (7)	0.0533 (3)
O26	0.6888 (12)	0.2652 (11)	0.6587 (9)	0.063 (4)	0.434 (12)
O27	0.7138 (7)	−0.0238 (7)	0.6715 (4)	0.039 (2)	0.434 (12)
O28	0.8913 (7)	0.138 (2)	0.6800 (6)	0.093 (6)	0.434 (12)
O26A	0.8903 (7)	0.2787 (11)	0.7015 (6)	0.074 (2)	0.566 (12)
O27A	0.8177 (15)	−0.0076 (8)	0.6870 (7)	0.115 (6)	0.566 (12)
O28A	0.6753 (10)	0.235 (2)	0.6701 (10)	0.109 (6)	0.566 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0336 (15)	0.0316 (15)	0.0258 (13)	0.0032 (12)	0.0123 (11)	0.0008 (11)
C2	0.0327 (15)	0.0305 (15)	0.0276 (13)	−0.0006 (12)	0.0142 (11)	0.0016 (11)
C3	0.0305 (15)	0.0277 (14)	0.0249 (13)	−0.0006 (12)	0.0077 (11)	0.0011 (11)
C4	0.0288 (14)	0.0267 (14)	0.0220 (12)	−0.0006 (11)	0.0085 (10)	−0.0003 (10)
O5	0.0378 (11)	0.0260 (10)	0.0245 (9)	−0.0026 (8)	0.0112 (8)	−0.0017 (8)
O6	0.0363 (11)	0.0317 (11)	0.0238 (9)	0.0047 (9)	0.0053 (8)	−0.0036 (8)
C7	0.0411 (16)	0.0258 (15)	0.0239 (13)	0.0045 (12)	0.0080 (11)	−0.0005 (11)
O8	0.0576 (14)	0.0338 (12)	0.0235 (9)	0.0153 (11)	0.0117 (9)	0.0003 (9)
C9	0.071 (2)	0.0285 (17)	0.0331 (16)	0.0007 (16)	0.0170 (16)	0.0024 (13)
C10	0.0428 (18)	0.042 (2)	0.0556 (19)	0.0086 (16)	0.0216 (15)	−0.0026 (16)
C11	0.0317 (15)	0.0285 (15)	0.0232 (12)	−0.0037 (12)	0.0089 (11)	0.0035 (11)
N12	0.0320 (12)	0.0271 (12)	0.0213 (10)	−0.0037 (10)	0.0083 (9)	−0.0014 (9)
C13	0.0438 (17)	0.0425 (19)	0.0320 (14)	−0.0032 (15)	0.0199 (13)	0.0026 (13)
C14	0.0395 (17)	0.0455 (19)	0.0325 (14)	0.0001 (15)	0.0019 (12)	0.0118 (15)
C15	0.064 (2)	0.0266 (16)	0.0340 (16)	−0.0035 (15)	0.0214 (15)	−0.0020 (13)
O16	0.0346 (12)	0.0409 (13)	0.0544 (13)	0.0037 (10)	0.0242 (10)	−0.0032 (11)
C17	0.055 (2)	0.051 (2)	0.058 (2)	0.0229 (19)	0.0277 (18)	0.0015 (19)
C18	0.0295 (14)	0.0293 (15)	0.0397 (15)	0.0087 (13)	0.0150 (12)	0.0041 (13)
C19	0.0292 (17)	0.0359 (18)	0.085 (3)	−0.0051 (14)	0.0198 (17)	0.0035 (18)
C20	0.0311 (18)	0.047 (2)	0.071 (3)	−0.0012 (16)	0.0001 (17)	−0.020 (2)
C21	0.0426 (19)	0.052 (2)	0.0374 (17)	0.0237 (17)	−0.0054 (14)	−0.0122 (16)
C22	0.0429 (18)	0.0407 (18)	0.0365 (16)	0.0116 (14)	0.0178 (14)	0.0057 (13)
C23	0.0291 (14)	0.0267 (14)	0.0343 (15)	−0.0008 (11)	0.0073 (12)	−0.0011 (11)
C24	0.086 (3)	0.113 (4)	0.037 (2)	0.054 (3)	−0.005 (2)	−0.022 (2)
S25	0.0711 (7)	0.0562 (6)	0.0434 (4)	0.0187 (5)	0.0335 (4)	0.0176 (4)
O26	0.110 (10)	0.025 (3)	0.026 (4)	0.011 (4)	−0.006 (4)	−0.004 (3)
O27	0.055 (4)	0.034 (3)	0.028 (3)	−0.011 (3)	0.017 (3)	−0.012 (2)
O28	0.060 (5)	0.185 (16)	0.046 (4)	−0.043 (7)	0.034 (3)	−0.015 (6)
O26A	0.087 (5)	0.082 (5)	0.076 (4)	−0.001 (4)	0.057 (4)	0.013 (4)
O27A	0.261 (18)	0.043 (3)	0.077 (5)	0.007 (6)	0.105 (8)	−0.005 (3)
O28A	0.050 (5)	0.211 (15)	0.057 (5)	0.017 (6)	0.008 (4)	0.027 (6)

C1—O16	1.400 (4)	C14—H14A	0.98
C1—O5	1.411 (3)	C14—H14B	0.98
C1—C2	1.508 (4)	C14—H14C	0.98
C1—H1	1	C15—H15A	0.98
C2—O6	1.421 (4)	C15—H15B	0.98
C2—C3	1.537 (4)	C15—H15C	0.98
C2—H2	1	O16—C17	1.431 (5)
C3—O8	1.414 (4)	C17—H17A	0.98
C3—C4	1.557 (4)	C17—H17B	0.98
C3—H3	1	C17—H17C	0.98
C4—O5	1.442 (3)	C18—C23	1.377 (4)
C4—C11	1.522 (4)	C18—C19	1.391 (5)
C4—H4	1	C18—S25	1.771 (3)
O6—C7	1.439 (3)	C19—C20	1.383 (6)
C7—O8	1.447 (3)	C19—H19	0.95
C7—C9	1.503 (4)	C20—C21	1.393 (6)
C7—C10	1.510 (5)	C20—H20	0.95
C9—H9A	0.98	C21—C22	1.383 (5)
C9—H9B	0.98	C21—C24	1.508 (5)
C9—H9C	0.98	C22—C23	1.393 (4)
C10—H10A	0.98	C22—H22	0.95
C10—H10B	0.98	C23—H23	0.95
C10—H10C	0.98	C24—H24A	0.98
C11—N12	1.516 (3)	C24—H24B	0.98
C11—H11A	0.99	C24—H24C	0.98
C11—H11B	0.99	S25—O27A	1.334 (6)
N12—C13	1.493 (4)	S25—O28	1.377 (7)
N12—C15	1.494 (4)	S25—O28A	1.396 (9)
N12—C14	1.507 (4)	S25—O26	1.438 (9)
C13—H13A	0.98	S25—O27	1.582 (6)
C13—H13B	0.98	S25—O26A	1.599 (7)
C13—H13C	0.98
O16—C1—O5	112.6 (2)	N12—C14—H14A	109.5
O16—C1—C2	105.5 (3)	N12—C14—H14B	109.5
O5—C1—C2	106.5 (2)	H14A—C14—H14B	109.5
O16—C1—H1	110.7	N12—C14—H14C	109.5
O5—C1—H1	110.7	H14A—C14—H14C	109.5
C2—C1—H1	110.7	H14B—C14—H14C	109.5
O6—C2—C1	111.3 (2)	N12—C15—H15A	109.5
O6—C2—C3	102.1 (2)	N12—C15—H15B	109.5
C1—C2—C3	103.7 (2)	H15A—C15—H15B	109.5
O6—C2—H2	113	N12—C15—H15C	109.5
C1—C2—H2	113	H15A—C15—H15C	109.5
C3—C2—H2	113	H15B—C15—H15C	109.5
O8—C3—C2	105.2 (2)	C1—O16—C17	114.8 (3)
O8—C3—C4	112.7 (2)	O16—C17—H17A	109.5
C2—C3—C4	103.3 (2)	O16—C17—H17B	109.5
O8—C3—H3	111.7	H17A—C17—H17B	109.5
C2—C3—H3	111.7	O16—C17—H17C	109.5
C4—C3—H3	111.7	H17A—C17—H17C	109.5
O5—C4—C11	112.3 (2)	H17B—C17—H17C	109.5
O5—C4—C3	107.0 (2)	C23—C18—C19	119.6 (3)
C11—C4—C3	110.6 (2)	C23—C18—S25	119.9 (2)
O5—C4—H4	109	C19—C18—S25	120.4 (3)
C11—C4—H4	109	C20—C19—C18	119.7 (3)
C3—C4—H4	109	C20—C19—H19	120.2
C1—O5—C4	109.2 (2)	C18—C19—H19	120.2
C2—O6—C7	107.1 (2)	C19—C20—C21	121.2 (3)
O6—C7—O8	104.7 (2)	C19—C20—H20	119.4
O6—C7—C9	111.6 (2)	C21—C20—H20	119.4
O8—C7—C9	109.0 (3)	C22—C21—C20	118.4 (3)
O6—C7—C10	109.0 (3)	C22—C21—C24	121.1 (5)
O8—C7—C10	108.9 (3)	C20—C21—C24	120.4 (4)
C9—C7—C10	113.4 (3)	C21—C22—C23	120.7 (3)
C3—O8—C7	109.1 (2)	C21—C22—H22	119.7
C7—C9—H9A	109.5	C23—C22—H22	119.7
C7—C9—H9B	109.5	C18—C23—C22	120.3 (3)
H9A—C9—H9B	109.5	C18—C23—H23	119.9
C7—C9—H9C	109.5	C22—C23—H23	119.9
H9A—C9—H9C	109.5	C21—C24—H24A	109.5
H9B—C9—H9C	109.5	C21—C24—H24B	109.5
C7—C10—H10A	109.5	H24A—C24—H24B	109.5
C7—C10—H10B	109.5	C21—C24—H24C	109.5
H10A—C10—H10B	109.5	H24A—C24—H24C	109.5
C7—C10—H10C	109.5	H24B—C24—H24C	109.5
H10A—C10—H10C	109.5	O27A—S25—O28	65.0 (8)
H10B—C10—H10C	109.5	O27A—S25—O28A	131.0 (9)
N12—C11—C4	116.1 (2)	O28—S25—O28A	134.3 (8)
N12—C11—H11A	108.3	O27A—S25—O26	135.9 (7)
C4—C11—H11A	108.3	O28—S25—O26	121.2 (8)
N12—C11—H11B	108.3	O27A—S25—O27	45.1 (6)
C4—C11—H11B	108.3	O28—S25—O27	106.7 (7)
H11A—C11—H11B	107.4	O28A—S25—O27	89.6 (7)
C13—N12—C15	108.5 (2)	O26—S25—O27	99.6 (5)
C13—N12—C14	108.1 (2)	O27A—S25—O26A	109.6 (6)
C15—N12—C14	108.8 (3)	O28A—S25—O26A	104.6 (7)
C13—N12—C11	111.8 (2)	O26—S25—O26A	91.2 (7)
C15—N12—C11	112.8 (2)	O27—S25—O26A	149.6 (3)
C14—N12—C11	106.7 (2)	O27A—S25—C18	106.1 (4)
N12—C13—H13A	109.5	O28—S25—C18	112.6 (3)
N12—C13—H13B	109.5	O28A—S25—C18	103.0 (6)
H13A—C13—H13B	109.5	O26—S25—C18	109.3 (5)
N12—C13—H13C	109.5	O27—S25—C18	105.6 (2)
H13A—C13—H13C	109.5	O26A—S25—C18	97.4 (3)
H13B—C13—H13C	109.5
O16—C1—C2—O6	−163.4 (2)	C9—C7—O8—C3	105.0 (3)
O5—C1—C2—O6	76.7 (3)	C10—C7—O8—C3	−130.9 (3)
O16—C1—C2—C3	87.6 (3)	O5—C4—C11—N12	70.6 (3)
O5—C1—C2—C3	−32.4 (3)	C3—C4—C11—N12	−170.0 (2)
O6—C2—C3—O8	24.8 (3)	C4—C11—N12—C13	60.4 (3)
C1—C2—C3—O8	140.5 (2)	C4—C11—N12—C15	−62.1 (3)
O6—C2—C3—C4	−93.5 (3)	C4—C11—N12—C14	178.4 (3)
C1—C2—C3—C4	22.2 (3)	O5—C1—O16—C17	−71.4 (3)
O8—C3—C4—O5	−118.6 (2)	C2—C1—O16—C17	172.8 (3)
C2—C3—C4—O5	−5.5 (3)	C23—C18—C19—C20	1.6 (5)
O8—C3—C4—C11	118.8 (3)	S25—C18—C19—C20	179.5 (3)
C2—C3—C4—C11	−128.1 (2)	C18—C19—C20—C21	0.4 (6)
O16—C1—O5—C4	−85.3 (3)	C19—C20—C21—C22	−1.6 (6)
C2—C1—O5—C4	30.0 (3)	C19—C20—C21—C24	177.7 (4)
C11—C4—O5—C1	106.6 (3)	C20—C21—C22—C23	0.8 (5)
C3—C4—O5—C1	−14.9 (3)	C24—C21—C22—C23	−178.5 (3)
C1—C2—O6—C7	−144.6 (2)	C19—C18—C23—C22	−2.4 (5)
C3—C2—O6—C7	−34.5 (3)	S25—C18—C23—C22	179.6 (2)
C2—O6—C7—O8	31.5 (3)	C21—C22—C23—C18	1.2 (5)
C2—O6—C7—C9	−86.3 (3)	C23—C18—S25—O27	−24.9 (4)
C2—O6—C7—C10	147.8 (3)	C19—C18—S25—O27	157.2 (4)
C2—C3—O8—C7	−6.3 (3)	C23—C18—S25—O26A	175.2 (4)
C4—C3—O8—C7	105.6 (3)	C19—C18—S25—O26A	−2.7 (4)
O6—C7—O8—C3	−14.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O28Ai	0.98	2.45	3.412 (15)	167
C13—H13B···O28Aii	0.98	2.44	3.308 (13)	148
C14—H14B···O26Ai	0.98	2.30	3.251 (9)	163
C14—H14C···O27Aiii	0.98	2.22	3.161 (8)	162
C15—H15C···O5	0.98	2.41	2.964 (4)	115
C19—H19···O26A	0.95	2.26	2.712 (9)	108

Conformation of the furanoic ring	Conformation of the dioxolane ring	C1 substitution	C2–C3 substitution	C4 substitution	Reference
Envelope on the O5 atom (E0)	Envelope on C7 (E1)	H	2,3-O-isopropylidene	CH2NMe3(+), OTs(-)	Dmochowska et al. (2006); Skorupa et al. (2004)
Twisted about the O5–C1 bond (0T1)	Envelope on C7 (E0)	H	2,3-O-isopropylidene	CH2NMe3(+), I(-)	Dmochowska et al. (2006)
Envelope on the C1 atom (E1)	Twisted about the O6-C2 bond(0T1)	OCH3	2,3-O-isopropylidene	CH2NMe3(+), OTs(-)	this work
Envelope on the O5 atom (E0)	Twisted about the O18-C20 bond (2T3)	H	2,3-O-isopropylidene	CH2OTs	Dmochowska et al. (2009)
Envelope on the C3 atom (E3)		H	cis-2,3-dihydroxy	CH2OTs	Dmochowska et al. (2009)
Envelope on the C1 atom (E2)		H	trans-2,3-dihydroxy	CH2OTs	Dibrov et al. (2010)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O28A i	0.98	2.45	3.412 (15)	167
C13—H13B⋯O28A ii	0.98	2.44	3.308 (13)	148
C14—H14B⋯O26A i	0.98	2.30	3.251 (9)	163
C14—H14C⋯O27A iii	0.98	2.22	3.161 (8)	162
C15—H15C⋯O5	0.98	2.41	2.964 (4)	115
C19—H19⋯O26A	0.95	2.26	2.712 (9)	108

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