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organic compounds
The crystal structure of the title compound, C24H32O10, is stabilized by weak C—HO hydrogen bonds. The six-membered glucopyranosyl ring adopts a chair conformation.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024573/lh2114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024573/lh2114Isup2.hkl |
CCDC reference: 618977
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.048
- wR factor = 0.128
- Data-to-parameter ratio = 10.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.64 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G 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 27.50 From the CIF: _reflns_number_total 3374 Count of symmetry unique reflns 3402 Completeness (_total/calc) 99.18% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
C24H32O10 | Dx = 1.230 Mg m−3 |
Mr = 480.50 | Melting point = 411–413 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5849 reflections |
a = 8.093 (2) Å | θ = 3.7–27.5° |
b = 10.932 (4) Å | µ = 0.10 mm−1 |
c = 29.318 (11) Å | T = 173 K |
V = 2593.8 (15) Å3 | Block, colourless |
Z = 4 | 0.14 × 0.12 × 0.08 mm |
F(000) = 1024 |
Data collection top
Bruker Nonius KappaCCD area-detector diffractometer | 3374 independent reflections |
Radiation source: fine-focus sealed tube | 2317 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω and φ scans | θmax = 27.5°, θmin = 3.7° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −10→10 |
Tmin = 0.987, Tmax = 0.992 | k = −14→14 |
5849 measured reflections | l = −37→38 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.064P)2 + 0.45P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.004 |
3374 reflections | Δρmax = 0.27 e Å−3 |
318 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.5652 (2) | 0.96766 (19) | 0.12280 (7) | 0.0357 (5) | |
O2 | 0.6020 (3) | 1.2129 (2) | 0.11657 (8) | 0.0465 (6) | |
O3 | 0.7981 (17) | 1.3574 (16) | 0.1244 (4) | 0.087 (3) | 0.50 |
O3' | 0.7583 (18) | 1.3726 (16) | 0.1020 (4) | 0.087 (3) | 0.50 |
O4 | 0.5564 (2) | 1.06700 (18) | 0.00395 (7) | 0.0330 (5) | |
O5 | 0.4511 (4) | 1.2566 (3) | 0.00541 (10) | 0.0664 (8) | |
O6 | 0.2287 (2) | 0.96709 (19) | 0.01897 (7) | 0.0343 (5) | |
O7 | 0.2047 (3) | 0.7899 (2) | −0.01980 (8) | 0.0524 (6) | |
O8 | 0.2464 (2) | 0.76002 (18) | 0.08389 (7) | 0.0354 (5) | |
O9 | 0.0011 (3) | 0.8474 (2) | 0.09916 (9) | 0.0514 (7) | |
O10 | 0.4367 (2) | 0.8083 (2) | 0.15850 (7) | 0.0391 (5) | |
C1 | 0.6268 (3) | 1.0173 (3) | 0.08130 (10) | 0.0330 (7) | |
H1 | 0.7040 | 0.9614 | 0.0677 | 0.040* | |
C2 | 0.4849 (3) | 1.0385 (3) | 0.04782 (10) | 0.0300 (6) | |
H2 | 0.4181 | 1.1047 | 0.0589 | 0.036* | |
C3 | 0.3766 (3) | 0.9263 (3) | 0.04229 (10) | 0.0297 (7) | |
H3 | 0.4363 | 0.8660 | 0.0251 | 0.036* | |
C4 | 0.3300 (3) | 0.8752 (3) | 0.08870 (10) | 0.0317 (7) | |
H4 | 0.2600 | 0.9330 | 0.1040 | 0.038* | |
C5 | 0.4860 (4) | 0.8526 (3) | 0.11604 (10) | 0.0344 (7) | |
H5 | 0.5573 | 0.7940 | 0.1017 | 0.041* | |
C6 | 0.7163 (4) | 1.1338 (3) | 0.09304 (12) | 0.0410 (8) | |
H6A | 0.7536 | 1.1738 | 0.0658 | 0.049* | |
H6B | 0.8091 | 1.1175 | 0.1125 | 0.049* | |
C7 | 0.6511 (5) | 1.3261 (4) | 0.12562 (16) | 0.0632 (11) | |
C8 | 0.5256 (6) | 1.3958 (4) | 0.15248 (17) | 0.0776 (14) | |
H8A | 0.5435 | 1.4838 | 0.1482 | 0.093* | |
H8B | 0.5366 | 1.3754 | 0.1849 | 0.093* | |
H8C | 0.4146 | 1.3741 | 0.1420 | 0.093* | |
C9 | 0.5324 (4) | 1.1811 (3) | −0.01349 (11) | 0.0402 (8) | |
C10 | 0.6145 (4) | 1.1959 (3) | −0.05834 (12) | 0.0484 (9) | |
H10A | 0.6316 | 1.2830 | −0.0645 | 0.058* | |
H10B | 0.5448 | 1.1604 | −0.0823 | 0.058* | |
H10C | 0.7215 | 1.1539 | −0.0579 | 0.058* | |
C11 | 0.1524 (4) | 0.8893 (3) | −0.01034 (11) | 0.0388 (8) | |
C12 | −0.0054 (4) | 0.9436 (3) | −0.02714 (14) | 0.0533 (10) | |
H12A | −0.0122 | 0.9341 | −0.0603 | 0.064* | |
H12B | −0.0089 | 1.0307 | −0.0193 | 0.064* | |
H12C | −0.0990 | 0.9015 | −0.0128 | 0.064* | |
C13 | 0.0819 (4) | 0.7575 (3) | 0.09222 (10) | 0.0364 (7) | |
C14 | 0.0208 (5) | 0.6293 (3) | 0.09203 (13) | 0.0527 (9) | |
H14A | −0.0994 | 0.6290 | 0.0960 | 0.063* | |
H14B | 0.0725 | 0.5838 | 0.1170 | 0.063* | |
H14C | 0.0489 | 0.5906 | 0.0629 | 0.063* | |
C15 | 0.5551 (4) | 0.7567 (3) | 0.18655 (10) | 0.0340 (7) | |
C16 | 0.7236 (4) | 0.7620 (3) | 0.17865 (11) | 0.0412 (8) | |
H16 | 0.7624 | 0.8036 | 0.1519 | 0.049* | |
C17 | 0.8298 (4) | 0.7068 (3) | 0.20939 (11) | 0.0431 (8) | |
H17 | 0.9468 | 0.7090 | 0.2042 | 0.052* | |
C18 | 0.7733 (4) | 0.6469 (3) | 0.24831 (11) | 0.0407 (8) | |
C19 | 0.6020 (4) | 0.6435 (3) | 0.25486 (12) | 0.0463 (9) | |
H19 | 0.5580 | 0.6031 | 0.2813 | 0.056* | |
C20 | 0.4954 (4) | 0.6967 (3) | 0.22457 (11) | 0.0435 (8) | |
H20 | 0.3781 | 0.6913 | 0.2290 | 0.052* | |
C21 | 0.8876 (4) | 0.5848 (4) | 0.28278 (13) | 0.0511 (9) | |
C22 | 0.8502 (5) | 0.6345 (4) | 0.33105 (13) | 0.0698 (12) | |
H22A | 0.9202 | 0.5924 | 0.3534 | 0.084* | |
H22B | 0.7337 | 0.6200 | 0.3384 | 0.084* | |
H22C | 0.8730 | 0.7225 | 0.3320 | 0.084* | |
C23 | 1.0680 (4) | 0.6075 (5) | 0.27326 (16) | 0.0775 (15) | |
H23A | 1.1352 | 0.5667 | 0.2965 | 0.093* | |
H23B | 1.0899 | 0.6956 | 0.2739 | 0.093* | |
H23C | 1.0963 | 0.5749 | 0.2431 | 0.093* | |
C24 | 0.8550 (6) | 0.4496 (4) | 0.28294 (17) | 0.0755 (13) | |
H24A | 0.9244 | 0.4103 | 0.3061 | 0.091* | |
H24B | 0.8811 | 0.4156 | 0.2529 | 0.091* | |
H24C | 0.7384 | 0.4347 | 0.2900 | 0.091* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0365 (10) | 0.0395 (12) | 0.0312 (11) | −0.0042 (10) | −0.0002 (9) | 0.0008 (10) |
O2 | 0.0489 (13) | 0.0420 (14) | 0.0485 (13) | −0.0095 (11) | 0.0019 (11) | −0.0127 (11) |
O3 | 0.064 (6) | 0.062 (4) | 0.135 (10) | −0.027 (4) | 0.017 (6) | −0.025 (8) |
O3' | 0.064 (6) | 0.062 (4) | 0.135 (10) | −0.027 (4) | 0.017 (6) | −0.025 (8) |
O4 | 0.0364 (10) | 0.0299 (11) | 0.0326 (11) | 0.0003 (9) | 0.0031 (9) | 0.0023 (9) |
O5 | 0.0892 (19) | 0.0372 (14) | 0.0728 (18) | 0.0195 (15) | 0.0224 (16) | 0.0115 (13) |
O6 | 0.0325 (10) | 0.0309 (12) | 0.0393 (12) | 0.0001 (9) | −0.0083 (9) | −0.0019 (10) |
O7 | 0.0551 (14) | 0.0392 (14) | 0.0629 (16) | 0.0032 (12) | −0.0125 (12) | −0.0189 (12) |
O8 | 0.0356 (11) | 0.0294 (12) | 0.0412 (12) | −0.0034 (9) | 0.0060 (9) | −0.0028 (10) |
O9 | 0.0349 (12) | 0.0482 (15) | 0.0712 (17) | −0.0017 (12) | 0.0076 (12) | −0.0078 (13) |
O10 | 0.0318 (10) | 0.0512 (14) | 0.0341 (11) | 0.0043 (11) | 0.0048 (9) | 0.0105 (10) |
C1 | 0.0288 (13) | 0.0366 (17) | 0.0337 (16) | 0.0021 (14) | 0.0003 (12) | 0.0023 (14) |
C2 | 0.0303 (14) | 0.0280 (15) | 0.0317 (15) | 0.0021 (13) | 0.0022 (12) | −0.0008 (13) |
C3 | 0.0297 (14) | 0.0261 (15) | 0.0332 (15) | 0.0036 (13) | −0.0017 (12) | −0.0041 (13) |
C4 | 0.0307 (14) | 0.0284 (16) | 0.0361 (16) | 0.0002 (13) | 0.0020 (13) | −0.0019 (13) |
C5 | 0.0307 (15) | 0.0396 (18) | 0.0330 (16) | 0.0004 (14) | 0.0031 (13) | 0.0026 (14) |
C6 | 0.0326 (15) | 0.048 (2) | 0.0420 (18) | −0.0051 (15) | −0.0019 (15) | 0.0001 (17) |
C7 | 0.060 (2) | 0.046 (2) | 0.084 (3) | −0.012 (2) | 0.010 (2) | −0.015 (2) |
C8 | 0.094 (3) | 0.048 (2) | 0.091 (3) | −0.008 (3) | 0.025 (3) | −0.020 (2) |
C9 | 0.0398 (17) | 0.0362 (19) | 0.0447 (19) | −0.0043 (16) | −0.0039 (15) | 0.0055 (15) |
C10 | 0.0488 (18) | 0.049 (2) | 0.048 (2) | −0.0091 (18) | −0.0031 (17) | 0.0131 (17) |
C11 | 0.0411 (17) | 0.0340 (18) | 0.0412 (18) | −0.0057 (15) | −0.0059 (15) | −0.0026 (15) |
C12 | 0.0489 (19) | 0.044 (2) | 0.067 (2) | −0.0018 (18) | −0.0238 (19) | −0.0024 (19) |
C13 | 0.0374 (16) | 0.0415 (19) | 0.0302 (15) | −0.0069 (15) | 0.0023 (13) | −0.0016 (15) |
C14 | 0.056 (2) | 0.048 (2) | 0.054 (2) | −0.0150 (18) | 0.0050 (19) | −0.0059 (18) |
C15 | 0.0327 (14) | 0.0342 (17) | 0.0352 (16) | 0.0003 (14) | 0.0008 (13) | 0.0041 (14) |
C16 | 0.0389 (17) | 0.047 (2) | 0.0375 (17) | −0.0013 (16) | 0.0048 (14) | 0.0104 (16) |
C17 | 0.0352 (16) | 0.046 (2) | 0.048 (2) | −0.0020 (16) | 0.0006 (15) | 0.0091 (17) |
C18 | 0.0455 (18) | 0.0371 (19) | 0.0395 (19) | −0.0057 (16) | −0.0058 (15) | 0.0075 (15) |
C19 | 0.0470 (19) | 0.052 (2) | 0.0403 (19) | −0.0047 (17) | 0.0054 (16) | 0.0117 (17) |
C20 | 0.0360 (16) | 0.053 (2) | 0.0413 (18) | −0.0027 (17) | 0.0037 (15) | 0.0095 (16) |
C21 | 0.0439 (18) | 0.055 (2) | 0.055 (2) | 0.0002 (18) | −0.0054 (17) | 0.0196 (19) |
C22 | 0.066 (3) | 0.094 (3) | 0.050 (2) | 0.000 (3) | −0.009 (2) | 0.014 (2) |
C23 | 0.044 (2) | 0.111 (4) | 0.077 (3) | 0.007 (3) | −0.003 (2) | 0.045 (3) |
C24 | 0.075 (3) | 0.063 (3) | 0.089 (3) | 0.016 (2) | 0.012 (3) | 0.028 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.423 (3) | C10—H10A | 0.9800 |
O1—C5 | 1.425 (4) | C10—H10B | 0.9800 |
O2—C7 | 1.327 (4) | C10—H10C | 0.9800 |
O2—C6 | 1.442 (4) | C11—C12 | 1.492 (5) |
O3—C7 | 1.238 (14) | C12—H12A | 0.9800 |
O3'—C7 | 1.222 (16) | C12—H12B | 0.9800 |
O4—C9 | 1.362 (4) | C12—H12C | 0.9800 |
O4—C2 | 1.445 (3) | C13—C14 | 1.486 (5) |
O5—C9 | 1.192 (4) | C14—H14A | 0.9800 |
O6—C11 | 1.357 (4) | C14—H14B | 0.9800 |
O6—C3 | 1.448 (3) | C14—H14C | 0.9800 |
O7—C11 | 1.200 (4) | C15—C20 | 1.381 (4) |
O8—C13 | 1.354 (4) | C15—C16 | 1.385 (4) |
O8—C4 | 1.437 (4) | C16—C17 | 1.383 (5) |
O9—C13 | 1.197 (4) | C16—H16 | 0.9598 |
O10—C15 | 1.383 (4) | C17—C18 | 1.393 (4) |
O10—C5 | 1.394 (4) | C17—H17 | 0.9599 |
C1—C6 | 1.505 (4) | C18—C19 | 1.399 (5) |
C1—C2 | 1.528 (4) | C18—C21 | 1.529 (5) |
C1—H1 | 0.9600 | C19—C20 | 1.368 (5) |
C2—C3 | 1.516 (4) | C19—H19 | 0.9600 |
C2—H2 | 0.9600 | C20—H20 | 0.9600 |
C3—C4 | 1.518 (4) | C21—C24 | 1.501 (6) |
C3—H3 | 0.9600 | C21—C23 | 1.507 (5) |
C4—C5 | 1.516 (4) | C21—C22 | 1.546 (6) |
C4—H4 | 0.9600 | C22—H22A | 0.9800 |
C5—H5 | 0.9600 | C22—H22B | 0.9800 |
C6—H6A | 0.9600 | C22—H22C | 0.9800 |
C6—H6B | 0.9600 | C23—H23A | 0.9800 |
C7—C8 | 1.494 (6) | C23—H23B | 0.9800 |
C8—H8A | 0.9800 | C23—H23C | 0.9800 |
C8—H8B | 0.9800 | C24—H24A | 0.9800 |
C8—H8C | 0.9800 | C24—H24B | 0.9800 |
C9—C10 | 1.482 (5) | C24—H24C | 0.9800 |
C1—O1—C5 | 112.0 (2) | H10B—C10—H10C | 109.5 |
C7—O2—C6 | 117.6 (3) | O7—C11—O6 | 123.6 (3) |
C9—O4—C2 | 118.3 (2) | O7—C11—C12 | 125.9 (3) |
C11—O6—C3 | 118.8 (2) | O6—C11—C12 | 110.5 (3) |
C13—O8—C4 | 117.6 (2) | C11—C12—H12A | 109.5 |
C15—O10—C5 | 118.3 (2) | C11—C12—H12B | 109.5 |
O1—C1—C6 | 107.2 (2) | H12A—C12—H12B | 109.5 |
O1—C1—C2 | 110.1 (2) | C11—C12—H12C | 109.5 |
C6—C1—C2 | 112.3 (3) | H12A—C12—H12C | 109.5 |
O1—C1—H1 | 109.9 | H12B—C12—H12C | 109.5 |
C6—C1—H1 | 108.7 | O9—C13—O8 | 123.4 (3) |
C2—C1—H1 | 108.7 | O9—C13—C14 | 126.3 (3) |
O4—C2—C3 | 108.1 (2) | O8—C13—C14 | 110.2 (3) |
O4—C2—C1 | 107.7 (2) | C13—C14—H14A | 109.5 |
C3—C2—C1 | 112.3 (2) | C13—C14—H14B | 109.5 |
O4—C2—H2 | 111.4 | H14A—C14—H14B | 109.5 |
C3—C2—H2 | 108.7 | C13—C14—H14C | 109.5 |
C1—C2—H2 | 108.7 | H14A—C14—H14C | 109.5 |
O6—C3—C2 | 106.2 (2) | H14B—C14—H14C | 109.5 |
O6—C3—C4 | 109.3 (2) | C20—C15—O10 | 115.6 (3) |
C2—C3—C4 | 110.2 (2) | C20—C15—C16 | 119.9 (3) |
O6—C3—H3 | 112.3 | O10—C15—C16 | 124.5 (3) |
C2—C3—H3 | 108.7 | C17—C16—C15 | 119.0 (3) |
C4—C3—H3 | 110.0 | C17—C16—H16 | 122.4 |
O8—C4—C5 | 107.5 (2) | C15—C16—H16 | 118.6 |
O8—C4—C3 | 110.6 (2) | C16—C17—C18 | 122.3 (3) |
C5—C4—C3 | 109.1 (2) | C16—C17—H17 | 119.9 |
O8—C4—H4 | 110.2 | C18—C17—H17 | 117.8 |
C5—C4—H4 | 110.6 | C17—C18—C19 | 116.7 (3) |
C3—C4—H4 | 108.9 | C17—C18—C21 | 123.5 (3) |
O10—C5—O1 | 108.1 (2) | C19—C18—C21 | 119.8 (3) |
O10—C5—C4 | 106.9 (2) | C20—C19—C18 | 121.6 (3) |
O1—C5—C4 | 107.7 (2) | C20—C19—H19 | 119.0 |
O10—C5—H5 | 109.4 | C18—C19—H19 | 119.3 |
O1—C5—H5 | 112.3 | C19—C20—C15 | 120.3 (3) |
C4—C5—H5 | 112.2 | C19—C20—H20 | 120.7 |
O2—C6—C1 | 108.0 (2) | C15—C20—H20 | 119.0 |
O2—C6—H6A | 109.1 | C24—C21—C23 | 109.4 (4) |
C1—C6—H6A | 110.2 | C24—C21—C18 | 109.4 (3) |
O2—C6—H6B | 109.2 | C23—C21—C18 | 113.0 (3) |
C1—C6—H6B | 110.8 | C24—C21—C22 | 108.0 (3) |
H6A—C6—H6B | 109.5 | C23—C21—C22 | 107.5 (4) |
O3'—C7—O2 | 119.1 (9) | C18—C21—C22 | 109.3 (3) |
O3—C7—O2 | 122.6 (9) | C21—C22—H22A | 109.5 |
O3'—C7—C8 | 124.7 (9) | C21—C22—H22B | 109.5 |
O3—C7—C8 | 121.8 (9) | H22A—C22—H22B | 109.5 |
O2—C7—C8 | 112.2 (3) | C21—C22—H22C | 109.5 |
C7—C8—H8A | 109.5 | H22A—C22—H22C | 109.5 |
C7—C8—H8B | 109.5 | H22B—C22—H22C | 109.5 |
H8A—C8—H8B | 109.5 | C21—C23—H23A | 109.5 |
C7—C8—H8C | 109.5 | C21—C23—H23B | 109.5 |
H8A—C8—H8C | 109.5 | H23A—C23—H23B | 109.5 |
H8B—C8—H8C | 109.5 | C21—C23—H23C | 109.5 |
O5—C9—O4 | 122.6 (3) | H23A—C23—H23C | 109.5 |
O5—C9—C10 | 125.8 (3) | H23B—C23—H23C | 109.5 |
O4—C9—C10 | 111.6 (3) | C21—C24—H24A | 109.5 |
C9—C10—H10A | 109.5 | C21—C24—H24B | 109.5 |
C9—C10—H10B | 109.5 | H24A—C24—H24B | 109.5 |
H10A—C10—H10B | 109.5 | C21—C24—H24C | 109.5 |
C9—C10—H10C | 109.5 | H24A—C24—H24C | 109.5 |
H10A—C10—H10C | 109.5 | H24B—C24—H24C | 109.5 |
C5—O1—C1—C6 | −176.6 (2) | O1—C1—C6—O2 | −56.9 (3) |
C5—O1—C1—C2 | 61.0 (3) | C2—C1—C6—O2 | 64.2 (3) |
C9—O4—C2—C3 | 124.2 (3) | C6—O2—C7—O3' | 24.7 (8) |
C9—O4—C2—C1 | −114.2 (3) | C6—O2—C7—O3 | −16.9 (9) |
O1—C1—C2—O4 | −169.6 (2) | C6—O2—C7—C8 | −176.5 (3) |
C6—C1—C2—O4 | 71.0 (3) | C2—O4—C9—O5 | −2.2 (4) |
O1—C1—C2—C3 | −50.7 (3) | C2—O4—C9—C10 | 179.5 (2) |
C6—C1—C2—C3 | −170.1 (2) | C3—O6—C11—O7 | −3.6 (5) |
C11—O6—C3—C2 | 146.7 (2) | C3—O6—C11—C12 | 174.4 (3) |
C11—O6—C3—C4 | −94.5 (3) | C4—O8—C13—O9 | 7.1 (4) |
O4—C2—C3—O6 | −74.6 (3) | C4—O8—C13—C14 | −172.1 (3) |
C1—C2—C3—O6 | 166.7 (2) | C5—O10—C15—C20 | −169.7 (3) |
O4—C2—C3—C4 | 167.1 (2) | C5—O10—C15—C16 | 10.2 (5) |
C1—C2—C3—C4 | 48.4 (3) | C20—C15—C16—C17 | −0.3 (6) |
C13—O8—C4—C5 | 133.4 (3) | O10—C15—C16—C17 | 179.8 (3) |
C13—O8—C4—C3 | −107.6 (3) | C15—C16—C17—C18 | −0.5 (6) |
O6—C3—C4—O8 | 71.4 (3) | C16—C17—C18—C19 | 0.7 (5) |
C2—C3—C4—O8 | −172.2 (2) | C16—C17—C18—C21 | 179.8 (3) |
O6—C3—C4—C5 | −170.6 (2) | C17—C18—C19—C20 | −0.1 (6) |
C2—C3—C4—C5 | −54.2 (3) | C21—C18—C19—C20 | −179.2 (3) |
C15—O10—C5—O1 | −77.4 (3) | C18—C19—C20—C15 | −0.6 (6) |
C15—O10—C5—C4 | 166.8 (3) | O10—C15—C20—C19 | −179.3 (3) |
C1—O1—C5—O10 | 177.2 (2) | C16—C15—C20—C19 | 0.8 (5) |
C1—O1—C5—C4 | −67.6 (3) | C17—C18—C21—C24 | −115.6 (4) |
O8—C4—C5—O10 | −61.2 (3) | C19—C18—C21—C24 | 63.5 (5) |
C3—C4—C5—O10 | 178.8 (2) | C17—C18—C21—C23 | 6.6 (6) |
O8—C4—C5—O1 | −177.2 (2) | C19—C18—C21—C23 | −174.3 (4) |
C3—C4—C5—O1 | 62.8 (3) | C17—C18—C21—C22 | 126.3 (4) |
C7—O2—C6—C1 | −172.8 (3) | C19—C18—C21—C22 | −54.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.96 | 2.54 | 2.932 (4) | 104 |
C2—H2···O5 | 0.96 | 2.30 | 2.702 (4) | 104 |
C4—H4···O9 | 0.96 | 2.30 | 2.697 (4) | 104 |
C10—H10B···O3i | 0.98 | 2.36 | 3.263 (16) | 154 |
C10—H10B···O3′i | 0.98 | 2.42 | 3.241 (17) | 142 |
C12—H12B···O5i | 0.98 | 2.38 | 3.358 (5) | 173 |
C16—H16···O1 | 0.96 | 2.55 | 3.063 (4) | 114 |
C16—H16···O9ii | 0.96 | 2.52 | 3.368 (4) | 147 |
C24—H24C···O10iii | 0.98 | 2.49 | 3.303 (5) | 140 |
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+1/2. |
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