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The crystal structure of the title compound, C16H13FN2O6, was determined in order to establish the relative stereochemistry between the nucleoside base and the epoxide ring oxy­gen. This analysis allowed us to establish that the relationship of these two groups is cis. The furan­ose ring adopts an envelope conformation in which the oxy­gen is displaced above the plane (°E). The pseudorotational phase angle (P) is 88.5° and the puckering amplitude (τm) is 29.8°. The conformation about the C4—C5 bond is gauchetrans (ap) and the nucleoside base adopts the anti orientation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012352/cf6257sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012352/cf6257Isup2.hkl
Contains datablock I

CCDC reference: 217620

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.052
  • wR factor = 0.151
  • Data-to-parameter ratio = 8.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.834 0.981 Tmin' and Tmax expected: 0.960 0.991 RR' = 0.878 Please check that your absorption correction is appropriate. REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 1839 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1939 Completeness (_total/calc) 94.84% Alert C: < 95% complete General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 1839 Count of symmetry unique reflns 1939 Completeness (_total/calc) 94.84% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

2',3'-Anhydro-β-D-lyxofuranosyl nucleosides are important intermediates in the synthesis of nucleoside derivatives. Modification of these structures can be readily done through reactions involving the epoxide moiety (Huryn & Okabe, 1992; Roussev et al., 1997; Miah et al., 1998; Hirota et al., 1999; Hirota et al., 2000). Because nucleophilic opening of the epoxide ring in these compounds usually proceeds such that the nucleophile attacks regioselectively at C3', they have found particular application in the synthesis of β-arabinofuranosyl nucleosides (Codington et al., 1962; Hollenberg et al., 1977). Some 2',3'-anhydro-β-D-lyxofuranosyl nucleosides, or their corresponding 5' triphosphates, have also been shown to possess antiviral activity (Krayevsky et al., 1988; Dimoglo et al., 1997; Webb et al., 1988).

We have recently developed a highly convergent method for the synthesis of 2',3'-anhydro-β-D-lyxofuranosyl nucleosides that proceeds via the coupling of glycosyl sulfoxide (II) and a silylated nucleoside base, e.g. (III), mediated by trifluoromethanesulfonic acid anhydride (Callam et al., 2003). This approach is significantly more efficient than previously developed methods for the synthesis of compounds of this type, of which all have involved the installation of the epoxide ring on a preformed nucleoside. However, unambiguously determining the stereochemistry at the anomeric center in (I) was not possible using NMR spectroscopy and we therefore crystallized this compound so that the structure could be proven. The key issue was the relative stereochemistry between the epoxide oxygen and the nucleoside base.

The structure of (I) in the crystal is given in Fig. 1 and it is clear that there is a cis relationship between the nucleoside base and the epoxide oxygen. This is the relative stereochemistry that would have been predicted for a product formed by condensation of (II) and (III), given previous results on the glycosylation of alcohols by (II) (Gadikota et al., 2003). Note also that the absolute configuration for the structure was assigned on the basis of the known configuration of (II), which was synthesized from D-arabinose (Gadikota et al., 2003). The furanose ring in (I) adopts an envelope conformation, in which the ring oxygen is displaced above the plane (°E). The pseudorotational phase angle (P) is 88.5° and the puckering amplitude (τm) is 29.8° (Altona & Sundaralingam, 1972). In this regard, the structure is similar to other 2',3'-anhydro-β-D-lyxofuranosyl nucleotides for which crystal structures have been determined, e.g. (IV) and (V) (Gurskaya et al., 1990, 1996) or for which molecular-mechanics calculations have been carried out, e.g. (IV), (VI) and (VII) (Koole et al., 1991). In these compounds, the furanose and epoxide O atoms are on the same side of the furanose ring, resulting in a boat-like structure. In addition, the five-membered rings in these systems are generally less puckered than other nucleoside derivatives, which typically have τm magnitudes in the range 34–40° (Sanger, 1984). Similar structural features have been observed in ab initio and density functional theory calculations on 2,3-anhydro-β-D-lyxofuranosyl glycosides (Callam et al., 2001) and in the crystal structure of a 2,3-anhydro-α-D-lyxofuranosyl thioglycoside (Gallucci et al., 2000).

The orientation about the C4—C5 bond in (I) is gauche–trans (ap) (Sanger, 1984). This bond adopts the same orientation in the crystal structure of (IV) and in low-energy geometries obtained from molecular mechanics calculations of (IV), (VI) and (VII), thus indicating that the presence of the benozate ester on O3 in (I) does not alter the favored rotamer around the C4–C5 bond, as compared to the unprotected nucleosides. In the crystal structure of (V), however, the orientation of this bond differs from that in (I), (IV), (VI) and (VII), which is likely due to the presence of the additional hydroxymethyl group substituent at C4. Finally, in (I) the nucleoside base adopts the anti-conformation, which is the same as in compounds (IV)–(VII).

Experimental top

Sulfoxide (II) (0.5 mmol), 2,6-di-tert-butyl-4-methyl pyridine (2.5 mmol), and 4 Å molecular sieves (0.1 g) were dried for 3 h under vacuum in the presence of P2O5. To this mixture was added CH2Cl2 (10 ml) and the reaction mixture was cooled to 195 K. Triflic anhydride (0.6 mmol) was added and the mixture was stirred for 10 min before a solution of the persilylated nucleoside [(III), 0.6 mmol; Nishimura & Iwai, 1964] in CH2Cl2 (1.0 ml) was added dropwise by syringe over 2 min. After 15 min, the reaction mixture turned dark brown–green and a saturated aqueous solution of NaHCO3 was added, before the solution was allowed to warm to room temperature. The resulting solution was filtered through Celite, dried, filtered, and concentrated, to yield a crude oil that was purified by chromatography (2:1, hexanes/EtOAc), yielding (I) (0.35 mmol, 70%) as an oil. The product was recrystallized from 10:1 dichloromethane–hexane (m.p.: 366–367 K).

Refinement top

All H atoms were refined using a riding model, with bond lengths of 0.86 (N—-H), 0.93 (aryl H), 0.97 (CH2), and 0.98 Å (epoxide ring H). For all H atoms, Uiso(H) = 1.2Ueq(parent). Friedel pair reflections were merged prior to final refinement, as the refined Flack (1983) parameter was meaningless.

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2001); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A plot of the molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small circles of an arbitrary radius.
1-(2',3'-Anhydro-5'-O-benzoyl-β-D-lyxofuranoyl)-5-fluorouracil top
Crystal data top
C16H13FN2O6F(000) = 360
Mr = 348.28Dx = 1.506 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 96 reflections
a = 7.3537 (8) Åθ = 2.8–25.3°
b = 5.5149 (8) ŵ = 0.12 mm1
c = 19.290 (2) ÅT = 298 K
β = 100.928 (9)°Plate, colorless
V = 768.13 (17) Å30.32 × 0.20 × 0.07 mm
Z = 2
Data collection top
Bruker P4
diffractometer
980 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
θ/2θ scansh = 99
Absorption correction: ψ scan
(XPREP; Bruker, 2001)
k = 77
Tmin = 0.834, Tmax = 0.981l = 2525
3910 measured reflections3 standard reflections every 97 reflections
1839 independent reflections intensity decay: none
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)] = 0.052H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0707P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1839 reflectionsΔρmax = 0.27 e Å3
227 parametersΔρmin = 0.27 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.039 (8)
Crystal data top
C16H13FN2O6V = 768.13 (17) Å3
Mr = 348.28Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.3537 (8) ŵ = 0.12 mm1
b = 5.5149 (8) ÅT = 298 K
c = 19.290 (2) Å0.32 × 0.20 × 0.07 mm
β = 100.928 (9)°
Data collection top
Bruker P4
diffractometer
980 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XPREP; Bruker, 2001)
Rint = 0.048
Tmin = 0.834, Tmax = 0.9813 standard reflections every 97 reflections
3910 measured reflections intensity decay: none
1839 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.151H-atom parameters constrained
S = 1.05Δρmax = 0.27 e Å3
1839 reflectionsΔρmin = 0.27 e Å3
227 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
F10.8732 (4)0.4285 (7)0.19297 (15)0.0615 (9)
O10.5109 (4)0.3444 (7)0.18779 (16)0.0470 (9)
O20.2866 (5)0.0274 (7)0.1889 (2)0.0594 (11)
O30.5312 (6)0.5828 (10)0.3127 (2)0.0737 (13)
O40.4104 (8)0.6893 (13)0.4046 (3)0.123 (2)
O51.0030 (5)0.3851 (8)0.06968 (17)0.0545 (10)
O60.6325 (5)0.2691 (8)0.00678 (18)0.0598 (11)
N10.6133 (5)0.0793 (8)0.11036 (18)0.0387 (9)
N20.8221 (5)0.0490 (8)0.0413 (2)0.0451 (11)
H20.87330.02630.00530.054*
C10.4609 (6)0.2329 (10)0.1215 (2)0.0415 (11)
H10.43930.35810.08480.050*
C20.2817 (6)0.1024 (11)0.1230 (3)0.0514 (13)
H2A0.19910.05190.07940.062*
C30.2094 (7)0.2134 (10)0.1808 (3)0.0494 (13)
H30.07590.23810.17690.059*
C40.3443 (7)0.4048 (10)0.2140 (3)0.0482 (13)
H40.29980.56530.19670.058*
C50.3866 (8)0.4056 (13)0.2916 (3)0.0682 (17)
H5A0.27730.44850.31020.082*
H5B0.42810.24640.30920.082*
C60.5287 (10)0.7106 (14)0.3701 (3)0.0715 (18)
C70.6879 (10)0.8800 (13)0.3863 (3)0.0686 (17)
C80.6836 (12)1.0581 (15)0.4361 (3)0.089 (2)
H80.58561.06500.46020.107*
C90.8265 (16)1.2282 (19)0.4504 (5)0.114 (3)
H90.82221.35140.48290.136*
C100.9705 (15)1.213 (2)0.4168 (5)0.117 (3)
H101.06661.32440.42700.140*
C110.9779 (11)1.0343 (17)0.3675 (4)0.099 (3)
H111.07811.02680.34450.118*
C120.8366 (10)0.8664 (15)0.3522 (3)0.0764 (19)
H120.84150.74500.31910.092*
C130.6756 (6)0.1014 (10)0.1576 (2)0.0416 (11)
H130.62560.11800.19820.050*
C140.8082 (6)0.2546 (10)0.1459 (2)0.0413 (11)
C150.8867 (6)0.2409 (10)0.0842 (2)0.0411 (11)
C160.6836 (6)0.1120 (10)0.0497 (2)0.0412 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0523 (18)0.065 (2)0.0735 (19)0.0231 (18)0.0278 (14)0.0224 (19)
O10.0360 (17)0.050 (2)0.0567 (19)0.0027 (17)0.0123 (14)0.0085 (17)
O20.049 (2)0.0325 (19)0.103 (3)0.0025 (18)0.031 (2)0.006 (2)
O30.077 (3)0.082 (3)0.066 (2)0.012 (3)0.023 (2)0.029 (3)
O40.123 (4)0.152 (6)0.112 (4)0.020 (5)0.066 (3)0.052 (4)
O50.0420 (19)0.060 (2)0.066 (2)0.006 (2)0.0232 (16)0.005 (2)
O60.049 (2)0.068 (3)0.065 (2)0.007 (2)0.0185 (17)0.023 (2)
N10.0327 (19)0.043 (2)0.0426 (19)0.005 (2)0.0116 (16)0.004 (2)
N20.038 (2)0.056 (3)0.045 (2)0.001 (2)0.0169 (17)0.003 (2)
C10.035 (2)0.037 (3)0.053 (3)0.001 (2)0.008 (2)0.008 (2)
C20.038 (3)0.046 (3)0.070 (3)0.001 (3)0.010 (2)0.009 (3)
C30.034 (2)0.036 (3)0.080 (4)0.004 (2)0.016 (2)0.005 (3)
C40.043 (3)0.035 (3)0.069 (3)0.009 (2)0.019 (2)0.002 (3)
C50.070 (4)0.068 (4)0.073 (4)0.010 (4)0.029 (3)0.018 (4)
C60.086 (5)0.070 (4)0.059 (3)0.010 (4)0.016 (3)0.015 (4)
C70.086 (4)0.064 (4)0.051 (3)0.007 (4)0.002 (3)0.006 (3)
C80.120 (6)0.074 (5)0.067 (4)0.019 (5)0.004 (4)0.017 (4)
C90.162 (10)0.078 (6)0.083 (5)0.003 (8)0.023 (6)0.019 (5)
C100.129 (9)0.089 (7)0.108 (7)0.027 (7)0.037 (6)0.003 (7)
C110.090 (5)0.096 (7)0.101 (5)0.020 (6)0.005 (4)0.005 (5)
C120.080 (5)0.075 (5)0.071 (4)0.002 (4)0.008 (3)0.005 (4)
C130.036 (2)0.044 (3)0.048 (2)0.008 (2)0.017 (2)0.006 (2)
C140.036 (2)0.043 (3)0.047 (2)0.007 (3)0.014 (2)0.010 (3)
C150.033 (2)0.043 (3)0.049 (3)0.000 (3)0.011 (2)0.003 (3)
C160.030 (2)0.045 (3)0.048 (3)0.002 (2)0.006 (2)0.004 (3)
Geometric parameters (Å, º) top
F1—C141.344 (6)C3—H30.980
O1—C11.404 (5)C4—C51.469 (7)
O1—C41.450 (6)C4—H40.980
O2—C31.441 (6)C5—H5A0.970
O2—C21.452 (7)C5—H5B0.970
O3—C61.315 (7)C6—C71.484 (10)
O3—C51.445 (8)C7—C81.378 (9)
O4—C61.197 (8)C7—C121.382 (9)
O5—C151.238 (6)C8—C91.396 (12)
O6—C161.208 (6)C8—H80.930
N1—C131.370 (6)C9—C101.345 (12)
N1—C161.377 (6)C9—H90.930
N1—C11.453 (6)C10—C111.377 (13)
N2—C151.372 (6)C10—H100.930
N2—C161.384 (6)C11—C121.381 (10)
N2—H20.860C11—H110.930
C1—C21.507 (7)C12—H120.930
C1—H10.980C13—C141.341 (7)
C2—C31.457 (7)C13—H130.930
C2—H2A0.980C14—C151.420 (6)
C3—C41.506 (8)
C1—O1—C4109.0 (3)O3—C5—H5B110.3
C3—O2—C260.5 (3)C4—C5—H5B110.3
C6—O3—C5118.3 (5)H5A—C5—H5B108.6
C13—N1—C16121.9 (4)O4—C6—O3122.9 (7)
C13—N1—C1119.7 (4)O4—C6—C7124.9 (6)
C16—N1—C1118.2 (4)O3—C6—C7112.2 (5)
C15—N2—C16127.1 (4)C8—C7—C12119.7 (7)
C15—N2—H2116.5C8—C7—C6118.3 (7)
C16—N2—H2116.5C12—C7—C6122.0 (6)
O1—C1—N1108.3 (3)C7—C8—C9120.0 (8)
O1—C1—C2105.7 (4)C7—C8—H8120.0
N1—C1—C2115.2 (4)C9—C8—H8120.0
O1—C1—H1109.2C10—C9—C8119.6 (9)
N1—C1—H1109.2C10—C9—H9120.2
C2—C1—H1109.2C8—C9—H9120.2
O2—C2—C359.4 (3)C9—C10—C11121.1 (10)
O2—C2—C1112.1 (4)C9—C10—H10119.5
C3—C2—C1105.2 (4)C11—C10—H10119.5
O2—C2—H2A121.3C10—C11—C12120.0 (9)
C3—C2—H2A121.3C10—C11—H11120.0
C1—C2—H2A121.3C12—C11—H11120.0
O2—C3—C260.1 (4)C11—C12—C7119.6 (7)
O2—C3—C4112.7 (4)C11—C12—H12120.2
C2—C3—C4108.3 (4)C7—C12—H12120.2
O2—C3—H3120.3C14—C13—N1120.6 (4)
C2—C3—H3120.3C14—C13—H13119.7
C4—C3—H3120.3N1—C13—H13119.7
O1—C4—C5109.0 (4)C13—C14—F1120.8 (4)
O1—C4—C3102.8 (4)C13—C14—C15122.1 (4)
C5—C4—C3115.5 (5)F1—C14—C15117.1 (4)
O1—C4—H4109.7O5—C15—N2122.3 (4)
C5—C4—H4109.7O5—C15—C14124.3 (5)
C3—C4—H4109.7N2—C15—C14113.4 (4)
O3—C5—C4107.0 (5)O6—C16—N1124.0 (5)
O3—C5—H5A110.3O6—C16—N2121.3 (4)
C4—C5—H5A110.3N1—C16—N2114.7 (4)
C4—O1—C1—N1154.4 (4)O3—C6—C7—C8167.2 (6)
C4—O1—C1—C230.4 (5)O4—C6—C7—C12168.3 (8)
C13—N1—C1—O157.7 (5)O3—C6—C7—C1211.5 (9)
C16—N1—C1—O1126.0 (5)C12—C7—C8—C91.9 (10)
C13—N1—C1—C260.3 (5)C6—C7—C8—C9176.9 (7)
C16—N1—C1—C2115.9 (5)C7—C8—C9—C101.9 (13)
C3—O2—C2—C195.1 (5)C8—C9—C10—C111.2 (15)
O1—C1—C2—O244.1 (5)C9—C10—C11—C120.4 (14)
N1—C1—C2—O275.4 (5)C10—C11—C12—C70.4 (11)
O1—C1—C2—C318.6 (5)C8—C7—C12—C111.1 (10)
N1—C1—C2—C3138.1 (4)C6—C7—C12—C11177.6 (6)
C2—O2—C3—C498.7 (5)C16—N1—C13—C140.3 (7)
C1—C2—C3—O2107.0 (4)C1—N1—C13—C14175.8 (5)
O2—C2—C3—C4106.2 (4)N1—C13—C14—F1178.3 (4)
C1—C2—C3—C40.8 (6)N1—C13—C14—C151.3 (8)
C1—O1—C4—C5152.3 (5)C16—N2—C15—O5175.0 (5)
C1—O1—C4—C329.2 (5)C16—N2—C15—C145.4 (7)
O2—C3—C4—O148.0 (5)C13—C14—C15—O5176.5 (5)
C2—C3—C4—O116.5 (5)F1—C14—C15—O53.8 (7)
O2—C3—C4—C570.6 (6)C13—C14—C15—N23.9 (7)
C2—C3—C4—C5135.1 (5)F1—C14—C15—N2175.8 (4)
C6—O3—C5—C4144.5 (5)C13—N1—C16—O6180.0 (5)
O1—C4—C5—O358.9 (6)C1—N1—C16—O63.9 (7)
C3—C4—C5—O3174.1 (5)C13—N1—C16—N20.8 (6)
C5—O3—C6—O41.3 (10)C1—N1—C16—N2176.9 (4)
C5—O3—C6—C7178.5 (6)C15—N2—C16—O6176.8 (5)
O4—C6—C7—C813.0 (11)C15—N2—C16—N13.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O5i0.862.012.846 (5)165
Symmetry code: (i) x+2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC16H13FN2O6
Mr348.28
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)7.3537 (8), 5.5149 (8), 19.290 (2)
β (°) 100.928 (9)
V3)768.13 (17)
Z2
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.32 × 0.20 × 0.07
Data collection
DiffractometerBruker P4
diffractometer
Absorption correctionψ scan
(XPREP; Bruker, 2001)
Tmin, Tmax0.834, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
3910, 1839, 980
Rint0.048
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.151, 1.05
No. of reflections1839
No. of parameters227
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.27

Computer programs: XSCANS (Bruker, 1996), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Bruker, 2001), SHELXL97.

Selected geometric parameters (Å, º) top
O1—C11.404 (5)N1—C11.453 (6)
O1—C41.450 (6)C1—C21.507 (7)
O2—C31.441 (6)C2—C31.457 (7)
O2—C21.452 (7)C3—C41.506 (8)
O3—C51.445 (8)C4—C51.469 (7)
C1—O1—C4109.0 (3)O2—C2—C359.4 (3)
C3—O2—C260.5 (3)C3—C2—C1105.2 (4)
O1—C1—N1108.3 (3)O2—C3—C260.1 (4)
O1—C1—C2105.7 (4)C2—C3—C4108.3 (4)
N1—C1—C2115.2 (4)O1—C4—C3102.8 (4)
C4—O1—C1—C230.4 (5)C1—O1—C4—C329.2 (5)
C13—N1—C1—O157.7 (5)C2—C3—C4—O116.5 (5)
C16—N1—C1—O1126.0 (5)O1—C4—C5—O358.9 (6)
O1—C1—C2—C318.6 (5)C3—C4—C5—O3174.1 (5)
C1—C2—C3—C40.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O5i0.862.012.846 (5)165
Symmetry code: (i) x+2, y+1/2, z.
 

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