Acta Cryst. (2008). E64, o379 [ doi:10.1107/S1600536807068195 ]
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-L-rhamnopyranoside hemihydrateIn the title compound, C12H15NO7·0.5H2O, there are two independent molecules in the asymmetric unit, together with one water molecule. The pyranoside rings each have close to a 1C4 chair conformation and the nitro groups are almost coplanar with the benzene rings. The water molecule links the two independent molecules through O-H
O hydrogen bonds. All the hydroxyl groups are involved in hydrogen-bond interactions, giving rise to a three-dimensional network.
The title compound is commercialy available (Sigma Chemical Company) or can be easily prepared following the described procedure of Garegg et al. (1978). The title compound, (I), was crystallized from methanol by slow evaporation of the solvent.
In the absence of significant anomalous scattering effects, Friedel pairs were merged. The positional and displacement parameters for the H atoms bound to O were refined. The methyl H atoms were constrained to an ideal geometry, with C—H = 0.98Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in calculated positions (C—H = 0.95–1.00 Å), with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2006); cell refinement: SMART (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1995); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
![[Figure 1]](./bv2086fig1thm.gif)
| Fig. 1. The molecular structure and atom-labelling scheme for (I). Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./bv2086fig2thm.gif)
| Fig. 2. The crystal packing of the structure, showing the network of hydrogen bonds (dotted lines). |
| C12H15NO7·0.5H2O | F000 = 620 |
| Mr = 294.26 | Dx = 1.441 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: P 2yb | Cell parameters from 8274 reflections |
| a = 10.5371 (15) Å | θ = 2.4–27.4º |
| b = 6.8681 (8) Å | µ = 0.12 mm−1 |
| c = 19.135 (3) Å | T = 100 (2) K |
| β = 101.543 (7)º | Plate, colourless |
| V = 1356.8 (3) Å3 | 0.6 × 0.58 × 0.23 mm |
| Z = 4 |
| Bruker APEXII diffractometer | 3147 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.051 |
| T = 100(2) K | θmax = 27.4º |
| CCD rotation images, thin slices scans | θmin = 3.5º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −13→12 |
| Tmin = 0.923, Tmax = 0.972 | k = −8→8 |
| 14281 measured reflections | l = −24→21 |
| 3340 independent reflections |
| 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)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0398P)2 + 0.2743P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max = 0.001 |
| 3340 reflections | Δρmax = 0.38 e Å−3 |
| 396 parameters | Δρmin = −0.24 e Å−3 |
| 1 restraint | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C12H15NO7·0.5H2O | V = 1356.8 (3) Å3 |
| Mr = 294.26 | Z = 4 |
| Monoclinic, P21 | Mo Kα |
| a = 10.5371 (15) Å | µ = 0.12 mm−1 |
| b = 6.8681 (8) Å | T = 100 (2) K |
| c = 19.135 (3) Å | 0.6 × 0.58 × 0.23 mm |
| β = 101.543 (7)º |
| Bruker APEXII diffractometer | 3340 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 3147 reflections with I > 2σ(I) |
| Tmin = 0.923, Tmax = 0.972 | Rint = 0.051 |
| 14281 measured reflections |
| R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.080 | Δρmax = 0.38 e Å−3 |
| S = 1.04 | Δρmin = −0.24 e Å−3 |
| 3340 reflections | Absolute structure: ? |
| 396 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| N113 | 0.06897 (18) | 1.3356 (3) | −0.12305 (9) | 0.0208 (4) | |
| O114 | −0.04061 (15) | 1.3222 (3) | −0.16072 (8) | 0.0285 (4) | |
| O115 | 0.16860 (16) | 1.3419 (3) | −0.14777 (8) | 0.0320 (4) | |
| C110 | 0.0816 (2) | 1.3456 (3) | −0.04511 (10) | 0.0169 (4) | |
| C109 | −0.0304 (2) | 1.3374 (3) | −0.01675 (11) | 0.0181 (4) | |
| H109 | −0.1132 | 1.326 | −0.0471 | 0.022* | |
| C108 | −0.01818 (19) | 1.3462 (3) | 0.05646 (11) | 0.0176 (4) | |
| H108 | −0.0933 | 1.3403 | 0.0768 | 0.021* | |
| C107 | 0.10436 (19) | 1.3638 (3) | 0.10079 (10) | 0.0154 (4) | |
| C112 | 0.21624 (19) | 1.3726 (3) | 0.07163 (11) | 0.0184 (4) | |
| H112 | 0.2992 | 1.3849 | 0.1018 | 0.022* | |
| C111 | 0.20393 (19) | 1.3632 (3) | −0.00206 (11) | 0.0179 (4) | |
| H111 | 0.2786 | 1.3688 | −0.0228 | 0.021* | |
| O101 | 0.10387 (13) | 1.3698 (2) | 0.17252 (7) | 0.0173 (3) | |
| C101 | 0.21582 (18) | 1.4443 (3) | 0.22070 (10) | 0.0150 (4) | |
| H101 | 0.2387 | 1.574 | 0.203 | 0.018* | |
| C102 | 0.17225 (19) | 1.4730 (3) | 0.29214 (10) | 0.0143 (4) | |
| H102 | 0.0905 | 1.551 | 0.2848 | 0.017* | |
| O102 | 0.27280 (15) | 1.5708 (2) | 0.34038 (8) | 0.0188 (3) | |
| H12 | 0.259 (3) | 1.692 (6) | 0.3366 (17) | 0.05* | |
| C103 | 0.15121 (19) | 1.2737 (3) | 0.32381 (10) | 0.0136 (4) | |
| H103 | 0.0781 | 1.2065 | 0.2914 | 0.016* | |
| O103 | 0.11609 (15) | 1.3034 (2) | 0.39202 (7) | 0.0180 (3) | |
| H13 | 0.115 (3) | 1.197 (6) | 0.4126 (18) | 0.05* | |
| C104 | 0.2735 (2) | 1.1506 (3) | 0.32928 (10) | 0.0136 (4) | |
| H104 | 0.3475 | 1.2151 | 0.3619 | 0.016* | |
| O104 | 0.25457 (15) | 0.9597 (2) | 0.35459 (8) | 0.0173 (3) | |
| H14 | 0.246 (3) | 0.959 (6) | 0.3956 (19) | 0.05* | |
| C105 | 0.30432 (19) | 1.1288 (3) | 0.25488 (11) | 0.0151 (4) | |
| H105 | 0.2297 | 1.0641 | 0.2228 | 0.018* | |
| C106 | 0.4262 (2) | 1.0144 (3) | 0.25400 (12) | 0.0232 (5) | |
| H10A | 0.4425 | 1.0112 | 0.2054 | 0.035* | |
| H10B | 0.4157 | 0.8811 | 0.2703 | 0.035* | |
| H10C | 0.4995 | 1.0764 | 0.2858 | 0.035* | |
| O105 | 0.32371 (13) | 1.3205 (2) | 0.22692 (7) | 0.0154 (3) | |
| N213 | −0.39091 (16) | 0.4276 (3) | 0.01163 (9) | 0.0194 (4) | |
| O215 | −0.32520 (14) | 0.3120 (3) | −0.01531 (8) | 0.0235 (3) | |
| O214 | −0.46481 (17) | 0.5465 (3) | −0.02365 (8) | 0.0322 (4) | |
| C210 | −0.38055 (19) | 0.4233 (3) | 0.08925 (10) | 0.0168 (4) | |
| C209 | −0.4304 (2) | 0.5769 (3) | 0.12271 (11) | 0.0190 (4) | |
| H209 | −0.4724 | 0.6827 | 0.0955 | 0.023* | |
| C208 | −0.41803 (19) | 0.5738 (3) | 0.19635 (11) | 0.0180 (4) | |
| H208 | −0.4504 | 0.6787 | 0.2201 | 0.022* | |
| C207 | −0.35783 (18) | 0.4156 (3) | 0.23528 (10) | 0.0146 (4) | |
| C212 | −0.3100 (2) | 0.2609 (3) | 0.20071 (11) | 0.0180 (4) | |
| H212 | −0.2699 | 0.1532 | 0.2276 | 0.022* | |
| C211 | −0.32092 (19) | 0.2644 (3) | 0.12718 (11) | 0.0178 (4) | |
| H211 | −0.2883 | 0.1602 | 0.1033 | 0.021* | |
| O201 | −0.34096 (13) | 0.3963 (2) | 0.30809 (7) | 0.0153 (3) | |
| C201 | −0.37263 (19) | 0.5583 (3) | 0.34905 (10) | 0.0141 (4) | |
| H201 | −0.4677 | 0.5847 | 0.3353 | 0.017* | |
| C202 | −0.34018 (18) | 0.4911 (3) | 0.42743 (10) | 0.0139 (4) | |
| H202 | −0.3827 | 0.363 | 0.4323 | 0.017* | |
| O202 | −0.38516 (14) | 0.6325 (2) | 0.47115 (8) | 0.0168 (3) | |
| H22 | −0.464 (3) | 0.597 (6) | 0.4737 (17) | 0.05* | |
| C203 | −0.19271 (18) | 0.4703 (3) | 0.45089 (10) | 0.0122 (4) | |
| H203 | −0.1636 | 0.355 | 0.4263 | 0.015* | |
| O203 | −0.16051 (13) | 0.4396 (2) | 0.52635 (7) | 0.0148 (3) | |
| H23 | −0.114 (3) | 0.341 (6) | 0.5351 (17) | 0.05* | |
| C204 | −0.12210 (17) | 0.6509 (3) | 0.43223 (10) | 0.0123 (4) | |
| H204 | −0.1453 | 0.7623 | 0.4609 | 0.015* | |
| O204 | 0.01541 (13) | 0.6233 (2) | 0.45107 (7) | 0.0149 (3) | |
| H24 | 0.036 (3) | 0.533 (6) | 0.4294 (18) | 0.05* | |
| C206 | −0.1076 (2) | 0.8921 (3) | 0.33282 (11) | 0.0202 (4) | |
| H20A | −0.1367 | 0.9148 | 0.2815 | 0.03* | |
| H20B | −0.0128 | 0.8843 | 0.3443 | 0.03* | |
| H20C | −0.1365 | 0.9997 | 0.3595 | 0.03* | |
| C205 | −0.16438 (18) | 0.7030 (3) | 0.35314 (10) | 0.0131 (4) | |
| H205 | −0.1398 | 0.5948 | 0.3234 | 0.016* | |
| O205 | −0.30423 (13) | 0.7267 (2) | 0.33721 (7) | 0.0142 (3) | |
| O1 | 0.62208 (15) | 0.0270 (2) | 0.50941 (9) | 0.0203 (3) | |
| H1A | 0.628 (3) | −0.084 (6) | 0.4891 (18) | 0.05* | |
| H1B | 0.664 (3) | 0.021 (6) | 0.5520 (19) | 0.05* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N113 | 0.0260 (9) | 0.0160 (8) | 0.0201 (9) | −0.0018 (7) | 0.0036 (7) | −0.0005 (7) |
| O114 | 0.0280 (8) | 0.0352 (9) | 0.0194 (7) | −0.0047 (7) | −0.0025 (6) | −0.0013 (7) |
| O115 | 0.0295 (9) | 0.0478 (11) | 0.0201 (8) | −0.0030 (8) | 0.0083 (7) | −0.0006 (8) |
| C110 | 0.0221 (10) | 0.0125 (9) | 0.0154 (9) | −0.0003 (8) | 0.0023 (8) | 0.0008 (7) |
| C109 | 0.0173 (10) | 0.0138 (9) | 0.0216 (10) | −0.0015 (8) | 0.0003 (7) | −0.0003 (8) |
| C108 | 0.0162 (9) | 0.0151 (9) | 0.0222 (10) | −0.0013 (8) | 0.0057 (8) | 0.0005 (8) |
| C107 | 0.0174 (9) | 0.0125 (9) | 0.0163 (9) | 0.0001 (8) | 0.0030 (7) | 0.0007 (7) |
| C112 | 0.0153 (9) | 0.0205 (10) | 0.0185 (10) | −0.0014 (8) | 0.0014 (7) | 0.0014 (8) |
| C111 | 0.0184 (10) | 0.0166 (10) | 0.0195 (10) | −0.0010 (8) | 0.0056 (8) | 0.0022 (8) |
| O101 | 0.0152 (7) | 0.0213 (7) | 0.0151 (7) | −0.0021 (6) | 0.0026 (5) | 0.0011 (6) |
| C101 | 0.0138 (9) | 0.0137 (9) | 0.0169 (9) | −0.0009 (7) | 0.0019 (7) | 0.0010 (7) |
| C102 | 0.0155 (9) | 0.0105 (8) | 0.0160 (9) | 0.0034 (7) | 0.0010 (7) | 0.0014 (7) |
| O102 | 0.0267 (8) | 0.0091 (6) | 0.0192 (7) | 0.0000 (6) | 0.0010 (6) | −0.0003 (5) |
| C103 | 0.0157 (9) | 0.0122 (8) | 0.0135 (9) | −0.0005 (7) | 0.0039 (7) | −0.0007 (7) |
| O103 | 0.0260 (8) | 0.0131 (7) | 0.0170 (7) | 0.0042 (6) | 0.0097 (6) | 0.0012 (6) |
| C104 | 0.0168 (9) | 0.0079 (8) | 0.0166 (9) | 0.0004 (7) | 0.0045 (7) | 0.0003 (7) |
| O104 | 0.0280 (8) | 0.0092 (6) | 0.0171 (7) | 0.0004 (6) | 0.0105 (6) | 0.0006 (5) |
| C105 | 0.0173 (10) | 0.0111 (8) | 0.0183 (10) | −0.0007 (8) | 0.0067 (7) | −0.0004 (7) |
| C106 | 0.0255 (11) | 0.0168 (10) | 0.0317 (12) | 0.0061 (8) | 0.0163 (9) | 0.0045 (9) |
| O105 | 0.0153 (7) | 0.0131 (6) | 0.0189 (7) | 0.0008 (5) | 0.0057 (5) | 0.0033 (5) |
| N213 | 0.0159 (8) | 0.0243 (9) | 0.0178 (8) | −0.0008 (7) | 0.0029 (7) | −0.0022 (7) |
| O215 | 0.0200 (7) | 0.0317 (8) | 0.0196 (7) | 0.0015 (7) | 0.0057 (6) | −0.0045 (7) |
| O214 | 0.0348 (9) | 0.0422 (10) | 0.0171 (8) | 0.0156 (8) | −0.0009 (6) | 0.0026 (7) |
| C210 | 0.0132 (9) | 0.0226 (10) | 0.0139 (9) | −0.0016 (8) | 0.0012 (7) | −0.0024 (8) |
| C209 | 0.0160 (10) | 0.0201 (10) | 0.0190 (10) | 0.0038 (8) | −0.0008 (8) | 0.0002 (8) |
| C208 | 0.0161 (10) | 0.0176 (9) | 0.0194 (10) | 0.0042 (8) | 0.0013 (8) | −0.0018 (8) |
| C207 | 0.0120 (9) | 0.0158 (9) | 0.0150 (9) | −0.0021 (7) | 0.0001 (7) | −0.0034 (7) |
| C212 | 0.0174 (9) | 0.0155 (9) | 0.0199 (10) | 0.0024 (8) | 0.0006 (8) | −0.0006 (8) |
| C211 | 0.0165 (10) | 0.0189 (10) | 0.0179 (10) | 0.0019 (8) | 0.0035 (8) | −0.0046 (8) |
| O201 | 0.0176 (7) | 0.0136 (7) | 0.0136 (7) | 0.0015 (6) | 0.0008 (5) | −0.0013 (5) |
| C201 | 0.0128 (9) | 0.0138 (9) | 0.0152 (9) | 0.0001 (8) | 0.0013 (7) | −0.0033 (7) |
| C202 | 0.0127 (9) | 0.0130 (9) | 0.0162 (9) | 0.0000 (7) | 0.0031 (7) | −0.0021 (7) |
| O202 | 0.0157 (7) | 0.0159 (7) | 0.0197 (7) | 0.0000 (6) | 0.0061 (6) | −0.0038 (6) |
| C203 | 0.0143 (9) | 0.0118 (8) | 0.0102 (8) | 0.0014 (7) | 0.0014 (7) | 0.0001 (7) |
| O203 | 0.0185 (7) | 0.0143 (7) | 0.0114 (6) | 0.0026 (6) | 0.0027 (5) | 0.0018 (5) |
| C204 | 0.0102 (8) | 0.0124 (8) | 0.0141 (9) | 0.0011 (7) | 0.0017 (7) | −0.0005 (7) |
| O204 | 0.0110 (6) | 0.0140 (7) | 0.0185 (7) | 0.0012 (5) | 0.0005 (5) | −0.0024 (6) |
| C206 | 0.0226 (10) | 0.0194 (10) | 0.0169 (10) | −0.0050 (9) | 0.0001 (8) | 0.0052 (8) |
| C205 | 0.0123 (9) | 0.0135 (8) | 0.0130 (9) | 0.0011 (7) | 0.0016 (7) | 0.0003 (7) |
| O205 | 0.0127 (7) | 0.0133 (7) | 0.0155 (7) | 0.0011 (5) | 0.0003 (5) | 0.0011 (5) |
| O1 | 0.0191 (7) | 0.0178 (8) | 0.0238 (8) | 0.0025 (6) | 0.0032 (6) | −0.0006 (6) |
| N113—O115 | 1.236 (2) | N213—O215 | 1.232 (2) |
| N113—O114 | 1.236 (2) | N213—C210 | 1.468 (3) |
| N113—C110 | 1.472 (3) | C210—C211 | 1.389 (3) |
| C110—C111 | 1.389 (3) | C210—C209 | 1.390 (3) |
| C110—C109 | 1.395 (3) | C209—C208 | 1.389 (3) |
| C109—C108 | 1.382 (3) | C209—H209 | 0.95 |
| C109—H109 | 0.95 | C208—C207 | 1.396 (3) |
| C108—C107 | 1.401 (3) | C208—H208 | 0.95 |
| C108—H108 | 0.95 | C207—O201 | 1.375 (2) |
| C107—O101 | 1.374 (2) | C207—C212 | 1.398 (3) |
| C107—C112 | 1.403 (3) | C212—C211 | 1.389 (3) |
| C112—C111 | 1.391 (3) | C212—H212 | 0.95 |
| C112—H112 | 0.95 | C211—H211 | 0.95 |
| C111—H111 | 0.95 | O201—C201 | 1.438 (2) |
| O101—C101 | 1.438 (2) | C201—O205 | 1.405 (2) |
| C101—O105 | 1.406 (2) | C201—C202 | 1.541 (3) |
| C101—C102 | 1.539 (3) | C201—H201 | 1 |
| C101—H101 | 1 | C202—O202 | 1.424 (2) |
| C102—O102 | 1.426 (2) | C202—C203 | 1.535 (3) |
| C102—C103 | 1.531 (3) | C202—H202 | 1 |
| C102—H102 | 1 | O202—H22 | 0.88 (3) |
| O102—H12 | 0.85 (4) | C203—O203 | 1.431 (2) |
| C103—O103 | 1.440 (2) | C203—C204 | 1.525 (3) |
| C103—C104 | 1.527 (3) | C203—H203 | 1 |
| C103—H103 | 1 | O203—H23 | 0.84 (4) |
| O103—H13 | 0.83 (4) | C204—O204 | 1.434 (2) |
| C104—O104 | 1.426 (2) | C204—C205 | 1.532 (3) |
| C104—C105 | 1.530 (3) | C204—H204 | 1 |
| C104—H104 | 1 | O204—H24 | 0.80 (4) |
| O104—H14 | 0.81 (4) | C206—C205 | 1.513 (3) |
| C105—O105 | 1.450 (2) | C206—H20A | 0.98 |
| C105—C106 | 1.508 (3) | C206—H20B | 0.98 |
| C105—H105 | 1 | C206—H20C | 0.98 |
| C106—H10A | 0.98 | C205—O205 | 1.453 (2) |
| C106—H10B | 0.98 | C205—H205 | 1 |
| C106—H10C | 0.98 | O1—H1A | 0.86 (4) |
| N213—O214 | 1.232 (2) | O1—H1B | 0.85 (4) |
| O115—N113—O114 | 123.06 (18) | O214—N213—C210 | 118.61 (17) |
| O115—N113—C110 | 118.34 (17) | O215—N213—C210 | 118.43 (17) |
| O114—N113—C110 | 118.61 (17) | C211—C210—C209 | 121.90 (18) |
| C111—C110—C109 | 121.97 (19) | C211—C210—N213 | 118.60 (18) |
| C111—C110—N113 | 119.34 (18) | C209—C210—N213 | 119.49 (18) |
| C109—C110—N113 | 118.69 (17) | C208—C209—C210 | 119.23 (19) |
| C108—C109—C110 | 118.56 (18) | C208—C209—H209 | 120.4 |
| C108—C109—H109 | 120.7 | C210—C209—H209 | 120.4 |
| C110—C109—H109 | 120.7 | C209—C208—C207 | 119.57 (19) |
| C109—C108—C107 | 120.32 (18) | C209—C208—H208 | 120.2 |
| C109—C108—H108 | 119.8 | C207—C208—H208 | 120.2 |
| C107—C108—H108 | 119.8 | O201—C207—C208 | 124.66 (18) |
| O101—C107—C108 | 114.84 (17) | O201—C207—C212 | 114.85 (18) |
| O101—C107—C112 | 124.57 (17) | C208—C207—C212 | 120.49 (18) |
| C108—C107—C112 | 120.59 (18) | C211—C212—C207 | 120.10 (19) |
| C111—C112—C107 | 119.06 (18) | C211—C212—H212 | 119.9 |
| C111—C112—H112 | 120.5 | C207—C212—H212 | 119.9 |
| C107—C112—H112 | 120.5 | C210—C211—C212 | 118.68 (18) |
| C110—C111—C112 | 119.49 (18) | C210—C211—H211 | 120.7 |
| C110—C111—H111 | 120.3 | C212—C211—H211 | 120.7 |
| C112—C111—H111 | 120.3 | C207—O201—C201 | 118.71 (15) |
| C107—O101—C101 | 118.97 (15) | O205—C201—O201 | 111.51 (15) |
| O105—C101—O101 | 112.63 (16) | O205—C201—C202 | 112.49 (16) |
| O105—C101—C102 | 112.46 (15) | O201—C201—C202 | 105.56 (15) |
| O101—C101—C102 | 105.23 (15) | O205—C201—H201 | 109.1 |
| O105—C101—H101 | 108.8 | O201—C201—H201 | 109.1 |
| O101—C101—H101 | 108.8 | C202—C201—H201 | 109.1 |
| C102—C101—H101 | 108.8 | O202—C202—C203 | 109.15 (15) |
| O102—C102—C103 | 108.21 (15) | O202—C202—C201 | 109.41 (15) |
| O102—C102—C101 | 108.67 (16) | C203—C202—C201 | 109.08 (15) |
| C103—C102—C101 | 109.26 (15) | O202—C202—H202 | 109.7 |
| O102—C102—H102 | 110.2 | C203—C202—H202 | 109.7 |
| C103—C102—H102 | 110.2 | C201—C202—H202 | 109.7 |
| C101—C102—H102 | 110.2 | C202—O202—H22 | 106 (2) |
| C102—O102—H12 | 108 (2) | O203—C203—C204 | 109.13 (14) |
| O103—C103—C104 | 112.48 (15) | O203—C203—C202 | 109.29 (15) |
| O103—C103—C102 | 108.43 (15) | C204—C203—C202 | 111.63 (15) |
| C104—C103—C102 | 109.58 (16) | O203—C203—H203 | 108.9 |
| O103—C103—H103 | 108.8 | C204—C203—H203 | 108.9 |
| C104—C103—H103 | 108.8 | C202—C203—H203 | 108.9 |
| C102—C103—H103 | 108.8 | C203—O203—H23 | 109 (2) |
| C103—O103—H13 | 110 (2) | O204—C204—C203 | 110.44 (15) |
| O104—C104—C103 | 111.05 (16) | O204—C204—C205 | 111.02 (15) |
| O104—C104—C105 | 107.24 (15) | C203—C204—C205 | 111.23 (15) |
| C103—C104—C105 | 108.90 (16) | O204—C204—H204 | 108 |
| O104—C104—H104 | 109.9 | C203—C204—H204 | 108 |
| C103—C104—H104 | 109.9 | C205—C204—H204 | 108 |
| C105—C104—H104 | 109.9 | C204—O204—H24 | 110 (2) |
| C104—O104—H14 | 113 (3) | C205—C206—H20A | 109.5 |
| O105—C105—C106 | 106.61 (16) | C205—C206—H20B | 109.5 |
| O105—C105—C104 | 109.04 (15) | H20A—C206—H20B | 109.5 |
| C106—C105—C104 | 113.64 (17) | C205—C206—H20C | 109.5 |
| O105—C105—H105 | 109.2 | H20A—C206—H20C | 109.5 |
| C106—C105—H105 | 109.2 | H20B—C206—H20C | 109.5 |
| C104—C105—H105 | 109.2 | O205—C205—C206 | 106.63 (15) |
| C105—C106—H10A | 109.5 | O205—C205—C204 | 108.41 (14) |
| C105—C106—H10B | 109.5 | C206—C205—C204 | 113.74 (16) |
| H10A—C106—H10B | 109.5 | O205—C205—H205 | 109.3 |
| C105—C106—H10C | 109.5 | C206—C205—H205 | 109.3 |
| H10A—C106—H10C | 109.5 | C204—C205—H205 | 109.3 |
| H10B—C106—H10C | 109.5 | C201—O205—C205 | 113.88 (14) |
| C101—O105—C105 | 114.15 (14) | H1A—O1—H1B | 109 (3) |
| O214—N213—O215 | 122.95 (17) | ||
| O115—N113—C110—C111 | 0.4 (3) | O214—N213—C210—C211 | 165.9 (2) |
| O114—N113—C110—C111 | −179.17 (19) | O215—N213—C210—C211 | −14.1 (3) |
| O115—N113—C110—C109 | −179.6 (2) | O214—N213—C210—C209 | −14.0 (3) |
| O114—N113—C110—C109 | 0.8 (3) | O215—N213—C210—C209 | 166.02 (19) |
| C111—C110—C109—C108 | −0.3 (3) | C211—C210—C209—C208 | 1.3 (3) |
| N113—C110—C109—C108 | 179.77 (18) | N213—C210—C209—C208 | −178.75 (17) |
| C110—C109—C108—C107 | 0.3 (3) | C210—C209—C208—C207 | −1.0 (3) |
| C109—C108—C107—O101 | −179.59 (18) | C209—C208—C207—O201 | −179.57 (18) |
| C109—C108—C107—C112 | 0.0 (3) | C209—C208—C207—C212 | 0.0 (3) |
| O101—C107—C112—C111 | 179.37 (18) | O201—C207—C212—C211 | −179.71 (17) |
| C108—C107—C112—C111 | −0.1 (3) | C208—C207—C212—C211 | 0.6 (3) |
| C109—C110—C111—C112 | 0.1 (3) | C209—C210—C211—C212 | −0.7 (3) |
| N113—C110—C111—C112 | −179.95 (18) | N213—C210—C211—C212 | 179.43 (17) |
| C107—C112—C111—C110 | 0.1 (3) | C207—C212—C211—C210 | −0.3 (3) |
| C108—C107—O101—C101 | −161.68 (17) | C208—C207—O201—C201 | −7.9 (3) |
| C112—C107—O101—C101 | 18.8 (3) | C212—C207—O201—C201 | 172.50 (17) |
| C107—O101—C101—O105 | −69.4 (2) | C207—O201—C201—O205 | −56.3 (2) |
| C107—O101—C101—C102 | 167.78 (16) | C207—O201—C201—C202 | −178.77 (15) |
| O105—C101—C102—O102 | 64.6 (2) | O205—C201—C202—O202 | 66.1 (2) |
| O101—C101—C102—O102 | −172.44 (15) | O201—C201—C202—O202 | −172.04 (14) |
| O105—C101—C102—C103 | −53.3 (2) | O205—C201—C202—C203 | −53.2 (2) |
| O101—C101—C102—C103 | 69.69 (19) | O201—C201—C202—C203 | 68.62 (19) |
| O102—C102—C103—O103 | 59.34 (19) | O202—C202—C203—O203 | 51.0 (2) |
| C101—C102—C103—O103 | 177.50 (14) | C201—C202—C203—O203 | 170.50 (15) |
| O102—C102—C103—C104 | −63.78 (19) | O202—C202—C203—C204 | −69.81 (19) |
| C101—C102—C103—C104 | 54.4 (2) | C201—C202—C203—C204 | 49.7 (2) |
| O103—C103—C104—O104 | 62.8 (2) | O203—C203—C204—O204 | 62.33 (19) |
| C102—C103—C104—O104 | −176.49 (15) | C202—C203—C204—O204 | −176.76 (14) |
| O103—C103—C104—C105 | −179.32 (15) | O203—C203—C204—C205 | −173.93 (14) |
| C102—C103—C104—C105 | −58.6 (2) | C202—C203—C204—C205 | −53.0 (2) |
| O104—C104—C105—O105 | 179.73 (15) | O204—C204—C205—O205 | 179.33 (14) |
| C103—C104—C105—O105 | 59.5 (2) | C203—C204—C205—O205 | 55.92 (19) |
| O104—C104—C105—C106 | −61.5 (2) | O204—C204—C205—C206 | −62.3 (2) |
| C103—C104—C105—C106 | 178.25 (17) | C203—C204—C205—C206 | 174.33 (16) |
| O101—C101—O105—C105 | −61.5 (2) | O201—C201—O205—C205 | −57.5 (2) |
| C102—C101—O105—C105 | 57.2 (2) | C202—C201—O205—C205 | 60.9 (2) |
| C106—C105—O105—C101 | 177.03 (16) | C206—C205—O205—C201 | 176.29 (15) |
| C104—C105—O105—C101 | −59.9 (2) | C204—C205—O205—C201 | −60.88 (19) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1A···O202i | 0.86 (3) | 1.97 (7) | 2.803 (7) | 159 (9) |
| O1—H1B···O102ii | 0.84 (8) | 2.06 (1) | 2.881 (8) | 162 (7) |
| O102—H12···O104iii | 0.84 (5) | 1.87 (3) | 2.695 (6) | 163 (8) |
| O103—H13···O203iv | 0.83 (0) | 2.12 (3) | 2.934 (2) | 165 (6) |
| O104—H14···O203iv | 0.80 (8) | 1.89 (5) | 2.663 (7) | 158 (5) |
| O202—H22···O1iv | 0.88 (0) | 1.82 (0) | 2.695 (8) | 173 (0) |
| O203—H23···O204v | 0.83 (7) | 1.80 (6) | 2.641 (8) | 176 (8) |
| O204—H24···O103vi | 0.79 (7) | 1.99 (1) | 2.776 (5) | 168 (4) |
| Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, y−3/2, −z+1; (iii) x, y+1, z; (iv) −x, y+1/2, −z+1; (v) −x, y−1/2, −z+1; (vi) x, y−1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1A···O202i | 0.86 (3) | 1.97 (7) | 2.803 (7) | 159 (9) |
| O1—H1B···O102ii | 0.84 (8) | 2.06 (1) | 2.881 (8) | 162 (7) |
| O102—H12···O104iii | 0.84 (5) | 1.87 (3) | 2.695 (6) | 163 (8) |
| O103—H13···O203iv | 0.83 (0) | 2.12 (3) | 2.934 (2) | 165 (6) |
| O104—H14···O203iv | 0.80 (8) | 1.89 (5) | 2.663 (7) | 158 (5) |
| O202—H22···O1iv | 0.88 (0) | 1.82 (0) | 2.695 (8) | 173 (0) |
| O203—H23···O204v | 0.83 (7) | 1.80 (6) | 2.641 (8) | 176 (8) |
| O204—H24···O103vi | 0.79 (7) | 1.99 (1) | 2.776 (5) | 168 (4) |
| Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, y−3/2, −z+1; (iii) x, y+1, z; (iv) −x, y+1/2, −z+1; (v) −x, y−1/2, −z+1; (vi) x, y−1, z. |
Altomare, A., Burla, M. C., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G. & Polidori, G. (1995). J. Appl. Cryst. 28, 842–846.
Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Fernandez-Castaño, C. & Foces-Foces, C. (1996). Acta Cryst. C52, 1586–1588.
Garegg, P. J., Hultberg, C. & Iversen, T. (1978). Carbohydr. Res. 62, 173–174. [Please check spelling of first author - Garegg here, but Garreg in _exptl_prep]
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
α-L-Rhamnosidases (E.C. 3.2.1.40) catalyze the hydrolysis of L-rhamnose from polysaccharides and glycosides. During in vitro studies, the activity of these enzymes is determined most of the time using the title compound, (I), following the amount of p-nitrophenolate ions released by monitoring the emmision at 400 nm.
The stucture of (I) is shown in Fig. 1. The molecular packing (Fig. 2) is stabilized by hydrogen bonds between all the hydroxyl groups and the water molecules.