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Extensive hydrogen bonding is present in the crystal structure of the title compound [systematic name: (R)-1-cyano-1-(phenyl­meth­yl)-β-D-glucopyranos­yl-(1→6)-β-D-glucopyran­oside], C20H27NO11·3H2O, involving all of the hydr­oxy groups. The water mol­ecules are also involved in the hydrogen bonding; in particular, one of them acts as a bridge between the endocyclic O atoms of the two sugar residues. The overall conformation of the disaccharide is described by the exo-anomeric conformations, φ′′H = 26° and φ′H = 38°, together with an antiperiplanar extended conformation of the constituent sugar residues, with ψ′′ = 155°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006227/wn6326sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006227/wn6326Isup2.hkl
Contains datablock I

CCDC reference: 270564

Key indicators

  • Single-crystal synchrotron study
  • T = 110 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.097
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.98 Ratio PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.40 Ratio
Author Response: This is probbaly due to the fact that the hydrogens are refined with a riding model.

Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H2Y .. H3Y .. 1.84 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT213_ALERT_2_C Atom O2' has ADP max/min Ratio ............. 3.20 prolat PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.53 Ratio PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 15 O7 -C7 -C8 -N1 172.00 3.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 C1 -C7 -C8 -N1 51.00 3.00 1.555 1.555 1.555 1.555 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 29
Alert level G ABSMU_01 Radiation type not identified. Calculation of _exptl_absorpt_correction_mu not performed. 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 45.94 From the CIF: _reflns_number_total 5454 Count of symmetry unique reflns 5630 Completeness (_total/calc) 96.87% 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
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 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 4 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 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1998); cell refinement: SMART; data reduction: SAINT (Siemens, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

(R)-1-cyano-1-(phenylmethyl)-β-D-glucopyranosyl-(1 6)-β-D– glucopyranoside top
Crystal data top
C20H33NO14F(000) = 544
Mr = 511.47Dx = 1.403 Mg m3
Monoclinic, P21Synchrotron radiation, λ = 0.891 Å
Hall symbol: P 2ybCell parameters from 999 reflections
a = 9.4794 (11) Åθ = 3.0–29.0°
b = 7.9025 (9) ŵ = 0.12 mm1
c = 16.2016 (19) ÅT = 110 K
β = 94.089 (3)°Plate, colorless
V = 1210.6 (2) Å30.20 × 0.10 × 0.02 mm
Z = 2
Data collection top
Bruker SMART 1K area-detector
diffractometer
5454 independent reflections
Radiation source: Beamline I711, Maxlab, Lund, Sweden5010 reflections with I > 2σ(I)
Silicon monochromatorRint = 0.031
Detector resolution: 10 pixels mm-1θmax = 45.9°, θmin = 1.6°
ω scan at different φ and 2θh = 1514
Absorption correction: part of the refinement model (ΔF)
(SADABS; Sheldrick, 2002)
k = 1012
Tmin = 0.98, Tmax = 1.00l = 1625
20604 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0714P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5454 reflectionsΔρmax = 0.50 e Å3
343 parametersΔρmin = 0.55 e Å3
10 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.051 (3)
Special details top

Experimental. Absolute structure known as it is a natural product.

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
xyzUiso*/Ueq
C10.88152 (12)0.31296 (17)0.87864 (8)0.0092 (2)
C20.99682 (13)0.40772 (18)0.85467 (8)0.0131 (2)
H20.98190.49740.81600.016*
C31.13334 (13)0.3706 (2)0.88753 (9)0.0157 (3)
H31.21110.43620.87190.019*
C41.15560 (13)0.2378 (2)0.94307 (10)0.0197 (3)
H41.24850.21330.96580.024*
C51.04178 (15)0.1403 (2)0.96545 (10)0.0222 (3)
H51.05750.04791.00250.027*
C60.90413 (14)0.1785 (2)0.93345 (9)0.0158 (3)
H60.82650.11270.94910.019*
C70.73589 (13)0.36194 (19)0.84184 (8)0.0125 (2)
H70.72570.48750.84640.015*
O70.72755 (9)0.31791 (13)0.75585 (6)0.01039 (17)
C80.62104 (14)0.2806 (3)0.88613 (10)0.0224 (3)
N10.53625 (15)0.2211 (3)0.92442 (12)0.0389 (5)
C1'0.64769 (11)0.42740 (15)0.70300 (7)0.00656 (19)
H1'0.66160.54760.72110.008*
C2'0.69827 (10)0.40125 (15)0.61680 (7)0.00594 (19)
H2'0.70080.27700.60520.007*
O2'0.83810 (8)0.46652 (13)0.61580 (6)0.01042 (18)
H2X0.89090.39290.59680.016*
C3'0.60074 (10)0.48632 (15)0.54979 (7)0.00522 (18)
H3'0.62070.61060.54930.006*
O3'0.63560 (9)0.41348 (12)0.47284 (6)0.00866 (16)
H3X0.58940.46240.43360.013*
C4'0.44438 (10)0.45777 (15)0.56317 (7)0.00505 (18)
H4'0.42250.33660.54990.006*
O4'0.35603 (9)0.55936 (12)0.50759 (6)0.00853 (16)
H4X0.35940.66060.52350.013*
C5'0.41182 (11)0.48762 (15)0.65324 (7)0.00556 (18)
H5'0.43040.60860.66840.007*
O5'0.50266 (8)0.37899 (12)0.70512 (6)0.00722 (16)
C6'0.26037 (11)0.44187 (15)0.66901 (8)0.0078 (2)
H6XA0.25010.43260.72920.009*
H6XB0.19490.53050.64620.009*
O6'0.22795 (8)0.28318 (12)0.62937 (6)0.00766 (16)
C1''0.12150 (10)0.18916 (15)0.66312 (7)0.00554 (18)
H1''0.05600.26530.69150.007*
C2''0.04170 (10)0.09484 (14)0.59197 (7)0.00477 (18)
H2''0.11050.03050.56000.006*
O2''0.03409 (8)0.21247 (12)0.53828 (6)0.00786 (16)
H2Y0.02180.25770.50690.012*
C3''0.06282 (10)0.02798 (14)0.62669 (7)0.00450 (18)
H3''0.13370.03710.65670.005*
O3''0.13500 (8)0.12627 (12)0.56258 (6)0.00721 (15)
H3Y0.13990.22740.57810.011*
C4''0.01806 (11)0.14764 (14)0.68725 (7)0.00527 (18)
H4''0.08980.21150.65730.006*
O4''0.07501 (9)0.26505 (12)0.72259 (6)0.00915 (16)
H4Y0.09670.34200.68820.014*
C5''0.09444 (11)0.04260 (15)0.75680 (7)0.00632 (19)
H5''0.02290.02300.78610.008*
O5''0.18930 (8)0.07326 (12)0.72073 (6)0.00724 (16)
C6''0.18368 (12)0.14633 (17)0.81940 (8)0.0103 (2)
H6YA0.23040.07070.86170.012*
H6YB0.12270.22620.84760.012*
O6''0.28803 (11)0.23813 (15)0.77847 (7)0.0182 (2)
H62C0.34640.28120.81390.027*
OW10.51979 (10)0.50771 (13)0.31483 (7)0.01277 (18)
H1W10.510 (2)0.610 (2)0.3052 (14)0.019*
H2W10.587 (2)0.476 (3)0.2876 (13)0.019*
OW20.30569 (13)0.3800 (2)0.19742 (9)0.0294 (3)
H1W20.357 (3)0.432 (4)0.2304 (15)0.044*
H2W20.238 (2)0.346 (4)0.2215 (16)0.044*
OW30.48522 (12)0.18508 (19)0.11009 (8)0.0241 (3)
H1W30.429 (2)0.254 (4)0.1276 (15)0.036*
H2W30.487 (3)0.205 (4)0.0598 (12)0.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0106 (4)0.0109 (5)0.0058 (5)0.0023 (4)0.0022 (4)0.0005 (4)
C20.0157 (5)0.0137 (6)0.0097 (6)0.0010 (4)0.0002 (4)0.0022 (5)
C30.0122 (5)0.0235 (7)0.0112 (6)0.0041 (5)0.0008 (4)0.0021 (5)
C40.0107 (4)0.0328 (8)0.0149 (7)0.0050 (5)0.0033 (4)0.0019 (6)
C50.0173 (5)0.0292 (8)0.0198 (7)0.0061 (5)0.0016 (5)0.0147 (6)
C60.0130 (5)0.0179 (6)0.0164 (6)0.0011 (4)0.0003 (4)0.0088 (5)
C70.0117 (4)0.0179 (6)0.0076 (5)0.0052 (4)0.0015 (4)0.0019 (5)
O70.0117 (3)0.0120 (4)0.0067 (4)0.0047 (3)0.0046 (3)0.0012 (3)
C80.0118 (5)0.0400 (10)0.0154 (7)0.0055 (6)0.0007 (5)0.0014 (6)
N10.0169 (5)0.0684 (14)0.0325 (9)0.0038 (7)0.0086 (6)0.0129 (10)
C1'0.0043 (4)0.0072 (5)0.0077 (5)0.0003 (3)0.0026 (3)0.0010 (4)
C2'0.0033 (3)0.0060 (5)0.0082 (5)0.0002 (3)0.0015 (3)0.0010 (4)
O2'0.0021 (3)0.0119 (4)0.0170 (5)0.0011 (3)0.0007 (3)0.0040 (4)
C3'0.0038 (3)0.0051 (4)0.0067 (5)0.0004 (3)0.0006 (3)0.0007 (4)
O3'0.0083 (3)0.0122 (4)0.0056 (4)0.0023 (3)0.0009 (3)0.0006 (3)
C4'0.0036 (3)0.0047 (4)0.0067 (5)0.0002 (3)0.0013 (3)0.0005 (4)
O4'0.0065 (3)0.0074 (4)0.0110 (4)0.0012 (3)0.0045 (3)0.0023 (3)
C5'0.0039 (3)0.0043 (4)0.0085 (5)0.0005 (3)0.0002 (3)0.0010 (4)
O5'0.0054 (3)0.0078 (4)0.0081 (4)0.0004 (3)0.0019 (3)0.0012 (3)
C6'0.0048 (4)0.0054 (5)0.0134 (6)0.0018 (3)0.0024 (4)0.0032 (4)
O6'0.0070 (3)0.0059 (4)0.0104 (4)0.0044 (3)0.0035 (3)0.0029 (3)
C1''0.0039 (3)0.0053 (4)0.0075 (5)0.0012 (3)0.0004 (3)0.0000 (4)
C2''0.0031 (3)0.0049 (4)0.0061 (5)0.0003 (3)0.0009 (3)0.0002 (3)
O2''0.0050 (3)0.0083 (4)0.0102 (4)0.0007 (3)0.0001 (3)0.0048 (3)
C3''0.0024 (3)0.0053 (4)0.0056 (5)0.0007 (3)0.0014 (3)0.0007 (4)
O3''0.0066 (3)0.0060 (4)0.0085 (4)0.0015 (3)0.0032 (3)0.0015 (3)
C4''0.0044 (3)0.0047 (4)0.0065 (5)0.0007 (3)0.0009 (3)0.0005 (4)
O4''0.0102 (3)0.0074 (4)0.0097 (4)0.0045 (3)0.0005 (3)0.0020 (3)
C5''0.0058 (4)0.0067 (4)0.0064 (5)0.0011 (3)0.0002 (3)0.0002 (4)
O5''0.0042 (3)0.0079 (4)0.0092 (4)0.0020 (3)0.0026 (3)0.0018 (3)
C6''0.0111 (4)0.0112 (5)0.0080 (5)0.0019 (4)0.0028 (4)0.0001 (4)
O6''0.0180 (4)0.0221 (6)0.0132 (5)0.0130 (4)0.0069 (3)0.0056 (4)
OW10.0103 (4)0.0129 (4)0.0153 (5)0.0006 (3)0.0025 (3)0.0023 (4)
OW20.0191 (5)0.0419 (8)0.0276 (7)0.0114 (5)0.0035 (4)0.0059 (6)
OW30.0215 (5)0.0312 (7)0.0191 (6)0.0058 (5)0.0030 (4)0.0008 (5)
Geometric parameters (Å, º) top
C1—C61.3915 (19)C5'—H5'1.0000
C1—C21.4024 (18)C6'—O6'1.4322 (15)
C1—C71.5145 (17)C6'—H6XA0.9900
C2—C31.3951 (19)C6'—H6XB0.9900
C2—H20.9500O6'—C1''1.3957 (13)
C3—C41.389 (2)C1''—O5''1.4275 (14)
C3—H30.9500C1''—C2''1.5271 (16)
C4—C51.394 (2)C1''—H1''1.0000
C4—H40.9500C2''—O2''1.4310 (14)
C5—C61.4021 (19)C2''—C3''1.5230 (15)
C5—H50.9500C2''—H2''1.0000
C6—H60.9500O2''—H2Y0.8400
C7—O71.4326 (16)C3''—O3''1.4315 (14)
C7—C81.492 (2)C3''—C4''1.5288 (16)
C7—H71.0000C3''—H3''1.0000
O7—C1'1.4009 (14)O3''—H3Y0.8400
C8—N11.150 (2)C4''—O4''1.4280 (14)
C1'—O5'1.4298 (13)C4''—C5''1.5385 (16)
C1'—C2'1.5227 (16)C4''—H4''1.0000
C1'—H1'1.0000O4''—H4Y0.8400
C2'—O2'1.4235 (13)C5''—O5''1.4364 (14)
C2'—C3'1.5304 (15)C5''—C6''1.5145 (17)
C2'—H2'1.0000C5''—H5''1.0000
O2'—H2X0.8400C6''—O6''1.4276 (16)
C3'—O3'1.4330 (15)C6''—H6YA0.9900
C3'—C4'1.5300 (14)C6''—H6YB0.9900
C3'—H3'1.0000O6''—H62C0.8400
O3'—H3X0.8400OW1—H1W10.824 (18)
C4'—O4'1.4315 (14)OW1—H2W10.843 (17)
C4'—C5'1.5311 (17)OW2—H1W20.811 (19)
C4'—H4'1.0000OW2—H2W20.821 (19)
O4'—H4X0.8400OW3—H1W30.832 (19)
C5'—O5'1.4428 (14)OW3—H2W30.832 (19)
C5'—C6'1.5196 (15)
C6—C1—C2119.80 (11)O5'—C5'—H5'109.8
C6—C1—C7122.75 (12)C6'—C5'—H5'109.8
C2—C1—C7117.45 (12)C4'—C5'—H5'109.8
C3—C2—C1120.14 (13)C1'—O5'—C5'111.22 (9)
C3—C2—H2119.9O6'—C6'—C5'107.94 (9)
C1—C2—H2119.9O6'—C6'—H6XA110.1
C4—C3—C2120.01 (13)C5'—C6'—H6XA110.1
C4—C3—H3120.0O6'—C6'—H6XB110.1
C2—C3—H3120.0C5'—C6'—H6XB110.1
C3—C4—C5120.08 (12)H6XA—C6'—H6XB108.4
C3—C4—H4120.0C1''—O6'—C6'115.37 (9)
C5—C4—H4120.0O6'—C1''—O5''107.06 (8)
C4—C5—C6120.13 (14)O6'—C1''—C2''107.29 (9)
C4—C5—H5119.9O5''—C1''—C2''110.86 (9)
C6—C5—H5119.9O6'—C1''—H1''110.5
C1—C6—C5119.81 (13)O5''—C1''—H1''110.5
C1—C6—H6120.1C2''—C1''—H1''110.5
C5—C6—H6120.1O2''—C2''—C3''109.08 (8)
O7—C7—C8111.81 (12)O2''—C2''—C1''110.00 (9)
O7—C7—C1107.84 (10)C3''—C2''—C1''109.42 (9)
C8—C7—C1112.12 (12)O2''—C2''—H2''109.4
O7—C7—H7108.3C3''—C2''—H2''109.4
C8—C7—H7108.3C1''—C2''—H2''109.4
C1—C7—H7108.3C2''—O2''—H2Y109.5
C1'—O7—C7115.74 (10)O3''—C3''—C2''111.57 (9)
N1—C8—C7176.11 (19)O3''—C3''—C4''108.78 (9)
O7—C1'—O5'107.38 (10)C2''—C3''—C4''108.76 (8)
O7—C1'—C2'106.57 (9)O3''—C3''—H3''109.2
O5'—C1'—C2'110.60 (9)C2''—C3''—H3''109.2
O7—C1'—H1'110.7C4''—C3''—H3''109.2
O5'—C1'—H1'110.7C3''—O3''—H3Y109.5
C2'—C1'—H1'110.7O4''—C4''—C3''111.30 (8)
O2'—C2'—C1'108.40 (9)O4''—C4''—C5''109.19 (9)
O2'—C2'—C3'110.41 (9)C3''—C4''—C5''108.94 (9)
C1'—C2'—C3'112.17 (9)O4''—C4''—H4''109.1
O2'—C2'—H2'108.6C3''—C4''—H4''109.1
C1'—C2'—H2'108.6C5''—C4''—H4''109.1
C3'—C2'—H2'108.6C4''—O4''—H4Y109.5
C2'—O2'—H2X109.5O5''—C5''—C6''106.35 (9)
O3'—C3'—C4'110.48 (9)O5''—C5''—C4''108.75 (9)
O3'—C3'—C2'106.00 (9)C6''—C5''—C4''114.18 (10)
C4'—C3'—C2'112.15 (9)O5''—C5''—H5''109.1
O3'—C3'—H3'109.4C6''—C5''—H5''109.1
C4'—C3'—H3'109.4C4''—C5''—H5''109.1
C2'—C3'—H3'109.4C1''—O5''—C5''114.16 (8)
C3'—O3'—H3X109.5O6''—C6''—C5''109.66 (10)
O4'—C4'—C3'110.94 (9)O6''—C6''—H6YA109.7
O4'—C4'—C5'111.37 (9)C5''—C6''—H6YA109.7
C3'—C4'—C5'112.06 (9)O6''—C6''—H6YB109.7
O4'—C4'—H4'107.4C5''—C6''—H6YB109.7
C3'—C4'—H4'107.4H6YA—C6''—H6YB108.2
C5'—C4'—H4'107.4C6''—O6''—H62C109.5
C4'—O4'—H4X109.5H1W1—OW1—H2W1105.6 (19)
O5'—C5'—C6'107.00 (10)H1W2—OW2—H2W2108 (2)
O5'—C5'—C4'108.12 (9)H1W3—OW3—H2W3106 (2)
C6'—C5'—C4'112.37 (9)
C6—C1—C2—C31.9 (2)O7—C1'—O5'—C5'178.97 (9)
C7—C1—C2—C3178.90 (13)C2'—C1'—O5'—C5'65.13 (12)
C1—C2—C3—C41.1 (2)C6'—C5'—O5'—C1'172.28 (9)
C2—C3—C4—C50.6 (2)C4'—C5'—O5'—C1'66.47 (11)
C3—C4—C5—C61.5 (3)O5'—C5'—C6'—O6'74.07 (12)
C2—C1—C6—C51.1 (2)C4'—C5'—C6'—O6'44.45 (13)
C7—C1—C6—C5179.78 (14)C5'—C6'—O6'—C1''154.93 (10)
C4—C5—C6—C10.6 (3)C6'—O6'—C1''—O5''94.69 (11)
C6—C1—C7—O7109.30 (15)C6'—O6'—C1''—C2''146.25 (9)
C2—C1—C7—O769.87 (16)O6'—C1''—C2''—O2''67.73 (11)
C6—C1—C7—C814.21 (19)O5''—C1''—C2''—O2''175.68 (8)
C2—C1—C7—C8166.63 (13)O6'—C1''—C2''—C3''172.45 (9)
C8—C7—O7—C1'91.22 (14)O5''—C1''—C2''—C3''55.87 (11)
C1—C7—O7—C1'145.08 (11)O2''—C2''—C3''—O3''62.77 (11)
O7—C7—C8—N1172 (3)C1''—C2''—C3''—O3''176.85 (8)
C1—C7—C8—N151 (3)O2''—C2''—C3''—C4''177.24 (9)
C7—O7—C1'—O5'83.22 (12)C1''—C2''—C3''—C4''56.86 (11)
C7—O7—C1'—C2'158.25 (10)O3''—C3''—C4''—O4''58.91 (12)
O7—C1'—C2'—O2'69.25 (11)C2''—C3''—C4''—O4''179.39 (9)
O5'—C1'—C2'—O2'174.35 (9)O3''—C3''—C4''—C5''179.36 (8)
O7—C1'—C2'—C3'168.59 (9)C2''—C3''—C4''—C5''58.93 (11)
O5'—C1'—C2'—C3'52.19 (12)O4''—C4''—C5''—O5''179.14 (9)
O2'—C2'—C3'—O3'75.00 (11)C3''—C4''—C5''—O5''59.11 (11)
C1'—C2'—C3'—O3'163.99 (9)O4''—C4''—C5''—C6''60.57 (12)
O2'—C2'—C3'—C4'164.35 (9)C3''—C4''—C5''—C6''177.68 (9)
C1'—C2'—C3'—C4'43.34 (13)O6'—C1''—O5''—C5''175.61 (9)
O3'—C3'—C4'—O4'70.91 (12)C2''—C1''—O5''—C5''58.88 (12)
C2'—C3'—C4'—O4'171.08 (9)C6''—C5''—O5''—C1''176.51 (9)
O3'—C3'—C4'—C5'163.92 (9)C4''—C5''—O5''—C1''60.09 (12)
C2'—C3'—C4'—C5'45.90 (13)O5''—C5''—C6''—O6''61.27 (13)
O4'—C4'—C5'—O5'178.90 (8)C4''—C5''—C6''—O6''58.66 (13)
C3'—C4'—C5'—O5'56.16 (12)H1''—C1''—O6'—C6'25.7
O4'—C4'—C5'—C6'61.05 (12)H1'—C1'—O7—C737.8
C3'—C4'—C5'—C6'174.02 (10)C1'—O7—C7—H728.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2X···O2i0.841.882.701 (1)166
O3—H3X···OW10.842.022.813 (2)157
O4—H4X···O3ii0.842.002.817 (1)164
O2—H2Y···O3iii0.841.852.690 (1)175
O3—H3Y···O40.842.402.835 (1)113
O3—H3Y···O2iv0.842.513.346 (1)176
O4—H4Y···O2iv0.841.992.823 (1)174
O6—H62C···OW3v0.841.962.774 (1)162
OW1—H1W1···O5ii0.82 (2)2.14 (2)2.958 (2)173 (2)
OW1—H2W1···O5ii0.84 (2)2.26 (2)2.904 (1)133 (2)
OW1—H2W1···O6ii0.84 (2)2.36 (2)3.126 (2)151 (2)
OW2—H1W2···OW10.81 (3)2.07 (3)2.864 (2)165 (3)
OW2—H2W2···O4iii0.82 (2)2.04 (2)2.860 (2)174 (2)
OW3—H1W3···OW20.83 (2)1.95 (2)2.760 (2)164 (2)
OW3—H2W3···N1vi0.83 (2)2.28 (2)3.094 (2)167 (2)
C5—H5···Cgvii0.952.713.590 (2)155
C5—H5···Cgviii1.002.833.640 (2)138
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1/2, z+1; (iii) x, y+1/2, z+1; (iv) x1, y1, z; (v) x+1, y1/2, z+1; (vi) x, y, z1; (vii) x3, y1/2, z+2; (viii) x1, y, z.
 

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