Three different fluoro- or chloro-substituted 1′-de­oxy-1′-phenyl-β-D-ribo­furan­oses

Crystal structures are reported for three fluoro- or chloro-substituted 1′-de­oxy-1′-phenyl-β-D-ribo­furan­oses, namely 1′-de­oxy-1′-(2,4,5-tri­fluoro­phenyl)-β-D-ribo­furan­ose, C₁₁H₁₁F₃O₄, (I), 1′-de­oxy-1′-(2,4,6-tri­fluoro­phenyl)-β-D-ribo­furan­ose, C₁₁H₁₁F₃O₄, (II), and 1′-(4-chloro­phenyl)-1′-de­oxy-β-D-ribo­furan­ose, C₁₁H₁₃ClO₄, (III). The five-membered furan­ose ring of the three compounds has a conformation between a C2′-endo,C3′-exo twist and a C2′-endo envelope. The ribo­furan­ose groups of (I) and (III) are connected by inter­molecular O—H...O hydrogen bonds to six symmetry-related mol­ecules to form double layers, while the ribo­furan­ose group of (II) is connected by O—H...O hydrogen bonds to four symmetry-related mol­ecules to form single layers. The O...O contact distance of the O—H...O hydrogen bonds ranges from 2.7172 (15) to 2.8895 (19) Å. Neighbouring double layers of (I) are connected by a very weak inter­molecular C—F...π contact. The layers of (II) are connected by one C—H...O and two C—H...F contacts, while the double layers of (III) are connected by a C—H...Cl contact. The conformations of the mol­ecules are compared with those of seven related mol­ecules. The orientation of the benzene ring is coplanar with the H—C1′ bond or bisecting the H—C1′—C2′ angle, or inter­mediate between these positions. The orientation of the benzene ring is independent of the substitution pattern of the ring and depends mainly on crystal-packing effects.

S1. Introduction

The stability of nucleic acids is mainly determined by hydrogen bonding, base stacking and solvation. In order to probe these inter­actions, a common approach is to replace the natural nucleobases by nonpolar nucleoside isoesters (Gohlke et al., 2012). The shape and size of the modified base should be kept as similar as possible to that of the native base. This concept, introduced by Kool (2001), has been extended by us for RNA. A series of halogenated nucleosides was prepared and their ability to form duplexes was determined (Parsch & Engels, 2002). The crystal structures of a number of fluoro-substituted 1'-de­oxy-1'-phenyl-β-D-ribo­furan­oses have already been reported (Bats et al., 1999a,b, 2000). We report here the structures of three new compounds, namely 1'-de­oxy-1'-(2,4,5-tri­fluoro­phenyl)-β-D-ribo­furan­ose, (I), 1'-de­oxy-1'-(2,4,6-tri­fluoro­phenyl)-β-D-ribo­furan­ose, (II), and 1'-(4-chloro­phenyl)-1'-de­oxy-β-D-ribo­furan­ose, (III).

S2. Experimental

S2.1. Synthesis and crystallization

The title compounds were prepared using the procedure described by Krohn et al. (1992). Thus, 1-bromo-2,4,5-tri­fluoro­benzene [for (I)], 2,4,6-tri­fluoro­benzene [for (II)] or 1-bromo-4-chloro­benzene [for (III)] was reacted with n-butyl­lithium and subsequently with 2,3,5-tri-O-benzyl-D-ribono-1,4-lactone (Timpe et al., 1975; Barker & Fletcher, 1961) to give the corresponding fluoro- or chloro-substituted 2',3',5'-tri-O-benzyl-1'-de­oxy-1'-phenyl-β-D-ribo­furan­ose. Next, the O-benzyl protecting groups were removed using palladium hydroxide on a carbon matrix as catalyst. Compounds (I), (II) and (III) were obtained in yields of 94, 92 and 95%, respectively, and were all recrystallized from water. For full details of the syntheses, see Živković (2005).

S2.2. Refinement

Friedel opposites were merged for (I) and (II), but not for (III), which contains a Cl atom as anomalous scatterer. The C-bound H atoms were positioned geometrically and treated as riding, with C—H = 0.95 Å for aromatic, 0.99 Å for methyl­ene or 1.00 Å for methine C—H groups, and with U_iso(H) = 1.2U_eq(C). The O-bound H atoms were taken from difference Fourier syntheses, and their coordinates and isotropic displacement parameters were refined.

S3. Results and discussion

The molecular structure of (I) is shown in Fig. 1. The five-membered furan­ose ring has a conformation approximately between a C2'-endo envelope and a C2'-endo,C3'-exo twist. The phenyl group attached to C1' and the hy­droxy group attached to C2' are in pseudo-equatorial positions, and the hy­droxy group attached to C3' is in a pseudo-axial position with respect to the furan­ose ring. The tri­fluoro­phenyl group is planar [r.m.s. deviation of the C and F atoms from the plane = 0.0044 (14) Å]. The ribo­furan­ose groups are connected by inter­molecular O—H···O hydrogen bonds (Table 2 and Fig. 2) to form double layers parallel to (001). Each molecule is hydrogen-bonded to six symmetry-related molecules. The molecules within a double layer are further stabilized by a rather short inter­molecular C—H···O contact, with an H···O distance of 2.32 Å, and by four weak C—H···F inter­actions (involving atoms F2 and F5), with H···F distances between 2.59 and 2.75 Å (Table 2). There is only one relevant inter­molecular inter­action among the double layers along the c-axis direction with a contact distance shorter than the van der Waals contact distance [Reference for vdW distances?]; this is a weak inter­molecular C—F···π contact [C5—F5···C4^vi; symmetry code: (vi) -x + 1/2, y + 1/2, -z + 1], with an F···C distance of 3.047 (2) Å and a C—F···C angle of 148.25 (10)°. This inter­action is expected to be very weak. Therefore, the crystal habit is an (001) plate.

The crystal structure of (I) is isomorphous with that of 1'-de­oxy-1'-(2-fluoro­phenyl)-β-D-ribo­furan­ose (Bats et al., 1999a). As the 2-fluoro substituent is the only F atom occuring in both compounds, this atom may be the stabilizing factor resulting in the observed crystal packing, while the 4-fluoro and 5-fluoro substituents have little effect on the packing of the structure. This is in agreement with the inter­molecular contacts presented in Table 2. Thus, also, the related compound 1'-de­oxy-1'-(2,4-di­fluoro­phenyl)-β-D-ribo­furan­ose (Bats et al., 2000) could be expected to have the same crystal structure. The space group of this structure is also C2 and the unit-cell dimensions show some similarity with those of (I). However, the hydrogen bonding within the double layers of the compound differs from that observed in (I), showing the crystal structures to be different.

The molecular structure of (II) is shown in Fig. 3. The five-membered furan­ose ring has an approximately C2'-endo envelope conformation. The tri­fluoro­phenyl group is in a pseudo-equatorial position with respect to the furan­ose ring. It adopts an orientation with the C2—F2 and C1'—H1A bonds in synperiplanar positions (torsion angle H1A—C1'—C1—C2 = -13°), resulting in an intra­molecular H1A···F2 distance of 2.35 Å, which is shorter than the van der Waals contact distance. The tri­fluoro­phenyl group shows a small deviation from planarity [r.m.s. deviation of the C and F atoms from the plane = 0.0270 (13) Å]. Substituent atoms C1' and F6 deviate from the benzene plane by 0.110 (2) Å in opposite directions. This deviation from planarity may result from a steric repulsion between atoms F6 and O4'. The observed F6···O4' distance of 2.8183 (15) Å is slightly shorter than the van der Waals contact distance. The ribo­furan­ose groups are connected by inter­molecular O—H···O hydrogen bonds (Table 3 and Fig. 4) to four symmetry-related molecules to form layers parallel to (010). The molecules within a layer are also stabilized by a very weak inter­molecular O—H···F and C—H···F contact (third and fifth entries in Table 3). The molecular layers are connected along the b-axis direction by an inter­molecular C—H···O inter­action, with an H···O distance of 2.55 Å, and by two inter­molecular C—H···F inter­actions (both involving the 4-fluoro substituent), with H···F distances of 2.53 and 2.62 Å (last three entries of Table 3).

The molecular structure of (III) is shown in Fig. 5. The crystal structure is isomorphous with that of one of the two polymorphs of 1'-de­oxy-1'-(4-fluoro­phenyl)-β-D-ribo­furan­ose reported by Bats et al. (2000). The ribo­furan­ose ring has a conformation near a C2'-endo,C3'-exo twist. The conformation of the molecule is rather similar to those observed in 1'-de­oxy-1'-(3-fluoro­phenyl)-β-D-ribo­furan­ose (Bats et al., 1999b) and 1'-de­oxy-1'-phenyl-β-D-ribo­furan­ose (Matulic-Adamic et al., 1996; Štambaský et al., 2011). The phenyl group attached to C1' and the hy­droxy group attached to C2' are in pseudo-equatorial positions, and the hy­droxy group attached to C3' is in a pseudo-axial position with respect to the five-membered ring. The shortest intra­molecular contact distance is 2.43 Å between atoms O4' and H6A. The benzene ring is planar [r.m.s. deviation of the C atoms from the plane = 0.0068 (11) Å]. The Cl atom is displaced by 0.064 (2) Å from the benzene plane as a result of crystal-packing effects. The ribo­furan­ose groups are connected by inter­molecular O—H···O hydrogen bonds (Table 4 and Fig. 6) to six symmetry-related molecules to form double layers parallel to (001). The molecules within a double layer are also connected by a weak inter­molecular C—H···O contact, with an H···O distance of 2.58 Å. The double layers are connected along the c-axis direction by a rather weak inter­molecular C—H···Cl contact, with an H···Cl distance of 2.74 Å.

The conformations of the ribo­furan­ose rings and the relative orientations of the phenyl substituents in (I), (II) and (III) are compared in Table 5 with the corresponding values observed in the crystal structures of related compounds. The conformation of the five-membered ring is characterized by the ring-puckering parameters q and ϕ as defined by Cremer & Pople (1975). The value of q (0.37–0.42 Å) is rather constant for all ten entries. The value of the rotation angle ϕ varies between 60 and 87° in nine structures. This corresponds to a conformation ranging from one inter­mediate between a C1'-exo,C2'-endo twist and a C2'-endo envelope to a C2'-endo,C3'-exo twist. Only one entry in Table 5 shows a very different conformation with ϕ = 275°, corresponding to an unsymmetrical C2'-exo,C3'-endo twist conformation. These findings are in agreement with the observation by Murray-Rust & Motherwell (1978) that conformations near C2'-endo and C3'-endo envelopes are most favoured. The torsion angle O4'—C1'—C1—C6 is in the range 2–50°. In three structures, a value between 45 and 50° is observed and the benzene ring is almost coplanar with the H—C1' bond (the H—C1'—C1—C2 torsion angle ranges from -16 to -4°). Five structures show an O4'—C1'—C1—C6 torsion angle between 2 and 9°. In this case, the benzene ring has an orientation bis­ecting the H—C1'—C2' angle. Two structures have an inter­mediate orientation of the benzene ring, with O4'—C1'—C1—C6 torsion angles of 27 and 29°. The relative orientation of the benzene ring does not depend on the substitution pattern of this ring. Even for the two polymorphs of the 4-fluoro­phenyl compound, large differences were observed (Bats et al., 2000). Thus, the orientation of the phenyl group is mainly determined by crystal-packing effects.

Related literature

For related literature, see: Barker & Fletcher (1961); Bats et al. (1999a, 1999b, 2000); Cremer & Pople (1975); Gohlke et al. (2012); Kool (2001); Krohn et al. (1992); Matulic-Adamic, Beigelman, Portmann, Egli & Usman (1996); Murray-Rust & Motherwell (1978); Parsch & Engels (2002); Timpe et al. (1975); Štambaský et al. (2011); Živković (2005).

Computing details

For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SMART (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I), viewed down [010]. C-bound H atoms have been omitted for clarity. Intermolecular O—H···O hydrogen bonds are shown as dashed lines.
	Fig. 3. The molecular structure of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 4. The crystal packing of (II), viewed down [001]. C-bound H atoms have been omitted for clarity. Intermolecular O—H···O hydrogen bonds are shown as dashed lines.
	Fig. 5. The molecular structure of (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 6. The crystal packing of (III), viewed down [010]. C-bound H atoms have been omitted for clarity. Intermolecular O—H···O hydrogen bonds are shown as dashed lines.

(I) 1'-Deoxy-1'-(2,4,5-trifluorophenyl)-β-D-ribofuranose

Crystal data

C11H11F3O4	F(000) = 544
Mr = 264.20	Dx = 1.653 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 84 reflections
a = 13.248 (2) Å	θ = 3–23°
b = 4.9913 (10) Å	µ = 0.16 mm^−1
c = 16.312 (6) Å	T = 143 K
β = 100.18 (2)°	Plate, colourless
V = 1061.6 (5) Å^3	0.60 × 0.38 × 0.10 mm
Z = 4

Data collection

Siemens SMART 1K CCD area-detector diffractometer	1924 independent reflections
Radiation source: normal-focus sealed tube	1774 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 31.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −19→19
Tmin = 0.853, Tmax = 0.984	k = −7→7
11403 measured reflections	l = −22→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.3P] where P = (Fo^2 + 2Fc^2)/3
1924 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.34 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F2	−0.01656 (7)	0.2424 (2)	0.29412 (7)	0.0294 (3)
F4	0.10539 (9)	0.9400 (3)	0.47910 (7)	0.0363 (3)
F5	0.28911 (8)	0.9152 (3)	0.43078 (7)	0.0333 (3)
O2'	0.03839 (8)	0.3322 (3)	0.10934 (8)	0.0205 (2)
H2B	0.0174 (19)	0.183 (7)	0.0987 (16)	0.037 (7)*
O3'	0.16450 (8)	−0.0876 (3)	0.07279 (8)	0.0206 (2)
H3B	0.134 (2)	−0.083 (8)	0.0205 (18)	0.055 (8)*
O4'	0.27512 (8)	0.1283 (3)	0.24105 (7)	0.0208 (2)
O5'	0.43560 (8)	0.3197 (3)	0.08891 (8)	0.0212 (2)
H5C	0.4692 (19)	0.185 (7)	0.0912 (15)	0.037 (7)*
C1'	0.16895 (10)	0.2009 (3)	0.23188 (9)	0.0164 (3)
H1A	0.1261	0.0370	0.2338	0.020*
C2'	0.14429 (10)	0.3297 (3)	0.14487 (9)	0.0155 (3)
H2A	0.1699	0.5186	0.1489	0.019*
C3'	0.21087 (10)	0.1656 (3)	0.09543 (9)	0.0158 (3)
H3A	0.2264	0.2658	0.0460	0.019*
C4'	0.30682 (10)	0.1185 (3)	0.16077 (9)	0.0158 (3)
H4A	0.3355	−0.0627	0.1523	0.019*
C5'	0.38994 (10)	0.3280 (3)	0.16230 (10)	0.0186 (3)
H5A	0.3602	0.5079	0.1673	0.022*
H5B	0.4438	0.2987	0.2119	0.022*
C1	0.15409 (11)	0.3905 (3)	0.30037 (9)	0.0174 (3)
C2	0.06057 (11)	0.4104 (4)	0.32753 (10)	0.0204 (3)
C3	0.04071 (12)	0.5920 (4)	0.38678 (11)	0.0249 (3)
H3C	−0.0244	0.5999	0.4034	0.030*
C4	0.11933 (13)	0.7610 (4)	0.42062 (10)	0.0243 (3)
C5	0.21418 (12)	0.7470 (4)	0.39567 (10)	0.0228 (3)
C6	0.23187 (12)	0.5644 (3)	0.33689 (10)	0.0207 (3)
H6A	0.2974	0.5562	0.3209	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F2	0.0197 (4)	0.0350 (6)	0.0353 (6)	−0.0076 (4)	0.0097 (4)	−0.0119 (5)
F4	0.0459 (6)	0.0344 (6)	0.0304 (6)	−0.0013 (6)	0.0118 (5)	−0.0145 (5)
F5	0.0366 (5)	0.0330 (6)	0.0291 (5)	−0.0148 (5)	0.0024 (4)	−0.0079 (5)
O2'	0.0145 (4)	0.0224 (6)	0.0241 (6)	0.0021 (4)	0.0024 (4)	0.0015 (5)
O3'	0.0241 (5)	0.0171 (5)	0.0209 (5)	−0.0057 (4)	0.0048 (4)	−0.0021 (5)
O4'	0.0160 (4)	0.0288 (6)	0.0184 (5)	0.0059 (4)	0.0054 (4)	0.0059 (5)
O5'	0.0153 (4)	0.0239 (6)	0.0258 (6)	0.0016 (5)	0.0075 (4)	0.0072 (5)
C1'	0.0135 (5)	0.0179 (7)	0.0186 (7)	0.0005 (5)	0.0045 (5)	0.0020 (5)
C2'	0.0135 (5)	0.0146 (6)	0.0185 (7)	0.0011 (5)	0.0034 (5)	0.0021 (5)
C3'	0.0162 (5)	0.0145 (6)	0.0176 (7)	−0.0017 (5)	0.0051 (5)	0.0015 (5)
C4'	0.0151 (5)	0.0141 (6)	0.0191 (7)	0.0009 (5)	0.0051 (5)	0.0014 (5)
C5'	0.0163 (5)	0.0173 (6)	0.0227 (7)	−0.0022 (5)	0.0050 (5)	0.0004 (6)
C1	0.0187 (6)	0.0176 (7)	0.0162 (6)	0.0000 (5)	0.0039 (5)	0.0021 (5)
C2	0.0186 (6)	0.0227 (7)	0.0203 (7)	−0.0013 (6)	0.0045 (5)	−0.0017 (6)
C3	0.0233 (7)	0.0293 (8)	0.0238 (8)	0.0017 (6)	0.0089 (6)	−0.0038 (7)
C4	0.0327 (8)	0.0237 (8)	0.0167 (7)	0.0020 (6)	0.0050 (6)	−0.0022 (6)
C5	0.0267 (7)	0.0213 (7)	0.0194 (7)	−0.0062 (6)	0.0013 (6)	0.0001 (6)
C6	0.0206 (6)	0.0229 (7)	0.0186 (7)	−0.0034 (6)	0.0034 (5)	0.0016 (6)

Geometric parameters (Å, º)

F2—C2	1.3590 (19)	C2'—H2A	1.0000
F4—C4	1.343 (2)	C3'—C4'	1.526 (2)
F5—C5	1.3482 (19)	C3'—H3A	1.0000
O2'—C2'	1.4202 (17)	C4'—C5'	1.516 (2)
O2'—H2B	0.80 (3)	C4'—H4A	1.0000
O3'—C3'	1.4249 (19)	C5'—H5A	0.9900
O3'—H3B	0.88 (3)	C5'—H5B	0.9900
O4'—C1'	1.4347 (16)	C1—C2	1.3912 (19)
O4'—C4'	1.4450 (18)	C1—C6	1.397 (2)
O5'—C5'	1.4342 (19)	C2—C3	1.384 (2)
O5'—H5C	0.80 (3)	C3—C4	1.378 (3)
C1'—C1	1.503 (2)	C3—H3C	0.9500
C1'—C2'	1.540 (2)	C4—C5	1.389 (2)
C1'—H1A	1.0000	C5—C6	1.373 (2)
C2'—C3'	1.533 (2)	C6—H6A	0.9500
C2'—O2'—H2B	111.1 (19)	C5'—C4'—H4A	109.5
C3'—O3'—H3B	109 (2)	C3'—C4'—H4A	109.5
C1'—O4'—C4'	110.53 (11)	O5'—C5'—C4'	112.25 (13)
C5'—O5'—H5C	107.3 (18)	O5'—C5'—H5A	109.2
O4'—C1'—C1	109.66 (12)	C4'—C5'—H5A	109.2
O4'—C1'—C2'	104.25 (11)	O5'—C5'—H5B	109.2
C1—C1'—C2'	112.82 (13)	C4'—C5'—H5B	109.2
O4'—C1'—H1A	110.0	H5A—C5'—H5B	107.9
C1—C1'—H1A	110.0	C2—C1—C6	116.82 (14)
C2'—C1'—H1A	110.0	C2—C1—C1'	121.49 (13)
O2'—C2'—C3'	114.11 (12)	C6—C1—C1'	121.62 (13)
O2'—C2'—C1'	114.41 (11)	F2—C2—C3	117.51 (13)
C3'—C2'—C1'	102.34 (12)	F2—C2—C1	118.50 (14)
O2'—C2'—H2A	108.6	C3—C2—C1	123.99 (15)
C3'—C2'—H2A	108.6	C4—C3—C2	117.22 (14)
C1'—C2'—H2A	108.6	C4—C3—H3C	121.4
O3'—C3'—C4'	108.19 (12)	C2—C3—H3C	121.4
O3'—C3'—C2'	110.39 (11)	F4—C4—C3	120.17 (15)
C4'—C3'—C2'	101.57 (12)	F4—C4—C5	119.11 (15)
O3'—C3'—H3A	112.1	C3—C4—C5	120.71 (15)
C4'—C3'—H3A	112.1	F5—C5—C6	120.43 (15)
C2'—C3'—H3A	112.1	F5—C5—C4	118.70 (15)
O4'—C4'—C5'	106.77 (12)	C6—C5—C4	120.86 (15)
O4'—C4'—C3'	106.75 (11)	C5—C6—C1	120.40 (14)
C5'—C4'—C3'	114.73 (12)	C5—C6—H6A	119.8
O4'—C4'—H4A	109.5	C1—C6—H6A	119.8
C4'—O4'—C1'—C1	−139.83 (13)	C2'—C1'—C1—C2	90.39 (17)
C4'—O4'—C1'—C2'	−18.78 (15)	O4'—C1'—C1—C6	29.32 (19)
O4'—C1'—C2'—O2'	158.76 (13)	C2'—C1'—C1—C6	−86.40 (16)
C1—C1'—C2'—O2'	−82.33 (15)	C6—C1—C2—F2	−179.26 (14)
O4'—C1'—C2'—C3'	34.80 (14)	C1'—C1—C2—F2	3.8 (2)
C1—C1'—C2'—C3'	153.71 (11)	C6—C1—C2—C3	0.9 (2)
O2'—C2'—C3'—O3'	−46.41 (17)	C1'—C1—C2—C3	−176.06 (16)
C1'—C2'—C3'—O3'	77.75 (13)	F2—C2—C3—C4	179.76 (16)
O2'—C2'—C3'—C4'	−160.99 (12)	C1—C2—C3—C4	−0.4 (3)
C1'—C2'—C3'—C4'	−36.84 (13)	C2—C3—C4—F4	−179.28 (16)
C1'—O4'—C4'—C5'	118.09 (13)	C2—C3—C4—C5	0.0 (3)
C1'—O4'—C4'—C3'	−5.08 (16)	F4—C4—C5—F5	−0.4 (2)
O3'—C3'—C4'—O4'	−89.60 (13)	C3—C4—C5—F5	−179.64 (17)
C2'—C3'—C4'—O4'	26.60 (15)	F4—C4—C5—C6	179.14 (16)
O3'—C3'—C4'—C5'	152.34 (12)	C3—C4—C5—C6	−0.1 (3)
C2'—C3'—C4'—C5'	−91.46 (14)	F5—C5—C6—C1	−179.84 (15)
O4'—C4'—C5'—O5'	173.95 (12)	C4—C5—C6—C1	0.6 (2)
C3'—C4'—C5'—O5'	−68.01 (16)	C2—C1—C6—C5	−1.0 (2)
O4'—C1'—C1—C2	−153.89 (14)	C1'—C1—C6—C5	175.95 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2′—H2B···O5′^i	0.80 (3)	2.10 (3)	2.8895 (19)	166 (3)
O3′—H3B···O5′^ii	0.88 (3)	1.92 (3)	2.7738 (19)	164 (4)
O5′—H5C···O2′^iii	0.80 (3)	1.98 (3)	2.7795 (18)	171 (3)
C2′—H2A···O3′^iv	1.00	2.32	3.166 (2)	142
C5′—H5A···F2^v	0.99	2.67	3.081 (2)	105
C5′—H5B···F2^v	0.99	2.59	3.081 (2)	110
C6—H6A···F2^v	0.95	2.74	3.6340 (19)	157
C3—H3C···F5^i	0.95	2.75	3.640 (2)	157

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

(II) 1'-Deoxy-1'-(2,4,6-trifluorophenyl)-β-D-ribofuranose

Crystal data

C11H11F3O4	F(000) = 544
Mr = 264.20	Dx = 1.558 Mg m^−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 81 reflections
a = 11.209 (3) Å	θ = 3–23°
b = 20.221 (5) Å	µ = 0.15 mm^−1
c = 4.9699 (12) Å	T = 142 K
V = 1126.4 (5) Å^3	Rod, colourless
Z = 4	0.55 × 0.30 × 0.14 mm

Data collection

Siemens SMART 1K CCD area-detector diffractometer	2255 independent reflections
Radiation source: normal-focus sealed tube	2139 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 32.0°, θmin = 2.0°
Absorption correction: numerical (SHELXTL; Sheldrick, 2008)	h = −16→16
Tmin = 0.930, Tmax = 0.980	k = −30→29
19902 measured reflections	l = −7→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.04P)^2 + 0.25P] where P = (Fo^2 + 2Fc^2)/3
2255 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F2	0.56794 (9)	0.93713 (5)	1.2726 (2)	0.0287 (2)
F4	0.86049 (13)	1.05097 (6)	0.7823 (3)	0.0540 (4)
F6	0.74939 (8)	0.83724 (4)	0.52339 (19)	0.02270 (19)
O2'	0.38744 (9)	0.84093 (5)	0.8066 (2)	0.0192 (2)
H2B	0.361 (2)	0.8379 (11)	0.951 (5)	0.029 (6)*
O3'	0.41764 (10)	0.72085 (5)	1.1058 (2)	0.0222 (2)
H3B	0.343 (2)	0.7266 (11)	1.092 (5)	0.035 (6)*
O4'	0.67037 (8)	0.76384 (4)	0.9713 (2)	0.01536 (18)
O5'	0.77418 (9)	0.65233 (5)	0.6885 (2)	0.0196 (2)
H5C	0.810 (2)	0.6522 (12)	0.547 (5)	0.037 (7)*
C1'	0.59144 (11)	0.82024 (6)	0.9738 (3)	0.0134 (2)
H1A	0.5572	0.8247	1.1587	0.016*
C2'	0.49068 (11)	0.80116 (6)	0.7814 (3)	0.0145 (2)
H2A	0.5208	0.8045	0.5925	0.017*
C3'	0.47447 (11)	0.72775 (7)	0.8522 (3)	0.0160 (2)
H3A	0.4323	0.7027	0.7069	0.019*
C4'	0.60384 (11)	0.70527 (6)	0.8871 (3)	0.0139 (2)
H4A	0.6077	0.6713	1.0330	0.017*
C5'	0.65670 (12)	0.67670 (7)	0.6325 (3)	0.0182 (2)
H5A	0.6057	0.6403	0.5656	0.022*
H5B	0.6606	0.7113	0.4916	0.022*
C1	0.65950 (12)	0.88247 (6)	0.9098 (3)	0.0160 (2)
C2	0.64719 (14)	0.93884 (7)	1.0673 (3)	0.0219 (3)
C3	0.71151 (18)	0.99670 (8)	1.0297 (4)	0.0318 (4)
H3C	0.7001	1.0344	1.1406	0.038*
C4	0.79263 (17)	0.99621 (8)	0.8226 (4)	0.0332 (4)
C5	0.80965 (15)	0.94338 (8)	0.6513 (4)	0.0283 (3)
H5D	0.8663	0.9448	0.5093	0.034*
C6	0.73965 (13)	0.88817 (7)	0.6978 (3)	0.0190 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F2	0.0350 (5)	0.0259 (4)	0.0252 (4)	0.0076 (4)	0.0023 (4)	−0.0077 (4)
F4	0.0719 (9)	0.0297 (5)	0.0603 (8)	−0.0302 (6)	−0.0085 (8)	0.0141 (6)
F6	0.0219 (4)	0.0274 (4)	0.0188 (4)	0.0012 (3)	0.0038 (3)	−0.0005 (3)
O2'	0.0130 (4)	0.0255 (5)	0.0191 (5)	0.0059 (4)	−0.0005 (4)	0.0036 (4)
O3'	0.0131 (4)	0.0271 (5)	0.0266 (5)	0.0007 (4)	0.0062 (4)	0.0076 (4)
O4'	0.0113 (4)	0.0140 (4)	0.0208 (4)	0.0005 (3)	−0.0038 (4)	−0.0014 (4)
O5'	0.0147 (4)	0.0260 (5)	0.0181 (5)	0.0031 (4)	0.0027 (4)	−0.0010 (4)
C1'	0.0123 (5)	0.0146 (5)	0.0131 (5)	0.0017 (4)	−0.0013 (4)	0.0001 (4)
C2'	0.0106 (5)	0.0197 (5)	0.0133 (5)	0.0021 (4)	−0.0013 (4)	0.0012 (5)
C3'	0.0107 (5)	0.0186 (5)	0.0186 (6)	−0.0015 (4)	−0.0006 (4)	−0.0003 (5)
C4'	0.0120 (5)	0.0142 (5)	0.0155 (5)	−0.0011 (4)	−0.0004 (4)	−0.0015 (4)
C5'	0.0145 (5)	0.0224 (6)	0.0176 (5)	0.0017 (5)	−0.0015 (5)	−0.0051 (5)
C1	0.0152 (5)	0.0149 (5)	0.0179 (6)	0.0008 (4)	−0.0030 (5)	0.0010 (4)
C2	0.0257 (7)	0.0182 (6)	0.0217 (6)	0.0031 (5)	−0.0039 (6)	−0.0008 (5)
C3	0.0444 (9)	0.0164 (6)	0.0346 (8)	−0.0017 (6)	−0.0103 (8)	0.0000 (7)
C4	0.0412 (9)	0.0201 (6)	0.0384 (9)	−0.0122 (6)	−0.0109 (8)	0.0109 (7)
C5	0.0259 (7)	0.0308 (7)	0.0283 (8)	−0.0084 (6)	−0.0023 (6)	0.0117 (7)
C6	0.0182 (6)	0.0200 (5)	0.0189 (6)	−0.0003 (5)	−0.0019 (5)	0.0039 (5)

Geometric parameters (Å, º)

F2—C2	1.3532 (19)	C2'—H2A	1.0000
F4—C4	1.3582 (18)	C3'—C4'	1.5296 (18)
F6—C6	1.3506 (17)	C3'—H3A	1.0000
O2'—C2'	1.4147 (16)	C4'—C5'	1.5120 (19)
O2'—H2B	0.78 (3)	C4'—H4A	1.0000
O3'—C3'	1.4194 (18)	C5'—H5A	0.9900
O3'—H3B	0.85 (3)	C5'—H5B	0.9900
O4'—C1'	1.4435 (15)	C1—C6	1.389 (2)
O4'—C4'	1.4608 (15)	C1—C2	1.3898 (19)
O5'—C5'	1.4332 (16)	C2—C3	1.387 (2)
O5'—H5C	0.81 (3)	C3—C4	1.373 (3)
C1'—C1	1.5054 (18)	C3—H3C	0.9500
C1'—C2'	1.5293 (18)	C4—C5	1.379 (3)
C1'—H1A	1.0000	C5—C6	1.384 (2)
C2'—C3'	1.5363 (18)	C5—H5D	0.9500
C2'—O2'—H2B	110.3 (18)	C5'—C4'—H4A	109.1
C3'—O3'—H3B	111.0 (17)	C3'—C4'—H4A	109.1
C1'—O4'—C4'	109.28 (9)	O5'—C5'—C4'	109.19 (11)
C5'—O5'—H5C	106.6 (18)	O5'—C5'—H5A	109.8
O4'—C1'—C1	110.37 (10)	C4'—C5'—H5A	109.8
O4'—C1'—C2'	104.36 (10)	O5'—C5'—H5B	109.8
C1—C1'—C2'	116.94 (11)	C4'—C5'—H5B	109.8
O4'—C1'—H1A	108.3	H5A—C5'—H5B	108.3
C1—C1'—H1A	108.3	C6—C1—C2	115.04 (13)
C2'—C1'—H1A	108.3	C6—C1—C1'	123.86 (12)
O2'—C2'—C1'	113.91 (11)	C2—C1—C1'	121.08 (12)
O2'—C2'—C3'	115.61 (11)	F2—C2—C3	117.68 (13)
C1'—C2'—C3'	100.83 (10)	F2—C2—C1	117.96 (13)
O2'—C2'—H2A	108.7	C3—C2—C1	124.35 (15)
C1'—C2'—H2A	108.7	C4—C3—C2	116.05 (15)
C3'—C2'—H2A	108.7	C4—C3—H3C	122.0
O3'—C3'—C4'	107.18 (11)	C2—C3—H3C	122.0
O3'—C3'—C2'	110.58 (11)	F4—C4—C3	118.39 (17)
C4'—C3'—C2'	101.60 (10)	F4—C4—C5	117.58 (17)
O3'—C3'—H3A	112.3	C3—C4—C5	124.03 (15)
C4'—C3'—H3A	112.3	C4—C5—C6	116.32 (16)
C2'—C3'—H3A	112.3	C4—C5—H5D	121.8
O4'—C4'—C5'	110.46 (10)	C6—C5—H5D	121.8
O4'—C4'—C3'	105.99 (10)	F6—C6—C5	117.52 (14)
C5'—C4'—C3'	112.96 (11)	F6—C6—C1	118.40 (12)
O4'—C4'—H4A	109.1	C5—C6—C1	124.07 (14)
C4'—O4'—C1'—C1	−149.30 (10)	C2'—C1'—C1—C6	−72.05 (16)
C4'—O4'—C1'—C2'	−22.87 (13)	O4'—C1'—C1—C2	−131.69 (13)
O4'—C1'—C2'—O2'	163.85 (11)	C2'—C1'—C1—C2	109.27 (15)
C1—C1'—C2'—O2'	−73.93 (15)	C6—C1—C2—F2	178.17 (12)
O4'—C1'—C2'—C3'	39.36 (12)	C1'—C1—C2—F2	−3.0 (2)
C1—C1'—C2'—C3'	161.58 (11)	C6—C1—C2—C3	−2.4 (2)
O2'—C2'—C3'—O3'	−50.08 (15)	C1'—C1—C2—C3	176.40 (14)
C1'—C2'—C3'—O3'	73.24 (12)	F2—C2—C3—C4	178.85 (15)
O2'—C2'—C3'—C4'	−163.61 (11)	C1—C2—C3—C4	−0.6 (2)
C1'—C2'—C3'—C4'	−40.29 (12)	C2—C3—C4—F4	−178.05 (15)
C1'—O4'—C4'—C5'	119.36 (11)	C2—C3—C4—C5	2.1 (3)
C1'—O4'—C4'—C3'	−3.32 (14)	F4—C4—C5—C6	179.75 (15)
O3'—C3'—C4'—O4'	−88.31 (12)	C3—C4—C5—C6	−0.4 (3)
C2'—C3'—C4'—O4'	27.74 (13)	C4—C5—C6—F6	176.13 (14)
O3'—C3'—C4'—C5'	150.61 (11)	C4—C5—C6—C1	−3.0 (2)
C2'—C3'—C4'—C5'	−93.35 (12)	C2—C1—C6—F6	−174.87 (12)
O4'—C4'—C5'—O5'	65.94 (14)	C1'—C1—C6—F6	6.4 (2)
C3'—C4'—C5'—O5'	−175.56 (11)	C2—C1—C6—C5	4.3 (2)
O4'—C1'—C1—C6	46.99 (17)	C1'—C1—C6—C5	−174.46 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2′—H2B···O5′^i	0.78 (3)	2.05 (3)	2.8157 (17)	168 (2)
O3′—H3B···O4′^i	0.85 (3)	1.97 (3)	2.8151 (16)	175 (2)
O3′—H3B···F6^i	0.85 (3)	2.53 (2)	2.8865 (15)	106.1 (19)
O5′—H5C···O2′^ii	0.81 (3)	1.97 (3)	2.7719 (17)	175 (3)
C3′—H3A···F6^iii	1.00	2.48	3.4024 (17)	153
C4′—H4A···F4^iv	1.00	2.62	3.5489 (19)	154
C5′—H5A···F4^v	0.99	2.53	3.2788 (19)	132
C3—H3C···O5′^vi	0.95	2.55	3.448 (2)	159

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

(III) 1'-(4-Chlorophenyl)-1'-deoxy-β-D-ribofuranose

Crystal data

C11H13ClO4	F(000) = 512
Mr = 244.66	Dx = 1.478 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 167 reflections
a = 6.7097 (9) Å	θ = 3–23°
b = 6.8447 (9) Å	µ = 0.34 mm^−1
c = 23.948 (4) Å	T = 145 K
V = 1099.9 (3) Å^3	Rod, colourless
Z = 4	0.50 × 0.20 × 0.14 mm

Data collection

Siemens SMART 1K CCD area-detector diffractometer	4164 independent reflections
Radiation source: normal-focus sealed tube	3470 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 33.5°, θmin = 1.7°
Absorption correction: numerical (SHELXTL; Sheldrick, 2008)	h = −10→10
Tmin = 0.872, Tmax = 0.955	k = −10→10
24334 measured reflections	l = −35→37

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.037P)^2 + 0.36P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4164 reflections	Δρmax = 0.31 e Å^−3
157 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Absolute structure: Flack (1983), with 1707 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl4	0.33378 (9)	1.10912 (7)	0.462908 (19)	0.05133 (16)
O2'	−0.06740 (14)	0.54119 (15)	0.67752 (4)	0.0202 (2)
H2B	−0.144 (4)	0.462 (4)	0.6741 (11)	0.065 (8)*
O3'	0.13673 (16)	0.38253 (16)	0.76749 (4)	0.0218 (2)
H3B	0.126 (3)	0.295 (3)	0.7843 (9)	0.035 (6)*
O4'	0.46384 (14)	0.53336 (14)	0.68725 (5)	0.0240 (2)
O5'	0.72931 (14)	0.19941 (15)	0.66821 (5)	0.0230 (2)
H5C	0.760 (3)	0.116 (3)	0.6873 (8)	0.031 (5)*
C1'	0.28076 (18)	0.62872 (18)	0.67316 (6)	0.0176 (2)
H1A	0.2426	0.7172	0.7046	0.021*
C2'	0.12592 (18)	0.46453 (18)	0.66913 (6)	0.0164 (2)
H2A	0.1336	0.4022	0.6314	0.020*
C3'	0.19912 (18)	0.32019 (19)	0.71343 (6)	0.0174 (2)
H3A	0.1523	0.1845	0.7053	0.021*
C4'	0.42579 (18)	0.33727 (18)	0.70708 (6)	0.0170 (2)
H4A	0.4888	0.3213	0.7446	0.020*
C5'	0.51630 (18)	0.1898 (2)	0.66741 (6)	0.0217 (3)
H5A	0.4730	0.0568	0.6782	0.026*
H5B	0.4679	0.2156	0.6291	0.026*
C1	0.3010 (2)	0.7494 (2)	0.62077 (6)	0.0204 (2)
C2	0.1382 (2)	0.8597 (2)	0.60277 (6)	0.0256 (3)
H2C	0.0184	0.8584	0.6239	0.031*
C3	0.1488 (3)	0.9712 (2)	0.55445 (7)	0.0316 (3)
H3C	0.0371	1.0448	0.5421	0.038*
C4	0.3260 (3)	0.9730 (2)	0.52456 (6)	0.0324 (4)
C5	0.4898 (3)	0.8700 (2)	0.54195 (7)	0.0350 (4)
H5D	0.6107	0.8759	0.5214	0.042*
C6	0.4770 (2)	0.7562 (2)	0.59032 (7)	0.0291 (3)
H6A	0.5894	0.6832	0.6024	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0823 (4)	0.0445 (2)	0.02714 (19)	−0.0267 (3)	0.0062 (2)	0.00768 (19)
O2'	0.0119 (4)	0.0181 (4)	0.0307 (5)	−0.0001 (3)	−0.0003 (4)	−0.0017 (4)
O3'	0.0243 (5)	0.0194 (5)	0.0219 (4)	−0.0012 (4)	0.0055 (4)	0.0016 (4)
O4'	0.0125 (4)	0.0151 (4)	0.0445 (6)	−0.0013 (3)	−0.0030 (4)	0.0025 (4)
O5'	0.0137 (4)	0.0193 (5)	0.0359 (6)	0.0011 (3)	0.0003 (4)	0.0007 (4)
C1'	0.0144 (5)	0.0138 (5)	0.0245 (6)	0.0001 (4)	−0.0016 (5)	−0.0013 (5)
C2'	0.0121 (5)	0.0153 (5)	0.0217 (6)	−0.0005 (4)	−0.0003 (4)	−0.0012 (5)
C3'	0.0150 (5)	0.0153 (5)	0.0218 (6)	−0.0013 (4)	0.0014 (5)	−0.0009 (5)
C4'	0.0149 (5)	0.0140 (6)	0.0222 (6)	−0.0007 (4)	−0.0016 (4)	−0.0010 (4)
C5'	0.0149 (5)	0.0190 (6)	0.0311 (7)	−0.0007 (4)	−0.0009 (5)	−0.0060 (5)
C1	0.0217 (6)	0.0156 (5)	0.0238 (6)	−0.0025 (5)	0.0032 (5)	−0.0023 (5)
C2	0.0259 (6)	0.0242 (7)	0.0266 (6)	−0.0004 (5)	0.0041 (6)	0.0039 (5)
C3	0.0389 (8)	0.0266 (7)	0.0295 (7)	−0.0031 (7)	0.0004 (7)	0.0058 (6)
C4	0.0508 (10)	0.0247 (7)	0.0216 (6)	−0.0157 (7)	0.0073 (7)	−0.0009 (6)
C5	0.0405 (9)	0.0303 (8)	0.0341 (8)	−0.0092 (7)	0.0180 (7)	−0.0057 (7)
C6	0.0262 (7)	0.0233 (6)	0.0378 (8)	−0.0029 (6)	0.0105 (6)	−0.0047 (6)

Geometric parameters (Å, º)

Cl4—C4	1.7466 (16)	C3'—H3A	1.0000
O2'—C2'	1.4136 (15)	C4'—C5'	1.5134 (18)
O2'—H2B	0.75 (3)	C4'—H4A	1.0000
O3'—C3'	1.4259 (16)	C5'—H5A	0.9900
O3'—H3B	0.73 (2)	C5'—H5B	0.9900
O4'—C1'	1.4314 (16)	C1—C6	1.389 (2)
O4'—C4'	1.4465 (16)	C1—C2	1.396 (2)
O5'—C5'	1.4309 (15)	C2—C3	1.388 (2)
O5'—H5C	0.76 (2)	C2—H2C	0.9500
C1'—C1	1.5085 (19)	C3—C4	1.388 (2)
C1'—C2'	1.5336 (18)	C3—H3C	0.9500
C1'—H1A	1.0000	C4—C5	1.370 (3)
C2'—C3'	1.5308 (18)	C5—C6	1.399 (2)
C2'—H2A	1.0000	C5—H5D	0.9500
C3'—C4'	1.5329 (17)	C6—H6A	0.9500
C2'—O2'—H2B	110 (2)	C5'—C4'—H4A	108.8
C3'—O3'—H3B	106.5 (17)	C3'—C4'—H4A	108.8
C1'—O4'—C4'	110.43 (9)	O5'—C5'—C4'	111.21 (11)
C5'—O5'—H5C	103.9 (16)	O5'—C5'—H5A	109.4
O4'—C1'—C1	111.63 (11)	C4'—C5'—H5A	109.4
O4'—C1'—C2'	105.19 (10)	O5'—C5'—H5B	109.4
C1—C1'—C2'	114.20 (11)	C4'—C5'—H5B	109.4
O4'—C1'—H1A	108.5	H5A—C5'—H5B	108.0
C1—C1'—H1A	108.5	C6—C1—C2	119.02 (14)
C2'—C1'—H1A	108.5	C6—C1—C1'	122.12 (13)
O2'—C2'—C3'	115.81 (11)	C2—C1—C1'	118.86 (12)
O2'—C2'—C1'	109.91 (10)	C3—C2—C1	120.99 (14)
C3'—C2'—C1'	102.23 (10)	C3—C2—H2C	119.5
O2'—C2'—H2A	109.5	C1—C2—H2C	119.5
C3'—C2'—H2A	109.5	C2—C3—C4	118.57 (16)
C1'—C2'—H2A	109.5	C2—C3—H3C	120.7
O3'—C3'—C2'	110.00 (11)	C4—C3—H3C	120.7
O3'—C3'—C4'	111.01 (11)	C5—C4—C3	121.73 (15)
C2'—C3'—C4'	101.56 (10)	C5—C4—Cl4	120.49 (13)
O3'—C3'—H3A	111.3	C3—C4—Cl4	117.77 (14)
C2'—C3'—H3A	111.3	C4—C5—C6	119.27 (15)
C4'—C3'—H3A	111.3	C4—C5—H5D	120.4
O4'—C4'—C5'	109.99 (11)	C6—C5—H5D	120.4
O4'—C4'—C3'	106.17 (10)	C1—C6—C5	120.39 (15)
C5'—C4'—C3'	114.17 (11)	C1—C6—H6A	119.8
O4'—C4'—H4A	108.8	C5—C6—H6A	119.8
C4'—O4'—C1'—C1	−140.13 (11)	O4'—C4'—C5'—O5'	67.30 (14)
C4'—O4'—C1'—C2'	−15.76 (14)	C3'—C4'—C5'—O5'	−173.49 (12)
O4'—C1'—C2'—O2'	156.80 (11)	O4'—C1'—C1—C6	2.25 (18)
C1—C1'—C2'—O2'	−80.47 (14)	C2'—C1'—C1—C6	−116.91 (15)
O4'—C1'—C2'—C3'	33.27 (13)	O4'—C1'—C1—C2	−176.90 (12)
C1—C1'—C2'—C3'	156.00 (11)	C2'—C1'—C1—C2	63.94 (16)
O2'—C2'—C3'—O3'	−38.88 (14)	C6—C1—C2—C3	1.6 (2)
C1'—C2'—C3'—O3'	80.59 (12)	C1'—C1—C2—C3	−179.21 (14)
O2'—C2'—C3'—C4'	−156.52 (11)	C1—C2—C3—C4	−0.8 (2)
C1'—C2'—C3'—C4'	−37.04 (12)	C2—C3—C4—C5	−0.8 (2)
C1'—O4'—C4'—C5'	115.65 (12)	C2—C3—C4—Cl4	178.33 (12)
C1'—O4'—C4'—C3'	−8.35 (14)	C3—C4—C5—C6	1.6 (2)
O3'—C3'—C4'—O4'	−88.24 (13)	Cl4—C4—C5—C6	−177.54 (13)
C2'—C3'—C4'—O4'	28.66 (13)	C2—C1—C6—C5	−0.8 (2)
O3'—C3'—C4'—C5'	150.41 (11)	C1'—C1—C6—C5	−179.97 (14)
C2'—C3'—C4'—C5'	−92.69 (13)	C4—C5—C6—C1	−0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2′—H2B···O5′^i	0.75 (3)	1.99 (3)	2.7172 (15)	162 (3)
O3′—H3B···O2′^ii	0.73 (2)	2.00 (2)	2.7220 (15)	172 (2)
O5′—H5C···O3′^iii	0.76 (2)	2.05 (2)	2.8077 (15)	174 (2)
C4′—H4A···O4′^iii	1.00	2.58	3.3584 (17)	135
C3—H3C···Cl4^iv	0.95	2.74	3.5902 (19)	150

Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+3/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x−1/2, −y+5/2, −z+1.