Two independent molecules in the crystal structure of the title nucleoside, 1-(2-deoxy-α-D-ribofuranosyl)-5-methyluracil, C10H14N2O5, form a dimer connected by two inter-base hydrogen bonds. The ring puckering modes are envelope C4′-endo and half-chair C3′-exo-C4′-endo, respectively, which are quite uncommon conformations for 2′-deoxyriboses.
Supporting information
CCDC reference: 271873
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.001 Å
- R factor = 0.032
- wR factor = 0.086
- Data-to-parameter ratio = 19.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 0.85 mm
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.802 0.938
Tmin' and Tmax expected: 0.904 0.938
RR' = 0.887
Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.07
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.25
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 20
Alert level G
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 40.53
From the CIF: _reflns_number_total 6311
Count of symmetry unique reflns 7184
Completeness (_total/calc) 87.85%
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
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
1-(2-Deoxy-
α-
D-ribofuranosyl)-5-methyluracil
top
Crystal data top
C10H14N2O5 | Z = 2 |
Mr = 242.23 | F(000) = 256 |
Triclinic, P1 | Dx = 1.438 Mg m−3 |
a = 5.838 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.883 (4) Å | Cell parameters from 7621 reflections |
c = 10.576 (4) Å | θ = 2.1–40.5° |
α = 107.225 (14)° | µ = 0.12 mm−1 |
β = 100.203 (14)° | T = 105 K |
γ = 98.894 (14)° | Block, colourless |
V = 559.5 (4) Å3 | 0.85 × 0.75 × 0.55 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 6311 independent reflections |
Radiation source: fine-focus sealed tube | 6021 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 8.3 pixels mm-1 | θmax = 40.5°, θmin = 2.1° |
Sets of exposures each taken over 0.3° ω rotation scans | h = −9→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −17→17 |
Tmin = 0.802, Tmax = 0.938 | l = −19→19 |
10979 measured reflections | |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0624P)2 + 0.0016P] where P = (Fo2 + 2Fc2)/3 |
6311 reflections | (Δ/σ)max < 0.001 |
327 parameters | Δρmax = 0.56 e Å−3 |
3 restraints | Δρmin = −0.18 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. Data were collected by measuring two sets of exposures with the detector set at
2θ = 29° and three sets of exposures with the detector set at 2θ = 55°,
crystal-to-detector distance 5.00 cm. Refinement of F2 against ALL
reflections. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O2A | 0.99446 (13) | 0.60401 (9) | 0.20607 (7) | 0.02154 (12) | |
O4A | 0.53074 (15) | 0.79306 (11) | −0.06091 (7) | 0.02684 (16) | |
O3'A | 0.38596 (13) | 0.80434 (11) | 0.55607 (8) | 0.02685 (16) | |
H3'A | 0.338 (5) | 0.850 (3) | 0.621 (3) | 0.040* | |
O4'A | 0.89252 (10) | 0.84899 (6) | 0.53619 (6) | 0.01408 (9) | |
O5'A | 1.21317 (12) | 0.89927 (8) | 0.78953 (7) | 0.02065 (11) | |
H5'A | 1.302 (4) | 0.871 (2) | 0.843 (2) | 0.031* | |
N1A | 0.73696 (12) | 0.73467 (8) | 0.30135 (7) | 0.01455 (10) | |
N3A | 0.75051 (13) | 0.69610 (9) | 0.07467 (7) | 0.01668 (11) | |
H3A | 0.805 (3) | 0.646 (2) | 0.0082 (19) | 0.020* | |
C2A | 0.83777 (14) | 0.67390 (9) | 0.19547 (7) | 0.01493 (11) | |
C4A | 0.58619 (14) | 0.77987 (10) | 0.05303 (8) | 0.01652 (12) | |
C5A | 0.49125 (14) | 0.84449 (9) | 0.16944 (7) | 0.01536 (11) | |
C6A | 0.56658 (13) | 0.81612 (9) | 0.28648 (7) | 0.01512 (11) | |
H61A | 0.4994 | 0.8538 | 0.3615 | 0.018* | |
C7A | 0.31675 (18) | 0.93993 (12) | 0.15600 (10) | 0.02313 (16) | |
H71A | 0.2520 | 0.9637 | 0.2373 | 0.035* | |
H72A | 0.1863 | 0.8885 | 0.0752 | 0.035* | |
H73A | 0.3985 | 1.0296 | 0.1467 | 0.035* | |
C1'A | 0.81025 (14) | 0.70905 (8) | 0.43197 (7) | 0.01396 (11) | |
H11A | 0.9434 | 0.6565 | 0.4281 | 0.017* | |
C2'A | 0.60614 (16) | 0.62447 (10) | 0.47267 (8) | 0.01959 (14) | |
H21A | 0.4595 | 0.5897 | 0.3983 | 0.024* | |
H22A | 0.6523 | 0.5400 | 0.4939 | 0.024* | |
C3'A | 0.56696 (14) | 0.73461 (10) | 0.59950 (8) | 0.01779 (13) | |
H31A | 0.5245 | 0.6875 | 0.6664 | 0.021* | |
C4'A | 0.81051 (13) | 0.84212 (9) | 0.65648 (7) | 0.01402 (11) | |
H41A | 0.7875 | 0.9399 | 0.7075 | 0.017* | |
C5'A | 0.98963 (15) | 0.79587 (10) | 0.74950 (8) | 0.01805 (13) | |
H51A | 0.9311 | 0.7923 | 0.8310 | 0.022* | |
H52A | 1.0104 | 0.6979 | 0.7009 | 0.022* | |
O2B | −0.07623 (14) | 0.52463 (8) | 0.85938 (7) | 0.02202 (12) | |
O4B | 0.46198 (14) | 0.39902 (10) | 1.14759 (7) | 0.02398 (13) | |
O3'B | 0.22204 (13) | 0.06900 (8) | 0.48502 (7) | 0.01989 (11) | |
H3'B | 0.148 (4) | 0.000 (2) | 0.503 (2) | 0.030* | |
O4'B | 0.18710 (15) | 0.38733 (8) | 0.55097 (7) | 0.02310 (13) | |
O5'B | −0.23065 (16) | 0.30407 (12) | 0.31947 (10) | 0.03125 (17) | |
H5'B | −0.292 (5) | 0.324 (3) | 0.264 (3) | 0.047* | |
N1B | 0.14988 (15) | 0.36854 (9) | 0.76382 (7) | 0.01881 (12) | |
N3B | 0.20318 (14) | 0.46219 (9) | 0.99941 (7) | 0.01726 (11) | |
H3B | 0.147 (3) | 0.515 (2) | 1.0612 (19) | 0.021* | |
C2B | 0.08264 (15) | 0.45638 (9) | 0.87243 (8) | 0.01610 (12) | |
C4B | 0.37674 (14) | 0.38616 (9) | 1.02740 (8) | 0.01623 (12) | |
C5B | 0.44383 (15) | 0.29765 (9) | 0.90897 (8) | 0.01755 (12) | |
C6B | 0.32851 (17) | 0.29357 (10) | 0.78413 (9) | 0.01985 (14) | |
H61B | 0.3721 | 0.2364 | 0.7064 | 0.024* | |
C7B | 0.63390 (18) | 0.21410 (12) | 0.93006 (10) | 0.02398 (16) | |
H71B | 0.6656 | 0.1644 | 0.8421 | 0.036* | |
H72B | 0.5793 | 0.1422 | 0.9714 | 0.036* | |
H73B | 0.7804 | 0.2813 | 0.9905 | 0.036* | |
C1'B | 0.01834 (16) | 0.34594 (9) | 0.62248 (8) | 0.01850 (13) | |
H11B | −0.1010 | 0.4087 | 0.6256 | 0.022* | |
C2'B | −0.11032 (15) | 0.18592 (9) | 0.54249 (9) | 0.01833 (13) | |
H21B | −0.1105 | 0.1273 | 0.6039 | 0.022* | |
H22B | −0.2772 | 0.1792 | 0.4970 | 0.022* | |
C3'B | 0.03540 (15) | 0.13386 (9) | 0.43691 (8) | 0.01636 (12) | |
H31B | −0.0711 | 0.0663 | 0.3487 | 0.020* | |
C4'B | 0.15448 (15) | 0.27520 (9) | 0.42040 (8) | 0.01661 (12) | |
H41B | 0.3147 | 0.2661 | 0.4021 | 0.020* | |
C5'B | 0.00923 (18) | 0.31191 (11) | 0.30524 (9) | 0.02135 (14) | |
H51B | 0.0801 | 0.4109 | 0.3084 | 0.026* | |
H52B | 0.0114 | 0.2426 | 0.2163 | 0.026* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2A | 0.0249 (3) | 0.0316 (3) | 0.0164 (2) | 0.0168 (3) | 0.0098 (2) | 0.0118 (2) |
O4A | 0.0293 (3) | 0.0467 (4) | 0.0142 (2) | 0.0207 (3) | 0.0081 (2) | 0.0163 (3) |
O3'A | 0.0170 (3) | 0.0507 (5) | 0.0211 (3) | 0.0143 (3) | 0.0076 (2) | 0.0187 (3) |
O4'A | 0.0161 (2) | 0.0163 (2) | 0.01037 (19) | 0.00158 (16) | 0.00391 (15) | 0.00579 (17) |
O5'A | 0.0162 (2) | 0.0279 (3) | 0.0176 (3) | 0.0032 (2) | 0.00028 (18) | 0.0102 (2) |
N1A | 0.0158 (2) | 0.0199 (3) | 0.0106 (2) | 0.0067 (2) | 0.00457 (17) | 0.0068 (2) |
N3A | 0.0188 (3) | 0.0243 (3) | 0.0107 (2) | 0.0090 (2) | 0.00591 (19) | 0.0077 (2) |
C2A | 0.0161 (3) | 0.0198 (3) | 0.0114 (3) | 0.0061 (2) | 0.0052 (2) | 0.0066 (2) |
C4A | 0.0159 (3) | 0.0245 (3) | 0.0118 (3) | 0.0069 (2) | 0.0045 (2) | 0.0080 (2) |
C5A | 0.0144 (3) | 0.0209 (3) | 0.0122 (3) | 0.0056 (2) | 0.00331 (19) | 0.0065 (2) |
C6A | 0.0149 (3) | 0.0198 (3) | 0.0116 (3) | 0.0054 (2) | 0.00392 (19) | 0.0052 (2) |
C7A | 0.0232 (4) | 0.0334 (4) | 0.0191 (3) | 0.0158 (3) | 0.0068 (3) | 0.0119 (3) |
C1'A | 0.0165 (3) | 0.0162 (3) | 0.0106 (2) | 0.0042 (2) | 0.00425 (19) | 0.0055 (2) |
C2'A | 0.0225 (3) | 0.0197 (3) | 0.0146 (3) | −0.0019 (3) | 0.0053 (2) | 0.0056 (3) |
C3'A | 0.0142 (3) | 0.0275 (3) | 0.0143 (3) | 0.0037 (2) | 0.0052 (2) | 0.0102 (3) |
C4'A | 0.0154 (3) | 0.0183 (3) | 0.0106 (2) | 0.0056 (2) | 0.00430 (19) | 0.0065 (2) |
C5'A | 0.0179 (3) | 0.0238 (3) | 0.0144 (3) | 0.0038 (2) | 0.0021 (2) | 0.0106 (3) |
O2B | 0.0280 (3) | 0.0273 (3) | 0.0167 (2) | 0.0160 (3) | 0.0077 (2) | 0.0097 (2) |
O4B | 0.0249 (3) | 0.0342 (3) | 0.0134 (2) | 0.0113 (3) | 0.0015 (2) | 0.0080 (2) |
O3'B | 0.0238 (3) | 0.0188 (2) | 0.0212 (3) | 0.0084 (2) | 0.0065 (2) | 0.0101 (2) |
O4'B | 0.0349 (4) | 0.0170 (2) | 0.0140 (2) | −0.0024 (2) | 0.0051 (2) | 0.0046 (2) |
O5'B | 0.0259 (3) | 0.0491 (5) | 0.0319 (4) | 0.0173 (3) | 0.0084 (3) | 0.0271 (4) |
N1B | 0.0250 (3) | 0.0218 (3) | 0.0114 (2) | 0.0111 (2) | 0.0040 (2) | 0.0052 (2) |
N3B | 0.0196 (3) | 0.0211 (3) | 0.0117 (2) | 0.0072 (2) | 0.00407 (19) | 0.0047 (2) |
C2B | 0.0199 (3) | 0.0173 (3) | 0.0127 (3) | 0.0063 (2) | 0.0049 (2) | 0.0057 (2) |
C4B | 0.0158 (3) | 0.0187 (3) | 0.0135 (3) | 0.0040 (2) | 0.0022 (2) | 0.0052 (2) |
C5B | 0.0183 (3) | 0.0195 (3) | 0.0150 (3) | 0.0066 (2) | 0.0032 (2) | 0.0051 (2) |
C6B | 0.0240 (3) | 0.0224 (3) | 0.0140 (3) | 0.0114 (3) | 0.0039 (2) | 0.0045 (3) |
C7B | 0.0226 (4) | 0.0280 (4) | 0.0223 (4) | 0.0122 (3) | 0.0035 (3) | 0.0075 (3) |
C1'B | 0.0259 (4) | 0.0183 (3) | 0.0124 (3) | 0.0083 (3) | 0.0033 (2) | 0.0057 (2) |
C2'B | 0.0195 (3) | 0.0200 (3) | 0.0167 (3) | 0.0041 (2) | 0.0061 (2) | 0.0070 (3) |
C3'B | 0.0188 (3) | 0.0153 (3) | 0.0147 (3) | 0.0031 (2) | 0.0038 (2) | 0.0050 (2) |
C4'B | 0.0198 (3) | 0.0177 (3) | 0.0132 (3) | 0.0034 (2) | 0.0037 (2) | 0.0070 (2) |
C5'B | 0.0260 (4) | 0.0260 (4) | 0.0165 (3) | 0.0081 (3) | 0.0058 (2) | 0.0121 (3) |
Geometric parameters (Å, º) top
O2A—C2A | 1.2375 (11) | O2B—C2B | 1.2399 (11) |
O4A—C4A | 1.2417 (11) | O4B—C4B | 1.2411 (11) |
O3'A—C3'A | 1.4294 (12) | O3'B—C3'B | 1.4387 (11) |
O3'A—H3'A | 0.83 (3) | O3'B—H3'B | 0.84 (2) |
O4'A—C1'A | 1.4361 (11) | O4'B—C1'B | 1.4257 (12) |
O4'A—C4'A | 1.4523 (10) | O4'B—C4'B | 1.4514 (12) |
O5'A—C5'A | 1.4361 (12) | O5'B—C5'B | 1.4276 (14) |
O5'A—H5'A | 0.84 (2) | O5'B—H5'B | 0.72 (3) |
N1A—C2A | 1.3804 (10) | N1B—C2B | 1.3790 (11) |
N1A—C6A | 1.3889 (11) | N1B—C6B | 1.3916 (12) |
N1A—C1'A | 1.4788 (11) | N1B—C1'B | 1.4889 (12) |
N3A—C2A | 1.3820 (11) | N3B—C2B | 1.3817 (12) |
N3A—C4A | 1.3921 (12) | N3B—C4B | 1.3928 (12) |
N3A—H3A | 0.874 (19) | N3B—H3B | 0.857 (19) |
C4A—C5A | 1.4548 (12) | C4B—C5B | 1.4555 (12) |
C5A—C6A | 1.3620 (11) | C5B—C6B | 1.3576 (13) |
C5A—C7A | 1.5077 (13) | C5B—C7B | 1.5058 (13) |
C6A—H61A | 0.9500 | C6B—H61B | 0.9500 |
C7A—H71A | 0.9800 | C7B—H71B | 0.9800 |
C7A—H72A | 0.9800 | C7B—H72B | 0.9800 |
C7A—H73A | 0.9800 | C7B—H73B | 0.9800 |
C1'A—C2'A | 1.5462 (12) | C1'B—C2'B | 1.5479 (14) |
C1'A—H11A | 1.0000 | C1'B—H11B | 1.0000 |
C2'A—C3'A | 1.5354 (13) | C2'B—C3'B | 1.5385 (12) |
C2'A—H21A | 0.9900 | C2'B—H21B | 0.9900 |
C2'A—H22A | 0.9900 | C2'B—H22B | 0.9900 |
C3'A—C4'A | 1.5375 (13) | C3'B—C4'B | 1.5337 (13) |
C3'A—H31A | 1.0000 | C3'B—H31B | 1.0000 |
C4'A—C5'A | 1.5232 (11) | C4'B—C5'B | 1.5247 (12) |
C4'A—H41A | 1.0000 | C4'B—H41B | 1.0000 |
C5'A—H51A | 0.9900 | C5'B—H51B | 0.9900 |
C5'A—H52A | 0.9900 | C5'B—H52B | 0.9900 |
| | | |
C3'A—O3'A—H3'A | 111.0 (18) | C3'B—O3'B—H3'B | 103.1 (15) |
C1'A—O4'A—C4'A | 108.80 (6) | C1'B—O4'B—C4'B | 110.33 (7) |
C5'A—O5'A—H5'A | 104.3 (15) | C5'B—O5'B—H5'B | 106 (2) |
C2A—N1A—C6A | 121.45 (7) | C2B—N1B—C6B | 121.11 (7) |
C2A—N1A—C1'A | 118.62 (7) | C2B—N1B—C1'B | 119.38 (7) |
C6A—N1A—C1'A | 119.92 (6) | C6B—N1B—C1'B | 119.39 (7) |
C2A—N3A—C4A | 126.74 (7) | C2B—N3B—C4B | 126.93 (7) |
C2A—N3A—H3A | 111.5 (13) | C2B—N3B—H3B | 109.8 (13) |
C4A—N3A—H3A | 121.7 (13) | C4B—N3B—H3B | 123.1 (13) |
O2A—C2A—N1A | 123.23 (7) | O2B—C2B—N1B | 123.42 (8) |
O2A—C2A—N3A | 121.66 (7) | O2B—C2B—N3B | 121.40 (7) |
N1A—C2A—N3A | 115.11 (7) | N1B—C2B—N3B | 115.17 (7) |
O4A—C4A—N3A | 119.13 (8) | O4B—C4B—N3B | 119.09 (8) |
O4A—C4A—C5A | 125.35 (8) | O4B—C4B—C5B | 125.55 (8) |
N3A—C4A—C5A | 115.52 (7) | N3B—C4B—C5B | 115.36 (7) |
C6A—C5A—C4A | 117.91 (7) | C6B—C5B—C4B | 117.81 (8) |
C6A—C5A—C7A | 123.05 (7) | C6B—C5B—C7B | 123.27 (8) |
C4A—C5A—C7A | 119.04 (7) | C4B—C5B—C7B | 118.92 (8) |
C5A—C6A—N1A | 123.11 (7) | C5B—C6B—N1B | 123.55 (8) |
C5A—C6A—H61A | 118.4 | C5B—C6B—H61B | 118.2 |
N1A—C6A—H61A | 118.4 | N1B—C6B—H61B | 118.2 |
C5A—C7A—H71A | 109.5 | C5B—C7B—H71B | 109.5 |
C5A—C7A—H72A | 109.5 | C5B—C7B—H72B | 109.5 |
H71A—C7A—H72A | 109.5 | H71B—C7B—H72B | 109.5 |
C5A—C7A—H73A | 109.5 | C5B—C7B—H73B | 109.5 |
H71A—C7A—H73A | 109.5 | H71B—C7B—H73B | 109.5 |
H72A—C7A—H73A | 109.5 | H72B—C7B—H73B | 109.5 |
O4'A—C1'A—N1A | 107.00 (7) | O4'B—C1'B—N1B | 107.95 (8) |
O4'A—C1'A—C2'A | 106.88 (6) | O4'B—C1'B—C2'B | 107.49 (7) |
N1A—C1'A—C2'A | 114.23 (7) | N1B—C1'B—C2'B | 113.28 (7) |
O4'A—C1'A—H11A | 109.5 | O4'B—C1'B—H11B | 109.3 |
N1A—C1'A—H11A | 109.5 | N1B—C1'B—H11B | 109.3 |
C2'A—C1'A—H11A | 109.5 | C2'B—C1'B—H11B | 109.3 |
C3'A—C2'A—C1'A | 104.76 (7) | C3'B—C2'B—C1'B | 104.46 (7) |
C3'A—C2'A—H21A | 110.8 | C3'B—C2'B—H21B | 110.9 |
C1'A—C2'A—H21A | 110.8 | C1'B—C2'B—H21B | 110.9 |
C3'A—C2'A—H22A | 110.8 | C3'B—C2'B—H22B | 110.9 |
C1'A—C2'A—H22A | 110.8 | C1'B—C2'B—H22B | 110.9 |
H21A—C2'A—H22A | 108.9 | H21B—C2'B—H22B | 108.9 |
O3'A—C3'A—C2'A | 108.18 (7) | O3'B—C3'B—C4'B | 107.56 (7) |
O3'A—C3'A—C4'A | 110.65 (8) | O3'B—C3'B—C2'B | 112.97 (7) |
C2'A—C3'A—C4'A | 102.43 (7) | C4'B—C3'B—C2'B | 103.19 (7) |
O3'A—C3'A—H31A | 111.7 | O3'B—C3'B—H31B | 110.9 |
C2'A—C3'A—H31A | 111.7 | C4'B—C3'B—H31B | 110.9 |
C4'A—C3'A—H31A | 111.7 | C2'B—C3'B—H31B | 110.9 |
O4'A—C4'A—C5'A | 111.17 (7) | O4'B—C4'B—C5'B | 111.39 (8) |
O4'A—C4'A—C3'A | 104.27 (6) | O4'B—C4'B—C3'B | 105.66 (7) |
C5'A—C4'A—C3'A | 113.54 (7) | C5'B—C4'B—C3'B | 113.17 (7) |
O4'A—C4'A—H41A | 109.2 | O4'B—C4'B—H41B | 108.8 |
C5'A—C4'A—H41A | 109.2 | C5'B—C4'B—H41B | 108.8 |
C3'A—C4'A—H41A | 109.2 | C3'B—C4'B—H41B | 108.8 |
O5'A—C5'A—C4'A | 108.52 (7) | O5'B—C5'B—C4'B | 109.34 (7) |
O5'A—C5'A—H51A | 110.0 | O5'B—C5'B—H51B | 109.8 |
C4'A—C5'A—H51A | 110.0 | C4'B—C5'B—H51B | 109.8 |
O5'A—C5'A—H52A | 110.0 | O5'B—C5'B—H52B | 109.8 |
C4'A—C5'A—H52A | 110.0 | C4'B—C5'B—H52B | 109.8 |
H51A—C5'A—H52A | 108.4 | H51B—C5'B—H52B | 108.3 |
| | | |
C2A—N1A—C1'A—O4'A | 124.84 (8) | C2B—N1B—C1'B—O4'B | 123.87 (9) |
C4'A—O4'A—C1'A—C2'A | 17.59 (8) | C4'B—O4'B—C1'B—C2'B | 8.61 (9) |
O4'A—C1'A—C2'A—C3'A | 5.50 (8) | O4'B—C1'B—C2'B—C3'B | 10.72 (9) |
C1'A—C2'A—C3'A—C4'A | −24.58 (8) | C1'B—C2'B—C3'B—C4'B | −24.45 (8) |
C2'A—C3'A—C4'A—O4'A | 35.38 (8) | C2'B—C3'B—C4'B—O4'B | 30.05 (9) |
C3'A—C4'A—O4'A—C1'A | −33.64 (8) | C3'B—C4'B—O4'B—C1'B | −24.65 (9) |
O4'A—C4'A—C5'A—O5'A | 59.34 (9) | O4'B—C4'B—C5'B—O5'B | −68.49 (10) |
C6A—N1A—C2A—O2A | 178.02 (8) | C6B—N1B—C2B—O2B | −179.61 (9) |
C1'A—N1A—C2A—O2A | −3.22 (12) | C1'B—N1B—C2B—O2B | −3.66 (13) |
C6A—N1A—C2A—N3A | −2.18 (11) | C6B—N1B—C2B—N3B | −0.55 (12) |
C1'A—N1A—C2A—N3A | 176.59 (7) | C1'B—N1B—C2B—N3B | 175.39 (8) |
C4A—N3A—C2A—O2A | −175.73 (9) | C4B—N3B—C2B—O2B | 176.99 (9) |
C4A—N3A—C2A—N1A | 4.46 (12) | C4B—N3B—C2B—N1B | −2.09 (12) |
C2A—N3A—C4A—O4A | 177.70 (9) | C2B—N3B—C4B—O4B | −177.20 (9) |
C2A—N3A—C4A—C5A | −2.87 (13) | C2B—N3B—C4B—C5B | 3.35 (12) |
O4A—C4A—C5A—C6A | 178.33 (10) | O4B—C4B—C5B—C6B | 178.62 (10) |
N3A—C4A—C5A—C6A | −1.06 (12) | N3B—C4B—C5B—C6B | −1.96 (12) |
O4A—C4A—C5A—C7A | −2.10 (14) | O4B—C4B—C5B—C7B | −0.63 (14) |
N3A—C4A—C5A—C7A | 178.51 (8) | N3B—C4B—C5B—C7B | 178.79 (8) |
C4A—C5A—C6A—N1A | 3.14 (12) | C4B—C5B—C6B—N1B | −0.36 (14) |
C7A—C5A—C6A—N1A | −176.41 (8) | C7B—C5B—C6B—N1B | 178.86 (9) |
C2A—N1A—C6A—C5A | −1.50 (12) | C2B—N1B—C6B—C5B | 1.73 (14) |
C1'A—N1A—C6A—C5A | 179.75 (8) | C1'B—N1B—C6B—C5B | −174.21 (9) |
C4'A—O4'A—C1'A—N1A | 140.35 (6) | C4'B—O4'B—C1'B—N1B | 131.14 (8) |
C6A—N1A—C1'A—O4'A | −56.38 (9) | C6B—N1B—C1'B—O4'B | −60.12 (11) |
C2A—N1A—C1'A—C2'A | −117.10 (8) | C2B—N1B—C1'B—C2'B | −117.23 (9) |
C6A—N1A—C1'A—C2'A | 61.68 (10) | C6B—N1B—C1'B—C2'B | 58.79 (11) |
N1A—C1'A—C2'A—C3'A | −112.64 (8) | N1B—C1'B—C2'B—C3'B | −108.45 (8) |
C1'A—C2'A—C3'A—O3'A | 92.32 (9) | C1'B—C2'B—C3'B—O3'B | 91.40 (8) |
C1'A—O4'A—C4'A—C5'A | 89.07 (8) | C1'B—O4'B—C4'B—C5'B | 98.63 (9) |
O3'A—C3'A—C4'A—O4'A | −79.74 (8) | O3'B—C3'B—C4'B—O4'B | −89.59 (8) |
O3'A—C3'A—C4'A—C5'A | 159.11 (7) | O3'B—C3'B—C4'B—C5'B | 148.27 (7) |
C2'A—C3'A—C4'A—C5'A | −85.77 (8) | C2'B—C3'B—C4'B—C5'B | −92.09 (9) |
C3'A—C4'A—C5'A—O5'A | 176.54 (6) | C3'B—C4'B—C5'B—O5'B | 50.39 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3′A—H3′A···O5′Ai | 0.83 (3) | 2.00 (2) | 2.7923 (14) | 161 (3) |
O5′A—H5′A···O4Aii | 0.84 (2) | 1.93 (2) | 2.7546 (12) | 170 (2) |
N3A—H3A···O2Biii | 0.874 (19) | 1.979 (19) | 2.8531 (12) | 177.9 (18) |
C6A—H61A···O3′A | 0.95 | 2.43 | 3.2371 (15) | 143 |
O3′B—H3′B···O4′Aiv | 0.84 (2) | 2.09 (2) | 2.9144 (12) | 166 (2) |
O5′B—H5′B···O4Bv | 0.72 (3) | 2.09 (3) | 2.7893 (13) | 162 (3) |
N3B—H3B···O2Avi | 0.857 (19) | 1.961 (19) | 2.8078 (12) | 169.7 (19) |
C6B—H61B···O3′B | 0.95 | 2.35 | 3.1682 (16) | 144 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z+1; (iii) x+1, y, z−1; (iv) x−1, y−1, z; (v) x−1, y, z−1; (vi) x−1, y, z+1. |