Octa-O-acetyl-α,α-trehalose ethanol disolvate

Färnbäck, M.; Eriksson, L.; Widmalm, G.

doi:10.1107/S1600536804018707

Octa-O-acetyl-α,α-trehalose ethanol disolvate

The glycosidic torsion angles φ_H and φ_H′ of the title compound, C₂₈H₃₈O₁₉·2C₂H₅OH, with values of −40.2 and −42.6°, respectively, are closely similar to those in the structure of the same compound crystallized from ethyl acetate. Of particular interest is that the solvent molecules in this structure take up a similar volume to those in the ethyl acetate solvate, thereby highlighting relationships between solvent and solute in these crystal structures.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018707/cf6368sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018707/cf6368Isup2.hkl Contains datablock I

CCDC reference: 251641

checkCIF report

Key indicators

Single-crystal synchrotron study
T = 110 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.043
wR factor = 0.112
Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.35 Ratio

Author Response: We cant locate exactly wich atom that this concern However there are large differences in Ueq. depending on where the atoms are, in the central ring systems or in the acetyl groups or even solvent molecules.

PLAT220_ALERT_2_A Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       6.48 Ratio

PLAT221_ALERT_4_A Large Solvent/Anion  C     Ueq(max)/Ueq(min) ...      10.00 Ratio

PLAT221_ALERT_4_A Large Solvent/Anion  C     Ueq(max)/Ueq(min) ...       5.68 Ratio

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.50 Ratio

PLAT223_ALERT_4_A Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       8.87 Ratio

PLAT223_ALERT_4_A Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...      10.00 Ratio

PLAT413_ALERT_2_A Short Inter XH3 .. XHn     HM2C   ..  H31C    ..       1.83 Ang.

Author Response: The H31C hydrogen is part of an disordered solvent molecule.

PLAT413_ALERT_2_A Short Inter XH3 .. XHn     HM4B   ..  H42A    ..       1.31 Ang.

Author Response: The H31C hydrogen is part of an disordered solvent molecule.

PLAT413_ALERT_2_A Short Inter XH3 .. XHn     HM4E   ..  H31A    ..       1.77 Ang.

Author Response: The H31C hydrogen is part of an disordered solvent molecule.

PLAT432_ALERT_2_A Short Inter X...Y Contact  CO3'   ..  C31     ..       2.69 Ang.

Author Response: The C31 carbon is part of an disordered solvent molecule.


Alert level B
PLAT213_ALERT_2_B Atom O2#     has ADP max/min Ratio .............       4.10 prolat
PLAT420_ALERT_2_B D-H Without Acceptor      >O31    -  >H31    ...          ?
PLAT432_ALERT_2_B Short Inter X...Y Contact  CM4    ..  C42     ..       3.06 Ang.

Author Response: The C31 carbon is part of an disordered solvent molecule.


Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          6
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        CC6
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for       CC6'
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors  for        C42
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        C32
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        C12
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O31    ..  CC6     ..       2.99 Ang.

Author Response: The C31 carbon is part of an disordered solvent molecule.

PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         50

Alert level G
  ABSMU_01  Radiation type not identified. Calculation of
            _exptl_absorpt_correction_mu not performed.
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           46.00
           From the CIF: _reflns_number_total               9124
           Count of symmetry unique reflns         9266
           Completeness (_total/calc)             98.47%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

  11 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
  10 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1998); cell refinement: SMART; data reduction: SAINT (Siemens, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

octa O-acetyl α-D-glucopyranosyl α-D-glycopyranoside top

Crystal data top

C₂₈H₃₈O₁₉·2C₂H₆O	F(000) = 1640
M_r = 770.72	D_x = 1.324 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Synchrotron radiation, λ = 0.891 Å
Hall symbol: P 2ac 2ab	Cell parameters from 999 reflections
a = 13.756 (4) Å	θ = 3.0–29.0°
b = 15.667 (4) Å	µ = 0.11 mm⁻¹
c = 17.934 (4) Å	T = 110 K
V = 3865.0 (17) Å³	Needle, colourless
Z = 4	0.20 × 0.05 × 0.03 mm

Data collection top

Bruker SMART 1K area-detector diffractometer	9124 independent reflections
Radiation source: Beamline I711, MAXLAB, Lund	4887 reflections with I > 2σ(I)
Silicon monochromator	R_int = 0.090
Detector resolution: 10 pixels mm^-1	θ_max = 46.0°, θ_min = 2.2°
ω scans	h = −22→22
Absorption correction: numerical (X-RED; Stoe & Cie, 1997)	k = 0→25
T_min = 0.97, T_max = 1.00	l = 0→28
76752 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
9124 reflections	(Δ/σ)_max = 0.002
478 parameters	Δρ_max = 0.39 e Å⁻³
135 restraints	Δρ_min = −0.36 e Å⁻³

Special details top

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

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

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.28079 (13)	0.55174 (11)	0.75155 (9)	0.0134 (3)
H1	0.2509	0.6085	0.7534	0.016*
O1	0.25112 (10)	0.50389 (7)	0.81516 (6)	0.0152 (2)
C2	0.24364 (12)	0.50442 (11)	0.68324 (9)	0.0113 (3)
H2	0.2571	0.5382	0.6384	0.014*
O2	0.14078 (9)	0.48801 (8)	0.68828 (7)	0.0167 (3)
CC2	0.08023 (14)	0.54704 (12)	0.65623 (10)	0.0184 (4)
CO2	0.11075 (11)	0.61238 (9)	0.62876 (8)	0.0296 (3)
CM2	−0.02239 (16)	0.51861 (15)	0.66084 (12)	0.0303 (5)
HM2A	−0.0519	0.5421	0.7048	0.045*
HM2B	−0.0247	0.4574	0.6631	0.045*
HM2C	−0.0571	0.5379	0.6176	0.045*
C3	0.29360 (14)	0.41752 (11)	0.67684 (9)	0.0136 (3)
H3	0.2731	0.3800	0.7176	0.016*
O3	0.26332 (9)	0.38269 (7)	0.60558 (6)	0.0144 (3)
CC3	0.23110 (16)	0.29952 (11)	0.60306 (10)	0.0212 (4)
CO3	0.23339 (18)	0.25375 (9)	0.65657 (9)	0.0524 (6)
CM3	0.20021 (18)	0.27647 (12)	0.52682 (11)	0.0274 (5)
HM3A	0.1416	0.3066	0.5146	0.041*
HM3B	0.1886	0.2161	0.5242	0.041*
HM3C	0.2504	0.2917	0.4921	0.041*
C4	0.40333 (13)	0.42875 (11)	0.67749 (10)	0.0150 (4)
H4	0.4250	0.4574	0.6319	0.018*
O4	0.44916 (10)	0.34583 (8)	0.68442 (7)	0.0201 (3)
CC4	0.48369 (16)	0.30805 (12)	0.62208 (11)	0.0232 (4)
CO4	0.48151 (14)	0.33990 (10)	0.56161 (8)	0.0396 (4)
CM4	0.52662 (19)	0.22184 (14)	0.64109 (14)	0.0349 (5)
HM4A	0.5089	0.2066	0.6911	0.052*
HM4B	0.5961	0.2245	0.6371	0.052*
HM4C	0.5021	0.1797	0.6071	0.052*
C5	0.43444 (14)	0.47989 (12)	0.74646 (10)	0.0183 (4)
H5	0.4198	0.4473	0.7917	0.022*
O5	0.38364 (9)	0.56062 (7)	0.74814 (7)	0.0155 (3)
C6	0.54163 (17)	0.50000 (17)	0.74355 (13)	0.0376 (6)
H6A	0.5784	0.4481	0.7350	0.045*
H6B	0.5548	0.5392	0.7029	0.045*
O6	0.57027 (14)	0.53807 (13)	0.81349 (11)	0.0563 (6)
CC6	0.6466 (2)	0.50805 (18)	0.84957 (14)	0.0450 (6)
CO6	0.6855 (2)	0.44118 (17)	0.83163 (13)	0.0932 (10)
CM6	0.6721 (2)	0.56142 (18)	0.91649 (16)	0.0486 (7)
HM6A	0.6968	0.5253	0.9553	0.073*
HM6B	0.6150	0.5905	0.9339	0.073*
HM6C	0.7207	0.6026	0.9029	0.073*
C1'	0.24873 (14)	0.55405 (10)	0.88158 (9)	0.0148 (3)
H1'	0.3063	0.5908	0.8837	0.018*
C2'	0.24893 (14)	0.49315 (10)	0.94771 (9)	0.0146 (3)
H2'	0.2554	0.5262	0.9938	0.018*
O2'	0.32870 (10)	0.43254 (8)	0.94292 (7)	0.0192 (3)
CC2'	0.41797 (15)	0.45920 (13)	0.96553 (10)	0.0204 (4)
CO2'	0.43281 (12)	0.53196 (9)	0.98697 (8)	0.0298 (3)
CM2'	0.49064 (17)	0.38815 (14)	0.96177 (13)	0.0305 (5)
HM2D	0.4857	0.3601	0.9143	0.046*
HM2E	0.4778	0.3478	1.0009	0.046*
HM2F	0.5549	0.4110	0.9677	0.046*
C3'	0.15748 (14)	0.43985 (10)	0.95188 (9)	0.0147 (3)
H3'	0.1583	0.3964	0.9126	0.018*
O3'	0.15708 (10)	0.39919 (7)	1.02417 (7)	0.0196 (3)
CC3'	0.14600 (15)	0.31334 (11)	1.02840 (10)	0.0201 (4)
CO3'	0.13131 (16)	0.26935 (10)	0.97429 (9)	0.0476 (5)
CM3'	0.15445 (17)	0.28343 (12)	1.10724 (11)	0.0250 (4)
HM3D	0.1100	0.3149	1.1380	0.038*
HM3E	0.2196	0.2925	1.1246	0.038*
HM3F	0.1392	0.2237	1.1098	0.038*
C4'	0.06628 (14)	0.49501 (11)	0.94445 (9)	0.0172 (4)
H4'	0.0547	0.5269	0.9906	0.021*
O4'	−0.01600 (10)	0.43943 (10)	0.92821 (8)	0.0264 (3)
CC4'	−0.0745 (2)	0.41796 (17)	0.98399 (14)	0.0396 (6)
CO4'	−0.0649 (2)	0.44221 (17)	1.04726 (11)	0.0785 (8)
CM4'	−0.1493 (2)	0.35468 (18)	0.95714 (16)	0.0491 (7)
HM4D	−0.1770	0.3744	0.9111	0.074*
HM4E	−0.1996	0.3490	0.9939	0.074*
HM4F	−0.1188	0.3003	0.9493	0.074*
C5'	0.07398 (15)	0.55647 (12)	0.87814 (10)	0.0196 (4)
H5'	0.0741	0.5240	0.8315	0.023*
O5'	0.16301 (10)	0.60518 (7)	0.88411 (6)	0.0194 (3)
C6'	−0.00977 (18)	0.62028 (14)	0.87757 (11)	0.0302 (5)
H6'1	−0.0708	0.5910	0.8865	0.036*
H6'2	−0.0006	0.6624	0.9166	0.036*
O6'	−0.01189 (14)	0.66172 (10)	0.80526 (8)	0.0385 (4)
CC6'	−0.0089 (2)	0.74721 (17)	0.80312 (14)	0.0415 (6)
CO6'	0.0040 (3)	0.78865 (14)	0.85772 (12)	0.0871 (9)
CM6'	−0.0215 (3)	0.78101 (19)	0.72529 (15)	0.0605 (9)
HM6D	−0.0672	0.8273	0.7258	0.091*
HM6E	−0.0453	0.7363	0.6935	0.091*
HM6F	0.0400	0.8010	0.7069	0.091*
C11	0.6694 (3)	0.7219 (3)	0.6639 (2)	0.0253 (11)*	0.486 (5)
H11A	0.6672	0.7468	0.6150	0.038*	0.486 (5)
H11B	0.6848	0.7652	0.6999	0.038*	0.486 (5)
H11C	0.6072	0.6974	0.6755	0.038*	0.486 (5)
C12	0.7466 (4)	0.6528 (3)	0.6658 (2)	0.0213 (12)*	0.486 (5)
H12A	0.7329	0.6107	0.6276	0.026*	0.486 (5)
H12B	0.8096	0.6778	0.6553	0.026*	0.486 (5)
O11	0.7489 (4)	0.6134 (3)	0.7348 (3)	0.183 (2)*	0.486 (5)
H11	0.7615	0.6488	0.7671	0.274*	0.486 (5)
C21	0.2489 (3)	0.8932 (3)	0.8718 (2)	0.0305 (10)*	0.590 (6)
H21A	0.2411	0.9508	0.8543	0.046*	0.590 (6)
H21B	0.3142	0.8853	0.8894	0.046*	0.590 (6)
H21C	0.2040	0.8827	0.9117	0.046*	0.590 (6)
C22	0.2292 (4)	0.8325 (3)	0.8093 (3)	0.0469 (13)*	0.590 (6)
H22A	0.1631	0.8433	0.7930	0.056*	0.590 (6)
H22B	0.2714	0.8493	0.7685	0.056*	0.590 (6)
O21	0.2380 (3)	0.7478 (2)	0.8163 (2)	0.0671 (14)*	0.590 (6)
H21	0.1995	0.7306	0.8478	0.101*	0.590 (6)
C31	0.8009 (8)	0.6341 (6)	0.6022 (4)	0.111 (3)*	0.514 (5)
H31A	0.7917	0.6715	0.5604	0.167*	0.514 (5)
H31B	0.7823	0.5771	0.5885	0.167*	0.514 (5)
H31C	0.8681	0.6346	0.6166	0.167*	0.514 (5)
C32	0.7381 (11)	0.6644 (9)	0.6676 (5)	0.121 (5)*	0.514 (5)
H32A	0.7548	0.7231	0.6791	0.145*	0.514 (5)
H32B	0.6704	0.6633	0.6525	0.145*	0.514 (5)
O31	0.7489 (4)	0.6134 (3)	0.7348 (3)	0.183 (2)*	0.514 (5)
H31	0.8044	0.6186	0.7510	0.274*	0.514 (5)
C41	0.250 (2)	0.8826 (15)	0.8813 (11)	0.221 (13)*	0.410 (6)
H41A	0.2252	0.8802	0.9312	0.331*	0.410 (6)
H41B	0.2050	0.9121	0.8498	0.331*	0.410 (6)
H41C	0.3113	0.9123	0.8813	0.331*	0.410 (6)
C42	0.265 (3)	0.7905 (14)	0.8516 (7)	0.34 (2)*	0.410 (6)
H42A	0.3216	0.7647	0.8754	0.408*	0.410 (6)
H42B	0.2089	0.7558	0.8626	0.408*	0.410 (6)
O41	0.2803 (4)	0.7954 (3)	0.7723 (3)	0.0597 (19)*	0.410 (6)
H41	0.2553	0.7538	0.7522	0.090*	0.410 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0186 (9)	0.0106 (8)	0.0110 (7)	0.0017 (7)	0.0029 (6)	0.0002 (6)
O1	0.0276 (7)	0.0079 (5)	0.0100 (5)	0.0001 (5)	0.0039 (5)	−0.0010 (4)
C2	0.0070 (8)	0.0131 (7)	0.0137 (7)	0.0004 (6)	0.0017 (6)	0.0018 (6)
O2	0.0161 (7)	0.0179 (6)	0.0161 (6)	0.0012 (5)	0.0014 (5)	0.0011 (5)
CC2	0.0178 (10)	0.0223 (10)	0.0152 (8)	0.0066 (8)	−0.0003 (7)	−0.0054 (7)
CO2	0.0301 (8)	0.0206 (7)	0.0381 (8)	0.0061 (6)	−0.0062 (6)	0.0053 (6)
CM2	0.0246 (11)	0.0348 (12)	0.0316 (11)	0.0019 (9)	−0.0039 (9)	−0.0090 (9)
C3	0.0262 (10)	0.0088 (7)	0.0057 (7)	−0.0007 (7)	−0.0008 (6)	−0.0010 (6)
O3	0.0257 (7)	0.0088 (5)	0.0088 (5)	−0.0010 (5)	−0.0040 (5)	−0.0008 (4)
CC3	0.0391 (12)	0.0085 (8)	0.0160 (9)	−0.0033 (8)	−0.0024 (8)	−0.0011 (7)
CO3	0.1174 (18)	0.0142 (7)	0.0257 (8)	−0.0197 (9)	−0.0158 (10)	0.0099 (6)
CM3	0.0483 (14)	0.0130 (9)	0.0208 (10)	−0.0064 (8)	−0.0041 (9)	−0.0037 (8)
C4	0.0164 (9)	0.0126 (8)	0.0158 (8)	0.0083 (7)	0.0004 (7)	0.0018 (7)
O4	0.0263 (8)	0.0177 (6)	0.0164 (6)	0.0117 (5)	0.0036 (5)	0.0010 (5)
CC4	0.0308 (12)	0.0141 (9)	0.0247 (10)	0.0114 (8)	0.0037 (8)	0.0002 (8)
CO4	0.0722 (13)	0.0262 (8)	0.0205 (7)	0.0260 (8)	0.0137 (8)	0.0020 (6)
CM4	0.0436 (15)	0.0198 (10)	0.0413 (13)	0.0179 (10)	0.0064 (11)	0.0067 (9)
C5	0.0186 (10)	0.0215 (9)	0.0148 (8)	0.0088 (8)	0.0002 (7)	−0.0022 (7)
O5	0.0207 (7)	0.0107 (6)	0.0151 (6)	−0.0005 (5)	0.0017 (5)	−0.0021 (5)
C6	0.0259 (13)	0.0495 (14)	0.0372 (12)	0.0041 (11)	−0.0121 (10)	−0.0177 (11)
O6	0.0470 (11)	0.0593 (12)	0.0628 (12)	0.0133 (10)	−0.0271 (10)	−0.0392 (10)
CC6	0.0494 (16)	0.0520 (16)	0.0335 (13)	0.0022 (13)	−0.0118 (11)	−0.0003 (11)
CO6	0.138 (3)	0.0786 (17)	0.0632 (15)	0.0564 (17)	−0.0336 (15)	−0.0252 (13)
CM6	0.0446 (17)	0.0511 (16)	0.0500 (15)	−0.0190 (13)	−0.0175 (12)	0.0022 (12)
C1'	0.0195 (9)	0.0120 (8)	0.0130 (7)	0.0047 (7)	0.0041 (7)	−0.0038 (6)
C2'	0.0220 (9)	0.0078 (7)	0.0140 (8)	0.0059 (7)	0.0013 (7)	−0.0039 (6)
O2'	0.0246 (8)	0.0103 (6)	0.0227 (6)	0.0082 (5)	0.0000 (5)	−0.0010 (5)
CC2'	0.0278 (11)	0.0197 (9)	0.0135 (8)	0.0031 (8)	0.0003 (7)	0.0015 (7)
CO2'	0.0306 (9)	0.0256 (8)	0.0333 (8)	0.0009 (7)	−0.0056 (6)	0.0005 (6)
CM2'	0.0284 (12)	0.0283 (11)	0.0347 (12)	0.0077 (9)	−0.0010 (9)	0.0037 (9)
C3'	0.0257 (10)	0.0087 (7)	0.0096 (7)	0.0049 (7)	0.0004 (7)	0.0002 (6)
O3'	0.0344 (8)	0.0099 (5)	0.0146 (6)	0.0009 (6)	−0.0009 (6)	0.0017 (5)
CC3'	0.0260 (11)	0.0091 (8)	0.0253 (9)	−0.0068 (7)	0.0034 (8)	−0.0004 (7)
CO3'	0.0955 (16)	0.0214 (8)	0.0260 (8)	−0.0261 (9)	−0.0019 (9)	−0.0001 (6)
CM3'	0.0356 (12)	0.0132 (8)	0.0262 (10)	−0.0056 (8)	−0.0022 (9)	0.0043 (7)
C4'	0.0226 (10)	0.0148 (8)	0.0141 (8)	0.0049 (8)	0.0006 (7)	−0.0012 (7)
O4'	0.0197 (7)	0.0355 (8)	0.0240 (7)	0.0022 (6)	−0.0002 (6)	−0.0002 (6)
CC4'	0.0416 (15)	0.0422 (14)	0.0351 (13)	−0.0136 (12)	0.0075 (11)	0.0008 (11)
CO4'	0.0939 (18)	0.0978 (18)	0.0437 (12)	−0.0619 (15)	0.0295 (11)	−0.0166 (11)
CM4'	0.0470 (17)	0.0478 (15)	0.0524 (15)	−0.0123 (13)	0.0016 (13)	0.0020 (12)
C5'	0.0281 (11)	0.0176 (9)	0.0130 (8)	0.0089 (8)	−0.0001 (7)	−0.0012 (7)
O5'	0.0328 (8)	0.0113 (6)	0.0140 (6)	0.0091 (6)	0.0038 (5)	−0.0013 (5)
C6'	0.0400 (13)	0.0298 (11)	0.0208 (10)	0.0207 (10)	0.0018 (9)	0.0035 (8)
O6'	0.0630 (12)	0.0296 (8)	0.0230 (7)	0.0270 (8)	−0.0059 (7)	0.0068 (6)
CC6'	0.0507 (17)	0.0319 (13)	0.0419 (14)	0.0023 (12)	−0.0003 (12)	0.0077 (11)
CO6'	0.185 (3)	0.0341 (11)	0.0426 (12)	−0.0289 (15)	0.0104 (15)	0.0054 (9)
CM6'	0.097 (3)	0.0415 (15)	0.0429 (15)	0.0109 (16)	−0.0116 (16)	0.0138 (13)

Geometric parameters (Å, º) top

C1—O5	1.423 (2)	C3'—H3'	0.980
C1—O1	1.425 (2)	O3'—CC3'	1.356 (2)
C1—C2	1.520 (2)	CC3'—CO3'	1.207 (2)
C1—H1	0.980	CC3'—CM3'	1.494 (3)
O1—C1'	1.428 (2)	CM3'—HM3D	0.960
C2—O2	1.441 (2)	CM3'—HM3E	0.960
C2—C3	1.529 (2)	CM3'—HM3F	0.960
C2—H2	0.980	C4'—O4'	1.458 (2)
O2—CC2	1.371 (2)	C4'—C5'	1.534 (2)
CC2—CO2	1.211 (2)	C4'—H4'	0.980
CC2—CM2	1.483 (3)	O4'—CC4'	1.327 (3)
CM2—HM2A	0.960	CC4'—CO4'	1.204 (3)
CM2—HM2B	0.960	CC4'—CM4'	1.507 (4)
CM2—HM2C	0.960	CM4'—HM4D	0.960
C3—O3	1.4507 (19)	CM4'—HM4E	0.960
C3—C4	1.520 (3)	CM4'—HM4F	0.960
C3—H3	0.980	C5'—O5'	1.447 (3)
O3—CC3	1.377 (2)	C5'—C6'	1.525 (3)
CC3—CO3	1.198 (2)	C5'—H5'	0.980
CC3—CM3	1.477 (3)	C6'—O6'	1.451 (3)
CM3—HM3A	0.960	C6'—H6'1	0.970
CM3—HM3B	0.960	C6'—H6'2	0.970
CM3—HM3C	0.960	O6'—CC6'	1.341 (3)
C4—O4	1.449 (2)	CC6'—CO6'	1.188 (3)
C4—C5	1.535 (3)	CC6'—CM6'	1.503 (4)
C4—H4	0.980	CM6'—HM6D	0.960
O4—CC4	1.351 (2)	CM6'—HM6E	0.960
CC4—CO4	1.194 (2)	CM6'—HM6F	0.960
CC4—CM4	1.513 (3)	C11—C12	1.517 (6)
CM4—HM4A	0.960	C11—H11A	0.960
CM4—HM4B	0.960	C11—H11B	0.960
CM4—HM4C	0.960	C11—H11C	0.960
C5—O5	1.445 (2)	C12—O11	1.383 (6)
C5—C6	1.509 (3)	C12—H12A	0.970
C5—H5	0.980	C12—H12B	0.970
C6—O6	1.444 (3)	O11—H11	0.820
C6—H6A	0.970	C21—C22	1.494 (5)
C6—H6B	0.970	C21—H21A	0.960
O6—CC6	1.320 (3)	C21—H21B	0.960
CC6—CO6	1.219 (4)	C21—H21C	0.960
CC6—CM6	1.504 (4)	C22—O21	1.338 (5)
CM6—HM6A	0.960	C22—H22A	0.970
CM6—HM6B	0.960	C22—H22B	0.970
CM6—HM6C	0.960	O21—H21	0.820
C1'—O5'	1.426 (2)	C31—C32	1.533 (9)
C1'—C2'	1.522 (2)	C31—H31A	0.960
C1'—H1'	0.980	C31—H31B	0.960
C2'—O2'	1.454 (2)	C31—H31C	0.960
C2'—C3'	1.512 (3)	C32—H32A	0.970
C2'—H2'	0.980	C32—H32B	0.970
O2'—CC2'	1.359 (3)	C41—C42	1.551 (10)
CC2'—CO2'	1.220 (3)	C41—H41A	0.960
CC2'—CM2'	1.498 (3)	C41—H41B	0.960
CM2'—HM2D	0.960	C41—H41C	0.960
CM2'—HM2E	0.960	C42—O41	1.439 (10)
CM2'—HM2F	0.960	C42—H42A	0.970
C3'—O3'	1.445 (2)	C42—H42B	0.970
C3'—C4'	1.529 (3)	O41—H41	0.820

O5—C1—O1	111.75 (14)	C2'—C3'—C4'	111.49 (14)
O5—C1—C2	110.32 (13)	O3'—C3'—H3'	109.8
O1—C1—C2	106.99 (13)	C2'—C3'—H3'	109.8
O5—C1—H1	109.2	C4'—C3'—H3'	109.8
O1—C1—H1	109.2	CC3'—O3'—C3'	119.22 (14)
C2—C1—H1	109.2	CO3'—CC3'—O3'	122.70 (17)
C1—O1—C1'	112.65 (12)	CO3'—CC3'—CM3'	126.49 (17)
O2—C2—C1	111.50 (13)	O3'—CC3'—CM3'	110.81 (15)
O2—C2—C3	106.68 (13)	CC3'—CM3'—HM3D	109.5
C1—C2—C3	110.10 (13)	CC3'—CM3'—HM3E	109.5
O2—C2—H2	109.5	HM3D—CM3'—HM3E	109.5
C1—C2—H2	109.5	CC3'—CM3'—HM3F	109.5
C3—C2—H2	109.5	HM3D—CM3'—HM3F	109.5
CC2—O2—C2	116.74 (14)	HM3E—CM3'—HM3F	109.5
CO2—CC2—O2	122.01 (18)	O4'—C4'—C3'	108.47 (14)
CO2—CC2—CM2	127.35 (19)	O4'—C4'—C5'	105.89 (14)
O2—CC2—CM2	110.64 (17)	C3'—C4'—C5'	111.44 (15)
CC2—CM2—HM2A	109.5	O4'—C4'—H4'	110.3
CC2—CM2—HM2B	109.5	C3'—C4'—H4'	110.3
HM2A—CM2—HM2B	109.5	C5'—C4'—H4'	110.3
CC2—CM2—HM2C	109.5	CC4'—O4'—C4'	118.14 (16)
HM2A—CM2—HM2C	109.5	CO4'—CC4'—O4'	124.3 (2)
HM2B—CM2—HM2C	109.5	CO4'—CC4'—CM4'	125.7 (2)
O3—C3—C4	109.61 (14)	O4'—CC4'—CM4'	109.8 (2)
O3—C3—C2	105.78 (13)	CC4'—CM4'—HM4D	109.5
C4—C3—C2	110.04 (14)	CC4'—CM4'—HM4E	109.5
O3—C3—H3	110.4	HM4D—CM4'—HM4E	109.5
C4—C3—H3	110.4	CC4'—CM4'—HM4F	109.5
C2—C3—H3	110.4	HM4D—CM4'—HM4F	109.5
CC3—O3—C3	118.50 (12)	HM4E—CM4'—HM4F	109.5
CO3—CC3—O3	122.12 (16)	O5'—C5'—C6'	107.10 (16)
CO3—CC3—CM3	127.06 (17)	O5'—C5'—C4'	109.40 (15)
O3—CC3—CM3	110.75 (15)	C6'—C5'—C4'	111.37 (16)
CC3—CM3—HM3A	109.5	O5'—C5'—H5'	109.6
CC3—CM3—HM3B	109.5	C6'—C5'—H5'	109.6
HM3A—CM3—HM3B	109.5	C4'—C5'—H5'	109.6
CC3—CM3—HM3C	109.5	C1'—O5'—C5'	113.65 (12)
HM3A—CM3—HM3C	109.5	O6'—C6'—C5'	108.32 (16)
HM3B—CM3—HM3C	109.5	O6'—C6'—H6'1	110.0
O4—C4—C3	109.20 (15)	C5'—C6'—H6'1	110.0
O4—C4—C5	106.12 (14)	O6'—C6'—H6'2	110.0
C3—C4—C5	110.10 (14)	C5'—C6'—H6'2	110.0
O4—C4—H4	110.4	H6'1—C6'—H6'2	108.4
C3—C4—H4	110.4	CC6'—O6'—C6'	118.17 (19)
C5—C4—H4	110.4	CO6'—CC6'—O6'	121.8 (2)
CC4—O4—C4	118.33 (13)	CO6'—CC6'—CM6'	126.2 (3)
CO4—CC4—O4	124.02 (17)	O6'—CC6'—CM6'	112.0 (2)
CO4—CC4—CM4	125.98 (18)	CC6'—CM6'—HM6D	109.5
O4—CC4—CM4	109.98 (16)	CC6'—CM6'—HM6E	109.5
CC4—CM4—HM4A	109.5	HM6D—CM6'—HM6E	109.5
CC4—CM4—HM4B	109.5	CC6'—CM6'—HM6F	109.5
HM4A—CM4—HM4B	109.5	HM6D—CM6'—HM6F	109.5
CC4—CM4—HM4C	109.5	HM6E—CM6'—HM6F	109.5
HM4A—CM4—HM4C	109.5	C12—C11—H11A	109.5
HM4B—CM4—HM4C	109.5	C12—C11—H11B	109.5
O5—C5—C6	106.89 (17)	H11A—C11—H11B	109.5
O5—C5—C4	109.81 (14)	C12—C11—H11C	109.5
C6—C5—C4	110.71 (15)	H11A—C11—H11C	109.5
O5—C5—H5	109.8	H11B—C11—H11C	109.5
C6—C5—H5	109.8	O11—C12—C11	110.9 (4)
C4—C5—H5	109.8	O11—C12—H12A	109.5
C1—O5—C5	113.34 (14)	C11—C12—H12A	109.5
O6—C6—C5	108.84 (19)	O11—C12—H12B	109.5
O6—C6—H6A	109.9	C11—C12—H12B	109.5
C5—C6—H6A	109.9	H12A—C12—H12B	108.1
O6—C6—H6B	109.9	C12—O11—H11	109.5
C5—C6—H6B	109.9	C22—C21—H21A	109.5
H6A—C6—H6B	108.3	C22—C21—H21B	109.5
CC6—O6—C6	119.7 (2)	H21A—C21—H21B	109.5
CO6—CC6—O6	121.7 (2)	C22—C21—H21C	109.5
CO6—CC6—CM6	125.9 (3)	H21A—C21—H21C	109.5
O6—CC6—CM6	112.2 (2)	H21B—C21—H21C	109.5
CC6—CM6—HM6A	109.5	O21—C22—C21	123.1 (4)
CC6—CM6—HM6B	109.5	O21—C22—H22A	106.6
HM6A—CM6—HM6B	109.5	C21—C22—H22A	106.6
CC6—CM6—HM6C	109.5	O21—C22—H22B	106.6
HM6A—CM6—HM6C	109.5	C21—C22—H22B	106.6
HM6B—CM6—HM6C	109.5	H22A—C22—H22B	106.5
O5'—C1'—O1	110.78 (14)	C22—O21—H21	109.5
O5'—C1'—C2'	109.20 (14)	C32—C31—H31A	109.5
O1—C1'—C2'	107.76 (13)	C32—C31—H31B	109.5
O5'—C1'—H1'	109.7	H31A—C31—H31B	109.5
O1—C1'—H1'	109.7	C32—C31—H31C	109.5
C2'—C1'—H1'	109.7	H31A—C31—H31C	109.5
O2'—C2'—C3'	105.68 (13)	H31B—C31—H31C	109.5
O2'—C2'—C1'	111.39 (14)	C31—C32—H32A	108.8
C3'—C2'—C1'	112.54 (15)	C31—C32—H32B	108.8
O2'—C2'—H2'	109.0	H32A—C32—H32B	107.7
C3'—C2'—H2'	109.0	C42—C41—H41A	109.5
C1'—C2'—H2'	109.0	C42—C41—H41B	109.5
CC2'—O2'—C2'	117.62 (14)	H41A—C41—H41B	109.5
CO2'—CC2'—O2'	122.16 (18)	C42—C41—H41C	109.5
CO2'—CC2'—CM2'	126.6 (2)	H41A—C41—H41C	109.5
O2'—CC2'—CM2'	111.18 (17)	H41B—C41—H41C	109.5
CC2'—CM2'—HM2D	109.5	O41—C42—C41	108.0 (10)
CC2'—CM2'—HM2E	109.5	O41—C42—H42A	110.1
HM2D—CM2'—HM2E	109.5	C41—C42—H42A	110.1
CC2'—CM2'—HM2F	109.5	O41—C42—H42B	110.1
HM2D—CM2'—HM2F	109.5	C41—C42—H42B	110.1
HM2E—CM2'—HM2F	109.5	H42A—C42—H42B	108.4
O3'—C3'—C2'	106.93 (14)	C42—O41—H41	109.5
O3'—C3'—C4'	108.92 (14)

O5—C1—O1—C1'	80.75 (17)	C1—O1—C1'—C2'	−161.96 (15)
C2—C1—O1—C1'	−158.39 (14)	O5'—C1'—C2'—O2'	173.07 (13)
O5—C1—C2—O2	175.00 (13)	O1—C1'—C2'—O2'	52.68 (19)
O1—C1—C2—O2	53.24 (17)	O5'—C1'—C2'—C3'	54.60 (18)
O5—C1—C2—C3	56.79 (17)	O1—C1'—C2'—C3'	−65.80 (18)
O1—C1—C2—C3	−64.97 (17)	C3'—C2'—O2'—CC2'	−156.39 (14)
C1—C2—O2—CC2	93.32 (16)	C1'—C2'—O2'—CC2'	81.10 (18)
C3—C2—O2—CC2	−146.45 (13)	C2'—O2'—CC2'—CO2'	−2.4 (2)
C2—O2—CC2—CO2	−4.2 (2)	C2'—O2'—CC2'—CM2'	176.38 (15)
C2—O2—CC2—CM2	175.80 (15)	O2'—C2'—C3'—O3'	70.28 (15)
O2—C2—C3—O3	66.20 (16)	C1'—C2'—C3'—O3'	−167.94 (13)
C1—C2—C3—O3	−172.66 (13)	O2'—C2'—C3'—C4'	−170.78 (13)
O2—C2—C3—C4	−175.49 (13)	C1'—C2'—C3'—C4'	−48.99 (17)
C1—C2—C3—C4	−54.35 (18)	C2'—C3'—O3'—CC3'	−126.98 (17)
C4—C3—O3—CC3	108.98 (18)	C4'—C3'—O3'—CC3'	112.42 (18)
C2—C3—O3—CC3	−132.42 (16)	C3'—O3'—CC3'—CO3'	−3.9 (3)
C3—O3—CC3—CO3	−5.0 (3)	C3'—O3'—CC3'—CM3'	176.09 (16)
C3—O3—CC3—CM3	177.93 (17)	O3'—C3'—C4'—O4'	−77.79 (16)
O3—C3—C4—O4	−73.87 (16)	C2'—C3'—C4'—O4'	164.46 (13)
C2—C3—C4—O4	170.20 (12)	O3'—C3'—C4'—C5'	166.03 (14)
O3—C3—C4—C5	169.99 (13)	C2'—C3'—C4'—C5'	48.28 (18)
C2—C3—C4—C5	54.06 (18)	C3'—C4'—O4'—CC4'	99.6 (2)
C3—C4—O4—CC4	99.41 (19)	C5'—C4'—O4'—CC4'	−140.69 (19)
C5—C4—O4—CC4	−141.94 (17)	C4'—O4'—CC4'—CO4'	0.9 (4)
C4—O4—CC4—CO4	2.4 (3)	C4'—O4'—CC4'—CM4'	−175.15 (18)
C4—O4—CC4—CM4	−178.90 (17)	O4'—C4'—C5'—O5'	−171.10 (13)
O4—C4—C5—O5	−173.96 (14)	C3'—C4'—C5'—O5'	−53.34 (18)
C3—C4—C5—O5	−55.90 (19)	O4'—C4'—C5'—C6'	70.70 (19)
O4—C4—C5—C6	68.2 (2)	C3'—C4'—C5'—C6'	−171.54 (17)
C3—C4—C5—C6	−173.70 (17)	O1—C1'—O5'—C5'	56.33 (17)
O1—C1—O5—C5	57.99 (17)	C2'—C1'—O5'—C5'	−62.21 (17)
C2—C1—O5—C5	−60.91 (17)	C6'—C5'—O5'—C1'	−177.06 (14)
C6—C5—O5—C1	−179.55 (15)	C4'—C5'—O5'—C1'	62.11 (17)
C4—C5—O5—C1	60.31 (18)	O5'—C5'—C6'—O6'	74.3 (2)
O5—C5—C6—O6	67.8 (2)	C4'—C5'—C6'—O6'	−166.11 (17)
C4—C5—C6—O6	−172.59 (18)	C5'—C6'—O6'—CC6'	−125.3 (2)
C5—C6—O6—CC6	129.8 (3)	C6'—O6'—CC6'—CO6'	6.8 (4)
C6—O6—CC6—CO6	−11.1 (4)	C6'—O6'—CC6'—CM6'	−174.4 (2)
C6—O6—CC6—CM6	173.6 (2)	H1—C1—O1—C1'	−40.2
C1—O1—C1'—O5'	78.64 (18)	H1'—C1'—O1—C1	−42.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···CO3ⁱ	0.82	2.15	2.948 (6)	168
O21—H21···O5′	0.82	2.13	2.746 (6)	132

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

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