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The organic components of 2-meth­oxy-3-methyl-6-oxo-4-(2,3,4-tri-O-acetyl-β-D-xylopyran­osylamino)-1,6-dihydro­pyri­midine-5-carbaldehyde 0.065-hydrate, C18H23N3O10·0.065H2O, (I), which crystallizes with Z′ = 2 in the space group P212121, are linked into a three-dimensional framework structure by a combination of four C—H...O hydrogen bonds. In 2-methyl­sulfanyl-6-oxo-4-(2,3,4-tri-O-acetyl-β-D-xylopyran­osyl­amino)-1,6-dihydro­pyrimidine-5-car­baldehyde, C17H21N3O9S, (II), where the pyrimidine fragment is disordered with two different conformations for the methyl­sulfanyl substituent, mol­ecules are linked into chains of rings by a combination of N—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109019374/gg3202sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109019374/gg3202Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109019374/gg3202IIsup3.hkl
Contains datablock II

CCDC references: 742242; 742243

Comment top

5-Substituted aminopyrimidine derivatives are useful intermediates for the preparation of fused pyrimidine systems, and we have previously reported the preparation of 5-formyl-6-glycosylaminopyrimidines under Vilsmeier–Haack conditions (Negrillo et al., 1988). We report here the structures of two representative examples of 6-oxo-4-(2,3,4-tri-O-acetyl-β-D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehydes, viz. (I) and (II) (Figs. 1 and 2), of which (I) is a partial hydrate containing 0.065 (3) molecules of water per molecule of the organic component. Compounds (I) and (II) both crystallize in the space group P212121, but with Z' values of 2 and 1, respectively, and so that their unit-cell dimensions show no obvious simple relationship to one another. In compound (II), the pyrimidine component is disordered, and this disorder was modelled using two sets of sites with refined occupancies 0.899 (2) and 0.101 (2); an unexpected feature of the disorder is that the methylsulfanyl substituent adopts different conformations in the two disorder components.

The xylopyranose rings in both compounds adopt almost perfect chair conformations, with all of the non-H substituents occupying equatorial sites, giving the absolute configuration in (II) as (x1R,x2R,x3S,x4R), where x = 2 or 4, with the absolute configuration in (I) set to be identical. The pyrimidine rings are all planar despite the heavy degree of substitution. The formyl groups are all oriented so that intramolecular N—H···O hydrogen bonds (Tables 2 and 4) can form; these interactions may play a role in controlling the orientation of the formyl group (Cobo et al., 2008). The methoxy C atoms in (I) are oriented on the same side of the pyrimidine ring as the formyl O atom, whereas in (II) the methylsulfanyl C atoms is oriented to the opposite side in the major component and to the same side in the minor component (Tables 1 and 3, and Figs. 1 and 2); no obvious simple explanation for these differences presents itself. The bond lengths within the pyrimidine systems (Tables 1 and 3) provide some evidence for the polarization of the electronic structures. In particular, the formyl C—O distances are all long for their type (Allen et al., 1987), as are the exocyclic C—N bonds, while the C—C bonds linking the formyl unit to the ring are all long, suggesting the importance of the polarized forms (Ia) and (IIa) (see scheme). The intramolecular N—H···O hydrogen bonds can thus be regarded as charge-assisted hydrogen bonds (Gilli et al., 1994).

In compound (I), the organic components are linked by four C—H···O hydrogen bonds (Table 2) to form a three-dimensional framework structure of some complexity; however, the formation of this framework can readily be analysed in terms of three distinct one-dimensional substructures. One of the hydrogen bonds links the two molecules within the selected asymmetric unit, while the other three give rise, in various combinations, to the three substructures, The simplest of the substructures, along [100], depends on just one hydrogen bond and involves only the type 2 molecules, containing atom N31 (Fig. 1). Atom C45 at (x, y, z) acts as hydrogen-bond donor to atom O34 at (1/2+x, 1/2-y, 1-z), so linking type 2 molecules related by the 21 screw axis along (x, 1/4, 1/2) into a C(9) (Bernstein et al., 1995) chain running parallel to the [100] direction (Fig. 3).

In a somewhat similar manner, the substructure along [010] involves only the type 1 molecules, containing atom N11 (Fig. 1), but now two hydrogen bonds are involved. Atoms C24 and C51 at (x, y, z) act as hydrogen-bond donors, respectively, to atom O14 at (1-x, 1/2+y, 1.5-z) and O241 at (1-x, -1/2+y, 1.5-z), so linking type 1 molecules related by the 21 screw axis along (1/2, y, 3/4) into a C(10)C(12)[R22(10)] chain of rings running parallel to the [010] direction (Fig. 4). The final substructure, along [001], involves both types of molecule and all four of the C—H···O hydrogen bonds (Fig. 5). The combination of the chains parallel to [100], [010] and [001] suffices to link all of the molecules of (I) into a continuous framework structure.

The hydrogen-bonded structure of compound (II), is much simpler than that of (I) and involves only two hydrogen bonds, one each of the N—H···O and C—H···O types (Table 4). The same pattern of hydrogen bonds is evident for both components of the disordered pyrimidine unit, so that the disorder has no effect on the supramolecular aggregation. Atoms N13n and C22n (n = A or B) at (x, y, z) act as hydrogen-bond donors, respectively, to atom O221 at (1-x, 1/2+y, 1.5-z) and O14n at (1-x, 1/2+y, 1.5-z), thereby linking molecules related by the 21 screw axis along (1/2, y, 3/4) into a C(8)C(11)[R22(9)] chain of rings running parallel to the [010] direction (Fig. 6).

There are thus both similarities and differences between the chains of rings along [010] formed in compound (II) and by the type 1 molecules in compound (I). Each chain is formed from molecules related by the 21 screw axis along (1/2, y, 3/4) and each is built from two hydrogen bonds acting in the two opposite directions along [010]. However, in (I), these hydrogen bonds are both of the C—H···O type, while in (II) there is one each of the N—H···O and C—H···O types, although the same two acceptor O atoms are involved in both structures. The use of different donor atoms in the two structures necessarily leads to different hydrogen-bond motifs and to different graph-set descriptors, C(10)C(12)[R22(10)] in (I) and C(8)C(11)[R22(9)] in (II).

Related literature top

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Cobo et al. (2008); Flack (1983); Gilli et al. (1994); Hooft et al. (2008); Negrillo et al. (1988).

Experimental top

Samples of (I) and (II) were prepared according to the published procedure of Negrillo et al. (1988) and were recrystallized from ethanol.

Refinement top

With the exception of the H atoms of the water component in (I) and the H atoms in the minor component of the pyrimidine unit in (II), all H atoms were located in difference maps. Those which could not be located directly were included in calculated positions, and then all H atoms bonded to C or N atoms were treated as riding atoms in geometrically idealized positions, with C—H = 0.95 (formyl), 0.98 (CH3), 0.99 (CH2) or 1.00Å (aliphatic C—H) and N—H = 0.88Å, and with Uiso(H) = kUeq(carrier), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and k = 1.2 for all other H atoms. For the partial water component of (I), the O—H and H···H distances were subject to the restraints 0.84 (1) and 1.34 (1)Å, respectively, and the refined occupancy was 0.065 (3) molecules of water per molecule of the organic component. For (II), all atoms apart from those of the sugar moiety were included in the disorder model, with the bond distances and one-angle nonbonded distances in the minor B component constrained to have the same values as the corresponding distances in the major A component, subject to an s.u. of 0.005Å, while the distances N16n—C16n (n = A or B) were both subject to the distance constraint 1.40 (2)Å. In addition, it was necessary to constrain corresponding atoms in the two components to have the same anisotropic displacement parameter components, apart from atoms S1n and C17n, which were subject to rigid-bond restraints, via DELU and ISOR, with s.u. values 0.015 and 0.010Å2, respectively. Subject to these conditions, the refined occupancies for the two disorder components were 0.899 (2) and 0.101 (2), respectively. For (II), the correct absolute configuration was established by means of the Flack x parameter (Flack, 1983) of -0.02 (7) and the Hooft y parameter (Hooft et al., 2008) of -0.003 (31), calculated in each case for 1900 Bijvoet pairs from a possible maximum of 1911, i.e. 99.4% coverage. In the absence of significant resonant scattering in (I), it was not possible to determine the absolute configuration directly; accordingly, the Friedel-equivalent reflections were merged prior to the final refinements, and the absolute configuration was set by reference to that in (II).

Computing details top

For both compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The independent components of compound (I), showing the atom-labelling scheme for (a) a type 1 molecule together with the partially occupied water site, and (b) a type 2 molecule. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular structure of compound (II), showing the major and minor orientations of the pyrimidine unit, together with atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded chain of type 2 molecules running parallel to [100]. For the sake of clarity, the partial water molecule and H atoms not involved in the motif shown have been omitted.
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded chain of rings, built from type 1 molecules and running parallel to [010]. For the sake of clarity, the partial water molecule and H atoms not involved in the motif shown have been omitted.
[Figure 5] Fig. 5. A stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded chain, including both of types of molecule and running parallel to [001]. For the sake of clarity, the partial water molecule and H atoms not involved in the motif shown have been omitted.
[Figure 6] Fig. 6. A stereoview of part of the crystal structure of compound (II), showing the formation of a hydrogen-bonded chain of rings running parallel to [010]. For the sake of clarity, the minor orientation of the disordered pyrimidine unit and H atoms not involved in the motifs shown have been omitted.
(I) 2-Methoxy-3-methyl-6-oxo-4-(2,3,4-tri-O-acetyl-β-D-xylopyranosylamino)- 1,6-dihydropyrimidine-5-carbaldehyde 0.065-hydrate top
Crystal data top
C18H23N3O10·0.065H2OF(000) = 1861
Mr = 442.57Dx = 1.378 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5407 reflections
a = 14.3816 (2) Åθ = 3.2–27.5°
b = 14.7626 (2) ŵ = 0.11 mm1
c = 20.1025 (3) ÅT = 120 K
V = 4267.96 (10) Å3Block, colourless
Z = 80.22 × 0.20 × 0.18 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
5407 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode4925 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.2°
ϕ and ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1919
Tmin = 0.975, Tmax = 0.980l = 2626
70888 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0543P)2 + 0.5385P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
5407 reflectionsΔρmax = 0.24 e Å3
581 parametersΔρmin = 0.20 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0044 (6)
Crystal data top
C18H23N3O10·0.065H2OV = 4267.96 (10) Å3
Mr = 442.57Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 14.3816 (2) ŵ = 0.11 mm1
b = 14.7626 (2) ÅT = 120 K
c = 20.1025 (3) Å0.22 × 0.20 × 0.18 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
5407 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
4925 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.980Rint = 0.041
70888 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0333 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.24 e Å3
5407 reflectionsΔρmin = 0.20 e Å3
581 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N110.55855 (11)0.24150 (11)0.62212 (8)0.0215 (3)
C120.54814 (13)0.15386 (13)0.61908 (9)0.0218 (4)
N130.48420 (11)0.10372 (10)0.65175 (8)0.0230 (3)
C140.42119 (13)0.14549 (13)0.69612 (9)0.0219 (4)
C150.43334 (13)0.24172 (13)0.70370 (9)0.0203 (4)
C160.50035 (13)0.28629 (12)0.66423 (9)0.0198 (4)
O120.60332 (10)0.10425 (10)0.58065 (7)0.0289 (3)
C1210.67981 (15)0.15069 (16)0.54824 (12)0.0338 (5)
H12A0.72010.17820.58200.051*
H12B0.65520.19810.51900.051*
H12C0.71580.10720.52190.051*
C130.47977 (16)0.00484 (13)0.64318 (11)0.0303 (5)
H13A0.46290.00930.59710.045*
H13B0.43290.02030.67340.045*
H13C0.54060.02170.65340.045*
O140.36304 (11)0.09911 (10)0.72463 (7)0.0308 (3)
C510.37858 (14)0.28639 (13)0.75333 (10)0.0228 (4)
H510.33480.25090.77720.027*
O510.38407 (10)0.36808 (9)0.76745 (7)0.0268 (3)
N160.51011 (11)0.37678 (10)0.66764 (8)0.0215 (3)
H160.47350.40730.69470.026*
C210.57743 (13)0.42591 (12)0.62928 (10)0.0210 (4)
H210.58090.40090.58310.025*
C220.54980 (13)0.52631 (13)0.62743 (10)0.0212 (4)
H220.53910.54910.67360.025*
C230.62576 (13)0.58076 (12)0.59419 (10)0.0208 (4)
H230.62950.56490.54590.025*
C240.71839 (13)0.56305 (13)0.62761 (10)0.0225 (4)
H240.71740.58550.67450.027*
C250.73790 (14)0.46158 (13)0.62595 (11)0.0252 (4)
H25A0.73960.43980.57940.030*
H25B0.79880.44860.64680.030*
O260.66507 (9)0.41678 (9)0.66179 (7)0.0246 (3)
O220.46700 (9)0.53734 (9)0.58827 (7)0.0243 (3)
C2210.38547 (14)0.54845 (13)0.62114 (11)0.0277 (4)
O2210.37893 (11)0.54460 (11)0.68085 (8)0.0378 (4)
C2220.30731 (15)0.56670 (17)0.57410 (13)0.0382 (5)
H22A0.30630.63130.56280.057*
H22B0.24830.54980.59510.057*
H22C0.31610.53100.53350.057*
O230.60521 (10)0.67618 (9)0.60197 (6)0.0238 (3)
C2310.58914 (15)0.72517 (14)0.54637 (10)0.0282 (4)
O2310.58183 (14)0.69321 (12)0.49217 (8)0.0451 (5)
C2320.5801 (2)0.82334 (15)0.56262 (13)0.0454 (6)
H23A0.51450.83810.57010.068*
H23B0.60400.85960.52550.068*
H23C0.61590.83690.60290.068*
O240.78850 (9)0.61050 (9)0.58946 (7)0.0251 (3)
C2410.83126 (14)0.68144 (15)0.61893 (11)0.0294 (4)
O2410.82119 (13)0.70105 (14)0.67621 (9)0.0523 (5)
C2420.89103 (17)0.73180 (15)0.57108 (12)0.0371 (5)
H24A0.95610.72760.58520.056*
H24B0.87210.79550.57000.056*
H24C0.88420.70540.52660.056*
N310.56643 (11)0.23884 (11)0.39917 (8)0.0224 (3)
C320.56474 (13)0.15069 (13)0.39628 (10)0.0229 (4)
N330.50463 (11)0.09540 (11)0.42829 (8)0.0235 (4)
C340.43784 (14)0.13218 (14)0.47255 (10)0.0235 (4)
C350.43767 (14)0.22933 (13)0.47719 (10)0.0231 (4)
C360.50126 (13)0.27904 (13)0.43867 (9)0.0206 (4)
O320.62713 (10)0.10542 (10)0.36094 (8)0.0296 (3)
C3210.69918 (16)0.15819 (16)0.32828 (12)0.0359 (5)
H32A0.72950.19770.36090.054*
H32B0.67130.19530.29310.054*
H32C0.74540.11720.30880.054*
C330.50724 (16)0.00296 (14)0.41756 (13)0.0350 (5)
H33A0.45420.03120.44010.052*
H33B0.56530.02750.43570.052*
H33C0.50400.01580.36980.052*
O340.38674 (10)0.08067 (10)0.50337 (8)0.0313 (3)
C530.37410 (14)0.27053 (14)0.52295 (10)0.0264 (4)
H530.33470.23110.54750.032*
O530.36572 (10)0.35231 (10)0.53346 (7)0.0308 (3)
N360.50076 (11)0.37048 (11)0.43931 (8)0.0238 (3)
H360.45950.39860.46420.029*
C410.56495 (13)0.42343 (13)0.40099 (10)0.0223 (4)
H410.58550.38780.36130.027*
C420.52077 (13)0.51266 (13)0.37773 (10)0.0219 (4)
H420.49790.54900.41640.026*
C430.59237 (13)0.56491 (12)0.33805 (9)0.0206 (4)
H430.60590.53240.29550.025*
C440.68144 (13)0.57653 (12)0.37760 (10)0.0214 (4)
H440.67070.61840.41590.026*
C450.71626 (13)0.48519 (14)0.40262 (11)0.0262 (4)
H45A0.73250.44580.36450.031*
H45B0.77260.49370.43020.031*
O460.64374 (9)0.44355 (9)0.44162 (7)0.0251 (3)
O420.44569 (9)0.49149 (10)0.33244 (7)0.0259 (3)
C4210.35756 (14)0.49991 (14)0.35479 (11)0.0287 (4)
O4210.33856 (11)0.52294 (13)0.41028 (9)0.0425 (4)
C4220.28865 (16)0.47422 (18)0.30211 (12)0.0388 (5)
H42A0.23600.51640.30330.058*
H42B0.26630.41250.31030.058*
H42C0.31860.47700.25840.058*
O430.55693 (10)0.65436 (9)0.32390 (7)0.0236 (3)
C4310.55734 (14)0.68219 (14)0.26010 (10)0.0259 (4)
O4320.57219 (12)0.63377 (11)0.21329 (7)0.0385 (4)
C4320.53632 (19)0.78155 (15)0.25651 (12)0.0383 (5)
H43A0.47030.79160.26620.057*
H43B0.55050.80400.21180.057*
H43C0.57440.81400.28920.057*
O440.74702 (9)0.61608 (9)0.33157 (7)0.0249 (3)
C4410.80981 (14)0.67443 (14)0.35627 (11)0.0296 (4)
O4410.82016 (14)0.68736 (15)0.41453 (9)0.0567 (6)
C4420.86416 (17)0.71843 (16)0.30227 (12)0.0375 (5)
H44A0.92800.72890.31750.056*
H44B0.83530.77650.29060.056*
H44C0.86500.67900.26310.056*
O610.7788 (10)0.2493 (10)0.6595 (7)0.043 (4)*0.130 (6)
H610.740 (9)0.253 (15)0.690 (6)0.051*0.130 (6)
H620.829 (6)0.270 (14)0.675 (8)0.051*0.130 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0203 (7)0.0230 (8)0.0211 (8)0.0004 (6)0.0013 (7)0.0005 (6)
C120.0206 (9)0.0234 (9)0.0212 (9)0.0021 (7)0.0038 (7)0.0010 (7)
N130.0281 (8)0.0175 (7)0.0232 (8)0.0003 (6)0.0010 (7)0.0008 (6)
C140.0230 (9)0.0231 (9)0.0197 (9)0.0023 (8)0.0040 (7)0.0015 (7)
C150.0205 (9)0.0215 (9)0.0189 (9)0.0023 (7)0.0032 (7)0.0004 (7)
C160.0192 (8)0.0217 (9)0.0186 (9)0.0002 (7)0.0039 (7)0.0001 (7)
O120.0277 (7)0.0257 (7)0.0334 (8)0.0052 (6)0.0043 (6)0.0024 (6)
C1210.0267 (10)0.0395 (12)0.0353 (12)0.0055 (9)0.0077 (9)0.0008 (10)
C130.0409 (12)0.0160 (9)0.0339 (11)0.0018 (9)0.0018 (9)0.0000 (8)
O140.0370 (8)0.0258 (7)0.0296 (8)0.0098 (6)0.0050 (7)0.0008 (6)
C510.0220 (9)0.0259 (10)0.0205 (9)0.0016 (8)0.0009 (7)0.0024 (7)
O510.0277 (7)0.0248 (7)0.0281 (7)0.0016 (6)0.0010 (6)0.0040 (6)
N160.0221 (8)0.0188 (7)0.0236 (8)0.0025 (6)0.0016 (6)0.0007 (6)
C210.0206 (9)0.0205 (9)0.0221 (9)0.0017 (7)0.0004 (7)0.0006 (7)
C220.0218 (9)0.0195 (8)0.0224 (9)0.0000 (7)0.0003 (8)0.0006 (7)
C230.0254 (9)0.0160 (8)0.0211 (9)0.0009 (7)0.0007 (8)0.0014 (7)
C240.0221 (9)0.0223 (9)0.0230 (9)0.0041 (7)0.0039 (8)0.0005 (8)
C250.0211 (9)0.0234 (9)0.0313 (10)0.0015 (7)0.0016 (8)0.0040 (8)
O260.0214 (6)0.0244 (7)0.0280 (7)0.0020 (6)0.0008 (6)0.0065 (6)
O220.0214 (6)0.0247 (7)0.0269 (7)0.0002 (5)0.0005 (6)0.0001 (6)
C2210.0242 (10)0.0202 (9)0.0388 (12)0.0014 (8)0.0044 (9)0.0002 (9)
O2210.0343 (8)0.0411 (9)0.0380 (9)0.0081 (7)0.0120 (7)0.0045 (7)
C2220.0253 (11)0.0385 (12)0.0510 (15)0.0052 (9)0.0019 (10)0.0018 (11)
O230.0332 (7)0.0175 (6)0.0206 (7)0.0007 (5)0.0005 (6)0.0007 (5)
C2310.0307 (10)0.0285 (10)0.0254 (10)0.0086 (9)0.0022 (8)0.0032 (8)
O2310.0688 (12)0.0439 (9)0.0227 (8)0.0301 (9)0.0047 (8)0.0021 (7)
C2320.0746 (18)0.0262 (11)0.0353 (12)0.0105 (12)0.0039 (13)0.0051 (10)
O240.0260 (7)0.0230 (7)0.0262 (7)0.0060 (5)0.0051 (6)0.0016 (6)
C2410.0216 (9)0.0310 (10)0.0357 (12)0.0047 (8)0.0034 (8)0.0064 (9)
O2410.0450 (10)0.0715 (13)0.0406 (10)0.0319 (10)0.0149 (8)0.0264 (9)
C2420.0366 (12)0.0310 (11)0.0436 (13)0.0134 (10)0.0062 (10)0.0011 (10)
N310.0223 (8)0.0219 (8)0.0228 (8)0.0030 (6)0.0019 (7)0.0011 (6)
C320.0209 (9)0.0252 (9)0.0227 (9)0.0014 (7)0.0002 (7)0.0010 (7)
N330.0238 (8)0.0211 (8)0.0257 (9)0.0037 (6)0.0004 (7)0.0037 (6)
C340.0206 (9)0.0280 (10)0.0220 (9)0.0037 (8)0.0038 (7)0.0053 (8)
C350.0205 (9)0.0263 (9)0.0225 (9)0.0033 (8)0.0020 (8)0.0032 (8)
C360.0202 (9)0.0232 (9)0.0184 (9)0.0024 (7)0.0024 (7)0.0011 (7)
O320.0289 (7)0.0241 (7)0.0359 (8)0.0008 (6)0.0086 (6)0.0008 (6)
C3210.0329 (11)0.0331 (11)0.0419 (13)0.0036 (9)0.0151 (10)0.0024 (10)
C330.0354 (11)0.0218 (10)0.0477 (14)0.0029 (9)0.0038 (10)0.0038 (9)
O340.0287 (7)0.0307 (8)0.0343 (8)0.0086 (6)0.0035 (6)0.0097 (6)
C530.0232 (10)0.0326 (11)0.0232 (10)0.0029 (8)0.0003 (8)0.0045 (8)
O530.0271 (7)0.0340 (8)0.0315 (8)0.0016 (6)0.0033 (6)0.0002 (6)
N360.0223 (8)0.0227 (8)0.0263 (9)0.0005 (6)0.0035 (7)0.0008 (7)
C410.0207 (9)0.0229 (9)0.0232 (10)0.0008 (7)0.0001 (8)0.0017 (7)
C420.0203 (9)0.0233 (9)0.0221 (9)0.0001 (7)0.0025 (7)0.0013 (8)
C430.0221 (9)0.0185 (8)0.0212 (9)0.0030 (7)0.0008 (7)0.0006 (7)
C440.0203 (9)0.0219 (9)0.0220 (9)0.0016 (7)0.0021 (7)0.0020 (7)
C450.0190 (9)0.0283 (10)0.0312 (11)0.0002 (8)0.0012 (8)0.0074 (9)
O460.0201 (6)0.0286 (7)0.0267 (7)0.0037 (6)0.0027 (6)0.0063 (6)
O420.0203 (6)0.0312 (7)0.0261 (7)0.0025 (6)0.0029 (6)0.0008 (6)
C4210.0221 (9)0.0272 (10)0.0369 (12)0.0011 (8)0.0020 (9)0.0056 (9)
O4210.0255 (8)0.0589 (11)0.0430 (10)0.0004 (7)0.0039 (7)0.0091 (9)
C4220.0269 (11)0.0461 (13)0.0436 (13)0.0027 (10)0.0106 (10)0.0087 (11)
O430.0291 (7)0.0204 (6)0.0214 (7)0.0042 (6)0.0008 (6)0.0031 (5)
C4310.0237 (9)0.0289 (10)0.0252 (10)0.0016 (8)0.0028 (8)0.0053 (8)
O4320.0512 (10)0.0420 (9)0.0223 (8)0.0132 (8)0.0023 (7)0.0017 (7)
C4320.0513 (14)0.0282 (11)0.0354 (12)0.0019 (10)0.0056 (11)0.0092 (9)
O440.0259 (7)0.0242 (7)0.0245 (7)0.0053 (6)0.0047 (6)0.0009 (6)
C4410.0270 (10)0.0273 (10)0.0346 (12)0.0058 (9)0.0035 (8)0.0020 (9)
O4410.0566 (11)0.0799 (14)0.0338 (10)0.0407 (11)0.0010 (8)0.0073 (10)
C4420.0397 (13)0.0329 (11)0.0400 (13)0.0124 (10)0.0121 (10)0.0047 (10)
Geometric parameters (Å, º) top
N11—C121.304 (2)C32—N331.352 (2)
C12—N131.351 (3)N33—C341.417 (3)
N13—C141.413 (2)C34—C351.437 (3)
C14—C151.439 (3)C35—C361.405 (3)
C15—C161.411 (3)C36—N311.364 (2)
C16—N111.362 (2)C32—O321.325 (2)
C12—O121.328 (2)N33—C331.468 (3)
N13—C131.471 (2)C34—O341.226 (2)
C14—O141.223 (2)C35—C531.432 (3)
C15—C511.432 (3)C53—O531.232 (3)
C51—O511.241 (2)C36—N361.350 (2)
C16—N161.345 (2)O32—C3211.453 (2)
O12—C1211.451 (3)C321—H32A0.9800
C121—H12A0.9800C321—H32B0.9800
C121—H12B0.9800C321—H32C0.9800
C121—H12C0.9800C33—H33A0.9800
C13—H13A0.9800C33—H33B0.9800
C13—H13B0.9800C33—H33C0.9800
C13—H13C0.9800C53—H530.9500
C51—H510.9500N36—C411.434 (2)
N16—C211.435 (2)N36—H360.8800
N16—H160.8800C41—O461.428 (2)
C21—O261.426 (2)C41—C421.536 (3)
C21—C221.535 (3)C41—H411.0000
C21—H211.0000C42—O421.446 (2)
C22—O221.437 (2)C42—C431.514 (3)
C22—C231.512 (3)C42—H421.0000
C22—H221.0000C43—O431.444 (2)
C23—O231.448 (2)C43—C441.517 (3)
C23—C241.515 (3)C43—H431.0000
C23—H231.0000C44—O441.444 (2)
C24—O241.448 (2)C44—C451.524 (3)
C24—C251.524 (3)C44—H441.0000
C24—H241.0000C45—O461.442 (2)
C25—O261.433 (2)C45—H45A0.9900
C25—H25A0.9900C45—H45B0.9900
C25—H25B0.9900O42—C4211.351 (2)
O22—C2211.356 (2)C421—O4211.198 (3)
C221—O2211.205 (3)C421—C4221.499 (3)
C221—C2221.494 (3)C422—H42A0.9800
C222—H22A0.9800C422—H42B0.9800
C222—H22B0.9800C422—H42C0.9800
C222—H22C0.9800O43—C4311.347 (2)
O23—C2311.351 (2)C431—O4321.201 (3)
C231—O2311.192 (3)C431—C4321.499 (3)
C231—C2321.491 (3)C432—H43A0.9800
C232—H23A0.9800C432—H43B0.9800
C232—H23B0.9800C432—H43C0.9800
C232—H23C0.9800O44—C4411.343 (2)
O24—C2411.351 (2)C441—O4411.196 (3)
C241—O2411.196 (3)C441—C4421.487 (3)
C241—C2421.489 (3)C442—H44A0.9800
C242—H24A0.9800C442—H44B0.9800
C242—H24B0.9800C442—H44C0.9800
C242—H24C0.9800O61—H610.839 (11)
N31—C321.303 (2)O61—H620.840 (11)
C12—N11—C16116.12 (17)N31—C32—O32121.00 (17)
N11—C12—O12120.39 (18)N31—C32—N33126.42 (18)
N11—C12—N13126.81 (18)O32—C32—N33112.56 (16)
O12—C12—N13112.80 (16)C32—N33—C34120.05 (16)
C12—N13—C14120.28 (15)C32—N33—C33120.71 (18)
C12—N13—C13121.07 (17)C34—N33—C33119.24 (17)
C14—N13—C13118.63 (17)O34—C34—N33119.07 (18)
O14—C14—N13119.33 (17)O34—C34—C35125.8 (2)
O14—C14—C15125.86 (19)N33—C34—C35115.10 (17)
N13—C14—C15114.81 (16)C36—C35—C53123.19 (18)
C16—C15—C51123.55 (17)C36—C35—C34118.97 (18)
C16—C15—C14118.92 (17)C53—C35—C34117.81 (17)
C51—C15—C14117.48 (17)N36—C36—N31116.38 (17)
N16—C16—N11116.73 (17)N36—C36—C35120.90 (18)
N16—C16—C15120.38 (18)N31—C36—C35122.72 (17)
N11—C16—C15122.89 (16)C32—O32—C321117.04 (16)
C12—O12—C121116.99 (16)O32—C321—H32A109.5
O12—C121—H12A109.5O32—C321—H32B109.5
O12—C121—H12B109.5H32A—C321—H32B109.5
H12A—C121—H12B109.5O32—C321—H32C109.5
O12—C121—H12C109.5H32A—C321—H32C109.5
H12A—C121—H12C109.5H32B—C321—H32C109.5
H12B—C121—H12C109.5N33—C33—H33A109.5
N13—C13—H13A109.5N33—C33—H33B109.5
N13—C13—H13B109.5H33A—C33—H33B109.5
H13A—C13—H13B109.5N33—C33—H33C109.5
N13—C13—H13C109.5H33A—C33—H33C109.5
H13A—C13—H13C109.5H33B—C33—H33C109.5
H13B—C13—H13C109.5O53—C53—C35126.08 (18)
O51—C51—C15124.87 (18)O53—C53—H53117.0
O51—C51—H51117.6C35—C53—H53117.0
C15—C51—H51117.6C36—N36—C41122.44 (17)
C16—N16—C21123.04 (17)C36—N36—H36118.8
C16—N16—H16118.5C41—N36—H36118.8
C21—N16—H16118.5O46—C41—N36108.48 (15)
O26—C21—N16107.59 (15)O46—C41—C42108.91 (15)
O26—C21—C22109.34 (15)N36—C41—C42111.39 (15)
N16—C21—C22109.05 (15)O46—C41—H41109.3
O26—C21—H21110.3N36—C41—H41109.3
N16—C21—H21110.3C42—C41—H41109.3
C22—C21—H21110.3O42—C42—C43106.63 (15)
O22—C22—C23107.24 (15)O42—C42—C41108.38 (15)
O22—C22—C21109.71 (15)C43—C42—C41108.42 (15)
C23—C22—C21109.69 (15)O42—C42—H42111.1
O22—C22—H22110.0C43—C42—H42111.1
C23—C22—H22110.0C41—C42—H42111.1
C21—C22—H22110.0O43—C43—C42109.25 (15)
O23—C23—C22108.79 (15)O43—C43—C44107.33 (15)
O23—C23—C24107.43 (15)C42—C43—C44110.85 (15)
C22—C23—C24110.34 (15)O43—C43—H43109.8
O23—C23—H23110.1C42—C43—H43109.8
C22—C23—H23110.1C44—C43—H43109.8
C24—C23—H23110.1O44—C44—C43105.15 (15)
O24—C24—C23107.10 (15)O44—C44—C45110.77 (15)
O24—C24—C25109.61 (16)C43—C44—C45110.51 (15)
C23—C24—C25108.77 (16)O44—C44—H44110.1
O24—C24—H24110.4C43—C44—H44110.1
C23—C24—H24110.4C45—C44—H44110.1
C25—C24—H24110.4O46—C45—C44108.60 (15)
O26—C25—C24107.94 (16)O46—C45—H45A110.0
O26—C25—H25A110.1C44—C45—H45A110.0
C24—C25—H25A110.1O46—C45—H45B110.0
O26—C25—H25B110.1C44—C45—H45B110.0
C24—C25—H25B110.1H45A—C45—H45B108.4
H25A—C25—H25B108.4C41—O46—C45110.58 (14)
C21—O26—C25111.83 (14)C421—O42—C42118.11 (15)
C221—O22—C22117.61 (15)O421—C421—O42123.38 (19)
O221—C221—O22123.2 (2)O421—C421—C422125.4 (2)
O221—C221—C222125.5 (2)O42—C421—C422111.23 (19)
O22—C221—C222111.35 (18)C421—C422—H42A109.5
C221—C222—H22A109.5C421—C422—H42B109.5
C221—C222—H22B109.5H42A—C422—H42B109.5
H22A—C222—H22B109.5C421—C422—H42C109.5
C221—C222—H22C109.5H42A—C422—H42C109.5
H22A—C222—H22C109.5H42B—C422—H42C109.5
H22B—C222—H22C109.5C431—O43—C43117.72 (15)
C231—O23—C23117.80 (15)O432—C431—O43124.43 (18)
O231—C231—O23124.01 (19)O432—C431—C432125.5 (2)
O231—C231—C232125.3 (2)O43—C431—C432110.09 (18)
O23—C231—C232110.72 (18)C431—C432—H43A109.5
C231—C232—H23A109.5C431—C432—H43B109.5
C231—C232—H23B109.5H43A—C432—H43B109.5
H23A—C232—H23B109.5C431—C432—H43C109.5
C231—C232—H23C109.5H43A—C432—H43C109.5
H23A—C232—H23C109.5H43B—C432—H43C109.5
H23B—C232—H23C109.5C441—O44—C44117.49 (15)
C241—O24—C24117.37 (15)O441—C441—O44123.2 (2)
O241—C241—O24123.7 (2)O441—C441—C442125.4 (2)
O241—C241—C242124.8 (2)O44—C441—C442111.33 (18)
O24—C241—C242111.50 (18)C441—C442—H44A109.5
C241—C242—H24A109.5C441—C442—H44B109.5
C241—C242—H24B109.5H44A—C442—H44B109.5
H24A—C242—H24B109.5C441—C442—H44C109.5
C241—C242—H24C109.5H44A—C442—H44C109.5
H24A—C242—H24C109.5H44B—C442—H44C109.5
H24B—C242—H24C109.5H61—O61—H62106.0 (18)
C32—N31—C36116.60 (16)
C16—N11—C12—O12178.30 (16)C36—N31—C32—O32177.81 (17)
C16—N11—C12—N132.0 (3)C36—N31—C32—N330.3 (3)
N11—C12—N13—C141.9 (3)N31—C32—N33—C343.2 (3)
O12—C12—N13—C14178.47 (16)O32—C32—N33—C34175.03 (16)
N11—C12—N13—C13179.44 (19)N31—C32—N33—C33176.5 (2)
O12—C12—N13—C130.2 (3)O32—C32—N33—C335.2 (3)
C12—N13—C14—O14179.10 (18)C32—N33—C34—O34176.75 (18)
C13—N13—C14—O142.2 (3)C33—N33—C34—O343.5 (3)
C12—N13—C14—C151.5 (2)C32—N33—C34—C352.7 (3)
C13—N13—C14—C15177.27 (17)C33—N33—C34—C35177.00 (19)
O14—C14—C15—C16176.34 (18)O34—C34—C35—C36179.66 (18)
N13—C14—C15—C164.3 (2)N33—C34—C35—C360.2 (3)
O14—C14—C15—C516.1 (3)O34—C34—C35—C531.7 (3)
N13—C14—C15—C51173.29 (16)N33—C34—C35—C53177.73 (16)
C12—N11—C16—N16179.74 (17)C32—N31—C36—N36177.29 (18)
C12—N11—C16—C151.2 (3)C32—N31—C36—C352.9 (3)
C51—C15—C16—N166.0 (3)C53—C35—C36—N365.1 (3)
C14—C15—C16—N16176.58 (17)C34—C35—C36—N36177.08 (18)
C51—C15—C16—N11173.04 (17)C53—C35—C36—N31174.69 (17)
C14—C15—C16—N114.4 (3)C34—C35—C36—N313.2 (3)
N11—C12—O12—C1215.9 (3)N31—C32—O32—C3212.6 (3)
N13—C12—O12—C121174.44 (16)N33—C32—O32—C321175.78 (17)
C16—C15—C51—O510.5 (3)C36—C35—C53—O531.4 (3)
C14—C15—C51—O51176.94 (19)C34—C35—C53—O53179.2 (2)
N11—C16—N16—C210.3 (3)N31—C36—N36—C410.2 (3)
C15—C16—N16—C21179.43 (17)C35—C36—N36—C41179.60 (17)
C16—N16—C21—O2679.7 (2)C36—N36—C41—O4692.8 (2)
C16—N16—C21—C22161.82 (17)C36—N36—C41—C42147.33 (18)
O26—C21—C22—O22173.52 (14)O46—C41—C42—O42175.52 (14)
N16—C21—C22—O2269.08 (19)N36—C41—C42—O4264.9 (2)
O26—C21—C22—C2356.0 (2)O46—C41—C42—C4360.14 (19)
N16—C21—C22—C23173.36 (15)N36—C41—C42—C43179.75 (15)
O22—C22—C23—O2369.56 (18)O42—C42—C43—O4371.68 (18)
C21—C22—C23—O23171.35 (15)C41—C42—C43—O43171.81 (14)
O22—C22—C23—C24172.82 (15)O42—C42—C43—C44170.24 (15)
C21—C22—C23—C2453.7 (2)C41—C42—C43—C4453.7 (2)
O23—C23—C24—O2466.78 (18)O43—C43—C44—O4468.13 (17)
C22—C23—C24—O24174.77 (15)C42—C43—C44—O44172.64 (14)
O23—C23—C24—C25174.83 (16)O43—C43—C44—C45172.30 (15)
C22—C23—C24—C2556.4 (2)C42—C43—C44—C4553.1 (2)
O24—C24—C25—O26177.61 (14)O44—C44—C45—O46172.96 (15)
C23—C24—C25—O2660.8 (2)C43—C44—C45—O4656.8 (2)
N16—C21—O26—C25178.25 (14)N36—C41—O46—C45171.58 (14)
C22—C21—O26—C2563.43 (19)C42—C41—O46—C4567.01 (19)
C24—C25—O26—C2165.9 (2)C44—C45—O46—C4164.8 (2)
C23—C22—O22—C221138.99 (16)C43—C42—O42—C421138.41 (17)
C21—C22—O22—C221101.93 (19)C41—C42—O42—C421105.05 (19)
C22—O22—C221—O2214.1 (3)C42—O42—C421—O4210.9 (3)
C22—O22—C221—C222175.25 (17)C42—O42—C421—C422179.22 (17)
C22—C23—O23—C231116.71 (18)C42—C43—O43—C431127.34 (18)
C24—C23—O23—C231123.84 (18)C44—C43—O43—C431112.41 (18)
C23—O23—C231—O2317.7 (3)C43—O43—C431—O43211.4 (3)
C23—O23—C231—C232173.46 (19)C43—O43—C431—C432168.84 (17)
C23—C24—O24—C241112.56 (18)C43—C44—O44—C441146.39 (17)
C25—C24—O24—C241129.59 (19)C45—C44—O44—C44194.2 (2)
C24—O24—C241—O2417.8 (3)C44—O44—C441—O4418.2 (3)
C24—O24—C241—C242171.66 (17)C44—O44—C441—C442172.60 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N16—H16···O510.882.032.707 (2)133
N36—H36···O530.882.062.725 (2)132
C24—H24···O14i1.002.343.237 (3)148
C44—H44···O2311.002.283.213 (3)155
C45—H45B···O34ii0.992.383.245 (3)145
C51—H51···O241iii0.952.543.442 (3)159
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1/2, y+1/2, z+1; (iii) x+1, y1/2, z+3/2.
(II) 2-methylsulfanyl-6-oxo-4-(2,3,4-tri-O-acetyl-β-D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehyde top
Crystal data top
C17H21N3O9SF(000) = 928
Mr = 443.44Dx = 1.494 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4481 reflections
a = 6.9294 (1) Åθ = 3.3–27.5°
b = 10.7415 (2) ŵ = 0.22 mm1
c = 26.4825 (5) ÅT = 120 K
V = 1971.15 (6) Å3Block, colourless
Z = 40.44 × 0.35 × 0.30 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
4482 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode4065 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.3°
ϕ and ω scansh = 86
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 139
Tmin = 0.885, Tmax = 0.936l = 3434
12812 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0577P)2 + 0.0098P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max = 0.001
S = 1.14Δρmax = 0.42 e Å3
4482 reflectionsΔρmin = 0.45 e Å3
327 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
40 restraintsExtinction coefficient: 0.039 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (7)
Crystal data top
C17H21N3O9SV = 1971.15 (6) Å3
Mr = 443.44Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.9294 (1) ŵ = 0.22 mm1
b = 10.7415 (2) ÅT = 120 K
c = 26.4825 (5) Å0.44 × 0.35 × 0.30 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
4482 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
4065 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 0.936Rint = 0.031
12812 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.096Δρmax = 0.42 e Å3
S = 1.14Δρmin = 0.45 e Å3
4482 reflectionsAbsolute structure: Flack (1983)
327 parametersAbsolute structure parameter: 0.02 (7)
40 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N11A0.2117 (3)0.88401 (15)0.69071 (6)0.0192 (4)0.899 (2)
C12A0.2137 (3)0.98938 (18)0.71673 (8)0.0183 (4)0.899 (2)
N13A0.2512 (3)0.99686 (15)0.76673 (6)0.0197 (4)0.899 (2)
H13A0.24441.07010.78150.024*0.899 (2)
C14A0.3007 (4)0.89276 (19)0.79600 (7)0.0194 (4)0.899 (2)
C15A0.2951 (7)0.7777 (2)0.76919 (9)0.0192 (6)0.899 (2)
C16A0.2517 (5)0.77804 (18)0.71710 (9)0.0175 (6)0.899 (2)
S1A0.16492 (8)1.12014 (5)0.67968 (2)0.02615 (19)0.899 (2)
C17A0.1898 (3)1.25098 (19)0.72224 (8)0.0275 (5)0.899 (2)
H17A0.10521.23900.75150.041*0.899 (2)
H17B0.15381.32780.70460.041*0.899 (2)
H17C0.32411.25700.73360.041*0.899 (2)
O14A0.3420 (3)0.90748 (14)0.84079 (6)0.0273 (4)0.899 (2)
C51A0.3352 (4)0.6648 (2)0.79630 (8)0.0207 (5)0.899 (2)
H51A0.35490.67210.83170.025*0.899 (2)
O51A0.3465 (9)0.55923 (17)0.77805 (12)0.0241 (4)0.899 (2)
N16A0.2544 (6)0.6701 (3)0.6922 (2)0.0207 (7)0.899 (2)
H16A0.28870.60380.70950.025*0.899 (2)
N11B0.226 (4)0.9040 (8)0.7040 (4)0.0192 (4)0.101 (2)
C12B0.229 (3)0.9958 (7)0.7374 (3)0.0183 (4)0.101 (2)
N13B0.253 (3)0.9795 (8)0.7876 (3)0.0197 (4)0.101 (2)
H13B0.23131.04280.80780.024*0.101 (2)
C14B0.312 (4)0.8664 (10)0.8087 (4)0.0194 (4)0.101 (2)
C15B0.323 (8)0.7666 (12)0.7733 (5)0.0192 (6)0.101 (2)
C16B0.281 (7)0.7897 (11)0.7219 (5)0.0175 (6)0.101 (2)
S1B0.1630 (7)1.1402 (4)0.71288 (19)0.0254 (15)0.101 (2)
C17B0.158 (3)1.1174 (12)0.6450 (2)0.026 (4)0.101 (2)
H17D0.07941.04390.63710.039*0.101 (2)
H17E0.28921.10500.63250.039*0.101 (2)
H17F0.10101.19080.62880.039*0.101 (2)
O14B0.363 (3)0.8653 (12)0.8531 (4)0.0273 (4)0.101 (2)
C51B0.371 (5)0.6449 (9)0.7916 (6)0.0207 (5)0.101 (2)
H51B0.43760.64120.82300.025*0.101 (2)
O51B0.337 (9)0.5446 (11)0.7709 (14)0.0241 (4)0.101 (2)
N16B0.228 (7)0.687 (4)0.693 (2)0.0207 (7)0.101 (2)
H16B0.19830.62370.71260.025*0.101 (2)
C210.2073 (3)0.65075 (16)0.63997 (6)0.0206 (4)
H210.13070.72220.62640.025*
C220.3924 (3)0.63106 (15)0.60911 (6)0.0182 (4)
H220.47970.57030.62640.022*
C230.3431 (2)0.58661 (15)0.55639 (6)0.0179 (3)
H230.27630.65420.53720.022*
C240.2143 (3)0.47314 (16)0.56016 (6)0.0196 (4)
H240.28560.40390.57710.024*
C250.0354 (2)0.50570 (18)0.59043 (6)0.0222 (4)
H25A0.03400.57580.57430.027*
H25B0.05270.43320.59200.027*
O260.09607 (18)0.54000 (12)0.64029 (4)0.0231 (3)
O220.48698 (18)0.75006 (11)0.60321 (4)0.0203 (3)
C2210.6450 (3)0.77542 (17)0.63151 (7)0.0230 (4)
O2210.7116 (2)0.70511 (13)0.66180 (6)0.0379 (4)
C2220.7170 (3)0.90289 (16)0.62015 (7)0.0282 (4)
H22A0.63770.96430.63800.042*
H22B0.70940.91800.58370.042*
H22C0.85140.91040.63130.042*
O230.51873 (17)0.55138 (11)0.53106 (4)0.0205 (3)
C2310.5649 (3)0.61331 (17)0.48826 (6)0.0203 (4)
O2310.4777 (2)0.70263 (12)0.47298 (5)0.0283 (3)
C2320.7360 (3)0.55551 (18)0.46332 (7)0.0289 (4)
H23A0.73380.57450.42710.043*
H23B0.73220.46510.46810.043*
H23C0.85450.58900.47830.043*
O240.16847 (18)0.43814 (12)0.50885 (4)0.0213 (3)
C2410.1315 (3)0.31614 (18)0.50083 (7)0.0242 (4)
O2410.1123 (2)0.24259 (12)0.53471 (5)0.0364 (4)
C2420.1192 (3)0.28741 (19)0.44560 (7)0.0284 (4)
H24A0.10500.19740.44090.043*
H24B0.23700.31590.42870.043*
H24C0.00730.33020.43100.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N11A0.0203 (8)0.0205 (8)0.0169 (9)0.0021 (8)0.0017 (8)0.0022 (7)
C12A0.0148 (9)0.0200 (9)0.0202 (10)0.0016 (8)0.0005 (9)0.0040 (8)
N13A0.0227 (8)0.0198 (8)0.0165 (9)0.0006 (7)0.0000 (9)0.0031 (7)
C14A0.0181 (9)0.0210 (11)0.0190 (10)0.0004 (9)0.0021 (10)0.0001 (8)
C15A0.014 (2)0.0233 (10)0.0205 (9)0.0006 (8)0.0015 (8)0.0009 (8)
C16A0.0127 (17)0.0190 (9)0.0210 (8)0.0028 (9)0.0003 (8)0.0022 (7)
S1A0.0284 (3)0.0221 (3)0.0279 (4)0.0005 (2)0.0055 (2)0.0027 (2)
C17A0.0233 (10)0.0214 (10)0.0378 (12)0.0001 (9)0.0029 (9)0.0005 (9)
O14A0.0369 (9)0.0255 (9)0.0195 (8)0.0000 (8)0.0038 (7)0.0025 (6)
C51A0.0174 (14)0.0289 (11)0.0158 (9)0.0030 (9)0.0043 (8)0.0016 (8)
O51A0.0313 (10)0.0235 (8)0.0175 (13)0.0019 (11)0.0007 (11)0.0018 (7)
N16A0.0288 (19)0.0175 (14)0.0158 (7)0.0057 (11)0.0002 (11)0.0011 (11)
N11B0.0203 (8)0.0205 (8)0.0169 (9)0.0021 (8)0.0017 (8)0.0022 (7)
C12B0.0148 (9)0.0200 (9)0.0202 (10)0.0016 (8)0.0005 (9)0.0040 (8)
N13B0.0227 (8)0.0198 (8)0.0165 (9)0.0006 (7)0.0000 (9)0.0031 (7)
C14B0.0181 (9)0.0210 (11)0.0190 (10)0.0004 (9)0.0021 (10)0.0001 (8)
C15B0.014 (2)0.0233 (10)0.0205 (9)0.0006 (8)0.0015 (8)0.0009 (8)
C16B0.0127 (17)0.0190 (9)0.0210 (8)0.0028 (9)0.0003 (8)0.0022 (7)
S1B0.027 (2)0.027 (3)0.022 (3)0.007 (2)0.002 (2)0.0047 (19)
C17B0.041 (8)0.030 (7)0.007 (6)0.002 (7)0.012 (6)0.003 (6)
O14B0.0369 (9)0.0255 (9)0.0195 (8)0.0000 (8)0.0038 (7)0.0025 (6)
C51B0.0174 (14)0.0289 (11)0.0158 (9)0.0030 (9)0.0043 (8)0.0016 (8)
O51B0.0313 (10)0.0235 (8)0.0175 (13)0.0019 (11)0.0007 (11)0.0018 (7)
N16B0.0288 (19)0.0175 (14)0.0158 (7)0.0057 (11)0.0002 (11)0.0011 (11)
C210.0233 (9)0.0215 (9)0.0170 (8)0.0023 (7)0.0002 (7)0.0000 (7)
C220.0225 (8)0.0135 (8)0.0187 (8)0.0001 (7)0.0010 (7)0.0014 (7)
C230.0195 (8)0.0167 (8)0.0176 (8)0.0033 (7)0.0012 (7)0.0017 (6)
C240.0241 (9)0.0178 (8)0.0170 (8)0.0010 (7)0.0013 (7)0.0011 (7)
C250.0210 (9)0.0268 (10)0.0189 (8)0.0028 (8)0.0003 (7)0.0023 (7)
O260.0252 (6)0.0270 (7)0.0173 (6)0.0038 (6)0.0023 (5)0.0005 (5)
O220.0234 (6)0.0166 (6)0.0209 (6)0.0014 (5)0.0024 (5)0.0033 (5)
C2210.0253 (9)0.0228 (9)0.0208 (8)0.0011 (8)0.0007 (8)0.0025 (7)
O2210.0441 (8)0.0278 (7)0.0418 (8)0.0048 (7)0.0221 (7)0.0091 (7)
C2220.0340 (11)0.0244 (10)0.0261 (9)0.0052 (9)0.0000 (8)0.0035 (7)
O230.0214 (6)0.0204 (6)0.0195 (6)0.0028 (5)0.0034 (5)0.0020 (5)
C2310.0226 (8)0.0180 (9)0.0205 (8)0.0053 (7)0.0013 (7)0.0016 (7)
O2310.0316 (7)0.0249 (7)0.0286 (7)0.0023 (6)0.0040 (6)0.0068 (6)
C2320.0303 (10)0.0243 (9)0.0321 (10)0.0019 (8)0.0127 (9)0.0021 (8)
O240.0277 (6)0.0180 (6)0.0183 (6)0.0005 (6)0.0013 (5)0.0010 (5)
C2410.0232 (9)0.0206 (10)0.0287 (10)0.0002 (8)0.0015 (8)0.0039 (8)
O2410.0530 (9)0.0219 (7)0.0342 (7)0.0069 (7)0.0004 (7)0.0032 (6)
C2420.0326 (10)0.0256 (10)0.0271 (9)0.0004 (8)0.0017 (8)0.0065 (8)
Geometric parameters (Å, º) top
N11A—C12A1.325 (2)N16B—C211.46 (5)
C12A—N13A1.352 (2)N16B—H16B0.8800
N13A—C14A1.403 (3)C21—O261.417 (2)
C14A—C15A1.425 (3)C21—C221.535 (2)
C15A—C16A1.412 (2)C21—H211.0000
C16A—N11A1.364 (2)C22—O221.445 (2)
C12A—S1A1.746 (2)C22—C231.515 (2)
N13A—H13A0.8800C22—H221.0000
C14A—O14A1.230 (2)C23—O231.440 (2)
C15A—C51A1.436 (3)C23—C241.514 (2)
C51A—O51A1.236 (3)C23—H231.0000
C16A—N16A1.335 (3)C24—O241.4452 (19)
S1A—C17A1.810 (2)C24—C251.517 (2)
C17A—H17A0.9800C24—H241.0000
C17A—H17B0.9800C25—O261.4337 (19)
C17A—H17C0.9800C25—H25A0.9900
C51A—H51A0.9500C25—H25B0.9900
N16A—C211.435 (5)O22—C2211.355 (2)
N16A—H16A0.8800C221—O2211.194 (2)
N11B—C12B1.325 (5)C221—C2221.488 (3)
N11B—C16B1.370 (5)C222—H22A0.9800
C12B—N13B1.350 (5)C222—H22B0.9800
C12B—S1B1.743 (4)C222—H22C0.9800
N13B—C14B1.398 (5)O23—C2311.353 (2)
N13B—H13B0.8800C231—O2311.204 (2)
C14B—O14B1.229 (5)C231—C2321.493 (3)
C14B—C15B1.426 (5)C232—H23A0.9800
C15B—C16B1.412 (4)C232—H23B0.9800
C15B—C51B1.435 (5)C232—H23C0.9800
C16B—N16B1.40 (2)O24—C2411.352 (2)
S1B—C17B1.813 (5)C241—O2411.203 (2)
C17B—H17D0.9800C241—C2421.497 (2)
C17B—H17E0.9800C242—H24A0.9800
C17B—H17F0.9800C242—H24B0.9800
C51B—O51B1.233 (6)C242—H24C0.9800
C51B—H51B0.9500
C12A—N11A—C16A116.38 (16)N16A—C21—H21110.9
N11A—C12A—N13A124.20 (17)N16B—C21—H21101.3
N11A—C12A—S1A113.14 (14)C22—C21—H21110.9
N13A—C12A—S1A122.66 (15)O22—C22—C23106.34 (13)
C12A—N13A—C14A122.73 (16)O22—C22—C21108.35 (13)
C12A—N13A—H13A118.6C23—C22—C21110.23 (14)
C14A—N13A—H13A118.6O22—C22—H22110.6
O14A—C14A—N13A119.14 (17)C23—C22—H22110.6
O14A—C14A—C15A126.70 (19)C21—C22—H22110.6
N13A—C14A—C15A114.15 (16)O23—C23—C24108.50 (13)
C16A—C15A—C14A119.36 (18)O23—C23—C22108.76 (14)
C16A—C15A—C51A122.11 (17)C24—C23—C22109.02 (13)
C14A—C15A—C51A118.53 (17)O23—C23—H23110.2
N16A—C16A—N11A118.3 (3)C24—C23—H23110.2
N16A—C16A—C15A118.6 (3)C22—C23—H23110.2
N11A—C16A—C15A123.08 (17)O24—C24—C23106.08 (13)
C12A—S1A—C17A104.85 (9)O24—C24—C25112.16 (14)
O51A—C51A—C15A126.29 (19)C23—C24—C25109.32 (14)
O51A—C51A—H51A116.9O24—C24—H24109.7
C15A—C51A—H51A116.9C23—C24—H24109.7
C16A—N16A—C21126.8 (4)C25—C24—H24109.7
C16A—N16A—H16A116.6O26—C25—C24107.82 (14)
C21—N16A—H16A116.6O26—C25—H25A110.1
C12B—N11B—C16B115.5 (4)C24—C25—H25A110.1
N11B—C12B—N13B124.2 (4)O26—C25—H25B110.1
N11B—C12B—S1B114.1 (4)C24—C25—H25B110.1
N13B—C12B—S1B121.0 (4)H25A—C25—H25B108.5
C12B—N13B—C14B122.9 (4)C21—O26—C25111.70 (13)
C12B—N13B—H13B118.5C221—O22—C22119.00 (13)
C14B—N13B—H13B118.5O221—C221—O22123.83 (17)
O14B—C14B—N13B118.4 (5)O221—C221—C222126.01 (18)
O14B—C14B—C15B127.4 (6)O22—C221—C222110.14 (15)
N13B—C14B—C15B113.9 (3)C221—C222—H22A109.5
C16B—C15B—C14B119.4 (3)C221—C222—H22B109.5
C16B—C15B—C51B122.3 (4)H22A—C222—H22B109.5
C14B—C15B—C51B118.3 (4)C221—C222—H22C109.5
N11B—C16B—N16B116 (2)H22A—C222—H22C109.5
N11B—C16B—C15B123.2 (4)H22B—C222—H22C109.5
N16B—C16B—C15B116 (3)C231—O23—C23117.44 (13)
C12B—S1B—C17B104.8 (3)O231—C231—O23123.71 (16)
S1B—C17B—H17D109.5O231—C231—C232125.55 (16)
S1B—C17B—H17E109.5O23—C231—C232110.74 (16)
H17D—C17B—H17E109.5C231—C232—H23A109.5
S1B—C17B—H17F109.5C231—C232—H23B109.5
H17D—C17B—H17F109.5H23A—C232—H23B109.5
H17E—C17B—H17F109.5C231—C232—H23C109.5
O51B—C51B—C15B126.8 (7)H23A—C232—H23C109.5
O51B—C51B—H51B116.6H23B—C232—H23C109.5
C15B—C51B—H51B116.6C241—O24—C24116.20 (13)
C16B—N16B—C21140 (5)O241—C241—O24122.72 (17)
C16B—N16B—H16B110.1O241—C241—C242125.93 (18)
C21—N16B—H16B110.1O24—C241—C242111.35 (16)
O26—C21—N16A103.8 (2)C241—C242—H24A109.5
O26—C21—N16B106 (2)C241—C242—H24B109.5
O26—C21—C22109.98 (13)H24A—C242—H24B109.5
N16A—C21—C22110.0 (2)C241—C242—H24C109.5
N16B—C21—C22118 (2)H24A—C242—H24C109.5
O26—C21—H21110.9H24B—C242—H24C109.5
C16A—N11A—C12A—N13A0.4 (4)C14B—C15B—C51B—O51B158 (5)
C16A—N11A—C12A—S1A179.0 (2)N11B—C16B—N16B—C2137 (8)
N11A—C12A—N13A—C14A2.8 (3)C15B—C16B—N16B—C21165 (5)
S1A—C12A—N13A—C14A176.44 (18)C16A—N16A—C21—O26137.7 (4)
C12A—N13A—C14A—O14A176.5 (2)C16A—N16A—C21—N16B36 (14)
C12A—N13A—C14A—C15A4.0 (4)C16A—N16A—C21—C22104.6 (4)
O14A—C14A—C15A—C16A177.6 (3)C16B—N16B—C21—O26164 (5)
N13A—C14A—C15A—C16A3.0 (5)C16B—N16B—C21—N16A115 (17)
O14A—C14A—C15A—C51A2.1 (5)C16B—N16B—C21—C2273 (6)
N13A—C14A—C15A—C51A177.3 (3)O26—C21—C22—O22171.45 (13)
C12A—N11A—C16A—N16A178.9 (3)N16A—C21—C22—O2274.7 (2)
C12A—N11A—C16A—C15A0.6 (5)N16B—C21—C22—O2268 (2)
C14A—C15A—C16A—N16A177.5 (4)O26—C21—C22—C2355.47 (17)
C51A—C15A—C16A—N16A2.2 (6)N16A—C21—C22—C23169.3 (2)
C14A—C15A—C16A—N11A0.9 (6)N16B—C21—C22—C23176 (2)
C51A—C15A—C16A—N11A179.5 (3)O22—C22—C23—O2371.26 (16)
N11A—C12A—S1A—C17A176.69 (18)C21—C22—C23—O23171.51 (13)
N13A—C12A—S1A—C17A2.7 (2)O22—C22—C23—C24170.61 (12)
C16A—C15A—C51A—O51A3.9 (7)C21—C22—C23—C2453.37 (18)
C14A—C15A—C51A—O51A175.7 (5)O23—C23—C24—O2463.37 (16)
N11A—C16A—N16A—C214.2 (6)C22—C23—C24—O24178.33 (13)
C15A—C16A—N16A—C21177.4 (4)O23—C23—C24—C25175.49 (13)
C16B—N11B—C12B—N13B10 (4)C22—C23—C24—C2557.20 (18)
C16B—N11B—C12B—S1B179 (3)O24—C24—C25—O26179.47 (13)
N11B—C12B—N13B—C14B12 (4)C23—C24—C25—O2662.10 (18)
S1B—C12B—N13B—C14B177.9 (18)N16A—C21—O26—C25179.94 (19)
C12B—N13B—C14B—O14B167 (2)N16B—C21—O26—C25169.9 (19)
C12B—N13B—C14B—C15B7 (4)C22—C21—O26—C2562.23 (17)
O14B—C14B—C15B—C16B171 (4)C24—C25—O26—C2165.48 (18)
N13B—C14B—C15B—C16B2 (6)C23—C22—O22—C221137.55 (15)
O14B—C14B—C15B—C51B10 (6)C21—C22—O22—C221103.97 (16)
N13B—C14B—C15B—C51B177 (4)C22—O22—C221—O2210.6 (3)
C12B—N11B—C16B—N16B162 (4)C22—O22—C221—C222179.02 (13)
C12B—N11B—C16B—C15B6 (6)C24—C23—O23—C231121.87 (15)
C14B—C15B—C16B—N11B2 (7)C22—C23—O23—C231119.67 (15)
C51B—C15B—C16B—N11B177 (4)C23—O23—C231—O2317.1 (2)
C14B—C15B—C16B—N16B158 (4)C23—O23—C231—C232172.85 (14)
C51B—C15B—C16B—N16B20 (7)C23—C24—O24—C241151.74 (14)
N11B—C12B—S1B—C17B11 (2)C25—C24—O24—C24188.97 (19)
N13B—C12B—S1B—C17B177.9 (19)C24—O24—C241—O2419.5 (3)
C16B—C15B—C51B—O51B20 (8)C24—O24—C241—C242170.37 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N13A—H13A···O221i0.882.112.942 (2)157
N13B—H13B···O221i0.881.962.780 (9)155
N16A—H16A···O51A0.881.922.645 (6)139
N16B—H16B···O51B0.882.012.68 (6)132
C22—H22···O14Aii1.002.313.304 (2)171
C22—H22···O14Bii1.002.523.468 (15)159
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC18H23N3O10·0.065H2OC17H21N3O9S
Mr442.57443.44
Crystal system, space groupOrthorhombic, P212121Orthorhombic, P212121
Temperature (K)120120
a, b, c (Å)14.3816 (2), 14.7626 (2), 20.1025 (3)6.9294 (1), 10.7415 (2), 26.4825 (5)
V3)4267.96 (10)1971.15 (6)
Z84
Radiation typeMo KαMo Kα
µ (mm1)0.110.22
Crystal size (mm)0.22 × 0.20 × 0.180.44 × 0.35 × 0.30
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Bruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.975, 0.9800.885, 0.936
No. of measured, independent and
observed [I > 2σ(I)] reflections
70888, 5407, 4925 12812, 4482, 4065
Rint0.0410.031
(sin θ/λ)max1)0.6500.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.088, 1.08 0.038, 0.096, 1.14
No. of reflections54074482
No. of parameters581327
No. of restraints340
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.200.42, 0.45
Absolute structure?Flack (1983)
Absolute structure parameter?0.02 (7)

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) for (I) top
N11—C121.304 (2)N31—C321.303 (2)
C12—N131.351 (3)C32—N331.352 (2)
N13—C141.413 (2)N33—C341.417 (3)
C14—C151.439 (3)C34—C351.437 (3)
C15—C161.411 (3)C35—C361.405 (3)
C16—N111.362 (2)C36—N311.364 (2)
C12—O121.328 (2)C32—O321.325 (2)
C14—O141.223 (2)C34—O341.226 (2)
C15—C511.432 (3)C35—C531.432 (3)
C51—O511.241 (2)C53—O531.232 (3)
C16—N161.345 (2)C36—N361.350 (2)
N11—C12—O12—C1215.9 (3)N31—C32—O32—C3212.6 (3)
C16—C15—C51—O510.5 (3)C36—C35—C53—O531.4 (3)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N16—H16···O510.882.032.707 (2)133
N36—H36···O530.882.062.725 (2)132
C24—H24···O14i1.002.343.237 (3)148
C44—H44···O2311.002.283.213 (3)155
C45—H45B···O34ii0.992.383.245 (3)145
C51—H51···O241iii0.952.543.442 (3)159
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1/2, y+1/2, z+1; (iii) x+1, y1/2, z+3/2.
Selected geometric parameters (Å, º) for (II) top
N11A—C12A1.325 (2)C12A—S1A1.746 (2)
C12A—N13A1.352 (2)C14A—O14A1.230 (2)
N13A—C14A1.403 (3)C15A—C51A1.436 (3)
C14A—C15A1.425 (3)C51A—O51A1.236 (3)
C15A—C16A1.412 (2)C16A—N16A1.335 (3)
C16A—N11A1.364 (2)
N11A—C12A—S1A—C17A176.69 (18)N11B—C12B—S1B—C17B11 (2)
C16A—C15A—C51A—O51A3.9 (7)C16B—C15B—C51B—O51B20 (8)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N13A—H13A···O221i0.882.112.942 (2)157
N13B—H13B···O221i0.881.962.780 (9)155
N16A—H16A···O51A0.881.922.645 (6)139
N16B—H16B···O51B0.882.012.68 (6)132
C22—H22···O14Aii1.002.313.304 (2)171
C22—H22···O14Bii1.002.523.468 (15)159
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2.
 

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