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The title compound, C28H28O6S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502516X/ob6555sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680502516X/ob65552sup2.hkl
Contains datablock 2

CCDC reference: 283969

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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
C28H28O6SF(000) = 1040
Mr = 492.57Dx = 1.239 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 11.725 (2) Åθ = 7.7–10.6°
b = 20.396 (3) ŵ = 0.16 mm1
c = 11.040 (2) ÅT = 295 K
V = 2640.1 (8) Å3Block, colourless
Z = 40.35 × 0.20 × 0.15 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.011
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.5°
Graphite monochromatorh = 015
ω scansk = 1026
3971 measured reflectionsl = 1414
3548 independent reflections3 standard reflections every 150 reflections
2276 reflections with I > 2σ(I) intensity decay: 0.2%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.03Δρmax = 0.57 e Å3
3548 reflectionsΔρmin = 0.25 e Å3
317 parametersExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
0 restraintsExtinction coefficient: 0.0076 (14)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 139 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute 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
xyzUiso*/Ueq
S10.62705 (10)0.07990 (5)0.29830 (10)0.0521 (3)
O10.7890 (2)0.08912 (12)0.4631 (2)0.0450 (8)
O20.7189 (3)0.21242 (16)0.2311 (3)0.0700 (11)
O30.9391 (2)0.24934 (12)0.3008 (2)0.0477 (9)
O40.9805 (3)0.32486 (16)0.4414 (3)0.0706 (13)
O51.0077 (2)0.12655 (15)0.3887 (3)0.0518 (10)
O61.1656 (3)0.1882 (2)0.4125 (4)0.0947 (16)
C10.7149 (3)0.13059 (19)0.3941 (4)0.0420 (12)
C20.7850 (3)0.17506 (18)0.3115 (4)0.0443 (12)
C30.8697 (4)0.21383 (17)0.3864 (4)0.0427 (11)
C40.9410 (4)0.1689 (2)0.4655 (4)0.0463 (12)
C50.8635 (4)0.12621 (19)0.5412 (3)0.0467 (12)
C60.9258 (4)0.0772 (2)0.6198 (4)0.0653 (17)
C70.5506 (5)0.0326 (2)0.4073 (5)0.0733 (19)
C80.6625 (6)0.2583 (4)0.2857 (6)0.098 (3)
C90.5777 (5)0.2887 (3)0.1842 (7)0.081 (2)
C100.4689 (6)0.2701 (3)0.1895 (6)0.092 (3)
C110.3866 (7)0.2935 (5)0.1169 (9)0.126 (4)
C120.4195 (13)0.3360 (6)0.0296 (8)0.153 (6)
C130.5287 (15)0.3586 (5)0.0136 (10)0.161 (6)
C140.6088 (8)0.3326 (4)0.0989 (10)0.124 (4)
C150.9862 (4)0.3061 (2)0.3375 (4)0.0490 (14)
C161.0427 (3)0.34192 (18)0.2375 (4)0.0430 (12)
C171.0345 (4)0.3222 (2)0.1188 (4)0.0603 (17)
C181.0820 (5)0.3592 (3)0.0267 (5)0.0740 (19)
C191.1397 (4)0.4166 (2)0.0551 (4)0.0647 (17)
C201.1500 (4)0.4358 (2)0.1723 (5)0.0637 (18)
C211.1029 (4)0.3986 (2)0.2652 (4)0.0577 (16)
C221.1195 (4)0.1399 (2)0.3700 (5)0.0627 (16)
C231.1722 (4)0.0912 (3)0.2883 (5)0.0633 (16)
C241.2782 (5)0.1039 (4)0.2420 (7)0.109 (3)
C251.3284 (5)0.0593 (5)0.1633 (8)0.129 (4)
C261.2746 (5)0.0025 (5)0.1329 (8)0.119 (4)
C271.1692 (5)0.0114 (3)0.1805 (7)0.103 (3)
C281.1194 (4)0.0332 (3)0.2586 (5)0.0747 (19)
H10.668300.155900.447500.0470*
H20.829400.146800.262800.0520*
H30.829500.244000.437200.0500*
H40.989700.193800.516300.0540*
H50.818400.153500.591500.0550*
H6A0.872900.055700.671500.0780*
H6B0.962700.045600.570000.0780*
H6C0.981100.099400.667500.0780*
H7A0.514100.061300.463100.0880*
H7B0.496100.006300.368000.0880*
H7C0.603200.005500.450500.0880*
H8A0.622100.243600.349600.1260*
H8B0.715300.292800.308300.1260*
H100.447800.238900.247500.1090*
H110.310100.281400.122700.1540*
H120.366200.353400.027100.1780*
H130.553000.388300.049400.1920*
H140.685800.346700.095800.1450*
H170.994200.282900.100700.0720*
H181.075000.345000.055000.0880*
H191.173300.441700.007900.0760*
H201.188500.475500.191000.0740*
H211.111900.411400.347400.0660*
H241.317300.143700.262900.1270*
H251.401500.069400.129100.1580*
H261.310000.027100.079700.1440*
H271.131600.050400.159500.1280*
H281.047400.023700.293200.0900*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0570 (6)0.0519 (6)0.0473 (5)0.0133 (6)0.0038 (6)0.0042 (5)
O10.0475 (15)0.0414 (14)0.0462 (15)0.0006 (13)0.0048 (13)0.0058 (12)
O20.074 (2)0.0609 (19)0.075 (2)0.0036 (18)0.018 (2)0.0060 (18)
O30.0556 (17)0.0434 (14)0.0442 (15)0.0149 (13)0.0028 (15)0.0012 (14)
O40.091 (3)0.074 (2)0.0467 (18)0.038 (2)0.0068 (19)0.0091 (17)
O50.0391 (15)0.0572 (17)0.0592 (18)0.0052 (13)0.0005 (15)0.0006 (15)
O60.058 (2)0.105 (3)0.121 (3)0.026 (2)0.002 (2)0.037 (3)
C10.045 (2)0.042 (2)0.039 (2)0.0039 (18)0.0001 (18)0.0014 (18)
C20.049 (2)0.041 (2)0.043 (2)0.0050 (18)0.0072 (19)0.0058 (18)
C30.045 (2)0.0410 (18)0.042 (2)0.0072 (19)0.002 (2)0.0061 (17)
C40.048 (2)0.050 (2)0.041 (2)0.003 (2)0.0081 (19)0.0024 (19)
C50.048 (2)0.050 (2)0.042 (2)0.003 (2)0.008 (2)0.0039 (18)
C60.070 (3)0.062 (3)0.064 (3)0.004 (3)0.018 (3)0.014 (3)
C70.085 (4)0.063 (3)0.072 (3)0.029 (3)0.009 (3)0.008 (3)
C80.095 (5)0.130 (5)0.069 (4)0.020 (4)0.011 (3)0.041 (4)
C90.070 (4)0.051 (3)0.122 (5)0.017 (3)0.021 (4)0.002 (3)
C100.091 (5)0.078 (4)0.108 (5)0.001 (4)0.022 (4)0.014 (4)
C110.084 (5)0.166 (8)0.129 (7)0.031 (6)0.028 (6)0.061 (7)
C120.242 (14)0.151 (10)0.066 (5)0.132 (10)0.034 (7)0.027 (6)
C130.291 (16)0.092 (6)0.099 (7)0.043 (9)0.064 (10)0.013 (5)
C140.133 (7)0.085 (5)0.155 (8)0.025 (5)0.042 (7)0.008 (5)
C150.048 (2)0.046 (2)0.053 (3)0.010 (2)0.004 (2)0.0027 (19)
C160.042 (2)0.042 (2)0.045 (2)0.0053 (18)0.0043 (18)0.0011 (18)
C170.073 (3)0.057 (3)0.051 (3)0.017 (2)0.000 (3)0.001 (2)
C180.098 (4)0.074 (3)0.050 (3)0.021 (3)0.007 (3)0.008 (3)
C190.069 (3)0.059 (3)0.066 (3)0.008 (3)0.010 (3)0.019 (2)
C200.064 (3)0.049 (2)0.078 (4)0.013 (2)0.003 (3)0.007 (2)
C210.061 (3)0.053 (2)0.059 (3)0.015 (2)0.002 (2)0.002 (2)
C220.044 (2)0.071 (3)0.073 (3)0.006 (2)0.003 (3)0.000 (3)
C230.038 (2)0.082 (3)0.070 (3)0.004 (2)0.000 (2)0.003 (3)
C240.053 (3)0.122 (5)0.153 (7)0.017 (4)0.019 (4)0.036 (5)
C250.054 (3)0.178 (8)0.156 (8)0.001 (5)0.030 (4)0.055 (7)
C260.061 (4)0.155 (7)0.142 (7)0.014 (5)0.007 (4)0.052 (6)
C270.067 (4)0.100 (5)0.143 (6)0.010 (4)0.008 (4)0.030 (5)
C280.054 (3)0.076 (3)0.094 (4)0.003 (3)0.009 (3)0.009 (3)
Geometric parameters (Å, º) top
S1—C11.802 (4)C23—C281.375 (8)
S1—C71.784 (5)C24—C251.389 (12)
O1—C11.432 (5)C25—C261.361 (13)
O1—C51.442 (5)C26—C271.373 (9)
O2—C21.403 (5)C27—C281.383 (9)
O2—C81.295 (8)C1—H10.9600
O3—C31.442 (5)C2—H20.9400
O3—C151.345 (5)C3—H30.9600
O4—C151.211 (5)C4—H40.9500
O5—C41.441 (5)C5—H50.9500
O5—C221.355 (5)C6—H6A0.9500
O6—C221.218 (6)C6—H6B0.9500
C1—C21.526 (6)C6—H6C0.9500
C2—C31.515 (6)C7—H7A0.9500
C3—C41.517 (6)C7—H7B0.9400
C4—C51.511 (6)C7—H7C0.9600
C5—C61.512 (6)C8—H8A0.9000
C8—C91.621 (10)C8—H8B0.9700
C9—C101.332 (9)C10—H100.9400
C9—C141.350 (12)C11—H110.9300
C10—C111.342 (11)C12—H120.9500
C11—C121.352 (15)C13—H130.9700
C12—C131.37 (2)C14—H140.9500
C13—C141.432 (17)C17—H170.9500
C15—C161.480 (6)C18—H180.9500
C16—C171.374 (6)C19—H190.9500
C16—C211.389 (6)C20—H200.9500
C17—C181.383 (7)C21—H210.9500
C18—C191.388 (7)C24—H240.9600
C19—C201.357 (7)C25—H250.9600
C20—C211.390 (7)C26—H260.9400
C22—C231.477 (7)C27—H270.9400
C23—C241.369 (8)C28—H280.9500
S1···O23.003 (4)C23···H13viii3.0100
S1···C83.665 (8)C28···H13viii2.9200
S1···H6Ai3.1000H1···C82.7500
S1···H18ii3.1500H1···H52.3700
S1···H20iii3.0400H1···H8A2.1600
O1···O52.799 (3)H1···O4v2.5500
O2···O32.797 (4)H2···O52.5400
O2···S13.003 (4)H3···O42.4200
O3···C83.253 (7)H3···C82.5900
O3···O63.183 (4)H3···H52.5200
O3···O22.797 (4)H3···H8B2.1900
O3···O52.804 (4)H3···O6v2.8900
O3···C223.169 (5)H4···O42.8000
O4···C1iv3.417 (5)H4···O62.3600
O4···C43.226 (5)H4···C153.0200
O5···O12.799 (3)H4···H6C2.5500
O5···O32.804 (4)H4···H8Aiv2.5000
O6···C153.300 (6)H5···H12.3700
O6···O33.183 (4)H5···H32.5200
O1···H7C2.7700H6A···S1ix3.1000
O1···H20iii2.8900H6B···O52.6500
O2···H18ii2.8300H6C···H42.5500
O3···H172.4000H6C···C9iv3.0300
O3···H8B2.7700H6C···C10iv3.1000
O4···H42.8000H7A···O4v2.5800
O4···H212.5600H7A···H21v2.4500
O4···H32.4200H7C···O12.7700
O4···H1iv2.5500H8A···C12.6000
O4···H7Aiv2.5800H8A···C32.9900
O5···H282.3900H8A···H12.1600
O5···H22.5400H8A···H102.3400
O5···H6B2.6500H8A···H4v2.5000
O6···H42.3600H8B···O32.7700
O6···H242.5900H8B···C32.5700
O6···H3iv2.8900H8B···H32.1900
C1···O4v3.417 (5)H10···H8A2.3400
C4···O43.226 (5)H10···H24x2.4800
C8···O33.253 (7)H12···C19x3.0900
C8···S13.665 (8)H13···C23ii3.0100
C15···O63.300 (6)H13···C28ii2.9200
C22···O33.169 (5)H17···O32.4000
C1···H8A2.6000H17···C12viii2.9500
C3···H8B2.5700H18···S1viii3.1500
C3···H8A2.9900H18···O2viii2.8300
C7···H21v3.0300H18···C9viii3.0800
C8···H32.5900H18···C10viii3.0400
C8···H12.7500H20···S1vii3.0400
C9···H6Cv3.0300H20···O1vii2.8900
C9···H18ii3.0800H21···O42.5600
C10···H18ii3.0400H21···C7iv3.0300
C10···H6Cv3.1000H21···H7Aiv2.4500
C12···H17ii2.9500H24···O62.5900
C15···H43.0200H24···H10vi2.4800
C18···H25ii3.0900H25···C18viii3.0900
C19···H12vi3.0900H27···C21iii3.0500
C20···H28vii2.9500H28···O52.3900
C21···H27vii3.0500H28···C20iii2.9500
C1—S1—C7101.6 (2)O3—C3—H3110.00
C1—O1—C5112.1 (3)C2—C3—H3109.00
C2—O2—C8112.3 (4)C4—C3—H3109.00
C3—O3—C15117.8 (3)O5—C4—H4110.00
C4—O5—C22119.6 (3)C3—C4—H4110.00
S1—C1—O1108.7 (2)C5—C4—H4110.00
S1—C1—C2107.3 (3)O1—C5—H5109.00
O1—C1—C2110.0 (3)C4—C5—H5109.00
O2—C2—C1113.8 (3)C6—C5—H5109.00
O2—C2—C3115.1 (3)C5—C6—H6A110.00
C1—C2—C3109.7 (4)C5—C6—H6B110.00
O3—C3—C2105.9 (3)C5—C6—H6C109.00
O3—C3—C4111.7 (4)H6A—C6—H6B109.00
C2—C3—C4111.1 (3)H6A—C6—H6C109.00
O5—C4—C3108.8 (3)H6B—C6—H6C109.00
O5—C4—C5107.9 (3)S1—C7—H7A109.00
C3—C4—C5109.6 (4)S1—C7—H7B110.00
O1—C5—C4109.6 (3)S1—C7—H7C109.00
O1—C5—C6106.8 (3)H7A—C7—H7B110.00
C4—C5—C6114.1 (4)H7A—C7—H7C109.00
O2—C8—C9105.5 (5)H7B—C7—H7C110.00
C8—C9—C10116.6 (6)O2—C8—H8A113.00
C8—C9—C14124.8 (6)O2—C8—H8B109.00
C10—C9—C14118.6 (7)C9—C8—H8A110.00
C9—C10—C11124.1 (7)C9—C8—H8B107.00
C10—C11—C12116.6 (9)H8A—C8—H8B112.00
C11—C12—C13125.0 (11)C9—C10—H10118.00
C12—C13—C14113.8 (10)C11—C10—H10117.00
C9—C14—C13121.8 (9)C10—C11—H11124.00
O3—C15—O4122.3 (4)C12—C11—H11120.00
O3—C15—C16112.6 (3)C11—C12—H12121.00
O4—C15—C16125.1 (4)C13—C12—H12114.00
C15—C16—C17122.4 (4)C12—C13—H13125.00
C15—C16—C21118.3 (4)C14—C13—H13121.00
C17—C16—C21119.3 (4)C9—C14—H14119.00
C16—C17—C18120.9 (4)C13—C14—H14119.00
C17—C18—C19119.4 (5)C16—C17—H17119.00
C18—C19—C20120.1 (4)C18—C17—H17120.00
C19—C20—C21120.7 (4)C17—C18—H18120.00
C16—C21—C20119.6 (4)C19—C18—H18121.00
O5—C22—O6122.2 (4)C18—C19—H19119.00
O5—C22—C23111.3 (4)C20—C19—H19120.00
O6—C22—C23126.4 (5)C19—C20—H20120.00
C22—C23—C24118.7 (6)C21—C20—H20120.00
C22—C23—C28122.4 (4)C16—C21—H21120.00
C24—C23—C28118.9 (6)C20—C21—H21121.00
C23—C24—C25119.6 (7)C23—C24—H24120.00
C24—C25—C26121.0 (6)C25—C24—H24120.00
C25—C26—C27119.9 (8)C24—C25—H25119.00
C26—C27—C28118.9 (6)C26—C25—H25120.00
C23—C28—C27121.6 (5)C25—C26—H26120.00
S1—C1—H1110.00C27—C26—H26120.00
O1—C1—H1110.00C26—C27—H27120.00
C2—C1—H1111.00C28—C27—H27121.00
O2—C2—H2106.00C23—C28—H28119.00
C1—C2—H2106.00C27—C28—H28120.00
C3—C2—H2106.00
C7—S1—C1—O161.8 (3)O2—C8—C9—C10102.3 (7)
C7—S1—C1—C2179.2 (3)C8—C9—C10—C11176.0 (7)
C5—O1—C1—S1179.2 (2)C10—C9—C14—C131.0 (13)
C5—O1—C1—C262.0 (4)C14—C9—C10—C111.7 (12)
C1—O1—C5—C6172.9 (3)C8—C9—C14—C13178.5 (8)
C1—O1—C5—C463.0 (4)C9—C10—C11—C123.6 (13)
C8—O2—C2—C356.9 (6)C10—C11—C12—C132.8 (16)
C8—O2—C2—C170.9 (5)C11—C12—C13—C140.4 (16)
C2—O2—C8—C9171.7 (4)C12—C13—C14—C91.6 (14)
C15—O3—C3—C486.4 (4)O4—C15—C16—C216.1 (7)
C3—O3—C15—O46.6 (6)O4—C15—C16—C17171.9 (4)
C3—O3—C15—C16172.6 (3)O3—C15—C16—C177.4 (6)
C15—O3—C3—C2152.5 (3)O3—C15—C16—C21174.7 (4)
C22—O5—C4—C3101.6 (4)C21—C16—C17—C182.2 (7)
C22—O5—C4—C5139.7 (4)C15—C16—C21—C20175.5 (4)
C4—O5—C22—O62.7 (7)C17—C16—C21—C202.5 (6)
C4—O5—C22—C23179.6 (4)C15—C16—C17—C18175.7 (4)
S1—C1—C2—C3174.0 (3)C16—C17—C18—C190.7 (8)
O1—C1—C2—O2173.5 (3)C17—C18—C19—C200.5 (8)
O1—C1—C2—C356.0 (4)C18—C19—C20—C210.2 (7)
S1—C1—C2—O255.4 (4)C19—C20—C21—C161.3 (7)
C1—C2—C3—C453.1 (4)O5—C22—C23—C24168.0 (5)
O2—C2—C3—O355.6 (4)O5—C22—C23—C2813.0 (7)
O2—C2—C3—C4177.1 (4)O6—C22—C23—C248.7 (9)
C1—C2—C3—O3174.6 (3)O6—C22—C23—C28170.3 (5)
O3—C3—C4—O554.6 (4)C24—C23—C28—C272.0 (9)
O3—C3—C4—C5172.3 (3)C22—C23—C24—C25178.9 (6)
C2—C3—C4—O563.5 (4)C28—C23—C24—C252.1 (10)
C2—C3—C4—C554.2 (5)C22—C23—C28—C27179.0 (6)
C3—C4—C5—C6177.4 (3)C23—C24—C25—C261.1 (12)
O5—C4—C5—O160.6 (4)C24—C25—C26—C270.1 (13)
O5—C4—C5—C659.1 (4)C25—C26—C27—C280.3 (12)
C3—C4—C5—O157.7 (4)C26—C27—C28—C230.8 (10)
O2—C8—C9—C1480.1 (9)
Symmetry codes: (i) x+3/2, y, z1/2; (ii) x1/2, y+1/2, z; (iii) x+2, y1/2, z+1/2; (iv) x+1/2, y+1/2, z+1; (v) x1/2, 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) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O4v0.962.553.417 (5)151
C2—H2···O50.942.542.920 (4)104
C4—H4···O60.952.362.726 (6)102
C7—H7A···O4v0.952.583.452 (6)152
C17—H17···O30.952.402.738 (5)100
C28—H28···O50.952.392.721 (6)100
Symmetry code: (v) x1/2, y+1/2, z+1.
 

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