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In the title compound, C22H24N4O11, the N-glycosidic torsion angles O′—C′—N—C and O′—C′—N—N are −34.1 (6) and 148.8 (3)°, respectively. The mol­ecule displays an α-D configuration with the ribo­furan­ose moiety in an O′-exo–C′-endo pucker. There are only weak C—H...O and C—H...N intra- and intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100005394/jz1388sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100005394/jz1388Isup2.hkl
Contains datablock I

CCDC reference: 147672

Comment top

The Dimroth reaction of glycosyl azides with dimethyl-3-oxo-glutarate (DOG) was recently used to produce the intermediates for further cyclizations to various 8-aza-3-deazaguanine nucleosides. The stereochemistry followed a favourable path even with 1,2-cis glycosyl azides, in sharp contrast to the condensations with cyanoacetamide, which were reported to yield 1,2-trans nucleosides exclusively (Štimac et al., 1999). Herein, we report the crystal structure of the only product (I) between 2,3-O-isopropylidene-5-O– (4-nitrobenzoyl)-α-D-ribofuranosyl azide and DOG, which revealed the glycosidation site N1 of the 4-methoxycarbonyl-1,2,3-triazol-5-yl acetate, and the α-anomeric configuration of the nucleoside. The molecule with the atomic numbering scheme is depicted in Fig. 1. Selected geometric parameters are presented in Table 1. The absolute configuration was assigned to agree with the known chirality of the sugar moiety (α-D-ribofuranose).

A survey of the Cambridge Structural Database (Allen & Kennard, 1993) revealed 18 examples where the aglycon moiety of the nucleoside was either the 1,2,4-triazole derivative alone (BESZII, BESZOO, FULRAF, JAZVEL, JAZVIP, JAZVOV, RIBVAR, RFRTZL, VAWMIP, VAWMOV, VICFUI, VICGAP, VIRAZL), or the 1,2,4-triazole derivative as part of the bicyclic system (CAFVAJ, CAFVEN, DIHNIR, VAPZOB, VAWMEL). Only in the structure determination of 2-β-D-ribofuranosyl-1,2,3-triazole-4,5-dicarboxamide dihydrate (JAZYUE) was the 1,2,3-triazole derivative an aglycon to ribofuranose (Sanghvi et al., 1990).

The orientation of the heterocyclic base relative to the sugar moiety (defined as anti or syn) is determined by the torsion angle about the N-glycosidic bond, explicitly, for purines and pyrimidines. In the cases of modified nucleosides with e.g. a five-membered base ring system, the sequence of atoms is chosen as far as possible to correspond closely with the normal substrates (Sundaralingham, 1975; IUPAC-IUB Joint Commission on Biochemical Nomenclature, 1983). The appropriate torsion angles O4'—C1'—N1—C5 and O4'—C1'—N1—N2 in this study are −34.1 (6) and 148.8 (3)°, respectively, suggesting high anti-configuration. The conformation about the C4'—C5' bond [O4'—C4'—C5'—O11 − 59.6 (4)°] is in the gauche range. The ribofuranose moiety exists in an O4'-exo-C4'-endo pucker. The corresponding Cremer–Pople (Cremer & Pople, 1975) puckering parameters q2 and ϕ2 are 0.246 (4) Å and 161.7 (10)° (Spek, 1998; Farrugia, 2000), respectively, suggesting the twisted form around the bond C4'—O4'. The bond lengths and angles are normal and in agreement with the values for the related compounds. The bond lengths N1—C5 1.341 (5), N1—N2 1.354 (4), N2—N3 1.289 (5), N3—C4 1.360 (6) and C4—C5 1.399 (6) Å in the 1,2,3-triazole ring suggest considerable delocalization of electrons and the prevalent double bond character of N2—N3 bonds. The triazole moiety is planar to within 0.005 (3) Å, and the phenyl part of the para-nitrobenzoyl group to within 0.011 (3) Å. The dihedral angles between the para-nitro group –NO2 (N11, O111, O112), the carboxylate group –COO (C10, O11, O12), and the phenyl ring (C11–C16) are 10.8 (4) and 5.8 (3)°, respectively.

Because the –OH groups of the molecule are protected with either the para-nitrobenzoate or the isopropylidene group, the molecule is essentially hydrophobic. There are only weak C—H···O and C—H···N intra- and intermolecular interactions (Table 1), which control the packing. Although the data were collected at 150 K, there is still appreciable thermal motion of the terminal C32 atom.

Experimental top

The title compound was the only isolated product from the reaction between a solution of 2,3-O-isopropylidene-5-O-(4-nitrobenzoyl)-α-D-ribofuranosyl azide (4 mmol) in dimethyl sulfoxide (5 ml) and dimethyl-3-oxoglutarate (8 mmol) together with finely ground K2CO3 (4 mmol). The heterogenous mixture was stirred at 318 K for 72 h. The precipitate was washed with water, dried in air and dissolved in CHCl3 (30 ml). The solution was washed with 1M Na2CO3 (2 x 16 ml), 0.1M HCl (16 ml) and brine (16 ml) and finally dried with Na2SO4. Solvent was removed and the residue was purified by chromatography on silica gel, first with 0.2% ethanol in CH2Cl2, followed by CH2Cl2–ether mixture. The fragile, plate-like, elongated crystals with melting point 477–479 K were obtained after several recrystallization from ethyl acetate. Details are given by Štimac et al. (1999).

Refinement top

All H atoms were found in the difference electron density map and were placed at the calculated positions with isotropic displacement parameters taken from those of the attached heavy atoms and multiplied by 1.5. With the absence of suitable anomalous scatterers for Mo Kα radiation, the determination of the absolute configuration was not possible. The absolute configuration was assigned to agree with the known chirality of the ribofuranose moiety and the Friedel diffraction data were merged accordingly. Three strong reflections 131, 109 and 0014 were omitted from the refinement in the final stage due to inaccuracy in measurement.

Computing details top

Data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1971), PLATON (Spek, 1998), ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1971) view of the molecule with atomic numbering. Anisotropic displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.
methyl {1-[2,3-O-isopropylidene-5-O-(4-nitrobenzoyl)-α-D– ribofuranosyl]-4-methoxycarbonyl-1,2,3-triazol-5-yl} acetate top
Crystal data top
C22H24N4O11Dx = 1.440 Mg m3
Dm = 1.42 (5) Mg m3
Dm measured by flotation
Mr = 520.45Melting point = 204–206 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 8.845 (2) ÅCell parameters from 28700 reflections
b = 9.931 (2) Åθ = 3–25°
c = 27.325 (5) ŵ = 0.12 mm1
V = 2400.2 (8) Å3T = 150 K
Z = 4Needles, colourless
F(000) = 10880.35 × 0.13 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
2111 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
301 frames in 5 sets of ω scans. Rotation/frame=2°. Crystal–detector distance=45 mm. Measuring time=200 s/°.h = 1010
24551 measured reflectionsk = 1111
2358 independent reflectionsl = 3231
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.122Calculated w = 1/[σ2(Fo2) + (0.0546P)2 + 1.5179P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.038
2358 reflectionsΔρmax = 0.54 e Å3
335 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0067 (16)
Crystal data top
C22H24N4O11V = 2400.2 (8) Å3
Mr = 520.45Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.845 (2) ŵ = 0.12 mm1
b = 9.931 (2) ÅT = 150 K
c = 27.325 (5) Å0.35 × 0.13 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
2111 reflections with I > 2σ(I)
24551 measured reflectionsRint = 0.057
2358 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.09Δρmax = 0.54 e Å3
2358 reflectionsΔρmin = 0.24 e Å3
335 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1'0.6307 (4)0.8855 (4)0.18894 (14)0.0376 (9)
H10.69610.89150.21870.056*
C2'0.4774 (4)0.8216 (4)0.20306 (14)0.0378 (9)
H20.46500.81480.23930.057*
C3'0.4820 (4)0.6825 (4)0.17878 (14)0.0392 (9)
H30.45400.60890.20200.059*
C4'0.6409 (5)0.6661 (4)0.15912 (15)0.0379 (9)
H40.63460.62510.12580.057*
O4'0.7006 (3)0.8011 (3)0.15439 (9)0.0373 (7)
C5'0.7432 (5)0.5803 (4)0.19017 (14)0.0417 (10)
H50.84490.57390.17520.063*
H60.70130.48830.19360.063*
O20.3545 (3)0.8892 (3)0.18087 (11)0.0440 (7)
C10.2650 (5)0.7883 (4)0.15631 (16)0.0453 (10)
O30.3766 (3)0.6952 (3)0.13990 (10)0.0454 (7)
C20.1880 (5)0.8498 (6)0.11333 (18)0.0622 (13)
H70.11280.91520.12470.093*
H80.26300.89550.09280.093*
H90.13770.77930.09430.093*
C30.1558 (5)0.7230 (5)0.19226 (19)0.0545 (12)
H100.08100.78960.20290.082*
H110.10410.64760.17630.082*
H120.21200.68980.22070.082*
O110.7515 (3)0.6456 (3)0.23720 (9)0.0403 (7)
O120.9497 (3)0.5140 (3)0.25665 (10)0.0470 (7)
C100.8659 (4)0.6053 (4)0.26637 (14)0.0387 (9)
C110.8791 (4)0.6907 (4)0.31113 (15)0.0380 (9)
C121.0027 (5)0.6691 (5)0.34182 (16)0.0482 (11)
H131.07180.59880.33450.072*
C131.0260 (5)0.7470 (5)0.38204 (17)0.0510 (11)
H141.11000.73160.40300.076*
C140.9246 (5)0.8488 (4)0.39157 (15)0.0442 (10)
C150.8003 (5)0.8719 (4)0.36319 (15)0.0469 (10)
H150.73040.94090.37150.070*
C160.7779 (5)0.7930 (4)0.32216 (15)0.0428 (10)
H160.69320.80870.30150.064*
N110.9517 (5)0.9355 (4)0.43481 (15)0.0591 (11)
O1110.8537 (5)1.0111 (4)0.44807 (15)0.0944 (14)
O1121.0716 (5)0.9275 (5)0.45604 (16)0.0865 (12)
N10.6159 (4)1.0186 (3)0.16730 (11)0.0373 (8)
N20.6226 (4)1.1245 (4)0.19845 (13)0.0483 (9)
N30.6018 (4)1.2321 (4)0.17292 (16)0.0529 (10)
C40.5828 (5)1.1970 (4)0.12519 (18)0.0493 (11)
C50.5904 (4)1.0568 (4)0.12095 (14)0.0361 (9)
C200.5770 (5)0.9642 (4)0.07831 (14)0.0386 (9)
H170.51660.88460.08790.058*
H180.52261.01080.05160.058*
C210.7284 (5)0.9183 (4)0.05990 (13)0.0394 (10)
O210.8440 (3)0.9786 (3)0.06469 (10)0.0489 (8)
O220.7165 (4)0.8023 (3)0.03613 (10)0.0545 (8)
C220.8542 (7)0.7580 (6)0.0119 (2)0.0814 (19)
H190.83510.67300.00520.122*
H200.88650.82650.01170.122*
H210.93390.74460.03630.122*
C310.5648 (7)1.3016 (6)0.0904 (2)0.0708 (15)
O310.5500 (5)1.4199 (3)0.0977 (2)0.0924 (14)
O320.5689 (8)1.2559 (4)0.04509 (18)0.119 (2)
C320.5566 (18)1.3652 (8)0.0091 (3)0.194 (6)
H220.55661.32720.02400.291*
H230.46221.41480.01450.291*
H240.64261.42650.01280.291*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1'0.034 (2)0.046 (2)0.033 (2)0.006 (2)0.0025 (17)0.0025 (18)
C2'0.035 (2)0.042 (2)0.0363 (19)0.0078 (19)0.0037 (17)0.0011 (18)
C3'0.033 (2)0.041 (2)0.043 (2)0.0055 (19)0.0012 (18)0.0012 (19)
C4'0.034 (2)0.036 (2)0.044 (2)0.0064 (18)0.0032 (18)0.0044 (19)
O4'0.0333 (14)0.0381 (15)0.0405 (14)0.0030 (13)0.0074 (12)0.0011 (13)
C5'0.036 (2)0.043 (2)0.046 (2)0.003 (2)0.0047 (19)0.0060 (19)
O20.0284 (13)0.0425 (16)0.0610 (17)0.0063 (13)0.0026 (13)0.0015 (15)
C10.032 (2)0.047 (2)0.057 (2)0.003 (2)0.004 (2)0.003 (2)
O30.0318 (14)0.0539 (17)0.0505 (16)0.0021 (15)0.0034 (13)0.0108 (15)
C20.043 (2)0.073 (3)0.070 (3)0.006 (3)0.006 (2)0.001 (3)
C30.034 (2)0.049 (3)0.081 (3)0.011 (2)0.009 (2)0.005 (2)
O110.0367 (14)0.0422 (15)0.0420 (14)0.0053 (13)0.0012 (12)0.0004 (13)
O120.0396 (16)0.0448 (16)0.0566 (16)0.0098 (15)0.0042 (14)0.0007 (14)
C100.031 (2)0.037 (2)0.048 (2)0.001 (2)0.0067 (19)0.0085 (19)
C110.0276 (19)0.042 (2)0.045 (2)0.0009 (18)0.0039 (17)0.0087 (19)
C120.033 (2)0.052 (3)0.059 (2)0.011 (2)0.001 (2)0.004 (2)
C130.036 (2)0.060 (3)0.057 (3)0.003 (2)0.009 (2)0.003 (2)
C140.040 (2)0.046 (2)0.046 (2)0.002 (2)0.0027 (19)0.000 (2)
C150.047 (2)0.046 (2)0.048 (2)0.012 (2)0.001 (2)0.005 (2)
C160.037 (2)0.047 (2)0.045 (2)0.005 (2)0.0008 (19)0.006 (2)
N110.067 (3)0.055 (2)0.055 (2)0.006 (2)0.004 (2)0.001 (2)
O1110.104 (3)0.095 (3)0.084 (3)0.044 (3)0.024 (2)0.037 (2)
O1120.078 (3)0.093 (3)0.089 (3)0.005 (3)0.029 (2)0.021 (2)
N10.0351 (18)0.0349 (17)0.0420 (18)0.0102 (15)0.0050 (15)0.0060 (15)
N20.0409 (19)0.048 (2)0.056 (2)0.0089 (19)0.0123 (18)0.022 (2)
N30.040 (2)0.042 (2)0.077 (3)0.0011 (17)0.008 (2)0.022 (2)
C40.039 (2)0.037 (2)0.072 (3)0.004 (2)0.006 (2)0.000 (2)
C50.029 (2)0.034 (2)0.045 (2)0.0032 (17)0.0036 (18)0.0001 (17)
C200.040 (2)0.039 (2)0.037 (2)0.0070 (19)0.0032 (18)0.0010 (18)
C210.049 (2)0.039 (2)0.0308 (19)0.001 (2)0.0069 (18)0.0023 (18)
O210.0463 (17)0.0527 (18)0.0478 (16)0.0078 (16)0.0087 (14)0.0090 (15)
O220.069 (2)0.0442 (17)0.0509 (17)0.0097 (17)0.0159 (16)0.0172 (14)
C220.080 (4)0.084 (4)0.081 (4)0.036 (4)0.018 (3)0.047 (3)
C310.057 (3)0.064 (4)0.092 (4)0.008 (3)0.007 (3)0.000 (3)
O310.080 (3)0.0356 (19)0.161 (4)0.0039 (19)0.006 (3)0.012 (2)
O320.214 (7)0.048 (2)0.096 (3)0.018 (3)0.034 (4)0.032 (2)
C320.39 (2)0.087 (5)0.104 (6)0.012 (10)0.081 (9)0.030 (5)
Geometric parameters (Å, º) top
C1'—O4'1.406 (5)C13—C141.377 (6)
C1'—N11.454 (5)C14—C151.365 (6)
C1'—C2'1.546 (5)C14—N111.481 (6)
C2'—O21.415 (5)C15—C161.382 (6)
C2'—C3'1.533 (6)N11—O1111.203 (5)
C3'—O31.419 (5)N11—O1121.212 (5)
C3'—C4'1.513 (5)N1—C51.341 (5)
C4'—O4'1.446 (5)N1—N21.354 (4)
C4'—C5'1.505 (6)N2—N31.289 (5)
C5'—O111.441 (4)N3—C41.360 (6)
O2—C11.443 (5)C4—C51.399 (6)
C1—O31.425 (5)C4—C311.417 (7)
C1—C21.489 (6)C5—C201.489 (5)
C1—C31.522 (6)C20—C211.501 (6)
O11—C101.348 (5)C21—O211.192 (5)
O12—C101.201 (4)C21—O221.327 (5)
C10—C111.493 (6)O22—C221.455 (6)
C11—C161.387 (6)C31—O311.199 (6)
C11—C121.394 (6)C31—O321.319 (7)
C12—C131.360 (6)O32—C321.469 (8)
O4'—C1'—N1108.0 (3)C12—C13—C14118.1 (4)
O4'—C1'—C2'108.0 (3)C15—C14—C13122.8 (4)
N1—C1'—C2'113.3 (3)C15—C14—N11119.1 (4)
O2—C2'—C3'105.2 (3)C13—C14—N11118.1 (4)
O2—C2'—C1'111.9 (3)C14—C15—C16118.8 (4)
C3'—C2'—C1'103.8 (3)C15—C16—C11119.9 (4)
O3—C3'—C4'110.7 (3)O111—N11—O112121.8 (4)
O3—C3'—C2'103.1 (3)O111—N11—C14119.1 (4)
C4'—C3'—C2'106.0 (3)O112—N11—C14119.1 (4)
O4'—C4'—C5'110.8 (3)C5—N1—N2112.4 (3)
O4'—C4'—C3'105.7 (3)C5—N1—C1'131.0 (3)
C5'—C4'—C3'114.8 (3)N2—N1—C1'116.5 (3)
C1'—O4'—C4'109.4 (3)N3—N2—N1107.3 (3)
O11—C5'—C4'106.2 (3)N2—N3—C4108.9 (3)
C2'—O2—C1106.9 (3)N3—C4—C5109.2 (4)
O3—C1—O2102.5 (3)N3—C4—C31118.0 (4)
O3—C1—C2109.6 (4)C5—C4—C31132.8 (5)
O2—C1—C2109.4 (4)N1—C5—C4102.2 (4)
O3—C1—C3111.5 (4)N1—C5—C20125.3 (3)
O2—C1—C3110.1 (3)C4—C5—C20132.5 (4)
C2—C1—C3113.2 (4)C5—C20—C21112.3 (3)
C3'—O3—C1106.1 (3)O21—C21—O22123.9 (4)
C10—O11—C5'115.6 (3)O21—C21—C20125.1 (3)
O12—C10—O11123.8 (4)O22—C21—C20110.9 (4)
O12—C10—C11124.2 (4)C21—O22—C22114.8 (4)
O11—C10—C11112.0 (3)O31—C31—O32119.7 (6)
C16—C11—C12119.2 (4)O31—C31—C4128.3 (6)
C16—C11—C10122.9 (4)O32—C31—C4112.0 (5)
C12—C11—C10117.8 (4)C31—O32—C32111.8 (5)
C13—C12—C11121.2 (4)
O4'—C1'—C2'—O2104.3 (3)C12—C13—C14—N11178.8 (4)
N1—C1'—C2'—O215.2 (4)C13—C14—C15—C162.4 (7)
O4'—C1'—C2'—C3'8.6 (4)N11—C14—C15—C16178.3 (4)
N1—C1'—C2'—C3'128.2 (3)C14—C15—C16—C111.4 (6)
O2—C2'—C3'—O39.2 (4)C12—C11—C16—C150.0 (6)
C1'—C2'—C3'—O3108.4 (3)C10—C11—C16—C15177.3 (4)
O2—C2'—C3'—C4'125.6 (3)C15—C14—N11—O11110.5 (6)
C1'—C2'—C3'—C4'8.0 (4)C13—C14—N11—O111168.8 (5)
O3—C3'—C4'—O4'89.7 (4)C15—C14—N11—O112170.0 (4)
C2'—C3'—C4'—O4'21.4 (4)C13—C14—N11—O11210.7 (6)
O3—C3'—C4'—C5'147.9 (3)O4'—C1'—N1—C534.1 (5)
C2'—C3'—C4'—C5'101.0 (4)C2'—C1'—N1—C585.4 (5)
N1—C1'—O4'—C4'145.9 (3)O4'—C1'—N1—N2148.8 (3)
C2'—C1'—O4'—C4'23.1 (4)C2'—C1'—N1—N291.7 (4)
C5'—C4'—O4'—C1'96.9 (3)C5—N1—N2—N30.0 (4)
C3'—C4'—O4'—C1'28.1 (4)C1'—N1—N2—N3177.6 (3)
O4'—C4'—C5'—O1159.6 (4)N1—N2—N3—C40.5 (5)
C3'—C4'—C5'—O1160.1 (4)N2—N3—C4—C50.9 (5)
C3'—C2'—O2—C115.6 (4)N2—N3—C4—C31177.3 (4)
C1'—C2'—O2—C1127.6 (3)N2—N1—C5—C40.5 (5)
C2'—O2—C1—O334.6 (4)C1'—N1—C5—C4177.7 (4)
C2'—O2—C1—C2150.8 (3)N2—N1—C5—C20180.0 (4)
C2'—O2—C1—C384.2 (4)C1'—N1—C5—C202.8 (7)
C4'—C3'—O3—C1144.0 (3)N3—C4—C5—N10.8 (5)
C2'—C3'—O3—C131.1 (4)C31—C4—C5—N1176.9 (5)
O2—C1—O3—C3'41.1 (4)N3—C4—C5—C20179.7 (4)
C2—C1—O3—C3'157.2 (4)C31—C4—C5—C202.5 (9)
C3—C1—O3—C3'76.7 (4)N1—C5—C20—C2179.4 (5)
C4'—C5'—O11—C10163.8 (3)C4—C5—C20—C2199.9 (5)
C5'—O11—C10—O125.9 (5)C5—C20—C21—O2125.6 (6)
C5'—O11—C10—C11172.1 (3)C5—C20—C21—O22156.1 (3)
O12—C10—C11—C16178.0 (4)O21—C21—O22—C225.4 (6)
O11—C10—C11—C164.1 (5)C20—C21—O22—C22173.0 (4)
O12—C10—C11—C124.7 (6)N3—C4—C31—O317.5 (9)
O11—C10—C11—C12173.3 (3)C5—C4—C31—O31174.9 (6)
C16—C11—C12—C130.5 (6)N3—C4—C31—O32171.1 (5)
C10—C11—C12—C13177.0 (4)C5—C4—C31—O326.5 (9)
C11—C12—C13—C140.4 (7)O31—C31—O32—C321.1 (11)
C12—C13—C14—C151.9 (7)C4—C31—O32—C32177.6 (8)

Experimental details

Crystal data
Chemical formulaC22H24N4O11
Mr520.45
Crystal system, space groupOrthorhombic, P212121
Temperature (K)150
a, b, c (Å)8.845 (2), 9.931 (2), 27.325 (5)
V3)2400.2 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.35 × 0.13 × 0.13
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
24551, 2358, 2111
Rint0.057
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.122, 1.09
No. of reflections2358
No. of parameters335
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.24

Computer programs: KappaCCD Reference Manual (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1971), PLATON (Spek, 1998), ORTEP-3 (Farrugia, 1999).

Selected geometric parameters (Å, º) top
C1'—O4'1.406 (5)C14—N111.481 (6)
C1'—N11.454 (5)N11—O1111.203 (5)
C1'—C2'1.546 (5)N11—O1121.212 (5)
C2'—C3'1.533 (6)N1—C51.341 (5)
C3'—C4'1.513 (5)N1—N21.354 (4)
C4'—O4'1.446 (5)N2—N31.289 (5)
C4'—C5'1.505 (6)N3—C41.360 (6)
C5'—O111.441 (4)C4—C51.399 (6)
O4'—C1'—C2'—C3'8.6 (4)O4'—C4'—C5'—O1159.6 (4)
C1'—C2'—C3'—C4'8.0 (4)C3'—C4'—C5'—O1160.1 (4)
C2'—C3'—C4'—O4'21.4 (4)O4'—C1'—N1—C534.1 (5)
C2'—C1'—O4'—C4'23.1 (4)O4'—C1'—N1—N2148.8 (3)
C3'—C4'—O4'—C1'28.1 (4)
 

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