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The title compound, C
28H
28O
6S, is a protected fucose donor, synthesized as part of our investigations into the preparation of complex oligosaccharides. The benzoyl groups are equatorial and axial, while the thioether and ether groups are equatorial. The carboxylate O atoms form a number of intra- and intermolecular C—H
O interactions.
Supporting information
CCDC reference: 283969
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.009 Å
- R factor = 0.047
- wR factor = 0.142
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.83 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.09 Ratio
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C9 -C14 1.35 Ang.
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.29
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 27.50
From the CIF: _reflns_number_total 3548
Count of symmetry unique reflns 3409
Completeness (_total/calc) 104.08%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 139
Fraction of Friedel pairs measured 0.041
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 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: MSC/AFC7 Diffractometer Control Software for Windows (Molecular Structure
Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer ControlSoftware for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003).
Methyl
2-
O-benzyl-3,4-
O-dibenzoyl-1-thio-
β-
L-fucopyranoside
top
Crystal data top
C28H28O6S | F(000) = 1040 |
Mr = 492.57 | Dx = 1.239 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 11.725 (2) Å | θ = 7.7–10.6° |
b = 20.396 (3) Å | µ = 0.16 mm−1 |
c = 11.040 (2) Å | T = 295 K |
V = 2640.1 (8) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.20 × 0.15 mm |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.011 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 2.5° |
Graphite monochromator | h = 0→15 |
ω scans | k = −10→26 |
3971 measured reflections | l = −14→14 |
3548 independent reflections | 3 standard reflections every 150 reflections |
2276 reflections with I > 2σ(I) | intensity decay: 0.2% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0607P)2 + 1.0014P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.142 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.57 e Å−3 |
3548 reflections | Δρmin = −0.25 e Å−3 |
317 parameters | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0076 (14) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 139 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.19 (15) |
Special details top
Experimental. The scan width was (0.84 + 0.30tanθ)° with an ω scan speed of 16° per minute
(up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were
recorded at each end of the scan, and the scan time:background time ratio was
2:1. |
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 e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | |
S1 | 0.62705 (10) | 0.07990 (5) | 0.29830 (10) | 0.0521 (3) | |
O1 | 0.7890 (2) | 0.08912 (12) | 0.4631 (2) | 0.0450 (8) | |
O2 | 0.7189 (3) | 0.21242 (16) | 0.2311 (3) | 0.0700 (11) | |
O3 | 0.9391 (2) | 0.24934 (12) | 0.3008 (2) | 0.0477 (9) | |
O4 | 0.9805 (3) | 0.32486 (16) | 0.4414 (3) | 0.0706 (13) | |
O5 | 1.0077 (2) | 0.12655 (15) | 0.3887 (3) | 0.0518 (10) | |
O6 | 1.1656 (3) | 0.1882 (2) | 0.4125 (4) | 0.0947 (16) | |
C1 | 0.7149 (3) | 0.13059 (19) | 0.3941 (4) | 0.0420 (12) | |
C2 | 0.7850 (3) | 0.17506 (18) | 0.3115 (4) | 0.0443 (12) | |
C3 | 0.8697 (4) | 0.21383 (17) | 0.3864 (4) | 0.0427 (11) | |
C4 | 0.9410 (4) | 0.1689 (2) | 0.4655 (4) | 0.0463 (12) | |
C5 | 0.8635 (4) | 0.12621 (19) | 0.5412 (3) | 0.0467 (12) | |
C6 | 0.9258 (4) | 0.0772 (2) | 0.6198 (4) | 0.0653 (17) | |
C7 | 0.5506 (5) | 0.0326 (2) | 0.4073 (5) | 0.0733 (19) | |
C8 | 0.6625 (6) | 0.2583 (4) | 0.2857 (6) | 0.098 (3) | |
C9 | 0.5777 (5) | 0.2887 (3) | 0.1842 (7) | 0.081 (2) | |
C10 | 0.4689 (6) | 0.2701 (3) | 0.1895 (6) | 0.092 (3) | |
C11 | 0.3866 (7) | 0.2935 (5) | 0.1169 (9) | 0.126 (4) | |
C12 | 0.4195 (13) | 0.3360 (6) | 0.0296 (8) | 0.153 (6) | |
C13 | 0.5287 (15) | 0.3586 (5) | 0.0136 (10) | 0.161 (6) | |
C14 | 0.6088 (8) | 0.3326 (4) | 0.0989 (10) | 0.124 (4) | |
C15 | 0.9862 (4) | 0.3061 (2) | 0.3375 (4) | 0.0490 (14) | |
C16 | 1.0427 (3) | 0.34192 (18) | 0.2375 (4) | 0.0430 (12) | |
C17 | 1.0345 (4) | 0.3222 (2) | 0.1188 (4) | 0.0603 (17) | |
C18 | 1.0820 (5) | 0.3592 (3) | 0.0267 (5) | 0.0740 (19) | |
C19 | 1.1397 (4) | 0.4166 (2) | 0.0551 (4) | 0.0647 (17) | |
C20 | 1.1500 (4) | 0.4358 (2) | 0.1723 (5) | 0.0637 (18) | |
C21 | 1.1029 (4) | 0.3986 (2) | 0.2652 (4) | 0.0577 (16) | |
C22 | 1.1195 (4) | 0.1399 (2) | 0.3700 (5) | 0.0627 (16) | |
C23 | 1.1722 (4) | 0.0912 (3) | 0.2883 (5) | 0.0633 (16) | |
C24 | 1.2782 (5) | 0.1039 (4) | 0.2420 (7) | 0.109 (3) | |
C25 | 1.3284 (5) | 0.0593 (5) | 0.1633 (8) | 0.129 (4) | |
C26 | 1.2746 (5) | 0.0025 (5) | 0.1329 (8) | 0.119 (4) | |
C27 | 1.1692 (5) | −0.0114 (3) | 0.1805 (7) | 0.103 (3) | |
C28 | 1.1194 (4) | 0.0332 (3) | 0.2586 (5) | 0.0747 (19) | |
H1 | 0.66830 | 0.15590 | 0.44750 | 0.0470* | |
H2 | 0.82940 | 0.14680 | 0.26280 | 0.0520* | |
H3 | 0.82950 | 0.24400 | 0.43720 | 0.0500* | |
H4 | 0.98970 | 0.19380 | 0.51630 | 0.0540* | |
H5 | 0.81840 | 0.15350 | 0.59150 | 0.0550* | |
H6A | 0.87290 | 0.05570 | 0.67150 | 0.0780* | |
H6B | 0.96270 | 0.04560 | 0.57000 | 0.0780* | |
H6C | 0.98110 | 0.09940 | 0.66750 | 0.0780* | |
H7A | 0.51410 | 0.06130 | 0.46310 | 0.0880* | |
H7B | 0.49610 | 0.00630 | 0.36800 | 0.0880* | |
H7C | 0.60320 | 0.00550 | 0.45050 | 0.0880* | |
H8A | 0.62210 | 0.24360 | 0.34960 | 0.1260* | |
H8B | 0.71530 | 0.29280 | 0.30830 | 0.1260* | |
H10 | 0.44780 | 0.23890 | 0.24750 | 0.1090* | |
H11 | 0.31010 | 0.28140 | 0.12270 | 0.1540* | |
H12 | 0.36620 | 0.35340 | −0.02710 | 0.1780* | |
H13 | 0.55300 | 0.38830 | −0.04940 | 0.1920* | |
H14 | 0.68580 | 0.34670 | 0.09580 | 0.1450* | |
H17 | 0.99420 | 0.28290 | 0.10070 | 0.0720* | |
H18 | 1.07500 | 0.34500 | −0.05500 | 0.0880* | |
H19 | 1.17330 | 0.44170 | −0.00790 | 0.0760* | |
H20 | 1.18850 | 0.47550 | 0.19100 | 0.0740* | |
H21 | 1.11190 | 0.41140 | 0.34740 | 0.0660* | |
H24 | 1.31730 | 0.14370 | 0.26290 | 0.1270* | |
H25 | 1.40150 | 0.06940 | 0.12910 | 0.1580* | |
H26 | 1.31000 | −0.02710 | 0.07970 | 0.1440* | |
H27 | 1.13160 | −0.05040 | 0.15950 | 0.1280* | |
H28 | 1.04740 | 0.02370 | 0.29320 | 0.0900* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0570 (6) | 0.0519 (6) | 0.0473 (5) | −0.0133 (6) | −0.0038 (6) | −0.0042 (5) |
O1 | 0.0475 (15) | 0.0414 (14) | 0.0462 (15) | −0.0006 (13) | −0.0048 (13) | 0.0058 (12) |
O2 | 0.074 (2) | 0.0609 (19) | 0.075 (2) | 0.0036 (18) | −0.018 (2) | 0.0060 (18) |
O3 | 0.0556 (17) | 0.0434 (14) | 0.0442 (15) | −0.0149 (13) | 0.0028 (15) | 0.0012 (14) |
O4 | 0.091 (3) | 0.074 (2) | 0.0467 (18) | −0.038 (2) | 0.0068 (19) | −0.0091 (17) |
O5 | 0.0391 (15) | 0.0572 (17) | 0.0592 (18) | −0.0052 (13) | 0.0005 (15) | −0.0006 (15) |
O6 | 0.058 (2) | 0.105 (3) | 0.121 (3) | −0.026 (2) | 0.002 (2) | −0.037 (3) |
C1 | 0.045 (2) | 0.042 (2) | 0.039 (2) | −0.0039 (18) | 0.0001 (18) | 0.0014 (18) |
C2 | 0.049 (2) | 0.041 (2) | 0.043 (2) | −0.0050 (18) | −0.0072 (19) | 0.0058 (18) |
C3 | 0.045 (2) | 0.0410 (18) | 0.042 (2) | −0.0072 (19) | 0.002 (2) | 0.0061 (17) |
C4 | 0.048 (2) | 0.050 (2) | 0.041 (2) | −0.003 (2) | −0.0081 (19) | 0.0024 (19) |
C5 | 0.048 (2) | 0.050 (2) | 0.042 (2) | −0.003 (2) | −0.008 (2) | 0.0039 (18) |
C6 | 0.070 (3) | 0.062 (3) | 0.064 (3) | −0.004 (3) | −0.018 (3) | 0.014 (3) |
C7 | 0.085 (4) | 0.063 (3) | 0.072 (3) | −0.029 (3) | 0.009 (3) | −0.008 (3) |
C8 | 0.095 (5) | 0.130 (5) | 0.069 (4) | 0.020 (4) | −0.011 (3) | −0.041 (4) |
C9 | 0.070 (4) | 0.051 (3) | 0.122 (5) | 0.017 (3) | −0.021 (4) | 0.002 (3) |
C10 | 0.091 (5) | 0.078 (4) | 0.108 (5) | −0.001 (4) | −0.022 (4) | −0.014 (4) |
C11 | 0.084 (5) | 0.166 (8) | 0.129 (7) | 0.031 (6) | −0.028 (6) | −0.061 (7) |
C12 | 0.242 (14) | 0.151 (10) | 0.066 (5) | 0.132 (10) | −0.034 (7) | −0.027 (6) |
C13 | 0.291 (16) | 0.092 (6) | 0.099 (7) | 0.043 (9) | 0.064 (10) | 0.013 (5) |
C14 | 0.133 (7) | 0.085 (5) | 0.155 (8) | 0.025 (5) | 0.042 (7) | −0.008 (5) |
C15 | 0.048 (2) | 0.046 (2) | 0.053 (3) | −0.010 (2) | −0.004 (2) | 0.0027 (19) |
C16 | 0.042 (2) | 0.042 (2) | 0.045 (2) | −0.0053 (18) | −0.0043 (18) | 0.0011 (18) |
C17 | 0.073 (3) | 0.057 (3) | 0.051 (3) | −0.017 (2) | 0.000 (3) | −0.001 (2) |
C18 | 0.098 (4) | 0.074 (3) | 0.050 (3) | −0.021 (3) | 0.007 (3) | 0.008 (3) |
C19 | 0.069 (3) | 0.059 (3) | 0.066 (3) | −0.008 (3) | 0.010 (3) | 0.019 (2) |
C20 | 0.064 (3) | 0.049 (2) | 0.078 (4) | −0.013 (2) | 0.003 (3) | 0.007 (2) |
C21 | 0.061 (3) | 0.053 (2) | 0.059 (3) | −0.015 (2) | −0.002 (2) | −0.002 (2) |
C22 | 0.044 (2) | 0.071 (3) | 0.073 (3) | −0.006 (2) | −0.003 (3) | 0.000 (3) |
C23 | 0.038 (2) | 0.082 (3) | 0.070 (3) | 0.004 (2) | 0.000 (2) | −0.003 (3) |
C24 | 0.053 (3) | 0.122 (5) | 0.153 (7) | −0.017 (4) | 0.019 (4) | −0.036 (5) |
C25 | 0.054 (3) | 0.178 (8) | 0.156 (8) | −0.001 (5) | 0.030 (4) | −0.055 (7) |
C26 | 0.061 (4) | 0.155 (7) | 0.142 (7) | 0.014 (5) | 0.007 (4) | −0.052 (6) |
C27 | 0.067 (4) | 0.100 (5) | 0.143 (6) | 0.010 (4) | 0.008 (4) | −0.030 (5) |
C28 | 0.054 (3) | 0.076 (3) | 0.094 (4) | −0.003 (3) | 0.009 (3) | −0.009 (3) |
Geometric parameters (Å, º) top
S1—C1 | 1.802 (4) | C23—C28 | 1.375 (8) |
S1—C7 | 1.784 (5) | C24—C25 | 1.389 (12) |
O1—C1 | 1.432 (5) | C25—C26 | 1.361 (13) |
O1—C5 | 1.442 (5) | C26—C27 | 1.373 (9) |
O2—C2 | 1.403 (5) | C27—C28 | 1.383 (9) |
O2—C8 | 1.295 (8) | C1—H1 | 0.9600 |
O3—C3 | 1.442 (5) | C2—H2 | 0.9400 |
O3—C15 | 1.345 (5) | C3—H3 | 0.9600 |
O4—C15 | 1.211 (5) | C4—H4 | 0.9500 |
O5—C4 | 1.441 (5) | C5—H5 | 0.9500 |
O5—C22 | 1.355 (5) | C6—H6A | 0.9500 |
O6—C22 | 1.218 (6) | C6—H6B | 0.9500 |
C1—C2 | 1.526 (6) | C6—H6C | 0.9500 |
C2—C3 | 1.515 (6) | C7—H7A | 0.9500 |
C3—C4 | 1.517 (6) | C7—H7B | 0.9400 |
C4—C5 | 1.511 (6) | C7—H7C | 0.9600 |
C5—C6 | 1.512 (6) | C8—H8A | 0.9000 |
C8—C9 | 1.621 (10) | C8—H8B | 0.9700 |
C9—C10 | 1.332 (9) | C10—H10 | 0.9400 |
C9—C14 | 1.350 (12) | C11—H11 | 0.9300 |
C10—C11 | 1.342 (11) | C12—H12 | 0.9500 |
C11—C12 | 1.352 (15) | C13—H13 | 0.9700 |
C12—C13 | 1.37 (2) | C14—H14 | 0.9500 |
C13—C14 | 1.432 (17) | C17—H17 | 0.9500 |
C15—C16 | 1.480 (6) | C18—H18 | 0.9500 |
C16—C17 | 1.374 (6) | C19—H19 | 0.9500 |
C16—C21 | 1.389 (6) | C20—H20 | 0.9500 |
C17—C18 | 1.383 (7) | C21—H21 | 0.9500 |
C18—C19 | 1.388 (7) | C24—H24 | 0.9600 |
C19—C20 | 1.357 (7) | C25—H25 | 0.9600 |
C20—C21 | 1.390 (7) | C26—H26 | 0.9400 |
C22—C23 | 1.477 (7) | C27—H27 | 0.9400 |
C23—C24 | 1.369 (8) | C28—H28 | 0.9500 |
| | | |
S1···O2 | 3.003 (4) | C23···H13viii | 3.0100 |
S1···C8 | 3.665 (8) | C28···H13viii | 2.9200 |
S1···H6Ai | 3.1000 | H1···C8 | 2.7500 |
S1···H18ii | 3.1500 | H1···H5 | 2.3700 |
S1···H20iii | 3.0400 | H1···H8A | 2.1600 |
O1···O5 | 2.799 (3) | H1···O4v | 2.5500 |
O2···O3 | 2.797 (4) | H2···O5 | 2.5400 |
O2···S1 | 3.003 (4) | H3···O4 | 2.4200 |
O3···C8 | 3.253 (7) | H3···C8 | 2.5900 |
O3···O6 | 3.183 (4) | H3···H5 | 2.5200 |
O3···O2 | 2.797 (4) | H3···H8B | 2.1900 |
O3···O5 | 2.804 (4) | H3···O6v | 2.8900 |
O3···C22 | 3.169 (5) | H4···O4 | 2.8000 |
O4···C1iv | 3.417 (5) | H4···O6 | 2.3600 |
O4···C4 | 3.226 (5) | H4···C15 | 3.0200 |
O5···O1 | 2.799 (3) | H4···H6C | 2.5500 |
O5···O3 | 2.804 (4) | H4···H8Aiv | 2.5000 |
O6···C15 | 3.300 (6) | H5···H1 | 2.3700 |
O6···O3 | 3.183 (4) | H5···H3 | 2.5200 |
O1···H7C | 2.7700 | H6A···S1ix | 3.1000 |
O1···H20iii | 2.8900 | H6B···O5 | 2.6500 |
O2···H18ii | 2.8300 | H6C···H4 | 2.5500 |
O3···H17 | 2.4000 | H6C···C9iv | 3.0300 |
O3···H8B | 2.7700 | H6C···C10iv | 3.1000 |
O4···H4 | 2.8000 | H7A···O4v | 2.5800 |
O4···H21 | 2.5600 | H7A···H21v | 2.4500 |
O4···H3 | 2.4200 | H7C···O1 | 2.7700 |
O4···H1iv | 2.5500 | H8A···C1 | 2.6000 |
O4···H7Aiv | 2.5800 | H8A···C3 | 2.9900 |
O5···H28 | 2.3900 | H8A···H1 | 2.1600 |
O5···H2 | 2.5400 | H8A···H10 | 2.3400 |
O5···H6B | 2.6500 | H8A···H4v | 2.5000 |
O6···H4 | 2.3600 | H8B···O3 | 2.7700 |
O6···H24 | 2.5900 | H8B···C3 | 2.5700 |
O6···H3iv | 2.8900 | H8B···H3 | 2.1900 |
C1···O4v | 3.417 (5) | H10···H8A | 2.3400 |
C4···O4 | 3.226 (5) | H10···H24x | 2.4800 |
C8···O3 | 3.253 (7) | H12···C19x | 3.0900 |
C8···S1 | 3.665 (8) | H13···C23ii | 3.0100 |
C15···O6 | 3.300 (6) | H13···C28ii | 2.9200 |
C22···O3 | 3.169 (5) | H17···O3 | 2.4000 |
C1···H8A | 2.6000 | H17···C12viii | 2.9500 |
C3···H8B | 2.5700 | H18···S1viii | 3.1500 |
C3···H8A | 2.9900 | H18···O2viii | 2.8300 |
C7···H21v | 3.0300 | H18···C9viii | 3.0800 |
C8···H3 | 2.5900 | H18···C10viii | 3.0400 |
C8···H1 | 2.7500 | H20···S1vii | 3.0400 |
C9···H6Cv | 3.0300 | H20···O1vii | 2.8900 |
C9···H18ii | 3.0800 | H21···O4 | 2.5600 |
C10···H18ii | 3.0400 | H21···C7iv | 3.0300 |
C10···H6Cv | 3.1000 | H21···H7Aiv | 2.4500 |
C12···H17ii | 2.9500 | H24···O6 | 2.5900 |
C15···H4 | 3.0200 | H24···H10vi | 2.4800 |
C18···H25ii | 3.0900 | H25···C18viii | 3.0900 |
C19···H12vi | 3.0900 | H27···C21iii | 3.0500 |
C20···H28vii | 2.9500 | H28···O5 | 2.3900 |
C21···H27vii | 3.0500 | H28···C20iii | 2.9500 |
| | | |
C1—S1—C7 | 101.6 (2) | O3—C3—H3 | 110.00 |
C1—O1—C5 | 112.1 (3) | C2—C3—H3 | 109.00 |
C2—O2—C8 | 112.3 (4) | C4—C3—H3 | 109.00 |
C3—O3—C15 | 117.8 (3) | O5—C4—H4 | 110.00 |
C4—O5—C22 | 119.6 (3) | C3—C4—H4 | 110.00 |
S1—C1—O1 | 108.7 (2) | C5—C4—H4 | 110.00 |
S1—C1—C2 | 107.3 (3) | O1—C5—H5 | 109.00 |
O1—C1—C2 | 110.0 (3) | C4—C5—H5 | 109.00 |
O2—C2—C1 | 113.8 (3) | C6—C5—H5 | 109.00 |
O2—C2—C3 | 115.1 (3) | C5—C6—H6A | 110.00 |
C1—C2—C3 | 109.7 (4) | C5—C6—H6B | 110.00 |
O3—C3—C2 | 105.9 (3) | C5—C6—H6C | 109.00 |
O3—C3—C4 | 111.7 (4) | H6A—C6—H6B | 109.00 |
C2—C3—C4 | 111.1 (3) | H6A—C6—H6C | 109.00 |
O5—C4—C3 | 108.8 (3) | H6B—C6—H6C | 109.00 |
O5—C4—C5 | 107.9 (3) | S1—C7—H7A | 109.00 |
C3—C4—C5 | 109.6 (4) | S1—C7—H7B | 110.00 |
O1—C5—C4 | 109.6 (3) | S1—C7—H7C | 109.00 |
O1—C5—C6 | 106.8 (3) | H7A—C7—H7B | 110.00 |
C4—C5—C6 | 114.1 (4) | H7A—C7—H7C | 109.00 |
O2—C8—C9 | 105.5 (5) | H7B—C7—H7C | 110.00 |
C8—C9—C10 | 116.6 (6) | O2—C8—H8A | 113.00 |
C8—C9—C14 | 124.8 (6) | O2—C8—H8B | 109.00 |
C10—C9—C14 | 118.6 (7) | C9—C8—H8A | 110.00 |
C9—C10—C11 | 124.1 (7) | C9—C8—H8B | 107.00 |
C10—C11—C12 | 116.6 (9) | H8A—C8—H8B | 112.00 |
C11—C12—C13 | 125.0 (11) | C9—C10—H10 | 118.00 |
C12—C13—C14 | 113.8 (10) | C11—C10—H10 | 117.00 |
C9—C14—C13 | 121.8 (9) | C10—C11—H11 | 124.00 |
O3—C15—O4 | 122.3 (4) | C12—C11—H11 | 120.00 |
O3—C15—C16 | 112.6 (3) | C11—C12—H12 | 121.00 |
O4—C15—C16 | 125.1 (4) | C13—C12—H12 | 114.00 |
C15—C16—C17 | 122.4 (4) | C12—C13—H13 | 125.00 |
C15—C16—C21 | 118.3 (4) | C14—C13—H13 | 121.00 |
C17—C16—C21 | 119.3 (4) | C9—C14—H14 | 119.00 |
C16—C17—C18 | 120.9 (4) | C13—C14—H14 | 119.00 |
C17—C18—C19 | 119.4 (5) | C16—C17—H17 | 119.00 |
C18—C19—C20 | 120.1 (4) | C18—C17—H17 | 120.00 |
C19—C20—C21 | 120.7 (4) | C17—C18—H18 | 120.00 |
C16—C21—C20 | 119.6 (4) | C19—C18—H18 | 121.00 |
O5—C22—O6 | 122.2 (4) | C18—C19—H19 | 119.00 |
O5—C22—C23 | 111.3 (4) | C20—C19—H19 | 120.00 |
O6—C22—C23 | 126.4 (5) | C19—C20—H20 | 120.00 |
C22—C23—C24 | 118.7 (6) | C21—C20—H20 | 120.00 |
C22—C23—C28 | 122.4 (4) | C16—C21—H21 | 120.00 |
C24—C23—C28 | 118.9 (6) | C20—C21—H21 | 121.00 |
C23—C24—C25 | 119.6 (7) | C23—C24—H24 | 120.00 |
C24—C25—C26 | 121.0 (6) | C25—C24—H24 | 120.00 |
C25—C26—C27 | 119.9 (8) | C24—C25—H25 | 119.00 |
C26—C27—C28 | 118.9 (6) | C26—C25—H25 | 120.00 |
C23—C28—C27 | 121.6 (5) | C25—C26—H26 | 120.00 |
S1—C1—H1 | 110.00 | C27—C26—H26 | 120.00 |
O1—C1—H1 | 110.00 | C26—C27—H27 | 120.00 |
C2—C1—H1 | 111.00 | C28—C27—H27 | 121.00 |
O2—C2—H2 | 106.00 | C23—C28—H28 | 119.00 |
C1—C2—H2 | 106.00 | C27—C28—H28 | 120.00 |
C3—C2—H2 | 106.00 | | |
| | | |
C7—S1—C1—O1 | 61.8 (3) | O2—C8—C9—C10 | 102.3 (7) |
C7—S1—C1—C2 | −179.2 (3) | C8—C9—C10—C11 | 176.0 (7) |
C5—O1—C1—S1 | 179.2 (2) | C10—C9—C14—C13 | −1.0 (13) |
C5—O1—C1—C2 | 62.0 (4) | C14—C9—C10—C11 | −1.7 (12) |
C1—O1—C5—C6 | 172.9 (3) | C8—C9—C14—C13 | −178.5 (8) |
C1—O1—C5—C4 | −63.0 (4) | C9—C10—C11—C12 | 3.6 (13) |
C8—O2—C2—C3 | −56.9 (6) | C10—C11—C12—C13 | −2.8 (16) |
C8—O2—C2—C1 | 70.9 (5) | C11—C12—C13—C14 | 0.4 (16) |
C2—O2—C8—C9 | −171.7 (4) | C12—C13—C14—C9 | 1.6 (14) |
C15—O3—C3—C4 | −86.4 (4) | O4—C15—C16—C21 | 6.1 (7) |
C3—O3—C15—O4 | 6.6 (6) | O4—C15—C16—C17 | −171.9 (4) |
C3—O3—C15—C16 | −172.6 (3) | O3—C15—C16—C17 | 7.4 (6) |
C15—O3—C3—C2 | 152.5 (3) | O3—C15—C16—C21 | −174.7 (4) |
C22—O5—C4—C3 | 101.6 (4) | C21—C16—C17—C18 | −2.2 (7) |
C22—O5—C4—C5 | −139.7 (4) | C15—C16—C21—C20 | −175.5 (4) |
C4—O5—C22—O6 | −2.7 (7) | C17—C16—C21—C20 | 2.5 (6) |
C4—O5—C22—C23 | −179.6 (4) | C15—C16—C17—C18 | 175.7 (4) |
S1—C1—C2—C3 | −174.0 (3) | C16—C17—C18—C19 | 0.7 (8) |
O1—C1—C2—O2 | 173.5 (3) | C17—C18—C19—C20 | 0.5 (8) |
O1—C1—C2—C3 | −56.0 (4) | C18—C19—C20—C21 | −0.2 (7) |
S1—C1—C2—O2 | 55.4 (4) | C19—C20—C21—C16 | −1.3 (7) |
C1—C2—C3—C4 | 53.1 (4) | O5—C22—C23—C24 | 168.0 (5) |
O2—C2—C3—O3 | −55.6 (4) | O5—C22—C23—C28 | −13.0 (7) |
O2—C2—C3—C4 | −177.1 (4) | O6—C22—C23—C24 | −8.7 (9) |
C1—C2—C3—O3 | 174.6 (3) | O6—C22—C23—C28 | 170.3 (5) |
O3—C3—C4—O5 | −54.6 (4) | C24—C23—C28—C27 | −2.0 (9) |
O3—C3—C4—C5 | −172.3 (3) | C22—C23—C24—C25 | −178.9 (6) |
C2—C3—C4—O5 | 63.5 (4) | C28—C23—C24—C25 | 2.1 (10) |
C2—C3—C4—C5 | −54.2 (5) | C22—C23—C28—C27 | 179.0 (6) |
C3—C4—C5—C6 | 177.4 (3) | C23—C24—C25—C26 | −1.1 (12) |
O5—C4—C5—O1 | −60.6 (4) | C24—C25—C26—C27 | −0.1 (13) |
O5—C4—C5—C6 | 59.1 (4) | C25—C26—C27—C28 | 0.3 (12) |
C3—C4—C5—O1 | 57.7 (4) | C26—C27—C28—C23 | 0.8 (10) |
O2—C8—C9—C14 | −80.1 (9) | | |
Symmetry codes: (i) −x+3/2, −y, z−1/2; (ii) x−1/2, −y+1/2, −z; (iii) −x+2, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z+1; (v) x−1/2, −y+1/2, −z+1; (vi) x+1, y, z; (vii) −x+2, y+1/2, −z+1/2; (viii) x+1/2, −y+1/2, −z; (ix) −x+3/2, −y, z+1/2; (x) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O4v | 0.96 | 2.55 | 3.417 (5) | 151 |
C2—H2···O5 | 0.94 | 2.54 | 2.920 (4) | 104 |
C4—H4···O6 | 0.95 | 2.36 | 2.726 (6) | 102 |
C7—H7A···O4v | 0.95 | 2.58 | 3.452 (6) | 152 |
C17—H17···O3 | 0.95 | 2.40 | 2.738 (5) | 100 |
C28—H28···O5 | 0.95 | 2.39 | 2.721 (6) | 100 |
Symmetry code: (v) x−1/2, −y+1/2, −z+1. |
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