9(R)-[6(R)-Hydroxy­methyl-1-oxa-4-thia­cyclo­hexan-2-yl]hypoxanthine–water (4/3), a nucleoside analogue

The title compound, 9(R)-[6(R)-hydroxy­methyl-1-oxa-4-thia­cyclo­hexan-2-yl]-1,9-di­hydro-6H-purin-6-one–water (4/3), C₁₀H₁₂N₄O₃S·0.75H₂O, crystallizes in the triclinic space group P1 with four mol­ecules in the asymmetric unit and 0.75 waters of hydration per mol­ecule. The structure was refined to an R value of 0.072 for 3382 observed reflections. The four crystallographically independent mol­ecules are designated A, B, C and D. All four oxa­thia­ne rings adopt the chair conformation and the purine bases are in an anti orientation with respect to the sugar moieties. Molecules A and D and mol­ecules C and B are base paired by a single hydrogen bond of the type N—H...N. These base pairs are again hydrogen bonded to their translated pairs in the direction of a cell diagonal.

S1. Comment

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.

Related literature

For related literature, see: Berman et al. (1967); Birnbaum et al. (1984); Cremer & Pople (1975); Flack (1983); IUPAC-IUB (1983); Jeffrey et al. (1978); Taylor & Kennard (1982); Thewalt et al. (1970); Van Aerschot, Janssen & Herdewijn (1990).

S2. Experimental

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).

S3. Refinement

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).

Computing details

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.

Figures

Fig. 1. An ORTEPII (Johnson, 1976) plot of the molecule drawn at 30% probability.

(I)

Crystal data

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) Å^3	0.25 × 0.21 × 0.12 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.155	Calculated w = 1/[σ^2(Fo^2) + (0.1004P)^2] where P = (Fo^2 + 2Fc^2)/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)

Special details

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.

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

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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···N7D^i	0.86 (6)	1.96 (6)	2.816 (7)	176 (1)
O7′A—H7′A···O1W^ii	0.99 (4)	1.78 (4)	2.734 (5)	162.6 (3)
O7′C—H7′C···O7′A^iii	0.83 (6)	2.20 (5)	2.769 (8)	125.5 (5)
N1B—H1B···N7C^iv	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···O6D^v	0.84 (4)	1.92 (4)	2.728 (6)	161.7 (3)
N1C—H1C···N7B^vi	0.86 (6)	2.02 (6)	2.882 (6)	177 (1)
N1D—H1D···N7A^vii	0.86 (6)	1.97 (6)	2.829 (7)	174 (1)
O7′D—H7′D···O6B^vii	0.83 (6)	2.14 (4)	2.802 (8)	137.1 (5)
O2W—H1W2···O7′B^viii	0.82 (5)	2.20 (5)	2.938 (8)	149.5 (5)
O3W—H1W3···O6A^ix	0.85 (5)	2.00 (4)	2.833 (7)	167.2 (4)
O3W—H2W3···O7′D^x	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.