4-(3,4-Di­chloro­phenyl)-9-(4-methyl­phenyl­sulfonyl)-4,9-di­aza­tetra­cyclo[5.3.1.0^2,6.0^8,10]­un­decane-3,5-dione and 4-(4-chloro­phenyl)-9-(4-methyl­phenyl­sulfonyl)-4,9-di­aza­tetra­cyclo[5.3.1.0^2,6.0^8,10]­un­decane-3,5-dione

The title compounds, C₂₂H₁₈Cl₂N₂O₄S, (I), and C₂₂H₁₉ClN₂O₄S, (II), respectively, are structural cyclic imide analogues of pharmaceutical interest. The configurations exo-endo for (I) and endo-endo for (II) were established.

S1. Comment

Maleimides and aziridines are well known for the diversity of their applications in medicinal chemistry. A great number of compounds with an aziridine ring have been synthesized, many of which have shown significant cytotoxicity against some tumour cells, such as mitomycin C, which is a bioreductive alkylating agent used in anticancer therapy (Kim et al., 1996; Kumar et al., 1996). Maleimides have also presented activity against some types of tumour, together with other pharmacological properties such as sedative, hypnotic, antihypertensive and diuretic properties, and in chemotherapy for tuberculosis. An example of this is mitonafide, which is already used as a drug and which has also been used as a model in the development of new drugs with improved effectiveness and reduced adverse effects (Asbury et al., 1994; Cechinel Filho et al., 2003).

In order to obtain additional proof that the products we synthesized are the exo-endo, (I), and endo-endo, (II), imidobenzenesulfonylaziridines, we have determined the molecular and crystal structures of the title compounds by X-ray diffraction and the results are presented here. According to a recent search in the Cambridge Structural Database (CSD, 2003, Version 5.25; Allen, 2002), the title compounds are the first examples of di-substituted norbornane with p-toluenesulfonamide and maleimide groups to be characterized by X-ray diffraction. \sch

Compounds (I) (Fig. 1) and (II) (Fig. 2) show the endo configuration with respect to the maleimide ring [C4/C5/N6/C7/C8], which is essentially planar in both structures. The dihedral angles between the planes of the rings C4/C5/N6/C7/C8 and N1/C2/C10 [54.9 (1)° in (I) and 2.6 (2)° in (II)] clearly indicate the different configurations, exo and endo, respectively, with respect to the aziridine ring (N1/C2/C10). In addition, the torsion angles N1—C2—C3—C11 and C11—C3—C4—C5 (Tables 1 and 2) also confirm the configurations as exo-endo for (I) and endo-endo for (II).

The three-membered aziridine ring is an almost-perfect isosceles triangle in both stereoisomers, with the N1—C2 and N1—C10 bond lengths being equal within experimental error, and the sums of the internal angles are very close to 180° (Tables 1 and 2). The C—N bonds in the aziridine rings are about 0.1 Å longer than those in the maleimide rings. This results from a combination of factors, such as a high level of tension in the three-membered ring, the substitution of the phenylsulfonyl moiety at N1 [due to the electron-withdrawing effect from this group, as described by Govindasamy et al. (1998)] and the hybridization character at atoms N1 and N6. The sums of the angles around N1 [290.0° in (I) and 288.6° in (II)] and N6 [360.1° in (I) and 359.4° in (II)] indicate essentially sp³ and sp² hybridization, respectively. This is as expected and is in agreement with related structures (Kajfez et al., 2003; Matthews et al., 2001; Yoshihara et al., 1999; Massa et al., 1983). In the norbornane skeletons of both (I) and (II), the C2—C10 bond is a little shorter than the neighbouring C—C bonds (Tables 1 and 2). This should be induced by the restriction imposed by the formation of the aziridine ring and was also observed in the related structures reported by Matthews et al. (2001), and references therein.

The environment around the S atoms in both compounds is best described as a distorted tetrahedron, with angles raging from 101.02 (14) to 118.64 (10)°, as observed in similar structures (Massa et al., 1983; Seshadri et al., 2002). Other geometric parameters show normal values and are within the expected ranges.

The three-dimensional packing of the title compounds is strongly influenced by van der Waals interactions. There is no evidence of π–π stacking involving the phenyl rings. All O atoms in (I) and three O atoms (two from the maleimide ring and one from the sulfonyl moiety) in (II) participate in C—H···O interactions. The geometric parameters of these interactions are available in the archived CIF.

S2. Experimental

For the preparation of the exo-endo compound, (I), p-toluenesulfonylazide (2.00 g, 10.1 mmol) was added to a mixture of 4-(3',4'-dichlorophenyl)-4-azatricycle[5.2.1.0^2,6-endo]dec-8-ene-3,5-dione (2.50 g, 8.11 mmol) in acetonitrile (25 ml), prepared as described by Salakhov et al. (1979) and Chenier et al. (1992). The reaction was refluxed for 18 h and the solvent was evaporated in vacuo. The solid residue was triturated with methanol-chloroform (3:7) and filtered off with suction to give the crude product. The formation of the endo-endo isomer was also observed together with (I), but unfortunately the endo-endo isomer could not afford crystals for X-ray studies. The exo-endo and endo-endo isomers were isolated by column chromatography (silica gel, dichloromethane-hexane, 1:4). For the preparation of the endo-endo compound, (II), p-toluenesulfonylazide (2.92 g, 14.8 mmol) was added to 4-(4'-chlorophenyl)-4-azatricycle[5.2.1.0^2,6-endo]dec-8-ene-3,5-dione (2.00 g, 7.31 mmol) in acetonitrile (20 ml), prepared as described by Salakhov et al. (1979) and Chenier et al. (1992). The reaction was refluxed for 18 h and the solvent was evaporated in vacuo. The solid residue was triturated with methanol-chloroform (3:7) and filtered off with suction to give the crude product. The endo-endo and exo-endo products were purified by column chromatography (silica gel, ethyl acetate-acetone-hexane, 6:3:11). The exo-endo isomer could not afford crystals for X-ray analysis. Compounds (I) and (II) were crystallized from solutions in methanol-chloroform (1:2) by slow evaporation of the solvent mixture.

S3. Refinement

H atoms were placed in idealized positions and refined using a riding model, with C—H distances of 0.98, 0.97, 0.96 and 0.93 Å, and with U_iso(H) fixed at 1.2, 1.2, 1.5 and 1.2U_eq(C), for CH, CH₂, CH₃ and CH_arom, respectively. In (I), a C₂ rotation on the N6—C12 bond causes structural disorder at atom Cl2, which is partially bonded to atoms C14 and C16, with occupancy factors of 0.862 (3) and 0.138 (3), respectively. The complementary occupancy factors at atoms C14 and C16 are occupied by H atoms fixed geometrically. The H atoms on C27 were placed in the atom list using an idealized disordered model for a methyl group.

Computing details

For both compounds, data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: SET4 in CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrgia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I), with the atom-labelling scheme. Displacement ellipsoids are shown at the 40% probability level and H atoms have been omitted for clarity.
	Fig. 2. The molecular structure of (II), with the atom-labelling scheme. Displacement ellipsoids are shown at the 40% probability level and H atoms have been omitted for clarity.

(I) 4-(3,4-Dichlorophenyl)-9-(4-methylphenylsulfonyl)-4,9- diazatetracyclo[5.3.1.0^2,6.0^8,10]undecane-3,5-dione

Crystal data

C22H18Cl2N2O4S	F(000) = 984
Mr = 477.34	Dx = 1.489 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.856 (1) Å	θ = 6.6–12.2°
b = 15.689 (1) Å	µ = 0.44 mm^−1
c = 10.727 (1) Å	T = 293 K
β = 100.27 (1)°	Irregular plate, colourless
V = 2128.9 (3) Å^3	0.50 × 0.40 × 0.10 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	2300 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 25.1°, θmin = 1.6°
ω/2θ scans	h = −15→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
Tmin = 0.844, Tmax = 0.934	l = −12→12
3962 measured reflections	3 standard reflections every 200 reflections
3785 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)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 1.0126P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3785 reflections	Δρmax = 0.52 e Å^−3
291 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (9)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.34269 (8)	0.08587 (5)	0.30464 (8)	0.0425 (3)
O1	0.2869 (2)	0.06278 (16)	0.1819 (2)	0.0653 (8)
O2	0.4527 (2)	0.06481 (15)	0.3339 (3)	0.0573 (7)
Cl1	1.07173 (11)	0.26492 (11)	0.57310 (18)	0.1251 (7)
Cl2	1.00000 (12)	0.41038 (13)	0.3801 (2)	0.1323 (10)	0.863 (3)
Cl2'	0.9165 (7)	0.1692 (7)	0.6638 (9)	0.091 (4)	0.137 (3)
N1	0.3210 (2)	0.18931 (16)	0.3190 (2)	0.0358 (6)
C2	0.4030 (2)	0.24479 (19)	0.2774 (3)	0.0334 (7)
H2	0.4616	0.2200	0.2424	0.040*
C3	0.3635 (2)	0.3348 (2)	0.2418 (3)	0.0370 (8)
H3	0.3387	0.3452	0.1513	0.044*
C4	0.4536 (3)	0.3936 (2)	0.3076 (3)	0.0381 (8)
H4	0.4418	0.4524	0.2774	0.046*
C5	0.5643 (3)	0.3653 (2)	0.3002 (3)	0.0395 (8)
O3	0.60126 (19)	0.35337 (16)	0.2056 (2)	0.0525 (7)
N6	0.6188 (2)	0.35146 (17)	0.4237 (3)	0.0407 (7)
C7	0.5551 (3)	0.3626 (2)	0.5158 (3)	0.0410 (8)
O4	0.58547 (19)	0.35425 (18)	0.6279 (2)	0.0586 (7)
C8	0.4457 (2)	0.3874 (2)	0.4496 (3)	0.0378 (8)
H8	0.4258	0.4427	0.4807	0.045*
C9	0.3554 (2)	0.3217 (2)	0.4504 (3)	0.0351 (8)
H9	0.3238	0.3211	0.5271	0.042*
C10	0.3985 (2)	0.23697 (19)	0.4139 (3)	0.0309 (7)
H10	0.4541	0.2070	0.4719	0.037*
C11	0.2818 (3)	0.3494 (2)	0.3285 (3)	0.0418 (8)
H11A	0.2602	0.4086	0.3307	0.050*
H11B	0.2203	0.3129	0.3073	0.050*
C12	0.7279 (3)	0.3275 (2)	0.4551 (3)	0.0425 (8)
C13	0.8017 (3)	0.3743 (3)	0.4081 (4)	0.0569 (11)
H13	0.7809	0.4198	0.3539	0.068*
C14	0.9079 (3)	0.3535 (3)	0.4416 (5)	0.0724 (13)
H14	0.9582	0.3841	0.4077	0.087*	0.137 (3)
C15	0.9389 (3)	0.2878 (3)	0.5243 (5)	0.0669 (12)
C16	0.8644 (4)	0.2408 (3)	0.5700 (4)	0.0649 (12)
H16	0.8851	0.1955	0.6248	0.078*	0.863 (3)
C17	0.7583 (3)	0.2600 (2)	0.5349 (4)	0.0538 (10)
H17	0.7078	0.2274	0.5652	0.065*
C21	0.2794 (3)	0.0440 (2)	0.4239 (3)	0.0389 (8)
C22	0.3314 (3)	−0.0179 (2)	0.5025 (3)	0.0442 (9)
H22	0.3990	−0.0353	0.4940	0.053*
C23	0.2821 (3)	−0.0537 (2)	0.5937 (3)	0.0500 (9)
H23	0.3167	−0.0962	0.6457	0.060*
C24	0.1832 (3)	−0.0282 (2)	0.6098 (3)	0.0488 (9)
C25	0.1338 (3)	0.0360 (3)	0.5322 (4)	0.0579 (10)
H25	0.0679	0.0556	0.5438	0.069*
C26	0.1807 (3)	0.0715 (2)	0.4381 (4)	0.0507 (10)
H26	0.1459	0.1134	0.3852	0.061*
C27	0.1304 (4)	−0.0691 (3)	0.7100 (4)	0.0753 (13)
H27A	0.0621	−0.0438	0.7080	0.113*	0.50
H27B	0.1732	−0.0604	0.7919	0.113*	0.50
H27C	0.1224	−0.1292	0.6936	0.113*	0.50
H27D	0.1763	−0.1117	0.7544	0.113*	0.50
H27E	0.0653	−0.0952	0.6705	0.113*	0.50
H27F	0.1161	−0.0264	0.7688	0.113*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0591 (6)	0.0301 (4)	0.0411 (5)	−0.0069 (4)	0.0162 (4)	−0.0032 (4)
O1	0.112 (2)	0.0470 (15)	0.0371 (14)	−0.0260 (15)	0.0131 (15)	−0.0077 (12)
O2	0.0585 (16)	0.0403 (14)	0.082 (2)	0.0076 (12)	0.0352 (14)	0.0070 (13)
Cl1	0.0539 (8)	0.1333 (14)	0.1814 (17)	0.0327 (8)	0.0032 (9)	0.0173 (12)
Cl2	0.0524 (9)	0.1227 (15)	0.233 (2)	−0.0053 (9)	0.0550 (12)	0.0662 (15)
Cl2'	0.084 (7)	0.111 (8)	0.078 (6)	0.039 (6)	0.017 (5)	0.038 (5)
N1	0.0406 (15)	0.0310 (14)	0.0358 (16)	−0.0053 (12)	0.0066 (12)	0.0008 (12)
C2	0.0355 (18)	0.0326 (17)	0.0318 (17)	−0.0039 (14)	0.0050 (14)	−0.0018 (14)
C3	0.0433 (19)	0.0376 (18)	0.0297 (17)	0.0013 (15)	0.0050 (15)	0.0047 (14)
C4	0.045 (2)	0.0261 (17)	0.044 (2)	0.0009 (14)	0.0111 (16)	0.0042 (14)
C5	0.045 (2)	0.0305 (18)	0.046 (2)	−0.0068 (15)	0.0156 (17)	0.0040 (16)
O3	0.0599 (16)	0.0561 (16)	0.0479 (15)	−0.0016 (13)	0.0268 (13)	0.0039 (12)
N6	0.0384 (16)	0.0393 (16)	0.0472 (18)	−0.0050 (13)	0.0146 (14)	0.0021 (13)
C7	0.045 (2)	0.0362 (19)	0.044 (2)	−0.0089 (16)	0.0147 (17)	−0.0084 (16)
O4	0.0505 (15)	0.087 (2)	0.0383 (15)	−0.0037 (14)	0.0074 (12)	−0.0110 (14)
C8	0.0420 (19)	0.0313 (17)	0.0416 (19)	−0.0020 (15)	0.0116 (16)	−0.0074 (14)
C9	0.0370 (18)	0.0368 (18)	0.0344 (18)	−0.0007 (15)	0.0138 (15)	−0.0049 (15)
C10	0.0329 (17)	0.0306 (17)	0.0287 (17)	−0.0038 (14)	0.0044 (14)	0.0004 (13)
C11	0.0396 (19)	0.0352 (19)	0.050 (2)	0.0033 (15)	0.0053 (16)	0.0020 (16)
C12	0.0377 (19)	0.039 (2)	0.052 (2)	−0.0008 (16)	0.0109 (17)	−0.0039 (17)
C13	0.039 (2)	0.049 (2)	0.085 (3)	0.0022 (18)	0.020 (2)	0.014 (2)
C14	0.045 (2)	0.062 (3)	0.115 (4)	−0.005 (2)	0.025 (2)	0.009 (3)
C15	0.046 (2)	0.061 (3)	0.092 (3)	0.013 (2)	0.009 (2)	−0.003 (3)
C16	0.068 (3)	0.058 (3)	0.068 (3)	0.022 (2)	0.012 (2)	0.009 (2)
C17	0.056 (2)	0.042 (2)	0.064 (3)	0.0012 (19)	0.013 (2)	0.0047 (19)
C21	0.043 (2)	0.0328 (18)	0.0403 (19)	−0.0089 (15)	0.0068 (16)	−0.0021 (15)
C22	0.048 (2)	0.0401 (19)	0.046 (2)	0.0034 (16)	0.0119 (18)	0.0013 (17)
C23	0.066 (3)	0.041 (2)	0.041 (2)	−0.0026 (19)	0.0063 (19)	0.0072 (17)
C24	0.055 (2)	0.048 (2)	0.046 (2)	−0.0137 (19)	0.0148 (18)	0.0010 (18)
C25	0.046 (2)	0.058 (3)	0.073 (3)	−0.0058 (19)	0.021 (2)	0.006 (2)
C26	0.041 (2)	0.053 (2)	0.057 (2)	−0.0028 (18)	0.0053 (18)	0.0143 (18)
C27	0.080 (3)	0.079 (3)	0.070 (3)	−0.018 (3)	0.024 (2)	0.012 (2)

Geometric parameters (Å, º)

S1—O1	1.429 (3)	C11—H11A	0.97
S1—O2	1.431 (3)	C11—H11B	0.97
S1—N1	1.658 (3)	C12—C13	1.365 (5)
S1—C21	1.761 (3)	C12—C17	1.375 (5)
Cl1—C15	1.732 (4)	C13—C14	1.387 (5)
Cl2—C14	1.707 (4)	C13—H13	0.93
Cl2'—C16	1.575 (9)	C14—C15	1.373 (6)
N1—C10	1.493 (4)	C14—H14	0.93
N1—C2	1.495 (4)	C15—C16	1.367 (6)
C2—C10	1.481 (4)	C16—C17	1.381 (5)
C2—C3	1.526 (4)	C16—H16	0.93
C2—H2	0.98	C17—H17	0.93
C3—C11	1.539 (4)	C21—C26	1.375 (5)
C3—C4	1.548 (4)	C21—C22	1.378 (5)
C3—H3	0.98	C22—C23	1.376 (5)
C4—C5	1.507 (4)	C22—H22	0.93
C4—C8	1.548 (4)	C23—C24	1.373 (5)
C4—H4	0.98	C23—H23	0.93
C5—O3	1.209 (4)	C24—C25	1.387 (5)
C5—N6	1.401 (4)	C24—C27	1.513 (5)
N6—C7	1.402 (4)	C25—C26	1.382 (5)
N6—C12	1.433 (4)	C25—H25	0.93
C7—O4	1.203 (4)	C26—H26	0.93
C7—C8	1.510 (5)	C27—H27A	0.96
C8—C9	1.553 (4)	C27—H27B	0.96
C8—H8	0.98	C27—H27C	0.96
C9—C10	1.518 (4)	C27—H27D	0.96
C9—C11	1.533 (4)	C27—H27E	0.96
C9—H9	0.98	C27—H27F	0.96
C10—H10	0.98
O1—S1—O2	117.21 (18)	C13—C12—N6	119.2 (3)
O1—S1—N1	105.57 (15)	C17—C12—N6	120.4 (3)
O2—S1—N1	112.42 (14)	C12—C13—C14	119.6 (4)
O1—S1—C21	110.71 (16)	C12—C13—H13	120.2
O2—S1—C21	108.70 (16)	C14—C13—H13	120.2
N1—S1—C21	101.02 (14)	C15—C14—C13	120.2 (4)
C10—N1—C2	59.42 (18)	C15—C14—Cl2	120.1 (3)
C10—N1—S1	116.8 (2)	C13—C14—Cl2	119.7 (4)
C2—N1—S1	113.8 (2)	C15—C14—H14	119.9
C10—C2—N1	60.22 (19)	C13—C14—H14	119.9
C10—C2—C3	104.7 (3)	C16—C15—C14	119.7 (4)
N1—C2—C3	113.1 (3)	C16—C15—Cl1	119.8 (4)
C10—C2—H2	121.0	C14—C15—Cl1	120.5 (4)
N1—C2—H2	121.0	C15—C16—C17	120.4 (4)
C3—C2—H2	121.0	C15—C16—Cl2'	111.6 (5)
C2—C3—C11	102.6 (3)	C17—C16—Cl2'	128.0 (5)
C2—C3—C4	104.5 (2)	C15—C16—H16	119.9
C11—C3—C4	99.9 (3)	C17—C16—H16	119.8
C2—C3—H3	115.9	C12—C17—C16	119.7 (4)
C11—C3—H3	115.9	C12—C17—H17	120.2
C4—C3—H3	115.9	C16—C17—H17	120.2
C5—C4—C8	105.2 (3)	C26—C21—C22	120.6 (3)
C5—C4—C3	115.9 (3)	C26—C21—S1	121.2 (3)
C8—C4—C3	103.6 (2)	C22—C21—S1	118.1 (3)
C5—C4—H4	110.6	C23—C22—C21	119.2 (3)
C8—C4—H4	110.6	C23—C22—H22	120.4
C3—C4—H4	110.6	C21—C22—H22	120.4
O3—C5—N6	124.4 (3)	C24—C23—C22	121.7 (3)
O3—C5—C4	127.3 (3)	C24—C23—H23	119.2
N6—C5—C4	108.3 (3)	C22—C23—H23	119.2
C5—N6—C7	113.1 (3)	C23—C24—C25	118.1 (3)
C5—N6—C12	124.5 (3)	C23—C24—C27	120.6 (4)
C7—N6—C12	122.5 (3)	C25—C24—C27	121.3 (4)
O4—C7—N6	124.4 (3)	C26—C25—C24	121.2 (4)
O4—C7—C8	127.4 (3)	C26—C25—H25	119.4
N6—C7—C8	108.2 (3)	C24—C25—H25	119.4
C7—C8—C4	105.1 (3)	C21—C26—C25	119.1 (4)
C7—C8—C9	117.5 (3)	C21—C26—H26	120.4
C4—C8—C9	103.2 (2)	C25—C26—H26	120.4
C7—C8—H8	110.2	C24—C27—H27A	109.5
C4—C8—H8	110.2	C24—C27—H27B	109.5
C9—C8—H8	110.2	H27A—C27—H27B	109.5
C10—C9—C11	103.1 (2)	C24—C27—H27C	109.5
C10—C9—C8	105.8 (2)	H27A—C27—H27C	109.5
C11—C9—C8	98.9 (2)	H27B—C27—H27C	109.5
C10—C9—H9	115.6	C24—C27—H27D	109.5
C11—C9—H9	115.6	H27A—C27—H27D	141.1
C8—C9—H9	115.6	H27B—C27—H27D	56.3
C2—C10—N1	60.37 (18)	H27C—C27—H27D	56.3
C2—C10—C9	105.2 (2)	C24—C27—H27E	109.5
N1—C10—C9	112.6 (2)	H27A—C27—H27E	56.3
C2—C10—H10	121.0	H27B—C27—H27E	141.1
N1—C10—H10	121.0	H27C—C27—H27E	56.3
C9—C10—H10	121.0	H27D—C27—H27E	109.5
C9—C11—C3	95.1 (2)	C24—C27—H27F	109.5
C9—C11—H11A	112.7	H27A—C27—H27F	56.3
C3—C11—H11A	112.7	H27B—C27—H27F	56.3
C9—C11—H11B	112.7	H27C—C27—H27F	141.1
C3—C11—H11B	112.7	H27D—C27—H27F	109.5
H11A—C11—H11B	110.2	H27E—C27—H27F	109.5
C13—C12—C17	120.3 (3)
O1—S1—N1—C10	−158.3 (2)	S1—N1—C10—C9	−161.8 (2)
O2—S1—N1—C10	−29.4 (3)	C11—C9—C10—C2	31.8 (3)
C21—S1—N1—C10	86.3 (2)	C8—C9—C10—C2	−71.6 (3)
O1—S1—N1—C2	−91.9 (2)	C11—C9—C10—N1	−32.0 (3)
O2—S1—N1—C2	37.0 (3)	C8—C9—C10—N1	−135.4 (2)
C21—S1—N1—C2	152.7 (2)	C10—C9—C11—C3	−49.8 (3)
S1—N1—C2—C10	−108.2 (2)	C8—C9—C11—C3	58.8 (3)
C10—N1—C2—C3	−94.2 (3)	C2—C3—C11—C9	50.2 (3)
S1—N1—C2—C3	157.6 (2)	C4—C3—C11—C9	−57.2 (3)
C10—C2—C3—C11	−33.0 (3)	C5—N6—C12—C13	51.7 (5)
N1—C2—C3—C11	30.5 (3)	C7—N6—C12—C13	−128.9 (4)
C10—C2—C3—C4	70.9 (3)	C5—N6—C12—C17	−130.4 (4)
N1—C2—C3—C4	134.4 (3)	C7—N6—C12—C17	49.0 (5)
C2—C3—C4—C5	42.3 (3)	C17—C12—C13—C14	−0.2 (6)
C11—C3—C4—C5	148.3 (3)	N6—C12—C13—C14	177.7 (4)
C2—C3—C4—C8	−72.3 (3)	C12—C13—C14—C15	−1.8 (7)
C11—C3—C4—C8	33.6 (3)	C12—C13—C14—Cl2	178.5 (3)
C8—C4—C5—O3	173.1 (3)	C13—C14—C15—C16	2.4 (7)
C3—C4—C5—O3	59.3 (4)	Cl2—C14—C15—C16	−177.9 (4)
C8—C4—C5—N6	−4.8 (3)	C13—C14—C15—Cl1	−176.6 (4)
C3—C4—C5—N6	−118.6 (3)	Cl2—C14—C15—Cl1	3.1 (6)
O3—C5—N6—C7	−174.5 (3)	C14—C15—C16—C17	−1.0 (7)
C4—C5—N6—C7	3.4 (4)	Cl1—C15—C16—C17	178.0 (3)
O3—C5—N6—C12	4.9 (5)	C14—C15—C16—Cl2'	−179.6 (6)
C4—C5—N6—C12	−177.1 (3)	Cl1—C15—C16—Cl2'	−0.6 (7)
C5—N6—C7—O4	−179.8 (3)	C13—C12—C17—C16	1.6 (6)
C12—N6—C7—O4	0.8 (5)	N6—C12—C17—C16	−176.3 (3)
C5—N6—C7—C8	−0.5 (4)	C15—C16—C17—C12	−0.9 (6)
C12—N6—C7—C8	−179.9 (3)	Cl2'—C16—C17—C12	177.4 (6)
O4—C7—C8—C4	176.7 (3)	O1—S1—C21—C26	−66.2 (3)
N6—C7—C8—C4	−2.5 (3)	O2—S1—C21—C26	163.7 (3)
O4—C7—C8—C9	−69.4 (5)	N1—S1—C21—C26	45.3 (3)
N6—C7—C8—C9	111.4 (3)	O1—S1—C21—C22	113.4 (3)
C5—C4—C8—C7	4.4 (3)	O2—S1—C21—C22	−16.7 (3)
C3—C4—C8—C7	126.5 (3)	N1—S1—C21—C22	−135.2 (3)
C5—C4—C8—C9	−119.2 (3)	C26—C21—C22—C23	1.7 (5)
C3—C4—C8—C9	2.9 (3)	S1—C21—C22—C23	−177.9 (3)
C7—C8—C9—C10	−47.0 (3)	C21—C22—C23—C24	−1.2 (6)
C4—C8—C9—C10	68.0 (3)	C22—C23—C24—C25	−0.8 (6)
C7—C8—C9—C11	−153.4 (3)	C22—C23—C24—C27	179.5 (4)
C4—C8—C9—C11	−38.4 (3)	C23—C24—C25—C26	2.3 (6)
C3—C2—C10—N1	108.5 (3)	C27—C24—C25—C26	−178.0 (4)
N1—C2—C10—C9	−107.7 (3)	C22—C21—C26—C25	−0.3 (5)
C3—C2—C10—C9	0.8 (3)	S1—C21—C26—C25	179.3 (3)
S1—N1—C10—C2	103.1 (2)	C24—C25—C26—C21	−1.8 (6)
C2—N1—C10—C9	95.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4^i	0.98	2.47	3.440 (4)	170
C9—H9···O1^ii	0.98	2.57	3.317 (4)	134
C13—H13···O1^iii	0.93	2.41	3.253 (5)	150
C17—H17···O3^ii	0.93	2.55	3.451 (5)	164
C22—H22···O2^iv	0.93	2.45	3.097 (4)	127

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

(II) 4-(4-chlorophenyl)-9-(4-methylphenylsulfonyl)-4,9- diazatetracyclo[5.3.1.0^2,6.0^8,10]undecane-3,5-dione

Crystal data

C22H19ClN2O4S	Z = 2
Mr = 442.90	F(000) = 460
Triclinic, P1	Dx = 1.449 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.975 (2) Å	Cell parameters from 25 reflections
b = 10.167 (5) Å	θ = 8.6–17.6°
c = 12.876 (1) Å	µ = 0.32 mm^−1
α = 105.06 (2)°	T = 293 K
β = 109.89 (2)°	Irregular block, colourless
γ = 100.97 (3)°	0.43 × 0.40 × 0.36 mm
V = 1015.4 (6) Å^3

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.013
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 1.8°
Graphite monochromator	h = −10→10
ω/2θ scans	k = −11→12
3941 measured reflections	l = −15→0
3764 independent reflections	3 standard reflections every 200 reflections
3118 reflections with I > 2σ(I)	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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0472P)^2 + 0.3187P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3764 reflections	Δρmax = 0.24 e Å^−3
273 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (2)

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

	x	y	z	Uiso*/Ueq
S1	0.16108 (5)	0.38633 (5)	0.17523 (4)	0.04477 (15)
O1	0.01990 (17)	0.43054 (17)	0.12292 (14)	0.0661 (4)
O2	0.15124 (18)	0.30080 (15)	0.24661 (13)	0.0586 (4)
Cl1	0.98717 (8)	0.34187 (7)	0.62471 (5)	0.0712 (2)
N1	0.21359 (16)	0.29367 (14)	0.07313 (12)	0.0371 (3)
C2	0.0660 (2)	0.18945 (19)	−0.03435 (16)	0.0437 (4)
H2	−0.0467	0.1793	−0.0381	0.052*
C3	0.1022 (2)	0.06611 (19)	−0.10833 (15)	0.0455 (4)
H3	0.0188	−0.0275	−0.1373	0.055*
C4	0.2847 (2)	0.06683 (18)	−0.05316 (16)	0.0432 (4)
H4	0.2983	−0.0147	−0.1054	0.052*
C5	0.3653 (2)	0.07127 (18)	0.07114 (16)	0.0407 (4)
O3	0.32640 (17)	−0.01745 (15)	0.11178 (13)	0.0603 (4)
N6	0.50576 (16)	0.19196 (15)	0.13243 (13)	0.0370 (3)
C7	0.5095 (2)	0.28596 (19)	0.06819 (16)	0.0402 (4)
O4	0.60324 (17)	0.40581 (15)	0.11014 (13)	0.0587 (4)
C8	0.3848 (2)	0.20514 (19)	−0.05676 (16)	0.0440 (4)
H8	0.4443	0.1802	−0.1065	0.053*
C9	0.2503 (2)	0.2675 (2)	−0.11784 (16)	0.0478 (4)
H9	0.2858	0.3337	−0.1544	0.057*
C10	0.1617 (2)	0.32069 (19)	−0.04102 (16)	0.0435 (4)
H10	0.1129	0.3977	−0.0496	0.052*
C11	0.1128 (3)	0.1258 (2)	−0.20567 (17)	0.0587 (5)
H11A	0.0098	0.1407	−0.2498	0.070*
H11B	0.1490	0.0676	−0.2590	0.070*
C12	0.6191 (2)	0.22750 (17)	0.25190 (15)	0.0361 (4)
C13	0.5638 (2)	0.2101 (2)	0.33675 (17)	0.0450 (4)
H13	0.4504	0.1750	0.3167	0.054*
C14	0.6771 (2)	0.2448 (2)	0.45135 (18)	0.0503 (5)
H14	0.6404	0.2329	0.5087	0.060*
C15	0.8452 (2)	0.2972 (2)	0.48032 (16)	0.0464 (4)
C16	0.9009 (2)	0.3152 (2)	0.39598 (17)	0.0473 (4)
H16	1.0143	0.3506	0.4162	0.057*
C17	0.7882 (2)	0.28082 (19)	0.28178 (16)	0.0423 (4)
H17	0.8253	0.2932	0.2247	0.051*
C21	0.3377 (2)	0.53810 (19)	0.25751 (16)	0.0418 (4)
C22	0.4666 (2)	0.5314 (2)	0.35034 (19)	0.0529 (5)
H22	0.4620	0.4467	0.3658	0.063*
C23	0.6023 (2)	0.6515 (2)	0.4200 (2)	0.0600 (6)
H23	0.6892	0.6470	0.4825	0.072*
C24	0.6118 (3)	0.7784 (2)	0.3987 (2)	0.0565 (5)
C25	0.4814 (3)	0.7825 (2)	0.3044 (2)	0.0583 (5)
H25	0.4867	0.8671	0.2886	0.070*
C26	0.3438 (3)	0.6635 (2)	0.23312 (18)	0.0513 (5)
H26	0.2571	0.6676	0.1702	0.062*
C27	0.7591 (3)	0.9093 (3)	0.4793 (3)	0.0876 (8)
H27A	0.7473	0.9500	0.5511	0.131*
H27B	0.7643	0.9784	0.4410	0.131*
H27C	0.8595	0.8828	0.4971	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0332 (2)	0.0431 (3)	0.0551 (3)	0.01012 (18)	0.0199 (2)	0.0113 (2)
O1	0.0382 (7)	0.0698 (10)	0.0807 (11)	0.0257 (7)	0.0193 (7)	0.0118 (8)
O2	0.0590 (9)	0.0526 (8)	0.0657 (9)	0.0041 (7)	0.0367 (7)	0.0177 (7)
Cl1	0.0780 (4)	0.0752 (4)	0.0462 (3)	0.0208 (3)	0.0080 (3)	0.0248 (3)
N1	0.0299 (7)	0.0342 (7)	0.0417 (8)	0.0069 (6)	0.0111 (6)	0.0118 (6)
C2	0.0296 (8)	0.0405 (9)	0.0476 (10)	0.0047 (7)	0.0036 (7)	0.0154 (8)
C3	0.0425 (10)	0.0333 (9)	0.0402 (10)	0.0003 (7)	0.0019 (8)	0.0094 (7)
C4	0.0460 (10)	0.0323 (9)	0.0444 (10)	0.0104 (8)	0.0152 (8)	0.0082 (7)
C5	0.0338 (9)	0.0331 (9)	0.0513 (10)	0.0102 (7)	0.0129 (8)	0.0150 (8)
O3	0.0464 (8)	0.0490 (8)	0.0722 (10)	−0.0009 (6)	0.0072 (7)	0.0351 (7)
N6	0.0301 (7)	0.0358 (7)	0.0447 (8)	0.0085 (6)	0.0142 (6)	0.0160 (6)
C7	0.0353 (9)	0.0400 (9)	0.0488 (10)	0.0097 (7)	0.0201 (8)	0.0187 (8)
O4	0.0499 (8)	0.0464 (8)	0.0654 (9)	−0.0026 (6)	0.0114 (7)	0.0264 (7)
C8	0.0485 (10)	0.0440 (10)	0.0409 (10)	0.0111 (8)	0.0227 (8)	0.0134 (8)
C9	0.0545 (11)	0.0440 (10)	0.0380 (9)	0.0062 (8)	0.0128 (8)	0.0185 (8)
C10	0.0373 (9)	0.0367 (9)	0.0467 (10)	0.0091 (7)	0.0047 (8)	0.0178 (8)
C11	0.0664 (13)	0.0502 (12)	0.0375 (10)	0.0063 (10)	0.0043 (9)	0.0123 (9)
C12	0.0322 (8)	0.0336 (8)	0.0433 (9)	0.0122 (7)	0.0152 (7)	0.0140 (7)
C13	0.0381 (9)	0.0510 (11)	0.0559 (11)	0.0175 (8)	0.0251 (9)	0.0239 (9)
C14	0.0580 (12)	0.0580 (12)	0.0514 (11)	0.0260 (10)	0.0308 (10)	0.0277 (9)
C15	0.0512 (11)	0.0426 (10)	0.0422 (10)	0.0178 (8)	0.0134 (8)	0.0150 (8)
C16	0.0354 (9)	0.0489 (10)	0.0490 (11)	0.0083 (8)	0.0121 (8)	0.0147 (8)
C17	0.0353 (9)	0.0461 (10)	0.0442 (10)	0.0093 (7)	0.0180 (8)	0.0139 (8)
C21	0.0387 (9)	0.0384 (9)	0.0477 (10)	0.0117 (7)	0.0209 (8)	0.0101 (8)
C22	0.0450 (10)	0.0402 (10)	0.0678 (13)	0.0156 (8)	0.0169 (9)	0.0168 (9)
C23	0.0399 (10)	0.0544 (12)	0.0700 (14)	0.0136 (9)	0.0114 (10)	0.0133 (10)
C24	0.0510 (12)	0.0477 (11)	0.0651 (13)	0.0053 (9)	0.0316 (11)	0.0076 (10)
C25	0.0770 (15)	0.0401 (10)	0.0640 (13)	0.0097 (10)	0.0396 (12)	0.0198 (9)
C26	0.0608 (12)	0.0482 (11)	0.0477 (11)	0.0171 (9)	0.0234 (9)	0.0196 (9)
C27	0.0724 (17)	0.0571 (15)	0.098 (2)	−0.0093 (12)	0.0284 (15)	0.0020 (14)

Geometric parameters (Å, º)

S1—O2	1.4318 (15)	C10—H10	0.98
S1—O1	1.4334 (15)	C11—H11A	0.97
S1—N1	1.6688 (15)	C11—H11B	0.97
S1—C21	1.759 (2)	C12—C13	1.381 (2)
Cl1—C15	1.737 (2)	C12—C17	1.388 (2)
N1—C10	1.498 (2)	C13—C14	1.381 (3)
N1—C2	1.500 (2)	C13—H13	0.93
C2—C10	1.483 (3)	C14—C15	1.381 (3)
C2—C3	1.526 (3)	C14—H14	0.93
C2—H2	0.98	C15—C16	1.378 (3)
C3—C4	1.546 (3)	C16—C17	1.376 (3)
C3—C11	1.550 (3)	C16—H16	0.93
C3—H3	0.98	C17—H17	0.93
C4—C5	1.500 (3)	C21—C22	1.379 (3)
C4—C8	1.539 (3)	C21—C26	1.386 (3)
C4—H4	0.98	C22—C23	1.379 (3)
C5—O3	1.208 (2)	C22—H22	0.93
C5—N6	1.396 (2)	C23—C24	1.380 (3)
N6—C7	1.420 (2)	C23—H23	0.93
N6—C12	1.428 (2)	C24—C25	1.387 (3)
C7—O4	1.201 (2)	C24—C27	1.508 (3)
C7—C8	1.501 (3)	C25—C26	1.384 (3)
C8—C9	1.543 (3)	C25—H25	0.93
C8—H8	0.98	C26—H26	0.93
C9—C10	1.525 (3)	C27—H27A	0.96
C9—C11	1.551 (3)	C27—H27B	0.96
C9—H9	0.98	C27—H27C	0.96
O2—S1—O1	118.64 (10)	C2—C10—H10	120.5
O2—S1—N1	105.22 (8)	N1—C10—H10	120.5
O1—S1—N1	111.40 (9)	C9—C10—H10	120.5
O2—S1—C21	108.83 (9)	C3—C11—C9	94.45 (14)
O1—S1—C21	109.13 (10)	C3—C11—H11A	112.8
N1—S1—C21	102.35 (8)	C9—C11—H11A	112.8
C10—N1—C2	59.29 (11)	C3—C11—H11B	112.8
C10—N1—S1	116.28 (11)	C9—C11—H11B	112.8
C2—N1—S1	113.05 (11)	H11A—C11—H11B	110.3
C10—C2—N1	60.32 (11)	C13—C12—C17	120.11 (16)
C10—C2—C3	105.39 (16)	C13—C12—N6	121.51 (15)
N1—C2—C3	115.28 (14)	C17—C12—N6	118.38 (15)
C10—C2—H2	120.1	C14—C13—C12	119.93 (17)
N1—C2—H2	120.1	C14—C13—H13	120.0
C3—C2—H2	120.1	C12—C13—H13	120.0
C2—C3—C4	112.99 (14)	C15—C14—C13	119.63 (18)
C2—C3—C11	98.77 (15)	C15—C14—H14	120.2
C4—C3—C11	98.48 (16)	C13—C14—H14	120.2
C2—C3—H3	114.8	C16—C15—C14	120.63 (17)
C4—C3—H3	114.8	C16—C15—Cl1	119.87 (15)
C11—C3—H3	114.8	C14—C15—Cl1	119.50 (15)
C5—C4—C8	105.68 (14)	C17—C16—C15	119.84 (17)
C5—C4—C3	122.04 (15)	C17—C16—H16	120.1
C8—C4—C3	103.57 (14)	C15—C16—H16	120.1
C5—C4—H4	108.3	C16—C17—C12	119.85 (17)
C8—C4—H4	108.3	C16—C17—H17	120.1
C3—C4—H4	108.3	C12—C17—H17	120.1
O3—C5—N6	124.24 (17)	C22—C21—C26	120.82 (18)
O3—C5—C4	127.44 (16)	C22—C21—S1	118.41 (15)
N6—C5—C4	108.11 (15)	C26—C21—S1	120.71 (15)
C5—N6—C7	111.87 (14)	C23—C22—C21	119.37 (19)
C5—N6—C12	124.13 (14)	C23—C22—H22	120.3
C7—N6—C12	123.41 (14)	C21—C22—H22	120.3
O4—C7—N6	123.58 (17)	C22—C23—C24	121.3 (2)
O4—C7—C8	128.80 (17)	C22—C23—H23	119.3
N6—C7—C8	107.56 (14)	C24—C23—H23	119.3
C7—C8—C4	104.91 (15)	C23—C24—C25	118.37 (19)
C7—C8—C9	120.57 (15)	C23—C24—C27	120.0 (2)
C4—C8—C9	104.02 (14)	C25—C24—C27	121.6 (2)
C7—C8—H8	108.9	C26—C25—C24	121.5 (2)
C4—C8—H8	108.9	C26—C25—H25	119.3
C9—C8—H8	108.9	C24—C25—H25	119.3
C10—C9—C8	112.10 (14)	C25—C26—C21	118.6 (2)
C10—C9—C11	98.98 (16)	C25—C26—H26	120.7
C8—C9—C11	99.14 (15)	C21—C26—H26	120.7
C10—C9—H9	114.8	C24—C27—H27A	109.5
C8—C9—H9	114.8	C24—C27—H27B	109.5
C11—C9—H9	114.8	H27A—C27—H27B	109.5
C2—C10—N1	60.39 (11)	C24—C27—H27C	109.5
C2—C10—C9	104.75 (15)	H27A—C27—H27C	109.5
N1—C10—C9	114.59 (14)	H27B—C27—H27C	109.5
O2—S1—N1—C10	153.97 (12)	C8—C9—C10—C2	−67.60 (18)
O1—S1—N1—C10	24.16 (14)	C11—C9—C10—C2	36.14 (17)
C21—S1—N1—C10	−92.33 (13)	C8—C9—C10—N1	−3.8 (2)
O2—S1—N1—C2	88.10 (13)	C11—C9—C10—N1	99.95 (16)
O1—S1—N1—C2	−41.70 (14)	C2—C3—C11—C9	55.94 (17)
C21—S1—N1—C2	−158.19 (12)	C4—C3—C11—C9	−59.06 (17)
S1—N1—C2—C10	107.87 (13)	C10—C9—C11—C3	−56.47 (17)
C10—N1—C2—C3	93.93 (18)	C8—C9—C11—C3	57.81 (17)
S1—N1—C2—C3	−158.20 (13)	C5—N6—C12—C13	−40.5 (2)
C10—C2—C3—C4	67.77 (18)	C7—N6—C12—C13	129.92 (18)
N1—C2—C3—C4	3.7 (2)	C5—N6—C12—C17	139.57 (17)
C10—C2—C3—C11	−35.39 (17)	C7—N6—C12—C17	−50.0 (2)
N1—C2—C3—C11	−99.41 (17)	C17—C12—C13—C14	−0.5 (3)
C2—C3—C4—C5	53.6 (2)	N6—C12—C13—C14	179.61 (16)
C11—C3—C4—C5	156.92 (16)	C12—C13—C14—C15	0.2 (3)
C2—C3—C4—C8	−65.05 (19)	C13—C14—C15—C16	0.0 (3)
C11—C3—C4—C8	38.29 (17)	C13—C14—C15—Cl1	179.58 (14)
C8—C4—C5—O3	−179.35 (18)	C14—C15—C16—C17	0.1 (3)
C3—C4—C5—O3	63.0 (3)	Cl1—C15—C16—C17	−179.54 (14)
C8—C4—C5—N6	−4.42 (18)	C15—C16—C17—C12	−0.3 (3)
C3—C4—C5—N6	−122.02 (17)	C13—C12—C17—C16	0.5 (3)
O3—C5—N6—C7	−172.88 (17)	N6—C12—C17—C16	−179.57 (15)
C4—C5—N6—C7	11.99 (19)	O2—S1—C21—C22	23.34 (18)
O3—C5—N6—C12	−1.5 (3)	O1—S1—C21—C22	154.21 (16)
C4—C5—N6—C12	−176.63 (14)	N1—S1—C21—C22	−87.67 (16)
C5—N6—C7—O4	168.04 (17)	O2—S1—C21—C26	−153.60 (15)
C12—N6—C7—O4	−3.4 (3)	O1—S1—C21—C26	−22.74 (18)
C5—N6—C7—C8	−14.64 (19)	N1—S1—C21—C26	95.38 (16)
C12—N6—C7—C8	173.90 (14)	C26—C21—C22—C23	0.4 (3)
O4—C7—C8—C4	−171.94 (19)	S1—C21—C22—C23	−176.50 (16)
N6—C7—C8—C4	10.93 (18)	C21—C22—C23—C24	0.0 (3)
O4—C7—C8—C9	−55.3 (3)	C22—C23—C24—C25	−0.5 (3)
N6—C7—C8—C9	127.57 (16)	C22—C23—C24—C27	177.8 (2)
C5—C4—C8—C7	−4.00 (18)	C23—C24—C25—C26	0.6 (3)
C3—C4—C8—C7	125.40 (15)	C27—C24—C25—C26	−177.7 (2)
C5—C4—C8—C9	−131.51 (15)	C24—C25—C26—C21	−0.1 (3)
C3—C4—C8—C9	−2.12 (17)	C22—C21—C26—C25	−0.4 (3)
C7—C8—C9—C10	−48.3 (2)	S1—C21—C26—C25	176.45 (15)
C4—C8—C9—C10	68.79 (18)	N1—C2—C3—C11	−99.41 (17)
C7—C8—C9—C11	−151.95 (16)	N1—C2—C3—C4	3.7 (2)
C4—C8—C9—C11	−34.85 (18)	C5—C4—C3—C11	156.92 (16)
C3—C2—C10—N1	−110.67 (14)	C5—C4—C3—C2	53.6 (2)
N1—C2—C10—C9	110.20 (15)	N1—C10—C9—C8	−3.8 (2)
C3—C2—C10—C9	−0.47 (17)	N1—C10—C9—C11	99.95 (16)
S1—N1—C10—C2	−102.40 (13)	C7—C8—C9—C10	−48.3 (2)
C2—N1—C10—C9	−93.56 (17)	C7—C8—C9—C11	−151.95 (16)
S1—N1—C10—C9	164.05 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3^i	0.98	2.43	3.289 (2)	146
C9—H9···O4^ii	0.98	2.48	3.294 (3)	140
C10—H10···O1^iii	0.98	2.50	3.457 (3)	166

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