Polymorphs and pseudopolymorphs of N,N′-dithiobisphthalimide

Farrell, D.M.M.; Glidewell, C.; Low, J.N.; Skakle, J.M.S.; Zakaria, C.M.

doi:10.1107/S0108768101020006

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Polymorphs and pseudopolymorphs of N,N′-dithiobisphthalimide

D. M. M. Farrell, C. Glidewell, J. N. Low, J. M. S. Skakle and C. M. Zakaria

N,N′-Dithiobisphthalimide, C₁₆H₈N₂O₄S₂ (I), forms a wide range of polymorphs and solvates (pseudopolymorphs). When (I) is crystallized from methanol it yields a solvent-free polymorph (4), in Pna2₁ with Z′ = 1, in which the molecules are linked into chains by a single C—H

O hydrogen bond: crystallization from either acetonitrile or dimethylformamide produces a monoclinic polymorph (5), in P2₁/c with Z′ = 2, also solvent-free, in which the molecules are linked into molecular ladders. Nitromethane forms a monosolvate, C₁₆H₈N₂O₄S₂·CH₃NO₂ (6), in P2₁/c with Z′ = 1, in which the solvent molecules are linked to the molecules of (I) not only via a conventional C—H

O hydrogen bond but also via a polarized multicentre interaction involving all three C—H bonds of the solvent molecule. Chlorobenzene forms a precise hemisolvate, C₁₆H₈N₂O₄S₂·0.5C₆H₅Cl (7), in P ${\bar 1 }$ with Z′ = 1, while ethylbenzene forms an approximate hemisolvate 2C₁₆H₈N₂O₄S₂·0.913C₆H₅C₂H₅·0.087H₂O (8), in P2₁/c with eight molecules of (I) per unit cell. In both solvates the molecules of (I) are linked, in (7) by π

π stacking interactions augmented by weak C—H

O hydrogen bonds and in (8) by stronger C—H

O hydrogen bonds: the solvent molecules lie in isolated cavities, disordered across inversion centres in (7) and fully ordered in general positions in (8). Crystallization of (I) either from tetrahydrofuran or from wet tert-butanol yields isomorphous solvates (9) and (10), respectively, in C2/c with Z′ = 0.5, in which molecules of (I) lie across twofold rotation axes and are linked by π

π stacking interactions and very weak C—H

O hydrogen bonds, forming a framework enclosing continuous channels: highly disordered solvent molecules lie within these channels. p-Xylene and toluene form isomorphous hemisolvates (11) and (12) with unit cells metrically very similar to those of (9) and (10), but in P2₁/n with Z′ = 1: in these two solvates the molecules of (I) are linked into a framework by very short C—H

O hydrogen bonds; the solvent molecules lie within continuous channels, but they are localized across inversion centres so that the toluene is disordered across an inversion centre.

Keywords: polymorphs and pseudopolymorphs; hydrogen bonding; disorder.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101020006/na0132sup1.cif Contains datablocks global, 4, 5, 6, 7, 8, 9, 10, 11, 12
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01324sup2.hkl Contains datablock 4
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01325sup3.hkl Contains datablock 5
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01326sup4.hkl Contains datablock 6
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01327sup5.hkl Contains datablock 7
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01328sup6.hkl Contains datablock 8
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01329sup7.hkl Contains datablock 9
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na013210sup8.hkl Contains datablock VII
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na013211sup9.hkl Contains datablock VIII
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na013212sup10.hkl Contains datablock IX

CCDC references: 184899; 184900; 184901; 184902; 184903; 184904; 184905; 184906; 184907

Computing details top

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 2001). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999) for (4), (5), (6), (7), (8), (9), (10), (12); SHELXL97(Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999) for (11).

(4) N,N'-Dithiodiphthalimide top

Crystal data top

C₁₆H₈N₂O₄S₂	D_x = 1.573 Mg m⁻³
M_r = 356.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 2913 reflections
a = 7.1298 (2) Å	θ = 2.9–27.5°
b = 30.7247 (13) Å	µ = 0.38 mm⁻¹
c = 6.8691 (2) Å	T = 120 K
V = 1504.75 (9) Å³	Needle, colourless
Z = 4	0.35 × 0.08 × 0.07 mm
F(000) = 728

Data collection top

Kappa-CCD diffractometer	2913 independent reflections
Radiation source: fine-focus sealed X-ray tube	2154 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −5→9
T_min = 0.879, T_max = 0.974	k = −39→39
6890 measured reflections	l = −7→6

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0238P)² + 0.4375P] where P = (F_o² + 2F_c²)/3
2913 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	−0.08746 (14)	0.15565 (3)	0.03776 (18)	0.0382 (3)
N11	−0.1375 (4)	0.10631 (10)	0.1313 (5)	0.0340 (9)
C11	−0.0913 (6)	0.09242 (12)	0.3217 (7)	0.0365 (10)
O11	−0.0107 (4)	0.11402 (8)	0.4399 (4)	0.0419 (8)
C12	−0.2302 (6)	0.07319 (13)	0.0236 (8)	0.0362 (10)
O12	−0.2821 (4)	0.07721 (8)	−0.1422 (5)	0.0427 (8)
C13	−0.2414 (5)	0.03558 (12)	0.1549 (6)	0.0347 (10)
C14	−0.3158 (6)	−0.00545 (13)	0.1219 (8)	0.0454 (12)
C15	−0.3056 (6)	−0.03503 (14)	0.2745 (9)	0.0542 (15)
C16	−0.2281 (6)	−0.02398 (15)	0.4529 (8)	0.0506 (15)
C17	−0.1558 (6)	0.01772 (14)	0.4860 (6)	0.0428 (12)
C18	−0.1635 (5)	0.04685 (12)	0.3319 (7)	0.0348 (11)
S2	0.17069 (15)	0.15018 (3)	−0.08615 (17)	0.0346 (3)
N21	0.3147 (4)	0.16844 (9)	0.0906 (5)	0.0298 (8)
C21	0.3941 (6)	0.14221 (13)	0.2389 (6)	0.0303 (10)
O21	0.3961 (4)	0.10280 (8)	0.2396 (4)	0.0408 (8)
C22	0.3296 (5)	0.21368 (12)	0.1378 (6)	0.0262 (9)
O22	0.2645 (3)	0.24237 (8)	0.0410 (4)	0.0322 (6)
C23	0.4286 (5)	0.21544 (12)	0.3267 (6)	0.0255 (9)
C24	0.4720 (5)	0.25079 (11)	0.4412 (6)	0.0265 (9)
C25	0.5534 (5)	0.24308 (14)	0.6218 (6)	0.0336 (10)
C26	0.5911 (6)	0.20127 (14)	0.6794 (6)	0.0335 (10)
C27	0.5516 (5)	0.16499 (13)	0.5672 (7)	0.0345 (10)
C28	0.4672 (5)	0.17306 (11)	0.3908 (6)	0.0257 (9)
H14	−0.3711	−0.0130	0.0007	0.055*
H15	−0.3530	−0.0636	0.2561	0.065*
H16	−0.2241	−0.0450	0.5542	0.061*
H17	−0.1038	0.0257	0.6082	0.051*
H24	0.4471	0.2796	0.3982	0.032*
H25	0.5830	0.2668	0.7052	0.040*
H26	0.6475	0.1970	0.8032	0.040*
H27	0.5809	0.1363	0.6094	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0338 (6)	0.0238 (5)	0.0569 (7)	−0.0012 (5)	−0.0121 (6)	0.0059 (5)
N11	0.0283 (19)	0.0248 (17)	0.049 (2)	−0.0033 (15)	−0.0117 (17)	0.0070 (15)
C11	0.031 (2)	0.027 (2)	0.052 (3)	0.010 (2)	−0.001 (2)	0.000 (2)
O11	0.050 (2)	0.0380 (16)	0.038 (2)	0.0000 (14)	−0.0070 (16)	−0.0050 (14)
C12	0.026 (2)	0.038 (2)	0.044 (3)	−0.0016 (18)	−0.002 (2)	0.000 (2)
O12	0.0399 (19)	0.0403 (17)	0.048 (2)	−0.0100 (14)	−0.0122 (15)	−0.0013 (15)
C13	0.023 (2)	0.027 (2)	0.055 (3)	0.0004 (18)	0.001 (2)	0.004 (2)
C14	0.026 (2)	0.030 (2)	0.080 (4)	0.000 (2)	−0.005 (2)	0.004 (2)
C15	0.025 (3)	0.028 (2)	0.110 (5)	0.002 (2)	0.005 (3)	0.015 (3)
C16	0.031 (3)	0.040 (3)	0.081 (4)	0.005 (2)	0.006 (3)	0.026 (3)
C17	0.034 (2)	0.048 (3)	0.047 (3)	0.006 (2)	0.002 (2)	0.009 (2)
C18	0.020 (2)	0.031 (2)	0.054 (3)	−0.0002 (19)	0.006 (2)	0.003 (2)
S2	0.0422 (6)	0.0288 (5)	0.0327 (6)	−0.0080 (5)	−0.0086 (5)	−0.0006 (5)
N21	0.0308 (19)	0.0238 (17)	0.035 (2)	−0.0056 (15)	−0.0059 (15)	0.0005 (15)
C21	0.027 (2)	0.032 (2)	0.032 (3)	0.0001 (19)	0.0017 (18)	0.0032 (19)
O21	0.0424 (19)	0.0242 (16)	0.056 (2)	0.0029 (14)	−0.0101 (15)	0.0002 (14)
C22	0.023 (2)	0.025 (2)	0.031 (2)	−0.0035 (17)	0.0006 (18)	−0.0013 (17)
O22	0.0401 (17)	0.0248 (14)	0.0318 (15)	−0.0007 (12)	−0.0086 (14)	0.0069 (14)
C23	0.016 (2)	0.032 (2)	0.029 (2)	−0.0049 (17)	0.0050 (17)	0.0016 (19)
C24	0.025 (2)	0.029 (2)	0.026 (2)	0.0011 (17)	0.0006 (18)	−0.0003 (17)
C25	0.028 (2)	0.042 (3)	0.031 (2)	0.000 (2)	−0.0025 (19)	−0.0103 (19)
C26	0.024 (2)	0.053 (3)	0.024 (3)	−0.001 (2)	−0.0058 (18)	0.003 (2)
C27	0.027 (2)	0.033 (2)	0.043 (3)	0.0024 (18)	−0.002 (2)	0.007 (2)
C28	0.026 (2)	0.028 (2)	0.023 (2)	0.0002 (16)	0.0006 (18)	0.0005 (17)

Geometric parameters (Å, º) top

S1—N11	1.685 (3)	S2—N21	1.687 (3)
S1—S2	2.035 (2)	N21—C21	1.417 (5)
N11—C11	1.415 (5)	N21—C22	1.431 (4)
N11—C12	1.422 (5)	C21—O21	1.211 (4)
C11—O11	1.195 (5)	C21—C28	1.503 (6)
C11—C18	1.493 (5)	C22—O22	1.198 (4)
C12—O12	1.204 (5)	C22—C23	1.478 (5)
C12—C13	1.468 (6)	C23—C24	1.376 (5)
C13—C18	1.381 (6)	C23—C28	1.402 (5)
C13—C14	1.386 (5)	C24—C25	1.389 (5)
C14—C15	1.389 (7)	C24—H24	0.9500
C14—H14	0.9500	C25—C26	1.371 (5)
C15—C16	1.386 (6)	C25—H25	0.9500
C15—H15	0.9500	C26—C27	1.384 (5)
C16—C17	1.400 (6)	C26—H26	0.9500
C16—H16	0.9500	C27—C28	1.376 (5)
C17—C18	1.387 (5)	C27—H27	0.9500
C17—H17	0.9500

N11—S1—S2	106.1 (2)	N21—S2—S1	102.8 (2)
C11—N11—C12	111.9 (3)	C21—N21—C22	111.1 (3)
C11—N11—S1	125.1 (3)	C21—N21—S2	124.9 (3)
C12—N11—S1	123.0 (3)	C22—N21—S2	122.1 (3)
O11—C11—N11	124.9 (4)	O21—C21—N21	125.2 (4)
O11—C11—C18	130.9 (4)	O21—C21—C28	128.6 (4)
N11—C11—C18	104.2 (4)	N21—C21—C28	106.2 (3)
O12—C12—N11	124.2 (4)	O22—C22—N21	124.1 (3)
O12—C12—C13	130.2 (4)	O22—C22—C23	130.2 (3)
N11—C12—C13	105.6 (4)	N21—C22—C23	105.7 (3)
C18—C13—C14	121.7 (4)	C24—C23—C28	120.6 (3)
C18—C13—C12	108.8 (4)	C24—C23—C22	129.6 (3)
C14—C13—C12	129.5 (4)	C28—C23—C22	109.6 (3)
C13—C14—C15	116.8 (5)	C23—C24—C25	118.0 (3)
C13—C14—H14	121.6	C23—C24—H24	121.0
C15—C14—H14	121.6	C25—C24—H24	121.0
C16—C15—C14	121.8 (4)	C26—C25—C24	119.9 (4)
C16—C15—H15	119.1	C26—C25—H25	120.0
C14—C15—H15	119.1	C24—C25—H25	120.0
C15—C16—C17	121.0 (4)	C25—C26—C27	123.7 (4)
C15—C16—H16	119.5	C25—C26—H26	118.2
C17—C16—H16	119.5	C27—C26—H26	118.2
C18—C17—C16	116.9 (4)	C28—C27—C26	115.7 (4)
C18—C17—H17	121.6	C28—C27—H27	122.1
C16—C17—H17	121.6	C26—C27—H27	122.1
C13—C18—C17	121.7 (4)	C27—C28—C23	122.0 (3)
C13—C18—C11	109.4 (4)	C27—C28—C21	130.5 (3)
C17—C18—C11	128.8 (4)	C23—C28—C21	107.4 (3)

S2—S1—N11—C11	89.4 (3)	S1—S2—N21—C21	88.6 (3)
S2—S1—N11—C12	−89.5 (3)	S1—S2—N21—C22	−74.1 (3)
C12—N11—C11—O11	179.0 (4)	C22—N21—C21—O21	177.8 (4)
S1—N11—C11—O11	−0.1 (6)	S2—N21—C21—O21	13.4 (6)
C12—N11—C11—C18	−0.4 (4)	C22—N21—C21—C28	−0.8 (4)
S1—N11—C11—C18	−179.5 (3)	S2—N21—C21—C28	−165.1 (3)
C11—N11—C12—O12	−179.5 (4)	C21—N21—C22—O22	−176.0 (4)
S1—N11—C12—O12	−0.4 (6)	S2—N21—C22—O22	−11.1 (5)
C11—N11—C12—C13	−0.7 (4)	C21—N21—C22—C23	1.2 (4)
S1—N11—C12—C13	178.4 (3)	S2—N21—C22—C23	166.1 (2)
O12—C12—C13—C18	−179.7 (4)	O22—C22—C23—C24	0.0 (7)
N11—C12—C13—C18	1.6 (4)	N21—C22—C23—C24	−176.9 (4)
O12—C12—C13—C14	−0.2 (8)	O22—C22—C23—C28	175.7 (4)
N11—C12—C13—C14	−178.9 (4)	N21—C22—C23—C28	−1.2 (4)
C18—C13—C14—C15	−1.0 (6)	C28—C23—C24—C25	−0.5 (5)
C12—C13—C14—C15	179.5 (4)	C22—C23—C24—C25	174.8 (4)
C13—C14—C15—C16	1.2 (7)	C23—C24—C25—C26	1.1 (6)
C14—C15—C16—C17	−0.3 (7)	C24—C25—C26—C27	−0.4 (6)
C15—C16—C17—C18	−0.8 (6)	C25—C26—C27—C28	−1.0 (6)
C14—C13—C18—C17	−0.1 (6)	C26—C27—C28—C23	1.7 (6)
C12—C13—C18—C17	179.5 (4)	C26—C27—C28—C21	−175.7 (4)
C14—C13—C18—C11	178.5 (4)	C24—C23—C28—C27	−1.0 (6)
C12—C13—C18—C11	−1.9 (4)	C22—C23—C28—C27	−177.2 (3)
C16—C17—C18—C13	1.0 (6)	C24—C23—C28—C21	176.9 (3)
C16—C17—C18—C11	−177.4 (4)	C22—C23—C28—C21	0.7 (4)
O11—C11—C18—C13	−177.9 (4)	O21—C21—C28—C27	−0.8 (7)
N11—C11—C18—C13	1.5 (4)	N21—C21—C28—C27	177.7 (4)
O11—C11—C18—C17	0.6 (7)	O21—C21—C28—C23	−178.5 (4)
N11—C11—C18—C17	179.9 (4)	N21—C21—C28—C23	0.0 (4)
N11—S1—S2—N21	−95.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O21ⁱ	0.95	2.51	3.343 (6)	147

Symmetry code: (i) −x, −y, z+1/2.

(5) N,N'-Dithiodiphthalimide top

Crystal data top

C₁₆H₈N₂O₄S₂	F(000) = 1456
M_r = 356.36	D_x = 1.543 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5052 (2) Å	Cell parameters from 6776 reflections
b = 7.8740 (1) Å	θ = 3.0–27.5°
c = 29.2050 (5) Å	µ = 0.37 mm⁻¹
β = 98.9640 (5)°	T = 120 K
V = 3067.73 (8) Å³	Plate, colourless
Z = 8	0.20 × 0.07 × 0.02 mm

Data collection top

Kappa-CCD diffractometer	6776 independent reflections
Radiation source: fine-focus sealed X-ray tube	5280 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −17→17
T_min = 0.930, T_max = 0.993	k = −10→10
26075 measured reflections	l = −37→37

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0713P)²] where P = (F_o² + 2F_c²)/3
6776 reflections	(Δ/σ)_max = 0.002
433 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891 which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S11	−0.24420 (4)	0.57462 (6)	−0.071870 (16)	0.01934 (13)
N11	−0.14413 (11)	0.62029 (19)	−0.03194 (5)	0.0172 (3)
C11	−0.14047 (14)	0.5888 (2)	0.01631 (6)	0.0193 (4)
O11	−0.20470 (10)	0.51447 (17)	0.03304 (5)	0.0252 (3)
C12	−0.06080 (14)	0.7205 (2)	−0.04104 (7)	0.0179 (4)
O12	−0.04923 (10)	0.77010 (17)	−0.07869 (5)	0.0239 (3)
C13	0.00065 (14)	0.7459 (2)	0.00528 (7)	0.0179 (4)
C14	0.08970 (14)	0.8347 (2)	0.01665 (7)	0.0212 (4)
C15	0.13082 (15)	0.8414 (2)	0.06334 (7)	0.0253 (5)
C16	0.08536 (16)	0.7611 (3)	0.09709 (7)	0.0274 (5)
C17	−0.00435 (15)	0.6722 (2)	0.08535 (7)	0.0245 (5)
C18	−0.04603 (14)	0.6674 (2)	0.03898 (6)	0.0180 (4)
S21	−0.32300 (4)	0.79638 (6)	−0.078152 (16)	0.01968 (13)
N21	−0.38538 (12)	0.79693 (19)	−0.03214 (6)	0.0195 (4)
C21	−0.34291 (14)	0.8565 (2)	0.01249 (6)	0.0195 (4)
O21	−0.25950 (10)	0.91405 (18)	0.02228 (5)	0.0260 (3)
C22	−0.48416 (15)	0.7327 (2)	−0.03250 (7)	0.0200 (4)
O22	−0.53487 (10)	0.66983 (19)	−0.06555 (5)	0.0281 (3)
C23	−0.50626 (14)	0.7623 (2)	0.01514 (7)	0.0184 (4)
C24	−0.59268 (15)	0.7274 (2)	0.03343 (7)	0.0214 (4)
C25	−0.59058 (16)	0.7656 (2)	0.08019 (7)	0.0237 (4)
C26	−0.50607 (15)	0.8326 (2)	0.10724 (7)	0.0243 (4)
C27	−0.41994 (15)	0.8686 (3)	0.08847 (7)	0.0242 (4)
C28	−0.42202 (14)	0.8334 (2)	0.04208 (7)	0.0191 (4)
S31	0.10432 (4)	0.31123 (7)	0.194488 (19)	0.02881 (15)
N31	0.10882 (12)	0.4339 (2)	0.24233 (6)	0.0242 (4)
C31	0.11793 (14)	0.3694 (2)	0.28861 (7)	0.0232 (4)
O31	0.11131 (12)	0.22189 (17)	0.29834 (6)	0.0346 (4)
C32	0.12446 (15)	0.6130 (3)	0.24234 (7)	0.0228 (4)
O32	0.12819 (12)	0.69731 (19)	0.20820 (5)	0.0346 (4)
C33	0.13886 (14)	0.6646 (2)	0.29152 (7)	0.0200 (4)
C34	0.15675 (15)	0.8245 (3)	0.31067 (8)	0.0266 (5)
C35	0.17462 (16)	0.8354 (3)	0.35848 (8)	0.0300 (5)
C36	0.17290 (17)	0.6915 (3)	0.38643 (8)	0.0320 (5)
C37	0.15286 (16)	0.5319 (3)	0.36676 (7)	0.0275 (5)
C38	0.13674 (15)	0.5208 (2)	0.31913 (7)	0.0214 (4)
S41	0.25028 (4)	0.29204 (6)	0.186064 (17)	0.02413 (14)
N41	0.29752 (12)	0.1252 (2)	0.21909 (5)	0.0202 (4)
C41	0.33845 (14)	0.1370 (2)	0.26688 (7)	0.0201 (4)
O41	0.33890 (11)	0.26371 (18)	0.29007 (5)	0.0288 (3)
C42	0.31169 (14)	−0.0391 (2)	0.20078 (6)	0.0187 (4)
O42	0.28951 (10)	−0.07959 (18)	0.16090 (4)	0.0251 (3)
C43	0.36174 (14)	−0.1385 (2)	0.24097 (7)	0.0187 (4)
C44	0.38989 (15)	−0.3082 (2)	0.24283 (7)	0.0244 (5)
C45	0.43508 (15)	−0.3698 (3)	0.28582 (7)	0.0274 (5)
C46	0.45167 (16)	−0.2658 (3)	0.32464 (7)	0.0271 (5)
C47	0.42348 (15)	−0.0959 (3)	0.32242 (7)	0.0245 (4)
C48	0.37841 (14)	−0.0350 (2)	0.27983 (6)	0.0193 (4)
H14	0.1212	0.8885	−0.0064	0.025*
H15	0.1914	0.9024	0.0724	0.030*
H16	0.1159	0.7670	0.1286	0.033*
H17	−0.0356	0.6170	0.1083	0.029*
H24	−0.6503	0.6800	0.0151	0.026*
H25	−0.6488	0.7451	0.0939	0.028*
H26	−0.5071	0.8542	0.1392	0.029*
H27	−0.3621	0.9155	0.1068	0.029*
H34	0.1568	0.9226	0.2918	0.032*
H35	0.1884	0.9432	0.3727	0.036*
H36	0.1856	0.7029	0.4192	0.038*
H37	0.1504	0.4340	0.3855	0.033*
H44	0.3789	−0.3788	0.2162	0.029*
H45	0.4550	−0.4855	0.2886	0.033*
H46	0.4830	−0.3117	0.3533	0.032*
H47	0.4347	−0.0247	0.3490	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S11	0.0193 (3)	0.0183 (2)	0.0195 (2)	−0.00238 (18)	0.00014 (19)	−0.00025 (18)
N11	0.0147 (9)	0.0176 (8)	0.0189 (8)	−0.0031 (6)	0.0015 (6)	0.0018 (6)
C11	0.0217 (11)	0.0142 (9)	0.0220 (10)	0.0026 (7)	0.0032 (8)	0.0039 (7)
O11	0.0236 (8)	0.0284 (8)	0.0241 (7)	−0.0071 (6)	0.0053 (6)	0.0065 (6)
C12	0.0148 (10)	0.0151 (9)	0.0240 (10)	0.0021 (7)	0.0042 (8)	0.0022 (7)
O12	0.0262 (8)	0.0249 (8)	0.0214 (7)	−0.0022 (6)	0.0062 (6)	0.0058 (6)
C13	0.0181 (10)	0.0117 (9)	0.0241 (10)	0.0013 (7)	0.0035 (8)	0.0018 (7)
C14	0.0186 (11)	0.0155 (9)	0.0293 (11)	−0.0017 (7)	0.0035 (8)	0.0013 (8)
C15	0.0195 (11)	0.0190 (10)	0.0353 (12)	−0.0016 (8)	−0.0026 (9)	−0.0039 (9)
C16	0.0289 (13)	0.0243 (11)	0.0259 (11)	0.0011 (9)	−0.0058 (9)	−0.0011 (9)
C17	0.0275 (12)	0.0217 (10)	0.0237 (11)	0.0007 (8)	0.0020 (9)	0.0025 (8)
C18	0.0176 (10)	0.0151 (9)	0.0207 (10)	0.0006 (7)	0.0011 (7)	0.0010 (7)
S21	0.0175 (3)	0.0222 (3)	0.0195 (2)	0.00001 (18)	0.00318 (19)	0.00432 (18)
N21	0.0162 (9)	0.0225 (9)	0.0202 (8)	−0.0029 (6)	0.0037 (6)	0.0001 (6)
C21	0.0191 (11)	0.0164 (9)	0.0232 (10)	−0.0010 (8)	0.0035 (8)	−0.0004 (7)
O21	0.0198 (8)	0.0284 (8)	0.0298 (8)	−0.0086 (6)	0.0041 (6)	−0.0044 (6)
C22	0.0190 (11)	0.0167 (9)	0.0236 (10)	−0.0006 (7)	0.0012 (8)	0.0015 (8)
O22	0.0241 (8)	0.0356 (9)	0.0236 (8)	−0.0083 (6)	0.0004 (6)	−0.0037 (6)
C23	0.0200 (11)	0.0134 (9)	0.0214 (10)	0.0004 (7)	0.0020 (8)	0.0019 (7)
C24	0.0201 (11)	0.0185 (10)	0.0258 (10)	−0.0037 (8)	0.0037 (8)	−0.0007 (8)
C25	0.0257 (12)	0.0187 (10)	0.0286 (11)	−0.0023 (8)	0.0098 (9)	−0.0025 (8)
C26	0.0279 (12)	0.0221 (10)	0.0241 (11)	−0.0019 (8)	0.0074 (9)	−0.0040 (8)
C27	0.0238 (12)	0.0228 (10)	0.0256 (10)	−0.0053 (8)	0.0029 (8)	−0.0061 (8)
C28	0.0191 (11)	0.0139 (9)	0.0247 (10)	−0.0011 (7)	0.0040 (8)	−0.0008 (7)
S31	0.0245 (3)	0.0304 (3)	0.0297 (3)	0.0057 (2)	−0.0014 (2)	−0.0088 (2)
N31	0.0265 (10)	0.0198 (9)	0.0265 (9)	0.0045 (7)	0.0047 (7)	−0.0018 (7)
C31	0.0191 (11)	0.0185 (10)	0.0331 (11)	0.0022 (8)	0.0070 (8)	0.0023 (8)
O31	0.0460 (10)	0.0151 (7)	0.0448 (10)	0.0023 (6)	0.0139 (8)	0.0031 (7)
C32	0.0194 (11)	0.0211 (10)	0.0288 (11)	0.0044 (8)	0.0060 (8)	0.0040 (8)
O32	0.0432 (10)	0.0317 (9)	0.0295 (9)	0.0061 (7)	0.0076 (7)	0.0090 (7)
C33	0.0173 (11)	0.0183 (10)	0.0258 (10)	0.0029 (8)	0.0074 (8)	0.0014 (8)
C34	0.0239 (12)	0.0169 (10)	0.0416 (13)	0.0006 (8)	0.0134 (9)	0.0000 (9)
C35	0.0291 (13)	0.0257 (11)	0.0376 (13)	−0.0007 (9)	0.0126 (10)	−0.0110 (9)
C36	0.0319 (14)	0.0384 (13)	0.0280 (12)	0.0002 (10)	0.0121 (10)	−0.0068 (9)
C37	0.0303 (13)	0.0258 (11)	0.0288 (11)	0.0038 (9)	0.0115 (9)	0.0049 (9)
C38	0.0201 (11)	0.0177 (9)	0.0285 (11)	0.0038 (8)	0.0101 (8)	0.0019 (8)
S41	0.0291 (3)	0.0234 (3)	0.0201 (3)	0.0061 (2)	0.0045 (2)	0.00362 (19)
N41	0.0244 (9)	0.0193 (8)	0.0167 (8)	0.0032 (7)	0.0025 (6)	0.0000 (6)
C41	0.0188 (11)	0.0202 (10)	0.0212 (10)	−0.0023 (8)	0.0030 (8)	−0.0003 (8)
O41	0.0405 (10)	0.0227 (8)	0.0224 (8)	0.0003 (6)	0.0025 (7)	−0.0049 (6)
C42	0.0140 (10)	0.0212 (10)	0.0214 (10)	−0.0017 (7)	0.0047 (8)	−0.0020 (8)
O42	0.0284 (8)	0.0299 (8)	0.0170 (7)	−0.0001 (6)	0.0040 (6)	−0.0039 (6)
C43	0.0135 (10)	0.0198 (10)	0.0231 (10)	−0.0018 (7)	0.0036 (7)	0.0005 (8)
C44	0.0236 (12)	0.0194 (10)	0.0298 (11)	−0.0011 (8)	0.0035 (9)	−0.0031 (8)
C45	0.0253 (12)	0.0206 (10)	0.0357 (12)	0.0018 (8)	0.0026 (9)	0.0041 (9)
C46	0.0249 (12)	0.0279 (11)	0.0262 (11)	−0.0012 (9)	−0.0028 (9)	0.0074 (9)
C47	0.0263 (12)	0.0245 (11)	0.0213 (10)	−0.0047 (8)	−0.0009 (8)	0.0001 (8)
C48	0.0175 (11)	0.0192 (9)	0.0214 (10)	−0.0027 (7)	0.0039 (8)	0.0003 (8)

Geometric parameters (Å, º) top

S11—N11	1.681 (2)	S31—N31	1.692 (2)
S11—S21	2.0382 (7)	S31—S41	2.0298 (8)
N11—C11	1.424 (2)	N31—C32	1.426 (2)
N11—C12	1.433 (2)	N31—C31	1.431 (2)
C11—O11	1.211 (2)	C31—O31	1.202 (2)
C11—C18	1.478 (3)	C31—C38	1.486 (3)
C12—O12	1.200 (2)	C32—O32	1.205 (2)
C12—C13	1.486 (3)	C32—C33	1.476 (3)
C13—C14	1.386 (3)	C33—C34	1.383 (3)
C13—C18	1.394 (3)	C33—C38	1.393 (3)
C14—C15	1.391 (3)	C34—C35	1.382 (3)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.392 (3)	C35—C36	1.399 (3)
C15—H15	0.9500	C35—H35	0.9500
C16—C17	1.395 (3)	C36—C37	1.391 (3)
C16—H16	0.9500	C36—H36	0.9500
C17—C18	1.384 (3)	C37—C38	1.377 (3)
C17—H17	0.9500	C37—H37	0.9500
S21—N21	1.694 (2)	S41—N41	1.694 (2)
N21—C21	1.420 (2)	N41—C41	1.422 (2)
N21—C22	1.425 (3)	N41—C42	1.425 (2)
C21—O21	1.206 (2)	C41—O41	1.206 (2)
C21—C28	1.486 (3)	C41—C48	1.484 (3)
C22—O22	1.200 (2)	C42—O42	1.199 (2)
C22—C23	1.486 (3)	C42—C43	1.483 (3)
C23—C24	1.385 (3)	C43—C48	1.387 (3)
C23—C28	1.396 (3)	C43—C44	1.388 (3)
C24—C25	1.395 (3)	C44—C45	1.395 (3)
C24—H24	0.9500	C44—H44	0.9500
C25—C26	1.387 (3)	C45—C46	1.388 (3)
C25—H25	0.9500	C45—H45	0.9500
C26—C27	1.390 (3)	C46—C47	1.390 (3)
C26—H26	0.9500	C46—H46	0.9500
C27—C28	1.379 (3)	C47—C48	1.383 (3)
C27—H27	0.9500	C47—H47	0.9500

N11—S11—S21	103.37 (6)	N31—S31—S41	103.41 (6)
C11—N11—C12	111.9 (2)	C32—N31—C31	111.1 (2)
C11—N11—S11	123.3 (2)	C32—N31—S31	123.4 (2)
C12—N11—S11	124.0 (2)	C31—N31—S31	124.4 (2)
O11—C11—N11	124.5 (2)	O31—C31—N31	124.5 (2)
O11—C11—C18	130.1 (2)	O31—C31—C38	130.2 (2)
N11—C11—C18	105.4 (2)	N31—C31—C38	105.3 (2)
O12—C12—N11	124.6 (2)	O32—C32—N31	124.7 (2)
O12—C12—C13	131.0 (2)	O32—C32—C33	129.6 (2)
N11—C12—C13	104.4 (2)	N31—C32—C33	105.6 (2)
C14—C13—C18	121.7 (2)	C34—C33—C38	121.6 (2)
C14—C13—C12	128.8 (2)	C34—C33—C32	129.2 (2)
C18—C13—C12	109.5 (2)	C38—C33—C32	109.2 (2)
C13—C14—C15	117.0 (2)	C35—C34—C33	117.2 (2)
C13—C14—H14	121.5	C35—C34—H34	121.4
C15—C14—H14	121.5	C33—C34—H34	121.4
C14—C15—C16	121.6 (2)	C34—C35—C36	121.5 (2)
C14—C15—H15	119.2	C34—C35—H35	119.2
C16—C15—H15	119.2	C36—C35—H35	119.2
C15—C16—C17	121.1 (2)	C37—C36—C35	120.7 (2)
C15—C16—H16	119.5	C37—C36—H36	119.6
C17—C16—H16	119.5	C35—C36—H36	119.6
C18—C17—C16	117.4 (2)	C38—C37—C36	117.7 (2)
C18—C17—H17	121.3	C38—C37—H37	121.2
C16—C17—H17	121.3	C36—C37—H37	121.2
C17—C18—C13	121.3 (2)	C37—C38—C33	121.3 (2)
C17—C18—C11	129.9 (2)	C37—C38—C31	130.0 (2)
C13—C18—C11	108.9 (2)	C33—C38—C31	108.8 (2)
N21—S21—S11	104.36 (6)	N41—S41—S31	105.98 (6)
C21—N21—C22	111.6 (2)	C41—N41—C42	111.9 (2)
C21—N21—S21	123.3 (2)	C41—N41—S41	124.3 (2)
C22—N21—S21	125.0 (2)	C42—N41—S41	123.4 (2)
O21—C21—N21	124.8 (2)	O41—C41—N41	124.9 (2)
O21—C21—C28	129.6 (2)	O41—C41—C48	130.0 (2)
N21—C21—C28	105.6 (2)	N41—C41—C48	105.1 (2)
O22—C22—N21	124.7 (2)	O42—C42—N41	125.3 (2)
O22—C22—C23	130.2 (2)	O42—C42—C43	130.0 (2)
N21—C22—C23	105.2 (2)	N41—C42—C43	104.7 (2)
C24—C23—C28	121.6 (2)	C48—C43—C44	121.7 (2)
C24—C23—C22	129.4 (2)	C48—C43—C42	109.5 (2)
C28—C23—C22	109.0 (2)	C44—C43—C42	128.8 (2)
C23—C24—C25	116.5 (2)	C43—C44—C45	116.7 (2)
C23—C24—H24	121.8	C43—C44—H44	121.7
C25—C24—H24	121.8	C45—C44—H44	121.7
C26—C25—C24	121.9 (2)	C46—C45—C44	121.5 (2)
C26—C25—H25	119.0	C46—C45—H45	119.3
C24—C25—H25	119.0	C44—C45—H45	119.3
C25—C26—C27	121.2 (2)	C45—C46—C47	121.5 (2)
C25—C26—H26	119.4	C45—C46—H46	119.3
C27—C26—H26	119.4	C47—C46—H46	119.3
C28—C27—C26	117.1 (2)	C48—C47—C46	117.1 (2)
C28—C27—H27	121.4	C48—C47—H47	121.5
C26—C27—H27	121.4	C46—C47—H47	121.5
C27—C28—C23	121.6 (2)	C47—C48—C43	121.7 (2)
C27—C28—C21	129.8 (2)	C47—C48—C41	129.6 (2)
C23—C28—C21	108.6 (2)	C43—C48—C41	108.7 (2)

S21—S11—N11—C11	93.4 (2)	S41—S31—N31—C32	75.7 (2)
S21—S11—N11—C12	−75.4 (2)	S41—S31—N31—C31	−91.1 (2)
C12—N11—C11—O11	176.2 (2)	C32—N31—C31—O31	−177.6 (2)
S11—N11—C11—O11	6.2 (3)	S31—N31—C31—O31	−9.4 (3)
C12—N11—C11—C18	−2.8 (2)	C32—N31—C31—C38	2.2 (2)
S11—N11—C11—C18	−172.8 (2)	S31—N31—C31—C38	170.4 (2)
C11—N11—C12—O12	−176.7 (2)	C31—N31—C32—O32	174.4 (2)
S11—N11—C12—O12	−6.7 (3)	S31—N31—C32—O32	6.1 (3)
C11—N11—C12—C13	2.4 (2)	C31—N31—C32—C33	−3.1 (2)
S11—N11—C12—C13	172.4 (2)	S31—N31—C32—C33	−171.4 (2)
O12—C12—C13—C14	−0.7 (3)	O32—C32—C33—C34	2.6 (4)
N11—C12—C13—C14	−179.7 (2)	N31—C32—C33—C34	179.9 (2)
O12—C12—C13—C18	177.9 (2)	O32—C32—C33—C38	−174.5 (2)
N11—C12—C13—C18	−1.1 (2)	N31—C32—C33—C38	2.8 (2)
C18—C13—C14—C15	0.2 (3)	C38—C33—C34—C35	1.4 (3)
C12—C13—C14—C15	178.7 (2)	C32—C33—C34—C35	−175.5 (2)
C13—C14—C15—C16	0.7 (3)	C33—C34—C35—C36	−1.2 (3)
C14—C15—C16—C17	−0.8 (3)	C34—C35—C36—C37	−0.1 (3)
C15—C16—C17—C18	−0.1 (3)	C35—C36—C37—C38	1.1 (3)
C16—C17—C18—C13	1.1 (3)	C36—C37—C38—C33	−1.0 (3)
C16—C17—C18—C11	−178.1 (2)	C36—C37—C38—C31	177.3 (2)
C14—C13—C18—C17	−1.2 (3)	C34—C33—C38—C37	−0.3 (3)
C12—C13—C18—C17	−179.9 (2)	C32—C33—C38—C37	177.1 (2)
C14—C13—C18—C11	178.1 (2)	C34—C33—C38—C31	−178.9 (2)
C12—C13—C18—C11	−0.6 (2)	C32—C33—C38—C31	−1.5 (2)
O11—C11—C18—C17	2.4 (3)	O31—C31—C38—C37	0.9 (4)
N11—C11—C18—C17	−178.8 (2)	N31—C31—C38—C37	−178.8 (2)
O11—C11—C18—C13	−176.9 (2)	O31—C31—C38—C33	179.4 (2)
N11—C11—C18—C13	2.0 (2)	N31—C31—C38—C33	−0.4 (2)
N11—S11—S21—N21	−80.06 (8)	N31—S31—S41—N41	86.72 (9)
S11—S21—N21—C21	85.3 (2)	S31—S41—N41—C41	−86.9 (2)
S11—S21—N21—C22	−92.1 (2)	S31—S41—N41—C42	100.8 (2)
C22—N21—C21—O21	178.5 (2)	C42—N41—C41—O41	177.7 (2)
S21—N21—C21—O21	0.8 (3)	S41—N41—C41—O41	4.7 (3)
C22—N21—C21—C28	−2.0 (2)	C42—N41—C41—C48	−1.9 (2)
S21—N21—C21—C28	−179.7 (2)	S41—N41—C41—C48	−174.9 (2)
C21—N21—C22—O22	−177.4 (2)	C41—N41—C42—O42	−175.4 (2)
S21—N21—C22—O22	0.2 (3)	S41—N41—C42—O42	−2.4 (3)
C21—N21—C22—C23	2.8 (2)	C41—N41—C42—C43	2.4 (2)
S21—N21—C22—C23	−179.6 (2)	S41—N41—C42—C43	175.4 (2)
O22—C22—C23—C24	−1.4 (3)	O42—C42—C43—C48	175.7 (2)
N21—C22—C23—C24	178.4 (2)	N41—C42—C43—C48	−1.9 (2)
O22—C22—C23—C28	177.7 (2)	O42—C42—C43—C44	−4.5 (3)
N21—C22—C23—C28	−2.5 (2)	N41—C42—C43—C44	177.8 (2)
C28—C23—C24—C25	−0.6 (3)	C48—C43—C44—C45	0.5 (3)
C22—C23—C24—C25	178.3 (2)	C42—C43—C44—C45	−179.2 (2)
C23—C24—C25—C26	−0.9 (3)	C43—C44—C45—C46	−0.5 (3)
C24—C25—C26—C27	1.6 (3)	C44—C45—C46—C47	0.3 (3)
C25—C26—C27—C28	−0.6 (3)	C45—C46—C47—C48	−0.1 (3)
C26—C27—C28—C23	−0.9 (3)	C46—C47—C48—C43	0.1 (3)
C26—C27—C28—C21	−179.7 (2)	C46—C47—C48—C41	178.4 (2)
C24—C23—C28—C27	1.6 (3)	C44—C43—C48—C47	−0.3 (3)
C22—C23—C28—C27	−177.6 (2)	C42—C43—C48—C47	179.4 (2)
C24—C23—C28—C21	−179.5 (2)	C44—C43—C48—C41	−178.9 (2)
C22—C23—C28—C21	1.4 (2)	C42—C43—C48—C41	0.8 (2)
O21—C21—C28—C27	−1.4 (3)	O41—C41—C48—C47	2.6 (4)
N21—C21—C28—C27	179.2 (2)	N41—C41—C48—C47	−177.9 (2)
O21—C21—C28—C23	179.7 (2)	O41—C41—C48—C43	−179.0 (2)
N21—C21—C28—C23	0.3 (2)	N41—C41—C48—C43	0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O21ⁱ	0.95	2.53	3.358 (2)	146
C16—H16···O32	0.95	2.37	3.245 (2)	153
C34—H34···O31ⁱⁱ	0.95	2.45	3.198 (3)	136
C45—H45···O41ⁱⁱⁱ	0.95	2.53	3.175 (3)	126

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

(6) N,N'-Dithiodiphthalimide–nitromethane solvate (1/1) top

Crystal data top

C₁₆H₈N₂O₄S₂·CH₃NO₂	F(000) = 856
M_r = 417.41	D_x = 1.552 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.5545 (9) Å	Cell parameters from 3397 reflections
b = 4.8545 (2) Å	θ = 3.3–27.5°
c = 16.7095 (14) Å	µ = 0.34 mm⁻¹
β = 102.4670 (17)°	T = 120 K
V = 1786.40 (18) Å³	Lath, colourless
Z = 4	0.40 × 0.16 × 0.10 mm

Data collection top

Kappa-CCD diffractometer	3397 independent reflections
Radiation source: fine-focus sealed X-ray tube	2883 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ scans, and ω scans with κ offsets	θ_max = 26.1°, θ_min = 3.3°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −28→27
T_min = 0.876, T_max = 0.967	k = −6→5
8059 measured reflections	l = −21→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0343P)² + 1.0483P] where P = (F_o² + 2F_c²)/3
3397 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.20852 (2)	0.39105 (10)	0.19499 (3)	0.02150 (13)
N11	0.27521 (7)	0.2845 (3)	0.17624 (9)	0.0202 (3)
C11	0.30491 (8)	0.4105 (4)	0.11894 (11)	0.0210 (4)
O11	0.28414 (6)	0.5987 (3)	0.07467 (8)	0.0289 (3)
C12	0.30951 (8)	0.0618 (4)	0.21787 (11)	0.0194 (4)
O12	0.29242 (6)	−0.0874 (3)	0.26596 (8)	0.0255 (3)
C13	0.36660 (8)	0.0589 (4)	0.18706 (11)	0.0196 (4)
C14	0.41727 (9)	−0.1070 (4)	0.20966 (12)	0.0243 (4)
C15	0.46470 (9)	−0.0643 (4)	0.16969 (12)	0.0270 (4)
C16	0.46138 (9)	0.1373 (4)	0.11002 (13)	0.0273 (4)
C17	0.41018 (9)	0.3049 (4)	0.08780 (12)	0.0246 (4)
C18	0.36339 (8)	0.2616 (4)	0.12779 (11)	0.0201 (4)
S2	0.14412 (2)	0.16382 (10)	0.11990 (3)	0.02271 (13)
N21	0.12499 (7)	0.3532 (3)	0.03339 (9)	0.0198 (3)
C21	0.15479 (8)	0.3351 (4)	−0.03363 (12)	0.0212 (4)
O21	0.19511 (6)	0.1767 (3)	−0.03719 (9)	0.0297 (3)
C22	0.08065 (8)	0.5644 (4)	0.02087 (11)	0.0191 (4)
O22	0.05129 (6)	0.6320 (3)	0.07028 (8)	0.0241 (3)
C23	0.08005 (8)	0.6755 (4)	−0.06173 (11)	0.0186 (4)
C24	0.04340 (9)	0.8776 (4)	−0.10547 (12)	0.0245 (4)
C25	0.05291 (9)	0.9412 (4)	−0.18285 (13)	0.0283 (5)
C26	0.09724 (9)	0.8082 (4)	−0.21470 (12)	0.0285 (5)
C27	0.13443 (9)	0.6084 (4)	−0.17012 (12)	0.0257 (4)
C28	0.12431 (8)	0.5441 (4)	−0.09332 (11)	0.0198 (4)
C31	0.30711 (9)	1.0140 (5)	−0.08442 (12)	0.0286 (5)
N31	0.36677 (7)	0.9449 (3)	−0.10308 (10)	0.0245 (4)
O31	0.38564 (7)	1.0908 (3)	−0.15208 (9)	0.0337 (4)
O32	0.39413 (7)	0.7434 (3)	−0.07037 (10)	0.0418 (4)
H14	0.4196	−0.2444	0.2507	0.029*
H15	0.5001	−0.1756	0.1836	0.032*
H16	0.4945	0.1617	0.0839	0.033*
H17	0.4076	0.4429	0.0469	0.030*
H24	0.0131	0.9686	−0.0836	0.029*
H25	0.0286	1.0786	−0.2146	0.034*
H26	0.1022	0.8549	−0.2681	0.034*
H27	0.1654	0.5200	−0.1913	0.031*
H31A	0.2745	0.9471	−0.1288	0.043*
H31B	0.3037	1.2142	−0.0794	0.043*
H31C	0.3037	0.9262	−0.0328	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0184 (2)	0.0275 (3)	0.0180 (3)	−0.00009 (17)	0.00254 (18)	−0.00081 (18)
N11	0.0189 (7)	0.0228 (8)	0.0187 (8)	0.0004 (6)	0.0035 (6)	0.0031 (6)
C11	0.0221 (9)	0.0249 (10)	0.0161 (9)	−0.0047 (7)	0.0042 (8)	−0.0010 (8)
O11	0.0275 (7)	0.0311 (8)	0.0279 (8)	0.0024 (6)	0.0056 (6)	0.0106 (6)
C12	0.0205 (9)	0.0203 (9)	0.0153 (9)	−0.0029 (7)	−0.0008 (7)	−0.0018 (7)
O12	0.0248 (7)	0.0289 (8)	0.0227 (7)	−0.0034 (5)	0.0045 (6)	0.0060 (6)
C13	0.0207 (9)	0.0208 (9)	0.0167 (9)	−0.0044 (7)	0.0026 (7)	−0.0040 (7)
C14	0.0234 (9)	0.0232 (10)	0.0251 (11)	−0.0011 (7)	0.0022 (8)	−0.0003 (8)
C15	0.0209 (9)	0.0289 (11)	0.0305 (11)	0.0013 (7)	0.0040 (8)	−0.0037 (8)
C16	0.0231 (10)	0.0329 (11)	0.0281 (11)	−0.0041 (8)	0.0106 (8)	−0.0055 (9)
C17	0.0257 (10)	0.0278 (11)	0.0210 (10)	−0.0040 (8)	0.0063 (8)	0.0002 (8)
C18	0.0215 (9)	0.0224 (9)	0.0161 (9)	−0.0034 (7)	0.0030 (8)	−0.0022 (7)
S2	0.0203 (2)	0.0244 (3)	0.0219 (3)	−0.00259 (17)	0.00120 (19)	0.00366 (19)
N21	0.0189 (7)	0.0250 (8)	0.0156 (8)	0.0026 (6)	0.0038 (6)	−0.0007 (6)
C21	0.0189 (9)	0.0234 (10)	0.0214 (10)	−0.0015 (7)	0.0046 (8)	−0.0053 (8)
O21	0.0254 (7)	0.0315 (8)	0.0334 (9)	0.0085 (6)	0.0092 (6)	−0.0025 (6)
C22	0.0150 (8)	0.0220 (9)	0.0192 (10)	−0.0018 (7)	0.0009 (7)	−0.0052 (7)
O22	0.0210 (7)	0.0317 (8)	0.0210 (7)	0.0013 (5)	0.0077 (6)	−0.0063 (6)
C23	0.0173 (9)	0.0196 (9)	0.0180 (10)	−0.0021 (7)	0.0018 (7)	−0.0030 (7)
C24	0.0202 (9)	0.0259 (10)	0.0258 (11)	0.0005 (7)	0.0013 (8)	−0.0019 (8)
C25	0.0261 (10)	0.0272 (11)	0.0276 (11)	−0.0035 (8)	−0.0029 (9)	0.0055 (9)
C26	0.0314 (11)	0.0341 (11)	0.0190 (11)	−0.0104 (8)	0.0033 (9)	0.0032 (8)
C27	0.0251 (10)	0.0328 (11)	0.0204 (11)	−0.0049 (8)	0.0077 (8)	−0.0049 (8)
C28	0.0187 (9)	0.0210 (9)	0.0193 (10)	−0.0027 (7)	0.0033 (7)	−0.0030 (7)
C31	0.0230 (10)	0.0413 (12)	0.0235 (11)	0.0046 (8)	0.0095 (8)	−0.0020 (9)
N31	0.0248 (8)	0.0305 (9)	0.0187 (8)	0.0029 (7)	0.0057 (7)	0.0007 (7)
O31	0.0353 (8)	0.0332 (8)	0.0374 (9)	0.0025 (6)	0.0181 (7)	0.0081 (7)
O32	0.0362 (9)	0.0502 (10)	0.0415 (10)	0.0182 (7)	0.0137 (7)	0.0208 (8)

Geometric parameters (Å, º) top

S1—N11	1.683 (2)	C21—O21	1.202 (2)
S1—S2	2.0284 (7)	C21—C28	1.483 (3)
N11—C11	1.420 (2)	C22—O22	1.210 (2)
N11—C12	1.421 (2)	C22—C23	1.479 (3)
C11—O11	1.205 (2)	C23—C28	1.382 (3)
C11—C18	1.483 (3)	C23—C24	1.385 (3)
C12—O12	1.205 (2)	C24—C25	1.390 (3)
C12—C13	1.486 (3)	C24—H24	0.9500
C13—C14	1.382 (3)	C25—C26	1.389 (3)
C13—C18	1.387 (3)	C25—H25	0.9500
C14—C15	1.394 (3)	C26—C27	1.389 (3)
C14—H14	0.9500	C26—H26	0.9500
C15—C16	1.388 (3)	C27—C28	1.387 (3)
C15—H15	0.9500	C27—H27	0.9500
C16—C17	1.396 (3)	C31—N31	1.484 (2)
C16—H16	0.9500	C31—H31A	0.9800
C17—C18	1.382 (3)	C31—H31B	0.9800
C17—H17	0.9500	C31—H31C	0.9800
S2—N21	1.689 (2)	N31—O32	1.221 (2)
N21—C22	1.416 (2)	N31—O31	1.226 (2)
N21—C21	1.428 (2)

N11—S1—S2	105.50 (6)	O21—C21—C28	130.5 (2)
C11—N11—C12	111.8 (2)	N21—C21—C28	104.9 (2)
C11—N11—S1	124.3 (2)	O22—C22—N21	124.7 (2)
C12—N11—S1	123.8 (2)	O22—C22—C23	129.9 (2)
O11—C11—N11	124.3 (2)	N21—C22—C23	105.4 (2)
O11—C11—C18	130.6 (2)	C28—C23—C24	121.6 (2)
N11—C11—C18	105.2 (2)	C28—C23—C22	109.0 (2)
O12—C12—N11	124.4 (2)	C24—C23—C22	129.4 (2)
O12—C12—C13	130.6 (2)	C23—C24—C25	117.0 (2)
N11—C12—C13	105.0 (2)	C23—C24—H24	121.5
C14—C13—C18	121.4 (2)	C25—C24—H24	121.5
C14—C13—C12	129.6 (2)	C26—C25—C24	121.4 (2)
C18—C13—C12	109.0 (2)	C26—C25—H25	119.3
C13—C14—C15	117.2 (2)	C24—C25—H25	119.3
C13—C14—H14	121.4	C27—C26—C25	121.4 (2)
C15—C14—H14	121.4	C27—C26—H26	119.3
C16—C15—C14	121.4 (2)	C25—C26—H26	119.3
C16—C15—H15	119.3	C28—C27—C26	116.9 (2)
C14—C15—H15	119.3	C28—C27—H27	121.5
C15—C16—C17	121.0 (2)	C26—C27—H27	121.5
C15—C16—H16	119.5	C23—C28—C27	121.7 (2)
C17—C16—H16	119.5	C23—C28—C21	109.1 (2)
C18—C17—C16	117.2 (2)	C27—C28—C21	129.2 (2)
C18—C17—H17	121.4	N31—C31—H31A	109.5
C16—C17—H17	121.4	N31—C31—H31B	109.5
C17—C18—C13	121.7 (2)	H31A—C31—H31B	109.5
C17—C18—C11	129.3 (2)	N31—C31—H31C	109.5
C13—C18—C11	109.0 (2)	H31A—C31—H31C	109.5
N21—S2—S1	104.48 (6)	H31B—C31—H31C	109.5
C22—N21—C21	111.4 (2)	O32—N31—O31	123.2 (2)
C22—N21—S2	124.2 (2)	O32—N31—C31	118.7 (2)
C21—N21—S2	124.2 (2)	O31—N31—C31	118.1 (2)
O21—C21—N21	124.6 (2)

S2—S1—N11—C11	93.3 (2)	S1—S2—N21—C22	−86.1 (2)
S2—S1—N11—C12	−88.7 (2)	S1—S2—N21—C21	88.8 (2)
C12—N11—C11—O11	177.9 (2)	C22—N21—C21—O21	178.3 (2)
S1—N11—C11—O11	−3.8 (3)	S2—N21—C21—O21	2.9 (3)
C12—N11—C11—C18	−2.3 (2)	C22—N21—C21—C28	−2.6 (2)
S1—N11—C11—C18	176.0 (2)	S2—N21—C21—C28	−178.0 (2)
C11—N11—C12—O12	−175.6 (2)	C21—N21—C22—O22	−175.9 (2)
S1—N11—C12—O12	6.2 (3)	S2—N21—C22—O22	−0.4 (3)
C11—N11—C12—C13	3.2 (2)	C21—N21—C22—C23	3.5 (2)
S1—N11—C12—C13	−175.1 (2)	S2—N21—C22—C23	178.9 (2)
O12—C12—C13—C14	−4.6 (3)	O22—C22—C23—C28	176.3 (2)
N11—C12—C13—C14	176.7 (2)	N21—C22—C23—C28	−3.0 (2)
O12—C12—C13—C18	175.8 (2)	O22—C22—C23—C24	−3.5 (3)
N11—C12—C13—C18	−2.8 (2)	N21—C22—C23—C24	177.2 (2)
C18—C13—C14—C15	−0.7 (3)	C28—C23—C24—C25	0.4 (3)
C12—C13—C14—C15	179.7 (2)	C22—C23—C24—C25	−179.9 (2)
C13—C14—C15—C16	0.3 (3)	C23—C24—C25—C26	−0.1 (3)
C14—C15—C16—C17	−0.1 (3)	C24—C25—C26—C27	−0.8 (3)
C15—C16—C17—C18	0.2 (3)	C25—C26—C27—C28	1.4 (3)
C16—C17—C18—C13	−0.6 (3)	C24—C23—C28—C27	0.3 (3)
C16—C17—C18—C11	178.2 (2)	C22—C23—C28—C27	−179.5 (2)
C14—C13—C18—C17	0.9 (3)	C24—C23—C28—C21	−178.6 (2)
C12—C13—C18—C17	−179.5 (2)	C22—C23—C28—C21	1.5 (2)
C14—C13—C18—C11	−178.1 (2)	C26—C27—C28—C23	−1.1 (3)
C12—C13—C18—C11	1.5 (2)	C26—C27—C28—C21	177.6 (2)
O11—C11—C18—C17	1.3 (3)	O21—C21—C28—C23	179.6 (2)
N11—C11—C18—C17	−178.5 (2)	N21—C21—C28—C23	0.5 (2)
O11—C11—C18—C13	−179.9 (2)	O21—C21—C28—C27	0.8 (3)
N11—C11—C18—C13	0.4 (2)	N21—C21—C28—C27	−178.3 (2)
N11—S1—S2—N21	−90.90 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O32	0.95	2.41	3.352 (3)	172
C24—H24···O22ⁱ	0.95	2.46	3.334 (3)	153
C31—H31C···O11	0.98	2.51	3.463 (3)	165
C31—H31A···O21ⁱⁱ	0.98	2.82	2.914 (3)	85
C31—H31B···O21ⁱⁱ	0.98	2.70	2.914 (3)	93
C31—H31C···O21ⁱⁱ	0.98	2.72	2.914 (3)	91

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

(7) N,N'-Dithiodiphthalimide hemi(chlorobenzene) solvate top

Crystal data top

C₁₆H₈N₂O₄S₂·0.5(C₆H₅Cl)	Z = 2
M_r = 412.64	F(000) = 422
Triclinic, P1	D_x = 1.567 Mg m⁻³
a = 7.6257 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3369 (2) Å	Cell parameters from 3946 reflections
c = 11.6392 (2) Å	θ = 3.0–27.5°
α = 81.5440 (8)°	µ = 0.41 mm⁻¹
β = 77.8600 (8)°	T = 120 K
γ = 78.8480 (13)°	Block, colourless
V = 874.59 (12) Å³	0.34 × 0.30 × 0.28 mm

Data collection top

Kappa-CCD diffractometer	3946 independent reflections
Radiation source: fine-focus sealed X-ray tube	3616 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −9→9
T_min = 0.873, T_max = 0.894	k = −13→13
8059 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.056P)² + 0.3058P] where P = (F_o² + 2F_c²)/3
3946 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.35296 (6)	0.88571 (4)	0.43979 (4)	0.02869 (12)
N11	0.33665 (19)	0.72395 (13)	0.44954 (12)	0.0259 (3)
C11	0.2341 (2)	0.65337 (16)	0.54575 (14)	0.0258 (3)
O11	0.15461 (17)	0.69813 (13)	0.63585 (10)	0.0331 (3)
C12	0.4083 (2)	0.64658 (16)	0.35332 (14)	0.0253 (3)
O12	0.49770 (17)	0.68481 (12)	0.26090 (10)	0.0328 (3)
C13	0.3491 (2)	0.51658 (16)	0.39402 (14)	0.0257 (3)
C14	0.3799 (2)	0.40494 (17)	0.33493 (15)	0.0308 (4)
C15	0.3058 (3)	0.29571 (18)	0.39522 (17)	0.0340 (4)
C16	0.2069 (2)	0.29764 (18)	0.50985 (17)	0.0337 (4)
C17	0.1753 (2)	0.41066 (17)	0.56928 (15)	0.0298 (3)
C18	0.2483 (2)	0.51960 (16)	0.50859 (14)	0.0258 (3)
S2	0.13079 (6)	0.98197 (4)	0.37288 (4)	0.02938 (13)
N21	0.18274 (19)	0.96564 (13)	0.22729 (12)	0.0270 (3)
C21	0.1455 (2)	0.85774 (16)	0.17847 (14)	0.0264 (3)
O21	0.08687 (17)	0.76369 (12)	0.23590 (11)	0.0340 (3)
C22	0.2512 (2)	1.06297 (16)	0.13777 (15)	0.0276 (3)
O22	0.29537 (19)	1.16216 (12)	0.15667 (12)	0.0372 (3)
C23	0.2536 (2)	1.01210 (17)	0.02441 (15)	0.0279 (3)
C24	0.3017 (2)	1.0699 (2)	−0.09035 (16)	0.0346 (4)
C25	0.2868 (2)	0.9995 (2)	−0.18075 (16)	0.0406 (4)
C26	0.2277 (2)	0.8780 (2)	−0.15692 (17)	0.0394 (4)
C27	0.1793 (2)	0.82053 (19)	−0.04093 (16)	0.0337 (4)
C28	0.1931 (2)	0.89078 (17)	0.04864 (14)	0.0273 (3)
Cl31	0.57340 (11)	0.57934 (9)	−0.00109 (7)	0.0342 (2)	0.50
C31	0.8180 (3)	0.5458 (2)	−0.00114 (17)	0.0408 (4)
C32	0.9425 (3)	0.5443 (2)	−0.10678 (16)	0.0414 (4)
C33	0.8751 (3)	0.5023 (2)	0.10541 (17)	0.0412 (5)
H14	0.4485	0.4031	0.2568	0.037*
H15	0.3232	0.2178	0.3570	0.041*
H16	0.1598	0.2207	0.5487	0.040*
H17	0.1071	0.4126	0.6475	0.036*
H24	0.3425	1.1531	−0.1068	0.042*
H25	0.3181	1.0360	−0.2607	0.049*
H26	0.2199	0.8329	−0.2207	0.047*
H27	0.1389	0.7372	−0.0242	0.040*
H31	0.6925	0.5769	−0.0019	0.049*	0.50
H32	0.9029	0.5751	−0.1796	0.050*
H33	0.7891	0.5043	0.1775	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0357 (2)	0.0261 (2)	0.0267 (2)	−0.00862 (16)	−0.00918 (16)	−0.00171 (15)
N11	0.0303 (7)	0.0244 (6)	0.0234 (6)	−0.0059 (5)	−0.0054 (5)	−0.0017 (5)
C11	0.0259 (8)	0.0286 (8)	0.0235 (7)	−0.0045 (6)	−0.0080 (6)	0.0003 (6)
O11	0.0381 (7)	0.0362 (7)	0.0237 (6)	−0.0055 (5)	−0.0031 (5)	−0.0045 (5)
C12	0.0242 (7)	0.0274 (8)	0.0240 (7)	−0.0021 (6)	−0.0062 (6)	−0.0021 (6)
O12	0.0331 (6)	0.0346 (6)	0.0270 (6)	−0.0057 (5)	0.0003 (5)	0.0007 (5)
C13	0.0239 (7)	0.0292 (8)	0.0251 (7)	−0.0044 (6)	−0.0087 (6)	−0.0013 (6)
C14	0.0315 (8)	0.0329 (9)	0.0293 (8)	−0.0032 (7)	−0.0094 (7)	−0.0057 (7)
C15	0.0373 (9)	0.0294 (8)	0.0400 (9)	−0.0056 (7)	−0.0146 (8)	−0.0082 (7)
C16	0.0340 (9)	0.0300 (8)	0.0403 (9)	−0.0114 (7)	−0.0130 (7)	0.0019 (7)
C17	0.0272 (8)	0.0326 (8)	0.0296 (8)	−0.0074 (7)	−0.0070 (6)	0.0021 (7)
C18	0.0252 (7)	0.0281 (8)	0.0254 (7)	−0.0047 (6)	−0.0084 (6)	−0.0019 (6)
S2	0.0331 (2)	0.0269 (2)	0.0258 (2)	−0.00081 (16)	−0.00318 (16)	−0.00417 (15)
N21	0.0312 (7)	0.0253 (7)	0.0250 (6)	−0.0052 (5)	−0.0070 (5)	−0.0008 (5)
C21	0.0251 (7)	0.0253 (8)	0.0291 (8)	−0.0032 (6)	−0.0073 (6)	−0.0019 (6)
O21	0.0378 (7)	0.0300 (6)	0.0352 (7)	−0.0108 (5)	−0.0089 (5)	0.0024 (5)
C22	0.0261 (8)	0.0267 (8)	0.0287 (8)	−0.0029 (6)	−0.0072 (6)	0.0019 (6)
O22	0.0477 (8)	0.0268 (6)	0.0406 (7)	−0.0107 (5)	−0.0147 (6)	0.0005 (5)
C23	0.0219 (7)	0.0331 (8)	0.0278 (8)	−0.0032 (6)	−0.0060 (6)	−0.0008 (6)
C24	0.0258 (8)	0.0452 (10)	0.0309 (9)	−0.0076 (7)	−0.0054 (7)	0.0045 (7)
C25	0.0283 (9)	0.0634 (13)	0.0261 (8)	−0.0021 (8)	−0.0036 (7)	−0.0013 (8)
C26	0.0297 (9)	0.0575 (12)	0.0311 (9)	0.0033 (8)	−0.0083 (7)	−0.0152 (8)
C27	0.0300 (9)	0.0368 (9)	0.0355 (9)	−0.0004 (7)	−0.0097 (7)	−0.0095 (7)
C28	0.0238 (7)	0.0308 (8)	0.0268 (8)	−0.0015 (6)	−0.0067 (6)	−0.0031 (6)
Cl31	0.0262 (4)	0.0438 (5)	0.0317 (4)	−0.0036 (3)	−0.0063 (3)	−0.0031 (3)
C31	0.0353 (9)	0.0474 (11)	0.0329 (9)	0.0109 (8)	−0.0068 (8)	−0.0063 (8)
C32	0.0453 (11)	0.0468 (11)	0.0266 (8)	0.0078 (9)	−0.0091 (8)	−0.0031 (8)
C33	0.0425 (11)	0.0460 (11)	0.0274 (8)	0.0091 (8)	−0.0038 (7)	−0.0057 (8)

Geometric parameters (Å, º) top

S1—N11	1.686 (1)	C21—C28	1.482 (2)
S1—S2	2.0352 (6)	C22—O22	1.202 (2)
N11—C11	1.418 (2)	C22—C23	1.486 (2)
N11—C12	1.425 (2)	C23—C24	1.386 (2)
C11—O11	1.203 (2)	C23—C28	1.390 (2)
C11—C18	1.486 (2)	C24—C25	1.399 (3)
C12—O12	1.204 (2)	C24—H24	0.9500
C12—C13	1.480 (2)	C25—C26	1.387 (3)
C13—C14	1.386 (2)	C25—H25	0.9500
C13—C18	1.394 (2)	C26—C27	1.397 (3)
C14—C15	1.391 (3)	C26—H26	0.9500
C14—H14	0.9500	C27—C28	1.387 (2)
C15—C16	1.388 (3)	C27—H27	0.9500
C15—H15	0.9500	Cl31—C31	1.830 (2)
C16—C17	1.400 (3)	C31—C33	1.385 (3)
C16—H16	0.9500	C31—C32	1.387 (3)
C17—C18	1.386 (2)	C31—H31	0.9500
C17—H17	0.9500	C32—C33ⁱ	1.384 (3)
S2—N21	1.683 (2)	C32—H32	0.9500
N21—C21	1.423 (2)	C33—C32ⁱ	1.384 (3)
N21—C22	1.427 (2)	C33—H33	0.9500
C21—O21	1.201 (2)

N11—S1—S2	103.99 (5)	N21—C21—C28	104.9 (2)
C11—N11—C12	111.9 (2)	O22—C22—N21	124.6 (2)
C11—N11—S1	125.2 (2)	O22—C22—C23	130.6 (2)
C12—N11—S1	122.5 (2)	N21—C22—C23	104.8 (2)
O11—C11—N11	124.9 (2)	C24—C23—C28	121.8 (2)
O11—C11—C18	130.0 (2)	C24—C23—C22	129.2 (2)
N11—C11—C18	105.1 (2)	C28—C23—C22	109.0 (2)
O12—C12—N11	124.6 (2)	C23—C24—C25	116.5 (2)
O12—C12—C13	130.2 (2)	C23—C24—H24	121.7
N11—C12—C13	105.2 (2)	C25—C24—H24	121.7
C14—C13—C18	121.7 (2)	C26—C25—C24	121.8 (2)
C14—C13—C12	129.4 (2)	C26—C25—H25	119.1
C18—C13—C12	108.9 (2)	C24—C25—H25	119.1
C13—C14—C15	117.0 (2)	C25—C26—C27	121.3 (2)
C13—C14—H14	121.5	C25—C26—H26	119.4
C15—C14—H14	121.5	C27—C26—H26	119.4
C16—C15—C14	121.6 (2)	C28—C27—C26	116.9 (2)
C16—C15—H15	119.2	C28—C27—H27	121.6
C14—C15—H15	119.2	C26—C27—H27	121.6
C15—C16—C17	121.3 (2)	C27—C28—C23	121.7 (2)
C15—C16—H16	119.3	C27—C28—C21	129.0 (2)
C17—C16—H16	119.3	C23—C28—C21	109.3 (2)
C18—C17—C16	116.8 (2)	C33—C31—C32	120.5 (2)
C18—C17—H17	121.6	C33—C31—Cl31	118.2 (2)
C16—C17—H17	121.6	C32—C31—Cl31	120.5 (2)
C17—C18—C13	121.6 (2)	C33—C31—H31	119.7
C17—C18—C11	129.6 (2)	C32—C31—H31	119.7
C13—C18—C11	108.9 (2)	Cl31—C31—H31	8.6
N21—S2—S1	105.62 (5)	C33ⁱ—C32—C31	119.6 (2)
C21—N21—C22	112.0 (2)	C33ⁱ—C32—H32	120.2
C21—N21—S2	123.1 (2)	C31—C32—H32	120.2
C22—N21—S2	124.6 (2)	C32ⁱ—C33—C31	119.9 (2)
O21—C21—N21	124.4 (2)	C32ⁱ—C33—H33	120.0
O21—C21—C28	130.6 (2)	C31—C33—H33	120.0

S2—S1—N11—C11	−85.1 (2)	C22—N21—C21—O21	180.0 (2)
S2—S1—N11—C12	86.8 (2)	S2—N21—C21—O21	−5.9 (2)
C12—N11—C11—O11	−177.4 (2)	C22—N21—C21—C28	−0.4 (2)
S1—N11—C11—O11	−4.7 (2)	S2—N21—C21—C28	173.7 (2)
C12—N11—C11—C18	2.2 (2)	C21—N21—C22—O22	−178.8 (2)
S1—N11—C11—C18	174.9 (2)	S2—N21—C22—O22	7.2 (2)
C11—N11—C12—O12	178.9 (2)	C21—N21—C22—C23	1.0 (2)
S1—N11—C12—O12	5.9 (2)	S2—N21—C22—C23	−173.1 (2)
C11—N11—C12—C13	−1.4 (2)	O22—C22—C23—C24	−2.9 (3)
S1—N11—C12—C13	−174.3 (2)	N21—C22—C23—C24	177.4 (2)
O12—C12—C13—C14	−0.9 (3)	O22—C22—C23—C28	178.6 (2)
N11—C12—C13—C14	179.4 (2)	N21—C22—C23—C28	−1.2 (2)
O12—C12—C13—C18	179.6 (2)	C28—C23—C24—C25	−0.3 (3)
N11—C12—C13—C18	−0.1 (2)	C22—C23—C24—C25	−178.7 (2)
C18—C13—C14—C15	−0.1 (2)	C23—C24—C25—C26	−0.2 (3)
C12—C13—C14—C15	−179.5 (2)	C24—C25—C26—C27	0.3 (3)
C13—C14—C15—C16	−0.6 (3)	C25—C26—C27—C28	0.1 (3)
C14—C15—C16—C17	0.9 (3)	C26—C27—C28—C23	−0.6 (2)
C15—C16—C17—C18	−0.4 (3)	C26—C27—C28—C21	177.5 (2)
C16—C17—C18—C13	−0.3 (2)	C24—C23—C28—C27	0.7 (3)
C16—C17—C18—C11	178.0 (2)	C22—C23—C28—C27	179.4 (2)
C14—C13—C18—C17	0.5 (2)	C24—C23—C28—C21	−177.7 (2)
C12—C13—C18—C17	−180.0 (2)	C22—C23—C28—C21	0.9 (2)
C14—C13—C18—C11	−178.1 (2)	O21—C21—C28—C27	0.9 (3)
C12—C13—C18—C11	1.4 (2)	N21—C21—C28—C27	−178.6 (2)
O11—C11—C18—C17	−1.1 (3)	O21—C21—C28—C23	179.2 (2)
N11—C11—C18—C17	179.3 (2)	N21—C21—C28—C23	−0.3 (2)
O11—C11—C18—C13	177.4 (2)	C33—C31—C32—C33ⁱ	0.6 (4)
N11—C11—C18—C13	−2.2 (2)	Cl31—C31—C32—C33ⁱ	−169.4 (2)
N11—S1—S2—N21	−77.62 (7)	C32—C31—C33—C32ⁱ	−0.6 (4)
S1—S2—N21—C21	89.8 (2)	Cl31—C31—C33—C32ⁱ	169.7 (2)
S1—S2—N21—C22	−96.8 (2)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O22ⁱⁱ	0.95	2.54	3.299 (2)	137
C24—H24···O12ⁱⁱⁱ	0.95	2.55	3.384 (2)	147
C26—H26···O11^iv	0.95	2.51	3.445 (2)	170

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

(8) N,N'-Dithiodiphthalimide ethylbenzene/water solvate top

Crystal data top

C_19.652H_12.652N₂O_4.043S₂	F(000) = 1671.3
M_r = 405.63	D_x = 1.482 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.7600 (4) Å	Cell parameters from 8251 reflections
b = 16.4924 (4) Å	θ = 3.0–27.5°
c = 16.0450 (5) Å	µ = 0.32 mm⁻¹
β = 92.951 (1)°	T = 120 K
V = 3636.35 (18) Å³	Block, colourless
Z = 8	0.16 × 0.14 × 0.08 mm

Data collection top

Kappa-CCD diffractometer	8251 independent reflections
Radiation source: fine-focus sealed X-ray tube	5880 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −17→16
T_min = 0.950, T_max = 0.975	k = −21→21
32961 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0693P)² + 0.827P] where P = (F_o² + 2F_c²)/3
8251 reflections	(Δ/σ)_max = 0.001
510 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.56497 (4)	1.07875 (3)	0.55872 (3)	0.02625 (14)
N11	0.55669 (12)	1.14800 (10)	0.63540 (11)	0.0242 (4)
C11	0.53967 (14)	1.23220 (12)	0.61952 (13)	0.0240 (5)
O11	0.53913 (11)	1.26297 (9)	0.55175 (9)	0.0322 (4)
C12	0.55073 (14)	1.12898 (13)	0.72145 (13)	0.0248 (5)
O12	0.56016 (11)	1.06212 (9)	0.75050 (10)	0.0323 (4)
C13	0.52927 (14)	1.20738 (12)	0.76250 (13)	0.0243 (5)
C14	0.51381 (15)	1.22331 (14)	0.84514 (14)	0.0301 (5)
C15	0.49010 (16)	1.30300 (14)	0.86551 (15)	0.0329 (5)
C16	0.48295 (16)	1.36349 (14)	0.80512 (15)	0.0326 (5)
C17	0.49912 (15)	1.34722 (13)	0.72214 (15)	0.0292 (5)
C18	0.52244 (14)	1.26758 (12)	0.70216 (13)	0.0235 (4)
S2	0.70905 (4)	1.06824 (3)	0.53908 (3)	0.02599 (14)
N21	0.73548 (12)	1.14829 (10)	0.47877 (11)	0.0239 (4)
C21	0.76059 (14)	1.22620 (12)	0.51209 (13)	0.0232 (4)
O21	0.76493 (11)	1.24218 (9)	0.58506 (9)	0.0320 (4)
C22	0.73409 (14)	1.14744 (12)	0.39032 (13)	0.0222 (4)
O22	0.71210 (11)	1.09026 (9)	0.34688 (10)	0.0301 (4)
C23	0.76296 (14)	1.23073 (12)	0.36626 (13)	0.0217 (4)
C24	0.77293 (14)	1.26336 (12)	0.28811 (13)	0.0248 (5)
C25	0.79624 (16)	1.34537 (13)	0.28374 (14)	0.0295 (5)
C26	0.81024 (16)	1.39207 (13)	0.35550 (15)	0.0339 (5)
C27	0.80128 (16)	1.35845 (13)	0.43452 (15)	0.0305 (5)
C28	0.77743 (14)	1.27734 (12)	0.43800 (13)	0.0229 (4)
S3	0.92291 (4)	0.56524 (3)	0.14182 (3)	0.02608 (14)
N31	0.92976 (12)	0.60975 (10)	0.04778 (10)	0.0232 (4)
C31	0.96547 (14)	0.69004 (12)	0.03550 (14)	0.0243 (5)
O31	0.98486 (12)	0.73725 (9)	0.09097 (10)	0.0349 (4)
C32	0.91710 (14)	0.56715 (12)	−0.02893 (13)	0.0214 (4)
O32	0.89105 (10)	0.49746 (8)	−0.03568 (9)	0.0254 (3)
C33	0.94224 (14)	0.62580 (12)	−0.09418 (13)	0.0217 (4)
C34	0.93855 (15)	0.61659 (12)	−0.17949 (13)	0.0250 (4)
C35	0.96574 (15)	0.68249 (13)	−0.22713 (14)	0.0288 (5)
C36	0.99533 (15)	0.75499 (13)	−0.18917 (14)	0.0294 (5)
C37	0.99837 (15)	0.76437 (13)	−0.10277 (15)	0.0289 (5)
C38	0.97138 (14)	0.69848 (12)	−0.05592 (13)	0.0239 (4)
S4	0.78144 (4)	0.57415 (3)	0.17005 (3)	0.02595 (14)
N41	0.77117 (12)	0.65847 (9)	0.22876 (10)	0.0216 (4)
C41	0.74309 (14)	0.73648 (12)	0.19677 (13)	0.0218 (4)
O41	0.73820 (11)	0.75391 (9)	0.12413 (9)	0.0307 (4)
C42	0.77341 (15)	0.65643 (12)	0.31709 (13)	0.0229 (4)
O42	0.79904 (12)	0.59894 (9)	0.35859 (9)	0.0336 (4)
C43	0.73990 (14)	0.73778 (11)	0.34261 (13)	0.0207 (4)
C44	0.72588 (15)	0.76725 (12)	0.42186 (13)	0.0241 (5)
C45	0.69530 (15)	0.84712 (12)	0.42838 (14)	0.0272 (5)
C46	0.67987 (15)	0.89545 (12)	0.35765 (15)	0.0285 (5)
C47	0.69307 (14)	0.86513 (12)	0.27794 (14)	0.0259 (5)
C48	0.72332 (14)	0.78526 (12)	0.27189 (13)	0.0212 (4)
C51	0.24638 (19)	1.02434 (15)	0.91112 (16)	0.0337 (6)	0.913 (2)
C52	0.1637 (2)	1.05907 (15)	0.94109 (15)	0.0357 (6)	0.913 (2)
C53	0.0715 (2)	1.03501 (15)	0.91273 (16)	0.0345 (6)	0.913 (2)
C54	0.06071 (18)	0.97524 (14)	0.85275 (15)	0.0286 (6)	0.913 (2)
C55	0.14274 (18)	0.94107 (14)	0.82041 (16)	0.0302 (6)	0.913 (2)
C56	0.23430 (19)	0.96483 (15)	0.84988 (15)	0.0320 (6)	0.913 (2)
C57	0.3488 (2)	1.0484 (2)	0.9428 (2)	0.0528 (8)	0.913 (2)
C58	0.3795 (3)	1.0069 (3)	1.0246 (2)	0.0740 (11)	0.913 (2)
O61	0.3150 (10)	0.9561 (9)	0.8228 (10)	0.020*	0.087 (2)
H14	0.5190	1.1820	0.8864	0.036*
H15	0.4786	1.3161	0.9218	0.039*
H16	0.4666	1.4171	0.8210	0.039*
H17	0.4945	1.3885	0.6808	0.035*
H24	0.7642	1.2312	0.2392	0.030*
H25	0.8027	1.3699	0.2307	0.035*
H26	0.8262	1.4479	0.3506	0.041*
H27	0.8112	1.3900	0.4838	0.037*
H34	0.9182	0.5670	−0.2050	0.030*
H35	0.9641	0.6780	−0.2862	0.035*
H36	1.0139	0.7991	−0.2230	0.035*
H37	1.0182	0.8140	−0.0771	0.035*
H44	0.7368	0.7341	0.4699	0.029*
H45	0.6847	0.8692	0.4819	0.033*
H46	0.6599	0.9502	0.3639	0.034*
H47	0.6818	0.8979	0.2297	0.031*
H52	0.1704	1.1005	0.9822	0.043*	0.913 (2)
H53	0.0157	1.0596	0.9345	0.041*	0.913 (2)
H54	−0.0024	0.9577	0.8338	0.034*	0.913 (2)
H55	0.1359	0.9012	0.7778	0.036*	0.913 (2)
H56	0.2900	0.9402	0.8281	0.038*	0.913 (2)
H57A	0.3954	1.0339	0.9001	0.063*	0.913 (2)
H57B	0.3515	1.1079	0.9507	0.063*	0.913 (2)
H58A	0.3329	1.0201	1.0667	0.111*	0.913 (2)
H58B	0.4444	1.0259	1.0436	0.111*	0.913 (2)
H58C	0.3810	0.9481	1.0163	0.111*	0.913 (2)
H61A	0.3208	0.9160	0.7911	0.030*	0.087 (2)
H61B	0.2762	0.9491	0.8611	0.030*	0.087 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0304 (3)	0.0249 (3)	0.0240 (3)	−0.0028 (2)	0.0067 (2)	−0.0018 (2)
N11	0.0252 (9)	0.0244 (8)	0.0236 (9)	−0.0008 (7)	0.0052 (7)	0.0008 (7)
C11	0.0203 (11)	0.0254 (10)	0.0265 (12)	−0.0004 (8)	0.0038 (9)	0.0020 (9)
O11	0.0406 (9)	0.0313 (8)	0.0251 (9)	−0.0003 (7)	0.0052 (7)	0.0057 (7)
C12	0.0199 (10)	0.0312 (11)	0.0235 (11)	−0.0030 (8)	0.0036 (8)	0.0009 (9)
O12	0.0380 (9)	0.0286 (8)	0.0303 (9)	−0.0004 (6)	0.0031 (7)	0.0043 (7)
C13	0.0197 (10)	0.0288 (11)	0.0247 (11)	−0.0019 (8)	0.0030 (8)	−0.0005 (9)
C14	0.0250 (11)	0.0394 (12)	0.0259 (12)	−0.0050 (9)	0.0027 (9)	−0.0018 (10)
C15	0.0295 (12)	0.0422 (13)	0.0272 (12)	−0.0037 (10)	0.0038 (10)	−0.0100 (11)
C16	0.0287 (12)	0.0316 (11)	0.0377 (14)	−0.0028 (9)	0.0035 (10)	−0.0119 (11)
C17	0.0261 (11)	0.0273 (11)	0.0341 (13)	−0.0023 (9)	0.0014 (10)	−0.0033 (10)
C18	0.0187 (10)	0.0282 (11)	0.0235 (11)	−0.0029 (8)	0.0024 (8)	−0.0014 (9)
S2	0.0318 (3)	0.0220 (3)	0.0250 (3)	0.0050 (2)	0.0094 (2)	0.0060 (2)
N21	0.0297 (10)	0.0202 (8)	0.0224 (9)	0.0010 (7)	0.0074 (8)	0.0020 (7)
C21	0.0218 (10)	0.0266 (10)	0.0215 (11)	0.0022 (8)	0.0018 (8)	−0.0015 (9)
O21	0.0382 (9)	0.0357 (8)	0.0224 (8)	−0.0023 (7)	0.0044 (7)	−0.0045 (7)
C22	0.0215 (10)	0.0230 (10)	0.0226 (11)	0.0041 (8)	0.0056 (8)	−0.0005 (9)
O22	0.0404 (9)	0.0232 (7)	0.0270 (8)	−0.0011 (6)	0.0061 (7)	−0.0045 (7)
C23	0.0182 (10)	0.0230 (10)	0.0244 (11)	0.0033 (8)	0.0047 (8)	0.0000 (9)
C24	0.0219 (11)	0.0278 (10)	0.0250 (11)	0.0025 (8)	0.0054 (9)	0.0008 (9)
C25	0.0277 (12)	0.0304 (11)	0.0311 (12)	0.0041 (9)	0.0082 (10)	0.0108 (10)
C26	0.0353 (13)	0.0229 (10)	0.0442 (15)	−0.0020 (9)	0.0098 (11)	0.0051 (10)
C27	0.0329 (12)	0.0244 (10)	0.0346 (13)	−0.0014 (9)	0.0068 (10)	−0.0039 (10)
C28	0.0231 (11)	0.0230 (10)	0.0230 (11)	0.0026 (8)	0.0048 (8)	−0.0003 (9)
S3	0.0324 (3)	0.0263 (3)	0.0200 (3)	0.0073 (2)	0.0053 (2)	0.0010 (2)
N31	0.0278 (9)	0.0226 (8)	0.0195 (9)	0.0025 (7)	0.0050 (7)	−0.0017 (7)
C31	0.0233 (11)	0.0224 (10)	0.0276 (12)	0.0013 (8)	0.0054 (9)	−0.0028 (9)
O31	0.0423 (10)	0.0324 (8)	0.0302 (9)	−0.0053 (7)	0.0056 (7)	−0.0110 (7)
C32	0.0175 (10)	0.0245 (10)	0.0226 (11)	0.0061 (8)	0.0040 (8)	−0.0030 (9)
O32	0.0270 (8)	0.0216 (7)	0.0281 (8)	−0.0001 (6)	0.0051 (6)	−0.0014 (6)
C33	0.0186 (10)	0.0229 (10)	0.0240 (11)	0.0031 (8)	0.0046 (8)	0.0005 (9)
C34	0.0246 (11)	0.0252 (10)	0.0257 (11)	0.0034 (8)	0.0047 (9)	−0.0008 (9)
C35	0.0257 (11)	0.0374 (12)	0.0237 (11)	0.0072 (9)	0.0062 (9)	0.0051 (10)
C36	0.0245 (11)	0.0313 (11)	0.0331 (13)	0.0010 (9)	0.0081 (9)	0.0100 (10)
C37	0.0242 (11)	0.0242 (10)	0.0386 (13)	−0.0008 (8)	0.0041 (10)	0.0013 (10)
C38	0.0200 (10)	0.0248 (10)	0.0272 (12)	0.0020 (8)	0.0050 (9)	−0.0008 (9)
S4	0.0328 (3)	0.0233 (3)	0.0225 (3)	−0.0035 (2)	0.0087 (2)	−0.0057 (2)
N41	0.0280 (9)	0.0189 (8)	0.0184 (9)	0.0001 (7)	0.0051 (7)	−0.0011 (7)
C41	0.0201 (10)	0.0235 (10)	0.0220 (11)	−0.0028 (8)	0.0037 (8)	0.0016 (9)
O41	0.0386 (9)	0.0337 (8)	0.0202 (8)	−0.0005 (7)	0.0053 (7)	0.0048 (7)
C42	0.0251 (11)	0.0230 (10)	0.0210 (11)	−0.0016 (8)	0.0040 (8)	−0.0008 (9)
O42	0.0530 (10)	0.0237 (8)	0.0243 (9)	0.0049 (7)	0.0043 (7)	0.0039 (7)
C43	0.0188 (10)	0.0212 (9)	0.0221 (11)	−0.0012 (7)	0.0025 (8)	−0.0010 (8)
C44	0.0250 (11)	0.0270 (10)	0.0206 (11)	−0.0007 (8)	0.0034 (9)	−0.0009 (9)
C45	0.0242 (11)	0.0301 (11)	0.0277 (12)	−0.0022 (9)	0.0054 (9)	−0.0089 (10)
C46	0.0248 (11)	0.0208 (10)	0.0404 (14)	−0.0008 (8)	0.0066 (10)	−0.0049 (10)
C47	0.0225 (11)	0.0228 (10)	0.0325 (12)	−0.0004 (8)	0.0034 (9)	0.0041 (9)
C48	0.0178 (10)	0.0227 (9)	0.0233 (11)	−0.0024 (8)	0.0031 (8)	−0.0008 (9)
C51	0.0429 (15)	0.0324 (13)	0.0254 (13)	−0.0100 (11)	−0.0027 (11)	0.0098 (11)
C52	0.0615 (18)	0.0265 (12)	0.0188 (13)	−0.0032 (12)	0.0001 (12)	−0.0038 (10)
C53	0.0450 (16)	0.0322 (13)	0.0268 (14)	0.0074 (11)	0.0074 (12)	0.0021 (11)
C54	0.0349 (14)	0.0264 (12)	0.0247 (13)	−0.0018 (10)	0.0026 (10)	0.0037 (10)
C55	0.0407 (15)	0.0218 (11)	0.0286 (14)	−0.0038 (10)	0.0077 (11)	−0.0033 (10)
C56	0.0392 (15)	0.0287 (12)	0.0290 (14)	−0.0040 (10)	0.0109 (11)	0.0029 (11)
C57	0.0534 (19)	0.0547 (18)	0.050 (2)	−0.0076 (15)	−0.0007 (15)	0.0073 (15)
C58	0.057 (2)	0.112 (3)	0.052 (2)	−0.009 (2)	−0.0042 (17)	0.007 (2)

Geometric parameters (Å, º) top

S1—N11	1.687 (2)	C34—C35	1.391 (3)
S1—S2	2.0308 (7)	C34—H34	0.9500
N11—C12	1.422 (3)	C35—C36	1.393 (3)
N11—C11	1.429 (3)	C35—H35	0.9500
C11—O11	1.200 (2)	C36—C37	1.394 (3)
C11—C18	1.479 (3)	C36—H36	0.9500
C12—O12	1.202 (2)	C37—C38	1.383 (3)
C12—C13	1.488 (3)	C37—H37	0.9500
C13—C14	1.379 (3)	S4—N41	1.690 (2)
C13—C18	1.386 (3)	N41—C42	1.416 (3)
C14—C15	1.397 (3)	N41—C41	1.431 (3)
C14—H14	0.9500	C41—O41	1.199 (2)
C15—C16	1.391 (3)	C41—C48	1.486 (3)
C15—H15	0.9500	C42—O42	1.201 (2)
C16—C17	1.387 (3)	C42—C43	1.483 (3)
C16—H16	0.9500	C43—C44	1.384 (3)
C17—C18	1.393 (3)	C43—C48	1.388 (3)
C17—H17	0.9500	C44—C45	1.389 (3)
S2—N21	1.688 (2)	C44—H44	0.9500
N21—C22	1.418 (3)	C45—C46	1.394 (3)
N21—C21	1.427 (3)	C45—H45	0.9500
C21—O21	1.199 (2)	C46—C47	1.394 (3)
C21—C28	1.485 (3)	C46—H46	0.9500
C22—O22	1.202 (2)	C47—C48	1.386 (3)
C22—C23	1.487 (3)	C47—H47	0.9500
C23—C24	1.378 (3)	C51—C52	1.382 (4)
C23—C28	1.390 (3)	C51—C56	1.393 (4)
C24—C25	1.393 (3)	C51—C57	1.526 (4)
C24—H24	0.9500	C52—C53	1.384 (4)
C25—C26	1.390 (3)	C52—H52	0.9500
C25—H25	0.9500	C53—C54	1.380 (3)
C26—C27	1.395 (3)	C53—H53	0.9500
C26—H26	0.9500	C54—C55	1.386 (3)
C27—C28	1.379 (3)	C54—H54	0.9500
C27—H27	0.9500	C55—C56	1.380 (4)
S3—N31	1.685 (2)	C55—H55	0.9500
S3—S4	2.0266 (7)	C56—H56	0.9500
N31—C32	1.420 (3)	C57—C58	1.521 (5)
N31—C31	1.429 (3)	C57—H57A	0.9900
C31—O31	1.202 (3)	C57—H57B	0.9900
C31—C38	1.480 (3)	C58—H58A	0.9800
C32—O32	1.207 (2)	C58—H58B	0.9800
C32—C33	1.479 (3)	C58—H58C	0.9800
C33—C34	1.376 (3)	O61—H61A	0.8402
C33—C38	1.396 (3)	O61—H61B	0.8425

N11—S1—S2	105.91 (6)	C33—C34—C35	117.6 (2)
C12—N11—C11	111.7 (2)	C33—C34—H34	121.2
C12—N11—S1	124.6 (2)	C35—C34—H34	121.2
C11—N11—S1	123.0 (2)	C34—C35—C36	120.7 (2)
O11—C11—N11	124.5 (2)	C34—C35—H35	119.6
O11—C11—C18	130.7 (2)	C36—C35—H35	119.6
N11—C11—C18	104.8 (2)	C35—C36—C37	121.6 (2)
O12—C12—N11	124.7 (2)	C35—C36—H36	119.2
O12—C12—C13	130.2 (2)	C37—C36—H36	119.2
N11—C12—C13	105.1 (2)	C38—C37—C36	117.3 (2)
C14—C13—C18	121.8 (2)	C38—C37—H37	121.4
C14—C13—C12	129.4 (2)	C36—C37—H37	121.4
C18—C13—C12	108.7 (2)	C37—C38—C33	121.0 (2)
C13—C14—C15	117.0 (2)	C37—C38—C31	130.0 (2)
C13—C14—H14	121.5	C33—C38—C31	109.0 (2)
C15—C14—H14	121.5	N41—S4—S3	107.05 (6)
C16—C15—C14	121.4 (2)	C42—N41—C41	111.8 (2)
C16—C15—H15	119.3	C42—N41—S4	122.7 (2)
C14—C15—H15	119.3	C41—N41—S4	124.7 (2)
C17—C16—C15	121.4 (2)	O41—C41—N41	124.4 (2)
C17—C16—H16	119.3	O41—C41—C48	130.9 (2)
C15—C16—H16	119.3	N41—C41—C48	104.7 (2)
C16—C17—C18	117.0 (2)	O42—C42—N41	124.4 (2)
C16—C17—H17	121.5	O42—C42—C43	130.4 (2)
C18—C17—H17	121.5	N41—C42—C43	105.3 (2)
C13—C18—C17	121.5 (2)	C44—C43—C48	121.9 (2)
C13—C18—C11	109.6 (2)	C44—C43—C42	129.2 (2)
C17—C18—C11	128.9 (2)	C48—C43—C42	109.0 (2)
N21—S2—S1	105.26 (6)	C43—C44—C45	117.4 (2)
C22—N21—C21	112.0 (2)	C43—C44—H44	121.3
C22—N21—S2	125.0 (2)	C45—C44—H44	121.3
C21—N21—S2	123.0 (2)	C44—C45—C46	121.0 (2)
O21—C21—N21	124.3 (2)	C44—C45—H45	119.5
O21—C21—C28	130.9 (2)	C46—C45—H45	119.5
N21—C21—C28	104.8 (2)	C47—C46—C45	121.4 (2)
O22—C22—N21	125.3 (2)	C47—C46—H46	119.3
O22—C22—C23	129.6 (2)	C45—C46—H46	119.3
N21—C22—C23	105.1 (2)	C48—C47—C46	117.3 (2)
C24—C23—C28	121.4 (2)	C48—C47—H47	121.3
C24—C23—C22	129.6 (2)	C46—C47—H47	121.3
C28—C23—C22	109.0 (2)	C47—C48—C43	121.1 (2)
C23—C24—C25	117.3 (2)	C47—C48—C41	129.7 (2)
C23—C24—H24	121.3	C43—C48—C41	109.2 (2)
C25—C24—H24	121.3	C52—C51—C56	117.8 (2)
C26—C25—C24	121.2 (2)	C52—C51—C57	122.7 (3)
C26—C25—H25	119.4	C56—C51—C57	119.5 (3)
C24—C25—H25	119.4	C51—C52—C53	121.6 (2)
C25—C26—C27	121.2 (2)	C51—C52—H52	119.2
C25—C26—H26	119.4	C53—C52—H52	119.2
C27—C26—H26	119.4	C54—C53—C52	119.8 (2)
C28—C27—C26	117.0 (2)	C54—C53—H53	120.1
C28—C27—H27	121.5	C52—C53—H53	120.1
C26—C27—H27	121.5	C53—C54—C55	119.4 (2)
C27—C28—C23	121.8 (2)	C53—C54—H54	120.3
C27—C28—C21	129.1 (2)	C55—C54—H54	120.3
C23—C28—C21	109.1 (2)	C56—C55—C54	120.2 (2)
N31—S3—S4	105.50 (6)	C56—C55—H55	119.9
C32—N31—C31	111.5 (2)	C54—C55—H55	119.9
C32—N31—S3	123.4 (2)	C55—C56—C51	121.0 (2)
C31—N31—S3	124.2 (2)	C55—C56—H56	119.5
O31—C31—N31	124.2 (2)	C51—C56—H56	119.5
O31—C31—C38	130.7 (2)	C58—C57—C51	112.4 (3)
N31—C31—C38	105.1 (2)	C58—C57—H57A	109.1
O32—C32—N31	124.8 (2)	C51—C57—H57A	109.1
O32—C32—C33	129.7 (2)	C58—C57—H57B	109.1
N31—C32—C33	105.5 (2)	C51—C57—H57B	109.1
C34—C33—C38	121.8 (2)	H57A—C57—H57B	107.9
C34—C33—C32	129.3 (2)	H61A—O61—H61B	114.8
C38—C33—C32	108.8 (2)

S2—S1—N11—C12	−95.9 (2)	S3—N31—C31—C38	172.0 (2)
S2—S1—N11—C11	94.2 (2)	C31—N31—C32—O32	177.3 (2)
C12—N11—C11—O11	−178.7 (2)	S3—N31—C32—O32	7.6 (3)
S1—N11—C11—O11	−7.6 (3)	C31—N31—C32—C33	−2.7 (2)
C12—N11—C11—C18	0.3 (2)	S3—N31—C32—C33	−172.4 (2)
S1—N11—C11—C18	171.4 (2)	O32—C32—C33—C34	2.9 (4)
C11—N11—C12—O12	178.4 (2)	N31—C32—C33—C34	−177.2 (2)
S1—N11—C12—O12	7.4 (3)	O32—C32—C33—C38	−178.1 (2)
C11—N11—C12—C13	−0.5 (2)	N31—C32—C33—C38	1.9 (2)
S1—N11—C12—C13	−171.5 (2)	C38—C33—C34—C35	0.5 (3)
O12—C12—C13—C14	−0.6 (4)	C32—C33—C34—C35	179.4 (2)
N11—C12—C13—C14	178.2 (2)	C33—C34—C35—C36	−0.1 (3)
O12—C12—C13—C18	−178.2 (2)	C34—C35—C36—C37	−0.3 (3)
N11—C12—C13—C18	0.6 (2)	C35—C36—C37—C38	0.4 (3)
C18—C13—C14—C15	0.5 (3)	C36—C37—C38—C33	−0.1 (3)
C12—C13—C14—C15	−176.9 (2)	C36—C37—C38—C31	−178.9 (2)
C13—C14—C15—C16	−0.3 (3)	C34—C33—C38—C37	−0.4 (3)
C14—C15—C16—C17	0.0 (3)	C32—C33—C38—C37	−179.5 (2)
C15—C16—C17—C18	0.2 (3)	C34—C33—C38—C31	178.7 (2)
C14—C13—C18—C17	−0.3 (3)	C32—C33—C38—C31	−0.5 (2)
C12—C13—C18—C17	177.5 (2)	O31—C31—C38—C37	−2.1 (4)
C14—C13—C18—C11	−178.3 (2)	N31—C31—C38—C37	177.8 (2)
C12—C13—C18—C11	−0.4 (2)	O31—C31—C38—C33	179.0 (2)
C16—C17—C18—C13	−0.1 (3)	N31—C31—C38—C33	−1.1 (2)
C16—C17—C18—C11	177.5 (2)	N31—S3—S4—N41	−94.51 (9)
O11—C11—C18—C13	179.0 (2)	S3—S4—N41—C42	−96.6 (2)
N11—C11—C18—C13	0.1 (2)	S3—S4—N41—C41	94.6 (2)
O11—C11—C18—C17	1.2 (4)	C42—N41—C41—O41	178.1 (2)
N11—C11—C18—C17	−177.7 (2)	S4—N41—C41—O41	−12.0 (3)
N11—S1—S2—N21	−80.14 (9)	C42—N41—C41—C48	−2.0 (2)
S1—S2—N21—C22	−93.1 (2)	S4—N41—C41—C48	167.9 (2)
S1—S2—N21—C21	85.8 (2)	C41—N41—C42—O42	−176.5 (2)
C22—N21—C21—O21	178.7 (2)	S4—N41—C42—O42	13.4 (3)
S2—N21—C21—O21	−0.3 (3)	C41—N41—C42—C43	2.8 (2)
C22—N21—C21—C28	−0.8 (2)	S4—N41—C42—C43	−167.4 (2)
S2—N21—C21—C28	−179.9 (2)	O42—C42—C43—C44	−2.9 (4)
C21—N21—C22—O22	−177.4 (2)	N41—C42—C43—C44	177.9 (2)
S2—N21—C22—O22	1.6 (3)	O42—C42—C43—C48	176.7 (2)
C21—N21—C22—C23	1.5 (2)	N41—C42—C43—C48	−2.5 (2)
S2—N21—C22—C23	−179.5 (2)	C48—C43—C44—C45	−0.7 (3)
O22—C22—C23—C24	−0.8 (4)	C42—C43—C44—C45	178.9 (2)
N21—C22—C23—C24	−179.7 (2)	C43—C44—C45—C46	−0.3 (3)
O22—C22—C23—C28	177.3 (2)	C44—C45—C46—C47	1.0 (3)
N21—C22—C23—C28	−1.6 (2)	C45—C46—C47—C48	−0.8 (3)
C28—C23—C24—C25	−1.2 (3)	C46—C47—C48—C43	−0.2 (3)
C22—C23—C24—C25	176.7 (2)	C46—C47—C48—C41	179.8 (2)
C23—C24—C25—C26	0.9 (3)	C44—C43—C48—C47	0.9 (3)
C24—C25—C26—C27	−0.1 (3)	C42—C43—C48—C47	−178.8 (2)
C25—C26—C27—C28	−0.4 (3)	C44—C43—C48—C41	−179.1 (2)
C26—C27—C28—C23	0.1 (3)	C42—C43—C48—C41	1.3 (2)
C26—C27—C28—C21	−178.2 (2)	O41—C41—C48—C47	0.3 (4)
C24—C23—C28—C27	0.8 (3)	N41—C41—C48—C47	−179.6 (2)
C22—C23—C28—C27	−177.5 (2)	O41—C41—C48—C43	−179.7 (2)
C24—C23—C28—C21	179.4 (2)	N41—C41—C48—C43	0.4 (2)
C22—C23—C28—C21	1.1 (2)	C56—C51—C52—C53	1.1 (4)
O21—C21—C28—C27	−1.3 (4)	C57—C51—C52—C53	−178.6 (2)
N21—C21—C28—C27	178.3 (2)	C51—C52—C53—C54	−0.3 (4)
O21—C21—C28—C23	−179.7 (2)	C52—C53—C54—C55	−1.2 (4)
N21—C21—C28—C23	−0.2 (2)	C53—C54—C55—C56	2.0 (4)
S4—S3—N31—C32	−90.4 (2)	C54—C55—C56—C51	−1.3 (4)
S4—S3—N31—C31	101.2 (2)	C52—C51—C56—C55	−0.3 (4)
C32—N31—C31—O31	−177.7 (2)	C57—C51—C56—C55	179.4 (2)
S3—N31—C31—O31	−8.1 (3)	C52—C51—C57—C58	80.9 (4)
C32—N31—C31—C38	2.4 (2)	C56—C51—C57—C58	−98.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C35—H35···O31ⁱ	0.95	2.45	3.230 (3)	140
C44—H44···O41ⁱⁱ	0.95	2.48	3.258 (2)	139
C46—H46···O22	0.95	2.44	3.249 (2)	143

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

(9) N,N'-Dithiophthalimide top

Crystal data top

C₁₆H₈N₂O₄S₂	F(000) = 728
M_r = 356.36	D_x = 1.337 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.4180 (6) Å	Cell parameters from 1993 reflections
b = 16.0502 (7) Å	θ = 3.2–27.5°
c = 7.6616 (3) Å	µ = 0.32 mm⁻¹
β = 93.369 (2)°	T = 120 K
V = 1769.92 (13) Å³	Block, colourless
Z = 4	0.10 × 0.10 × 0.08 mm

Data collection top

Kappa-CCD diffractometer	1993 independent reflections
Radiation source: fine-focus sealed X-ray tube	1633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −18→18
T_min = 0.969, T_max = 0.975	k = −19→20
5857 measured reflections	l = −8→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0708P)² + 0.747P] where P = (F_o² + 2F_c²)/3
1993 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.45335 (3)	0.43029 (3)	0.14438 (6)	0.02559 (19)
N1	0.37127 (10)	0.36113 (10)	0.1932 (2)	0.0250 (4)
C1	0.37362 (13)	0.27454 (12)	0.1518 (2)	0.0268 (4)
O1	0.43557 (10)	0.24085 (9)	0.08144 (19)	0.0328 (4)
C2	0.28882 (13)	0.38302 (13)	0.2784 (2)	0.0268 (4)
O2	0.27199 (10)	0.45160 (9)	0.3303 (2)	0.0362 (4)
C3	0.23485 (14)	0.30446 (13)	0.2849 (2)	0.0286 (5)
C4	0.14930 (14)	0.29010 (15)	0.3534 (3)	0.0339 (5)
C5	0.11631 (15)	0.20843 (17)	0.3485 (3)	0.0410 (6)
C6	0.16707 (17)	0.14456 (15)	0.2784 (3)	0.0401 (6)
C7	0.25319 (16)	0.15902 (14)	0.2083 (3)	0.0345 (5)
C8	0.28509 (14)	0.24047 (12)	0.2134 (2)	0.0277 (4)
H4	0.1147	0.3340	0.4016	0.041*
H5	0.0579	0.1963	0.3940	0.049*
H6	0.1428	0.0895	0.2780	0.048*
H7	0.2879	0.1153	0.1598	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0206 (3)	0.0216 (3)	0.0352 (3)	−0.00148 (17)	0.0071 (2)	0.00603 (18)
N1	0.0217 (8)	0.0231 (8)	0.0306 (8)	−0.0061 (6)	0.0065 (6)	0.0010 (6)
C1	0.0294 (10)	0.0264 (10)	0.0243 (9)	−0.0063 (8)	0.0004 (8)	0.0029 (7)
O1	0.0359 (8)	0.0279 (8)	0.0354 (8)	0.0016 (6)	0.0076 (6)	−0.0011 (6)
C2	0.0222 (9)	0.0322 (11)	0.0262 (9)	−0.0032 (8)	0.0030 (7)	0.0024 (8)
O2	0.0317 (8)	0.0335 (8)	0.0444 (9)	−0.0017 (6)	0.0119 (7)	−0.0029 (7)
C3	0.0277 (10)	0.0360 (11)	0.0219 (9)	−0.0093 (8)	0.0013 (7)	0.0025 (8)
C4	0.0275 (10)	0.0484 (13)	0.0258 (10)	−0.0082 (9)	0.0025 (8)	0.0048 (9)
C5	0.0331 (12)	0.0616 (16)	0.0280 (10)	−0.0232 (11)	−0.0008 (9)	0.0105 (10)
C6	0.0435 (13)	0.0445 (13)	0.0314 (11)	−0.0256 (11)	−0.0058 (9)	0.0090 (10)
C7	0.0433 (12)	0.0329 (11)	0.0267 (10)	−0.0145 (9)	−0.0046 (9)	0.0047 (8)
C8	0.0294 (10)	0.0314 (10)	0.0220 (9)	−0.0101 (8)	−0.0008 (8)	0.0050 (8)

Geometric parameters (Å, º) top

S1—N1	1.681 (2)	C3—C8	1.388 (3)
S1—S1ⁱ	2.0428 (9)	C4—C5	1.394 (3)
N1—C1	1.426 (3)	C4—H4	0.9500
N1—C2	1.433 (2)	C5—C6	1.386 (4)
C1—O1	1.199 (2)	C5—H5	0.9500
C1—C8	1.491 (3)	C6—C7	1.401 (3)
C2—O2	1.200 (2)	C6—H6	0.9500
C2—C3	1.484 (3)	C7—C8	1.386 (3)
C3—C4	1.388 (3)	C7—H7	0.9500

N1—S1—S1ⁱ	105.25 (6)	C3—C4—H4	121.5
C1—N1—C2	111.8 (2)	C5—C4—H4	121.5
C1—N1—S1	124.6 (2)	C6—C5—C4	121.3 (2)
C2—N1—S1	123.6 (2)	C6—C5—H5	119.4
O1—C1—N1	124.6 (2)	C4—C5—H5	119.4
O1—C1—C8	130.7 (2)	C5—C6—C7	121.7 (2)
N1—C1—C8	104.8 (2)	C5—C6—H6	119.1
O2—C2—N1	124.4 (2)	C7—C6—H6	119.1
O2—C2—C3	130.7 (2)	C8—C7—C6	116.5 (2)
N1—C2—C3	104.9 (2)	C8—C7—H7	121.8
C4—C3—C8	121.5 (2)	C6—C7—H7	121.8
C4—C3—C2	129.3 (2)	C7—C8—C3	122.0 (2)
C8—C3—C2	109.2 (2)	C7—C8—C1	128.8 (2)
C3—C4—C5	117.1 (2)	C3—C8—C1	109.3 (2)

C1—N1—S1—S1ⁱ	−90.3 (2)	N1—S1—S1ⁱ—N1ⁱ	93.59 (8)
C2—N1—S1—S1ⁱ	91.3 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱⁱ	0.95	2.55	3.344 (3)	142

Symmetry code: (ii) x−1/2, −y+1/2, z+1/2.

(10) N,N'-Dithiodiphthalimide top

Crystal data top

C₁₆H₈N₂O₄S₂	F(000) = 728
M_r = 356.36	D_x = 1.357 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.3752 (5) Å	Cell parameters from 1974 reflections
b = 15.9349 (10) Å	θ = 3.2–27.5°
c = 7.631 (10) Å	µ = 0.33 mm⁻¹
β = 93.845 (2)°	T = 120 K
V = 1744 (2) Å³	Block, colourless
Z = 4	0.15 × 0.10 × 0.08 mm

Data collection top

Kappa-CCD diffractometer	1974 independent reflections
Radiation source: fine-focus sealed X-ray tube	1437 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −17→18
T_min = 0.953, T_max = 0.974	k = −20→20
5498 measured reflections	l = −9→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0908P)²] where P = (F_o² + 2F_c²)/3
1974 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.45331 (4)	0.42910 (4)	0.14377 (8)	0.0327 (3)
N1	0.37002 (13)	0.36043 (12)	0.1929 (3)	0.0316 (5)
C1	0.37124 (18)	0.27298 (15)	0.1537 (3)	0.0349 (6)
O1	0.43325 (13)	0.23770 (11)	0.0852 (2)	0.0426 (5)
C2	0.28837 (16)	0.38382 (15)	0.2762 (3)	0.0338 (6)
O2	0.27204 (12)	0.45353 (11)	0.3267 (2)	0.0421 (5)
C3	0.23349 (18)	0.30530 (16)	0.2848 (3)	0.0367 (6)
C4	0.14755 (18)	0.29256 (19)	0.3544 (3)	0.0419 (7)
C5	0.1135 (2)	0.2100 (2)	0.3504 (3)	0.0481 (8)
C6	0.1628 (2)	0.14529 (18)	0.2812 (3)	0.0487 (8)
C7	0.2491 (2)	0.15860 (16)	0.2104 (3)	0.0426 (7)
C8	0.28220 (17)	0.24009 (16)	0.2143 (3)	0.0351 (6)
H4	0.1137	0.3374	0.4020	0.050*
H5	0.0551	0.1986	0.3966	0.058*
H6	0.1377	0.0902	0.2815	0.058*
H7	0.2831	0.1140	0.1623	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0307 (4)	0.0232 (4)	0.0462 (4)	−0.0030 (2)	0.0170 (3)	0.0037 (2)
N1	0.0322 (10)	0.0238 (10)	0.0413 (11)	−0.0070 (8)	0.0199 (9)	−0.0037 (8)
C1	0.0481 (14)	0.0265 (13)	0.0323 (13)	−0.0076 (11)	0.0190 (11)	−0.0040 (10)
O1	0.0570 (11)	0.0305 (10)	0.0434 (10)	−0.0007 (8)	0.0262 (9)	−0.0035 (8)
C2	0.0363 (13)	0.0306 (13)	0.0362 (13)	−0.0094 (10)	0.0155 (11)	−0.0072 (10)
O2	0.0427 (10)	0.0293 (10)	0.0570 (12)	−0.0069 (8)	0.0239 (9)	−0.0101 (8)
C3	0.0450 (14)	0.0353 (14)	0.0317 (12)	−0.0172 (12)	0.0178 (11)	−0.0082 (10)
C4	0.0425 (15)	0.0495 (17)	0.0358 (14)	−0.0181 (12)	0.0178 (11)	−0.0093 (12)
C5	0.0541 (16)	0.0584 (19)	0.0339 (14)	−0.0319 (15)	0.0177 (12)	−0.0059 (13)
C6	0.0722 (19)	0.0429 (16)	0.0321 (14)	−0.0344 (15)	0.0116 (13)	−0.0075 (12)
C7	0.0639 (17)	0.0347 (14)	0.0312 (13)	−0.0196 (13)	0.0189 (13)	−0.0083 (11)
C8	0.0470 (14)	0.0319 (13)	0.0279 (12)	−0.0144 (11)	0.0150 (11)	−0.0055 (10)

Geometric parameters (Å, º) top

S1—N1	1.683 (2)	C3—C4	1.392 (3)
S1—S1ⁱ	2.034 (2)	C4—C5	1.403 (4)
N1—C2	1.422 (3)	C4—H4	0.9500
N1—C1	1.426 (3)	C5—C6	1.377 (5)
C1—O1	1.203 (3)	C5—H5	0.9500
C1—C8	1.485 (3)	C6—C7	1.403 (4)
C2—O2	1.204 (3)	C6—H6	0.9500
C2—C3	1.483 (3)	C7—C8	1.383 (3)
C3—C8	1.382 (4)	C7—H7	0.9500

N1—S1—S1ⁱ	105.30 (9)	C3—C4—H4	121.8
C2—N1—C1	111.9 (2)	C5—C4—H4	121.8
C2—N1—S1	123.4 (2)	C6—C5—C4	121.5 (2)
C1—N1—S1	124.8 (2)	C6—C5—H5	119.2
O1—C1—N1	124.6 (2)	C4—C5—H5	119.2
O1—C1—C8	130.5 (2)	C5—C6—C7	121.7 (2)
N1—C1—C8	104.9 (2)	C5—C6—H6	119.1
O2—C2—N1	124.7 (2)	C7—C6—H6	119.1
O2—C2—C3	130.4 (2)	C8—C7—C6	116.5 (3)
N1—C2—C3	104.9 (2)	C8—C7—H7	121.8
C8—C3—C4	121.6 (2)	C6—C7—H7	121.8
C8—C3—C2	109.4 (2)	C3—C8—C7	122.1 (2)
C4—C3—C2	128.9 (2)	C3—C8—C1	109.0 (2)
C3—C4—C5	116.5 (3)	C7—C8—C1	128.8 (2)

C1—N1—S1—S1ⁱ	−90.0 (2)	N1—S1—S1ⁱ—N1ⁱ	95.2 (2)
C2—N1—S1—S1ⁱ	91.4 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱⁱ	0.95	2.55	3.353 (5)	142

Symmetry code: (ii) x−1/2, −y+1/2, z+1/2.

(11) N,N'-Dithiodiphthalimide hemi(p-xylene) solvate top

Crystal data top

C₁₆H₈N₂O₄S₂·0.5(C₈H₁₀)	F(000) = 844
M_r = 409.44	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.2629 (5) Å	Cell parameters from 4089 reflections
b = 16.1851 (4) Å	θ = 2.9–29.8°
c = 7.7835 (2) Å	µ = 0.33 mm⁻¹
β = 94.3917 (9)°	T = 120 K
V = 1791.52 (9) Å³	Block, colourless
Z = 4	0.25 × 0.15 × 0.10 mm

Data collection top

Kappa-CCD diffractometer	4089 independent reflections
Radiation source: fine-focus sealed X-ray tube	3275 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
φ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −14→18
T_min = 0.922, T_max = 0.968	k = −20→20
14107 measured reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0651P)² + 0.0637P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
4089 reflections	Δρ_max = 0.37 e Å⁻³
255 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (2)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S11	0.44791 (3)	0.55977 (2)	0.85382 (5)	0.02330 (15)
N11	0.36024 (9)	0.61984 (8)	0.79190 (16)	0.0197 (3)
C11	0.34979 (11)	0.70516 (10)	0.83041 (18)	0.0179 (3)
O11	0.40523 (8)	0.74560 (7)	0.90378 (14)	0.0251 (3)
C12	0.28322 (11)	0.58913 (10)	0.70206 (19)	0.0188 (3)
O12	0.27727 (8)	0.51960 (7)	0.65138 (15)	0.0295 (3)
C13	0.21971 (11)	0.66113 (10)	0.68942 (19)	0.0184 (3)
C14	0.13444 (11)	0.66653 (10)	0.61582 (19)	0.0220 (4)
C15	0.09067 (12)	0.74383 (11)	0.6185 (2)	0.0244 (4)
C16	0.13126 (12)	0.81247 (11)	0.68982 (19)	0.0225 (4)
C17	0.21709 (11)	0.80689 (10)	0.76358 (19)	0.0195 (3)
C18	0.25971 (10)	0.72993 (10)	0.76244 (18)	0.0168 (3)
S21	0.54868 (3)	0.56149 (2)	0.65421 (5)	0.02299 (15)
N21	0.62227 (9)	0.63917 (8)	0.69718 (17)	0.0206 (3)
C21	0.61083 (11)	0.72280 (10)	0.64417 (19)	0.0192 (3)
O21	0.54461 (8)	0.74750 (7)	0.57230 (14)	0.0263 (3)
C22	0.70568 (11)	0.62875 (10)	0.78474 (19)	0.0190 (4)
O22	0.72926 (8)	0.56534 (7)	0.84908 (15)	0.0251 (3)
C23	0.75191 (11)	0.71100 (10)	0.77728 (19)	0.0176 (3)
C24	0.83635 (11)	0.73462 (10)	0.83965 (19)	0.0212 (4)
C25	0.86181 (12)	0.81752 (10)	0.8206 (2)	0.0234 (4)
C26	0.80422 (12)	0.87378 (10)	0.7429 (2)	0.0237 (4)
C27	0.71934 (12)	0.84895 (10)	0.6794 (2)	0.0216 (4)
C28	0.69480 (11)	0.76677 (10)	0.69752 (18)	0.0183 (3)
C31	0.97302 (11)	0.53536 (10)	0.3443 (2)	0.0204 (4)
C32	0.92293 (11)	0.55176 (9)	0.5017 (2)	0.0216 (4)
C33	0.94951 (11)	0.51713 (10)	0.6542 (2)	0.0205 (3)
C34	0.94193 (13)	0.57073 (10)	0.1796 (2)	0.0263 (4)
H14	0.1036	0.6200	0.5629	0.026*
H15	0.0284	0.7484	0.5668	0.029*
H16	0.0985	0.8636	0.6867	0.027*
H17	0.2485	0.8535	0.8153	0.023*
H24	0.8788	0.6963	0.8961	0.025*
H25	0.9227	0.8346	0.8648	0.028*
H26	0.8233	0.9297	0.7333	0.028*
H27	0.6765	0.8869	0.6228	0.026*
H32	0.8704	0.5880	0.4939	0.026*
H33	0.9176	0.5277	0.7547	0.025*
H34A	0.9924	0.5664	0.1014	0.040*
H34B	0.9259	0.6290	0.1949	0.040*
H34C	0.8864	0.5408	0.1307	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S11	0.0149 (2)	0.0213 (3)	0.0325 (3)	0.00118 (15)	−0.00616 (18)	0.00755 (16)
N11	0.0129 (7)	0.0196 (7)	0.0251 (7)	0.0007 (5)	−0.0076 (5)	0.0022 (5)
C11	0.0161 (8)	0.0192 (8)	0.0179 (7)	−0.0015 (6)	−0.0028 (6)	0.0012 (6)
O11	0.0206 (6)	0.0242 (6)	0.0284 (6)	−0.0039 (5)	−0.0120 (5)	0.0000 (5)
C12	0.0140 (8)	0.0197 (8)	0.0220 (7)	−0.0031 (6)	−0.0033 (6)	0.0036 (7)
O12	0.0244 (7)	0.0195 (6)	0.0424 (7)	−0.0023 (5)	−0.0120 (5)	−0.0011 (5)
C13	0.0137 (8)	0.0215 (8)	0.0194 (7)	−0.0032 (6)	−0.0023 (6)	0.0028 (6)
C14	0.0165 (8)	0.0275 (8)	0.0209 (8)	−0.0045 (7)	−0.0053 (6)	0.0020 (7)
C15	0.0150 (9)	0.0340 (10)	0.0230 (8)	0.0010 (7)	−0.0056 (6)	0.0041 (7)
C16	0.0193 (9)	0.0269 (9)	0.0209 (8)	0.0064 (7)	−0.0015 (6)	0.0036 (7)
C17	0.0185 (8)	0.0203 (8)	0.0193 (7)	−0.0007 (6)	−0.0018 (6)	−0.0003 (6)
C18	0.0130 (8)	0.0207 (8)	0.0161 (7)	−0.0018 (6)	−0.0027 (6)	0.0023 (6)
S21	0.0156 (2)	0.0188 (2)	0.0335 (3)	0.00016 (15)	−0.00514 (18)	−0.00611 (16)
N21	0.0140 (7)	0.0177 (7)	0.0287 (7)	−0.0004 (5)	−0.0077 (5)	−0.0021 (6)
C21	0.0182 (9)	0.0200 (8)	0.0192 (7)	0.0029 (6)	−0.0002 (6)	−0.0014 (6)
O21	0.0203 (7)	0.0282 (6)	0.0287 (6)	0.0059 (5)	−0.0080 (5)	0.0003 (5)
C22	0.0144 (8)	0.0191 (8)	0.0232 (8)	0.0011 (6)	−0.0017 (6)	−0.0036 (6)
O22	0.0207 (7)	0.0185 (6)	0.0344 (7)	0.0017 (4)	−0.0084 (5)	0.0002 (5)
C23	0.0164 (8)	0.0181 (8)	0.0182 (7)	0.0008 (6)	0.0003 (6)	−0.0023 (6)
C24	0.0188 (9)	0.0230 (8)	0.0212 (8)	0.0012 (6)	−0.0024 (6)	−0.0023 (7)
C25	0.0224 (9)	0.0245 (9)	0.0229 (8)	−0.0037 (7)	−0.0003 (7)	−0.0046 (7)
C26	0.0275 (10)	0.0177 (8)	0.0258 (8)	−0.0038 (7)	0.0015 (7)	−0.0020 (7)
C27	0.0240 (9)	0.0190 (8)	0.0217 (8)	0.0029 (6)	0.0001 (6)	0.0002 (6)
C28	0.0177 (8)	0.0198 (8)	0.0172 (7)	0.0012 (6)	−0.0003 (6)	−0.0023 (6)
C31	0.0185 (8)	0.0144 (7)	0.0273 (8)	−0.0033 (6)	−0.0052 (6)	−0.0004 (6)
C32	0.0158 (8)	0.0165 (8)	0.0316 (8)	0.0015 (6)	−0.0043 (7)	−0.0011 (7)
C33	0.0182 (8)	0.0187 (8)	0.0243 (8)	−0.0018 (6)	0.0007 (6)	−0.0036 (6)
C34	0.0258 (10)	0.0252 (9)	0.0270 (8)	0.0023 (7)	−0.0044 (7)	0.0010 (7)

Geometric parameters (Å, º) top

S11—N11	1.628 (2)	C22—O22	1.180 (2)
S11—S21	2.1960 (6)	C22—C23	1.489 (2)
N11—C12	1.351 (2)	C23—C24	1.320 (2)
N11—C11	1.423 (2)	C23—C28	1.337 (2)
C11—O11	1.145 (2)	C24—C25	1.401 (2)
C11—C18	1.410 (2)	C24—H24	0.9500
C12—O12	1.193 (2)	C25—C26	1.339 (2)
C12—C13	1.475 (2)	C25—H25	0.9500
C13—C14	1.307 (2)	C26—C27	1.334 (2)
C13—C18	1.356 (2)	C26—H26	0.9500
C14—C15	1.399 (2)	C27—C28	1.385 (2)
C14—H14	0.9500	C27—H27	0.9500
C15—C16	1.352 (2)	C31—C33ⁱ	1.393 (2)
C15—H15	0.9500	C31—C34	1.442 (2)
C16—C17	1.315 (2)	C31—C32	1.489 (2)
C16—H16	0.9500	C32—C33	1.341 (2)
C17—C18	1.386 (2)	C32—H32	0.9500
C17—H17	0.9500	C33—C31ⁱ	1.393 (2)
S21—N21	1.656 (2)	C33—H33	0.9500
N21—C22	1.336 (2)	C34—H34A	0.9800
N21—C21	1.421 (2)	C34—H34B	0.9800
C21—O21	1.133 (2)	C34—H34C	0.9800
C21—C28	1.427 (2)

N11—S11—S21	108.21 (5)	O22—C22—C23	133.0 (2)
C12—N11—C11	111.8 (2)	N21—C22—C23	104.3 (2)
C12—N11—S11	120.6 (2)	C24—C23—C28	118.8 (2)
C11—N11—S11	127.4 (2)	C24—C23—C22	129.7 (2)
O11—C11—C18	126.8 (2)	C28—C23—C22	111.5 (2)
O11—C11—N11	125.5 (2)	C23—C24—C25	118.4 (2)
C18—C11—N11	107.7 (2)	C23—C24—H24	120.8
O12—C12—N11	123.5 (2)	C25—C24—H24	120.8
O12—C12—C13	134.1 (2)	C26—C25—C24	123.0 (2)
N11—C12—C13	102.4 (2)	C26—C25—H25	118.5
C14—C13—C18	118.5 (2)	C24—C25—H25	118.5
C14—C13—C12	128.9 (2)	C27—C26—C25	118.1 (2)
C18—C13—C12	112.6 (2)	C27—C26—H26	121.0
C13—C14—C15	117.0 (2)	C25—C26—H26	121.0
C13—C14—H14	121.5	C26—C27—C28	118.7 (2)
C15—C14—H14	121.5	C26—C27—H27	120.6
C16—C15—C14	124.3 (2)	C28—C27—H27	120.6
C16—C15—H15	117.9	C23—C28—C27	123.1 (2)
C14—C15—H15	117.9	C23—C28—C21	105.5 (2)
C17—C16—C15	118.6 (2)	C27—C28—C21	131.5 (2)
C17—C16—H16	120.7	C33ⁱ—C31—C34	116.1 (2)
C15—C16—H16	120.7	C33ⁱ—C31—C32	122.2 (2)
C16—C17—C18	116.9 (2)	C34—C31—C32	121.8 (2)
C16—C17—H17	121.5	C33—C32—C31	122.2 (2)
C18—C17—H17	121.5	C33—C32—H32	118.9
C13—C18—C17	124.7 (2)	C31—C32—H32	118.9
C13—C18—C11	105.4 (2)	C32—C33—C31ⁱ	115.6 (2)
C17—C18—C11	129.8 (2)	C32—C33—H33	122.2
N21—S21—S11	107.81 (5)	C31ⁱ—C33—H33	122.2
C22—N21—C21	110.3 (2)	C31—C34—H34A	109.5
C22—N21—S21	122.2 (2)	C31—C34—H34B	109.5
C21—N21—S21	127.4 (2)	H34A—C34—H34B	109.5
O21—C21—N21	123.5 (2)	C31—C34—H34C	109.5
O21—C21—C28	128.1 (2)	H34A—C34—H34C	109.5
N21—C21—C28	108.4 (2)	H34B—C34—H34C	109.5
O22—C22—N21	122.7 (2)

S21—S11—N11—C12	92.1 (2)	S11—S21—N21—C21	−87.3 (2)
S21—S11—N11—C11	−92.4 (2)	C22—N21—C21—O21	−177.6 (2)
C12—N11—C11—O11	−179.3 (2)	S21—N21—C21—O21	5.2 (2)
S11—N11—C11—O11	4.9 (2)	C22—N21—C21—C28	2.2 (2)
C12—N11—C11—C18	0.8 (2)	S21—N21—C21—C28	−175.1 (2)
S11—N11—C11—C18	−175.1 (2)	C21—N21—C22—O22	176.2 (2)
C11—N11—C12—O12	177.7 (2)	S21—N21—C22—O22	−6.3 (2)
S11—N11—C12—O12	−6.1 (2)	C21—N21—C22—C23	−3.2 (2)
C11—N11—C12—C13	−1.7 (2)	S21—N21—C22—C23	174.1 (2)
S11—N11—C12—C13	174.5 (2)	O22—C22—C23—C24	2.3 (3)
O12—C12—C13—C14	1.0 (3)	N21—C22—C23—C24	−178.3 (2)
N11—C12—C13—C14	−179.6 (2)	O22—C22—C23—C28	−176.0 (2)
O12—C12—C13—C18	−177.2 (2)	N21—C22—C23—C28	3.5 (2)
N11—C12—C13—C18	2.2 (2)	C28—C23—C24—C25	0.6 (2)
C18—C13—C14—C15	−0.1 (2)	C22—C23—C24—C25	−177.5 (2)
C12—C13—C14—C15	−178.2 (2)	C23—C24—C25—C26	0.4 (2)
C13—C14—C15—C16	0.9 (2)	C24—C25—C26—C27	−0.8 (2)
C14—C15—C16—C17	−0.8 (3)	C25—C26—C27—C28	0.3 (2)
C15—C16—C17—C18	−0.1 (2)	C24—C23—C28—C27	−1.1 (2)
C14—C13—C18—C17	−0.8 (2)	C22—C23—C28—C27	177.4 (2)
C12—C13—C18—C17	177.6 (2)	C24—C23—C28—C21	179.4 (2)
C14—C13—C18—C11	179.9 (2)	C22—C23—C28—C21	−2.1 (2)
C12—C13—C18—C11	−1.8 (2)	C26—C27—C28—C23	0.6 (2)
C16—C17—C18—C13	0.8 (2)	C26—C27—C28—C21	180.0 (2)
C16—C17—C18—C11	−179.9 (2)	O21—C21—C28—C23	179.9 (2)
O11—C11—C18—C13	−179.3 (2)	N21—C21—C28—C23	0.1 (2)
N11—C11—C18—C13	0.6 (2)	O21—C21—C28—C27	0.4 (3)
O11—C11—C18—C17	1.4 (3)	N21—C21—C28—C27	−179.4 (2)
N11—C11—C18—C17	−178.7 (2)	C33ⁱ—C31—C32—C33	0.1 (3)
N11—S11—S21—N21	88.19 (7)	C34—C31—C32—C33	177.9 (2)
S11—S21—N21—C22	95.7 (2)	C31—C32—C33—C31ⁱ	−0.1 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O11ⁱⁱ	0.95	2.09	3.023 (2)	168
C26—H26···O22ⁱⁱⁱ	0.95	2.39	3.209 (2)	144

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

(12) N,N'-Dithiodiphthalimide hemi(toluene) solvate top

Crystal data top

C₁₆H₈N₂O₄S₂·0.5(C₇H₈)	F(000) = 828
M_r = 402.45	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.3126 (4) Å	Cell parameters from 3467 reflections
b = 16.1270 (4) Å	θ = 2.9–28.0°
c = 7.6990 (2) Å	µ = 0.33 mm⁻¹
β = 94.3216 (13)°	T = 120 K
V = 1772.03 (8) Å³	Block, colourless
Z = 4	0.25 × 0.10 × 0.10 mm

Data collection top

Kappa-CCD diffractometer	3467 independent reflections
Radiation source: fine-focus sealed X-ray tube	2827 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
φ scans and ω scans with κ offsets	θ_max = 26.1°, θ_min = 2.9°
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997)	h = −17→17
T_min = 0.922, T_max = 0.968	k = −19→19
9295 measured reflections	l = −9→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0598P)² + 0.3414P] where P = (F_o² + 2F_c²)/3
3467 reflections	(Δ/σ)_max = 0.013
254 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S11	0.45099 (3)	0.56413 (3)	0.84701 (6)	0.02201 (15)
N11	0.36287 (9)	0.62401 (9)	0.78652 (18)	0.0183 (3)
C11	0.35383 (11)	0.71011 (10)	0.8215 (2)	0.0177 (4)
O11	0.41027 (8)	0.75112 (7)	0.89157 (16)	0.0254 (3)
C12	0.28390 (11)	0.59261 (11)	0.7018 (2)	0.0181 (4)
O12	0.27627 (9)	0.52211 (7)	0.65630 (17)	0.0280 (3)
C13	0.22172 (11)	0.66510 (10)	0.6876 (2)	0.0171 (4)
C14	0.13540 (12)	0.67066 (11)	0.6173 (2)	0.0218 (4)
C15	0.09288 (12)	0.74823 (11)	0.6175 (2)	0.0243 (4)
C16	0.13516 (12)	0.81782 (11)	0.6836 (2)	0.0222 (4)
C17	0.22203 (12)	0.81232 (11)	0.7543 (2)	0.0200 (4)
C18	0.26316 (11)	0.73477 (10)	0.7558 (2)	0.0168 (4)
S21	0.54978 (3)	0.56663 (3)	0.64296 (6)	0.02252 (15)
N21	0.62373 (10)	0.64399 (9)	0.68640 (19)	0.0200 (3)
C21	0.61335 (12)	0.72849 (11)	0.6353 (2)	0.0195 (4)
O21	0.54773 (9)	0.75469 (8)	0.56332 (16)	0.0270 (3)
C22	0.70713 (11)	0.63222 (11)	0.7743 (2)	0.0180 (4)
O22	0.72952 (9)	0.56787 (7)	0.83850 (17)	0.0251 (3)
C23	0.75400 (11)	0.71398 (10)	0.7688 (2)	0.0170 (4)
C24	0.83880 (12)	0.73624 (11)	0.8317 (2)	0.0197 (4)
C25	0.86557 (13)	0.81908 (11)	0.8146 (2)	0.0228 (4)
C26	0.80857 (13)	0.87663 (11)	0.7380 (2)	0.0235 (4)
C27	0.72397 (13)	0.85359 (11)	0.6737 (2)	0.0212 (4)
C28	0.69815 (11)	0.77117 (10)	0.6900 (2)	0.0177 (4)
C31	0.97524 (13)	0.53541 (13)	0.3440 (3)	0.0312 (5)
C32	0.92401 (13)	0.55233 (12)	0.5000 (3)	0.0319 (5)
C33	0.94843 (13)	0.51694 (12)	0.6542 (3)	0.0289 (4)
C34	0.9462 (3)	0.5640 (3)	0.1649 (5)	0.0336 (10)	0.50
H14	0.1033	0.6236	0.5683	0.026*
H15	0.0302	0.7527	0.5682	0.029*
H16	0.1031	0.8694	0.6792	0.027*
H17	0.2546	0.8594	0.8019	0.024*
H24	0.8805	0.6969	0.8871	0.024*
H25	0.9266	0.8353	0.8590	0.027*
H26	0.8284	0.9326	0.7300	0.028*
H27	0.6820	0.8926	0.6178	0.025*
H31	0.9546	0.5618	0.2376	0.037*	0.50
H32	0.8723	0.5894	0.4905	0.038*
H33	0.9156	0.5271	0.7548	0.035*
H34A	0.9948	0.5496	0.0870	0.050*	0.50
H34B	0.9374	0.6243	0.1652	0.050*	0.50
H34C	0.8872	0.5370	0.1242	0.050*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S11	0.0147 (3)	0.0193 (3)	0.0309 (3)	0.00157 (17)	−0.00561 (19)	0.00599 (17)
N11	0.0123 (7)	0.0168 (7)	0.0245 (8)	−0.0004 (6)	−0.0073 (6)	0.0023 (6)
C11	0.0161 (8)	0.0180 (9)	0.0184 (9)	−0.0010 (7)	−0.0027 (7)	0.0007 (7)
O11	0.0210 (7)	0.0224 (7)	0.0304 (7)	−0.0030 (6)	−0.0132 (5)	−0.0021 (5)
C12	0.0138 (8)	0.0200 (9)	0.0199 (9)	−0.0039 (7)	−0.0025 (7)	0.0028 (7)
O12	0.0258 (7)	0.0180 (7)	0.0383 (8)	−0.0029 (6)	−0.0109 (6)	−0.0017 (6)
C13	0.0138 (8)	0.0207 (9)	0.0165 (8)	−0.0022 (7)	−0.0013 (7)	0.0016 (7)
C14	0.0157 (8)	0.0294 (10)	0.0195 (9)	−0.0052 (8)	−0.0043 (7)	0.0014 (7)
C15	0.0155 (9)	0.0360 (11)	0.0202 (9)	0.0038 (8)	−0.0059 (7)	0.0037 (8)
C16	0.0193 (9)	0.0262 (10)	0.0208 (9)	0.0098 (8)	−0.0015 (7)	0.0026 (7)
C17	0.0199 (9)	0.0208 (9)	0.0187 (9)	0.0023 (7)	−0.0031 (7)	−0.0004 (7)
C18	0.0139 (8)	0.0209 (9)	0.0151 (8)	−0.0014 (7)	−0.0026 (7)	0.0015 (7)
S21	0.0150 (3)	0.0193 (3)	0.0323 (3)	0.00033 (17)	−0.0041 (2)	−0.00819 (17)
N21	0.0148 (7)	0.0168 (7)	0.0271 (8)	0.0002 (6)	−0.0059 (6)	−0.0030 (6)
C21	0.0180 (9)	0.0214 (9)	0.0192 (9)	0.0032 (8)	0.0014 (7)	−0.0020 (7)
O21	0.0221 (7)	0.0306 (7)	0.0268 (7)	0.0070 (6)	−0.0073 (5)	−0.0003 (6)
C22	0.0128 (8)	0.0192 (9)	0.0216 (9)	0.0017 (7)	−0.0018 (7)	−0.0046 (7)
O22	0.0218 (7)	0.0172 (7)	0.0348 (8)	0.0019 (5)	−0.0083 (6)	0.0002 (5)
C23	0.0169 (8)	0.0166 (8)	0.0176 (9)	0.0016 (7)	0.0004 (7)	−0.0035 (7)
C24	0.0181 (9)	0.0200 (9)	0.0205 (9)	0.0004 (7)	−0.0018 (7)	−0.0022 (7)
C25	0.0205 (9)	0.0244 (9)	0.0233 (10)	−0.0056 (8)	0.0007 (7)	−0.0056 (7)
C26	0.0286 (10)	0.0169 (9)	0.0251 (10)	−0.0035 (8)	0.0034 (8)	−0.0015 (7)
C27	0.0251 (9)	0.0179 (9)	0.0209 (9)	0.0031 (8)	0.0031 (7)	0.0002 (7)
C28	0.0169 (8)	0.0191 (9)	0.0169 (9)	0.0024 (7)	0.0003 (7)	−0.0019 (7)
C31	0.0235 (10)	0.0315 (11)	0.0369 (12)	−0.0051 (9)	−0.0085 (8)	0.0135 (9)
C32	0.0198 (10)	0.0278 (10)	0.0464 (13)	−0.0014 (8)	−0.0081 (9)	0.0092 (9)
C33	0.0225 (10)	0.0312 (10)	0.0328 (11)	−0.0063 (9)	0.0000 (8)	0.0057 (9)
C34	0.033 (2)	0.037 (2)	0.030 (2)	−0.0008 (18)	−0.0039 (18)	0.0098 (17)

Geometric parameters (Å, º) top

S11—N11	1.628 (2)	C22—O22	1.183 (2)
S11—S21	2.1918 (7)	C22—C23	1.481 (2)
N11—C12	1.360 (2)	C23—C24	1.322 (2)
N11—C11	1.422 (2)	C23—C28	1.336 (2)
C11—O11	1.147 (2)	C24—C25	1.399 (3)
C11—C18	1.414 (2)	C24—H24	0.9500
C12—O12	1.192 (2)	C25—C26	1.342 (3)
C12—C13	1.468 (2)	C25—H25	0.9500
C13—C14	1.314 (2)	C26—C27	1.326 (3)
C13—C18	1.358 (2)	C26—H26	0.9500
C14—C15	1.391 (3)	C27—C28	1.388 (2)
C14—H14	0.9500	C27—H27	0.9500
C15—C16	1.356 (3)	C31—C33ⁱ	1.380 (3)
C15—H15	0.9500	C31—C34	1.483 (4)
C16—C17	1.322 (2)	C31—C32	1.479 (3)
C16—H16	0.9500	C31—H31	0.9500
C17—C18	1.382 (2)	C32—C33	1.340 (3)
C17—H17	0.9500	C32—H32	0.9500
S21—N21	1.654 (2)	C33—C31ⁱ	1.380 (3)
N21—C22	1.341 (2)	C33—H33	0.9500
N21—C21	1.423 (2)	C34—H34A	0.9800
C21—O21	1.136 (2)	C34—H34B	0.9800
C21—C28	1.431 (2)	C34—H34C	0.9800

N11—S11—S21	108.16 (6)	N21—C22—C23	104.3 (2)
C12—N11—C11	111.7 (2)	C24—C23—C28	118.7 (2)
C12—N11—S11	121.0 (2)	C24—C23—C22	129.5 (2)
C11—N11—S11	127.2 (2)	C28—C23—C22	111.8 (2)
O11—C11—C18	127.0 (2)	C23—C24—C25	118.4 (2)
O11—C11—N11	125.5 (2)	C23—C24—H24	120.8
C18—C11—N11	107.5 (2)	C25—C24—H24	120.8
O12—C12—N11	123.4 (2)	C26—C25—C24	122.7 (2)
O12—C12—C13	134.1 (2)	C26—C25—H25	118.7
N11—C12—C13	102.5 (2)	C24—C25—H25	118.7
C14—C13—C18	118.2 (2)	C27—C26—C25	118.5 (2)
C14—C13—C12	129.1 (2)	C27—C26—H26	120.7
C18—C13—C12	112.7 (2)	C25—C26—H26	120.7
C13—C14—C15	117.3 (2)	C26—C27—C28	118.5 (2)
C13—C14—H14	121.3	C26—C27—H27	120.8
C15—C14—H14	121.3	C28—C27—H27	120.8
C16—C15—C14	124.2 (2)	C23—C28—C27	123.2 (2)
C16—C15—H15	117.9	C23—C28—C21	105.5 (2)
C14—C15—H15	117.9	C27—C28—C21	131.3 (2)
C17—C16—C15	118.6 (2)	C33ⁱ—C31—C34	111.4 (2)
C17—C16—H16	120.7	C33ⁱ—C31—C32	123.1 (2)
C15—C16—H16	120.7	C34—C31—C32	125.2 (2)
C16—C17—C18	116.8 (2)	C33ⁱ—C31—H31	118.5
C16—C17—H17	121.6	C32—C31—H31	118.5
C18—C17—H17	121.6	C33—C32—C31	121.9 (2)
C13—C18—C17	124.9 (2)	C33—C32—H32	119.0
C13—C18—C11	105.6 (2)	C31—C32—H32	119.0
C17—C18—C11	129.5 (2)	C32—C33—C31ⁱ	115.0 (2)
N21—S21—S11	107.85 (6)	C32—C33—H33	122.5
C22—N21—C21	110.2 (2)	C31ⁱ—C33—H33	122.5
C22—N21—S21	121.8 (2)	C31—C34—H34A	109.5
C21—N21—S21	127.9 (2)	C31—C34—H34B	109.5
O21—C21—N21	123.8 (2)	H34A—C34—H34B	109.5
O21—C21—C28	128.1 (2)	C31—C34—H34C	109.5
N21—C21—C28	108.1 (2)	H34A—C34—H34C	109.5
O22—C22—N21	122.5 (2)	H34B—C34—H34C	109.5
O22—C22—C23	133.1 (2)

S21—S11—N11—C12	94.3 (2)	S11—S21—N21—C21	−87.5 (2)
S21—S11—N11—C11	−90.2 (2)	C22—N21—C21—O21	−177.8 (2)
C12—N11—C11—O11	179.9 (2)	S21—N21—C21—O21	4.6 (3)
S11—N11—C11—O11	3.9 (3)	C22—N21—C21—C28	2.4 (2)
C12—N11—C11—C18	0.4 (2)	S21—N21—C21—C28	−175.2 (2)
S11—N11—C11—C18	−175.5 (2)	C21—N21—C22—O22	175.7 (2)
C11—N11—C12—O12	178.5 (2)	S21—N21—C22—O22	−6.6 (2)
S11—N11—C12—O12	−5.3 (2)	C21—N21—C22—C23	−3.3 (2)
C11—N11—C12—C13	−1.2 (2)	S21—N21—C22—C23	174.5 (2)
S11—N11—C12—C13	175.1 (2)	O22—C22—C23—C24	3.2 (3)
O12—C12—C13—C14	0.7 (3)	N21—C22—C23—C24	−178.0 (2)
N11—C12—C13—C14	−179.7 (2)	O22—C22—C23—C28	−175.5 (2)
O12—C12—C13—C18	−178.0 (2)	N21—C22—C23—C28	3.3 (2)
N11—C12—C13—C18	1.6 (2)	C28—C23—C24—C25	0.9 (3)
C18—C13—C14—C15	0.3 (3)	C22—C23—C24—C25	−177.8 (2)
C12—C13—C14—C15	−178.4 (2)	C23—C24—C25—C26	0.3 (3)
C13—C14—C15—C16	0.7 (3)	C24—C25—C26—C27	−1.0 (3)
C14—C15—C16—C17	−0.7 (3)	C25—C26—C27—C28	0.5 (3)
C15—C16—C17—C18	−0.3 (3)	C24—C23—C28—C27	−1.4 (3)
C14—C13—C18—C17	−1.3 (3)	C22—C23—C28—C27	177.5 (2)
C12—C13—C18—C17	177.6 (2)	C24—C23—C28—C21	179.3 (2)
C14—C13—C18—C11	179.8 (2)	C22—C23—C28—C21	−1.9 (2)
C12—C13—C18—C11	−1.4 (2)	C26—C27—C28—C23	0.7 (3)
C16—C17—C18—C13	1.3 (3)	C26—C27—C28—C21	179.8 (2)
C16—C17—C18—C11	180.0 (2)	O21—C21—C28—C23	180.0 (2)
O11—C11—C18—C13	−178.9 (2)	N21—C21—C28—C23	−0.2 (2)
N11—C11—C18—C13	0.6 (2)	O21—C21—C28—C27	0.7 (3)
O11—C11—C18—C17	2.3 (3)	N21—C21—C28—C27	−179.5 (2)
N11—C11—C18—C17	−178.3 (2)	C33ⁱ—C31—C32—C33	−0.5 (3)
N11—S11—S21—N21	89.05 (8)	C34—C31—C32—C33	172.4 (3)
S11—S21—N21—C22	95.1 (2)	C31—C32—C33—C31ⁱ	0.5 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O11ⁱⁱ	0.95	2.11	3.029 (2)	163
C26—H26···O22ⁱⁱⁱ	0.95	2.38	3.179 (2)	142

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

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