Methyl
L-sorboside monohydrate, C
7H
14O
6·H
2O, was prepared from the rare sugar
L-sorbose, C
6H
12O
6, and crystallized. It was confirmed that methyl
L-sorboside formed α-pyranose with a
2C5 conformation and crystallized with one water molecule of crystallization. In the crystal, molecules are linked by O—H

O hydrogen bonds, forming a three-dimensional network. The unit-cell volume of the title compound, methyl
L-sorboside monohydrate, is 481.13 (2) Å
3 (
Z = 2), which is about 108.16 Å
3 (29.0%) greater than that of half the amount of the chemical α-
L-sorbose [745.94 (2) Å
3 (
Z = 4)].
Supporting information
CCDC reference: 2120624
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.048
- wR factor = 0.125
- Data-to-parameter ratio = 10.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........ 6.31 Note
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0062 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 31 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 66 %
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 11 Report
PLAT791_ALERT_4_G Model has Chirality at C12 (Sohnke SpGr) R Verify
PLAT791_ALERT_4_G Model has Chirality at C13 (Sohnke SpGr) S Verify
PLAT791_ALERT_4_G Model has Chirality at C14 (Sohnke SpGr) R Verify
PLAT791_ALERT_4_G Model has Chirality at C15 (Sohnke SpGr) S Verify
PLAT791_ALERT_4_G Model has Chirality at C22 (Sohnke SpGr) R Verify
PLAT791_ALERT_4_G Model has Chirality at C23 (Sohnke SpGr) S Verify
PLAT791_ALERT_4_G Model has Chirality at C24 (Sohnke SpGr) R Verify
PLAT791_ALERT_4_G Model has Chirality at C25 (Sohnke SpGr) S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
10 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
9 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: RAPID-AUTO (Rigaku, 2009); cell refinement: CrystalStructure (Rigaku, 2019); data reduction: RAPID-AUTO (Rigaku, 2009); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Methyl
α-
l-sorboside monohydrate
top
Crystal data top
C7H14O6·H2O | Z = 2 |
Mr = 212.20 | F(000) = 228 |
Triclinic, P1 | Dx = 1.465 Mg m−3 |
a = 6.7320 (5) Å | Cu Kα radiation, λ = 1.54187 Å |
b = 7.7574 (5) Å | Cell parameters from 5608 reflections |
c = 10.6128 (8) Å | θ = 4.4–68.4° |
α = 82.458 (6)° | µ = 1.15 mm−1 |
β = 72.596 (5)° | T = 296 K |
γ = 65.476 (5)° | Block, clear light colourless |
V = 481.13 (6) Å3 | 0.1 × 0.1 × 0.1 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2751 reflections with I > 2σ(I) |
ω scans | Rint = 0.045 |
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) | θmax = 68.2°, θmin = 4.4° |
Tmin = 0.698, Tmax = 1.000 | h = −8→8 |
5541 measured reflections | k = −9→9 |
2880 independent reflections | l = −12→12 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0704P)2 + 0.106P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.125 | (Δ/σ)max < 0.001 |
S = 1.13 | Δρmax = 0.26 e Å−3 |
2880 reflections | Δρmin = −0.44 e Å−3 |
272 parameters | Absolute structure: Flack x determined using 1053 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
3 restraints | Absolute structure parameter: 0.10 (17) |
Primary atom site location: iterative | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. H atoms were positioned geometrically (C—H = 0.98, 0.97 or 0.96 Å, and O—H = 0.82 Å) and refined using as riding with Uiso(H) =
1.2Ueq(C(H) or C(H,H) groups) or Uiso(H) =
1.5Ueq(C(H,H,H) or O), allowing for free rotation of the OH groups
and crystallization water molecules (O3(H3A,H3B) and O4(H4A,H4B)). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.3171 (6) | −0.0810 (5) | 0.6471 (5) | 0.0640 (11) | |
H3A | 0.382215 | −0.200873 | 0.640005 | 0.096* | |
H3B | 0.176598 | −0.058481 | 0.675652 | 0.096* | |
O4 | 0.3946 (9) | 0.0979 (7) | 0.4096 (5) | 0.0750 (13) | |
H4A | 0.330101 | 0.051068 | 0.478141 | 0.113* | |
H4B | 0.327723 | 0.101353 | 0.352282 | 0.113* | |
O11 | 0.8495 (5) | −0.0155 (4) | 0.6286 (3) | 0.0423 (7) | |
H11 | 0.842 (12) | 0.045 (11) | 0.540 (8) | 0.08 (2)* | |
O12 | 0.4941 (5) | 0.3476 (4) | 0.8818 (3) | 0.0373 (7) | |
O13 | 0.4864 (4) | 0.5035 (4) | 0.6457 (3) | 0.0361 (6) | |
H13 | 0.483156 | 0.457826 | 0.581277 | 0.054* | |
O14 | 0.8089 (5) | 0.6575 (4) | 0.6023 (3) | 0.0394 (7) | |
H14 | 0.841401 | 0.738990 | 0.622566 | 0.059* | |
O15 | 1.0305 (5) | 0.5731 (5) | 0.8089 (4) | 0.0514 (9) | |
H15 | 1.166424 | 0.550381 | 0.782309 | 0.077* | |
O16 | 0.8842 (5) | 0.1669 (4) | 0.8198 (3) | 0.0382 (7) | |
C11 | 0.6562 (7) | 0.0918 (6) | 0.7280 (5) | 0.0398 (10) | |
H11A | 0.627277 | 0.008418 | 0.801180 | 0.048* | |
H11B | 0.525403 | 0.144048 | 0.692746 | 0.048* | |
C12 | 0.6836 (6) | 0.2508 (5) | 0.7784 (4) | 0.0287 (8) | |
C13 | 0.7011 (6) | 0.4015 (5) | 0.6724 (4) | 0.0285 (8) | |
H13A | 0.812148 | 0.338344 | 0.591341 | 0.034* | |
C14 | 0.7743 (6) | 0.5397 (5) | 0.7129 (4) | 0.0279 (8) | |
H14A | 0.652616 | 0.617405 | 0.785360 | 0.033* | |
C15 | 0.9857 (7) | 0.4371 (6) | 0.7581 (5) | 0.0360 (9) | |
H15A | 1.113508 | 0.370500 | 0.683889 | 0.043* | |
C16 | 0.9460 (8) | 0.2978 (7) | 0.8656 (5) | 0.0433 (10) | |
H16A | 1.082904 | 0.228958 | 0.894020 | 0.052* | |
H16B | 0.826033 | 0.365798 | 0.940980 | 0.052* | |
C17 | 0.4524 (9) | 0.2445 (8) | 1.0017 (5) | 0.0505 (12) | |
H17A | 0.432290 | 0.135576 | 0.983637 | 0.076* | |
H17B | 0.317821 | 0.324424 | 1.063570 | 0.076* | |
H17C | 0.579122 | 0.204193 | 1.038288 | 0.076* | |
O21 | −0.0310 (5) | 1.0841 (4) | 0.3619 (3) | 0.0416 (7) | |
H21 | −0.088305 | 1.198374 | 0.348118 | 0.062* | |
O22 | 0.2120 (5) | 0.7111 (4) | 0.1172 (3) | 0.0358 (6) | |
O23 | 0.0693 (5) | 0.5868 (5) | 0.3561 (3) | 0.0382 (7) | |
H23 | −0.000861 | 0.594835 | 0.434404 | 0.057* | |
O24 | 0.4907 (6) | 0.3936 (4) | 0.4191 (3) | 0.0407 (7) | |
H24 | 0.461466 | 0.303180 | 0.412308 | 0.061* | |
O25 | 0.8573 (5) | 0.4521 (5) | 0.2383 (4) | 0.0505 (9) | |
H25 | 0.950779 | 0.489488 | 0.245670 | 0.076* | |
O26 | 0.3751 (5) | 0.8804 (4) | 0.1895 (3) | 0.0359 (7) | |
C21 | −0.0209 (7) | 0.9850 (6) | 0.2564 (5) | 0.0399 (10) | |
H21A | −0.034544 | 1.068125 | 0.179979 | 0.048* | |
H21B | −0.146711 | 0.945625 | 0.280896 | 0.048* | |
C22 | 0.2012 (6) | 0.8120 (5) | 0.2214 (4) | 0.0299 (8) | |
C23 | 0.2295 (6) | 0.6684 (5) | 0.3348 (4) | 0.0275 (8) | |
H23A | 0.200807 | 0.734529 | 0.415127 | 0.033* | |
C24 | 0.4663 (7) | 0.5142 (5) | 0.3059 (4) | 0.0295 (8) | |
H24A | 0.490914 | 0.439397 | 0.230901 | 0.035* | |
C25 | 0.6379 (6) | 0.5996 (6) | 0.2730 (5) | 0.0348 (9) | |
H25A | 0.621075 | 0.667012 | 0.349958 | 0.042* | |
C26 | 0.5985 (7) | 0.7374 (6) | 0.1591 (5) | 0.0424 (10) | |
H26A | 0.706826 | 0.796123 | 0.138250 | 0.051* | |
H26B | 0.623581 | 0.668881 | 0.081840 | 0.051* | |
C27 | 0.1985 (9) | 0.8085 (7) | −0.0053 (4) | 0.0485 (12) | |
H27A | 0.243717 | 0.718954 | −0.073325 | 0.073* | |
H27B | 0.297456 | 0.874770 | −0.027087 | 0.073* | |
H27C | 0.045401 | 0.897626 | 0.001903 | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0457 (19) | 0.048 (2) | 0.090 (3) | −0.0091 (17) | −0.0201 (19) | −0.004 (2) |
O4 | 0.098 (3) | 0.062 (3) | 0.098 (3) | −0.054 (3) | −0.047 (3) | 0.016 (3) |
O11 | 0.0536 (18) | 0.0270 (15) | 0.0462 (17) | −0.0171 (13) | −0.0100 (14) | −0.0037 (13) |
O12 | 0.0428 (15) | 0.0325 (15) | 0.0320 (14) | −0.0159 (12) | −0.0030 (12) | 0.0017 (12) |
O13 | 0.0333 (14) | 0.0382 (16) | 0.0424 (15) | −0.0142 (12) | −0.0193 (12) | 0.0026 (12) |
O14 | 0.0534 (18) | 0.0294 (15) | 0.0389 (15) | −0.0254 (14) | −0.0056 (13) | 0.0026 (12) |
O15 | 0.0384 (15) | 0.0462 (19) | 0.082 (2) | −0.0216 (14) | −0.0207 (16) | −0.0160 (17) |
O16 | 0.0411 (15) | 0.0254 (14) | 0.0507 (17) | −0.0103 (12) | −0.0219 (13) | 0.0033 (12) |
C11 | 0.043 (2) | 0.030 (2) | 0.050 (2) | −0.0201 (18) | −0.0071 (19) | −0.0055 (19) |
C12 | 0.0268 (17) | 0.0219 (17) | 0.0372 (19) | −0.0091 (14) | −0.0091 (15) | −0.0007 (15) |
C13 | 0.0302 (18) | 0.0288 (19) | 0.0299 (17) | −0.0135 (16) | −0.0102 (14) | −0.0007 (15) |
C14 | 0.0286 (17) | 0.0256 (18) | 0.0302 (18) | −0.0129 (15) | −0.0048 (15) | −0.0033 (15) |
C15 | 0.0282 (17) | 0.031 (2) | 0.051 (2) | −0.0111 (16) | −0.0104 (17) | −0.0108 (18) |
C16 | 0.049 (2) | 0.040 (2) | 0.054 (3) | −0.020 (2) | −0.031 (2) | 0.003 (2) |
C17 | 0.063 (3) | 0.053 (3) | 0.039 (2) | −0.031 (2) | −0.009 (2) | 0.005 (2) |
O21 | 0.0458 (16) | 0.0250 (14) | 0.0488 (18) | −0.0019 (13) | −0.0207 (13) | −0.0058 (13) |
O22 | 0.0518 (16) | 0.0281 (14) | 0.0327 (14) | −0.0150 (13) | −0.0201 (12) | 0.0003 (11) |
O23 | 0.0395 (15) | 0.0497 (17) | 0.0363 (14) | −0.0298 (14) | −0.0083 (12) | 0.0002 (13) |
O24 | 0.0595 (18) | 0.0286 (15) | 0.0457 (16) | −0.0187 (14) | −0.0329 (14) | 0.0089 (13) |
O25 | 0.0264 (14) | 0.0376 (17) | 0.086 (2) | −0.0052 (12) | −0.0183 (15) | −0.0139 (17) |
O26 | 0.0357 (15) | 0.0260 (14) | 0.0492 (17) | −0.0154 (12) | −0.0142 (13) | 0.0061 (12) |
C21 | 0.035 (2) | 0.029 (2) | 0.052 (3) | −0.0013 (17) | −0.0217 (18) | −0.0054 (18) |
C22 | 0.0272 (18) | 0.028 (2) | 0.036 (2) | −0.0089 (15) | −0.0130 (16) | −0.0019 (16) |
C23 | 0.0271 (17) | 0.0285 (19) | 0.0293 (18) | −0.0117 (15) | −0.0100 (14) | −0.0002 (15) |
C24 | 0.0337 (18) | 0.0232 (18) | 0.0335 (19) | −0.0082 (15) | −0.0157 (15) | −0.0015 (15) |
C25 | 0.0250 (17) | 0.025 (2) | 0.053 (2) | −0.0048 (15) | −0.0132 (17) | −0.0078 (17) |
C26 | 0.030 (2) | 0.040 (2) | 0.055 (3) | −0.0174 (18) | −0.0025 (19) | 0.001 (2) |
C27 | 0.064 (3) | 0.048 (3) | 0.033 (2) | −0.018 (2) | −0.022 (2) | 0.007 (2) |
Geometric parameters (Å, º) top
O3—H3A | 0.8500 | C17—H17B | 0.9600 |
O3—H3B | 0.8500 | C17—H17C | 0.9600 |
O4—H4A | 0.8502 | O21—H21 | 0.8200 |
O4—H4B | 0.8500 | O21—C21 | 1.409 (5) |
O11—H11 | 1.00 (8) | O22—C22 | 1.405 (5) |
O11—C11 | 1.417 (5) | O22—C27 | 1.423 (5) |
O12—C12 | 1.407 (5) | O23—H23 | 0.8200 |
O12—C17 | 1.429 (5) | O23—C23 | 1.413 (5) |
O13—H13 | 0.8200 | O24—H24 | 0.8200 |
O13—C13 | 1.425 (4) | O24—C24 | 1.429 (5) |
O14—H14 | 0.8200 | O25—H25 | 0.8200 |
O14—C14 | 1.414 (4) | O25—C25 | 1.417 (5) |
O15—H15 | 0.8200 | O26—C22 | 1.413 (5) |
O15—C15 | 1.416 (5) | O26—C26 | 1.420 (5) |
O16—C12 | 1.411 (5) | C21—H21A | 0.9700 |
O16—C16 | 1.429 (6) | C21—H21B | 0.9700 |
C11—H11A | 0.9700 | C21—C22 | 1.519 (5) |
C11—H11B | 0.9700 | C22—C23 | 1.528 (5) |
C11—C12 | 1.505 (6) | C23—H23A | 0.9800 |
C12—C13 | 1.529 (5) | C23—C24 | 1.512 (5) |
C13—H13A | 0.9800 | C24—H24A | 0.9800 |
C13—C14 | 1.505 (5) | C24—C25 | 1.493 (6) |
C14—H14A | 0.9800 | C25—H25A | 0.9800 |
C14—C15 | 1.503 (5) | C25—C26 | 1.514 (6) |
C15—H15A | 0.9800 | C26—H26A | 0.9700 |
C15—C16 | 1.508 (6) | C26—H26B | 0.9700 |
C16—H16A | 0.9700 | C27—H27A | 0.9600 |
C16—H16B | 0.9700 | C27—H27B | 0.9600 |
C17—H17A | 0.9600 | C27—H27C | 0.9600 |
| | | |
H3A—O3—H3B | 104.5 | H17B—C17—H17C | 109.5 |
H4A—O4—H4B | 104.5 | C21—O21—H21 | 109.5 |
C11—O11—H11 | 111 (4) | C22—O22—C27 | 117.3 (3) |
C12—O12—C17 | 117.3 (3) | C23—O23—H23 | 109.5 |
C13—O13—H13 | 109.5 | C24—O24—H24 | 109.5 |
C14—O14—H14 | 109.5 | C25—O25—H25 | 109.5 |
C15—O15—H15 | 109.5 | C22—O26—C26 | 114.6 (3) |
C12—O16—C16 | 114.6 (3) | O21—C21—H21A | 109.5 |
O11—C11—H11A | 109.0 | O21—C21—H21B | 109.5 |
O11—C11—H11B | 109.0 | O21—C21—C22 | 110.9 (3) |
O11—C11—C12 | 112.8 (3) | H21A—C21—H21B | 108.1 |
H11A—C11—H11B | 107.8 | C22—C21—H21A | 109.5 |
C12—C11—H11A | 109.0 | C22—C21—H21B | 109.5 |
C12—C11—H11B | 109.0 | O22—C22—O26 | 112.4 (3) |
O12—C12—O16 | 111.9 (3) | O22—C22—C21 | 111.3 (3) |
O12—C12—C11 | 111.3 (3) | O22—C22—C23 | 104.6 (3) |
O12—C12—C13 | 105.2 (3) | O26—C22—C21 | 106.0 (3) |
O16—C12—C11 | 106.1 (3) | O26—C22—C23 | 110.0 (3) |
O16—C12—C13 | 110.3 (3) | C21—C22—C23 | 112.7 (3) |
C11—C12—C13 | 112.2 (3) | O23—C23—C22 | 109.2 (3) |
O13—C13—C12 | 109.5 (3) | O23—C23—H23A | 108.8 |
O13—C13—H13A | 108.7 | O23—C23—C24 | 109.6 (3) |
O13—C13—C14 | 108.8 (3) | C22—C23—H23A | 108.8 |
C12—C13—H13A | 108.7 | C24—C23—C22 | 111.5 (3) |
C14—C13—C12 | 112.4 (3) | C24—C23—H23A | 108.8 |
C14—C13—H13A | 108.7 | O24—C24—C23 | 109.4 (3) |
O14—C14—C13 | 107.0 (3) | O24—C24—H24A | 109.3 |
O14—C14—H14A | 109.1 | O24—C24—C25 | 109.4 (3) |
O14—C14—C15 | 111.6 (3) | C23—C24—H24A | 109.3 |
C13—C14—H14A | 109.1 | C25—C24—C23 | 110.1 (3) |
C15—C14—C13 | 110.8 (3) | C25—C24—H24A | 109.3 |
C15—C14—H14A | 109.1 | O25—C25—C24 | 108.6 (3) |
O15—C15—C14 | 107.9 (3) | O25—C25—H25A | 109.6 |
O15—C15—H15A | 110.1 | O25—C25—C26 | 110.9 (3) |
O15—C15—C16 | 109.7 (4) | C24—C25—H25A | 109.6 |
C14—C15—H15A | 110.1 | C24—C25—C26 | 108.5 (3) |
C14—C15—C16 | 108.9 (3) | C26—C25—H25A | 109.6 |
C16—C15—H15A | 110.1 | O26—C26—C25 | 111.7 (3) |
O16—C16—C15 | 110.9 (4) | O26—C26—H26A | 109.3 |
O16—C16—H16A | 109.5 | O26—C26—H26B | 109.3 |
O16—C16—H16B | 109.5 | C25—C26—H26A | 109.3 |
C15—C16—H16A | 109.5 | C25—C26—H26B | 109.3 |
C15—C16—H16B | 109.5 | H26A—C26—H26B | 108.0 |
H16A—C16—H16B | 108.1 | O22—C27—H27A | 109.5 |
O12—C17—H17A | 109.5 | O22—C27—H27B | 109.5 |
O12—C17—H17B | 109.5 | O22—C27—H27C | 109.5 |
O12—C17—H17C | 109.5 | H27A—C27—H27B | 109.5 |
H17A—C17—H17B | 109.5 | H27A—C27—H27C | 109.5 |
H17A—C17—H17C | 109.5 | H27B—C27—H27C | 109.5 |
| | | |
O11—C11—C12—O12 | −176.7 (3) | O21—C21—C22—O22 | 179.4 (3) |
O11—C11—C12—O16 | −54.8 (4) | O21—C21—C22—O26 | −58.1 (4) |
O11—C11—C12—C13 | 65.6 (4) | O21—C21—C22—C23 | 62.3 (5) |
O12—C12—C13—O13 | −50.8 (4) | O22—C22—C23—O23 | −52.9 (4) |
O12—C12—C13—C14 | 70.2 (4) | O22—C22—C23—C24 | 68.4 (4) |
O13—C13—C14—O14 | −65.1 (3) | O23—C23—C24—O24 | −64.1 (4) |
O13—C13—C14—C15 | 173.1 (3) | O23—C23—C24—C25 | 175.6 (3) |
O14—C14—C15—O15 | 67.4 (4) | O24—C24—C25—O25 | 63.4 (4) |
O14—C14—C15—C16 | −173.6 (3) | O24—C24—C25—C26 | −176.0 (3) |
O15—C15—C16—O16 | 175.8 (3) | O25—C25—C26—O26 | 176.8 (3) |
O16—C12—C13—O13 | −171.6 (3) | O26—C22—C23—O23 | −173.8 (3) |
O16—C12—C13—C14 | −50.6 (4) | O26—C22—C23—C24 | −52.5 (4) |
C11—C12—C13—O13 | 70.4 (4) | C21—C22—C23—O23 | 68.1 (4) |
C11—C12—C13—C14 | −168.6 (3) | C21—C22—C23—C24 | −170.6 (3) |
C12—O16—C16—C15 | −60.5 (5) | C22—O26—C26—C25 | −59.1 (5) |
C12—C13—C14—O14 | 173.5 (3) | C22—C23—C24—O24 | 174.8 (3) |
C12—C13—C14—C15 | 51.7 (4) | C22—C23—C24—C25 | 54.6 (4) |
C13—C14—C15—O15 | −173.4 (3) | C23—C24—C25—O25 | −176.3 (3) |
C13—C14—C15—C16 | −54.4 (4) | C23—C24—C25—C26 | −55.8 (4) |
C14—C15—C16—O16 | 57.9 (5) | C24—C25—C26—O26 | 57.6 (5) |
C16—O16—C12—O12 | −61.3 (4) | C26—O26—C22—O22 | −60.8 (4) |
C16—O16—C12—C11 | 177.1 (4) | C26—O26—C22—C21 | 177.4 (4) |
C16—O16—C12—C13 | 55.4 (4) | C26—O26—C22—C23 | 55.3 (4) |
C17—O12—C12—O16 | −53.3 (5) | C27—O22—C22—O26 | −58.5 (4) |
C17—O12—C12—C11 | 65.2 (5) | C27—O22—C22—C21 | 60.3 (5) |
C17—O12—C12—C13 | −173.1 (4) | C27—O22—C22—C23 | −177.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O3 | 0.85 | 1.94 | 2.729 (7) | 154 |
O11—H11···O21i | 1.00 (8) | 1.87 (8) | 2.799 (4) | 154 (6) |
O13—H13···O24 | 0.82 | 1.83 | 2.643 (4) | 169 |
O14—H14···O11ii | 0.82 | 1.94 | 2.719 (4) | 159 |
O15—H15···O13iii | 0.82 | 2.12 | 2.898 (4) | 158 |
O21—H21···O25iv | 0.82 | 2.10 | 2.874 (4) | 157 |
O23—H23···O14v | 0.82 | 1.84 | 2.653 (4) | 169 |
O24—H24···O4 | 0.82 | 1.83 | 2.650 (5) | 176 |
O25—H25···O23iii | 0.82 | 1.97 | 2.709 (5) | 150 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x−1, y+1, z; (v) x−1, y, z. |