Di­methyl 3,4,5,5-tetra­phenyl-1,3-thia­zolidine-2,2-di­carboxyl­ate and 3,3-di­chloro-2,2,4,4,3′-penta­methyl-r-2′,t-4′-di­phenyl­cyclo­butane-1-spiro-5′-1,3-thia­zolidine

The first of the title compounds, C₃₁H₂₇NO₄S, (V), crystallizes in the monoclinic space group P2₁/c with two independent mol­ecules in the asymmetric unit, while the second, C₂₃H₂₇Cl₂NS, (IX), crystallizes in the orthorhombic space group Pbca with one mol­ecule in the asymmetric unit. In both crystal structures, the 1,3-thia­zolidine ring adopts a half-chair conformation. The crystal structures are stabilized by weak C—H...O and C—H...Cl hydrogen bonds in (V) and (IX), respectively.

S1. Comment

1,3-Thiazolidines are known to exhibit biological activity (Hwu et al., 1999; Pellegrini et al., 1999) and are also explored as valuable starting materials for the preparation of more complex structures (Bringmann et al., 2000; Jin & Kim, 2002). The title compounds, (V) and (IX), were obtained by the [3 + 2] dipolar cycloaddition of an azomethine ylide, generated in situ by thermal ring-opening of the appropriate aziridine in the presence of thiobenzophenone, (IV), or 3,3-dichloro-2,2,4,4-tetramethylcyclobutanethione, (VIII) (see Scheme), according to the general protocol of Mlostoń & Skrzypek (1990). \sch

Sometimes, desulfurization of 1,3-thiazolidines with Raney nickel results unexpectedly in ring contraction and the formation of the corresponding azetidine derivative (Mlostoń Urbaniak & Heimgartner, 2002; Mlostoń Urbaniak et al., 2002; Urbaniak et al., 2004). For this reason, our studies of this group of compounds concern not only the elucidation of their structures, conformations and configurations, but also the determination of the influence of the location of the ester groups on the course of the desulfurization reaction. Detailed studies of 1,3-thiazolidine derivatives show that the regioselectivity of the [3 + 2] cycloaddition leading to the formation of the five-membered heterocyclic ring is dependent on the type of thioketone used (Domagała Linden et al., 2003).

Another aim of the present work was an analysis of the hydrogen bonding, one of the most important interactions influencing the arrangement of molecules in molecular organic crystals (Desiraju, 1989; Jeffrey & Saenger, 1994; Desiraju & Steiner, 1999). Studies of hydrogen-bond interactions have shown that the H-atom-donating and -accepting abilities of molecules determine the architecture of crystals. In recent years, the role of C—H···X hydrogen bonds in the crystal engineering has been extensively studied. Among C—H···X interactions, the C—H···O type is most often investigated because it occurs most frequently in crystals. For the crystal structures reported here, not only C—H···O interactions occur but also C—H···S and C—H···N ones, which are not well known because of their rare occurrence in crystals (Taylor & Kennard, 1982; Desiraju, 1995; Desiraju & Steiner, 1999). The contacts mentioned above have been investigated previously, both theoretically and experimentally (Domagała Grabowski et al., 2003; Domagała Grabowski et al., 2004). C—H···π contacts are another type of interaction investigated here for the crystal structures of (V) and (IX). Such interactions often have an influence on the crystal packing (Ciunik et al., 1998; Ciunik & Jarosz, 1998).

The asymmetric unit of compound (V) contains two independent molecules (denoted A and B) which have the same five-membered heterocyclic ring conformation and opposite absolute configurations. The chiral centre is at atom C4. In Fig. 1, the phenyl substituent is attached in the S configuration in molecule A, whereas in molecule B this configuration is R. Compound (IX) crystallizes with one molecule in the asymmetric unit. There are two centres of opposite chirality in this molecule, at atoms C2 and C4.

The bond lengths and angles in the title structures are generally in good agreement with expected values (Allen et al., 1987). However, in (V), there is a slight elongation of the C4A—C5A and C4B—C5B bonds in comparison with the expected values (both ca 1.56 Å), and the C—S bonds are asymmetric, similar to what was observed in our previously reported structures. C—C bond lengths in the range 1.56–1.61 Å have been observed frequently in spirocyclic thiazolidine, thiazole, oxathiolane and dithiolane ring systems (Linden et al., 1998; Domagała Grabowski et al., 2003; Domagała Grabowski et al., 2004). Moreover, the C2A—N3A—C4A and C2B—N3B—C4B bond angles are larger then the corresponding angle in compound (IX). Steric hindrance is probably responsible for the observed geometry of the thiazolidine ring. In both compounds, the 1,3-thiazolidine rings adopt half-chair conformations.

The puckering parameters (Cremer & Pople, 1975) for (V), for the atom sequence C5/S1/C2/N3/C4, are q₂ = 0.5439 (14) Å and ϕ₂ = −161.4 (1)°, and q₂ = 0.5355 (15) Å and ϕ₂=18.4 (2)°, for molecules A and B, respectively, with pseudo-twofold axes passing through atom N3 and the mid-point of the C5—S1 bond [asymmetry parameters (Nardelli, 1983) Δ = 0.0135 (6) for molecule A and 0.0127 (6) for molecule B]. For compound (IX), the puckering parameters for the same sequence of atoms are q₂ = 0.5000 (16) Å and ϕ₂ = −17.2 (2)°. The pseudo-twofold axis passes through atom S1 and the mid-point of the N3—C4 bond [Δ = 0.0050 (7)]. In both compounds, the substituents attached at N3 are nearly in the plane of the N3/C2/S1/C5/C4 ring, whereas those at C4 occupy pseudo-axial positions. In compound (V), the planes of the phenyl rings at C4, as well as of those at C2 and C4 in (IX), lie almost perpendicular to the mean planes of the 1,3-thiazolidine rings, with interplanar angles of 85.9 (1) and 88.6 (1)° for molecules A and B, respectively, in (V), and 79.3 (1) and 89.1 (1)°, respectively, in (IX). In contrast, the planes of the phenyl substituents at N3A and N3B of (V) lie almost parallel to the planes of the respective 1,3-thiazolidine rings, with interplanar angles of 16.1 (1) and 19.6 (1)°, respectively. In compound (IX), the chloro-substituted cyclobutane ring is nearly perpendicular to the central 1,3-thiazolidine ring; the angle between these planes is 85.59 (5)°. This four-membered ring is more puckered than that in a previously reported structure (Domagała, Małecka et al., 2004), where there was a carboxyl group instead of Cl atoms. The puckering parameter for the C54/C56/C5/C51 sequence of atoms is q₂ = 0.209 (2) Å, and the pseudo-mirror plane passes through atoms C54 and C5 [Δ = 0.0002 (11)]. The general rule for predicting the conformation of cyclobutane compounds in the solid state (Margulis, 1969; Adman & Margulis, 1969) would suggest that such ring puckering is connected with the asymmetric arrangement of the substituents. The internal bond lengths and angles are consistent with those previously reported (Shirrell & Williams, 1973; Shirrell & Williams, 1974). It is worth mentioning that the C54—C51 [1.564 (2) Å] and C54—C56 [1.551 (2) Å] bond lengths are significantly shorter than those on the spiro side of the ring [C5—C51 1.585 (2) and C5—C56 1.592 (2) Å], and consequently the C51—C54—C56 angle is the largest [92.3 (1)°] of the C—C—C angles. Presumably, this is a result of the interaction between the cyclobutane and 1,3-thiazolidine rings.

Because of the attached substituents on the 1,3-thiazolidine ring, the title compounds have slightly different abilities to form hydrogen bonds. The criterion of H···A distances shorter than the corresponding sum of the van der Waals radii was applied as the definition of hydrogen bonds. Geometric parameters for possible hydrogen bonds in (V) and (IX) are given in Tables 2 and 4, respectively. In both compounds, the molecular structures are stabilized by intramolecular C—H···S and C—H···N interactions. These interactions were the subject of our previous experimental and theoretical investigations on the group of 1,3-thiazolidine derivatives (Domagała Grabowski et al., 2003; Domagała Grabowski et al., 2004).

The use of the Bader theory (Bader, 1990) has shown that only C—H···S interactions fulfil not only the geometric but also the topological criteria for the existence of hydrogen bonds. The most reasonable explanation for the lack of the topological confirmation of C—H···N interactions could be too small a C—H—N angle, in spite of an appropriate H-atom-acceptor distance. Nevertheless, it is important to take into consideration such interactions and their influence on molecular structures (Desiraju & Steiner, 1999).

The presence of carboxymethyl groups in (V) gives another type of intramolecular contact stabilizing the molecular structure, namely C–H···O interactions. Among all intramolecular C—H···O interactions, two clearly stand out, these being C46—H46···O28 in molecules A and B. The length of this H···O contact is distinctly shorter, by about 0.2 Å, than the remaining intramolecular contacts, and, more importantly, the C—H···O angle is clearly near linearity, at 166°. As is known, C—H···O interactions are mostly electrostatic in nature, so a geometry close to linear favours the existence of these hydrogen bonds. In compound (IX), atom C58 is involved in two intramolecular interactions, C58—H58···Cl59 and C58—H58···S1.

While intramolecular hydrogen bonds play a crucial role in stabilizing molecular structures, the most important interactions responsible for the architecture of crystals are intermolecular interactions. There are many C—H···O contacts for compound (V). Among these, the C27A—H27A···O24ⁱ contact differs in geometry from the others in that the H···O distance is the shortest, at 2.37 Å, and the angle is the smallest, at 108° [symmetry code: (i) Please provide missing symmetry code]. It is worth mentioning that atom O28B takes part in three hydrogen bonds. As an acceptor, it is involved in two intermolecular hydrogen bonds, connecting two symmetrically independent molecules A and B [C42A—H42A···O28B and C44A—H44A···O28Bⁱⁱ], and in one intramolecular hydrogen bond [C46B—H46B···O28B] [symmetry code: (ii) Please provide missing symmetry code]. What is more, the crystal packing is also stabilized by C—H···π interactions, C23B—H234···Cg1^iv [Cg1 denotes the centroid of the phenyl ring attached at N3A; symmetry code: (iv) Please provide missing symmetry code] (Ciunik et al., 1998; Ciunik & Jarosz, 1998; Desiraju & Steiner, 1999). In compound (IX), just as in compound (V), a stabilizing C23—H23···Cg2ⁱⁱ interaction is observed, where Cg2 denotes the centroid of the phenyl ring attached at C4. However, the most significant intermolecular connections in (IX) are C—H···Cl interactions, which hold the molecules together to form dimers (Fig. 3) of graph-set motif R₂²(10) (Bernstein et al., 1995).

The two Domagała et al. (2003) references and the two Domagała et al. (2004) references were not uniquely cited in the original CIF. Please check that they have been correctly differentiated in all citations above.

S2. Experimental

Compounds (V) and (IX) were obtained by [3 + 2] dipolar cycloaddition of the corresponding azomethine ylide, generated in situ by thermal ring-opening of dimethyl 1,3-diphenylaziridine-2,2-dicarboxylate with thiobenzophenone for (V), and 1,3-diphenyl-2-methylaziridine with 3,3-dichloro-2,2,4,4-tetramethylcyclobuthanethione for (IX), according to the general procedures of Mloston & Skrzypek (1990) and Urbaniak et al. (2004). Both compounds were characterized using the methods of elemental analysis, and IR and NMR spectroscopy. Crystals suitable for X-ray crystallography were obtained by slow evaporation of methanol and dichloromethane? solutions of the compounds at room temperature [m.p. 426–428 K for (V) and 467–469 K for (IX)].

S3. Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å. For methoxy H atoms, U_iso(H) = 1.5U_eq(C); for all other H atoms, U_iso(H) = 1.2U_eq(C).

Computing details

For both compounds, data collection: IPDS (Stoe, 1998); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: PARST (Nardelli, 1996).

Figures

	Fig. 1. A view of the two symmetry-independent 1,3-thiazolidine molecules of (V), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by small spheres of arbitrary radii.
	Fig. 2. A view of the molecule of (IX), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by small spheres of arbitrary radii.
	Fig. 3. A view of the dimer formed by the intermolecular C—H···Cl interactions (dashed lines) in the structure of (IX).

(V) Dimethyl 3,4,5,5-tetraphenyl-1,3-thiazolidine-2,2-dicarboxylate

Crystal data

C31H27NO4S	F(000) = 2144
Mr = 509.6	Dx = 1.304 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8000 reflections
a = 19.4758 (9) Å	θ = 2.4–25.9°
b = 12.2344 (6) Å	µ = 0.16 mm^−1
c = 22.1493 (10) Å	T = 173 K
β = 100.380 (5)°	Cut block, colourless
V = 5191.2 (4) Å^3	0.4 × 0.3 × 0.3 mm
Z = 8

Data collection

Stoe IPDS diffractometer	Rint = 0.041
Graphite monochromator	θmax = 25.9°, θmin = 2.3°
rotation scans	h = −23→23
35574 measured reflections	k = −14→14
9960 independent reflections	l = −27→27
7484 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0653P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.092	(Δ/σ)max = 0.001
S = 0.91	Δρmax = 0.42 e Å^−3
9960 reflections	Δρmin = −0.18 e Å^−3
671 parameters

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.

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

	x	y	z	Uiso*/Ueq
S1A	0.168640 (18)	−0.01970 (3)	0.628864 (17)	0.02382 (9)
O28A	0.16746 (6)	−0.07898 (10)	0.77107 (6)	0.0369 (3)
O26A	0.05324 (6)	−0.06197 (9)	0.73130 (5)	0.0335 (3)
O24A	0.03513 (5)	0.18011 (9)	0.68123 (5)	0.0314 (3)
O22A	0.02068 (6)	0.03813 (9)	0.61706 (6)	0.0366 (3)
N3A	0.18029 (6)	0.13404 (10)	0.71165 (6)	0.0230 (3)
C2A	0.12987 (7)	0.04993 (12)	0.68754 (7)	0.0231 (3)
C4A	0.23371 (7)	0.15922 (12)	0.67469 (7)	0.0222 (3)
H4A	0.2354	0.2406	0.6707	0.027*
C5A	0.20552 (7)	0.11260 (11)	0.60957 (7)	0.0227 (3)
C25A	0.12095 (8)	−0.03850 (12)	0.73579 (7)	0.0260 (3)
C27A	0.03449 (9)	−0.14388 (15)	0.77265 (9)	0.0377 (4)
H271	−0.0133	−0.1689	0.7576	0.057*
H272	0.0374	−0.1122	0.8137	0.057*
H273	0.0667	−0.2059	0.7747	0.057*
C21A	0.05649 (7)	0.09897 (12)	0.66143 (7)	0.0234 (3)
C23A	−0.04985 (10)	0.0769 (2)	0.59468 (12)	0.0616 (7)
H231	−0.0677	0.0440	0.5546	0.092*
H232	−0.0494	0.1567	0.5906	0.092*
H233	−0.0800	0.0564	0.6238	0.092*
C31A	0.17967 (8)	0.19062 (12)	0.76656 (7)	0.0251 (3)
C32A	0.12971 (8)	0.17106 (14)	0.80364 (7)	0.0320 (4)
H32A	0.0945	0.1178	0.7914	0.038*
C33A	0.13099 (9)	0.22830 (17)	0.85777 (8)	0.0399 (4)
H33A	0.0972	0.2125	0.8825	0.048*
C34A	0.18072 (9)	0.30818 (17)	0.87646 (8)	0.0421 (4)
H34A	0.1808	0.3480	0.9133	0.051*
C35A	0.23020 (9)	0.32867 (15)	0.84022 (8)	0.0373 (4)
H35A	0.2644	0.3836	0.8523	0.045*
C36A	0.23080 (8)	0.27054 (13)	0.78670 (7)	0.0293 (3)
H36A	0.2661	0.2847	0.7632	0.035*
C41A	0.30693 (7)	0.12141 (12)	0.70359 (7)	0.0240 (3)
C42A	0.36364 (8)	0.18332 (14)	0.69317 (7)	0.0298 (3)
H42A	0.3558	0.2478	0.6690	0.036*
C43A	0.43145 (8)	0.15211 (15)	0.71763 (8)	0.0348 (4)
H43A	0.4698	0.1947	0.7101	0.042*
C44A	0.44288 (8)	0.05856 (15)	0.75312 (8)	0.0351 (4)
H44A	0.4892	0.0368	0.7700	0.042*
C45A	0.38710 (8)	−0.00323 (14)	0.76395 (8)	0.0335 (4)
H45A	0.3952	−0.0677	0.7881	0.040*
C46A	0.31898 (8)	0.02832 (13)	0.73973 (7)	0.0281 (3)
H46A	0.2808	−0.0139	0.7480	0.034*
C51A	0.26284 (8)	0.09357 (12)	0.57176 (7)	0.0248 (3)
C56A	0.30456 (9)	−0.00012 (14)	0.57861 (8)	0.0327 (4)
H56A	0.2964	−0.0556	0.6065	0.039*
C55A	0.35776 (9)	−0.01310 (15)	0.54512 (9)	0.0397 (4)
H55A	0.3852	−0.0778	0.5497	0.048*
C54A	0.37095 (9)	0.06766 (16)	0.50505 (9)	0.0396 (4)
H54A	0.4072	0.0586	0.4820	0.048*
C53A	0.33099 (9)	0.16154 (15)	0.49887 (8)	0.0363 (4)
H53A	0.3404	0.2178	0.4719	0.044*
C52A	0.27713 (8)	0.17455 (13)	0.53170 (7)	0.0290 (3)
H52A	0.2498	0.2393	0.5268	0.035*
C57A	0.14517 (7)	0.18187 (12)	0.57412 (7)	0.0246 (3)
C62A	0.12531 (8)	0.28232 (13)	0.59384 (7)	0.0282 (3)
H62A	0.1503	0.3128	0.6308	0.034*
C61A	0.06922 (9)	0.33961 (14)	0.56034 (8)	0.0357 (4)
H61A	0.0565	0.4087	0.5745	0.043*
C60A	0.03205 (9)	0.29645 (16)	0.50659 (9)	0.0403 (4)
H60A	−0.0064	0.3351	0.4839	0.048*
C59A	0.05153 (9)	0.19634 (16)	0.48624 (8)	0.0418 (4)
H59A	0.0264	0.1659	0.4493	0.050*
C58A	0.10771 (9)	0.14013 (15)	0.51950 (8)	0.0351 (4)
H58A	0.1209	0.0718	0.5047	0.042*
S1B	0.277582 (18)	0.45509 (3)	0.597706 (18)	0.02473 (9)
O28B	0.43732 (6)	0.41394 (9)	0.65193 (5)	0.0309 (3)
O26B	0.43770 (6)	0.38051 (9)	0.55254 (5)	0.0322 (3)
O24B	0.36676 (6)	0.61151 (10)	0.48222 (5)	0.0374 (3)
O22B	0.31230 (6)	0.44934 (9)	0.47339 (5)	0.0334 (3)
N3B	0.36629 (6)	0.61611 (10)	0.60960 (6)	0.0237 (3)
C2B	0.35602 (7)	0.51403 (12)	0.57558 (7)	0.0239 (3)
C4B	0.30735 (7)	0.65659 (12)	0.63654 (7)	0.0230 (3)
H4B	0.3007	0.7352	0.6246	0.028*
C5B	0.24177 (7)	0.59388 (12)	0.60260 (7)	0.0242 (3)
C25B	0.41551 (7)	0.43038 (12)	0.59874 (7)	0.0244 (3)
C27B	0.49296 (9)	0.30046 (15)	0.57116 (9)	0.0394 (4)
H275	0.5076	0.2698	0.5346	0.059*
H274	0.4755	0.2417	0.5944	0.059*
H276	0.5329	0.3361	0.5970	0.059*
C21B	0.34620 (8)	0.53195 (13)	0.50471 (7)	0.0267 (3)
C23B	0.29729 (10)	0.46379 (16)	0.40705 (8)	0.0418 (4)
H234	0.2741	0.3982	0.3878	0.063*
H235	0.3410	0.4757	0.3920	0.063*
H236	0.2666	0.5272	0.3968	0.063*
C31B	0.42905 (7)	0.67534 (12)	0.61689 (7)	0.0241 (3)
C32B	0.48451 (8)	0.64282 (13)	0.58852 (8)	0.0289 (3)
H32B	0.4797	0.5798	0.5630	0.035*
C33B	0.54624 (8)	0.70147 (14)	0.59720 (8)	0.0345 (4)
H33B	0.5833	0.6777	0.5777	0.041*
C34B	0.55505 (9)	0.79353 (15)	0.63351 (9)	0.0397 (4)
H34B	0.5978	0.8329	0.6395	0.048*
C35B	0.50051 (9)	0.82762 (14)	0.66112 (9)	0.0368 (4)
H35B	0.5057	0.8917	0.6858	0.044*
C36B	0.43827 (8)	0.76971 (13)	0.65341 (7)	0.0283 (3)
H36B	0.4016	0.7942	0.6730	0.034*
C41B	0.31827 (7)	0.65233 (12)	0.70639 (7)	0.0238 (3)
C42B	0.28581 (8)	0.73117 (13)	0.73671 (7)	0.0284 (3)
H42B	0.2574	0.7851	0.7136	0.034*
C43B	0.29430 (9)	0.73224 (15)	0.80028 (8)	0.0351 (4)
H43B	0.2712	0.7859	0.8203	0.042*
C44B	0.33646 (9)	0.65502 (16)	0.83443 (8)	0.0392 (4)
H44B	0.3429	0.6558	0.8780	0.047*
C45B	0.36908 (9)	0.57666 (15)	0.80454 (8)	0.0377 (4)
H45B	0.3982	0.5237	0.8279	0.045*
C46B	0.35999 (8)	0.57417 (13)	0.74104 (8)	0.0287 (3)
H46B	0.3822	0.5192	0.7212	0.034*
C51B	0.18211 (7)	0.59086 (12)	0.63935 (7)	0.0250 (3)
C56B	0.18145 (8)	0.51752 (13)	0.68724 (8)	0.0294 (3)
H56B	0.2180	0.4656	0.6968	0.035*
C55B	0.12820 (9)	0.51907 (15)	0.72121 (8)	0.0352 (4)
H55B	0.1282	0.4678	0.7534	0.042*
C54B	0.07503 (9)	0.59537 (16)	0.70825 (9)	0.0398 (4)
H54B	0.0384	0.5964	0.7313	0.048*
C53B	0.07569 (9)	0.67015 (16)	0.66143 (9)	0.0387 (4)
H53B	0.0397	0.7233	0.6528	0.046*
C52B	0.12841 (8)	0.66792 (14)	0.62712 (8)	0.0312 (3)
H52B	0.1281	0.7193	0.5949	0.037*
C57B	0.21560 (7)	0.63573 (13)	0.53700 (7)	0.0267 (3)
C62B	0.16758 (9)	0.57191 (15)	0.49734 (8)	0.0369 (4)
H62B	0.1520	0.5047	0.5115	0.044*
C61B	0.14260 (10)	0.60520 (17)	0.43797 (9)	0.0465 (5)
H61B	0.1098	0.5610	0.4118	0.056*
C60B	0.16484 (10)	0.70236 (17)	0.41625 (8)	0.0448 (5)
H60B	0.1483	0.7244	0.3751	0.054*
C59B	0.21106 (10)	0.76671 (17)	0.45472 (9)	0.0444 (4)
H59B	0.2258	0.8343	0.4403	0.053*
C58B	0.23651 (9)	0.73370 (15)	0.51478 (8)	0.0358 (4)
H58B	0.2687	0.7790	0.5408	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.02508 (18)	0.02175 (17)	0.02552 (19)	−0.00006 (13)	0.00691 (14)	−0.00099 (14)
O28A	0.0275 (6)	0.0449 (7)	0.0386 (7)	0.0044 (5)	0.0065 (5)	0.0172 (6)
O26A	0.0251 (5)	0.0364 (6)	0.0394 (7)	−0.0042 (5)	0.0066 (5)	0.0123 (5)
O24A	0.0259 (5)	0.0323 (6)	0.0357 (6)	0.0052 (5)	0.0049 (5)	−0.0057 (5)
O22A	0.0255 (6)	0.0372 (6)	0.0418 (7)	0.0041 (5)	−0.0080 (5)	−0.0113 (5)
N3A	0.0203 (6)	0.0268 (6)	0.0218 (6)	−0.0012 (5)	0.0038 (5)	−0.0016 (5)
C2A	0.0214 (7)	0.0241 (7)	0.0239 (7)	0.0011 (6)	0.0042 (6)	−0.0002 (6)
C4A	0.0227 (7)	0.0224 (7)	0.0215 (7)	−0.0002 (5)	0.0042 (6)	0.0006 (6)
C5A	0.0245 (7)	0.0206 (7)	0.0231 (7)	−0.0015 (5)	0.0042 (6)	0.0015 (6)
C25A	0.0253 (7)	0.0269 (8)	0.0274 (8)	0.0003 (6)	0.0093 (6)	0.0003 (6)
C27A	0.0350 (9)	0.0379 (9)	0.0418 (10)	−0.0056 (7)	0.0109 (7)	0.0126 (8)
C21A	0.0221 (7)	0.0251 (8)	0.0235 (7)	−0.0007 (6)	0.0058 (6)	0.0013 (6)
C23A	0.0304 (10)	0.0643 (13)	0.0784 (16)	0.0115 (9)	−0.0215 (10)	−0.0239 (12)
C31A	0.0239 (7)	0.0297 (8)	0.0206 (7)	0.0058 (6)	0.0007 (6)	−0.0008 (6)
C32A	0.0265 (8)	0.0414 (9)	0.0278 (8)	0.0005 (7)	0.0042 (6)	−0.0021 (7)
C33A	0.0333 (9)	0.0606 (12)	0.0274 (9)	0.0041 (8)	0.0095 (7)	−0.0051 (8)
C34A	0.0400 (10)	0.0573 (12)	0.0279 (9)	0.0062 (8)	0.0027 (7)	−0.0153 (8)
C35A	0.0353 (9)	0.0405 (9)	0.0333 (9)	0.0010 (7)	−0.0013 (7)	−0.0104 (8)
C36A	0.0282 (8)	0.0325 (8)	0.0264 (8)	0.0020 (6)	0.0029 (6)	−0.0020 (7)
C41A	0.0225 (7)	0.0285 (8)	0.0209 (7)	0.0009 (6)	0.0035 (6)	−0.0022 (6)
C42A	0.0269 (8)	0.0338 (8)	0.0280 (8)	−0.0032 (6)	0.0035 (6)	0.0015 (7)
C43A	0.0225 (8)	0.0489 (10)	0.0334 (9)	−0.0052 (7)	0.0057 (6)	−0.0014 (8)
C44A	0.0234 (8)	0.0490 (10)	0.0313 (9)	0.0062 (7)	0.0003 (6)	−0.0021 (8)
C45A	0.0320 (8)	0.0359 (9)	0.0309 (9)	0.0073 (7)	0.0010 (7)	0.0035 (7)
C46A	0.0251 (7)	0.0309 (8)	0.0282 (8)	0.0006 (6)	0.0045 (6)	0.0017 (7)
C51A	0.0250 (7)	0.0280 (8)	0.0215 (7)	−0.0020 (6)	0.0041 (6)	−0.0026 (6)
C56A	0.0356 (9)	0.0309 (8)	0.0340 (9)	0.0030 (7)	0.0127 (7)	0.0030 (7)
C55A	0.0386 (9)	0.0391 (9)	0.0451 (10)	0.0080 (7)	0.0173 (8)	0.0004 (8)
C54A	0.0323 (9)	0.0513 (11)	0.0393 (10)	0.0011 (8)	0.0173 (8)	0.0011 (8)
C53A	0.0356 (9)	0.0430 (10)	0.0321 (9)	−0.0043 (7)	0.0113 (7)	0.0075 (8)
C52A	0.0288 (8)	0.0313 (8)	0.0267 (8)	−0.0003 (6)	0.0047 (6)	0.0022 (7)
C57A	0.0242 (7)	0.0283 (8)	0.0220 (8)	−0.0006 (6)	0.0061 (6)	0.0049 (6)
C62A	0.0248 (7)	0.0292 (8)	0.0303 (8)	−0.0001 (6)	0.0038 (6)	0.0013 (7)
C61A	0.0318 (8)	0.0329 (9)	0.0428 (10)	0.0059 (7)	0.0077 (7)	0.0056 (8)
C60A	0.0313 (9)	0.0492 (11)	0.0379 (10)	0.0076 (8)	−0.0005 (7)	0.0142 (8)
C59A	0.0411 (10)	0.0522 (11)	0.0278 (9)	0.0016 (8)	−0.0057 (7)	0.0034 (8)
C58A	0.0395 (9)	0.0372 (9)	0.0264 (8)	0.0036 (7)	−0.0001 (7)	−0.0015 (7)
S1B	0.02015 (17)	0.02430 (18)	0.0307 (2)	−0.00195 (13)	0.00710 (14)	−0.00094 (15)
O28B	0.0288 (6)	0.0339 (6)	0.0297 (6)	0.0045 (5)	0.0042 (5)	−0.0009 (5)
O26B	0.0308 (6)	0.0366 (6)	0.0306 (6)	0.0087 (5)	0.0089 (5)	−0.0023 (5)
O24B	0.0408 (7)	0.0415 (7)	0.0307 (6)	−0.0075 (5)	0.0089 (5)	0.0034 (5)
O22B	0.0379 (6)	0.0342 (6)	0.0271 (6)	−0.0020 (5)	0.0029 (5)	−0.0053 (5)
N3B	0.0200 (6)	0.0246 (6)	0.0276 (7)	−0.0022 (5)	0.0071 (5)	−0.0033 (5)
C2B	0.0191 (7)	0.0264 (7)	0.0273 (8)	−0.0027 (6)	0.0072 (6)	−0.0019 (6)
C4B	0.0186 (7)	0.0236 (7)	0.0274 (8)	0.0002 (5)	0.0052 (6)	0.0008 (6)
C5B	0.0216 (7)	0.0237 (7)	0.0272 (8)	0.0012 (6)	0.0042 (6)	0.0000 (6)
C25B	0.0204 (7)	0.0247 (7)	0.0291 (9)	−0.0038 (6)	0.0075 (6)	−0.0033 (6)
C27B	0.0365 (9)	0.0442 (10)	0.0395 (10)	0.0165 (8)	0.0126 (8)	−0.0003 (8)
C21B	0.0223 (7)	0.0302 (8)	0.0287 (8)	0.0024 (6)	0.0074 (6)	−0.0007 (7)
C23B	0.0478 (10)	0.0503 (11)	0.0259 (9)	0.0053 (8)	0.0028 (8)	−0.0065 (8)
C31B	0.0219 (7)	0.0250 (7)	0.0254 (8)	−0.0006 (6)	0.0041 (6)	0.0045 (6)
C32B	0.0276 (8)	0.0286 (8)	0.0316 (8)	−0.0018 (6)	0.0085 (6)	−0.0004 (7)
C33B	0.0243 (8)	0.0371 (9)	0.0449 (10)	−0.0018 (6)	0.0137 (7)	0.0023 (8)
C34B	0.0276 (8)	0.0394 (10)	0.0532 (11)	−0.0116 (7)	0.0100 (8)	−0.0025 (9)
C35B	0.0330 (9)	0.0314 (9)	0.0466 (10)	−0.0091 (7)	0.0087 (7)	−0.0070 (8)
C36B	0.0244 (7)	0.0286 (8)	0.0329 (8)	−0.0019 (6)	0.0079 (6)	−0.0010 (7)
C41B	0.0180 (7)	0.0254 (7)	0.0282 (8)	−0.0036 (5)	0.0050 (6)	−0.0007 (6)
C42B	0.0248 (7)	0.0291 (8)	0.0317 (9)	0.0026 (6)	0.0059 (6)	−0.0008 (7)
C43B	0.0358 (9)	0.0383 (9)	0.0330 (9)	0.0054 (7)	0.0108 (7)	−0.0057 (7)
C44B	0.0427 (10)	0.0497 (11)	0.0261 (9)	0.0047 (8)	0.0084 (7)	0.0013 (8)
C45B	0.0377 (9)	0.0417 (10)	0.0331 (9)	0.0119 (7)	0.0046 (7)	0.0072 (8)
C46B	0.0246 (7)	0.0307 (8)	0.0313 (8)	0.0040 (6)	0.0064 (6)	0.0002 (7)
C51B	0.0186 (7)	0.0292 (8)	0.0267 (8)	−0.0035 (6)	0.0029 (6)	−0.0042 (6)
C56B	0.0247 (7)	0.0304 (8)	0.0334 (9)	−0.0014 (6)	0.0065 (6)	−0.0002 (7)
C55B	0.0337 (9)	0.0389 (9)	0.0356 (9)	−0.0043 (7)	0.0133 (7)	0.0029 (8)
C54B	0.0267 (8)	0.0537 (11)	0.0428 (10)	−0.0008 (7)	0.0162 (7)	−0.0033 (9)
C53B	0.0262 (8)	0.0502 (11)	0.0406 (10)	0.0093 (7)	0.0086 (7)	−0.0002 (8)
C52B	0.0255 (8)	0.0361 (9)	0.0320 (9)	0.0022 (6)	0.0050 (6)	0.0002 (7)
C57B	0.0205 (7)	0.0335 (8)	0.0268 (8)	0.0053 (6)	0.0063 (6)	0.0015 (7)
C62B	0.0330 (9)	0.0400 (10)	0.0358 (9)	−0.0008 (7)	0.0007 (7)	−0.0013 (8)
C61B	0.0441 (10)	0.0545 (12)	0.0354 (10)	0.0057 (9)	−0.0076 (8)	−0.0056 (9)
C60B	0.0431 (10)	0.0614 (13)	0.0278 (9)	0.0179 (9)	0.0004 (8)	0.0053 (9)
C59B	0.0443 (10)	0.0508 (11)	0.0382 (10)	0.0048 (8)	0.0075 (8)	0.0145 (9)
C58B	0.0333 (8)	0.0394 (9)	0.0333 (9)	−0.0025 (7)	0.0022 (7)	0.0050 (7)

Geometric parameters (Å, º)

S1A—C2A	1.827 (2)	S1B—C2B	1.834 (1)
S1A—C5A	1.852 (2)	S1B—C5B	1.846 (2)
O28A—C25A	1.1922 (19)	O28B—C25B	1.1953 (19)
O26A—C25A	1.3356 (18)	O26B—C25B	1.3287 (19)
O26A—C27A	1.448 (2)	O26B—C27B	1.4586 (19)
O24A—C21A	1.1902 (18)	O24B—C21B	1.1949 (19)
O22A—C21A	1.3263 (19)	O22B—C21B	1.3317 (19)
O22A—C23A	1.453 (2)	O22B—C23B	1.456 (2)
N3A—C31A	1.4014 (19)	N3B—C31B	1.4051 (18)
N3A—C2A	1.456 (2)	N3B—C2B	1.454 (2)
N3A—C4A	1.468 (2)	N3B—C4B	1.472 (2)
C2A—C25A	1.552 (2)	C2B—C25B	1.562 (2)
C2A—C21A	1.5617 (19)	C2B—C21B	1.562 (2)
C4A—C41A	1.5259 (19)	C4B—C41B	1.524 (2)
C4A—C5A	1.556 (2)	C4B—C5B	1.562 (2)
C4A—H4A	1.0000	C4B—H4B	1.0000
C5A—C51A	1.529 (2)	C5B—C51B	1.535 (2)
C5A—C57A	1.544 (2)	C5B—C57B	1.538 (2)
C27A—H271	0.9800	C27B—H275	0.9800
C27A—H272	0.9800	C27B—H274	0.9800
C27A—H273	0.9800	C27B—H276	0.9800
C23A—H231	0.9800	C23B—H234	0.9800
C23A—H232	0.9800	C23B—H235	0.9800
C23A—H233	0.9800	C23B—H236	0.9800
C31A—C32A	1.402 (2)	C31B—C32B	1.402 (2)
C31A—C36A	1.409 (2)	C31B—C36B	1.402 (2)
C32A—C33A	1.385 (2)	C32B—C33B	1.383 (2)
C32A—H32A	0.9500	C32B—H32B	0.9500
C33A—C34A	1.386 (3)	C33B—C34B	1.377 (3)
C33A—H33A	0.9500	C33B—H33B	0.9500
C34A—C35A	1.384 (3)	C34B—C35B	1.382 (3)
C34A—H34A	0.9500	C34B—H34B	0.9500
C35A—C36A	1.384 (2)	C35B—C36B	1.388 (2)
C35A—H35A	0.9500	C35B—H35B	0.9500
C36A—H36A	0.9500	C36B—H36B	0.9500
C41A—C46A	1.388 (2)	C41B—C42B	1.391 (2)
C41A—C42A	1.392 (2)	C41B—C46B	1.393 (2)
C42A—C43A	1.388 (2)	C42B—C43B	1.388 (2)
C42A—H42A	0.9500	C42B—H42B	0.9500
C43A—C44A	1.384 (3)	C43B—C44B	1.384 (3)
C43A—H43A	0.9500	C43B—H43B	0.9500
C44A—C45A	1.380 (2)	C44B—C45B	1.383 (3)
C44A—H44A	0.9500	C44B—H44B	0.9500
C45A—C46A	1.393 (2)	C45B—C46B	1.386 (2)
C45A—H45A	0.9500	C45B—H45B	0.9500
C46A—H46A	0.9500	C46B—H46B	0.9500
C51A—C52A	1.391 (2)	C51B—C56B	1.391 (2)
C51A—C56A	1.397 (2)	C51B—C52B	1.398 (2)
C56A—C55A	1.388 (2)	C56B—C55B	1.387 (2)
C56A—H56A	0.9500	C56B—H56B	0.9500
C55A—C54A	1.383 (3)	C55B—C54B	1.385 (3)
C55A—H55A	0.9500	C55B—H55B	0.9500
C54A—C53A	1.380 (3)	C54B—C53B	1.385 (3)
C54A—H54A	0.9500	C54B—H54B	0.9500
C53A—C52A	1.389 (2)	C53B—C52B	1.383 (2)
C53A—H53A	0.9500	C53B—H53B	0.9500
C52A—H52A	0.9500	C52B—H52B	0.9500
C57A—C62A	1.383 (2)	C57B—C58B	1.385 (2)
C57A—C58A	1.392 (2)	C57B—C62B	1.400 (2)
C62A—C61A	1.394 (2)	C62B—C61B	1.379 (3)
C62A—H62A	0.9500	C62B—H62B	0.9500
C61A—C60A	1.382 (3)	C61B—C60B	1.381 (3)
C61A—H61A	0.9500	C61B—H61B	0.9500
C60A—C59A	1.382 (3)	C60B—C59B	1.371 (3)
C60A—H60A	0.9500	C60B—H60B	0.9500
C59A—C58A	1.387 (2)	C59B—C58B	1.393 (3)
C59A—H59A	0.9500	C59B—H59B	0.9500
C58A—H58A	0.9500	C58B—H58B	0.9500
C2A—S1A—C5A	89.1 (1)	C2B—S1B—C5B	89.8 (1)
C25A—O26A—C27A	117.36 (12)	C25B—O26B—C27B	114.60 (13)
C21A—O22A—C23A	114.07 (13)	C21B—O22B—C23B	115.09 (13)
C31A—N3A—C2A	123.83 (12)	C31B—N3B—C2B	122.57 (12)
C31A—N3A—C4A	119.88 (12)	C31B—N3B—C4B	120.38 (12)
C2A—N3A—C4A	116.3 (1)	C2B—N3B—C4B	117.0 (1)
N3A—C2A—C25A	113.08 (12)	N3B—C2B—C25B	111.60 (12)
N3A—C2A—C21A	112.09 (12)	N3B—C2B—C21B	112.38 (12)
C25A—C2A—C21A	108.31 (11)	C25B—C2B—C21B	111.79 (12)
N3A—C2A—S1A	104.6 (1)	N3B—C2B—S1B	104.0 (1)
C25A—C2A—S1A	106.06 (10)	C25B—C2B—S1B	105.02 (10)
C21A—C2A—S1A	112.55 (10)	C21B—C2B—S1B	111.51 (10)
N3A—C4A—C41A	113.90 (12)	N3B—C4B—C41B	115.07 (12)
N3A—C4A—C5A	105.8 (1)	N3B—C4B—C5B	105.6 (1)
C41A—C4A—C5A	115.13 (12)	C41B—C4B—C5B	115.10 (12)
N3A—C4A—H4A	107.2	N3B—C4B—H4B	106.8
C41A—C4A—H4A	107.2	C41B—C4B—H4B	106.8
C5A—C4A—H4A	107.2	C5B—C4B—H4B	106.8
C51A—C5A—C57A	111.65 (12)	C51B—C5B—C57B	110.81 (12)
C51A—C5A—C4A	113.14 (11)	C51B—C5B—C4B	112.85 (12)
C57A—C5A—C4A	112.29 (12)	C57B—C5B—C4B	113.22 (12)
C51A—C5A—S1A	110.19 (10)	C51B—C5B—S1B	109.83 (10)
C57A—C5A—S1A	107.80 (10)	C57B—C5B—S1B	108.36 (10)
C4A—C5A—S1A	101.1 (1)	C4B—C5B—S1B	101.3 (1)
O28A—C25A—O26A	125.66 (14)	O28B—C25B—O26B	125.08 (14)
O28A—C25A—C2A	125.07 (13)	O28B—C25B—C2B	123.02 (13)
O26A—C25A—C2A	109.27 (12)	O26B—C25B—C2B	111.90 (13)
O26A—C27A—H271	109.5	O26B—C27B—H275	109.5
O26A—C27A—H272	109.5	O26B—C27B—H274	109.5
H271—C27A—H272	109.5	H275—C27B—H274	109.5
O26A—C27A—H273	109.5	O26B—C27B—H276	109.5
H271—C27A—H273	109.5	H275—C27B—H276	109.5
H272—C27A—H273	109.5	H274—C27B—H276	109.5
O24A—C21A—O22A	124.67 (13)	O24B—C21B—O22B	124.96 (15)
O24A—C21A—C2A	122.77 (13)	O24B—C21B—C2B	122.93 (14)
O22A—C21A—C2A	112.51 (12)	O22B—C21B—C2B	112.10 (13)
O22A—C23A—H231	109.5	O22B—C23B—H234	109.5
O22A—C23A—H232	109.5	O22B—C23B—H235	109.5
H231—C23A—H232	109.5	H234—C23B—H235	109.5
O22A—C23A—H233	109.5	O22B—C23B—H236	109.5
H231—C23A—H233	109.5	H234—C23B—H236	109.5
H232—C23A—H233	109.5	H235—C23B—H236	109.5
N3A—C31A—C32A	122.64 (14)	C32B—C31B—C36B	117.61 (14)
N3A—C31A—C36A	120.08 (14)	C32B—C31B—N3B	121.79 (14)
C32A—C31A—C36A	117.28 (14)	C36B—C31B—N3B	120.61 (13)
C33A—C32A—C31A	120.97 (16)	C33B—C32B—C31B	120.73 (15)
C33A—C32A—H32A	119.5	C33B—C32B—H32B	119.6
C31A—C32A—H32A	119.5	C31B—C32B—H32B	119.6
C32A—C33A—C34A	121.19 (17)	C34B—C33B—C32B	121.29 (15)
C32A—C33A—H33A	119.4	C34B—C33B—H33B	119.4
C34A—C33A—H33A	119.4	C32B—C33B—H33B	119.4
C35A—C34A—C33A	118.48 (16)	C33B—C34B—C35B	118.72 (15)
C35A—C34A—H34A	120.8	C33B—C34B—H34B	120.6
C33A—C34A—H34A	120.8	C35B—C34B—H34B	120.6
C34A—C35A—C36A	121.20 (16)	C34B—C35B—C36B	121.02 (16)
C34A—C35A—H35A	119.4	C34B—C35B—H35B	119.5
C36A—C35A—H35A	119.4	C36B—C35B—H35B	119.5
C35A—C36A—C31A	120.85 (15)	C35B—C36B—C31B	120.63 (15)
C35A—C36A—H36A	119.6	C35B—C36B—H36B	119.7
C31A—C36A—H36A	119.6	C31B—C36B—H36B	119.7
C46A—C41A—C42A	119.03 (14)	C42B—C41B—C46B	118.74 (14)
C46A—C41A—C4A	122.62 (13)	C42B—C41B—C4B	118.30 (13)
C42A—C41A—C4A	118.34 (13)	C46B—C41B—C4B	122.95 (13)
C43A—C42A—C41A	120.87 (15)	C43B—C42B—C41B	121.00 (15)
C43A—C42A—H42A	119.6	C43B—C42B—H42B	119.5
C41A—C42A—H42A	119.6	C41B—C42B—H42B	119.5
C44A—C43A—C42A	119.60 (15)	C44B—C43B—C42B	119.91 (16)
C44A—C43A—H43A	120.2	C44B—C43B—H43B	120.0
C42A—C43A—H43A	120.2	C42B—C43B—H43B	120.0
C45A—C44A—C43A	120.06 (15)	C45B—C44B—C43B	119.35 (16)
C45A—C44A—H44A	120.0	C45B—C44B—H44B	120.3
C43A—C44A—H44A	120.0	C43B—C44B—H44B	120.3
C44A—C45A—C46A	120.43 (16)	C44B—C45B—C46B	121.02 (16)
C44A—C45A—H45A	119.8	C44B—C45B—H45B	119.5
C46A—C45A—H45A	119.8	C46B—C45B—H45B	119.5
C41A—C46A—C45A	120.00 (15)	C45B—C46B—C41B	119.97 (15)
C41A—C46A—H46A	120.0	C45B—C46B—H46B	120.0
C45A—C46A—H46A	120.0	C41B—C46B—H46B	120.0
C52A—C51A—C56A	118.32 (14)	C56B—C51B—C52B	118.25 (14)
C52A—C51A—C5A	119.37 (13)	C56B—C51B—C5B	122.13 (13)
C56A—C51A—C5A	122.20 (14)	C52B—C51B—C5B	119.51 (14)
C55A—C56A—C51A	120.75 (16)	C55B—C56B—C51B	121.02 (15)
C55A—C56A—H56A	119.6	C55B—C56B—H56B	119.5
C51A—C56A—H56A	119.6	C51B—C56B—H56B	119.5
C54A—C55A—C56A	120.28 (16)	C54B—C55B—C56B	120.07 (16)
C54A—C55A—H55A	119.9	C54B—C55B—H55B	120.0
C56A—C55A—H55A	119.9	C56B—C55B—H55B	120.0
C53A—C54A—C55A	119.44 (16)	C53B—C54B—C55B	119.53 (16)
C53A—C54A—H54A	120.3	C53B—C54B—H54B	120.2
C55A—C54A—H54A	120.3	C55B—C54B—H54B	120.2
C54A—C53A—C52A	120.60 (16)	C52B—C53B—C54B	120.42 (16)
C54A—C53A—H53A	119.7	C52B—C53B—H53B	119.8
C52A—C53A—H53A	119.7	C54B—C53B—H53B	119.8
C53A—C52A—C51A	120.59 (15)	C53B—C52B—C51B	120.68 (16)
C53A—C52A—H52A	119.7	C53B—C52B—H52B	119.7
C51A—C52A—H52A	119.7	C51B—C52B—H52B	119.7
C62A—C57A—C58A	117.90 (14)	C58B—C57B—C62B	117.77 (15)
C62A—C57A—C5A	123.91 (13)	C58B—C57B—C5B	123.73 (14)
C58A—C57A—C5A	118.18 (14)	C62B—C57B—C5B	118.50 (14)
C57A—C62A—C61A	121.05 (15)	C61B—C62B—C57B	120.97 (17)
C57A—C62A—H62A	119.5	C61B—C62B—H62B	119.5
C61A—C62A—H62A	119.5	C57B—C62B—H62B	119.5
C60A—C61A—C62A	120.34 (16)	C62B—C61B—C60B	120.50 (18)
C60A—C61A—H61A	119.8	C62B—C61B—H61B	119.7
C62A—C61A—H61A	119.8	C60B—C61B—H61B	119.7
C59A—C60A—C61A	119.19 (16)	C59B—C60B—C61B	119.33 (17)
C59A—C60A—H60A	120.4	C59B—C60B—H60B	120.3
C61A—C60A—H60A	120.4	C61B—C60B—H60B	120.3
C60A—C59A—C58A	120.21 (16)	C60B—C59B—C58B	120.51 (18)
C60A—C59A—H59A	119.9	C60B—C59B—H59B	119.7
C58A—C59A—H59A	119.9	C58B—C59B—H59B	119.7
C59A—C58A—C57A	121.30 (16)	C57B—C58B—C59B	120.90 (17)
C59A—C58A—H58A	119.3	C57B—C58B—H58B	119.5
C57A—C58A—H58A	119.3	C59B—C58B—H58B	119.5
C31A—N3A—C2A—C25A	−50.02 (18)	C31B—N3B—C2B—C25B	52.54 (18)
C4A—N3A—C2A—C25A	130.45 (13)	C4B—N3B—C2B—C25B	−127.73 (13)
C31A—N3A—C2A—C21A	72.77 (17)	C31B—N3B—C2B—C21B	−73.96 (17)
C4A—N3A—C2A—C21A	−106.76 (14)	C4B—N3B—C2B—C21B	105.77 (14)
C31A—N3A—C2A—S1A	−164.98 (11)	C31B—N3B—C2B—S1B	165.26 (11)
C4A—N3A—C2A—S1A	15.49 (14)	C4B—N3B—C2B—S1B	−15.01 (15)
C5A—S1A—C2A—N3A	−34.93 (10)	C5B—S1B—C2B—N3B	34.30 (10)
C5A—S1A—C2A—C25A	−154.71 (10)	C5B—S1B—C2B—C25B	151.68 (10)
C5A—S1A—C2A—C21A	87.03 (11)	C5B—S1B—C2B—C21B	−87.07 (11)
C31A—N3A—C4A—C41A	70.64 (16)	C31B—N3B—C4B—C41B	−69.57 (17)
C2A—N3A—C4A—C41A	−109.81 (14)	C2B—N3B—C4B—C41B	110.70 (14)
C31A—N3A—C4A—C5A	−161.87 (12)	C31B—N3B—C4B—C5B	162.32 (12)
C2A—N3A—C4A—C5A	17.68 (16)	C2B—N3B—C4B—C5B	−17.42 (16)
N3A—C4A—C5A—C51A	−159.20 (12)	N3B—C4B—C5B—C51B	157.99 (12)
C41A—C4A—C5A—C51A	−32.46 (17)	C41B—C4B—C5B—C51B	29.90 (17)
N3A—C4A—C5A—C57A	73.30 (14)	N3B—C4B—C5B—C57B	−75.12 (14)
C41A—C4A—C5A—C57A	−159.96 (12)	C41B—C4B—C5B—C57B	156.78 (12)
N3A—C4A—C5A—S1A	−41.38 (12)	N3B—C4B—C5B—S1B	40.66 (12)
C41A—C4A—C5A—S1A	85.36 (12)	C41B—C4B—C5B—S1B	−87.44 (12)
C2A—S1A—C5A—C51A	164.00 (10)	C2B—S1B—C5B—C51B	−162.96 (10)
C2A—S1A—C5A—C57A	−73.93 (10)	C2B—S1B—C5B—C57B	75.87 (10)
C2A—S1A—C5A—C4A	44.06 (9)	C2B—S1B—C5B—C4B	−43.44 (10)
C27A—O26A—C25A—O28A	−0.2 (2)	C27B—O26B—C25B—O28B	0.0 (2)
C27A—O26A—C25A—C2A	179.62 (13)	C27B—O26B—C25B—C2B	−179.48 (13)
N3A—C2A—C25A—O28A	−42.6 (2)	N3B—C2B—C25B—O28B	44.28 (19)
C21A—C2A—C25A—O28A	−167.42 (15)	C21B—C2B—C25B—O28B	171.10 (14)
S1A—C2A—C25A—O28A	71.54 (18)	S1B—C2B—C25B—O28B	−67.83 (16)
N3A—C2A—C25A—O26A	137.63 (13)	N3B—C2B—C25B—O26B	−136.23 (13)
C21A—C2A—C25A—O26A	12.77 (16)	C21B—C2B—C25B—O26B	−9.41 (17)
S1A—C2A—C25A—O26A	−108.27 (12)	S1B—C2B—C25B—O26B	111.66 (12)
C23A—O22A—C21A—O24A	−1.8 (2)	C23B—O22B—C21B—O24B	−3.4 (2)
C23A—O22A—C21A—C2A	175.75 (16)	C23B—O22B—C21B—C2B	176.20 (13)
N3A—C2A—C21A—O24A	−30.6 (2)	N3B—C2B—C21B—O24B	22.71 (19)
C25A—C2A—C21A—O24A	94.86 (17)	C25B—C2B—C21B—O24B	−103.68 (17)
S1A—C2A—C21A—O24A	−148.20 (13)	S1B—C2B—C21B—O24B	139.10 (13)
N3A—C2A—C21A—O22A	151.79 (13)	N3B—C2B—C21B—O22B	−156.85 (12)
C25A—C2A—C21A—O22A	−82.76 (15)	C25B—C2B—C21B—O22B	76.76 (15)
S1A—C2A—C21A—O22A	34.17 (16)	S1B—C2B—C21B—O22B	−40.46 (15)
C2A—N3A—C31A—C32A	−0.1 (2)	C2B—N3B—C31B—C32B	3.9 (2)
C4A—N3A—C31A—C32A	179.44 (14)	C4B—N3B—C31B—C32B	−175.78 (14)
C2A—N3A—C31A—C36A	179.6 (1)	C2B—N3B—C31B—C36B	−175.8 (1)
C4A—N3A—C31A—C36A	−0.8 (2)	C4B—N3B—C31B—C36B	4.4 (2)
N3A—C31A—C32A—C33A	179.70 (15)	C36B—C31B—C32B—C33B	0.9 (2)
C36A—C31A—C32A—C33A	0.0 (2)	N3B—C31B—C32B—C33B	−178.93 (15)
C31A—C32A—C33A—C34A	1.3 (3)	C31B—C32B—C33B—C34B	−0.4 (3)
C32A—C33A—C34A—C35A	−1.0 (3)	C32B—C33B—C34B—C35B	−0.6 (3)
C33A—C34A—C35A—C36A	−0.5 (3)	C33B—C34B—C35B—C36B	1.0 (3)
C34A—C35A—C36A—C31A	1.8 (3)	C34B—C35B—C36B—C31B	−0.5 (3)
N3A—C31A—C36A—C35A	178.76 (14)	C32B—C31B—C36B—C35B	−0.4 (2)
C32A—C31A—C36A—C35A	−1.5 (2)	N3B—C31B—C36B—C35B	179.35 (15)
N3A—C4A—C41A—C46A	32.5 (2)	N3B—C4B—C41B—C42B	149.05 (13)
C5A—C4A—C41A—C46A	−89.98 (17)	C5B—C4B—C41B—C42B	−87.74 (16)
N3A—C4A—C41A—C42A	−147.34 (14)	N3B—C4B—C41B—C46B	−30.0 (2)
C5A—C4A—C41A—C42A	90.14 (17)	C5B—C4B—C41B—C46B	93.22 (16)
C46A—C41A—C42A—C43A	0.9 (2)	C46B—C41B—C42B—C43B	−0.3 (2)
C4A—C41A—C42A—C43A	−179.17 (14)	C4B—C41B—C42B—C43B	−179.37 (14)
C41A—C42A—C43A—C44A	−0.3 (3)	C41B—C42B—C43B—C44B	1.0 (3)
C42A—C43A—C44A—C45A	0.1 (3)	C42B—C43B—C44B—C45B	−0.7 (3)
C43A—C44A—C45A—C46A	−0.5 (3)	C43B—C44B—C45B—C46B	−0.2 (3)
C42A—C41A—C46A—C45A	−1.3 (2)	C44B—C45B—C46B—C41B	0.9 (3)
C4A—C41A—C46A—C45A	178.80 (14)	C42B—C41B—C46B—C45B	−0.7 (2)
C44A—C45A—C46A—C41A	1.1 (3)	C4B—C41B—C46B—C45B	178.38 (15)
C57A—C5A—C51A—C52A	33.57 (18)	C57B—C5B—C51B—C56B	151.99 (14)
C4A—C5A—C51A—C52A	−94.27 (16)	C4B—C5B—C51B—C56B	−79.85 (18)
S1A—C5A—C51A—C52A	153.33 (12)	S1B—C5B—C51B—C56B	32.30 (18)
C57A—C5A—C51A—C56A	−150.33 (14)	C57B—C5B—C51B—C52B	−31.76 (19)
C4A—C5A—C51A—C56A	81.83 (17)	C4B—C5B—C51B—C52B	96.39 (16)
S1A—C5A—C51A—C56A	−30.57 (18)	S1B—C5B—C51B—C52B	−151.45 (12)
C52A—C51A—C56A—C55A	−1.6 (2)	C52B—C51B—C56B—C55B	1.3 (2)
C5A—C51A—C56A—C55A	−177.72 (15)	C5B—C51B—C56B—C55B	177.63 (15)
C51A—C56A—C55A—C54A	1.0 (3)	C51B—C56B—C55B—C54B	−0.9 (3)
C56A—C55A—C54A—C53A	0.3 (3)	C56B—C55B—C54B—C53B	−0.3 (3)
C55A—C54A—C53A—C52A	−1.1 (3)	C55B—C54B—C53B—C52B	1.0 (3)
C54A—C53A—C52A—C51A	0.5 (3)	C54B—C53B—C52B—C51B	−0.5 (3)
C56A—C51A—C52A—C53A	0.8 (2)	C56B—C51B—C52B—C53B	−0.7 (2)
C5A—C51A—C52A—C53A	177.07 (14)	C5B—C51B—C52B—C53B	−177.05 (15)
C51A—C5A—C57A—C62A	−119.16 (15)	C51B—C5B—C57B—C58B	113.62 (16)
C4A—C5A—C57A—C62A	9.1 (2)	C4B—C5B—C57B—C58B	−14.3 (2)
S1A—C5A—C57A—C62A	119.68 (14)	S1B—C5B—C57B—C58B	−125.82 (14)
C51A—C5A—C57A—C58A	61.89 (18)	C51B—C5B—C57B—C62B	−65.99 (18)
C4A—C5A—C57A—C58A	−169.82 (14)	C4B—C5B—C57B—C62B	166.06 (14)
S1A—C5A—C57A—C58A	−59.27 (16)	S1B—C5B—C57B—C62B	54.58 (16)
C58A—C57A—C62A—C61A	0.5 (2)	C58B—C57B—C62B—C61B	0.7 (3)
C5A—C57A—C62A—C61A	−178.48 (15)	C5B—C57B—C62B—C61B	−179.71 (16)
C57A—C62A—C61A—C60A	0.3 (3)	C57B—C62B—C61B—C60B	0.3 (3)
C62A—C61A—C60A—C59A	−0.5 (3)	C62B—C61B—C60B—C59B	−1.3 (3)
C61A—C60A—C59A—C58A	0.0 (3)	C61B—C60B—C59B—C58B	1.2 (3)
C60A—C59A—C58A—C57A	0.8 (3)	C62B—C57B—C58B—C59B	−0.7 (2)
C62A—C57A—C58A—C59A	−1.0 (3)	C5B—C57B—C58B—C59B	179.69 (16)
C5A—C57A—C58A—C59A	178.02 (16)	C60B—C59B—C58B—C57B	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C32A—H32A···O24A	0.95	2.62	2.993 (2)	104
C46A—H46A···O28A	0.95	2.49	3.413 (2)	166
C46A—H46A···N3A	0.95	2.68	2.958 (2)	98
C56A—H56A···S1A	0.95	2.66	3.060 (2)	106
C32B—H32B···O26B	0.95	2.57	3.392 (2)	145
C32B—H32B···O24B	0.95	2.60	3.001 (2)	106
C46B—H46B···O28B	0.95	2.40	3.328 (2)	166
C46B—H46B···N3B	0.95	2.71	2.980 (2)	97
C56B—H56B···S1B	0.95	2.66	3.060 (2)	106
C42A—H42A···O28B	0.95	2.65	3.366 (2)	133
C27A—H271···O24A^i	0.98	2.37	2.832 (2)	108
C44A—H44A···O28B^ii	0.95	2.53	3.351 (2)	145
C43B—H43B···O28A^iii	0.95	2.68	3.358 (2)	128
C23B—H234···Cg1^iv	0.98	2.79	3.743 (2)	165

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y+1, z; (iv) x, −y+1/2, z−1/2.

(IX) 3,3-dichloro-2,2,4,4,3'-pentamethyl-r-2',t-4'-diphenylcyclobutane-1-spiro-5'- 1,3-thiazolidine

Crystal data

C23H27Cl2NS	F(000) = 1776
Mr = 420.42	Dx = 1.323 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8000 reflections
a = 11.3371 (8) Å	θ = 2.4–25.9°
b = 12.7769 (9) Å	µ = 0.42 mm^−1
c = 29.1481 (18) Å	T = 173 K
V = 4222.2 (5) Å^3	Prism, colourless
Z = 8	0.5 × 0.5 × 0.4 mm

Data collection

Stoe IPDS diffractometer	Rint = 0.060
Graphite monochromator	θmax = 25.9°, θmin = 2.5°
rotation scans	h = −13→13
32423 measured reflections	k = −15→15
4063 independent reflections	l = −35→35
3125 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.0538P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.080	(Δ/σ)max < 0.001
S = 0.92	Δρmax = 0.32 e Å^−3
4063 reflections	Δρmin = −0.16 e Å^−3
249 parameters

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.

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

	x	y	z	Uiso*/Ueq
Cl59	−0.06327 (4)	0.00823 (3)	0.081549 (16)	0.03360 (12)
Cl55	−0.05151 (4)	0.21163 (4)	0.040544 (17)	0.03888 (13)
S1	0.19634 (4)	−0.01487 (3)	0.149753 (14)	0.02398 (11)
N3	0.29553 (12)	0.14914 (10)	0.18573 (5)	0.0224 (3)
C2	0.30491 (14)	0.03571 (13)	0.19138 (6)	0.0235 (3)
H2	0.3858	0.0124	0.1823	0.028*
C4	0.29345 (14)	0.17190 (12)	0.13602 (5)	0.0210 (3)
H4	0.2753	0.2481	0.1325	0.025*
C5	0.18453 (14)	0.11070 (12)	0.11907 (5)	0.0209 (3)
C51	0.15755 (15)	0.09918 (13)	0.06595 (6)	0.0254 (4)
C54	0.02618 (15)	0.12423 (13)	0.07809 (6)	0.0265 (4)
C56	0.06009 (14)	0.16607 (12)	0.12627 (6)	0.0239 (3)
C21	0.27834 (15)	−0.00240 (14)	0.23934 (6)	0.0259 (4)
C22	0.19372 (17)	0.04546 (19)	0.26663 (7)	0.0414 (5)
H22	0.1512	0.1040	0.2552	0.050*
C23	0.17096 (18)	0.0083 (2)	0.31045 (7)	0.0465 (6)
H23	0.1139	0.0421	0.3291	0.056*
C24	0.23102 (18)	−0.07789 (18)	0.32702 (7)	0.0412 (5)
H24	0.2142	−0.1040	0.3568	0.049*
C25	0.3151 (2)	−0.12580 (17)	0.30035 (7)	0.0437 (5)
H25	0.3563	−0.1851	0.3117	0.052*
C26	0.33995 (18)	−0.08749 (15)	0.25676 (7)	0.0355 (4)
H26	0.3996	−0.1198	0.2388	0.043*
C31	0.38530 (15)	0.20666 (14)	0.21152 (6)	0.0296 (4)
H312	0.4639	0.1834	0.2019	0.036*
H311	0.3751	0.1933	0.2444	0.036*
H313	0.3770	0.2818	0.2055	0.036*
C41	0.41013 (14)	0.15127 (13)	0.11112 (6)	0.0232 (3)
C46	0.44409 (15)	0.05380 (14)	0.09399 (6)	0.0271 (4)
H46	0.3930	−0.0046	0.0976	0.033*
C45	0.55156 (16)	0.04098 (15)	0.07176 (6)	0.0329 (4)
H45	0.5729	−0.0257	0.0599	0.039*
C44	0.62769 (16)	0.12490 (16)	0.06677 (7)	0.0350 (4)
H44	0.7010	0.1162	0.0514	0.042*
C43	0.59606 (16)	0.22143 (16)	0.08431 (7)	0.0343 (4)
H43	0.6485	0.2790	0.0815	0.041*
C42	0.48816 (15)	0.23472 (14)	0.10605 (6)	0.0268 (4)
H42	0.4672	0.3017	0.1176	0.032*
C53	0.17927 (18)	−0.00580 (15)	0.04236 (6)	0.0342 (4)
H533	0.1366	−0.0077	0.0131	0.041*
H531	0.1513	−0.0626	0.0621	0.041*
H532	0.2639	−0.0145	0.0367	0.041*
C52	0.21475 (17)	0.18426 (16)	0.03604 (6)	0.0335 (4)
H522	0.1783	0.1839	0.0056	0.040*
H523	0.2994	0.1703	0.0331	0.040*
H521	0.2030	0.2529	0.0504	0.040*
C58	−0.01715 (15)	0.13254 (16)	0.16647 (6)	0.0315 (4)
H581	0.0150	0.1613	0.1950	0.038*
H582	−0.0186	0.0560	0.1684	0.038*
H583	−0.0975	0.1588	0.1619	0.038*
C57	0.06729 (16)	0.28597 (13)	0.12793 (7)	0.0327 (4)
H571	0.1135	0.3113	0.1018	0.039*
H572	0.1054	0.3077	0.1566	0.039*
H573	−0.0124	0.3155	0.1265	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl59	0.0328 (2)	0.0282 (2)	0.0398 (2)	−0.00905 (17)	−0.00980 (18)	0.00327 (19)
Cl55	0.0367 (2)	0.0360 (2)	0.0439 (3)	−0.00075 (19)	−0.0154 (2)	0.0136 (2)
S1	0.0282 (2)	0.01873 (19)	0.0250 (2)	−0.00206 (16)	−0.00309 (16)	0.00257 (16)
N3	0.0237 (7)	0.0231 (7)	0.0206 (7)	−0.0005 (5)	−0.0012 (5)	0.0000 (6)
C2	0.0231 (8)	0.0245 (8)	0.0229 (8)	0.0014 (6)	−0.0010 (6)	0.0016 (7)
C4	0.0215 (7)	0.0181 (7)	0.0233 (8)	0.0001 (6)	−0.0008 (6)	0.0013 (6)
C5	0.0233 (8)	0.0184 (7)	0.0209 (8)	0.0002 (6)	−0.0003 (6)	0.0011 (6)
C51	0.0283 (8)	0.0267 (9)	0.0212 (8)	−0.0008 (7)	−0.0029 (7)	0.0014 (7)
C54	0.0260 (8)	0.0237 (8)	0.0297 (9)	−0.0019 (7)	−0.0073 (7)	0.0054 (7)
C56	0.0200 (8)	0.0231 (8)	0.0287 (9)	0.0002 (6)	−0.0019 (6)	−0.0004 (7)
C21	0.0243 (8)	0.0298 (9)	0.0235 (8)	−0.0027 (7)	−0.0035 (6)	0.0033 (7)
C22	0.0312 (10)	0.0592 (13)	0.0337 (10)	0.0138 (9)	0.0037 (8)	0.0140 (9)
C23	0.0311 (10)	0.0774 (16)	0.0311 (10)	0.0067 (10)	0.0071 (8)	0.0113 (10)
C24	0.0380 (11)	0.0588 (13)	0.0269 (10)	−0.0139 (10)	−0.0052 (8)	0.0147 (9)
C25	0.0637 (14)	0.0349 (10)	0.0326 (10)	0.0033 (10)	−0.0102 (10)	0.0101 (9)
C26	0.0463 (11)	0.0318 (10)	0.0285 (10)	0.0075 (8)	−0.0034 (8)	0.0023 (8)
C31	0.0308 (9)	0.0307 (9)	0.0272 (9)	−0.0034 (7)	−0.0056 (7)	−0.0026 (7)
C41	0.0231 (8)	0.0260 (8)	0.0205 (8)	0.0009 (6)	−0.0011 (6)	0.0037 (7)
C46	0.0278 (9)	0.0248 (9)	0.0287 (9)	0.0004 (7)	0.0007 (7)	0.0008 (7)
C45	0.0342 (9)	0.0333 (10)	0.0312 (9)	0.0093 (8)	0.0042 (8)	−0.0006 (8)
C44	0.0270 (9)	0.0438 (11)	0.0343 (10)	0.0037 (8)	0.0080 (7)	0.0032 (9)
C43	0.0289 (9)	0.0371 (10)	0.0367 (10)	−0.0068 (8)	0.0038 (8)	0.0053 (8)
C42	0.0266 (8)	0.0246 (8)	0.0292 (9)	−0.0010 (7)	−0.0003 (7)	0.0013 (7)
C53	0.0406 (10)	0.0359 (10)	0.0262 (9)	0.0013 (8)	−0.0034 (7)	−0.0078 (8)
C52	0.0347 (9)	0.0412 (11)	0.0245 (9)	−0.0045 (8)	−0.0016 (7)	0.0080 (8)
C58	0.0232 (9)	0.0384 (10)	0.0329 (9)	−0.0002 (7)	0.0032 (7)	−0.0020 (8)
C57	0.0263 (9)	0.0242 (9)	0.0475 (11)	0.0048 (7)	−0.0028 (8)	−0.0043 (8)

Geometric parameters (Å, º)

Cl59—C54	1.7986 (17)	C25—H25	0.9500
Cl55—C54	1.7945 (17)	C26—H26	0.9500
S1—C5	1.842 (2)	C31—H312	0.9800
S1—C2	1.845 (2)	C31—H311	0.9800
N3—C2	1.462 (2)	C31—H313	0.9800
N3—C31	1.463 (2)	C41—C42	1.393 (2)
N3—C4	1.478 (2)	C41—C46	1.396 (2)
C2—C21	1.511 (2)	C46—C45	1.390 (3)
C2—H2	1.0000	C46—H46	0.9500
C4—C41	1.532 (2)	C45—C44	1.384 (3)
C4—C5	1.543 (2)	C45—H45	0.9500
C4—H4	1.0000	C44—C43	1.382 (3)
C5—C51	1.585 (2)	C44—H44	0.9500
C5—C56	1.592 (2)	C43—C42	1.388 (3)
C51—C53	1.527 (2)	C43—H43	0.9500
C51—C52	1.537 (2)	C42—H42	0.9500
C51—C54	1.564 (2)	C53—H533	0.9800
C54—C56	1.551 (2)	C53—H531	0.9800
C56—C58	1.524 (2)	C53—H532	0.9800
C56—C57	1.535 (2)	C52—H522	0.9800
C21—C22	1.388 (3)	C52—H523	0.9800
C21—C26	1.388 (3)	C52—H521	0.9800
C22—C23	1.387 (3)	C58—H581	0.9800
C22—H22	0.9500	C58—H582	0.9800
C23—C24	1.381 (3)	C58—H583	0.9800
C23—H23	0.9500	C57—H571	0.9800
C24—C25	1.374 (3)	C57—H572	0.9800
C24—H24	0.9500	C57—H573	0.9800
C25—C26	1.390 (3)
C5—S1—C2	93.6 (1)	C24—C25—H25	120.0
C2—N3—C31	112.91 (13)	C26—C25—H25	120.0
C2—N3—C4	107.8 (1)	C21—C26—C25	120.53 (19)
C31—N3—C4	114.59 (13)	C21—C26—H26	119.7
N3—C2—C21	114.15 (14)	C25—C26—H26	119.7
N3—C2—S1	103.0 (1)	N3—C31—H312	109.5
C21—C2—S1	111.26 (11)	N3—C31—H311	109.5
N3—C2—H2	109.4	H312—C31—H311	109.5
C21—C2—H2	109.4	N3—C31—H313	109.5
S1—C2—H2	109.4	H312—C31—H313	109.5
N3—C4—C41	114.63 (13)	H311—C31—H313	109.5
N3—C4—C5	103.1 (1)	C42—C41—C46	118.01 (16)
C41—C4—C5	116.90 (13)	C42—C41—C4	117.84 (15)
N3—C4—H4	107.2	C46—C41—C4	124.14 (15)
C41—C4—H4	107.2	C45—C46—C41	120.92 (16)
C5—C4—H4	107.2	C45—C46—H46	119.5
C4—C5—C51	120.95 (13)	C41—C46—H46	119.5
C4—C5—C56	116.22 (13)	C44—C45—C46	120.29 (17)
C51—C5—C56	89.94 (12)	C44—C45—H45	119.9
C4—C5—S1	103.2 (1)	C46—C45—H45	119.9
C51—C5—S1	114.04 (11)	C43—C44—C45	119.37 (17)
C56—C5—S1	112.81 (11)	C43—C44—H44	120.3
C53—C51—C52	107.31 (15)	C45—C44—H44	120.3
C53—C51—C54	115.79 (15)	C44—C43—C42	120.44 (17)
C52—C51—C54	112.67 (14)	C44—C43—H43	119.8
C53—C51—C5	119.36 (14)	C42—C43—H43	119.8
C52—C51—C5	114.02 (14)	C43—C42—C41	120.96 (17)
C54—C51—C5	86.78 (12)	C43—C42—H42	119.5
C56—C54—C51	92.25 (12)	C41—C42—H42	119.5
C56—C54—Cl55	117.34 (12)	C51—C53—H533	109.5
C51—C54—Cl55	117.18 (12)	C51—C53—H531	109.5
C56—C54—Cl59	111.90 (12)	H533—C53—H531	109.5
C51—C54—Cl59	112.40 (12)	C51—C53—H532	109.5
Cl55—C54—Cl59	105.68 (9)	H533—C53—H532	109.5
C58—C56—C57	106.67 (15)	H531—C53—H532	109.5
C58—C56—C54	117.17 (14)	C51—C52—H522	109.5
C57—C56—C54	112.69 (15)	C51—C52—H523	109.5
C58—C56—C5	119.04 (14)	H522—C52—H523	109.5
C57—C56—C5	113.61 (13)	C51—C52—H521	109.5
C54—C56—C5	86.97 (12)	H522—C52—H521	109.5
C22—C21—C26	118.88 (17)	H523—C52—H521	109.5
C22—C21—C2	121.74 (16)	C56—C58—H581	109.5
C26—C21—C2	119.38 (16)	C56—C58—H582	109.5
C23—C22—C21	120.35 (19)	H581—C58—H582	109.5
C23—C22—H22	119.8	C56—C58—H583	109.5
C21—C22—H22	119.8	H581—C58—H583	109.5
C24—C23—C22	120.2 (2)	H582—C58—H583	109.5
C24—C23—H23	119.9	C56—C57—H571	109.5
C22—C23—H23	119.9	C56—C57—H572	109.5
C25—C24—C23	119.95 (18)	H571—C57—H572	109.5
C25—C24—H24	120.0	C56—C57—H573	109.5
C23—C24—H24	120.0	H571—C57—H573	109.5
C24—C25—C26	120.04 (19)	H572—C57—H573	109.5
C31—N3—C2—C21	66.56 (18)	C51—C54—C56—C57	99.09 (15)
C4—N3—C2—C21	−165.80 (13)	Cl55—C54—C56—C57	−23.25 (18)
C31—N3—C2—S1	−172.70 (11)	Cl59—C54—C56—C57	−145.65 (12)
C4—N3—C2—S1	−45.06 (13)	C51—C54—C56—C5	−15.29 (12)
C5—S1—C2—N3	15.46 (11)	Cl55—C54—C56—C5	−137.63 (12)
C5—S1—C2—C21	138.15 (12)	Cl59—C54—C56—C5	99.98 (12)
C2—N3—C4—C41	−69.17 (16)	C4—C5—C56—C58	−100.41 (17)
C31—N3—C4—C41	57.50 (18)	C51—C5—C56—C58	134.65 (15)
C2—N3—C4—C5	58.99 (15)	S1—C5—C56—C58	18.45 (19)
C31—N3—C4—C5	−174.34 (13)	C4—C5—C56—C57	26.5 (2)
N3—C4—C5—C51	−171.31 (13)	C51—C5—C56—C57	−98.42 (16)
C41—C4—C5—C51	−44.6 (2)	S1—C5—C56—C57	145.38 (13)
N3—C4—C5—C56	81.59 (15)	C4—C5—C56—C54	140.00 (14)
C41—C4—C5—C56	−151.68 (14)	C51—C5—C56—C54	15.06 (12)
N3—C4—C5—S1	−42.40 (13)	S1—C5—C56—C54	−101.14 (12)
C41—C4—C5—S1	84.33 (14)	N3—C2—C21—C22	34.8 (2)
C2—S1—C5—C4	15.55 (11)	S1—C2—C21—C22	−81.24 (19)
C2—S1—C5—C51	148.60 (12)	N3—C2—C21—C26	−145.21 (17)
C2—S1—C5—C56	−110.65 (12)	S1—C2—C21—C26	98.8 (2)
C4—C5—C51—C53	106.16 (18)	C26—C21—C22—C23	−0.4 (3)
C56—C5—C51—C53	−132.87 (16)	C2—C21—C22—C23	179.66 (19)
S1—C5—C51—C53	−17.8 (2)	C21—C22—C23—C24	−1.1 (3)
C4—C5—C51—C52	−22.5 (2)	C22—C23—C24—C25	1.2 (3)
C56—C5—C51—C52	98.48 (15)	C23—C24—C25—C26	0.1 (3)
S1—C5—C51—C52	−146.43 (13)	C22—C21—C26—C25	1.7 (3)
C4—C5—C51—C54	−135.91 (14)	C2—C21—C26—C25	−178.35 (17)
C56—C5—C51—C54	−14.94 (12)	C24—C25—C26—C21	−1.6 (3)
S1—C5—C51—C54	100.15 (12)	N3—C4—C41—C42	−93.56 (17)
C53—C51—C54—C56	136.57 (15)	C5—C4—C41—C42	145.61 (15)
C52—C51—C54—C56	−99.37 (15)	N3—C4—C41—C46	85.2 (2)
C5—C51—C54—C56	15.36 (12)	C5—C4—C41—C46	−35.6 (2)
C53—C51—C54—Cl55	−100.96 (16)	C42—C41—C46—C45	−1.2 (3)
C52—C51—C54—Cl55	23.10 (19)	C4—C41—C46—C45	−179.95 (16)
C5—C51—C54—Cl55	137.83 (12)	C41—C46—C45—C44	0.8 (3)
C53—C51—C54—Cl59	21.74 (18)	C46—C45—C44—C43	0.3 (3)
C52—C51—C54—Cl59	145.80 (13)	C45—C44—C43—C42	−1.1 (3)
C5—C51—C54—Cl59	−99.47 (12)	C44—C43—C42—C41	0.7 (3)
C51—C54—C56—C58	−136.57 (15)	C46—C41—C42—C43	0.4 (3)
Cl55—C54—C56—C58	101.09 (16)	C4—C41—C42—C43	179.27 (16)
Cl59—C54—C56—C58	−21.31 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···N3	0.95	2.67	2.941 (3)	97
C46—H46···S1	0.95	2.70	3.362 (2)	127
C53—H531···S1	0.98	2.68	3.138 (2)	109
C58—H582···S1	0.98	2.66	3.105 (2)	108
C58—H582···Cl59	0.98	2.65	2.987 (2)	100
C53—H533···Cl59^i	0.98	2.88	3.844 (2)	167
C23—H23···Cg2^ii	0.95	2.89	3.778 (2)	157

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