4-Nitro­phenyl α-l-rhamnopyran­oside hemihydrate

Pauline Peltier; Richard Daniellou; Thierry Roisnel; Caroline Nugier-Chauvin; Vincent Ferrières

doi:10.1107/S1600536807068195

. 2008 Jan 9;64(Pt 2):o379. doi: 10.1107/S1600536807068195

4-Nitrophenyl α-l-rhamnopyranoside hemihydrate

Pauline Peltier ^a, Richard Daniellou ^a,^*, Thierry Roisnel ^b, Caroline Nugier-Chauvin ^a, Vincent Ferrières ^a

PMCID: PMC2960228 PMID: 21201409

Abstract

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 ¹ C ₄ 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 ▶). For related literature, see: Garegg et al. (1978 ▶).

Experimental

Crystal data

C₁₂H₁₅NO₇·0.5H₂O
M _r = 294.26
Monoclinic,
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 ▶) T _min = 0.923, T _max = 0.972
14281 measured reflections
3340 independent reflections
3147 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.080
S = 1.04
3340 reflections
396 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068195/bv2086sup1.cif

e-64-0o379-sup1.cif^{(27.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068195/bv2086Isup2.hkl

e-64-0o379-Isup2.hkl^{(167KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

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⋯O203^iv	0.83 (0)	2.12 (3)	2.934 (2)	165 (6)
O104—H14⋯O203^iv	0.80 (8)	1.89 (5)	2.663 (7)	158 (5)
O202—H22⋯O1^iv	0.88 (0)	1.82 (0)	2.695 (8)	173 (0)
O203—H23⋯O204^v	0.83 (7)	1.80 (6)	2.641 (8)	176 (8)
O204—H24⋯O103^vi	0.79 (7)	1.99 (1)	2.776 (5)	168 (4)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

PP is grateful to the Région Bretagne for a grant.

supplementary crystallographic information

Comment

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.

Experimental

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.