Supramolecular structures of substituted α,α′-trehalose derivatives

The structures of five substituted α,α′-trehalose trehalose derivatives have been determined, and these are compared with those of four previously published analogues. In 2,2′,3,3′,4,4′-hexaacetato-6,6′-bis-O-methylsulfonyl-α,α′-trehalose, C₂₆H₃₈O₂₁S₂, where the molecules lie across twofold rotation axes in the space group C2, a single C—H⋯O=S hydrogen bond links the molecules into sheets. 2,2′,3,3′,4,4′-Hexaacetato-6,6′-bis-O-(4-toluenesulfonyl)-α,α′-trehalose, C₃₈H₄₆O₂₁S₂, crystallizes with Z′ = 2 in the space group P2₁2₁2₁ and a combination of three C—H⋯O hydrogen bonds, each having a carbonyl O atom as an acceptor, and a C—H⋯π(arene) hydrogen bond link the molecules into a three-dimensional framework. 2,2′,3,3′,4,4′-Hexaacetato-6,6′-diazido-α,α′-trehalose, C₂₄H₃₂N₆O₁₅, crystallizes as a partial ethanol solvate and three C—H⋯O hydrogen bonds link the substituted trehalose molecules into a three-dimensional framework. In 2,2′,3,3′-tetraacetato-6,6′-bis(N-acetylamino)-α,α′-trehalose dihydrate, C₂₄H₃₆N₂O₁₅·2H₂O, the substituted trehalose molecules lie across twofold rotation axes in the space group P2₁2₁2 and a three-dimensional framework is generated by the combination of O—H⋯O and N—H⋯O hydrogen bonds. The diaminotrehalose molecules in 6,6′-diamino-α,α′-trehalose dihydrate, C₁₂H₂₄N₂O₉.2(H₂O), lie across twofold rotation axes in the space group P4₃2₁2: a single O—H⋯N hydrogen bond links the trehalose molecules into sheets, which are linked into a three-dimensional framework by O—H⋯O hydrogen bonds.

1. Introduction

Recent reports on the structures of the multiply substituted α,α′-trehalose derivatives (1) [see (I)], which crystallizes as an ethyl acetate monosolvate (Baddeley et al., 2001), (2), which crystallizes as a partial (0.7 mol) hydrate (Clow et al., 2001), (3) (Baddeley et al., 2002) and (4) (Baddeley et al., 2003) indicate that, despite the wide variation of the substituents, particularly those at the 6 and 6′ positions, the pyranose rings all adopt very similar chair conformations, as judged by the ring-puckering parameters (Cremer & Pople, 1975).

In (1)–(3) there are no direction-specific interactions between the molecules, but in (4) a single O—H⋯O hydrogen bond links the molecules into helical C12 (Bernstein et al., 1995) chains, which are weakly reinforced by a C—H⋯O=C hydrogen bond. Two further C—H⋯O contacts were reported in (4), but both of these involve methyl C—H bonds. Since it is now well established (Riddell & Rogerson, 1996, 1997) that in the solid state methyl groups, H₃C—X, generally undergo very rapid rotation about their C—X bonds, even at very low temperatures, such that the H-atom sites identified from diffraction data generally represent the minima in the corresponding rotational potential functions, rather than statically occupied sites, it is unlikely that contacts involving methyl C—H bonds such as those reported will, or can, have any structural significance.

In this paper, we report the molecular and supramolecular structures of further examples of substituted α,α′-trehalose derivatives, (5)–(9) [see (I)], where the substituents were selected to afford the possibility of other types of direction-specific intermolecular interactions: for example, (5) and (6) both offer the possibility of C—H⋯O=S hydrogen bonds, while both C—H⋯π(arene) hydrogen bonds and aromatic π⋯π stacking interactions could occur in (6); C—H⋯N hydrogen bonds could in principle occur in (7); O—H⋯O and N—H⋯O hydrogen bonds could both occur in (8); and O—H⋯O, N—H⋯O, and O—H⋯N hydrogen bonds are all possible in (9).

2. Experimental

2.1. Syntheses

Compound (5): A solution of 2,2′,3,3′,4,4′-hexa-O-acetyl-α,α′-trehalose (10 g, 16.8 mmol) and methanesulfonyl chloride (5.8 g, 4 cm³, 50.5 mmol) in acetonitrile (30 cm³) and pyridine (10 cm³) was stirred for 3 h, and rotary evaporated to leave an oily solid. After shaking the residue with water, a solid was collected, washed with water, dried in vacuo at 330 K and recrystallized from ethanol; yield 10.4 g (92%), m.p. 441 K, lit. m.p. 441–442 K; (Birch & Richardson, 1968); [α]_D (CHCl₃) 146.2°, lit. [α]_D (CHCl₃) 143° (Birch & Richardson, 1968). NMR (CDCl₃): δ(¹H) 2.01 (s, 3H, Me), 2.05 (s, 3H, Me), 2.08 (3, 3H, Me), 3.01 (s, 3H, Me), 4.11 (td, 1H, J = 2.14, 6.22, H-5), 4.14 (dd, 1H, J = 2.14, 11.10, H-6′), 4.22 (dd, 1H, J = 6.22, 11.10, H-6), 4.98 (t, 1H, J = ca 9), 5.01 (dd, 1H, J = 3.85, 10.37, H-2), 5.28 (d, 1H, J = 3.85, H-1), 5.46 (t, 1H, J = 10.37, H-3): δ(¹³C) 20.6, 37.7, 66.5, 68.2, 68.4, 69.6, 69.7, 92.6, 169.6, 169.8, 169.9. IR (KBr, cm⁻¹): 2972, 2932, 1760, 1743, 1357, 1219, 1178, 1143, 1037, 1018, 989, 955, 811.

Compound (6): A solution of 2,2′,3,3′,4,4′-hexa-O-acetyl-α,α′-trehalose (10 g, 16.8 mmol) and 4-toluenesulfonyl chloride (9.6 g, 50.5 mmol) in acetonitrile (30 cm³) and pyridine (10 cm³) was stirred for 24 h and DMAP (ca 10 mg) added. After stirring for a further 5 h, the solution was evaporated to a syrupy residue, which was poured into water with vigorous stirring. The off-white precipitate was filtered off, washed with water and air dried. The resulting solid was washed with boiling ethanol, dried at 330 K in vacuum and recrystallized from ethanol; yield 11.4 g (90.4%), m.p. 431–434 K, lit. m.p. 443–445 K (Birch & Richardson, 1968). NMR (CDCl₃): δ(¹H) 1.98 (s, 3H, Me), 2.01 (s, 3H, Me), 2.06 (s, 3H, Me), 2.43 (s, 3H, Me), 4.02 (m, 2H), 4.10 (m, 1H), 4.90 (m, 3H), 5.38 (m, 1H), 7.32 (d, 2H, J = 7.95), 7.72 (d, 2H, J = 8.35): δ(¹³C) 20.6, 21.6, 67.6, 68.2, 68.6, 69.2, 69.8, 92.8, 128.0, 129.9, 132.4, 145.3, 169.5, 169.6, 169.9. IR (KBr, cm⁻¹): 2963, 1754, 1371, 1221, 1178, 1081, 1039, 979, (810, 669, 554). MS (ES⁺, MeCN): 667.4 [100%], 796.4 [30%], 925.5 [20%, M + Na], 458.4 [18%], 417.4 [15%], 771.5 [10%, M − CH₃C₆H₄SO₂ + Na].

Compound (7): To a solution of 2,2′,3,3′,4,4′-hexa-O-acetyl-6,6′-di-O-methanesulfonyl-α,α′-trehalose (10.0 g, 14.9 mmol) in DMSO (60 cm³) was added sodium azide (3.0 g, 46 mmol) and the solution heated to 350 K. After 1 h, TLC with ethyl acetate:light petroleum (boiling range 313–333 K) (2:1 v/v) as eluent showed complete reaction. The solution was poured into water (200 cm³) and the solid was collected, dried and recrystallized from ethanol as a partial solvate; yield 8.5 g (94%), m.p. 413 K, lit. m.p. 387–389 K (Birch & Richardson, 1968), 392–393 K (Kurita et al., 1994), 394–398 K (Liav & Goren, 1980); [α]_D (CHCl₃) 127°, lit. [α]_D (CHCl₃) 134° (Birch & Richardson, 1968), (CHCl₃) 138° (Kurita et al., 1994). NMR (CDCl₃): δ(¹H) 2.02 (s, 3H, Me), 2.05 (s, 3H, Me), 2.11 (s, 3H, Me), 3.16 (dd, 1H, J = 2.44, 13.32, H-6′), 3.36 (dd, 1H, J = 7.39, 13.32, H-6), 4.08 (m, 1H, J = 2.44, 7.39, 9.1, H-5), 4.98 (dd, 1H, 9.4, 9.9, H-4), 5.07 (dd, 1H, J = 3.82, 10.31, H-2), 5.31 (d, 1H, J = 3.82, H-1), 5.45 (dd, 1H, J = 9.4, 10.31, H-3): δ(¹³C) 20.7, 51.0, 67.7, 69.8, 69.9, 92.7, 169.6, 170.0. IR (KBr, cm⁻¹): 2101, 1740, 1211, 1033, 1014. MS (ES⁺, MeCN): 667.2 [100%, M + Na], 105.1 [50%], 642.2 [20%].

Compound (8): To a solution of 2,2′,3,3′,4,4′-hexa-O-acetyl-6,6′-di-O-azido-α,α′-trehalose (10.0 g, 16.4 cm³) in thf (80 cm³) was added triphenylphosphine (9.0 g, 34.4 mmol) and water (2 cm³). After stirring for 1 h, TLC, using ethyl acetate: light petroleum (2:1 v/v) as eluent, indicated the consumption of the starting material. The suspension was filtered and the solid 2,2′,3,3′,4,4′-hexa-O-acetyl-6,6′-diamino-6,6′-dideoxy-α,α′-tre­halose was washed with dichloromethane and dried; yield 4.9 g (51%), m.p. 418–428 K. NMR (CDCl₃): δ(¹H) 1.95 (s, 3H, Me), 2.05 (s, 3H, Me), 2.07 (s, 3H, Me), 3.14 (dd, 1H, J = 7.59, 14.15, H-6), 3.42 (t, 1H, J = 9.57, H-4), 3.68 (m, 1H, H-5), 3.81 (dd, 1H, J = 2.61, 14.15, H-6′), 4.85 (dd, 1H, J = 3.58, 10.3, H-2), 5.33 (d, 1H, J = 3.58, H-1), 5.34 (m, 1H, J = 10.3, H-3): δ(¹³C) 21.3, 22.8, 40.8, 71.7, 72.0, 72.1, 72.4, 73.4, 94.4, 175.5. MS (ES⁺): 579.0 [100%], 301.0 [80%], 615.1 [45%, M + Na].

A solution of the foregoing 2,2′,3,3′,4,4′-hexa-O-acetyl-6,6′-diamino-6,6′-dideoxy-α,α′-trehalose (0.5 g) in pyridine (10 cm³) was allowed to stand overnight. Diethyl ether was added to precipitate the rearranged product, (8), which was recrystallized from aqueous ethanol as the dihydrate, m.p. 477 K; lit. m.p. (from ethanol/ether) 470–473 K (Liav & Goren, 1980); [α]_D (MeOH) 123.2°, lit. [α]_D (MeOH/water, 3:1) 130° (Liav & Goren, 1980). NMR (CDCl₃): δ(¹H) 1.80 (s, 3H, Me), 1.98 (s, 3H, Me), 2.02 (s, 3H, Me), 2.91 (m, 1H, H-6), 3.38 (t, 1H, J = 9.15, H-4), 3.54 (m, 1H, H-5), 3.70 (m, 1H, H-6′), 4.79 (dd, 1H, J = 3.66, 10.37, H-2), 5.18 (m, 2H, H-1 and H-3), 7.81 (t, J = 4.28, NHCOCH₃): δ(¹³C) 20.3, 20.8, 22.4, 69.0, 69.8, 71.4, 71.7, 90.6, 169.7, 169.9. IR (KBr, cm⁻¹): 3615–3096, 2867, 1739, 1643, 1571, 1437, 1378, 1236, 1141, 1047, 1017. MS (ES⁺): 615.3 [100%, M + Na], 573.3 [6%, M − Ac + Na], 1207.7 [2%, 2M + Na], 531.3 [1%, M − 2Ac + Na].

Compound (9): A suspension of 2,2′,3,3′,4,4′-hexa-O-acetyl-6,6′-di-O-azido-α,α′-trehalose (5.0 g, 7.8 mmol) and sodium methoxide (42.2 mg, 0.78 mmol) in methanol (40 cm³) was stirred for 4.5 h. The colourless solution was neutralized with DOWEX 50 W X-8 resin and the resin filtered off. The resin was washed with methanol, and the filtrates and washings were combined and evaporated to leave a white product, 6,6′-diazido-6,6′-dideoxy-α,α′-trehalose, which was crystallized from ethanol; yield 2.05 g (67%), m. p. 474–476 K; [α]_D (water) 153°; lit. m.p. 482–484 K (Birch & Richardson, 1968), 463–465 K (Kurita et al., 1994), lit. [α]_D (water) 158° (Birch & Richardson, 1968). NMR (CDCl₃): δ(¹H) 3.29(t, 1H, J = 9.23, H-3/4), 3.39 (dd, 1H, J = 6.16, 13.68, H-6), 3.51 (m, 2H, J = 2.39, 13.68, H-6′, H-2), 3.66 (t, 1H, J = 9.23, H-3/4), 3.81 (ddd, 1H, J = 2.39, 5.81, 9.92, H-5), 5.03 (d, 1H, J = 3.76, H-1): δ(¹³C) 51.9, 71.5, 71.9, 72.1, 73.3, 94.8. IR (KBr, cm⁻¹): 3537–3263, 2947, 2918, 2200, 2106, 1601, 1446, 1415, 1344, 1288, 1147, 1105, 1070, 1043, 984, 930, 584, 567. MS (ES+): 415.1 ([100%, M + Na], 455.3 [32%], 432.9 [25%, M + Na + H₂O].

The foregoing 6,6′-diazido-6,6′-dideoxy-α,α′-trehalose (0.5 g, 1.27 mmol) and triphenylphosphine (1.34 g, 5.10 mmol) were dissolved in DMF (10 cm³). After 2 h when effervescence had ceased, ammonium hydroxide solution (30%, 4 cm³) was added and a precipitate formed. Ethanol (50 cm³) was added and the reaction mixture was heated at 330 K for 2 h to ensure complete dissolution. Crystals of 6,6′-diamino-6,6′-dideoxy-α,α′-trehalose dihydrate were obtained on cooling; 260 mg (60%); m.p. 498–500 K; lit. m.p. 473 K (Kurita et al., 1994). NMR (CDCl₃): δ(¹H) 2.70 (dd, 1H, J = 7.63, 13.73, H-6), 2.95 (dd, 1H, J = 2.44, 13.73, H-6′), 3.29 (t, 1H, J = 9.77, H-3/4), 3.62 (dd, 1H, J = 3.36, 10.07, H-2), 3.71 (m, 1H, H-5), 3.80 (t, 1H, J = 9.77, H-3/4), 5.17 (d, 1H, J = 3.36, H-1)): δ(¹³C) 44.0, 73.6, 73.8, 74.9, 75.0, 95.4. IR (KBr, cm⁻¹): 3544–3315, 2930, 2904, 1638, 1615, 1382, 1155, 1105, 1087, 1038, 1016, 986, 939.

2.2. Data collection, structure solution and refinement

Diffraction data for (5)–(9) were collected at 120 (2) K using a Nonius Kappa-CCD diffractometer, using graphite-monochromated Mo Kα radiation (λ = 0.71073 Å). Other details of cell data, data collection and refinement are summarized in Table 1, together with details of the software employed (Ferguson, 1999; Nonius, 1997; Otwinowski & Minor, 1997; Sheldrick, 1997a,b; Spek, 2003).

Table 1
Experimental details

	(5)	(6)	(7)	(8)	(9)
Crystal data
Chemical formula	C26H38O21S2	C38H46O21S2	C24H32N6O15·0.35C2H6O	C24H36N2O15·2H2O	C12H24N2O9·2H2O
Mr	750.68	902.89	660.68	628.58	376.36
Cell setting, space group	Monoclinic, C2	Orthorhombic, P212121	Orthorhombic, P212121	Orthorhombic, P21212	Tetragonal, P43212
a, b, c (Å)	21.3279 (8), 8.9299 (4), 8.8382 (4)	18.1484 (9), 21.1046 (9), 23.4224 (14)	12.2281 (4), 15.5803 (6), 18.1066 (8)	8.8385 (2), 21.8363 (8), 8.0831 (2)	8.6093 (2), 8.6093 (2), 22.1566 (8)
β (°)	99.4537 (17)	90.00	90.00	90.00	90.00
V (Å^3)	1660.43 (12)	8971.1 (8)	3449.6 (2)	1560.04 (8)	1642.25 (8)
Z	2	8	4	2	4
Dx (Mg m^−3)	1.501	1.337	1.272	1.338	1.522
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα	Mo Kα
No. of reflections for cell parameters	3048	14 269	4368	2067	1163
θ range (°)	3.3–27.5	3.0–24.4	3.1–27.5	2.5–27.5	3.0–27.5
μ (mm^−1)	0.25	0.20	0.11	0.11	0.13
Temperature (K)	120 (2)	120 (2)	150 (2)	120 (2)	120 (2)
Crystal form, colour	Block, colourless	Lath, colourless	Block, colourless	Block, colourless	Block, colourless
Crystal size (mm)	0.30 × 0.25 × 0.15	0.30 × 0.10 × 0.02	0.50 × 0.30 × 0.25	0.30 × 0.20 × 0.15	0.15 × 0.15 × 0.10
Data collection
Diffractometer	Kappa-CCD	Kappa-CCD	Kappa-CCD	Kappa-CCD	Kappa-CCD
Data collection method	φ scans, and ω scans with κ offsets	φ scans, and ω scans with κ offsets	φ scans, and ω scans with κ offsets	φ scans, and ω scans with κ offsets	φ scans, and ω scans with κ offsets
Absorption correction	Multi-scan	Multi-scan	Multi-scan	Multi-scan	Multi-scan
Tmin	0.934	0.949	0.942	0.960	0.972
Tmax	0.964	0.996	0.974	0.983	0.987
No. of measured, independent and observed reflections	6104, 3048, 2781	34 701, 14 269, 8221	17 686, 4368, 2580	13 388, 2067, 1658	8561, 1163, 951
Criterion for observed reflections	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)	I > 2σ(I)
Rint	0.059	0.110	0.104	0.091	0.055
θmax (°)	27.5	25.0	27.5	27.5	27.5
Range of h, k, l	−27 → h → 26	−20 → h → 20	−12 → h → 15	−11 → h → 11	−9 → h → 11
	−10 → k → 11	−24 → k → 24	−18 → k → 20	−28 → k → 27	−11 → k → 11
	−11 → l → 11	−26 → l → 26	−23 → l → 23	−9 → l → 10	−20 → l → 28
Refinement
Refinement on	F^2	F^2	F^2	F^2	F^2
R[F^2 > 2σ(F^2)], wR(F^2), S	0.051, 0.145, 1.05	0.060, 0.136, 0.96	0.070, 0.191, 0.99	0.055, 0.148, 1.12	0.043, 0.126, 0.98
No. of reflections	3048	14 269	4368	2067	1163
No. of parameters	227	1113	439	215	115
H-atom treatment	Constrained to parent site	Constrained to parent site	Constrained to parent site	Constrained to parent site	Constrained to parent site
Weighting scheme	w = 1/[σ^2(Fo^2) + (0.1014P)^2], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0479P)^2], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.1153P)^2], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0967P)^2 + 0.0109P], where P = (Fo^2 + 2Fc^2)/3	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.9377P], where P = (Fo^2 + 2Fc^2)/3
(Δ/σ)max	<0.0001	0.001	<0.0001	<0.0001	<0.0001
Δρmax, Δρmin (e Å^−3)	0.48, −0.62	0.86, −0.28	0.43, −0.43	0.47, −0.41	0.24, −0.35
Extinction method	SHELXL	None	None	None	None
Extinction coefficient	0.0065 (18)	–	–	–	–
Absolute structure	Flack (1983), 1018 Friedel pairs	Flack (1983), 6179 Friedel pairs	–	–	–
Flack parameter	0.16 (10)	−0.02 (8)	–	–	–
Computer programs used: Kappa-CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SHELXS97 (Sheldrick, 1997b), SHELXL97 (Sheldrick, 1997a), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

For (5) the systematic absences permitted C2 and Cm as possible space groups: in view of the enantiopure nature of the chiral compound, the space group C2 was selected and confirmed by the analysis. For each of (6) and (7) the space group P2₁2₁2₁ was uniquely assigned from the systematic absences: similarly P2₁2₁2 was uniquely assigned for (8). For (9) the systematic absences permitted one of the enantiomeric pair P4₁2₁2 and P4₃2₁2: space group P4₃2₁2 was selected by reference to the known absolute configuration of the compound. The structures were all solved by direct methods and refined with all data on F². A weighting scheme based upon P = [F_o² + 2F_c²]/3 was employed in order to reduce the statistical bias (Wilson, 1976). In (5), (8) and (9) the disaccharide unit lies across a twofold rotation axis, while in (6) there are two independent disaccharide molecules in the asymmetric unit. In (7) there is a partially occupied ethanol: when the C and O atoms of this unit were refined isotropically, the site-occupancy factor refined to 0.35 (2). Thereafter this occupancy was fixed at 0.35, while the C and O atoms were refined anisotropically. In all the compounds the absolute structure was set from the known absolute configuration of the enantiopure chiral α,α′-trehalose starting material: in the case of (5) and (6) this was confirmed by the values of the Flack parameter (Flack, 1983), 0.16 (10) and −0.02 (8), respectively. For (7)–(9) the absence of any significant anomalous scatterers meant that the Flack parameters for these compounds [values 4.1 (18), −0.1 (17) and 0 (3), respectively] were inconclusive (Flack & Bernardinelli, 2000): hence the Friedel-equivalent reflections were merged prior to the final refinements of (7)–(9). All H atoms were located in difference maps and in (5)–(8) they were fully ordered. The H atoms bonded to C atoms were all treated as riding atoms with distances 0.95 Å (aromatic), 0.98 Å (CH₃), 0.99 Å (CH₂) or 1.00 Å (aliphatic CH). The H atoms bonded to N or O in (8) were allowed to ride on their parent atoms at the positions found from the difference maps, with distances N—H 0.81 Å; O—H 0.82 Å (in the trehalose component) and 0.96 and 0.98 Å in the water molecule. In (9) the H atoms bonded to O2 and O4 in the trehalose component were both modelled as riding atoms using two sites with 0.50 occupancy and O—H distances of 0.84 Å; the H atoms bonded to N were allowed to ride at the positions found from the difference maps with N—H distances 0.95 and 1.00 Å; the H atoms of the water molecule were likewise allowed to ride at the positions found from the difference maps with O—H distances 0.94 and 0.99 Å. Examination of the refined structures using PLATON (Spek, 2003) showed small voids in (6), each of volume ca 37 ų; however, these contained no significant electron density as they are probably too small to accommodate even a water molecule.

Supramolecular analyses were made and the diagrams were prepared with the aid of PLATON. The pyranose ring-puckering parameters are given in Table 2 and parameters for selected hydrogen bonds are given in Table 3.¹ Figs. 1–15 show the molecular aggregates, with the atom-labelling schemes, and aspects of the supramolecular structures.

Table 2
Ring-puckering parameters for pyranose rings (Å, ^o)

Ring-puckering parameters are for the atom sequence (O5, C1, C2, C3, C4, C5).

	Q (Å)	θ (°)	φ (°)
(1)	0.549 (2)	4.5 (3)	14 (3)
	0.563 (2)	4.3 (3)	106 (4)
(2)	0.56 (1)	9 (1)	94 (7)
	0.57 (1)	3 (1)	322 (21)
(3)	0.592 (2)	4.5 (2)	246 (2)
(4)	0.571 (5)	4.5 (5)	319 (5)
	0.568 (5)	5.5 (5)	317 (5)
(5)	0.579 (3)	4.9 (3)	122 (4)
(6)	0.553 (5)	3.9 (5)	11 (7)
	0.544 (5)	5.5 (5)	354 (5)
	0.554 (5)	6.3 (5)	357 (5)
	0.569 (5)	4.4 (5)	308 (7)
(7)	0.558 (4)	8.7 (4)	332 (3)
	0.546 (5)	5.1 (5)	347 (6)
(8)	0.567 (3)	8.4 (3)	75 (2)
(9)	0.580 (3)	4.3 (3)	245 (4)

Table 3
Selected hydrogen-bond parameters (Å, °)

D—H⋯A	H⋯A	D⋯A	D—H⋯A
(5)
C6—H6A⋯O61^i	2.43	3.221 (4)	136
(6)
C4C—H4C⋯O41D^ii	2.46	3.365 (7)	150
C6C—H6F⋯O41D^ii	2.49	3.272 (6)	136
C55C—H55C⋯O31B^iii	2.41	3.313 (7)	160
C53D—H53D⋯Cg1^iv†	2.66	3.418 (7)	137
(7)
C6A—H6B⋯O41B^v	2.32	3.268 (6)	160
C6B—H6C⋯O31A^vi	2.48	3.363 (8)	149
C6B—H6D⋯O41A^vii	2.52	3.400 (7)	148
(8)
N1—H1A⋯O6W	2.05	2.835 (4)	165
O4—H4A⋯O61^vi	1.81	2.606 (3)	162
O6W—H6C⋯O31^viii	2.21	3.009 (4)	137
O6W—H6D⋯O4^ix	1.93	2.865 (3)	164
(9)
O3—H3A⋯N1^iii	1.88	2.711 (3)	168
O4—H4B⋯O4^x	2.01	2.833 (3)	165
O6W—H6C⋯O3	1.74	2.667 (3)	155
O6W—H6D⋯O6W^x	1.75	2.733 (5)	165
Symmetry codes: (i) ; (ii) ; (iii) x, 1 + y, z; (iv) ; (v) ; (vi) ; (vii) ; (viii) 1 - x, 1 - y, -1 + z; (ix) x, y, -1 + z; (x) .

†Cg1 is the centroid of the ring C51C–C56C.

Figure 1 The molecule of (5) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The atoms marked `a' are at the symmetry position (1 - x, y, 1 - z). For the sake of clarity the H atoms have been omitted.

Figure 2 Stereoview of part of the crystal structure of (5) showing the formation of a (001) sheet of R^44(36) rings. For the sake of clarity, the H atoms bonded to C atoms but not taking part in the motif shown are omitted.

Figure 3 The two independent molecules of (6) showing the atom-labelling scheme: (a) molecule A; (b) molecule B. Displacement ellipsoids are drawn at the 30% probability level. For the sake of clarity the H atoms have been omitted.

Figure 4 Stereoview of part of the crystal structure of (6), showing the formation of a C(13)C(13)[R^12(6)] chain of rings along [100]. For the sake of clarity, the H atoms bonded to C atoms but not taking part in the motif shown are omitted.

Figure 5 Stereoview of part of the crystal structure of (6) showing the formation of a chain along [001] generated by the C—H⋯π(arene) hydrogen bond. For the sake of clarity, the H atoms bonded to C atoms but not taking part in the motif shown are omitted.

Figure 6 The trehalose molecule of (7) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. For the sake of clarity, the partial ethanol solvate molecule is omitted.

Figure 7 Stereoview of part of the crystal structure of (7) showing the formation of a C(12) helical chain along [100]. For the sake of clarity the ethanol molecule is omitted and the H atoms bonded to C atoms but not taking part in the motif shown are omitted.

Figure 8 Stereoview of part of the crystal structure of (7) showing the formation of a chain of rings along [001]. For the sake of clarity the ethanol molecule is omitted and the H atoms bonded to C atoms but not taking part in the motif shown are omitted.

Figure 9 Stereoview of part of the crystal structure of (7) showing the formation of a chain along [010]. For the sake of clarity the ethanol molecule is omitted and the H atoms bonded to C atoms but not taking part in the motif shown are omitted.

Figure 10 The molecule of (8), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The atoms marked `a' are at the symmetry position (1 - x, 1 - y, z).

Figure 11 Stereoview of part of the crystal structure of (8) showing the formation of a (001) sheet of R4^4(44) rings. For the sake of clarity the water molecule is omitted, as are the H atoms bonded to C atoms.

Figure 12 Stereoview of part of the crystal structure of (8) showing the formation of a molecular ladder along [001]. For the sake of clarity, the H atoms bonded to C atoms are omitted.

Figure 13 The independent molecular components of compound (9) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. The atoms marked `a' are at the symmetry position (y, x, -z).

Figure 14 Stereoview of part of the crystal structure of (9) showing the formation of a (001) sheet of R4^4(44) rings. For the sake of clarity the water molecule is omitted, as are the H atoms bonded to C atoms.

Figure 15 Stereoview of part of the crystal structure of (9) showing the formation of a chain of rings along [001], which links the (001) sheets. For the sake of clarity, the H atoms bonded to C atoms are omitted.

3. Results and discussion

3.1. Pyranose ring conformations

For each of (5)–(9) the ring-puckering parameters for the pyranose rings, corresponding to the atom sequence (O5, C1, C2, C3, C4, C5) for each independent ring, are collected in Table 2, along with those for the previously published structures of (1)–(4) by way of comparison. It is clear that the gross conformations of these rings are largely independent both of the degree of substitution and of the steric bulk of the substituents. In every case the value of the parameter θ is less than 10°, indicating only a small distortion of the ring shape from the expected chair conformation; a regular chair conformer of exact D_3d(m) symmetry has a θ value of zero (Boeyens, 1978).

Consistent with this deduction, the total puckering amplitude Q lies in the range 0.54–0.58 Å for (5)–(9), only a little less than the Q value of 0.63 Å calculated for the chair conformer of cyclohexane. However, the φ values in (5)–(9) are all close to N × 60°, where N takes the values N = 2 in (5), N = 0, 5 or 6 in (6), N = 6 in (7), N = 1 in (8) and N = 4 in (9), indicating that the distortions from the chair conformation are all towards the boat conformation. Thus, the rings are slightly flattened, allowing the ring angle C—O—C to increase somewhat beyond the tetrahedral angle: in fact, in (5)–(9) the ring C—O—C angles lie in the range 113.0 (3)° for ring A in (7) to 114.9 (4)° for ring D of (6), with a mean value of ca 113.7°.

Similar distortions of the chair conformation towards the boat form are also evident in (1), (3) and (4), although in (2) the uncertainties associated with the φ values preclude any analysis of the nature of the ring distortion in this compound.

3.2. Supramolecular structures

Where amino or hydroxyl groups are available, as in (8) and (9), the supramolecular aggregation is dominated by hard (Braga et al., 1995; Desiraju & Steiner, 1999) hydrogen bonds of O—H⋯O, O—H⋯N and N—H⋯O types, and where these are present, the supramolecular structures are three dimensional. In derivatives where hard hydrogen bonds are not possible, soft hydrogen bonds of C—H⋯O type become dominant, giving a two-dimensional structure in (5) or three-dimensional structures as in (6) and (7). The structures of most of the compounds described here exhibit a substantial number of C—H⋯O contacts in which the H⋯O distances are close to the sum of their van der Waals radii. In general, we have considered only C—H⋯O interactions where the H⋯O distance is less than 2.55 Å and where the C—H⋯O angle exceeds 135°; however, contacts involving methyl groups have been discounted because of the rotational properties of these groups. Furthermore, because of the large numbers of contacts present, we have considered only the minimum numbers of the strongest interactions which suffice to define the dimensionality of the supramolecular structures.

3.2.1. Compound (5)

Molecules of (5) (Fig. 1) lie across the rotation axes in the space group C2 and the reference molecule was selected as that across the axis along (½, y, ½). A single C—H⋯O=S hydrogen bond (Table 3) links the molecules into sheets in which each molecule acts as a double donor and as a double acceptor of hydrogen bonds, such that each molecule is linked to four others. Atom C6 at (x, y, z), which is adjacent to the very electronegative sulfonyl unit, and which forms part of the molecule across the axis along (½, y, ½), acts as a hydrogen-bond donor, via H6A, to sulfonyl O61 at (½ − x, ½ + y, 1 − z), which forms part of the molecule whose central atom O1 is at (0, ½ + y, ½). Similarly, O61 at (x, y, z) accepts a hydrogen bond from C6 at (½ − x, −½ + y, 1 − z), part of the molecule whose O1 atom is at (0, −½ + y, ½). Propagation of this hydrogen bond by rotation then generates a deeply puckered (001) sheet in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of R₄⁴(36) (Bernstein et al., 1995) ring (Fig. 2).

There are no direction-specific interactions between adjacent sheets, but there is one rather short non-bonded contact, probably attractive, within the sheet. The atoms O31 at (x, y, z) and C61 at (1 - x, 1 + y, 1 - z) are separated by only 2.973 (4) Å, rather less than the sum of the van der Waals radii, 3.22 Å (Bondi, 1964): since O31 is a carbonyl O, while methyl C61 is bonded to a sulfonyl group, these two atoms will be polarized as O^δ− and C^δ+. Since the methyl group is almost certainly undergoing rapid rotation about the C—S bond, the associated C—H⋯O interaction is unlikely to be structurally significant.

3.2.2. Compound (6)

Although (6) is very similar in chemical type to (5), both its crystallization behaviour and its supramolecular structure are rather different. Compound (6) (Fig. 3) crystallizes with Z′ = 2 in space group P2₁2₁2₁ [cf. Z′ = 0.5 in C2 for (5)] and its supramolecular structure is based on a combination of three C—H⋯O hydrogen bonds, with carbonyl O, rather than sulfonyl O, as the acceptor in each, together with a C—H⋯π(arene) hydrogen bond (Table 3). On the other hand, aromatic π⋯π stacking interactions are absent from the structure of (6).

The molecules of type B, with O1B as the central atom, form a single three-dimensional framework from which the type A molecules, having O1A as the central atom, are pendent. The formation of the framework structure is most readily analysed in terms of the one-dimensional sub-structures (Gregson et al., 2000) generated by the C—H⋯O and C—H⋯π(arene) hydrogen bonds in turn.

In the type B molecule at (x, y, z), atoms C4C and C6C both act as hydrogen-bond donors, via H4C and H6F, respectively, to carbonyl atom O41D in the type B molecule at (−½ + x, − y, −z), so producing a C(13)C(13)[R¹₂(6)] chain of rings running parallel to the [100] direction and generated by the 2₁ screw axis along (x, ¾, 0) (Fig. 4). A second, antiparallel chain of this type is generated by the 2₁ axis along (−x, ¼, ½). The [100] chain is modestly reinforced by a dipolar interaction between nearly antiparallel carbonyl groups. The carbonyl group C21C—O21C in the type B molecule at (x, y, z) and the carbonyl group C21D—O21D in the type B molecule at (−½ + x, − y, −z) lie in the same [100] chain of rings: the O21C⋯C21Dⁱ and C21C⋯O21Dⁱ distances [symmetry code: (i) ] are 2.958 (7) and 3.221 (7) Å, so forming a nearly rhomboidal type II (Allen et al., 1998) interaction.

The C—H⋯π(arene) hydrogen bond also involves only the type B molecules and it gives rise to a chain parallel to [001]. The phenyl atom C53D in the type B molecule at (x, y, z) acts as a hydrogen-bond donor to the phenyl ring C51C—C56C in the type B molecule at (), giving a chain generated by the 2₁ screw axis along (¼, 1, z) (Fig. 5). The combination of the [100] and [001] chains, when propagated by the space group generates a continuous three-dimensional framework of type B molecules, to which the type A molecules are linked via a third C—H⋯O hydrogen bond. The phenyl atom C55C in the type B molecule at (x, y, z) acts as a hydrogen-bond donor to the carbonyl O31B atom in the type A molecule at (x, 1 + y, z): had the asymmetric unit been selected so that the two independent molecules were linked within it by this C—H⋯O hydrogen bond, one of the molecules would necessarily have fallen entirely outside the unit cell.

3.2.3. Compound (7)

Compound (7) crystallizes as a partial ethanol solvate in the space group P2₁2₁2₁ (Fig. 6): because of the low occupancy, 0.35, of the ethanol sites, only the interactions between disaccharide molecules will be discussed. The supramolecular aggregation is dominated by three C—H⋯O hydrogen bonds (Table 3), all involving ring C—H bonds as donors and carbonyl O as acceptors; together they link the molecules into a continuous three-dimensional framework.

Atom C6B in the molecule at (x, y, z) acts as a hydrogen-bond donor, via H6C, to the carbonyl atom O31A in the molecule at (), so forming a simple C(12) chain running parallel to the [100] direction, and generated by the 2₁ screw axis along (x, ¼, ½) (Fig. 7). A second chain of this type, antiparallel to the first, is generated by the 2₁ axis along (−x, ¾, 0).

In a more complex motif, atoms C6A and C6B in the molecule at (x, y, z) act as hydrogen-bond donors, via H6B and H6D, respectively, to the carbonyl O atoms O41B in the molecule at () and O41A in the molecule at () so forming a C(13)C(13)[R₂²(14)] chain of rings running parallel to the [001] direction and which is generated by the 2₁ screw axis along (¾, ½, z) (Fig. 8). A second chain of this type, antiparallel to the first, is generated by the 2₁ axis along (¼, 0, −z).

The [100] and [001] chains are each generated by the repetition of just one of the interactions described above: the combination of the two interactions together generates a chain running parallel to the [010] direction (Fig. 9), and the combination of the [100], [010] and [001] chains generates the three-dimensional framework structure.

3.2.4. Compound (8)

In (8) the substituted trehalose molecules lie across a twofold rotation axis in the space group P2₁2₁2, selected for the reference molecule as that along (½, ½, z), while the water molecule lies in a general position. In the selected asymmetric unit the water molecule is linked to the disaccharide by means of an N—H⋯O hydrogen bond (Table 3), so forming a compact three-molecule aggregate (Fig. 10). The supramolecular aggregation is then determined by the six hydroxyl or water O—H bonds available in each three-molecule aggregate for external hydrogen-bond formation. The construction of the resulting three-dimensional framework structure can then most readily be analysed in terms of the effect of each distinct hydrogen bond in turn.

The hydroxyl O4 atoms at (x, y, z) and (1 - x, 1 - y, z) both lie in the reference disaccharide molecule whose central atom O1 lies at (½, ½, z). These two hydroxyl atoms act as hydrogen-bond donors, respectively, to atoms O61 at (−½ + x, ½ − y, 1 − z) and at ( − x, ½ + y, 1 − z), which themselves lie in molecules whose central atoms are at (0, 0, 1 − z) and (1, 1, 1 − z), respectively. Similarly, the two atoms of type O61 in the reference molecule across (½, ½, z) accept hydrogen bonds from the O4 atoms at (½ + x, ½ − y, 1 − z) and (½ − x, ½ + y, 1 − z), which lie, respectively, in molecules where the O1 atoms are at (1, 0, 1 − z) and (0, 1, 1 − z). In this manner, a single O—H⋯O hydrogen bond generates a (001) sheet in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of R₄⁴(44) ring (Fig. 11).

The (001) sheets are formed solely by the disaccharide components and they are linked into a three-dimensional framework by the water molecules. The water atom O6W at (x, y, z) acts as a hydrogen-bond donor, via H6D, to the hydroxyl atom O4 at (x, y, -1 + z), so generating by translation a C²₂(8) chain parallel to the [001] direction, and the action of the twofold rotation axis converts this chain into a molecular ladder, in which parallel C₂²(8) chains act as the uprights and the disaccharide molecules as the rungs (Fig. 12). The combination of the [001] chains with the (001) sheets is sufficient to produce a three-dimensional structure, but this is further reinforced by a third O—H⋯O hydrogen bond. The water atom O6W at (x, y, z), which lies in the reference (001) sheet, acts as a hydrogen-bond donor via H6C to the acetato atom O31 at (1 - x, 1 - y, -1 + z), which lies in the adjacent sheet along [001], again linking adjacent sheets.

3.2.5. Compound (9)

The diaminotrehalose molecules in (9) lie across twofold rotation axes in the space group P4₃2₁2, selected for the reference molecule as that having z = 0, x = y; there is also a water molecule lying in a general position and in the selected asymmetric unit (Fig. 13) this water molecule is linked to the disaccharide via an O—H⋯O hydrogen bond (Table 3). With no acyl substituents present, there is an extensive series of hydrogen bonds present in the structure, encompassing O—H⋯O, O—H⋯N and N—H⋯O types. However, the three-dimensional nature of the supramolecular structure can be readily established in terms of just two hydrogen bonds, in addition to that within the asymmetric unit; one of these hydrogen bonds generates sheets and the second links the sheets into a three-dimensional framework. The other hydrogen bonds can be regarded as reinforcing elaborations.

The hydroxyl atom O3 at (x, y, z) acts as a hydrogen-bond donor to the amino atom N1 at (x, 1 + y, z), so generating by translation a C(7) chain running parallel to the [010] direction: the action of the twofold axes through the molecules generates a similar chain running parallel to the [100] direction and the combination of these two chain motifs generates a (001) sheet in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of R⁴₄(44) ring and involving only a single O—H⋯N hydrogen bond (Fig. 14). It may be noted here that although the gross topology of the (001) sheets in (8) and (9) is the same, the sheet in (8) is generated by a combination of twofold rotation and screw axes, whereas that in (9) is generated by a combination of translation and twofold rotation axes.

There are two interactions which link the (001) sheets into a continuous framework. Atom O4 at (x, y, z) lies in the (001) sheet whose twofold rotation axes are at z = 0; this atom acts as a hydrogen-bond donor, via H4B, to O4 at (), which lies in the sheet with its axes at z = ½. Although the occupancy of the H4B site is only 0.5, there is no necessary correlation between the occupancy of the H4A and H4B sites throughout a given sheet and hence 50% of the H4B sites in any sheet will be available to form this hydrogen bond. In an entirely similar way, the water atom O6W, which is linked to the z = 0 sheet via O3 (Table 3), acts as a hydrogen-bond donor, via H6D, to O6W at (), which is linked to the sheet at z = ½. Propagation of these interactions by rotation and translation then links each (001) sheet to the two adjacent sheets, forming a chain of rings along the [001] direction (Fig. 15).

4. Concluding comments

It is striking how little the conformations of the pyranose rings in substituted α,α′-trehalose molecules are affected either by the extent of the substitution or by the steric bulk of the substituents: this is clearly illustrated at the extremes of the range of substitution considered here by (3) and (9) [see (I)], where the ring-puckering behaviour is essentially identical for the two compounds. On the other hand, the direction-specific intermolecular forces are very strongly influenced by the substitution pattern, with (4)–(9) forming a supramolecular structure (4) in one dimension, (5) in two dimensions and (6)–(9) three dimensions, while (1)–(3) contain effectively isolated molecules.

Supporting information

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

In full text version

(5) 2,2',3,3',4,4'-Hexaacetato-6,6'-bis-O-methylsulfonyl-α,α'-trehalose

Crystal data

C26H38O21S2	F(000) = 788
Mr = 750.68	Dx = 1.501 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3048 reflections
a = 21.3279 (8) Å	θ = 3.3–27.5°
b = 8.9299 (4) Å	µ = 0.25 mm^−1
c = 8.8382 (4) Å	T = 120 K
β = 99.4537 (17)°	Block, colourless
V = 1660.43 (12) Å^3	0.30 × 0.25 × 0.15 mm
Z = 2

Data collection

Kappa-CCD diffractometer	3048 independent reflections
Radiation source: rotating anode	2781 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −27→26
Tmin = 0.934, Tmax = 0.964	k = −10→11
6104 measured reflections	l = −11→11

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.1014P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.145	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.48 e Å^−3
3048 reflections	Δρmin = −0.62 e Å^−3
227 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0065 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1018 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.16 (10)

Special details

Experimental. ?.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.48997 (13)	0.6069 (4)	0.3623 (3)	0.0165 (6)
C2	0.48718 (13)	0.7206 (4)	0.2339 (3)	0.0179 (7)
C3	0.43143 (13)	0.8265 (4)	0.2393 (3)	0.0160 (6)
C4	0.37131 (13)	0.7332 (4)	0.2258 (3)	0.0170 (6)
C5	0.37716 (13)	0.6118 (3)	0.3488 (3)	0.0169 (6)
O5	0.43313 (9)	0.5223 (3)	0.3446 (2)	0.0172 (5)
O4	0.32153 (9)	0.8347 (3)	0.2519 (2)	0.0190 (5)
C41	0.26512 (14)	0.8250 (4)	0.1554 (4)	0.0205 (7)
C42	0.22101 (15)	0.9469 (4)	0.1858 (4)	0.0259 (7)
O41	0.25405 (11)	0.7303 (4)	0.0591 (3)	0.0346 (6)
O3	0.42296 (10)	0.9264 (3)	0.1097 (2)	0.0189 (5)
C31	0.43967 (14)	1.0730 (4)	0.1390 (4)	0.0219 (7)
C32	0.41495 (17)	1.1692 (4)	0.0048 (4)	0.0305 (8)
O31	0.46981 (11)	1.1150 (3)	0.2575 (3)	0.0283 (6)
O2	0.54540 (9)	0.8073 (3)	0.2558 (2)	0.0188 (5)
C21	0.59471 (14)	0.7434 (4)	0.1995 (3)	0.0208 (7)
O21	0.58974 (10)	0.6302 (3)	0.1271 (3)	0.0256 (5)
C22	0.65478 (15)	0.8328 (5)	0.2437 (4)	0.0283 (8)
O1	0.5000	0.6900 (3)	0.5000	0.0176 (7)
C6	0.32139 (15)	0.5049 (4)	0.3221 (4)	0.0204 (7)
O6	0.32225 (11)	0.4119 (3)	0.4579 (3)	0.0244 (5)
S1	0.33306 (4)	0.23747 (10)	0.45198 (9)	0.0242 (2)
C61	0.41110 (16)	0.2172 (5)	0.5466 (4)	0.0287 (8)
O61	0.29125 (12)	0.1756 (3)	0.5459 (3)	0.0392 (7)
O62	0.32804 (12)	0.1905 (3)	0.2964 (3)	0.0312 (6)
H1	0.5268	0.5381	0.3601	0.020*
H2	0.4817	0.6682	0.1326	0.021*
H3	0.4380	0.8846	0.3374	0.019*
H4	0.3611	0.6877	0.1213	0.020*
H5	0.3798	0.6593	0.4521	0.020*
H42A	0.2301	1.0378	0.1310	0.039*
H42B	0.2269	0.9674	0.2961	0.039*
H42C	0.1770	0.9157	0.1501	0.039*
H32A	0.3684	1.1713	−0.0096	0.046*
H32B	0.4287	1.1284	−0.0874	0.046*
H32C	0.4315	1.2711	0.0230	0.046*
H22A	0.6739	0.8085	0.3494	0.042*
H22B	0.6448	0.9399	0.2362	0.042*
H22C	0.6847	0.8082	0.1744	0.042*
H6A	0.2811	0.5621	0.3014	0.025*
H6B	0.3242	0.4410	0.2320	0.025*
H61A	0.4159	0.2675	0.6464	0.043*
H61B	0.4403	0.2623	0.4847	0.043*
H61C	0.4210	0.1106	0.5618	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0130 (13)	0.0192 (16)	0.0167 (14)	0.0019 (12)	0.0007 (11)	−0.0027 (13)
C2	0.0163 (14)	0.0199 (16)	0.0169 (15)	−0.0007 (13)	0.0012 (11)	0.0004 (13)
C3	0.0159 (14)	0.0173 (15)	0.0147 (14)	0.0005 (13)	0.0020 (11)	0.0034 (13)
C4	0.0174 (14)	0.0163 (14)	0.0169 (14)	0.0032 (14)	0.0016 (10)	−0.0037 (14)
C5	0.0162 (13)	0.0175 (16)	0.0163 (14)	0.0042 (12)	0.0007 (11)	−0.0018 (12)
O5	0.0153 (10)	0.0165 (11)	0.0192 (11)	0.0003 (9)	0.0012 (8)	−0.0006 (9)
O4	0.0164 (10)	0.0179 (11)	0.0223 (11)	0.0034 (10)	0.0019 (8)	−0.0011 (10)
C41	0.0175 (14)	0.0208 (16)	0.0226 (16)	0.0034 (14)	0.0018 (12)	0.0016 (15)
C42	0.0212 (16)	0.0225 (17)	0.0332 (19)	0.0039 (14)	0.0017 (13)	−0.0006 (15)
O41	0.0268 (12)	0.0408 (15)	0.0323 (13)	0.0085 (13)	−0.0071 (10)	−0.0157 (14)
O3	0.0210 (10)	0.0182 (11)	0.0168 (11)	−0.0003 (10)	0.0004 (8)	0.0041 (9)
C31	0.0168 (15)	0.0166 (16)	0.0334 (19)	−0.0012 (13)	0.0079 (13)	−0.0006 (14)
C32	0.0304 (19)	0.0276 (19)	0.0323 (19)	−0.0007 (16)	0.0012 (14)	0.0121 (17)
O31	0.0262 (11)	0.0232 (13)	0.0339 (14)	−0.0001 (10)	0.0003 (10)	−0.0028 (11)
O2	0.0121 (10)	0.0225 (12)	0.0223 (11)	−0.0006 (9)	0.0041 (8)	−0.0025 (9)
C21	0.0189 (15)	0.0267 (18)	0.0167 (14)	0.0043 (15)	0.0022 (11)	0.0047 (15)
O21	0.0242 (11)	0.0252 (13)	0.0282 (13)	0.0035 (10)	0.0062 (9)	−0.0052 (11)
C22	0.0185 (15)	0.0338 (19)	0.0322 (18)	−0.0017 (15)	0.0030 (13)	0.0002 (16)
O1	0.0177 (15)	0.0187 (16)	0.0152 (15)	0.000	−0.0009 (11)	0.000
C6	0.0207 (15)	0.0197 (16)	0.0208 (16)	0.0032 (13)	0.0027 (12)	0.0036 (14)
O6	0.0330 (12)	0.0164 (12)	0.0253 (12)	0.0010 (10)	0.0087 (10)	0.0042 (10)
S1	0.0225 (4)	0.0189 (4)	0.0310 (5)	−0.0012 (3)	0.0038 (3)	0.0041 (4)
C61	0.0259 (16)	0.031 (2)	0.0279 (17)	0.0031 (15)	−0.0004 (13)	0.0033 (15)
O61	0.0334 (14)	0.0284 (14)	0.0592 (19)	−0.0037 (11)	0.0181 (13)	0.0114 (14)
O62	0.0327 (14)	0.0230 (14)	0.0345 (14)	0.0007 (10)	−0.0042 (10)	−0.0036 (11)

Geometric parameters (Å, º)

C1—O1	1.412 (3)	C31—O31	1.196 (4)
C1—O5	1.415 (4)	C31—C32	1.489 (5)
C1—C2	1.517 (4)	C32—H32A	0.98
C1—H1	1.00	C32—H32B	0.98
C2—O2	1.449 (4)	C32—H32C	0.98
C2—C3	1.526 (4)	O2—C21	1.360 (4)
C2—H2	1.00	C21—O21	1.192 (4)
C3—O3	1.440 (4)	C21—C22	1.506 (5)
C3—C4	1.517 (4)	C22—H22A	0.98
C3—H3	1.00	C22—H22B	0.98
C4—O4	1.443 (4)	C22—H22C	0.98
C4—C5	1.526 (4)	O1—C1^i	1.412 (3)
C4—H4	1.00	C6—O6	1.457 (4)
C5—O5	1.442 (3)	C6—H6A	0.99
C5—C6	1.513 (4)	C6—H6B	0.99
C5—H5	1.00	O6—S1	1.577 (3)
O4—C41	1.359 (4)	S1—O62	1.425 (3)
C41—O41	1.196 (4)	S1—O61	1.426 (3)
C41—C42	1.492 (5)	S1—C61	1.745 (3)
C42—H42A	0.98	C61—H61A	0.98
C42—H42B	0.98	C61—H61B	0.98
C42—H42C	0.98	C61—H61C	0.98
O3—C31	1.371 (4)
O1—C1—O5	112.4 (2)	C31—O3—C3	116.5 (2)
O1—C1—C2	105.9 (3)	O31—C31—O3	123.4 (3)
O5—C1—C2	110.3 (2)	O31—C31—C32	125.9 (3)
O1—C1—H1	109.4	O3—C31—C32	110.7 (3)
O5—C1—H1	109.4	C31—C32—H32A	109.5
C2—C1—H1	109.4	C31—C32—H32B	109.5
O2—C2—C1	109.3 (2)	H32A—C32—H32B	109.5
O2—C2—C3	108.7 (3)	C31—C32—H32C	109.5
C1—C2—C3	109.0 (2)	H32A—C32—H32C	109.5
O2—C2—H2	109.9	H32B—C32—H32C	109.5
C1—C2—H2	109.9	C21—O2—C2	115.1 (3)
C3—C2—H2	109.9	O21—C21—O2	123.1 (3)
O3—C3—C4	106.5 (2)	O21—C21—C22	125.9 (3)
O3—C3—C2	110.8 (2)	O2—C21—C22	111.0 (3)
C4—C3—C2	108.1 (3)	C21—C22—H22A	109.5
O3—C3—H3	110.5	C21—C22—H22B	109.5
C4—C3—H3	110.5	H22A—C22—H22B	109.5
C2—C3—H3	110.5	C21—C22—H22C	109.5
O4—C4—C3	106.1 (3)	H22A—C22—H22C	109.5
O4—C4—C5	108.0 (2)	H22B—C22—H22C	109.5
C3—C4—C5	111.4 (2)	C1—O1—C1^i	116.5 (3)
O4—C4—H4	110.4	O6—C6—C5	109.2 (2)
C3—C4—H4	110.4	O6—C6—H6A	109.8
C5—C4—H4	110.4	C5—C6—H6A	109.8
O5—C5—C6	106.2 (2)	O6—C6—H6B	109.8
O5—C5—C4	110.3 (2)	C5—C6—H6B	109.8
C6—C5—C4	111.5 (2)	H6A—C6—H6B	108.3
O5—C5—H5	109.6	C6—O6—S1	121.2 (2)
C6—C5—H5	109.6	O62—S1—O61	119.53 (17)
C4—C5—H5	109.6	O62—S1—O6	109.56 (14)
C1—O5—C5	113.5 (2)	O61—S1—O6	104.76 (16)
C41—O4—C4	117.3 (2)	O62—S1—C61	110.27 (17)
O41—C41—O4	122.9 (3)	O61—S1—C61	108.62 (17)
O41—C41—C42	126.0 (3)	O6—S1—C61	102.68 (17)
O4—C41—C42	111.1 (3)	S1—C61—H61A	109.5
C41—C42—H42A	109.5	S1—C61—H61B	109.5
C41—C42—H42B	109.5	H61A—C61—H61B	109.5
H42A—C42—H42B	109.5	S1—C61—H61C	109.5
C41—C42—H42C	109.5	H61A—C61—H61C	109.5
H42A—C42—H42C	109.5	H61B—C61—H61C	109.5
H42B—C42—H42C	109.5
O1—C1—C2—O2	57.2 (3)	C3—C4—O4—C41	135.4 (3)
O5—C1—C2—O2	179.1 (2)	C5—C4—O4—C41	−105.1 (3)
O1—C1—C2—C3	−61.5 (3)	C4—O4—C41—O41	5.5 (5)
O5—C1—C2—C3	60.5 (3)	C4—O4—C41—C42	−173.9 (3)
O2—C2—C3—O3	67.0 (3)	C4—C3—O3—C31	134.6 (2)
C1—C2—C3—O3	−173.9 (2)	C2—C3—O3—C31	−108.1 (3)
O2—C2—C3—C4	−176.7 (2)	C3—O3—C31—O31	12.8 (4)
C1—C2—C3—C4	−57.6 (3)	C3—O3—C31—C32	−166.9 (3)
O3—C3—C4—O4	−68.4 (3)	C1—C2—O2—C21	84.3 (3)
C2—C3—C4—O4	172.6 (2)	C3—C2—O2—C21	−156.8 (2)
O3—C3—C4—C5	174.4 (2)	C2—O2—C21—O21	5.6 (4)
C2—C3—C4—C5	55.3 (3)	C2—O2—C21—C22	−173.4 (3)
O4—C4—C5—O5	−170.1 (2)	O5—C1—O1—C1^i	64.9 (2)
C3—C4—C5—O5	−54.0 (3)	C2—C1—O1—C1^i	−174.5 (2)
O4—C4—C5—C6	72.1 (3)	O5—C5—C6—O6	71.7 (3)
C3—C4—C5—C6	−171.8 (2)	C4—C5—C6—O6	−168.1 (2)
O1—C1—O5—C5	57.4 (3)	C5—C6—O6—S1	−115.1 (3)
C2—C1—O5—C5	−60.6 (3)	C6—O6—S1—O62	−11.8 (3)
C6—C5—O5—C1	177.8 (2)	C6—O6—S1—O61	−141.1 (2)
C4—C5—O5—C1	56.8 (3)	C6—O6—S1—C61	105.4 (2)

Symmetry code: (i) −x+1, y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O61^ii	0.99	2.43	3.221 (4)	136

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

(6) 2,2',3,3',4,4'-Hexaacetato-6,6'-bis-O-(4-toluenesulfonyl)-α,α'-trehalose

Crystal data

C38H46O21S2	F(000) = 3792
Mr = 902.89	Dx = 1.337 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14269 reflections
a = 18.1484 (9) Å	θ = 3.0–24.4°
b = 21.1046 (9) Å	µ = 0.20 mm^−1
c = 23.4224 (14) Å	T = 120 K
V = 8971.1 (8) Å^3	Lath, colourless
Z = 8	0.30 × 0.10 × 0.02 mm

Data collection

Kappa-CCD diffractometer	14269 independent reflections
Radiation source: rotating anode	8221 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.110
ϕ scans, and ω scans with κ offsets	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −20→20
Tmin = 0.949, Tmax = 0.996	k = −24→24
34701 measured reflections	l = −26→26

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0479P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max = 0.001
14269 reflections	Δρmax = 0.86 e Å^−3
1113 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Absolute structure: Flack (1983), 6179 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.2823 (2)	0.2825 (2)	0.0073 (2)	0.0240 (13)
C2A	0.3524 (3)	0.2477 (2)	−0.0090 (2)	0.0209 (12)
C3A	0.3628 (3)	0.1895 (2)	0.0276 (2)	0.0226 (13)
C4A	0.3566 (3)	0.2053 (2)	0.0899 (2)	0.0256 (13)
C5A	0.2864 (3)	0.2426 (2)	0.1029 (2)	0.0251 (13)
O5A	0.28341 (17)	0.29753 (15)	0.06555 (15)	0.0257 (9)
O1A	0.22043 (16)	0.24330 (15)	−0.00622 (14)	0.0249 (9)
O2A	0.35004 (17)	0.22817 (15)	−0.06771 (16)	0.0278 (9)
C21A	0.3768 (3)	0.2699 (3)	−0.1062 (3)	0.0321 (15)
O21A	0.3993 (2)	0.32150 (19)	−0.09272 (18)	0.0475 (11)
C22A	0.3755 (3)	0.2434 (3)	−0.1657 (2)	0.0432 (16)
O3A	0.43702 (16)	0.16739 (15)	0.01695 (15)	0.0259 (9)
C31A	0.4483 (3)	0.1042 (3)	0.0099 (2)	0.0329 (15)
O31A	0.3990 (2)	0.06620 (18)	0.0117 (2)	0.0488 (12)
C32A	0.5276 (3)	0.0907 (2)	0.0007 (3)	0.0364 (16)
O4A	0.34950 (17)	0.14673 (15)	0.12111 (16)	0.0307 (9)
C41A	0.4095 (3)	0.1235 (3)	0.1484 (3)	0.0374 (15)
O41A	0.4663 (2)	0.1520 (2)	0.1512 (2)	0.0762 (17)
C42A	0.3947 (3)	0.0584 (3)	0.1700 (3)	0.0480 (17)
C6A	0.2842 (3)	0.2678 (2)	0.1620 (2)	0.0299 (14)
O51A	0.20846 (18)	0.28854 (15)	0.17302 (16)	0.0325 (9)
S1A	0.19409 (8)	0.34989 (7)	0.21051 (7)	0.0371 (4)
O52A	0.1169 (2)	0.34868 (18)	0.22094 (17)	0.0456 (11)
O53A	0.2455 (2)	0.35042 (18)	0.25691 (16)	0.0487 (11)
C51A	0.2149 (3)	0.4122 (2)	0.1643 (2)	0.0327 (14)
C52A	0.2674 (4)	0.4566 (3)	0.1781 (3)	0.0567 (19)
C53A	0.2793 (4)	0.5059 (3)	0.1410 (3)	0.064 (2)
C54A	0.2437 (3)	0.5117 (3)	0.0905 (3)	0.0475 (18)
C55A	0.1915 (3)	0.4670 (3)	0.0766 (3)	0.0504 (18)
C56A	0.1764 (3)	0.4182 (3)	0.1134 (3)	0.0370 (16)
C57A	0.2600 (3)	0.5654 (3)	0.0501 (3)	0.077 (3)
C1B	0.1545 (3)	0.2796 (2)	−0.0103 (2)	0.0263 (13)
C2B	0.0881 (3)	0.2371 (2)	0.0005 (2)	0.0282 (14)
C3B	0.0769 (3)	0.1899 (2)	−0.0471 (2)	0.0288 (14)
C4B	0.0797 (3)	0.2214 (2)	−0.1045 (2)	0.0319 (14)
C5B	0.1469 (3)	0.2642 (2)	−0.1104 (2)	0.0273 (13)
O5B	0.14840 (17)	0.30854 (15)	−0.06373 (15)	0.0260 (9)
O2B	0.09614 (18)	0.20283 (17)	0.05266 (17)	0.0340 (10)
C21B	0.0684 (3)	0.2324 (3)	0.1003 (3)	0.0358 (15)
O21B	0.0433 (2)	0.2837 (2)	0.09920 (17)	0.0432 (11)
C22B	0.0728 (3)	0.1894 (3)	0.1515 (3)	0.0501 (18)
O3B	0.00380 (17)	0.16370 (16)	−0.03715 (16)	0.0304 (9)
C31B	−0.0083 (3)	0.1016 (3)	−0.0475 (3)	0.0350 (15)
O31B	0.0384 (2)	0.06656 (18)	−0.0658 (2)	0.0513 (12)
C32B	−0.0855 (3)	0.0836 (2)	−0.0334 (3)	0.0422 (17)
O4B	0.08762 (18)	0.17426 (17)	−0.14887 (16)	0.0368 (10)
C41B	0.0255 (4)	0.1507 (3)	−0.1735 (3)	0.0422 (16)
O41B	−0.0349 (2)	0.1690 (2)	−0.16320 (19)	0.0553 (12)
C42B	0.0444 (4)	0.0988 (3)	−0.2147 (3)	0.062 (2)
C6B	0.1439 (3)	0.3029 (3)	−0.1642 (3)	0.0407 (16)
O51B	0.21530 (18)	0.33562 (17)	−0.16801 (17)	0.0393 (10)
S1B	0.22312 (8)	0.38606 (7)	−0.21745 (7)	0.0391 (4)
O52B	0.1631 (2)	0.42937 (18)	−0.2143 (2)	0.0565 (12)
O53B	0.2342 (2)	0.35406 (19)	−0.27059 (17)	0.0514 (12)
C51B	0.3047 (3)	0.4211 (3)	−0.1951 (3)	0.0411 (16)
C52B	0.3048 (4)	0.4568 (3)	−0.1444 (3)	0.056 (2)
C53B	0.3710 (5)	0.4814 (3)	−0.1263 (3)	0.065 (2)
C54B	0.4359 (4)	0.4721 (3)	−0.1559 (4)	0.066 (2)
C55B	0.4346 (4)	0.4389 (3)	−0.2070 (3)	0.068 (2)
C56B	0.3682 (3)	0.4130 (3)	−0.2261 (3)	0.0545 (19)
C57B	0.5094 (4)	0.4962 (4)	−0.1326 (4)	0.108 (3)
C1C	0.2152 (2)	0.7826 (2)	−0.0120 (2)	0.0233 (12)
C2C	0.1473 (3)	0.7443 (2)	0.0038 (2)	0.0234 (13)
C3C	0.1361 (3)	0.6884 (2)	−0.0362 (2)	0.0255 (14)
C4C	0.1406 (3)	0.7091 (2)	−0.0979 (2)	0.0242 (13)
C5C	0.2090 (3)	0.7488 (2)	−0.1090 (2)	0.0249 (13)
O5C	0.21055 (16)	0.80155 (15)	−0.06949 (15)	0.0244 (8)
O1B	0.27881 (16)	0.74521 (15)	−0.00206 (14)	0.0240 (8)
O2C	0.15398 (18)	0.71882 (16)	0.06037 (16)	0.0305 (9)
C21C	0.1158 (3)	0.7479 (3)	0.1021 (3)	0.0312 (14)
O21C	0.0805 (2)	0.79616 (18)	0.09450 (16)	0.0404 (10)
C22C	0.1211 (3)	0.7134 (3)	0.1575 (3)	0.0476 (17)
O3C	0.06341 (16)	0.66463 (16)	−0.02448 (15)	0.0283 (9)
C31C	0.0524 (3)	0.6003 (3)	−0.0233 (3)	0.0374 (16)
O31C	0.1010 (2)	0.56270 (18)	−0.02933 (19)	0.0470 (12)
C32C	−0.0276 (3)	0.5870 (3)	−0.0140 (3)	0.0467 (18)
O4C	0.14873 (18)	0.65245 (16)	−0.13194 (15)	0.0318 (9)
C41C	0.0888 (3)	0.6276 (3)	−0.1574 (3)	0.0456 (16)
O41C	0.0292 (2)	0.6525 (2)	−0.1559 (2)	0.0702 (15)
C42C	0.1069 (4)	0.5649 (3)	−0.1829 (3)	0.068 (2)
C6C	0.2073 (3)	0.7761 (2)	−0.1675 (2)	0.0282 (13)
O51C	0.28161 (18)	0.79889 (15)	−0.18183 (15)	0.0298 (9)
S1C	0.28957 (8)	0.86651 (7)	−0.21056 (7)	0.0346 (4)
O52C	0.2343 (2)	0.87298 (17)	−0.25370 (16)	0.0433 (10)
O53C	0.36546 (19)	0.87061 (17)	−0.22487 (17)	0.0427 (11)
C51C	0.2692 (3)	0.9178 (2)	−0.1541 (2)	0.0296 (14)
C52C	0.3192 (3)	0.9232 (2)	−0.1094 (2)	0.0315 (14)
C53C	0.3026 (3)	0.9607 (2)	−0.0635 (3)	0.0355 (15)
C54C	0.2374 (3)	0.9940 (2)	−0.0610 (3)	0.0363 (16)
C55C	0.1885 (3)	0.9888 (3)	−0.1057 (3)	0.0383 (16)
C56C	0.2038 (3)	0.9509 (2)	−0.1522 (3)	0.0372 (15)
C57C	0.2201 (3)	1.0356 (3)	−0.0099 (3)	0.060 (2)
C1D	0.3426 (3)	0.7828 (2)	0.0067 (2)	0.0240 (13)
C2D	0.4106 (3)	0.7436 (2)	−0.0076 (2)	0.0247 (13)
C3D	0.4203 (3)	0.6900 (2)	0.0338 (2)	0.0272 (14)
C4D	0.4186 (3)	0.7145 (2)	0.0951 (2)	0.0241 (13)
C5D	0.3485 (3)	0.7524 (2)	0.1051 (2)	0.0253 (13)
O5D	0.34661 (17)	0.80267 (15)	0.06396 (16)	0.0264 (9)
O2D	0.40426 (18)	0.71665 (16)	−0.06365 (16)	0.0297 (9)
C21D	0.4286 (3)	0.7525 (3)	−0.1076 (3)	0.0348 (15)
O21D	0.4498 (2)	0.80604 (18)	−0.10127 (17)	0.0391 (10)
C22D	0.4257 (3)	0.7168 (3)	−0.1634 (3)	0.0434 (16)
O3D	0.49263 (16)	0.66269 (16)	0.02471 (16)	0.0288 (9)
C31D	0.4965 (3)	0.6027 (3)	0.0054 (3)	0.0385 (16)
O31D	0.4427 (2)	0.57111 (19)	−0.0049 (2)	0.0618 (15)
C32D	0.5741 (3)	0.5820 (3)	−0.0018 (3)	0.0451 (17)
O4D	0.41842 (18)	0.66013 (16)	0.13239 (15)	0.0304 (9)
C41D	0.4828 (3)	0.6448 (3)	0.1586 (3)	0.0436 (17)
O41D	0.5365 (2)	0.6759 (2)	0.1561 (2)	0.0807 (18)
C42D	0.4768 (3)	0.5823 (3)	0.1885 (3)	0.067 (2)
C6D	0.3447 (3)	0.7820 (3)	0.1628 (2)	0.0346 (15)
O51D	0.2722 (2)	0.80853 (16)	0.17204 (17)	0.0400 (10)
S1D	0.25718 (8)	0.88184 (7)	0.16115 (8)	0.0430 (4)
O52D	0.2203 (2)	0.8892 (2)	0.10723 (17)	0.0550 (12)
O53D	0.3236 (2)	0.91536 (18)	0.1719 (2)	0.0542 (13)
C51D	0.1933 (3)	0.8966 (3)	0.2159 (3)	0.0372 (15)
C52D	0.2177 (3)	0.9151 (3)	0.2686 (3)	0.0541 (19)
C53D	0.1667 (4)	0.9279 (3)	0.3117 (3)	0.057 (2)
C54D	0.0926 (3)	0.9211 (3)	0.3018 (3)	0.0447 (17)
C55D	0.0688 (3)	0.9012 (3)	0.2489 (3)	0.0498 (18)
C56D	0.1198 (3)	0.8887 (3)	0.2058 (3)	0.0465 (17)
C57D	0.0368 (3)	0.9342 (3)	0.3492 (3)	0.068 (2)
H1A	0.2790	0.3225	−0.0153	0.029*
H2A	0.3954	0.2767	−0.0034	0.025*
H3A	0.3261	0.1561	0.0169	0.027*
H4A	0.4010	0.2293	0.1030	0.031*
H5A	0.2424	0.2152	0.0960	0.030*
H22A	0.3751	0.2783	−0.1933	0.065*
H22B	0.3311	0.2176	−0.1708	0.065*
H22C	0.4193	0.2172	−0.1718	0.065*
H32A	0.5355	0.0448	0.0007	0.055*
H32B	0.5565	0.1100	0.0315	0.055*
H32C	0.5431	0.1084	−0.0360	0.055*
H42A	0.4383	0.0425	0.1901	0.072*
H42B	0.3834	0.0304	0.1378	0.072*
H42C	0.3527	0.0594	0.1962	0.072*
H6A	0.2986	0.2344	0.1896	0.036*
H6B	0.3187	0.3039	0.1660	0.036*
H52A	0.2949	0.4531	0.2124	0.068*
H53A	0.3140	0.5376	0.1514	0.077*
H55A	0.1657	0.4700	0.0414	0.060*
H56A	0.1393	0.3882	0.1040	0.044*
H57A	0.2716	0.6037	0.0720	0.116*
H57B	0.2168	0.5733	0.0260	0.116*
H57C	0.3021	0.5542	0.0259	0.116*
H1B	0.1557	0.3134	0.0197	0.032*
H2B	0.0431	0.2643	0.0034	0.034*
H3B	0.1149	0.1557	−0.0448	0.035*
H4B	0.0337	0.2465	−0.1109	0.038*
H5B	0.1928	0.2380	−0.1100	0.033*
H22D	0.0716	0.2149	0.1865	0.075*
H22E	0.1188	0.1651	0.1501	0.075*
H22F	0.0308	0.1602	0.1512	0.075*
H32D	−0.0896	0.0373	−0.0322	0.063*
H32E	−0.1188	0.1003	−0.0627	0.063*
H32F	−0.0989	0.1012	0.0038	0.063*
H42D	0.0082	0.0645	−0.2113	0.093*
H42E	0.0937	0.0823	−0.2060	0.093*
H42F	0.0438	0.1155	−0.2537	0.093*
H6C	0.1364	0.2752	−0.1978	0.049*
H6D	0.1031	0.3339	−0.1624	0.049*
H52B	0.2608	0.4638	−0.1234	0.068*
H53B	0.3721	0.5056	−0.0921	0.078*
H55B	0.4784	0.4338	−0.2287	0.081*
H56B	0.3670	0.3896	−0.2608	0.065*
H57D	0.5230	0.4715	−0.0988	0.162*
H57E	0.5047	0.5409	−0.1222	0.162*
H57F	0.5476	0.4915	−0.1619	0.162*
H1C	0.2174	0.8212	0.0127	0.028*
H2C	0.1030	0.7724	0.0020	0.028*
H3C	0.1737	0.6549	−0.0283	0.031*
H4C	0.0952	0.7328	−0.1092	0.029*
H5C	0.2542	0.7223	−0.1040	0.030*
H22G	0.1210	0.7439	0.1890	0.071*
H22H	0.1669	0.6887	0.1585	0.071*
H22I	0.0789	0.6847	0.1615	0.071*
H32G	−0.0358	0.5411	−0.0141	0.070*
H32H	−0.0565	0.6066	−0.0446	0.070*
H32I	−0.0429	0.6046	0.0229	0.070*
H42G	0.0723	0.5330	−0.1688	0.102*
H42H	0.1573	0.5529	−0.1723	0.102*
H42I	0.1032	0.5676	−0.2246	0.102*
H6E	0.1916	0.7435	−0.1953	0.034*
H6F	0.1718	0.8117	−0.1691	0.034*
H52C	0.3647	0.9009	−0.1106	0.038*
H53C	0.3367	0.9638	−0.0329	0.043*
H55C	0.1435	1.0118	−0.1045	0.046*
H56C	0.1694	0.9476	−0.1826	0.045*
H57G	0.1702	1.0528	−0.0137	0.090*
H57H	0.2556	1.0706	−0.0081	0.090*
H57I	0.2235	1.0104	0.0252	0.090*
H1D	0.3406	0.8207	−0.0188	0.029*
H2D	0.4551	0.7715	−0.0062	0.030*
H3D	0.3811	0.6572	0.0280	0.033*
H4D	0.4629	0.7414	0.1027	0.029*
H5D	0.3048	0.7243	0.0995	0.030*
H22J	0.4290	0.7468	−0.1952	0.065*
H22K	0.3791	0.6934	−0.1659	0.065*
H22L	0.4670	0.6869	−0.1653	0.065*
H32J	0.5763	0.5356	−0.0021	0.068*
H32K	0.6039	0.5983	0.0299	0.068*
H32L	0.5935	0.5985	−0.0380	0.068*
H42J	0.4701	0.5486	0.1602	0.100*
H42K	0.4345	0.5830	0.2145	0.100*
H42L	0.5220	0.5745	0.2103	0.100*
H61G	0.3552	0.7497	0.1923	0.042*
H61H	0.3823	0.8158	0.1659	0.042*
H52D	0.2690	0.9192	0.2758	0.065*
H53D	0.1834	0.9414	0.3481	0.068*
H55D	0.0176	0.8960	0.2418	0.060*
H56D	0.1033	0.8747	0.1694	0.056*
H57J	0.0220	0.8941	0.3669	0.102*
H57K	−0.0066	0.9551	0.3330	0.102*
H57L	0.0592	0.9617	0.3781	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.018 (3)	0.025 (3)	0.028 (4)	−0.001 (2)	−0.001 (2)	0.003 (3)
C2A	0.023 (3)	0.020 (3)	0.020 (3)	−0.006 (2)	−0.002 (2)	−0.002 (3)
C3A	0.015 (3)	0.021 (3)	0.031 (4)	−0.003 (2)	0.002 (2)	−0.005 (3)
C4A	0.023 (3)	0.019 (3)	0.035 (4)	0.000 (2)	−0.001 (3)	0.009 (3)
C5A	0.019 (3)	0.028 (3)	0.028 (4)	−0.003 (2)	0.003 (3)	0.001 (3)
O5A	0.029 (2)	0.023 (2)	0.025 (2)	0.0047 (16)	0.0020 (17)	0.0026 (18)
O1A	0.0178 (19)	0.029 (2)	0.027 (2)	−0.0007 (16)	−0.0023 (17)	−0.0005 (17)
O2A	0.030 (2)	0.031 (2)	0.023 (2)	−0.0010 (17)	0.0035 (18)	0.0014 (19)
C21A	0.031 (3)	0.043 (4)	0.023 (4)	0.011 (3)	0.006 (3)	0.004 (3)
O21A	0.068 (3)	0.040 (3)	0.034 (3)	−0.005 (2)	0.005 (2)	0.003 (2)
C22A	0.042 (4)	0.063 (4)	0.025 (4)	0.006 (3)	0.004 (3)	0.000 (3)
O3A	0.0163 (19)	0.020 (2)	0.041 (3)	0.0006 (15)	0.0064 (17)	−0.0020 (18)
C31A	0.027 (3)	0.035 (4)	0.037 (4)	−0.002 (3)	0.002 (3)	−0.001 (3)
O31A	0.025 (2)	0.031 (2)	0.090 (4)	−0.0022 (18)	0.008 (2)	−0.007 (2)
C32A	0.026 (3)	0.029 (3)	0.054 (5)	0.011 (2)	0.004 (3)	−0.004 (3)
O4A	0.026 (2)	0.027 (2)	0.039 (3)	0.0023 (16)	0.0018 (18)	0.0059 (19)
C41A	0.027 (3)	0.048 (4)	0.037 (4)	0.003 (3)	−0.004 (3)	0.008 (3)
O41A	0.053 (3)	0.063 (3)	0.112 (5)	−0.005 (2)	−0.035 (3)	0.045 (3)
C42A	0.061 (4)	0.035 (4)	0.048 (5)	0.014 (3)	−0.001 (3)	0.015 (3)
C6A	0.026 (3)	0.033 (3)	0.031 (4)	0.006 (2)	−0.002 (3)	−0.001 (3)
O51A	0.031 (2)	0.030 (2)	0.036 (3)	0.0050 (17)	0.0093 (18)	−0.0025 (19)
S1A	0.0472 (10)	0.0394 (9)	0.0246 (9)	0.0129 (7)	0.0019 (8)	0.0007 (8)
O52A	0.042 (2)	0.055 (3)	0.040 (3)	0.0207 (19)	0.017 (2)	0.007 (2)
O53A	0.063 (3)	0.052 (3)	0.031 (3)	0.021 (2)	−0.010 (2)	0.000 (2)
C51A	0.043 (4)	0.029 (3)	0.026 (4)	0.008 (3)	−0.001 (3)	−0.002 (3)
C52A	0.061 (5)	0.063 (5)	0.046 (5)	−0.011 (4)	−0.029 (4)	0.011 (4)
C53A	0.064 (5)	0.052 (5)	0.076 (6)	−0.031 (4)	−0.024 (4)	0.009 (4)
C54A	0.034 (4)	0.035 (4)	0.074 (6)	−0.006 (3)	−0.015 (4)	0.016 (4)
C55A	0.043 (4)	0.052 (4)	0.056 (5)	−0.010 (3)	−0.014 (3)	0.028 (4)
C56A	0.027 (3)	0.042 (4)	0.042 (4)	−0.008 (3)	−0.010 (3)	0.007 (3)
C57A	0.037 (4)	0.055 (4)	0.140 (8)	−0.004 (3)	−0.009 (4)	0.048 (5)
C1B	0.020 (3)	0.026 (3)	0.034 (4)	0.002 (2)	−0.004 (3)	0.005 (3)
C2B	0.025 (3)	0.034 (4)	0.026 (4)	−0.003 (2)	0.001 (3)	0.005 (3)
C3B	0.015 (3)	0.038 (4)	0.033 (4)	0.003 (2)	0.000 (3)	0.002 (3)
C4B	0.027 (3)	0.032 (3)	0.037 (4)	0.000 (3)	−0.004 (3)	−0.005 (3)
C5B	0.021 (3)	0.026 (3)	0.034 (4)	0.003 (2)	0.005 (3)	0.002 (3)
O5B	0.0208 (19)	0.030 (2)	0.027 (2)	0.0038 (15)	0.0007 (17)	0.0067 (19)
O2B	0.029 (2)	0.043 (2)	0.030 (3)	0.0044 (18)	0.0002 (18)	0.009 (2)
C21B	0.031 (3)	0.046 (4)	0.030 (4)	−0.011 (3)	−0.008 (3)	0.003 (3)
O21B	0.052 (3)	0.048 (3)	0.030 (3)	0.009 (2)	0.002 (2)	0.003 (2)
C22B	0.039 (4)	0.071 (5)	0.040 (5)	−0.013 (3)	0.005 (3)	0.013 (4)
O3B	0.019 (2)	0.026 (2)	0.046 (3)	−0.0023 (16)	0.0036 (17)	−0.001 (2)
C31B	0.030 (3)	0.032 (4)	0.043 (4)	0.008 (3)	0.005 (3)	0.008 (3)
O31B	0.032 (2)	0.036 (2)	0.086 (4)	0.0040 (19)	0.010 (2)	−0.006 (3)
C32B	0.029 (3)	0.032 (4)	0.066 (5)	−0.004 (3)	0.012 (3)	0.005 (3)
O4B	0.026 (2)	0.050 (3)	0.035 (3)	−0.0034 (18)	−0.0035 (19)	−0.002 (2)
C41B	0.041 (4)	0.048 (4)	0.038 (4)	−0.007 (3)	−0.007 (3)	0.000 (3)
O41B	0.032 (3)	0.078 (3)	0.056 (3)	−0.018 (2)	−0.008 (2)	−0.003 (3)
C42B	0.069 (5)	0.068 (5)	0.050 (5)	−0.010 (4)	−0.006 (4)	−0.012 (4)
C6B	0.030 (3)	0.057 (4)	0.035 (4)	−0.002 (3)	−0.001 (3)	0.011 (3)
O51B	0.033 (2)	0.042 (2)	0.044 (3)	−0.0020 (18)	−0.0007 (19)	0.021 (2)
S1B	0.0467 (9)	0.0360 (9)	0.0346 (10)	0.0003 (7)	0.0029 (8)	0.0049 (8)
O52B	0.062 (3)	0.045 (3)	0.063 (3)	0.014 (2)	−0.009 (3)	0.006 (3)
O53B	0.060 (3)	0.059 (3)	0.034 (3)	−0.013 (2)	0.009 (2)	−0.007 (2)
C51B	0.052 (4)	0.034 (4)	0.037 (4)	−0.008 (3)	0.001 (3)	0.002 (3)
C52B	0.079 (6)	0.043 (4)	0.047 (5)	−0.006 (4)	−0.003 (4)	−0.001 (4)
C53B	0.108 (7)	0.053 (5)	0.034 (5)	−0.024 (4)	−0.010 (5)	0.001 (4)
C54B	0.080 (6)	0.068 (5)	0.051 (6)	−0.039 (4)	−0.014 (5)	0.007 (5)
C55B	0.050 (5)	0.081 (6)	0.073 (6)	−0.033 (4)	0.002 (4)	0.016 (5)
C56B	0.052 (4)	0.066 (5)	0.046 (5)	−0.022 (3)	0.002 (4)	−0.002 (4)
C57B	0.106 (7)	0.130 (8)	0.088 (8)	−0.073 (6)	−0.028 (6)	0.015 (6)
C1C	0.020 (3)	0.033 (3)	0.017 (3)	0.008 (2)	−0.004 (2)	−0.002 (3)
C2C	0.021 (3)	0.025 (3)	0.024 (4)	−0.001 (2)	−0.003 (3)	0.000 (3)
C3C	0.014 (3)	0.029 (3)	0.034 (4)	0.000 (2)	0.004 (2)	0.009 (3)
C4C	0.022 (3)	0.022 (3)	0.028 (4)	0.007 (2)	−0.001 (2)	−0.006 (3)
C5C	0.025 (3)	0.023 (3)	0.026 (4)	0.001 (2)	0.000 (3)	−0.001 (3)
O5C	0.025 (2)	0.024 (2)	0.024 (2)	−0.0011 (15)	−0.0018 (17)	−0.0004 (18)
O1B	0.0168 (19)	0.0234 (19)	0.032 (2)	−0.0021 (15)	−0.0002 (17)	0.0043 (17)
O2C	0.026 (2)	0.038 (2)	0.028 (3)	0.0049 (17)	0.0001 (18)	0.012 (2)
C21C	0.026 (3)	0.037 (4)	0.031 (4)	−0.007 (3)	0.006 (3)	−0.004 (3)
O21C	0.046 (2)	0.048 (3)	0.027 (3)	0.006 (2)	0.009 (2)	−0.004 (2)
C22C	0.048 (4)	0.067 (5)	0.028 (4)	−0.001 (3)	−0.004 (3)	0.019 (4)
O3C	0.0164 (19)	0.029 (2)	0.039 (3)	−0.0013 (16)	0.0035 (17)	0.0014 (19)
C31C	0.028 (4)	0.033 (4)	0.051 (5)	−0.004 (3)	−0.002 (3)	−0.001 (3)
O31C	0.032 (2)	0.027 (2)	0.082 (4)	0.0029 (19)	0.007 (2)	0.005 (2)
C32C	0.039 (4)	0.028 (4)	0.074 (5)	0.000 (3)	0.011 (3)	−0.002 (3)
O4C	0.030 (2)	0.029 (2)	0.036 (3)	−0.0014 (17)	0.0008 (18)	−0.0074 (19)
C41C	0.040 (4)	0.050 (4)	0.047 (5)	−0.007 (3)	0.003 (3)	−0.013 (4)
O41C	0.052 (3)	0.064 (3)	0.094 (4)	0.007 (2)	−0.032 (3)	−0.037 (3)
C42C	0.068 (5)	0.045 (4)	0.090 (6)	−0.011 (3)	0.005 (4)	−0.038 (4)
C6C	0.023 (3)	0.033 (3)	0.029 (4)	−0.002 (2)	0.002 (3)	0.000 (3)
O51C	0.028 (2)	0.031 (2)	0.031 (2)	−0.0003 (17)	0.0079 (17)	0.0010 (18)
S1C	0.0397 (9)	0.0381 (9)	0.0260 (9)	−0.0022 (7)	0.0030 (8)	0.0034 (7)
O52C	0.057 (3)	0.045 (3)	0.028 (3)	−0.003 (2)	−0.006 (2)	0.006 (2)
O53C	0.040 (2)	0.047 (3)	0.042 (3)	−0.0103 (19)	0.0186 (19)	0.003 (2)
C51C	0.030 (3)	0.029 (3)	0.029 (4)	−0.004 (2)	−0.002 (3)	−0.001 (3)
C52C	0.031 (3)	0.027 (3)	0.037 (4)	0.004 (2)	0.000 (3)	−0.003 (3)
C53C	0.027 (3)	0.038 (4)	0.041 (4)	0.000 (3)	−0.008 (3)	−0.004 (3)
C54C	0.029 (3)	0.030 (3)	0.050 (5)	−0.007 (3)	0.002 (3)	−0.014 (3)
C55C	0.030 (3)	0.032 (4)	0.053 (5)	0.004 (3)	0.000 (3)	−0.005 (3)
C56C	0.026 (3)	0.040 (4)	0.045 (4)	0.001 (3)	−0.008 (3)	0.006 (3)
C57C	0.029 (4)	0.069 (5)	0.082 (6)	−0.006 (3)	−0.001 (4)	−0.035 (4)
C1D	0.024 (3)	0.027 (3)	0.021 (4)	−0.002 (2)	0.001 (2)	0.000 (3)
C2D	0.028 (3)	0.026 (3)	0.020 (4)	−0.003 (2)	−0.006 (3)	−0.001 (3)
C3D	0.016 (3)	0.031 (3)	0.035 (4)	−0.004 (2)	0.000 (3)	−0.004 (3)
C4D	0.017 (3)	0.025 (3)	0.031 (4)	0.001 (2)	−0.001 (2)	0.009 (3)
C5D	0.020 (3)	0.029 (3)	0.027 (4)	−0.001 (2)	−0.001 (3)	0.003 (3)
O5D	0.0203 (19)	0.026 (2)	0.033 (3)	−0.0017 (15)	−0.0016 (17)	−0.0020 (19)
O2D	0.028 (2)	0.034 (2)	0.028 (3)	−0.0054 (17)	0.0040 (18)	0.000 (2)
C21D	0.026 (3)	0.043 (4)	0.035 (4)	0.010 (3)	−0.002 (3)	−0.003 (4)
O21D	0.049 (3)	0.035 (3)	0.033 (3)	0.007 (2)	0.005 (2)	0.005 (2)
C22D	0.038 (4)	0.059 (4)	0.033 (4)	0.005 (3)	−0.002 (3)	−0.011 (3)
O3D	0.017 (2)	0.026 (2)	0.043 (3)	0.0028 (16)	0.0040 (17)	−0.003 (2)
C31D	0.030 (4)	0.036 (4)	0.049 (5)	0.000 (3)	0.000 (3)	0.007 (3)
O31D	0.030 (2)	0.037 (3)	0.119 (5)	−0.002 (2)	0.008 (3)	−0.017 (3)
C32D	0.039 (4)	0.035 (4)	0.061 (5)	0.012 (3)	0.006 (3)	0.001 (3)
O4D	0.024 (2)	0.035 (2)	0.033 (2)	0.0011 (16)	−0.0035 (17)	0.007 (2)
C41D	0.036 (4)	0.057 (4)	0.037 (4)	−0.006 (3)	−0.003 (3)	0.018 (4)
O41D	0.044 (3)	0.091 (4)	0.107 (5)	−0.024 (3)	−0.033 (3)	0.062 (3)
C42D	0.043 (4)	0.062 (5)	0.097 (7)	0.006 (3)	−0.017 (4)	0.046 (5)
C6D	0.033 (3)	0.041 (4)	0.030 (4)	0.012 (3)	0.003 (3)	−0.001 (3)
O51D	0.039 (2)	0.032 (2)	0.049 (3)	0.0003 (18)	0.013 (2)	0.000 (2)
S1D	0.0421 (9)	0.0417 (10)	0.0451 (12)	0.0001 (7)	0.0117 (8)	−0.0023 (9)
O52D	0.058 (3)	0.074 (3)	0.033 (3)	0.021 (2)	0.005 (2)	0.001 (2)
O53D	0.038 (3)	0.049 (3)	0.075 (4)	−0.010 (2)	0.019 (2)	0.001 (2)
C51D	0.033 (4)	0.043 (4)	0.035 (4)	−0.001 (3)	0.008 (3)	−0.015 (3)
C52D	0.036 (4)	0.067 (5)	0.059 (5)	−0.015 (3)	0.006 (4)	−0.030 (4)
C53D	0.057 (5)	0.060 (5)	0.053 (5)	−0.018 (4)	0.016 (4)	−0.025 (4)
C54D	0.049 (4)	0.036 (4)	0.049 (5)	−0.002 (3)	0.014 (4)	−0.013 (3)
C55D	0.034 (4)	0.060 (5)	0.056 (5)	−0.001 (3)	0.001 (4)	−0.012 (4)
C56D	0.041 (4)	0.055 (4)	0.043 (5)	0.008 (3)	0.003 (3)	−0.004 (4)
C57D	0.061 (5)	0.083 (5)	0.059 (6)	−0.011 (4)	0.036 (4)	−0.017 (4)

Geometric parameters (Å, º)

C1A—O5A	1.401 (6)	C1C—O5C	1.406 (6)
C1A—O1A	1.429 (5)	C1C—O1B	1.418 (5)
C1A—C2A	1.518 (6)	C1C—C2C	1.519 (6)
C1A—H1A	1.00	C1C—H1C	1.00
C2A—O2A	1.436 (6)	C2C—O2C	1.436 (6)
C2A—C3A	1.509 (7)	C2C—C3C	1.520 (7)
C2A—H2A	1.00	C2C—H2C	1.00
C3A—O3A	1.448 (5)	C3C—O3C	1.439 (5)
C3A—C4A	1.502 (7)	C3C—C4C	1.511 (7)
C3A—H3A	1.00	C3C—H3C	1.00
C4A—O4A	1.441 (5)	C4C—O4C	1.444 (6)
C4A—C5A	1.528 (6)	C4C—C5C	1.520 (6)
C4A—H4A	1.00	C4C—H4C	1.00
C5A—O5A	1.452 (6)	C5C—O5C	1.447 (6)
C5A—C6A	1.484 (7)	C5C—C6C	1.489 (7)
C5A—H5A	1.00	C5C—H5C	1.00
O1A—C1B	1.424 (5)	O1B—C1D	1.417 (5)
O2A—C21A	1.350 (6)	O2C—C21C	1.346 (6)
C21A—O21A	1.205 (6)	C21C—O21C	1.216 (6)
C21A—C22A	1.502 (8)	C21C—C22C	1.493 (8)
C22A—H22A	0.98	C22C—H22G	0.98
C22A—H22B	0.98	C22C—H22H	0.98
C22A—H22C	0.98	C22C—H22I	0.98
O3A—C31A	1.360 (6)	O3C—C31C	1.372 (6)
C31A—O31A	1.203 (6)	C31C—O31C	1.195 (6)
C31A—C32A	1.481 (7)	C31C—C32C	1.495 (7)
C32A—H32A	0.98	C32C—H32G	0.98
C32A—H32B	0.98	C32C—H32H	0.98
C32A—H32C	0.98	C32C—H32I	0.98
O4A—C41A	1.354 (6)	O4C—C41C	1.346 (6)
C41A—O41A	1.195 (6)	C41C—O41C	1.203 (6)
C41A—C42A	1.489 (7)	C41C—C42C	1.489 (8)
C42A—H42A	0.98	C42C—H42G	0.98
C42A—H42B	0.98	C42C—H42H	0.98
C42A—H42C	0.98	C42C—H42I	0.98
C6A—O51A	1.466 (5)	C6C—O51C	1.470 (5)
C6A—H6A	0.99	C6C—H6E	0.99
C6A—H6B	0.99	C6C—H6F	0.99
O51A—S1A	1.586 (4)	O51C—S1C	1.584 (3)
S1A—O52A	1.422 (4)	S1C—O53C	1.420 (4)
S1A—O53A	1.433 (4)	S1C—O52C	1.430 (4)
S1A—C51A	1.745 (6)	S1C—C51C	1.748 (5)
C51A—C52A	1.374 (8)	C51C—C56C	1.378 (7)
C51A—C56A	1.388 (7)	C51C—C52C	1.392 (7)
C52A—C53A	1.373 (8)	C52C—C53C	1.367 (7)
C52A—H52A	0.95	C52C—H52C	0.95
C53A—C54A	1.354 (9)	C53C—C54C	1.378 (7)
C53A—H53A	0.95	C53C—H53C	0.95
C54A—C55A	1.376 (8)	C54C—C55C	1.378 (8)
C54A—C57A	1.506 (8)	C54C—C57C	1.517 (8)
C55A—C56A	1.371 (7)	C55C—C56C	1.380 (8)
C55A—H55A	0.95	C55C—H55C	0.95
C56A—H56A	0.95	C56C—H56C	0.95
C57A—H57A	0.98	C57C—H57G	0.98
C57A—H57B	0.98	C57C—H57H	0.98
C57A—H57C	0.98	C57C—H57I	0.98
C1B—O5B	1.397 (6)	C1D—O5D	1.408 (6)
C1B—C2B	1.525 (7)	C1D—C2D	1.523 (7)
C1B—H1B	1.00	C1D—H1D	1.00
C2B—O2B	1.427 (6)	C2D—O2D	1.434 (6)
C2B—C3B	1.509 (7)	C2D—C3D	1.501 (7)
C2B—H2B	1.00	C2D—H2D	1.00
C3B—O3B	1.457 (6)	C3D—O3D	1.450 (6)
C3B—C4B	1.501 (7)	C3D—C4D	1.526 (7)
C3B—H3B	1.00	C3D—H3D	1.00
C4B—O4B	1.445 (6)	C4D—O4D	1.443 (6)
C4B—C5B	1.524 (7)	C4D—C5D	1.521 (6)
C4B—H4B	1.00	C4D—H4D	1.00
C5B—O5B	1.439 (6)	C5D—O5D	1.433 (6)
C5B—C6B	1.502 (7)	C5D—C6D	1.489 (7)
C5B—H5B	1.00	C5D—H5D	1.00
O2B—C21B	1.373 (7)	O2D—C21D	1.352 (7)
C21B—O21B	1.175 (6)	C21D—O21D	1.204 (6)
C21B—C22B	1.507 (8)	C21D—C22D	1.509 (8)
C22B—H22D	0.98	C22D—H22J	0.98
C22B—H22E	0.98	C22D—H22K	0.98
C22B—H22F	0.98	C22D—H22L	0.98
O3B—C31B	1.351 (6)	O3D—C31D	1.346 (7)
C31B—O31B	1.204 (6)	C31D—O31D	1.208 (6)
C31B—C32B	1.489 (7)	C31D—C32D	1.484 (7)
C32B—H32D	0.98	C32D—H32J	0.98
C32B—H32E	0.98	C32D—H32K	0.98
C32B—H32F	0.98	C32D—H32L	0.98
O4B—C41B	1.360 (6)	O4D—C41D	1.358 (6)
C41B—O41B	1.188 (6)	C41D—O41D	1.177 (6)
C41B—C42B	1.502 (8)	C41D—C42D	1.497 (8)
C42B—H42D	0.98	C42D—H42J	0.98
C42B—H42E	0.98	C42D—H42K	0.98
C42B—H42F	0.98	C42D—H42L	0.98
C6B—O51B	1.471 (6)	C6D—O51D	1.446 (5)
C6B—H6C	0.99	C6D—H61G	0.99
C6B—H6D	0.99	C6D—H61H	0.99
O51B—S1B	1.579 (4)	O51D—S1D	1.592 (4)
S1B—O52B	1.424 (4)	S1D—O53D	1.421 (4)
S1B—O53B	1.430 (4)	S1D—O52D	1.438 (4)
S1B—C51B	1.736 (6)	S1D—C51D	1.756 (6)
C51B—C56B	1.375 (8)	C51D—C56D	1.365 (7)
C51B—C52B	1.406 (8)	C51D—C52D	1.369 (8)
C52B—C53B	1.374 (9)	C52D—C53D	1.397 (8)
C52B—H52B	0.95	C52D—H52D	0.95
C53B—C54B	1.381 (9)	C53D—C54D	1.372 (8)
C53B—H53B	0.95	C53D—H53D	0.95
C54B—C55B	1.386 (10)	C54D—C55D	1.378 (8)
C54B—C57B	1.529 (9)	C54D—C57D	1.527 (8)
C55B—C56B	1.396 (8)	C55D—C56D	1.395 (8)
C55B—H55B	0.95	C55D—H55D	0.95
C56B—H56B	0.95	C56D—H56D	0.95
C57B—H57D	0.98	C57D—H57J	0.98
C57B—H57E	0.98	C57D—H57K	0.98
C57B—H57F	0.98	C57D—H57L	0.98
O5A—C1A—O1A	111.0 (4)	O5C—C1C—O1B	111.4 (4)
O5A—C1A—C2A	110.0 (4)	O5C—C1C—C2C	109.6 (4)
O1A—C1A—C2A	108.9 (4)	O1B—C1C—C2C	109.0 (4)
O5A—C1A—H1A	109.0	O5C—C1C—H1C	108.9
O1A—C1A—H1A	109.0	O1B—C1C—H1C	108.9
C2A—C1A—H1A	109.0	C2C—C1C—H1C	108.9
O2A—C2A—C3A	108.3 (4)	O2C—C2C—C1C	110.9 (4)
O2A—C2A—C1A	110.7 (4)	O2C—C2C—C3C	106.8 (4)
C3A—C2A—C1A	110.8 (4)	C1C—C2C—C3C	111.7 (4)
O2A—C2A—H2A	109.0	O2C—C2C—H2C	109.1
C3A—C2A—H2A	109.0	C1C—C2C—H2C	109.1
C1A—C2A—H2A	109.0	C3C—C2C—H2C	109.1
O3A—C3A—C4A	108.0 (4)	O3C—C3C—C4C	109.5 (4)
O3A—C3A—C2A	106.3 (4)	O3C—C3C—C2C	106.0 (4)
C4A—C3A—C2A	111.2 (4)	C4C—C3C—C2C	111.0 (4)
O3A—C3A—H3A	110.4	O3C—C3C—H3C	110.1
C4A—C3A—H3A	110.4	C4C—C3C—H3C	110.1
C2A—C3A—H3A	110.4	C2C—C3C—H3C	110.1
O4A—C4A—C3A	108.0 (4)	O4C—C4C—C3C	107.2 (4)
O4A—C4A—C5A	105.5 (4)	O4C—C4C—C5C	106.2 (4)
C3A—C4A—C5A	111.7 (4)	C3C—C4C—C5C	111.5 (4)
O4A—C4A—H4A	110.5	O4C—C4C—H4C	110.6
C3A—C4A—H4A	110.5	C3C—C4C—H4C	110.6
C5A—C4A—H4A	110.5	C5C—C4C—H4C	110.6
O5A—C5A—C6A	106.0 (4)	O5C—C5C—C6C	106.9 (4)
O5A—C5A—C4A	108.8 (4)	O5C—C5C—C4C	109.4 (4)
C6A—C5A—C4A	113.1 (4)	C6C—C5C—C4C	110.7 (4)
O5A—C5A—H5A	109.6	O5C—C5C—H5C	109.9
C6A—C5A—H5A	109.6	C6C—C5C—H5C	109.9
C4A—C5A—H5A	109.6	C4C—C5C—H5C	109.9
C1A—O5A—C5A	113.9 (4)	C1C—O5C—C5C	113.2 (4)
C1B—O1A—C1A	111.3 (3)	C1D—O1B—C1C	112.2 (4)
C21A—O2A—C2A	116.2 (4)	C21C—O2C—C2C	117.1 (4)
O21A—C21A—O2A	122.4 (5)	O21C—C21C—O2C	123.2 (5)
O21A—C21A—C22A	125.8 (6)	O21C—C21C—C22C	124.7 (6)
O2A—C21A—C22A	111.8 (5)	O2C—C21C—C22C	112.0 (5)
C21A—C22A—H22A	109.5	C21C—C22C—H22G	109.5
C21A—C22A—H22B	109.5	C21C—C22C—H22H	109.5
H22A—C22A—H22B	109.5	H22G—C22C—H22H	109.5
C21A—C22A—H22C	109.5	C21C—C22C—H22I	109.5
H22A—C22A—H22C	109.5	H22G—C22C—H22I	109.5
H22B—C22A—H22C	109.5	H22H—C22C—H22I	109.5
C31A—O3A—C3A	118.5 (4)	C31C—O3C—C3C	118.9 (4)
O31A—C31A—O3A	122.5 (5)	O31C—C31C—O3C	123.2 (5)
O31A—C31A—C32A	126.9 (5)	O31C—C31C—C32C	127.5 (5)
O3A—C31A—C32A	110.6 (4)	O3C—C31C—C32C	109.3 (5)
C31A—C32A—H32A	109.5	C31C—C32C—H32G	109.5
C31A—C32A—H32B	109.5	C31C—C32C—H32H	109.5
H32A—C32A—H32B	109.5	H32G—C32C—H32H	109.5
C31A—C32A—H32C	109.5	C31C—C32C—H32I	109.5
H32A—C32A—H32C	109.5	H32G—C32C—H32I	109.5
H32B—C32A—H32C	109.5	H32H—C32C—H32I	109.5
C41A—O4A—C4A	118.5 (4)	C41C—O4C—C4C	119.0 (4)
O41A—C41A—O4A	122.5 (5)	O41C—C41C—O4C	123.0 (6)
O41A—C41A—C42A	126.9 (5)	O41C—C41C—C42C	126.7 (6)
O4A—C41A—C42A	110.5 (5)	O4C—C41C—C42C	110.2 (5)
C41A—C42A—H42A	109.5	C41C—C42C—H42G	109.5
C41A—C42A—H42B	109.5	C41C—C42C—H42H	109.5
H42A—C42A—H42B	109.5	H42G—C42C—H42H	109.5
C41A—C42A—H42C	109.5	C41C—C42C—H42I	109.5
H42A—C42A—H42C	109.5	H42G—C42C—H42I	109.5
H42B—C42A—H42C	109.5	H42H—C42C—H42I	109.5
O51A—C6A—C5A	107.2 (4)	O51C—C6C—C5C	108.5 (4)
O51A—C6A—H6A	110.3	O51C—C6C—H6E	110.0
C5A—C6A—H6A	110.3	C5C—C6C—H6E	110.0
O51A—C6A—H6B	110.3	O51C—C6C—H6F	110.0
C5A—C6A—H6B	110.3	C5C—C6C—H6F	110.0
H6A—C6A—H6B	108.5	H6E—C6C—H6F	108.4
C6A—O51A—S1A	119.7 (3)	C6C—O51C—S1C	118.3 (3)
O52A—S1A—O53A	120.8 (3)	O53C—S1C—O52C	120.5 (2)
O52A—S1A—O51A	104.0 (2)	O53C—S1C—O51C	104.1 (2)
O53A—S1A—O51A	108.6 (2)	O52C—S1C—O51C	108.8 (2)
O52A—S1A—C51A	109.5 (3)	O53C—S1C—C51C	110.2 (2)
O53A—S1A—C51A	108.9 (3)	O52C—S1C—C51C	109.1 (2)
O51A—S1A—C51A	103.7 (2)	O51C—S1C—C51C	102.6 (2)
C52A—C51A—C56A	119.3 (5)	C56C—C51C—C52C	119.7 (5)
C52A—C51A—S1A	121.2 (5)	C56C—C51C—S1C	121.4 (4)
C56A—C51A—S1A	119.5 (4)	C52C—C51C—S1C	118.8 (4)
C53A—C52A—C51A	118.5 (6)	C53C—C52C—C51C	119.7 (5)
C53A—C52A—H52A	120.8	C53C—C52C—H52C	120.1
C51A—C52A—H52A	120.8	C51C—C52C—H52C	120.2
C54A—C53A—C52A	123.1 (6)	C52C—C53C—C54C	121.2 (5)
C54A—C53A—H53A	118.5	C52C—C53C—H53C	119.4
C52A—C53A—H53A	118.5	C54C—C53C—H53C	119.4
C53A—C54A—C55A	118.3 (6)	C55C—C54C—C53C	118.7 (6)
C53A—C54A—C57A	121.6 (6)	C55C—C54C—C57C	120.8 (5)
C55A—C54A—C57A	120.1 (6)	C53C—C54C—C57C	120.5 (5)
C56A—C55A—C54A	120.3 (6)	C54C—C55C—C56C	121.1 (5)
C56A—C55A—H55A	119.9	C54C—C55C—H55C	119.5
C54A—C55A—H55A	119.9	C56C—C55C—H55C	119.5
C55A—C56A—C51A	120.5 (5)	C51C—C56C—C55C	119.6 (5)
C55A—C56A—H56A	119.8	C51C—C56C—H56C	120.2
C51A—C56A—H56A	119.8	C55C—C56C—H56C	120.2
C54A—C57A—H57A	109.5	C54C—C57C—H57G	109.5
C54A—C57A—H57B	109.5	C54C—C57C—H57H	109.5
H57A—C57A—H57B	109.5	H57G—C57C—H57H	109.5
C54A—C57A—H57C	109.5	C54C—C57C—H57I	109.5
H57A—C57A—H57C	109.5	H57G—C57C—H57I	109.5
H57B—C57A—H57C	109.5	H57H—C57C—H57I	109.5
O5B—C1B—O1A	111.2 (4)	O5D—C1D—O1B	110.3 (4)
O5B—C1B—C2B	110.0 (4)	O5D—C1D—C2D	109.3 (4)
O1A—C1B—C2B	109.7 (4)	O1B—C1D—C2D	109.0 (4)
O5B—C1B—H1B	108.6	O5D—C1D—H1D	109.4
O1A—C1B—H1B	108.6	O1B—C1D—H1D	109.4
C2B—C1B—H1B	108.6	C2D—C1D—H1D	109.4
O2B—C2B—C3B	108.2 (4)	O2D—C2D—C3D	107.6 (4)
O2B—C2B—C1B	111.1 (4)	O2D—C2D—C1D	110.6 (4)
C3B—C2B—C1B	111.8 (4)	C3D—C2D—C1D	111.2 (4)
O2B—C2B—H2B	108.6	O2D—C2D—H2D	109.1
C3B—C2B—H2B	108.6	C3D—C2D—H2D	109.1
C1B—C2B—H2B	108.6	C1D—C2D—H2D	109.1
O3B—C3B—C4B	110.0 (4)	O3D—C3D—C2D	108.1 (4)
O3B—C3B—C2B	104.8 (4)	O3D—C3D—C4D	106.9 (4)
C4B—C3B—C2B	111.5 (4)	C2D—C3D—C4D	110.5 (4)
O3B—C3B—H3B	110.2	O3D—C3D—H3D	110.4
C4B—C3B—H3B	110.2	C2D—C3D—H3D	110.4
C2B—C3B—H3B	110.2	C4D—C3D—H3D	110.4
O4B—C4B—C3B	110.0 (4)	O4D—C4D—C5D	108.8 (4)
O4B—C4B—C5B	105.3 (4)	O4D—C4D—C3D	107.4 (4)
C3B—C4B—C5B	111.7 (5)	C5D—C4D—C3D	109.9 (4)
O4B—C4B—H4B	109.9	O4D—C4D—H4D	110.2
C3B—C4B—H4B	109.9	C5D—C4D—H4D	110.2
C5B—C4B—H4B	109.9	C3D—C4D—H4D	110.2
O5B—C5B—C6B	106.5 (4)	O5D—C5D—C6D	107.4 (4)
O5B—C5B—C4B	109.4 (4)	O5D—C5D—C4D	107.8 (4)
C6B—C5B—C4B	111.6 (5)	C6D—C5D—C4D	113.6 (4)
O5B—C5B—H5B	109.8	O5D—C5D—H5D	109.3
C6B—C5B—H5B	109.8	C6D—C5D—H5D	109.3
C4B—C5B—H5B	109.8	C4D—C5D—H5D	109.3
C1B—O5B—C5B	113.5 (4)	C1D—O5D—C5D	114.9 (4)
C21B—O2B—C2B	115.2 (4)	C21D—O2D—C2D	116.7 (4)
O21B—C21B—O2B	123.0 (6)	O21D—C21D—O2D	122.4 (6)
O21B—C21B—C22B	126.3 (6)	O21D—C21D—C22D	126.0 (6)
O2B—C21B—C22B	110.6 (5)	O2D—C21D—C22D	111.7 (5)
C21B—C22B—H22D	109.5	C21D—C22D—H22J	109.5
C21B—C22B—H22E	109.5	C21D—C22D—H22K	109.5
H22D—C22B—H22E	109.5	H22J—C22D—H22K	109.5
C21B—C22B—H22F	109.5	C21D—C22D—H22L	109.5
H22D—C22B—H22F	109.5	H22J—C22D—H22L	109.5
H22E—C22B—H22F	109.5	H22K—C22D—H22L	109.5
C31B—O3B—C3B	119.2 (4)	C31D—O3D—C3D	118.1 (4)
O31B—C31B—O3B	123.1 (5)	O31D—C31D—O3D	123.0 (5)
O31B—C31B—C32B	125.8 (5)	O31D—C31D—C32D	125.6 (6)
O3B—C31B—C32B	111.2 (5)	O3D—C31D—C32D	111.4 (5)
C31B—C32B—H32D	109.5	C31D—C32D—H32J	109.5
C31B—C32B—H32E	109.5	C31D—C32D—H32K	109.5
H32D—C32B—H32E	109.5	H32J—C32D—H32K	109.5
C31B—C32B—H32F	109.5	C31D—C32D—H32L	109.5
H32D—C32B—H32F	109.5	H32J—C32D—H32L	109.5
H32E—C32B—H32F	109.5	H32K—C32D—H32L	109.5
C41B—O4B—C4B	118.3 (4)	C41D—O4D—C4D	117.4 (4)
O41B—C41B—O4B	124.2 (6)	O41D—C41D—O4D	123.9 (6)
O41B—C41B—C42B	125.4 (6)	O41D—C41D—C42D	125.0 (6)
O4B—C41B—C42B	110.5 (5)	O4D—C41D—C42D	111.0 (5)
C41B—C42B—H42D	109.5	C41D—C42D—H42J	109.5
C41B—C42B—H42E	109.5	C41D—C42D—H42K	109.5
H42D—C42B—H42E	109.5	H42J—C42D—H42K	109.5
C41B—C42B—H42F	109.5	C41D—C42D—H42L	109.5
H42D—C42B—H42F	109.5	H42J—C42D—H42L	109.5
H42E—C42B—H42F	109.5	H42K—C42D—H42L	109.5
O51B—C6B—C5B	105.9 (4)	O51D—C6D—C5D	109.9 (4)
O51B—C6B—H6C	110.6	O51D—C6D—H61G	109.7
C5B—C6B—H6C	110.6	C5D—C6D—H61G	109.7
O51B—C6B—H6D	110.6	O51D—C6D—H61H	109.7
C5B—C6B—H6D	110.6	C5D—C6D—H61H	109.7
H6C—C6B—H6D	108.7	H61G—C6D—H61H	108.2
C6B—O51B—S1B	116.1 (3)	C6D—O51D—S1D	120.5 (3)
O52B—S1B—O53B	117.2 (3)	O53D—S1D—O52D	119.8 (3)
O52B—S1B—O51B	109.0 (2)	O53D—S1D—O51D	108.1 (2)
O53B—S1B—O51B	109.4 (2)	O52D—S1D—O51D	109.0 (2)
O52B—S1B—C51B	111.3 (3)	O53D—S1D—C51D	110.0 (3)
O53B—S1B—C51B	110.1 (3)	O52D—S1D—C51D	108.3 (3)
O51B—S1B—C51B	98.2 (2)	O51D—S1D—C51D	99.7 (2)
C56B—C51B—C52B	120.8 (6)	C56D—C51D—C52D	120.5 (6)
C56B—C51B—S1B	120.2 (5)	C56D—C51D—S1D	119.8 (5)
C52B—C51B—S1B	119.0 (5)	C52D—C51D—S1D	119.7 (4)
C53B—C52B—C51B	117.7 (7)	C51D—C52D—C53D	119.5 (6)
C53B—C52B—H52B	121.2	C51D—C52D—H52D	120.2
C51B—C52B—H52B	121.2	C53D—C52D—H52D	120.2
C52B—C53B—C54B	122.5 (7)	C54D—C53D—C52D	120.5 (6)
C52B—C53B—H53B	118.8	C54D—C53D—H53D	119.7
C54B—C53B—H53B	118.8	C52D—C53D—H53D	119.7
C53B—C54B—C55B	119.4 (7)	C53D—C54D—C55D	119.4 (6)
C53B—C54B—C57B	121.2 (8)	C53D—C54D—C57D	120.6 (6)
C55B—C54B—C57B	119.4 (8)	C55D—C54D—C57D	120.0 (6)
C54B—C55B—C56B	119.3 (7)	C54D—C55D—C56D	120.1 (6)
C54B—C55B—H55B	120.3	C54D—C55D—H55D	120.0
C56B—C55B—H55B	120.3	C56D—C55D—H55D	120.0
C51B—C56B—C55B	120.3 (7)	C51D—C56D—C55D	120.0 (6)
C51B—C56B—H56B	119.8	C51D—C56D—H56D	120.0
C55B—C56B—H56B	119.8	C55D—C56D—H56D	120.0
C54B—C57B—H57D	109.5	C54D—C57D—H57J	109.5
C54B—C57B—H57E	109.5	C54D—C57D—H57K	109.5
H57D—C57B—H57E	109.5	H57J—C57D—H57K	109.5
C54B—C57B—H57F	109.5	C54D—C57D—H57L	109.5
H57D—C57B—H57F	109.5	H57J—C57D—H57L	109.5
H57E—C57B—H57F	109.5	H57K—C57D—H57L	109.5
O5A—C1A—C2A—O2A	176.1 (4)	O5C—C1C—C2C—O2C	174.0 (4)
O1A—C1A—C2A—O2A	54.3 (5)	O1B—C1C—C2C—O2C	51.9 (5)
O5A—C1A—C2A—C3A	56.0 (5)	O5C—C1C—C2C—C3C	55.0 (5)
O1A—C1A—C2A—C3A	−65.8 (5)	O1B—C1C—C2C—C3C	−67.1 (5)
O2A—C2A—C3A—O3A	69.6 (5)	O2C—C2C—C3C—O3C	70.3 (5)
C1A—C2A—C3A—O3A	−168.8 (4)	C1C—C2C—C3C—O3C	−168.3 (4)
O2A—C2A—C3A—C4A	−173.1 (4)	O2C—C2C—C3C—C4C	−170.9 (4)
C1A—C2A—C3A—C4A	−51.5 (5)	C1C—C2C—C3C—C4C	−49.5 (6)
O3A—C3A—C4A—O4A	−77.1 (4)	O3C—C3C—C4C—O4C	−77.9 (5)
C2A—C3A—C4A—O4A	166.6 (4)	C2C—C3C—C4C—O4C	165.4 (4)
O3A—C3A—C4A—C5A	167.3 (4)	O3C—C3C—C4C—C5C	166.2 (4)
C2A—C3A—C4A—C5A	51.1 (5)	C2C—C3C—C4C—C5C	49.6 (5)
O4A—C4A—C5A—O5A	−170.5 (4)	O4C—C4C—C5C—O5C	−171.0 (4)
C3A—C4A—C5A—O5A	−53.4 (5)	C3C—C4C—C5C—O5C	−54.6 (5)
O4A—C4A—C5A—C6A	72.0 (5)	O4C—C4C—C5C—C6C	71.5 (5)
C3A—C4A—C5A—C6A	−170.9 (4)	C3C—C4C—C5C—C6C	−172.1 (4)
O1A—C1A—O5A—C5A	58.6 (5)	O1B—C1C—O5C—C5C	58.2 (5)
C2A—C1A—O5A—C5A	−61.9 (5)	C2C—C1C—O5C—C5C	−62.4 (5)
C6A—C5A—O5A—C1A	−177.8 (4)	C6C—C5C—O5C—C1C	−177.6 (4)
C4A—C5A—O5A—C1A	60.3 (5)	C4C—C5C—O5C—C1C	62.5 (5)
O5A—C1A—O1A—C1B	78.4 (5)	O5C—C1C—O1B—C1D	82.7 (5)
C2A—C1A—O1A—C1B	−160.4 (4)	C2C—C1C—O1B—C1D	−156.2 (4)
C3A—C2A—O2A—C21A	−148.5 (4)	C1C—C2C—O2C—C21C	103.2 (5)
C1A—C2A—O2A—C21A	89.9 (5)	C3C—C2C—O2C—C21C	−134.9 (4)
C2A—O2A—C21A—O21A	−2.3 (7)	C2C—O2C—C21C—O21C	−4.7 (7)
C2A—O2A—C21A—C22A	176.9 (4)	C2C—O2C—C21C—C22C	174.2 (4)
C4A—C3A—O3A—C31A	103.8 (5)	C4C—C3C—O3C—C31C	100.5 (5)
C2A—C3A—O3A—C31A	−136.7 (4)	C2C—C3C—O3C—C31C	−139.7 (5)
C3A—O3A—C31A—O31A	0.5 (8)	C3C—O3C—C31C—O31C	3.1 (9)
C3A—O3A—C31A—C32A	−178.8 (5)	C3C—O3C—C31C—C32C	−176.5 (5)
C3A—C4A—O4A—C41A	101.8 (5)	C3C—C4C—O4C—C41C	98.6 (5)
C5A—C4A—O4A—C41A	−138.6 (5)	C5C—C4C—O4C—C41C	−142.1 (5)
C4A—O4A—C41A—O41A	5.8 (9)	C4C—O4C—C41C—O41C	4.4 (9)
C4A—O4A—C41A—C42A	−170.9 (4)	C4C—O4C—C41C—C42C	−171.7 (5)
O5A—C5A—C6A—O51A	74.2 (4)	O5C—C5C—C6C—O51C	76.3 (5)
C4A—C5A—C6A—O51A	−166.6 (4)	C4C—C5C—C6C—O51C	−164.7 (4)
C5A—C6A—O51A—S1A	−143.4 (3)	C5C—C6C—O51C—S1C	−134.8 (4)
C6A—O51A—S1A—O52A	−169.5 (4)	C6C—O51C—S1C—O53C	−173.2 (4)
C6A—O51A—S1A—O53A	−39.7 (4)	C6C—O51C—S1C—O52C	−43.6 (4)
C6A—O51A—S1A—C51A	76.0 (4)	C6C—O51C—S1C—C51C	71.9 (4)
O52A—S1A—C51A—C52A	126.7 (5)	O53C—S1C—C51C—C56C	142.1 (4)
O53A—S1A—C51A—C52A	−7.3 (6)	O52C—S1C—C51C—C56C	7.8 (5)
O51A—S1A—C51A—C52A	−122.8 (5)	O51C—S1C—C51C—C56C	−107.5 (5)
O52A—S1A—C51A—C56A	−51.5 (5)	O53C—S1C—C51C—C52C	−40.3 (5)
O53A—S1A—C51A—C56A	174.6 (4)	O52C—S1C—C51C—C52C	−174.7 (4)
O51A—S1A—C51A—C56A	59.1 (5)	O51C—S1C—C51C—C52C	70.0 (4)
C56A—C51A—C52A—C53A	0.8 (10)	C56C—C51C—C52C—C53C	0.8 (8)
S1A—C51A—C52A—C53A	−177.4 (5)	S1C—C51C—C52C—C53C	−176.8 (4)
C51A—C52A—C53A—C54A	−2.7 (11)	C51C—C52C—C53C—C54C	−0.7 (8)
C52A—C53A—C54A—C55A	2.4 (11)	C52C—C53C—C54C—C55C	0.1 (8)
C52A—C53A—C54A—C57A	−178.0 (7)	C52C—C53C—C54C—C57C	−179.7 (5)
C53A—C54A—C55A—C56A	−0.1 (10)	C53C—C54C—C55C—C56C	0.4 (9)
C57A—C54A—C55A—C56A	−179.8 (6)	C57C—C54C—C55C—C56C	−179.8 (5)
C54A—C55A—C56A—C51A	−1.7 (9)	C52C—C51C—C56C—C55C	−0.3 (8)
C52A—C51A—C56A—C55A	1.4 (9)	S1C—C51C—C56C—C55C	177.3 (4)
S1A—C51A—C56A—C55A	179.6 (5)	C54C—C55C—C56C—C51C	−0.3 (9)
C1A—O1A—C1B—O5B	81.9 (5)	C1C—O1B—C1D—O5D	83.6 (5)
C1A—O1A—C1B—C2B	−156.2 (4)	C1C—O1B—C1D—C2D	−156.5 (4)
O5B—C1B—C2B—O2B	174.9 (4)	O5D—C1D—C2D—O2D	173.5 (4)
O1A—C1B—C2B—O2B	52.3 (6)	O1B—C1D—C2D—O2D	52.9 (5)
O5B—C1B—C2B—C3B	54.0 (6)	O5D—C1D—C2D—C3D	54.1 (5)
O1A—C1B—C2B—C3B	−68.6 (6)	O1B—C1D—C2D—C3D	−66.6 (5)
O2B—C2B—C3B—O3B	69.9 (5)	O2D—C2D—C3D—O3D	69.8 (5)
C1B—C2B—C3B—O3B	−167.5 (4)	C1D—C2D—C3D—O3D	−169.0 (4)
O2B—C2B—C3B—C4B	−171.1 (4)	O2D—C2D—C3D—C4D	−173.6 (4)
C1B—C2B—C3B—C4B	−48.6 (6)	C1D—C2D—C3D—C4D	−52.3 (5)
O3B—C3B—C4B—O4B	−78.7 (5)	O3D—C3D—C4D—O4D	−70.1 (5)
C2B—C3B—C4B—O4B	165.6 (4)	C2D—C3D—C4D—O4D	172.6 (4)
O3B—C3B—C4B—C5B	164.8 (4)	O3D—C3D—C4D—C5D	171.7 (4)
C2B—C3B—C4B—C5B	49.0 (6)	C2D—C3D—C4D—C5D	54.4 (5)
O4B—C4B—C5B—O5B	−173.4 (4)	O4D—C4D—C5D—O5D	−174.6 (4)
C3B—C4B—C5B—O5B	−54.0 (5)	C3D—C4D—C5D—O5D	−57.3 (5)
O4B—C4B—C5B—C6B	69.0 (5)	O4D—C4D—C5D—C6D	66.6 (5)
C3B—C4B—C5B—C6B	−171.6 (5)	C3D—C4D—C5D—C6D	−176.1 (4)
O1A—C1B—O5B—C5B	59.9 (5)	O1B—C1D—O5D—C5D	58.6 (5)
C2B—C1B—O5B—C5B	−61.8 (5)	C2D—C1D—O5D—C5D	−61.2 (5)
C6B—C5B—O5B—C1B	−177.4 (4)	C6D—C5D—O5D—C1D	−174.1 (4)
C4B—C5B—O5B—C1B	61.9 (5)	C4D—C5D—O5D—C1D	63.2 (5)
C3B—C2B—O2B—C21B	−146.7 (4)	C3D—C2D—O2D—C21D	−150.4 (4)
C1B—C2B—O2B—C21B	90.3 (5)	C1D—C2D—O2D—C21D	88.0 (5)
C2B—O2B—C21B—O21B	−3.9 (7)	C2D—O2D—C21D—O21D	−5.1 (7)
C2B—O2B—C21B—C22B	174.2 (4)	C2D—O2D—C21D—C22D	174.6 (4)
C4B—C3B—O3B—C31B	97.5 (5)	C2D—C3D—O3D—C31D	−114.8 (5)
C2B—C3B—O3B—C31B	−142.6 (5)	C4D—C3D—O3D—C31D	126.3 (5)
C3B—O3B—C31B—O31B	−1.5 (8)	C3D—O3D—C31D—O31D	0.5 (8)
C3B—O3B—C31B—C32B	178.6 (5)	C3D—O3D—C31D—C32D	179.8 (5)
C3B—C4B—O4B—C41B	91.9 (5)	C5D—C4D—O4D—C41D	−138.2 (5)
C5B—C4B—O4B—C41B	−147.6 (5)	C3D—C4D—O4D—C41D	102.9 (5)
C4B—O4B—C41B—O41B	4.5 (9)	C4D—O4D—C41D—O41D	6.2 (9)
C4B—O4B—C41B—C42B	−175.2 (5)	C4D—O4D—C41D—C42D	−171.4 (5)
O5B—C5B—C6B—O51B	67.5 (5)	O5D—C5D—C6D—O51D	69.8 (5)
C4B—C5B—C6B—O51B	−173.3 (4)	C4D—C5D—C6D—O51D	−171.1 (4)
C5B—C6B—O51B—S1B	−173.1 (3)	C5D—C6D—O51D—S1D	−96.9 (5)
C6B—O51B—S1B—O52B	52.3 (4)	C6D—O51D—S1D—O53D	−29.9 (5)
C6B—O51B—S1B—O53B	−77.0 (4)	C6D—O51D—S1D—O52D	101.9 (4)
C6B—O51B—S1B—C51B	168.3 (4)	C6D—O51D—S1D—C51D	−144.7 (4)
O52B—S1B—C51B—C56B	−134.8 (5)	O53D—S1D—C51D—C56D	157.1 (5)
O53B—S1B—C51B—C56B	−3.2 (6)	O52D—S1D—C51D—C56D	24.4 (6)
O51B—S1B—C51B—C56B	111.1 (5)	O51D—S1D—C51D—C56D	−89.5 (5)
O52B—S1B—C51B—C52B	46.3 (6)	O53D—S1D—C51D—C52D	−23.9 (6)
O53B—S1B—C51B—C52B	177.9 (5)	O52D—S1D—C51D—C52D	−156.6 (5)
O51B—S1B—C51B—C52B	−67.8 (5)	O51D—S1D—C51D—C52D	89.6 (5)
C56B—C51B—C52B—C53B	−2.0 (9)	C56D—C51D—C52D—C53D	−2.1 (10)
S1B—C51B—C52B—C53B	176.8 (5)	S1D—C51D—C52D—C53D	178.9 (5)
C51B—C52B—C53B—C54B	0.1 (10)	C51D—C52D—C53D—C54D	1.0 (10)
C52B—C53B—C54B—C55B	2.4 (11)	C52D—C53D—C54D—C55D	0.3 (10)
C52B—C53B—C54B—C57B	−175.7 (7)	C52D—C53D—C54D—C57D	179.1 (6)
C53B—C54B—C55B—C56B	−2.8 (11)	C53D—C54D—C55D—C56D	−0.7 (10)
C57B—C54B—C55B—C56B	175.3 (6)	C57D—C54D—C55D—C56D	−179.4 (6)
C52B—C51B—C56B—C55B	1.6 (10)	C52D—C51D—C56D—C55D	1.8 (9)
S1B—C51B—C56B—C55B	−177.3 (5)	S1D—C51D—C56D—C55D	−179.2 (5)
C54B—C55B—C56B—C51B	0.9 (11)	C54D—C55D—C56D—C51D	−0.4 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4C—H4C···O41D^i	1.00	2.46	3.365 (7)	150
C6C—H6F···O41D^i	0.99	2.49	3.272 (6)	136
C55C—H55C···O31B^ii	0.95	2.41	3.313 (7)	160
C53D—H53D···Cg1^iii	0.95	2.66	3.418 (7)	137

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x, y+1, z; (iii) −x+1/2, −y+2, z+1/2.

(7) 2,2',3,3',4,4'-Hexaacetato-6,6'-diazido-α,α'-trehalose ethanol solvate

Crystal data

C24H32N6O15·0.35(C2H6O)	F(000) = 1388.4
Mr = 660.68	Dx = 1.272 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4368 reflections
a = 12.2281 (4) Å	θ = 3.1–27.5°
b = 15.5803 (6) Å	µ = 0.11 mm^−1
c = 18.1066 (8) Å	T = 150 K
V = 3449.6 (2) Å^3	Block, colourless
Z = 4	0.50 × 0.30 × 0.25 mm

Data collection

Kappa-CCD diffractometer	4368 independent reflections
Radiation source: rotating anode	2580 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −12→15
Tmin = 0.942, Tmax = 0.974	k = −18→20
17686 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.191	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.1153P)^2] where P = (Fo^2 + 2Fc^2)/3
4368 reflections	(Δ/σ)max < 0.001
439 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.7273 (4)	0.5181 (3)	0.4466 (3)	0.0365 (10)
C2A	0.7742 (4)	0.4712 (3)	0.3810 (2)	0.0336 (10)
C3A	0.8923 (4)	0.4959 (3)	0.3658 (2)	0.0330 (10)
C4A	0.9075 (3)	0.5916 (3)	0.3666 (2)	0.0319 (10)
C5A	0.8580 (3)	0.6310 (3)	0.4358 (2)	0.0323 (9)
O5A	0.7436 (2)	0.60728 (18)	0.43835 (16)	0.0345 (7)
O2A	0.7729 (3)	0.3800 (2)	0.39166 (17)	0.0405 (8)
C21A	0.6879 (4)	0.3350 (3)	0.3645 (3)	0.0465 (13)
O21A	0.6104 (3)	0.3700 (3)	0.3364 (2)	0.0626 (11)
C22A	0.7051 (5)	0.2414 (3)	0.3729 (4)	0.0600 (16)
O3A	0.9178 (2)	0.4638 (2)	0.29326 (16)	0.0368 (7)
C31A	1.0100 (4)	0.4164 (3)	0.2837 (3)	0.0431 (12)
O31A	1.0708 (3)	0.4003 (3)	0.3329 (2)	0.0623 (11)
C32A	1.0201 (5)	0.3898 (4)	0.2051 (3)	0.0566 (15)
O4A	1.0246 (2)	0.6075 (2)	0.36833 (17)	0.0380 (8)
C41A	1.0734 (4)	0.6307 (3)	0.3050 (3)	0.0400 (11)
O41A	1.0256 (3)	0.6505 (3)	0.2501 (2)	0.0739 (13)
C42A	1.1956 (4)	0.6277 (4)	0.3128 (3)	0.0519 (14)
C6A	0.8601 (4)	0.7286 (3)	0.4344 (3)	0.0400 (11)
N61A	0.8151 (4)	0.7641 (3)	0.5034 (3)	0.0507 (11)
N62A	0.7133 (5)	0.7705 (4)	0.5022 (3)	0.0755 (16)
N63A	0.6214 (6)	0.7808 (6)	0.5069 (5)	0.130 (3)
O1A	0.7745 (3)	0.4874 (2)	0.51250 (16)	0.0361 (7)
C1B	0.7050 (4)	0.4999 (3)	0.5742 (2)	0.0368 (11)
C2B	0.7717 (4)	0.4976 (3)	0.6441 (2)	0.0361 (11)
C3B	0.8181 (4)	0.4091 (3)	0.6604 (2)	0.0368 (11)
C4B	0.7299 (4)	0.3419 (3)	0.6550 (3)	0.0412 (11)
C5B	0.6655 (4)	0.3517 (3)	0.5831 (3)	0.0431 (12)
O5B	0.6234 (3)	0.4363 (2)	0.57713 (17)	0.0434 (8)
O2B	0.8642 (3)	0.5549 (2)	0.64116 (18)	0.0393 (8)
C21B	0.8466 (4)	0.6365 (3)	0.6612 (3)	0.0432 (12)
O21B	0.7572 (4)	0.6626 (2)	0.6776 (3)	0.0691 (12)
C22B	0.9484 (5)	0.6890 (3)	0.6601 (3)	0.0539 (14)
O3B	0.8586 (3)	0.4111 (2)	0.73484 (17)	0.0398 (8)
C31B	0.9673 (4)	0.4051 (3)	0.7473 (3)	0.0474 (13)
O31B	1.0329 (4)	0.3954 (4)	0.6980 (3)	0.1026 (19)
C32B	0.9931 (4)	0.4164 (3)	0.8266 (3)	0.0473 (13)
O4B	0.7800 (3)	0.2568 (2)	0.65226 (18)	0.0443 (9)
C41B	0.7822 (4)	0.2105 (3)	0.7152 (3)	0.0413 (11)
O41B	0.7506 (3)	0.2380 (2)	0.77264 (19)	0.0526 (9)
C42B	0.8330 (4)	0.1250 (3)	0.7022 (3)	0.0532 (14)
C6B	0.5673 (5)	0.2906 (4)	0.5805 (3)	0.0564 (15)
N61B	0.5151 (5)	0.2915 (4)	0.5069 (3)	0.0709 (15)
N62B	0.4528 (7)	0.3508 (6)	0.4967 (3)	0.090 (2)
N63B	0.3935 (8)	0.4041 (8)	0.4793 (5)	0.146 (4)
O100	0.3909 (11)	0.5325 (8)	1.0278 (6)	0.072 (3)	0.35
C101	0.3130 (10)	0.5005 (8)	1.0798 (7)	0.050 (4)	0.35
C102	0.2538 (10)	0.4881 (8)	1.1251 (7)	0.088 (7)	0.35
H1A	0.6468	0.5069	0.4484	0.044*
H2A	0.7293	0.4853	0.3365	0.040*
H3A	0.9414	0.4686	0.4032	0.040*
H4A	0.8743	0.6179	0.3215	0.038*
H5A	0.8967	0.6092	0.4807	0.039*
H22A	0.7674	0.2235	0.3426	0.090*
H22B	0.6393	0.2107	0.3569	0.090*
H22C	0.7200	0.2281	0.4248	0.090*
H32A	1.0878	0.3571	0.1984	0.085*
H32B	1.0216	0.4408	0.1735	0.085*
H32C	0.9574	0.3538	0.1916	0.085*
H42A	1.2243	0.6863	0.3163	0.078*
H42B	1.2274	0.5991	0.2697	0.078*
H42C	1.2149	0.5958	0.3576	0.078*
H6A	0.9363	0.7487	0.4279	0.048*
H6B	0.8166	0.7495	0.3920	0.048*
H1B	0.6692	0.5574	0.5699	0.044*
H2B	0.7238	0.5152	0.6863	0.043*
H3B	0.8789	0.3956	0.6254	0.044*
H4B	0.6795	0.3461	0.6983	0.049*
H5B	0.7147	0.3397	0.5402	0.052*
H22D	0.9504	0.7261	0.7038	0.081*
H22E	0.9496	0.7246	0.6154	0.081*
H22F	1.0122	0.6510	0.6603	0.081*
H32D	0.9817	0.4765	0.8405	0.071*
H32E	1.0695	0.4006	0.8355	0.071*
H32F	0.9451	0.3796	0.8562	0.071*
H42D	0.8338	0.0923	0.7484	0.080*
H42E	0.9081	0.1327	0.6845	0.080*
H42F	0.7906	0.0936	0.6650	0.080*
H6C	0.5919	0.2316	0.5922	0.068*
H6D	0.5132	0.3080	0.6184	0.068*
H100	0.3970 (10)	0.4977 (8)	0.9940 (7)	0.109*	0.35
H10A	0.2618	0.4809	1.0409	0.060*	0.35
H10B	0.3563	0.4483	1.0906	0.060*	0.35
H10C	0.1791	0.4930	1.1061	0.132*	0.35
H10D	0.2648	0.5302	1.1647	0.132*	0.35
H10E	0.2653	0.4301	1.1447	0.132*	0.35

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.020 (2)	0.048 (3)	0.041 (2)	−0.007 (2)	−0.001 (2)	0.004 (2)
C2A	0.019 (2)	0.045 (2)	0.037 (2)	−0.003 (2)	−0.0033 (19)	0.002 (2)
C3A	0.020 (2)	0.045 (3)	0.034 (2)	0.0021 (19)	−0.0006 (18)	0.002 (2)
C4A	0.013 (2)	0.047 (2)	0.035 (2)	−0.0022 (19)	−0.0002 (18)	0.003 (2)
C5A	0.016 (2)	0.046 (2)	0.034 (2)	−0.0018 (19)	−0.0015 (18)	0.003 (2)
O5A	0.0159 (15)	0.0456 (17)	0.0418 (16)	0.0010 (13)	0.0018 (13)	0.0002 (14)
O2A	0.0285 (18)	0.0421 (17)	0.0509 (18)	−0.0054 (15)	−0.0080 (15)	−0.0033 (15)
C21A	0.037 (3)	0.054 (3)	0.049 (3)	−0.009 (3)	0.000 (3)	−0.010 (3)
O21A	0.036 (2)	0.068 (2)	0.085 (3)	−0.008 (2)	−0.019 (2)	−0.006 (2)
C22A	0.054 (4)	0.051 (3)	0.075 (4)	−0.015 (3)	−0.005 (3)	−0.004 (3)
O3A	0.0211 (16)	0.0537 (19)	0.0355 (16)	0.0093 (15)	−0.0023 (13)	−0.0058 (14)
C31A	0.025 (3)	0.052 (3)	0.052 (3)	0.004 (2)	0.004 (2)	−0.004 (2)
O31A	0.035 (2)	0.095 (3)	0.056 (2)	0.028 (2)	−0.0089 (18)	−0.007 (2)
C32A	0.034 (3)	0.076 (4)	0.060 (3)	0.013 (3)	0.004 (3)	−0.015 (3)
O4A	0.0140 (14)	0.057 (2)	0.0433 (18)	−0.0028 (14)	0.0025 (13)	0.0059 (15)
C41A	0.022 (2)	0.049 (3)	0.049 (3)	−0.003 (2)	0.006 (2)	0.001 (2)
O41A	0.039 (2)	0.128 (4)	0.055 (2)	−0.010 (2)	0.005 (2)	0.035 (3)
C42A	0.020 (3)	0.059 (3)	0.077 (4)	−0.002 (2)	0.016 (2)	0.004 (3)
C6A	0.027 (3)	0.053 (3)	0.040 (2)	0.002 (2)	−0.003 (2)	0.003 (2)
N61A	0.043 (3)	0.057 (3)	0.052 (3)	0.009 (2)	−0.004 (2)	−0.010 (2)
N62A	0.056 (4)	0.098 (4)	0.072 (3)	0.011 (3)	0.009 (3)	−0.036 (3)
N63A	0.043 (4)	0.196 (8)	0.152 (7)	0.016 (5)	0.030 (4)	−0.085 (6)
O1A	0.0240 (17)	0.0496 (17)	0.0346 (16)	−0.0017 (14)	0.0030 (13)	0.0027 (14)
C1B	0.026 (2)	0.048 (3)	0.036 (2)	−0.006 (2)	0.0053 (19)	−0.005 (2)
C2B	0.027 (3)	0.045 (2)	0.036 (2)	−0.006 (2)	0.006 (2)	−0.002 (2)
C3B	0.032 (3)	0.044 (3)	0.035 (2)	−0.006 (2)	0.010 (2)	−0.005 (2)
C4B	0.036 (3)	0.045 (3)	0.043 (3)	−0.008 (2)	0.010 (2)	−0.003 (2)
C5B	0.034 (3)	0.054 (3)	0.041 (3)	−0.011 (2)	0.006 (2)	0.000 (2)
O5B	0.0256 (17)	0.062 (2)	0.0429 (18)	−0.0110 (15)	0.0048 (14)	0.0022 (16)
O2B	0.0272 (17)	0.0419 (18)	0.0489 (18)	−0.0037 (14)	0.0057 (15)	−0.0024 (15)
C21B	0.041 (3)	0.043 (3)	0.045 (3)	0.000 (2)	−0.002 (2)	−0.003 (2)
O21B	0.046 (3)	0.051 (2)	0.110 (3)	0.003 (2)	0.007 (2)	−0.013 (2)
C22B	0.044 (3)	0.050 (3)	0.067 (3)	−0.013 (2)	−0.002 (3)	0.004 (3)
O3B	0.0251 (17)	0.0524 (19)	0.0420 (17)	−0.0032 (15)	0.0022 (14)	−0.0021 (15)
C31B	0.031 (3)	0.048 (3)	0.063 (3)	0.018 (2)	0.004 (3)	−0.004 (3)
O31B	0.049 (3)	0.183 (6)	0.076 (3)	0.053 (4)	0.011 (2)	−0.020 (3)
C32B	0.029 (3)	0.052 (3)	0.061 (3)	0.012 (2)	−0.004 (2)	−0.002 (3)
O4B	0.045 (2)	0.0426 (18)	0.0451 (19)	−0.0080 (16)	0.0135 (16)	−0.0029 (15)
C41B	0.029 (3)	0.049 (3)	0.046 (3)	−0.008 (2)	0.000 (2)	−0.003 (2)
O41B	0.049 (2)	0.065 (2)	0.043 (2)	0.0018 (19)	0.0064 (17)	−0.0025 (17)
C42B	0.036 (3)	0.057 (3)	0.066 (3)	−0.003 (2)	0.005 (3)	−0.004 (3)
C6B	0.051 (3)	0.074 (4)	0.044 (3)	−0.032 (3)	0.000 (3)	−0.005 (3)
N61B	0.064 (4)	0.096 (4)	0.053 (3)	−0.026 (3)	−0.007 (3)	−0.012 (3)
N62B	0.077 (5)	0.139 (7)	0.054 (3)	−0.018 (5)	−0.015 (3)	−0.010 (4)
N63B	0.116 (7)	0.226 (11)	0.098 (6)	0.057 (8)	−0.042 (5)	−0.040 (6)
O100	0.073 (9)	0.087 (8)	0.057 (7)	0.007 (7)	0.022 (6)	−0.014 (6)
C101	0.034 (8)	0.066 (10)	0.050 (9)	0.002 (7)	−0.012 (7)	0.029 (8)
C102	0.049 (11)	0.138 (18)	0.077 (13)	−0.024 (12)	−0.014 (10)	0.083 (13)

Geometric parameters (Å, º)

C1A—O1A	1.409 (5)	C2B—O2B	1.441 (5)
C1A—O5A	1.411 (5)	C2B—C3B	1.521 (7)
C1A—C2A	1.508 (6)	C2B—H2B	1.00
C1A—H1A	1.00	C3B—O3B	1.436 (6)
C2A—O2A	1.434 (6)	C3B—C4B	1.506 (6)
C2A—C3A	1.520 (6)	C3B—H3B	1.00
C2A—H2A	1.00	C4B—O4B	1.461 (6)
C3A—O3A	1.440 (5)	C4B—C5B	1.529 (7)
C3A—C4A	1.504 (6)	C4B—H4B	1.00
C3A—H3A	1.00	C5B—O5B	1.419 (6)
C4A—O4A	1.454 (5)	C5B—C6B	1.533 (7)
C4A—C5A	1.520 (6)	C5B—H5B	1.00
C4A—H4A	1.00	O2B—C21B	1.340 (6)
C5A—O5A	1.448 (5)	C21B—O21B	1.203 (6)
C5A—C6A	1.521 (6)	C21B—C22B	1.490 (7)
C5A—H5A	1.00	C22B—H22D	0.98
O2A—C21A	1.346 (6)	C22B—H22E	0.98
C21A—O21A	1.205 (6)	C22B—H22F	0.98
C21A—C22A	1.482 (8)	O3B—C31B	1.352 (6)
C22A—H22A	0.98	C31B—O31B	1.210 (7)
C22A—H22B	0.98	C31B—C32B	1.480 (8)
C22A—H22C	0.98	C32B—H32D	0.98
O3A—C31A	1.359 (6)	C32B—H32E	0.98
C31A—O31A	1.188 (6)	C32B—H32F	0.98
C31A—C32A	1.487 (7)	O4B—C41B	1.350 (6)
C32A—H32A	0.98	C41B—O41B	1.189 (6)
C32A—H32B	0.98	C41B—C42B	1.489 (8)
C32A—H32C	0.98	C42B—H42D	0.98
O4A—C41A	1.342 (6)	C42B—H42E	0.98
C41A—O41A	1.194 (6)	C42B—H42F	0.98
C41A—C42A	1.503 (7)	C6B—N61B	1.478 (8)
C42A—H42A	0.98	C6B—H6C	0.99
C42A—H42B	0.98	C6B—H6D	0.99
C42A—H42C	0.98	N61B—N62B	1.211 (10)
C6A—N61A	1.473 (7)	N62B—N63B	1.146 (11)
C6A—H6A	0.99	O100—C101	1.430 (18)
C6A—H6B	0.99	O100—H100	0.822 (18)
N61A—N62A	1.249 (7)	C101—C102	1.1108
N62A—N63A	1.138 (8)	C101—H10A	0.99
O1A—C1B	1.417 (5)	C101—H10B	0.99
C1B—O5B	1.407 (6)	C102—H10C	0.98
C1B—C2B	1.506 (6)	C102—H10D	0.98
C1B—H1B	1.00	C102—H10E	0.98
O1A—C1A—O5A	111.5 (3)	O2B—C2B—C1B	112.3 (3)
O1A—C1A—C2A	110.3 (3)	O2B—C2B—C3B	106.0 (4)
O5A—C1A—C2A	109.9 (4)	C1B—C2B—C3B	112.8 (4)
O1A—C1A—H1A	108.4	O2B—C2B—H2B	108.5
O5A—C1A—H1A	108.4	C1B—C2B—H2B	108.5
C2A—C1A—H1A	108.4	C3B—C2B—H2B	108.5
O2A—C2A—C1A	111.7 (3)	O3B—C3B—C4B	108.9 (4)
O2A—C2A—C3A	106.6 (3)	O3B—C3B—C2B	106.9 (3)
C1A—C2A—C3A	112.4 (3)	C4B—C3B—C2B	110.5 (4)
O2A—C2A—H2A	108.7	O3B—C3B—H3B	110.1
C1A—C2A—H2A	108.7	C4B—C3B—H3B	110.1
C3A—C2A—H2A	108.7	C2B—C3B—H3B	110.1
O3A—C3A—C4A	109.1 (3)	O4B—C4B—C3B	109.4 (4)
O3A—C3A—C2A	106.5 (3)	O4B—C4B—C5B	106.2 (4)
C4A—C3A—C2A	111.5 (4)	C3B—C4B—C5B	110.8 (4)
O3A—C3A—H3A	109.9	O4B—C4B—H4B	110.1
C4A—C3A—H3A	109.9	C3B—C4B—H4B	110.1
C2A—C3A—H3A	109.9	C5B—C4B—H4B	110.1
O4A—C4A—C3A	106.9 (3)	O5B—C5B—C4B	110.1 (4)
O4A—C4A—C5A	107.8 (3)	O5B—C5B—C6B	106.9 (4)
C3A—C4A—C5A	111.0 (4)	C4B—C5B—C6B	111.5 (4)
O4A—C4A—H4A	110.3	O5B—C5B—H5B	109.4
C3A—C4A—H4A	110.3	C4B—C5B—H5B	109.4
C5A—C4A—H4A	110.3	C6B—C5B—H5B	109.4
O5A—C5A—C4A	107.9 (3)	C1B—O5B—C5B	113.6 (3)
O5A—C5A—C6A	105.8 (3)	C21B—O2B—C2B	116.9 (4)
C4A—C5A—C6A	112.5 (4)	O21B—C21B—O2B	122.2 (5)
O5A—C5A—H5A	110.2	O21B—C21B—C22B	125.3 (5)
C4A—C5A—H5A	110.2	O2B—C21B—C22B	112.6 (5)
C6A—C5A—H5A	110.2	C21B—C22B—H22D	109.5
C1A—O5A—C5A	113.0 (3)	C21B—C22B—H22E	109.5
C21A—O2A—C2A	118.3 (4)	H22D—C22B—H22E	109.5
O21A—C21A—O2A	121.8 (5)	C21B—C22B—H22F	109.5
O21A—C21A—C22A	126.8 (5)	H22D—C22B—H22F	109.5
O2A—C21A—C22A	111.4 (5)	H22E—C22B—H22F	109.5
C21A—C22A—H22A	109.5	C31B—O3B—C3B	119.6 (4)
C21A—C22A—H22B	109.5	O31B—C31B—O3B	122.6 (5)
H22A—C22A—H22B	109.5	O31B—C31B—C32B	126.1 (5)
C21A—C22A—H22C	109.5	O3B—C31B—C32B	111.3 (4)
H22A—C22A—H22C	109.5	C31B—C32B—H32D	109.5
H22B—C22A—H22C	109.5	C31B—C32B—H32E	109.5
C31A—O3A—C3A	119.0 (3)	H32D—C32B—H32E	109.5
O31A—C31A—O3A	122.6 (4)	C31B—C32B—H32F	109.5
O31A—C31A—C32A	127.4 (5)	H32D—C32B—H32F	109.5
O3A—C31A—C32A	110.0 (4)	H32E—C32B—H32F	109.5
C31A—C32A—H32A	109.5	C41B—O4B—C4B	117.7 (4)
C31A—C32A—H32B	109.5	O41B—C41B—O4B	122.6 (5)
H32A—C32A—H32B	109.5	O41B—C41B—C42B	126.7 (5)
C31A—C32A—H32C	109.5	O4B—C41B—C42B	110.6 (4)
H32A—C32A—H32C	109.5	C41B—C42B—H42D	109.5
H32B—C32A—H32C	109.5	C41B—C42B—H42E	109.5
C41A—O4A—C4A	117.7 (3)	H42D—C42B—H42E	109.5
O41A—C41A—O4A	124.3 (4)	C41B—C42B—H42F	109.5
O41A—C41A—C42A	125.0 (5)	H42D—C42B—H42F	109.5
O4A—C41A—C42A	110.6 (4)	H42E—C42B—H42F	109.5
C41A—C42A—H42A	109.5	N61B—C6B—C5B	111.1 (4)
C41A—C42A—H42B	109.5	N61B—C6B—H6C	109.4
H42A—C42A—H42B	109.5	C5B—C6B—H6C	109.4
C41A—C42A—H42C	109.5	N61B—C6B—H6D	109.4
H42A—C42A—H42C	109.5	C5B—C6B—H6D	109.4
H42B—C42A—H42C	109.5	H6C—C6B—H6D	108.0
N61A—C6A—C5A	110.8 (4)	N62B—N61B—C6B	114.7 (6)
N61A—C6A—H6A	109.5	N63B—N62B—N61B	172.7 (8)
C5A—C6A—H6A	109.5	C101—O100—H100	108.7 (17)
N61A—C6A—H6B	109.5	C102—C101—O100	168.9 (7)
C5A—C6A—H6B	109.5	C102—C101—H10A	93.4
H6A—C6A—H6B	108.1	O100—C101—H10A	93.4
N62A—N61A—C6A	112.8 (4)	C102—C101—H10B	93.4
N63A—N62A—N61A	173.7 (7)	O100—C101—H10B	93.4
C1A—O1A—C1B	112.0 (3)	H10A—C101—H10B	103.1
O5B—C1B—O1A	111.0 (3)	C101—C102—H10C	109.5
O5B—C1B—C2B	109.6 (4)	C101—C102—H10D	109.5
O1A—C1B—C2B	109.5 (4)	H10C—C102—H10D	109.5
O5B—C1B—H1B	108.9	C101—C102—H10E	109.5
O1A—C1B—H1B	108.9	H10C—C102—H10E	109.5
C2B—C1B—H1B	108.9	H10D—C102—H10E	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6B···O41B^i	0.99	2.32	3.268 (6)	160
C6B—H6C···O31A^ii	0.99	2.48	3.363 (8)	149
C6B—H6D···O41A^iii	0.99	2.52	3.400 (7)	148

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) −x+3/2, −y+1, z+1/2.

(8) 2,2',3,3'-Tetraacetato-6,6'-bis(N-acetylamino)-α,α'-trehalose dihydrate

Crystal data

C24H36N2O15·2(H2O)	F(000) = 668
Mr = 628.58	Dx = 1.338 Mg m^−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 2067 reflections
a = 8.8385 (2) Å	θ = 2.5–27.5°
b = 21.8363 (8) Å	µ = 0.11 mm^−1
c = 8.0831 (2) Å	T = 120 K
V = 1560.04 (8) Å^3	Block, colourless
Z = 2	0.30 × 0.20 × 0.15 mm

Data collection

Kappa-CCD diffractometer	2067 independent reflections
Radiation source: rotating anode	1658 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.960, Tmax = 0.983	k = −28→27
13388 measured reflections	l = −9→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0967P)^2 + 0.0109P] where P = (Fo^2 + 2Fc^2)/3
2067 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

Experimental. ?.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5000	0.5000	0.4133 (3)	0.0203 (5)
O2	0.2355 (2)	0.54797 (8)	0.5288 (3)	0.0277 (5)
O3	0.1489 (2)	0.43759 (11)	0.6972 (3)	0.0401 (6)
O4	0.3628 (2)	0.34172 (10)	0.6395 (3)	0.0393 (6)
O5	0.37591 (19)	0.42726 (8)	0.2523 (2)	0.0226 (4)
O21	0.0861 (2)	0.58510 (9)	0.3284 (3)	0.0364 (5)
O31	0.2831 (3)	0.48702 (15)	0.8978 (3)	0.0586 (7)
O61	0.6545 (3)	0.24019 (11)	0.3050 (4)	0.0574 (8)
N1	0.5457 (3)	0.31774 (11)	0.1653 (3)	0.0317 (6)
C1	0.3683 (3)	0.48644 (11)	0.3225 (3)	0.0205 (5)
C2	0.2395 (3)	0.48866 (12)	0.4482 (3)	0.0239 (6)
C3	0.2746 (3)	0.44260 (13)	0.5831 (4)	0.0276 (6)
C4	0.3005 (3)	0.37896 (12)	0.5128 (4)	0.0293 (6)
C5	0.4137 (3)	0.38047 (12)	0.3698 (3)	0.0240 (6)
C6	0.4163 (3)	0.32100 (12)	0.2744 (4)	0.0339 (7)
C21	0.1520 (3)	0.59248 (13)	0.4567 (4)	0.0290 (6)
C22	0.1565 (4)	0.65001 (14)	0.5568 (5)	0.0403 (8)
C31	0.1770 (4)	0.4547 (2)	0.8561 (5)	0.0522 (10)
C32	0.0645 (6)	0.4261 (3)	0.9678 (6)	0.0852 (17)
C61	0.6580 (4)	0.27806 (13)	0.1897 (4)	0.0363 (7)
C62	0.7924 (4)	0.28368 (16)	0.0767 (4)	0.0444 (9)
O6W	0.5812 (3)	0.38698 (13)	−0.1289 (3)	0.0538 (7)
H4A	0.2937	0.3204	0.6746	0.082 (16)*
H1A	0.5423	0.3408	0.0871	0.054 (13)*
H1	0.3521	0.5178	0.2341	0.042 (9)*
H2	0.1404	0.4793	0.3943	0.017 (7)*
H3	0.3669	0.4560	0.6448	0.028 (8)*
H4	0.2023	0.3612	0.4744	0.044 (10)*
H5	0.5171	0.3886	0.4147	0.020 (7)*
H6A	0.4194	0.2862	0.3529	0.046 (10)*
H6B	0.3224	0.3175	0.2084	0.023 (7)*
H22A	0.2154	0.6812	0.4979	0.062 (12)*
H22B	0.2040	0.6416	0.6640	0.088 (16)*
H22C	0.0533	0.6650	0.5745	0.16 (3)*
H32A	0.1057	0.3875	1.0105	0.054 (12)*
H32B	−0.0290	0.4178	0.9066	0.067 (14)*
H32C	0.0429	0.4537	1.0603	0.13 (3)*
H62A	0.8749	0.3045	0.1351	0.074 (15)*
H62B	0.7640	0.3075	−0.0212	0.070 (13)*
H62C	0.8257	0.2428	0.0427	0.067 (13)*
H6C	0.5873	0.4269	−0.0731	0.20 (4)*
H6D	0.4972	0.3785	−0.2002	0.083 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0199 (11)	0.0165 (12)	0.0243 (13)	−0.0040 (10)	0.000	0.000
O2	0.0257 (9)	0.0233 (10)	0.0342 (11)	0.0041 (7)	−0.0032 (9)	−0.0064 (9)
O3	0.0360 (11)	0.0474 (13)	0.0369 (12)	−0.0028 (10)	0.0115 (10)	0.0066 (11)
O4	0.0395 (11)	0.0316 (11)	0.0468 (13)	−0.0038 (10)	−0.0017 (11)	0.0215 (11)
O5	0.0294 (9)	0.0122 (8)	0.0261 (9)	−0.0006 (7)	−0.0015 (8)	0.0001 (7)
O21	0.0401 (10)	0.0246 (11)	0.0444 (13)	0.0037 (9)	−0.0096 (11)	0.0029 (10)
O31	0.0585 (16)	0.077 (2)	0.0405 (13)	−0.0033 (15)	0.0057 (13)	−0.0039 (14)
O61	0.0596 (16)	0.0379 (13)	0.0747 (18)	0.0193 (11)	0.0137 (15)	0.0270 (14)
N1	0.0408 (13)	0.0160 (11)	0.0382 (13)	0.0057 (9)	0.0014 (11)	0.0009 (11)
C1	0.0242 (12)	0.0107 (11)	0.0267 (12)	−0.0007 (9)	−0.0044 (11)	0.0006 (10)
C2	0.0224 (12)	0.0200 (13)	0.0293 (13)	−0.0016 (10)	−0.0020 (11)	−0.0017 (11)
C3	0.0271 (13)	0.0259 (13)	0.0297 (14)	−0.0025 (11)	0.0033 (12)	0.0046 (12)
C4	0.0289 (12)	0.0213 (14)	0.0376 (16)	−0.0053 (11)	−0.0005 (13)	0.0082 (13)
C5	0.0253 (11)	0.0138 (12)	0.0329 (14)	0.0003 (10)	−0.0011 (12)	0.0047 (11)
C6	0.0367 (15)	0.0133 (13)	0.0518 (19)	−0.0016 (11)	0.0003 (14)	−0.0017 (13)
C21	0.0231 (12)	0.0218 (14)	0.0422 (17)	0.0009 (10)	0.0007 (13)	0.0003 (13)
C22	0.0374 (15)	0.0286 (16)	0.055 (2)	0.0026 (13)	0.0012 (16)	−0.0114 (15)
C31	0.0485 (19)	0.072 (3)	0.0366 (19)	0.004 (2)	0.0104 (17)	0.0075 (19)
C32	0.065 (3)	0.143 (5)	0.048 (2)	−0.008 (3)	0.015 (2)	0.025 (3)
C61	0.0462 (17)	0.0156 (13)	0.0469 (18)	0.0062 (12)	−0.0008 (16)	0.0022 (13)
C62	0.0507 (19)	0.0359 (17)	0.0467 (19)	0.0148 (16)	0.0054 (16)	−0.0003 (16)
O6W	0.0628 (15)	0.0539 (17)	0.0449 (14)	0.0059 (13)	−0.0089 (13)	0.0137 (13)

Geometric parameters (Å, º)

O1—C1	1.407 (3)	C3—H3	1.00
O1—C1^i	1.407 (3)	C4—C5	1.530 (4)
O2—C21	1.352 (3)	C4—H4	1.00
O2—C2	1.450 (3)	C5—C6	1.510 (4)
O3—C31	1.360 (5)	C5—H5	1.00
O3—C3	1.448 (3)	C6—H6A	0.99
O4—C4	1.419 (4)	C6—H6B	0.99
O4—H4A	0.8191	C21—C22	1.495 (4)
O5—C1	1.413 (3)	C22—H22A	0.98
O5—C5	1.434 (3)	C22—H22B	0.9801
O21—C21	1.201 (4)	C22—H22C	0.9799
O31—C31	1.221 (5)	C31—C32	1.481 (6)
O61—C61	1.246 (4)	C32—H32A	0.98
N1—C61	1.332 (4)	C32—H32B	0.98
N1—C6	1.445 (4)	C32—H32C	0.9799
N1—H1A	0.8091	C61—C62	1.503 (5)
C1—C2	1.527 (4)	C62—H62A	0.98
C1—H1	1.00	C62—H62B	0.98
C2—C3	1.516 (4)	C62—H62C	0.9801
C2—H2	1.00	O6W—H6C	0.9834
C3—C4	1.519 (4)	O6W—H6D	0.9582
C1—O1—C1^i	117.1 (3)	C6—C5—H5	108.9
C21—O2—C2	117.5 (2)	C4—C5—H5	109.1
C31—O3—C3	116.1 (3)	N1—C6—C5	111.5 (2)
C4—O4—H4A	106.6	N1—C6—H6A	109.4
C1—O5—C5	113.4 (2)	C5—C6—H6A	109.4
C61—N1—C6	122.1 (3)	N1—C6—H6B	109.3
C61—N1—H1A	123.3	C5—C6—H6B	109.2
C6—N1—H1A	114.6	H6A—C6—H6B	108.0
O1—C1—O5	111.27 (18)	O21—C21—O2	122.7 (3)
O1—C1—C2	105.2 (2)	O21—C21—C22	126.4 (3)
O5—C1—C2	109.35 (19)	O2—C21—C22	110.9 (3)
O1—C1—H1	110.3	C21—C22—H22A	109.5
O5—C1—H1	110.2	C21—C22—H22B	109.3
C2—C1—H1	110.3	H22A—C22—H22B	109.5
O2—C2—C3	105.9 (2)	C21—C22—H22C	109.5
O2—C2—C1	110.2 (2)	H22A—C22—H22C	109.5
C3—C2—C1	107.8 (2)	H22B—C22—H22C	109.5
O2—C2—H2	110.9	O31—C31—O3	124.0 (3)
C3—C2—H2	110.9	O31—C31—C32	126.3 (4)
C1—C2—H2	110.9	O3—C31—C32	109.7 (4)
O3—C3—C2	110.6 (2)	C31—C32—H32A	109.2
O3—C3—C4	106.5 (2)	C31—C32—H32B	109.6
C2—C3—C4	111.6 (2)	H32A—C32—H32B	109.5
O3—C3—H3	109.3	C31—C32—H32C	109.6
C2—C3—H3	109.3	H32A—C32—H32C	109.5
C4—C3—H3	109.4	H32B—C32—H32C	109.5
O4—C4—C3	108.2 (2)	O61—C61—N1	121.6 (3)
O4—C4—C5	107.7 (2)	O61—C61—C62	121.8 (3)
C3—C4—C5	111.2 (2)	N1—C61—C62	116.5 (3)
O4—C4—H4	109.9	C61—C62—H62A	109.5
C3—C4—H4	109.9	C61—C62—H62B	109.4
C5—C4—H4	110.0	H62A—C62—H62B	109.5
O5—C5—C6	106.2 (2)	C61—C62—H62C	109.5
O5—C5—C4	111.3 (2)	H62A—C62—H62C	109.5
C6—C5—C4	112.2 (2)	H62B—C62—H62C	109.5
O5—C5—H5	109.1	H6C—O6W—H6D	119.4
C1^i—O1—C1—O5	74.52 (17)	O3—C3—C4—C5	170.8 (2)
C1^i—O1—C1—C2	−167.1 (2)	C2—C3—C4—C5	49.9 (3)
C5—O5—C1—O1	51.5 (3)	C1—O5—C5—C6	179.9 (2)
C5—O5—C1—C2	−64.3 (2)	C1—O5—C5—C4	57.5 (3)
C21—O2—C2—C3	−154.8 (2)	O4—C4—C5—O5	−167.3 (2)
C21—O2—C2—C1	88.8 (3)	C3—C4—C5—O5	−48.9 (3)
O1—C1—C2—O2	57.0 (2)	O4—C4—C5—C6	73.9 (3)
O5—C1—C2—O2	176.65 (19)	C3—C4—C5—C6	−167.7 (2)
O1—C1—C2—C3	−58.1 (2)	C61—N1—C6—C5	112.4 (3)
O5—C1—C2—C3	61.5 (3)	O5—C5—C6—N1	71.3 (3)
C31—O3—C3—C2	−116.8 (3)	C4—C5—C6—N1	−166.9 (2)
C31—O3—C3—C4	121.7 (3)	C2—O2—C21—O21	−2.1 (4)
O2—C2—C3—O3	68.2 (3)	C2—O2—C21—C22	178.6 (2)
C1—C2—C3—O3	−173.8 (2)	C3—O3—C31—O31	19.0 (6)
O2—C2—C3—C4	−173.4 (2)	C3—O3—C31—C32	−158.5 (4)
C1—C2—C3—C4	−55.4 (3)	C6—N1—C61—O61	2.5 (5)
O3—C3—C4—O4	−71.2 (3)	C6—N1—C61—C62	−174.3 (3)
C2—C3—C4—O4	168.0 (2)

Symmetry code: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6W	0.81	2.05	2.835 (4)	165
O4—H4A···O61^ii	0.82	1.81	2.606 (3)	162
O6W—H6C···O31^iii	0.98	2.21	3.009 (4)	137
O6W—H6D···O4^iv	0.96	1.93	2.865 (3)	164

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

(9) 6,6'-diamino-α,α'-trehalose dihydrate

Crystal data

C12H24N2O9·2(H2O)	Dx = 1.522 Mg m^−3
Mr = 376.36	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212	Cell parameters from 1163 reflections
Hall symbol: P 4nw 2abw	θ = 3.0–27.5°
a = 8.6093 (2) Å	µ = 0.13 mm^−1
c = 22.1566 (8) Å	T = 120 K
V = 1642.25 (8) Å^3	Block, colourless
Z = 4	0.15 × 0.15 × 0.10 mm
F(000) = 808

Data collection

Kappa-CCD diffractometer	1163 independent reflections
Radiation source: rotating anode	951 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ϕ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→11
Tmin = 0.972, Tmax = 0.987	k = −11→11
8561 measured reflections	l = −20→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.9377P] where P = (Fo^2 + 2Fc^2)/3
1163 reflections	(Δ/σ)max < 0.001
115 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4945 (2)	0.4945 (2)	0.0000	0.0150 (5)
O2	0.3645 (2)	0.7739 (2)	0.03877 (8)	0.0202 (4)
O3	0.5061 (3)	0.7766 (2)	0.15877 (8)	0.0262 (5)
O4	0.6403 (2)	0.4922 (2)	0.19747 (7)	0.0184 (4)
O5	0.3713 (2)	0.3621 (2)	0.07921 (7)	0.0153 (4)
O6W	0.3753 (3)	0.8426 (3)	0.26482 (9)	0.0420 (6)
N1	0.4929 (3)	0.0674 (3)	0.11205 (10)	0.0263 (6)
C1	0.3671 (3)	0.4936 (3)	0.04081 (10)	0.0148 (5)
C2	0.3706 (3)	0.6426 (3)	0.07738 (10)	0.0153 (5)
C3	0.5113 (3)	0.6462 (3)	0.11967 (10)	0.0161 (5)
C4	0.5079 (3)	0.4998 (3)	0.15854 (11)	0.0144 (5)
C5	0.5062 (3)	0.3566 (3)	0.11789 (10)	0.0134 (5)
C6	0.4944 (3)	0.2040 (3)	0.15198 (11)	0.0172 (5)
H2A	0.4587	0.7994	0.0386	0.030*	0.50
H2B	0.2747	0.8119	0.0384	0.030*	0.50
H3A	0.4948	0.8607	0.1400	0.039*
H4A	0.6961	0.5720	0.2002	0.028*	0.50
H4B	0.5892	0.4461	0.2243	0.028*	0.50
H6C	0.4383	0.8455	0.2278	0.050*
H6D	0.2846	0.7714	0.2586	0.050*
H1A	0.5895	0.0725	0.0871	0.032*
H1B	0.3980	0.0792	0.0906	0.032*
H1	0.2685	0.4908	0.0170	0.018*
H2	0.2751	0.6444	0.1031	0.018*
H3	0.6092	0.6488	0.0954	0.019*
H4	0.4114	0.5005	0.1837	0.017*
H5	0.6022	0.3558	0.0925	0.016*
H6A	0.5834	0.1955	0.1800	0.021*
H6B	0.3981	0.2045	0.1764	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0163 (7)	0.0163 (7)	0.0124 (11)	−0.0037 (11)	0.0026 (7)	−0.0026 (7)
O2	0.0208 (10)	0.0177 (10)	0.0221 (9)	0.0045 (8)	0.0016 (8)	0.0081 (7)
O3	0.0419 (13)	0.0141 (10)	0.0226 (9)	0.0020 (9)	−0.0020 (10)	−0.0043 (8)
O4	0.0199 (10)	0.0196 (10)	0.0158 (8)	−0.0038 (8)	−0.0046 (7)	0.0026 (8)
O5	0.0160 (10)	0.0148 (9)	0.0152 (8)	−0.0034 (8)	−0.0017 (7)	0.0023 (7)
O6W	0.0506 (15)	0.0415 (14)	0.0340 (12)	−0.0024 (12)	0.0119 (11)	−0.0068 (10)
N1	0.0361 (15)	0.0127 (11)	0.0302 (12)	0.0007 (11)	−0.0020 (12)	−0.0002 (9)
C1	0.0143 (12)	0.0161 (12)	0.0141 (11)	0.0008 (11)	0.0007 (9)	0.0034 (10)
C2	0.0176 (13)	0.0140 (13)	0.0144 (11)	0.0042 (11)	0.0010 (10)	0.0028 (10)
C3	0.0193 (14)	0.0125 (13)	0.0165 (11)	−0.0011 (12)	−0.0001 (11)	−0.0005 (10)
C4	0.0154 (12)	0.0141 (12)	0.0136 (10)	0.0001 (11)	0.0000 (10)	0.0000 (10)
C5	0.0121 (13)	0.0145 (13)	0.0135 (10)	0.0001 (11)	−0.0007 (10)	0.0013 (9)
C6	0.0200 (14)	0.0138 (13)	0.0179 (11)	0.0018 (11)	−0.0022 (12)	0.0017 (10)

Geometric parameters (Å, º)

O1—C1^i	1.421 (3)	N1—H1A	0.9992
O1—C1	1.421 (3)	N1—H1B	0.9509
O2—C2	1.418 (3)	C1—C2	1.518 (3)
O2—H2A	0.84	C1—H1	1.00
O2—H2B	0.8399	C2—C3	1.532 (4)
O3—C3	1.419 (3)	C2—H2	1.00
O3—H3A	0.8401	C3—C4	1.527 (3)
O4—C4	1.431 (3)	C3—H3	1.00
O4—H4A	0.8398	C4—C5	1.527 (3)
O4—H4B	0.8399	C4—H4	1.00
O5—C1	1.416 (3)	C5—C6	1.519 (3)
O5—C5	1.444 (3)	C5—H5	1.00
O6W—H6C	0.9833	C6—H6A	0.99
O6W—H6D	1.0025	C6—H6B	0.99
N1—C6	1.472 (3)
C1^i—O1—C1	113.4 (3)	O3—C3—C4	107.95 (18)
C2—O2—H2A	100.1	O3—C3—C2	111.4 (2)
C2—O2—H2B	110.5	C4—C3—C2	108.2 (2)
H2A—O2—H2B	141.9	O3—C3—H3	109.7
C3—O3—H3A	112.6	C4—C3—H3	109.7
C4—O4—H4A	117.5	C2—C3—H3	109.7
C4—O4—H4B	91.8	O4—C4—C5	109.0 (2)
H4A—O4—H4B	129.4	O4—C4—C3	111.2 (2)
C1—O5—C5	113.80 (19)	C5—C4—C3	109.51 (18)
H6C—O6W—H6D	109.3	O4—C4—H4	109.0
C6—N1—H1A	106.8	C5—C4—H4	109.0
C6—N1—H1B	102.8	C3—C4—H4	109.0
H1A—N1—H1B	115.7	O5—C5—C6	105.7 (2)
O5—C1—O1	111.51 (18)	O5—C5—C4	109.3 (2)
O5—C1—C2	110.75 (17)	C6—C5—C4	113.93 (18)
O1—C1—C2	108.7 (2)	O5—C5—H5	109.3
O5—C1—H1	108.6	C6—C5—H5	109.3
O1—C1—H1	108.6	C4—C5—H5	109.3
C2—C1—H1	108.6	N1—C6—C5	113.15 (19)
O2—C2—C1	110.53 (17)	N1—C6—H6A	108.9
O2—C2—C3	112.5 (2)	C5—C6—H6A	108.9
C1—C2—C3	111.0 (2)	N1—C6—H6B	108.9
O2—C2—H2	107.5	C5—C6—H6B	108.9
C1—C2—H2	107.5	H6A—C6—H6B	107.8
C3—C2—H2	107.5
C5—O5—C1—O1	62.7 (2)	O3—C3—C4—O4	−61.8 (3)
C5—O5—C1—C2	−58.5 (3)	C2—C3—C4—O4	177.47 (19)
C1^i—O1—C1—O5	63.61 (16)	O3—C3—C4—C5	177.6 (3)
C1^i—O1—C1—C2	−174.0 (2)	C2—C3—C4—C5	56.9 (3)
O5—C1—C2—O2	−179.3 (2)	C1—O5—C5—C6	−176.42 (18)
O1—C1—C2—O2	57.9 (2)	C1—O5—C5—C4	60.6 (2)
O5—C1—C2—C3	55.2 (3)	O4—C4—C5—O5	179.02 (18)
O1—C1—C2—C3	−67.7 (2)	C3—C4—C5—O5	−59.1 (3)
O2—C2—C3—O3	62.1 (3)	O4—C4—C5—C6	61.1 (3)
C1—C2—C3—O3	−173.4 (2)	C3—C4—C5—C6	−177.0 (3)
O2—C2—C3—C4	−179.36 (19)	O5—C5—C6—N1	60.0 (3)
C1—C2—C3—C4	−54.9 (3)	C4—C5—C6—N1	180.0 (3)

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O6W^ii	0.84	1.91	2.721 (3)	163
O2—H2B···O4^iii	0.84	2.07	2.806 (3)	146
O3—H3A···N1^iv	0.84	1.88	2.711 (3)	168
O4—H4A···O2^v	0.84	1.98	2.806 (3)	167
O4—H4B···O4^vi	0.84	2.01	2.833 (3)	165
O6W—H6C···O3	0.98	1.74	2.667 (3)	155
O6W—H6D···O6W^vi	1.00	1.75	2.733 (5)	166
N1—H1A···O6W^vii	1.00	2.41	3.062 (3)	123
N1—H1B···O4^viii	0.95	2.45	3.349 (3)	157

Symmetry codes: (ii) −y+3/2, x+1/2, z−1/4; (iii) x−1/2, −y+3/2, −z+1/4; (iv) x, y+1, z; (v) x+1/2, −y+3/2, −z+1/4; (vi) −y+1, −x+1, −z+1/2; (vii) −y+3/2, x−1/2, z−1/4; (viii) x−1/2, −y+1/2, −z+1/4.

 

Footnotes

‡Present address: Instituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro-RJ, Brazil.

¹Supplementary data for this paper are available from the IUCr electronic archives (Reference: NA5016 ). Services for accessing these data are described at the back of the journal.