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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101020006/na0132sup1.cif
Contains datablocks global, 4, 5, 6, 7, 8, 9, 10, 11, 12

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01324sup2.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01325sup3.hkl
Contains datablock 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01326sup4.hkl
Contains datablock 6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01327sup5.hkl
Contains datablock 7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01328sup6.hkl
Contains datablock 8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na01329sup7.hkl
Contains datablock 9

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na013210sup8.hkl
Contains datablock VII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101020006/na013211sup9.hkl
Contains datablock VIII

hkl

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
C16H8N2O4S2Dx = 1.573 Mg m3
Mr = 356.36Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 2913 reflections
a = 7.1298 (2) Åθ = 2.9–27.5°
b = 30.7247 (13) ŵ = 0.38 mm1
c = 6.8691 (2) ÅT = 120 K
V = 1504.75 (9) Å3Needle, colourless
Z = 40.35 × 0.08 × 0.07 mm
F(000) = 728
Data collection top
Kappa-CCD
diffractometer
2913 independent reflections
Radiation source: fine-focus sealed X-ray tube2154 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 59
Tmin = 0.879, Tmax = 0.974k = 3939
6890 measured reflectionsl = 76
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0238P)2 + 0.4375P]
where P = (Fo2 + 2Fc2)/3
2913 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = 0.31 e Å3
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
xyzUiso*/Ueq
S10.08746 (14)0.15565 (3)0.03776 (18)0.0382 (3)
N110.1375 (4)0.10631 (10)0.1313 (5)0.0340 (9)
C110.0913 (6)0.09242 (12)0.3217 (7)0.0365 (10)
O110.0107 (4)0.11402 (8)0.4399 (4)0.0419 (8)
C120.2302 (6)0.07319 (13)0.0236 (8)0.0362 (10)
O120.2821 (4)0.07721 (8)0.1422 (5)0.0427 (8)
C130.2414 (5)0.03558 (12)0.1549 (6)0.0347 (10)
C140.3158 (6)0.00545 (13)0.1219 (8)0.0454 (12)
C150.3056 (6)0.03503 (14)0.2745 (9)0.0542 (15)
C160.2281 (6)0.02398 (15)0.4529 (8)0.0506 (15)
C170.1558 (6)0.01772 (14)0.4860 (6)0.0428 (12)
C180.1635 (5)0.04685 (12)0.3319 (7)0.0348 (11)
S20.17069 (15)0.15018 (3)0.08615 (17)0.0346 (3)
N210.3147 (4)0.16844 (9)0.0906 (5)0.0298 (8)
C210.3941 (6)0.14221 (13)0.2389 (6)0.0303 (10)
O210.3961 (4)0.10280 (8)0.2396 (4)0.0408 (8)
C220.3296 (5)0.21368 (12)0.1378 (6)0.0262 (9)
O220.2645 (3)0.24237 (8)0.0410 (4)0.0322 (6)
C230.4286 (5)0.21544 (12)0.3267 (6)0.0255 (9)
C240.4720 (5)0.25079 (11)0.4412 (6)0.0265 (9)
C250.5534 (5)0.24308 (14)0.6218 (6)0.0336 (10)
C260.5911 (6)0.20127 (14)0.6794 (6)0.0335 (10)
C270.5516 (5)0.16499 (13)0.5672 (7)0.0345 (10)
C280.4672 (5)0.17306 (11)0.3908 (6)0.0257 (9)
H140.37110.01300.00070.055*
H150.35300.06360.25610.065*
H160.22410.04500.55420.061*
H170.10380.02570.60820.051*
H240.44710.27960.39820.032*
H250.58300.26680.70520.040*
H260.64750.19700.80320.040*
H270.58090.13630.60940.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0338 (6)0.0238 (5)0.0569 (7)0.0012 (5)0.0121 (6)0.0059 (5)
N110.0283 (19)0.0248 (17)0.049 (2)0.0033 (15)0.0117 (17)0.0070 (15)
C110.031 (2)0.027 (2)0.052 (3)0.010 (2)0.001 (2)0.000 (2)
O110.050 (2)0.0380 (16)0.038 (2)0.0000 (14)0.0070 (16)0.0050 (14)
C120.026 (2)0.038 (2)0.044 (3)0.0016 (18)0.002 (2)0.000 (2)
O120.0399 (19)0.0403 (17)0.048 (2)0.0100 (14)0.0122 (15)0.0013 (15)
C130.023 (2)0.027 (2)0.055 (3)0.0004 (18)0.001 (2)0.004 (2)
C140.026 (2)0.030 (2)0.080 (4)0.000 (2)0.005 (2)0.004 (2)
C150.025 (3)0.028 (2)0.110 (5)0.002 (2)0.005 (3)0.015 (3)
C160.031 (3)0.040 (3)0.081 (4)0.005 (2)0.006 (3)0.026 (3)
C170.034 (2)0.048 (3)0.047 (3)0.006 (2)0.002 (2)0.009 (2)
C180.020 (2)0.031 (2)0.054 (3)0.0002 (19)0.006 (2)0.003 (2)
S20.0422 (6)0.0288 (5)0.0327 (6)0.0080 (5)0.0086 (5)0.0006 (5)
N210.0308 (19)0.0238 (17)0.035 (2)0.0056 (15)0.0059 (15)0.0005 (15)
C210.027 (2)0.032 (2)0.032 (3)0.0001 (19)0.0017 (18)0.0032 (19)
O210.0424 (19)0.0242 (16)0.056 (2)0.0029 (14)0.0101 (15)0.0002 (14)
C220.023 (2)0.025 (2)0.031 (2)0.0035 (17)0.0006 (18)0.0013 (17)
O220.0401 (17)0.0248 (14)0.0318 (15)0.0007 (12)0.0086 (14)0.0069 (14)
C230.016 (2)0.032 (2)0.029 (2)0.0049 (17)0.0050 (17)0.0016 (19)
C240.025 (2)0.029 (2)0.026 (2)0.0011 (17)0.0006 (18)0.0003 (17)
C250.028 (2)0.042 (3)0.031 (2)0.000 (2)0.0025 (19)0.0103 (19)
C260.024 (2)0.053 (3)0.024 (3)0.001 (2)0.0058 (18)0.003 (2)
C270.027 (2)0.033 (2)0.043 (3)0.0024 (18)0.002 (2)0.007 (2)
C280.026 (2)0.028 (2)0.023 (2)0.0002 (16)0.0006 (18)0.0005 (17)
Geometric parameters (Å, º) top
S1—N111.685 (3)S2—N211.687 (3)
S1—S22.035 (2)N21—C211.417 (5)
N11—C111.415 (5)N21—C221.431 (4)
N11—C121.422 (5)C21—O211.211 (4)
C11—O111.195 (5)C21—C281.503 (6)
C11—C181.493 (5)C22—O221.198 (4)
C12—O121.204 (5)C22—C231.478 (5)
C12—C131.468 (6)C23—C241.376 (5)
C13—C181.381 (6)C23—C281.402 (5)
C13—C141.386 (5)C24—C251.389 (5)
C14—C151.389 (7)C24—H240.9500
C14—H140.9500C25—C261.371 (5)
C15—C161.386 (6)C25—H250.9500
C15—H150.9500C26—C271.384 (5)
C16—C171.400 (6)C26—H260.9500
C16—H160.9500C27—C281.376 (5)
C17—C181.387 (5)C27—H270.9500
C17—H170.9500
N11—S1—S2106.1 (2)N21—S2—S1102.8 (2)
C11—N11—C12111.9 (3)C21—N21—C22111.1 (3)
C11—N11—S1125.1 (3)C21—N21—S2124.9 (3)
C12—N11—S1123.0 (3)C22—N21—S2122.1 (3)
O11—C11—N11124.9 (4)O21—C21—N21125.2 (4)
O11—C11—C18130.9 (4)O21—C21—C28128.6 (4)
N11—C11—C18104.2 (4)N21—C21—C28106.2 (3)
O12—C12—N11124.2 (4)O22—C22—N21124.1 (3)
O12—C12—C13130.2 (4)O22—C22—C23130.2 (3)
N11—C12—C13105.6 (4)N21—C22—C23105.7 (3)
C18—C13—C14121.7 (4)C24—C23—C28120.6 (3)
C18—C13—C12108.8 (4)C24—C23—C22129.6 (3)
C14—C13—C12129.5 (4)C28—C23—C22109.6 (3)
C13—C14—C15116.8 (5)C23—C24—C25118.0 (3)
C13—C14—H14121.6C23—C24—H24121.0
C15—C14—H14121.6C25—C24—H24121.0
C16—C15—C14121.8 (4)C26—C25—C24119.9 (4)
C16—C15—H15119.1C26—C25—H25120.0
C14—C15—H15119.1C24—C25—H25120.0
C15—C16—C17121.0 (4)C25—C26—C27123.7 (4)
C15—C16—H16119.5C25—C26—H26118.2
C17—C16—H16119.5C27—C26—H26118.2
C18—C17—C16116.9 (4)C28—C27—C26115.7 (4)
C18—C17—H17121.6C28—C27—H27122.1
C16—C17—H17121.6C26—C27—H27122.1
C13—C18—C17121.7 (4)C27—C28—C23122.0 (3)
C13—C18—C11109.4 (4)C27—C28—C21130.5 (3)
C17—C18—C11128.8 (4)C23—C28—C21107.4 (3)
S2—S1—N11—C1189.4 (3)S1—S2—N21—C2188.6 (3)
S2—S1—N11—C1289.5 (3)S1—S2—N21—C2274.1 (3)
C12—N11—C11—O11179.0 (4)C22—N21—C21—O21177.8 (4)
S1—N11—C11—O110.1 (6)S2—N21—C21—O2113.4 (6)
C12—N11—C11—C180.4 (4)C22—N21—C21—C280.8 (4)
S1—N11—C11—C18179.5 (3)S2—N21—C21—C28165.1 (3)
C11—N11—C12—O12179.5 (4)C21—N21—C22—O22176.0 (4)
S1—N11—C12—O120.4 (6)S2—N21—C22—O2211.1 (5)
C11—N11—C12—C130.7 (4)C21—N21—C22—C231.2 (4)
S1—N11—C12—C13178.4 (3)S2—N21—C22—C23166.1 (2)
O12—C12—C13—C18179.7 (4)O22—C22—C23—C240.0 (7)
N11—C12—C13—C181.6 (4)N21—C22—C23—C24176.9 (4)
O12—C12—C13—C140.2 (8)O22—C22—C23—C28175.7 (4)
N11—C12—C13—C14178.9 (4)N21—C22—C23—C281.2 (4)
C18—C13—C14—C151.0 (6)C28—C23—C24—C250.5 (5)
C12—C13—C14—C15179.5 (4)C22—C23—C24—C25174.8 (4)
C13—C14—C15—C161.2 (7)C23—C24—C25—C261.1 (6)
C14—C15—C16—C170.3 (7)C24—C25—C26—C270.4 (6)
C15—C16—C17—C180.8 (6)C25—C26—C27—C281.0 (6)
C14—C13—C18—C170.1 (6)C26—C27—C28—C231.7 (6)
C12—C13—C18—C17179.5 (4)C26—C27—C28—C21175.7 (4)
C14—C13—C18—C11178.5 (4)C24—C23—C28—C271.0 (6)
C12—C13—C18—C111.9 (4)C22—C23—C28—C27177.2 (3)
C16—C17—C18—C131.0 (6)C24—C23—C28—C21176.9 (3)
C16—C17—C18—C11177.4 (4)C22—C23—C28—C210.7 (4)
O11—C11—C18—C13177.9 (4)O21—C21—C28—C270.8 (7)
N11—C11—C18—C131.5 (4)N21—C21—C28—C27177.7 (4)
O11—C11—C18—C170.6 (7)O21—C21—C28—C23178.5 (4)
N11—C11—C18—C17179.9 (4)N21—C21—C28—C230.0 (4)
N11—S1—S2—N2195.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O21i0.952.513.343 (6)147
Symmetry code: (i) x, y, z+1/2.
(5) N,N'-Dithiodiphthalimide top
Crystal data top
C16H8N2O4S2F(000) = 1456
Mr = 356.36Dx = 1.543 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.5052 (2) ÅCell parameters from 6776 reflections
b = 7.8740 (1) Åθ = 3.0–27.5°
c = 29.2050 (5) ŵ = 0.37 mm1
β = 98.9640 (5)°T = 120 K
V = 3067.73 (8) Å3Plate, colourless
Z = 80.20 × 0.07 × 0.02 mm
Data collection top
Kappa-CCD
diffractometer
6776 independent reflections
Radiation source: fine-focus sealed X-ray tube5280 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1717
Tmin = 0.930, Tmax = 0.993k = 1010
26075 measured reflectionsl = 3737
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0713P)2]
where P = (Fo2 + 2Fc2)/3
6776 reflections(Δ/σ)max = 0.002
433 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.60 e Å3
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
xyzUiso*/Ueq
S110.24420 (4)0.57462 (6)0.071870 (16)0.01934 (13)
N110.14413 (11)0.62029 (19)0.03194 (5)0.0172 (3)
C110.14047 (14)0.5888 (2)0.01631 (6)0.0193 (4)
O110.20470 (10)0.51447 (17)0.03304 (5)0.0252 (3)
C120.06080 (14)0.7205 (2)0.04104 (7)0.0179 (4)
O120.04923 (10)0.77010 (17)0.07869 (5)0.0239 (3)
C130.00065 (14)0.7459 (2)0.00528 (7)0.0179 (4)
C140.08970 (14)0.8347 (2)0.01665 (7)0.0212 (4)
C150.13082 (15)0.8414 (2)0.06334 (7)0.0253 (5)
C160.08536 (16)0.7611 (3)0.09709 (7)0.0274 (5)
C170.00435 (15)0.6722 (2)0.08535 (7)0.0245 (5)
C180.04603 (14)0.6674 (2)0.03898 (6)0.0180 (4)
S210.32300 (4)0.79638 (6)0.078152 (16)0.01968 (13)
N210.38538 (12)0.79693 (19)0.03214 (6)0.0195 (4)
C210.34291 (14)0.8565 (2)0.01249 (6)0.0195 (4)
O210.25950 (10)0.91405 (18)0.02228 (5)0.0260 (3)
C220.48416 (15)0.7327 (2)0.03250 (7)0.0200 (4)
O220.53487 (10)0.66983 (19)0.06555 (5)0.0281 (3)
C230.50626 (14)0.7623 (2)0.01514 (7)0.0184 (4)
C240.59268 (15)0.7274 (2)0.03343 (7)0.0214 (4)
C250.59058 (16)0.7656 (2)0.08019 (7)0.0237 (4)
C260.50607 (15)0.8326 (2)0.10724 (7)0.0243 (4)
C270.41994 (15)0.8686 (3)0.08847 (7)0.0242 (4)
C280.42202 (14)0.8334 (2)0.04208 (7)0.0191 (4)
S310.10432 (4)0.31123 (7)0.194488 (19)0.02881 (15)
N310.10882 (12)0.4339 (2)0.24233 (6)0.0242 (4)
C310.11793 (14)0.3694 (2)0.28861 (7)0.0232 (4)
O310.11131 (12)0.22189 (17)0.29834 (6)0.0346 (4)
C320.12446 (15)0.6130 (3)0.24234 (7)0.0228 (4)
O320.12819 (12)0.69731 (19)0.20820 (5)0.0346 (4)
C330.13886 (14)0.6646 (2)0.29152 (7)0.0200 (4)
C340.15675 (15)0.8245 (3)0.31067 (8)0.0266 (5)
C350.17462 (16)0.8354 (3)0.35848 (8)0.0300 (5)
C360.17290 (17)0.6915 (3)0.38643 (8)0.0320 (5)
C370.15286 (16)0.5319 (3)0.36676 (7)0.0275 (5)
C380.13674 (15)0.5208 (2)0.31913 (7)0.0214 (4)
S410.25028 (4)0.29204 (6)0.186064 (17)0.02413 (14)
N410.29752 (12)0.1252 (2)0.21909 (5)0.0202 (4)
C410.33845 (14)0.1370 (2)0.26688 (7)0.0201 (4)
O410.33890 (11)0.26371 (18)0.29007 (5)0.0288 (3)
C420.31169 (14)0.0391 (2)0.20078 (6)0.0187 (4)
O420.28951 (10)0.07959 (18)0.16090 (4)0.0251 (3)
C430.36174 (14)0.1385 (2)0.24097 (7)0.0187 (4)
C440.38989 (15)0.3082 (2)0.24283 (7)0.0244 (5)
C450.43508 (15)0.3698 (3)0.28582 (7)0.0274 (5)
C460.45167 (16)0.2658 (3)0.32464 (7)0.0271 (5)
C470.42348 (15)0.0959 (3)0.32242 (7)0.0245 (4)
C480.37841 (14)0.0350 (2)0.27983 (6)0.0193 (4)
H140.12120.88850.00640.025*
H150.19140.90240.07240.030*
H160.11590.76700.12860.033*
H170.03560.61700.10830.029*
H240.65030.68000.01510.026*
H250.64880.74510.09390.028*
H260.50710.85420.13920.029*
H270.36210.91550.10680.029*
H340.15680.92260.29180.032*
H350.18840.94320.37270.036*
H360.18560.70290.41920.038*
H370.15040.43400.38550.033*
H440.37890.37880.21620.029*
H450.45500.48550.28860.033*
H460.48300.31170.35330.032*
H470.43470.02470.34900.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0193 (3)0.0183 (2)0.0195 (2)0.00238 (18)0.00014 (19)0.00025 (18)
N110.0147 (9)0.0176 (8)0.0189 (8)0.0031 (6)0.0015 (6)0.0018 (6)
C110.0217 (11)0.0142 (9)0.0220 (10)0.0026 (7)0.0032 (8)0.0039 (7)
O110.0236 (8)0.0284 (8)0.0241 (7)0.0071 (6)0.0053 (6)0.0065 (6)
C120.0148 (10)0.0151 (9)0.0240 (10)0.0021 (7)0.0042 (8)0.0022 (7)
O120.0262 (8)0.0249 (8)0.0214 (7)0.0022 (6)0.0062 (6)0.0058 (6)
C130.0181 (10)0.0117 (9)0.0241 (10)0.0013 (7)0.0035 (8)0.0018 (7)
C140.0186 (11)0.0155 (9)0.0293 (11)0.0017 (7)0.0035 (8)0.0013 (8)
C150.0195 (11)0.0190 (10)0.0353 (12)0.0016 (8)0.0026 (9)0.0039 (9)
C160.0289 (13)0.0243 (11)0.0259 (11)0.0011 (9)0.0058 (9)0.0011 (9)
C170.0275 (12)0.0217 (10)0.0237 (11)0.0007 (8)0.0020 (9)0.0025 (8)
C180.0176 (10)0.0151 (9)0.0207 (10)0.0006 (7)0.0011 (7)0.0010 (7)
S210.0175 (3)0.0222 (3)0.0195 (2)0.00001 (18)0.00318 (19)0.00432 (18)
N210.0162 (9)0.0225 (9)0.0202 (8)0.0029 (6)0.0037 (6)0.0001 (6)
C210.0191 (11)0.0164 (9)0.0232 (10)0.0010 (8)0.0035 (8)0.0004 (7)
O210.0198 (8)0.0284 (8)0.0298 (8)0.0086 (6)0.0041 (6)0.0044 (6)
C220.0190 (11)0.0167 (9)0.0236 (10)0.0006 (7)0.0012 (8)0.0015 (8)
O220.0241 (8)0.0356 (9)0.0236 (8)0.0083 (6)0.0004 (6)0.0037 (6)
C230.0200 (11)0.0134 (9)0.0214 (10)0.0004 (7)0.0020 (8)0.0019 (7)
C240.0201 (11)0.0185 (10)0.0258 (10)0.0037 (8)0.0037 (8)0.0007 (8)
C250.0257 (12)0.0187 (10)0.0286 (11)0.0023 (8)0.0098 (9)0.0025 (8)
C260.0279 (12)0.0221 (10)0.0241 (11)0.0019 (8)0.0074 (9)0.0040 (8)
C270.0238 (12)0.0228 (10)0.0256 (10)0.0053 (8)0.0029 (8)0.0061 (8)
C280.0191 (11)0.0139 (9)0.0247 (10)0.0011 (7)0.0040 (8)0.0008 (7)
S310.0245 (3)0.0304 (3)0.0297 (3)0.0057 (2)0.0014 (2)0.0088 (2)
N310.0265 (10)0.0198 (9)0.0265 (9)0.0045 (7)0.0047 (7)0.0018 (7)
C310.0191 (11)0.0185 (10)0.0331 (11)0.0022 (8)0.0070 (8)0.0023 (8)
O310.0460 (10)0.0151 (7)0.0448 (10)0.0023 (6)0.0139 (8)0.0031 (7)
C320.0194 (11)0.0211 (10)0.0288 (11)0.0044 (8)0.0060 (8)0.0040 (8)
O320.0432 (10)0.0317 (9)0.0295 (9)0.0061 (7)0.0076 (7)0.0090 (7)
C330.0173 (11)0.0183 (10)0.0258 (10)0.0029 (8)0.0074 (8)0.0014 (8)
C340.0239 (12)0.0169 (10)0.0416 (13)0.0006 (8)0.0134 (9)0.0000 (9)
C350.0291 (13)0.0257 (11)0.0376 (13)0.0007 (9)0.0126 (10)0.0110 (9)
C360.0319 (14)0.0384 (13)0.0280 (12)0.0002 (10)0.0121 (10)0.0068 (9)
C370.0303 (13)0.0258 (11)0.0288 (11)0.0038 (9)0.0115 (9)0.0049 (9)
C380.0201 (11)0.0177 (9)0.0285 (11)0.0038 (8)0.0101 (8)0.0019 (8)
S410.0291 (3)0.0234 (3)0.0201 (3)0.0061 (2)0.0045 (2)0.00362 (19)
N410.0244 (9)0.0193 (8)0.0167 (8)0.0032 (7)0.0025 (6)0.0000 (6)
C410.0188 (11)0.0202 (10)0.0212 (10)0.0023 (8)0.0030 (8)0.0003 (8)
O410.0405 (10)0.0227 (8)0.0224 (8)0.0003 (6)0.0025 (7)0.0049 (6)
C420.0140 (10)0.0212 (10)0.0214 (10)0.0017 (7)0.0047 (8)0.0020 (8)
O420.0284 (8)0.0299 (8)0.0170 (7)0.0001 (6)0.0040 (6)0.0039 (6)
C430.0135 (10)0.0198 (10)0.0231 (10)0.0018 (7)0.0036 (7)0.0005 (8)
C440.0236 (12)0.0194 (10)0.0298 (11)0.0011 (8)0.0035 (9)0.0031 (8)
C450.0253 (12)0.0206 (10)0.0357 (12)0.0018 (8)0.0026 (9)0.0041 (9)
C460.0249 (12)0.0279 (11)0.0262 (11)0.0012 (9)0.0028 (9)0.0074 (9)
C470.0263 (12)0.0245 (11)0.0213 (10)0.0047 (8)0.0009 (8)0.0001 (8)
C480.0175 (11)0.0192 (9)0.0214 (10)0.0027 (7)0.0039 (8)0.0003 (8)
Geometric parameters (Å, º) top
S11—N111.681 (2)S31—N311.692 (2)
S11—S212.0382 (7)S31—S412.0298 (8)
N11—C111.424 (2)N31—C321.426 (2)
N11—C121.433 (2)N31—C311.431 (2)
C11—O111.211 (2)C31—O311.202 (2)
C11—C181.478 (3)C31—C381.486 (3)
C12—O121.200 (2)C32—O321.205 (2)
C12—C131.486 (3)C32—C331.476 (3)
C13—C141.386 (3)C33—C341.383 (3)
C13—C181.394 (3)C33—C381.393 (3)
C14—C151.391 (3)C34—C351.382 (3)
C14—H140.9500C34—H340.9500
C15—C161.392 (3)C35—C361.399 (3)
C15—H150.9500C35—H350.9500
C16—C171.395 (3)C36—C371.391 (3)
C16—H160.9500C36—H360.9500
C17—C181.384 (3)C37—C381.377 (3)
C17—H170.9500C37—H370.9500
S21—N211.694 (2)S41—N411.694 (2)
N21—C211.420 (2)N41—C411.422 (2)
N21—C221.425 (3)N41—C421.425 (2)
C21—O211.206 (2)C41—O411.206 (2)
C21—C281.486 (3)C41—C481.484 (3)
C22—O221.200 (2)C42—O421.199 (2)
C22—C231.486 (3)C42—C431.483 (3)
C23—C241.385 (3)C43—C481.387 (3)
C23—C281.396 (3)C43—C441.388 (3)
C24—C251.395 (3)C44—C451.395 (3)
C24—H240.9500C44—H440.9500
C25—C261.387 (3)C45—C461.388 (3)
C25—H250.9500C45—H450.9500
C26—C271.390 (3)C46—C471.390 (3)
C26—H260.9500C46—H460.9500
C27—C281.379 (3)C47—C481.383 (3)
C27—H270.9500C47—H470.9500
N11—S11—S21103.37 (6)N31—S31—S41103.41 (6)
C11—N11—C12111.9 (2)C32—N31—C31111.1 (2)
C11—N11—S11123.3 (2)C32—N31—S31123.4 (2)
C12—N11—S11124.0 (2)C31—N31—S31124.4 (2)
O11—C11—N11124.5 (2)O31—C31—N31124.5 (2)
O11—C11—C18130.1 (2)O31—C31—C38130.2 (2)
N11—C11—C18105.4 (2)N31—C31—C38105.3 (2)
O12—C12—N11124.6 (2)O32—C32—N31124.7 (2)
O12—C12—C13131.0 (2)O32—C32—C33129.6 (2)
N11—C12—C13104.4 (2)N31—C32—C33105.6 (2)
C14—C13—C18121.7 (2)C34—C33—C38121.6 (2)
C14—C13—C12128.8 (2)C34—C33—C32129.2 (2)
C18—C13—C12109.5 (2)C38—C33—C32109.2 (2)
C13—C14—C15117.0 (2)C35—C34—C33117.2 (2)
C13—C14—H14121.5C35—C34—H34121.4
C15—C14—H14121.5C33—C34—H34121.4
C14—C15—C16121.6 (2)C34—C35—C36121.5 (2)
C14—C15—H15119.2C34—C35—H35119.2
C16—C15—H15119.2C36—C35—H35119.2
C15—C16—C17121.1 (2)C37—C36—C35120.7 (2)
C15—C16—H16119.5C37—C36—H36119.6
C17—C16—H16119.5C35—C36—H36119.6
C18—C17—C16117.4 (2)C38—C37—C36117.7 (2)
C18—C17—H17121.3C38—C37—H37121.2
C16—C17—H17121.3C36—C37—H37121.2
C17—C18—C13121.3 (2)C37—C38—C33121.3 (2)
C17—C18—C11129.9 (2)C37—C38—C31130.0 (2)
C13—C18—C11108.9 (2)C33—C38—C31108.8 (2)
N21—S21—S11104.36 (6)N41—S41—S31105.98 (6)
C21—N21—C22111.6 (2)C41—N41—C42111.9 (2)
C21—N21—S21123.3 (2)C41—N41—S41124.3 (2)
C22—N21—S21125.0 (2)C42—N41—S41123.4 (2)
O21—C21—N21124.8 (2)O41—C41—N41124.9 (2)
O21—C21—C28129.6 (2)O41—C41—C48130.0 (2)
N21—C21—C28105.6 (2)N41—C41—C48105.1 (2)
O22—C22—N21124.7 (2)O42—C42—N41125.3 (2)
O22—C22—C23130.2 (2)O42—C42—C43130.0 (2)
N21—C22—C23105.2 (2)N41—C42—C43104.7 (2)
C24—C23—C28121.6 (2)C48—C43—C44121.7 (2)
C24—C23—C22129.4 (2)C48—C43—C42109.5 (2)
C28—C23—C22109.0 (2)C44—C43—C42128.8 (2)
C23—C24—C25116.5 (2)C43—C44—C45116.7 (2)
C23—C24—H24121.8C43—C44—H44121.7
C25—C24—H24121.8C45—C44—H44121.7
C26—C25—C24121.9 (2)C46—C45—C44121.5 (2)
C26—C25—H25119.0C46—C45—H45119.3
C24—C25—H25119.0C44—C45—H45119.3
C25—C26—C27121.2 (2)C45—C46—C47121.5 (2)
C25—C26—H26119.4C45—C46—H46119.3
C27—C26—H26119.4C47—C46—H46119.3
C28—C27—C26117.1 (2)C48—C47—C46117.1 (2)
C28—C27—H27121.4C48—C47—H47121.5
C26—C27—H27121.4C46—C47—H47121.5
C27—C28—C23121.6 (2)C47—C48—C43121.7 (2)
C27—C28—C21129.8 (2)C47—C48—C41129.6 (2)
C23—C28—C21108.6 (2)C43—C48—C41108.7 (2)
S21—S11—N11—C1193.4 (2)S41—S31—N31—C3275.7 (2)
S21—S11—N11—C1275.4 (2)S41—S31—N31—C3191.1 (2)
C12—N11—C11—O11176.2 (2)C32—N31—C31—O31177.6 (2)
S11—N11—C11—O116.2 (3)S31—N31—C31—O319.4 (3)
C12—N11—C11—C182.8 (2)C32—N31—C31—C382.2 (2)
S11—N11—C11—C18172.8 (2)S31—N31—C31—C38170.4 (2)
C11—N11—C12—O12176.7 (2)C31—N31—C32—O32174.4 (2)
S11—N11—C12—O126.7 (3)S31—N31—C32—O326.1 (3)
C11—N11—C12—C132.4 (2)C31—N31—C32—C333.1 (2)
S11—N11—C12—C13172.4 (2)S31—N31—C32—C33171.4 (2)
O12—C12—C13—C140.7 (3)O32—C32—C33—C342.6 (4)
N11—C12—C13—C14179.7 (2)N31—C32—C33—C34179.9 (2)
O12—C12—C13—C18177.9 (2)O32—C32—C33—C38174.5 (2)
N11—C12—C13—C181.1 (2)N31—C32—C33—C382.8 (2)
C18—C13—C14—C150.2 (3)C38—C33—C34—C351.4 (3)
C12—C13—C14—C15178.7 (2)C32—C33—C34—C35175.5 (2)
C13—C14—C15—C160.7 (3)C33—C34—C35—C361.2 (3)
C14—C15—C16—C170.8 (3)C34—C35—C36—C370.1 (3)
C15—C16—C17—C180.1 (3)C35—C36—C37—C381.1 (3)
C16—C17—C18—C131.1 (3)C36—C37—C38—C331.0 (3)
C16—C17—C18—C11178.1 (2)C36—C37—C38—C31177.3 (2)
C14—C13—C18—C171.2 (3)C34—C33—C38—C370.3 (3)
C12—C13—C18—C17179.9 (2)C32—C33—C38—C37177.1 (2)
C14—C13—C18—C11178.1 (2)C34—C33—C38—C31178.9 (2)
C12—C13—C18—C110.6 (2)C32—C33—C38—C311.5 (2)
O11—C11—C18—C172.4 (3)O31—C31—C38—C370.9 (4)
N11—C11—C18—C17178.8 (2)N31—C31—C38—C37178.8 (2)
O11—C11—C18—C13176.9 (2)O31—C31—C38—C33179.4 (2)
N11—C11—C18—C132.0 (2)N31—C31—C38—C330.4 (2)
N11—S11—S21—N2180.06 (8)N31—S31—S41—N4186.72 (9)
S11—S21—N21—C2185.3 (2)S31—S41—N41—C4186.9 (2)
S11—S21—N21—C2292.1 (2)S31—S41—N41—C42100.8 (2)
C22—N21—C21—O21178.5 (2)C42—N41—C41—O41177.7 (2)
S21—N21—C21—O210.8 (3)S41—N41—C41—O414.7 (3)
C22—N21—C21—C282.0 (2)C42—N41—C41—C481.9 (2)
S21—N21—C21—C28179.7 (2)S41—N41—C41—C48174.9 (2)
C21—N21—C22—O22177.4 (2)C41—N41—C42—O42175.4 (2)
S21—N21—C22—O220.2 (3)S41—N41—C42—O422.4 (3)
C21—N21—C22—C232.8 (2)C41—N41—C42—C432.4 (2)
S21—N21—C22—C23179.6 (2)S41—N41—C42—C43175.4 (2)
O22—C22—C23—C241.4 (3)O42—C42—C43—C48175.7 (2)
N21—C22—C23—C24178.4 (2)N41—C42—C43—C481.9 (2)
O22—C22—C23—C28177.7 (2)O42—C42—C43—C444.5 (3)
N21—C22—C23—C282.5 (2)N41—C42—C43—C44177.8 (2)
C28—C23—C24—C250.6 (3)C48—C43—C44—C450.5 (3)
C22—C23—C24—C25178.3 (2)C42—C43—C44—C45179.2 (2)
C23—C24—C25—C260.9 (3)C43—C44—C45—C460.5 (3)
C24—C25—C26—C271.6 (3)C44—C45—C46—C470.3 (3)
C25—C26—C27—C280.6 (3)C45—C46—C47—C480.1 (3)
C26—C27—C28—C230.9 (3)C46—C47—C48—C430.1 (3)
C26—C27—C28—C21179.7 (2)C46—C47—C48—C41178.4 (2)
C24—C23—C28—C271.6 (3)C44—C43—C48—C470.3 (3)
C22—C23—C28—C27177.6 (2)C42—C43—C48—C47179.4 (2)
C24—C23—C28—C21179.5 (2)C44—C43—C48—C41178.9 (2)
C22—C23—C28—C211.4 (2)C42—C43—C48—C410.8 (2)
O21—C21—C28—C271.4 (3)O41—C41—C48—C472.6 (4)
N21—C21—C28—C27179.2 (2)N41—C41—C48—C47177.9 (2)
O21—C21—C28—C23179.7 (2)O41—C41—C48—C43179.0 (2)
N21—C21—C28—C230.3 (2)N41—C41—C48—C430.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O21i0.952.533.358 (2)146
C16—H16···O320.952.373.245 (2)153
C34—H34···O31ii0.952.453.198 (3)136
C45—H45···O41iii0.952.533.175 (3)126
Symmetry codes: (i) x, y+2, z; (ii) x, y+1, z; (iii) x, y1, z.
(6) N,N'-Dithiodiphthalimide–nitromethane solvate (1/1) top
Crystal data top
C16H8N2O4S2·CH3NO2F(000) = 856
Mr = 417.41Dx = 1.552 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 22.5545 (9) ÅCell parameters from 3397 reflections
b = 4.8545 (2) Åθ = 3.3–27.5°
c = 16.7095 (14) ŵ = 0.34 mm1
β = 102.4670 (17)°T = 120 K
V = 1786.40 (18) Å3Lath, colourless
Z = 40.40 × 0.16 × 0.10 mm
Data collection top
Kappa-CCD
diffractometer
3397 independent reflections
Radiation source: fine-focus sealed X-ray tube2883 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ scans, and ω scans with κ offsetsθmax = 26.1°, θmin = 3.3°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 2827
Tmin = 0.876, Tmax = 0.967k = 65
8059 measured reflectionsl = 2120
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0343P)2 + 1.0483P]
where P = (Fo2 + 2Fc2)/3
3397 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.38 e Å3
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
xyzUiso*/Ueq
S10.20852 (2)0.39105 (10)0.19499 (3)0.02150 (13)
N110.27521 (7)0.2845 (3)0.17624 (9)0.0202 (3)
C110.30491 (8)0.4105 (4)0.11894 (11)0.0210 (4)
O110.28414 (6)0.5987 (3)0.07467 (8)0.0289 (3)
C120.30951 (8)0.0618 (4)0.21787 (11)0.0194 (4)
O120.29242 (6)0.0874 (3)0.26596 (8)0.0255 (3)
C130.36660 (8)0.0589 (4)0.18706 (11)0.0196 (4)
C140.41727 (9)0.1070 (4)0.20966 (12)0.0243 (4)
C150.46470 (9)0.0643 (4)0.16969 (12)0.0270 (4)
C160.46138 (9)0.1373 (4)0.11002 (13)0.0273 (4)
C170.41018 (9)0.3049 (4)0.08780 (12)0.0246 (4)
C180.36339 (8)0.2616 (4)0.12779 (11)0.0201 (4)
S20.14412 (2)0.16382 (10)0.11990 (3)0.02271 (13)
N210.12499 (7)0.3532 (3)0.03339 (9)0.0198 (3)
C210.15479 (8)0.3351 (4)0.03363 (12)0.0212 (4)
O210.19511 (6)0.1767 (3)0.03719 (9)0.0297 (3)
C220.08065 (8)0.5644 (4)0.02087 (11)0.0191 (4)
O220.05129 (6)0.6320 (3)0.07028 (8)0.0241 (3)
C230.08005 (8)0.6755 (4)0.06173 (11)0.0186 (4)
C240.04340 (9)0.8776 (4)0.10547 (12)0.0245 (4)
C250.05291 (9)0.9412 (4)0.18285 (13)0.0283 (5)
C260.09724 (9)0.8082 (4)0.21470 (12)0.0285 (5)
C270.13443 (9)0.6084 (4)0.17012 (12)0.0257 (4)
C280.12431 (8)0.5441 (4)0.09332 (11)0.0198 (4)
C310.30711 (9)1.0140 (5)0.08442 (12)0.0286 (5)
N310.36677 (7)0.9449 (3)0.10308 (10)0.0245 (4)
O310.38564 (7)1.0908 (3)0.15208 (9)0.0337 (4)
O320.39413 (7)0.7434 (3)0.07037 (10)0.0418 (4)
H140.41960.24440.25070.029*
H150.50010.17560.18360.032*
H160.49450.16170.08390.033*
H170.40760.44290.04690.030*
H240.01310.96860.08360.029*
H250.02861.07860.21460.034*
H260.10220.85490.26810.034*
H270.16540.52000.19130.031*
H31A0.27450.94710.12880.043*
H31B0.30371.21420.07940.043*
H31C0.30370.92620.03280.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0184 (2)0.0275 (3)0.0180 (3)0.00009 (17)0.00254 (18)0.00081 (18)
N110.0189 (7)0.0228 (8)0.0187 (8)0.0004 (6)0.0035 (6)0.0031 (6)
C110.0221 (9)0.0249 (10)0.0161 (9)0.0047 (7)0.0042 (8)0.0010 (8)
O110.0275 (7)0.0311 (8)0.0279 (8)0.0024 (6)0.0056 (6)0.0106 (6)
C120.0205 (9)0.0203 (9)0.0153 (9)0.0029 (7)0.0008 (7)0.0018 (7)
O120.0248 (7)0.0289 (8)0.0227 (7)0.0034 (5)0.0045 (6)0.0060 (6)
C130.0207 (9)0.0208 (9)0.0167 (9)0.0044 (7)0.0026 (7)0.0040 (7)
C140.0234 (9)0.0232 (10)0.0251 (11)0.0011 (7)0.0022 (8)0.0003 (8)
C150.0209 (9)0.0289 (11)0.0305 (11)0.0013 (7)0.0040 (8)0.0037 (8)
C160.0231 (10)0.0329 (11)0.0281 (11)0.0041 (8)0.0106 (8)0.0055 (9)
C170.0257 (10)0.0278 (11)0.0210 (10)0.0040 (8)0.0063 (8)0.0002 (8)
C180.0215 (9)0.0224 (9)0.0161 (9)0.0034 (7)0.0030 (8)0.0022 (7)
S20.0203 (2)0.0244 (3)0.0219 (3)0.00259 (17)0.00120 (19)0.00366 (19)
N210.0189 (7)0.0250 (8)0.0156 (8)0.0026 (6)0.0038 (6)0.0007 (6)
C210.0189 (9)0.0234 (10)0.0214 (10)0.0015 (7)0.0046 (8)0.0053 (8)
O210.0254 (7)0.0315 (8)0.0334 (9)0.0085 (6)0.0092 (6)0.0025 (6)
C220.0150 (8)0.0220 (9)0.0192 (10)0.0018 (7)0.0009 (7)0.0052 (7)
O220.0210 (7)0.0317 (8)0.0210 (7)0.0013 (5)0.0077 (6)0.0063 (6)
C230.0173 (9)0.0196 (9)0.0180 (10)0.0021 (7)0.0018 (7)0.0030 (7)
C240.0202 (9)0.0259 (10)0.0258 (11)0.0005 (7)0.0013 (8)0.0019 (8)
C250.0261 (10)0.0272 (11)0.0276 (11)0.0035 (8)0.0029 (9)0.0055 (9)
C260.0314 (11)0.0341 (11)0.0190 (11)0.0104 (8)0.0033 (9)0.0032 (8)
C270.0251 (10)0.0328 (11)0.0204 (11)0.0049 (8)0.0077 (8)0.0049 (8)
C280.0187 (9)0.0210 (9)0.0193 (10)0.0027 (7)0.0033 (7)0.0030 (7)
C310.0230 (10)0.0413 (12)0.0235 (11)0.0046 (8)0.0095 (8)0.0020 (9)
N310.0248 (8)0.0305 (9)0.0187 (8)0.0029 (7)0.0057 (7)0.0007 (7)
O310.0353 (8)0.0332 (8)0.0374 (9)0.0025 (6)0.0181 (7)0.0081 (7)
O320.0362 (9)0.0502 (10)0.0415 (10)0.0182 (7)0.0137 (7)0.0208 (8)
Geometric parameters (Å, º) top
S1—N111.683 (2)C21—O211.202 (2)
S1—S22.0284 (7)C21—C281.483 (3)
N11—C111.420 (2)C22—O221.210 (2)
N11—C121.421 (2)C22—C231.479 (3)
C11—O111.205 (2)C23—C281.382 (3)
C11—C181.483 (3)C23—C241.385 (3)
C12—O121.205 (2)C24—C251.390 (3)
C12—C131.486 (3)C24—H240.9500
C13—C141.382 (3)C25—C261.389 (3)
C13—C181.387 (3)C25—H250.9500
C14—C151.394 (3)C26—C271.389 (3)
C14—H140.9500C26—H260.9500
C15—C161.388 (3)C27—C281.387 (3)
C15—H150.9500C27—H270.9500
C16—C171.396 (3)C31—N311.484 (2)
C16—H160.9500C31—H31A0.9800
C17—C181.382 (3)C31—H31B0.9800
C17—H170.9500C31—H31C0.9800
S2—N211.689 (2)N31—O321.221 (2)
N21—C221.416 (2)N31—O311.226 (2)
N21—C211.428 (2)
N11—S1—S2105.50 (6)O21—C21—C28130.5 (2)
C11—N11—C12111.8 (2)N21—C21—C28104.9 (2)
C11—N11—S1124.3 (2)O22—C22—N21124.7 (2)
C12—N11—S1123.8 (2)O22—C22—C23129.9 (2)
O11—C11—N11124.3 (2)N21—C22—C23105.4 (2)
O11—C11—C18130.6 (2)C28—C23—C24121.6 (2)
N11—C11—C18105.2 (2)C28—C23—C22109.0 (2)
O12—C12—N11124.4 (2)C24—C23—C22129.4 (2)
O12—C12—C13130.6 (2)C23—C24—C25117.0 (2)
N11—C12—C13105.0 (2)C23—C24—H24121.5
C14—C13—C18121.4 (2)C25—C24—H24121.5
C14—C13—C12129.6 (2)C26—C25—C24121.4 (2)
C18—C13—C12109.0 (2)C26—C25—H25119.3
C13—C14—C15117.2 (2)C24—C25—H25119.3
C13—C14—H14121.4C27—C26—C25121.4 (2)
C15—C14—H14121.4C27—C26—H26119.3
C16—C15—C14121.4 (2)C25—C26—H26119.3
C16—C15—H15119.3C28—C27—C26116.9 (2)
C14—C15—H15119.3C28—C27—H27121.5
C15—C16—C17121.0 (2)C26—C27—H27121.5
C15—C16—H16119.5C23—C28—C27121.7 (2)
C17—C16—H16119.5C23—C28—C21109.1 (2)
C18—C17—C16117.2 (2)C27—C28—C21129.2 (2)
C18—C17—H17121.4N31—C31—H31A109.5
C16—C17—H17121.4N31—C31—H31B109.5
C17—C18—C13121.7 (2)H31A—C31—H31B109.5
C17—C18—C11129.3 (2)N31—C31—H31C109.5
C13—C18—C11109.0 (2)H31A—C31—H31C109.5
N21—S2—S1104.48 (6)H31B—C31—H31C109.5
C22—N21—C21111.4 (2)O32—N31—O31123.2 (2)
C22—N21—S2124.2 (2)O32—N31—C31118.7 (2)
C21—N21—S2124.2 (2)O31—N31—C31118.1 (2)
O21—C21—N21124.6 (2)
S2—S1—N11—C1193.3 (2)S1—S2—N21—C2286.1 (2)
S2—S1—N11—C1288.7 (2)S1—S2—N21—C2188.8 (2)
C12—N11—C11—O11177.9 (2)C22—N21—C21—O21178.3 (2)
S1—N11—C11—O113.8 (3)S2—N21—C21—O212.9 (3)
C12—N11—C11—C182.3 (2)C22—N21—C21—C282.6 (2)
S1—N11—C11—C18176.0 (2)S2—N21—C21—C28178.0 (2)
C11—N11—C12—O12175.6 (2)C21—N21—C22—O22175.9 (2)
S1—N11—C12—O126.2 (3)S2—N21—C22—O220.4 (3)
C11—N11—C12—C133.2 (2)C21—N21—C22—C233.5 (2)
S1—N11—C12—C13175.1 (2)S2—N21—C22—C23178.9 (2)
O12—C12—C13—C144.6 (3)O22—C22—C23—C28176.3 (2)
N11—C12—C13—C14176.7 (2)N21—C22—C23—C283.0 (2)
O12—C12—C13—C18175.8 (2)O22—C22—C23—C243.5 (3)
N11—C12—C13—C182.8 (2)N21—C22—C23—C24177.2 (2)
C18—C13—C14—C150.7 (3)C28—C23—C24—C250.4 (3)
C12—C13—C14—C15179.7 (2)C22—C23—C24—C25179.9 (2)
C13—C14—C15—C160.3 (3)C23—C24—C25—C260.1 (3)
C14—C15—C16—C170.1 (3)C24—C25—C26—C270.8 (3)
C15—C16—C17—C180.2 (3)C25—C26—C27—C281.4 (3)
C16—C17—C18—C130.6 (3)C24—C23—C28—C270.3 (3)
C16—C17—C18—C11178.2 (2)C22—C23—C28—C27179.5 (2)
C14—C13—C18—C170.9 (3)C24—C23—C28—C21178.6 (2)
C12—C13—C18—C17179.5 (2)C22—C23—C28—C211.5 (2)
C14—C13—C18—C11178.1 (2)C26—C27—C28—C231.1 (3)
C12—C13—C18—C111.5 (2)C26—C27—C28—C21177.6 (2)
O11—C11—C18—C171.3 (3)O21—C21—C28—C23179.6 (2)
N11—C11—C18—C17178.5 (2)N21—C21—C28—C230.5 (2)
O11—C11—C18—C13179.9 (2)O21—C21—C28—C270.8 (3)
N11—C11—C18—C130.4 (2)N21—C21—C28—C27178.3 (2)
N11—S1—S2—N2190.90 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O320.952.413.352 (3)172
C24—H24···O22i0.952.463.334 (3)153
C31—H31C···O110.982.513.463 (3)165
C31—H31A···O21ii0.982.822.914 (3)85
C31—H31B···O21ii0.982.702.914 (3)93
C31—H31C···O21ii0.982.722.914 (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
Mr = 412.64F(000) = 422
Triclinic, P1Dx = 1.567 Mg m3
a = 7.6257 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3369 (2) ÅCell parameters from 3946 reflections
c = 11.6392 (2) Åθ = 3.0–27.5°
α = 81.5440 (8)°µ = 0.41 mm1
β = 77.8600 (8)°T = 120 K
γ = 78.8480 (13)°Block, colourless
V = 874.59 (12) Å30.34 × 0.30 × 0.28 mm
Data collection top
Kappa-CCD
diffractometer
3946 independent reflections
Radiation source: fine-focus sealed X-ray tube3616 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 99
Tmin = 0.873, Tmax = 0.894k = 1313
8059 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.056P)2 + 0.3058P]
where P = (Fo2 + 2Fc2)/3
3946 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.52 e Å3
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
xyzUiso*/UeqOcc. (<1)
S10.35296 (6)0.88571 (4)0.43979 (4)0.02869 (12)
N110.33665 (19)0.72395 (13)0.44954 (12)0.0259 (3)
C110.2341 (2)0.65337 (16)0.54575 (14)0.0258 (3)
O110.15461 (17)0.69813 (13)0.63585 (10)0.0331 (3)
C120.4083 (2)0.64658 (16)0.35332 (14)0.0253 (3)
O120.49770 (17)0.68481 (12)0.26090 (10)0.0328 (3)
C130.3491 (2)0.51658 (16)0.39402 (14)0.0257 (3)
C140.3799 (2)0.40494 (17)0.33493 (15)0.0308 (4)
C150.3058 (3)0.29571 (18)0.39522 (17)0.0340 (4)
C160.2069 (2)0.29764 (18)0.50985 (17)0.0337 (4)
C170.1753 (2)0.41066 (17)0.56928 (15)0.0298 (3)
C180.2483 (2)0.51960 (16)0.50859 (14)0.0258 (3)
S20.13079 (6)0.98197 (4)0.37288 (4)0.02938 (13)
N210.18274 (19)0.96564 (13)0.22729 (12)0.0270 (3)
C210.1455 (2)0.85774 (16)0.17847 (14)0.0264 (3)
O210.08687 (17)0.76369 (12)0.23590 (11)0.0340 (3)
C220.2512 (2)1.06297 (16)0.13777 (15)0.0276 (3)
O220.29537 (19)1.16216 (12)0.15667 (12)0.0372 (3)
C230.2536 (2)1.01210 (17)0.02441 (15)0.0279 (3)
C240.3017 (2)1.0699 (2)0.09035 (16)0.0346 (4)
C250.2868 (2)0.9995 (2)0.18075 (16)0.0406 (4)
C260.2277 (2)0.8780 (2)0.15692 (17)0.0394 (4)
C270.1793 (2)0.82053 (19)0.04093 (16)0.0337 (4)
C280.1931 (2)0.89078 (17)0.04864 (14)0.0273 (3)
Cl310.57340 (11)0.57934 (9)0.00109 (7)0.0342 (2)0.50
C310.8180 (3)0.5458 (2)0.00114 (17)0.0408 (4)
C320.9425 (3)0.5443 (2)0.10678 (16)0.0414 (4)
C330.8751 (3)0.5023 (2)0.10541 (17)0.0412 (5)
H140.44850.40310.25680.037*
H150.32320.21780.35700.041*
H160.15980.22070.54870.040*
H170.10710.41260.64750.036*
H240.34251.15310.10680.042*
H250.31811.03600.26070.049*
H260.21990.83290.22070.047*
H270.13890.73720.02420.040*
H310.69250.57690.00190.049*0.50
H320.90290.57510.17960.050*
H330.78910.50430.17750.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0357 (2)0.0261 (2)0.0267 (2)0.00862 (16)0.00918 (16)0.00171 (15)
N110.0303 (7)0.0244 (6)0.0234 (6)0.0059 (5)0.0054 (5)0.0017 (5)
C110.0259 (8)0.0286 (8)0.0235 (7)0.0045 (6)0.0080 (6)0.0003 (6)
O110.0381 (7)0.0362 (7)0.0237 (6)0.0055 (5)0.0031 (5)0.0045 (5)
C120.0242 (7)0.0274 (8)0.0240 (7)0.0021 (6)0.0062 (6)0.0021 (6)
O120.0331 (6)0.0346 (6)0.0270 (6)0.0057 (5)0.0003 (5)0.0007 (5)
C130.0239 (7)0.0292 (8)0.0251 (7)0.0044 (6)0.0087 (6)0.0013 (6)
C140.0315 (8)0.0329 (9)0.0293 (8)0.0032 (7)0.0094 (7)0.0057 (7)
C150.0373 (9)0.0294 (8)0.0400 (9)0.0056 (7)0.0146 (8)0.0082 (7)
C160.0340 (9)0.0300 (8)0.0403 (9)0.0114 (7)0.0130 (7)0.0019 (7)
C170.0272 (8)0.0326 (8)0.0296 (8)0.0074 (7)0.0070 (6)0.0021 (7)
C180.0252 (7)0.0281 (8)0.0254 (7)0.0047 (6)0.0084 (6)0.0019 (6)
S20.0331 (2)0.0269 (2)0.0258 (2)0.00081 (16)0.00318 (16)0.00417 (15)
N210.0312 (7)0.0253 (7)0.0250 (6)0.0052 (5)0.0070 (5)0.0008 (5)
C210.0251 (7)0.0253 (8)0.0291 (8)0.0032 (6)0.0073 (6)0.0019 (6)
O210.0378 (7)0.0300 (6)0.0352 (7)0.0108 (5)0.0089 (5)0.0024 (5)
C220.0261 (8)0.0267 (8)0.0287 (8)0.0029 (6)0.0072 (6)0.0019 (6)
O220.0477 (8)0.0268 (6)0.0406 (7)0.0107 (5)0.0147 (6)0.0005 (5)
C230.0219 (7)0.0331 (8)0.0278 (8)0.0032 (6)0.0060 (6)0.0008 (6)
C240.0258 (8)0.0452 (10)0.0309 (9)0.0076 (7)0.0054 (7)0.0045 (7)
C250.0283 (9)0.0634 (13)0.0261 (8)0.0021 (8)0.0036 (7)0.0013 (8)
C260.0297 (9)0.0575 (12)0.0311 (9)0.0033 (8)0.0083 (7)0.0152 (8)
C270.0300 (9)0.0368 (9)0.0355 (9)0.0004 (7)0.0097 (7)0.0095 (7)
C280.0238 (7)0.0308 (8)0.0268 (8)0.0015 (6)0.0067 (6)0.0031 (6)
Cl310.0262 (4)0.0438 (5)0.0317 (4)0.0036 (3)0.0063 (3)0.0031 (3)
C310.0353 (9)0.0474 (11)0.0329 (9)0.0109 (8)0.0068 (8)0.0063 (8)
C320.0453 (11)0.0468 (11)0.0266 (8)0.0078 (9)0.0091 (8)0.0031 (8)
C330.0425 (11)0.0460 (11)0.0274 (8)0.0091 (8)0.0038 (7)0.0057 (8)
Geometric parameters (Å, º) top
S1—N111.686 (1)C21—C281.482 (2)
S1—S22.0352 (6)C22—O221.202 (2)
N11—C111.418 (2)C22—C231.486 (2)
N11—C121.425 (2)C23—C241.386 (2)
C11—O111.203 (2)C23—C281.390 (2)
C11—C181.486 (2)C24—C251.399 (3)
C12—O121.204 (2)C24—H240.9500
C12—C131.480 (2)C25—C261.387 (3)
C13—C141.386 (2)C25—H250.9500
C13—C181.394 (2)C26—C271.397 (3)
C14—C151.391 (3)C26—H260.9500
C14—H140.9500C27—C281.387 (2)
C15—C161.388 (3)C27—H270.9500
C15—H150.9500Cl31—C311.830 (2)
C16—C171.400 (3)C31—C331.385 (3)
C16—H160.9500C31—C321.387 (3)
C17—C181.386 (2)C31—H310.9500
C17—H170.9500C32—C33i1.384 (3)
S2—N211.683 (2)C32—H320.9500
N21—C211.423 (2)C33—C32i1.384 (3)
N21—C221.427 (2)C33—H330.9500
C21—O211.201 (2)
N11—S1—S2103.99 (5)N21—C21—C28104.9 (2)
C11—N11—C12111.9 (2)O22—C22—N21124.6 (2)
C11—N11—S1125.2 (2)O22—C22—C23130.6 (2)
C12—N11—S1122.5 (2)N21—C22—C23104.8 (2)
O11—C11—N11124.9 (2)C24—C23—C28121.8 (2)
O11—C11—C18130.0 (2)C24—C23—C22129.2 (2)
N11—C11—C18105.1 (2)C28—C23—C22109.0 (2)
O12—C12—N11124.6 (2)C23—C24—C25116.5 (2)
O12—C12—C13130.2 (2)C23—C24—H24121.7
N11—C12—C13105.2 (2)C25—C24—H24121.7
C14—C13—C18121.7 (2)C26—C25—C24121.8 (2)
C14—C13—C12129.4 (2)C26—C25—H25119.1
C18—C13—C12108.9 (2)C24—C25—H25119.1
C13—C14—C15117.0 (2)C25—C26—C27121.3 (2)
C13—C14—H14121.5C25—C26—H26119.4
C15—C14—H14121.5C27—C26—H26119.4
C16—C15—C14121.6 (2)C28—C27—C26116.9 (2)
C16—C15—H15119.2C28—C27—H27121.6
C14—C15—H15119.2C26—C27—H27121.6
C15—C16—C17121.3 (2)C27—C28—C23121.7 (2)
C15—C16—H16119.3C27—C28—C21129.0 (2)
C17—C16—H16119.3C23—C28—C21109.3 (2)
C18—C17—C16116.8 (2)C33—C31—C32120.5 (2)
C18—C17—H17121.6C33—C31—Cl31118.2 (2)
C16—C17—H17121.6C32—C31—Cl31120.5 (2)
C17—C18—C13121.6 (2)C33—C31—H31119.7
C17—C18—C11129.6 (2)C32—C31—H31119.7
C13—C18—C11108.9 (2)Cl31—C31—H318.6
N21—S2—S1105.62 (5)C33i—C32—C31119.6 (2)
C21—N21—C22112.0 (2)C33i—C32—H32120.2
C21—N21—S2123.1 (2)C31—C32—H32120.2
C22—N21—S2124.6 (2)C32i—C33—C31119.9 (2)
O21—C21—N21124.4 (2)C32i—C33—H33120.0
O21—C21—C28130.6 (2)C31—C33—H33120.0
S2—S1—N11—C1185.1 (2)C22—N21—C21—O21180.0 (2)
S2—S1—N11—C1286.8 (2)S2—N21—C21—O215.9 (2)
C12—N11—C11—O11177.4 (2)C22—N21—C21—C280.4 (2)
S1—N11—C11—O114.7 (2)S2—N21—C21—C28173.7 (2)
C12—N11—C11—C182.2 (2)C21—N21—C22—O22178.8 (2)
S1—N11—C11—C18174.9 (2)S2—N21—C22—O227.2 (2)
C11—N11—C12—O12178.9 (2)C21—N21—C22—C231.0 (2)
S1—N11—C12—O125.9 (2)S2—N21—C22—C23173.1 (2)
C11—N11—C12—C131.4 (2)O22—C22—C23—C242.9 (3)
S1—N11—C12—C13174.3 (2)N21—C22—C23—C24177.4 (2)
O12—C12—C13—C140.9 (3)O22—C22—C23—C28178.6 (2)
N11—C12—C13—C14179.4 (2)N21—C22—C23—C281.2 (2)
O12—C12—C13—C18179.6 (2)C28—C23—C24—C250.3 (3)
N11—C12—C13—C180.1 (2)C22—C23—C24—C25178.7 (2)
C18—C13—C14—C150.1 (2)C23—C24—C25—C260.2 (3)
C12—C13—C14—C15179.5 (2)C24—C25—C26—C270.3 (3)
C13—C14—C15—C160.6 (3)C25—C26—C27—C280.1 (3)
C14—C15—C16—C170.9 (3)C26—C27—C28—C230.6 (2)
C15—C16—C17—C180.4 (3)C26—C27—C28—C21177.5 (2)
C16—C17—C18—C130.3 (2)C24—C23—C28—C270.7 (3)
C16—C17—C18—C11178.0 (2)C22—C23—C28—C27179.4 (2)
C14—C13—C18—C170.5 (2)C24—C23—C28—C21177.7 (2)
C12—C13—C18—C17180.0 (2)C22—C23—C28—C210.9 (2)
C14—C13—C18—C11178.1 (2)O21—C21—C28—C270.9 (3)
C12—C13—C18—C111.4 (2)N21—C21—C28—C27178.6 (2)
O11—C11—C18—C171.1 (3)O21—C21—C28—C23179.2 (2)
N11—C11—C18—C17179.3 (2)N21—C21—C28—C230.3 (2)
O11—C11—C18—C13177.4 (2)C33—C31—C32—C33i0.6 (4)
N11—C11—C18—C132.2 (2)Cl31—C31—C32—C33i169.4 (2)
N11—S1—S2—N2177.62 (7)C32—C31—C33—C32i0.6 (4)
S1—S2—N21—C2189.8 (2)Cl31—C31—C33—C32i169.7 (2)
S1—S2—N21—C2296.8 (2)
Symmetry code: (i) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O22ii0.952.543.299 (2)137
C24—H24···O12iii0.952.553.384 (2)147
C26—H26···O11iv0.952.513.445 (2)170
Symmetry codes: (ii) x, y1, z; (iii) x+1, y+2, z; (iv) x, y, z1.
(8) N,N'-Dithiodiphthalimide ethylbenzene/water solvate top
Crystal data top
C19.652H12.652N2O4.043S2F(000) = 1671.3
Mr = 405.63Dx = 1.482 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.7600 (4) ÅCell parameters from 8251 reflections
b = 16.4924 (4) Åθ = 3.0–27.5°
c = 16.0450 (5) ŵ = 0.32 mm1
β = 92.951 (1)°T = 120 K
V = 3636.35 (18) Å3Block, colourless
Z = 80.16 × 0.14 × 0.08 mm
Data collection top
Kappa-CCD
diffractometer
8251 independent reflections
Radiation source: fine-focus sealed X-ray tube5880 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1716
Tmin = 0.950, Tmax = 0.975k = 2121
32961 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0693P)2 + 0.827P]
where P = (Fo2 + 2Fc2)/3
8251 reflections(Δ/σ)max = 0.001
510 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.51 e Å3
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
xyzUiso*/UeqOcc. (<1)
S10.56497 (4)1.07875 (3)0.55872 (3)0.02625 (14)
N110.55669 (12)1.14800 (10)0.63540 (11)0.0242 (4)
C110.53967 (14)1.23220 (12)0.61952 (13)0.0240 (5)
O110.53913 (11)1.26297 (9)0.55175 (9)0.0322 (4)
C120.55073 (14)1.12898 (13)0.72145 (13)0.0248 (5)
O120.56016 (11)1.06212 (9)0.75050 (10)0.0323 (4)
C130.52927 (14)1.20738 (12)0.76250 (13)0.0243 (5)
C140.51381 (15)1.22331 (14)0.84514 (14)0.0301 (5)
C150.49010 (16)1.30300 (14)0.86551 (15)0.0329 (5)
C160.48295 (16)1.36349 (14)0.80512 (15)0.0326 (5)
C170.49912 (15)1.34722 (13)0.72214 (15)0.0292 (5)
C180.52244 (14)1.26758 (12)0.70216 (13)0.0235 (4)
S20.70905 (4)1.06824 (3)0.53908 (3)0.02599 (14)
N210.73548 (12)1.14829 (10)0.47877 (11)0.0239 (4)
C210.76059 (14)1.22620 (12)0.51209 (13)0.0232 (4)
O210.76493 (11)1.24218 (9)0.58506 (9)0.0320 (4)
C220.73409 (14)1.14744 (12)0.39032 (13)0.0222 (4)
O220.71210 (11)1.09026 (9)0.34688 (10)0.0301 (4)
C230.76296 (14)1.23073 (12)0.36626 (13)0.0217 (4)
C240.77293 (14)1.26336 (12)0.28811 (13)0.0248 (5)
C250.79624 (16)1.34537 (13)0.28374 (14)0.0295 (5)
C260.81024 (16)1.39207 (13)0.35550 (15)0.0339 (5)
C270.80128 (16)1.35845 (13)0.43452 (15)0.0305 (5)
C280.77743 (14)1.27734 (12)0.43800 (13)0.0229 (4)
S30.92291 (4)0.56524 (3)0.14182 (3)0.02608 (14)
N310.92976 (12)0.60975 (10)0.04778 (10)0.0232 (4)
C310.96547 (14)0.69004 (12)0.03550 (14)0.0243 (5)
O310.98486 (12)0.73725 (9)0.09097 (10)0.0349 (4)
C320.91710 (14)0.56715 (12)0.02893 (13)0.0214 (4)
O320.89105 (10)0.49746 (8)0.03568 (9)0.0254 (3)
C330.94224 (14)0.62580 (12)0.09418 (13)0.0217 (4)
C340.93855 (15)0.61659 (12)0.17949 (13)0.0250 (4)
C350.96574 (15)0.68249 (13)0.22713 (14)0.0288 (5)
C360.99533 (15)0.75499 (13)0.18917 (14)0.0294 (5)
C370.99837 (15)0.76437 (13)0.10277 (15)0.0289 (5)
C380.97138 (14)0.69848 (12)0.05592 (13)0.0239 (4)
S40.78144 (4)0.57415 (3)0.17005 (3)0.02595 (14)
N410.77117 (12)0.65847 (9)0.22876 (10)0.0216 (4)
C410.74309 (14)0.73648 (12)0.19677 (13)0.0218 (4)
O410.73820 (11)0.75391 (9)0.12413 (9)0.0307 (4)
C420.77341 (15)0.65643 (12)0.31709 (13)0.0229 (4)
O420.79904 (12)0.59894 (9)0.35859 (9)0.0336 (4)
C430.73990 (14)0.73778 (11)0.34261 (13)0.0207 (4)
C440.72588 (15)0.76725 (12)0.42186 (13)0.0241 (5)
C450.69530 (15)0.84712 (12)0.42838 (14)0.0272 (5)
C460.67987 (15)0.89545 (12)0.35765 (15)0.0285 (5)
C470.69307 (14)0.86513 (12)0.27794 (14)0.0259 (5)
C480.72332 (14)0.78526 (12)0.27189 (13)0.0212 (4)
C510.24638 (19)1.02434 (15)0.91112 (16)0.0337 (6)0.913 (2)
C520.1637 (2)1.05907 (15)0.94109 (15)0.0357 (6)0.913 (2)
C530.0715 (2)1.03501 (15)0.91273 (16)0.0345 (6)0.913 (2)
C540.06071 (18)0.97524 (14)0.85275 (15)0.0286 (6)0.913 (2)
C550.14274 (18)0.94107 (14)0.82041 (16)0.0302 (6)0.913 (2)
C560.23430 (19)0.96483 (15)0.84988 (15)0.0320 (6)0.913 (2)
C570.3488 (2)1.0484 (2)0.9428 (2)0.0528 (8)0.913 (2)
C580.3795 (3)1.0069 (3)1.0246 (2)0.0740 (11)0.913 (2)
O610.3150 (10)0.9561 (9)0.8228 (10)0.020*0.087 (2)
H140.51901.18200.88640.036*
H150.47861.31610.92180.039*
H160.46661.41710.82100.039*
H170.49451.38850.68080.035*
H240.76421.23120.23920.030*
H250.80271.36990.23070.035*
H260.82621.44790.35060.041*
H270.81121.39000.48380.037*
H340.91820.56700.20500.030*
H350.96410.67800.28620.035*
H361.01390.79910.22300.035*
H371.01820.81400.07710.035*
H440.73680.73410.46990.029*
H450.68470.86920.48190.033*
H460.65990.95020.36390.034*
H470.68180.89790.22970.031*
H520.17041.10050.98220.043*0.913 (2)
H530.01571.05960.93450.041*0.913 (2)
H540.00240.95770.83380.034*0.913 (2)
H550.13590.90120.77780.036*0.913 (2)
H560.29000.94020.82810.038*0.913 (2)
H57A0.39541.03390.90010.063*0.913 (2)
H57B0.35151.10790.95070.063*0.913 (2)
H58A0.33291.02011.06670.111*0.913 (2)
H58B0.44441.02591.04360.111*0.913 (2)
H58C0.38100.94811.01630.111*0.913 (2)
H61A0.32080.91600.79110.030*0.087 (2)
H61B0.27620.94910.86110.030*0.087 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0304 (3)0.0249 (3)0.0240 (3)0.0028 (2)0.0067 (2)0.0018 (2)
N110.0252 (9)0.0244 (8)0.0236 (9)0.0008 (7)0.0052 (7)0.0008 (7)
C110.0203 (11)0.0254 (10)0.0265 (12)0.0004 (8)0.0038 (9)0.0020 (9)
O110.0406 (9)0.0313 (8)0.0251 (9)0.0003 (7)0.0052 (7)0.0057 (7)
C120.0199 (10)0.0312 (11)0.0235 (11)0.0030 (8)0.0036 (8)0.0009 (9)
O120.0380 (9)0.0286 (8)0.0303 (9)0.0004 (6)0.0031 (7)0.0043 (7)
C130.0197 (10)0.0288 (11)0.0247 (11)0.0019 (8)0.0030 (8)0.0005 (9)
C140.0250 (11)0.0394 (12)0.0259 (12)0.0050 (9)0.0027 (9)0.0018 (10)
C150.0295 (12)0.0422 (13)0.0272 (12)0.0037 (10)0.0038 (10)0.0100 (11)
C160.0287 (12)0.0316 (11)0.0377 (14)0.0028 (9)0.0035 (10)0.0119 (11)
C170.0261 (11)0.0273 (11)0.0341 (13)0.0023 (9)0.0014 (10)0.0033 (10)
C180.0187 (10)0.0282 (11)0.0235 (11)0.0029 (8)0.0024 (8)0.0014 (9)
S20.0318 (3)0.0220 (3)0.0250 (3)0.0050 (2)0.0094 (2)0.0060 (2)
N210.0297 (10)0.0202 (8)0.0224 (9)0.0010 (7)0.0074 (8)0.0020 (7)
C210.0218 (10)0.0266 (10)0.0215 (11)0.0022 (8)0.0018 (8)0.0015 (9)
O210.0382 (9)0.0357 (8)0.0224 (8)0.0023 (7)0.0044 (7)0.0045 (7)
C220.0215 (10)0.0230 (10)0.0226 (11)0.0041 (8)0.0056 (8)0.0005 (9)
O220.0404 (9)0.0232 (7)0.0270 (8)0.0011 (6)0.0061 (7)0.0045 (7)
C230.0182 (10)0.0230 (10)0.0244 (11)0.0033 (8)0.0047 (8)0.0000 (9)
C240.0219 (11)0.0278 (10)0.0250 (11)0.0025 (8)0.0054 (9)0.0008 (9)
C250.0277 (12)0.0304 (11)0.0311 (12)0.0041 (9)0.0082 (10)0.0108 (10)
C260.0353 (13)0.0229 (10)0.0442 (15)0.0020 (9)0.0098 (11)0.0051 (10)
C270.0329 (12)0.0244 (10)0.0346 (13)0.0014 (9)0.0068 (10)0.0039 (10)
C280.0231 (11)0.0230 (10)0.0230 (11)0.0026 (8)0.0048 (8)0.0003 (9)
S30.0324 (3)0.0263 (3)0.0200 (3)0.0073 (2)0.0053 (2)0.0010 (2)
N310.0278 (9)0.0226 (8)0.0195 (9)0.0025 (7)0.0050 (7)0.0017 (7)
C310.0233 (11)0.0224 (10)0.0276 (12)0.0013 (8)0.0054 (9)0.0028 (9)
O310.0423 (10)0.0324 (8)0.0302 (9)0.0053 (7)0.0056 (7)0.0110 (7)
C320.0175 (10)0.0245 (10)0.0226 (11)0.0061 (8)0.0040 (8)0.0030 (9)
O320.0270 (8)0.0216 (7)0.0281 (8)0.0001 (6)0.0051 (6)0.0014 (6)
C330.0186 (10)0.0229 (10)0.0240 (11)0.0031 (8)0.0046 (8)0.0005 (9)
C340.0246 (11)0.0252 (10)0.0257 (11)0.0034 (8)0.0047 (9)0.0008 (9)
C350.0257 (11)0.0374 (12)0.0237 (11)0.0072 (9)0.0062 (9)0.0051 (10)
C360.0245 (11)0.0313 (11)0.0331 (13)0.0010 (9)0.0081 (9)0.0100 (10)
C370.0242 (11)0.0242 (10)0.0386 (13)0.0008 (8)0.0041 (10)0.0013 (10)
C380.0200 (10)0.0248 (10)0.0272 (12)0.0020 (8)0.0050 (9)0.0008 (9)
S40.0328 (3)0.0233 (3)0.0225 (3)0.0035 (2)0.0087 (2)0.0057 (2)
N410.0280 (9)0.0189 (8)0.0184 (9)0.0001 (7)0.0051 (7)0.0011 (7)
C410.0201 (10)0.0235 (10)0.0220 (11)0.0028 (8)0.0037 (8)0.0016 (9)
O410.0386 (9)0.0337 (8)0.0202 (8)0.0005 (7)0.0053 (7)0.0048 (7)
C420.0251 (11)0.0230 (10)0.0210 (11)0.0016 (8)0.0040 (8)0.0008 (9)
O420.0530 (10)0.0237 (8)0.0243 (9)0.0049 (7)0.0043 (7)0.0039 (7)
C430.0188 (10)0.0212 (9)0.0221 (11)0.0012 (7)0.0025 (8)0.0010 (8)
C440.0250 (11)0.0270 (10)0.0206 (11)0.0007 (8)0.0034 (9)0.0009 (9)
C450.0242 (11)0.0301 (11)0.0277 (12)0.0022 (9)0.0054 (9)0.0089 (10)
C460.0248 (11)0.0208 (10)0.0404 (14)0.0008 (8)0.0066 (10)0.0049 (10)
C470.0225 (11)0.0228 (10)0.0325 (12)0.0004 (8)0.0034 (9)0.0041 (9)
C480.0178 (10)0.0227 (9)0.0233 (11)0.0024 (8)0.0031 (8)0.0008 (9)
C510.0429 (15)0.0324 (13)0.0254 (13)0.0100 (11)0.0027 (11)0.0098 (11)
C520.0615 (18)0.0265 (12)0.0188 (13)0.0032 (12)0.0001 (12)0.0038 (10)
C530.0450 (16)0.0322 (13)0.0268 (14)0.0074 (11)0.0074 (12)0.0021 (11)
C540.0349 (14)0.0264 (12)0.0247 (13)0.0018 (10)0.0026 (10)0.0037 (10)
C550.0407 (15)0.0218 (11)0.0286 (14)0.0038 (10)0.0077 (11)0.0033 (10)
C560.0392 (15)0.0287 (12)0.0290 (14)0.0040 (10)0.0109 (11)0.0029 (11)
C570.0534 (19)0.0547 (18)0.050 (2)0.0076 (15)0.0007 (15)0.0073 (15)
C580.057 (2)0.112 (3)0.052 (2)0.009 (2)0.0042 (17)0.007 (2)
Geometric parameters (Å, º) top
S1—N111.687 (2)C34—C351.391 (3)
S1—S22.0308 (7)C34—H340.9500
N11—C121.422 (3)C35—C361.393 (3)
N11—C111.429 (3)C35—H350.9500
C11—O111.200 (2)C36—C371.394 (3)
C11—C181.479 (3)C36—H360.9500
C12—O121.202 (2)C37—C381.383 (3)
C12—C131.488 (3)C37—H370.9500
C13—C141.379 (3)S4—N411.690 (2)
C13—C181.386 (3)N41—C421.416 (3)
C14—C151.397 (3)N41—C411.431 (3)
C14—H140.9500C41—O411.199 (2)
C15—C161.391 (3)C41—C481.486 (3)
C15—H150.9500C42—O421.201 (2)
C16—C171.387 (3)C42—C431.483 (3)
C16—H160.9500C43—C441.384 (3)
C17—C181.393 (3)C43—C481.388 (3)
C17—H170.9500C44—C451.389 (3)
S2—N211.688 (2)C44—H440.9500
N21—C221.418 (3)C45—C461.394 (3)
N21—C211.427 (3)C45—H450.9500
C21—O211.199 (2)C46—C471.394 (3)
C21—C281.485 (3)C46—H460.9500
C22—O221.202 (2)C47—C481.386 (3)
C22—C231.487 (3)C47—H470.9500
C23—C241.378 (3)C51—C521.382 (4)
C23—C281.390 (3)C51—C561.393 (4)
C24—C251.393 (3)C51—C571.526 (4)
C24—H240.9500C52—C531.384 (4)
C25—C261.390 (3)C52—H520.9500
C25—H250.9500C53—C541.380 (3)
C26—C271.395 (3)C53—H530.9500
C26—H260.9500C54—C551.386 (3)
C27—C281.379 (3)C54—H540.9500
C27—H270.9500C55—C561.380 (4)
S3—N311.685 (2)C55—H550.9500
S3—S42.0266 (7)C56—H560.9500
N31—C321.420 (3)C57—C581.521 (5)
N31—C311.429 (3)C57—H57A0.9900
C31—O311.202 (3)C57—H57B0.9900
C31—C381.480 (3)C58—H58A0.9800
C32—O321.207 (2)C58—H58B0.9800
C32—C331.479 (3)C58—H58C0.9800
C33—C341.376 (3)O61—H61A0.8402
C33—C381.396 (3)O61—H61B0.8425
N11—S1—S2105.91 (6)C33—C34—C35117.6 (2)
C12—N11—C11111.7 (2)C33—C34—H34121.2
C12—N11—S1124.6 (2)C35—C34—H34121.2
C11—N11—S1123.0 (2)C34—C35—C36120.7 (2)
O11—C11—N11124.5 (2)C34—C35—H35119.6
O11—C11—C18130.7 (2)C36—C35—H35119.6
N11—C11—C18104.8 (2)C35—C36—C37121.6 (2)
O12—C12—N11124.7 (2)C35—C36—H36119.2
O12—C12—C13130.2 (2)C37—C36—H36119.2
N11—C12—C13105.1 (2)C38—C37—C36117.3 (2)
C14—C13—C18121.8 (2)C38—C37—H37121.4
C14—C13—C12129.4 (2)C36—C37—H37121.4
C18—C13—C12108.7 (2)C37—C38—C33121.0 (2)
C13—C14—C15117.0 (2)C37—C38—C31130.0 (2)
C13—C14—H14121.5C33—C38—C31109.0 (2)
C15—C14—H14121.5N41—S4—S3107.05 (6)
C16—C15—C14121.4 (2)C42—N41—C41111.8 (2)
C16—C15—H15119.3C42—N41—S4122.7 (2)
C14—C15—H15119.3C41—N41—S4124.7 (2)
C17—C16—C15121.4 (2)O41—C41—N41124.4 (2)
C17—C16—H16119.3O41—C41—C48130.9 (2)
C15—C16—H16119.3N41—C41—C48104.7 (2)
C16—C17—C18117.0 (2)O42—C42—N41124.4 (2)
C16—C17—H17121.5O42—C42—C43130.4 (2)
C18—C17—H17121.5N41—C42—C43105.3 (2)
C13—C18—C17121.5 (2)C44—C43—C48121.9 (2)
C13—C18—C11109.6 (2)C44—C43—C42129.2 (2)
C17—C18—C11128.9 (2)C48—C43—C42109.0 (2)
N21—S2—S1105.26 (6)C43—C44—C45117.4 (2)
C22—N21—C21112.0 (2)C43—C44—H44121.3
C22—N21—S2125.0 (2)C45—C44—H44121.3
C21—N21—S2123.0 (2)C44—C45—C46121.0 (2)
O21—C21—N21124.3 (2)C44—C45—H45119.5
O21—C21—C28130.9 (2)C46—C45—H45119.5
N21—C21—C28104.8 (2)C47—C46—C45121.4 (2)
O22—C22—N21125.3 (2)C47—C46—H46119.3
O22—C22—C23129.6 (2)C45—C46—H46119.3
N21—C22—C23105.1 (2)C48—C47—C46117.3 (2)
C24—C23—C28121.4 (2)C48—C47—H47121.3
C24—C23—C22129.6 (2)C46—C47—H47121.3
C28—C23—C22109.0 (2)C47—C48—C43121.1 (2)
C23—C24—C25117.3 (2)C47—C48—C41129.7 (2)
C23—C24—H24121.3C43—C48—C41109.2 (2)
C25—C24—H24121.3C52—C51—C56117.8 (2)
C26—C25—C24121.2 (2)C52—C51—C57122.7 (3)
C26—C25—H25119.4C56—C51—C57119.5 (3)
C24—C25—H25119.4C51—C52—C53121.6 (2)
C25—C26—C27121.2 (2)C51—C52—H52119.2
C25—C26—H26119.4C53—C52—H52119.2
C27—C26—H26119.4C54—C53—C52119.8 (2)
C28—C27—C26117.0 (2)C54—C53—H53120.1
C28—C27—H27121.5C52—C53—H53120.1
C26—C27—H27121.5C53—C54—C55119.4 (2)
C27—C28—C23121.8 (2)C53—C54—H54120.3
C27—C28—C21129.1 (2)C55—C54—H54120.3
C23—C28—C21109.1 (2)C56—C55—C54120.2 (2)
N31—S3—S4105.50 (6)C56—C55—H55119.9
C32—N31—C31111.5 (2)C54—C55—H55119.9
C32—N31—S3123.4 (2)C55—C56—C51121.0 (2)
C31—N31—S3124.2 (2)C55—C56—H56119.5
O31—C31—N31124.2 (2)C51—C56—H56119.5
O31—C31—C38130.7 (2)C58—C57—C51112.4 (3)
N31—C31—C38105.1 (2)C58—C57—H57A109.1
O32—C32—N31124.8 (2)C51—C57—H57A109.1
O32—C32—C33129.7 (2)C58—C57—H57B109.1
N31—C32—C33105.5 (2)C51—C57—H57B109.1
C34—C33—C38121.8 (2)H57A—C57—H57B107.9
C34—C33—C32129.3 (2)H61A—O61—H61B114.8
C38—C33—C32108.8 (2)
S2—S1—N11—C1295.9 (2)S3—N31—C31—C38172.0 (2)
S2—S1—N11—C1194.2 (2)C31—N31—C32—O32177.3 (2)
C12—N11—C11—O11178.7 (2)S3—N31—C32—O327.6 (3)
S1—N11—C11—O117.6 (3)C31—N31—C32—C332.7 (2)
C12—N11—C11—C180.3 (2)S3—N31—C32—C33172.4 (2)
S1—N11—C11—C18171.4 (2)O32—C32—C33—C342.9 (4)
C11—N11—C12—O12178.4 (2)N31—C32—C33—C34177.2 (2)
S1—N11—C12—O127.4 (3)O32—C32—C33—C38178.1 (2)
C11—N11—C12—C130.5 (2)N31—C32—C33—C381.9 (2)
S1—N11—C12—C13171.5 (2)C38—C33—C34—C350.5 (3)
O12—C12—C13—C140.6 (4)C32—C33—C34—C35179.4 (2)
N11—C12—C13—C14178.2 (2)C33—C34—C35—C360.1 (3)
O12—C12—C13—C18178.2 (2)C34—C35—C36—C370.3 (3)
N11—C12—C13—C180.6 (2)C35—C36—C37—C380.4 (3)
C18—C13—C14—C150.5 (3)C36—C37—C38—C330.1 (3)
C12—C13—C14—C15176.9 (2)C36—C37—C38—C31178.9 (2)
C13—C14—C15—C160.3 (3)C34—C33—C38—C370.4 (3)
C14—C15—C16—C170.0 (3)C32—C33—C38—C37179.5 (2)
C15—C16—C17—C180.2 (3)C34—C33—C38—C31178.7 (2)
C14—C13—C18—C170.3 (3)C32—C33—C38—C310.5 (2)
C12—C13—C18—C17177.5 (2)O31—C31—C38—C372.1 (4)
C14—C13—C18—C11178.3 (2)N31—C31—C38—C37177.8 (2)
C12—C13—C18—C110.4 (2)O31—C31—C38—C33179.0 (2)
C16—C17—C18—C130.1 (3)N31—C31—C38—C331.1 (2)
C16—C17—C18—C11177.5 (2)N31—S3—S4—N4194.51 (9)
O11—C11—C18—C13179.0 (2)S3—S4—N41—C4296.6 (2)
N11—C11—C18—C130.1 (2)S3—S4—N41—C4194.6 (2)
O11—C11—C18—C171.2 (4)C42—N41—C41—O41178.1 (2)
N11—C11—C18—C17177.7 (2)S4—N41—C41—O4112.0 (3)
N11—S1—S2—N2180.14 (9)C42—N41—C41—C482.0 (2)
S1—S2—N21—C2293.1 (2)S4—N41—C41—C48167.9 (2)
S1—S2—N21—C2185.8 (2)C41—N41—C42—O42176.5 (2)
C22—N21—C21—O21178.7 (2)S4—N41—C42—O4213.4 (3)
S2—N21—C21—O210.3 (3)C41—N41—C42—C432.8 (2)
C22—N21—C21—C280.8 (2)S4—N41—C42—C43167.4 (2)
S2—N21—C21—C28179.9 (2)O42—C42—C43—C442.9 (4)
C21—N21—C22—O22177.4 (2)N41—C42—C43—C44177.9 (2)
S2—N21—C22—O221.6 (3)O42—C42—C43—C48176.7 (2)
C21—N21—C22—C231.5 (2)N41—C42—C43—C482.5 (2)
S2—N21—C22—C23179.5 (2)C48—C43—C44—C450.7 (3)
O22—C22—C23—C240.8 (4)C42—C43—C44—C45178.9 (2)
N21—C22—C23—C24179.7 (2)C43—C44—C45—C460.3 (3)
O22—C22—C23—C28177.3 (2)C44—C45—C46—C471.0 (3)
N21—C22—C23—C281.6 (2)C45—C46—C47—C480.8 (3)
C28—C23—C24—C251.2 (3)C46—C47—C48—C430.2 (3)
C22—C23—C24—C25176.7 (2)C46—C47—C48—C41179.8 (2)
C23—C24—C25—C260.9 (3)C44—C43—C48—C470.9 (3)
C24—C25—C26—C270.1 (3)C42—C43—C48—C47178.8 (2)
C25—C26—C27—C280.4 (3)C44—C43—C48—C41179.1 (2)
C26—C27—C28—C230.1 (3)C42—C43—C48—C411.3 (2)
C26—C27—C28—C21178.2 (2)O41—C41—C48—C470.3 (4)
C24—C23—C28—C270.8 (3)N41—C41—C48—C47179.6 (2)
C22—C23—C28—C27177.5 (2)O41—C41—C48—C43179.7 (2)
C24—C23—C28—C21179.4 (2)N41—C41—C48—C430.4 (2)
C22—C23—C28—C211.1 (2)C56—C51—C52—C531.1 (4)
O21—C21—C28—C271.3 (4)C57—C51—C52—C53178.6 (2)
N21—C21—C28—C27178.3 (2)C51—C52—C53—C540.3 (4)
O21—C21—C28—C23179.7 (2)C52—C53—C54—C551.2 (4)
N21—C21—C28—C230.2 (2)C53—C54—C55—C562.0 (4)
S4—S3—N31—C3290.4 (2)C54—C55—C56—C511.3 (4)
S4—S3—N31—C31101.2 (2)C52—C51—C56—C550.3 (4)
C32—N31—C31—O31177.7 (2)C57—C51—C56—C55179.4 (2)
S3—N31—C31—O318.1 (3)C52—C51—C57—C5880.9 (4)
C32—N31—C31—C382.4 (2)C56—C51—C57—C5898.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C35—H35···O31i0.952.453.230 (3)140
C44—H44···O41ii0.952.483.258 (2)139
C46—H46···O220.952.443.249 (2)143
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+3/2, z+1/2.
(9) N,N'-Dithiophthalimide top
Crystal data top
C16H8N2O4S2F(000) = 728
Mr = 356.36Dx = 1.337 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 14.4180 (6) ÅCell parameters from 1993 reflections
b = 16.0502 (7) Åθ = 3.2–27.5°
c = 7.6616 (3) ŵ = 0.32 mm1
β = 93.369 (2)°T = 120 K
V = 1769.92 (13) Å3Block, colourless
Z = 40.10 × 0.10 × 0.08 mm
Data collection top
Kappa-CCD
diffractometer
1993 independent reflections
Radiation source: fine-focus sealed X-ray tube1633 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1818
Tmin = 0.969, Tmax = 0.975k = 1920
5857 measured reflectionsl = 89
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0708P)2 + 0.747P]
where P = (Fo2 + 2Fc2)/3
1993 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.56 e Å3
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
xyzUiso*/Ueq
S10.45335 (3)0.43029 (3)0.14438 (6)0.02559 (19)
N10.37127 (10)0.36113 (10)0.1932 (2)0.0250 (4)
C10.37362 (13)0.27454 (12)0.1518 (2)0.0268 (4)
O10.43557 (10)0.24085 (9)0.08144 (19)0.0328 (4)
C20.28882 (13)0.38302 (13)0.2784 (2)0.0268 (4)
O20.27199 (10)0.45160 (9)0.3303 (2)0.0362 (4)
C30.23485 (14)0.30446 (13)0.2849 (2)0.0286 (5)
C40.14930 (14)0.29010 (15)0.3534 (3)0.0339 (5)
C50.11631 (15)0.20843 (17)0.3485 (3)0.0410 (6)
C60.16707 (17)0.14456 (15)0.2784 (3)0.0401 (6)
C70.25319 (16)0.15902 (14)0.2083 (3)0.0345 (5)
C80.28509 (14)0.24047 (12)0.2134 (2)0.0277 (4)
H40.11470.33400.40160.041*
H50.05790.19630.39400.049*
H60.14280.08950.27800.048*
H70.28790.11530.15980.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0206 (3)0.0216 (3)0.0352 (3)0.00148 (17)0.0071 (2)0.00603 (18)
N10.0217 (8)0.0231 (8)0.0306 (8)0.0061 (6)0.0065 (6)0.0010 (6)
C10.0294 (10)0.0264 (10)0.0243 (9)0.0063 (8)0.0004 (8)0.0029 (7)
O10.0359 (8)0.0279 (8)0.0354 (8)0.0016 (6)0.0076 (6)0.0011 (6)
C20.0222 (9)0.0322 (11)0.0262 (9)0.0032 (8)0.0030 (7)0.0024 (8)
O20.0317 (8)0.0335 (8)0.0444 (9)0.0017 (6)0.0119 (7)0.0029 (7)
C30.0277 (10)0.0360 (11)0.0219 (9)0.0093 (8)0.0013 (7)0.0025 (8)
C40.0275 (10)0.0484 (13)0.0258 (10)0.0082 (9)0.0025 (8)0.0048 (9)
C50.0331 (12)0.0616 (16)0.0280 (10)0.0232 (11)0.0008 (9)0.0105 (10)
C60.0435 (13)0.0445 (13)0.0314 (11)0.0256 (11)0.0058 (9)0.0090 (10)
C70.0433 (12)0.0329 (11)0.0267 (10)0.0145 (9)0.0046 (9)0.0047 (8)
C80.0294 (10)0.0314 (10)0.0220 (9)0.0101 (8)0.0008 (8)0.0050 (8)
Geometric parameters (Å, º) top
S1—N11.681 (2)C3—C81.388 (3)
S1—S1i2.0428 (9)C4—C51.394 (3)
N1—C11.426 (3)C4—H40.9500
N1—C21.433 (2)C5—C61.386 (4)
C1—O11.199 (2)C5—H50.9500
C1—C81.491 (3)C6—C71.401 (3)
C2—O21.200 (2)C6—H60.9500
C2—C31.484 (3)C7—C81.386 (3)
C3—C41.388 (3)C7—H70.9500
N1—S1—S1i105.25 (6)C3—C4—H4121.5
C1—N1—C2111.8 (2)C5—C4—H4121.5
C1—N1—S1124.6 (2)C6—C5—C4121.3 (2)
C2—N1—S1123.6 (2)C6—C5—H5119.4
O1—C1—N1124.6 (2)C4—C5—H5119.4
O1—C1—C8130.7 (2)C5—C6—C7121.7 (2)
N1—C1—C8104.8 (2)C5—C6—H6119.1
O2—C2—N1124.4 (2)C7—C6—H6119.1
O2—C2—C3130.7 (2)C8—C7—C6116.5 (2)
N1—C2—C3104.9 (2)C8—C7—H7121.8
C4—C3—C8121.5 (2)C6—C7—H7121.8
C4—C3—C2129.3 (2)C7—C8—C3122.0 (2)
C8—C3—C2109.2 (2)C7—C8—C1128.8 (2)
C3—C4—C5117.1 (2)C3—C8—C1109.3 (2)
C1—N1—S1—S1i90.3 (2)N1—S1—S1i—N1i93.59 (8)
C2—N1—S1—S1i91.3 (2)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1ii0.952.553.344 (3)142
Symmetry code: (ii) x1/2, y+1/2, z+1/2.
(10) N,N'-Dithiodiphthalimide top
Crystal data top
C16H8N2O4S2F(000) = 728
Mr = 356.36Dx = 1.357 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 14.3752 (5) ÅCell parameters from 1974 reflections
b = 15.9349 (10) Åθ = 3.2–27.5°
c = 7.631 (10) ŵ = 0.33 mm1
β = 93.845 (2)°T = 120 K
V = 1744 (2) Å3Block, colourless
Z = 40.15 × 0.10 × 0.08 mm
Data collection top
Kappa-CCD
diffractometer
1974 independent reflections
Radiation source: fine-focus sealed X-ray tube1437 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1718
Tmin = 0.953, Tmax = 0.974k = 2020
5498 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0908P)2]
where P = (Fo2 + 2Fc2)/3
1974 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.66 e Å3
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
xyzUiso*/Ueq
S10.45331 (4)0.42910 (4)0.14377 (8)0.0327 (3)
N10.37002 (13)0.36043 (12)0.1929 (3)0.0316 (5)
C10.37124 (18)0.27298 (15)0.1537 (3)0.0349 (6)
O10.43325 (13)0.23770 (11)0.0852 (2)0.0426 (5)
C20.28837 (16)0.38382 (15)0.2762 (3)0.0338 (6)
O20.27204 (12)0.45353 (11)0.3267 (2)0.0421 (5)
C30.23349 (18)0.30530 (16)0.2848 (3)0.0367 (6)
C40.14755 (18)0.29256 (19)0.3544 (3)0.0419 (7)
C50.1135 (2)0.2100 (2)0.3504 (3)0.0481 (8)
C60.1628 (2)0.14529 (18)0.2812 (3)0.0487 (8)
C70.2491 (2)0.15860 (16)0.2104 (3)0.0426 (7)
C80.28220 (17)0.24009 (16)0.2143 (3)0.0351 (6)
H40.11370.33740.40200.050*
H50.05510.19860.39660.058*
H60.13770.09020.28150.058*
H70.28310.11400.16230.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0307 (4)0.0232 (4)0.0462 (4)0.0030 (2)0.0170 (3)0.0037 (2)
N10.0322 (10)0.0238 (10)0.0413 (11)0.0070 (8)0.0199 (9)0.0037 (8)
C10.0481 (14)0.0265 (13)0.0323 (13)0.0076 (11)0.0190 (11)0.0040 (10)
O10.0570 (11)0.0305 (10)0.0434 (10)0.0007 (8)0.0262 (9)0.0035 (8)
C20.0363 (13)0.0306 (13)0.0362 (13)0.0094 (10)0.0155 (11)0.0072 (10)
O20.0427 (10)0.0293 (10)0.0570 (12)0.0069 (8)0.0239 (9)0.0101 (8)
C30.0450 (14)0.0353 (14)0.0317 (12)0.0172 (12)0.0178 (11)0.0082 (10)
C40.0425 (15)0.0495 (17)0.0358 (14)0.0181 (12)0.0178 (11)0.0093 (12)
C50.0541 (16)0.0584 (19)0.0339 (14)0.0319 (15)0.0177 (12)0.0059 (13)
C60.0722 (19)0.0429 (16)0.0321 (14)0.0344 (15)0.0116 (13)0.0075 (12)
C70.0639 (17)0.0347 (14)0.0312 (13)0.0196 (13)0.0189 (13)0.0083 (11)
C80.0470 (14)0.0319 (13)0.0279 (12)0.0144 (11)0.0150 (11)0.0055 (10)
Geometric parameters (Å, º) top
S1—N11.683 (2)C3—C41.392 (3)
S1—S1i2.034 (2)C4—C51.403 (4)
N1—C21.422 (3)C4—H40.9500
N1—C11.426 (3)C5—C61.377 (5)
C1—O11.203 (3)C5—H50.9500
C1—C81.485 (3)C6—C71.403 (4)
C2—O21.204 (3)C6—H60.9500
C2—C31.483 (3)C7—C81.383 (3)
C3—C81.382 (4)C7—H70.9500
N1—S1—S1i105.30 (9)C3—C4—H4121.8
C2—N1—C1111.9 (2)C5—C4—H4121.8
C2—N1—S1123.4 (2)C6—C5—C4121.5 (2)
C1—N1—S1124.8 (2)C6—C5—H5119.2
O1—C1—N1124.6 (2)C4—C5—H5119.2
O1—C1—C8130.5 (2)C5—C6—C7121.7 (2)
N1—C1—C8104.9 (2)C5—C6—H6119.1
O2—C2—N1124.7 (2)C7—C6—H6119.1
O2—C2—C3130.4 (2)C8—C7—C6116.5 (3)
N1—C2—C3104.9 (2)C8—C7—H7121.8
C8—C3—C4121.6 (2)C6—C7—H7121.8
C8—C3—C2109.4 (2)C3—C8—C7122.1 (2)
C4—C3—C2128.9 (2)C3—C8—C1109.0 (2)
C3—C4—C5116.5 (3)C7—C8—C1128.8 (2)
C1—N1—S1—S1i90.0 (2)N1—S1—S1i—N1i95.2 (2)
C2—N1—S1—S1i91.4 (2)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1ii0.952.553.353 (5)142
Symmetry code: (ii) x1/2, 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
Mr = 409.44Dx = 1.518 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 14.2629 (5) ÅCell parameters from 4089 reflections
b = 16.1851 (4) Åθ = 2.9–29.8°
c = 7.7835 (2) ŵ = 0.33 mm1
β = 94.3917 (9)°T = 120 K
V = 1791.52 (9) Å3Block, colourless
Z = 40.25 × 0.15 × 0.10 mm
Data collection top
Kappa-CCD
diffractometer
4089 independent reflections
Radiation source: fine-focus sealed X-ray tube3275 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1418
Tmin = 0.922, Tmax = 0.968k = 2020
14107 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0651P)2 + 0.0637P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
4089 reflectionsΔρmax = 0.37 e Å3
255 parametersΔρmin = 0.44 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (2)
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
xyzUiso*/Ueq
S110.44791 (3)0.55977 (2)0.85382 (5)0.02330 (15)
N110.36024 (9)0.61984 (8)0.79190 (16)0.0197 (3)
C110.34979 (11)0.70516 (10)0.83041 (18)0.0179 (3)
O110.40523 (8)0.74560 (7)0.90378 (14)0.0251 (3)
C120.28322 (11)0.58913 (10)0.70206 (19)0.0188 (3)
O120.27727 (8)0.51960 (7)0.65138 (15)0.0295 (3)
C130.21971 (11)0.66113 (10)0.68942 (19)0.0184 (3)
C140.13444 (11)0.66653 (10)0.61582 (19)0.0220 (4)
C150.09067 (12)0.74383 (11)0.6185 (2)0.0244 (4)
C160.13126 (12)0.81247 (11)0.68982 (19)0.0225 (4)
C170.21709 (11)0.80689 (10)0.76358 (19)0.0195 (3)
C180.25971 (10)0.72993 (10)0.76244 (18)0.0168 (3)
S210.54868 (3)0.56149 (2)0.65421 (5)0.02299 (15)
N210.62227 (9)0.63917 (8)0.69718 (17)0.0206 (3)
C210.61083 (11)0.72280 (10)0.64417 (19)0.0192 (3)
O210.54461 (8)0.74750 (7)0.57230 (14)0.0263 (3)
C220.70568 (11)0.62875 (10)0.78474 (19)0.0190 (4)
O220.72926 (8)0.56534 (7)0.84908 (15)0.0251 (3)
C230.75191 (11)0.71100 (10)0.77728 (19)0.0176 (3)
C240.83635 (11)0.73462 (10)0.83965 (19)0.0212 (4)
C250.86181 (12)0.81752 (10)0.8206 (2)0.0234 (4)
C260.80422 (12)0.87378 (10)0.7429 (2)0.0237 (4)
C270.71934 (12)0.84895 (10)0.6794 (2)0.0216 (4)
C280.69480 (11)0.76677 (10)0.69752 (18)0.0183 (3)
C310.97302 (11)0.53536 (10)0.3443 (2)0.0204 (4)
C320.92293 (11)0.55176 (9)0.5017 (2)0.0216 (4)
C330.94951 (11)0.51713 (10)0.6542 (2)0.0205 (3)
C340.94193 (13)0.57073 (10)0.1796 (2)0.0263 (4)
H140.10360.62000.56290.026*
H150.02840.74840.56680.029*
H160.09850.86360.68670.027*
H170.24850.85350.81530.023*
H240.87880.69630.89610.025*
H250.92270.83460.86480.028*
H260.82330.92970.73330.028*
H270.67650.88690.62280.026*
H320.87040.58800.49390.026*
H330.91760.52770.75470.025*
H34A0.99240.56640.10140.040*
H34B0.92590.62900.19490.040*
H34C0.88640.54080.13070.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0149 (2)0.0213 (3)0.0325 (3)0.00118 (15)0.00616 (18)0.00755 (16)
N110.0129 (7)0.0196 (7)0.0251 (7)0.0007 (5)0.0076 (5)0.0022 (5)
C110.0161 (8)0.0192 (8)0.0179 (7)0.0015 (6)0.0028 (6)0.0012 (6)
O110.0206 (6)0.0242 (6)0.0284 (6)0.0039 (5)0.0120 (5)0.0000 (5)
C120.0140 (8)0.0197 (8)0.0220 (7)0.0031 (6)0.0033 (6)0.0036 (7)
O120.0244 (7)0.0195 (6)0.0424 (7)0.0023 (5)0.0120 (5)0.0011 (5)
C130.0137 (8)0.0215 (8)0.0194 (7)0.0032 (6)0.0023 (6)0.0028 (6)
C140.0165 (8)0.0275 (8)0.0209 (8)0.0045 (7)0.0053 (6)0.0020 (7)
C150.0150 (9)0.0340 (10)0.0230 (8)0.0010 (7)0.0056 (6)0.0041 (7)
C160.0193 (9)0.0269 (9)0.0209 (8)0.0064 (7)0.0015 (6)0.0036 (7)
C170.0185 (8)0.0203 (8)0.0193 (7)0.0007 (6)0.0018 (6)0.0003 (6)
C180.0130 (8)0.0207 (8)0.0161 (7)0.0018 (6)0.0027 (6)0.0023 (6)
S210.0156 (2)0.0188 (2)0.0335 (3)0.00016 (15)0.00514 (18)0.00611 (16)
N210.0140 (7)0.0177 (7)0.0287 (7)0.0004 (5)0.0077 (5)0.0021 (6)
C210.0182 (9)0.0200 (8)0.0192 (7)0.0029 (6)0.0002 (6)0.0014 (6)
O210.0203 (7)0.0282 (6)0.0287 (6)0.0059 (5)0.0080 (5)0.0003 (5)
C220.0144 (8)0.0191 (8)0.0232 (8)0.0011 (6)0.0017 (6)0.0036 (6)
O220.0207 (7)0.0185 (6)0.0344 (7)0.0017 (4)0.0084 (5)0.0002 (5)
C230.0164 (8)0.0181 (8)0.0182 (7)0.0008 (6)0.0003 (6)0.0023 (6)
C240.0188 (9)0.0230 (8)0.0212 (8)0.0012 (6)0.0024 (6)0.0023 (7)
C250.0224 (9)0.0245 (9)0.0229 (8)0.0037 (7)0.0003 (7)0.0046 (7)
C260.0275 (10)0.0177 (8)0.0258 (8)0.0038 (7)0.0015 (7)0.0020 (7)
C270.0240 (9)0.0190 (8)0.0217 (8)0.0029 (6)0.0001 (6)0.0002 (6)
C280.0177 (8)0.0198 (8)0.0172 (7)0.0012 (6)0.0003 (6)0.0023 (6)
C310.0185 (8)0.0144 (7)0.0273 (8)0.0033 (6)0.0052 (6)0.0004 (6)
C320.0158 (8)0.0165 (8)0.0316 (8)0.0015 (6)0.0043 (7)0.0011 (7)
C330.0182 (8)0.0187 (8)0.0243 (8)0.0018 (6)0.0007 (6)0.0036 (6)
C340.0258 (10)0.0252 (9)0.0270 (8)0.0023 (7)0.0044 (7)0.0010 (7)
Geometric parameters (Å, º) top
S11—N111.628 (2)C22—O221.180 (2)
S11—S212.1960 (6)C22—C231.489 (2)
N11—C121.351 (2)C23—C241.320 (2)
N11—C111.423 (2)C23—C281.337 (2)
C11—O111.145 (2)C24—C251.401 (2)
C11—C181.410 (2)C24—H240.9500
C12—O121.193 (2)C25—C261.339 (2)
C12—C131.475 (2)C25—H250.9500
C13—C141.307 (2)C26—C271.334 (2)
C13—C181.356 (2)C26—H260.9500
C14—C151.399 (2)C27—C281.385 (2)
C14—H140.9500C27—H270.9500
C15—C161.352 (2)C31—C33i1.393 (2)
C15—H150.9500C31—C341.442 (2)
C16—C171.315 (2)C31—C321.489 (2)
C16—H160.9500C32—C331.341 (2)
C17—C181.386 (2)C32—H320.9500
C17—H170.9500C33—C31i1.393 (2)
S21—N211.656 (2)C33—H330.9500
N21—C221.336 (2)C34—H34A0.9800
N21—C211.421 (2)C34—H34B0.9800
C21—O211.133 (2)C34—H34C0.9800
C21—C281.427 (2)
N11—S11—S21108.21 (5)O22—C22—C23133.0 (2)
C12—N11—C11111.8 (2)N21—C22—C23104.3 (2)
C12—N11—S11120.6 (2)C24—C23—C28118.8 (2)
C11—N11—S11127.4 (2)C24—C23—C22129.7 (2)
O11—C11—C18126.8 (2)C28—C23—C22111.5 (2)
O11—C11—N11125.5 (2)C23—C24—C25118.4 (2)
C18—C11—N11107.7 (2)C23—C24—H24120.8
O12—C12—N11123.5 (2)C25—C24—H24120.8
O12—C12—C13134.1 (2)C26—C25—C24123.0 (2)
N11—C12—C13102.4 (2)C26—C25—H25118.5
C14—C13—C18118.5 (2)C24—C25—H25118.5
C14—C13—C12128.9 (2)C27—C26—C25118.1 (2)
C18—C13—C12112.6 (2)C27—C26—H26121.0
C13—C14—C15117.0 (2)C25—C26—H26121.0
C13—C14—H14121.5C26—C27—C28118.7 (2)
C15—C14—H14121.5C26—C27—H27120.6
C16—C15—C14124.3 (2)C28—C27—H27120.6
C16—C15—H15117.9C23—C28—C27123.1 (2)
C14—C15—H15117.9C23—C28—C21105.5 (2)
C17—C16—C15118.6 (2)C27—C28—C21131.5 (2)
C17—C16—H16120.7C33i—C31—C34116.1 (2)
C15—C16—H16120.7C33i—C31—C32122.2 (2)
C16—C17—C18116.9 (2)C34—C31—C32121.8 (2)
C16—C17—H17121.5C33—C32—C31122.2 (2)
C18—C17—H17121.5C33—C32—H32118.9
C13—C18—C17124.7 (2)C31—C32—H32118.9
C13—C18—C11105.4 (2)C32—C33—C31i115.6 (2)
C17—C18—C11129.8 (2)C32—C33—H33122.2
N21—S21—S11107.81 (5)C31i—C33—H33122.2
C22—N21—C21110.3 (2)C31—C34—H34A109.5
C22—N21—S21122.2 (2)C31—C34—H34B109.5
C21—N21—S21127.4 (2)H34A—C34—H34B109.5
O21—C21—N21123.5 (2)C31—C34—H34C109.5
O21—C21—C28128.1 (2)H34A—C34—H34C109.5
N21—C21—C28108.4 (2)H34B—C34—H34C109.5
O22—C22—N21122.7 (2)
S21—S11—N11—C1292.1 (2)S11—S21—N21—C2187.3 (2)
S21—S11—N11—C1192.4 (2)C22—N21—C21—O21177.6 (2)
C12—N11—C11—O11179.3 (2)S21—N21—C21—O215.2 (2)
S11—N11—C11—O114.9 (2)C22—N21—C21—C282.2 (2)
C12—N11—C11—C180.8 (2)S21—N21—C21—C28175.1 (2)
S11—N11—C11—C18175.1 (2)C21—N21—C22—O22176.2 (2)
C11—N11—C12—O12177.7 (2)S21—N21—C22—O226.3 (2)
S11—N11—C12—O126.1 (2)C21—N21—C22—C233.2 (2)
C11—N11—C12—C131.7 (2)S21—N21—C22—C23174.1 (2)
S11—N11—C12—C13174.5 (2)O22—C22—C23—C242.3 (3)
O12—C12—C13—C141.0 (3)N21—C22—C23—C24178.3 (2)
N11—C12—C13—C14179.6 (2)O22—C22—C23—C28176.0 (2)
O12—C12—C13—C18177.2 (2)N21—C22—C23—C283.5 (2)
N11—C12—C13—C182.2 (2)C28—C23—C24—C250.6 (2)
C18—C13—C14—C150.1 (2)C22—C23—C24—C25177.5 (2)
C12—C13—C14—C15178.2 (2)C23—C24—C25—C260.4 (2)
C13—C14—C15—C160.9 (2)C24—C25—C26—C270.8 (2)
C14—C15—C16—C170.8 (3)C25—C26—C27—C280.3 (2)
C15—C16—C17—C180.1 (2)C24—C23—C28—C271.1 (2)
C14—C13—C18—C170.8 (2)C22—C23—C28—C27177.4 (2)
C12—C13—C18—C17177.6 (2)C24—C23—C28—C21179.4 (2)
C14—C13—C18—C11179.9 (2)C22—C23—C28—C212.1 (2)
C12—C13—C18—C111.8 (2)C26—C27—C28—C230.6 (2)
C16—C17—C18—C130.8 (2)C26—C27—C28—C21180.0 (2)
C16—C17—C18—C11179.9 (2)O21—C21—C28—C23179.9 (2)
O11—C11—C18—C13179.3 (2)N21—C21—C28—C230.1 (2)
N11—C11—C18—C130.6 (2)O21—C21—C28—C270.4 (3)
O11—C11—C18—C171.4 (3)N21—C21—C28—C27179.4 (2)
N11—C11—C18—C17178.7 (2)C33i—C31—C32—C330.1 (3)
N11—S11—S21—N2188.19 (7)C34—C31—C32—C33177.9 (2)
S11—S21—N21—C2295.7 (2)C31—C32—C33—C31i0.1 (2)
Symmetry code: (i) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O11ii0.952.093.023 (2)168
C26—H26···O22iii0.952.393.209 (2)144
Symmetry codes: (ii) x1/2, y+3/2, z1/2; (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
Mr = 402.45Dx = 1.508 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 14.3126 (4) ÅCell parameters from 3467 reflections
b = 16.1270 (4) Åθ = 2.9–28.0°
c = 7.6990 (2) ŵ = 0.33 mm1
β = 94.3216 (13)°T = 120 K
V = 1772.03 (8) Å3Block, colourless
Z = 40.25 × 0.10 × 0.10 mm
Data collection top
Kappa-CCD
diffractometer
3467 independent reflections
Radiation source: fine-focus sealed X-ray tube2827 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ scans and ω scans with κ offsetsθmax = 26.1°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1717
Tmin = 0.922, Tmax = 0.968k = 1919
9295 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0598P)2 + 0.3414P]
where P = (Fo2 + 2Fc2)/3
3467 reflections(Δ/σ)max = 0.013
254 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.41 e Å3
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
xyzUiso*/UeqOcc. (<1)
S110.45099 (3)0.56413 (3)0.84701 (6)0.02201 (15)
N110.36287 (9)0.62401 (9)0.78652 (18)0.0183 (3)
C110.35383 (11)0.71011 (10)0.8215 (2)0.0177 (4)
O110.41027 (8)0.75112 (7)0.89157 (16)0.0254 (3)
C120.28390 (11)0.59261 (11)0.7018 (2)0.0181 (4)
O120.27627 (9)0.52211 (7)0.65630 (17)0.0280 (3)
C130.22172 (11)0.66510 (10)0.6876 (2)0.0171 (4)
C140.13540 (12)0.67066 (11)0.6173 (2)0.0218 (4)
C150.09288 (12)0.74823 (11)0.6175 (2)0.0243 (4)
C160.13516 (12)0.81782 (11)0.6836 (2)0.0222 (4)
C170.22203 (12)0.81232 (11)0.7543 (2)0.0200 (4)
C180.26316 (11)0.73477 (10)0.7558 (2)0.0168 (4)
S210.54978 (3)0.56663 (3)0.64296 (6)0.02252 (15)
N210.62373 (10)0.64399 (9)0.68640 (19)0.0200 (3)
C210.61335 (12)0.72849 (11)0.6353 (2)0.0195 (4)
O210.54773 (9)0.75469 (8)0.56332 (16)0.0270 (3)
C220.70713 (11)0.63222 (11)0.7743 (2)0.0180 (4)
O220.72952 (9)0.56787 (7)0.83850 (17)0.0251 (3)
C230.75400 (11)0.71398 (10)0.7688 (2)0.0170 (4)
C240.83880 (12)0.73624 (11)0.8317 (2)0.0197 (4)
C250.86557 (13)0.81908 (11)0.8146 (2)0.0228 (4)
C260.80857 (13)0.87663 (11)0.7380 (2)0.0235 (4)
C270.72397 (13)0.85359 (11)0.6737 (2)0.0212 (4)
C280.69815 (11)0.77117 (10)0.6900 (2)0.0177 (4)
C310.97524 (13)0.53541 (13)0.3440 (3)0.0312 (5)
C320.92401 (13)0.55233 (12)0.5000 (3)0.0319 (5)
C330.94843 (13)0.51694 (12)0.6542 (3)0.0289 (4)
C340.9462 (3)0.5640 (3)0.1649 (5)0.0336 (10)0.50
H140.10330.62360.56830.026*
H150.03020.75270.56820.029*
H160.10310.86940.67920.027*
H170.25460.85940.80190.024*
H240.88050.69690.88710.024*
H250.92660.83530.85900.027*
H260.82840.93260.73000.028*
H270.68200.89260.61780.025*
H310.95460.56180.23760.037*0.50
H320.87230.58940.49050.038*
H330.91560.52710.75480.035*
H34A0.99480.54960.08700.050*0.50
H34B0.93740.62430.16520.050*0.50
H34C0.88720.53700.12420.050*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0147 (3)0.0193 (3)0.0309 (3)0.00157 (17)0.00561 (19)0.00599 (17)
N110.0123 (7)0.0168 (7)0.0245 (8)0.0004 (6)0.0073 (6)0.0023 (6)
C110.0161 (8)0.0180 (9)0.0184 (9)0.0010 (7)0.0027 (7)0.0007 (7)
O110.0210 (7)0.0224 (7)0.0304 (7)0.0030 (6)0.0132 (5)0.0021 (5)
C120.0138 (8)0.0200 (9)0.0199 (9)0.0039 (7)0.0025 (7)0.0028 (7)
O120.0258 (7)0.0180 (7)0.0383 (8)0.0029 (6)0.0109 (6)0.0017 (6)
C130.0138 (8)0.0207 (9)0.0165 (8)0.0022 (7)0.0013 (7)0.0016 (7)
C140.0157 (8)0.0294 (10)0.0195 (9)0.0052 (8)0.0043 (7)0.0014 (7)
C150.0155 (9)0.0360 (11)0.0202 (9)0.0038 (8)0.0059 (7)0.0037 (8)
C160.0193 (9)0.0262 (10)0.0208 (9)0.0098 (8)0.0015 (7)0.0026 (7)
C170.0199 (9)0.0208 (9)0.0187 (9)0.0023 (7)0.0031 (7)0.0004 (7)
C180.0139 (8)0.0209 (9)0.0151 (8)0.0014 (7)0.0026 (7)0.0015 (7)
S210.0150 (3)0.0193 (3)0.0323 (3)0.00033 (17)0.0041 (2)0.00819 (17)
N210.0148 (7)0.0168 (7)0.0271 (8)0.0002 (6)0.0059 (6)0.0030 (6)
C210.0180 (9)0.0214 (9)0.0192 (9)0.0032 (8)0.0014 (7)0.0020 (7)
O210.0221 (7)0.0306 (7)0.0268 (7)0.0070 (6)0.0073 (5)0.0003 (6)
C220.0128 (8)0.0192 (9)0.0216 (9)0.0017 (7)0.0018 (7)0.0046 (7)
O220.0218 (7)0.0172 (7)0.0348 (8)0.0019 (5)0.0083 (6)0.0002 (5)
C230.0169 (8)0.0166 (8)0.0176 (9)0.0016 (7)0.0004 (7)0.0035 (7)
C240.0181 (9)0.0200 (9)0.0205 (9)0.0004 (7)0.0018 (7)0.0022 (7)
C250.0205 (9)0.0244 (9)0.0233 (10)0.0056 (8)0.0007 (7)0.0056 (7)
C260.0286 (10)0.0169 (9)0.0251 (10)0.0035 (8)0.0034 (8)0.0015 (7)
C270.0251 (9)0.0179 (9)0.0209 (9)0.0031 (8)0.0031 (7)0.0002 (7)
C280.0169 (8)0.0191 (9)0.0169 (9)0.0024 (7)0.0003 (7)0.0019 (7)
C310.0235 (10)0.0315 (11)0.0369 (12)0.0051 (9)0.0085 (8)0.0135 (9)
C320.0198 (10)0.0278 (10)0.0464 (13)0.0014 (8)0.0081 (9)0.0092 (9)
C330.0225 (10)0.0312 (10)0.0328 (11)0.0063 (9)0.0000 (8)0.0057 (9)
C340.033 (2)0.037 (2)0.030 (2)0.0008 (18)0.0039 (18)0.0098 (17)
Geometric parameters (Å, º) top
S11—N111.628 (2)C22—O221.183 (2)
S11—S212.1918 (7)C22—C231.481 (2)
N11—C121.360 (2)C23—C241.322 (2)
N11—C111.422 (2)C23—C281.336 (2)
C11—O111.147 (2)C24—C251.399 (3)
C11—C181.414 (2)C24—H240.9500
C12—O121.192 (2)C25—C261.342 (3)
C12—C131.468 (2)C25—H250.9500
C13—C141.314 (2)C26—C271.326 (3)
C13—C181.358 (2)C26—H260.9500
C14—C151.391 (3)C27—C281.388 (2)
C14—H140.9500C27—H270.9500
C15—C161.356 (3)C31—C33i1.380 (3)
C15—H150.9500C31—C341.483 (4)
C16—C171.322 (2)C31—C321.479 (3)
C16—H160.9500C31—H310.9500
C17—C181.382 (2)C32—C331.340 (3)
C17—H170.9500C32—H320.9500
S21—N211.654 (2)C33—C31i1.380 (3)
N21—C221.341 (2)C33—H330.9500
N21—C211.423 (2)C34—H34A0.9800
C21—O211.136 (2)C34—H34B0.9800
C21—C281.431 (2)C34—H34C0.9800
N11—S11—S21108.16 (6)N21—C22—C23104.3 (2)
C12—N11—C11111.7 (2)C24—C23—C28118.7 (2)
C12—N11—S11121.0 (2)C24—C23—C22129.5 (2)
C11—N11—S11127.2 (2)C28—C23—C22111.8 (2)
O11—C11—C18127.0 (2)C23—C24—C25118.4 (2)
O11—C11—N11125.5 (2)C23—C24—H24120.8
C18—C11—N11107.5 (2)C25—C24—H24120.8
O12—C12—N11123.4 (2)C26—C25—C24122.7 (2)
O12—C12—C13134.1 (2)C26—C25—H25118.7
N11—C12—C13102.5 (2)C24—C25—H25118.7
C14—C13—C18118.2 (2)C27—C26—C25118.5 (2)
C14—C13—C12129.1 (2)C27—C26—H26120.7
C18—C13—C12112.7 (2)C25—C26—H26120.7
C13—C14—C15117.3 (2)C26—C27—C28118.5 (2)
C13—C14—H14121.3C26—C27—H27120.8
C15—C14—H14121.3C28—C27—H27120.8
C16—C15—C14124.2 (2)C23—C28—C27123.2 (2)
C16—C15—H15117.9C23—C28—C21105.5 (2)
C14—C15—H15117.9C27—C28—C21131.3 (2)
C17—C16—C15118.6 (2)C33i—C31—C34111.4 (2)
C17—C16—H16120.7C33i—C31—C32123.1 (2)
C15—C16—H16120.7C34—C31—C32125.2 (2)
C16—C17—C18116.8 (2)C33i—C31—H31118.5
C16—C17—H17121.6C32—C31—H31118.5
C18—C17—H17121.6C33—C32—C31121.9 (2)
C13—C18—C17124.9 (2)C33—C32—H32119.0
C13—C18—C11105.6 (2)C31—C32—H32119.0
C17—C18—C11129.5 (2)C32—C33—C31i115.0 (2)
N21—S21—S11107.85 (6)C32—C33—H33122.5
C22—N21—C21110.2 (2)C31i—C33—H33122.5
C22—N21—S21121.8 (2)C31—C34—H34A109.5
C21—N21—S21127.9 (2)C31—C34—H34B109.5
O21—C21—N21123.8 (2)H34A—C34—H34B109.5
O21—C21—C28128.1 (2)C31—C34—H34C109.5
N21—C21—C28108.1 (2)H34A—C34—H34C109.5
O22—C22—N21122.5 (2)H34B—C34—H34C109.5
O22—C22—C23133.1 (2)
S21—S11—N11—C1294.3 (2)S11—S21—N21—C2187.5 (2)
S21—S11—N11—C1190.2 (2)C22—N21—C21—O21177.8 (2)
C12—N11—C11—O11179.9 (2)S21—N21—C21—O214.6 (3)
S11—N11—C11—O113.9 (3)C22—N21—C21—C282.4 (2)
C12—N11—C11—C180.4 (2)S21—N21—C21—C28175.2 (2)
S11—N11—C11—C18175.5 (2)C21—N21—C22—O22175.7 (2)
C11—N11—C12—O12178.5 (2)S21—N21—C22—O226.6 (2)
S11—N11—C12—O125.3 (2)C21—N21—C22—C233.3 (2)
C11—N11—C12—C131.2 (2)S21—N21—C22—C23174.5 (2)
S11—N11—C12—C13175.1 (2)O22—C22—C23—C243.2 (3)
O12—C12—C13—C140.7 (3)N21—C22—C23—C24178.0 (2)
N11—C12—C13—C14179.7 (2)O22—C22—C23—C28175.5 (2)
O12—C12—C13—C18178.0 (2)N21—C22—C23—C283.3 (2)
N11—C12—C13—C181.6 (2)C28—C23—C24—C250.9 (3)
C18—C13—C14—C150.3 (3)C22—C23—C24—C25177.8 (2)
C12—C13—C14—C15178.4 (2)C23—C24—C25—C260.3 (3)
C13—C14—C15—C160.7 (3)C24—C25—C26—C271.0 (3)
C14—C15—C16—C170.7 (3)C25—C26—C27—C280.5 (3)
C15—C16—C17—C180.3 (3)C24—C23—C28—C271.4 (3)
C14—C13—C18—C171.3 (3)C22—C23—C28—C27177.5 (2)
C12—C13—C18—C17177.6 (2)C24—C23—C28—C21179.3 (2)
C14—C13—C18—C11179.8 (2)C22—C23—C28—C211.9 (2)
C12—C13—C18—C111.4 (2)C26—C27—C28—C230.7 (3)
C16—C17—C18—C131.3 (3)C26—C27—C28—C21179.8 (2)
C16—C17—C18—C11180.0 (2)O21—C21—C28—C23180.0 (2)
O11—C11—C18—C13178.9 (2)N21—C21—C28—C230.2 (2)
N11—C11—C18—C130.6 (2)O21—C21—C28—C270.7 (3)
O11—C11—C18—C172.3 (3)N21—C21—C28—C27179.5 (2)
N11—C11—C18—C17178.3 (2)C33i—C31—C32—C330.5 (3)
N11—S11—S21—N2189.05 (8)C34—C31—C32—C33172.4 (3)
S11—S21—N21—C2295.1 (2)C31—C32—C33—C31i0.5 (3)
Symmetry code: (i) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O11ii0.952.113.029 (2)163
C26—H26···O22iii0.952.383.179 (2)142
Symmetry codes: (ii) x1/2, y+3/2, z1/2; (iii) x+3/2, y+1/2, z+3/2.
 

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