4-Amino­pyridinium 2-(anthracen-9-yl)-3-oxo-3H-inden-1-olate monohydrate

The title compound, 2C₅H₇N₂⁺·2C₂₃H₁₃O₂⁻·H₂O, formed as a by-product in the attempted synthesis of a nonlinear optical candidate mol­ecule, contains two independent 4-amino­pyridinium cations and 2-(anthracen-9-yl)-3-oxo-3H-inden-1-olate anions with one solvent water mol­ecule. This is the first reported structure containing these anions. The two anions are not planar, having different inter­planar angles between the anthracenyl and inden-1-olate moieties of 59.07 (5) and 83.92 (5)°. The crystal packing, which involves strong classical hydrogen bonds and one C—H...π inter­action, appears to account for both the nonplanarity and this difference.

S1. Comment

Organic ionic salts have long been considered as promising materials for use in nonlinear optics (NLO) (Marder et al., 1994). This is because such compounds can exhibit large first-order hyperpolarizabilities (β), can be easily tuned (for example, by changing the counterion), and have high melting points and crystal hardnesses (Yang et al., 2007). By way of example, the crystalline organic salt 4-dimethylamino-N-methyl-4-stilbazolium tosylate (DAST) is a very promising NLO material and has been shown to have a very large NLO susceptibility, with r₁₁ values of 53 pm V^-1 at 1310 nm and 92 pm V^-1 at 720 nm (Pan et al., 1996). In our previous work, we have successfully synthesized a series of ionic chromophores in order to observe the impact on the second-order NLO response of changing the donor group, the polarity of the solvent or the counterion (i.e. tosylate, 2-naphthalene sulfonate and iodide) (Teshome et al., 2010). As part of our ongoing work to develop novel NLO materials, we were interested in preparing a compound containing an electron-rich indanedione acceptor, a dihydroanthracene-azo interconnection and a 1,4-dihydropyridinylidene donor unit [viz. compound (3) in the first scheme].

Our initial attempt to prepare this target molecule by adding 2-anthracen-9-yl-indan-1,3-dione to the diazonium salt of 4-aminopyridine (first scheme) was unsuccessful, as we only recovered the original diketone unchanged. One possible reason for this is the lack of stability of the diazonium salt of 4-aminopyridine, (2), which has been reported to be very unstable (Bunsel & Keum, 1983), so it may have decomposed before reacting with the anthracenyl component. Consequently, we decided to prepare the diazonium salt in situ by dissolving the amine and diketone together at 273–278 K and adding sodium nitrite and hydrochloric acid. This resulted in the rapid appearance of an orange precipitate which, following isolation and characterization, was found to be the title compound, (I), and not the desired diazo intermediate. As a matter of procedure we then resynthesized (I) using the method described in the Experimental section, which involves coupling the sodium salt of 2-anthracen-9-yl-indan-1,3-dione with 4-aminopyridinium chloride.

Only one structure, 1-n-butyl-3-(indan-1,3-dionyl-2)pyridinium [Cambridge Structural Database (CSD, Version 5.32 with November 2010 updates; Allen, 2002) refcode DUCWUT; Magomedova & Bel'skii, 1986], has been reported in which deprotonation of the indan-1,3-dione ring has occurred, but in that case the coordinated pyridinium ring is formally charged, giving overall molecular neutrality. There are 25 structures in the CSD containing the neutral -1H-indene-1,3(2H)-dione entity, for example JOTGII (Kolev et al., 1992), but (I) represents the first report of a unique 3-oxo-3H-inden-1-olate anion coupled with the (more commonly observed) 4-aminopyridinium cation.

A view of the asymmetric unit contents and atom-labelling scheme of (I) is shown in Fig. 1. Along with a single water molecule, there are two independent cations and anions, with the labels of the second matching the first with an appended apostrophe (e.g. C2 and C2'). There are minor differences in bond lengths and angles between the two anions, with examples given in Table 1. The non-hydrogen bond lengths have an r.m.s. fit of 0.0055 Å for the two anions, compared with an r.m.s. fit of 0.0044 Å for the two cations (PLATON; Spek, 2009). As shown in Table 1, the anions have quite different geometries from a typical -1H-indene-1,3(2H)-dione molecule (JOTGII), particularly with respect to the bond lengths of the five-membered ring, but they are somewhat similar to those found in the two independent molecules in the DUCWUT structure. Specifically, the C1—C2 and C2—C3 distances average to shorter distances of 1.420 (14) Å in (I) and 1.429 (5) Å in DUCWUT, compared with 1.526 (4) Å in JOTGII [an average of 1.538 (11) Å was found for these bonds in four similar molecules, SEZKAK (Kumar et al., 2007), CEZCAM (Das et al., 2007) and HOHWIK (Siaka et al., 1998; two symmetry-independent molecules)]. Likewise, the C3—C4 and C1—C9 bonds average to longer values of 1.507 (7) Å in (I) and 1.504 (8) Å in DUCWUT, compared with 1.479 (1) Å for JOTGII. Of all the remaining bond lengths in the anions, including the six-membered ring, only two are significantly different: the average of the C5—C6 and C7–C8 bonds in (I), at 1.404 (3) Å, is slightly longer than its counterparts of 1.391 (13) Å in DUCWUT and 1.377 (6) Å in JOTGII [an average value of 1.375 (8) Å was found in the set of similar structures noted above]. The C6—C7 distances are shorter, at 1.379 (2) and 1.363 (11) Å in (I) and DUCWUT, respectively, compared with 1.395 (4) Å in JOTGII. The geometry of the anthracenyl part of the anion is identical with that reported for 3-(9-anthryl)-1-methoxy-1H-2,3-dihydrobenz(de)anthracene (PAMRIE; Langer & Becker, 1992) and 2-(9-anthryl)-2-propanol (VAFNEV01; Langer & Becker, 1993), except for the connection link (C2—C10) bonds which are single-bond lengths in these compounds. The likely source of these variations in geometry is discussed below.

The individual five- and six-membered rings vary from being statistically planar [e.g. atoms C11–C16, mean out-of-plane distance of the constituent atoms = 0.003 (2) Å; atoms C4'–C9', mean out-of-plane distance = 0.001 (2) Å] to approximately planar [e.g. atoms C1–C4/C9 = 0.026 (2) Å]. Both the 3-oxo-3H-inden-1-olate and anthracyl rings are essentially planar, with average mean out-of-plane distances for both independent anions of 0.013 (2) and 0.038 (2) Å, respectively. The most significant difference between the two anions involves the relative orientations of these anthracenyl and indan-1,3,-dione rings: the interplanar angles are 59.07 (5) and 83.92 (5)° for the anions containing atoms O1 and O1', respectively. Even more significant is the fact that, in the only really comparative structure (DUWCUT), the interplanar angles are much closer to, but not exactly, zero, at 6.1 (2) and 10.4 (2)° for the two independent molecules. Examination of the intermolecular packing (Fig. 2) confirms that these ring orientations allow close hydrogen-bonding contacts between anion and cation acceptors and donors, and a C—H···π interaction. It seems likely that the anion charge here is localized on the 3-oxo-3H-inden-1-olate rings, rather than partially delocalized through both rings as seen in DUCWUT; indeed, this would enhance the acceptor status of the O atoms. This is consistent with the fact that the link bond C2—C10 is significantly shorter in DUCWUT by 0.048 (7) Å, and with the bond-length differences noted above with shorter average C1—C2 and C2—C3 distances.

Over 88 compounds containing the 4-aminopyridinium cation are found in the CSD and those reported here show identical dimensions. For example, the average C24—N30(amino) distance here is 1.332 (2) Å, compared with 1.328 (2) Å in 4-aminopyridinium picrate (KUVLAP; Ramesh et al., 2010).

Overall, the crystal packing of (I) is dominated by strong (classical) hydrogen bonds (Table 2 and Fig. 2), building a three-dimensional matrix based on D(2) primary graph-set motifs (Bernstein et al., 1995) using all amine and water H atoms. These motifs combine to generate three discrete D¹₂(3) secondary motifs which involve bifurcated interactions at the acceptor atoms (e.g. O2, entries 1 and 5 in Table 2) and sets of D²₂(n) motifs, where n = 4, 5, 7, 8 or 9. Thus, the ketone O atoms act as acceptors for both amine and pyridinium donors of the 4-aminopyridinium cation. The single water molecule acts as a hydrogen-bond donor to the two independent anions, and as an acceptor to the amino H atom of one 4-aminopyridinium cation. The alignment of the anthracyl groups permits a significant C—H···π interaction (last entry in Table 2) between two symmetry-independent anions. There are also very weak C—H···O interactions with water atom O5W, which are included in Table 2 for completeness, and other fortuitous weak C—H···π interactions, but no significant π–π interactions.

This packing is in striking contrast with that of the related compound DUCWUT, where lattice binding is provided by C—H···O interactions only, with no C—H···π-type or other interactions involving the pyridinium ring atoms. It is noteworthy that, although the D(2) motif interactions are observed in DUWUT, there are also several intramolecular C—H···O interactions displaying the S(6) motif that are only possible because of the near coplanarity of the adjacent indan-1,3-dionyl and pyridinium rings (dihedral angle ~0°; Table 1, last entry).

The formation of this unexpected product, (I), is considered to be due to the negative charge on the 2-anthracenyl indanedione anion residing predominately across the 1–3 diketone system. Therefore, it is not able to impart the requisite negative charge on to the anthracene unit to make it sufficiently reactive toward the diazonium salt derived from 4-aminopyridine. Consequently, formation of the title salt occurs in preference and the equilibrium of the reaction is presumably driven by precipitation. Alternative synthetic routes are under investigation.

Related literature

For related literature, see: Allen (2002); Bernstein et al. (1995); Bunsel & Keum (1983); Das et al. (2007); Kolev et al. (1992); Kumar et al. (2007); Langer & Becker (1992, 1993); Magomedova & Bel'skii (1986); Marder et al. (1994); Pan et al. (1996); Ramesh et al. (2010); Siaka et al. (1998); Spek (2009); Teshome et al. (2010); Yang et al. (2007).

S2. Experimental

To a cooled solution of 2-anthracen-9-yl-indan-1,3-dione (1.6 g) in distilled water (40 ml) was added KOH (1 g), and the mixture was stirred for 30 min. A solution of 4-aminopyridinium chloride (0.7 g) in distilled water (10 ml) was then added dropwise, whereupon a red solid formed almost immediately. After 10 min, the solid product was collected by filtration, washed with several small portions of distilled water and air-dried to give a red powder. The crude product was purified by recrystallization from ethanol. Crystals of (I) were obtained by dissolving the compound in chloroform–acetone–toluene (4:5:1 v/v) and allowing the solution to evaporate slowly, whereupon dark-red crystals formed [m.p. 491–493 K (decomposition)].

Spectroscopic analysis: ¹H NMR (DMSO-d₆, 500 MHz, δ, p.p.m.): 8.33 (s, 1H), 8.02–7.95 (m, 3H), 7.88 (d, J = 5.0 Hz, 2H), 7.50 (s, 2H), 7.40 (t, 2H), 7.30 (m, 3H), 7.22 (s, 2H), 6.60 (d, J = 5.0 Hz, 2H), 2.04 (s, 2H); ¹³C NMR (DMSO-d₆, 125 MHz, δ, p.p.m.): 188.4, 182.5, 158.4, 141.4, 140.8, 134.6, 133.8, 133.1, 131.4, 130.8, 129.3, 128.9, 127.9, 126.8, 124.7, 123.6, 123.5, 117.1, 108.5, 103.7. Mass spectroscopy, negative mode: found m/z 321.0915; C₂₃H₁₃O₂ requires m/z 321.0916, Δ = 0.3 p.p.m. Positive mode, found m/z 95.0618; C₅H₇N₂ requires m/z 95.0609, Δ = 9.5 p.p.m.

S3. Refinement

Ten reflections affected by the beam stop were omitted from the final refinement. Aromatic ring H atoms were constrained to an ideal geometry, with C—H = 0.95 Å and with U_iso(H) = 1.2U_eq(C). All N-bound H atoms were placed in positions determined from a difference Fourier map and refined freely, with U_iso(H) = 1.2U_eq(N). Water H atoms were located in a difference Fourier map and then refined freely, with U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005) and SADABS (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. The molecular structure and atom-numbering scheme for the asymmetric unit of (I). Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. A partial packing diagram of the unit-cell contents of (I), showing key interactions [contact atoms are shown as balls; see Table 2 (Mercury; Macrae et al., 2008)]. H atoms have been omitted for clarity. [Symmetry codes: (i) x + 1, y, z; (ii) -x + 2, -y + 1, -z + 1; (iii) -x + 1, -y, -z; (iv) x - 1, y, z - 1; (v) x, y, z + 1.]

4-Aminopyridinium 2-(anthracen-9-yl)-3-oxo-3H-inden-1-olate monohydrate

Crystal data

2C5H7N2^+·2C23H13O2^−·H2O	Z = 2
Mr = 850.94	F(000) = 892
Triclinic, P1	Dx = 1.318 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1990 (3) Å	Cell parameters from 9869 reflections
b = 13.9977 (6) Å	θ = 2.3–30.4°
c = 17.9153 (7) Å	µ = 0.09 mm^−1
α = 100.962 (2)°	T = 116 K
β = 97.628 (2)°	Block, red
γ = 105.265 (2)°	0.70 × 0.31 × 0.18 mm
V = 2143.78 (14) Å^3

Data collection

Bruker APEXII CCD diffractometer	7568 independent reflections
Graphite monochromator	6771 reflections with I > 2σ(I)
Detector resolution: 8.333 pixels mm^-1	Rint = 0.036
ϕ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −10→10
Tmin = 0.637, Tmax = 0.746	k = −16→16
41534 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.032P)^2 + 1.1299P] where P = (Fo^2 + 2Fc^2)/3
7568 reflections	(Δ/σ)max < 0.001
610 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.86467 (13)	0.17884 (9)	0.43690 (6)	0.0230 (3)
O2	0.90595 (13)	0.40933 (9)	0.67461 (6)	0.0210 (3)
C1	0.90919 (17)	0.25205 (12)	0.49499 (9)	0.0163 (3)
C2	0.84918 (17)	0.26511 (12)	0.56506 (9)	0.0165 (3)
C3	0.92742 (17)	0.36418 (12)	0.61096 (9)	0.0159 (3)
C4	1.05001 (17)	0.41386 (12)	0.57041 (9)	0.0162 (3)
C5	1.15955 (18)	0.50755 (12)	0.59197 (10)	0.0194 (3)
H5	1.1672	0.5538	0.6396	0.023*
C6	1.25988 (18)	0.53273 (12)	0.54117 (10)	0.0203 (4)
H6	1.3360	0.5972	0.5545	0.024*
C7	1.24922 (18)	0.46518 (13)	0.47231 (10)	0.0206 (4)
H7	1.3185	0.4835	0.4389	0.025*
C8	1.13748 (18)	0.36993 (12)	0.45097 (9)	0.0186 (3)
H8	1.1299	0.3232	0.4036	0.022*
C9	1.03891 (17)	0.34607 (12)	0.50072 (9)	0.0158 (3)
C10	0.72140 (17)	0.18681 (12)	0.58140 (9)	0.0157 (3)
C11	0.58225 (17)	0.20747 (12)	0.59306 (9)	0.0165 (3)
C12	0.55839 (19)	0.30393 (13)	0.59045 (10)	0.0204 (4)
H12	0.6397	0.3569	0.5827	0.024*
C13	0.42200 (19)	0.32161 (13)	0.59880 (10)	0.0243 (4)
H13	0.4096	0.3865	0.5971	0.029*
C14	0.29859 (19)	0.24372 (14)	0.60993 (10)	0.0244 (4)
H14	0.2035	0.2564	0.6152	0.029*
C15	0.31569 (18)	0.15164 (13)	0.61311 (10)	0.0223 (4)
H15	0.2322	0.1004	0.6211	0.027*
C16	0.45660 (18)	0.12929 (12)	0.60478 (9)	0.0181 (3)
C17	0.47146 (18)	0.03300 (12)	0.60415 (9)	0.0198 (3)
H17	0.3872	−0.0188	0.6108	0.024*
C18	0.60729 (18)	0.01093 (12)	0.59402 (9)	0.0181 (3)
C19	0.62289 (19)	−0.08794 (12)	0.59445 (10)	0.0221 (4)
H19	0.5383	−0.1397	0.6009	0.027*
C20	0.7557 (2)	−0.10939 (13)	0.58587 (10)	0.0247 (4)
H20	0.7641	−0.1754	0.5869	0.030*
C21	0.8823 (2)	−0.03319 (13)	0.57540 (10)	0.0222 (4)
H21	0.9755	−0.0485	0.5696	0.027*
C22	0.87214 (18)	0.06147 (13)	0.57359 (9)	0.0189 (3)
H22	0.9585	0.1110	0.5661	0.023*
C23	0.73496 (17)	0.08857 (12)	0.58264 (9)	0.0156 (3)
O1'	0.42132 (13)	0.20381 (9)	0.01015 (7)	0.0245 (3)
O2'	0.04183 (13)	0.34312 (10)	0.09840 (7)	0.0287 (3)
C1'	0.34140 (18)	0.24437 (12)	0.05129 (9)	0.0178 (3)
C2'	0.20833 (18)	0.27011 (12)	0.02745 (9)	0.0183 (3)
C3'	0.15690 (18)	0.31186 (13)	0.09448 (10)	0.0207 (4)
C4'	0.26892 (18)	0.31249 (13)	0.16478 (9)	0.0201 (4)
C5'	0.2737 (2)	0.34343 (15)	0.24305 (10)	0.0305 (4)
H5'	0.1984	0.3716	0.2616	0.037*
C6'	0.3936 (2)	0.33191 (15)	0.29439 (10)	0.0301 (4)
H6'	0.3994	0.3528	0.3486	0.036*
C7'	0.50317 (19)	0.29089 (14)	0.26773 (10)	0.0250 (4)
H7'	0.5830	0.2836	0.3037	0.030*
C8'	0.49766 (19)	0.25991 (13)	0.18811 (10)	0.0220 (4)
H8'	0.5730	0.2319	0.1692	0.026*
C9'	0.37980 (17)	0.27128 (12)	0.13811 (9)	0.0176 (3)
C10'	0.14152 (18)	0.25457 (12)	−0.05583 (9)	0.0184 (3)
C11'	0.02273 (19)	0.16579 (13)	−0.09512 (9)	0.0207 (4)
C12'	−0.0475 (2)	0.09019 (14)	−0.05684 (10)	0.0274 (4)
H12'	−0.0156	0.1004	−0.0025	0.033*
C13'	−0.1591 (2)	0.00397 (15)	−0.09666 (11)	0.0369 (5)
H13'	−0.2032	−0.0454	−0.0699	0.044*
C14'	−0.2108 (2)	−0.01330 (16)	−0.17746 (12)	0.0431 (5)
H14'	−0.2894	−0.0737	−0.2045	0.052*
C15'	−0.1482 (2)	0.05620 (15)	−0.21624 (11)	0.0365 (5)
H15'	−0.1839	0.0439	−0.2704	0.044*
C16'	−0.0298 (2)	0.14744 (13)	−0.17748 (10)	0.0245 (4)
C17'	0.0395 (2)	0.21682 (13)	−0.21767 (10)	0.0240 (4)
H17'	0.0066	0.2033	−0.2722	0.029*
C18'	0.15583 (19)	0.30550 (13)	−0.18000 (10)	0.0205 (4)
C19'	0.2229 (2)	0.37928 (14)	−0.22081 (10)	0.0246 (4)
H19'	0.1937	0.3649	−0.2756	0.030*
C20'	0.3271 (2)	0.46902 (14)	−0.18280 (11)	0.0295 (4)
H20'	0.3713	0.5166	−0.2109	0.035*
C21'	0.3704 (2)	0.49196 (14)	−0.10113 (11)	0.0310 (4)
H21'	0.4404	0.5563	−0.0746	0.037*
C22'	0.31302 (19)	0.42310 (13)	−0.06011 (11)	0.0254 (4)
H22'	0.3455	0.4397	−0.0054	0.030*
C23'	0.20500 (18)	0.32634 (13)	−0.09751 (10)	0.0195 (3)
O5W	0.92879 (15)	0.39664 (10)	0.23334 (8)	0.0275 (3)
H5W1	0.974 (2)	0.3872 (17)	0.1918 (14)	0.041*
H5W2	0.980 (3)	0.4554 (18)	0.2632 (13)	0.041*
C24	0.73817 (19)	0.32855 (13)	0.93506 (10)	0.0232 (4)
C25	0.87778 (19)	0.38332 (13)	0.91918 (10)	0.0243 (4)
H25	0.9676	0.4082	0.9586	0.029*
C26	0.8840 (2)	0.40052 (14)	0.84769 (11)	0.0262 (4)
H26	0.9793	0.4364	0.8373	0.031*
N27	0.75841 (18)	0.36803 (12)	0.79094 (9)	0.0288 (4)
H27	0.773 (2)	0.3759 (15)	0.7438 (13)	0.035*
C28	0.6201 (2)	0.32122 (16)	0.80525 (11)	0.0337 (4)
H28	0.5314	0.3013	0.7654	0.040*
C29	0.6067 (2)	0.30236 (15)	0.87608 (11)	0.0308 (4)
H29	0.5084	0.2714	0.8860	0.037*
N30	0.73216 (19)	0.30329 (13)	1.00307 (9)	0.0299 (4)
H30A	0.821 (2)	0.3192 (16)	1.0385 (13)	0.036*
H30B	0.641 (2)	0.2692 (16)	1.0137 (12)	0.036*
C24'	0.82090 (19)	0.12900 (13)	0.23086 (10)	0.0232 (4)
C25'	0.7987 (2)	0.13074 (14)	0.15164 (10)	0.0287 (4)
H25'	0.8261	0.1937	0.1368	0.034*
C26'	0.7380 (2)	0.04225 (15)	0.09695 (11)	0.0324 (4)
H26'	0.7218	0.0442	0.0439	0.039*
N27'	0.70022 (19)	−0.04846 (13)	0.11595 (10)	0.0330 (4)
H27'	0.661 (2)	−0.1065 (17)	0.0772 (13)	0.040*
C28'	0.7259 (2)	−0.05313 (15)	0.19079 (12)	0.0351 (5)
H28'	0.7026	−0.1177	0.2034	0.042*
C29'	0.7842 (2)	0.03232 (14)	0.24836 (11)	0.0303 (4)
H29'	0.8005	0.0273	0.3008	0.036*
N30'	0.87372 (19)	0.21402 (12)	0.28657 (9)	0.0294 (4)
H31'	0.896 (2)	0.2761 (17)	0.2731 (12)	0.035*
H32'	0.880 (2)	0.2079 (16)	0.3372 (13)	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0296 (6)	0.0190 (6)	0.0165 (6)	0.0024 (5)	0.0055 (5)	0.0014 (5)
O2	0.0237 (6)	0.0209 (6)	0.0152 (6)	0.0025 (5)	0.0070 (5)	0.0004 (5)
C1	0.0183 (8)	0.0153 (8)	0.0155 (8)	0.0061 (6)	0.0020 (6)	0.0036 (7)
C2	0.0164 (8)	0.0167 (8)	0.0167 (8)	0.0048 (6)	0.0026 (6)	0.0054 (6)
C3	0.0156 (8)	0.0186 (8)	0.0143 (8)	0.0057 (6)	0.0017 (6)	0.0057 (7)
C4	0.0159 (8)	0.0176 (8)	0.0170 (8)	0.0065 (6)	0.0033 (6)	0.0068 (7)
C5	0.0196 (8)	0.0174 (8)	0.0194 (9)	0.0041 (7)	0.0041 (7)	0.0016 (7)
C6	0.0179 (8)	0.0168 (8)	0.0253 (9)	0.0017 (6)	0.0047 (7)	0.0074 (7)
C7	0.0197 (8)	0.0222 (9)	0.0251 (9)	0.0076 (7)	0.0108 (7)	0.0114 (7)
C8	0.0227 (8)	0.0190 (8)	0.0172 (8)	0.0093 (7)	0.0071 (7)	0.0052 (7)
C9	0.0156 (7)	0.0170 (8)	0.0158 (8)	0.0057 (6)	0.0023 (6)	0.0056 (6)
C10	0.0172 (8)	0.0170 (8)	0.0105 (8)	0.0022 (6)	0.0016 (6)	0.0021 (6)
C11	0.0183 (8)	0.0183 (8)	0.0105 (8)	0.0035 (6)	0.0010 (6)	0.0019 (6)
C12	0.0210 (8)	0.0192 (9)	0.0202 (9)	0.0044 (7)	0.0030 (7)	0.0054 (7)
C13	0.0280 (9)	0.0215 (9)	0.0250 (9)	0.0111 (7)	0.0032 (7)	0.0051 (7)
C14	0.0189 (8)	0.0313 (10)	0.0245 (9)	0.0113 (7)	0.0046 (7)	0.0042 (8)
C15	0.0169 (8)	0.0281 (10)	0.0196 (9)	0.0025 (7)	0.0037 (7)	0.0053 (7)
C16	0.0179 (8)	0.0215 (9)	0.0137 (8)	0.0036 (7)	0.0023 (6)	0.0052 (7)
C17	0.0188 (8)	0.0193 (9)	0.0183 (8)	−0.0007 (7)	0.0041 (6)	0.0056 (7)
C18	0.0212 (8)	0.0169 (8)	0.0132 (8)	0.0026 (7)	0.0013 (6)	0.0023 (6)
C19	0.0267 (9)	0.0160 (8)	0.0198 (9)	0.0008 (7)	0.0025 (7)	0.0040 (7)
C20	0.0355 (10)	0.0173 (9)	0.0219 (9)	0.0108 (7)	0.0031 (7)	0.0036 (7)
C21	0.0269 (9)	0.0243 (9)	0.0176 (9)	0.0127 (7)	0.0045 (7)	0.0031 (7)
C22	0.0196 (8)	0.0214 (9)	0.0148 (8)	0.0050 (7)	0.0040 (6)	0.0035 (7)
C23	0.0187 (8)	0.0166 (8)	0.0093 (8)	0.0033 (6)	0.0007 (6)	0.0017 (6)
O1'	0.0224 (6)	0.0305 (7)	0.0186 (6)	0.0077 (5)	0.0063 (5)	−0.0005 (5)
O2'	0.0264 (7)	0.0434 (8)	0.0180 (6)	0.0180 (6)	0.0023 (5)	0.0022 (6)
C1'	0.0192 (8)	0.0130 (8)	0.0167 (8)	−0.0020 (6)	0.0042 (6)	0.0017 (6)
C2'	0.0184 (8)	0.0185 (8)	0.0155 (8)	0.0016 (6)	0.0029 (6)	0.0035 (7)
C3'	0.0202 (8)	0.0216 (9)	0.0177 (9)	0.0034 (7)	0.0026 (7)	0.0033 (7)
C4'	0.0194 (8)	0.0224 (9)	0.0159 (8)	0.0036 (7)	0.0025 (6)	0.0028 (7)
C5'	0.0270 (9)	0.0465 (12)	0.0186 (9)	0.0153 (9)	0.0045 (7)	0.0028 (8)
C6'	0.0286 (9)	0.0451 (12)	0.0129 (9)	0.0096 (8)	0.0018 (7)	0.0016 (8)
C7'	0.0219 (9)	0.0290 (10)	0.0200 (9)	0.0046 (7)	−0.0031 (7)	0.0049 (7)
C8'	0.0200 (8)	0.0212 (9)	0.0232 (9)	0.0043 (7)	0.0035 (7)	0.0044 (7)
C9'	0.0165 (8)	0.0146 (8)	0.0172 (8)	−0.0018 (6)	0.0029 (6)	0.0021 (6)
C10'	0.0192 (8)	0.0212 (9)	0.0145 (8)	0.0069 (7)	0.0032 (6)	0.0022 (7)
C11'	0.0230 (8)	0.0219 (9)	0.0162 (9)	0.0057 (7)	0.0042 (7)	0.0030 (7)
C12'	0.0333 (10)	0.0273 (10)	0.0167 (9)	0.0022 (8)	0.0039 (7)	0.0041 (7)
C13'	0.0476 (12)	0.0255 (10)	0.0271 (11)	−0.0074 (9)	0.0061 (9)	0.0076 (8)
C14'	0.0490 (13)	0.0324 (11)	0.0260 (11)	−0.0151 (9)	−0.0035 (9)	0.0006 (9)
C15'	0.0449 (12)	0.0333 (11)	0.0173 (10)	−0.0048 (9)	−0.0025 (8)	0.0021 (8)
C16'	0.0273 (9)	0.0247 (9)	0.0171 (9)	0.0032 (7)	0.0016 (7)	0.0029 (7)
C17'	0.0297 (9)	0.0262 (9)	0.0127 (8)	0.0057 (7)	0.0010 (7)	0.0021 (7)
C18'	0.0224 (8)	0.0224 (9)	0.0189 (9)	0.0096 (7)	0.0055 (7)	0.0052 (7)
C19'	0.0287 (9)	0.0301 (10)	0.0188 (9)	0.0113 (8)	0.0071 (7)	0.0091 (8)
C20'	0.0289 (10)	0.0282 (10)	0.0338 (11)	0.0053 (8)	0.0093 (8)	0.0154 (8)
C21'	0.0281 (10)	0.0244 (10)	0.0342 (11)	−0.0011 (8)	0.0018 (8)	0.0073 (8)
C22'	0.0228 (9)	0.0254 (10)	0.0231 (9)	0.0027 (7)	−0.0001 (7)	0.0034 (7)
C23'	0.0176 (8)	0.0221 (9)	0.0196 (9)	0.0074 (7)	0.0039 (6)	0.0044 (7)
O5W	0.0327 (7)	0.0208 (7)	0.0273 (7)	0.0049 (6)	0.0114 (6)	0.0016 (6)
C24	0.0246 (9)	0.0270 (9)	0.0203 (9)	0.0109 (7)	0.0074 (7)	0.0047 (7)
C25	0.0209 (8)	0.0247 (9)	0.0273 (10)	0.0073 (7)	0.0060 (7)	0.0047 (8)
C26	0.0250 (9)	0.0251 (10)	0.0335 (11)	0.0102 (7)	0.0133 (8)	0.0095 (8)
N27	0.0351 (9)	0.0347 (9)	0.0207 (8)	0.0109 (7)	0.0130 (7)	0.0101 (7)
C28	0.0295 (10)	0.0440 (12)	0.0244 (10)	0.0062 (9)	0.0032 (8)	0.0086 (9)
C29	0.0228 (9)	0.0434 (12)	0.0244 (10)	0.0041 (8)	0.0072 (7)	0.0098 (9)
N30	0.0234 (8)	0.0455 (10)	0.0207 (8)	0.0071 (7)	0.0040 (7)	0.0121 (7)
C24'	0.0245 (9)	0.0236 (9)	0.0213 (9)	0.0066 (7)	0.0069 (7)	0.0042 (7)
C25'	0.0357 (10)	0.0282 (10)	0.0216 (10)	0.0071 (8)	0.0076 (8)	0.0066 (8)
C26'	0.0356 (10)	0.0397 (12)	0.0205 (10)	0.0097 (9)	0.0087 (8)	0.0033 (8)
N27'	0.0368 (9)	0.0291 (9)	0.0269 (9)	0.0083 (7)	0.0054 (7)	−0.0057 (7)
C28'	0.0451 (12)	0.0245 (10)	0.0336 (11)	0.0087 (9)	0.0064 (9)	0.0051 (8)
C29'	0.0406 (11)	0.0285 (10)	0.0213 (10)	0.0099 (8)	0.0044 (8)	0.0060 (8)
N30'	0.0438 (10)	0.0225 (8)	0.0184 (8)	0.0044 (7)	0.0067 (7)	0.0035 (7)

Geometric parameters (Å, º)

O1—C1	1.2494 (19)	C8'—C9'	1.375 (2)
O2—C3	1.2610 (19)	C8'—H8'	0.9500
C1—C2	1.437 (2)	C10'—C11'	1.408 (2)
C1—C9	1.502 (2)	C10'—C23'	1.414 (2)
C2—C3	1.414 (2)	C11'—C12'	1.429 (2)
C2—C10	1.485 (2)	C11'—C16'	1.441 (2)
C3—C4	1.510 (2)	C12'—C13'	1.358 (3)
C4—C5	1.376 (2)	C12'—H12'	0.9500
C4—C9	1.391 (2)	C13'—C14'	1.415 (3)
C5—C6	1.406 (2)	C13'—H13'	0.9500
C5—H5	0.9500	C14'—C15'	1.352 (3)
C6—C7	1.379 (2)	C14'—H14'	0.9500
C6—H6	0.9500	C15'—C16'	1.424 (2)
C7—C8	1.400 (2)	C15'—H15'	0.9500
C7—H7	0.9500	C16'—C17'	1.389 (2)
C8—C9	1.377 (2)	C17'—C18'	1.390 (2)
C8—H8	0.9500	C17'—H17'	0.9500
C10—C23	1.417 (2)	C18'—C19'	1.433 (2)
C10—C11	1.417 (2)	C18'—C23'	1.436 (2)
C11—C12	1.432 (2)	C19'—C20'	1.352 (3)
C11—C16	1.436 (2)	C19'—H19'	0.9500
C12—C13	1.363 (2)	C20'—C21'	1.415 (3)
C12—H12	0.9500	C20'—H20'	0.9500
C13—C14	1.417 (2)	C21'—C22'	1.361 (3)
C13—H13	0.9500	C21'—H21'	0.9500
C14—C15	1.350 (2)	C22'—C23'	1.428 (2)
C14—H14	0.9500	C22'—H22'	0.9500
C15—C16	1.431 (2)	O5W—H5W1	0.90 (2)
C15—H15	0.9500	O5W—H5W2	0.86 (2)
C16—C17	1.388 (2)	C24—N30	1.336 (2)
C17—C18	1.390 (2)	C24—C25	1.407 (2)
C17—H17	0.9500	C24—C29	1.412 (2)
C18—C19	1.430 (2)	C25—C26	1.353 (3)
C18—C23	1.441 (2)	C25—H25	0.9500
C19—C20	1.354 (2)	C26—N27	1.345 (2)
C19—H19	0.9500	C26—H26	0.9500
C20—C21	1.417 (2)	N27—C28	1.351 (2)
C20—H20	0.9500	N27—H27	0.89 (2)
C21—C22	1.359 (2)	C28—C29	1.359 (3)
C21—H21	0.9500	C28—H28	0.9500
C22—C23	1.430 (2)	C29—H29	0.9500
C22—H22	0.9500	N30—H30A	0.91 (2)
O1'—C1'	1.2691 (19)	N30—H30B	0.91 (2)
O2'—C3'	1.252 (2)	C24'—N30'	1.328 (2)
C1'—C2'	1.401 (2)	C24'—C29'	1.412 (3)
C1'—C9'	1.499 (2)	C24'—C25'	1.413 (2)
C2'—C3'	1.427 (2)	C25'—C26'	1.355 (3)
C2'—C10'	1.488 (2)	C25'—H25'	0.9500
C3'—C4'	1.515 (2)	C26'—N27'	1.346 (3)
C4'—C5'	1.378 (2)	C26'—H26'	0.9500
C4'—C9'	1.391 (2)	N27'—C28'	1.347 (3)
C5'—C6'	1.403 (3)	N27'—H27'	0.91 (2)
C5'—H5'	0.9500	C28'—C29'	1.352 (3)
C6'—C7'	1.379 (3)	C28'—H28'	0.9500
C6'—H6'	0.9500	C29'—H29'	0.9500
C7'—C8'	1.400 (2)	N30'—H31'	0.92 (2)
C7'—H7'	0.9500	N30'—H32'	0.92 (2)
O1—C1—C2	128.78 (15)	C9'—C8'—H8'	121.1
O1—C1—C9	123.27 (14)	C7'—C8'—H8'	121.1
C2—C1—C9	107.93 (13)	C8'—C9'—C4'	121.82 (15)
C3—C2—C1	108.24 (13)	C8'—C9'—C1'	130.58 (15)
C3—C2—C10	128.04 (14)	C4'—C9'—C1'	107.60 (14)
C1—C2—C10	123.66 (14)	C11'—C10'—C23'	119.38 (15)
O2—C3—C2	129.61 (15)	C11'—C10'—C2'	120.81 (15)
O2—C3—C4	122.26 (14)	C23'—C10'—C2'	119.67 (14)
C2—C3—C4	108.12 (13)	C10'—C11'—C12'	122.54 (15)
C5—C4—C9	121.13 (15)	C10'—C11'—C16'	119.90 (15)
C5—C4—C3	131.02 (15)	C12'—C11'—C16'	117.54 (15)
C9—C4—C3	107.85 (13)	C13'—C12'—C11'	121.22 (17)
C4—C5—C6	117.85 (15)	C13'—C12'—H12'	119.4
C4—C5—H5	121.1	C11'—C12'—H12'	119.4
C6—C5—H5	121.1	C12'—C13'—C14'	120.94 (18)
C7—C6—C5	120.92 (15)	C12'—C13'—H13'	119.5
C7—C6—H6	119.5	C14'—C13'—H13'	119.5
C5—C6—H6	119.5	C15'—C14'—C13'	120.04 (17)
C6—C7—C8	120.78 (15)	C15'—C14'—H14'	120.0
C6—C7—H7	119.6	C13'—C14'—H14'	120.0
C8—C7—H7	119.6	C14'—C15'—C16'	121.35 (18)
C9—C8—C7	118.00 (15)	C14'—C15'—H15'	119.3
C9—C8—H8	121.0	C16'—C15'—H15'	119.3
C7—C8—H8	121.0	C17'—C16'—C15'	121.49 (16)
C8—C9—C4	121.32 (15)	C17'—C16'—C11'	119.55 (15)
C8—C9—C1	130.98 (15)	C15'—C16'—C11'	118.91 (16)
C4—C9—C1	107.70 (13)	C16'—C17'—C18'	121.55 (16)
C23—C10—C11	118.94 (14)	C16'—C17'—H17'	119.2
C23—C10—C2	120.17 (14)	C18'—C17'—H17'	119.2
C11—C10—C2	120.84 (14)	C17'—C18'—C19'	121.65 (16)
C10—C11—C12	122.17 (14)	C17'—C18'—C23'	119.30 (15)
C10—C11—C16	120.26 (14)	C19'—C18'—C23'	118.98 (15)
C12—C11—C16	117.53 (14)	C20'—C19'—C18'	121.23 (17)
C13—C12—C11	121.62 (16)	C20'—C19'—H19'	119.4
C13—C12—H12	119.2	C18'—C19'—H19'	119.4
C11—C12—H12	119.2	C19'—C20'—C21'	119.95 (17)
C12—C13—C14	120.34 (16)	C19'—C20'—H20'	120.0
C12—C13—H13	119.8	C21'—C20'—H20'	120.0
C14—C13—H13	119.8	C22'—C21'—C20'	120.89 (17)
C15—C14—C13	120.24 (15)	C22'—C21'—H21'	119.6
C15—C14—H14	119.9	C20'—C21'—H21'	119.6
C13—C14—H14	119.9	C21'—C22'—C23'	121.42 (17)
C14—C15—C16	121.58 (16)	C21'—C22'—H22'	119.3
C14—C15—H15	119.2	C23'—C22'—H22'	119.3
C16—C15—H15	119.2	C10'—C23'—C22'	122.33 (15)
C17—C16—C15	121.49 (15)	C10'—C23'—C18'	120.19 (15)
C17—C16—C11	119.76 (14)	C22'—C23'—C18'	117.41 (15)
C15—C16—C11	118.68 (15)	H5W1—O5W—H5W2	108 (2)
C16—C17—C18	121.28 (15)	N30—C24—C25	120.88 (16)
C16—C17—H17	119.4	N30—C24—C29	122.28 (16)
C18—C17—H17	119.4	C25—C24—C29	116.84 (16)
C17—C18—C19	121.13 (15)	C26—C25—C24	119.91 (16)
C17—C18—C23	119.76 (15)	C26—C25—H25	120.0
C19—C18—C23	119.11 (14)	C24—C25—H25	120.0
C20—C19—C18	121.38 (16)	N27—C26—C25	121.60 (16)
C20—C19—H19	119.3	N27—C26—H26	119.2
C18—C19—H19	119.3	C25—C26—H26	119.2
C19—C20—C21	119.86 (16)	C26—N27—C28	120.34 (16)
C19—C20—H20	120.1	C26—N27—H27	116.9 (13)
C21—C20—H20	120.1	C28—N27—H27	122.7 (13)
C22—C21—C20	120.81 (15)	N27—C28—C29	120.62 (18)
C22—C21—H21	119.6	N27—C28—H28	119.7
C20—C21—H21	119.6	C29—C28—H28	119.7
C21—C22—C23	121.77 (15)	C28—C29—C24	120.33 (17)
C21—C22—H22	119.1	C28—C29—H29	119.8
C23—C22—H22	119.1	C24—C29—H29	119.8
C10—C23—C22	122.97 (14)	C24—N30—H30A	119.2 (13)
C10—C23—C18	119.98 (14)	C24—N30—H30B	120.7 (13)
C22—C23—C18	117.05 (14)	H30A—N30—H30B	120.1 (19)
O1'—C1'—C2'	128.88 (15)	N30'—C24'—C29'	121.25 (17)
O1'—C1'—C9'	122.32 (14)	N30'—C24'—C25'	121.88 (17)
C2'—C1'—C9'	108.79 (14)	C29'—C24'—C25'	116.87 (16)
C1'—C2'—C3'	108.77 (14)	C26'—C25'—C24'	119.77 (18)
C1'—C2'—C10'	122.07 (14)	C26'—C25'—H25'	120.1
C3'—C2'—C10'	129.16 (14)	C24'—C25'—H25'	120.1
O2'—C3'—C2'	128.94 (15)	N27'—C26'—C25'	121.65 (18)
O2'—C3'—C4'	123.68 (15)	N27'—C26'—H26'	119.2
C2'—C3'—C4'	107.37 (14)	C25'—C26'—H26'	119.2
C5'—C4'—C9'	120.67 (15)	C26'—N27'—C28'	120.10 (17)
C5'—C4'—C3'	131.86 (15)	C26'—N27'—H27'	118.9 (14)
C9'—C4'—C3'	107.46 (14)	C28'—N27'—H27'	120.9 (14)
C4'—C5'—C6'	117.80 (16)	N27'—C28'—C29'	121.29 (18)
C4'—C5'—H5'	121.1	N27'—C28'—H28'	119.4
C6'—C5'—H5'	121.1	C29'—C28'—H28'	119.4
C7'—C6'—C5'	121.35 (16)	C28'—C29'—C24'	120.23 (18)
C7'—C6'—H6'	119.3	C28'—C29'—H29'	119.9
C5'—C6'—H6'	119.3	C24'—C29'—H29'	119.9
C6'—C7'—C8'	120.48 (16)	C24'—N30'—H31'	119.0 (13)
C6'—C7'—H7'	119.8	C24'—N30'—H32'	117.7 (13)
C8'—C7'—H7'	119.8	H31'—N30'—H32'	123.1 (18)
C9'—C8'—C7'	117.88 (16)
O1—C1—C2—C3	−174.50 (15)	O2'—C3'—C4'—C5'	0.4 (3)
C9—C1—C2—C3	3.94 (17)	C2'—C3'—C4'—C5'	−179.40 (19)
O1—C1—C2—C10	2.8 (3)	O2'—C3'—C4'—C9'	179.25 (16)
C9—C1—C2—C10	−178.73 (14)	C2'—C3'—C4'—C9'	−0.55 (18)
C1—C2—C3—O2	175.76 (16)	C9'—C4'—C5'—C6'	0.0 (3)
C10—C2—C3—O2	−1.4 (3)	C3'—C4'—C5'—C6'	178.71 (18)
C1—C2—C3—C4	−3.81 (17)	C4'—C5'—C6'—C7'	−0.1 (3)
C10—C2—C3—C4	179.01 (14)	C5'—C6'—C7'—C8'	0.3 (3)
O2—C3—C4—C5	2.9 (3)	C6'—C7'—C8'—C9'	−0.3 (3)
C2—C3—C4—C5	−177.46 (16)	C7'—C8'—C9'—C4'	0.3 (2)
O2—C3—C4—C9	−177.38 (14)	C7'—C8'—C9'—C1'	−178.94 (16)
C2—C3—C4—C9	2.23 (17)	C5'—C4'—C9'—C8'	−0.1 (3)
C9—C4—C5—C6	0.1 (2)	C3'—C4'—C9'—C8'	−179.09 (15)
C3—C4—C5—C6	179.79 (15)	C5'—C4'—C9'—C1'	179.27 (16)
C4—C5—C6—C7	−0.5 (2)	C3'—C4'—C9'—C1'	0.27 (17)
C5—C6—C7—C8	0.4 (2)	O1'—C1'—C9'—C8'	0.2 (3)
C6—C7—C8—C9	0.1 (2)	C2'—C1'—C9'—C8'	179.38 (16)
C7—C8—C9—C4	−0.4 (2)	O1'—C1'—C9'—C4'	−179.10 (15)
C7—C8—C9—C1	−179.93 (15)	C2'—C1'—C9'—C4'	0.11 (18)
C5—C4—C9—C8	0.3 (2)	C1'—C2'—C10'—C11'	95.13 (19)
C3—C4—C9—C8	−179.39 (14)	C3'—C2'—C10'—C11'	−85.7 (2)
C5—C4—C9—C1	179.93 (14)	C1'—C2'—C10'—C23'	−80.5 (2)
C3—C4—C9—C1	0.20 (16)	C3'—C2'—C10'—C23'	98.7 (2)
O1—C1—C9—C8	−4.5 (3)	C23'—C10'—C11'—C12'	−179.66 (16)
C2—C1—C9—C8	177.01 (16)	C2'—C10'—C11'—C12'	4.7 (2)
O1—C1—C9—C4	176.01 (14)	C23'—C10'—C11'—C16'	1.8 (2)
C2—C1—C9—C4	−2.53 (17)	C2'—C10'—C11'—C16'	−173.79 (15)
C3—C2—C10—C23	−124.32 (17)	C10'—C11'—C12'—C13'	−178.22 (18)
C1—C2—C10—C23	58.9 (2)	C16'—C11'—C12'—C13'	0.3 (3)
C3—C2—C10—C11	58.1 (2)	C11'—C12'—C13'—C14'	−0.7 (3)
C1—C2—C10—C11	−118.71 (17)	C12'—C13'—C14'—C15'	0.4 (4)
C23—C10—C11—C12	−178.22 (14)	C13'—C14'—C15'—C16'	0.2 (4)
C2—C10—C11—C12	−0.6 (2)	C14'—C15'—C16'—C17'	177.1 (2)
C23—C10—C11—C16	−0.9 (2)	C14'—C15'—C16'—C11'	−0.5 (3)
C2—C10—C11—C16	176.73 (14)	C10'—C11'—C16'—C17'	1.2 (3)
C10—C11—C12—C13	177.44 (16)	C12'—C11'—C16'—C17'	−177.38 (16)
C16—C11—C12—C13	0.1 (2)	C10'—C11'—C16'—C15'	178.87 (17)
C11—C12—C13—C14	−0.4 (3)	C12'—C11'—C16'—C15'	0.3 (3)
C12—C13—C14—C15	0.7 (3)	C15'—C16'—C17'—C18'	−179.51 (18)
C13—C14—C15—C16	−0.6 (3)	C11'—C16'—C17'—C18'	−1.9 (3)
C14—C15—C16—C17	−176.69 (16)	C16'—C17'—C18'—C19'	−177.28 (16)
C14—C15—C16—C11	0.2 (2)	C16'—C17'—C18'—C23'	−0.4 (3)
C10—C11—C16—C17	−0.4 (2)	C17'—C18'—C19'—C20'	174.59 (17)
C12—C11—C16—C17	177.01 (15)	C23'—C18'—C19'—C20'	−2.3 (2)
C10—C11—C16—C15	−177.41 (14)	C18'—C19'—C20'—C21'	−0.8 (3)
C12—C11—C16—C15	0.0 (2)	C19'—C20'—C21'—C22'	2.6 (3)
C15—C16—C17—C18	178.30 (15)	C20'—C21'—C22'—C23'	−1.4 (3)
C11—C16—C17—C18	1.4 (2)	C11'—C10'—C23'—C22'	172.70 (15)
C16—C17—C18—C19	179.14 (15)	C2'—C10'—C23'—C22'	−11.7 (2)
C16—C17—C18—C23	−1.0 (2)	C11'—C10'—C23'—C18'	−4.2 (2)
C17—C18—C19—C20	−178.91 (16)	C2'—C10'—C23'—C18'	171.49 (14)
C23—C18—C19—C20	1.2 (2)	C21'—C22'—C23'—C10'	−178.62 (17)
C18—C19—C20—C21	−0.7 (3)	C21'—C22'—C23'—C18'	−1.7 (2)
C19—C20—C21—C22	−0.2 (3)	C17'—C18'—C23'—C10'	3.5 (2)
C20—C21—C22—C23	0.5 (2)	C19'—C18'—C23'—C10'	−179.55 (15)
C11—C10—C23—C22	−178.23 (14)	C17'—C18'—C23'—C22'	−173.52 (15)
C2—C10—C23—C22	4.1 (2)	C19'—C18'—C23'—C22'	3.4 (2)
C11—C10—C23—C18	1.3 (2)	N30—C24—C25—C26	174.32 (17)
C2—C10—C23—C18	−176.36 (14)	C29—C24—C25—C26	−5.8 (3)
C21—C22—C23—C10	179.66 (15)	C24—C25—C26—N27	1.2 (3)
C21—C22—C23—C18	0.1 (2)	C25—C26—N27—C28	3.2 (3)
C17—C18—C23—C10	−0.3 (2)	C26—N27—C28—C29	−2.8 (3)
C19—C18—C23—C10	179.50 (15)	N27—C28—C29—C24	−2.1 (3)
C17—C18—C23—C22	179.19 (14)	N30—C24—C29—C28	−173.90 (19)
C19—C18—C23—C22	−1.0 (2)	C25—C24—C29—C28	6.2 (3)
O1'—C1'—C2'—C3'	178.68 (16)	N30'—C24'—C25'—C26'	−177.03 (18)
C9'—C1'—C2'—C3'	−0.46 (18)	C29'—C24'—C25'—C26'	2.9 (3)
O1'—C1'—C2'—C10'	−2.0 (3)	C24'—C25'—C26'—N27'	−1.1 (3)
C9'—C1'—C2'—C10'	178.87 (14)	C25'—C26'—N27'—C28'	−1.7 (3)
C1'—C2'—C3'—O2'	−179.17 (17)	C26'—N27'—C28'—C29'	2.5 (3)
C10'—C2'—C3'—O2'	1.6 (3)	N27'—C28'—C29'—C24'	−0.6 (3)
C1'—C2'—C3'—C4'	0.62 (18)	N30'—C24'—C29'—C28'	177.86 (18)
C10'—C2'—C3'—C4'	−178.66 (15)	C25'—C24'—C29'—C28'	−2.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5W—H5W1···O2′^i	0.90 (2)	1.91 (2)	2.8064 (19)	169 (2)
O5W—H5W2···O2^ii	0.86 (2)	1.94 (2)	2.8043 (18)	177 (2)
N27—H27···O2	0.90 (2)	1.89 (2)	2.705 (2)	150.4 (18)
N27′—H27′···O1′^iii	0.92 (2)	1.79 (2)	2.695 (2)	169 (2)
N30—H30A···O2′^iv	0.91 (2)	2.08 (2)	2.975 (2)	167.5 (19)
N30—H30B···O1′^v	0.91 (2)	1.97 (2)	2.863 (2)	164.3 (19)
N30′—H31′···O5W	0.92 (2)	1.92 (2)	2.842 (2)	173 (2)
N30′—H32′···O1	0.92 (2)	1.92 (2)	2.8364 (19)	171 (2)
C5—H5···O5W^ii	0.95	2.59	3.451 (2)	151
C5′—H5′···O5W^vi	0.95	2.59	3.435 (2)	148
C15′—H15′···Cg1^vii	0.95	2.51	3.452 (2)	170

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