supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsdisplay schemesimilar papers buy article online

tk2163 scheme

Acta Cryst. (2007). E63, m1948    [ doi:10.1107/S1600536807029273 ]

Disodium 2,2'-dithiobis(ethanesulfonate) trihydrate (dimesna trihydrate)

M. Bambagiotti-Alberti, G. Bartolucci, B. Bruni, M. Di Vaira and M. Passaponti

Abstract top

The structure of the title compound, poly[[di-[mu]-aqua-[mu]4-[2,2'-dithiobis(ethanesulfonato)]-disodium(I)] monohydrate], {[Na2(C4H8O6S4)(H2O)2]·H2O}n, otherwise known as dimesna trihydrate, exhibits layers formed by the anions parallel to the ab face, connected by layers formed by the Na+ cations and coordinating water molecules.

Comment top

Dimesna, the disulfide readily formed from mesna (Bambagiotti-Alberti et al., 2007) by oxidation (Li et al., 2003), has been shown to protect against cisplatin-induced nephrotoxicity, due to its conversion in the kidneys into the monomeric mesna which, contrary to dimesna, is effective in inactivating urotoxic metabolites from cisplatin chemotherapy (Verschraagen et al., 2004). On the other hand, direct use of mesna as an aid, instead of dimesna, is discouraged by owing to interference with chemotherapy.

Crystals of dimesna were obtained in the form of the trihydrate (I); the contents of the asymmetric unit are shown in Fig. 1. Corresponding bond distances in the two chemically equivalent parts of the anion are in substantial agreement, as they are with values previously found for mesna. The value of the S—S distance, 2.0338 (10) Å, agrees with values recently reported for this bond in similar environments [2.032 (1) Å (Ren & Zhao, 2006); 2.045 (1) Å (Bolte & Sakhaii, 2004)]. The S3 and S4 atoms are in antiperiplanar positions with respect to the connecting ethyl chain, whereas the S1 and S2 atoms in the other part of the anion are in an a-synclinal arrangement. In the crystal structure, the anionic portions of dimesna are arranged in layers parallel to the ab-face, with interposed layers formed by the cations and two of the water molecules (Fig. 2). The third water molecule (O7) occupies channels parallel to a in the anionic layer, forming chains of hydrogen-bonded water molecules which, in addition, are similarly linked to O atoms of sulfonate residues. The closest approach between S atoms of different anions in a layer is 3.845 (1) Å. Both Na+ cations are six-coordinated by O atoms, four of these, in both coordination spheres, belonging to different anions, whereas two are common and are provided by the O8 and O9 water molecules. The latter water O atoms, as well as the sulfonate O1 and O5 atoms, bridge between symmetry-related cations, forming chains along a, whereas the O2 and O4 (also coordinating) sulfonate O atoms provide bridges between the chains. The sulfonate O3 and O6 sulfonate atoms, are not engaged in coordination to Na, but accept hydrogen bonds from water molecules.

Related literature top

For related literature, see: Bambagiotti-Alberti et al. (2007); Bolte & Sakhaii (2004); Li et al. (2003); Ren & Zhao (2006); Verschraagen et al. (2004).

Experimental top

Samples of dimesna, in microcrystalline form, were kindly provided by SIMS (SIMS srl, Reggello Firenze, Italy). Crystals suitable for X-ray diffraction were obtained by slow evaporation from water-methanol solutions of (I).

Refinement top

The structure is pseudo centrosymmetric, but its intrinsically noncentrosymmetric nature is proved by the absence of symmetry for the symmetry–independent anion in the final model. It was refined as a racemic twin (thanks are expressed to a reviewer for pointing out this possibility), with 0.52 (2) main component. Aliphatic H atoms were in geometrically generated positions, riding. Assigned values of bond distances: secondary CH2 0.99 Å. The positional parameters of water H atoms were refined, with a common soft restraint on O—H distances (0.76 (2) Å final value). The restraints U(H) = 1.2Ueq(C) and U(H) = 1.5Ueq(O) on thermal parameters were applied.

Computing details top

Data collection: CrysAlisPro CCD (Oxford Diffraction, 2006); cell refinement: CrysAlisPro CCD; data reduction: CrysAlisPro RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the contents of the asymmetric unit in (I). Displacement ellipsoids are drawn at the 50% probability level. Cordinative bonds to Na+ ions are denoted by thin lines and a hydrogen bond by a dashed line.
[Figure 2] Fig. 2. A view of the crystal packing in (I), viewed along the a axis. Thin lines denote cordinative bonds to Na+ ions and dashed lines represent hydrogen bonds.
poly[[di-µ-aqua-µ4-[2,2'-dithiobis(ethanesulfonato)]-disodium(I)] monohydrate] top
Crystal data top
[Na2(C4H8O6S4)(H2O)2]·H2OF000 = 392
Mr = 380.37Dx = 1.806 Mg m−3
Monoclinic, PaCu Kα radiation
λ = 1.54180 Å
Hall symbol: P -2yaCell parameters from 2793 reflections
a = 5.7328 (2) Åθ = 11.1–44.5º
b = 10.9152 (4) ŵ = 7.22 mm−1
c = 11.2665 (4) ÅT = 150 (2) K
β = 97.106 (4)ºPrism, colourless
V = 699.58 (4) Å30.15 × 0.10 × 0.05 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur PX Ultra CCD
diffractometer		2346 independent reflections
Radiation source: fine-focus sealed tube2246 reflections with I > 2σ(I)
Monochromator: Oxford Diffraction, Enhance ULTRA assemblyRint = 0.034
T = 150(2) Kθmax = 72.2º
ω scansθmin = 4.0º
Absorption correction: multi-scan
[ABSPACK from CrysAlisPro RED (Oxford Diffraction, 2006)]		h = −7→5
Tmin = 0.498, Tmax = 1.000k = −13→13
8713 measured reflectionsl = −13→13
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.026  w = 1/[σ2(Fo2) + (0.0548P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.33 e Å−3
2346 reflectionsΔρmin = −0.40 e Å−3
192 parametersExtinction correction: none
8 restraintsAbsolute structure: Flack & Bernardinelli (1999); 977 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.0 (4)
Secondary atom site location: difference Fourier map
Crystal data top
[Na2(C4H8O6S4)(H2O)2]·H2OV = 699.58 (4) Å3
Mr = 380.37Z = 2
Monoclinic, PaCu Kα
a = 5.7328 (2) ŵ = 7.22 mm−1
b = 10.9152 (4) ÅT = 150 (2) K
c = 11.2665 (4) Å0.15 × 0.10 × 0.05 mm
β = 97.106 (4)º
Data collection top
Oxford Diffraction Xcalibur PX Ultra CCD
diffractometer		2346 independent reflections
Absorption correction: multi-scan
[ABSPACK from CrysAlisPro RED (Oxford Diffraction, 2006)]		2246 reflections with I > 2σ(I)
Tmin = 0.498, Tmax = 1.000Rint = 0.034
8713 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.069Δρmax = 0.33 e Å−3
S = 1.04Δρmin = −0.40 e Å−3
2346 reflectionsAbsolute structure: Flack & Bernardinelli (1999); 977 Friedel pairs
192 parametersFlack parameter: 0.0 (4)
8 restraints
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 > 2sigma(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
S10.44292 (10)0.31465 (5)0.07585 (5)0.01495 (15)
O10.5960 (4)0.41544 (17)0.12214 (18)0.0202 (4)
O20.2687 (4)0.28386 (18)0.15533 (17)0.0193 (4)
O30.5760 (4)0.20872 (19)0.04342 (18)0.0219 (4)
C10.2838 (5)0.3722 (2)−0.0587 (2)0.0180 (6)
H110.24010.4585−0.04570.022*
H120.38830.3714−0.12240.022*
C20.0601 (6)0.2998 (3)−0.1022 (3)0.0228 (6)
H21−0.02690.3449−0.17000.027*
H22−0.04050.2983−0.03680.027*
S20.10126 (14)0.14314 (6)−0.14969 (7)0.02739 (18)
S30.32883 (13)0.15983 (7)−0.27364 (6)0.02457 (16)
C30.1429 (6)0.2132 (3)−0.4068 (3)0.0211 (6)
H310.07540.2937−0.38940.025*
H320.24140.2250−0.47210.025*
C4−0.0557 (5)0.1259 (2)−0.4490 (2)0.0181 (6)
H41−0.15680.1147−0.38470.022*
H420.01020.0451−0.46680.022*
S4−0.22768 (11)0.18324 (5)−0.57943 (5)0.01576 (15)
O4−0.0636 (4)0.21572 (19)−0.66323 (17)0.0189 (4)
O5−0.3898 (4)0.08517 (19)−0.62452 (17)0.0227 (5)
O6−0.3523 (4)0.2900 (2)−0.53982 (18)0.0240 (5)
Na10.22800 (19)0.09442 (9)0.25452 (9)0.0182 (2)
Na2−0.02409 (19)0.40532 (10)0.23478 (10)0.0192 (2)
O7−0.3003 (5)0.4610 (2)−0.3525 (3)0.0491 (7)
H71−0.423 (5)0.473 (6)−0.335 (5)0.074*
H72−0.325 (11)0.398 (3)−0.381 (5)0.074*
O8−0.0935 (4)0.03360 (18)0.11922 (19)0.0198 (4)
H81−0.184 (6)0.084 (3)0.102 (4)0.030*
H82−0.074 (7)−0.014 (3)0.072 (3)0.030*
O90.3065 (4)0.45846 (17)0.3702 (2)0.0212 (4)
H910.391 (6)0.406 (3)0.388 (4)0.032*
H920.297 (7)0.488 (3)0.431 (2)0.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0134 (3)0.0140 (3)0.0169 (3)0.0005 (2)−0.0004 (2)0.0005 (2)
O10.0185 (11)0.0191 (10)0.0218 (10)−0.0035 (8)−0.0019 (8)−0.0010 (8)
O20.0186 (11)0.0204 (9)0.0192 (10)0.0000 (8)0.0040 (9)0.0006 (8)
O30.0204 (11)0.0197 (9)0.0256 (11)0.0053 (9)0.0032 (9)−0.0008 (8)
C10.0193 (15)0.0162 (13)0.0172 (13)0.0011 (10)−0.0036 (11)0.0001 (10)
C20.0181 (16)0.0301 (15)0.0191 (14)−0.0019 (12)−0.0017 (12)−0.0032 (11)
S20.0381 (5)0.0249 (3)0.0179 (3)−0.0104 (3)−0.0015 (3)−0.0007 (3)
S30.0230 (4)0.0286 (3)0.0202 (3)0.0046 (3)−0.0052 (3)−0.0050 (3)
C30.0220 (15)0.0237 (13)0.0174 (14)−0.0011 (12)0.0011 (11)0.0019 (11)
C40.0198 (15)0.0189 (13)0.0148 (13)−0.0006 (11)−0.0012 (11)0.0028 (10)
S40.0148 (3)0.0180 (3)0.0142 (3)0.0006 (2)0.0007 (2)0.0008 (2)
O40.0191 (11)0.0206 (9)0.0175 (10)0.0018 (8)0.0049 (8)0.0022 (7)
O50.0206 (12)0.0248 (10)0.0208 (11)−0.0052 (8)−0.0045 (9)0.0018 (7)
O60.0243 (12)0.0270 (10)0.0205 (10)0.0105 (9)0.0015 (9)−0.0017 (9)
Na10.0159 (6)0.0188 (5)0.0197 (5)0.0001 (4)0.0012 (5)−0.0005 (4)
Na20.0167 (6)0.0177 (5)0.0221 (6)0.0006 (4)−0.0014 (5)0.0003 (4)
O70.0488 (17)0.0285 (13)0.0649 (19)−0.0014 (12)−0.0139 (15)−0.0125 (12)
O80.0162 (10)0.0190 (10)0.0233 (10)0.0021 (8)−0.0020 (8)0.0002 (7)
O90.0180 (10)0.0216 (10)0.0233 (10)0.0029 (8)0.0000 (8)−0.0028 (8)
Geometric parameters (Å, °) top
S1—O31.457 (2)O4—Na1iii2.406 (2)
S1—O21.461 (2)O5—Na1iv2.435 (2)
S1—O11.4626 (19)O5—Na1v2.527 (2)
S1—C11.784 (3)Na1—O82.338 (2)
O1—Na2i2.384 (2)Na1—O8vi2.389 (2)
O1—Na2ii2.476 (2)Na1—O4vii2.406 (2)
O2—Na12.376 (2)Na1—O5viii2.435 (2)
O2—Na22.397 (2)Na1—O5ix2.527 (2)
C1—C21.534 (4)Na1—Na1x3.5305 (12)
C1—H110.9900Na1—Na1vi3.5305 (12)
C1—H120.9900Na2—O92.354 (2)
C2—S21.816 (3)Na2—O1xi2.384 (2)
C2—H210.9900Na2—O4vii2.392 (2)
C2—H220.9900Na2—O9xii2.419 (2)
S2—S32.0338 (10)Na2—O1xii2.476 (2)
S3—C31.825 (3)Na2—Na2ii3.5339 (12)
C3—C41.515 (4)Na2—Na2xii3.5339 (12)
C3—H310.9900O7—H710.763 (15)
C3—H320.9900O7—H720.764 (15)
C4—S41.779 (3)O8—Na1x2.389 (2)
C4—H410.9900O8—H810.763 (15)
C4—H420.9900O8—H820.764 (15)
S4—O41.456 (2)O9—Na2ii2.419 (2)
S4—O61.465 (2)O9—H910.766 (15)
S4—O51.467 (2)O9—H920.763 (15)
O4—Na2iii2.392 (2)
O3—S1—O2112.97 (12)O8—Na1—O5ix83.66 (7)
O3—S1—O1112.14 (12)O2—Na1—O5ix167.79 (8)
O2—S1—O1112.34 (12)O8vi—Na1—O5ix93.13 (8)
O3—S1—C1107.16 (12)O4vii—Na1—O5ix88.53 (7)
O2—S1—C1106.57 (13)O5viii—Na1—O5ix87.02 (7)
O1—S1—C1105.04 (12)O8—Na1—Na1x42.24 (6)
S1—O1—Na2i128.56 (12)O2—Na1—Na1x129.43 (6)
S1—O1—Na2ii125.78 (12)O8vi—Na1—Na1x94.03 (6)
Na2i—O1—Na2ii93.29 (7)O4vii—Na1—Na1x73.65 (5)
S1—O2—Na1127.08 (12)O5viii—Na1—Na1x130.55 (6)
S1—O2—Na2131.69 (12)O5ix—Na1—Na1x43.60 (5)
Na1—O2—Na2101.06 (8)O8—Na1—Na1vi114.13 (7)
C2—C1—S1114.2 (2)O2—Na1—Na1vi112.41 (6)
C2—C1—H11108.7O8vi—Na1—Na1vi41.13 (6)
S1—C1—H11108.7O4vii—Na1—Na1vi157.52 (5)
C2—C1—H12108.7O5viii—Na1—Na1vi45.69 (5)
S1—C1—H12108.7O5ix—Na1—Na1vi79.53 (6)
H11—C1—H12107.6Na1x—Na1—Na1vi108.56 (5)
C1—C2—S2116.4 (2)O9—Na2—O1xi160.56 (8)
C1—C2—H21108.2O9—Na2—O4vii91.05 (8)
S2—C2—H21108.2O1xi—Na2—O4vii99.28 (8)
C1—C2—H22108.2O9—Na2—O280.42 (8)
S2—C2—H22108.2O1xi—Na2—O2117.56 (8)
H21—C2—H22107.3O4vii—Na2—O279.24 (7)
C2—S2—S3103.64 (11)O9—Na2—O9xii78.08 (7)
C3—S3—S2103.52 (11)O1xi—Na2—O9xii84.01 (8)
C4—C3—S3113.44 (19)O4vii—Na2—O9xii99.18 (8)
C4—C3—H31108.9O2—Na2—O9xii158.42 (9)
S3—C3—H31108.9O9—Na2—O1xii83.39 (8)
C4—C3—H32108.9O1xi—Na2—O1xii89.09 (7)
S3—C3—H32108.9O4vii—Na2—O1xii168.28 (9)
H31—C3—H32107.7O2—Na2—O1xii89.64 (7)
C3—C4—S4110.91 (18)O9xii—Na2—O1xii89.79 (7)
C3—C4—H41109.5O9—Na2—Na2ii42.94 (6)
S4—C4—H41109.5O1xi—Na2—Na2ii131.34 (6)
C3—C4—H42109.5O4vii—Na2—Na2ii129.14 (6)
S4—C4—H42109.5O2—Na2—Na2ii73.63 (5)
H41—C4—H42108.0O9xii—Na2—Na2ii91.69 (6)
O4—S4—O6112.47 (13)O1xii—Na2—Na2ii42.33 (5)
O4—S4—O5112.68 (12)O9—Na2—Na2xii116.35 (6)
O6—S4—O5111.96 (13)O1xi—Na2—Na2xii44.37 (5)
O4—S4—C4106.54 (13)O4vii—Na2—Na2xii112.40 (6)
O6—S4—C4105.63 (13)O2—Na2—Na2xii158.24 (5)
O5—S4—C4106.99 (12)O9xii—Na2—Na2xii41.53 (6)
S4—O4—Na2iii129.00 (12)O1xii—Na2—Na2xii79.32 (6)
S4—O4—Na1iii130.60 (12)Na2ii—Na2—Na2xii108.41 (6)
Na2iii—O4—Na1iii100.33 (8)H71—O7—H7297 (6)
S4—O5—Na1iv130.65 (12)Na1—O8—Na1x96.63 (9)
S4—O5—Na1v123.57 (13)Na1—O8—H81115 (3)
Na1iv—O5—Na1v90.70 (7)Na1x—O8—H81104 (3)
O8—Na1—O293.20 (8)Na1—O8—H82119 (3)
O8—Na1—O8vi77.48 (7)Na1x—O8—H8299 (3)
O2—Na1—O8vi97.72 (8)H81—O8—H82118 (4)
O8—Na1—O4vii82.99 (8)Na2—O9—Na2ii95.53 (9)
O2—Na1—O4vii79.37 (7)Na2—O9—H91115 (3)
O8vi—Na1—O4vii160.09 (8)Na2ii—O9—H91110 (3)
O8—Na1—O5viii159.28 (9)Na2—O9—H92123 (3)
O2—Na1—O5viii99.53 (8)Na2ii—O9—H92113 (3)
O8vi—Na1—O5viii84.62 (8)H91—O9—H92101 (4)
O4vii—Na1—O5viii115.29 (8)
O3—S1—O1—Na2i−32.55 (19)Na2—O2—Na1—O8vi159.45 (8)
O2—S1—O1—Na2i95.97 (16)S1—O2—Na1—O4vii175.00 (14)
C1—S1—O1—Na2i−148.59 (15)Na2—O2—Na1—O4vii−0.59 (9)
O3—S1—O1—Na2ii−164.23 (12)S1—O2—Na1—O5viii60.84 (16)
O2—S1—O1—Na2ii−35.72 (17)Na2—O2—Na1—O5viii−114.75 (8)
C1—S1—O1—Na2ii79.73 (16)S1—O2—Na1—O5ix−177.4 (3)
O3—S1—O2—Na19.99 (19)Na2—O2—Na1—O5ix7.0 (4)
O1—S1—O2—Na1−118.08 (14)S1—O2—Na1—Na1x−126.68 (13)
C1—S1—O2—Na1127.41 (14)Na2—O2—Na1—Na1x57.72 (10)
O3—S1—O2—Na2−175.80 (14)S1—O2—Na1—Na1vi15.03 (16)
O1—S1—O2—Na256.13 (19)Na2—O2—Na1—Na1vi−160.57 (5)
C1—S1—O2—Na2−58.39 (18)S1—O2—Na2—O9−81.77 (16)
O3—S1—C1—C279.0 (2)Na1—O2—Na2—O993.52 (9)
O2—S1—C1—C2−42.2 (2)S1—O2—Na2—O1xi90.38 (17)
O1—S1—C1—C2−161.6 (2)Na1—O2—Na2—O1xi−94.33 (9)
S1—C1—C2—S2−65.8 (3)S1—O2—Na2—O4vii−174.69 (15)
C1—C2—S2—S3−53.8 (2)Na1—O2—Na2—O4vii0.60 (9)
C2—S2—S3—C3−77.94 (14)S1—O2—Na2—O9xii−86.9 (3)
S2—S3—C3—C4−59.4 (2)Na1—O2—Na2—O9xii88.3 (2)
S3—C3—C4—S4−179.55 (16)S1—O2—Na2—O1xii1.59 (17)
C3—C4—S4—O450.4 (2)Na1—O2—Na2—O1xii176.88 (8)
C3—C4—S4—O6−69.4 (2)S1—O2—Na2—Na2ii−38.18 (14)
C3—C4—S4—O5171.12 (19)Na1—O2—Na2—Na2ii137.11 (8)
O6—S4—O4—Na2iii−11.5 (2)S1—O2—Na2—Na2xii60.6 (3)
O5—S4—O4—Na2iii116.17 (15)Na1—O2—Na2—Na2xii−124.15 (16)
C4—S4—O4—Na2iii−126.80 (15)O2—Na1—O8—Na1x−152.21 (8)
O6—S4—O4—Na1iii171.83 (14)O8vi—Na1—O8—Na1x110.59 (12)
O5—S4—O4—Na1iii−60.48 (19)O4vii—Na1—O8—Na1x−73.34 (7)
C4—S4—O4—Na1iii56.55 (18)O5viii—Na1—O8—Na1x79.7 (3)
O4—S4—O5—Na1iv−88.73 (18)O5ix—Na1—O8—Na1x15.95 (8)
O6—S4—O5—Na1iv39.24 (19)Na1vi—Na1—O8—Na1x91.46 (8)
C4—S4—O5—Na1iv154.52 (15)O1xi—Na2—O9—Na2ii−82.5 (3)
O4—S4—O5—Na1v37.37 (16)O4vii—Na2—O9—Na2ii155.11 (8)
O6—S4—O5—Na1v165.33 (12)O2—Na2—O9—Na2ii76.21 (7)
C4—S4—O5—Na1v−79.39 (16)O9xii—Na2—O9—Na2ii−105.73 (11)
S1—O2—Na1—O8−102.75 (15)O1xii—Na2—O9—Na2ii−14.54 (7)
Na2—O2—Na1—O881.66 (9)Na2xii—Na2—O9—Na2ii−89.14 (8)
S1—O2—Na1—O8vi−24.95 (16)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1, z; (iii) x, y, z−1; (iv) x−1, y, z−1; (v) x−1/2, −y, z−1; (vi) x+1/2, −y, z; (vii) x, y, z+1; (viii) x+1, y, z+1; (ix) x+1/2, −y, z+1; (x) x−1/2, −y, z; (xi) x−1, y, z; (xii) x−1/2, −y+1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H72···O60.764 (15)2.14 (3)2.806 (3)147 (6)
O7—H71···O7xii0.763 (15)2.27 (3)2.9901 (15)158 (6)
O8—H81···O3xi0.763 (15)1.990 (15)2.752 (3)175 (4)
O8—H82···O3x0.764 (15)2.33 (3)2.979 (3)144 (4)
O9—H91···O6viii0.766 (15)2.029 (17)2.783 (3)168 (4)
Symmetry codes: (xii) x−1/2, −y+1, z; (xi) x−1, y, z; (x) x−1/2, −y, z; (viii) x+1, y, z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H72···O60.764 (15)2.14 (3)2.806 (3)147 (6)
O7—H71···O7i0.763 (15)2.27 (3)2.9901 (15)158 (6)
O8—H81···O3ii0.763 (15)1.990 (15)2.752 (3)175 (4)
O8—H82···O3iii0.764 (15)2.33 (3)2.979 (3)144 (4)
O9—H91···O6iv0.766 (15)2.029 (17)2.783 (3)168 (4)
Symmetry codes: (i) x−1/2, −y+1, z; (ii) x−1, y, z; (iii) x−1/2, −y, z; (iv) x+1, y, z+1.
Acknowledgements top

The authors acknowledge financial support from the Italian Ministero dell'Istruzione, dell'Universitá e della Ricerca.

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Bambagiotti-Alberti, M., Bruni, B., Di Vaira, M. & Giannellini, V. (2007). Acta Cryst. E63, o1796–?.

Bolte, M. & Sakhaii, P. (2004). Acta Cryst. E60, o1682–o1683.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Flack, H. D. & Bernardinelli, G. (1999). Acta Cryst. A55, 908–915.

Li, Y.-S., Wang, Y., Church, J. S., Garzena, F., Zhang, Z. & An, D. (2003). Spectrochim. Acta Part A59, 1791–1798.

Oxford Diffraction (2006). CrysAlisPro CCD and CrysAlisPro RED. Versions 1.171.29.2. ABSPACK in CrysAlisPro RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.

Ren, B.-D. & Zhao, Y.-J. (2006). Acta Cryst. E62, m170–m171.

Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Verschraagen, M., Boven, E., Torun, E., Erkelens, C. A. M., Hausheer, F. H. & van der Vijgh, initials? (2004). British Journal of Cancer 90 (8), 1654–1659.