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(2R)-α-(β-D-Gluco­pyran­osyl­oxy)-4-hydroxy­benzene­aceto­nitrile (taxiphyllin) dihydrate, C14H17NO7·2H2O, is a naturally occurring cyano­genetic glycoside which has been isolated from Henriettella fascicularis (Sw.) C. Wright (Melastomataceae). Its structure is stabilized by a wealth of intermolecular O—H...O and O—H...N hydrogen bonds spun into a three-dimensional network. Further stabilization arises from an intramolecular O—H...O bond and weak intermolecular C—H...O interactions. The very anisotropic growth speeds of the basal pinacoids from methanol mirror a certain structural inhomogeneity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103001355/ln1156sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103001355/ln1156Isup2.hkl
Contains datablock I

CCDC reference: 208036

Comment top

Henriettella fascicularis (Sw.) C. Wright (Melastomataceae) occurs mainly in the provinces of Herrera, Darién and Panama, Republic of Panama (Woodson et al., 1965). The methanol extract of the branches of H. fascicularis yields the cyanogenetic glycoside dhurrin, which has previously been isolated from Cercocarpus ledifolius Nutt. (Rosaceae) (Nahrstedt & Limmer, 1982). The occurrence of dhurrin in H. fascicularis represents the first report of cyanogenetic glycosides in the genus Henriettella. The presence of this compound, toxic for humans and herbivores, in H. fascicularis supports the absence of any ethnomedical claim for this plant in Panamanian traditional medicine. The crystal structure of dhurrin from H. fascicularis as the dihydrate, (I), is presented here. \sch

The average bond lengths in the molecule of (I) (Fig. 1) fall well within the ranges listed in International Tables for Crystallography (1992, Vol. C). Following the example of Desiraju (1996), normalized O—H and C—H distances were used for the preparation of Table 1, rather than those obtained directly from the refined model. These normalized distances were based on neutron work, namely on α-D-glucose (Brown & Levy, 1979; O—D 0.966–0.973 Å, C—O—D 106.70–112.13° and C—D 1.094–1.107 Å), on methanol from a powder study (Torrie et al., 1989; O—D 1.010 Å, C—O—D 110.17° and C—D 1.058–1.089 Å) and on heavy water at 223 K (Peterson & Levy, 1957; O—D 1.011–1.015 Å and D—O—D 109.10–109.87°).

The χ2 value (goodness of fit) of 0.860 is quite remarkable, since it has been achieved with experimental weights. Indeed, a δRexp versus δRstat normal probability plot (NPP; Abrahams & Keve, 1971) displays a slope of 0.731 (1) and a δRexp axis intercept of 0.037 (1). Since the NPP is perfectly straight between ±2 with the expected bent tails, this low χ2 value means that the experimental standard uncertainties have been overestimated by 27% on average (this is contrary to the usual tendency of underestimating s.u.). The very small intercept and the other usual plots confirm the sound nature of this data collection, which is furthermore mirrored in only 12 inconsistent equivalents. Despite the presence of one N and quite a few O atoms and the good quality of the data, the structure does not possess a high enough enantiomorph discriminating capacity (Flack & Bernardinelli, 2000) to furnish the absolute configuration of the six asymmetric C atoms. Since the cyanogenic glycosides belong to the secondary metabolism products of plants, which typically consist of an α-hydroxynitrile type aglycone and a D-glucose moiety (Vetter 2000), we have given preference to the configuration shown in Fig. 1. The relative configurations are therefore R,R,R,S,S,R for atoms C1A, C2, C2A, C3A, C4A and C5A, respectively.

The structure of (I) may be said to be built up of three types of (001) layers (Fig. 2), namely sheets of p-hydroxymandelonitrile, followed by such of β-D-glucopyranoside and finally walls of water molecules. The aromatic moieties are not quite parallel within their layer, with a pair of molecules related by a twofold axis spanning an angle of roughly 30°. These pairs are then piled on top each other, much resembling a stack of shuttlecocks. A similar situation exists in the structure of phenol (Scheringer, 1963; Zavodnik et al. 1987), which consists of layers of phenol rings, and O—H···O chains and such of pure phenol rings. In the structure of phenol, the phenol rings also span an angle of ~40°, but are shifted with respect to each other, much in the way of a zip.

In (I), as well as in phenol, the strong O—H···O hydrogen bonds determine the packing. In phenol (three equally strong H···O bonds of 1.73 Å and O—H···O angles of 159°), this leads to a rather unfavourable packing (k 0.67; Kitaigorodski, 1979). In (I), with somewhat weaker hydrogen bonds (Table 1), the packing, thanks to the presence of sugar and water moieties, is more compact (k 0.73), but is still looser than that of suberin A, a molecule quite similar to (I) (Olafsdottir et al., 1991), for which k 0.75. The absence of phenol rings in suberin A allows for stronger hydrogen bonds (H···O 1.80–2.02 Å and O—H···O 153–162°) and quite a few respectable C—H···O and C—H···N hydrogen interactions; the hydrogen-bond network is three-dimensional and very strong. This explains the much higher melting point of suberin A (471.5 K) compared with that of (I) (406.5 K). Please clarify − 409 K given in CIF data tables.

The van der Waals shape of (I) is much more unwieldy than that of suberin A and it is probably only because of the water molecules that its k value is even this high. It is noteworthy that benzene and its derivatives do not seem to lend themselves to compact packing, since even pure benzene (k 0.659; Bacon et al., 1964) and benzoic acid (k 0.693; Feld et al., 1981) display rather low k values.

The shortest C—C distance between two phenol rings in (I) is 3.396 (5) Å; this distance is 3.09 Å in benzene at 138 K (Bacon et al., 1964). This, together with their non-parallelism, indicates the absence of any ππ stacking interaction (Magistrato et al., 2001).

The ten atoms H7O, O7, C3—C8, C2 and H2 lie in a plane with a mean deviation of 0.042 Å. The sugar moieties and the water molecules are connected via a quite complex three-dimensional network of strong hydrogen bonds (Table 1). All but two of these are two-centre bonds, but atoms H6O and H22W are involved in three-centre bonds. Neither of these satisfies the 0.2 Å criterion (Taylor et al., 1984). This failure might be linked to the fact that the difference maps indicate some degree of disorder that needs to be clarified using a low-temperature or neutron study. Five of the bonds lie within the range expected for ice (Jeffrey & Sänger, 1991).

Besides the one listed in Table 1, there are also other weak C—H···O interactions which are not included, since, in view of the low acidity of the participating H atoms, their contribution to the cohesive energy would have to be checked by non-trivial experimental (IR or NMR spectrosocopies) or theoretical (SCF-MO or MP2 ab initio computations) means. The same assessment would also have to be applied to the intramolecular O6—H6O···O5 bond.

The growth speeds of the basal pinacoids in methanol are very anisotropic indeed, with vc < va << vb. It might be conjectured that the small vc and va speeds are related to a certain incompatibility of the packing of the aromatic and sugar moieties. The sugar and water moieties, on the other hand, are easily fixed with respect to each other by a wealth of rather strong hydrogen bonds (Table 1), and thus growth can proceed quickly along [010].

Table 1. Normalized inter- and intramolecular hydrogen-bond geometry in (I)

Experimental top

Branches of Henriettella fascicularis (660 g) were extracted with dichloromethane and the ensuing residue three times with MeOH at room temperature. The solvent was removed by evaporation at reduced pressure, and the residue was successfully fractionated with EtOAc and water. The EtOAc fraction was separated by medium-pressure liquid chromatography (MPLC) on a LiChroprep RP-18 column (450 × 20 mm) using MeOH-H2O (25:75), to yield a fraction containing the title compound, and then using MeOH-H2O (35:65) to obtain a fraction containing ellagic acid (3,3'-dimethyl ether-O-β-D-glucopyranoside; 16 mg, 0.002% w/w). The title compound was further purified through gel filtration on Sephadex LH-20 (45 × 3 cm), using MeOH 100% (3.7 mg, 0.006% w/w); m.p. 405–408 K. Please clarify − 409 K given in CIF data tables. Spectroscopic analysis: [α]25D −32.0° (c 0.0029, MeOH); 1H NMR (500 MHz, CD3OD, δ, p.p.m.): 7.39 (2H, d, J = 8.3 Hz, H4, H8), 6.84 (2H,d, J = 8.3 Hz, H5, H7), 5.80 (1H, s, H2), 4.17 (1H, d, J = 6.3 Hz, H1A), 3.90 (1H, d, J = 10.7 Hz, H6A1), 3.68 (1H, dd, J = 5.8, 6.4 Hz, H6A2), 3.28 (3H, m, H2A, H4A, H5A; signal pattern unclear due to overlapping), 3.18 (1H, t, J = 6.3, 8.3 Hz, H3A); 13C NMR (125 MHz, CD3OD, δ, p.p.m.): 160.3 (C6), 130.9 (C4, C8), 125.1 (C3), 119.7 (C1), 116.8 (C5, C7), 101.0 (C1A), 78.3 (C3A), 77.9 (C5A), 74.7 (C2A), 71.5 (C4A), 67.9 (C2), 62.8 (C6A). Crystals of (I) grew as [010] laths from evaporating methanol; the measured specimen was bounded by {100}, {010} and {001} pinacoids.

Refinement top

364 Friedel pairs were averaged. H atoms bonded to C were placed in calculated positions (C—H = 0.93–0.98 Å) and then refined using a riding model with Uiso(H) = 1.2Ueq(C). The hydroxy and water H atoms were located in difference Fourier maps, but refined under restraints (O—H = 0.82 Å) with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2001).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. Intramolecular hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. The hydrogen bonds (dashed lines) in the ac plane of (I).
(2R)-α-(β-D-Glucopyranosyloxy)-4-hydroxybenzeneacetonitrile dihydrate top
Crystal data top
C14H17NO7·2H2OF(000) = 736
Mr = 347.32Dx = 1.434 Mg m3
Monoclinic, C2Melting point: 409 K
Hall symbol: C 2yMo Kα radiation, λ = 0.71073 Å
a = 16.055 (4) ÅCell parameters from 754 reflections
b = 6.2858 (17) Åθ = 2.6–25.9°
c = 16.895 (5) ŵ = 0.12 mm1
β = 109.299 (5)°T = 293 K
V = 1609.2 (8) Å3Lath, colourless
Z = 40.35 × 0.03 × 0.01 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1049 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω scansh = 1818
3421 measured reflectionsk = 77
1551 independent reflectionsl = 1820
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H atoms treated by a mixture of independent and constrained refinement
S = 0.84Weighting scheme based on measured s.u.'s
1551 reflections(Δ/σ)max < 0.001
234 parametersΔρmax = 0.17 e Å3
7 restraintsΔρmin = 0.15 e Å3
Crystal data top
C14H17NO7·2H2OV = 1609.2 (8) Å3
Mr = 347.32Z = 4
Monoclinic, C2Mo Kα radiation
a = 16.055 (4) ŵ = 0.12 mm1
b = 6.2858 (17) ÅT = 293 K
c = 16.895 (5) Å0.35 × 0.03 × 0.01 mm
β = 109.299 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1049 reflections with I > 2σ(I)
3421 measured reflectionsRint = 0.058
1551 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0337 restraints
wR(F2) = 0.047H atoms treated by a mixture of independent and constrained refinement
S = 0.84Δρmax = 0.17 e Å3
1551 reflectionsΔρmin = 0.15 e Å3
234 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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O10.21942 (14)1.0239 (4)0.23026 (12)0.0326 (6)
O20.24078 (14)0.7259 (4)0.31082 (12)0.0314 (6)
O30.24867 (16)0.5232 (4)0.46412 (13)0.0485 (7)
H3O0.29370.48640.50140.073*
O40.43406 (15)0.3770 (4)0.39617 (14)0.0418 (6)
H4O0.42250.30950.43280.063*
O50.50862 (14)0.7739 (4)0.36573 (14)0.0373 (6)
H5O0.54400.67830.36760.056*
O60.39185 (16)0.9918 (4)0.22364 (14)0.0443 (7)
H6O0.44330.96030.23040.066*
O70.1490 (2)0.8818 (4)0.15585 (13)0.0543 (8)
H7O0.14330.75640.17000.081*
O1W0.09012 (18)0.5805 (5)0.48741 (17)0.0553 (8)
H11W0.1353 (11)0.531 (6)0.482 (2)0.083*
H12W0.0472 (13)0.522 (6)0.4539 (19)0.083*
O2W0.6178 (2)0.4254 (4)0.3809 (2)0.0627 (9)
H22W0.581 (2)0.342 (5)0.386 (3)0.094*
H21W0.651 (2)0.362 (5)0.361 (2)0.094*
N0.0492 (2)1.3428 (7)0.18401 (18)0.0650 (12)
C10.0847 (3)1.1895 (7)0.1784 (2)0.0419 (11)
C20.1313 (2)0.9954 (6)0.17032 (18)0.0349 (9)
H20.10330.87270.18700.042*
C30.1324 (2)0.9623 (6)0.08199 (19)0.0322 (9)
C40.1117 (2)0.7675 (6)0.04304 (19)0.0390 (10)
H40.09470.65610.07060.047*
C50.1158 (2)0.7355 (6)0.0371 (2)0.0433 (10)
H50.10190.60360.06310.052*
C60.1408 (2)0.9025 (6)0.0775 (2)0.0373 (9)
C70.1607 (2)1.0987 (6)0.0396 (2)0.0409 (10)
H70.17701.21070.06730.049*
C80.1562 (2)1.1279 (6)0.0397 (2)0.0406 (10)
H80.16931.26050.06520.049*
C1A0.2688 (2)0.8345 (6)0.25021 (18)0.0293 (9)
H1A0.25920.74660.20010.035*
C2A0.3651 (2)0.8951 (6)0.28808 (18)0.0279 (8)
H2A0.37180.99820.33330.034*
C3A0.4209 (2)0.6991 (5)0.3236 (2)0.0283 (9)
H3A0.42200.60870.27670.034*
C4A0.3843 (2)0.5705 (5)0.37996 (19)0.0280 (8)
H4A0.39240.64710.43250.034*
C5A0.2868 (2)0.5256 (5)0.33529 (18)0.0289 (8)
H5A0.28050.44140.28480.035*
C6A0.2417 (2)0.4098 (6)0.38847 (19)0.0383 (9)
H6AB0.17980.39030.35620.046*
H6AA0.26800.27010.40280.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0307 (13)0.0321 (16)0.0303 (12)0.0082 (13)0.0037 (11)0.0005 (12)
O20.0292 (14)0.0326 (15)0.0341 (13)0.0062 (12)0.0126 (11)0.0092 (12)
O30.0436 (17)0.071 (2)0.0347 (14)0.0104 (16)0.0177 (12)0.0063 (15)
O40.0417 (16)0.0355 (16)0.0517 (16)0.0114 (14)0.0201 (13)0.0152 (13)
O50.0239 (14)0.0395 (17)0.0435 (14)0.0010 (12)0.0043 (12)0.0033 (13)
O60.0397 (16)0.0499 (18)0.0506 (15)0.0076 (15)0.0246 (13)0.0198 (13)
O70.092 (2)0.0439 (17)0.0315 (14)0.0010 (18)0.0262 (14)0.0029 (13)
O1W0.0359 (16)0.062 (2)0.067 (2)0.0001 (16)0.0158 (15)0.0186 (16)
O2W0.058 (2)0.057 (2)0.087 (2)0.0142 (16)0.0419 (18)0.0159 (18)
N0.063 (3)0.086 (3)0.049 (2)0.041 (2)0.0228 (18)0.010 (2)
C10.034 (2)0.063 (3)0.028 (2)0.017 (2)0.0102 (17)0.005 (2)
C20.028 (2)0.048 (3)0.0304 (19)0.002 (2)0.0118 (16)0.0065 (17)
C30.029 (2)0.038 (2)0.0264 (19)0.0020 (17)0.0051 (16)0.0005 (17)
C40.042 (2)0.038 (3)0.037 (2)0.003 (2)0.0133 (18)0.006 (2)
C50.058 (3)0.030 (2)0.040 (2)0.005 (2)0.0136 (19)0.0043 (19)
C60.041 (2)0.036 (3)0.032 (2)0.003 (2)0.0086 (18)0.002 (2)
C70.058 (3)0.036 (3)0.032 (2)0.005 (2)0.019 (2)0.0012 (18)
C80.051 (3)0.036 (2)0.034 (2)0.007 (2)0.0129 (19)0.0036 (18)
C1A0.032 (2)0.036 (3)0.0206 (18)0.0034 (18)0.0101 (16)0.0005 (16)
C2A0.029 (2)0.031 (2)0.0245 (18)0.0018 (18)0.0096 (16)0.0013 (16)
C3A0.025 (2)0.030 (2)0.0289 (18)0.0005 (17)0.0085 (15)0.0053 (17)
C4A0.031 (2)0.025 (2)0.0260 (18)0.0050 (17)0.0071 (16)0.0000 (17)
C5A0.028 (2)0.031 (2)0.0270 (18)0.0036 (19)0.0081 (15)0.0027 (17)
C6A0.028 (2)0.042 (2)0.041 (2)0.0004 (19)0.0062 (18)0.008 (2)
Geometric parameters (Å, º) top
O1—C1A1.409 (4)C3—C41.378 (5)
O1—C21.453 (4)C3—C81.386 (5)
O2—C1A1.422 (3)C4—C51.392 (4)
O2—C5A1.449 (4)C4—H40.9300
O3—C6A1.435 (4)C5—C61.382 (5)
O3—H3O0.8200C5—H50.9300
O4—C4A1.431 (4)C6—C71.378 (5)
O4—H4O0.8200C7—C81.377 (4)
O5—C3A1.431 (4)C7—H70.9300
O5—H5O0.8200C8—H80.9300
O6—C2A1.431 (3)C1A—C2A1.513 (4)
O6—H6O0.8200C1A—H1A0.9800
O7—C61.379 (4)C2A—C3A1.525 (5)
O7—H7O0.8200C2A—H2A0.9800
O1W—H11W0.822 (5)C3A—C4A1.508 (4)
O1W—H12W0.820 (5)C3A—H3A0.9800
O2W—H22W0.821 (5)C4A—C5A1.523 (4)
O2W—H21W0.823 (5)C4A—H4A0.9800
N—C11.139 (5)C5A—C6A1.514 (4)
C1—C21.462 (5)C5A—H5A0.9800
C2—C31.512 (4)C6A—H6AB0.9700
C2—H20.9800C6A—H6AA0.9700
C1A—O1—C2113.8 (3)O1—C1A—C2A107.7 (3)
C1A—O2—C5A111.7 (2)O2—C1A—C2A109.8 (2)
C6A—O3—H3O109.5O1—C1A—H1A110.8
C4A—O4—H4O109.5O2—C1A—H1A110.8
C3A—O5—H5O109.5C2A—C1A—H1A110.8
C2A—O6—H6O109.5O6—C2A—C1A107.8 (2)
C6—O7—H7O109.5O6—C2A—C3A111.0 (3)
H11W—O1W—H12W108.9 (12)C1A—C2A—C3A110.4 (3)
H22W—O2W—H21W109.3 (13)O6—C2A—H2A109.2
N—C1—C2178.8 (4)C1A—C2A—H2A109.2
O1—C2—C1104.0 (3)C3A—C2A—H2A109.2
O1—C2—C3112.3 (3)O5—C3A—C4A112.8 (3)
C1—C2—C3112.4 (3)O5—C3A—C2A106.5 (3)
O1—C2—H2109.3C4A—C3A—C2A112.4 (3)
C1—C2—H2109.3O5—C3A—H3A108.4
C3—C2—H2109.3C4A—C3A—H3A108.4
C4—C3—C8119.1 (3)C2A—C3A—H3A108.4
C4—C3—C2120.9 (3)O4—C4A—C3A105.5 (3)
C8—C3—C2120.0 (3)O4—C4A—C5A110.8 (3)
C3—C4—C5120.8 (4)C3A—C4A—C5A109.7 (2)
C3—C4—H4119.6O4—C4A—H4A110.2
C5—C4—H4119.6C3A—C4A—H4A110.2
C6—C5—C4119.0 (4)C5A—C4A—H4A110.2
C6—C5—H5120.5O2—C5A—C6A106.8 (2)
C4—C5—H5120.5O2—C5A—C4A108.9 (3)
C7—C6—O7116.7 (3)C6A—C5A—C4A114.2 (2)
C7—C6—C5120.7 (3)O2—C5A—H5A109.0
O7—C6—C5122.5 (3)C6A—C5A—H5A109.0
C8—C7—C6119.5 (4)C4A—C5A—H5A109.0
C8—C7—H7120.2O3—C6A—C5A112.2 (3)
C6—C7—H7120.2O3—C6A—H6AB109.2
C7—C8—C3120.9 (3)C5A—C6A—H6AB109.2
C7—C8—H8119.6O3—C6A—H6AA109.2
C3—C8—H8119.6C5A—C6A—H6AA109.2
O1—C1A—O2106.9 (2)H6AB—C6A—H6AA107.9
C1A—O1—C2—C1163.5 (3)O1—C1A—C2A—O667.5 (3)
C1A—O1—C2—C374.8 (3)O2—C1A—C2A—O6176.5 (3)
O1—C2—C3—C4110.2 (4)O1—C1A—C2A—C3A171.2 (2)
C1—C2—C3—C4132.9 (4)O2—C1A—C2A—C3A55.1 (3)
O1—C2—C3—C868.5 (4)O6—C2A—C3A—O566.6 (3)
C1—C2—C3—C848.4 (4)C1A—C2A—C3A—O5173.9 (2)
C8—C3—C4—C51.0 (5)O6—C2A—C3A—C4A169.5 (3)
C2—C3—C4—C5177.7 (3)C1A—C2A—C3A—C4A50.0 (3)
C3—C4—C5—C60.2 (5)O5—C3A—C4A—O469.3 (3)
C4—C5—C6—C70.6 (6)C2A—C3A—C4A—O4170.4 (3)
C4—C5—C6—O7178.0 (3)O5—C3A—C4A—C5A171.4 (3)
O7—C6—C7—C8178.2 (3)C2A—C3A—C4A—C5A51.0 (3)
C5—C6—C7—C80.5 (6)C1A—O2—C5A—C6A171.2 (2)
C6—C7—C8—C30.4 (6)C1A—O2—C5A—C4A65.1 (3)
C4—C3—C8—C71.1 (5)O4—C4A—C5A—O2172.9 (2)
C2—C3—C8—C7177.6 (3)C3A—C4A—C5A—O256.8 (3)
C2—O1—C1A—O280.7 (3)O4—C4A—C5A—C6A67.9 (4)
C2—O1—C1A—C2A161.4 (2)C3A—C4A—C5A—C6A176.1 (3)
C5A—O2—C1A—O1179.2 (2)O2—C5A—C6A—O362.9 (3)
C5A—O2—C1A—C2A64.2 (3)C4A—C5A—C6A—O357.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O2Wi0.971.922.849 (4)159
O4—H4O···O1Wii0.971.892.828 (3)164
O5—H5O···O2W0.971.812.764 (4)170
O6—H6O···Niii0.972.092.970 (4)150
O7—H7O···O6iv0.971.752.694 (4)166
O1W—H11W···O31.011.782.725 (4)157
O1W—H12W···O5v1.011.952.807 (3)140
O2W—H21W···O2iii1.011.892.901 (3)175
O2W—H22W···O41.012.293.060 (4)132
O2W—H22W···O1Wiii1.012.222.943 (4)127
C3A—H3A···O7iv1.102.343.342 (4)151
O6—H6O···O50.972.432.860 (3)107
Symmetry codes: (i) x1, y, z1; (ii) x3/2, y1/2, z1; (iii) x+1/2, y1/2, z; (iv) x3/2, y1/2, z2; (v) x1/2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC14H17NO7·2H2O
Mr347.32
Crystal system, space groupMonoclinic, C2
Temperature (K)293
a, b, c (Å)16.055 (4), 6.2858 (17), 16.895 (5)
β (°) 109.299 (5)
V3)1609.2 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.35 × 0.03 × 0.01
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3421, 1551, 1049
Rint0.058
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.047, 0.84
No. of reflections1551
No. of parameters234
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.15

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SIR97 (Altomare et al., 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL and PLATON (Spek, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O2Wi0.971.922.849 (4)159
O4—H4O···O1Wii0.971.892.828 (3)164
O5—H5O···O2W0.971.812.764 (4)170
O6—H6O···Niii0.972.092.970 (4)150
O7—H7O···O6iv0.971.752.694 (4)166
O1W—H11W···O31.011.782.725 (4)157
O1W—H12W···O5v1.011.952.807 (3)140
O2W—H21W···O2iii1.011.892.901 (3)175
O2W—H22W···O41.012.293.060 (4)132
O2W—H22W···O1Wiii1.012.222.943 (4)127
C3A—H3A···O7iv1.102.343.342 (4)151
O6—H6O···O50.972.432.860 (3)107
Symmetry codes: (i) x1, y, z1; (ii) x3/2, y1/2, z1; (iii) x+1/2, y1/2, z; (iv) x3/2, y1/2, z2; (v) x1/2, y1/2, z.
 

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