5-Phenyl­uridine trihydrate

The title compound (systematic name: 2,4-dihydr­oxy-5-phenyl-1-β-D-ribofuran­osylpyrimidine trihydrate), crystallized as the trihydrate, C₁₅H₁₆N₂O₆·3H₂O, stabilized by hydrogen bonds to the uracil O atoms. Two statistically disordered water solvent mol­ecules occupy channels along the a axis; the site occupancy factors are ca 0.6 and 0.4. The heterocyclic base is almost planar and is oriented anti with respect to the puckered sugar moiety. The sugar ring adopts a conformation intermediate between twist and envelope.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• H-atom completeness 73%
• Disorder in solvent or counterion
• R factor = 0.053
• wR factor = 0.185
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) .......        O2W

Author Response: ...The H atoms are missing in all three water molecules, and this is acknowledged in the text.

PLAT430_ALERT_2_A Short Inter D...A Contact  O3W'   ..  O1W'    ..       2.03 Ang.

Author Response: ...Disordered refinement of the two of the three water molecules result in the observed short inter D...A contacts.

Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O1     ..  O1W     ..       2.80 Ang.

Author Response: ...Disordered refinement of the two of the three water molecules result in the observed short inter D...A contacts.

PLAT430_ALERT_2_B Short Inter D...A Contact  O1     ..  O1W'    ..       2.81 Ang.

Author Response: ...Disordered refinement of the two of the three water molecules result in the observed short inter D...A contacts.

PLAT430_ALERT_2_B Short Inter D...A Contact  O3W'   ..  O2W     ..       2.72 Ang.

Author Response: ...Disordered refinement of the two of the three water molecules result in the observed short inter D...A contacts.

PLAT430_ALERT_2_B Short Inter D...A Contact  O2W    ..  O3W     ..       2.78 Ang.

Author Response: ...Disordered refinement of the two of the three water molecules result in the observed short inter D...A contacts.

Alert level C
ABSTY03_ALERT_1_C  The _exptl_absorpt_correction_type has been given as none.
            However values have been given for Tmin and Tmax. Remove
            these if an absorption correction has not been applied.
  From the CIF: _exptl_absorpt_correction_T_min   0.948
  From the CIF: _exptl_absorpt_correction_T_max   0.984
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           374.35
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   15.00  180.16
           H         1.01   16.00   16.13
           N        14.01    2.00   28.01
           O        16.00    9.00  143.99
           Calculated formula weight              368.30
DIFMN02_ALERT_2_C  The minimum difference density is < -0.1*ZMAX*0.75
            _refine_diff_density_min given =     -0.628
            Test value =     -0.600
DIFMN03_ALERT_1_C  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.634
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     374.35
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.63 e/A   
PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............      -0.63 e/A   
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      40.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       >O1W
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O1W'
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      >O3W'
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O3W
PLAT430_ALERT_2_C Short Inter D...A Contact  O2     ..  O2W     ..       2.88 Ang.

Author Response: ...Disordered refinement of the two of the three water molecules result in the observed short inter D...A contacts.

PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C15 H22 N2 O9
            Atom count from the _atom_site data:  C15 H16 N2 O9
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C15 H22 N2 O9
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         60.00     60.00    0.00
           H         88.00     64.00   24.00
           N          8.00      8.00    0.00
           O         36.00     36.00    0.00
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           30.04
           From the CIF: _reflns_number_total               2879
           Count of symmetry unique reflns         2890
           Completeness (_total/calc)             99.62%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3'    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4'    = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         12

   2 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  21 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

  15 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  17 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Research has been focused towards finding biologically active analogues of uridine, a naturally occurring compound, and modification of the uracil ring concentrates on position 5. Examples of the latest investigations for the development of new drugs include e.g. the synthesis of ethynyl uridine derivatives as antiviral drugs against Flaviviridae (Aucagne et al., 2006), especially HCV, studies of other alkynyl-uridines as potent inhibitors of Mycobacteria (Rai et al., 2005), and e.g. uridine and estradiol conjugates exhibiting binding affinity and cytotoxicity against cell lines with and without an estrogen receptor (Ali, H. et al., 2006). Modern synthetic methods include coupling reactions with catalysis by organometallic compounds, which enables the introduction of diverse substituents of an aliphatic or aromatic nature. Although the synthesis and biological activity of uridine derivatives has been studied intensively, their structural parameters from crystallographic measurements, important for behavior in biological systems, have rarely been discussed and published. In this paper we describe the structural properties of 5-phenyluridine prepared by the Suzuki coupling from 5-iodouridine and phenylboronic acid.

A selection of geometric parameters is given in Table 1. The heterocyclic base moiety is almost planar, with a maximum deviation of 0.019 (3) Å for the C1 atom. The N-glycosidic torsion angle χ (C1–N1–C1'–O4') is -169.8 (2)° which corresponds to an anti orientation of the base moiety. The sugar ring, C1'–C2'–C3'–C4'–O4', adopts a mixed twisted- envelope ³T₂/³E conformation (C3'-exo / C2'-endo) with puckering parameters q₂ = 0.384 (3) Å and φ₂ = 64.2 (4)° (Cremer & Pople, 1975). The conformation of the side chain, as defined by the torsion angle O5'–C5'–C4'–C3' of 53.5 (3)°, is +sc. The phenyl and uracil rings are not co-planar (Fig.1), with a dihedral angle between the mean planes of 38.02 (9)°. The crystal packing is determined by a network of hydrogen bonds (Table 2) with π-π interactions (3.455 Å) observed between the phenyl and uracil moieties. This packing creates channels along the a axis which hosts the solvent molecules (Fig. 2).

Related literature

For related literature, see: Ali et al. (2006); Aucagne et al. (2006); Cremer & Pople (1975); Flack (1983); Flack & Bernardinelli (2000); Flynn et al. (1991); Rai et al. (2005).

S2. Experimental

5-phenyluridine was prepared by the Suzuki coupling reaction of 5-iodouridine (0.277 g, 0.75 mmol) and phenylboronic acid (0.081 g, 0.90 mmol) (Flynn et al. 1991), yield 0.203 g (84%). Analytical data are identical with that published. The final product was obtained from slow evaporation of an aqueous solution (10 mg ml^-1) at room temperature. MS: m/z 321.

S3. Refinement

The aromatic, methylene, methine, amine and hydroxyl H atoms were placed in geometrically idealized positions (C—H = 0.93–0.98, N—H = 0.86 and O—H = 0.82 Å) and constrained to ride on their parent atoms with U_iso(H) = 1.2U_eq(C,N,O). Water molecules O1W and O3W refined with large thermal vibrations and were subsequently refined disordered over two sites as O1W/O1W' and O3W/O3W' respectively. Refinement was kept stable with the use of anisotropic restraints and free variables were incorporated to refine occupation parameters to one. Possible hydogen coordinates from the Fourier difference map could not be refined satisfactory. Refinement of the Flack parameter (Flack, 1983) led to an inconclusive value (Flack & Bernardinelli, 2000) of -10 (10). This is generally the case with light atom Mo Kα data where f" is nearly zero. The Friedel equivalents were therefore merged before final refinement with a MERG 4 command. The conformation of the title compound was assigned from the absolute configuration of the starting material.

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The structure of (1) showing the displacement ellipsoids parameters at 50% probability.
	Fig. 2. The crystal packing of (1) viewed down the crystallographic a axis

2,4-dihydroxy-5-phenyl-1-β-D-ribofuranosylpyrimidine trihydrate

Crystal data

C15H16N2O6·3H2O	F(000) = 792
Mr = 374.35	Dx = 1.433 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2838 reflections
a = 7.3627 (1) Å	θ = 3.9–30°
b = 14.0874 (3) Å	µ = 0.12 mm^−1
c = 16.7287 (3) Å	T = 295 K
V = 1735.12 (5) Å^3	Prismatic, colourless
Z = 4	0.45 × 0.24 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer	2338 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 30.0°, θmin = 1.9°
φ and ω scans	h = −10→10
5050 measured reflections	k = −19→19
2879 independent reflections	l = −23→23

Refinement

Refinement on F^2	12 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.1267P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.185	(Δ/σ)max < 0.001
S = 1.16	Δρmax = 0.63 e Å^−3
2879 reflections	Δρmin = −0.63 e Å^−3
255 parameters

Special details

Experimental. The diffraction data were collected at room temperature using a Nonius Kappa CCD diffractometer with graphite-monochromated Mo Kα (λ = 0.7107 Å) using an exposure time of 40 s/frame. A total of 204 frames were collected with a frame width of 2.0° covering up to θ = 30.04° with 99.6% completeness accomplished.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.8933 (4)	0.55845 (14)	0.57391 (13)	0.0405 (5)
O2	0.7725 (3)	0.33876 (14)	0.38352 (11)	0.0349 (5)
N1	0.9232 (3)	0.40257 (16)	0.60850 (12)	0.0262 (4)
N2	0.8299 (3)	0.44486 (15)	0.48118 (14)	0.0296 (5)
H2	0.7984	0.4885	0.448	0.036*
C1	0.8832 (4)	0.47460 (19)	0.55542 (16)	0.0283 (5)
C2	0.8209 (4)	0.35266 (17)	0.45353 (15)	0.0254 (5)
C3	0.8698 (4)	0.28058 (17)	0.51060 (15)	0.0246 (5)
C4	0.9212 (4)	0.30928 (18)	0.58495 (15)	0.0250 (5)
H4	0.9567	0.2633	0.6216	0.03*
C5	0.8662 (4)	0.17852 (19)	0.48985 (16)	0.0286 (5)
C6	0.9221 (4)	0.1455 (2)	0.41495 (19)	0.0365 (6)
H6	0.9593	0.1886	0.3762	0.044*
C7	0.9225 (5)	0.0498 (3)	0.3980 (2)	0.0496 (9)
H7	0.9604	0.0289	0.348	0.059*
C8	0.8669 (5)	−0.0158 (2)	0.4549 (3)	0.0585 (11)
H8	0.8687	−0.0804	0.4433	0.07*
C9	0.8084 (6)	0.0157 (2)	0.5297 (3)	0.0521 (9)
H9	0.7698	−0.0275	0.5681	0.063*
C10	0.8083 (5)	0.1124 (2)	0.5461 (2)	0.0392 (7)
H10	0.7687	0.1334	0.5958	0.047*
C1'	0.9934 (4)	0.43348 (18)	0.68847 (14)	0.0255 (5)
H1'	1.0928	0.4789	0.6812	0.031*
C2'	0.8448 (4)	0.47799 (17)	0.73959 (15)	0.0264 (5)
H2'	0.75	0.5086	0.7076	0.032*
O2'	0.9353 (3)	0.54254 (13)	0.79151 (12)	0.0327 (5)
H2O'	0.8655	0.5595	0.8269	0.039*
C3'	0.7751 (4)	0.39195 (18)	0.78564 (15)	0.0285 (5)
H3'	0.6943	0.3544	0.7515	0.034*
O3'	0.6828 (3)	0.41854 (14)	0.85632 (14)	0.0433 (6)
H3O'	0.6012	0.3804	0.8654	0.052*
C4'	0.9494 (4)	0.33734 (19)	0.80117 (15)	0.0307 (6)
H4'	1.0118	0.3665	0.8467	0.037*
O4'	1.0571 (3)	0.35341 (14)	0.73006 (11)	0.0318 (4)
C5'	0.9330 (5)	0.2329 (2)	0.81655 (18)	0.0395 (7)
H51'	1.0535	0.2055	0.8211	0.047*
H52'	0.8706	0.2229	0.8669	0.047*
O5'	0.8359 (3)	0.18558 (16)	0.75411 (14)	0.0437 (6)
H5O'	0.8947	0.1397	0.7387	0.052*
O1W	0.831 (2)	0.7382 (6)	0.5078 (5)	0.083 (4)	0.63 (3)
O1W'	0.715 (5)	0.7221 (11)	0.5193 (16)	0.114 (7)	0.37 (3)
O2W	0.5372 (5)	0.6628 (3)	0.7329 (2)	0.0838 (12)
O3W	0.6219 (14)	0.8252 (13)	0.6464 (15)	0.107 (6)	0.43 (3)
O3W'	0.549 (3)	0.7790 (12)	0.6033 (9)	0.118 (7)	0.57 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0665 (14)	0.0226 (9)	0.0324 (10)	−0.0004 (9)	−0.0019 (11)	−0.0011 (8)
O2	0.0495 (11)	0.0311 (9)	0.0242 (9)	0.0031 (9)	−0.0093 (9)	0.0009 (7)
N1	0.0367 (11)	0.0226 (9)	0.0192 (9)	0.0029 (9)	−0.0005 (9)	−0.0021 (7)
N2	0.0426 (12)	0.0211 (9)	0.0251 (10)	0.0032 (9)	−0.0038 (10)	0.0027 (8)
C1	0.0362 (13)	0.0233 (11)	0.0253 (12)	0.0017 (10)	0.0000 (10)	0.0018 (9)
C2	0.0302 (12)	0.0228 (11)	0.0232 (11)	−0.0002 (10)	−0.0016 (9)	−0.0008 (9)
C3	0.0285 (11)	0.0216 (10)	0.0237 (11)	0.0007 (9)	0.0005 (10)	0.0012 (9)
C4	0.0312 (12)	0.0214 (10)	0.0223 (11)	0.0023 (10)	−0.0004 (10)	−0.0005 (9)
C5	0.0302 (12)	0.0247 (12)	0.0310 (13)	0.0036 (10)	−0.0073 (10)	−0.0027 (10)
C6	0.0360 (14)	0.0333 (14)	0.0402 (15)	0.0040 (12)	−0.0022 (13)	−0.0079 (12)
C7	0.0438 (17)	0.0410 (17)	0.064 (2)	0.0118 (15)	−0.0104 (17)	−0.0229 (16)
C8	0.057 (2)	0.0272 (14)	0.091 (3)	0.0060 (15)	−0.029 (2)	−0.0150 (17)
C9	0.065 (2)	0.0270 (13)	0.064 (2)	−0.0065 (15)	−0.019 (2)	0.0062 (15)
C10	0.0516 (17)	0.0263 (13)	0.0398 (15)	−0.0017 (13)	−0.0094 (14)	0.0039 (11)
C1'	0.0319 (11)	0.0246 (11)	0.0201 (11)	0.0000 (10)	−0.0009 (9)	−0.0017 (9)
C2'	0.0345 (11)	0.0219 (10)	0.0228 (11)	0.0007 (10)	−0.0003 (10)	−0.0030 (9)
O2'	0.0423 (10)	0.0277 (9)	0.0280 (9)	−0.0076 (8)	0.0058 (8)	−0.0098 (8)
C3'	0.0364 (12)	0.0233 (10)	0.0257 (11)	−0.0026 (10)	0.0032 (11)	−0.0065 (9)
O3'	0.0565 (13)	0.0341 (10)	0.0394 (11)	−0.0134 (10)	0.0207 (10)	−0.0118 (9)
C4'	0.0435 (14)	0.0290 (12)	0.0195 (11)	0.0016 (12)	−0.0015 (10)	−0.0011 (9)
O4'	0.0359 (9)	0.0343 (9)	0.0251 (9)	0.0084 (8)	−0.0018 (8)	0.0004 (7)
C5'	0.0590 (18)	0.0265 (12)	0.0329 (13)	0.0037 (14)	−0.0046 (14)	0.0040 (11)
O5'	0.0514 (12)	0.0286 (10)	0.0512 (14)	0.0065 (10)	−0.0038 (11)	−0.0063 (10)
O1W	0.108 (9)	0.060 (4)	0.080 (4)	0.015 (5)	−0.009 (4)	0.018 (3)
O1W'	0.113 (17)	0.084 (8)	0.146 (13)	−0.011 (9)	−0.050 (13)	0.024 (8)
O2W	0.075 (2)	0.122 (3)	0.0549 (18)	0.036 (2)	−0.0032 (16)	−0.0002 (19)
O3W	0.046 (5)	0.096 (9)	0.178 (14)	0.021 (5)	0.011 (7)	0.008 (10)
O3W'	0.125 (11)	0.108 (9)	0.121 (9)	0.054 (9)	0.045 (8)	0.049 (7)

Geometric parameters (Å, º)

O1—C1	1.223 (3)	C9—H9	0.93
O2—C2	1.240 (3)	C10—H10	0.93
N1—C4	1.372 (3)	C1'—O4'	1.406 (3)
N1—C1	1.380 (3)	C1'—C2'	1.524 (4)
N1—C1'	1.499 (3)	C1'—H1'	0.98
N2—C1	1.368 (3)	C2'—O2'	1.423 (3)
N2—C2	1.380 (3)	C2'—C3'	1.525 (4)
N2—H2	0.86	C2'—H2'	0.98
C2—C3	1.439 (3)	O2'—H2O'	0.82
C3—C4	1.362 (3)	C3'—O3'	1.414 (3)
C3—C5	1.479 (4)	C3'—C4'	1.519 (4)
C4—H4	0.93	C3'—H3'	0.98
C5—C10	1.391 (4)	O3'—H3O'	0.82
C5—C6	1.398 (4)	C4'—O4'	1.447 (3)
C6—C7	1.378 (4)	C4'—C5'	1.499 (4)
C6—H6	0.93	C4'—H4'	0.98
C7—C8	1.389 (6)	C5'—O5'	1.430 (4)
C7—H7	0.93	C5'—H51'	0.97
C8—C9	1.395 (7)	C5'—H52'	0.97
C8—H8	0.93	O5'—H5O'	0.82
C9—C10	1.389 (4)
C4—N1—C1	121.1 (2)	C5—C10—H10	119.2
C4—N1—C1'	122.6 (2)	O4'—C1'—N1	108.89 (19)
C1—N1—C1'	115.7 (2)	O4'—C1'—C2'	107.0 (2)
C1—N2—C2	127.3 (2)	N1—C1'—C2'	111.9 (2)
C1—N2—H2	116.3	O4'—C1'—H1'	109.7
C2—N2—H2	116.3	N1—C1'—H1'	109.7
O1—C1—N2	122.9 (2)	C2'—C1'—H1'	109.7
O1—C1—N1	122.3 (3)	O2'—C2'—C1'	105.6 (2)
N2—C1—N1	114.8 (2)	O2'—C2'—C3'	110.9 (2)
O2—C2—N2	118.6 (2)	C1'—C2'—C3'	101.4 (2)
O2—C2—C3	125.9 (2)	O2'—C2'—H2'	112.7
N2—C2—C3	115.4 (2)	C1'—C2'—H2'	112.7
C4—C3—C2	117.8 (2)	C3'—C2'—H2'	112.7
C4—C3—C5	120.5 (2)	C2'—O2'—H2O'	109.5
C2—C3—C5	121.7 (2)	O3'—C3'—C4'	113.4 (2)
C3—C4—N1	123.4 (2)	O3'—C3'—C2'	111.9 (2)
C3—C4—H4	118.3	C4'—C3'—C2'	101.8 (2)
N1—C4—H4	118.3	O3'—C3'—H3'	109.8
C10—C5—C6	118.3 (3)	C4'—C3'—H3'	109.8
C10—C5—C3	119.8 (3)	C2'—C3'—H3'	109.8
C6—C5—C3	121.9 (3)	C3'—O3'—H3O'	109.5
C7—C6—C5	120.7 (3)	O4'—C4'—C5'	109.8 (2)
C7—C6—H6	119.7	O4'—C4'—C3'	104.1 (2)
C5—C6—H6	119.7	C5'—C4'—C3'	117.3 (3)
C6—C7—C8	120.7 (4)	O4'—C4'—H4'	108.4
C6—C7—H7	119.7	C5'—C4'—H4'	108.4
C8—C7—H7	119.7	C3'—C4'—H4'	108.4
C7—C8—C9	119.5 (3)	C1'—O4'—C4'	110.48 (19)
C7—C8—H8	120.2	O5'—C5'—C4'	111.8 (2)
C9—C8—H8	120.2	O5'—C5'—H51'	109.2
C10—C9—C8	119.3 (4)	C4'—C5'—H51'	109.2
C10—C9—H9	120.3	O5'—C5'—H52'	109.2
C8—C9—H9	120.3	C4'—C5'—H52'	109.2
C9—C10—C5	121.5 (3)	H51'—C5'—H52'	107.9
C9—C10—H10	119.2	C5'—O5'—H5O'	109.5
C2—N2—C1—O1	177.3 (3)	C8—C9—C10—C5	−0.3 (5)
C2—N2—C1—N1	−3.4 (4)	C6—C5—C10—C9	1.2 (5)
C4—N1—C1—O1	−176.1 (3)	C3—C5—C10—C9	−178.0 (3)
C1'—N1—C1—O1	−4.5 (4)	C4—N1—C1'—O4'	1.7 (3)
C4—N1—C1—N2	4.5 (4)	C1—N1—C1'—O4'	−169.9 (2)
C1'—N1—C1—N2	176.2 (2)	C4—N1—C1'—C2'	−116.3 (3)
C1—N2—C2—O2	−178.6 (3)	C1—N1—C1'—C2'	72.1 (3)
C1—N2—C2—C3	1.5 (4)	O4'—C1'—C2'—O2'	88.5 (2)
O2—C2—C3—C4	179.5 (3)	N1—C1'—C2'—O2'	−152.3 (2)
N2—C2—C3—C4	−0.7 (4)	O4'—C1'—C2'—C3'	−27.3 (2)
O2—C2—C3—C5	0.0 (4)	N1—C1'—C2'—C3'	91.9 (2)
N2—C2—C3—C5	179.8 (2)	O2'—C2'—C3'—O3'	47.3 (3)
C2—C3—C4—N1	2.1 (4)	C1'—C2'—C3'—O3'	159.1 (2)
C5—C3—C4—N1	−178.4 (2)	O2'—C2'—C3'—C4'	−74.2 (2)
C1—N1—C4—C3	−4.2 (4)	C1'—C2'—C3'—C4'	37.6 (2)
C1'—N1—C4—C3	−175.3 (2)	O3'—C3'—C4'—O4'	−155.9 (2)
C4—C3—C5—C10	38.3 (4)	C2'—C3'—C4'—O4'	−35.4 (2)
C2—C3—C5—C10	−142.2 (3)	O3'—C3'—C4'—C5'	82.7 (3)
C4—C3—C5—C6	−140.9 (3)	C2'—C3'—C4'—C5'	−156.9 (2)
C2—C3—C5—C6	38.7 (4)	N1—C1'—O4'—C4'	−115.8 (2)
C10—C5—C6—C7	−1.1 (4)	C2'—C1'—O4'—C4'	5.3 (3)
C3—C5—C6—C7	178.1 (3)	C5'—C4'—O4'—C1'	145.6 (2)
C5—C6—C7—C8	0.2 (5)	C3'—C4'—O4'—C1'	19.3 (3)
C6—C7—C8—C9	0.7 (6)	O4'—C4'—C5'—O5'	−64.2 (3)
C7—C8—C9—C10	−0.6 (6)	C3'—C4'—C5'—O5'	54.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3′^i	0.86	2.02	2.842 (3)	159
O2′—H2O′···O2^ii	0.82	2	2.740 (3)	151
O3′—H3O′···O3W^iii	0.82	1.83	2.600 (9)	157
O3′—H3O′···O3W′^iii	0.82	1.88	2.691 (9)	169
O5′—H5O′···O2′^iv	0.82	1.92	2.735 (3)	171

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+2, y−1/2, −z+3/2.