In the title compound, C
28H
32O
11·0.16H
2O, the substituted benzene rings are twisted slightly away from the furan ring. The dihedral angle between the two benzene rings is 8.8 (1)°. In the crystal structure, the molecules exist as C—H
O hydrogen-bonded dimers.
Supporting information
CCDC reference: 277221
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- H-atom completeness 100%
- Disorder in main residue
- R factor = 0.064
- wR factor = 0.180
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O12 .. 2.78 Ang.
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.20 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.35 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O11
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27'
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 16.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O12
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C28 H32.32 O11.16
Atom count from the _atom_site data: C28 H32 O11.16
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 4
From the CIF: _chemical_formula_sum C28 H32.32 O11.16
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 112.00 112.00 0.00
H 129.28 128.00 1.28
O 44.64 44.64 0.00
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 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
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
Diethyl 2,5-bis(3,4,5-trimethoxyphenyl)furan-3,4-dicarboxylate 0.16-hydrate
top
Crystal data top
C28H32O11·0.16H2O | F(000) = 1158 |
Mr = 547.42 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/n | Melting point: 99 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4402 (7) Å | Cell parameters from 2494 reflections |
b = 22.1502 (19) Å | θ = 2.7–23.8° |
c = 14.5043 (12) Å | µ = 0.11 mm−1 |
β = 95.835 (2)° | T = 292 K |
V = 2697.6 (4) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.20 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5270 independent reflections |
Radiation source: fine-focus sealed tube | 3426 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.949, Tmax = 0.979 | k = −27→25 |
14583 measured reflections | l = −16→17 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0817P)2 + 0.3534P] where P = (Fo2 + 2Fc2)/3 |
5270 reflections | (Δ/σ)max = 0.001 |
389 parameters | Δρmax = 0.23 e Å−3 |
4 restraints | Δρmin = −0.24 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 | Uiso*/Ueq | Occ. (<1) |
C1 | 0.5932 (3) | 0.98670 (13) | 0.79491 (17) | 0.0482 (7) | |
C2 | 0.5775 (3) | 1.04782 (13) | 0.81169 (18) | 0.0536 (8) | |
C3 | 0.4824 (3) | 1.08288 (12) | 0.74931 (18) | 0.0498 (7) | |
C4 | 0.4028 (3) | 1.05710 (12) | 0.67128 (18) | 0.0478 (7) | |
H4 | 0.3371 | 1.0807 | 0.6305 | 0.057* | |
C5 | 0.4204 (3) | 0.99602 (11) | 0.65342 (16) | 0.0392 (6) | |
C6 | 0.5158 (3) | 0.96049 (12) | 0.71583 (17) | 0.0456 (7) | |
H6 | 0.5276 | 0.9195 | 0.7046 | 0.055* | |
C7 | 0.7055 (4) | 0.89323 (14) | 0.8503 (2) | 0.0661 (9) | |
H7A | 0.6054 | 0.8739 | 0.8568 | 0.099* | |
H7B | 0.7846 | 0.8784 | 0.8971 | 0.099* | |
H7C | 0.7376 | 0.8846 | 0.7901 | 0.099* | |
C8 | 0.5819 (6) | 1.0850 (2) | 0.9639 (2) | 0.1207 (18) | |
H8A | 0.4964 | 1.1126 | 0.9468 | 0.181* | |
H8B | 0.6532 | 1.1023 | 1.0126 | 0.181* | |
H8C | 0.5393 | 1.0479 | 0.9852 | 0.181* | |
C9 | 0.4006 (4) | 1.18221 (13) | 0.7042 (2) | 0.0768 (11) | |
H9A | 0.4488 | 1.1774 | 0.6475 | 0.115* | |
H9B | 0.4141 | 1.2231 | 0.7255 | 0.115* | |
H9C | 0.2891 | 1.1731 | 0.6936 | 0.115* | |
C10 | 0.3338 (3) | 0.97104 (11) | 0.56840 (16) | 0.0381 (6) | |
C11 | 0.3005 (3) | 0.91598 (11) | 0.52696 (16) | 0.0393 (6) | |
C12 | 0.1944 (3) | 0.92798 (11) | 0.44451 (16) | 0.0389 (6) | |
C13 | 0.1729 (3) | 0.98809 (11) | 0.43940 (16) | 0.0378 (6) | |
C14 | 0.0899 (3) | 1.03036 (11) | 0.37345 (17) | 0.0410 (6) | |
C15 | 0.0162 (3) | 1.01051 (13) | 0.28898 (18) | 0.0516 (7) | |
H15 | 0.0143 | 0.9695 | 0.2749 | 0.062* | |
C16 | −0.0545 (4) | 1.05162 (14) | 0.22576 (18) | 0.0535 (7) | |
C17 | −0.0515 (3) | 1.11275 (13) | 0.24669 (18) | 0.0508 (7) | |
C18 | 0.0215 (3) | 1.13257 (12) | 0.33107 (19) | 0.0490 (7) | |
C19 | 0.0922 (3) | 1.09151 (12) | 0.39452 (17) | 0.0452 (7) | |
H19 | 0.1411 | 1.1049 | 0.4512 | 0.054* | |
C20 | −0.1133 (5) | 0.97652 (17) | 0.1104 (2) | 0.0907 (13) | |
H20A | −0.0032 | 0.9651 | 0.1134 | 0.136* | |
H20B | −0.1615 | 0.9727 | 0.0479 | 0.136* | |
H20C | −0.1673 | 0.9507 | 0.1502 | 0.136* | |
C21 | −0.2687 (4) | 1.16817 (17) | 0.1789 (2) | 0.0797 (11) | |
H21A | −0.3296 | 1.1315 | 0.1742 | 0.120* | |
H21B | −0.3010 | 1.1936 | 0.1268 | 0.120* | |
H21C | −0.2867 | 1.1888 | 0.2352 | 0.120* | |
C22 | 0.1191 (4) | 1.21677 (14) | 0.4222 (2) | 0.0737 (10) | |
H22A | 0.0780 | 1.2039 | 0.4783 | 0.111* | |
H22B | 0.1196 | 1.2601 | 0.4196 | 0.111* | |
H22C | 0.2257 | 1.2019 | 0.4210 | 0.111* | |
C23 | 0.1129 (4) | 0.88253 (12) | 0.38017 (17) | 0.0449 (7) | |
C24 | 0.1304 (5) | 0.82479 (15) | 0.2438 (2) | 0.0760 (10) | |
H24A | 0.1809 | 0.8297 | 0.1871 | 0.091* | |
H24B | 0.0182 | 0.8343 | 0.2304 | 0.091* | |
C25 | 0.1481 (5) | 0.76137 (16) | 0.2759 (2) | 0.0883 (12) | |
H25A | 0.2582 | 0.7533 | 0.2953 | 0.132* | |
H25B | 0.1115 | 0.7347 | 0.2261 | 0.132* | |
H25C | 0.0862 | 0.7551 | 0.3270 | 0.132* | |
C26 | 0.3589 (4) | 0.85588 (12) | 0.55658 (19) | 0.0530 (7) | |
C27 | 0.2935 (11) | 0.7505 (3) | 0.5429 (7) | 0.060 (3) | 0.467 (12) |
H27A | 0.1985 | 0.7280 | 0.5210 | 0.071* | 0.467 (12) |
H27B | 0.3048 | 0.7508 | 0.6101 | 0.071* | 0.467 (12) |
C28 | 0.4375 (10) | 0.7242 (5) | 0.5063 (5) | 0.074 (3) | 0.467 (12) |
H28A | 0.4277 | 0.7277 | 0.4400 | 0.110* | 0.467 (12) |
H28B | 0.4468 | 0.6824 | 0.5234 | 0.110* | 0.467 (12) |
H28C | 0.5306 | 0.7455 | 0.5321 | 0.110* | 0.467 (12) |
C27' | 0.3727 (11) | 0.7545 (3) | 0.5108 (6) | 0.071 (3) | 0.533 (12) |
H27C | 0.4776 | 0.7586 | 0.5444 | 0.085* | 0.533 (12) |
H27D | 0.3838 | 0.7386 | 0.4495 | 0.085* | 0.533 (12) |
C28' | 0.2687 (11) | 0.7153 (6) | 0.5617 (6) | 0.105 (3) | 0.533 (12) |
H28D | 0.2604 | 0.7319 | 0.6222 | 0.158* | 0.533 (12) |
H28E | 0.3137 | 0.6755 | 0.5677 | 0.158* | 0.533 (12) |
H28F | 0.1648 | 0.7132 | 0.5282 | 0.158* | 0.533 (12) |
O1 | 0.6889 (3) | 0.95594 (10) | 0.86066 (13) | 0.0682 (6) | |
O2 | 0.6644 (3) | 1.07344 (10) | 0.88719 (15) | 0.0795 (7) | |
O3 | 0.4741 (3) | 1.14250 (9) | 0.77218 (14) | 0.0682 (6) | |
O4 | 0.2574 (2) | 1.01462 (7) | 0.51448 (11) | 0.0415 (4) | |
O5 | −0.1250 (3) | 1.03710 (11) | 0.13980 (14) | 0.0796 (7) | |
O6 | −0.1068 (3) | 1.15451 (10) | 0.17984 (14) | 0.0693 (6) | |
O7 | 0.0212 (3) | 1.19369 (9) | 0.34460 (14) | 0.0670 (6) | |
O8 | −0.0213 (3) | 0.86536 (10) | 0.38455 (14) | 0.0672 (6) | |
O9 | 0.2030 (3) | 0.86633 (9) | 0.31456 (13) | 0.0648 (6) | |
O10 | 0.4587 (3) | 0.84448 (10) | 0.61832 (17) | 0.0965 (9) | |
O11 | 0.2865 (3) | 0.81276 (9) | 0.50560 (17) | 0.0896 (9) | |
O12 | 0.5861 (17) | 0.6377 (7) | 0.5183 (8) | 0.076 (4) | 0.16 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0519 (17) | 0.0528 (17) | 0.0370 (14) | 0.0005 (13) | −0.0089 (12) | 0.0025 (12) |
C2 | 0.0578 (19) | 0.0563 (19) | 0.0431 (16) | −0.0074 (14) | −0.0120 (14) | −0.0084 (13) |
C3 | 0.0581 (18) | 0.0408 (16) | 0.0481 (15) | −0.0024 (13) | −0.0057 (14) | −0.0113 (13) |
C4 | 0.0566 (18) | 0.0415 (16) | 0.0421 (15) | −0.0005 (13) | −0.0099 (13) | −0.0016 (12) |
C5 | 0.0435 (15) | 0.0381 (14) | 0.0350 (13) | −0.0037 (11) | −0.0017 (11) | −0.0009 (11) |
C6 | 0.0538 (17) | 0.0387 (15) | 0.0423 (14) | −0.0013 (12) | −0.0056 (13) | −0.0014 (11) |
C7 | 0.070 (2) | 0.062 (2) | 0.0631 (19) | 0.0075 (16) | −0.0088 (16) | 0.0110 (16) |
C8 | 0.187 (5) | 0.119 (4) | 0.050 (2) | 0.029 (3) | −0.019 (3) | −0.027 (2) |
C9 | 0.088 (3) | 0.0385 (17) | 0.096 (3) | 0.0003 (16) | −0.029 (2) | −0.0122 (17) |
C10 | 0.0448 (15) | 0.0331 (13) | 0.0353 (13) | 0.0017 (11) | −0.0013 (11) | 0.0027 (10) |
C11 | 0.0418 (15) | 0.0369 (14) | 0.0376 (13) | 0.0004 (11) | −0.0039 (11) | 0.0006 (11) |
C12 | 0.0417 (15) | 0.0391 (14) | 0.0347 (13) | −0.0028 (11) | −0.0014 (11) | −0.0004 (11) |
C13 | 0.0434 (15) | 0.0374 (14) | 0.0307 (12) | −0.0033 (11) | −0.0050 (11) | −0.0022 (10) |
C14 | 0.0445 (15) | 0.0405 (15) | 0.0372 (13) | −0.0002 (11) | 0.0001 (11) | 0.0035 (11) |
C15 | 0.0644 (19) | 0.0438 (16) | 0.0434 (15) | −0.0013 (13) | −0.0096 (14) | −0.0007 (12) |
C16 | 0.0585 (19) | 0.0616 (19) | 0.0369 (15) | 0.0022 (15) | −0.0115 (13) | 0.0039 (13) |
C17 | 0.0510 (17) | 0.0564 (18) | 0.0433 (15) | 0.0049 (14) | −0.0036 (13) | 0.0145 (13) |
C18 | 0.0540 (17) | 0.0411 (16) | 0.0521 (16) | 0.0050 (13) | 0.0066 (14) | 0.0084 (12) |
C19 | 0.0498 (17) | 0.0431 (16) | 0.0416 (14) | 0.0038 (12) | −0.0011 (12) | 0.0014 (12) |
C20 | 0.123 (3) | 0.084 (3) | 0.057 (2) | 0.001 (2) | −0.033 (2) | −0.0167 (18) |
C21 | 0.067 (2) | 0.083 (3) | 0.083 (2) | 0.0085 (19) | −0.0204 (19) | 0.0105 (19) |
C22 | 0.091 (3) | 0.0452 (19) | 0.083 (2) | −0.0065 (17) | −0.003 (2) | 0.0017 (16) |
C23 | 0.0538 (18) | 0.0381 (15) | 0.0408 (15) | −0.0012 (13) | −0.0047 (13) | −0.0008 (11) |
C24 | 0.103 (3) | 0.068 (2) | 0.0562 (19) | −0.023 (2) | 0.0036 (18) | −0.0236 (16) |
C25 | 0.114 (3) | 0.063 (2) | 0.084 (3) | −0.019 (2) | −0.007 (2) | −0.0256 (19) |
C26 | 0.068 (2) | 0.0407 (16) | 0.0456 (15) | 0.0073 (14) | −0.0155 (14) | −0.0055 (12) |
C27 | 0.057 (6) | 0.047 (6) | 0.075 (6) | 0.000 (5) | 0.009 (4) | 0.007 (5) |
C28 | 0.094 (7) | 0.052 (6) | 0.069 (5) | 0.007 (5) | −0.019 (5) | −0.016 (4) |
C27' | 0.080 (7) | 0.041 (5) | 0.088 (6) | 0.009 (6) | −0.015 (5) | −0.014 (5) |
C28' | 0.131 (8) | 0.068 (7) | 0.116 (7) | −0.002 (6) | 0.010 (6) | 0.021 (5) |
O1 | 0.0853 (16) | 0.0610 (14) | 0.0513 (12) | 0.0076 (11) | −0.0270 (11) | 0.0027 (10) |
O2 | 0.0906 (18) | 0.0776 (16) | 0.0622 (14) | −0.0047 (13) | −0.0312 (13) | −0.0228 (12) |
O3 | 0.0909 (17) | 0.0439 (12) | 0.0640 (13) | 0.0039 (11) | −0.0204 (12) | −0.0165 (10) |
O4 | 0.0521 (11) | 0.0336 (10) | 0.0360 (9) | −0.0006 (8) | −0.0092 (8) | 0.0005 (7) |
O5 | 0.1030 (19) | 0.0786 (17) | 0.0492 (12) | 0.0088 (14) | −0.0317 (12) | −0.0010 (11) |
O6 | 0.0738 (16) | 0.0721 (15) | 0.0602 (13) | 0.0155 (12) | −0.0020 (11) | 0.0259 (11) |
O7 | 0.0901 (16) | 0.0411 (12) | 0.0667 (13) | 0.0087 (11) | −0.0078 (12) | 0.0086 (10) |
O8 | 0.0538 (13) | 0.0713 (15) | 0.0751 (14) | −0.0174 (11) | −0.0001 (11) | −0.0200 (11) |
O9 | 0.0752 (15) | 0.0632 (14) | 0.0570 (12) | −0.0202 (11) | 0.0117 (11) | −0.0258 (10) |
O10 | 0.137 (2) | 0.0487 (13) | 0.0886 (17) | 0.0238 (14) | −0.0644 (16) | −0.0148 (12) |
O11 | 0.123 (2) | 0.0331 (12) | 0.0991 (17) | 0.0072 (12) | −0.0566 (16) | −0.0068 (11) |
O12 | 0.089 (10) | 0.089 (11) | 0.051 (7) | 0.038 (8) | 0.009 (7) | −0.008 (7) |
Geometric parameters (Å, º) top
C1—O1 | 1.367 (3) | C18—O7 | 1.368 (3) |
C1—C2 | 1.384 (4) | C18—C19 | 1.385 (3) |
C1—C6 | 1.388 (3) | C19—H19 | 0.93 |
C2—O2 | 1.377 (3) | C20—O5 | 1.414 (4) |
C2—C3 | 1.385 (4) | C20—H20A | 0.96 |
C3—O3 | 1.365 (3) | C20—H20B | 0.96 |
C3—C4 | 1.380 (3) | C20—H20C | 0.96 |
C4—C5 | 1.388 (4) | C21—O6 | 1.398 (4) |
C4—H4 | 0.93 | C21—H21A | 0.96 |
C5—C6 | 1.393 (3) | C21—H21B | 0.96 |
C5—C10 | 1.476 (3) | C21—H21C | 0.96 |
C6—H6 | 0.93 | C22—O7 | 1.421 (4) |
C7—O1 | 1.406 (4) | C22—H22A | 0.96 |
C7—H7A | 0.96 | C22—H22B | 0.96 |
C7—H7B | 0.96 | C22—H22C | 0.96 |
C7—H7C | 0.96 | C23—O8 | 1.202 (3) |
C8—O2 | 1.395 (5) | C23—O9 | 1.327 (3) |
C8—H8A | 0.96 | C24—O9 | 1.466 (3) |
C8—H8B | 0.96 | C24—C25 | 1.483 (5) |
C8—H8C | 0.96 | C24—H24A | 0.97 |
C9—O3 | 1.416 (4) | C24—H24B | 0.97 |
C9—H9A | 0.96 | C25—H25A | 0.96 |
C9—H9B | 0.96 | C25—H25B | 0.96 |
C9—H9C | 0.96 | C25—H25C | 0.96 |
C10—O4 | 1.363 (3) | C26—O10 | 1.193 (3) |
C10—C11 | 1.376 (3) | C26—O11 | 1.319 (3) |
C11—C12 | 1.444 (3) | C27—O11 | 1.480 (7) |
C11—C26 | 1.468 (4) | C27—C28 | 1.493 (8) |
C12—C13 | 1.345 (3) | C27—H27A | 0.97 |
C12—C23 | 1.492 (3) | C27—H27B | 0.97 |
C13—O4 | 1.372 (3) | C28—H28A | 0.96 |
C13—C14 | 1.465 (3) | C28—H28B | 0.96 |
C14—C15 | 1.388 (3) | C28—H28C | 0.96 |
C14—C19 | 1.388 (3) | C27'—O11 | 1.480 (7) |
C15—C16 | 1.384 (4) | C27'—C28' | 1.483 (8) |
C15—H15 | 0.93 | C27'—H27C | 0.97 |
C16—O5 | 1.364 (3) | C27'—H27D | 0.97 |
C16—C17 | 1.387 (4) | C28'—H28D | 0.96 |
C17—C18 | 1.385 (4) | C28'—H28E | 0.96 |
C17—O6 | 1.386 (3) | C28'—H28F | 0.96 |
| | | |
O1—C1—C2 | 115.2 (2) | C14—C19—H19 | 120.0 |
O1—C1—C6 | 124.3 (3) | O5—C20—H20A | 109.5 |
C2—C1—C6 | 120.6 (2) | O5—C20—H20B | 109.5 |
O2—C2—C1 | 119.3 (2) | H20A—C20—H20B | 109.5 |
O2—C2—C3 | 121.0 (3) | O5—C20—H20C | 109.5 |
C1—C2—C3 | 119.5 (2) | H20A—C20—H20C | 109.5 |
O3—C3—C4 | 124.5 (2) | H20B—C20—H20C | 109.5 |
O3—C3—C2 | 115.1 (2) | O6—C21—H21A | 109.5 |
C4—C3—C2 | 120.4 (3) | O6—C21—H21B | 109.5 |
C3—C4—C5 | 120.3 (2) | H21A—C21—H21B | 109.5 |
C3—C4—H4 | 119.9 | O6—C21—H21C | 109.5 |
C5—C4—H4 | 119.9 | H21A—C21—H21C | 109.5 |
C4—C5—C6 | 119.7 (2) | H21B—C21—H21C | 109.5 |
C4—C5—C10 | 117.9 (2) | O7—C22—H22A | 109.5 |
C6—C5—C10 | 122.4 (2) | O7—C22—H22B | 109.5 |
C1—C6—C5 | 119.6 (2) | H22A—C22—H22B | 109.5 |
C1—C6—H6 | 120.2 | O7—C22—H22C | 109.5 |
C5—C6—H6 | 120.2 | H22A—C22—H22C | 109.5 |
O1—C7—H7A | 109.5 | H22B—C22—H22C | 109.5 |
O1—C7—H7B | 109.5 | O8—C23—O9 | 124.3 (2) |
H7A—C7—H7B | 109.5 | O8—C23—C12 | 123.8 (3) |
O1—C7—H7C | 109.5 | O9—C23—C12 | 111.7 (2) |
H7A—C7—H7C | 109.5 | O9—C24—C25 | 110.7 (3) |
H7B—C7—H7C | 109.5 | O9—C24—H24A | 109.5 |
O2—C8—H8A | 109.5 | C25—C24—H24A | 109.5 |
O2—C8—H8B | 109.5 | O9—C24—H24B | 109.5 |
H8A—C8—H8B | 109.5 | C25—C24—H24B | 109.5 |
O2—C8—H8C | 109.5 | H24A—C24—H24B | 108.1 |
H8A—C8—H8C | 109.5 | C24—C25—H25A | 109.5 |
H8B—C8—H8C | 109.5 | C24—C25—H25B | 109.5 |
O3—C9—H9A | 109.5 | H25A—C25—H25B | 109.5 |
O3—C9—H9B | 109.5 | C24—C25—H25C | 109.5 |
H9A—C9—H9B | 109.5 | H25A—C25—H25C | 109.5 |
O3—C9—H9C | 109.5 | H25B—C25—H25C | 109.5 |
H9A—C9—H9C | 109.5 | O10—C26—O11 | 121.3 (3) |
H9B—C9—H9C | 109.5 | O10—C26—C11 | 127.0 (2) |
O4—C10—C11 | 108.3 (2) | O11—C26—C11 | 111.7 (2) |
O4—C10—C5 | 112.3 (2) | O11—C27—C28 | 103.8 (8) |
C11—C10—C5 | 139.4 (2) | O11—C27—H27A | 111.0 |
C10—C11—C12 | 106.3 (2) | C28—C27—H27A | 111.0 |
C10—C11—C26 | 128.9 (2) | O11—C27—H27B | 111.0 |
C12—C11—C26 | 124.8 (2) | C28—C27—H27B | 111.0 |
C13—C12—C11 | 107.3 (2) | H27A—C27—H27B | 109.0 |
C13—C12—C23 | 125.6 (2) | O11—C27'—C28' | 102.9 (9) |
C11—C12—C23 | 127.0 (2) | O11—C27'—H27C | 111.2 |
C12—C13—O4 | 108.9 (2) | C28'—C27'—H27C | 111.2 |
C12—C13—C14 | 136.2 (2) | O11—C27'—H27D | 111.2 |
O4—C13—C14 | 114.8 (2) | C28'—C27'—H27D | 111.2 |
C15—C14—C19 | 119.9 (2) | H27C—C27'—H27D | 109.1 |
C15—C14—C13 | 121.0 (2) | C27'—C28'—H28D | 109.5 |
C19—C14—C13 | 119.0 (2) | C27'—C28'—H28E | 109.5 |
C16—C15—C14 | 120.1 (3) | H28D—C28'—H28E | 109.5 |
C16—C15—H15 | 120.0 | C27'—C28'—H28F | 109.5 |
C14—C15—H15 | 120.0 | H28D—C28'—H28F | 109.5 |
O5—C16—C15 | 124.7 (3) | H28E—C28'—H28F | 109.5 |
O5—C16—C17 | 115.3 (2) | C1—O1—C7 | 118.4 (2) |
C15—C16—C17 | 120.0 (2) | C2—O2—C8 | 116.2 (3) |
C18—C17—O6 | 119.6 (3) | C3—O3—C9 | 117.5 (2) |
C18—C17—C16 | 120.0 (2) | C10—O4—C13 | 109.25 (18) |
O6—C17—C16 | 120.1 (2) | C16—O5—C20 | 117.5 (2) |
O7—C18—C17 | 115.7 (2) | C17—O6—C21 | 114.2 (2) |
O7—C18—C19 | 124.1 (2) | C18—O7—C22 | 117.4 (2) |
C17—C18—C19 | 120.1 (3) | C23—O9—C24 | 116.3 (2) |
C18—C19—C14 | 119.9 (2) | C26—O11—C27 | 118.1 (4) |
C18—C19—H19 | 120.0 | C26—O11—C27' | 113.9 (4) |
| | | |
O1—C1—C2—O2 | 4.3 (4) | O6—C17—C18—O7 | 5.3 (4) |
C6—C1—C2—O2 | −175.4 (3) | C16—C17—C18—O7 | 178.7 (3) |
O1—C1—C2—C3 | −179.7 (3) | O6—C17—C18—C19 | −173.1 (3) |
C6—C1—C2—C3 | 0.6 (4) | C16—C17—C18—C19 | 0.3 (4) |
O2—C2—C3—O3 | −4.2 (4) | O7—C18—C19—C14 | −178.3 (3) |
C1—C2—C3—O3 | 179.8 (3) | C17—C18—C19—C14 | 0.0 (4) |
O2—C2—C3—C4 | 176.5 (3) | C15—C14—C19—C18 | −0.3 (4) |
C1—C2—C3—C4 | 0.5 (5) | C13—C14—C19—C18 | 176.7 (2) |
O3—C3—C4—C5 | 179.2 (3) | C13—C12—C23—O8 | −78.8 (4) |
C2—C3—C4—C5 | −1.6 (4) | C11—C12—C23—O8 | 96.2 (4) |
C3—C4—C5—C6 | 1.5 (4) | C13—C12—C23—O9 | 97.4 (3) |
C3—C4—C5—C10 | −179.3 (3) | C11—C12—C23—O9 | −87.6 (3) |
O1—C1—C6—C5 | 179.7 (3) | C10—C11—C26—O10 | −7.6 (5) |
C2—C1—C6—C5 | −0.6 (4) | C12—C11—C26—O10 | 171.6 (3) |
C4—C5—C6—C1 | −0.5 (4) | C10—C11—C26—O11 | 172.4 (3) |
C10—C5—C6—C1 | −179.6 (2) | C12—C11—C26—O11 | −8.3 (4) |
C4—C5—C10—O4 | 5.3 (3) | C2—C1—O1—C7 | 177.4 (3) |
C6—C5—C10—O4 | −175.6 (2) | C6—C1—O1—C7 | −2.9 (4) |
C4—C5—C10—C11 | −171.6 (3) | C1—C2—O2—C8 | −102.4 (4) |
C6—C5—C10—C11 | 7.5 (5) | C3—C2—O2—C8 | 81.6 (4) |
O4—C10—C11—C12 | −1.5 (3) | C4—C3—O3—C9 | −10.9 (4) |
C5—C10—C11—C12 | 175.5 (3) | C2—C3—O3—C9 | 169.9 (3) |
O4—C10—C11—C26 | 177.9 (3) | C11—C10—O4—C13 | 1.0 (3) |
C5—C10—C11—C26 | −5.2 (6) | C5—C10—O4—C13 | −176.9 (2) |
C10—C11—C12—C13 | 1.5 (3) | C12—C13—O4—C10 | 0.0 (3) |
C26—C11—C12—C13 | −177.9 (3) | C14—C13—O4—C10 | −177.6 (2) |
C10—C11—C12—C23 | −174.3 (3) | C15—C16—O5—C20 | −5.5 (5) |
C26—C11—C12—C23 | 6.3 (4) | C17—C16—O5—C20 | 172.1 (3) |
C11—C12—C13—O4 | −0.9 (3) | C18—C17—O6—C21 | −96.1 (3) |
C23—C12—C13—O4 | 174.9 (2) | C16—C17—O6—C21 | 90.5 (4) |
C11—C12—C13—C14 | 175.9 (3) | C17—C18—O7—C22 | −168.8 (3) |
C23—C12—C13—C14 | −8.3 (5) | C19—C18—O7—C22 | 9.6 (4) |
C12—C13—C14—C15 | −4.6 (5) | O8—C23—O9—C24 | 0.1 (4) |
O4—C13—C14—C15 | 172.0 (2) | C12—C23—O9—C24 | −176.1 (2) |
C12—C13—C14—C19 | 178.4 (3) | C25—C24—O9—C23 | −84.7 (4) |
O4—C13—C14—C19 | −4.9 (4) | O10—C26—O11—C27 | 18.6 (6) |
C19—C14—C15—C16 | 0.2 (4) | C11—C26—O11—C27 | −161.4 (5) |
C13—C14—C15—C16 | −176.7 (3) | O10—C26—O11—C27' | −18.7 (6) |
C14—C15—C16—O5 | 177.6 (3) | C11—C26—O11—C27' | 161.3 (5) |
C14—C15—C16—C17 | 0.1 (5) | C28—C27—O11—C26 | −91.5 (7) |
O5—C16—C17—C18 | −178.0 (3) | C28—C27—O11—C27' | 0.1 (7) |
C15—C16—C17—C18 | −0.4 (5) | C28'—C27'—O11—C26 | 110.9 (6) |
O5—C16—C17—O6 | −4.7 (4) | C28'—C27'—O11—C27 | 5.7 (9) |
C15—C16—C17—O6 | 173.0 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O10 | 0.93 | 2.13 | 2.949 (3) | 147 |
C9—H9C···O8i | 0.96 | 2.57 | 3.490 (4) | 161 |
C22—H22A···O8i | 0.96 | 2.59 | 3.510 (4) | 160 |
C25—H25B···O10ii | 0.96 | 2.60 | 3.540 (4) | 166 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1/2, −y+3/2, z−1/2. |