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Crystals of 4,2′-anhydro-5-(β-D-arabinofuranosyl)uracil, (I), obtained from an aqueous solution, were characterized as the dihydrate, C9H10N2O5·2H2O, (Ia). In air, these crystals slowly transform to the monohydrate, C9H10N2O5·H2O, (Ib), but remain crystalline. The solid-state transformation proceeds with the loss of one water molecule and a rearrangement of hydrogen-bonded layers of molecules. The furanose ring in (I) has an approximate C4′-exo,O4′-endo twist conformation. The central five-membered ring is slightly puckered. The uracil group is planar within experimental uncertainty.
Supporting information
CCDC references: 150846; 150847
For both compounds, data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL; software used to prepare material for publication: CIF in SHELXL97.
(Ia) 4,2'-Anhydro-5-(
β-
D-arabinofuranosyl)-uracil dihydrate
top
Crystal data top
C9H10N2O5·2H2O | F(000) = 276 |
Mr = 262.22 | Dx = 1.549 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0315 (7) Å | Cell parameters from 207 reflections |
b = 7.2490 (8) Å | θ = 3–23° |
c = 12.8693 (19) Å | µ = 0.14 mm−1 |
β = 91.921 (9)° | T = 135 K |
V = 562.36 (12) Å3 | Block, colorless |
Z = 2 | 0.60 × 0.54 × 0.34 mm |
Data collection top
Siemens_SMART diffractometer | 1970 independent reflections |
Radiation source: normal-focus sealed tube | 1942 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 32.3°, θmin = 1.6° |
Absorption correction: numerical (SHELXTL; sheldrick, 1996) | h = −8→8 |
Tmin = 0.916, Tmax = 0.961 | k = −9→10 |
10536 measured reflections | l = −17→19 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | All H-atom parameters refined |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.38 | (Δ/σ)max < 0.001 |
1970 reflections | Δρmax = 0.31 e Å−3 |
220 parameters | Δρmin = −0.27 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.31 (2) |
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 | x | y | z | Uiso*/Ueq | |
O4 | 0.51583 (11) | 0.04216 (15) | 0.12081 (5) | 0.01925 (17) | |
O3' | 0.54763 (12) | 0.07751 (11) | 0.38795 (6) | 0.01560 (16) | |
O2 | 0.32296 (12) | 0.08300 (12) | −0.22573 (6) | 0.01750 (17) | |
O4' | 0.07803 (12) | 0.20057 (12) | 0.22666 (6) | 0.01488 (16) | |
O5' | 0.24383 (11) | 0.55290 (11) | 0.26988 (6) | 0.01481 (15) | |
O7 | 0.73319 (15) | 0.33605 (14) | 0.50065 (7) | 0.0237 (2) | |
O8 | 0.87328 (15) | −0.19923 (15) | 0.38915 (8) | 0.0269 (2) | |
N3 | 0.43995 (13) | 0.06573 (16) | −0.05461 (6) | 0.01728 (19) | |
N1 | 0.05786 (12) | 0.05147 (15) | −0.10669 (6) | 0.01471 (17) | |
C5 | 0.14705 (14) | 0.03136 (15) | 0.07033 (7) | 0.01359 (18) | |
C1' | 0.14462 (15) | 0.02506 (15) | 0.18590 (7) | 0.01374 (18) | |
C2' | 0.39391 (16) | 0.00618 (14) | 0.21572 (7) | 0.01415 (18) | |
C4 | 0.36934 (14) | 0.04718 (16) | 0.03989 (7) | 0.01440 (18) | |
C3' | 0.44064 (15) | 0.15504 (14) | 0.29785 (7) | 0.01272 (17) | |
C2 | 0.27836 (15) | 0.06767 (15) | −0.13220 (7) | 0.01375 (18) | |
C4' | 0.20713 (15) | 0.22824 (14) | 0.32095 (7) | 0.01268 (17) | |
C5' | 0.19396 (17) | 0.42956 (15) | 0.35201 (7) | 0.01447 (18) | |
C6 | −0.00968 (16) | 0.03286 (17) | −0.00785 (8) | 0.01563 (19) | |
H1' | 0.068 (3) | −0.071 (3) | 0.2142 (15) | 0.024 (4)* | |
H2' | 0.434 (3) | −0.120 (3) | 0.2418 (13) | 0.015 (4)* | |
H3' | 0.534 (2) | 0.251 (3) | 0.2706 (12) | 0.012 (3)* | |
H03' | 0.607 (3) | 0.166 (4) | 0.4247 (14) | 0.035 (5)* | |
H4' | 0.149 (3) | 0.152 (3) | 0.3787 (15) | 0.028 (5)* | |
H01 | −0.035 (2) | 0.049 (3) | −0.1579 (12) | 0.015 (3)* | |
H5'B | 0.045 (3) | 0.460 (3) | 0.3735 (13) | 0.018 (4)* | |
H5'A | 0.290 (2) | 0.452 (2) | 0.4128 (12) | 0.010 (3)* | |
H05' | 0.394 (3) | 0.548 (4) | 0.2608 (14) | 0.028 (4)* | |
H6 | −0.156 (3) | 0.023 (3) | −0.0006 (13) | 0.020 (4)* | |
H07B | 0.655 (4) | 0.403 (4) | 0.5295 (17) | 0.041 (6)* | |
H07A | 0.845 (5) | 0.329 (5) | 0.530 (2) | 0.060 (7)* | |
H08A | 0.785 (4) | −0.112 (4) | 0.3901 (15) | 0.033 (5)* | |
H08B | 0.839 (3) | −0.275 (3) | 0.3434 (16) | 0.027 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.0105 (3) | 0.0353 (4) | 0.0118 (3) | 0.0043 (3) | −0.0006 (2) | −0.0022 (3) |
O3' | 0.0172 (3) | 0.0148 (4) | 0.0144 (3) | 0.0023 (3) | −0.0051 (2) | −0.0010 (3) |
O2 | 0.0154 (3) | 0.0248 (4) | 0.0123 (3) | −0.0006 (3) | 0.0006 (2) | 0.0004 (3) |
O4' | 0.0133 (3) | 0.0167 (3) | 0.0144 (3) | 0.0036 (3) | −0.0021 (2) | −0.0034 (3) |
O5' | 0.0133 (3) | 0.0154 (3) | 0.0156 (3) | 0.0013 (3) | −0.0008 (2) | 0.0035 (3) |
O7 | 0.0205 (4) | 0.0246 (4) | 0.0255 (4) | 0.0018 (3) | −0.0065 (3) | −0.0094 (4) |
O8 | 0.0211 (4) | 0.0255 (5) | 0.0333 (4) | 0.0097 (3) | −0.0091 (3) | −0.0103 (4) |
N3 | 0.0109 (3) | 0.0286 (5) | 0.0123 (3) | 0.0004 (3) | −0.0003 (2) | −0.0008 (4) |
N1 | 0.0109 (3) | 0.0195 (4) | 0.0136 (3) | −0.0006 (3) | −0.0015 (2) | −0.0026 (3) |
C5 | 0.0115 (3) | 0.0169 (4) | 0.0124 (3) | −0.0017 (3) | 0.0005 (3) | −0.0022 (3) |
C1' | 0.0139 (3) | 0.0146 (4) | 0.0127 (3) | −0.0008 (3) | 0.0007 (3) | −0.0015 (3) |
C2' | 0.0149 (4) | 0.0155 (4) | 0.0120 (3) | 0.0033 (3) | 0.0002 (3) | −0.0008 (3) |
C4 | 0.0101 (3) | 0.0193 (4) | 0.0137 (4) | 0.0021 (3) | −0.0011 (3) | −0.0021 (4) |
C3' | 0.0131 (4) | 0.0120 (4) | 0.0129 (3) | 0.0019 (3) | −0.0009 (3) | −0.0002 (3) |
C2 | 0.0114 (3) | 0.0161 (5) | 0.0137 (4) | 0.0005 (3) | −0.0005 (3) | −0.0015 (4) |
C4' | 0.0123 (3) | 0.0140 (4) | 0.0117 (4) | 0.0022 (3) | −0.0006 (3) | −0.0004 (3) |
C5' | 0.0175 (4) | 0.0136 (4) | 0.0124 (4) | 0.0032 (3) | 0.0008 (3) | −0.0001 (3) |
C6 | 0.0107 (3) | 0.0207 (5) | 0.0155 (4) | −0.0022 (4) | 0.0009 (3) | −0.0035 (4) |
Geometric parameters (Å, º) top
O4—C4 | 1.3434 (11) | N1—C6 | 1.3554 (12) |
O4—C2' | 1.4699 (11) | N1—C2 | 1.3855 (11) |
O3'—C3' | 1.4237 (11) | C5—C6 | 1.3573 (12) |
O2—C2 | 1.2470 (11) | C5—C4 | 1.4140 (12) |
O4'—C4' | 1.4338 (11) | C5—C1' | 1.4886 (13) |
O4'—C1' | 1.4384 (13) | C1'—C2' | 1.5453 (14) |
O5'—C5' | 1.4243 (12) | C2'—C3' | 1.5301 (14) |
N3—C4 | 1.3089 (12) | C3'—C4' | 1.5433 (13) |
N3—C2 | 1.3719 (11) | C4'—C5' | 1.5159 (14) |
| | | |
C4—O4—C2' | 108.33 (7) | N3—C4—C5 | 127.36 (8) |
C4'—O4'—C1' | 106.38 (7) | O4—C4—C5 | 112.84 (8) |
C4—N3—C2 | 115.60 (8) | O3'—C3'—C2' | 110.62 (8) |
C6—N1—C2 | 123.50 (8) | O3'—C3'—C4' | 111.75 (8) |
C6—C5—C4 | 115.93 (8) | C2'—C3'—C4' | 103.15 (8) |
C6—C5—C1' | 135.31 (8) | O2—C2—N3 | 122.17 (8) |
C4—C5—C1' | 108.69 (8) | O2—C2—N1 | 118.43 (8) |
O4'—C1'—C5 | 110.45 (8) | N3—C2—N1 | 119.40 (8) |
O4'—C1'—C2' | 105.61 (8) | O4'—C4'—C5' | 109.03 (8) |
C5—C1'—C2' | 102.04 (7) | O4'—C4'—C3' | 105.19 (7) |
O4—C2'—C3' | 111.29 (8) | C5'—C4'—C3' | 115.98 (8) |
O4—C2'—C1' | 106.72 (7) | O5'—C5'—C4' | 113.23 (8) |
C3'—C2'—C1' | 105.32 (8) | N1—C6—C5 | 118.21 (8) |
N3—C4—O4 | 119.80 (8) | | |
| | | |
C4'—O4'—C1'—C5 | −143.17 (8) | O4—C2'—C3'—O3' | −116.80 (8) |
C4'—O4'—C1'—C2' | −33.57 (10) | C1'—C2'—C3'—O3' | 127.93 (8) |
C6—C5—C1'—O4' | −74.03 (16) | O4—C2'—C3'—C4' | 123.57 (8) |
C4—C5—C1'—O4' | 102.78 (10) | C1'—C2'—C3'—C4' | 8.30 (9) |
C6—C5—C1'—C2' | 174.06 (13) | C4—N3—C2—O2 | −179.41 (11) |
C4—C5—C1'—C2' | −9.14 (11) | C4—N3—C2—N1 | 0.34 (16) |
C4—O4—C2'—C3' | −124.69 (9) | C6—N1—C2—O2 | 179.55 (11) |
C4—O4—C2'—C1' | −10.29 (12) | C6—N1—C2—N3 | −0.21 (17) |
O4'—C1'—C2'—O4 | −103.94 (9) | C1'—O4'—C4'—C5' | 164.36 (8) |
C5—C1'—C2'—O4 | 11.57 (11) | C1'—O4'—C4'—C3' | 39.35 (9) |
O4'—C1'—C2'—C3' | 14.45 (10) | O3'—C3'—C4'—O4' | −147.44 (8) |
C5—C1'—C2'—C3' | 129.95 (8) | C2'—C3'—C4'—O4' | −28.59 (9) |
C2—N3—C4—O4 | 179.41 (10) | O3'—C3'—C4'—C5' | 92.01 (10) |
C2—N3—C4—C5 | −0.82 (19) | C2'—C3'—C4'—C5' | −149.14 (8) |
C2'—O4—C4—N3 | −175.65 (11) | O4'—C4'—C5'—O5' | −51.00 (10) |
C2'—O4—C4—C5 | 4.55 (13) | C3'—C4'—C5'—O5' | 67.46 (10) |
C6—C5—C4—N3 | 1.09 (19) | C2—N1—C6—C5 | 0.49 (18) |
C1'—C5—C4—N3 | −176.41 (12) | C4—C5—C6—N1 | −0.84 (16) |
C6—C5—C4—O4 | −179.13 (10) | C1'—C5—C6—N1 | 175.80 (12) |
C1'—C5—C4—O4 | 3.37 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3′—H03′···O7 | 0.87 (2) | 1.73 (2) | 2.600 (1) | 178 (2) |
O5′—H05′···O2i | 0.92 (2) | 1.80 (2) | 2.701 (1) | 167 (2) |
N1—H01···O5′ii | 0.85 (2) | 1.88 (2) | 2.732 (1) | 178 (2) |
O7—H07A···O8iii | 0.76 (3) | 1.97 (3) | 2.736 (1) | 177 (3) |
O7—H07B···O3′iv | 0.78 (3) | 2.08 (3) | 2.855 (1) | 178 (2) |
O8—H08A···O3′ | 0.83 (3) | 1.98 (3) | 2.807 (1) | 174 (3) |
O8—H08B···O2v | 0.83 (2) | 2.05 (2) | 2.855 (1) | 164 (2) |
C2′—H2′···O2v | 1.00 (2) | 2.62 (2) | 3.511 (1) | 149 (2) |
C3′—H3′···O2i | 0.97 (2) | 2.63 (2) | 3.551 (1) | 159 (2) |
C6—H6···O4vi | 0.89 (2) | 2.57 (2) | 3.355 (1) | 148 (2) |
C6—H6···N3vi | 0.89 (2) | 2.53 (2) | 3.362 (1) | 155 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x, y−1/2, −z; (iii) −x+2, y+1/2, −z+1; (iv) −x+1, y+1/2, −z+1; (v) −x+1, y−1/2, −z; (vi) x−1, y, z. |
(Ib) 4,2'-Anhydro-5-(
β-
D-arabinofuranosyl)-uracil monohydrate
top
Crystal data top
C9H10N2O5·H2O | F(000) = 256 |
Mr = 244.21 | Dx = 1.540 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.024 (2) Å | Cell parameters from 54 reflections |
b = 7.218 (3) Å | θ = 3–23° |
c = 12.357 (4) Å | µ = 0.13 mm−1 |
β = 101.40 (4)° | T = 137 K |
V = 526.7 (3) Å3 | Rod, colorless |
Z = 2 | 0.56 × 0.35 × 0.07 mm |
Data collection top
Siemens_SMART diffractometer | 1808 independent reflections |
Radiation source: normal-focus sealed tube | 1443 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.109 |
ω scans | θmax = 32.0°, θmin = 1.7° |
Absorption correction: numerical (SHELXTL; sheldrick, 1996) | h = −8→8 |
Tmin = 0.946, Tmax = 0.991 | k = −10→10 |
10608 measured reflections | l = −18→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.110 | All H atom parameters refined |
S = 1.38 | w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3 |
1808 reflections | (Δ/σ)max = 0.001 |
202 parameters | Δρmax = 0.43 e Å−3 |
1 restraint | Δρmin = −0.34 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O4 | 0.4691 (3) | 0.9064 (3) | 0.87753 (14) | 0.0244 (4) | |
O4' | −0.0308 (4) | 0.7577 (2) | 0.76255 (15) | 0.0211 (4) | |
O2 | 0.4446 (3) | 0.8582 (3) | 1.24412 (14) | 0.0221 (4) | |
N1 | 0.1218 (4) | 0.8988 (3) | 1.11709 (18) | 0.0194 (4) | |
C4 | 0.3619 (4) | 0.9015 (4) | 0.96299 (19) | 0.0182 (5) | |
O5' | 0.0949 (3) | 0.3985 (3) | 0.70732 (14) | 0.0218 (4) | |
O3' | 0.3844 (4) | 0.8541 (3) | 0.59891 (16) | 0.0281 (5) | |
N3 | 0.4782 (4) | 0.8798 (3) | 1.06380 (17) | 0.0216 (5) | |
C5 | 0.1256 (4) | 0.9224 (3) | 0.9298 (2) | 0.0182 (5) | |
C2 | 0.3536 (4) | 0.8776 (3) | 1.1454 (2) | 0.0187 (5) | |
C6 | 0.0065 (5) | 0.9211 (4) | 1.0125 (2) | 0.0208 (5) | |
C1' | 0.0657 (5) | 0.9306 (3) | 0.8067 (2) | 0.0198 (5) | |
C2' | 0.3013 (5) | 0.9414 (4) | 0.7758 (2) | 0.0205 (5) | |
C5' | 0.0051 (5) | 0.5322 (4) | 0.6246 (2) | 0.0229 (6) | |
C4' | 0.0512 (5) | 0.7293 (4) | 0.6625 (2) | 0.0208 (5) | |
C3' | 0.3020 (5) | 0.7879 (3) | 0.6914 (2) | 0.0189 (5) | |
O8 | 0.3314 (4) | 0.6415 (3) | 1.41947 (17) | 0.0277 (5) | |
H4' | −0.031 (6) | 0.802 (5) | 0.603 (2) | 0.021 (8)* | |
H5B' | 0.062 (6) | 0.505 (5) | 0.554 (2) | 0.025 (8)* | |
H3' | 0.396 (6) | 0.692 (4) | 0.729 (2) | 0.013 (7)* | |
H03' | 0.359 (8) | 0.783 (7) | 0.540 (3) | 0.050 (12)* | |
H2' | 0.346 (6) | 1.048 (6) | 0.747 (3) | 0.030 (9)* | |
H6 | −0.156 (6) | 0.943 (4) | 1.002 (2) | 0.016 (7)* | |
H05' | 0.252 (8) | 0.401 (7) | 0.723 (3) | 0.049 (11)* | |
H5A' | −0.164 (7) | 0.515 (5) | 0.606 (3) | 0.031 (9)* | |
H01 | 0.062 (7) | 0.903 (6) | 1.173 (3) | 0.036 (10)* | |
H1' | −0.029 (6) | 1.029 (5) | 0.774 (3) | 0.026 (9)* | |
H08B | 0.333 (8) | 0.707 (7) | 1.364 (4) | 0.045 (12)* | |
H08A | 0.436 (12) | 0.565 (11) | 1.421 (4) | 0.09 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4 | 0.0174 (9) | 0.0357 (11) | 0.0210 (8) | −0.0051 (9) | 0.0058 (7) | −0.0036 (9) |
O4' | 0.0213 (10) | 0.0189 (9) | 0.0242 (10) | −0.0045 (7) | 0.0072 (8) | −0.0027 (7) |
O2 | 0.0222 (10) | 0.0220 (10) | 0.0233 (9) | 0.0008 (8) | 0.0072 (8) | 0.0003 (7) |
N1 | 0.0164 (10) | 0.0189 (10) | 0.0239 (10) | −0.0010 (9) | 0.0062 (8) | −0.0026 (9) |
C4 | 0.0170 (12) | 0.0152 (11) | 0.0234 (11) | −0.0018 (10) | 0.0066 (9) | −0.0026 (10) |
O5' | 0.0224 (10) | 0.0160 (8) | 0.0286 (9) | −0.0029 (8) | 0.0089 (8) | 0.0003 (7) |
O3' | 0.0390 (13) | 0.0229 (10) | 0.0256 (10) | −0.0133 (9) | 0.0143 (9) | −0.0039 (8) |
N3 | 0.0161 (11) | 0.0255 (12) | 0.0238 (10) | 0.0008 (9) | 0.0055 (8) | −0.0027 (9) |
C5 | 0.0178 (12) | 0.0134 (11) | 0.0236 (11) | 0.0013 (10) | 0.0045 (9) | −0.0013 (9) |
C2 | 0.0182 (12) | 0.0127 (11) | 0.0264 (12) | −0.0006 (10) | 0.0075 (10) | −0.0018 (10) |
C6 | 0.0172 (12) | 0.0170 (11) | 0.0285 (13) | 0.0016 (10) | 0.0055 (10) | −0.0042 (10) |
C1' | 0.0204 (13) | 0.0130 (11) | 0.0251 (12) | 0.0008 (10) | 0.0018 (10) | −0.0012 (10) |
C2' | 0.0220 (14) | 0.0174 (12) | 0.0221 (12) | −0.0043 (10) | 0.0044 (10) | 0.0015 (10) |
C5' | 0.0263 (16) | 0.0222 (13) | 0.0201 (13) | −0.0074 (11) | 0.0041 (11) | −0.0016 (10) |
C4' | 0.0220 (14) | 0.0203 (12) | 0.0195 (12) | −0.0015 (10) | 0.0023 (10) | 0.0007 (10) |
C3' | 0.0224 (14) | 0.0148 (11) | 0.0195 (12) | −0.0043 (10) | 0.0039 (10) | 0.0008 (9) |
O8 | 0.0368 (13) | 0.0220 (10) | 0.0269 (11) | 0.0082 (9) | 0.0128 (10) | 0.0011 (8) |
Geometric parameters (Å, º) top
O4—C4 | 1.343 (3) | O5'—C5' | 1.432 (3) |
O4—C2' | 1.471 (3) | O3'—C3' | 1.416 (3) |
O4'—C4' | 1.434 (3) | N3—C2 | 1.371 (3) |
O4'—C1' | 1.438 (3) | C5—C6 | 1.360 (4) |
O2—C2 | 1.242 (3) | C5—C1' | 1.494 (4) |
N1—C6 | 1.350 (4) | C1'—C2' | 1.543 (4) |
N1—C2 | 1.379 (3) | C2'—C3' | 1.522 (4) |
C4—N3 | 1.313 (3) | C5'—C4' | 1.506 (4) |
C4—C5 | 1.409 (4) | C4'—C3' | 1.542 (4) |
| | | |
C4—O4—C2' | 108.67 (19) | O4'—C1'—C5 | 110.5 (2) |
C4'—O4'—C1' | 105.6 (2) | O4'—C1'—C2' | 105.8 (2) |
C6—N1—C2 | 124.0 (2) | C5—C1'—C2' | 101.8 (2) |
N3—C4—O4 | 120.0 (2) | O4—C2'—C3' | 111.5 (2) |
N3—C4—C5 | 127.4 (2) | O4—C2'—C1' | 106.9 (2) |
O4—C4—C5 | 112.6 (2) | C3'—C2'—C1' | 105.1 (2) |
C4—N3—C2 | 115.6 (2) | O5'—C5'—C4' | 113.2 (2) |
C6—C5—C4 | 115.7 (2) | O4'—C4'—C5' | 109.2 (2) |
C6—C5—C1' | 135.1 (3) | O4'—C4'—C3' | 104.5 (2) |
C4—C5—C1' | 109.1 (2) | C5'—C4'—C3' | 116.3 (2) |
O2—C2—N3 | 121.6 (2) | O3'—C3'—C2' | 110.9 (2) |
O2—C2—N1 | 119.3 (2) | O3'—C3'—C4' | 112.9 (2) |
N3—C2—N1 | 119.1 (2) | C2'—C3'—C4' | 102.9 (2) |
N1—C6—C5 | 118.2 (3) | | |
| | | |
C2'—O4—C4—N3 | −177.1 (2) | C4—C5—C1'—C2' | −8.2 (2) |
C2'—O4—C4—C5 | 2.7 (3) | C4—O4—C2'—C3' | −122.2 (2) |
O4—C4—N3—C2 | 179.7 (2) | C4—O4—C2'—C1' | −7.9 (3) |
C5—C4—N3—C2 | −0.1 (4) | O4'—C1'—C2'—O4 | −106.0 (2) |
N3—C4—C5—C6 | 0.6 (4) | C5—C1'—C2'—O4 | 9.5 (2) |
O4—C4—C5—C6 | −179.2 (2) | O4'—C1'—C2'—C3' | 12.6 (3) |
N3—C4—C5—C1' | −176.3 (3) | C5—C1'—C2'—C3' | 128.1 (2) |
O4—C4—C5—C1' | 3.9 (3) | C1'—O4'—C4'—C5' | 166.7 (2) |
C4—N3—C2—O2 | −179.9 (2) | C1'—O4'—C4'—C3' | 41.6 (2) |
C4—N3—C2—N1 | −0.4 (3) | O5'—C5'—C4'—O4' | −54.6 (3) |
C6—N1—C2—O2 | 179.9 (2) | O5'—C5'—C4'—C3' | 63.3 (3) |
C6—N1—C2—N3 | 0.3 (4) | O4—C2'—C3'—O3' | −112.0 (2) |
C2—N1—C6—C5 | 0.2 (4) | C1'—C2'—C3'—O3' | 132.6 (2) |
C4—C5—C6—N1 | −0.6 (3) | O4—C2'—C3'—C4' | 127.0 (2) |
C1'—C5—C6—N1 | 175.3 (3) | C1'—C2'—C3'—C4' | 11.6 (3) |
C4'—O4'—C1'—C5 | −143.3 (2) | O4'—C4'—C3'—O3' | −151.8 (2) |
C4'—O4'—C1'—C2' | −33.8 (3) | C5'—C4'—C3'—O3' | 87.7 (3) |
C6—C5—C1'—O4' | −72.2 (4) | O4'—C4'—C3'—C2' | −32.2 (2) |
C4—C5—C1'—O4' | 103.9 (2) | C5'—C4'—C3'—C2' | −152.7 (2) |
C6—C5—C1'—C2' | 175.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3′—H03′···O8i | 0.88 (4) | 1.79 (4) | 2.663 (3) | 175 (5) |
O5′—H05′···O2ii | 0.93 (5) | 1.82 (5) | 2.735 (3) | 169 (5) |
N1—H01···O5′iii | 0.84 (4) | 1.91 (4) | 2.744 (3) | 175 (4) |
O8—H08B···O2 | 0.83 (5) | 2.06 (5) | 2.862 (3) | 162 (5) |
O8—H08A···O3′ii | 0.84 (8) | 1.91 (8) | 2.728 (3) | 165 (7) |
C2′—H2′···O2iv | 0.91 (4) | 2.56 (4) | 3.406 (4) | 155 (3) |
C3′—H3′···O2ii | 0.95 (3) | 2.59 (3) | 3.479 (3) | 155 (2) |
C6—H6···O4v | 0.97 (4) | 2.48 (3) | 3.337 (4) | 146 (2) |
C6—H6···N3v | 0.97 (4) | 2.51 (4) | 3.379 (4) | 148 (2) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, y−1/2, −z+2; (iii) −x, y+1/2, −z+2; (iv) −x+1, y+1/2, −z+2; (v) x−1, y, z. |
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