2-Benzyl-myo-inositol monohydrate

Fröhlich, R.F.G.; Gainsford, G.J.; Painter, G.F.

doi:10.1107/S1600536809041750

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2782

https://doi.org/10.1107/S1600536809041750

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2-Benzyl-myo-inositol monohydrate

Richard F. G. Fröhlich,^a Graeme J. Gainsford ^a ^* and Gavin F. Painter ^a

^aIndustrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand
^*Correspondence e-mail: g.gainsford@irl.cri.nz

(Received 1 October 2009; accepted 13 October 2009; online 17 October 2009)

The title structure, C₁₃H₁₈O₆·H₂O, contains two independent 2-benzyl-myo-inositol and water molecules. In the crystal, the molecules are strongly hydrogen bonded into an infinite two dimensional network utilizing all OH protons.

Related literature

For puckering parameters, see: Cremer & Pople (1975 ). For related structures, see: Khan et al. (2007 ); Simperler et al. (2006 ); Gibson et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₈O₆·H₂O
M_r = 288.29
Monoclinic, P 2₁ /c
a = 7.4616 (3) Å
b = 33.7688 (13) Å
c = 10.4528 (4) Å
β = 90.616 (2)°
V = 2633.63 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 121 K
0.75 × 0.72 × 0.31 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.657, T_max = 0.746
67666 measured reflections
8428 independent reflections
7368 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.110
S = 1.08
8428 reflections
385 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1′—H1′O⋯O1Wⁱ	0.84	1.87	2.7052 (11)	175
O1—H1O⋯O6′ⁱ	0.84	1.94	2.7768 (10)	171
O2′—H2′O⋯O2Wⁱⁱ	0.84	1.90	2.7267 (12)	166
O2—H2O⋯O3′ⁱⁱⁱ	0.84	2.04	2.7755 (10)	145
O3′—H3′O⋯O4^iv	0.84	2.01	2.8420 (10)	174
O3—H3O⋯O2′^iv	0.84	2.09	2.9290 (11)	172
O4′—H4′O⋯O6^v	0.84	1.91	2.7389 (10)	168
O4—H4O⋯O5′	0.84	1.87	2.6858 (10)	165
O5′—H5′O⋯O4′ⁱⁱⁱ	0.84	1.86	2.6943 (11)	175
O5—H5O⋯O4ⁱⁱ	0.84	2.57	3.3617 (11)	157
O6′—H6′O⋯O5	0.84	2.13	2.8523 (11)	144
O6—H6O⋯O1′ⁱⁱ	0.84	2.05	2.8831 (10)	173
O1W—H1WB⋯O2	0.85 (2)	1.96 (2)	2.8108 (12)	174.2 (19)
O2W—H2WA⋯O1	0.85 (2)	1.91 (2)	2.7521 (11)	173.3 (18)
O1W—H1WA⋯Cg1^vi	0.82 (2)	2.59 (2)	3.2647 (11)	140.9 (19)
O2W—H2WB⋯Cg2ⁱ	0.83 (2)	2.59 (2)	3.3335 (11)	149.9 (19)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+2; (iv) -x, -y+1, -z+2; (v) x, y, z+1; (vi) x+1, y, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT and SADABS (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ), Mercury (Macrae, 2006 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809041750/ez2193sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041750/ez2193Isup2.hkl

checkCIF report

Comment top

The enzyme myo-inositol oxygenase (MIOX) is over expressed in the kidney tissue of patients suffering from type II diabetes mellitus and defects in the metabolism of inositol sugars are also strongly associated with diabetes. Because MIOX is responsible for the first committed step in the catabolism of inositols, we were interested in developing chemical inhibitors of this enzyme. 2-Benzyl-myo-inositol is a candidate substrate-like (enzyme) inhibitor: specifically, inclusion of the equatorial benzyl group was designed to take advantage of a hydrophobic binding pocket identified adjacent to the MIOX active site.

The asymmetric unit of the title compound (I) contains two independent 2-benzyl-myo-inositol molecules and two waters of crystallization. The two molecules (Fig. 1) are essentially identical with chirality designations for carbons 1,2,4, & 6 of of R,S,R, & S and with the non-hydrogen atoms having a r.m.s. bond fit of 0.0043Å & the bond angles an r.m.s. fit of 1.93° (Spek, 2009). There is a slight twist between the two rings; torsion angles φ are C2—C7—C8—C13 - 88.67 (13),-92.34 (12)° for unprimed & primed molecules respectively. The inositol rings are in chair conformations with Cremer & Pople (1975) parameters Q, θ, φ of 0.5601 (10),0.5689 (10) Å, 176.85 (10),172.98 (10)° and 275.6 (19),333.1 (8)° respectively compared with 0.576 (2) Å, 177.9 (2) and 245 (7)° for a "parent" myo-inositol (Khan et al., 2007).

An extensive set of 14 hydrogen bonds involves nearly all available donors and acceptors (Table 1); all the hydrogen donors were located from difference maps, but with only the water hydrogen atomic positions refined with restrained thermal parameters. The two remaining water hydrogen atoms (H1WB & H2WB) are involved in O–H···π interactions with the phenyl rings (Table 1: Cg1,Cg2 are the centres of phenyl rings C8—C13 & C8'-C13' respectively). Overall, the molecules are strongly hydrogen bonded into an infinite two dimensional network with the benzyl groups making van der Waal contacts between the layers (Fig. 2). One antiparallel "double chain" link is observed in the complex system reflecting aspects of myo-inositol packing (Simperler et al., 2006).

Related literature top

For puckering parameters, see: Cremer & Pople (1975). For related structures, see: Khan et al. (2007); Simperler et al. (2006); Gibson et al. (2009)

Experimental top

2-Benzyl-1,3,4,5,6-penta-O-benzyl-myo-inositol (78 mg, 0.11 mmol) (Gibson et al., 2009) was dissolved in THF (5 ml) and palladium hydroxide (20% on carbon, wet, 65 mg) was added; the air was replaced with hydrogen (gasbag, 1 atm) and the mixture was stirred at RT for 1 h. The flask was aerated and left overnight. Next morning the solution was filtered through a pad of filter-aid, rinsed with MeOH and preabsorbed on silica (~0.5 g) and purified by chromatography (9 g silica, CHCl₃/MeOH = 3:1 v/v) which gave the product as a white solid. This was recrystallized from MeOH (25 mg, 85%). ¹H-NMR (500 MHz, methanol-d4) δ 7.47–7.37 (m, 2H), 7.28–7.22 (m, 2H), 7.21–7.15 (m, 1H), 3.56 (t, J = 9.4 Hz, 2H), 3.05 (s, 2H), 2.99 (d, J = 9.4 Hz, 2H), 2.84 (t, J = 9.4 Hz, 1H); ¹³C-NMR (126 MHz, methanol-d4) δ 138.4, 131.8, 129.1, 127.4, 77.9, 75.8, 75.4, 72.4, 40.8; HRMS (M+Na)+ C₁₃H₁₈O₆Na: calcd 293.1001; found 293.1004; micro anal. for C₁₃H₁₈O₆.H₂O: C (calcd. 54.16%) 54.64; H (6.99%) 6.97.

Structure description top

For puckering parameters, see: Cremer & Pople (1975). For related structures, see: Khan et al. (2007); Simperler et al. (2006); Gibson et al. (2009)

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT and SADABS (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), Mercury (Macrae, 2006) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Asymmetric unit contents of (I) (Farrugia, 1997).
	Fig. 2. Packing diagram (Macrae et al., 2006) of (I) viewed down the a axis with some atom labels. Some hydrogen bonds are shown as dashed lines (see text); H atoms not involved in hydrogen bonds are omitted for clarity.

2-Benzyl-myo-inositol monohydrate top

Crystal data top

C₁₃H₁₈O₆·H₂O	F(000) = 1232
M_r = 288.29	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9735 reflections
a = 7.4616 (3) Å	θ = 2.4–31.2°
b = 33.7688 (13) Å	µ = 0.12 mm⁻¹
c = 10.4528 (4) Å	T = 121 K
β = 90.616 (2)°	Block, colourless
V = 2633.63 (18) Å³	0.75 × 0.72 × 0.31 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	8428 independent reflections
Radiation source: fine-focus sealed tube	7368 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.333 pixels mm^-1	θ_max = 31.3°, θ_min = 2.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (Blessing, 1995)	k = −48→48
T_min = 0.657, T_max = 0.746	l = −15→14
67666 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0524P)² + 1.1394P] where P = (F_o² + 2F_c²)/3
8428 reflections	(Δ/σ)_max = 0.001
385 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₃H₁₈O₆·H₂O	V = 2633.63 (18) Å³
M_r = 288.29	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4616 (3) Å	µ = 0.12 mm⁻¹
b = 33.7688 (13) Å	T = 121 K
c = 10.4528 (4) Å	0.75 × 0.72 × 0.31 mm
β = 90.616 (2)°

Data collection top

Bruker APEXII CCD diffractometer	8428 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	7368 reflections with I > 2σ(I)
T_min = 0.657, T_max = 0.746	R_int = 0.031
67666 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.54 e Å⁻³
8428 reflections	Δρ_min = −0.26 e Å⁻³
385 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.50902 (10)	0.38866 (2)	0.32399 (7)	0.01471 (14)
H1O	0.5917	0.4055	0.3203	0.018*
O2	0.60347 (10)	0.41015 (2)	0.57055 (7)	0.01483 (14)
H2O	0.6332	0.4083	0.6481	0.018*
O3	0.35266 (11)	0.39608 (3)	0.76876 (7)	0.01909 (16)
H3O	0.2746	0.4030	0.8216	0.023*
O4	0.11845 (10)	0.46202 (2)	0.71154 (7)	0.01597 (14)
H4O	0.1612	0.4703	0.7812	0.019*
O5	0.19999 (12)	0.50334 (2)	0.48900 (8)	0.01982 (16)
H5O	0.1448	0.5105	0.4224	0.024*
O6	0.27845 (11)	0.45380 (2)	0.26950 (7)	0.01601 (14)
H6O	0.2020	0.4367	0.2481	0.019*
C1	0.37784 (12)	0.40152 (3)	0.41306 (8)	0.01044 (16)
H1	0.2638	0.3871	0.3933	0.013*
C2	0.43530 (12)	0.39073 (3)	0.55006 (9)	0.01108 (16)
C3	0.29331 (13)	0.40579 (3)	0.64287 (9)	0.01208 (16)
H3	0.1781	0.3916	0.6249	0.014*
C4	0.26177 (13)	0.45019 (3)	0.62932 (9)	0.01216 (16)
H4	0.3735	0.4648	0.6539	0.015*
C5	0.20777 (13)	0.46107 (3)	0.49359 (9)	0.01271 (17)
H5	0.0865	0.4499	0.4737	0.015*
C6	0.34184 (13)	0.44575 (3)	0.39682 (8)	0.01132 (16)
H6	0.4574	0.4602	0.4102	0.014*
C7	0.46317 (14)	0.34555 (3)	0.56367 (10)	0.01558 (18)
H7A	0.5610	0.3374	0.5060	0.019*
H7B	0.5029	0.3398	0.6524	0.019*
C8	0.30059 (15)	0.32061 (3)	0.53398 (10)	0.01688 (19)
C9	0.27011 (18)	0.30651 (4)	0.41014 (12)	0.0247 (2)
H9	0.3523	0.3128	0.3444	0.030*
C10	0.1205 (2)	0.28331 (4)	0.38195 (15)	0.0364 (3)
H10	0.1021	0.2737	0.2974	0.044*
C11	−0.0017 (2)	0.27418 (4)	0.47645 (18)	0.0414 (4)
H11	−0.1040	0.2585	0.4569	0.050*
C12	0.0266 (2)	0.28815 (4)	0.59964 (16)	0.0351 (3)
H12	−0.0569	0.2821	0.6648	0.042*
C13	0.17685 (17)	0.31106 (4)	0.62839 (12)	0.0240 (2)
H13	0.1954	0.3203	0.7133	0.029*
O1'	−0.02235 (10)	0.60830 (2)	0.78156 (7)	0.01499 (14)
H1'O	0.0179	0.6122	0.7079	0.018*
O2'	−0.10251 (10)	0.58343 (2)	1.02760 (7)	0.01449 (14)
H2'O	−0.1853	0.5942	0.9849	0.017*
O3'	0.15758 (10)	0.59222 (2)	1.22426 (6)	0.01522 (14)
H3'O	0.0710	0.5777	1.2446	0.018*
O4'	0.35488 (10)	0.52508 (2)	1.15761 (7)	0.01644 (15)
H4'O	0.3179	0.5032	1.1854	0.020*
O5'	0.30650 (11)	0.49278 (2)	0.90825 (7)	0.01634 (15)
H5'O	0.4134	0.4869	0.8924	0.020*
O6'	0.23721 (11)	0.55224 (2)	0.71019 (7)	0.01714 (15)
H6'O	0.1979	0.5327	0.6691	0.021*
C1'	0.11963 (12)	0.59546 (3)	0.86443 (8)	0.01071 (16)
H1'	0.2284	0.6118	0.8465	0.013*
C2'	0.06277 (12)	0.60309 (3)	1.00248 (8)	0.01054 (16)
C3'	0.20310 (12)	0.58499 (3)	1.09446 (8)	0.01089 (16)
H3'	0.3202	0.5983	1.0781	0.013*
C4'	0.22744 (13)	0.54078 (3)	1.06806 (9)	0.01159 (16)
H4'	0.1101	0.5269	1.0788	0.014*
C5'	0.29354 (13)	0.53434 (3)	0.93189 (9)	0.01157 (16)
H5'	0.4140	0.5469	0.9220	0.014*
C6'	0.16254 (13)	0.55231 (3)	0.83577 (8)	0.01145 (16)
H6'	0.0490	0.5366	0.8351	0.014*
C7'	0.03668 (14)	0.64794 (3)	1.02676 (10)	0.01511 (18)
H7'A	−0.0651	0.6572	0.9732	0.018*
H7'B	0.0029	0.6516	1.1173	0.018*
C8'	0.19624 (14)	0.67385 (3)	0.99995 (10)	0.01606 (18)
C9'	0.22323 (17)	0.68948 (3)	0.87823 (11)	0.0222 (2)
H9'	0.1402	0.6836	0.8113	0.027*
C10'	0.3703 (2)	0.71355 (4)	0.85360 (15)	0.0336 (3)
H10'	0.3870	0.7241	0.7703	0.040*
C11'	0.4927 (2)	0.72223 (4)	0.95047 (18)	0.0396 (4)
H11'	0.5936	0.7385	0.9336	0.048*
C12'	0.4666 (2)	0.70707 (4)	1.07170 (17)	0.0365 (3)
H12'	0.5497	0.7130	1.1384	0.044*
C13'	0.31951 (17)	0.68313 (4)	1.09646 (12)	0.0249 (2)
H13'	0.3028	0.6730	1.1802	0.030*
O1W	0.91098 (12)	0.37731 (3)	0.45945 (8)	0.02411 (18)
H1WA	0.923 (3)	0.3553 (6)	0.4917 (19)	0.036*
H1WB	0.817 (3)	0.3882 (6)	0.4883 (18)	0.036*
O2W	0.40295 (12)	0.38183 (3)	0.07198 (8)	0.02373 (18)
H2WA	0.429 (3)	0.3826 (6)	0.1511 (19)	0.036*
H2WB	0.429 (3)	0.3596 (6)	0.0440 (18)	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0152 (3)	0.0176 (3)	0.0114 (3)	0.0019 (3)	0.0024 (2)	−0.0026 (2)
O2	0.0117 (3)	0.0222 (4)	0.0106 (3)	−0.0032 (3)	−0.0024 (2)	−0.0004 (2)
O3	0.0227 (4)	0.0257 (4)	0.0089 (3)	0.0054 (3)	0.0015 (3)	0.0026 (3)
O4	0.0161 (3)	0.0180 (4)	0.0138 (3)	0.0009 (3)	0.0039 (2)	−0.0048 (3)
O5	0.0290 (4)	0.0106 (3)	0.0199 (4)	0.0039 (3)	0.0008 (3)	0.0001 (3)
O6	0.0208 (4)	0.0157 (3)	0.0114 (3)	−0.0009 (3)	−0.0036 (3)	0.0036 (2)
C1	0.0105 (4)	0.0115 (4)	0.0093 (4)	0.0011 (3)	−0.0002 (3)	−0.0004 (3)
C2	0.0104 (4)	0.0128 (4)	0.0100 (4)	0.0004 (3)	−0.0009 (3)	0.0004 (3)
C3	0.0127 (4)	0.0143 (4)	0.0093 (4)	0.0009 (3)	0.0007 (3)	0.0009 (3)
C4	0.0120 (4)	0.0128 (4)	0.0117 (4)	0.0000 (3)	0.0020 (3)	−0.0020 (3)
C5	0.0142 (4)	0.0106 (4)	0.0133 (4)	0.0010 (3)	0.0004 (3)	−0.0005 (3)
C6	0.0128 (4)	0.0114 (4)	0.0097 (4)	0.0000 (3)	−0.0005 (3)	0.0007 (3)
C7	0.0160 (4)	0.0140 (4)	0.0168 (4)	0.0033 (3)	−0.0009 (3)	0.0019 (3)
C8	0.0198 (5)	0.0103 (4)	0.0205 (5)	0.0029 (3)	−0.0010 (4)	0.0024 (3)
C9	0.0327 (6)	0.0165 (5)	0.0249 (5)	0.0020 (4)	−0.0045 (4)	−0.0022 (4)
C10	0.0483 (9)	0.0182 (6)	0.0424 (8)	−0.0022 (5)	−0.0191 (6)	−0.0043 (5)
C11	0.0362 (8)	0.0206 (6)	0.0672 (11)	−0.0098 (5)	−0.0168 (7)	0.0085 (6)
C12	0.0281 (6)	0.0232 (6)	0.0541 (9)	−0.0047 (5)	0.0015 (6)	0.0147 (6)
C13	0.0252 (6)	0.0179 (5)	0.0288 (6)	0.0012 (4)	0.0028 (4)	0.0072 (4)
O1'	0.0140 (3)	0.0199 (4)	0.0110 (3)	0.0031 (3)	−0.0019 (2)	0.0028 (2)
O2'	0.0097 (3)	0.0198 (4)	0.0139 (3)	−0.0019 (3)	0.0002 (2)	0.0035 (2)
O3'	0.0168 (3)	0.0196 (4)	0.0093 (3)	−0.0008 (3)	0.0001 (2)	−0.0013 (2)
O4'	0.0172 (3)	0.0157 (3)	0.0163 (3)	0.0016 (3)	−0.0048 (3)	0.0046 (3)
O5'	0.0170 (4)	0.0108 (3)	0.0212 (3)	0.0024 (3)	−0.0001 (3)	−0.0027 (3)
O6'	0.0246 (4)	0.0159 (3)	0.0111 (3)	−0.0030 (3)	0.0038 (3)	−0.0034 (2)
C1'	0.0106 (4)	0.0115 (4)	0.0100 (4)	0.0008 (3)	−0.0007 (3)	0.0004 (3)
C2'	0.0094 (4)	0.0119 (4)	0.0103 (4)	0.0001 (3)	0.0007 (3)	0.0004 (3)
C3'	0.0110 (4)	0.0120 (4)	0.0096 (4)	0.0002 (3)	−0.0006 (3)	−0.0001 (3)
C4'	0.0114 (4)	0.0118 (4)	0.0115 (4)	0.0004 (3)	−0.0016 (3)	0.0014 (3)
C5'	0.0116 (4)	0.0102 (4)	0.0129 (4)	0.0007 (3)	−0.0003 (3)	−0.0004 (3)
C6'	0.0121 (4)	0.0121 (4)	0.0101 (4)	−0.0003 (3)	0.0001 (3)	0.0001 (3)
C7'	0.0161 (4)	0.0129 (4)	0.0163 (4)	0.0039 (3)	0.0016 (3)	−0.0010 (3)
C8'	0.0190 (5)	0.0099 (4)	0.0193 (4)	0.0026 (3)	−0.0009 (3)	−0.0018 (3)
C9'	0.0282 (6)	0.0156 (5)	0.0227 (5)	0.0010 (4)	0.0026 (4)	0.0021 (4)
C10'	0.0416 (8)	0.0177 (5)	0.0417 (7)	−0.0033 (5)	0.0149 (6)	0.0036 (5)
C11'	0.0317 (7)	0.0208 (6)	0.0666 (10)	−0.0102 (5)	0.0100 (7)	−0.0067 (6)
C12'	0.0286 (7)	0.0259 (6)	0.0547 (9)	−0.0043 (5)	−0.0089 (6)	−0.0121 (6)
C13'	0.0264 (6)	0.0202 (5)	0.0278 (6)	0.0008 (4)	−0.0070 (4)	−0.0047 (4)
O1W	0.0194 (4)	0.0309 (5)	0.0221 (4)	0.0063 (3)	0.0047 (3)	0.0091 (3)
O2W	0.0206 (4)	0.0337 (5)	0.0168 (4)	0.0071 (3)	−0.0031 (3)	−0.0046 (3)

Geometric parameters (Å, º) top

O1—C1	1.4259 (11)	O2'—C2'	1.4275 (11)
O1—H1O	0.8400	O2'—H2'O	0.8400
O2—C2	1.4299 (12)	O3'—C3'	1.4233 (11)
O2—H2O	0.8400	O3'—H3'O	0.8400
O3—C3	1.4222 (11)	O4'—C4'	1.4291 (11)
O3—H3O	0.8400	O4'—H4'O	0.8400
O4—C4	1.4358 (12)	O5'—C5'	1.4284 (12)
O4—H4O	0.8400	O5'—H5'O	0.8400
O5—C5	1.4293 (12)	O6'—C6'	1.4315 (11)
O5—H5O	0.8400	O6'—H6'O	0.8400
O6—C6	1.4336 (11)	C1'—C6'	1.5223 (13)
O6—H6O	0.8400	C1'—C2'	1.5303 (12)
C1—C6	1.5268 (13)	C1'—H1'	1.0000
C1—C2	1.5343 (12)	C2'—C3'	1.5403 (13)
C1—H1	1.0000	C2'—C7'	1.5481 (14)
C2—C3	1.5312 (13)	C3'—C4'	1.5295 (13)
C2—C7	1.5460 (14)	C3'—H3'	1.0000
C3—C4	1.5240 (14)	C4'—C5'	1.5269 (13)
C3—H3	1.0000	C4'—H4'	1.0000
C4—C5	1.5159 (13)	C5'—C6'	1.5206 (13)
C4—H4	1.0000	C5'—H5'	1.0000
C5—C6	1.5209 (13)	C6'—H6'	1.0000
C5—H5	1.0000	C7'—C8'	1.5064 (15)
C6—H6	1.0000	C7'—H7'A	0.9900
C7—C8	1.5064 (15)	C7'—H7'B	0.9900
C7—H7A	0.9900	C8'—C13'	1.3935 (16)
C7—H7B	0.9900	C8'—C9'	1.3941 (15)
C8—C9	1.3957 (16)	C9'—C10'	1.3921 (18)
C8—C13	1.3964 (16)	C9'—H9'	0.9500
C9—C10	1.3925 (19)	C10'—C11'	1.387 (2)
C9—H9	0.9500	C10'—H10'	0.9500
C10—C11	1.386 (3)	C11'—C12'	1.382 (3)
C10—H10	0.9500	C11'—H11'	0.9500
C11—C12	1.385 (3)	C12'—C13'	1.390 (2)
C11—H11	0.9500	C12'—H12'	0.9500
C12—C13	1.3921 (19)	C13'—H13'	0.9500
C12—H12	0.9500	O1W—H1WA	0.82 (2)
C13—H13	0.9500	O1W—H1WB	0.85 (2)
O1'—C1'	1.4286 (11)	O2W—H2WA	0.85 (2)
O1'—H1'O	0.8400	O2W—H2WB	0.83 (2)

C1—O1—H1O	109.5	C2'—O2'—H2'O	109.5
C2—O2—H2O	109.5	C3'—O3'—H3'O	109.5
C3—O3—H3O	109.5	C4'—O4'—H4'O	109.5
C4—O4—H4O	109.5	C5'—O5'—H5'O	109.5
C5—O5—H5O	109.5	C6'—O6'—H6'O	109.5
C6—O6—H6O	109.5	O1'—C1'—C6'	109.10 (7)
O1—C1—C6	110.28 (7)	O1'—C1'—C2'	108.02 (7)
O1—C1—C2	110.50 (7)	C6'—C1'—C2'	114.06 (8)
C6—C1—C2	112.54 (7)	O1'—C1'—H1'	108.5
O1—C1—H1	107.8	C6'—C1'—H1'	108.5
C6—C1—H1	107.8	C2'—C1'—H1'	108.5
C2—C1—H1	107.8	O2'—C2'—C1'	110.12 (7)
O2—C2—C3	111.39 (8)	O2'—C2'—C3'	106.47 (7)
O2—C2—C1	105.48 (7)	C1'—C2'—C3'	109.16 (7)
C3—C2—C1	108.91 (8)	O2'—C2'—C7'	108.32 (8)
O2—C2—C7	108.77 (8)	C1'—C2'—C7'	110.85 (8)
C3—C2—C7	111.27 (8)	C3'—C2'—C7'	111.82 (8)
C1—C2—C7	110.87 (8)	O3'—C3'—C4'	111.68 (8)
O3—C3—C4	111.05 (8)	O3'—C3'—C2'	111.06 (8)
O3—C3—C2	107.39 (8)	C4'—C3'—C2'	110.85 (7)
C4—C3—C2	112.03 (8)	O3'—C3'—H3'	107.7
O3—C3—H3	108.8	C4'—C3'—H3'	107.7
C4—C3—H3	108.8	C2'—C3'—H3'	107.7
C2—C3—H3	108.8	O4'—C4'—C5'	109.79 (8)
O4—C4—C5	107.50 (8)	O4'—C4'—C3'	108.87 (8)
O4—C4—C3	109.47 (8)	C5'—C4'—C3'	110.32 (7)
C5—C4—C3	111.39 (8)	O4'—C4'—H4'	109.3
O4—C4—H4	109.5	C5'—C4'—H4'	109.3
C5—C4—H4	109.5	C3'—C4'—H4'	109.3
C3—C4—H4	109.5	O5'—C5'—C6'	108.79 (8)
O5—C5—C4	106.49 (8)	O5'—C5'—C4'	108.92 (8)
O5—C5—C6	110.13 (8)	C6'—C5'—C4'	110.32 (8)
C4—C5—C6	111.71 (8)	O5'—C5'—H5'	109.6
O5—C5—H5	109.5	C6'—C5'—H5'	109.6
C4—C5—H5	109.5	C4'—C5'—H5'	109.6
C6—C5—H5	109.5	O6'—C6'—C5'	110.57 (8)
O6—C6—C5	109.88 (8)	O6'—C6'—C1'	105.48 (7)
O6—C6—C1	110.16 (7)	C5'—C6'—C1'	112.77 (8)
C5—C6—C1	112.02 (8)	O6'—C6'—H6'	109.3
O6—C6—H6	108.2	C5'—C6'—H6'	109.3
C5—C6—H6	108.2	C1'—C6'—H6'	109.3
C1—C6—H6	108.2	C8'—C7'—C2'	115.90 (8)
C8—C7—C2	115.18 (8)	C8'—C7'—H7'A	108.3
C8—C7—H7A	108.5	C2'—C7'—H7'A	108.3
C2—C7—H7A	108.5	C8'—C7'—H7'B	108.3
C8—C7—H7B	108.5	C2'—C7'—H7'B	108.3
C2—C7—H7B	108.5	H7'A—C7'—H7'B	107.4
H7A—C7—H7B	107.5	C13'—C8'—C9'	118.36 (11)
C9—C8—C13	118.31 (11)	C13'—C8'—C7'	120.85 (10)
C9—C8—C7	120.31 (10)	C9'—C8'—C7'	120.79 (10)
C13—C8—C7	121.38 (10)	C10'—C9'—C8'	120.78 (12)
C10—C9—C8	120.70 (13)	C10'—C9'—H9'	119.6
C10—C9—H9	119.7	C8'—C9'—H9'	119.6
C8—C9—H9	119.7	C11'—C10'—C9'	120.16 (13)
C11—C10—C9	120.40 (14)	C11'—C10'—H10'	119.9
C11—C10—H10	119.8	C9'—C10'—H10'	119.9
C9—C10—H10	119.8	C12'—C11'—C10'	119.53 (13)
C12—C11—C10	119.47 (13)	C12'—C11'—H11'	120.2
C12—C11—H11	120.3	C10'—C11'—H11'	120.2
C10—C11—H11	120.3	C11'—C12'—C13'	120.35 (13)
C11—C12—C13	120.26 (14)	C11'—C12'—H12'	119.8
C11—C12—H12	119.9	C13'—C12'—H12'	119.8
C13—C12—H12	119.9	C12'—C13'—C8'	120.83 (13)
C12—C13—C8	120.86 (13)	C12'—C13'—H13'	119.6
C12—C13—H13	119.6	C8'—C13'—H13'	119.6
C8—C13—H13	119.6	H1WA—O1W—H1WB	109.3 (18)
C1'—O1'—H1'O	109.5	H2WA—O2W—H2WB	108.5 (18)

O1—C1—C2—O2	59.12 (9)	O1'—C1'—C2'—O2'	56.69 (10)
C6—C1—C2—O2	−64.64 (10)	C6'—C1'—C2'—O2'	−64.78 (10)
O1—C1—C2—C3	178.79 (8)	O1'—C1'—C2'—C3'	173.24 (7)
C6—C1—C2—C3	55.03 (10)	C6'—C1'—C2'—C3'	51.76 (10)
O1—C1—C2—C7	−58.46 (10)	O1'—C1'—C2'—C7'	−63.16 (10)
C6—C1—C2—C7	177.78 (8)	C6'—C1'—C2'—C7'	175.36 (8)
O2—C2—C3—O3	−62.82 (10)	O2'—C2'—C3'—O3'	−62.52 (10)
C1—C2—C3—O3	−178.74 (8)	C1'—C2'—C3'—O3'	178.63 (7)
C7—C2—C3—O3	58.74 (10)	C7'—C2'—C3'—O3'	55.61 (10)
O2—C2—C3—C4	59.37 (10)	O2'—C2'—C3'—C4'	62.25 (9)
C1—C2—C3—C4	−56.55 (10)	C1'—C2'—C3'—C4'	−56.59 (10)
C7—C2—C3—C4	−179.06 (8)	C7'—C2'—C3'—C4'	−179.61 (8)
O3—C3—C4—O4	−64.21 (10)	O3'—C3'—C4'—O4'	−54.04 (10)
C2—C3—C4—O4	175.71 (7)	C2'—C3'—C4'—O4'	−178.46 (7)
O3—C3—C4—C5	177.05 (8)	O3'—C3'—C4'—C5'	−174.57 (7)
C2—C3—C4—C5	56.96 (10)	C2'—C3'—C4'—C5'	61.00 (10)
O4—C4—C5—O5	65.91 (10)	O4'—C4'—C5'—O5'	62.81 (10)
C3—C4—C5—O5	−174.17 (8)	C3'—C4'—C5'—O5'	−177.20 (7)
O4—C4—C5—C6	−173.82 (8)	O4'—C4'—C5'—C6'	−177.84 (8)
C3—C4—C5—C6	−53.90 (11)	C3'—C4'—C5'—C6'	−57.86 (10)
O5—C5—C6—O6	−66.62 (10)	O5'—C5'—C6'—O6'	−70.13 (10)
C4—C5—C6—O6	175.27 (8)	C4'—C5'—C6'—O6'	170.45 (8)
O5—C5—C6—C1	170.59 (8)	O5'—C5'—C6'—C1'	172.04 (8)
C4—C5—C6—C1	52.47 (11)	C4'—C5'—C6'—C1'	52.62 (10)
O1—C1—C6—O6	59.58 (10)	O1'—C1'—C6'—O6'	67.44 (9)
C2—C1—C6—O6	−176.54 (7)	C2'—C1'—C6'—O6'	−171.68 (8)
O1—C1—C6—C5	−177.79 (7)	O1'—C1'—C6'—C5'	−171.78 (7)
C2—C1—C6—C5	−53.91 (10)	C2'—C1'—C6'—C5'	−50.90 (11)
O2—C2—C7—C8	−175.19 (8)	O2'—C2'—C7'—C8'	−177.69 (8)
C3—C2—C7—C8	61.74 (11)	C1'—C2'—C7'—C8'	−56.77 (11)
C1—C2—C7—C8	−59.64 (11)	C3'—C2'—C7'—C8'	65.30 (11)
C2—C7—C8—C9	91.19 (12)	C2'—C7'—C8'—C13'	−92.33 (12)
C2—C7—C8—C13	−88.68 (12)	C2'—C7'—C8'—C9'	88.33 (12)
C13—C8—C9—C10	−0.38 (17)	C13'—C8'—C9'—C10'	0.40 (17)
C7—C8—C9—C10	179.75 (11)	C7'—C8'—C9'—C10'	179.76 (11)
C8—C9—C10—C11	0.7 (2)	C8'—C9'—C10'—C11'	0.1 (2)
C9—C10—C11—C12	−0.4 (2)	C9'—C10'—C11'—C12'	−0.5 (2)
C10—C11—C12—C13	−0.2 (2)	C10'—C11'—C12'—C13'	0.3 (2)
C11—C12—C13—C8	0.5 (2)	C11'—C12'—C13'—C8'	0.2 (2)
C9—C8—C13—C12	−0.21 (17)	C9'—C8'—C13'—C12'	−0.58 (18)
C7—C8—C13—C12	179.66 (11)	C7'—C8'—C13'—C12'	−179.94 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1′—H1′O···O1Wⁱ	0.84	1.87	2.7052 (11)	175
O1—H1O···O6′ⁱ	0.84	1.94	2.7768 (10)	171
O2′—H2′O···O2Wⁱⁱ	0.84	1.90	2.7267 (12)	166
O2—H2O···O3′ⁱⁱⁱ	0.84	2.04	2.7755 (10)	145
O3′—H3′O···O4^iv	0.84	2.01	2.8420 (10)	174
O3—H3O···O2′^iv	0.84	2.09	2.9290 (11)	172
O4′—H4′O···O6^v	0.84	1.91	2.7389 (10)	168
O4—H4O···O5′	0.84	1.87	2.6858 (10)	165
O5′—H5′O···O4′ⁱⁱⁱ	0.84	1.86	2.6943 (11)	175
O5—H5O···O4ⁱⁱ	0.84	2.57	3.3617 (11)	157
O6′—H6′O···O5	0.84	2.13	2.8523 (11)	144
O6—H6O···O1′ⁱⁱ	0.84	2.05	2.8831 (10)	173
O1W—H1WB···O2	0.85 (2)	1.96 (2)	2.8108 (12)	174.2 (19)
O2W—H2WA···O1	0.85 (2)	1.91 (2)	2.7521 (11)	173.3 (18)
O1W—H1WA···Cg1^vi	0.82 (2)	2.59 (2)	3.2647 (11)	140.9 (19)
O2W—H2WB···Cg2ⁱ	0.83 (2)	2.59 (2)	3.3335 (11)	149.9 (19)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+1, −z+2; (v) x, y, z+1; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₈O₆·H₂O
M_r	288.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	121
a, b, c (Å)	7.4616 (3), 33.7688 (13), 10.4528 (4)
β (°)	90.616 (2)
V (Å³)	2633.63 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.75 × 0.72 × 0.31

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.657, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	67666, 8428, 7368
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.730

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.08
No. of reflections	8428
No. of parameters	385
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT and SADABS (Bruker, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), Mercury (Macrae, 2006) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1'—H1'O···O1Wⁱ	0.84	1.87	2.7052 (11)	175
O1—H1O···O6'ⁱ	0.84	1.94	2.7768 (10)	171
O2'—H2'O···O2Wⁱⁱ	0.84	1.90	2.7267 (12)	166
O2—H2O···O3'ⁱⁱⁱ	0.84	2.04	2.7755 (10)	145
O3'—H3'O···O4^iv	0.84	2.01	2.8420 (10)	174
O3—H3O···O2'^iv	0.84	2.09	2.9290 (11)	172
O4'—H4'O···O6^v	0.84	1.91	2.7389 (10)	168
O4—H4O···O5'	0.84	1.87	2.6858 (10)	165
O5'—H5'O···O4'ⁱⁱⁱ	0.84	1.86	2.6943 (11)	175
O5—H5O···O4ⁱⁱ	0.84	2.57	3.3617 (11)	157
O6'—H6'O···O5	0.84	2.13	2.8523 (11)	144
O6—H6O···O1'ⁱⁱ	0.84	2.05	2.8831 (10)	173
O1W—H1WB···O2	0.85 (2)	1.96 (2)	2.8108 (12)	174.2 (19)
O2W—H2WA···O1	0.85 (2)	1.91 (2)	2.7521 (11)	173.3 (18)
O1W—H1WA···Cg1^vi	0.82 (2)	2.59 (2)	3.2647 (11)	140.9 (19)
O2W—H2WB···Cg2ⁱ	0.83 (2)	2.59 (2)	3.3335 (11)	149.9 (19)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x, −y+1, −z+2; (v) x, y, z+1; (vi) x+1, y, z.

Acknowledgements

This work was supported by the New Zealand Foundation for Research Science and Technology (grant contract No. C08X0701). We thank Drs J. Wikaira and C. Fitchett of the University of Canterbury for their assistance.

References

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