(2S,3S,4R,4a'R,5R,5a'R,11a'R,12′S,12a'R)-5-(Acet­oxy­meth­yl)-2′,2′,10′,10′-tetra­methyl­octa­hydro-3H,8′H-spiro­[furan-2,7′-[1,3]dioxino[4′,5′:5,6]pyrano[3,2-d][1,3,6]trioxocine]-3,4,12′-triyl tri­acetate

While the crystal structure analysis of the title compound, C₂₆H₃₈O₁₅, a synthetic derivative of sucrose, was originally reported 40 years ago [Drew et al. (1979). Carbohydr. Res. 71, 35–42], the present work has allowed for the determination of its absolute configuration through the application of resonant scattering techniques.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.098
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         78 %

Alert level G
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O2'            109.8 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT791_ALERT_4_G Model has Chirality at C1          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C2          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C2'         (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C3          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C3'         (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C4'         (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C5'         (Chiral SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  15 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

(2S,3S,4R,4a'R,5R,5a'R,11a'R,12'S,12a'R)-5-(Acetoxymethyl)-2',2',10',10'-tetramethyloctahydro-3H,8'H-spiro[furan-2,7'-[1,3]dioxino[4',5':5,6]pyrano[3,2-d][1,3,6]trioxocine]-3,4,12'-triyl triacetate

Crystal data

C26H38O15	F(000) = 628
Mr = 590.56	Dx = 1.329 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 11.1629 (2) Å	Cell parameters from 6926 reflections
b = 8.7778 (1) Å	θ = 5.0–73.6°
c = 15.3748 (3) Å	µ = 0.94 mm^−1
β = 101.558 (2)°	T = 150 K
V = 1475.96 (4) Å^3	Block, colourless
Z = 2	0.26 × 0.2 × 0.15 mm

Data collection

Rigaku Oxfird Diffraction SuperNova, Dual, Cu at home/near, EosS2 diffractometer	5289 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	5113 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.026
Detector resolution: 8.1297 pixels mm^-1	θmax = 73.7°, θmin = 4.0°
ω scans	h = −13→11
Absorption correction: integration (CrysAlis PRO; Rigaku OD, 2018)	k = −10→10
Tmin = 0.920, Tmax = 1.000	l = −18→17
10371 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0668P)^2 + 0.0718P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5289 reflections	Δρmax = 0.19 e Å^−3
378 parameters	Δρmin = −0.29 e Å^−3
1 restraint	Absolute structure: Flack x determined using 2026 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.05 (8)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. The H atoms attached to the carbon atoms were introduced in calculated positions and treated as riding: C—H = 0.96–0.98 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

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

	x	y	z	Uiso*/Ueq
O1	0.66805 (13)	0.44758 (16)	0.23465 (9)	0.0194 (4)
O1'	0.59371 (14)	0.76853 (18)	0.21908 (10)	0.0230 (4)
O2	0.79603 (14)	0.70874 (17)	0.21177 (10)	0.0212 (4)
O2'	0.46513 (13)	0.48539 (18)	0.24952 (10)	0.0227 (4)
O3	1.03877 (13)	0.61194 (18)	0.27262 (10)	0.0231 (4)
O3'	0.60065 (13)	0.29538 (19)	0.09135 (10)	0.0233 (4)
O4	1.05077 (13)	0.29710 (18)	0.32930 (10)	0.0226 (4)
O4'	0.30285 (14)	0.2773 (2)	0.09726 (11)	0.0293 (5)
O5	0.76401 (13)	0.42594 (17)	0.38307 (10)	0.0202 (4)
O6	0.98841 (14)	0.11966 (18)	0.42674 (11)	0.0258 (4)
O6'	0.47916 (15)	0.2898 (2)	0.40486 (11)	0.0300 (5)
O11	1.0621 (2)	0.5190 (3)	0.14086 (14)	0.0498 (7)
O17	0.6223 (2)	0.4819 (3)	−0.00490 (13)	0.0438 (6)
O20	0.2460 (2)	0.0736 (3)	0.16760 (14)	0.0447 (6)
O23	0.61677 (18)	0.1156 (2)	0.46666 (14)	0.0417 (6)
C1	0.72380 (18)	0.5291 (2)	0.31234 (13)	0.0180 (5)
C1'	0.5461 (2)	0.6575 (2)	0.15460 (14)	0.0239 (6)
C2	0.83133 (18)	0.6213 (2)	0.29037 (13)	0.0181 (5)
C2'	0.54969 (17)	0.4956 (2)	0.19222 (13)	0.0195 (5)
C3	0.93376 (17)	0.5178 (2)	0.27383 (13)	0.0187 (5)
C3'	0.50360 (18)	0.3786 (2)	0.11750 (14)	0.0210 (5)
C4	0.96673 (18)	0.4064 (2)	0.34956 (13)	0.0188 (5)
C4'	0.42079 (18)	0.2699 (3)	0.15538 (14)	0.0232 (6)
C5	0.85467 (18)	0.3224 (2)	0.36547 (14)	0.0195 (5)
C5'	0.41843 (19)	0.3324 (3)	0.24868 (14)	0.0235 (6)
C6	0.8952 (2)	0.2196 (3)	0.44536 (15)	0.0238 (6)
C6'	0.4918 (2)	0.2320 (3)	0.31931 (15)	0.0264 (6)
C7	1.0907 (2)	0.1927 (3)	0.40087 (14)	0.0247 (6)
C8	1.1721 (2)	0.2719 (3)	0.47857 (16)	0.0332 (7)
C9	1.1574 (3)	0.0669 (3)	0.36347 (19)	0.0400 (8)
C10	1.0970 (2)	0.5994 (3)	0.20445 (16)	0.0308 (7)
C12	1.2079 (3)	0.6986 (4)	0.2192 (2)	0.0475 (10)
C13	0.71093 (19)	0.8288 (2)	0.21280 (15)	0.0238 (6)
C14	0.7437 (2)	0.9332 (3)	0.29265 (19)	0.0354 (7)
C15	0.7081 (2)	0.9135 (3)	0.12672 (18)	0.0346 (7)
C16	0.6578 (2)	0.3652 (3)	0.03229 (16)	0.0303 (7)
C18	0.7696 (3)	0.2792 (4)	0.0219 (2)	0.0444 (9)
C19	0.2232 (2)	0.1664 (3)	0.10960 (19)	0.0351 (8)
C21	0.1074 (3)	0.1793 (4)	0.0416 (3)	0.0563 (10)
C22	0.5493 (2)	0.2184 (3)	0.47446 (16)	0.0305 (7)
C24	0.5324 (3)	0.2839 (4)	0.56148 (17)	0.0451 (9)
H1	0.66400	0.59930	0.32900	0.0220*
H1'A	0.59270	0.65990	0.10770	0.0290*
H2	0.86320	0.68960	0.34000	0.0220*
H1'B	0.46220	0.68350	0.12850	0.0290*
H3	0.90920	0.46360	0.21730	0.0220*
H3'	0.45590	0.43140	0.06580	0.0250*
H6'A	0.46210	0.12800	0.31200	0.0320*
H4	1.00430	0.46160	0.40360	0.0230*
H4'	0.45320	0.16580	0.15870	0.0280*
H6'B	0.57720	0.23260	0.31460	0.0320*
H5	0.82070	0.26050	0.31330	0.0230*
H5'	0.33360	0.33590	0.25680	0.0280*
H6A	0.92700	0.28040	0.49760	0.0290*
H6B	0.82640	0.16080	0.45670	0.0290*
H8A	1.23400	0.32900	0.45770	0.0500*
H8B	1.21000	0.19720	0.52080	0.0500*
H8C	1.12360	0.33970	0.50640	0.0500*
H9A	1.10380	0.02140	0.31360	0.0600*
H9B	1.18300	−0.00900	0.40830	0.0600*
H9C	1.22770	0.10820	0.34470	0.0600*
H12A	1.18400	0.80200	0.20450	0.0710*
H12B	1.26230	0.66470	0.18210	0.0710*
H12C	1.24860	0.69300	0.28030	0.0710*
H14A	0.73220	0.88010	0.34500	0.0530*
H14B	0.69200	1.02160	0.28380	0.0530*
H14C	0.82760	0.96410	0.29970	0.0530*
H15A	0.78360	0.96760	0.13000	0.0520*
H15B	0.64130	0.98450	0.11710	0.0520*
H15C	0.69750	0.84220	0.07850	0.0520*
H18A	0.82900	0.28350	0.07640	0.0670*
H18B	0.80310	0.32390	−0.02490	0.0670*
H18C	0.74830	0.17490	0.00760	0.0670*
H21A	0.07330	0.27910	0.04430	0.0840*
H21B	0.05000	0.10430	0.05330	0.0840*
H21C	0.12450	0.16260	−0.01640	0.0840*
H24A	0.60370	0.34140	0.58760	0.0680*
H24B	0.52070	0.20270	0.60080	0.0680*
H24C	0.46210	0.34930	0.55170	0.0680*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0172 (6)	0.0165 (7)	0.0227 (7)	0.0008 (5)	−0.0002 (5)	−0.0012 (5)
O1'	0.0229 (7)	0.0158 (7)	0.0291 (7)	0.0017 (6)	0.0022 (6)	−0.0014 (6)
O2	0.0232 (7)	0.0156 (7)	0.0239 (7)	0.0026 (6)	0.0023 (5)	0.0035 (5)
O2'	0.0216 (7)	0.0198 (8)	0.0273 (7)	−0.0001 (6)	0.0061 (5)	−0.0025 (6)
O3	0.0203 (7)	0.0241 (8)	0.0251 (7)	−0.0018 (6)	0.0053 (5)	0.0021 (6)
O3'	0.0244 (7)	0.0231 (8)	0.0236 (7)	−0.0032 (6)	0.0076 (6)	−0.0003 (6)
O4	0.0247 (7)	0.0219 (8)	0.0216 (7)	0.0079 (6)	0.0053 (5)	0.0048 (6)
O4'	0.0220 (7)	0.0296 (9)	0.0348 (8)	−0.0077 (7)	0.0024 (6)	−0.0061 (7)
O5	0.0198 (6)	0.0190 (7)	0.0217 (7)	0.0031 (5)	0.0039 (5)	0.0031 (5)
O6	0.0242 (7)	0.0188 (8)	0.0347 (8)	0.0043 (6)	0.0067 (6)	0.0072 (6)
O6'	0.0287 (8)	0.0359 (9)	0.0256 (8)	0.0057 (7)	0.0056 (6)	0.0014 (7)
O11	0.0547 (12)	0.0615 (15)	0.0396 (10)	−0.0008 (11)	0.0250 (9)	−0.0083 (10)
O17	0.0611 (12)	0.0369 (11)	0.0387 (10)	−0.0029 (10)	0.0230 (9)	0.0094 (8)
O20	0.0497 (11)	0.0409 (11)	0.0503 (11)	−0.0190 (9)	0.0264 (9)	−0.0098 (9)
O23	0.0404 (10)	0.0386 (11)	0.0480 (11)	0.0102 (9)	0.0137 (8)	0.0165 (9)
C1	0.0197 (8)	0.0137 (9)	0.0194 (9)	0.0002 (7)	0.0009 (7)	−0.0001 (7)
C1'	0.0241 (10)	0.0187 (11)	0.0260 (10)	0.0000 (8)	−0.0017 (8)	0.0017 (8)
C2	0.0203 (9)	0.0137 (9)	0.0191 (9)	−0.0008 (7)	0.0010 (7)	−0.0006 (7)
C2'	0.0172 (8)	0.0171 (10)	0.0230 (9)	−0.0004 (7)	0.0010 (7)	−0.0005 (8)
C3	0.0196 (9)	0.0163 (9)	0.0197 (9)	−0.0009 (8)	0.0030 (7)	−0.0002 (7)
C3'	0.0201 (9)	0.0200 (10)	0.0218 (9)	−0.0027 (8)	0.0014 (7)	−0.0004 (8)
C4	0.0187 (9)	0.0181 (10)	0.0188 (9)	0.0009 (7)	0.0021 (7)	−0.0005 (7)
C4'	0.0206 (9)	0.0219 (11)	0.0270 (10)	−0.0024 (8)	0.0046 (8)	−0.0011 (8)
C5	0.0200 (9)	0.0149 (10)	0.0224 (9)	0.0007 (7)	0.0016 (7)	−0.0007 (7)
C5'	0.0216 (9)	0.0218 (11)	0.0280 (11)	−0.0032 (8)	0.0073 (8)	−0.0023 (8)
C6	0.0210 (9)	0.0214 (11)	0.0291 (10)	0.0026 (8)	0.0055 (8)	0.0066 (8)
C6'	0.0289 (11)	0.0233 (11)	0.0293 (11)	−0.0011 (8)	0.0111 (8)	0.0008 (8)
C7	0.0228 (9)	0.0256 (11)	0.0263 (10)	0.0066 (9)	0.0061 (8)	0.0095 (9)
C8	0.0250 (10)	0.0414 (14)	0.0302 (11)	−0.0009 (10)	−0.0016 (8)	0.0134 (11)
C9	0.0433 (14)	0.0352 (14)	0.0456 (14)	0.0212 (12)	0.0189 (12)	0.0131 (12)
C10	0.0282 (11)	0.0326 (13)	0.0342 (12)	0.0082 (9)	0.0128 (9)	0.0089 (10)
C12	0.0312 (13)	0.0523 (18)	0.0643 (19)	−0.0029 (13)	0.0224 (12)	0.0116 (15)
C13	0.0222 (9)	0.0144 (9)	0.0328 (11)	0.0012 (8)	0.0008 (8)	0.0017 (8)
C14	0.0350 (12)	0.0178 (11)	0.0483 (14)	0.0034 (9)	−0.0040 (10)	−0.0093 (10)
C15	0.0332 (11)	0.0249 (12)	0.0439 (14)	0.0042 (10)	0.0034 (10)	0.0152 (10)
C16	0.0367 (12)	0.0307 (13)	0.0261 (11)	−0.0106 (10)	0.0126 (9)	−0.0043 (9)
C18	0.0444 (15)	0.0461 (17)	0.0505 (15)	−0.0060 (13)	0.0285 (12)	−0.0051 (14)
C19	0.0281 (11)	0.0363 (15)	0.0447 (14)	−0.0138 (10)	0.0164 (10)	−0.0206 (12)
C21	0.0255 (12)	0.059 (2)	0.082 (2)	−0.0139 (13)	0.0054 (14)	−0.0300 (19)
C22	0.0220 (10)	0.0339 (13)	0.0348 (12)	−0.0023 (9)	0.0040 (9)	0.0080 (10)
C24	0.0412 (14)	0.062 (2)	0.0297 (12)	0.0069 (14)	0.0016 (10)	0.0038 (13)

Geometric parameters (Å, º)

O1—C1	1.424 (2)	C16—C18	1.494 (4)
O1—C2'	1.416 (2)	C19—C21	1.495 (5)
O1'—C1'	1.416 (2)	C22—C24	1.502 (4)
O1'—C13	1.433 (3)	C1—H1	0.9800
O2—C2	1.419 (2)	C1'—H1'A	0.9700
O2—C13	1.421 (2)	C1'—H1'B	0.9700
O2'—C2'	1.417 (2)	C2—H2	0.9800
O2'—C5'	1.440 (3)	C3—H3	0.9800
O3—C3	1.437 (2)	C3'—H3'	0.9800
O3—C10	1.344 (3)	C4—H4	0.9800
O3'—C3'	1.430 (3)	C4'—H4'	0.9800
O3'—C16	1.356 (3)	C5—H5	0.9800
O4—C4	1.419 (2)	C5'—H5'	0.9800
O4—C7	1.433 (3)	C6—H6A	0.9700
O4'—C4'	1.437 (3)	C6—H6B	0.9700
O4'—C19	1.357 (3)	C6'—H6'A	0.9700
O5—C1	1.417 (2)	C6'—H6'B	0.9700
O5—C5	1.426 (2)	C8—H8A	0.9600
O6—C6	1.433 (3)	C8—H8B	0.9600
O6—C7	1.434 (3)	C8—H8C	0.9600
O6'—C6'	1.443 (3)	C9—H9A	0.9600
O6'—C22	1.347 (3)	C9—H9B	0.9600
O11—C10	1.205 (3)	C9—H9C	0.9600
O17—C16	1.201 (4)	C12—H12A	0.9600
O20—C19	1.197 (4)	C12—H12B	0.9600
O23—C22	1.197 (3)	C12—H12C	0.9600
C1—C2	1.540 (3)	C14—H14A	0.9600
C1'—C2'	1.532 (3)	C14—H14B	0.9600
C2—C3	1.521 (3)	C14—H14C	0.9600
C2'—C3'	1.550 (3)	C15—H15A	0.9600
C3—C4	1.509 (3)	C15—H15B	0.9600
C3'—C4'	1.523 (3)	C15—H15C	0.9600
C4—C5	1.514 (3)	C18—H18A	0.9600
C4'—C5'	1.541 (3)	C18—H18B	0.9600
C5—C6	1.518 (3)	C18—H18C	0.9600
C5'—C6'	1.507 (3)	C21—H21A	0.9600
C7—C8	1.517 (3)	C21—H21B	0.9600
C7—C9	1.509 (4)	C21—H21C	0.9600
C10—C12	1.493 (4)	C24—H24A	0.9600
C13—C14	1.517 (3)	C24—H24B	0.9600
C13—C15	1.513 (3)	C24—H24C	0.9600
C1—O1—C2'	116.59 (15)	C3—C2—H2	109.00
C1'—O1'—C13	115.27 (16)	O3—C3—H3	111.00
C2—O2—C13	117.63 (16)	C2—C3—H3	111.00
C2'—O2'—C5'	109.79 (15)	C4—C3—H3	111.00
C3—O3—C10	119.09 (17)	O3'—C3'—H3'	109.00
C3'—O3'—C16	116.24 (17)	C2'—C3'—H3'	109.00
C4—O4—C7	112.42 (16)	C4'—C3'—H3'	109.00
C4'—O4'—C19	115.15 (19)	O4—C4—H4	109.00
C1—O5—C5	112.92 (15)	C3—C4—H4	109.00
C6—O6—C7	115.61 (18)	C5—C4—H4	109.00
C6'—O6'—C22	114.40 (19)	O4'—C4'—H4'	111.00
O1—C1—O5	109.91 (14)	C3'—C4'—H4'	111.00
O1—C1—C2	107.99 (15)	C5'—C4'—H4'	111.00
O5—C1—C2	111.29 (16)	O5—C5—H5	110.00
O1'—C1'—C2'	113.36 (17)	C4—C5—H5	110.00
O2—C2—C1	112.04 (16)	C6—C5—H5	110.00
O2—C2—C3	105.69 (16)	O2'—C5'—H5'	109.00
C1—C2—C3	111.58 (15)	C4'—C5'—H5'	109.00
O1—C2'—O2'	111.79 (15)	C6'—C5'—H5'	109.00
O1—C2'—C1'	113.68 (16)	O6—C6—H6A	110.00
O1—C2'—C3'	106.55 (15)	O6—C6—H6B	110.00
O2'—C2'—C1'	108.85 (16)	C5—C6—H6A	110.00
O2'—C2'—C3'	104.79 (15)	C5—C6—H6B	110.00
C1'—C2'—C3'	110.80 (16)	H6A—C6—H6B	108.00
O3—C3—C2	107.52 (14)	O6'—C6'—H6'A	110.00
O3—C3—C4	108.01 (16)	O6'—C6'—H6'B	110.00
C2—C3—C4	109.48 (16)	C5'—C6'—H6'A	110.00
O3'—C3'—C2'	112.91 (16)	C5'—C6'—H6'B	110.00
O3'—C3'—C4'	109.86 (16)	H6'A—C6'—H6'B	108.00
C2'—C3'—C4'	105.57 (17)	C7—C8—H8A	110.00
O4—C4—C3	109.79 (16)	C7—C8—H8B	109.00
O4—C4—C5	108.07 (15)	C7—C8—H8C	109.00
C3—C4—C5	111.03 (16)	H8A—C8—H8B	110.00
O4'—C4'—C3'	106.53 (18)	H8A—C8—H8C	109.00
O4'—C4'—C5'	112.23 (17)	H8B—C8—H8C	109.00
C3'—C4'—C5'	104.94 (19)	C7—C9—H9A	109.00
O5—C5—C4	111.17 (15)	C7—C9—H9B	109.00
O5—C5—C6	109.46 (17)	C7—C9—H9C	110.00
C4—C5—C6	107.36 (17)	H9A—C9—H9B	109.00
O2'—C5'—C4'	105.47 (18)	H9A—C9—H9C	109.00
O2'—C5'—C6'	113.30 (18)	H9B—C9—H9C	110.00
C4'—C5'—C6'	110.8 (2)	C10—C12—H12A	109.00
O6—C6—C5	108.23 (17)	C10—C12—H12B	109.00
O6'—C6'—C5'	108.24 (19)	C10—C12—H12C	110.00
O4—C7—O6	110.89 (17)	H12A—C12—H12B	109.00
O4—C7—C8	110.9 (2)	H12A—C12—H12C	109.00
O4—C7—C9	106.07 (18)	H12B—C12—H12C	110.00
O6—C7—C8	111.79 (18)	C13—C14—H14A	110.00
O6—C7—C9	105.1 (2)	C13—C14—H14B	109.00
C8—C7—C9	111.9 (2)	C13—C14—H14C	109.00
O3—C10—O11	123.5 (2)	H14A—C14—H14B	109.00
O3—C10—C12	110.5 (2)	H14A—C14—H14C	109.00
O11—C10—C12	126.0 (2)	H14B—C14—H14C	109.00
O1'—C13—O2	110.40 (15)	C13—C15—H15A	109.00
O1'—C13—C14	104.12 (17)	C13—C15—H15B	109.00
O1'—C13—C15	112.41 (18)	C13—C15—H15C	109.00
O2—C13—C14	113.81 (18)	H15A—C15—H15B	109.00
O2—C13—C15	104.57 (18)	H15A—C15—H15C	110.00
C14—C13—C15	111.75 (18)	H15B—C15—H15C	109.00
O3'—C16—O17	123.3 (2)	C16—C18—H18A	109.00
O3'—C16—C18	111.0 (2)	C16—C18—H18B	109.00
O17—C16—C18	125.7 (2)	C16—C18—H18C	109.00
O4'—C19—O20	123.0 (2)	H18A—C18—H18B	110.00
O4'—C19—C21	110.3 (2)	H18A—C18—H18C	109.00
O20—C19—C21	126.7 (3)	H18B—C18—H18C	110.00
O6'—C22—O23	123.3 (2)	C19—C21—H21A	110.00
O6'—C22—C24	111.9 (2)	C19—C21—H21B	109.00
O23—C22—C24	124.9 (2)	C19—C21—H21C	109.00
O1—C1—H1	109.00	H21A—C21—H21B	109.00
O5—C1—H1	109.00	H21A—C21—H21C	110.00
C2—C1—H1	109.00	H21B—C21—H21C	109.00
O1'—C1'—H1'A	109.00	C22—C24—H24A	109.00
O1'—C1'—H1'B	109.00	C22—C24—H24B	109.00
C2'—C1'—H1'A	109.00	C22—C24—H24C	110.00
C2'—C1'—H1'B	109.00	H24A—C24—H24B	109.00
H1'A—C1'—H1'B	108.00	H24A—C24—H24C	110.00
O2—C2—H2	109.00	H24B—C24—H24C	109.00
C1—C2—H2	109.00
C2'—O1—C1—O5	127.72 (16)	C6—O6—C7—C8	72.3 (2)
C2'—O1—C1—C2	−110.71 (17)	C6—O6—C7—C9	−166.16 (19)
C1—O1—C2'—O2'	−59.4 (2)	C22—O6'—C6'—C5'	−174.31 (19)
C1—O1—C2'—C1'	64.3 (2)	C6'—O6'—C22—O23	0.0 (3)
C1—O1—C2'—C3'	−173.37 (15)	C6'—O6'—C22—C24	179.8 (2)
C13—O1'—C1'—C2'	107.1 (2)	O1—C1—C2—O2	50.69 (19)
C1'—O1'—C13—O2	−53.1 (2)	O1—C1—C2—C3	−67.60 (19)
C1'—O1'—C13—C14	−175.61 (17)	O5—C1—C2—O2	171.41 (15)
C1'—O1'—C13—C15	63.3 (2)	O5—C1—C2—C3	53.1 (2)
C13—O2—C2—C1	65.6 (2)	O1'—C1'—C2'—O1	−56.7 (2)
C13—O2—C2—C3	−172.65 (16)	O1'—C1'—C2'—O2'	68.6 (2)
C2—O2—C13—O1'	−67.5 (2)	O1'—C1'—C2'—C3'	−176.64 (17)
C2—O2—C13—C14	49.1 (2)	O2—C2—C3—O3	69.91 (18)
C2—O2—C13—C15	171.34 (17)	O2—C2—C3—C4	−172.99 (15)
C5'—O2'—C2'—O1	−83.67 (18)	C1—C2—C3—O3	−168.07 (15)
C5'—O2'—C2'—C1'	149.92 (16)	C1—C2—C3—C4	−51.0 (2)
C5'—O2'—C2'—C3'	31.35 (19)	O1—C2'—C3'—O3'	−21.2 (2)
C2'—O2'—C5'—C4'	−30.2 (2)	O1—C2'—C3'—C4'	98.89 (18)
C2'—O2'—C5'—C6'	91.2 (2)	O2'—C2'—C3'—O3'	−139.76 (16)
C10—O3—C3—C2	−129.51 (19)	O2'—C2'—C3'—C4'	−19.7 (2)
C10—O3—C3—C4	112.4 (2)	C1'—C2'—C3'—O3'	102.99 (19)
C3—O3—C10—O11	4.3 (4)	C1'—C2'—C3'—C4'	−136.97 (17)
C3—O3—C10—C12	−176.0 (2)	O3—C3—C4—O4	−70.72 (19)
C16—O3'—C3'—C2'	−82.6 (2)	O3—C3—C4—C5	169.85 (15)
C16—O3'—C3'—C4'	159.83 (18)	C2—C3—C4—O4	172.49 (15)
C3'—O3'—C16—O17	−8.5 (3)	C2—C3—C4—C5	53.1 (2)
C3'—O3'—C16—C18	170.6 (2)	O3'—C3'—C4'—O4'	−116.56 (19)
C7—O4—C4—C3	176.87 (16)	O3'—C3'—C4'—C5'	124.25 (18)
C7—O4—C4—C5	−61.9 (2)	C2'—C3'—C4'—O4'	121.41 (18)
C4—O4—C7—O6	55.2 (2)	C2'—C3'—C4'—C5'	2.2 (2)
C4—O4—C7—C8	−69.6 (2)	O4—C4—C5—O5	−177.86 (15)
C4—O4—C7—C9	168.74 (19)	O4—C4—C5—C6	62.5 (2)
C19—O4'—C4'—C3'	167.35 (19)	C3—C4—C5—O5	−57.4 (2)
C19—O4'—C4'—C5'	−78.3 (3)	C3—C4—C5—C6	−177.09 (16)
C4'—O4'—C19—O20	4.0 (4)	O4'—C4'—C5'—O2'	−99.5 (2)
C4'—O4'—C19—C21	−176.1 (2)	O4'—C4'—C5'—C6'	137.5 (2)
C5—O5—C1—O1	62.2 (2)	C3'—C4'—C5'—O2'	15.8 (2)
C5—O5—C1—C2	−57.4 (2)	C3'—C4'—C5'—C6'	−107.2 (2)
C1—O5—C5—C4	59.9 (2)	O5—C5—C6—O6	−178.50 (16)
C1—O5—C5—C6	178.32 (16)	C4—C5—C6—O6	−57.7 (2)
C7—O6—C6—C5	54.2 (2)	O2'—C5'—C6'—O6'	65.7 (2)
C6—O6—C7—O4	−52.0 (2)	C4'—C5'—C6'—O6'	−175.99 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1′	0.98	2.27	2.783 (2)	112
C1—H1···O2′	0.98	2.52	2.881 (3)	102
C1′—H1′A···O17	0.97	2.40	3.154 (3)	134
C3—H3···O11	0.98	2.31	2.721 (3)	104
C6′—H6′B···O1	0.97	2.57	3.189 (3)	122
C6—H6B···O23	0.97	2.41	3.318 (3)	156
C12—H12A···O20^i	0.96	2.58	3.432 (4)	148
C21—H21A···O11^ii	0.96	2.59	3.433 (4)	146
C24—H24C···O23^iii	0.96	2.49	3.339 (4)	147

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