Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010799/de1134sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010799/de1134Isup2.hkl |
CCDC reference: 164643
The synthesis of the title compound has been described by Van Aerschot et al. (1990). Colorless prismatic crystals were grown by slow evaporation from methanol at room temperature (293 K).
H atoms of hydroxyl O atoms and water molecules were located from a difference map and not refined. Other H atoms were obtained from stereochemical considerations and were refined isotropically in riding mode. The numbering scheme is shown in Fig. 1 and consistent with the rules of the IUPAC-IUB commission on biochemical nomenclature (IUPAC-IUB, 1983).
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL93.
C10H12N4O3S·0.75H2O | Z = 4 |
Mr = 281.81 | F(000) = 590 |
Triclinic, P1 | Dx = 1.451 Mg m−3 |
a = 7.995 (2) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 9.261 (2) Å | Cell parameters from 25 reflections |
c = 18.062 (2) Å | θ = 9.6–14.4° |
α = 98.29 (1)° | µ = 0.27 mm−1 |
β = 94.47 (1)° | T = 293 K |
γ = 101.21 (1)° | Plate, colorless |
V = 1290.4 (4) Å3 | 0.25 × 0.21 × 0.12 mm |
Enraf-Nonius CAD-4 diffractometer | 3382 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.1°, θmin = 1.2° |
ω–2θ scans | h = −9→9 |
Absorption correction: emperical via ψ scan (north et al., 1968) ? | k = −11→10 |
Tmin = 0.848, Tmax = 0.973 | l = 0→21 |
4559 measured reflections | 3 standard reflections every 100 reflections |
4559 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full with fixed elements per cycle | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.155 | Calculated w = 1/[σ2(Fo2) + (0.1004P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = −0.007 |
4559 reflections | Δρmax = 0.42 e Å−3 |
673 parameters | Δρmin = −0.53 e Å−3 |
4 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (9) |
C10H12N4O3S·0.75H2O | γ = 101.21 (1)° |
Mr = 281.81 | V = 1290.4 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.995 (2) Å | Mo Kα radiation |
b = 9.261 (2) Å | µ = 0.27 mm−1 |
c = 18.062 (2) Å | T = 293 K |
α = 98.29 (1)° | 0.25 × 0.21 × 0.12 mm |
β = 94.47 (1)° |
Enraf-Nonius CAD-4 diffractometer | 3382 reflections with I > 2σ(I) |
Absorption correction: emperical via ψ scan (north et al., 1968) ? | Rint = 0.000 |
Tmin = 0.848, Tmax = 0.973 | 3 standard reflections every 100 reflections |
4559 measured reflections | intensity decay: none |
4559 independent reflections |
R[F2 > 2σ(F2)] = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.155 | Δρmax = 0.42 e Å−3 |
S = 0.96 | Δρmin = −0.53 e Å−3 |
4559 reflections | Absolute structure: Flack (1983) |
673 parameters | Absolute structure parameter: 0.04 (9) |
4 restraints |
Experimental. Data collection CAD-4 Software (Enraf–Nonius,1989). Cell refinement: CAD-4 Software. Program(s) used to solve structure:SHELXL86 (Sheldrick,1986). Program(s) used to refine structure: SHELXL93 (Sheldrick,1993). Moleculer graphics: ORTEP II (Johnson,1976). Software used to prepare material for publication: SHELXL93 and PARST93 (Nardelli,1995). |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
O1'A | 0.2401 (4) | 0.1350 (4) | 0.4721 (2) | 0.0443 (7) | |
C2'A | 0.3876 (5) | 0.0944 (4) | 0.4459 (3) | 0.0399 (9) | |
H2'A | 0.395 (5) | −0.005 (4) | 0.457 (3) | 0.048* | |
C3'A | 0.5520 (7) | 0.2076 (6) | 0.4808 (3) | 0.0576 (12) | |
H13A | 0.544 (7) | 0.307 (6) | 0.472 (3) | 0.069* | |
H23A | 0.650 (7) | 0.181 (6) | 0.458 (3) | 0.069* | |
S4'A | 0.5776 (2) | 0.2049 (2) | 0.58210 (9) | 0.0706 (4) | |
C5'A | 0.3608 (7) | 0.2255 (6) | 0.6026 (3) | 0.0571 (12) | |
H15A | 0.345 (7) | 0.208 (6) | 0.653 (3) | 0.068* | |
H25A | 0.349 (7) | 0.327 (6) | 0.599 (3) | 0.068* | |
C6'A | 0.2274 (6) | 0.1204 (6) | 0.5494 (3) | 0.0495 (10) | |
H6'A | 0.242 (6) | 0.019 (6) | 0.555 (3) | 0.059* | |
C7'A | 0.0467 (8) | 0.1294 (7) | 0.5662 (3) | 0.0616 (13) | |
H17A | 0.040 (8) | 0.129 (7) | 0.619 (3) | 0.074* | |
H27A | 0.023 (8) | 0.223 (7) | 0.555 (3) | 0.074* | |
O7'A | −0.0828 (6) | 0.0101 (5) | 0.5254 (2) | 0.0687 (11) | |
N9A | 0.3689 (5) | 0.0915 (4) | 0.3643 (2) | 0.0446 (8) | |
C8A | 0.4536 (6) | 0.1873 (5) | 0.3227 (3) | 0.0423 (9) | |
H8A | 0.536 (6) | 0.271 (5) | 0.344 (3) | 0.051* | |
N7A | 0.4082 (6) | 0.1512 (4) | 0.2504 (2) | 0.0477 (8) | |
C5A | 0.2830 (5) | 0.0230 (4) | 0.2446 (3) | 0.0377 (8) | |
C6A | 0.1814 (6) | −0.0689 (5) | 0.1795 (3) | 0.0465 (10) | |
N1A | 0.0709 (5) | −0.1868 (4) | 0.2004 (3) | 0.0486 (9) | |
H1A | 0.004 (5) | −0.247 (4) | 0.165 (3) | 0.058* | |
C2A | 0.0576 (7) | −0.2169 (5) | 0.2696 (3) | 0.0495 (10) | |
H2A | −0.021 (7) | −0.302 (5) | 0.275 (3) | 0.059* | |
N3A | 0.1462 (5) | −0.1359 (4) | 0.3314 (2) | 0.0463 (8) | |
C4A | 0.2591 (6) | −0.0146 (5) | 0.3131 (3) | 0.0456 (9) | |
O6A | 0.1926 (5) | −0.0514 (5) | 0.1144 (2) | 0.0630 (9) | |
H7'A | −0.102 | 0.029 | 0.473 | 0.070* | |
O1'B | 0.9698 (4) | 0.5115 (3) | 0.3727 (2) | 0.0389 (6) | |
C2'B | 1.1034 (6) | 0.4301 (4) | 0.3719 (2) | 0.0383 (8) | |
H2'B | 1.064 (6) | 0.336 (4) | 0.390 (2) | 0.046* | |
C3'B | 1.2625 (6) | 0.5170 (6) | 0.4211 (3) | 0.0533 (11) | |
H13B | 1.302 (6) | 0.610 (6) | 0.403 (3) | 0.064* | |
H23B | 1.353 (6) | 0.461 (6) | 0.418 (3) | 0.064* | |
S4'B | 1.2210 (2) | 0.5544 (2) | 0.51735 (8) | 0.0603 (3) | |
C5'B | 1.0406 (6) | 0.6425 (6) | 0.5027 (3) | 0.0522 (12) | |
H15B | 0.991 (6) | 0.660 (6) | 0.549 (3) | 0.063* | |
H25B | 1.079 (6) | 0.738 (6) | 0.487 (3) | 0.063* | |
C6'B | 0.9051 (6) | 0.5438 (5) | 0.4429 (3) | 0.0421 (9) | |
H6'B | 0.860 (6) | 0.450 (5) | 0.461 (3) | 0.051* | |
C7'B | 0.7617 (7) | 0.6206 (7) | 0.4275 (3) | 0.0622 (15) | |
H17B | 0.705 (7) | 0.636 (7) | 0.473 (3) | 0.075* | |
H27B | 0.808 (7) | 0.718 (7) | 0.415 (3) | 0.075* | |
O7'B | 0.6376 (5) | 0.5358 (5) | 0.3668 (2) | 0.0626 (9) | |
N9B | 1.1294 (4) | 0.3973 (4) | 0.2935 (2) | 0.0369 (7) | |
C8B | 1.2296 (5) | 0.4838 (5) | 0.2539 (3) | 0.0440 (9) | |
H8B | 1.310 (5) | 0.568 (5) | 0.277 (3) | 0.053* | |
N7B | 1.2063 (5) | 0.4425 (4) | 0.1817 (2) | 0.0396 (7) | |
C5B | 1.0761 (5) | 0.3147 (4) | 0.1722 (2) | 0.0353 (8) | |
C6B | 0.9959 (5) | 0.2195 (4) | 0.1058 (2) | 0.0372 (8) | |
N1B | 0.8628 (5) | 0.1108 (4) | 0.1213 (2) | 0.0454 (9) | |
H1B | 0.799 (5) | 0.053 (4) | 0.084 (2) | 0.054* | |
C2B | 0.8285 (6) | 0.0908 (5) | 0.1906 (3) | 0.0465 (10) | |
H2B | 0.743 (6) | 0.009 (5) | 0.194 (3) | 0.056* | |
N3B | 0.9022 (5) | 0.1731 (4) | 0.2540 (2) | 0.0447 (8) | |
C4B | 1.0290 (5) | 0.2872 (4) | 0.2401 (2) | 0.0360 (8) | |
O6B | 1.0193 (5) | 0.2285 (4) | 0.0393 (2) | 0.0575 (9) | |
H7'B | 0.656 | 0.539 | 0.322 | 0.070* | |
O1'C | 0.5874 (4) | 0.8178 (4) | 0.7811 (2) | 0.0484 (7) | |
C2'C | 0.4390 (5) | 0.7703 (5) | 0.8159 (3) | 0.0403 (8) | |
H2'C | 0.398 (5) | 0.663 (5) | 0.798 (3) | 0.048* | |
C3'C | 0.2984 (9) | 0.8463 (9) | 0.7988 (3) | 0.071 (2) | |
H13C | 0.337 (9) | 0.953 (9) | 0.816 (3) | 0.085* | |
H23C | 0.203 (9) | 0.811 (9) | 0.826 (3) | 0.085* | |
S4'C | 0.2273 (2) | 0.8148 (3) | 0.69994 (11) | 0.0965 (7) | |
C5'C | 0.4381 (4) | 0.8699 (7) | 0.6702 (3) | 0.0640 (13) | |
H15C | 0.429 (4) | 0.852 (7) | 0.616 (3) | 0.077* | |
H25C | 0.479 (4) | 0.976 (7) | 0.687 (3) | 0.077* | |
C6'C | 0.5640 (6) | 0.7877 (5) | 0.6999 (3) | 0.0464 (10) | |
H6'C | 0.525 (6) | 0.680 (5) | 0.682 (3) | 0.056* | |
C7'C | 0.7432 (7) | 0.8426 (7) | 0.6751 (3) | 0.0602 (13) | |
H17C | 0.775 (7) | 0.951 (7) | 0.686 (3) | 0.072* | |
H27C | 0.828 (7) | 0.802 (7) | 0.702 (3) | 0.072* | |
O7'C | 0.7386 (8) | 0.7961 (6) | 0.5986 (3) | 0.087 (2) | |
H7'C | 0.722 | 0.865 | 0.576 | 0.070* | |
N9C | 0.4967 (4) | 0.7918 (4) | 0.8952 (2) | 0.0409 (7) | |
C8C | 0.6119 (7) | 0.9115 (5) | 0.9368 (3) | 0.0541 (13) | |
H8C | 0.673 (7) | 0.988 (5) | 0.915 (3) | 0.065* | |
N7C | 0.6286 (6) | 0.9095 (5) | 1.0071 (2) | 0.0523 (10) | |
C5C | 0.5097 (5) | 0.7815 (5) | 1.0164 (3) | 0.0406 (9) | |
C6C | 0.4673 (5) | 0.7257 (5) | 1.0841 (3) | 0.0428 (10) | |
N1C | 0.3415 (5) | 0.5938 (4) | 1.0637 (2) | 0.0467 (9) | |
H1C | 0.304 (5) | 0.549 (4) | 1.099 (2) | 0.056* | |
C2C | 0.2727 (6) | 0.5288 (6) | 0.9936 (3) | 0.0546 (12) | |
H2C | 0.190 (6) | 0.441 (6) | 0.989 (3) | 0.066* | |
N3C | 0.3123 (6) | 0.5785 (4) | 0.9319 (3) | 0.0509 (10) | |
C4C | 0.4312 (4) | 0.7096 (4) | 0.9467 (2) | 0.0357 (9) | |
O6C | 0.5208 (6) | 0.7770 (4) | 1.1486 (2) | 0.0580 (8) | |
O1'D | 0.8935 (5) | 0.3484 (4) | 0.8874 (2) | 0.0550 (8) | |
C2'D | 0.7552 (7) | 0.4235 (6) | 0.8901 (3) | 0.0522 (11) | |
H2'D | 0.647 (7) | 0.355 (6) | 0.870 (3) | 0.063* | |
C3'D | 0.7896 (16) | 0.5506 (11) | 0.8451 (4) | 0.105 (3) | |
H13D | 0.904 (16) | 0.611 (11) | 0.861 (4) | 0.126* | |
H23D | 0.707 (16) | 0.614 (11) | 0.853 (4) | 0.126* | |
S4'D | 0.7717 (5) | 0.4699 (4) | 0.74679 (12) | 0.1313 (14) | |
C5'D | 0.9295 (12) | 0.3608 (9) | 0.7580 (4) | 0.086 (2) | |
H15D | 0.932 (12) | 0.299 (9) | 0.710 (4) | 0.104* | |
H25D | 1.041 (12) | 0.427 (9) | 0.771 (4) | 0.104* | |
C6'D | 0.9015 (7) | 0.2654 (6) | 0.8152 (3) | 0.0549 (12) | |
H6'D | 0.793 (7) | 0.193 (6) | 0.800 (3) | 0.066* | |
C7'D | 1.0447 (12) | 0.1820 (8) | 0.8307 (5) | 0.086 (2) | |
H17D | 1.060 (12) | 0.119 (8) | 0.785 (5) | 0.103* | |
H27D | 1.152 (12) | 0.253 (8) | 0.848 (5) | 0.103* | |
O7'D | 0.9961 (10) | 0.0885 (6) | 0.8895 (4) | 0.099 (2) | |
N9D | 0.7569 (5) | 0.4764 (5) | 0.9701 (2) | 0.0500 (9) | |
C8D | 0.8698 (7) | 0.5971 (7) | 1.0153 (3) | 0.0581 (12) | |
H8D | 0.947 (7) | 0.666 (7) | 0.995 (3) | 0.070* | |
N7D | 0.8597 (5) | 0.6057 (5) | 1.0850 (2) | 0.0487 (9) | |
C5D | 0.7336 (5) | 0.4799 (4) | 1.0920 (2) | 0.0372 (8) | |
C6D | 0.6671 (6) | 0.4308 (5) | 1.1561 (3) | 0.0481 (11) | |
N1D | 0.5394 (6) | 0.2967 (5) | 1.1333 (3) | 0.0533 (10) | |
H1D | 0.493 (6) | 0.255 (5) | 1.168 (3) | 0.064* | |
C2D | 0.4882 (6) | 0.2333 (5) | 1.0639 (3) | 0.0500 (10) | |
H2D | 0.399 (6) | 0.149 (5) | 1.057 (3) | 0.060* | |
N3D | 0.5476 (6) | 0.2738 (5) | 1.0023 (3) | 0.0582 (11) | |
C4D | 0.6706 (6) | 0.4029 (5) | 1.0210 (3) | 0.0421 (9) | |
O6D | 0.7096 (6) | 0.4837 (5) | 1.2214 (2) | 0.0603 (9) | |
H7'D | 0.982 | 0.160 | 0.920 | 0.070* | |
O1W | 0.7998 (6) | 0.0375 (5) | 0.3829 (2) | 0.0668 (10) | |
H1W1 | 0.751 | −0.051 | 0.371 | 0.070* | |
H2W1 | 0.827 | 0.071 | 0.344 | 0.070* | |
O2W | 0.5601 (6) | −0.2076 (5) | 0.3025 (3) | 0.0736 (12) | |
H1W2 | 0.581 | −0.291 | 0.303 | 0.070* | |
H2W2 | 0.610 | −0.170 | 0.255 | 0.070* | |
O3W | 0.1147 (8) | 0.8682 (6) | 0.9563 (3) | 0.0866 (14) | |
H1W3 | 0.122 | 0.885 | 1.004 | 0.070* | |
H2W3 | 0.087 | 0.950 | 0.940 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1'A | 0.033 (2) | 0.0577 (15) | 0.038 (2) | 0.0034 (12) | −0.0025 (13) | 0.0028 (13) |
C2'A | 0.027 (2) | 0.040 (2) | 0.048 (3) | 0.0000 (14) | 0.000 (2) | 0.005 (2) |
C3'A | 0.036 (2) | 0.077 (3) | 0.046 (3) | −0.005 (2) | −0.009 (2) | −0.006 (2) |
S4'A | 0.0496 (7) | 0.1015 (10) | 0.0514 (8) | 0.0010 (7) | −0.0123 (6) | 0.0117 (7) |
C5'A | 0.050 (3) | 0.077 (3) | 0.036 (3) | −0.003 (2) | −0.002 (2) | 0.007 (2) |
C6'A | 0.038 (2) | 0.057 (2) | 0.050 (3) | 0.003 (2) | 0.005 (2) | 0.006 (2) |
C7'A | 0.051 (3) | 0.087 (4) | 0.040 (3) | 0.011 (3) | 0.006 (2) | −0.004 (2) |
O7'A | 0.051 (2) | 0.088 (3) | 0.057 (3) | −0.012 (2) | 0.001 (2) | 0.021 (2) |
N9A | 0.037 (2) | 0.049 (2) | 0.039 (2) | −0.0059 (14) | −0.001 (2) | −0.0007 (14) |
C8A | 0.042 (2) | 0.037 (2) | 0.043 (2) | −0.0087 (15) | 0.000 (2) | 0.014 (2) |
N7A | 0.040 (2) | 0.047 (2) | 0.051 (2) | −0.0041 (5) | 0.005 (2) | 0.012 (2) |
C5A | 0.025 (2) | 0.043 (2) | 0.040 (2) | 0.0001 (14) | 0.001 (2) | 0.000 (2) |
C6A | 0.041 (2) | 0.064 (2) | 0.039 (2) | 0.025 (2) | 0.002 (2) | 0.005 (2) |
N1A | 0.034 (2) | 0.041 (2) | 0.062 (3) | −0.0052 (13) | −0.011 (2) | 0.004 (2) |
C2A | 0.040 (2) | 0.048 (2) | 0.052 (3) | −0.014 (2) | 0.001 (2) | 0.013 (2) |
N3A | 0.035 (2) | 0.051 (2) | 0.049 (2) | 0.0001 (14) | 0.008 (2) | 0.007 (2) |
C4A | 0.039 (2) | 0.050 (2) | 0.040 (2) | −0.002 (2) | 0.000 (2) | −0.001 (2) |
O6A | 0.044 (2) | 0.077 (2) | 0.056 (2) | −0.006 (2) | −0.015 (2) | 0.009 (2) |
O1'B | 0.0285 (14) | 0.0372 (13) | 0.040 (2) | −0.0068 (10) | −0.0107 (12) | −0.0026 (11) |
C2'B | 0.039 (2) | 0.042 (2) | 0.029 (2) | 0.009 (2) | −0.014 (2) | −0.0044 (14) |
C3'B | 0.025 (2) | 0.068 (3) | 0.057 (3) | 0.004 (2) | −0.008 (2) | −0.011 (2) |
S4'B | 0.0463 (7) | 0.0810 (8) | 0.0461 (7) | 0.0163 (6) | −0.0196 (5) | −0.0053 (6) |
C5'B | 0.038 (2) | 0.058 (2) | 0.052 (3) | 0.015 (2) | −0.019 (2) | −0.012 (2) |
C6'B | 0.026 (2) | 0.049 (2) | 0.043 (2) | 0.000 (2) | −0.007 (2) | −0.005 (2) |
C7'B | 0.038 (3) | 0.082 (3) | 0.054 (3) | 0.013 (2) | −0.008 (2) | −0.024 (3) |
O7'B | 0.034 (2) | 0.090 (2) | 0.050 (2) | 0.002 (2) | −0.012 (2) | −0.009 (2) |
N9B | 0.0191 (14) | 0.046 (2) | 0.040 (2) | −0.0032 (12) | −0.0054 (13) | 0.0086 (14) |
C8B | 0.027 (2) | 0.048 (2) | 0.051 (3) | −0.0023 (15) | −0.001 (2) | 0.007 (2) |
N7B | 0.026 (2) | 0.047 (2) | 0.041 (2) | −0.0049 (13) | −0.0041 (14) | 0.0113 (14) |
C5B | 0.033 (2) | 0.038 (2) | 0.034 (2) | 0.0072 (15) | 0.002 (2) | 0.0014 (14) |
C6B | 0.028 (2) | 0.046 (2) | 0.042 (2) | 0.009 (2) | 0.010 (2) | 0.016 (2) |
N1B | 0.040 (2) | 0.056 (2) | 0.032 (2) | −0.005 (2) | −0.008 (2) | 0.0046 (15) |
C2B | 0.030 (2) | 0.044 (2) | 0.058 (3) | −0.005 (2) | −0.004 (2) | 0.007 (2) |
N3B | 0.034 (2) | 0.055 (2) | 0.043 (2) | 0.0009 (15) | 0.005 (2) | 0.010 (2) |
C4B | 0.023 (2) | 0.043 (2) | 0.040 (2) | 0.004 (2) | 0.001 (2) | 0.005 (2) |
O6B | 0.052 (2) | 0.068 (2) | 0.042 (2) | −0.011 (2) | −0.007 (2) | 0.010 (2) |
O1'C | 0.031 (2) | 0.071 (2) | 0.037 (2) | 0.0005 (13) | −0.0037 (13) | 0.0075 (14) |
C2'C | 0.029 (2) | 0.048 (2) | 0.042 (2) | 0.0038 (14) | 0.003 (2) | 0.008 (2) |
C3'C | 0.065 (4) | 0.112 (5) | 0.038 (3) | 0.022 (4) | 0.002 (3) | 0.013 (3) |
S4'C | 0.0527 (9) | 0.185 (2) | 0.0514 (9) | 0.0267 (12) | −0.0082 (8) | 0.0222 (11) |
C5'C | 0.066 (4) | 0.082 (3) | 0.038 (3) | 0.005 (3) | 0.001 (3) | 0.008 (2) |
C6'C | 0.045 (3) | 0.054 (2) | 0.032 (2) | −0.003 (2) | −0.001 (2) | 0.002 (2) |
C7'C | 0.040 (3) | 0.091 (3) | 0.044 (3) | −0.006 (2) | 0.018 (2) | 0.009 (2) |
O7'C | 0.093 (4) | 0.091 (3) | 0.062 (3) | −0.014 (3) | 0.018 (3) | 0.001 (2) |
N9C | 0.028 (2) | 0.052 (2) | 0.039 (2) | −0.0091 (13) | 0.0039 (15) | 0.0172 (15) |
C8C | 0.060 (3) | 0.059 (2) | 0.024 (2) | −0.028 (2) | −0.013 (2) | 0.006 (2) |
N7C | 0.039 (2) | 0.058 (2) | 0.045 (2) | −0.025 (2) | −0.006 (2) | 0.012 (2) |
C5C | 0.033 (2) | 0.040 (2) | 0.044 (2) | 0.0041 (15) | −0.006 (2) | 0.001 (2) |
C6C | 0.027 (2) | 0.051 (2) | 0.051 (3) | −0.004 (2) | 0.009 (2) | 0.022 (2) |
N1C | 0.037 (2) | 0.057 (2) | 0.043 (2) | −0.006 (2) | 0.001 (2) | 0.024 (2) |
C2C | 0.020 (2) | 0.073 (3) | 0.056 (3) | −0.021 (2) | −0.002 (2) | 0.008 (2) |
N3C | 0.042 (2) | 0.049 (2) | 0.046 (2) | −0.015 (2) | −0.006 (2) | −0.005 (2) |
C4C | 0.017 (2) | 0.042 (2) | 0.048 (2) | 0.0069 (14) | −0.005 (2) | 0.013 (2) |
O6C | 0.060 (2) | 0.073 (2) | 0.029 (2) | −0.009 (2) | −0.008 (2) | 0.0073 (14) |
O1'D | 0.061 (2) | 0.052 (2) | 0.043 (2) | 0.0086 (15) | −0.011 (2) | −0.0067 (14) |
C2'D | 0.047 (3) | 0.055 (2) | 0.052 (3) | 0.012 (2) | 0.004 (2) | −0.001 (2) |
C3'D | 0.177 (10) | 0.108 (6) | 0.054 (4) | 0.087 (7) | 0.012 (5) | 0.015 (4) |
S4'D | 0.234 (4) | 0.150 (2) | 0.0453 (10) | 0.120 (3) | 0.0108 (15) | 0.0283 (11) |
C5'D | 0.094 (6) | 0.092 (4) | 0.066 (5) | 0.013 (4) | 0.028 (4) | −0.012 (3) |
C6'D | 0.054 (3) | 0.053 (2) | 0.055 (3) | 0.008 (2) | −0.003 (2) | 0.009 (2) |
C7'D | 0.095 (6) | 0.077 (4) | 0.084 (5) | 0.033 (4) | 0.004 (4) | −0.004 (4) |
O7'D | 0.123 (5) | 0.078 (3) | 0.085 (4) | 0.017 (3) | −0.015 (4) | −0.006 (3) |
N9D | 0.037 (2) | 0.069 (2) | 0.039 (2) | 0.007 (2) | 0.006 (2) | −0.005 (2) |
C8D | 0.039 (2) | 0.078 (3) | 0.055 (3) | 0.006 (2) | −0.006 (2) | 0.016 (3) |
N7D | 0.040 (2) | 0.058 (2) | 0.040 (2) | −0.007 (2) | −0.003 (2) | 0.009 (2) |
C5D | 0.039 (2) | 0.033 (2) | 0.037 (2) | 0.0040 (15) | −0.003 (2) | 0.004 (2) |
C6D | 0.037 (2) | 0.051 (2) | 0.058 (3) | 0.004 (2) | 0.006 (2) | 0.020 (2) |
N1D | 0.050 (2) | 0.058 (2) | 0.050 (3) | 0.001 (2) | 0.011 (2) | 0.011 (2) |
C2D | 0.036 (2) | 0.056 (2) | 0.052 (3) | −0.004 (2) | 0.007 (2) | 0.004 (2) |
N3D | 0.038 (2) | 0.065 (2) | 0.052 (3) | −0.012 (2) | −0.012 (2) | −0.015 (2) |
C4D | 0.030 (2) | 0.058 (2) | 0.039 (2) | 0.007 (2) | 0.007 (2) | 0.010 (2) |
O6D | 0.064 (2) | 0.081 (2) | 0.032 (2) | 0.008 (2) | 0.000 (2) | 0.007 (2) |
O1W | 0.055 (2) | 0.083 (2) | 0.053 (2) | −0.002 (2) | −0.006 (2) | 0.007 (2) |
O2W | 0.068 (3) | 0.080 (3) | 0.055 (3) | −0.019 (2) | −0.022 (2) | 0.016 (2) |
O3W | 0.092 (4) | 0.097 (3) | 0.066 (3) | 0.007 (3) | 0.005 (3) | 0.017 (3) |
O1'A—C2'A | 1.402 (5) | C2'C—C3'C | 1.474 (7) |
O1'A—C6'A | 1.431 (6) | C2'C—H2'C | 0.98 |
C2'A—N9A | 1.465 (6) | C3'C—S4'C | 1.796 (6) |
C2'A—C3'A | 1.539 (6) | C3'C—H13C | 0.97 |
C2'A—H2'A | 0.98 | C3'C—H23C | 0.97 |
C3'A—S4'A | 1.830 (6) | S4'C—C5'C | 1.8097 (12) |
C3'A—H13A | 0.97 | C5'C—C6'C | 1.487 (8) |
C3'A—H23A | 0.97 | C5'C—H15C | 0.97 |
S4'A—C5'A | 1.840 (6) | C5'C—H25C | 0.97 |
C5'A—C6'A | 1.475 (7) | C6'C—C7'C | 1.547 (6) |
C5'A—H15A | 0.97 | C6'C—H6'C | 0.98 |
C5'A—H25A | 0.97 | C7'C—O7'C | 1.383 (7) |
C6'A—C7'A | 1.515 (7) | C7'C—H17C | 0.97 |
C6'A—H6'A | 0.98 | C7'C—H27C | 0.97 |
C7'A—O7'A | 1.428 (7) | O7'C—H7'C | 0.827 (6) |
C7'A—H17A | 0.97 | N9C—C4C | 1.357 (5) |
C7'A—H27A | 0.97 | N9C—C8C | 1.377 (5) |
O7'A—H7'A | 0.986 (4) | C8C—N7C | 1.269 (6) |
N9A—C8A | 1.360 (5) | C8C—H8C | 0.93 |
N9A—C4A | 1.366 (6) | N7C—C5C | 1.408 (6) |
C8A—N7A | 1.303 (6) | C5C—C4C | 1.377 (6) |
C8A—H8A | 0.93 | C5C—C6C | 1.433 (6) |
N7A—C5A | 1.381 (6) | C6C—O6C | 1.204 (6) |
C5A—C4A | 1.351 (7) | C6C—N1C | 1.405 (6) |
C5A—C6A | 1.436 (6) | N1C—C2C | 1.346 (7) |
C6A—O6A | 1.217 (6) | N1C—H1C | 0.86 |
C6A—N1A | 1.383 (6) | C2C—N3C | 1.304 (7) |
N1A—C2A | 1.327 (7) | C2C—H2C | 0.93 |
N1A—H1A | 0.86 | N3C—C4C | 1.367 (5) |
C2A—N3A | 1.319 (6) | O1'D—C2'D | 1.417 (6) |
C2A—H2A | 0.93 | O1'D—C6'D | 1.428 (7) |
N3A—C4A | 1.395 (6) | C2'D—N9D | 1.454 (7) |
O1'B—C6'B | 1.420 (5) | C2'D—C3'D | 1.518 (10) |
O1'B—C2'B | 1.422 (5) | C2'D—H2'D | 0.98 |
C2'B—N9B | 1.444 (6) | C3'D—S4'D | 1.809 (8) |
C2'B—C3'B | 1.508 (6) | C3'D—H13D | 0.97 |
C2'B—H2'B | 0.98 | C3'D—H23D | 0.97 |
C3'B—S4'B | 1.793 (6) | S4'D—C5'D | 1.780 (9) |
C3'B—H13B | 0.97 | C5'D—C6'D | 1.456 (10) |
C3'B—H23B | 0.97 | C5'D—H15D | 0.97 |
S4'B—C5'B | 1.811 (5) | C5'D—H25D | 0.97 |
C5'B—C6'B | 1.525 (6) | C6'D—C7'D | 1.531 (8) |
C5'B—H15B | 0.97 | C6'D—H6'D | 0.98 |
C5'B—H25B | 0.97 | C7'D—O7'D | 1.492 (11) |
C6'B—C7'B | 1.491 (6) | C7'D—H17D | 0.97 |
C6'B—H6'B | 0.98 | C7'D—H27D | 0.97 |
C7'B—O7'B | 1.443 (6) | O7'D—H7'D | 0.830 (6) |
C7'B—H17B | 0.97 | N9D—C4D | 1.372 (6) |
C7'B—H27B | 0.97 | N9D—C8D | 1.401 (7) |
O7'B—H7'B | 0.837 (4) | C8D—N7D | 1.260 (7) |
N9B—C8B | 1.342 (6) | C8D—H8D | 0.93 |
N9B—C4B | 1.375 (5) | N7D—C5D | 1.412 (5) |
C8B—N7B | 1.294 (6) | C5D—C4D | 1.378 (6) |
C8B—H8B | 0.93 | C5D—C6D | 1.409 (6) |
N7B—C5B | 1.396 (5) | C6D—O6D | 1.206 (7) |
C5B—C4B | 1.355 (6) | C6D—N1D | 1.431 (7) |
C5B—C6B | 1.408 (6) | N1D—C2D | 1.304 (7) |
C6B—O6B | 1.242 (6) | N1D—H1D | 0.86 |
C6B—N1B | 1.391 (5) | C2D—N3D | 1.318 (7) |
N1B—C2B | 1.333 (7) | C2D—H2D | 0.93 |
N1B—H1B | 0.86 | N3D—C4D | 1.374 (6) |
C2B—N3B | 1.308 (6) | O1W—H1W1 | 0.826 (5) |
C2B—H2B | 0.93 | O1W—H2W1 | 0.841 (4) |
N3B—C4B | 1.381 (5) | O2W—H1W2 | 0.822 (5) |
O1'C—C2'C | 1.411 (5) | O2W—H2W2 | 1.053 (5) |
O1'C—C6'C | 1.444 (5) | O3W—H1W3 | 0.846 (5) |
C2'C—N9C | 1.443 (6) | O3W—H2W3 | 0.911 (6) |
C2'A—O1'A—C6'A | 112.6 (3) | O1'C—C2'C—C3'C | 113.8 (4) |
O1'A—C2'A—N9A | 106.3 (3) | N9C—C2'C—C3'C | 113.3 (4) |
O1'A—C2'A—C3'A | 112.0 (4) | O1'C—C2'C—H2'C | 108.1 (2) |
N9A—C2'A—C3'A | 108.9 (4) | N9C—C2'C—H2'C | 108.1 (2) |
O1'A—C2'A—H2'A | 109.8 (2) | C3'C—C2'C—H2'C | 108.1 (3) |
N9A—C2'A—H2'A | 109.8 (2) | C2'C—C3'C—S4'C | 112.2 (4) |
C3'A—C2'A—H2'A | 109.8 (3) | C2'C—C3'C—H13C | 109.2 (3) |
C2'A—C3'A—S4'A | 108.4 (4) | S4'C—C3'C—H13C | 109.2 (3) |
C2'A—C3'A—H13A | 110.0 (3) | C2'C—C3'C—H23C | 109.2 (3) |
S4'A—C3'A—H13A | 110.0 (2) | S4'C—C3'C—H23C | 109.2 (2) |
C2'A—C3'A—H23A | 110.0 (3) | H13C—C3'C—H23C | 107.9 |
S4'A—C3'A—H23A | 110.0 (2) | C3'C—S4'C—C5'C | 95.7 (3) |
H13A—C3'A—H23A | 108.4 | C6'C—C5'C—S4'C | 112.8 (4) |
C3'A—S4'A—C5'A | 98.4 (3) | C6'C—C5'C—H15C | 109.0 (3) |
C6'A—C5'A—S4'A | 111.6 (4) | S4'C—C5'C—H15C | 109.0 (2) |
C6'A—C5'A—H15A | 109.3 (3) | C6'C—C5'C—H25C | 109.0 (3) |
S4'A—C5'A—H15A | 109.3 (2) | S4'C—C5'C—H25C | 109.0 (2) |
C6'A—C5'A—H25A | 109.3 (3) | H15C—C5'C—H25C | 107.8 |
S4'A—C5'A—H25A | 109.3 (2) | O1'C—C6'C—C5'C | 110.5 (4) |
H15A—C5'A—H25A | 108.0 | O1'C—C6'C—C7'C | 105.3 (4) |
O1'A—C6'A—C5'A | 114.1 (4) | C5'C—C6'C—C7'C | 110.7 (4) |
O1'A—C6'A—C7'A | 108.1 (4) | O1'C—C6'C—H6'C | 110.1 (2) |
C5'A—C6'A—C7'A | 113.3 (4) | C5'C—C6'C—H6'C | 110.1 (3) |
O1'A—C6'A—H6'A | 107.0 (2) | C7'C—C6'C—H6'C | 110.1 (3) |
C5'A—C6'A—H6'A | 107.0 (3) | O7'C—C7'C—C6'C | 109.0 (5) |
C7'A—C6'A—H6'A | 107.0 (3) | O7'C—C7'C—H17C | 109.9 (3) |
O7'A—C7'A—C6'A | 114.2 (4) | C6'C—C7'C—H17C | 109.9 (3) |
O7'A—C7'A—H17A | 108.7 (3) | O7'C—C7'C—H27C | 109.9 (4) |
C6'A—C7'A—H17A | 108.7 (3) | C6'C—C7'C—H27C | 109.9 (3) |
O7'A—C7'A—H27A | 108.7 (3) | H17C—C7'C—H27C | 108.3 |
C6'A—C7'A—H27A | 108.7 (3) | C7'C—O7'C—H7'C | 108.8 (6) |
H17A—C7'A—H27A | 107.6 | C4C—N9C—C8C | 104.9 (4) |
C7'A—O7'A—H7'A | 108.4 (4) | C4C—N9C—C2'C | 127.1 (3) |
C8A—N9A—C4A | 105.0 (4) | C8C—N9C—C2'C | 127.4 (3) |
C8A—N9A—C2'A | 129.5 (4) | N7C—C8C—N9C | 114.7 (4) |
C4A—N9A—C2'A | 125.5 (3) | N7C—C8C—H8C | 122.6 (2) |
N7A—C8A—N9A | 114.1 (4) | N9C—C8C—H8C | 122.6 (2) |
N7A—C8A—H8A | 122.9 (2) | C8C—N7C—C5C | 104.4 (4) |
N9A—C8A—H8A | 122.9 (2) | C4C—C5C—N7C | 108.7 (4) |
C8A—N7A—C5A | 103.3 (4) | C4C—C5C—C6C | 121.8 (4) |
C4A—C5A—N7A | 110.8 (4) | N7C—C5C—C6C | 129.5 (4) |
C4A—C5A—C6A | 118.9 (4) | O6C—C6C—N1C | 122.5 (4) |
N7A—C5A—C6A | 130.3 (4) | O6C—C6C—C5C | 129.6 (4) |
O6A—C6A—N1A | 123.6 (5) | N1C—C6C—C5C | 107.8 (4) |
O6A—C6A—C5A | 126.1 (5) | C2C—N1C—C6C | 126.9 (4) |
N1A—C6A—C5A | 110.3 (4) | C2C—N1C—H1C | 116.6 (3) |
C2A—N1A—C6A | 126.9 (4) | C6C—N1C—H1C | 116.6 (2) |
C2A—N1A—H1A | 116.5 (3) | N3C—C2C—N1C | 125.5 (4) |
C6A—N1A—H1A | 116.5 (3) | N3C—C2C—H2C | 117.3 (3) |
N3A—C2A—N1A | 125.4 (4) | N1C—C2C—H2C | 117.3 (3) |
N3A—C2A—H2A | 117.3 (3) | C2C—N3C—C4C | 111.6 (4) |
N1A—C2A—H2A | 117.3 (3) | N9C—C4C—N3C | 126.4 (4) |
C2A—N3A—C4A | 109.8 (4) | N9C—C4C—C5C | 107.1 (4) |
C5A—C4A—N9A | 106.7 (4) | N3C—C4C—C5C | 126.5 (4) |
C5A—C4A—N3A | 128.7 (5) | C2'D—O1'D—C6'D | 113.9 (4) |
N9A—C4A—N3A | 124.6 (4) | O1'D—C2'D—N9D | 103.4 (4) |
C6'B—O1'B—C2'B | 116.5 (3) | O1'D—C2'D—C3'D | 108.8 (5) |
O1'B—C2'B—N9B | 104.9 (3) | N9D—C2'D—C3'D | 112.4 (5) |
O1'B—C2'B—C3'B | 111.4 (3) | O1'D—C2'D—H2'D | 110.7 (2) |
N9B—C2'B—C3'B | 113.4 (4) | N9D—C2'D—H2'D | 110.7 (3) |
O1'B—C2'B—H2'B | 109.0 (2) | C3'D—C2'D—H2'D | 110.7 (5) |
N9B—C2'B—H2'B | 109.0 (2) | C2'D—C3'D—S4'D | 107.8 (6) |
C3'B—C2'B—H2'B | 109.0 (3) | C2'D—C3'D—H13D | 110.1 (5) |
C2'B—C3'B—S4'B | 111.1 (4) | S4'D—C3'D—H13D | 110.1 (4) |
C2'B—C3'B—H13B | 109.4 (3) | C2'D—C3'D—H23D | 110.1 (4) |
S4'B—C3'B—H13B | 109.4 (2) | S4'D—C3'D—H23D | 110.1 (3) |
C2'B—C3'B—H23B | 109.4 (2) | H13D—C3'D—H23D | 108.5 |
S4'B—C3'B—H23B | 109.4 (2) | C5'D—S4'D—C3'D | 95.6 (4) |
H13B—C3'B—H23B | 108.0 | C6'D—C5'D—S4'D | 114.4 (5) |
C3'B—S4'B—C5'B | 97.9 (2) | C6'D—C5'D—H15D | 108.7 (3) |
C6'B—C5'B—S4'B | 110.5 (3) | S4'D—C5'D—H15D | 108.7 (3) |
C6'B—C5'B—H15B | 109.6 (3) | C6'D—C5'D—H25D | 108.7 (4) |
S4'B—C5'B—H15B | 109.6 (2) | S4'D—C5'D—H25D | 108.7 (3) |
C6'B—C5'B—H25B | 109.6 (3) | H15D—C5'D—H25D | 107.6 |
S4'B—C5'B—H25B | 109.6 (2) | O1'D—C6'D—C5'D | 112.2 (5) |
H15B—C5'B—H25B | 108.1 | O1'D—C6'D—C7'D | 102.7 (5) |
O1'B—C6'B—C7'B | 105.8 (4) | C5'D—C6'D—C7'D | 115.0 (6) |
O1'B—C6'B—C5'B | 112.7 (4) | O1'D—C6'D—H6'D | 108.9 (3) |
C7'B—C6'B—C5'B | 110.4 (4) | C5'D—C6'D—H6'D | 108.9 (4) |
O1'B—C6'B—H6'B | 109.3 (2) | C7'D—C6'D—H6'D | 108.9 (4) |
C7'B—C6'B—H6'B | 109.3 (3) | O7'D—C7'D—C6'D | 108.5 (7) |
C5'B—C6'B—H6'B | 109.3 (3) | O7'D—C7'D—H17D | 110.0 (3) |
O7'B—C7'B—C6'B | 112.0 (4) | C6'D—C7'D—H17D | 110.0 (4) |
O7'B—C7'B—H17B | 109.2 (3) | O7'D—C7'D—H27D | 110.0 (4) |
C6'B—C7'B—H17B | 109.2 (3) | C6'D—C7'D—H27D | 110.0 (4) |
O7'B—C7'B—H27B | 109.2 (3) | H17D—C7'D—H27D | 108.4 |
C6'B—C7'B—H27B | 109.2 (3) | C7'D—O7'D—H7'D | 93.7 (6) |
H17B—C7'B—H27B | 107.9 | C4D—N9D—C8D | 103.6 (4) |
C7'B—O7'B—H7'B | 119.7 (5) | C4D—N9D—C2'D | 127.3 (4) |
C8B—N9B—C4B | 104.6 (4) | C8D—N9D—C2'D | 128.1 (5) |
C8B—N9B—C2'B | 127.6 (4) | N7D—C8D—N9D | 115.2 (5) |
C4B—N9B—C2'B | 126.4 (3) | N7D—C8D—H8D | 122.4 (3) |
N7B—C8B—N9B | 115.5 (4) | N9D—C8D—H8D | 122.4 (3) |
N7B—C8B—H8B | 122.2 (2) | C8D—N7D—C5D | 104.8 (4) |
N9B—C8B—H8B | 122.2 (3) | C4D—C5D—C6D | 120.4 (4) |
C8B—N7B—C5B | 103.1 (4) | C4D—C5D—N7D | 108.7 (4) |
C4B—C5B—N7B | 109.9 (4) | C6D—C5D—N7D | 130.8 (4) |
C4B—C5B—C6B | 120.3 (4) | O6D—C6D—C5D | 128.5 (5) |
N7B—C5B—C6B | 129.8 (4) | O6D—C6D—N1D | 122.1 (5) |
O6B—C6B—N1B | 119.3 (4) | C5D—C6D—N1D | 109.3 (4) |
O6B—C6B—C5B | 129.3 (4) | C2D—N1D—C6D | 125.2 (4) |
N1B—C6B—C5B | 111.1 (4) | C2D—N1D—H1D | 117.4 (3) |
C2B—N1B—C6B | 123.9 (4) | C6D—N1D—H1D | 117.4 (3) |
C2B—N1B—H1B | 118.0 (3) | N1D—C2D—N3D | 127.7 (5) |
C6B—N1B—H1B | 118.0 (3) | N1D—C2D—H2D | 116.2 (3) |
N3B—C2B—N1B | 127.2 (4) | N3D—C2D—H2D | 116.2 (3) |
N3B—C2B—H2B | 116.4 (3) | C2D—N3D—C4D | 109.4 (4) |
N1B—C2B—H2B | 116.4 (3) | N9D—C4D—N3D | 124.5 (4) |
C2B—N3B—C4B | 110.0 (4) | N9D—C4D—C5D | 107.6 (4) |
C5B—C4B—N9B | 106.9 (4) | N3D—C4D—C5D | 127.9 (4) |
C5B—C4B—N3B | 127.2 (4) | H1W1—O1W—H2W1 | 108.3 (5) |
N9B—C4B—N3B | 125.9 (4) | H1W2—O2W—H2W2 | 106.3 (6) |
C2'C—O1'C—C6'C | 114.8 (4) | H1W3—O3W—H2W3 | 106.7 (6) |
O1'C—C2'C—N9C | 105.2 (3) | ||
C6'A—O1'A—C2'A—N9A | 171.0 (3) | C6'C—O1'C—C2'C—N9C | 172.1 (3) |
C6'A—O1'A—C2'A—C3'A | −70.1 (5) | C6'C—O1'C—C2'C—C3'C | −63.3 (5) |
O1'A—C2'A—C3'A—S4'A | 64.8 (4) | O1'C—C2'C—C3'C—S4'C | 60.8 (6) |
N9A—C2'A—C3'A—S4'A | −178.0 (3) | N9C—C2'C—C3'C—S4'C | −179.0 (4) |
C2'A—C3'A—S4'A—C5'A | −50.3 (4) | C2'C—C3'C—S4'C—C5'C | −51.9 (5) |
C3'A—S4'A—C5'A—C6'A | 48.5 (4) | C3'C—S4'C—C5'C—C6'C | 53.8 (5) |
C2'A—O1'A—C6'A—C5'A | 66.8 (5) | C2'C—O1'C—C6'C—C5'C | 62.8 (5) |
C2'A—O1'A—C6'A—C7'A | −166.2 (4) | C2'C—O1'C—C6'C—C7'C | −177.6 (4) |
S4'A—C5'A—C6'A—O1'A | −58.1 (5) | S4'C—C5'C—C6'C—O1'C | −61.8 (5) |
S4'A—C5'A—C6'A—C7'A | 177.6 (4) | S4'C—C5'C—C6'C—C7'C | −178.1 (4) |
O1'A—C6'A—C7'A—O7'A | 64.3 (6) | O1'C—C6'C—C7'C—O7'C | 170.3 (5) |
C5'A—C6'A—C7'A—O7'A | −168.3 (5) | C5'C—C6'C—C7'C—O7'C | −70.2 (6) |
O1'A—C2'A—N9A—C8A | 108.2 (5) | O1'C—C2'C—N9C—C4C | −148.6 (4) |
C3'A—C2'A—N9A—C8A | −12.7 (6) | C3'C—C2'C—N9C—C4C | 86.5 (5) |
O1'A—C2'A—N9A—C4A | −72.8 (5) | O1'C—C2'C—N9C—C8C | 41.8 (6) |
C3'A—C2'A—N9A—C4A | 166.3 (4) | C3'C—C2'C—N9C—C8C | −83.1 (7) |
C4A—N9A—C8A—N7A | −0.4 (5) | C4C—N9C—C8C—N7C | 2.2 (7) |
C2'A—N9A—C8A—N7A | 178.8 (4) | C2'C—N9C—C8C—N7C | 173.7 (5) |
N9A—C8A—N7A—C5A | 0.7 (5) | N9C—C8C—N7C—C5C | −2.8 (7) |
C8A—N7A—C5A—C4A | −0.8 (5) | C8C—N7C—C5C—C4C | 2.3 (5) |
C8A—N7A—C5A—C6A | 178.9 (4) | C8C—N7C—C5C—C6C | −177.4 (5) |
C4A—C5A—C6A—O6A | −177.6 (4) | C4C—C5C—C6C—O6C | −178.0 (5) |
N7A—C5A—C6A—O6A | 2.7 (7) | N7C—C5C—C6C—O6C | 1.6 (8) |
C4A—C5A—C6A—N1A | −0.1 (5) | C4C—C5C—C6C—N1C | 0.6 (5) |
N7A—C5A—C6A—N1A | −179.8 (4) | N7C—C5C—C6C—N1C | −179.7 (4) |
O6A—C6A—N1A—C2A | 176.5 (5) | O6C—C6C—N1C—C2C | 179.3 (5) |
C5A—C6A—N1A—C2A | −1.0 (6) | C5C—C6C—N1C—C2C | 0.6 (6) |
C6A—N1A—C2A—N3A | 1.9 (8) | C6C—N1C—C2C—N3C | 0.0 (9) |
N1A—C2A—N3A—C4A | −1.2 (7) | N1C—C2C—N3C—C4C | −1.6 (8) |
N7A—C5A—C4A—N9A | 0.6 (5) | C8C—N9C—C4C—N3C | −179.3 (4) |
C6A—C5A—C4A—N9A | −179.1 (3) | C2'C—N9C—C4C—N3C | 9.2 (6) |
N7A—C5A—C4A—N3A | −179.6 (4) | C8C—N9C—C4C—C5C | −0.5 (4) |
C6A—C5A—C4A—N3A | 0.7 (7) | C2'C—N9C—C4C—C5C | −172.1 (4) |
C8A—N9A—C4A—C5A | −0.2 (5) | C2C—N3C—C4C—N9C | −178.6 (4) |
C2'A—N9A—C4A—C5A | −179.4 (4) | C2C—N3C—C4C—C5C | 3.0 (6) |
C8A—N9A—C4A—N3A | −180.0 (4) | N7C—C5C—C4C—N9C | −1.0 (4) |
C2'A—N9A—C4A—N3A | 0.8 (7) | C6C—C5C—C4C—N9C | 178.7 (4) |
C2A—N3A—C4A—C5A | 0.0 (7) | N7C—C5C—C4C—N3C | 177.7 (4) |
C2A—N3A—C4A—N9A | 179.7 (4) | C6C—C5C—C4C—N3C | −2.6 (6) |
C6'B—O1'B—C2'B—N9B | 173.2 (3) | C6'D—O1'D—C2'D—N9D | 170.5 (4) |
C6'B—O1'B—C2'B—C3'B | −63.7 (5) | C6'D—O1'D—C2'D—C3'D | −69.9 (7) |
O1'B—C2'B—C3'B—S4'B | 61.7 (5) | O1'D—C2'D—C3'D—S4'D | 69.4 (8) |
N9B—C2'B—C3'B—S4'B | 179.8 (3) | N9D—C2'D—C3'D—S4'D | −176.7 (5) |
C2'B—C3'B—S4'B—C5'B | −54.3 (4) | C2'D—C3'D—S4'D—C5'D | −56.9 (7) |
C3'B—S4'B—C5'B—C6'B | 52.2 (4) | C3'D—S4'D—C5'D—C6'D | 52.9 (7) |
C2'B—O1'B—C6'B—C7'B | −176.8 (4) | C2'D—O1'D—C6'D—C5'D | 62.8 (7) |
C2'B—O1'B—C6'B—C5'B | 62.5 (4) | C2'D—O1'D—C6'D—C7'D | −173.1 (5) |
S4'B—C5'B—C6'B—O1'B | −58.4 (5) | S4'D—C5'D—C6'D—O1'D | −57.5 (7) |
S4'B—C5'B—C6'B—C7'B | −176.5 (4) | S4'D—C5'D—C6'D—C7'D | −174.5 (5) |
O1'B—C6'B—C7'B—O7'B | 53.1 (6) | O1'D—C6'D—C7'D—O7'D | 58.5 (7) |
C5'B—C6'B—C7'B—O7'B | 175.4 (5) | C5'D—C6'D—C7'D—O7'D | −179.3 (6) |
O1'B—C2'B—N9B—C8B | 86.0 (5) | O1'D—C2'D—N9D—C4D | −90.2 (5) |
C3'B—C2'B—N9B—C8B | −35.9 (5) | C3'D—C2'D—N9D—C4D | 152.7 (6) |
O1'B—C2'B—N9B—C4B | −78.4 (4) | O1'D—C2'D—N9D—C8D | 76.0 (6) |
C3'B—C2'B—N9B—C4B | 159.8 (4) | C3'D—C2'D—N9D—C8D | −41.1 (8) |
C4B—N9B—C8B—N7B | −0.2 (5) | C4D—N9D—C8D—N7D | −1.1 (6) |
C2'B—N9B—C8B—N7B | −167.2 (4) | C2'D—N9D—C8D—N7D | −169.8 (5) |
N9B—C8B—N7B—C5B | 0.1 (5) | N9D—C8D—N7D—C5D | 1.7 (6) |
C8B—N7B—C5B—C4B | 0.0 (4) | C8D—N7D—C5D—C4D | −1.7 (5) |
C8B—N7B—C5B—C6B | −179.7 (4) | C8D—N7D—C5D—C6D | −179.7 (4) |
C4B—C5B—C6B—O6B | 178.4 (4) | C4D—C5D—C6D—O6D | 178.7 (5) |
N7B—C5B—C6B—O6B | −1.9 (7) | N7D—C5D—C6D—O6D | −3.4 (8) |
C4B—C5B—C6B—N1B | 4.8 (5) | C4D—C5D—C6D—N1D | 1.7 (6) |
N7B—C5B—C6B—N1B | −175.5 (4) | N7D—C5D—C6D—N1D | 179.6 (4) |
O6B—C6B—N1B—C2B | 179.1 (4) | O6D—C6D—N1D—C2D | −179.7 (5) |
C5B—C6B—N1B—C2B | −6.5 (6) | C5D—C6D—N1D—C2D | −2.4 (7) |
C6B—N1B—C2B—N3B | 5.4 (7) | C6D—N1D—C2D—N3D | 3.7 (9) |
N1B—C2B—N3B—C4B | −1.4 (7) | N1D—C2D—N3D—C4D | −3.5 (8) |
N7B—C5B—C4B—N9B | −0.2 (4) | C8D—N9D—C4D—N3D | −178.5 (5) |
C6B—C5B—C4B—N9B | 179.6 (4) | C2'D—N9D—C4D—N3D | −9.7 (7) |
N7B—C5B—C4B—N3B | 178.5 (4) | C8D—N9D—C4D—C5D | −0.1 (5) |
C6B—C5B—C4B—N3B | −1.8 (6) | C2'D—N9D—C4D—C5D | 168.7 (4) |
C8B—N9B—C4B—C5B | 0.2 (4) | C2D—N3D—C4D—N9D | −179.1 (4) |
C2'B—N9B—C4B—C5B | 167.5 (3) | C2D—N3D—C4D—C5D | 2.8 (7) |
C8B—N9B—C4B—N3B | −178.4 (4) | C6D—C5D—C4D—N9D | 179.4 (4) |
C2'B—N9B—C4B—N3B | −11.2 (6) | N7D—C5D—C4D—N9D | 1.1 (5) |
C2B—N3B—C4B—C5B | −0.3 (6) | C6D—C5D—C4D—N3D | −2.3 (7) |
C2B—N3B—C4B—N9B | 178.1 (4) | N7D—C5D—C4D—N3D | 179.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2W | 0.83 (4) | 2.07 (5) | 2.804 (7) | 147.5 (4) |
O1W—H2W1···N3B | 0.84 (4) | 2.06 (4) | 2.901 (6) | 174.2 (4) |
N1A—H1A···N7Di | 0.86 (6) | 1.96 (6) | 2.816 (7) | 176 (1) |
O7′A—H7′A···O1Wii | 0.99 (4) | 1.78 (4) | 2.734 (5) | 162.6 (3) |
O7′C—H7′C···O7′Aiii | 0.83 (6) | 2.20 (5) | 2.769 (8) | 125.5 (5) |
N1B—H1B···N7Civ | 0.86 (5) | 2.00 (6) | 2.858 (6) | 172 (1) |
O2W—H2W2···O6C | 1.05 (6) | 1.95 (4) | 2.753 (7) | 130.2 (4) |
O7′B—H7′B···O6Dv | 0.84 (4) | 1.92 (4) | 2.728 (6) | 161.7 (3) |
N1C—H1C···N7Bvi | 0.86 (6) | 2.02 (6) | 2.882 (6) | 177 (1) |
N1D—H1D···N7Avii | 0.86 (6) | 1.97 (6) | 2.829 (7) | 174 (1) |
O7′D—H7′D···O6Bvii | 0.83 (6) | 2.14 (4) | 2.802 (8) | 137.1 (5) |
O2W—H1W2···O7′Bviii | 0.82 (5) | 2.20 (5) | 2.938 (8) | 149.5 (5) |
O3W—H1W3···O6Aix | 0.85 (5) | 2.00 (4) | 2.833 (7) | 167.2 (4) |
O3W—H2W3···O7′Dx | 0.91 (6) | 1.89 (7) | 2.793 (9) | 167.1 (5) |
Symmetry codes: (i) x−1, y−1, z−1; (ii) x−1, y, z; (iii) x+1, y+1, z; (iv) x, y−1, z−1; (v) x, y, z−1; (vi) x−1, y, z+1; (vii) x, y, z+1; (viii) x, y−1, z; (ix) x, y+1, z+1; (x) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H12N4O3S·0.75H2O |
Mr | 281.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.995 (2), 9.261 (2), 18.062 (2) |
α, β, γ (°) | 98.29 (1), 94.47 (1), 101.21 (1) |
V (Å3) | 1290.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.25 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Emperical via ψ scan (North et al., 1968) |
Tmin, Tmax | 0.848, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4559, 4559, 3382 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.072, 0.155, 0.96 |
No. of reflections | 4559 |
No. of parameters | 673 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.53 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.04 (9) |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS86 (Sheldrick, 1986), SHELXL93 (Sheldrick, 1993), ORTEPII (Johnson, 1976), SHELXL93.
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2W | .83 (4) | 2.07 (5) | 2.804 (7) | 147.5 (4) |
O1W—H2W1···N3B | .84 (4) | 2.06 (4) | 2.901 (6) | 174.2 (4) |
N1A—H1A···N7Di | .86 (6) | 1.96 (6) | 2.816 (7) | 176.1 (6) |
O7'A—H7'A···O1Wii | .99 (4) | 1.78 (4) | 2.734 (5) | 162.6 (3) |
O7'C—H7'C···O7'Aiii | .83 (6) | 2.20 (5) | 2.769 (8) | 125.5 (5) |
N1B—H1B···N7Civ | .86 (5) | 2.00 (6) | 2.858 (6) | 172.2 (5) |
O2W—H2W2···O6C | 1.05 (6) | 1.95 (4) | 2.753 (7) | 130.2 (4) |
O7'B—H7'B···O6Dv | .84 (4) | 1.92 (4) | 2.728 (6) | 161.7 (3) |
N1C—H1C···N7Bvi | .86 (6) | 2.02 (6) | 2.882 (6) | 177.1 (5) |
N1D—H1D···N7Avii | .86 (6) | 1.97 (6) | 2.829 (7) | 174.1 (5) |
O7'D—H7'D···O6Bvii | .83 (6) | 2.14 (4) | 2.802 (8) | 137.1 (5) |
O2W—H1W2···O7'Bviii | .82 (5) | 2.20 (5) | 2.938 (8) | 149.5 (5) |
O3W—H1W3···O6Aix | .85 (5) | 2.00 (4) | 2.833 (7) | 167.2 (4) |
O3W—H2W3···O7'Dx | .91 (6) | 1.89 (7) | 2.793 (9) | 167.1 (5) |
Symmetry codes: (i) x−1, y−1, z−1; (ii) x−1, y, z; (iii) x+1, y+1, z; (iv) x, y−1, z−1; (v) x, y, z−1; (vi) x−1, y, z+1; (vii) x, y, z+1; (viii) x, y−1, z; (ix) x, y+1, z+1; (x) x−1, y+1, z. |
A number of sugar modified nucleosides display anti-viral activity because of their ability to interfere with virally encoded enzymes. The structure analysis of the title compound, (I), is a continuation of our earlier work involving systematic conformational studies on modified nucleosides with the aim of understanding structure-function relationships. The synthesis of (I) has been described (Van Aerschot et al., 1990). \sch
The crystal structure has been determined and the absolute configuration is indicated by a Flack parameter of 0.04 (9) (Flack, 1983). There are four crystallographically independent molecules in the crystal structure designated A, B, C and D. All bond lengths and bond angles of the four hypoxanthine residues agree well with the values quoted by Taylor and others (Taylor et al., 1982). The C6—O6 bond lengths in the four molecules vary from 1.204 (6) to 1.242 (6) Å with an average value of 1.217 (6) Å which agrees well with the quoted value of 1.215 Å for C═O (Taylor et al., 1982). The pyrimidine rings and imidazole rings in the four molecules are planar within experimental error. The dihedral angles between pyrimidine and imidazole rings are 0.7 (2), 2.1 (1), 1.3 (2) and 0.2 (2) ° in molecules A, B, C and D, respectively. The bond lengths and bond angles of the sugar moieties of the four molecules agree well with each other within experimental error. The N-glycosidic bond lengths N9—C2' are in the range 1.443 (6)–1.465 (6) Å having an average value of 1.451 (6) Å which agrees well with the normal value of 1.464 (6) Å. In all four molecules, the C2'-O1' bond lengths lie in the range 1.402 (5)–1.422 (5) Å with an average value of 1.413 (5) Å. This is shorter than the adjacent bond length C6'-O1' lying in the range 1.420 (5)–1.444 (5) Å with an average value of 1.430 (6) Å. Similar shortening of bond lengths has been found in glucosides with an equatorial substituent at the anomeric carbon atom C1' (Berman et al., 1967; Jeffrey et al., 1978). This anomeric effect is commonly observed in other nucleosides (Birnbaum et al., 1984; Thewalt et al., 1970; Watson et al., 1965). The orientation of O7' with respect to the sugar moiety described by the torsion angle γ (O7'-C7'-C6'-C5') is different for all four molecules. In molecules, A, B and D, the γ values are -168.3 (5), 175.4 (5) and -179.3 (6) ° and they are in the gauche-trans (ap) orientation, whereas molecule C has γ = -70.2 (6)° which corresponds to a trans-gauche (-sc) orientation. The puckering parameters (Cremer & Pople, 1975) for the sequence C2'-C3'-S4'-C5'-C6'-O1' in the oxathiane ring are Q =. 631 (5) Å, ϕ2 = -134 (5) and θ2 = 175.2 (5) ° for A molecule, Q = 0.629 (5) Å, ϕ2 = -71 (4) and θ2 = 172.9 (4) ° for B molecule, Q = 0.623 (6) Å, ϕ2 = -44 (6) and θ2 = 173.9 (5) ° for C molecule and Q = 0.663 (8) Å, ϕ2 = -117 (3) and θ2 = 170.1 (7) ° for D molecule having an average value of Q = 0.639 (6) Å for total puckering amplitude Q and this value is close to the value 0.63 Å for an ideal cyclohexane ring (Cremer & Pople, 1975). Each molecule of the title compound has two protons capable of participating in hydrogen bonds and these are from nitrogen N1 of the purine bases and hydroxyl oxygen O7'of the sugar ring. There are hydrogen bonds between purine rings. Purine rings A and D and B and C form base pairs by a single hydrogen bond of the type N1—H···N7 and these paired bases are hydrogen bonded to their translated pairs in the direction of a axis. Bases in each pair are nearly parallel to each other, the dihedral angles between them being 170.9 (2)° for the AD base pairs and 171.1 (1)° for the BC base pairs.