`Segmented' crystals solved using synchrotron radiation: (2S,3R,4S,5R)-4-(10,10-dimethyl-3,3-dioxo-3[lambda]⁶-thia-4-aza­tricyclo­[5.2.1.0^1,5]decan-4-yl­carbonyl)-2,6-diphenyl­per­hydro­pyrrolo[3,4-c]pyrrole-1,3-dione

The title compound, C₂₉H₃₁N₃O₅S, forms needle-shaped `segmented' crystals, thereby inhibiting successful single-crystal data collection using conventional laboratory facilities. One crystallite of dimensions 0.15 × 0.03 × 0.01 mm yielded sufficent single-crystal diffraction data on the Australian Synchrotron PX1 beamline. The two independent mol­ecules in the asymmetric unit are nearly superimposable and show only minor conformational deviations from closely related compounds. The mol­ecules pack using one N-H...O hydrogen bond and several phenyl C-H...O(=S), phenyl C-H...O(=C) and methyl­ene C-H...O(=C) hydrogen bonds and weak C-H...[pi] inter­actions.

S1. Comment

The title compound, (I), originated from a continuing research programme designed to explore preparative routes to chiral pyrrolidine scaffolds. The previously used synthetic route to (I) was employed (Gainsford et al., 2009), with the 1,3-dipolar cycloaddition carried out with N-phenyl maleimide and benzaldehyde in the presence of silver acetate. This structural study was undertaken to confirm the stereochemistry. Two conventional laboratory data collections failed, possibly because of the crystal morphology: single acicular crystals are almost invariably multiple crystals, `segmented' along the needle axis. Eventually, a fragment 0.15 × 0.03 × 0.01 mm in size was obtained that proved to be a single-crystal, and data were collected from it using the Australian Synchrotron PX1 beamline (McPhillips et al., 2002). The known absolute configuration of the independent molecules was confirmed by the observed X-ray anomalous dispersion effects [3909 Bijvoet pairs, Flack x parameter 0.03 (4) (Flack, 1983); Hooft y parameter 0.04 (3) (Hooft et al., 2008)].

The asymmetric unit of (I) contains two independent molecules; molecule 1 is shown in Fig. 1, while the second molecule has identical labels with added primes (e.g. S1' instead of S1). The structural elements are very similar, with an r.m.s. bond fit for the two molecules of 0.0072 Å (PLATON; Spek, 2009). Selected dimensions are given in Table 1, and comparisons given in Table 3 with two related structures isomorphous by addition, the diethyl and dimethyl ester analogues, (II) [Cambridge Structural Database (CSD; Allen, 2002) refocde MOLGAW; Gainsford et al., 2009], and (III) (CSD refcode MIPPOQ; Garner et al., 2001), respectively. The bond length internal self-consistency raised an issue when it was observed that the S═O bond distances [average 1.440 (3) Å] are significantly longer than those in other reported 4-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl structures, where the mean for 24 values is 1.421 (1) Å (CSD, Version 5.30 with February 2009 updates?). However, the other structural parameters in this entity are normal (Tables 1 and 3). Specifically, the S—N average and ranges for the 12 reported compounds are 1.689 (1) and 1.657–1.706 Å, respectively, and the corresponding S—C values 1.779 (2) and 1.771–1.795 Å.

Conformational differences are shown in the overlap view in Fig. 2 and are quantified by the different torsion angles involving the S1—N2 (S1'—N2') bond (Table 1) and dihedral ϕ angles between the mean planes through selected ring atoms (Table 3). The five-membered pyrrole-1,3-dione rings (C3/C4/C6/C7/N3) are effectively planar [maximum out-of-plane deviation for atom C4 = 0.025 (3) Å], with the maximum dione O-atom deviation being 0.067 (2) Å for atom O2'. The two pyrrolidine rings (N1/C2–C5) are slightly different, possibly related to the single strong intermolecular hydrogen bond (entry 1, Table 2) involving atom N1 (see also the intramolecular interaction, last two entries, Table 2). So the ring can be described as an envelope on N1 in molecule 1, and as having a twist conformation on C5'—N1' in molecule 2, with Cremer & Pople (1975) Q₂ and ϕ₂ parameters of 0.399 (3) and 0.382 (3) Å and 171.9 (4) and 168.5 (5)°, respectively. The mean planes through these two five-membered rings subtend angles of 68.81 (16) and 68.70 (16)° to each other, respectively, compared with 73.93 (16)° in endo-methyl 3-(R,S)-(cis-3-benzyloxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-(S,R)-yl)-5-methyl-4,6-dioxo-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (CSD refcode VEMJOM; Grigg et al., 1999). The few structural differences with closely related structures (II) and (III) are shown in the torsion angles (last 4 entries, Table 3).

As in both previously reported structures, (II) and (III), there are a plethora of intermolecular contacts involving `non-conventional' C—H interactions with O-atom donors; donor atoms are the sultam O atoms (O4 and O4') and the carbonyl O atoms (O1, O2 and O3) (Table 2). In Table 2, entries 13 and 14 refer to C—H···π interactions (Cg1 and Cg2 are the ring centres for phenyl groups C8'–C13' and C14'–C19', respectively). For molecule 1 (unprimed labels), a conventional hydrogen bond (entry 1, Table 2) exists between the amine H atom on N1 and sultam atom O4. For completeness, the last two entries in Table 2 indicate the close intramolecular interaction between the amine H atoms on N1 and N1' and atoms O1 and O1', respectively.

There are four comments worth making about the intermolecular binding interactions in (I). Firstly, most involve atoms of symmetry-related molecules rather than being between the two independent molecules (the exceptions being entries 2, 3 and 10 in Table 2). Secondly, sultam atom O4 is trifurcated, utilizing interactions with the closest symmetry-related molecule along the a axis (entries 1, 6 and 8). Thirdly, all the interactions except one have been observed in closely related structures as follows [where the type, H···O distance in Å, C (or N)—H···O angle in ° and CSD refcode are given in the order listed in Table 2]: entry 1, N—H···O═S, 2.23, 158 (YEXTUQ; von Wangelin et al., 2001); entry 2, tertiary C—H···O═C (pyrrole-1,3-dione), 2.41, 136 (SALYEJ; Grigg et al., 1989); entry 3, N-phenyl C—H(para)···O═C (pyrrole-1,3-dione), 2.52, 146 (PICXOO; Harwood et al., 1993); entries 4 and 5, N-phenyl C—H(meta)···O═C (pyrrole-1,3-dione), 2.41, 141 (XOKFEI; Petrovskaia et al., 2001); entries 6–9, phenyl C—H(ortho)···O═S, 2.39, 156 (GASSOJ; Yong et al., 2005); entries 11 and 12, S-methylene C—H···O═C, 2.26, 156 (ISOGUS; Miyabe et al., 2004). Finally, the C—H···π interactions (entries 13 and 14) appear to `combine' with C—H···O interactions; in Table 2, the linked entries are 3 and 13, and 10 and 14. Entry 10, involving a C—H interaction with a three-coordinate N atom (N1'), has not been observed before (according to a CSD search). Thus, apart from this latter interaction, it has not been possible to assign relative significance to these `non-classical' interactions. A packing diagram to illustrate all these interactions is not feasible. Fig. 3 illustrates how the two independent chiral molecules are packed in the cell.

Finally, we note that even with on-site scrutiny, admittedly without the benefit of a microscope fitted with crossed polarizing light capacity, it was almost impossible to identify a `clean' single-crystal from the crystal batch. In the end, although the observed initial diffraction images gave some indication, it took six different crystal mountings using the intense (synchrotron) X-ray source before a succesful unique dataset was collected. We have since observed the segmentation pattern in the larger needles under high magnification using polarized light.

S2. Experimental

2-Amino-1-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone (185 mg, 680 µmol) was treated with benzaldehyde (69.0 µl, 680 µmol), N-phenylmaleimide (353 µl, 2.04 mmol) and silver acetate (5.70 mg, 34.0 µmol) in tetrahydrofuran (2.00 ml), as described previously by Gainsford et al. (2009), to give the title compound (250 mg, 69%) as an off-white solid (m.p. 537–539 K). [α]²¹_D = -17.9° (c 1.09, CHCl₃). The spectroscopic data were consistent with those previously reported by Garner et al. (2001) {compound (39a) in section 3.6.3, which has the alternative name [1R-[1α(3aR*,6S*,7aS*),3α,3aβ,6aβ]]-3H-3a,6-methano-2,1-benzisothiazole, hexahydro-8,8-dimethyl-1-[(hexahydro-4,6-dioxo-3,5- diphenylpyrrolo[3,4-c]pyrrol-1-yl)-carbonyl]-2,2-dioxide}. The crystallization solvent was dichloromethane, with crystals of (I) formed from the diffusion of ether into the solution.

S3. Refinement

A total of 18 reflections were omitted, 13 as outliers (mainly at the edge of resolution) and five partially screened by the backstop. The H atoms on N1 and N1' were located and refined. All C-bound H atoms were constrained to their expected geometries, with C—H = 0.98, 0.99 or 1.00 Å. Methyl H atoms were refined with U_iso = 1.5U_eq(C), and all other H atoms were refined with U_iso = 1.2U_eq(C,N).

Computing details

Data collection: ADSC Quantum 210r software (ADSC, 2009); cell refinement: XDS (Kabsch, 1993); data reduction: XDS (Kabsch, 1993; locally modified) and XPREP (Bruker, 2001); 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., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. Molecular structure of one of the independent molecules in the asymmetric unit of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Overlapped view of the two independent molecules of (I). Differently coloured bonds denote the primed molecule 2, and the single colour, molecule 1.
	Fig. 3. Packing view of the cell of (I), down the a axis. Primed (molecule 1) and unprimed (molecule 2) [Are these transposed?] molecules are shown in stick and ball modes, respectively. Two representative C—H···O interactions are shown. Only H atoms involved in interactions (Table 2) are shown for clarity. [Symmetry code (i): 1 - x, 1/2 + y, 1 - z.]

(2S,3R,4S,5R)- 4-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decan- 4-ylcarbonyl)-2,6-diphenylperhydropyrrolo[3,4-c]pyrrole-1,3-dione

Crystal data

C29H31N3O5S	Z = 4
Mr = 533.63	F(000) = 1128
Monoclinic, P21	Dx = 1.377 Mg m^−3
Hall symbol: P 2yb	Synchrotron radiation, λ = 0.77300 Å
a = 7.3990 (15) Å	µ = 0.17 mm^−1
b = 26.328 (5) Å	T = 100 K
c = 13.214 (3) Å	Needle, colourless
β = 91.17 (3)°	0.15 × 0.03 × 0.01 mm
V = 2573.6 (9) Å^3

Data collection

ADSC Quantum 210r CCD area-detector diffractometer	7637 reflections with I > 2σ(I)
Radiation source: synchrotron	Rint = 0.092
Graphite monochromator	θmax = 26.5°, θmin = 2.4°
ω scans	h = −8→8
29004 measured reflections	k = −29→29
8071 independent reflections	l = −15→15

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0698P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.111	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.32 e Å^−3
8071 reflections	Δρmin = −0.39 e Å^−3
693 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.042 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 3898 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.03 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S1	0.43917 (8)	0.60984 (2)	−0.03912 (5)	0.00826 (17)
O1	−0.0562 (2)	0.56960 (7)	−0.03283 (15)	0.0139 (4)
O2	0.0389 (3)	0.50335 (7)	0.14644 (15)	0.0153 (4)
O3	−0.3153 (3)	0.60776 (8)	0.33473 (15)	0.0160 (4)
O4	0.5256 (2)	0.59733 (7)	0.05610 (14)	0.0115 (4)
O5	0.4018 (3)	0.66279 (7)	−0.05720 (15)	0.0159 (4)
N1	−0.0548 (3)	0.65663 (9)	0.08923 (17)	0.0127 (5)
H1N	−0.163 (5)	0.6386 (12)	0.073 (2)	0.015*
N2	0.2457 (3)	0.57511 (8)	−0.05106 (17)	0.0099 (5)
N3	−0.1660 (3)	0.54675 (9)	0.24262 (17)	0.0093 (5)
C1	0.0873 (4)	0.58705 (10)	−0.0034 (2)	0.0102 (6)
C2	0.0979 (4)	0.62117 (10)	0.0899 (2)	0.0112 (6)
H2	0.2125	0.6412	0.0878	0.013*
C3	0.0931 (4)	0.59197 (10)	0.1930 (2)	0.0106 (6)
H3	0.2177	0.5872	0.2223	0.013*
C4	−0.0221 (4)	0.62646 (10)	0.2616 (2)	0.0101 (6)
H4	0.0466	0.6354	0.3251	0.012*
C5	−0.0568 (4)	0.67495 (11)	0.1953 (2)	0.0124 (6)
H5	0.0535	0.6966	0.2043	0.015*
C6	−0.0091 (4)	0.54209 (10)	0.1885 (2)	0.0101 (6)
C7	−0.1879 (4)	0.59548 (10)	0.2856 (2)	0.0105 (6)
C8	−0.2857 (4)	0.50497 (10)	0.2620 (2)	0.0098 (6)
C9	−0.2177 (4)	0.46170 (10)	0.3071 (2)	0.0104 (6)
H9	−0.0927	0.4594	0.3245	0.013*
C10	−0.3330 (4)	0.42141 (11)	0.3270 (2)	0.0137 (6)
H10	−0.2871	0.3915	0.3586	0.016*
C11	−0.5139 (4)	0.42472 (11)	0.3009 (2)	0.0138 (6)
H11	−0.5925	0.3972	0.3150	0.017*
C12	−0.5816 (4)	0.46789 (11)	0.2543 (2)	0.0120 (6)
H12	−0.7061	0.4697	0.2357	0.014*
C13	−0.4682 (4)	0.50860 (11)	0.2347 (2)	0.0106 (6)
H13	−0.5143	0.5385	0.2031	0.013*
C14	−0.2153 (4)	0.70892 (11)	0.2187 (2)	0.0114 (6)
C15	−0.1894 (4)	0.74933 (11)	0.2848 (2)	0.0144 (6)
H15	−0.0771	0.7531	0.3201	0.017*
C16	−0.3266 (4)	0.78439 (12)	0.2997 (2)	0.0193 (7)
H16	−0.3071	0.8121	0.3448	0.023*
C17	−0.4916 (4)	0.77934 (11)	0.2495 (2)	0.0165 (6)
H17	−0.5849	0.8035	0.2592	0.020*
C18	−0.5187 (4)	0.73868 (11)	0.1850 (2)	0.0210 (7)
H18	−0.6320	0.7347	0.1508	0.025*
C19	−0.3828 (4)	0.70382 (12)	0.1697 (2)	0.0210 (7)
H19	−0.4038	0.6760	0.1253	0.025*
C20	0.2436 (4)	0.54372 (11)	−0.1453 (2)	0.0132 (6)
H20	0.1790	0.5623	−0.2013	0.016*
C21	0.4429 (4)	0.53505 (11)	−0.1729 (2)	0.0101 (6)
C22	0.4390 (4)	0.52183 (12)	−0.2867 (2)	0.0181 (7)
H22A	0.5625	0.5206	−0.3141	0.022*
H22B	0.3657	0.5466	−0.3262	0.022*
C23	0.3500 (4)	0.46864 (12)	−0.2875 (2)	0.0218 (7)
H23A	0.2322	0.4693	−0.3244	0.026*
H23B	0.4294	0.4432	−0.3193	0.026*
C24	0.3249 (4)	0.45676 (11)	−0.1743 (2)	0.0170 (7)
H24	0.3133	0.4198	−0.1587	0.020*
C25	0.1677 (4)	0.48956 (12)	−0.1360 (3)	0.0230 (7)
H25A	0.0575	0.4850	−0.1788	0.028*
H25B	0.1395	0.4813	−0.0649	0.028*
C26	0.5508 (4)	0.58191 (11)	−0.1433 (2)	0.0115 (6)
H26A	0.5547	0.6060	−0.2007	0.014*
H26B	0.6762	0.5725	−0.1238	0.014*
C27	0.4911 (4)	0.48258 (10)	−0.1233 (2)	0.0119 (6)
C28	0.4928 (4)	0.48013 (12)	−0.0075 (2)	0.0175 (6)
H28A	0.3802	0.4946	0.0177	0.026*
H28B	0.5958	0.4996	0.0196	0.026*
H28C	0.5034	0.4447	0.0143	0.026*
C29	0.6735 (4)	0.46165 (12)	−0.1557 (2)	0.0202 (7)
H29A	0.6868	0.4266	−0.1318	0.030*
H29B	0.7708	0.4826	−0.1265	0.030*
H29C	0.6797	0.4624	−0.2297	0.030*
S1'	0.96047 (9)	0.71074 (2)	0.78294 (5)	0.00954 (17)
O1'	0.4582 (3)	0.74503 (8)	0.76936 (16)	0.0164 (5)
O2'	0.5816 (3)	0.81257 (7)	0.59133 (15)	0.0159 (5)
O3'	0.1922 (3)	0.71272 (8)	0.40683 (15)	0.0184 (5)
O4'	1.0290 (3)	0.72447 (8)	0.68553 (15)	0.0143 (4)
O5'	0.9412 (3)	0.65711 (8)	0.80263 (15)	0.0182 (5)
N1'	0.4635 (4)	0.65998 (10)	0.64918 (18)	0.0150 (5)
H1'N	0.370 (5)	0.6789 (13)	0.667 (3)	0.018*
N2'	0.7594 (3)	0.74061 (8)	0.79852 (17)	0.0101 (5)
N3'	0.3594 (3)	0.77212 (9)	0.49694 (17)	0.0098 (5)
C1'	0.6042 (4)	0.72859 (10)	0.7444 (2)	0.0109 (6)
C2'	0.6176 (4)	0.69453 (10)	0.6510 (2)	0.0132 (6)
H2'	0.7313	0.6741	0.6567	0.016*
C3'	0.6137 (4)	0.72296 (10)	0.5467 (2)	0.0096 (6)
H3'	0.7377	0.7256	0.5184	0.012*
C4'	0.4894 (4)	0.69021 (11)	0.4784 (2)	0.0131 (6)
H4'	0.5522	0.6808	0.4147	0.016*
C5'	0.4526 (4)	0.64229 (11)	0.5429 (2)	0.0137 (6)
H5'	0.5590	0.6194	0.5338	0.016*
C6'	0.5224 (4)	0.77457 (11)	0.5502 (2)	0.0108 (6)
C7'	0.3266 (4)	0.72358 (11)	0.4547 (2)	0.0126 (6)
C8'	0.2438 (4)	0.81536 (10)	0.48092 (19)	0.0103 (6)
C9'	0.3156 (4)	0.85898 (11)	0.4372 (2)	0.0138 (6)
H9'	0.4377	0.8597	0.4165	0.017*
C10'	0.2063 (4)	0.90125 (12)	0.4247 (2)	0.0182 (7)
H10'	0.2540	0.9313	0.3958	0.022*
C11'	0.0272 (4)	0.89993 (12)	0.4541 (2)	0.0162 (6)
H11'	−0.0476	0.9289	0.4444	0.019*
C12'	−0.0424 (4)	0.85650 (11)	0.4975 (2)	0.0145 (6)
H12'	−0.1645	0.8558	0.5184	0.017*
C13'	0.0661 (4)	0.81403 (11)	0.5106 (2)	0.0115 (6)
H13'	0.0184	0.7841	0.5398	0.014*
C14'	0.2868 (4)	0.60998 (11)	0.5210 (2)	0.0128 (6)
C15'	0.3029 (4)	0.56774 (11)	0.4580 (2)	0.0150 (6)
H15'	0.4130	0.5618	0.4242	0.018*
C16'	0.1600 (4)	0.53452 (11)	0.4444 (2)	0.0164 (6)
H16'	0.1728	0.5059	0.4013	0.020*
C17'	−0.0013 (3)	0.54246 (8)	0.49275 (15)	0.0142 (6)
H17'	−0.0987	0.5193	0.4837	0.017*
C18'	−0.0198 (3)	0.58475 (8)	0.55481 (15)	0.0199 (7)
H18'	−0.1301	0.5907	0.5884	0.024*
C19'	0.1236 (4)	0.61806 (12)	0.5673 (3)	0.0226 (7)
H19'	0.1095	0.6472	0.6088	0.027*
C20'	0.7554 (4)	0.76913 (10)	0.8951 (2)	0.0087 (6)
H20'	0.7062	0.7471	0.9498	0.010*
C21'	0.9533 (4)	0.78384 (10)	0.9209 (2)	0.0088 (6)
C22'	0.9586 (4)	0.79401 (12)	1.0359 (2)	0.0166 (6)
H221	1.0841	0.7987	1.0616	0.020*
H222	0.9011	0.7660	1.0736	0.020*
C23'	0.8486 (4)	0.84372 (11)	1.0438 (2)	0.0192 (7)
H231	0.9208	0.8708	1.0775	0.023*
H232	0.7365	0.8383	1.0820	0.023*
C24'	0.8048 (4)	0.85762 (12)	0.9322 (2)	0.0158 (6)
H24'	0.7764	0.8944	0.9210	0.019*
C25'	0.6570 (4)	0.82113 (11)	0.8936 (2)	0.0153 (6)
H251	0.6153	0.8302	0.8243	0.018*
H252	0.5521	0.8210	0.9390	0.018*
C26'	1.0762 (4)	0.74152 (11)	0.8851 (2)	0.0143 (6)
H261	1.1013	0.7172	0.9407	0.017*
H262	1.1925	0.7557	0.8623	0.017*
C27'	0.9730 (4)	0.83877 (10)	0.8767 (2)	0.0097 (6)
C28'	0.9583 (4)	0.84303 (11)	0.7612 (2)	0.0132 (6)
H281	0.9540	0.8789	0.7417	0.020*
H282	0.8478	0.8260	0.7370	0.020*
H283	1.0636	0.8269	0.7309	0.020*
C29'	1.1488 (4)	0.86562 (11)	0.9098 (2)	0.0165 (6)
H291	1.2518	0.8487	0.8788	0.025*
H292	1.1623	0.8641	0.9837	0.025*
H293	1.1444	0.9012	0.8881	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0077 (3)	0.0076 (4)	0.0094 (3)	−0.0002 (3)	−0.0004 (2)	0.0003 (3)
O1	0.0063 (10)	0.0143 (11)	0.0209 (11)	0.0008 (8)	0.0004 (8)	−0.0029 (8)
O2	0.0186 (11)	0.0105 (11)	0.0171 (11)	0.0056 (8)	0.0041 (8)	−0.0032 (8)
O3	0.0185 (11)	0.0112 (11)	0.0189 (10)	0.0011 (8)	0.0099 (9)	−0.0027 (8)
O4	0.0148 (10)	0.0090 (11)	0.0106 (10)	−0.0010 (8)	−0.0019 (8)	−0.0005 (7)
O5	0.0192 (11)	0.0065 (10)	0.0221 (11)	0.0028 (8)	0.0000 (8)	0.0014 (8)
N1	0.0176 (13)	0.0087 (13)	0.0120 (12)	0.0049 (10)	0.0065 (10)	−0.0009 (10)
N2	0.0089 (12)	0.0114 (12)	0.0094 (12)	−0.0001 (9)	−0.0017 (9)	−0.0053 (9)
N3	0.0103 (12)	0.0092 (12)	0.0087 (11)	0.0016 (9)	0.0022 (9)	−0.0003 (9)
C1	0.0097 (14)	0.0101 (14)	0.0107 (14)	0.0026 (11)	0.0009 (11)	0.0038 (11)
C2	0.0108 (13)	0.0068 (14)	0.0161 (15)	−0.0031 (10)	0.0052 (11)	−0.0018 (11)
C3	0.0082 (13)	0.0106 (15)	0.0132 (14)	0.0022 (11)	0.0006 (11)	0.0001 (11)
C4	0.0129 (14)	0.0093 (15)	0.0081 (13)	−0.0001 (11)	0.0013 (11)	−0.0037 (10)
C5	0.0180 (15)	0.0071 (14)	0.0124 (14)	−0.0015 (11)	0.0054 (11)	−0.0015 (11)
C6	0.0119 (14)	0.0089 (14)	0.0095 (13)	0.0035 (11)	0.0012 (11)	0.0031 (11)
C7	0.0164 (15)	0.0073 (14)	0.0077 (13)	0.0017 (11)	0.0000 (11)	−0.0014 (10)
C8	0.0116 (14)	0.0104 (14)	0.0073 (13)	0.0015 (11)	−0.0004 (10)	−0.0021 (11)
C9	0.0125 (14)	0.0084 (14)	0.0103 (14)	0.0019 (11)	−0.0020 (11)	−0.0033 (11)
C10	0.0251 (16)	0.0066 (14)	0.0094 (15)	0.0015 (12)	−0.0014 (12)	0.0012 (11)
C11	0.0189 (16)	0.0100 (14)	0.0126 (15)	−0.0034 (12)	0.0026 (12)	−0.0027 (11)
C12	0.0093 (14)	0.0143 (15)	0.0123 (14)	0.0007 (11)	0.0014 (11)	−0.0040 (11)
C13	0.0119 (14)	0.0105 (14)	0.0093 (14)	0.0039 (11)	−0.0004 (10)	0.0002 (10)
C14	0.0129 (14)	0.0109 (14)	0.0108 (14)	−0.0027 (12)	0.0049 (10)	0.0034 (11)
C15	0.0164 (15)	0.0192 (16)	0.0077 (14)	0.0040 (12)	−0.0001 (11)	0.0006 (11)
C16	0.0264 (17)	0.0207 (18)	0.0107 (15)	0.0041 (13)	−0.0007 (12)	−0.0069 (12)
C17	0.0204 (16)	0.0143 (16)	0.0150 (15)	0.0064 (12)	0.0059 (12)	−0.0034 (12)
C18	0.0117 (15)	0.0231 (18)	0.0280 (18)	0.0022 (13)	−0.0029 (13)	−0.0058 (14)
C19	0.0197 (16)	0.0155 (17)	0.0280 (17)	−0.0063 (13)	0.0039 (13)	−0.0113 (13)
C20	0.0102 (14)	0.0158 (16)	0.0133 (14)	0.0025 (11)	−0.0036 (11)	−0.0073 (12)
C21	0.0084 (14)	0.0142 (15)	0.0077 (14)	0.0011 (11)	0.0013 (10)	0.0003 (11)
C22	0.0221 (16)	0.0250 (18)	0.0073 (14)	0.0025 (13)	0.0002 (12)	−0.0034 (12)
C23	0.0166 (16)	0.0277 (19)	0.0210 (17)	0.0008 (13)	−0.0019 (12)	−0.0130 (14)
C24	0.0163 (16)	0.0142 (16)	0.0209 (17)	−0.0009 (12)	0.0076 (13)	−0.0103 (12)
C25	0.0089 (15)	0.0266 (18)	0.0336 (19)	−0.0079 (13)	0.0035 (13)	−0.0179 (14)
C26	0.0097 (14)	0.0152 (15)	0.0099 (14)	−0.0011 (11)	0.0036 (11)	−0.0003 (11)
C27	0.0149 (14)	0.0091 (15)	0.0118 (14)	−0.0020 (11)	0.0037 (11)	−0.0010 (11)
C28	0.0264 (16)	0.0150 (16)	0.0113 (15)	0.0013 (12)	0.0024 (12)	0.0029 (12)
C29	0.0166 (16)	0.0185 (17)	0.0254 (17)	0.0065 (13)	0.0011 (13)	−0.0003 (13)
S1'	0.0114 (3)	0.0074 (4)	0.0098 (3)	0.0031 (3)	−0.0021 (2)	−0.0025 (3)
O1'	0.0091 (11)	0.0191 (12)	0.0212 (11)	−0.0031 (8)	0.0015 (8)	−0.0024 (9)
O2'	0.0173 (11)	0.0120 (11)	0.0183 (11)	−0.0045 (8)	−0.0043 (8)	−0.0036 (9)
O3'	0.0229 (11)	0.0094 (10)	0.0224 (11)	0.0012 (9)	−0.0133 (9)	−0.0024 (9)
O4'	0.0163 (10)	0.0163 (11)	0.0103 (10)	0.0016 (8)	0.0037 (8)	−0.0039 (8)
O5'	0.0288 (12)	0.0079 (11)	0.0179 (11)	0.0030 (8)	−0.0027 (9)	0.0017 (8)
N1'	0.0194 (14)	0.0113 (13)	0.0139 (13)	−0.0067 (11)	−0.0082 (10)	−0.0006 (10)
N2'	0.0081 (11)	0.0085 (12)	0.0135 (12)	−0.0004 (9)	−0.0015 (9)	−0.0034 (9)
N3'	0.0118 (12)	0.0070 (12)	0.0104 (12)	−0.0009 (9)	−0.0016 (9)	−0.0014 (9)
C1'	0.0126 (15)	0.0072 (14)	0.0128 (15)	−0.0048 (11)	−0.0025 (11)	0.0050 (11)
C2'	0.0159 (15)	0.0114 (15)	0.0121 (14)	−0.0027 (11)	−0.0025 (11)	−0.0003 (11)
C3'	0.0082 (13)	0.0071 (14)	0.0137 (15)	0.0002 (10)	0.0015 (11)	−0.0017 (10)
C4'	0.0162 (15)	0.0100 (14)	0.0130 (14)	0.0018 (12)	−0.0002 (11)	−0.0044 (11)
C5'	0.0140 (15)	0.0086 (15)	0.0184 (15)	0.0009 (11)	−0.0047 (12)	−0.0038 (11)
C6'	0.0119 (14)	0.0106 (15)	0.0099 (13)	−0.0025 (12)	−0.0002 (11)	−0.0022 (11)
C7'	0.0190 (15)	0.0134 (15)	0.0054 (14)	−0.0041 (12)	0.0023 (12)	−0.0010 (11)
C8'	0.0156 (15)	0.0070 (14)	0.0081 (13)	0.0028 (11)	−0.0030 (11)	−0.0007 (11)
C9'	0.0160 (15)	0.0145 (15)	0.0112 (14)	−0.0009 (12)	0.0068 (11)	0.0026 (11)
C10'	0.0272 (18)	0.0159 (16)	0.0116 (15)	0.0026 (13)	0.0022 (13)	0.0036 (12)
C11'	0.0212 (16)	0.0153 (16)	0.0118 (15)	0.0061 (12)	−0.0067 (12)	0.0022 (11)
C12'	0.0097 (15)	0.0200 (17)	0.0138 (14)	0.0000 (12)	0.0007 (12)	−0.0045 (12)
C13'	0.0141 (14)	0.0092 (14)	0.0111 (13)	−0.0032 (11)	−0.0005 (11)	0.0006 (11)
C14'	0.0170 (15)	0.0086 (14)	0.0125 (14)	0.0011 (12)	−0.0089 (11)	0.0025 (11)
C15'	0.0220 (16)	0.0170 (16)	0.0060 (14)	−0.0030 (12)	0.0013 (12)	0.0013 (11)
C16'	0.0227 (16)	0.0156 (15)	0.0111 (14)	−0.0056 (12)	0.0018 (12)	−0.0070 (11)
C17'	0.0161 (16)	0.0125 (15)	0.0137 (14)	−0.0033 (12)	−0.0043 (12)	0.0010 (11)
C18'	0.0184 (16)	0.0203 (17)	0.0208 (17)	0.0026 (13)	−0.0026 (13)	−0.0071 (13)
C19'	0.0202 (16)	0.0137 (16)	0.0336 (18)	0.0054 (12)	−0.0073 (14)	−0.0139 (13)
C20'	0.0091 (13)	0.0087 (14)	0.0083 (13)	−0.0017 (11)	0.0039 (10)	−0.0015 (10)
C21'	0.0095 (14)	0.0083 (15)	0.0086 (13)	0.0000 (10)	−0.0011 (10)	0.0020 (11)
C22'	0.0255 (17)	0.0131 (15)	0.0112 (14)	−0.0062 (12)	0.0013 (12)	−0.0038 (11)
C23'	0.0258 (17)	0.0183 (17)	0.0139 (16)	−0.0010 (13)	0.0092 (13)	−0.0086 (12)
C24'	0.0123 (15)	0.0128 (15)	0.0221 (16)	0.0031 (12)	0.0000 (12)	−0.0045 (12)
C25'	0.0082 (14)	0.0174 (16)	0.0205 (16)	0.0028 (11)	0.0059 (11)	−0.0053 (12)
C26'	0.0138 (14)	0.0135 (15)	0.0152 (15)	0.0073 (11)	−0.0075 (12)	−0.0066 (12)
C27'	0.0100 (14)	0.0045 (14)	0.0146 (15)	0.0003 (10)	0.0000 (11)	0.0001 (11)
C28'	0.0141 (15)	0.0089 (15)	0.0165 (15)	−0.0064 (11)	−0.0021 (11)	0.0047 (11)
C29'	0.0143 (15)	0.0188 (17)	0.0162 (15)	−0.0067 (12)	−0.0044 (12)	−0.0015 (12)

Geometric parameters (Å, º)

S1—O4	1.438 (2)	S1'—O4'	1.439 (2)
S1—O5	1.440 (2)	S1'—O5'	1.443 (2)
S1—N2	1.703 (2)	S1'—N2'	1.699 (2)
S1—C26	1.779 (3)	S1'—C26'	1.780 (3)
O1—C1	1.213 (3)	O1'—C1'	1.215 (4)
O2—C6	1.218 (3)	O2'—C6'	1.216 (3)
O3—C7	1.200 (3)	O3'—C7'	1.202 (4)
N1—C2	1.465 (4)	N1'—C2'	1.458 (4)
N1—C5	1.482 (4)	N1'—C5'	1.480 (4)
N1—H1N	0.95 (3)	N1'—H1'N	0.89 (4)
N2—C1	1.378 (4)	N2'—C1'	1.377 (4)
N2—C20	1.495 (3)	N2'—C20'	1.482 (3)
N3—C6	1.381 (4)	N3'—C6'	1.386 (4)
N3—C7	1.414 (4)	N3'—C7'	1.414 (4)
N3—C8	1.439 (4)	N3'—C8'	1.437 (3)
C1—C2	1.527 (4)	C1'—C2'	1.530 (4)
C2—C3	1.565 (4)	C2'—C3'	1.568 (4)
C2—H2	1.0000	C2'—H2'	1.0000
C3—C6	1.516 (4)	C3'—C6'	1.519 (4)
C3—C4	1.551 (4)	C3'—C4'	1.540 (4)
C3—H3	1.0000	C3'—H3'	1.0000
C4—C7	1.512 (4)	C4'—C7'	1.519 (4)
C4—C5	1.567 (4)	C4'—C5'	1.550 (4)
C4—H4	1.0000	C4'—H4'	1.0000
C5—C14	1.512 (4)	C5'—C14'	1.516 (4)
C5—H5	1.0000	C5'—H5'	1.0000
C8—C9	1.377 (4)	C8'—C13'	1.380 (4)
C8—C13	1.394 (4)	C8'—C9'	1.395 (4)
C9—C10	1.390 (4)	C9'—C10'	1.384 (4)
C9—H9	0.9500	C9'—H9'	0.9500
C10—C11	1.378 (4)	C10'—C11'	1.389 (4)
C10—H10	0.9500	C10'—H10'	0.9500
C11—C12	1.382 (4)	C11'—C12'	1.384 (4)
C11—H11	0.9500	C11'—H11'	0.9500
C12—C13	1.389 (4)	C12'—C13'	1.385 (4)
C12—H12	0.9500	C12'—H12'	0.9500
C13—H13	0.9500	C13'—H13'	0.9500
C14—C15	1.387 (4)	C14'—C19'	1.382 (4)
C14—C19	1.393 (4)	C14'—C15'	1.395 (4)
C15—C16	1.389 (4)	C15'—C16'	1.381 (4)
C15—H15	0.9500	C15'—H15'	0.9500
C16—C17	1.384 (4)	C16'—C17'	1.381 (4)
C16—H16	0.9500	C16'—H16'	0.9500
C17—C18	1.380 (4)	C17'—C18'	1.391 (3)
C17—H17	0.9500	C17'—H17'	0.9500
C18—C19	1.379 (4)	C18'—C19'	1.384 (4)
C18—H18	0.9500	C18'—H18'	0.9500
C19—H19	0.9500	C19'—H19'	0.9500
C20—C25	1.539 (4)	C20'—C21'	1.546 (4)
C20—C21	1.543 (4)	C20'—C25'	1.551 (4)
C20—H20	1.0000	C20'—H20'	1.0000
C21—C26	1.516 (4)	C21'—C26'	1.519 (4)
C21—C22	1.544 (4)	C21'—C22'	1.542 (4)
C21—C27	1.567 (4)	C21'—C27'	1.568 (4)
C22—C23	1.547 (4)	C22'—C23'	1.546 (4)
C22—H22A	0.9900	C22'—H221	0.9900
C22—H22B	0.9900	C22'—H222	0.9900
C23—C24	1.543 (4)	C23'—C24'	1.547 (4)
C23—H23A	0.9900	C23'—H231	0.9900
C23—H23B	0.9900	C23'—H232	0.9900
C24—C25	1.542 (4)	C24'—C25'	1.535 (4)
C24—C27	1.547 (4)	C24'—C27'	1.540 (4)
C24—H24	1.0000	C24'—H24'	1.0000
C25—H25A	0.9900	C25'—H251	0.9900
C25—H25B	0.9900	C25'—H252	0.9900
C26—H26A	0.9900	C26'—H261	0.9900
C26—H26B	0.9900	C26'—H262	0.9900
C27—C29	1.527 (4)	C27'—C28'	1.532 (4)
C27—C28	1.531 (4)	C27'—C29'	1.536 (4)
C28—H28A	0.9800	C28'—H281	0.9800
C28—H28B	0.9800	C28'—H282	0.9800
C28—H28C	0.9800	C28'—H283	0.9800
C29—H29A	0.9800	C29'—H291	0.9800
C29—H29B	0.9800	C29'—H292	0.9800
C29—H29C	0.9800	C29'—H293	0.9800
O4—S1—O5	116.58 (12)	O4'—S1'—O5'	116.40 (12)
O4—S1—N2	108.42 (11)	O4'—S1'—N2'	108.51 (12)
O5—S1—N2	110.23 (11)	O5'—S1'—N2'	109.95 (12)
O4—S1—C26	112.19 (12)	O4'—S1'—C26'	113.05 (13)
O5—S1—C26	111.24 (13)	O5'—S1'—C26'	110.88 (13)
N2—S1—C26	96.25 (12)	N2'—S1'—C26'	96.10 (12)
C2—N1—C5	102.9 (2)	C2'—N1'—C5'	103.8 (2)
C2—N1—H1N	109.2 (19)	C2'—N1'—H1'N	105 (2)
C5—N1—H1N	110 (2)	C5'—N1'—H1'N	114 (2)
C1—N2—C20	120.8 (2)	C1'—N2'—C20'	122.2 (2)
C1—N2—S1	123.81 (19)	C1'—N2'—S1'	123.6 (2)
C20—N2—S1	111.60 (18)	C20'—N2'—S1'	111.83 (17)
C6—N3—C7	113.1 (2)	C6'—N3'—C7'	112.6 (2)
C6—N3—C8	123.5 (2)	C6'—N3'—C8'	123.2 (2)
C7—N3—C8	123.1 (2)	C7'—N3'—C8'	124.1 (2)
O1—C1—N2	120.9 (3)	O1'—C1'—N2'	120.9 (3)
O1—C1—C2	120.8 (2)	O1'—C1'—C2'	120.0 (2)
N2—C1—C2	118.2 (2)	N2'—C1'—C2'	119.1 (2)
N1—C2—C1	110.0 (2)	N1'—C2'—C1'	108.4 (2)
N1—C2—C3	106.7 (2)	N1'—C2'—C3'	106.5 (2)
C1—C2—C3	114.4 (2)	C1'—C2'—C3'	115.4 (2)
N1—C2—H2	108.5	N1'—C2'—H2'	108.8
C1—C2—H2	108.5	C1'—C2'—H2'	108.8
C3—C2—H2	108.5	C3'—C2'—H2'	108.8
C6—C3—C4	104.5 (2)	C6'—C3'—C4'	105.0 (2)
C6—C3—C2	114.3 (2)	C6'—C3'—C2'	113.6 (2)
C4—C3—C2	104.1 (2)	C4'—C3'—C2'	104.3 (2)
C6—C3—H3	111.2	C6'—C3'—H3'	111.2
C4—C3—H3	111.2	C4'—C3'—H3'	111.2
C2—C3—H3	111.2	C2'—C3'—H3'	111.2
C7—C4—C3	105.3 (2)	C7'—C4'—C3'	105.0 (2)
C7—C4—C5	115.6 (2)	C7'—C4'—C5'	115.9 (2)
C3—C4—C5	103.6 (2)	C3'—C4'—C5'	104.1 (2)
C7—C4—H4	110.6	C7'—C4'—H4'	110.5
C3—C4—H4	110.6	C3'—C4'—H4'	110.5
C5—C4—H4	110.6	C5'—C4'—H4'	110.5
N1—C5—C14	114.1 (2)	N1'—C5'—C14'	112.7 (2)
N1—C5—C4	105.0 (2)	N1'—C5'—C4'	105.0 (2)
C14—C5—C4	119.1 (2)	C14'—C5'—C4'	120.2 (2)
N1—C5—H5	105.9	N1'—C5'—H5'	106.0
C14—C5—H5	105.9	C14'—C5'—H5'	106.0
C4—C5—H5	105.9	C4'—C5'—H5'	106.0
O2—C6—N3	124.5 (2)	O2'—C6'—N3'	124.5 (3)
O2—C6—C3	126.4 (3)	O2'—C6'—C3'	126.4 (2)
N3—C6—C3	109.1 (2)	N3'—C6'—C3'	109.0 (2)
O3—C7—N3	124.0 (3)	O3'—C7'—N3'	123.8 (3)
O3—C7—C4	128.2 (2)	O3'—C7'—C4'	128.0 (3)
N3—C7—C4	107.8 (2)	N3'—C7'—C4'	108.2 (2)
C9—C8—C13	120.9 (3)	C13'—C8'—C9'	120.7 (3)
C9—C8—N3	119.3 (2)	C13'—C8'—N3'	120.4 (2)
C13—C8—N3	119.9 (2)	C9'—C8'—N3'	118.9 (2)
C8—C9—C10	119.5 (3)	C10'—C9'—C8'	119.0 (3)
C8—C9—H9	120.2	C10'—C9'—H9'	120.5
C10—C9—H9	120.2	C8'—C9'—H9'	120.5
C11—C10—C9	120.1 (3)	C9'—C10'—C11'	120.3 (3)
C11—C10—H10	120.0	C9'—C10'—H10'	119.8
C9—C10—H10	120.0	C11'—C10'—H10'	119.8
C10—C11—C12	120.3 (3)	C12'—C11'—C10'	120.1 (3)
C10—C11—H11	119.8	C12'—C11'—H11'	119.9
C12—C11—H11	119.8	C10'—C11'—H11'	119.9
C11—C12—C13	120.2 (3)	C11'—C12'—C13'	119.9 (3)
C11—C12—H12	119.9	C11'—C12'—H12'	120.0
C13—C12—H12	119.9	C13'—C12'—H12'	120.0
C12—C13—C8	119.0 (3)	C8'—C13'—C12'	119.9 (3)
C12—C13—H13	120.5	C8'—C13'—H13'	120.1
C8—C13—H13	120.5	C12'—C13'—H13'	120.1
C15—C14—C19	118.5 (3)	C19'—C14'—C15'	118.2 (3)
C15—C14—C5	119.0 (3)	C19'—C14'—C5'	122.7 (3)
C19—C14—C5	122.3 (3)	C15'—C14'—C5'	118.9 (3)
C14—C15—C16	120.5 (3)	C16'—C15'—C14'	120.5 (3)
C14—C15—H15	119.8	C16'—C15'—H15'	119.7
C16—C15—H15	119.8	C14'—C15'—H15'	119.7
C17—C16—C15	120.5 (3)	C15'—C16'—C17'	120.7 (3)
C17—C16—H16	119.7	C15'—C16'—H16'	119.7
C15—C16—H16	119.7	C17'—C16'—H16'	119.7
C18—C17—C16	119.1 (3)	C16'—C17'—C18'	119.34 (15)
C18—C17—H17	120.5	C16'—C17'—H17'	120.3
C16—C17—H17	120.5	C18'—C17'—H17'	120.3
C19—C18—C17	120.6 (3)	C19'—C18'—C17'	119.56 (16)
C19—C18—H18	119.7	C19'—C18'—H18'	120.2
C17—C18—H18	119.7	C17'—C18'—H18'	120.2
C18—C19—C14	120.8 (3)	C14'—C19'—C18'	121.6 (3)
C18—C19—H19	119.6	C14'—C19'—H19'	119.2
C14—C19—H19	119.6	C18'—C19'—H19'	119.2
N2—C20—C25	116.3 (2)	N2'—C20'—C21'	106.4 (2)
N2—C20—C21	106.6 (2)	N2'—C20'—C25'	117.0 (2)
C25—C20—C21	103.5 (2)	C21'—C20'—C25'	103.0 (2)
N2—C20—H20	110.0	N2'—C20'—H20'	110.0
C25—C20—H20	110.0	C21'—C20'—H20'	110.0
C21—C20—H20	110.0	C25'—C20'—H20'	110.0
C26—C21—C20	108.6 (2)	C26'—C21'—C22'	115.5 (2)
C26—C21—C22	115.7 (2)	C26'—C21'—C20'	108.5 (2)
C20—C21—C22	105.3 (2)	C22'—C21'—C20'	105.4 (2)
C26—C21—C27	119.7 (2)	C26'—C21'—C27'	120.0 (2)
C20—C21—C27	104.0 (2)	C22'—C21'—C27'	101.9 (2)
C22—C21—C27	102.0 (2)	C20'—C21'—C27'	104.1 (2)
C21—C22—C23	102.1 (2)	C21'—C22'—C23'	102.2 (2)
C21—C22—H22A	111.3	C21'—C22'—H221	111.3
C23—C22—H22A	111.3	C23'—C22'—H221	111.3
C21—C22—H22B	111.3	C21'—C22'—H222	111.3
C23—C22—H22B	111.3	C23'—C22'—H222	111.3
H22A—C22—H22B	109.2	H221—C22'—H222	109.2
C24—C23—C22	103.7 (2)	C22'—C23'—C24'	103.7 (2)
C24—C23—H23A	111.0	C22'—C23'—H231	111.0
C22—C23—H23A	111.0	C24'—C23'—H231	111.0
C24—C23—H23B	111.0	C22'—C23'—H232	111.0
C22—C23—H23B	111.0	C24'—C23'—H232	111.0
H23A—C23—H23B	109.0	H231—C23'—H232	109.0
C25—C24—C23	108.1 (3)	C25'—C24'—C27'	102.5 (2)
C25—C24—C27	102.1 (2)	C25'—C24'—C23'	107.6 (3)
C23—C24—C27	102.9 (2)	C27'—C24'—C23'	102.8 (2)
C25—C24—H24	114.2	C25'—C24'—H24'	114.2
C23—C24—H24	114.2	C27'—C24'—H24'	114.2
C27—C24—H24	114.2	C23'—C24'—H24'	114.2
C20—C25—C24	102.3 (2)	C24'—C25'—C20'	102.5 (2)
C20—C25—H25A	111.3	C24'—C25'—H251	111.3
C24—C25—H25A	111.3	C20'—C25'—H251	111.3
C20—C25—H25B	111.3	C24'—C25'—H252	111.3
C24—C25—H25B	111.3	C20'—C25'—H252	111.3
H25A—C25—H25B	109.2	H251—C25'—H252	109.2
C21—C26—S1	106.59 (19)	C21'—C26'—S1'	106.76 (19)
C21—C26—H26A	110.4	C21'—C26'—H261	110.4
S1—C26—H26A	110.4	S1'—C26'—H261	110.4
C21—C26—H26B	110.4	C21'—C26'—H262	110.4
S1—C26—H26B	110.4	S1'—C26'—H262	110.4
H26A—C26—H26B	108.6	H261—C26'—H262	108.6
C29—C27—C28	106.0 (2)	C28'—C27'—C29'	107.0 (2)
C29—C27—C24	114.7 (2)	C28'—C27'—C24'	114.2 (2)
C28—C27—C24	114.0 (2)	C29'—C27'—C24'	113.8 (2)
C29—C27—C21	113.3 (2)	C28'—C27'—C21'	115.7 (2)
C28—C27—C21	116.9 (2)	C29'—C27'—C21'	113.7 (2)
C24—C27—C21	91.9 (2)	C24'—C27'—C21'	92.2 (2)
C27—C28—H28A	109.5	C27'—C28'—H281	109.5
C27—C28—H28B	109.5	C27'—C28'—H282	109.5
H28A—C28—H28B	109.5	H281—C28'—H282	109.5
C27—C28—H28C	109.5	C27'—C28'—H283	109.5
H28A—C28—H28C	109.5	H281—C28'—H283	109.5
H28B—C28—H28C	109.5	H282—C28'—H283	109.5
C27—C29—H29A	109.5	C27'—C29'—H291	109.5
C27—C29—H29B	109.5	C27'—C29'—H292	109.5
H29A—C29—H29B	109.5	H291—C29'—H292	109.5
C27—C29—H29C	109.5	C27'—C29'—H293	109.5
H29A—C29—H29C	109.5	H291—C29'—H293	109.5
H29B—C29—H29C	109.5	H292—C29'—H293	109.5
O4—S1—N2—C1	78.6 (2)	O4'—S1'—N2'—C1'	69.4 (2)
O5—S1—N2—C1	−50.1 (2)	O5'—S1'—N2'—C1'	−58.9 (2)
C26—S1—N2—C1	−165.5 (2)	C26'—S1'—N2'—C1'	−173.8 (2)
O4—S1—N2—C20	−123.20 (19)	O4'—S1'—N2'—C20'	−127.73 (18)
O5—S1—N2—C20	108.10 (19)	O5'—S1'—N2'—C20'	103.92 (19)
C26—S1—N2—C20	−7.3 (2)	C26'—S1'—N2'—C20'	−10.9 (2)
C20—N2—C1—O1	5.0 (4)	C20'—N2'—C1'—O1'	6.8 (4)
S1—N2—C1—O1	161.3 (2)	S1'—N2'—C1'—O1'	167.9 (2)
C20—N2—C1—C2	−177.4 (2)	C20'—N2'—C1'—C2'	−173.9 (2)
S1—N2—C1—C2	−21.0 (3)	S1'—N2'—C1'—C2'	−12.8 (3)
C5—N1—C2—C1	163.3 (2)	C5'—N1'—C2'—C1'	160.9 (2)
C5—N1—C2—C3	38.7 (3)	C5'—N1'—C2'—C3'	36.2 (3)
O1—C1—C2—N1	−41.4 (3)	O1'—C1'—C2'—N1'	−40.0 (3)
N2—C1—C2—N1	141.0 (2)	N2'—C1'—C2'—N1'	140.7 (2)
O1—C1—C2—C3	78.7 (3)	O1'—C1'—C2'—C3'	79.2 (3)
N2—C1—C2—C3	−99.0 (3)	N2'—C1'—C2'—C3'	−100.1 (3)
N1—C2—C3—C6	93.2 (3)	N1'—C2'—C3'—C6'	96.4 (3)
C1—C2—C3—C6	−28.7 (3)	C1'—C2'—C3'—C6'	−23.9 (3)
N1—C2—C3—C4	−20.1 (3)	N1'—C2'—C3'—C4'	−17.4 (3)
C1—C2—C3—C4	−142.0 (2)	C1'—C2'—C3'—C4'	−137.7 (2)
C6—C3—C4—C7	−3.8 (3)	C6'—C3'—C4'—C7'	−4.9 (3)
C2—C3—C4—C7	116.4 (2)	C2'—C3'—C4'—C7'	114.8 (2)
C6—C3—C4—C5	−125.7 (2)	C6'—C3'—C4'—C5'	−127.1 (2)
C2—C3—C4—C5	−5.5 (3)	C2'—C3'—C4'—C5'	−7.4 (3)
C2—N1—C5—C14	−174.3 (2)	C2'—N1'—C5'—C14'	−173.6 (2)
C2—N1—C5—C4	−42.1 (3)	C2'—N1'—C5'—C4'	−41.1 (3)
C7—C4—C5—N1	−85.7 (3)	C7'—C4'—C5'—N1'	−85.2 (3)
C3—C4—C5—N1	29.1 (3)	C3'—C4'—C5'—N1'	29.5 (3)
C7—C4—C5—C14	43.7 (3)	C7'—C4'—C5'—C14'	42.9 (4)
C3—C4—C5—C14	158.4 (2)	C3'—C4'—C5'—C14'	157.6 (2)
C7—N3—C6—O2	178.8 (3)	C7'—N3'—C6'—O2'	178.3 (3)
C8—N3—C6—O2	4.7 (4)	C8'—N3'—C6'—O2'	2.4 (4)
C7—N3—C6—C3	0.3 (3)	C7'—N3'—C6'—C3'	−0.6 (3)
C8—N3—C6—C3	−173.7 (2)	C8'—N3'—C6'—C3'	−176.5 (2)
C4—C3—C6—O2	−176.1 (3)	C4'—C3'—C6'—O2'	−175.4 (3)
C2—C3—C6—O2	70.7 (4)	C2'—C3'—C6'—O2'	71.3 (4)
C4—C3—C6—N3	2.3 (3)	C4'—C3'—C6'—N3'	3.5 (3)
C2—C3—C6—N3	−110.8 (2)	C2'—C3'—C6'—N3'	−109.9 (3)
C6—N3—C7—O3	179.3 (3)	C6'—N3'—C7'—O3'	178.8 (3)
C8—N3—C7—O3	−6.6 (4)	C8'—N3'—C7'—O3'	−5.4 (4)
C6—N3—C7—C4	−2.9 (3)	C6'—N3'—C7'—C4'	−2.7 (3)
C8—N3—C7—C4	171.2 (2)	C8'—N3'—C7'—C4'	173.2 (2)
C3—C4—C7—O3	−178.2 (3)	C3'—C4'—C7'—O3'	−176.9 (3)
C5—C4—C7—O3	−64.5 (4)	C5'—C4'—C7'—O3'	−62.7 (4)
C3—C4—C7—N3	4.1 (3)	C3'—C4'—C7'—N3'	4.7 (3)
C5—C4—C7—N3	117.9 (2)	C5'—C4'—C7'—N3'	118.9 (2)
C6—N3—C8—C9	54.5 (4)	C6'—N3'—C8'—C13'	−124.1 (3)
C7—N3—C8—C9	−119.0 (3)	C7'—N3'—C8'—C13'	60.5 (3)
C6—N3—C8—C13	−125.2 (3)	C6'—N3'—C8'—C9'	54.4 (3)
C7—N3—C8—C13	61.3 (4)	C7'—N3'—C8'—C9'	−121.0 (3)
C13—C8—C9—C10	−0.9 (4)	C13'—C8'—C9'—C10'	0.5 (4)
N3—C8—C9—C10	179.3 (2)	N3'—C8'—C9'—C10'	−177.9 (3)
C8—C9—C10—C11	0.5 (4)	C8'—C9'—C10'—C11'	−0.7 (4)
C9—C10—C11—C12	0.4 (4)	C9'—C10'—C11'—C12'	0.9 (4)
C10—C11—C12—C13	−0.9 (4)	C10'—C11'—C12'—C13'	−0.8 (4)
C11—C12—C13—C8	0.5 (4)	C9'—C8'—C13'—C12'	−0.4 (4)
C9—C8—C13—C12	0.5 (4)	N3'—C8'—C13'—C12'	178.0 (2)
N3—C8—C13—C12	−179.8 (2)	C11'—C12'—C13'—C8'	0.5 (4)
N1—C5—C14—C15	−143.6 (3)	N1'—C5'—C14'—C19'	33.6 (4)
C4—C5—C14—C15	91.3 (3)	C4'—C5'—C14'—C19'	−91.0 (4)
N1—C5—C14—C19	30.7 (4)	N1'—C5'—C14'—C15'	−140.8 (3)
C4—C5—C14—C19	−94.3 (3)	C4'—C5'—C14'—C15'	94.6 (3)
C19—C14—C15—C16	−1.4 (4)	C19'—C14'—C15'—C16'	−1.3 (4)
C5—C14—C15—C16	173.1 (3)	C5'—C14'—C15'—C16'	173.5 (3)
C14—C15—C16—C17	0.5 (5)	C14'—C15'—C16'—C17'	0.0 (4)
C15—C16—C17—C18	0.6 (5)	C15'—C16'—C17'—C18'	0.8 (3)
C16—C17—C18—C19	−0.8 (5)	C16'—C17'—C18'—C19'	−0.2 (2)
C17—C18—C19—C14	−0.2 (5)	C15'—C14'—C19'—C18'	1.9 (4)
C15—C14—C19—C18	1.3 (5)	C5'—C14'—C19'—C18'	−172.7 (3)
C5—C14—C19—C18	−173.1 (3)	C17'—C18'—C19'—C14'	−1.2 (4)
C1—N2—C20—C25	−61.5 (3)	C1'—N2'—C20'—C21'	−169.4 (2)
S1—N2—C20—C25	139.6 (2)	S1'—N2'—C20'—C21'	27.5 (2)
C1—N2—C20—C21	−176.2 (2)	C1'—N2'—C20'—C25'	−55.0 (3)
S1—N2—C20—C21	24.8 (3)	S1'—N2'—C20'—C25'	141.9 (2)
N2—C20—C21—C26	−34.1 (3)	N2'—C20'—C21'—C26'	−34.3 (3)
C25—C20—C21—C26	−157.3 (2)	C25'—C20'—C21'—C26'	−157.9 (2)
N2—C20—C21—C22	−158.7 (2)	N2'—C20'—C21'—C22'	−158.6 (2)
C25—C20—C21—C22	78.2 (3)	C25'—C20'—C21'—C22'	77.8 (3)
N2—C20—C21—C27	94.4 (2)	N2'—C20'—C21'—C27'	94.6 (2)
C25—C20—C21—C27	−28.8 (3)	C25'—C20'—C21'—C27'	−29.0 (3)
C26—C21—C22—C23	170.5 (2)	C26'—C21'—C22'—C23'	170.5 (2)
C20—C21—C22—C23	−69.6 (3)	C20'—C21'—C22'—C23'	−69.7 (3)
C27—C21—C22—C23	38.8 (3)	C27'—C21'—C22'—C23'	38.7 (3)
C21—C22—C23—C24	−3.3 (3)	C21'—C22'—C23'—C24'	−3.5 (3)
C22—C23—C24—C25	73.8 (3)	C22'—C23'—C24'—C25'	74.2 (3)
C22—C23—C24—C27	−33.7 (3)	C22'—C23'—C24'—C27'	−33.6 (3)
N2—C20—C25—C24	−124.3 (3)	C27'—C24'—C25'—C20'	41.9 (3)
C21—C20—C25—C24	−7.8 (3)	C23'—C24'—C25'—C20'	−66.2 (3)
C23—C24—C25—C20	−65.6 (3)	N2'—C20'—C25'—C24'	−123.4 (3)
C27—C24—C25—C20	42.4 (3)	C21'—C20'—C25'—C24'	−7.2 (3)
C20—C21—C26—S1	28.8 (3)	C22'—C21'—C26'—S1'	144.6 (2)
C22—C21—C26—S1	147.0 (2)	C20'—C21'—C26'—S1'	26.5 (3)
C27—C21—C26—S1	−90.3 (3)	C27'—C21'—C26'—S1'	−92.7 (3)
O4—S1—C26—C21	99.94 (19)	O4'—S1'—C26'—C21'	103.5 (2)
O5—S1—C26—C21	−127.45 (19)	O5'—S1'—C26'—C21'	−123.7 (2)
N2—S1—C26—C21	−12.9 (2)	N2'—S1'—C26'—C21'	−9.6 (2)
C25—C24—C27—C29	−174.0 (3)	C25'—C24'—C27'—C28'	62.6 (3)
C23—C24—C27—C29	−61.9 (3)	C23'—C24'—C27'—C28'	174.2 (2)
C25—C24—C27—C28	63.5 (3)	C25'—C24'—C27'—C29'	−174.1 (2)
C23—C24—C27—C28	175.5 (2)	C23'—C24'—C27'—C29'	−62.5 (3)
C25—C24—C27—C21	−57.2 (3)	C25'—C24'—C27'—C21'	−56.9 (2)
C23—C24—C27—C21	54.9 (2)	C23'—C24'—C27'—C21'	54.7 (2)
C26—C21—C27—C29	−68.4 (3)	C26'—C21'—C27'—C28'	55.5 (3)
C20—C21—C27—C29	170.2 (2)	C22'—C21'—C27'—C28'	−175.5 (2)
C22—C21—C27—C29	60.8 (3)	C20'—C21'—C27'—C28'	−66.0 (3)
C26—C21—C27—C28	55.3 (3)	C26'—C21'—C27'—C29'	−69.0 (3)
C20—C21—C27—C28	−66.1 (3)	C22'—C21'—C27'—C29'	60.0 (3)
C22—C21—C27—C28	−175.5 (2)	C20'—C21'—C27'—C29'	169.5 (2)
C26—C21—C27—C24	173.6 (2)	C26'—C21'—C27'—C24'	173.7 (2)
C20—C21—C27—C24	52.2 (2)	C22'—C21'—C27'—C24'	−57.3 (2)
C22—C21—C27—C24	−57.2 (2)	C20'—C21'—C27'—C24'	52.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4^i	0.95 (3)	2.55 (4)	3.495 (3)	170 (2)
C4′—H4′···O3^ii	1.00	2.41	3.243 (4)	140
C11—H11···O2′^iii	0.95	2.55	3.321 (4)	138
C12—H12···O2^i	0.95	2.38	3.259 (4)	155
C12′—H12′···O2′^i	0.95	2.41	3.280 (4)	151
C13—H13···O4^i	0.95	2.51	3.320 (3)	144
C13′—H13′···O4′^i	0.95	2.48	3.317 (4)	147
C19—H19···O4^i	0.95	2.32	3.245 (4)	165
C19′—H19′···O4′^i	0.95	2.36	3.290 (4)	168
C26—H26A···N1′^iv	0.99	2.52	3.477 (4)	162
C26—H26B···O1^ii	0.99	2.30	3.243 (3)	160
C26′—H262···O1′^ii	0.99	2.36	3.242 (4)	149
C10—H10···Cg1^iii	0.95	2.69	3.486 (3)	142
C22—H22B···Cg2^iv	0.99	2.84	3.757 (3)	153
N1′—H1N′···O1′	0.89 (4)	2.29 (4)	2.746 (3)	112 (3)
N1—H1N···O1	0.95 (3)	2.43 (3)	2.802 (3)	103 (2)

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