2,2′-Anhydro-1-(3′,5′-di-O-acetyl-β-d- arabinofuranosyl)uracil, a cyclouridine nucleoside with a C4′- endo furanosyl conformation

Article abstract of DOI:10.1107/S0108270113000395

2,2′-Anhydro-1-(3′,5′-di-O-acetyl-β-d- arabinofuranosyl)uracil, C₁₃H₁₄N₂O₇, was obtained by refluxing 2′,3′-O-(methoxymethylene)uridine in acetic anhydride. The structure exhibits a nearly perfect C₄′- endo (⁴ E) conformation. The best four-atom plane of the five-membered furanose ring is O - C - C - C, involving the C atoms of the fused five-membered oxazolidine ring, and the torsion angle is only -0.4 (2)°. The oxazolidine ring is essentially coplanar with the six-membered uracil ring [r.m.s. deviation = 0.012 (5) A and dihedral angle = -3.2 (3)°]. The conformation at the exocyclic C - C bond is gauche-trans which is stabilized by various C - H...π and C - O...π interactions. Copyright

Full text of DOI:10.1107/S0108270113000395

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
However, when repeating this procedure in our laboratory, we
found that 2,20-anhydro-1-(30,50-di-O-acetyl-ꢀ-d-arabinofur-
anosyl)uracil, (I), was the main product instead of (II). The
expected product (II) formed but in low yield (23%) and was
found to be unstable in boiling acetic anhydride. 30,50-Di-
acetylated cyclouridine, (I), was obtained in 65% yield after
ISSN 0108-2701
2,20-Anhydro-1-(30,50-di-O-acetyl-
b-D-arabinofuranosyl)uracil, a
cyclouridine nucleoside with a
C40-endo furanosyl conformation
Ying Fu,* Yin-Xia He, Hong-Xia Hou, Wen-Bo Zhu, Hu-Lin
Li, Chao Wu and Fang-Yan Xian
Key Laboratory of Polymer Materials of Gansu Province, The Key Laboratory of
Ecological Environment Related Polymer Materials of the Ministry of Education,
Incorporated in the Local and Provincial College of Chemistry and Chemical
Engineering, Northwest Normal University, Lanzhou 730070, People’s Republic
of China
Correspondence e-mail: fuying@iccas.ac.cn
Received 28 November 2012
Accepted 4 January 2013
Online 12 February 2013
2,20-Anhydro-1-(30,50-di-O-acetyl-ꢀ-d-arabinofuranosyl)-
uracil, C13H14N2O7, was obtained by refluxing 20,30-O-(meth-
oxymethylene)uridine in acetic anhydride. The structure
exhibits a nearly perfect C40-endo (4E) conformation. The
best four-atom plane of the five-membered furanose ring is
O—C—C—C, involving the C atoms of the fused five-
membered oxazolidine ring, and the torsion angle is only
ꢀ0.4 (2)ꢁ. The oxazolidine ring is essentially coplanar with the
boiling for 5 h. To confirm its molecular structure, as well as to
provide the solid-state conformation of this fused polycyclic
˚
six-membered uracil ring [r.m.s. deviation = 0.012 (5) A and
dihedral angle = ꢀ3.2 (3)ꢁ]. The conformation at the exocyclic
C—C bond is gauche–trans which is stabilized by various C—
Hꢂ ꢂ ꢂꢁ and C—Oꢂ ꢂ ꢂꢁ interactions.
Comment
Conformationally restricted cyclonucleoside analogues are of
considerable importance in biochemistry, medicinal chemistry
and nucleoside-based drug discovery (Wnuk et al., 2002;
Bennett & Swayze, 2010). These compounds are key inter-
mediates for the synthesis of a considerable number of
nucleoside analogues (Dai et al., 2008; Belostotskii et al.,
2012). Besides their utility in synthetic chemistry, cyclo-
nucleosides, with a rigid fused polycyclic system, are good
reference compounds to correlate X-ray data with dihedral
angles obtained from proton–proton coupling constants
(Jardetzky, 1960; Cross & Schleich, 1973) and circular
dichroism (Miles et al. 1979).
In our attempt to synthesize deoxyuridine derivatives, we
tried to make use of a pivotal intermediate, 1-(5-O-
acetyl-2,3-dideoxy-ꢀ-d-glycero-pent-2-enofuranosyl)uracil,
(II), which was reported to be readily obtained from 20,30-O-
(methoxymethylene)uridine, (III) (Shiragami et al., 1988).
Figure 1
The molecular structure of (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 50% probability level.
282 # 2013 International Union of Crystallography
doi:10.1107/S0108270113000395
Acta Cryst. (2013). C69, 282–284

organic compounds
system, we report here the crystal structure of (I) (Fig. 1) and
compare it with those of related cyclouridine molecules.
The preferred sugar puckering modes in nucleosides are
C20-endo and C30-endo (Saenger, 1984), whereas the C40-endo
(4E) conformation was considered to be unlikely given the
short O20—O30 distance and the fact that some adjacent bonds
would be in an eclipsed conformation (Jardetzky, 1960).
However, with the cyclization of O20 and C20, the ribosyl
furanose ring changes to the arabinosyl configuration, thus
eliminating the steric congestion at O30. The fused oxazolidine
ring demands C10—N1 and C20—O20 to be eclipsed in order to
conform to the sp2 character of atoms N1 and C2 in the
pyrimidine ring. The X-ray study of (I) shows that the five-
membered furanosyl ring adopts a nearly perfect C40-endo
puckered conformation. The best four-atom plane, comprised
of atoms O40, C10, C20 and C30, is planar, as the O40—C10—
C20—C30 torsion angle is only ꢀ0.4 (2)ꢁ. Atom C40 is displaced
0
˚
by 0.491 (3) A to the same side of this plane as C5 . A
quantitative analysis of the ring conformations was performed
using the method of Cremer & Pople (1975) for the calculation
of puckering parameters. The polar parameters for the
Figure 2
The C—Hꢂ ꢂ ꢂꢁ and C—Oꢂ ꢂ ꢂꢁ interactions of (I) (dotted lines). H atoms
ꢁ
˚
furanose ring are Q = 0.316 (2) A and ’ = 143.3 (4) ,
comparable with an ideal envelope C40-endo conformation
(ideal ’ = 144ꢁ). This conformation is also found in cyclo-
nucleosides such as 2,20-anhydro-1-(ꢀ-d-arabinofuranosyl)-
uracil (Suck & Saenger, 1973) and 1,2-di-O-isopropylidene-
pentofuranose (Doboszewski et al. 2012).
have been omitted for clarity.
ꢀ2.1 (4)ꢁ, respectively, indicating that the C10—C9 bond is
trans and the C9—O9 bond cis to the C30—O30 bond.
Various C—Oꢂ ꢂ ꢂꢁ, C—Hꢂ ꢂ ꢂꢁ, C—Hꢂ ꢂ ꢂO and C—Hꢂ ꢂ ꢂN
hydrogen bonds are present in the structure of (I). The C—
Oꢂ ꢂ ꢂꢁ interactions that can be observed are an intramolecular
The exocyclic C40—C50 bond adopts a gauche–trans
conformation instead of the gauche–gauche conformation
commonly observed in nucleosides (Shefter & Trueblood,
1965). The corresponding dihedral angles, as defined by
˚
C7—O7ꢂ ꢂ ꢂCg interaction [O7ꢂ ꢂ ꢂCg = 3.595 (2) A; Cg is the
centroid of the N1/C2/N3/C4–C6 ring] and an intermolecular
i
i
˚
C9—O9ꢂ ꢂ ꢂCg interaction [O9ꢂ ꢂ ꢂCg = 3.3036 (12) A; symmetry
code: (i) x ꢀ 1, y, z]. Molecules are arranged in chains in a
head-to-tail fashion via C6—H6ꢂ ꢂ ꢂN3ii hydrogen bonds and
C10—H10ꢂ ꢂ ꢂO4iii short contacts [symmetry codes: (ii) x + 2,
Shefter & Trueblood (1965), are ’OO = 55.2 (3)ꢁ and ’OC
=
172.5 (2)ꢁ. This geometric arrangement may lessen the short
contacts that would occur if the conformation were gauche–
gauche and syn (Seshadri et al., 1983). In addition, a significant
intramolecular C50—H502ꢂ ꢂ ꢂꢁ(pyrimidine) hydrogen bond
and a C7—O7ꢂ ꢂ ꢂꢁ(pyrimidine) interaction were observed in
this molecule, which we believe are the other main forces
stabilizing the C40—C50 gauche–trans configuration. The
present geometry is very similar to that of the 50-O-tosyl and
50-O-acetylated analogues (Gautham et al., 1983; Seshadri et
al., 1983).
1
2
1
2
y ꢀ , ꢀz; (iii) ꢀx + 2, y + , ꢀz] along the [010] direction
(Table 1 and Fig. 2). These chains are further connected via
weak C8—H8Bꢂ ꢂ ꢂO7iv hydrogen bonds [symmetry code: (iv)
1
2
x + 1, y + , ꢀz + 1] into a sheet and these sheets are in turn
further connected via various weak C—Hꢂ ꢂ ꢂO short contacts
into a three-dimensional network.
Experimental
The uracil ring and the five-membered oxazolidine ring
fused at atoms N1 and C2 are both essentially planar. The
interplanar angle between the six- and five-membered rings is
about 2ꢁ. The glycosidic torsion angle ꢂ (O40—C10—N1—C6)
is ꢀ63.5 (3)ꢁ, reflecting a syn conformation. The value agrees
well with those for the similar fused-ring systems 2,20-anhydro-
1-ꢀ-d-arabino-furanosyl cytosine hydrochloride (ꢂCN = ꢀ61ꢁ;
Sundaralingam, 1973) and 2,20-anhydro-1-ꢀ-d-arabino-furan-
osyl uracil (ꢂCN = ꢀ 65.5ꢁ; Delbaere & James, 1973).
20,30-O-(Methoxymethylene)uridine, (III) (see Scheme), was pre-
pared according to a previously reported method (Shiragami et al.,
1988). All other chemicals were obtained commercially and used
without further purification. The title compound, (I), was prepared
according to a similar procedure used for the synthesis of 1-(5-O-
acetyl-2,3-dideoxy-ꢀ-d-glycero-pent-2-enofuranosy1)uracil, (II). A
solution of (III) (7.0 g, 21.3 mmol) in acetic anhydride (50 ml) was
boiled gently and the acetic acid which formed was boiled off. After
the disappearance of the starting material (about 5 h), the remaining
acetic anhydride was evaporated under reduced pressure, and the
residue was dissolved in chloroform (100 ml) and washed with
aqueous NaHCO3 (50 ml). The aqueous layer was extracted with
CHCl3 (50 ml). The combined organic layers were dried over Na2SO4,
concentrated and purified by silica-gel column chromatography
(CHCl3–MeOH 10:1 v/v) to give (I) (yield: 4.3 g, 65%; m.p. 461–
For the 50-O-acetyl group, the C8—C7—O50—C50 and O7—
C7—O50—C50 torsion angles are 177.0 (3) and ꢀ3.2 (4)ꢁ,
respectively, and thus the C8—C7 bond is trans and the
C7—O7 bond cis to the arabinose C50—O50 bond. This is the
same for the 30-O-acetyl group, as the C10—C9—O30—C30
and O9—C9—O30—C30 torsion angles are 178.4 (2) and
ꢃ
Acta Cryst. (2013). C69, 282–284
Fu et al. C13H14N2O7 283

organic compounds
463 K). Crystals suitable for X-ray diffraction analysis were crystal-
lized from a petroleum ether–ethyl acetate mixture (4:1 v/v).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement:
CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to
solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to
refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics:
OLEX2 (Dolomanov et al., 2009); software used to prepare material
for publication: OLEX2.
Crystal data
3
˚
C13H14N2O7
Mr = 310.26
Monoclinic, P21
V = 719.21 (5) A
Z = 2
Mo Kꢃ radiation
ꢄ = 0.12 mmꢀ1
T = 294 K
0.3 ꢄ 0.3 ꢄ 0.3 mm
˚
a = 8.1032 (3) A
˚
b = 10.0065 (3) A
The authors are grateful for financial support from the
National Natural Science Foundation of China (grant Nos.
212620302 and 20962017) and the Natural Science Foundation
of Gansu Province, China (grant No. 1107RJZA263).
˚
c = 8.8704 (4) A
ꢀ = 90.609 (4)ꢁ
Data collection
Agilent SuperNova (Dual, Cu at
zero, Eos) diffractometer
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
Tmin = 0.710, Tmax = 1.000
2985 measured reflections
2483 independent reflections
2160 reflections with I > 2ꢅ(I)
Rint = 0.015
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: FN3123). Services for accessing these data are
described at the back of the journal.
Refinement
R[F2 > 2ꢅ(F2)] = 0.039
wR(F2) = 0.091
S = 1.09
2483 reflections
201 parameters
1 restraint
H-atom parameteꢀrs3 constrained
References
˚
Áꢆmax = 0.14 e A
ꢀ3
˚
Áꢆmin = ꢀ0.17 e A
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire,
England.
Belostotskii, A. M., Genizi, E. & Hassner, A. (2012). Org. Biomol. Chem. 10,
6624–6628.
Bennett, C. F. & Swayze, E. E. (2010). Annu. Rev. Pharmacol. Toxicol. 50, 259–
293.
Absolute structure: Flack (1983),
933 Friedel pairs
Flack parameter: ꢀ0.2 (12)
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
Cross, B. P. & Schleich, T. (1973). Biopolymers, 12, 2381–2389.
Dai, Q., Frederiksen, J. K., Anderson, V. E., Harris, M. E. & Piccirilli, J. A.
(2008). J. Org. Chem. 73, 309–311.
Delbaere, L. T. J. & James, M. N. G. (1973). Acta Cryst. B29, 2905–2912.
Doboszewski, B., Silva, M. J. e, Nazarenko, A. Y. & Nemykin, V. N. (2012).
Acta Cryst. E68, o1109–o1110.
Table 1
Hydrogen-bond geometry (A, ).
ꢁ
˚
Cg is the centroid of the N1/C2/N3/C4–C6 ring.
D—Hꢂ ꢂ ꢂA
D—H
Hꢂ ꢂ ꢂA
Dꢂ ꢂ ꢂA
D—Hꢂ ꢂ ꢂA
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann,
H. (2009). J. Appl. Cryst. 42, 339–341.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Gautham, N., Seshadri, T. P. & Viswamitra, M. A. (1983). Acta Cryst. C39, 456–
458.
Jardetzky, C. D. (1960). J. Am. Chem. Soc. 82, 229–233.
Miles, D. W., Townsend, L. B., Miles, D. L. & Eyring, H. (1979). Proc. Natl
Acad. Sci. USA, 76, 553–556.
Saenger, W. (1984). In Principles of Nucleic Acid Structure. New York:
Springer-Verlag.
C10—H10ꢂ ꢂ ꢂO4i
C50—H50Aꢂ ꢂ ꢂO4ii
C50—H50Bꢂ ꢂ ꢂCg
C6—H6ꢂ ꢂ ꢂO9iii
C8—H8Cꢂ ꢂ ꢂO4iv
C6—H6ꢂ ꢂ ꢂN3i
0.98
0.97
0.97
0.93
0.96
0.93
0.98
0.98
2.36
2.59
2.50
2.42
2.48
2.68
2.37
2.62
3.308 (3)
3.537 (3)
3.026 (2)
3.313 (3)
3.272 (4)
3.226 (3)
3.311 (3)
3.340 (3)
162
166
114
162
140
118
161
130
v
C30—H30ꢂ ꢂ ꢂO40
iii
C40—H40ꢂ ꢂ ꢂO20
1
2
1
2
Symmetry codes: (i) ꢀx þ 2; y þ ; ꢀz; (ii) x ꢀ 1; y; z; (iii) ꢀx þ 1; y þ ; ꢀz; (iv)
1
2
1
2
ꢀx þ 2; y þ ; ꢀz þ 1; (v) ꢀx þ 1; y ꢀ ; ꢀz.
Seshadri, T. P., Gautham, N. & Viswamitra, M. A. (1983). Acta Cryst. C39,
1706–1708.
Shefter, E. & Trueblood, K. N. (1965). Acta Cryst. 18, 1067–1077.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Shiragami, H., Irie, Y., Shirae, H., Yokozeki, K. & Yasuda, N. (1988). J. Org.
Chem. 53, 5170–5173.
Suck, D. & Saenger, W. (1973). Acta Cryst. B29, 1323–1330.
Sundaralingam, M. (1973). Conformations of Biological Molecules and
Polymers, edited by E. D. Bergman & B. Pullman, pp. 417–455. New York:
Academic Press.
All H atoms were placed geometrically and refined using a riding
model, with C—H = 0.93 (aromatic), 0.96 (methyl), 0.97 (methylene)
˚
and 0.98 A (methine), and with Uiso(H) = 1.5Ueq(C) for methyl H
atoms and 1.2Ueq(C) otherwise. The chirality of (I) was known from
the synthetic route and the absolute structure was assigned on the
basis of the known chirality of the uridine used in the chemical
synthesis.
Wnuk, S. F., Chowdhury, S. M., Garcia, P. I. Jr & Robins, M. J. (2002). J. Org.
Chem. 67, 1816–1819.
ꢃ
284 Fu et al. C13H14N2O7
Acta Cryst. (2013). C69, 282–284

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 282-284 [doi:10.1107/S0108270113000395]
2,2′-Anhydro-1-(3′,5′-di-O-acetyl-β-D-arabinofuranosyl)uracil, a cyclouridine
nucleoside with a C4′-endo furanosyl conformation
Ying Fu, Yin-Xia He, Hong-Xia Hou, Wen-Bo Zhu, Hu-Lin Li, Chao Wu and Fang-Yan Xian
2,2′-Anhydro-1-(2′-deoxy-3′,5′-di-O-acety-β-D- arabinofuranosyl)uracil
Crystal data
C13H14N2O7
Dx = 1.433 Mg m−3
Mr = 310.26
Melting point = 461–463 K
Mo Kα radiation, λ = 0.7107 Å
Cell parameters from 1211 reflections
θ = 3.1–28.4°
Monoclinic, P21
a = 8.1032 (3) Å
b = 10.0065 (3) Å
c = 8.8704 (4) Å
β = 90.609 (4)°
V = 719.21 (5) Å3
Z = 2
µ = 0.12 mm−1
T = 294 K
Block, colourless
0.3 × 0.3 × 0.3 mm
F(000) = 324
Data collection
Agilent SuperNova (Dual, Cu at zero, Eos)
diffractometer
Radiation source: SuperNova (Mo) X-ray
Source
Mirror monochromator
Detector resolution: 16.0733 pixels mm-1
ω scans
Tmin = 0.710, Tmax = 1.000
2985 measured reflections
2483 independent reflections
2160 reflections with I > 2σ(I)
Rint = 0.015
θmax = 26.4°, θmin = 3.1°
h = −6→10
k = −12→12
l = −11→8
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.039
wR(F2) = 0.091
S = 1.09
2483 reflections
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0345P)2 + 0.0609P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.14 e Å−3
Δρmin = −0.17 e Å−3
201 parameters
1 restraint
Primary atom site location: structure-invariant
direct methods
Absolute structure: Flack (1983), 933 Friedel
pairs
Secondary atom site location: difference Fourier
map
Flack parameter: −0.2 (12)
Acta Cryst. (2013). C69, 282-284
sup-1

supplementary materials
Special details
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.20, Empirical absorption
correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is
used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
O2′
O3′
O4
0.7319 (2)
0.3797 (2)
1.1202 (3)
0.5843 (2)
0.4859 (3)
0.6470 (3)
0.1443 (2)
0.8368 (2)
0.9211 (3)
0.7165 (3)
0.7682
0.39998 (15)
0.55971 (17)
0.37929 (19)
0.70443 (14)
0.6532 (2)
0.5328 (3)
0.48121 (19)
0.58738 (17)
0.37845 (19)
0.6383 (2)
0.6938
−0.0785 (2)
−0.24786 (17)
0.2971 (2)
−0.02277 (19)
0.27176 (19)
0.4235 (2)
−0.1537 (2)
0.0164 (2)
0.1143 (2)
−0.0916 (3)
−0.1689
0.0440 (4)
0.0443 (4)
0.0594 (6)
0.0424 (4)
0.0570 (6)
0.0886 (8)
0.0605 (6)
0.0365 (5)
0.0416 (5)
0.0389 (6)
0.047*
O4′
O5′
O7
O9
N1
N3
C1′
H1′
C2
0.8376 (3)
0.6476 (3)
0.6637
0.4522 (2)
0.5074 (2)
0.5021
0.0244 (3)
−0.1578 (3)
−0.2670
0.0379 (6)
0.0396 (5)
0.048*
C2′
H2′
C3′
H3′
C4
0.4659 (3)
0.4262
0.5081 (2)
0.4195
−0.1176 (2)
−0.0882
0.0353 (5)
0.042*
1.0285 (3)
0.4557 (3)
0.3485
0.4446 (2)
0.6092 (2)
0.6544
0.2130 (3)
0.0112 (3)
0.0059
0.0430 (6)
0.0382 (5)
0.046*
C4′
H4′
C5
1.0296 (3)
1.0980
0.5895 (3)
0.6354
0.2110 (3)
0.2780
0.0466 (6)
0.056*
H5
C5′
H5′A
H5′B
C6
0.4762 (3)
0.3828
0.5453 (2)
0.4882
0.1656 (2)
0.1874
0.0433 (6)
0.052*
0.5761
0.4919
0.1698
0.052*
0.9345 (3)
0.9345
0.6582 (2)
0.7511
0.1148 (3)
0.1147
0.0412 (6)
0.049*
H6
C7
0.5792 (4)
0.5833 (5)
0.5352
0.6352 (3)
0.7582 (3)
0.7397
0.3962 (3)
0.4902 (4)
0.5865
0.0526 (7)
0.0828 (12)
0.124*
C8
H8A
H8B
H8C
C9
0.5218
0.8276
0.4406
0.124*
0.6956
0.7865
0.5044
0.124*
0.2144 (3)
0.1376 (4)
0.1457
0.5409 (3)
0.6010 (4)
0.5396
−0.2514 (3)
−0.3879 (3)
−0.4707
0.0469 (6)
0.0728 (10)
0.109*
C10
H10A
H10B
0.1940
0.6824
−0.4125
0.109*
Acta Cryst. (2013). C69, 282-284
sup-2

supplementary materials
H10C
0.0236
0.6199
−0.3690
0.109*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
O2′
O3′
O4
O4′
O5′
O7
O9
N1
N3
C1′
C2
0.0470 (11)
0.0443 (10)
0.0649 (14)
0.0427 (10)
0.0711 (14)
0.118 (2)
0.0286 (8)
0.0562 (11)
0.0395 (9)
0.0040 (8)
−0.0104 (9)
−0.0049 (7)
−0.0152 (11)
0.0009 (8)
−0.0056 (8)
0.0081 (8)
0.0488 (10)
0.0506 (11)
0.0265 (7)
0.0549 (11)
0.0762 (15)
0.0631 (13)
0.0264 (10)
0.0306 (10)
0.0307 (11)
0.0293 (12)
0.0336 (12)
0.0274 (11)
0.0408 (14)
0.0342 (11)
0.0447 (14)
0.0422 (14)
0.0317 (12)
0.0602 (18)
0.066 (2)
−0.0025 (8)
0.0135 (10)
0.0009 (7)
0.0625 (12)
0.0581 (11)
0.0444 (11)
0.0703 (14)
0.0703 (13)
0.0464 (12)
0.0484 (13)
0.0444 (15)
0.0463 (15)
0.0393 (12)
0.0360 (12)
0.0430 (15)
0.0433 (13)
0.0468 (15)
0.0410 (12)
0.0442 (15)
0.0401 (15)
0.0477 (18)
0.0450 (14)
0.0542 (17)
0.0053 (10)
−0.0029 (7)
−0.0116 (9)
0.0102 (14)
0.0039 (11)
0.0014 (9)
0.0133 (10)
0.0182 (17)
−0.0071 (10)
0.0004 (9)
−0.0170 (10)
−0.0367 (14)
0.0032 (10)
−0.0038 (9)
−0.0023 (11)
0.0012 (11)
0.0067 (11)
−0.0028 (10)
−0.0057 (10)
0.0031 (12)
−0.0029 (10)
−0.0052 (12)
−0.0029 (11)
0.0038 (12)
−0.0092 (13)
−0.021 (2)
0.0483 (12)
0.0367 (12)
0.0456 (13)
0.0415 (15)
0.0381 (14)
0.0460 (13)
0.0424 (13)
0.0451 (16)
0.0372 (14)
0.0483 (16)
0.0465 (15)
0.0477 (16)
0.0574 (18)
0.134 (4)
0.0065 (10)
−0.0004 (11)
0.0043 (10)
0.0037 (12)
−0.0002 (11)
0.0067 (12)
0.0004 (11)
0.0002 (13)
0.0003 (12)
−0.0029 (11)
−0.0141 (15)
−0.039 (2)
0.0044 (13)
0.019 (2)
0.0018 (9)
0.0035 (10)
−0.0015 (11)
0.0008 (11)
0.0009 (10)
0.0016 (11)
−0.0031 (10)
−0.0053 (12)
−0.0049 (11)
−0.0007 (11)
0.0072 (13)
0.0018 (15)
−0.0090 (13)
−0.0010 (17)
C2′
C3′
C4
C4′
C5
C5′
C6
C7
C8
C9
0.0467 (15)
0.062 (2)
0.0490 (15)
0.101 (3)
−0.0043 (12)
−0.0174 (15)
C10
Geometric parameters (Å, º)
O2′—C2
O2′—C2′
O3′—C3′
O3′—C9
O4—C4
O4′—C1′
O4′—C4′
O5′—C5′
O5′—C7
O7—C7
O9—C9
N1—C1′
N1—C2
N1—C6
N3—C2
N3—C4
C1′—H1′
C1′—C2′
C2′—H2′
1.350 (3)
C2′—C3′
C3′—H3′
C3′—C4′
C4—C5
1.518 (3)
1.451 (3)
1.440 (3)
1.353 (3)
1.234 (3)
1.404 (3)
1.447 (3)
1.434 (3)
1.343 (3)
1.186 (4)
1.200 (3)
1.452 (3)
1.355 (3)
1.370 (3)
1.276 (3)
1.394 (3)
0.9800
0.9800
1.528 (3)
1.450 (3)
0.9800
C4′—H4′
C4′—C5′
C5—H5
1.519 (3)
0.9300
C5—C6
1.335 (3)
0.9700
C5′—H5′A
C5′—H5′B
C6—H6
0.9700
0.9300
C7—C8
1.487 (4)
0.9600
C8—H8A
C8—H8B
C8—H8C
C9—C10
C10—H10A
C10—H10B
C10—H10C
0.9600
0.9600
1.482 (4)
0.9600
1.539 (3)
0.9800
0.9600
0.9600
Acta Cryst. (2013). C69, 282-284
sup-3

supplementary materials
C2—O2′—C2′
C9—O3′—C3′
C1′—O4′—C4′
C7—O5′—C5′
C2—N1—C1′
C2—N1—C6
C6—N1—C1′
C2—N3—C4
O4′—C1′—N1
O4′—C1′—H1′
O4′—C1′—C2′
N1—C1′—H1′
N1—C1′—C2′
C2′—C1′—H1′
O2′—C2—N1
N3—C2—O2′
N3—C2—N1
O2′—C2′—C1′
O2′—C2′—H2′
O2′—C2′—C3′
C1′—C2′—H2′
C3′—C2′—C1′
C3′—C2′—H2′
O3′—C3′—C2′
O3′—C3′—H3′
O3′—C3′—C4′
C2′—C3′—H3′
C2′—C3′—C4′
C4′—C3′—H3′
O4—C4—N3
O4—C4—C5
N3—C4—C5
O4′—C4′—C3′
O4′—C4′—H4′
109.45 (18)
116.16 (19)
109.56 (16)
117.7 (2)
112.8 (2)
118.7 (2)
128.20 (19)
116.2 (2)
112.9 (2)
111.8
O4′—C4′—C5′
C3′—C4′—H4′
C5′—C4′—C3′
C5′—C4′—H4′
C4—C5—H5
113.11 (18)
109.0
112.91 (19)
109.0
119.4
C6—C5—C4
121.3 (3)
119.4
C6—C5—H5
O5′—C5′—C4′
O5′—C5′—H5′A
O5′—C5′—H5′B
C4′—C5′—H5′A
C4′—C5′—H5′B
H5′A—C5′—H5′B
N1—C6—H6
106.28 (19)
110.5
110.5
107.0 (2)
111.8
110.5
110.5
101.02 (18)
111.8
108.7
121.1
110.4 (2)
121.8 (2)
127.8 (2)
106.17 (17)
111.8
C5—C6—N1
117.9 (2)
121.1
C5—C6—H6
O5′—C7—C8
O7—C7—O5′
O7—C7—C8
111.0 (3)
122.6 (3)
126.3 (3)
109.5
110.04 (18)
111.8
C7—C8—H8A
C7—C8—H8B
C7—C8—H8C
H8A—C8—H8B
H8A—C8—H8C
H8B—C8—H8C
O3′—C9—C10
O9—C9—O3′
O9—C9—C10
C9—C10—H10A
C9—C10—H10B
C9—C10—H10C
109.5
104.77 (19)
111.8
109.5
109.5
106.06 (17)
112.3
109.5
109.5
109.44 (19)
112.3
111.7 (3)
121.9 (2)
126.4 (3)
109.5
103.84 (18)
112.3
119.7 (2)
122.2 (3)
118.1 (2)
103.63 (18)
109.0
109.5
109.5
H10A—C10—H10B
H10A—C10—H10C
H10B—C10—H10C
109.5
109.5
109.5
O2′—C2′—C3′—O3′
O2′—C2′—C3′—C4′
O3′—C3′—C4′—O4′
O3′—C3′—C4′—C5′
O4—C4—C5—C6
O4′—C1′—C2′—O2′
O4′—C1′—C2′—C3′
O4′—C4′—C5′—O5′
N1—C1′—C2′—O2′
N1—C1′—C2′—C3′
N3—C4—C5—C6
C1′—O4′—C4′—C3′
C1′—O4′—C4′—C5′
C1′—N1—C2—O2′
−149.97 (18)
94.7 (2)
C2—N3—C4—O4
C2—N3—C4—C5
C2′—O2′—C2—N1
C2′—O2′—C2—N3
C2′—C3′—C4′—O4′
C2′—C3′—C4′—C5′
C3′—O3′—C9—O9
C3′—O3′—C9—C10
C3′—C4′—C5′—O5′
C4—N3—C2—O2′
C4—N3—C2—N1
C4—C5—C6—N1
C4′—O4′—C1′—N1
C4′—O4′—C1′—C2′
−175.8 (2)
3.3 (4)
−81.4 (2)
155.9 (2)
177.2 (2)
−116.8 (2)
−0.4 (2)
−2.7 (3)
176.5 (2)
31.5 (2)
−91.2 (2)
−2.1 (4)
178.4 (2)
172.5 (2)
178.7 (2)
−2.3 (4)
−0.8 (4)
−88.8 (2)
21.4 (2)
55.2 (3)
1.4 (2)
117.88 (19)
−1.9 (5)
−33.6 (2)
89.1 (2)
3.9 (3)
Acta Cryst. (2013). C69, 282-284
sup-4

supplementary materials
C1′—N1—C2—N3
C1′—N1—C6—C5
C1′—C2′—C3′—O3′
C1′—C2′—C3′—C4′
C2—O2′—C2′—C1′
C2—O2′—C2′—C3′
C2—N1—C1′—O4′
C2—N1—C1′—C2′
C2—N1—C6—C5
−175.3 (2)
175.9 (2)
96.3 (2)
−19.0 (2)
0.7 (2)
C5′—O5′—C7—O7
−3.2 (4)
C5′—O5′—C7—C8
C6—N1—C1′—O4′
C6—N1—C1′—C2′
C6—N1—C2—O2′
C6—N1—C2—N3
C7—O5′—C5′—C4′
C9—O3′—C3′—C2′
C9—O3′—C3′—C4′
177.0 (3)
−63.5 (3)
−177.4 (2)
178.7 (2)
−0.5 (4)
−112.2 (2)
110.7 (2)
−3.2 (3)
2.0 (4)
−148.2 (2)
165.25 (19)
−83.3 (2)
Hydrogen-bond geometry (Å, º)
Cg is the centroid of the N1/C2/N3/C4–C6 ring [Added text OK?].
D—H···A
D—H
H···A
D···A
D—H···A
C1′—H1′···O4i
C5′—H5′A···O4ii
C5′—H5′B···Cg
C6—H6···O9iii
C8—H8C···O4iv
C6—H6···N3i
0.98
0.97
0.97
0.93
0.96
0.93
0.98
0.98
2.36
2.59
2.50
2.42
2.48
2.68
2.37
2.62
3.308 (3)
3.537 (3)
3.026 (2)
3.313 (3)
3.272 (4)
3.226 (3)
3.311 (3)
3.340 (3)
162
166
114
162
140
118
161
130
C3′—H3′···O4′v
C4′—H4′···O2′iii
Symmetry codes: (i) −x+2, y+1/2, −z; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z; (iv) −x+2, y+1/2, −z+1; (v) −x+1, y−1/2, −z.
Acta Cryst. (2013). C69, 282-284
sup-5

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