Disordered 4,4′-di-O-isobutyroyl-2,2′,3,3′,6,6′-hex-O-acetyl-α,α′-trehalose

Baddeley, T.C.; Clow, S.M.; Cox, P.J.; Davidson, I.G.; Ryder, C.; Wardell, J.L.

doi:10.1107/S1600536803010729

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Disordered 4,4′-di-O-isobutyroyl-2,2′,3,3′,6,6′-hex-O-acetyl-α,α′-trehalose

T. C. Baddeley, S. M. Clow, P. J. Cox, I. G. Davidson, C. Ryder and J. L. Wardell

The twofold symmetry of the title compound, C₃₂H₄₆O₁₉, coincides with a crystallographic twofold axis. Weak C—H

O hydrogen bonding and a disordered isobutyroyl group are present.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010729/cm6042sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010729/cm6042Isup2.hkl Contains datablock I

CCDC reference: 214844

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.006 Å
R factor = 0.053
wR factor = 0.154
Data-to-parameter ratio = 7.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.132

PLAT_213  Alert C Atom O6      has ADP max/min Ratio ...........       3.10 prolate

PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      31.00 A   3

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.67
         From the CIF: _reflns_number_total               2206
         Count of symmetry unique reflns         2206
         Completeness (_total/calc)            100.00%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

Comment top

Recently we have determined the structures of a number of substituted trehalose derivatives. These have included hydrated or solvated forms, such as 2,2',3,3',4,4'-hexa-O-acetato-6,6'-bis-O-isobutanoyl-α,α'-trehalose 0.7-hydrate (Clow et al., 2001), 2,2',3,3',4,6,6'-hepta-O-pivaloyl-α,α'-trehalose (Baddeley et al., 2003) and 2,2',3,3',4,4',6,6'-hexa-O-acetato-α,α'-trehalose EtOAc solvate (Baddeley et al., 2001). The anyhdrous symmetrically substituted 2,2',3,3',4,4'-hexa-O-acetato-6,6'-bis-O-trityl-α,α'-trehalose (Baddeley et al., 2002) possesses molecular twofold symmetry that corresponds to a crystallographic twofold axis.

The disordered structure reported here, 2,2',3,3',4,6,6'-hepta-O-pivaloyl-α,α'-trehalose, (I), also possesses molecular twofold symmetry corresponding to a crystallographic twofold axis. As this axis passes through the bridging oxygen at (-x + 0.5, X+0.5, 1/4), the molecular geometry shown in Table 1 applies to both halves of the molecule. As expected, the pyranose ring has a ⁴C₁ conformation, as indicated by the puckering parameters (Cremer & Pople, 1975) calculated with PLATON (Spek, 2001) Q = 0.556 (4) Å, θ = 1.5 (4)° and ø = 52 (8)°.

The pseudo-torsion angle H1—C1···C1'-H1' of the glycosidic linkage is −89.1°. In the ditrityl hexaacetate derivative of α,α'-trehalose, where the bridging oxygen also lies on a twofold axis, the pseudo-torsion angle is −104.7° (Baddeley et al., 2002).

The substitution at C1,C1' is α,α' with C1—O1 = 1.417 (4) Å and the angle subtended at O1 = 113.1 (4)°. The absolute configuration adopted, see below, is R at C1, C2, C3, C4 and C5. Disorder is present in the isobutyroyl group with atoms O8, C13, C14, C15 and C16 disordered over two sites with fixed occupancies of 0.5. There are no O—H···O hydrogen bonds but there are weak C—H···O hydrogen bonds which are shown in Table 2 (disordered atoms excluded). The disordered structure of 2,2',3,3'4,6,6'-hepta-O-pivaloyl-α,α'-trehalose (Baddeley et al., 2003) also possesses C—H···O hydrogen bonds.

Experimental top

2,2',3,3',4,4'-Hexaacetyl-α,α'-trehalose, prepared according to the method of Bredereck (1930), was dissolved in 1:1 pyridine–water and stirred at room temperature for 48 h. At this time, thin-layer chromatography (EtOAc) showed the acyl migration to be complete. The solvent was removed under vacuum and the resulting solid recrystallized from DCM/MTBE. 2,2',3,3',6,6'-Hexaacetyl-α,α'-trehalose was dissolved in pyridine and 2.1 equivalents of isobutyroyl chloride added with stirring. After 4 h the solution was added to water. The resulting solid was collected, washed with water and dried. Recrystallization from ethanol gave 4,4'-di-O-isobutyroyl-2,2',3,3',6,6'-hex-O-acetyl-α,α'-trehalose (m.p. 397–399 K).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).

Figures top

Fig. 1. The atomic arrangement in the molecule (disorder excluded). Displacement ellipsoids are shown at the 50% probability level.

4,4'-Di-isobutyroyl-2,2',3,3',6,6'-hexacetyl-α,α'-trehalose top

Crystal data top

C₃₂H₄₆O₁₉	D_x = 1.229 Mg m⁻³
M_r = 734.69	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 5000 reflections
a = 14.9188 (9) Å	θ = 1.9–25.7°
c = 17.8355 (6) Å	µ = 0.10 mm⁻¹
V = 3969.7 (4) Å³	T = 150 K
Z = 4	Lozenge, colourless
F(000) = 1560	0.45 × 0.15 × 0.15 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	2206 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode	1414 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.132
Detector resolution: 9.091 pixels mm^-1	θ_max = 25.7°, θ_min = 1.9°
ϕ and ω scans to fill Ewald sphere	h = −17→18
Absorption correction: multi-scan using multiple and symmetry-related data measurements via SORTAV (Blessing, 1995, 1997)	k = −18→18
T_min = 0.956, T_max = 0.985	l = −20→21
50356 measured reflections

Refinement top

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)] = 0.053	H-atom parameters constrained
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.1016P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.003
2206 reflections	Δρ_max = 0.35 e Å⁻³
281 parameters	Δρ_min = −0.37 e Å⁻³
5 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0117 (18)

Crystal data top

C₃₂H₄₆O₁₉	Z = 4
M_r = 734.69	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 0.10 mm⁻¹
a = 14.9188 (9) Å	T = 150 K
c = 17.8355 (6) Å	0.45 × 0.15 × 0.15 mm
V = 3969.7 (4) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	2206 independent reflections
Absorption correction: multi-scan using multiple and symmetry-related data measurements via SORTAV (Blessing, 1995, 1997)	1414 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.985	R_int = 0.132
50356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	5 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	Δρ_max = 0.35 e Å⁻³
2206 reflections	Δρ_min = −0.37 e Å⁻³
281 parameters

Special details top

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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	Occ. (<1)
O1	0.50423 (15)	0.49577 (15)	0.2500	0.0428 (8)
O2	0.53377 (18)	0.59905 (16)	0.12323 (12)	0.0520 (7)
O3	0.6641 (2)	0.5604 (2)	0.07028 (16)	0.0684 (9)
O4	0.38070 (17)	0.5479 (2)	0.04240 (12)	0.0636 (8)
O5	0.50504 (16)	0.36524 (16)	0.17855 (11)	0.0486 (6)
O6	0.2879 (4)	0.6402 (3)	0.09708 (18)	0.149 (2)
O7	0.27419 (17)	0.4091 (2)	0.12429 (14)	0.0759 (10)
O8A	0.2417 (4)	0.4346 (6)	0.0022 (3)	0.081 (2)	0.50
O8B	0.2600 (5)	0.3428 (8)	0.0066 (4)	0.116 (3)	0.50
O9	0.4099 (2)	0.2209 (2)	0.24749 (17)	0.0754 (9)
O10	0.5227 (6)	0.1458 (4)	0.2006 (4)	0.221 (4)
C1	0.5363 (2)	0.4538 (2)	0.18394 (16)	0.0416 (8)
H1	0.6033	0.4535	0.1848	0.050*
C2	0.5048 (2)	0.5074 (2)	0.11790 (17)	0.0446 (8)
H2	0.5301	0.4805	0.0711	0.053*
C3	0.4035 (2)	0.5066 (3)	0.11277 (16)	0.0503 (10)
H3	0.3768	0.5409	0.1554	0.060*
C4	0.3701 (3)	0.4107 (3)	0.11322 (19)	0.0589 (11)
H4	0.3857	0.3807	0.0648	0.071*
C5	0.4093 (3)	0.3583 (3)	0.17849 (19)	0.0580 (11)
H5	0.3854	0.3833	0.2265	0.070*
C6	0.3892 (4)	0.2603 (3)	0.1750 (2)	0.0823 (15)
H6A	0.3251	0.2509	0.1629	0.099*
H6B	0.4258	0.2316	0.1354	0.099*
C7	0.4792 (5)	0.1653 (4)	0.2532 (4)	0.125 (3)
C8	0.4942 (6)	0.1368 (5)	0.3333 (4)	0.141 (3)
H8A	0.5523	0.1067	0.3375	0.169*
H8B	0.4465	0.0955	0.3485	0.169*
H8C	0.4935	0.1897	0.3659	0.169*
C9	0.6160 (3)	0.6164 (3)	0.09627 (19)	0.0578 (10)
C10	0.6376 (4)	0.7134 (3)	0.1029 (3)	0.0850 (16)
H10A	0.7027	0.7217	0.1002	0.102*
H10B	0.6155	0.7361	0.1511	0.102*
H10C	0.6089	0.7464	0.0619	0.102*
C11	0.3225 (3)	0.6138 (4)	0.0423 (2)	0.0780 (15)
C12	0.3098 (4)	0.6506 (4)	−0.0354 (2)	0.0891 (19)
H12A	0.2572	0.6899	−0.0362	0.107*
H12B	0.3010	0.6010	−0.0706	0.107*
H12C	0.3631	0.6849	−0.0499	0.107*
C13A	0.2166 (7)	0.4251 (8)	0.0653 (6)	0.065 (4)	0.50
C14A	0.1234 (9)	0.4089 (16)	0.0918 (9)	0.080 (5)	0.50
H14A	0.1051	0.4699	0.1093	0.116 (12)*	0.50
C15A	0.0616 (8)	0.3944 (13)	0.0264 (7)	0.115 (5)	0.50
H15A	−0.0001	0.3881	0.0445	0.116 (12)*	0.50
H15B	0.0792	0.3398	−0.0004	0.116 (12)*	0.50
H15C	0.0653	0.4458	−0.0077	0.116 (12)*	0.50
C16A	0.1064 (7)	0.3555 (10)	0.1568 (6)	0.109 (4)	0.50
H16A	0.0420	0.3552	0.1675	0.116 (12)*	0.50
H16B	0.1388	0.3807	0.1997	0.116 (12)*	0.50
H16C	0.1269	0.2940	0.1478	0.116 (12)*	0.50
C13B	0.2259 (7)	0.3700 (11)	0.0650 (5)	0.075 (4)	0.50
C14B	0.1267 (10)	0.3705 (12)	0.0763 (11)	0.091 (7)	0.50
H14B	0.1135	0.3591	0.1305	0.116 (12)*	0.50
C15B	0.1021 (11)	0.4660 (13)	0.0576 (12)	0.135 (5)	0.50
H15D	0.0374	0.4743	0.0639	0.116 (12)*	0.50
H15E	0.1187	0.4789	0.0055	0.116 (12)*	0.50
H15F	0.1342	0.5069	0.0912	0.116 (12)*	0.50
C16B	0.0834 (9)	0.3015 (10)	0.0311 (6)	0.108 (4)	0.50
H16D	0.0184	0.3038	0.0390	0.116 (12)*	0.50
H16E	0.1059	0.2424	0.0459	0.116 (12)*	0.50
H16F	0.0967	0.3118	−0.0220	0.116 (12)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0499 (13)	0.0499 (13)	0.0285 (14)	0.0067 (15)	−0.0048 (10)	−0.0048 (10)
O2	0.0677 (19)	0.0496 (15)	0.0387 (12)	−0.0017 (12)	−0.0011 (12)	−0.0013 (11)
O3	0.0553 (19)	0.081 (2)	0.0693 (18)	−0.0115 (17)	0.0050 (15)	0.0087 (17)
O4	0.0602 (18)	0.103 (2)	0.0280 (12)	0.0284 (17)	−0.0005 (11)	−0.0011 (12)
O5	0.0564 (17)	0.0494 (16)	0.0401 (12)	−0.0053 (12)	0.0068 (11)	−0.0095 (10)
O6	0.202 (5)	0.195 (5)	0.0499 (18)	0.140 (4)	0.039 (2)	0.021 (2)
O7	0.0459 (18)	0.145 (3)	0.0369 (14)	−0.0220 (17)	−0.0006 (12)	−0.0008 (16)
O8A	0.061 (4)	0.150 (7)	0.033 (3)	−0.014 (4)	−0.003 (3)	−0.009 (4)
O8B	0.084 (5)	0.214 (11)	0.050 (4)	−0.056 (6)	0.008 (4)	−0.027 (6)
O9	0.088 (2)	0.073 (2)	0.0650 (17)	−0.0203 (17)	0.0198 (17)	−0.0032 (16)
O10	0.336 (10)	0.143 (5)	0.184 (5)	0.120 (6)	0.151 (6)	0.036 (4)
C1	0.043 (2)	0.050 (2)	0.0320 (15)	0.0008 (16)	0.0009 (14)	−0.0074 (15)
C2	0.054 (2)	0.048 (2)	0.0322 (15)	−0.0011 (16)	0.0022 (14)	−0.0053 (14)
C3	0.046 (2)	0.078 (3)	0.0270 (16)	0.0072 (18)	0.0004 (14)	−0.0046 (16)
C4	0.047 (2)	0.095 (3)	0.0351 (18)	−0.014 (2)	0.0043 (15)	−0.0127 (18)
C5	0.060 (3)	0.079 (3)	0.0352 (18)	−0.021 (2)	0.0075 (17)	−0.0108 (18)
C6	0.112 (4)	0.085 (3)	0.050 (2)	−0.042 (3)	0.017 (3)	−0.015 (2)
C7	0.170 (7)	0.064 (4)	0.141 (6)	0.026 (4)	0.070 (5)	0.005 (4)
C8	0.185 (7)	0.094 (5)	0.144 (6)	0.051 (5)	0.034 (6)	0.036 (4)
C9	0.066 (3)	0.070 (3)	0.0380 (18)	−0.011 (2)	−0.0052 (19)	0.0030 (19)
C10	0.122 (5)	0.074 (3)	0.059 (3)	−0.031 (3)	−0.009 (3)	0.004 (2)
C11	0.077 (3)	0.116 (4)	0.041 (2)	0.038 (3)	0.009 (2)	0.006 (2)
C12	0.092 (4)	0.126 (5)	0.049 (2)	0.056 (3)	0.003 (2)	0.006 (3)
C13A	0.055 (6)	0.077 (8)	0.062 (7)	−0.007 (6)	−0.007 (5)	−0.006 (6)
C14A	0.057 (9)	0.111 (14)	0.071 (11)	−0.026 (8)	−0.013 (6)	0.016 (10)
C15A	0.061 (7)	0.189 (16)	0.095 (8)	0.003 (9)	−0.024 (6)	−0.011 (9)
C16A	0.051 (6)	0.166 (12)	0.109 (8)	−0.019 (7)	0.008 (5)	0.033 (8)
C13B	0.050 (7)	0.140 (13)	0.036 (5)	−0.019 (8)	0.002 (4)	0.010 (7)
C14B	0.075 (10)	0.136 (17)	0.062 (8)	−0.046 (10)	−0.002 (6)	−0.009 (10)
C15B	0.085 (11)	0.169 (18)	0.151 (15)	−0.020 (12)	0.018 (10)	−0.034 (14)
C16B	0.103 (9)	0.120 (11)	0.102 (8)	−0.039 (8)	0.012 (7)	−0.002 (8)

Geometric parameters (Å, º) top

O1—C1	1.417 (4)	C8—H8A	0.9800
O1—C1ⁱ	1.417 (4)	C8—H8B	0.9800
O2—C9	1.343 (5)	C8—H8C	0.9800
O2—C2	1.438 (4)	C9—C10	1.487 (6)
O3—C9	1.196 (5)	C10—H10A	0.9800
O4—C11	1.312 (5)	C10—H10B	0.9800
O4—C3	1.439 (4)	C10—H10C	0.9800
O5—C1	1.405 (4)	C11—C12	1.502 (5)
O5—C5	1.432 (5)	C12—H12A	0.9800
O6—C11	1.172 (5)	C12—H12B	0.9800
O7—C13A	1.379 (10)	C12—H12C	0.9800
O7—C13B	1.407 (10)	C13A—C14A	1.488 (13)
O7—C4	1.444 (5)	C14A—C16A	1.429 (18)
O8A—C13A	1.194 (11)	C14A—C15A	1.503 (15)
O8B—C13B	1.228 (11)	C14A—H14A	1.0000
O9—C7	1.329 (7)	C15A—H15A	0.9800
O9—C6	1.453 (6)	C15A—H15B	0.9800
O10—C7	1.176 (7)	C15A—H15C	0.9800
C1—C2	1.499 (5)	C16A—H16A	0.9800
C1—H1	1.0000	C16A—H16B	0.9800
C2—C3	1.514 (5)	C16A—H16C	0.9800
C2—H2	1.0000	C13B—C14B	1.493 (14)
C3—C4	1.515 (6)	C14B—C16B	1.460 (18)
C3—H3	1.0000	C14B—C15B	1.509 (16)
C4—C5	1.519 (6)	C14B—H14B	1.0000
C4—H4	1.0000	C15B—H15D	0.9800
C5—C6	1.494 (6)	C15B—H15E	0.9800
C5—H5	1.0000	C15B—H15F	0.9800
C6—H6A	0.9900	C16B—H16D	0.9800
C6—H6B	0.9900	C16B—H16E	0.9800
C7—C8	1.507 (10)	C16B—H16F	0.9800

C1—O1—C1ⁱ	113.1 (4)	C9—C10—H10B	109.5
C9—O2—C2	115.8 (3)	H10A—C10—H10B	109.5
C11—O4—C3	118.6 (3)	C9—C10—H10C	109.5
C1—O5—C5	113.5 (3)	H10A—C10—H10C	109.5
C13A—O7—C4	120.7 (5)	H10B—C10—H10C	109.5
C13B—O7—C4	114.3 (5)	O6—C11—O4	122.8 (4)
C7—O9—C6	119.0 (4)	O6—C11—C12	126.2 (4)
O5—C1—O1	111.1 (2)	O4—C11—C12	110.9 (3)
O5—C1—C2	110.1 (3)	C11—C12—H12A	109.5
O1—C1—C2	108.2 (3)	C11—C12—H12B	109.5
O5—C1—H1	109.1	H12A—C12—H12B	109.5
O1—C1—H1	109.1	C11—C12—H12C	109.5
C2—C1—H1	109.1	H12A—C12—H12C	109.5
O2—C2—C1	111.1 (3)	H12B—C12—H12C	109.5
O2—C2—C3	108.2 (3)	O8A—C13A—O7	122.9 (10)
C1—C2—C3	110.9 (3)	O8A—C13A—C14A	127.7 (10)
O2—C2—H2	108.9	O7—C13A—C14A	108.2 (9)
C1—C2—H2	108.9	C16A—C14A—C13A	120.9 (13)
C3—C2—H2	108.9	C16A—C14A—C15A	116.2 (14)
O4—C3—C2	106.6 (3)	C13A—C14A—C15A	110.5 (12)
O4—C3—C4	109.3 (3)	C16A—C14A—H14A	101.9
C2—C3—C4	109.6 (3)	C13A—C14A—H14A	101.9
O4—C3—H3	110.4	C15A—C14A—H14A	101.9
C2—C3—H3	110.4	C14A—C15A—H15A	109.5
C4—C3—H3	110.4	C14A—C15A—H15B	109.5
O7—C4—C3	110.0 (3)	H15A—C15A—H15B	109.5
O7—C4—C5	105.6 (3)	C14A—C15A—H15C	109.5
C3—C4—C5	111.3 (3)	H15A—C15A—H15C	109.5
O7—C4—H4	110.0	H15B—C15A—H15C	109.5
C3—C4—H4	110.0	C14A—C16A—H16A	109.5
C5—C4—H4	110.0	C14A—C16A—H16B	109.5
O5—C5—C6	105.7 (4)	H16A—C16A—H16B	109.5
O5—C5—C4	110.3 (3)	C14A—C16A—H16C	109.5
C6—C5—C4	113.2 (3)	H16A—C16A—H16C	109.5
O5—C5—H5	109.1	H16B—C16A—H16C	109.5
C6—C5—H5	109.1	O8B—C13B—O7	124.2 (9)
C4—C5—H5	109.1	O8B—C13B—C14B	121.8 (11)
O9—C6—C5	108.5 (3)	O7—C13B—C14B	113.8 (10)
O9—C6—H6A	110.0	C16B—C14B—C13B	111.2 (13)
C5—C6—H6A	110.0	C16B—C14B—C15B	115.9 (16)
O9—C6—H6B	110.0	C13B—C14B—C15B	102.5 (14)
C5—C6—H6B	110.0	C16B—C14B—H14B	109.0
H6A—C6—H6B	108.4	C13B—C14B—H14B	109.0
O10—C7—O9	121.5 (7)	C15B—C14B—H14B	109.0
O10—C7—C8	127.1 (7)	C14B—C15B—H15D	109.5
O9—C7—C8	111.3 (5)	C14B—C15B—H15E	109.5
C7—C8—H8A	109.5	H15D—C15B—H15E	109.5
C7—C8—H8B	109.5	C14B—C15B—H15F	109.5
H8A—C8—H8B	109.5	H15D—C15B—H15F	109.5
C7—C8—H8C	109.5	H15E—C15B—H15F	109.5
H8A—C8—H8C	109.5	C14B—C16B—H16D	109.5
H8B—C8—H8C	109.5	C14B—C16B—H16E	109.5
O3—C9—O2	123.5 (4)	H16D—C16B—H16E	109.5
O3—C9—C10	125.6 (5)	C14B—C16B—H16F	109.5
O2—C9—C10	110.9 (4)	H16D—C16B—H16F	109.5
C9—C10—H10A	109.5	H16E—C16B—H16F	109.5

C5—O5—C1—O1	58.4 (3)	C3—C4—C5—O5	−53.3 (4)
C5—O5—C1—C2	−61.4 (3)	O7—C4—C5—C6	69.1 (4)
C1ⁱ—O1—C1—O5	72.7 (2)	C3—C4—C5—C6	−171.5 (4)
C1ⁱ—O1—C1—C2	−166.4 (3)	C7—O9—C6—C5	−111.0 (5)
C9—O2—C2—C1	86.0 (3)	O5—C5—C6—O9	72.8 (4)
C9—O2—C2—C3	−152.1 (3)	C4—C5—C6—O9	−166.2 (4)
O5—C1—C2—O2	178.3 (3)	C6—O9—C7—O10	−1.8 (11)
O1—C1—C2—O2	56.7 (3)	C6—O9—C7—C8	175.8 (5)
O5—C1—C2—C3	58.0 (4)	C2—O2—C9—O3	−1.2 (5)
O1—C1—C2—C3	−63.6 (3)	C2—O2—C9—C10	178.5 (3)
C11—O4—C3—C2	−128.0 (4)	C3—O4—C11—O6	−0.4 (8)
C11—O4—C3—C4	113.6 (4)	C3—O4—C11—C12	177.9 (4)
O2—C2—C3—O4	66.2 (3)	C4—O7—C13A—O8A	5.3 (16)
C1—C2—C3—O4	−171.7 (3)	C4—O7—C13A—C14A	173.7 (11)
O2—C2—C3—C4	−175.6 (2)	O8A—C13A—C14A—C16A	147.4 (16)
C1—C2—C3—C4	−53.5 (3)	O7—C13A—C14A—C16A	−20 (2)
C13A—O7—C4—C3	80.3 (7)	O8A—C13A—C14A—C15A	7 (3)
C13B—O7—C4—C3	119.0 (8)	O7—C13A—C14A—C15A	−160.8 (15)
C13A—O7—C4—C5	−159.5 (7)	C4—O7—C13B—O8B	−3.3 (19)
C13B—O7—C4—C5	−120.8 (8)	C13A—O7—C13B—C14B	−69.4 (16)
O4—C3—C4—O7	−75.5 (3)	C4—O7—C13B—C14B	−178.8 (11)
C2—C3—C4—O7	168.0 (3)	O8B—C13B—C14B—C16B	27 (2)
O4—C3—C4—C5	167.8 (3)	O7—C13B—C14B—C16B	−157.8 (13)
C2—C3—C4—C5	51.3 (4)	O8B—C13B—C14B—C15B	−98 (2)
C1—O5—C5—C6	−178.2 (3)	O7—C13B—C14B—C15B	77.9 (16)
C1—O5—C5—C4	59.0 (4)	H1—C1—C1ⁱ—H1ⁱ	−89.1
O7—C4—C5—O5	−172.6 (3)

Symmetry code: (i) −y+1, −x+1, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱⁱ	1.00	2.53	3.487 (4)	161
C6—H6A···O6ⁱⁱⁱ	0.99	2.37	3.217 (8)	143
C8—H8B···O10^iv	0.98	2.53	3.412 (10)	150
C8—H8C···O3ⁱ	0.98	2.59	3.528 (8)	161
C12—H12B···O5ⁱⁱ	0.98	2.58	3.454 (5)	148

Symmetry codes: (i) −y+1, −x+1, −z+1/2; (ii) y, x, −z; (iii) −x+1/2, y−1/2, −z+1/4; (iv) −y+1/2, x−1/2, z+1/4.

Experimental details

Crystal data
Chemical formula	C₃₂H₄₆O₁₉
M_r	734.69
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	150
a, c (Å)	14.9188 (9), 17.8355 (6)
V (Å³)	3969.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.15 × 0.15

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan using multiple and symmetry-related data measurements via SORTAV (Blessing, 1995, 1997)
T_min, T_max	0.956, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	50356, 2206, 1414
R_int	0.132
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.155, 1.01
No. of reflections	2206
No. of parameters	281
No. of restraints	5
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.37

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top

O1—C1	1.417 (4)	C2—C3	1.514 (5)
O5—C5	1.432 (5)	C3—C4	1.515 (6)
C1—C2	1.499 (5)

C1—O1—C1ⁱ	113.1 (4)

H1—C1—C1ⁱ—H1ⁱ	−89.1

Symmetry code: (i) −y+1, −x+1, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱⁱ	1.00	2.53	3.487 (4)	161
C6—H6A···O6ⁱⁱⁱ	0.99	2.37	3.217 (8)	143
C8—H8B···O10^iv	0.98	2.53	3.412 (10)	150
C8—H8C···O3ⁱ	0.98	2.59	3.528 (8)	161
C12—H12B···O5ⁱⁱ	0.98	2.58	3.454 (5)	148

Symmetry codes: (i) −y+1, −x+1, −z+1/2; (ii) y, x, −z; (iii) −x+1/2, y−1/2, −z+1/4; (iv) −y+1/2, x−1/2, z+1/4.

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