Multicentre hydrogen bonds in a 2:1 aryl­sulfonyl­imidazol­one ­hydro­chloride salt

The title compound, (S)-(+)-4-[5-(2-oxo-4,5-di­hydro­imidazol-1-yl­sulfonyl)­indolin-1-yl­carbonyl]­anilinium chloride (S)-(+)-1-[1-(4-amino­benzoyl)­indoline-5-sulfonyl]-4-phenyl-4,5-di­hydro­imidazol-2-one, C₂₄H₂₃N₄O₄S⁺·Cl⁻·C₂₄H₂₂N₄O₄S, crystallizes in space group C2 from a CH₃OH/CH₂Cl₂ solution. In the crystal structure, there are two different conformers with their terminal C₆ aromatic rings mutually oriented at angles of 67.69 (14) and 61.16 (15)°. The distances of the terminal N atoms (of the two conformers) from the chloride ion are 3.110 (4) and 3.502 (4) Å. There are eight distinct hydrogen bonds, i.e. four N—H...Cl, three N—H...O and one N—H...N, with one N—H group involved in a bifurcated hydrogen bond with two acceptors sharing the H atom. C—H...O contacts assist in the overall hydrogen-bonding process.

S1. Comment

In the search for new anticancer agents, the free amine of the title compound, (I), was synthesized originally as a racemic mixture (Jung et al., 1998) with only the S enantiomer showing improved antitumor activity (Jung, 1999). Treatment of the free amine with anhydrous HCl/CH₃OH solvent and recrystallization from a CH₃OH/CH₂Cl₂ solution unexpectedly produced single crystals of the 2:1 hydrochloride salt. A 1:1 salt, however, could be formed, but only as an amorphous powder. Attempts to obtain a stoichiometric single-crystal of the 1:1 salt from various solvents have thus far failed. The present X-ray crystallographic study was undertaken in order to elucidate the structural characteristics of the 2:1 hydrochloride salt.

In the crystal structure, there exist two conformationally different molecules (A and B in Fig. 1). The Cl1···N1A/B distances are 3.110 (4) and 3.502 (4) Å in A and B, respectively. In addition, the bond lengths of the terminal amine N1A/B to the aromatic ring differ [N1A—C11A 1.475 (4) Å and N1B—C11B 1.388 (5) Å], indicating that molecule A is protonated as NH₃⁺ and molecule B exists in the free NH₂ amine form. In the solid-state IR spectrum, both NH₃⁺ and NH₂ stretching vibrations were identified; difference Fourier synthesis also verified the existence three and two H atoms at N1A and N1B, respectively. The torsion angles between the three aromatic rings differ in molecules A and B, as depicted in Fig. 2. The major differences are observed in the orientation of the terminal aniline group in comparison to the rest of the molecule. The angles of the N-substituted C₆ ring to the terminal phenyl-ring plane are 67.69 (14)° in A and 61.16 (15)° in B, while the indoline groups are oriented at angles of 68.22 (13) and 60.38 (14)° to the former plane in A and B, respectively. In the indoline group, both conformers differ (torsion angles in Table 1), with the C18B atom lying closer to the indoline ring plane in B [C18A—C19A—C20A—C25A −161.6 (4)° and C18B—C19B—C20B—C25B −173.7 (4)°].

The carbonyl plane is twisted from the phenyl plane in both conformations [C13A—C14A—C17A—O8A −31.4 (5)° and C13B—C14B—C17B—O8B −30.0 (6)°]. The longer Csp²—Csp² bond lengths [C14A—C17A 1.503 (5) Å and C14B—C17B 1.485 (5) Å] arise from the deviation from coplanarity of the amide carbonyl and phenyl-ring systems. The two amide groups of each molecule show a characteristic feature in both conformations. The former C—N bonds are shorter than the normal amide C—N bonds [N2A—C17A 1.368 (5) Å and N2B—C17B 1.382 (5) Å] attached to indoline ring. The lengths of the two amide C—N bonds of the imidazolone ring differ with the short N3A—C26A [1.314 (5) Å] and N3B—C26B [1.318 (5) Å] bonds having double-bond character compared with the longer N4A—C26A [1.402 (4) Å] and N4B—C26B [1.402 (4) Å] bonds on the opposite side of urea group.

The hydrogen-bonding parameters listed in Table 2 reveal the differences in the intermolecular relationships of the two molecules on packing. The distance of the terminal N atom to the central Cl1 ion shows remarkable inequality, with N1Aⁱⁱ···Cl1 [3.110 (4) Å; symmetry code: (ii) 1 − x, −1 + y, −z] substantially shorter than N1Bⁱⁱ···Cl1 [3.502 (4) Å]. The former constitutes a hydrogen bond, whereas the latter resides at the edge of conventional hydrogen bonds. All imidazolone NH groups in A and B act as donors to the Cl1 ion, forming hydrogen bonds of similar strength and geometry [N3Aⁱ···Cl1 3.106 (3) Å and N3B···Cl1 3.103 (3) Å]. Thus, the Cl ion is a fourfold acceptor, accepting two from the N1Aⁱⁱ and N1Bⁱⁱ terminal amines and two from the N3Aⁱ and N3B atoms of the imidazolone groups of molecules A and B [symmetry code: (i) x, y, 1 + z]. The N1Aⁱⁱ, N3Aⁱ and N3B atoms and the Cl1 ion are almost coplanar and perpendicular to the c axis, resulting in a `hydrogen-bonding channel' parallel to the c axis. The increased anisotropy of the N3A and N3B atoms may be due to the inherent loose packing through this channel with the Cl ion as an acceptor of hydrogen in the centre showing a synchronous positional disorder and atomic mobility in this direction.

As well as the four hydrogen bonds to the Cl1 ion, four more hydrogen bonds involving the N—H groups and O atoms of the imidazolone contribute to crystalline cohesion. N1Aⁱⁱⁱ donates its H1Aⁱⁱⁱ and H1Cⁱⁱⁱ atoms to the carbonyl O7Aⁱ and O7B atom of the imidazolone, and N1Bⁱⁱⁱ interacts with the neighbouring N1Aⁱⁱⁱ and O7B atoms [symmetry code: (iii) 1 − x, y, −z]. The O7B and N1Bⁱⁱⁱ acceptors share H1Cⁱⁱⁱ from N1Aⁱⁱⁱ, thus building a three-centre hydrogen bond, and O7B is an acceptor of two H atoms from N1Aⁱⁱⁱ and N1Bⁱⁱⁱ. In Fig. 3, all the hydrogen bonds around the Cl ion are shown explicitly. Furthermore, additional multi-centre interactions involving aliphatic C—H groups of A and B are present. These are depicted in Fig. 4 and listed in Table 2.

S2. Experimental

The free amine of the title compound was synthesized and purified as reported previously (Jung et al., 1998) from (S)-phenylglycinol (converted into its hydrochloride in CH₃OH saturated with HCl gas). After treatment of this CH₃OH/HCl solution with ethyl acetate, an amorphous powder of the hydrochloride salt was obtained. The elemental analysis and IR spectrum showed that all terminal amine groups are protonated in the 1:1 hydrochloride salt. [Elemental analysis, calculated for C₂₄H₂₃N₄O₄S⁺·Cl⁻: C 57.77, H 4.65, N 11.23%; found: C 57.0 (5), H 4.4 (3), N 10.86 (8)%. IR spectrum (ν_max, KBr, cm⁻¹): 3200, 2800.] The amorphous salt was then treated in CH₃OH/CH₂Cl₂ (7:1) co-solvent and slow evaporation produced single crystals of (I) suitablefor X-ray measurements. The elemental analysis and IR spectrum revealed (I) to have NH₂, NH and NH₃⁺ groups. [Elemental analysis, calculated for C₂₄H₂₃N₄O₄S⁺·Cl⁻·C₂₄H₂₂N₄O₄S: C 59.96, H 4.72, N 11.65; found: C 59.87 (5), H 4.45 (11), N 11.46 (13)%. IR spectrum (ν_max, KBr, cm⁻¹): 3330, 3200, 2800.]

S3. Refinement

The H atoms were treated using a riding model (C—H 0.93–0.98 Å and N—H 0.86–0.89 Å). The absolute structure was inferred not only from the absolute configuration of (S)-phenylglycinol used as starting material in the synthesis, but also determined by refining an enantiomorph-sensitive parameter to −0.07 (7) (Flack, 1983) using all 3715 Friedel pairs.

Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: WinGX (Farrugia, 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Johnson et al., 1998); software used to prepare material for publication: WinGX.

Figures

	Fig. 1. The molecular structure and atomic numbering scheme of (a) molecule A and (b) molecule B. Displacement ellipsoids are drawn at the 30% probability level for all non-H atoms. The interactions of the Cl1^ii ion [symmetry code: (ii) 1 − x,1 + y,-z] with N1A and N1B are highlighted with dashed lines.
	Fig. 2. Illustration of the conformational differences of the two conformers, with molecule A (thick lines) overlayed on molecule B (thin lines).
	Fig. 3. A view of the intermolecular hydrogen bonds around the Cl ion. Displacement ellipsoids are drawn at the 30% probability and the interactions are indicated with dashed lines connecting H and acceptor atoms [symmetry codes: (i) x, y, 1 + z; (ii) 1 − x, −1 + y, −z; (iii) 1 − x, y, −z].
	Fig. 4. Intermolecular C—H···O and N—H···Cl/N—H···N interactions between the conformers are depicted with displacement ellipsoids drawn at the 30% probability; symmetry codes are as given in Fig. 3.

[(S)-(+)-4-Phenyl-1-[1-(4-aminobenzoyl)indoline-5-sulfonyl]-4,5-dihydro- 2-imidazolone] 0.5-hydrochloride

Crystal data

C24H23N4O4S^+·Cl^−·C24H22N4O4S	Dx = 1.382 Mg m^−3
Mr = 961.49	Melting point: 489 K
Monoclinic, C2	Mo Kα radiation, λ = 0.71069 Å
a = 28.945 (3) Å	Cell parameters from 25 reflections
b = 6.5473 (9) Å	θ = 11.4–14.2°
c = 27.526 (2) Å	µ = 0.24 mm^−1
β = 117.622 (7)°	T = 294 K
V = 4621.9 (9) Å^3	Prism, pale brown
Z = 4	0.43 × 0.40 × 0.33 mm
F(000) = 2008

Data collection

Enraf-Nonius CAD-4 diffractometer	5916 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.2°, θmin = 2.1°
ω–2θ scans	h = 0→34
Absorption correction: ψ scan (North et al., 1968)	k = −7→7
Tmin = 0.905, Tmax = 0.926	l = −32→29
8420 measured reflections	3 standard reflections every 300 min
8252 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 1.0617P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
8252 reflections	Δρmax = 0.28 e Å^−3
605 parameters	Δρmin = −0.18 e Å^−3
1 restraint	Absolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (7)

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.

Hydrogen bonding and contacts ############################# N1A H1A O7A 0.89 1.90 2.768 (4) 166.0 2_654 yes N1A H1B Cl1 0.89 2.22 3.110 (4) 174.0 2_665 yes N1A H1C O7B 0.89 2.36 3.086 (4) 138.9 2_655 yes N1A H1C N1B 0.89 2.51 3.008 (4) 115.9. yes N1B H1D O7B 0.86 2.23 2.980 (4) 144.9 2_655 yes N1B H1E Cl1 0.86 2.66 3.502 (4) 165.8 2_665 yes N3A H3A Cl1 0.86 2.32 3.106 (3) 152.5 1_554 yes N3B H3B Cl1 0.86 2.33 3.103 (3) 149.9. yes

C18A H18A O8A 0.97 2.55 3.018 (4) 109.4 1_565 yes C19A H19B O8A 0.97 2.85 3.336 (5) 112.1 1_565 yes C27A H27A O5A 0.97 2.48 2.935 (4) 108.7 1_545 yes C28A H28A O5A 0.98 2.64 3.158 (5) 113.0 1_545 yes C18B H18C O8B 0.97 2.44 3.123 (5) 127.0 1_565 yes C19B H19D O8B 0.97 2.78 3.351 (5) 118.1 1_565 yes C27B H27C O5B 0.97 2.46 2.919 (4) 108.7 1_545 yes C28B H28B O5B 0.98 2.57 3.095 (5) 113.4 1_545 yes

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
S1A	0.71416 (3)	0.77234 (14)	−0.58890 (4)	0.0438 (2)
N1A	0.50142 (12)	0.8717 (5)	−0.28874 (13)	0.0580 (9)
H1A	0.4688	0.8287	−0.3005	0.087*
H1B	0.5033	1.0046	−0.2813	0.087*
H1C	0.5225	0.8036	−0.2585	0.087*
N2A	0.59478 (11)	0.8413 (4)	−0.46512 (12)	0.0472 (8)
N3A	0.60953 (12)	0.4745 (6)	−0.70211 (15)	0.0738 (11)
H3A	0.5770	0.4548	−0.7237	0.089*
N4A	0.68106 (11)	0.6194 (4)	−0.64197 (12)	0.0420 (7)
O5A	0.71481 (10)	0.9710 (4)	−0.60969 (10)	0.0555 (7)
O6A	0.76194 (9)	0.6676 (4)	−0.55732 (10)	0.0548 (7)
O7A	0.60350 (10)	0.8045 (4)	−0.67748 (10)	0.0629 (7)
O8A	0.57497 (12)	0.5143 (4)	−0.45563 (11)	0.0608 (8)
C11A	0.51750 (14)	0.8355 (6)	−0.33163 (14)	0.0465 (9)
C12A	0.49431 (15)	0.6838 (6)	−0.36947 (15)	0.0530 (10)
H12A	0.4669	0.6088	−0.3698	0.064*
C13A	0.51225 (15)	0.6434 (6)	−0.40746 (15)	0.0538 (10)
H13A	0.4975	0.5378	−0.4326	0.065*
C14A	0.55214 (13)	0.7604 (6)	−0.40788 (14)	0.0445 (9)
C15A	0.57369 (15)	0.9152 (6)	−0.37009 (15)	0.0570 (11)
H15A	0.6002	0.9951	−0.3703	0.068*
C16A	0.55648 (14)	0.9529 (7)	−0.33199 (16)	0.0578 (11)
H16A	0.5712	1.0577	−0.3066	0.069*
C17A	0.57400 (15)	0.6952 (6)	−0.44544 (15)	0.0460 (9)
C18A	0.58062 (16)	1.0619 (5)	−0.47330 (16)	0.0517 (10)
H18A	0.6056	1.1433	−0.4431	0.062*
H18B	0.5461	1.0842	−0.4767	0.062*
C19A	0.58203 (16)	1.1137 (6)	−0.52681 (16)	0.0551 (10)
H19A	0.5477	1.1014	−0.5581	0.066*
H19B	0.5952	1.2506	−0.5258	0.066*
C20A	0.61900 (14)	0.9545 (6)	−0.52841 (14)	0.0452 (9)
C21A	0.62372 (13)	0.7964 (6)	−0.49347 (13)	0.0424 (8)
C22A	0.65545 (15)	0.6296 (6)	−0.48706 (15)	0.0523 (10)
H22A	0.6582	0.5237	−0.4634	0.063*
C23A	0.68294 (15)	0.6244 (6)	−0.51676 (14)	0.0511 (10)
H23A	0.7046	0.5142	−0.5131	0.061*
C24A	0.67829 (13)	0.7829 (6)	−0.55182 (13)	0.0449 (8)
C25A	0.64627 (14)	0.9509 (6)	−0.55836 (14)	0.0457 (9)
H25A	0.6434	1.0570	−0.5821	0.055*
C26A	0.62749 (15)	0.6473 (6)	−0.67577 (16)	0.0502 (10)
C27A	0.69450 (14)	0.4040 (5)	−0.63966 (16)	0.0526 (10)
H27A	0.6964	0.3392	−0.6071	0.063*
H27B	0.7275	0.3857	−0.6403	0.063*
C28A	0.64877 (13)	0.3192 (6)	−0.69205 (16)	0.0518 (10)
H28A	0.6373	0.1885	−0.6840	0.062*
C29A	0.66129 (13)	0.2927 (7)	−0.73938 (15)	0.0514 (9)
C30A	0.68585 (16)	0.1178 (7)	−0.74233 (18)	0.0645 (12)
H30A	0.6930	0.0163	−0.7162	0.077*
C31A	0.70015 (18)	0.0884 (9)	−0.78298 (19)	0.0805 (15)
H31A	0.7170	−0.0312	−0.7840	0.097*
C32A	0.68948 (18)	0.2360 (11)	−0.8219 (2)	0.0846 (18)
H32A	0.6995	0.2187	−0.8492	0.102*
C33A	0.6643 (2)	0.4070 (10)	−0.8202 (2)	0.0899 (17)
H33A	0.6564	0.5064	−0.8471	0.108*
C34A	0.64993 (16)	0.4374 (8)	−0.77901 (19)	0.0720 (13)
H34A	0.6326	0.5562	−0.7785	0.086*
S1B	0.27780 (3)	0.78296 (14)	0.09839 (4)	0.0432 (2)
N1B	0.51914 (14)	0.9075 (7)	−0.17240 (14)	0.0867 (14)
H1D	0.5437	0.8304	−0.1712	0.104*
H1E	0.5106	1.0163	−0.1922	0.104*
N2B	0.39633 (12)	0.8567 (4)	−0.02600 (13)	0.0492 (8)
N3B	0.38135 (11)	0.4796 (5)	0.21321 (14)	0.0633 (10)
H3B	0.4135	0.4599	0.2363	0.076*
N4B	0.31097 (11)	0.6267 (4)	0.15125 (11)	0.0429 (7)
O5B	0.27804 (10)	0.9806 (4)	0.12061 (10)	0.0555 (7)
O6B	0.22975 (9)	0.6784 (4)	0.06720 (10)	0.0531 (7)
O7B	0.38956 (9)	0.8088 (4)	0.19059 (10)	0.0581 (7)
O8B	0.40642 (12)	0.5272 (4)	−0.04358 (12)	0.0703 (9)
C11B	0.49322 (16)	0.8564 (7)	−0.14248 (16)	0.0632 (12)
C12B	0.50564 (17)	0.6849 (7)	−0.11064 (17)	0.0661 (12)
H12B	0.5316	0.5982	−0.1094	0.079*
C13B	0.47998 (16)	0.6379 (6)	−0.07999 (16)	0.0589 (11)
H13B	0.4880	0.5179	−0.0596	0.071*
C14B	0.44237 (14)	0.7695 (7)	−0.07970 (14)	0.0519 (9)
C15B	0.42967 (16)	0.9417 (7)	−0.11270 (16)	0.0661 (12)
H15B	0.4039	1.0295	−0.1138	0.079*
C16B	0.45433 (16)	0.9856 (7)	−0.14383 (17)	0.0706 (13)
H16B	0.4450	1.1016	−0.1658	0.085*
C17B	0.41399 (16)	0.7076 (6)	−0.04886 (15)	0.0510 (10)
C18B	0.4179 (2)	1.0650 (6)	−0.0121 (2)	0.0761 (15)
H18C	0.4012	1.1549	−0.0435	0.091*
H18D	0.4552	1.0641	−0.0001	0.091*
C19B	0.40656 (16)	1.1352 (6)	0.03474 (16)	0.0587 (11)
H19C	0.4384	1.1436	0.0691	0.070*
H19D	0.3895	1.2674	0.0267	0.070*
C20B	0.37116 (14)	0.9728 (6)	0.03713 (14)	0.0465 (9)
C21B	0.36650 (13)	0.8148 (6)	0.00109 (14)	0.0435 (9)
C22B	0.33412 (14)	0.6482 (6)	−0.00618 (15)	0.0525 (10)
H22B	0.3306	0.5445	−0.0307	0.063*
C23B	0.30709 (14)	0.6415 (6)	0.02440 (14)	0.0473 (9)
H23B	0.2851	0.5321	0.0202	0.057*
C24B	0.31261 (13)	0.7956 (6)	0.06085 (13)	0.0437 (8)
C25B	0.34481 (14)	0.9622 (6)	0.06754 (14)	0.0479 (9)
H25B	0.3484	1.0652	0.0923	0.058*
C26B	0.36438 (14)	0.6526 (6)	0.18626 (15)	0.0456 (9)
C27B	0.29620 (14)	0.4132 (5)	0.14870 (15)	0.0493 (10)
H27C	0.2938	0.3476	0.1160	0.059*
H27D	0.2632	0.3987	0.1495	0.059*
C28B	0.34152 (13)	0.3249 (6)	0.20097 (15)	0.0500 (9)
H28B	0.3531	0.1957	0.1922	0.060*
C29B	0.32817 (12)	0.2918 (6)	0.24743 (14)	0.0470 (9)
C30B	0.30355 (15)	0.1123 (7)	0.24913 (17)	0.0582 (11)
H30B	0.2967	0.0131	0.2225	0.070*
C31B	0.28897 (16)	0.0780 (8)	0.28944 (19)	0.0738 (14)
H31B	0.2722	−0.0429	0.2898	0.089*
C32B	0.29920 (18)	0.2221 (10)	0.3290 (2)	0.0799 (17)
H32B	0.2891	0.2002	0.3561	0.096*
C33B	0.32398 (19)	0.3970 (10)	0.32865 (19)	0.0887 (17)
H33B	0.3313	0.4941	0.3559	0.106*
C34B	0.33852 (17)	0.4323 (8)	0.28775 (18)	0.0715 (13)
H34B	0.3555	0.5531	0.2879	0.086*
Cl1	0.49530 (4)	0.32892 (18)	0.25666 (6)	0.0866 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0473 (5)	0.0366 (5)	0.0482 (5)	−0.0009 (5)	0.0227 (5)	−0.0008 (5)
N1A	0.0577 (19)	0.063 (2)	0.056 (2)	−0.0062 (18)	0.0286 (17)	−0.0038 (17)
N2A	0.0629 (19)	0.0328 (18)	0.0512 (18)	0.0052 (15)	0.0310 (17)	−0.0030 (15)
N3A	0.0343 (18)	0.074 (3)	0.107 (3)	−0.0089 (18)	0.0274 (19)	−0.041 (2)
N4A	0.0411 (17)	0.0321 (16)	0.0473 (17)	0.0049 (14)	0.0158 (15)	−0.0016 (14)
O5A	0.0707 (18)	0.0358 (15)	0.0685 (17)	−0.0073 (14)	0.0395 (15)	0.0005 (14)
O6A	0.0452 (15)	0.0601 (18)	0.0530 (16)	0.0063 (13)	0.0176 (13)	−0.0020 (14)
O7A	0.0533 (15)	0.0611 (19)	0.0680 (17)	0.0178 (15)	0.0229 (14)	−0.0045 (16)
O8A	0.093 (2)	0.0349 (16)	0.0690 (18)	0.0053 (15)	0.0503 (17)	0.0006 (13)
C11A	0.049 (2)	0.056 (3)	0.0362 (19)	−0.0024 (19)	0.0209 (18)	−0.0061 (18)
C12A	0.055 (2)	0.054 (2)	0.055 (2)	−0.006 (2)	0.029 (2)	0.003 (2)
C13A	0.069 (3)	0.047 (2)	0.046 (2)	−0.013 (2)	0.027 (2)	−0.0095 (19)
C14A	0.045 (2)	0.043 (2)	0.0415 (19)	0.0015 (19)	0.0165 (17)	0.0005 (19)
C15A	0.055 (2)	0.070 (3)	0.058 (2)	−0.019 (2)	0.036 (2)	−0.020 (2)
C16A	0.053 (2)	0.065 (3)	0.058 (2)	−0.019 (2)	0.028 (2)	−0.024 (2)
C17A	0.056 (2)	0.039 (2)	0.040 (2)	0.0066 (18)	0.0199 (19)	−0.0011 (17)
C18A	0.070 (3)	0.034 (2)	0.062 (3)	0.0095 (19)	0.039 (2)	−0.0024 (19)
C19A	0.067 (3)	0.038 (2)	0.065 (3)	0.008 (2)	0.034 (2)	0.005 (2)
C20A	0.053 (2)	0.031 (2)	0.047 (2)	0.0047 (18)	0.019 (2)	−0.0040 (18)
C21A	0.052 (2)	0.037 (2)	0.0390 (18)	0.0016 (19)	0.0218 (17)	−0.0021 (18)
C22A	0.074 (3)	0.038 (2)	0.050 (2)	0.011 (2)	0.032 (2)	0.0093 (19)
C23A	0.064 (2)	0.041 (2)	0.052 (2)	0.016 (2)	0.030 (2)	0.0095 (19)
C24A	0.051 (2)	0.038 (2)	0.047 (2)	0.0033 (19)	0.0247 (18)	−0.002 (2)
C25A	0.058 (2)	0.034 (2)	0.048 (2)	0.0018 (19)	0.026 (2)	−0.0014 (18)
C26A	0.047 (2)	0.052 (3)	0.059 (2)	−0.003 (2)	0.030 (2)	−0.010 (2)
C27A	0.059 (2)	0.034 (2)	0.067 (3)	0.0002 (19)	0.031 (2)	−0.0039 (19)
C28A	0.051 (2)	0.037 (2)	0.078 (3)	−0.0102 (18)	0.039 (2)	−0.014 (2)
C29A	0.0381 (19)	0.053 (2)	0.058 (2)	−0.003 (2)	0.0178 (19)	−0.006 (2)
C30A	0.063 (3)	0.066 (3)	0.070 (3)	0.010 (2)	0.036 (2)	0.000 (2)
C31A	0.069 (3)	0.112 (4)	0.069 (3)	0.012 (3)	0.039 (3)	−0.009 (3)
C32A	0.054 (3)	0.141 (6)	0.058 (3)	−0.008 (3)	0.026 (3)	−0.007 (4)
C33A	0.077 (4)	0.117 (5)	0.057 (3)	−0.002 (4)	0.016 (3)	0.026 (3)
C34A	0.063 (3)	0.066 (3)	0.078 (3)	0.007 (2)	0.025 (3)	0.005 (3)
S1B	0.0468 (5)	0.0343 (5)	0.0445 (5)	0.0011 (5)	0.0177 (4)	0.0025 (5)
N1B	0.084 (3)	0.125 (4)	0.071 (3)	0.020 (3)	0.053 (2)	0.022 (3)
N2B	0.062 (2)	0.0360 (18)	0.055 (2)	0.0013 (16)	0.0310 (17)	0.0075 (15)
N3B	0.0324 (17)	0.063 (2)	0.081 (2)	0.0048 (17)	0.0144 (17)	0.035 (2)
N4B	0.0423 (17)	0.0334 (16)	0.0422 (17)	−0.0049 (14)	0.0105 (15)	0.0050 (14)
O5B	0.0735 (19)	0.0356 (15)	0.0615 (17)	0.0057 (14)	0.0348 (15)	0.0008 (13)
O6B	0.0411 (14)	0.0568 (17)	0.0513 (15)	−0.0009 (13)	0.0128 (12)	0.0011 (13)
O7B	0.0578 (16)	0.0541 (18)	0.0541 (15)	−0.0188 (15)	0.0190 (13)	0.0000 (14)
O8B	0.102 (2)	0.0446 (19)	0.082 (2)	−0.0106 (17)	0.057 (2)	−0.0044 (16)
C11B	0.055 (2)	0.084 (3)	0.048 (3)	0.001 (2)	0.021 (2)	0.008 (2)
C12B	0.065 (3)	0.069 (3)	0.062 (3)	0.015 (2)	0.027 (2)	0.002 (2)
C13B	0.070 (3)	0.052 (3)	0.056 (3)	0.005 (2)	0.030 (2)	0.005 (2)
C14B	0.051 (2)	0.054 (2)	0.046 (2)	0.004 (2)	0.0184 (19)	0.007 (2)
C15B	0.056 (3)	0.077 (3)	0.068 (3)	0.020 (2)	0.031 (2)	0.029 (3)
C16B	0.071 (3)	0.081 (3)	0.066 (3)	0.016 (3)	0.038 (3)	0.035 (3)
C17B	0.061 (3)	0.046 (3)	0.042 (2)	−0.003 (2)	0.020 (2)	0.0028 (18)
C18B	0.105 (4)	0.035 (2)	0.119 (4)	−0.012 (2)	0.077 (4)	−0.003 (3)
C19B	0.070 (3)	0.035 (2)	0.072 (3)	−0.006 (2)	0.034 (2)	0.003 (2)
C20B	0.051 (2)	0.035 (2)	0.046 (2)	0.0003 (18)	0.017 (2)	0.0069 (18)
C21B	0.046 (2)	0.038 (2)	0.0409 (19)	0.0042 (18)	0.0163 (18)	0.0059 (18)
C22B	0.059 (2)	0.046 (2)	0.048 (2)	−0.006 (2)	0.021 (2)	−0.008 (2)
C23B	0.052 (2)	0.040 (2)	0.046 (2)	−0.0108 (18)	0.0190 (19)	−0.0045 (18)
C24B	0.0451 (19)	0.041 (2)	0.0355 (17)	−0.0016 (19)	0.0105 (16)	0.0044 (19)
C25B	0.059 (2)	0.036 (2)	0.042 (2)	0.0016 (19)	0.018 (2)	0.0000 (18)
C26B	0.047 (2)	0.044 (2)	0.047 (2)	−0.0023 (19)	0.0227 (19)	0.0028 (19)
C27B	0.048 (2)	0.037 (2)	0.055 (2)	−0.0031 (18)	0.018 (2)	0.0038 (18)
C28B	0.043 (2)	0.041 (2)	0.063 (2)	0.0015 (18)	0.0222 (19)	0.011 (2)
C29B	0.0359 (18)	0.046 (2)	0.053 (2)	0.0040 (19)	0.0156 (18)	0.007 (2)
C30B	0.057 (3)	0.057 (3)	0.063 (3)	−0.011 (2)	0.030 (2)	−0.005 (2)
C31B	0.063 (3)	0.092 (4)	0.072 (3)	−0.017 (3)	0.036 (3)	0.005 (3)
C32B	0.056 (3)	0.129 (5)	0.059 (3)	0.001 (3)	0.030 (3)	0.005 (3)
C33B	0.081 (4)	0.123 (5)	0.053 (3)	0.001 (4)	0.024 (3)	−0.025 (3)
C34B	0.070 (3)	0.069 (3)	0.072 (3)	−0.015 (3)	0.030 (3)	−0.015 (3)
Cl1	0.0445 (6)	0.0603 (8)	0.1507 (12)	0.0005 (6)	0.0415 (7)	−0.0034 (8)

Geometric parameters (Å, º)

S1A—O6A	1.423 (3)	S1B—O6B	1.426 (3)
S1A—O5A	1.424 (3)	S1B—O5B	1.430 (3)
S1A—N4A	1.660 (3)	S1B—N4B	1.670 (3)
S1A—C24A	1.763 (3)	S1B—C24B	1.748 (3)
N1A—C11A	1.475 (4)	N1B—C11B	1.388 (5)
N1A—H1A	0.8900	N1B—H1D	0.8600
N1A—H1B	0.8900	N1B—H1E	0.8600
N1A—H1C	0.8900	N2B—C17B	1.382 (5)
N2A—C17A	1.368 (5)	N2B—C21B	1.405 (4)
N2A—C21A	1.416 (4)	N2B—C18B	1.475 (5)
N2A—C18A	1.490 (4)	N3B—C26B	1.318 (5)
N3A—C26A	1.314 (5)	N3B—C28B	1.452 (4)
N3A—C28A	1.452 (5)	N3B—H3B	0.8600
N3A—H3A	0.8600	N4B—C26B	1.402 (4)
N4A—C26A	1.402 (4)	N4B—C27B	1.454 (4)
N4A—C27A	1.457 (4)	O7B—C26B	1.229 (4)
O7A—C26A	1.230 (4)	O8B—C17B	1.222 (4)
O8A—C17A	1.221 (4)	C11B—C12B	1.366 (6)
C11A—C12A	1.368 (5)	C11B—C16B	1.394 (6)
C11A—C16A	1.369 (5)	C12B—C13B	1.392 (6)
C12A—C13A	1.392 (5)	C12B—H12B	0.9300
C12A—H12A	0.9300	C13B—C14B	1.391 (5)
C13A—C14A	1.390 (5)	C13B—H13B	0.9300
C13A—H13A	0.9300	C14B—C15B	1.387 (5)
C14A—C15A	1.377 (5)	C14B—C17B	1.485 (5)
C14A—C17A	1.503 (5)	C15B—C16B	1.376 (5)
C15A—C16A	1.376 (5)	C15B—H15B	0.9300
C15A—H15A	0.9300	C16B—H16B	0.9300
C16A—H16A	0.9300	C18B—C19B	1.540 (6)
C18A—C19A	1.530 (5)	C18B—H18C	0.9700
C18A—H18A	0.9700	C18B—H18D	0.9700
C18A—H18B	0.9700	C19B—C20B	1.499 (5)
C19A—C20A	1.509 (5)	C19B—H19C	0.9700
C19A—H19A	0.9700	C19B—H19D	0.9700
C19A—H19B	0.9700	C20B—C25B	1.371 (5)
C20A—C21A	1.376 (5)	C20B—C21B	1.396 (5)
C20A—C25A	1.381 (5)	C21B—C22B	1.391 (5)
C21A—C22A	1.385 (5)	C22B—C23B	1.391 (5)
C22A—C23A	1.380 (5)	C22B—H22B	0.9300
C22A—H22A	0.9300	C23B—C24B	1.379 (5)
C23A—C24A	1.380 (5)	C23B—H23B	0.9300
C23A—H23A	0.9300	C24B—C25B	1.391 (5)
C24A—C25A	1.396 (5)	C25B—H25B	0.9300
C25A—H25A	0.9300	C27B—C28B	1.541 (5)
C27A—C28A	1.539 (5)	C27B—H27C	0.9700
C27A—H27A	0.9700	C27B—H27D	0.9700
C27A—H27B	0.9700	C28B—C29B	1.513 (5)
C28A—C29A	1.515 (5)	C28B—H28B	0.9800
C28A—H28A	0.9800	C29B—C34B	1.364 (6)
C29A—C34A	1.365 (6)	C29B—C30B	1.386 (6)
C29A—C30A	1.370 (6)	C30B—C31B	1.376 (5)
C30A—C31A	1.375 (6)	C30B—H30B	0.9300
C30A—H30A	0.9300	C31B—C32B	1.365 (7)
C31A—C32A	1.367 (7)	C31B—H31B	0.9300
C31A—H31A	0.9300	C32B—C33B	1.353 (7)
C32A—C33A	1.348 (7)	C32B—H32B	0.9300
C32A—H32A	0.9300	C33B—C34B	1.392 (6)
C33A—C34A	1.392 (7)	C33B—H33B	0.9300
C33A—H33A	0.9300	C34B—H34B	0.9300
C34A—H34A	0.9300
O6A—S1A—O5A	119.69 (17)	C33A—C34A—H34A	120.0
O6A—S1A—N4A	104.36 (15)	O6B—S1B—O5B	120.15 (16)
O5A—S1A—N4A	107.86 (16)	O6B—S1B—N4B	103.69 (15)
O6A—S1A—C24A	109.38 (16)	O5B—S1B—N4B	107.15 (15)
O5A—S1A—C24A	108.54 (17)	O6B—S1B—C24B	109.59 (16)
N4A—S1A—C24A	106.17 (16)	O5B—S1B—C24B	108.67 (17)
C11A—N1A—H1A	109.5	N4B—S1B—C24B	106.74 (16)
C11A—N1A—H1B	109.5	C11B—N1B—H1D	120.0
H1A—N1A—H1B	109.5	C11B—N1B—H1E	120.0
C11A—N1A—H1C	109.5	H1D—N1B—H1E	120.0
H1A—N1A—H1C	109.5	C17B—N2B—C21B	123.5 (3)
H1B—N1A—H1C	109.5	C17B—N2B—C18B	124.8 (3)
C17A—N2A—C21A	123.7 (3)	C21B—N2B—C18B	109.5 (3)
C17A—N2A—C18A	126.7 (3)	C26B—N3B—C28B	114.9 (3)
C21A—N2A—C18A	108.0 (3)	C26B—N3B—H3B	122.6
C26A—N3A—C28A	115.1 (3)	C28B—N3B—H3B	122.6
C26A—N3A—H3A	122.5	C26B—N4B—C27B	110.8 (3)
C28A—N3A—H3A	122.5	C26B—N4B—S1B	122.0 (2)
C26A—N4A—C27A	110.2 (3)	C27B—N4B—S1B	120.6 (2)
C26A—N4A—S1A	121.0 (2)	C12B—C11B—N1B	121.7 (4)
C27A—N4A—S1A	120.8 (2)	C12B—C11B—C16B	119.0 (4)
C12A—C11A—C16A	121.1 (3)	N1B—C11B—C16B	119.3 (4)
C12A—C11A—N1A	120.0 (3)	C11B—C12B—C13B	121.0 (4)
C16A—C11A—N1A	118.8 (3)	C11B—C12B—H12B	119.5
C11A—C12A—C13A	119.2 (4)	C13B—C12B—H12B	119.5
C11A—C12A—H12A	120.4	C14B—C13B—C12B	120.3 (4)
C13A—C12A—H12A	120.4	C14B—C13B—H13B	119.8
C14A—C13A—C12A	120.1 (4)	C12B—C13B—H13B	119.8
C14A—C13A—H13A	119.9	C15B—C14B—C13B	118.1 (4)
C12A—C13A—H13A	119.9	C15B—C14B—C17B	123.2 (4)
C15A—C14A—C13A	119.1 (3)	C13B—C14B—C17B	118.4 (4)
C15A—C14A—C17A	122.8 (3)	C16B—C15B—C14B	121.4 (4)
C13A—C14A—C17A	117.7 (3)	C16B—C15B—H15B	119.3
C16A—C15A—C14A	120.7 (4)	C14B—C15B—H15B	119.3
C16A—C15A—H15A	119.7	C15B—C16B—C11B	120.1 (4)
C14A—C15A—H15A	119.7	C15B—C16B—H16B	119.9
C11A—C16A—C15A	119.7 (4)	C11B—C16B—H16B	119.9
C11A—C16A—H16A	120.2	O8B—C17B—N2B	120.3 (4)
C15A—C16A—H16A	120.2	O8B—C17B—C14B	120.6 (4)
O8A—C17A—N2A	121.8 (3)	N2B—C17B—C14B	119.1 (3)
O8A—C17A—C14A	119.7 (4)	N2B—C18B—C19B	105.3 (3)
N2A—C17A—C14A	118.5 (3)	N2B—C18B—H18C	110.7
N2A—C18A—C19A	103.4 (3)	C19B—C18B—H18C	110.7
N2A—C18A—H18A	111.1	N2B—C18B—H18D	110.7
C19A—C18A—H18A	111.1	C19B—C18B—H18D	110.7
N2A—C18A—H18B	111.1	H18C—C18B—H18D	108.8
C19A—C18A—H18B	111.1	C20B—C19B—C18B	103.9 (3)
H18A—C18A—H18B	109.0	C20B—C19B—H19C	111.0
C20A—C19A—C18A	102.2 (3)	C18B—C19B—H19C	111.0
C20A—C19A—H19A	111.3	C20B—C19B—H19D	111.0
C18A—C19A—H19A	111.3	C18B—C19B—H19D	111.0
C20A—C19A—H19B	111.3	H19C—C19B—H19D	109.0
C18A—C19A—H19B	111.3	C25B—C20B—C21B	119.9 (3)
H19A—C19A—H19B	109.2	C25B—C20B—C19B	130.4 (4)
C21A—C20A—C25A	120.4 (3)	C21B—C20B—C19B	109.7 (3)
C21A—C20A—C19A	109.9 (3)	C22B—C21B—C20B	121.3 (3)
C25A—C20A—C19A	129.7 (3)	C22B—C21B—N2B	128.0 (3)
C20A—C21A—C22A	121.8 (3)	C20B—C21B—N2B	110.6 (3)
C20A—C21A—N2A	109.7 (3)	C23B—C22B—C21B	117.9 (3)
C22A—C21A—N2A	128.4 (3)	C23B—C22B—H22B	121.0
C23A—C22A—C21A	118.3 (3)	C21B—C22B—H22B	121.0
C23A—C22A—H22A	120.8	C24B—C23B—C22B	120.7 (3)
C21A—C22A—H22A	120.8	C24B—C23B—H23B	119.7
C22A—C23A—C24A	120.0 (4)	C22B—C23B—H23B	119.7
C22A—C23A—H23A	120.0	C23B—C24B—C25B	121.0 (3)
C24A—C23A—H23A	120.0	C23B—C24B—S1B	119.4 (3)
C23A—C24A—C25A	121.8 (3)	C25B—C24B—S1B	119.6 (3)
C23A—C24A—S1A	118.9 (3)	C20B—C25B—C24B	119.2 (3)
C25A—C24A—S1A	119.4 (3)	C20B—C25B—H25B	120.4
C20A—C25A—C24A	117.7 (3)	C24B—C25B—H25B	120.4
C20A—C25A—H25A	121.1	O7B—C26B—N3B	127.7 (4)
C24A—C25A—H25A	121.1	O7B—C26B—N4B	125.6 (3)
O7A—C26A—N3A	128.9 (4)	N3B—C26B—N4B	106.7 (3)
O7A—C26A—N4A	124.4 (4)	N4B—C27B—C28B	102.2 (3)
N3A—C26A—N4A	106.7 (3)	N4B—C27B—H27C	111.3
N4A—C27A—C28A	102.2 (3)	C28B—C27B—H27C	111.3
N4A—C27A—H27A	111.3	N4B—C27B—H27D	111.3
C28A—C27A—H27A	111.3	C28B—C27B—H27D	111.3
N4A—C27A—H27B	111.3	H27C—C27B—H27D	109.2
C28A—C27A—H27B	111.3	N3B—C28B—C29B	113.0 (3)
H27A—C27A—H27B	109.2	N3B—C28B—C27B	101.3 (3)
N3A—C28A—C29A	113.2 (3)	C29B—C28B—C27B	113.7 (3)
N3A—C28A—C27A	100.5 (3)	N3B—C28B—H28B	109.5
C29A—C28A—C27A	113.7 (3)	C29B—C28B—H28B	109.5
N3A—C28A—H28A	109.7	C27B—C28B—H28B	109.5
C29A—C28A—H28A	109.7	C34B—C29B—C30B	117.8 (4)
C27A—C28A—H28A	109.7	C34B—C29B—C28B	123.0 (4)
C34A—C29A—C30A	118.2 (4)	C30B—C29B—C28B	119.1 (4)
C34A—C29A—C28A	122.9 (4)	C31B—C30B—C29B	121.4 (4)
C30A—C29A—C28A	118.9 (4)	C31B—C30B—H30B	119.3
C29A—C30A—C31A	121.7 (5)	C29B—C30B—H30B	119.3
C29A—C30A—H30A	119.1	C32B—C31B—C30B	119.7 (5)
C31A—C30A—H30A	119.1	C32B—C31B—H31B	120.2
C32A—C31A—C30A	119.6 (5)	C30B—C31B—H31B	120.2
C32A—C31A—H31A	120.2	C33B—C32B—C31B	120.0 (5)
C30A—C31A—H31A	120.2	C33B—C32B—H32B	120.0
C33A—C32A—C31A	119.4 (5)	C31B—C32B—H32B	120.0
C33A—C32A—H32A	120.3	C32B—C33B—C34B	120.4 (5)
C31A—C32A—H32A	120.3	C32B—C33B—H33B	119.8
C32A—C33A—C34A	121.1 (5)	C34B—C33B—H33B	119.8
C32A—C33A—H33A	119.5	C29B—C34B—C33B	120.7 (5)
C34A—C33A—H33A	119.5	C29B—C34B—H34B	119.6
C29A—C34A—C33A	120.0 (5)	C33B—C34B—H34B	119.6
C29A—C34A—H34A	120.0
O6A—S1A—N4A—C26A	165.3 (3)	O6B—S1B—N4B—C26B	167.1 (3)
O5A—S1A—N4A—C26A	−66.4 (3)	O5B—S1B—N4B—C26B	−64.8 (3)
C24A—S1A—N4A—C26A	49.8 (3)	C24B—S1B—N4B—C26B	51.4 (3)
O6A—S1A—N4A—C27A	19.5 (3)	O6B—S1B—N4B—C27B	18.2 (3)
O5A—S1A—N4A—C27A	147.8 (3)	O5B—S1B—N4B—C27B	146.2 (3)
C24A—S1A—N4A—C27A	−96.1 (3)	C24B—S1B—N4B—C27B	−97.5 (3)
C16A—C11A—C12A—C13A	2.7 (6)	N1B—C11B—C12B—C13B	178.7 (4)
N1A—C11A—C12A—C13A	−176.0 (3)	C16B—C11B—C12B—C13B	0.2 (7)
C11A—C12A—C13A—C14A	−2.0 (6)	C11B—C12B—C13B—C14B	−2.4 (6)
C12A—C13A—C14A—C15A	0.4 (6)	C12B—C13B—C14B—C15B	3.1 (6)
C12A—C13A—C14A—C17A	173.3 (3)	C12B—C13B—C14B—C17B	176.7 (4)
C13A—C14A—C15A—C16A	0.6 (6)	C13B—C14B—C15B—C16B	−1.8 (6)
C17A—C14A—C15A—C16A	−171.9 (4)	C17B—C14B—C15B—C16B	−175.1 (4)
C12A—C11A—C16A—C15A	−1.7 (6)	C14B—C15B—C16B—C11B	−0.3 (7)
N1A—C11A—C16A—C15A	177.0 (4)	C12B—C11B—C16B—C15B	1.1 (7)
C14A—C15A—C16A—C11A	0.0 (6)	N1B—C11B—C16B—C15B	−177.4 (4)
C21A—N2A—C17A—O8A	−7.0 (6)	C21B—N2B—C17B—O8B	−4.1 (6)
C18A—N2A—C17A—O8A	156.6 (4)	C18B—N2B—C17B—O8B	157.0 (4)
C18A—N2A—C17A—C14A	−26.8 (5)	C18B—N2B—C17B—C14B	−22.9 (6)
C21A—N2A—C17A—C14A	169.7 (3)	C21B—N2B—C17B—C14B	176.1 (3)
C15A—C14A—C17A—O8A	141.2 (4)	C15B—C14B—C17B—O8B	143.3 (4)
C13A—C14A—C17A—O8A	−31.4 (5)	C13B—C14B—C17B—O8B	−30.0 (6)
C15A—C14A—C17A—N2A	−35.6 (5)	C15B—C14B—C17B—N2B	−36.9 (6)
C13A—C14A—C17A—N2A	151.9 (3)	C13B—C14B—C17B—N2B	149.8 (4)
C17A—N2A—C18A—C19A	−141.4 (4)	C17B—N2B—C18B—C19B	−153.4 (3)
C21A—N2A—C18A—C19A	24.3 (4)	C21B—N2B—C18B—C19B	9.8 (4)
N2A—C18A—C19A—C20A	−24.8 (4)	N2B—C18B—C19B—C20B	−9.3 (4)
C18A—C19A—C20A—C21A	18.2 (4)	C18B—C19B—C20B—C21B	5.9 (4)
C18A—C19A—C20A—C25A	−161.6 (4)	C18B—C19B—C20B—C25B	−173.7 (4)
C25A—C20A—C21A—C22A	−0.1 (6)	C25B—C20B—C21B—C22B	2.2 (5)
C19A—C20A—C21A—C22A	−180.0 (3)	C19B—C20B—C21B—C22B	−177.5 (3)
C25A—C20A—C21A—N2A	176.3 (3)	C25B—C20B—C21B—N2B	179.7 (3)
C19A—C20A—C21A—N2A	−3.5 (4)	C19B—C20B—C21B—N2B	0.1 (4)
C17A—N2A—C21A—C20A	152.7 (3)	C17B—N2B—C21B—C22B	−25.6 (5)
C18A—N2A—C21A—C20A	−13.5 (4)	C17B—N2B—C21B—C20B	157.1 (3)
C17A—N2A—C21A—C22A	−31.1 (6)	C18B—N2B—C21B—C20B	−6.4 (4)
C18A—N2A—C21A—C22A	162.7 (4)	C18B—N2B—C21B—C22B	170.9 (4)
C20A—C21A—C22A—C23A	0.2 (6)	C20B—C21B—C22B—C23B	−1.2 (5)
N2A—C21A—C22A—C23A	−175.6 (3)	N2B—C21B—C22B—C23B	−178.2 (3)
C21A—C22A—C23A—C24A	−0.1 (6)	C21B—C22B—C23B—C24B	−0.2 (5)
C22A—C23A—C24A—C25A	0.1 (6)	C22B—C23B—C24B—C25B	0.7 (5)
C22A—C23A—C24A—S1A	179.7 (3)	C22B—C23B—C24B—S1B	179.7 (3)
O6A—S1A—C24A—C23A	−31.9 (4)	O6B—S1B—C24B—C23B	−30.6 (3)
O5A—S1A—C24A—C23A	−164.1 (3)	O5B—S1B—C24B—C23B	−163.7 (3)
N4A—S1A—C24A—C23A	80.2 (3)	N4B—S1B—C24B—C23B	81.0 (3)
O6A—S1A—C24A—C25A	147.8 (3)	O6B—S1B—C24B—C25B	148.4 (3)
O5A—S1A—C24A—C25A	15.6 (3)	O5B—S1B—C24B—C25B	15.3 (3)
N4A—S1A—C24A—C25A	−100.2 (3)	N4B—S1B—C24B—C25B	−99.9 (3)
C21A—C20A—C25A—C24A	0.0 (5)	C21B—C20B—C25B—C24B	−1.7 (5)
C19A—C20A—C25A—C24A	179.8 (4)	C19B—C20B—C25B—C24B	177.9 (4)
C23A—C24A—C25A—C20A	0.0 (5)	C23B—C24B—C25B—C20B	0.3 (5)
S1A—C24A—C25A—C20A	−179.6 (3)	S1B—C24B—C25B—C20B	−178.7 (3)
C28A—N3A—C26A—O7A	178.3 (4)	C28B—N3B—C26B—O7B	177.2 (4)
C28A—N3A—C26A—N4A	−4.0 (5)	C28B—N3B—C26B—N4B	−2.2 (5)
C27A—N4A—C26A—O7A	166.0 (4)	C27B—N4B—C26B—O7B	168.9 (4)
S1A—N4A—C26A—O7A	16.9 (5)	S1B—N4B—C26B—O7B	17.3 (5)
C27A—N4A—C26A—N3A	−11.9 (4)	C27B—N4B—C26B—N3B	−11.7 (4)
S1A—N4A—C26A—N3A	−161.0 (3)	S1B—N4B—C26B—N3B	−163.3 (3)
C26A—N4A—C27A—C28A	21.3 (4)	C26B—N4B—C27B—C28B	19.5 (4)
S1A—N4A—C27A—C28A	170.5 (2)	S1B—N4B—C27B—C28B	171.5 (2)
C26A—N3A—C28A—C29A	−105.0 (4)	C26B—N3B—C28B—C29B	−108.2 (4)
C26A—N3A—C28A—C27A	16.7 (5)	C26B—N3B—C28B—C27B	13.8 (4)
N4A—C27A—C28A—N3A	−21.4 (4)	N4B—C27B—C28B—N3B	−18.8 (4)
N4A—C27A—C28A—C29A	99.9 (4)	N4B—C27B—C28B—C29B	102.7 (4)
N3A—C28A—C29A—C34A	19.1 (5)	N3B—C28B—C29B—C34B	20.4 (5)
C27A—C28A—C29A—C34A	−94.8 (4)	C27B—C28B—C29B—C34B	−94.3 (4)
N3A—C28A—C29A—C30A	−162.0 (3)	N3B—C28B—C29B—C30B	−160.6 (3)
C27A—C28A—C29A—C30A	84.1 (4)	C27B—C28B—C29B—C30B	84.6 (4)
C34A—C29A—C30A—C31A	1.7 (6)	C34B—C29B—C30B—C31B	1.3 (6)
C28A—C29A—C30A—C31A	−177.3 (4)	C28B—C29B—C30B—C31B	−177.7 (4)
C29A—C30A—C31A—C32A	−0.4 (7)	C29B—C30B—C31B—C32B	−0.5 (7)
C30A—C31A—C32A—C33A	−1.1 (8)	C30B—C31B—C32B—C33B	−0.6 (7)
C31A—C32A—C33A—C34A	1.3 (8)	C31B—C32B—C33B—C34B	0.9 (8)
C30A—C29A—C34A—C33A	−1.4 (6)	C30B—C29B—C34B—C33B	−1.0 (6)
C28A—C29A—C34A—C33A	177.5 (4)	C28B—C29B—C34B—C33B	178.0 (4)
C32A—C33A—C34A—C29A	0.0 (7)	C32B—C33B—C34B—C29B	−0.1 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O7A^i	0.89	1.90	2.768 (4)	166
N1A—H1B···Cl1^ii	0.89	2.22	3.110 (4)	174
N1A—H1C···O7B^iii	0.89	2.36	3.086 (4)	139
N1A—H1C···N1B	0.89	2.51	3.008 (4)	116
N1B—H1D···O7B^iii	0.86	2.23	2.980 (4)	145
N1B—H1E···Cl1^ii	0.86	2.66	3.502 (4)	166
N3A—H3A···Cl1^iv	0.86	2.32	3.106 (3)	153
N3B—H3B···Cl1	0.86	2.33	3.103 (3)	150
C18A—H18A···O8A^v	0.97	2.55	3.018 (4)	109
C19A—H19B···O8A^v	0.97	2.85	3.336 (5)	112
C27A—H27A···O5A^vi	0.97	2.48	2.935 (4)	109
C28A—H28A···O5A^vi	0.98	2.64	3.158 (5)	113
C18B—H18C···O8B^v	0.97	2.44	3.123 (5)	127
C19B—H19D···O8B^v	0.97	2.78	3.351 (5)	118
C27B—H27C···O5B^vi	0.97	2.46	2.919 (4)	109
C28B—H28B···O5B^vi	0.98	2.57	3.095 (5)	113

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