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ISSN: 2056-9890

4-Nitro­phenyl α-L-rhamno­pyran­oside hemihydrate

aOrganic and Supramolecular Chemistry, Ecole Nationale Supérieure de Chimie, UMR CNRS 6226, Avenue du Général Leclerc, 35700 Rennes, France, and bCentre de Diffractométrie X, Université de Rennes 1, UMR CNRS 6226, 35042 Rennes, France
*Correspondence e-mail: richard.daniellou@ensc-rennes.fr

(Received 21 November 2007; accepted 21 December 2007; online 9 January 2008)

In 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.

Related literature

For a related structure, see Fernandez-Castaño & Foces-Foces (1996[Fernandez-Castaño, C. & Foces-Foces, C. (1996). Acta Cryst. C52, 1586-1588.]). For related literature, see: Garegg et al. (1978[Garegg, P. J., Hultberg, C. & Iversen, T. (1978). Carbohydr. Res. 62, 173-174.]).

[Scheme 1]

Experimental

Crystal data
  • C12H15NO7·0.5H2O

  • Mr = 294.26

  • Monoclinic, P 21

  • a = 10.5371 (15) Å

  • b = 6.8681 (8) Å

  • c = 19.135 (3) Å

  • β = 101.543 (7)°

  • V = 1356.8 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 100 (2) K

  • 0.6 × 0.58 × 0.23 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.923, Tmax = 0.972

  • 14281 measured reflections

  • 3340 independent reflections

  • 3147 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.080

  • S = 1.04

  • 3340 reflections

  • 396 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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-{\script{3\over 2}}, -z+1]; (iii) x, y+1, z; (iv) [-x, y+{\script{1\over 2}}, -z+1]; (v) [-x, y-{\script{1\over 2}}, -z+1]; (vi) x, y-1, z.

Data collection: SMART (Bruker, 2006[Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1995[Altomare, A., Burla, M. C., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G. & Polidori, G. (1995). J. Appl. Cryst. 28, 842-846.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

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.

Related literature top

For a related structure, see Fernandez-Castaño & Foces-Foces (1996). For related literature, see: Garegg et al. (1978).

Experimental top

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.

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure and atom-labelling scheme for (I). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of the structure, showing the network of hydrogen bonds (dotted lines).
4-Nitrophenyl α-L-rhamnopyranoside hemihydrate top
Crystal data top
C12H15NO7·0.5H2OF(000) = 620
Mr = 294.26Dx = 1.441 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8274 reflections
a = 10.5371 (15) Åθ = 2.4–27.4°
b = 6.8681 (8) ŵ = 0.12 mm1
c = 19.135 (3) ÅT = 100 K
β = 101.543 (7)°Plate, colourless
V = 1356.8 (3) Å30.6 × 0.58 × 0.23 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
3147 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
CCD rotation images, thin slices scansθmax = 27.4°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1312
Tmin = 0.923, Tmax = 0.972k = 88
14281 measured reflectionsl = 2421
3340 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0398P)2 + 0.2743P]
where P = (Fo2 + 2Fc2)/3
3340 reflections(Δ/σ)max = 0.001
396 parametersΔρmax = 0.38 e Å3
1 restraintΔρmin = 0.24 e Å3
Crystal data top
C12H15NO7·0.5H2OV = 1356.8 (3) Å3
Mr = 294.26Z = 4
Monoclinic, P21Mo Kα radiation
a = 10.5371 (15) ŵ = 0.12 mm1
b = 6.8681 (8) ÅT = 100 K
c = 19.135 (3) Å0.6 × 0.58 × 0.23 mm
β = 101.543 (7)°
Data collection top
Bruker APEXII
diffractometer
3340 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
3147 reflections with I > 2σ(I)
Tmin = 0.923, Tmax = 0.972Rint = 0.051
14281 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0321 restraint
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.38 e Å3
3340 reflectionsΔρmin = 0.24 e Å3
396 parameters
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
xyzUiso*/Ueq
N1130.06897 (18)1.3356 (3)0.12305 (9)0.0208 (4)
O1140.04061 (15)1.3222 (3)0.16072 (8)0.0285 (4)
O1150.16860 (16)1.3419 (3)0.14777 (8)0.0320 (4)
C1100.0816 (2)1.3456 (3)0.04511 (10)0.0169 (4)
C1090.0304 (2)1.3374 (3)0.01675 (11)0.0181 (4)
H1090.11321.3260.04710.022*
C1080.01818 (19)1.3462 (3)0.05646 (11)0.0176 (4)
H1080.09331.34030.07680.021*
C1070.10436 (19)1.3638 (3)0.10079 (10)0.0154 (4)
C1120.21624 (19)1.3726 (3)0.07163 (11)0.0184 (4)
H1120.29921.38490.10180.022*
C1110.20393 (19)1.3632 (3)0.00206 (11)0.0179 (4)
H1110.27861.36880.02280.021*
O1010.10387 (13)1.3698 (2)0.17252 (7)0.0173 (3)
C1010.21582 (18)1.4443 (3)0.22070 (10)0.0150 (4)
H1010.23871.5740.2030.018*
C1020.17225 (19)1.4730 (3)0.29214 (10)0.0143 (4)
H1020.09051.5510.28480.017*
O1020.27280 (15)1.5708 (2)0.34038 (8)0.0188 (3)
H120.259 (3)1.692 (6)0.3366 (17)0.05*
C1030.15121 (19)1.2737 (3)0.32381 (10)0.0136 (4)
H1030.07811.20650.29140.016*
O1030.11609 (15)1.3034 (2)0.39202 (7)0.0180 (3)
H130.115 (3)1.197 (6)0.4126 (18)0.05*
C1040.2735 (2)1.1506 (3)0.32928 (10)0.0136 (4)
H1040.34751.21510.36190.016*
O1040.25457 (15)0.9597 (2)0.35459 (8)0.0173 (3)
H140.246 (3)0.959 (6)0.3956 (19)0.05*
C1050.30432 (19)1.1288 (3)0.25488 (11)0.0151 (4)
H1050.22971.06410.22280.018*
C1060.4262 (2)1.0144 (3)0.25400 (12)0.0232 (5)
H10A0.44251.01120.20540.035*
H10B0.41570.88110.27030.035*
H10C0.49951.07640.28580.035*
O1050.32371 (13)1.3205 (2)0.22692 (7)0.0154 (3)
N2130.39091 (16)0.4276 (3)0.01163 (9)0.0194 (4)
O2150.32520 (14)0.3120 (3)0.01531 (8)0.0235 (3)
O2140.46481 (17)0.5465 (3)0.02365 (8)0.0322 (4)
C2100.38055 (19)0.4233 (3)0.08925 (10)0.0168 (4)
C2090.4304 (2)0.5769 (3)0.12271 (11)0.0190 (4)
H2090.47240.68270.09550.023*
C2080.41803 (19)0.5738 (3)0.19635 (11)0.0180 (4)
H2080.45040.67870.22010.022*
C2070.35783 (18)0.4156 (3)0.23528 (10)0.0146 (4)
C2120.3100 (2)0.2609 (3)0.20071 (11)0.0180 (4)
H2120.26990.15320.22760.022*
C2110.32092 (19)0.2644 (3)0.12718 (11)0.0178 (4)
H2110.28830.16020.10330.021*
O2010.34096 (13)0.3963 (2)0.30809 (7)0.0153 (3)
C2010.37263 (19)0.5583 (3)0.34905 (10)0.0141 (4)
H2010.46770.58470.33530.017*
C2020.34018 (18)0.4911 (3)0.42743 (10)0.0139 (4)
H2020.38270.3630.43230.017*
O2020.38516 (14)0.6325 (2)0.47115 (8)0.0168 (3)
H220.464 (3)0.597 (6)0.4737 (17)0.05*
C2030.19271 (18)0.4703 (3)0.45089 (10)0.0122 (4)
H2030.16360.3550.42630.015*
O2030.16051 (13)0.4396 (2)0.52635 (7)0.0148 (3)
H230.114 (3)0.341 (6)0.5351 (17)0.05*
C2040.12210 (17)0.6509 (3)0.43223 (10)0.0123 (4)
H2040.14530.76230.46090.015*
O2040.01541 (13)0.6233 (2)0.45107 (7)0.0149 (3)
H240.036 (3)0.533 (6)0.4294 (18)0.05*
C2060.1076 (2)0.8921 (3)0.33282 (11)0.0202 (4)
H20A0.13670.91480.28150.03*
H20B0.01280.88430.34430.03*
H20C0.13650.99970.35950.03*
C2050.16438 (18)0.7030 (3)0.35314 (10)0.0131 (4)
H2050.13980.59480.32340.016*
O2050.30423 (13)0.7267 (2)0.33721 (7)0.0142 (3)
O10.62208 (15)0.0270 (2)0.50941 (9)0.0203 (3)
H1A0.628 (3)0.084 (6)0.4891 (18)0.05*
H1B0.664 (3)0.021 (6)0.5520 (19)0.05*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1130.0260 (9)0.0160 (8)0.0201 (9)0.0018 (7)0.0036 (7)0.0005 (7)
O1140.0280 (8)0.0352 (9)0.0194 (7)0.0047 (7)0.0025 (6)0.0013 (7)
O1150.0295 (9)0.0478 (11)0.0201 (8)0.0030 (8)0.0083 (7)0.0006 (8)
C1100.0221 (10)0.0125 (9)0.0154 (9)0.0003 (8)0.0023 (8)0.0008 (7)
C1090.0173 (10)0.0138 (9)0.0216 (10)0.0015 (8)0.0003 (7)0.0003 (8)
C1080.0162 (9)0.0151 (9)0.0222 (10)0.0013 (8)0.0057 (8)0.0005 (8)
C1070.0174 (9)0.0125 (9)0.0163 (9)0.0001 (8)0.0030 (7)0.0007 (7)
C1120.0153 (9)0.0205 (10)0.0185 (10)0.0014 (8)0.0014 (7)0.0014 (8)
C1110.0184 (10)0.0166 (10)0.0195 (10)0.0010 (8)0.0056 (8)0.0022 (8)
O1010.0152 (7)0.0213 (7)0.0151 (7)0.0021 (6)0.0026 (5)0.0011 (6)
C1010.0138 (9)0.0137 (9)0.0169 (9)0.0009 (7)0.0019 (7)0.0010 (7)
C1020.0155 (9)0.0105 (8)0.0160 (9)0.0034 (7)0.0010 (7)0.0014 (7)
O1020.0267 (8)0.0091 (6)0.0192 (7)0.0000 (6)0.0010 (6)0.0003 (5)
C1030.0157 (9)0.0122 (8)0.0135 (9)0.0005 (7)0.0039 (7)0.0007 (7)
O1030.0260 (8)0.0131 (7)0.0170 (7)0.0042 (6)0.0097 (6)0.0012 (6)
C1040.0168 (9)0.0079 (8)0.0166 (9)0.0004 (7)0.0045 (7)0.0003 (7)
O1040.0280 (8)0.0092 (6)0.0171 (7)0.0004 (6)0.0105 (6)0.0006 (5)
C1050.0173 (10)0.0111 (8)0.0183 (10)0.0007 (8)0.0067 (7)0.0004 (7)
C1060.0255 (11)0.0168 (10)0.0317 (12)0.0061 (8)0.0163 (9)0.0045 (9)
O1050.0153 (7)0.0131 (6)0.0189 (7)0.0008 (5)0.0057 (5)0.0033 (5)
N2130.0159 (8)0.0243 (9)0.0178 (8)0.0008 (7)0.0029 (7)0.0022 (7)
O2150.0200 (7)0.0317 (8)0.0196 (7)0.0015 (7)0.0057 (6)0.0045 (7)
O2140.0348 (9)0.0422 (10)0.0171 (8)0.0156 (8)0.0009 (6)0.0026 (7)
C2100.0132 (9)0.0226 (10)0.0139 (9)0.0016 (8)0.0012 (7)0.0024 (8)
C2090.0160 (10)0.0201 (10)0.0190 (10)0.0038 (8)0.0008 (8)0.0002 (8)
C2080.0161 (10)0.0176 (9)0.0194 (10)0.0042 (8)0.0013 (8)0.0018 (8)
C2070.0120 (9)0.0158 (9)0.0150 (9)0.0021 (7)0.0001 (7)0.0034 (7)
C2120.0174 (9)0.0155 (9)0.0199 (10)0.0024 (8)0.0006 (8)0.0006 (8)
C2110.0165 (10)0.0189 (10)0.0179 (10)0.0019 (8)0.0035 (8)0.0046 (8)
O2010.0176 (7)0.0136 (7)0.0136 (7)0.0015 (6)0.0008 (5)0.0013 (5)
C2010.0128 (9)0.0138 (9)0.0152 (9)0.0001 (8)0.0013 (7)0.0033 (7)
C2020.0127 (9)0.0130 (9)0.0162 (9)0.0000 (7)0.0031 (7)0.0021 (7)
O2020.0157 (7)0.0159 (7)0.0197 (7)0.0000 (6)0.0061 (6)0.0038 (6)
C2030.0143 (9)0.0118 (8)0.0102 (8)0.0014 (7)0.0014 (7)0.0001 (7)
O2030.0185 (7)0.0143 (7)0.0114 (6)0.0026 (6)0.0027 (5)0.0018 (5)
C2040.0102 (8)0.0124 (8)0.0141 (9)0.0011 (7)0.0017 (7)0.0005 (7)
O2040.0110 (6)0.0140 (7)0.0185 (7)0.0012 (5)0.0005 (5)0.0024 (6)
C2060.0226 (10)0.0194 (10)0.0169 (10)0.0050 (9)0.0001 (8)0.0052 (8)
C2050.0123 (9)0.0135 (8)0.0130 (9)0.0011 (7)0.0016 (7)0.0003 (7)
O2050.0127 (7)0.0133 (7)0.0155 (7)0.0011 (5)0.0003 (5)0.0011 (5)
O10.0191 (7)0.0178 (8)0.0238 (8)0.0025 (6)0.0032 (6)0.0006 (6)
Geometric parameters (Å, º) top
N113—O1151.236 (2)N213—O2151.232 (2)
N113—O1141.236 (2)N213—C2101.468 (3)
N113—C1101.472 (3)C210—C2111.389 (3)
C110—C1111.389 (3)C210—C2091.390 (3)
C110—C1091.395 (3)C209—C2081.389 (3)
C109—C1081.382 (3)C209—H2090.95
C109—H1090.95C208—C2071.396 (3)
C108—C1071.401 (3)C208—H2080.95
C108—H1080.95C207—O2011.375 (2)
C107—O1011.374 (2)C207—C2121.398 (3)
C107—C1121.403 (3)C212—C2111.389 (3)
C112—C1111.391 (3)C212—H2120.95
C112—H1120.95C211—H2110.95
C111—H1110.95O201—C2011.438 (2)
O101—C1011.438 (2)C201—O2051.405 (2)
C101—O1051.406 (2)C201—C2021.541 (3)
C101—C1021.539 (3)C201—H2011
C101—H1011C202—O2021.424 (2)
C102—O1021.426 (2)C202—C2031.535 (3)
C102—C1031.531 (3)C202—H2021
C102—H1021O202—H220.88 (3)
O102—H120.85 (4)C203—O2031.431 (2)
C103—O1031.440 (2)C203—C2041.525 (3)
C103—C1041.527 (3)C203—H2031
C103—H1031O203—H230.84 (4)
O103—H130.83 (4)C204—O2041.434 (2)
C104—O1041.426 (2)C204—C2051.532 (3)
C104—C1051.530 (3)C204—H2041
C104—H1041O204—H240.80 (4)
O104—H140.81 (4)C206—C2051.513 (3)
C105—O1051.450 (2)C206—H20A0.98
C105—C1061.508 (3)C206—H20B0.98
C105—H1051C206—H20C0.98
C106—H10A0.98C205—O2051.453 (2)
C106—H10B0.98C205—H2051
C106—H10C0.98O1—H1A0.86 (4)
N213—O2141.232 (2)O1—H1B0.85 (4)
O115—N113—O114123.06 (18)O214—N213—C210118.61 (17)
O115—N113—C110118.34 (17)O215—N213—C210118.43 (17)
O114—N113—C110118.61 (17)C211—C210—C209121.90 (18)
C111—C110—C109121.97 (19)C211—C210—N213118.60 (18)
C111—C110—N113119.34 (18)C209—C210—N213119.49 (18)
C109—C110—N113118.69 (17)C208—C209—C210119.23 (19)
C108—C109—C110118.56 (18)C208—C209—H209120.4
C108—C109—H109120.7C210—C209—H209120.4
C110—C109—H109120.7C209—C208—C207119.57 (19)
C109—C108—C107120.32 (18)C209—C208—H208120.2
C109—C108—H108119.8C207—C208—H208120.2
C107—C108—H108119.8O201—C207—C208124.66 (18)
O101—C107—C108114.84 (17)O201—C207—C212114.85 (18)
O101—C107—C112124.57 (17)C208—C207—C212120.49 (18)
C108—C107—C112120.59 (18)C211—C212—C207120.10 (19)
C111—C112—C107119.06 (18)C211—C212—H212119.9
C111—C112—H112120.5C207—C212—H212119.9
C107—C112—H112120.5C210—C211—C212118.68 (18)
C110—C111—C112119.49 (18)C210—C211—H211120.7
C110—C111—H111120.3C212—C211—H211120.7
C112—C111—H111120.3C207—O201—C201118.71 (15)
C107—O101—C101118.97 (15)O205—C201—O201111.51 (15)
O105—C101—O101112.63 (16)O205—C201—C202112.49 (16)
O105—C101—C102112.46 (15)O201—C201—C202105.56 (15)
O101—C101—C102105.23 (15)O205—C201—H201109.1
O105—C101—H101108.8O201—C201—H201109.1
O101—C101—H101108.8C202—C201—H201109.1
C102—C101—H101108.8O202—C202—C203109.15 (15)
O102—C102—C103108.21 (15)O202—C202—C201109.41 (15)
O102—C102—C101108.67 (16)C203—C202—C201109.08 (15)
C103—C102—C101109.26 (15)O202—C202—H202109.7
O102—C102—H102110.2C203—C202—H202109.7
C103—C102—H102110.2C201—C202—H202109.7
C101—C102—H102110.2C202—O202—H22106 (2)
C102—O102—H12108 (2)O203—C203—C204109.13 (14)
O103—C103—C104112.48 (15)O203—C203—C202109.29 (15)
O103—C103—C102108.43 (15)C204—C203—C202111.63 (15)
C104—C103—C102109.58 (16)O203—C203—H203108.9
O103—C103—H103108.8C204—C203—H203108.9
C104—C103—H103108.8C202—C203—H203108.9
C102—C103—H103108.8C203—O203—H23109 (2)
C103—O103—H13110 (2)O204—C204—C203110.44 (15)
O104—C104—C103111.05 (16)O204—C204—C205111.02 (15)
O104—C104—C105107.24 (15)C203—C204—C205111.23 (15)
C103—C104—C105108.90 (16)O204—C204—H204108
O104—C104—H104109.9C203—C204—H204108
C103—C104—H104109.9C205—C204—H204108
C105—C104—H104109.9C204—O204—H24110 (2)
C104—O104—H14113 (3)C205—C206—H20A109.5
O105—C105—C106106.61 (16)C205—C206—H20B109.5
O105—C105—C104109.04 (15)H20A—C206—H20B109.5
C106—C105—C104113.64 (17)C205—C206—H20C109.5
O105—C105—H105109.2H20A—C206—H20C109.5
C106—C105—H105109.2H20B—C206—H20C109.5
C104—C105—H105109.2O205—C205—C206106.63 (15)
C105—C106—H10A109.5O205—C205—C204108.41 (14)
C105—C106—H10B109.5C206—C205—C204113.74 (16)
H10A—C106—H10B109.5O205—C205—H205109.3
C105—C106—H10C109.5C206—C205—H205109.3
H10A—C106—H10C109.5C204—C205—H205109.3
H10B—C106—H10C109.5C201—O205—C205113.88 (14)
C101—O105—C105114.15 (14)H1A—O1—H1B109 (3)
O214—N213—O215122.95 (17)
O115—N113—C110—C1110.4 (3)O214—N213—C210—C211165.9 (2)
O114—N113—C110—C111179.17 (19)O215—N213—C210—C21114.1 (3)
O115—N113—C110—C109179.6 (2)O214—N213—C210—C20914.0 (3)
O114—N113—C110—C1090.8 (3)O215—N213—C210—C209166.02 (19)
C111—C110—C109—C1080.3 (3)C211—C210—C209—C2081.3 (3)
N113—C110—C109—C108179.77 (18)N213—C210—C209—C208178.75 (17)
C110—C109—C108—C1070.3 (3)C210—C209—C208—C2071.0 (3)
C109—C108—C107—O101179.59 (18)C209—C208—C207—O201179.57 (18)
C109—C108—C107—C1120.0 (3)C209—C208—C207—C2120.0 (3)
O101—C107—C112—C111179.37 (18)O201—C207—C212—C211179.71 (17)
C108—C107—C112—C1110.1 (3)C208—C207—C212—C2110.6 (3)
C109—C110—C111—C1120.1 (3)C209—C210—C211—C2120.7 (3)
N113—C110—C111—C112179.95 (18)N213—C210—C211—C212179.43 (17)
C107—C112—C111—C1100.1 (3)C207—C212—C211—C2100.3 (3)
C108—C107—O101—C101161.68 (17)C208—C207—O201—C2017.9 (3)
C112—C107—O101—C10118.8 (3)C212—C207—O201—C201172.50 (17)
C107—O101—C101—O10569.4 (2)C207—O201—C201—O20556.3 (2)
C107—O101—C101—C102167.78 (16)C207—O201—C201—C202178.77 (15)
O105—C101—C102—O10264.6 (2)O205—C201—C202—O20266.1 (2)
O101—C101—C102—O102172.44 (15)O201—C201—C202—O202172.04 (14)
O105—C101—C102—C10353.3 (2)O205—C201—C202—C20353.2 (2)
O101—C101—C102—C10369.69 (19)O201—C201—C202—C20368.62 (19)
O102—C102—C103—O10359.34 (19)O202—C202—C203—O20351.0 (2)
C101—C102—C103—O103177.50 (14)C201—C202—C203—O203170.50 (15)
O102—C102—C103—C10463.78 (19)O202—C202—C203—C20469.81 (19)
C101—C102—C103—C10454.4 (2)C201—C202—C203—C20449.7 (2)
O103—C103—C104—O10462.8 (2)O203—C203—C204—O20462.33 (19)
C102—C103—C104—O104176.49 (15)C202—C203—C204—O204176.76 (14)
O103—C103—C104—C105179.32 (15)O203—C203—C204—C205173.93 (14)
C102—C103—C104—C10558.6 (2)C202—C203—C204—C20553.0 (2)
O104—C104—C105—O105179.73 (15)O204—C204—C205—O205179.33 (14)
C103—C104—C105—O10559.5 (2)C203—C204—C205—O20555.92 (19)
O104—C104—C105—C10661.5 (2)O204—C204—C205—C20662.3 (2)
C103—C104—C105—C106178.25 (17)C203—C204—C205—C206174.33 (16)
O101—C101—O105—C10561.5 (2)O201—C201—O205—C20557.5 (2)
C102—C101—O105—C10557.2 (2)C202—C201—O205—C20560.9 (2)
C106—C105—O105—C101177.03 (16)C206—C205—O205—C201176.29 (15)
C104—C105—O105—C10159.9 (2)C204—C205—O205—C20160.88 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O202i0.86 (3)1.97 (7)2.803 (7)159 (9)
O1—H1B···O102ii0.84 (8)2.06 (1)2.881 (8)162 (7)
O102—H12···O104iii0.84 (5)1.87 (3)2.695 (6)163 (8)
O103—H13···O203iv0.83 (1)2.12 (3)2.934 (2)165 (6)
O104—H14···O203iv0.80 (8)1.89 (5)2.663 (7)158 (5)
O202—H22···O1iv0.88 (1)1.82 (1)2.695 (8)173 (0)
O203—H23···O204v0.83 (7)1.80 (6)2.641 (8)176 (8)
O204—H24···O103vi0.79 (7)1.99 (1)2.776 (5)168 (4)
Symmetry codes: (i) x+1, y1, z; (ii) x+1, y3/2, z+1; (iii) x, y+1, z; (iv) x, y+1/2, z+1; (v) x, y1/2, z+1; (vi) x, y1, z.

Experimental details

Crystal data
Chemical formulaC12H15NO7·0.5H2O
Mr294.26
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)10.5371 (15), 6.8681 (8), 19.135 (3)
β (°) 101.543 (7)
V3)1356.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.6 × 0.58 × 0.23
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.923, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
14281, 3340, 3147
Rint0.051
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.080, 1.04
No. of reflections3340
No. of parameters396
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.38, 0.24

Computer programs: SMART (Bruker, 2006), SAINT (Bruker, 2006), SIR97 (Altomare et al., 1995), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O202i0.86 (3)1.97 (7)2.803 (7)159 (9)
O1—H1B···O102ii0.84 (8)2.06 (1)2.881 (8)162 (7)
O102—H12···O104iii0.84 (5)1.87 (3)2.695 (6)163 (8)
O103—H13···O203iv0.83 (0)2.12 (3)2.934 (2)165 (6)
O104—H14···O203iv0.80 (8)1.89 (5)2.663 (7)158 (5)
O202—H22···O1iv0.88 (0)1.82 (0)2.695 (8)173 (0)
O203—H23···O204v0.83 (7)1.80 (6)2.641 (8)176 (8)
O204—H24···O103vi0.79 (7)1.99 (1)2.776 (5)168 (4)
Symmetry codes: (i) x+1, y1, z; (ii) x+1, y3/2, z+1; (iii) x, y+1, z; (iv) x, y+1/2, z+1; (v) x, y1/2, z+1; (vi) x, y1, z.
 

Acknowledgements

PP is grateful to the Région Bretagne for a grant.

References

First citationAltomare, A., Burla, M. C., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G. & Polidori, G. (1995). J. Appl. Cryst. 28, 842–846.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationFernandez-Castaño, C. & Foces-Foces, C. (1996). Acta Cryst. C52, 1586–1588.  CSD CrossRef Web of Science IUCr Journals Google Scholar
First citationGaregg, P. J., Hultberg, C. & Iversen, T. (1978). Carbohydr. Res. 62, 173–174.  CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar

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