Ditrityl α,α-trehalose hexa­acetate

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

doi:10.1107/S1600536802005408

Ditrityl α,α-trehalose hexaacetate

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

A twofold rotation axis passes through the bridging O atom between the two sugar rings in the title compound, C₆₂H₆₂O₁₇. Otherwise the geometry is much as would be expected for this type of molecule. Neither solvent nor hydrogen bonds are present in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802005408/cf6162sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802005408/cf6162Isup2.hkl Contains datablock I

CCDC reference: 185766

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R factor = 0.043
wR factor = 0.101
Data-to-parameter ratio = 8.9

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No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.37
         From the CIF: _reflns_number_total               3235
         Count of symmetry unique reflns         3244
         Completeness (_total/calc)             99.72%
         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.

Comment top

Trehalose continues to attract much attention due to its role in bio-protection (Sussich et al., 2001) and in certain drug formulations (Hatley & Blair, 1999). A crystal to glass transition by milling has also been observed for this non-reducing disaccharide (Willart et al., 2001). In search of materials with useful solid-state properties, a number of derivatives of trehalose have been prepared (Clow et al., 2001; Baddeley et al., 2001) and in this context the ditrityl hexaacetyl derivative of trehalose, (I), is now reported.

The molecule contains a twofold rotation axis with the bridging O atom (O1) in the special position (1/2,1,z). Hence, the geometry in Table 1 applies equally to both sugar rings in the molecule. No water is present in the crystal structure, which contains a maximum potential solvent volume of 32.7 Å³ compared to an expected volume of 40 Å³ for a hydrogen-bonded water molecule (Spek, 2001). No hydrogen bonds are present. The substitution at C1,C1' is α,α, with C1—O1 = 1.417 (3) Å and the angle subtended at O1 = 113.4 (2)°. The absolute configuration adopted in this refinement (see below) is R at C1, C2, C4 and C5, and S at C3. The sugar ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) calculated with PLATON (Spek, 2001) of Q = 0.592 (2) Å, θ = 4.5 (2)° and ϕ = 246 (2)°.

Experimental top

The title compound was prepared by reacting anhydrous α,α-trehalose with trityl chloride in pyridine, followed by excess acetic anhydride after 30 min. The mixture was left stirring for 4 h, then evaporated to an oil and plunged into water. The precipitate was stirred in hot methanol and filtered when cool. Recrystallization of the product to form suitable crystals was from an ethyl acetate/methanol mixture, by slow evaporation.

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 title molecule. Displacement ellipsoids are shown at the 50% probability level.

2,3,4-tri-O-acetyl-6-O-trityl-1-O-(2,3,4-tri-O-acetyl-6-O-tritylα-D– glucopyranosyl)-α-D-glucopyranose top

Crystal data top

C₆₂H₆₂O₁₇	D_x = 1.276 Mg m⁻³
M_r = 1079.12	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2	Cell parameters from 5000 reflections
a = 15.0595 (4) Å	θ = 1.8–26.4°
b = 17.1977 (6) Å	µ = 0.09 mm⁻¹
c = 10.8465 (4) Å	T = 150 K
V = 2809.12 (16) Å³	Prism, colourless
Z = 2	0.50 × 0.30 × 0.20 mm
F(000) = 1140

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	3235 independent reflections
Radiation source: Enraf-Nonius FR591 rotating anode	2333 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.4°, θ_min = 1.8°
ϕ and ω scans	h = −18→18
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −21→21
T_min = 0.955, T_max = 0.982	l = −13→13
16774 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0568P)²] where P = (F_o² + 2F_c²)/3
3235 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₆₂H₆₂O₁₇	V = 2809.12 (16) Å³
M_r = 1079.12	Z = 2
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 15.0595 (4) Å	µ = 0.09 mm⁻¹
b = 17.1977 (6) Å	T = 150 K
c = 10.8465 (4) Å	0.50 × 0.30 × 0.20 mm

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	3235 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	2333 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.982	R_int = 0.078
16774 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
3235 reflections	Δρ_min = −0.25 e Å⁻³
363 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	0.5000	1.0000	0.8011 (2)	0.0259 (6)
O2	0.33569 (10)	0.98239 (10)	0.88892 (17)	0.0321 (5)
O3	0.20150 (13)	0.92560 (11)	0.8817 (2)	0.0458 (5)
O4	0.35539 (11)	0.81530 (10)	0.96958 (17)	0.0333 (5)
O5	0.48244 (11)	0.90000 (9)	0.65828 (16)	0.0281 (4)
O6	0.36533 (15)	0.89970 (13)	1.1280 (2)	0.0527 (6)
O7	0.51108 (12)	0.74591 (10)	0.88536 (18)	0.0349 (5)
O8	0.41558 (15)	0.65155 (12)	0.8283 (2)	0.0529 (6)
O9	0.51307 (11)	0.74806 (10)	0.57844 (17)	0.0306 (4)
C1	0.43883 (16)	0.95672 (14)	0.7293 (3)	0.0275 (6)
H1	0.4064	0.9930	0.6730	0.0493 (19)*
C2	0.37292 (16)	0.92010 (14)	0.8175 (3)	0.0266 (6)
H2	0.3246	0.8945	0.7691	0.0493 (19)*
C3	0.41827 (16)	0.85968 (14)	0.8983 (3)	0.0280 (6)
H3	0.4629	0.8850	0.9536	0.0493 (19)*
C4	0.46345 (16)	0.80181 (14)	0.8129 (2)	0.0291 (6)
H4	0.4181	0.7749	0.7607	0.0493 (19)*
C5	0.53040 (16)	0.84374 (14)	0.7314 (3)	0.0282 (6)
H5	0.5748	0.8712	0.7843	0.0493 (19)*
C6	0.57796 (17)	0.79057 (15)	0.6430 (3)	0.0321 (7)
H6A	0.6144	0.8213	0.5848	0.0493 (19)*
H6B	0.6176	0.7548	0.6887	0.0493 (19)*
C7	0.24836 (17)	0.97687 (16)	0.9191 (3)	0.0357 (7)
C8	0.2205 (2)	1.04135 (19)	1.0009 (4)	0.0587 (10)
H8A	0.1558	1.0404	1.0105	0.097 (5)*
H8B	0.2385	1.0911	0.9645	0.097 (5)*
H8C	0.2487	1.0353	1.0818	0.097 (5)*
C9	0.33984 (19)	0.83878 (18)	1.0864 (3)	0.0395 (7)
C10	0.2863 (2)	0.7796 (2)	1.1545 (3)	0.0594 (10)
H10A	0.3261	0.7411	1.1916	0.097 (5)*
H10B	0.2458	0.7535	1.0970	0.097 (5)*
H10C	0.2519	0.8053	1.2194	0.097 (5)*
C11	0.4794 (2)	0.67099 (16)	0.8839 (3)	0.0415 (7)
C12	0.5378 (2)	0.62098 (19)	0.9610 (4)	0.0698 (12)
H12A	0.5857	0.6525	0.9961	0.097 (5)*	0.34 (4)
H12B	0.5633	0.5796	0.9099	0.097 (5)*	0.34 (4)
H12C	0.5029	0.5978	1.0278	0.097 (5)*	0.34 (4)
H12D	0.5155	0.5674	0.9597	0.097 (5)*	0.66 (4)
H12E	0.5380	0.6404	1.0459	0.097 (5)*	0.66 (4)
H12F	0.5984	0.6222	0.9280	0.097 (5)*	0.66 (4)
C13	0.54362 (16)	0.70324 (15)	0.4741 (3)	0.0326 (6)
C14	0.46089 (17)	0.65837 (15)	0.4324 (3)	0.0340 (7)
C15	0.37963 (17)	0.66718 (17)	0.4898 (3)	0.0433 (8)
H15	0.3739	0.7023	0.5569	0.0493 (19)*
C16	0.3064 (2)	0.62515 (19)	0.4504 (4)	0.0517 (9)
H16	0.2509	0.6317	0.4907	0.0493 (19)*
C17	0.3134 (2)	0.57462 (18)	0.3543 (4)	0.0527 (9)
H17	0.2629	0.5463	0.3272	0.0493 (19)*
C18	0.3937 (2)	0.5649 (2)	0.2970 (4)	0.0622 (10)
H18	0.3992	0.5293	0.2304	0.0493 (19)*
C19	0.4663 (2)	0.60666 (19)	0.3358 (3)	0.0538 (9)
H19	0.5216	0.5997	0.2951	0.0493 (19)*
C20	0.56998 (18)	0.75812 (17)	0.3686 (3)	0.0404 (7)
C21	0.53403 (19)	0.83244 (18)	0.3648 (3)	0.0457 (8)
H21	0.4973	0.8499	0.4304	0.0493 (19)*
C22	0.5511 (3)	0.8812 (2)	0.2666 (4)	0.0683 (11)
H22	0.5267	0.9321	0.2659	0.0493 (19)*
C23	0.6021 (3)	0.8572 (4)	0.1714 (5)	0.0890 (15)
H23	0.6122	0.8907	0.1031	0.0493 (19)*
C24	0.6392 (3)	0.7843 (4)	0.1736 (4)	0.0929 (16)
H24	0.6765	0.7679	0.1079	0.0493 (19)*
C25	0.6227 (2)	0.7345 (2)	0.2708 (4)	0.0629 (10)
H25	0.6477	0.6838	0.2707	0.0493 (19)*
C26	0.61601 (17)	0.64760 (17)	0.5193 (3)	0.0391 (7)
C27	0.70605 (19)	0.6622 (2)	0.5029 (4)	0.0573 (10)
H27	0.7249	0.7062	0.4569	0.0493 (19)*
C28	0.7689 (2)	0.6116 (3)	0.5547 (5)	0.0768 (14)
H28	0.8304	0.6214	0.5425	0.0493 (19)*
C29	0.7433 (3)	0.5490 (3)	0.6220 (4)	0.0763 (13)
H29	0.7866	0.5152	0.6566	0.0493 (19)*
C30	0.6550 (3)	0.5348 (2)	0.6397 (4)	0.0664 (11)
H30	0.6371	0.4912	0.6872	0.0493 (19)*
C31	0.5916 (2)	0.58318 (18)	0.5892 (3)	0.0499 (9)
H31	0.5305	0.5724	0.6023	0.0493 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0268 (12)	0.0221 (12)	0.0289 (14)	−0.0037 (10)	0.000	0.000
O2	0.0256 (9)	0.0275 (9)	0.0433 (12)	0.0020 (8)	0.0038 (8)	−0.0062 (9)
O3	0.0306 (10)	0.0418 (11)	0.0651 (15)	−0.0037 (10)	0.0079 (11)	−0.0049 (11)
O4	0.0374 (10)	0.0309 (10)	0.0315 (11)	−0.0030 (9)	0.0051 (9)	0.0005 (9)
O5	0.0320 (9)	0.0242 (9)	0.0281 (10)	0.0031 (8)	−0.0005 (8)	−0.0023 (8)
O6	0.0643 (14)	0.0504 (13)	0.0434 (14)	−0.0062 (12)	0.0122 (12)	−0.0098 (11)
O7	0.0381 (10)	0.0244 (9)	0.0422 (11)	0.0028 (8)	−0.0040 (9)	0.0041 (9)
O8	0.0542 (13)	0.0343 (11)	0.0701 (17)	−0.0115 (11)	−0.0077 (12)	0.0092 (12)
O9	0.0267 (9)	0.0280 (9)	0.0371 (10)	−0.0030 (8)	0.0029 (8)	−0.0096 (9)
C1	0.0279 (13)	0.0245 (13)	0.0300 (15)	0.0004 (11)	−0.0020 (12)	−0.0034 (12)
C2	0.0258 (13)	0.0226 (13)	0.0314 (15)	0.0024 (11)	−0.0024 (12)	−0.0033 (12)
C3	0.0292 (13)	0.0246 (13)	0.0302 (16)	−0.0028 (11)	0.0031 (12)	0.0005 (12)
C4	0.0310 (14)	0.0225 (13)	0.0339 (16)	0.0048 (11)	−0.0021 (13)	0.0002 (12)
C5	0.0270 (13)	0.0244 (13)	0.0332 (15)	0.0027 (11)	−0.0001 (12)	−0.0026 (12)
C6	0.0264 (13)	0.0296 (14)	0.0403 (17)	−0.0004 (11)	0.0005 (13)	−0.0096 (14)
C7	0.0293 (14)	0.0333 (15)	0.0444 (18)	0.0027 (13)	0.0036 (14)	0.0005 (14)
C8	0.0430 (17)	0.056 (2)	0.077 (3)	0.0065 (16)	0.0142 (18)	−0.0245 (19)
C9	0.0422 (16)	0.0416 (17)	0.0346 (18)	0.0023 (14)	0.0042 (14)	0.0028 (15)
C10	0.076 (2)	0.060 (2)	0.043 (2)	−0.0112 (19)	0.0170 (19)	0.0044 (18)
C11	0.0456 (17)	0.0282 (15)	0.0507 (19)	0.0049 (14)	0.0069 (16)	0.0067 (15)
C12	0.075 (2)	0.0385 (19)	0.096 (3)	0.0071 (18)	−0.012 (2)	0.024 (2)
C13	0.0306 (13)	0.0318 (15)	0.0355 (16)	0.0030 (12)	0.0010 (13)	−0.0143 (13)
C14	0.0329 (14)	0.0263 (14)	0.0429 (17)	0.0009 (12)	−0.0060 (13)	−0.0026 (13)
C15	0.0327 (15)	0.0413 (17)	0.056 (2)	−0.0021 (13)	−0.0092 (15)	−0.0083 (16)
C16	0.0342 (16)	0.054 (2)	0.067 (2)	−0.0034 (15)	−0.0119 (16)	0.005 (2)
C17	0.0491 (19)	0.0426 (18)	0.067 (2)	−0.0118 (15)	−0.0262 (18)	−0.0005 (18)
C18	0.061 (2)	0.048 (2)	0.077 (3)	−0.0039 (17)	−0.017 (2)	−0.025 (2)
C19	0.0463 (18)	0.051 (2)	0.064 (2)	−0.0042 (16)	−0.0058 (18)	−0.0227 (19)
C20	0.0335 (15)	0.0457 (17)	0.0420 (18)	−0.0055 (14)	0.0007 (14)	−0.0112 (16)
C21	0.0407 (16)	0.0516 (19)	0.0449 (19)	−0.0015 (15)	0.0018 (15)	0.0049 (17)
C22	0.065 (2)	0.068 (2)	0.072 (3)	−0.013 (2)	0.001 (2)	0.021 (2)
C23	0.087 (3)	0.116 (4)	0.063 (3)	−0.031 (3)	0.004 (3)	0.025 (3)
C24	0.086 (3)	0.134 (5)	0.059 (3)	−0.025 (3)	0.041 (3)	−0.013 (3)
C25	0.060 (2)	0.071 (2)	0.058 (2)	−0.0094 (19)	0.0205 (19)	−0.021 (2)
C26	0.0332 (14)	0.0391 (17)	0.0451 (19)	0.0059 (13)	−0.0076 (14)	−0.0204 (16)
C27	0.0364 (16)	0.0569 (19)	0.078 (3)	0.0080 (16)	−0.0067 (17)	−0.0323 (19)
C28	0.0346 (18)	0.082 (3)	0.114 (4)	0.022 (2)	−0.028 (2)	−0.055 (3)
C29	0.075 (3)	0.064 (3)	0.089 (3)	0.037 (2)	−0.040 (3)	−0.038 (3)
C30	0.079 (3)	0.053 (2)	0.067 (3)	0.026 (2)	−0.024 (2)	−0.011 (2)
C31	0.0482 (18)	0.0445 (18)	0.057 (2)	0.0088 (15)	−0.0107 (17)	−0.0077 (18)

Geometric parameters (Å, º) top

O1—C1	1.417 (3)	C11—C12	1.487 (4)
O1—C1ⁱ	1.417 (3)	C13—C26	1.531 (4)
O2—C7	1.359 (3)	C13—C14	1.534 (4)
O2—C2	1.436 (3)	C13—C20	1.536 (4)
O3—C7	1.200 (3)	C14—C19	1.376 (4)
O4—C9	1.351 (3)	C14—C15	1.382 (4)
O4—C3	1.441 (3)	C15—C16	1.386 (4)
O5—C1	1.406 (3)	C16—C17	1.361 (5)
O5—C5	1.444 (3)	C17—C18	1.371 (5)
O6—C9	1.203 (4)	C18—C19	1.374 (4)
O7—C11	1.374 (3)	C20—C25	1.385 (5)
O7—C4	1.434 (3)	C20—C21	1.389 (4)
O8—C11	1.183 (4)	C21—C22	1.379 (5)
O9—C6	1.407 (3)	C22—C23	1.351 (6)
O9—C13	1.444 (3)	C23—C24	1.374 (6)
C1—C2	1.515 (4)	C24—C25	1.380 (6)
C2—C3	1.521 (4)	C26—C27	1.390 (4)
C3—C4	1.520 (4)	C26—C31	1.392 (5)
C4—C5	1.523 (4)	C27—C28	1.403 (5)
C5—C6	1.506 (4)	C28—C29	1.357 (6)
C7—C8	1.481 (4)	C29—C30	1.365 (6)
C9—C10	1.494 (4)	C30—C31	1.380 (5)

C1—O1—C1ⁱ	113.3 (3)	O9—C13—C26	108.0 (2)
C7—O2—C2	117.1 (2)	O9—C13—C14	104.0 (2)
C9—O4—C3	117.3 (2)	C26—C13—C14	111.0 (2)
C1—O5—C5	113.41 (19)	O9—C13—C20	109.8 (2)
C11—O7—C4	116.7 (2)	C26—C13—C20	116.0 (2)
C6—O9—C13	116.49 (18)	C14—C13—C20	107.4 (2)
O5—C1—O1	111.21 (18)	C19—C14—C15	117.8 (3)
O5—C1—C2	111.3 (2)	C19—C14—C13	120.1 (3)
O1—C1—C2	107.3 (2)	C15—C14—C13	122.1 (3)
O2—C2—C1	106.63 (19)	C14—C15—C16	120.5 (3)
O2—C2—C3	112.0 (2)	C17—C16—C15	120.5 (3)
C1—C2—C3	110.7 (2)	C16—C17—C18	119.5 (3)
O4—C3—C4	105.92 (18)	C17—C18—C19	120.0 (3)
O4—C3—C2	112.08 (19)	C18—C19—C14	121.5 (3)
C4—C3—C2	107.3 (2)	C25—C20—C21	118.0 (3)
O7—C4—C3	109.2 (2)	C25—C20—C13	122.6 (3)
O7—C4—C5	107.7 (2)	C21—C20—C13	119.1 (3)
C3—C4—C5	109.9 (2)	C22—C21—C20	120.7 (3)
O5—C5—C6	107.2 (2)	C23—C22—C21	120.7 (4)
O5—C5—C4	107.76 (19)	C22—C23—C24	119.8 (4)
C6—C5—C4	113.4 (2)	C23—C24—C25	120.4 (4)
O9—C6—C5	107.58 (19)	C24—C25—C20	120.4 (4)
O3—C7—O2	122.6 (3)	C27—C26—C31	118.1 (3)
O3—C7—C8	125.9 (3)	C27—C26—C13	122.7 (3)
O2—C7—C8	111.5 (3)	C31—C26—C13	118.9 (3)
O6—C9—O4	123.8 (3)	C26—C27—C28	119.6 (4)
O6—C9—C10	125.5 (3)	C29—C28—C27	121.1 (4)
O4—C9—C10	110.7 (3)	C28—C29—C30	119.6 (4)
O8—C11—O7	123.6 (3)	C29—C30—C31	120.7 (4)
O8—C11—C12	127.1 (3)	C30—C31—C26	120.9 (3)
O7—C11—C12	109.3 (3)

C5—O5—C1—O1	60.7 (2)	C26—C13—C14—C19	−61.7 (4)
C5—O5—C1—C2	−58.9 (3)	C20—C13—C14—C19	66.0 (3)
C1ⁱ—O1—C1—O5	63.35 (16)	O9—C13—C14—C15	1.5 (4)
C1ⁱ—O1—C1—C2	−174.7 (2)	C26—C13—C14—C15	117.4 (3)
C7—O2—C2—C1	143.4 (2)	C20—C13—C14—C15	−114.8 (3)
C7—O2—C2—C3	−95.4 (3)	C19—C14—C15—C16	−0.2 (5)
O5—C1—C2—O2	177.29 (19)	C13—C14—C15—C16	−179.4 (3)
O1—C1—C2—O2	55.4 (2)	C14—C15—C16—C17	−0.1 (5)
O5—C1—C2—C3	55.3 (3)	C15—C16—C17—C18	0.5 (5)
O1—C1—C2—C3	−66.6 (2)	C16—C17—C18—C19	−0.7 (5)
C9—O4—C3—C4	147.3 (2)	C17—C18—C19—C14	0.4 (6)
C9—O4—C3—C2	−96.0 (3)	C15—C14—C19—C18	0.1 (5)
O2—C2—C3—O4	70.2 (2)	C13—C14—C19—C18	179.3 (3)
C1—C2—C3—O4	−171.0 (2)	O9—C13—C20—C25	162.5 (3)
O2—C2—C3—C4	−173.96 (19)	C26—C13—C20—C25	39.7 (4)
C1—C2—C3—C4	−55.1 (3)	C14—C13—C20—C25	−85.1 (3)
C11—O7—C4—C3	112.1 (2)	O9—C13—C20—C21	−22.9 (3)
C11—O7—C4—C5	−128.6 (2)	C26—C13—C20—C21	−145.7 (3)
O4—C3—C4—O7	−63.1 (2)	C14—C13—C20—C21	89.5 (3)
C2—C3—C4—O7	177.00 (19)	C25—C20—C21—C22	−0.4 (5)
O4—C3—C4—C5	178.93 (19)	C13—C20—C21—C22	−175.2 (3)
C2—C3—C4—C5	59.0 (3)	C20—C21—C22—C23	0.9 (5)
C1—O5—C5—C6	−176.39 (19)	C21—C22—C23—C24	−1.7 (6)
C1—O5—C5—C4	61.3 (3)	C22—C23—C24—C25	1.9 (7)
O7—C4—C5—O5	179.94 (18)	C23—C24—C25—C20	−1.3 (6)
C3—C4—C5—O5	−61.2 (3)	C21—C20—C25—C24	0.6 (5)
O7—C4—C5—C6	61.5 (3)	C13—C20—C25—C24	175.2 (3)
C3—C4—C5—C6	−179.6 (2)	O9—C13—C26—C27	−100.6 (3)
C13—O9—C6—C5	169.7 (2)	C14—C13—C26—C27	146.1 (3)
O5—C5—C6—O9	−66.6 (3)	C20—C13—C26—C27	23.1 (4)
C4—C5—C6—O9	52.2 (3)	O9—C13—C26—C31	73.5 (3)
C2—O2—C7—O3	−5.1 (4)	C14—C13—C26—C31	−39.8 (4)
C2—O2—C7—C8	175.4 (2)	C20—C13—C26—C31	−162.7 (3)
C3—O4—C9—O6	10.8 (4)	C31—C26—C27—C28	1.1 (5)
C3—O4—C9—C10	−170.0 (2)	C13—C26—C27—C28	175.3 (3)
C4—O7—C11—O8	−1.1 (4)	C26—C27—C28—C29	−0.8 (5)
C4—O7—C11—C12	178.6 (3)	C27—C28—C29—C30	0.0 (6)
C6—O9—C13—C26	56.7 (3)	C28—C29—C30—C31	0.4 (6)
C6—O9—C13—C14	174.7 (2)	C29—C30—C31—C26	−0.1 (5)
C6—O9—C13—C20	−70.7 (3)	C27—C26—C31—C30	−0.6 (5)
O9—C13—C14—C19	−177.7 (3)	C13—C26—C31—C30	−175.0 (3)

Symmetry code: (i) −x+1, −y+2, z.

Experimental details

Crystal data
Chemical formula	C₆₂H₆₂O₁₇
M_r	1079.12
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	150
a, b, c (Å)	15.0595 (4), 17.1977 (6), 10.8465 (4)
V (Å³)	2809.12 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.30 × 0.20

Data collection
Diffractometer	Enraf Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995, 1997)
T_min, T_max	0.955, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	16774, 3235, 2333
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.101, 1.00
No. of reflections	3235
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

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 (3)	O5—C5	1.444 (3)
O5—C1	1.406 (3)

C1—O1—C1ⁱ	113.3 (3)	O9—C13—C26	108.0 (2)
C1—O5—C5	113.41 (19)	O9—C13—C14	104.0 (2)
O4—C3—C4	105.92 (18)	O9—C13—C20	109.8 (2)

C13—O9—C6—C5	169.7 (2)	C3—O4—C9—O6	10.8 (4)
C2—O2—C7—O3	−5.1 (4)	C4—O7—C11—O8	−1.1 (4)