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In each of the asymmetrically substituted disulfides 2-nitro-4′-methyldiphenyl disulfide, C13H11NO2S2 (1), 2-nitro-4′-chloro­diphenyl disulfide, C12H8ClNO2S2 (2), 2,4-dinitro-4′-methyldiphenyl disulfide, C13H10N2O4S2 (3), and 2,4-dinitrophenyl-2′-methoxycarbonylmethyl disulfide, C9H8N2O6S2 (4), and in both of the symmetrically substituted disulfides bis(2-nitrophenyl) disulfide, C12H8N2O4S2 (5), and bis(2-nitro-4-trifluoro­methylphenyl) disulfide, C14H6F6N2O4S2 (6), the 2-nitro groups are essentially coplanar with the adjacent aryl ring and the S atom remote from the nitrated aryl ring is also essentially coplanar and transoid to the nitro group. In S-(2-nitrophenyl) 2-nitrobenzene thiosulfonate, C12H8N2O6S2 (7), which contains three independent molecules in the asymmetric unit, all six of the independent nitro groups are twisted out of the plane of the adjacent aryl rings. The crystal structures of (1)–(3) contain isolated molecules, that of (4) contains centrosymmetric dimers held together by C—H...O hydrogen bonds, while in the structures of (5)—(7), respectively, the C—H...O hydrogen bonds generate one-, two- and three-dimensional arrays. The interplay between molecular conformation and supramolecular aggregation is discussed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100007114/na0107sup1.cif
Contains datablocks global, 1, 2, 3, 4, 5, 6, 7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007114/na01071sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007114/na01072sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007114/na01073sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007114/na01074sup5.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007114/na01075sup6.hkl
Contains datablock 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007114/na01076sup7.hkl
Contains datablock 6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100007114/na01077sup8.hkl
Contains datablock 7

CCDC references: 153341; 153342; 153343; 153344; 153345; 153346; 153347

Comment top

Comment in full text version

Experimental top

Synthesis in full text version

Refinement top

See full text version

Computing details top

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP (Johnson, 1976), PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top
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In full text version
(1) 2-Nitro-4'-methyldiphenyl disulfide top
Crystal data top
C13H11NO2S2F(000) = 576
Mr = 277.35Dx = 1.432 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.6384 (2) ÅCell parameters from 2935 reflections
b = 24.4389 (7) Åθ = 1.7–27.4°
c = 7.9478 (3) ŵ = 0.41 mm1
β = 93.6346 (10)°T = 150 K
V = 1286.82 (7) Å3Block, yellow
Z = 40.25 × 0.20 × 0.10 mm
Data collection top
Kappa-CCD
diffractometer
2935 independent reflections
Radiation source: fine-focus sealed X-ray tube1639 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
ϕ scans and ω scans with κ offsetsθmax = 27.4°, θmin = 1.7°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 88
Tmin = 0.905, Tmax = 0.961k = 3131
13605 measured reflectionsl = 1010
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) = 0.147H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0738P)2]
where P = (Fo2 + 2Fc2)/3
2935 reflections(Δ/σ)max = 0.001
164 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C13H11NO2S2V = 1286.82 (7) Å3
Mr = 277.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.6384 (2) ŵ = 0.41 mm1
b = 24.4389 (7) ÅT = 150 K
c = 7.9478 (3) Å0.25 × 0.20 × 0.10 mm
β = 93.6346 (10)°
Data collection top
Kappa-CCD
diffractometer
2935 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
1639 reflections with I > 2σ(I)
Tmin = 0.905, Tmax = 0.961Rint = 0.072
13605 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.03Δρmax = 0.23 e Å3
2935 reflectionsΔρmin = 0.25 e Å3
164 parameters
Special details top

Experimental. Kappa CCD diffractometer using the following programs. Collect: Data collection software, Hooft, 1998, is a graphical user interface written by Enraf–Nonius which encompasses the following programs. DENZO (Otwinowski and Minor, 1997) and indexing and data collection software package and a scaling package, SCALEPACK both of which programs are produced by the company HKL. Absorption corrections are performed by the SORTAV package, Blessing, 1995 and Blessing, 1997. 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. Low temperature data is collected using an Oxford Cryosystems cryostream, Cosier and Glazer, 1986.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.20408 (10)0.56546 (3)0.30150 (9)0.0696 (3)
S20.05205 (9)0.63845 (3)0.31321 (9)0.0659 (3)
C110.3654 (3)0.56755 (9)0.4884 (3)0.0545 (6)
C120.2964 (4)0.55147 (11)0.6414 (4)0.0681 (7)
C130.4224 (4)0.55274 (11)0.7852 (4)0.0716 (8)
C140.6219 (4)0.56912 (10)0.7816 (3)0.0610 (7)
C150.6889 (4)0.58499 (12)0.6283 (4)0.0659 (7)
C160.5642 (3)0.58387 (11)0.4836 (3)0.0631 (7)
C1410.7634 (4)0.56926 (12)0.9382 (4)0.0809 (9)
C210.2108 (3)0.68762 (10)0.2224 (3)0.0524 (6)
C220.1752 (4)0.74342 (12)0.2309 (3)0.0623 (7)
C230.3051 (5)0.78207 (12)0.1674 (4)0.0784 (9)
C240.4735 (5)0.76482 (14)0.0911 (4)0.0803 (9)
C250.5092 (4)0.71019 (13)0.0762 (3)0.0704 (8)
C260.3817 (4)0.67193 (12)0.1400 (3)0.0610 (7)
N220.0005 (5)0.76411 (14)0.3107 (3)0.0846 (8)
O2210.1195 (3)0.73069 (12)0.3618 (3)0.1044 (8)
O2220.0218 (4)0.81352 (12)0.3256 (3)0.1313 (10)
H120.16370.53970.64690.082*
H130.37270.54240.88730.086*
H150.82160.59670.62270.079*
H160.61400.59420.38160.076*
H14A0.89420.58180.91010.121*0.50
H14B0.77450.53280.98320.121*0.50
H14C0.71160.59321.02080.121*0.50
H14D0.69260.55681.03260.121*0.50
H14E0.81240.60570.95960.121*0.50
H14F0.87530.54530.92200.121*0.50
H230.27780.81920.17680.094*
H240.56250.79020.05000.096*
H250.62160.69850.02190.084*
H260.41000.63490.12810.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0775 (5)0.0550 (5)0.0750 (5)0.0089 (3)0.0060 (4)0.0064 (4)
S20.0507 (4)0.0754 (6)0.0712 (5)0.0005 (3)0.0007 (3)0.0013 (4)
C110.0611 (14)0.0408 (15)0.0617 (16)0.0012 (11)0.0054 (12)0.0020 (12)
C120.0622 (15)0.0628 (19)0.080 (2)0.0066 (13)0.0085 (14)0.0105 (15)
C130.0848 (19)0.063 (2)0.0685 (19)0.0036 (15)0.0154 (15)0.0097 (15)
C140.0782 (17)0.0417 (16)0.0629 (18)0.0030 (12)0.0025 (14)0.0005 (13)
C150.0601 (14)0.0641 (19)0.073 (2)0.0050 (13)0.0022 (13)0.0056 (15)
C160.0623 (15)0.0669 (19)0.0611 (17)0.0042 (13)0.0103 (13)0.0066 (14)
C1410.105 (2)0.062 (2)0.073 (2)0.0040 (15)0.0112 (17)0.0021 (15)
C210.0510 (13)0.0577 (17)0.0473 (14)0.0057 (12)0.0076 (10)0.0019 (12)
C220.0722 (16)0.0615 (19)0.0509 (16)0.0180 (14)0.0138 (13)0.0041 (14)
C230.123 (3)0.0494 (19)0.0589 (18)0.0121 (18)0.0224 (17)0.0051 (14)
C240.098 (2)0.077 (2)0.065 (2)0.0104 (18)0.0089 (17)0.0191 (17)
C250.0724 (17)0.075 (2)0.0630 (18)0.0039 (15)0.0032 (13)0.0146 (16)
C260.0663 (15)0.0539 (17)0.0626 (17)0.0062 (13)0.0034 (13)0.0024 (13)
N220.101 (2)0.089 (2)0.0613 (16)0.0453 (17)0.0129 (14)0.0099 (15)
O2210.0760 (15)0.125 (2)0.113 (2)0.0366 (14)0.0112 (13)0.0130 (16)
O2220.178 (2)0.091 (2)0.125 (2)0.0727 (19)0.0115 (17)0.0178 (15)
Geometric parameters (Å, º) top
S1—S22.0544 (10)C141—H14B0.9600
S1—C111.776 (3)C141—H14C0.9600
S2—C211.781 (2)C141—H14D0.9600
N22—O2211.224 (4)C141—H14E0.9600
N22—O2221.222 (4)C141—H14F0.9600
C11—C161.381 (3)C21—C221.386 (4)
C11—C121.384 (4)C21—C261.399 (3)
C12—C131.373 (4)C22—C231.395 (4)
C12—H120.9300C22—N221.453 (4)
C13—C141.386 (3)C23—C241.371 (4)
C13—H130.9300C23—H230.9300
C14—C151.379 (4)C24—C251.363 (4)
C14—C1411.511 (4)C24—H240.9300
C15—C161.374 (3)C25—C261.379 (4)
C15—H150.9300C25—H250.9300
C16—H160.9300C26—H260.9300
C141—H14A0.9600
C11—S1—S2102.07 (8)H14B—C141—H14D56.3
C21—S2—S1105.22 (8)H14C—C141—H14D56.3
O221—N22—O222123.1 (3)C14—C141—H14E109.5
O221—N22—C22117.7 (3)H14A—C141—H14E56.3
O222—N22—C22119.1 (3)H14B—C141—H14E141.1
C16—C11—C12118.5 (2)H14C—C141—H14E56.3
C16—C11—S1120.8 (2)H14D—C141—H14E109.5
C12—C11—S1120.73 (19)C14—C141—H14F109.5
C13—C12—C11120.4 (2)H14A—C141—H14F56.3
C13—C12—H12119.8H14B—C141—H14F56.3
C11—C12—H12119.8H14C—C141—H14F141.1
C12—C13—C14121.5 (3)H14D—C141—H14F109.5
C12—C13—H13119.3H14E—C141—H14F109.5
C14—C13—H13119.3C22—C21—C26116.0 (2)
C15—C14—C13117.5 (2)C22—C21—S2122.5 (2)
C15—C14—C141120.6 (3)C26—C21—S2121.5 (2)
C13—C14—C141121.9 (2)C21—C22—C23122.5 (3)
C16—C15—C14121.5 (2)C21—C22—N22120.5 (3)
C16—C15—H15119.2C23—C22—N22117.0 (3)
C14—C15—H15119.2C24—C23—C22119.5 (3)
C15—C16—C11120.6 (2)C24—C23—H23120.3
C15—C16—H16119.7C22—C23—H23120.3
C11—C16—H16119.7C25—C24—C23119.4 (3)
C14—C141—H14A109.5C25—C24—H24120.3
C14—C141—H14B109.5C23—C24—H24120.3
H14A—C141—H14B109.5C24—C25—C26121.2 (3)
C14—C141—H14C109.5C24—C25—H25119.4
H14A—C141—H14C109.5C26—C25—H25119.4
H14B—C141—H14C109.5C25—C26—C21121.4 (3)
C14—C141—H14D109.5C25—C26—H26119.3
H14A—C141—H14D141.1C21—C26—H26119.3
C11—S1—S2—C2185.36 (12)C141—C14—C15—C16178.4 (2)
S2—S1—C11—C1698.0 (2)C14—C15—C16—C111.1 (4)
S2—S1—C11—C1283.8 (2)C12—C11—C16—C151.2 (4)
S1—S2—C21—C22169.75 (17)S1—C11—C16—C15179.5 (2)
S1—S2—C21—C269.3 (2)C26—C21—C22—C232.4 (3)
C21—C22—N22—O2213.6 (4)S2—C21—C22—C23176.62 (19)
C23—C22—N22—O221177.6 (2)C26—C21—C22—N22178.8 (2)
C21—C22—N22—O222175.6 (2)S2—C21—C22—N222.2 (3)
C23—C22—N22—O2223.3 (4)C21—C22—C23—C241.0 (4)
C16—C11—C12—C131.1 (4)N22—C22—C23—C24179.9 (2)
S1—C11—C12—C13179.4 (2)C22—C23—C24—C251.1 (4)
C11—C12—C13—C141.1 (4)C23—C24—C25—C261.6 (4)
C12—C13—C14—C151.0 (4)C24—C25—C26—C210.1 (4)
C12—C13—C14—C141178.4 (2)C22—C21—C26—C251.9 (3)
C13—C14—C15—C161.0 (4)S2—C21—C26—C25177.17 (19)
(2) 2-Nitro-4'-chlorodiphenyl disulfide top
Crystal data top
C12H8ClNO2S2Z = 2
Mr = 297.76F(000) = 304
Triclinic, P1Dx = 1.619 Mg m3
a = 7.0434 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.8315 (5) ÅCell parameters from 2960 reflections
c = 11.3709 (8) Åθ = 2.9–30.2°
α = 82.576 (4)°µ = 0.65 mm1
β = 80.690 (3)°T = 150 K
γ = 83.189 (3)°Plate, yellow
V = 610.71 (7) Å30.20 × 0.15 × 0.02 mm
Data collection top
Kappa-CCD
diffractometer
2960 independent reflections
Radiation source: fine-focus sealed X-ray tube2327 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ scans and ω scans with κ offsetsθmax = 28.5°, θmin = 2.9°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 99
Tmin = 0.882, Tmax = 0.987k = 1010
6846 measured reflectionsl = 1315
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0627P)2]
where P = (Fo2 + 2Fc2)/3
2960 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C12H8ClNO2S2γ = 83.189 (3)°
Mr = 297.76V = 610.71 (7) Å3
Triclinic, P1Z = 2
a = 7.0434 (5) ÅMo Kα radiation
b = 7.8315 (5) ŵ = 0.65 mm1
c = 11.3709 (8) ÅT = 150 K
α = 82.576 (4)°0.20 × 0.15 × 0.02 mm
β = 80.690 (3)°
Data collection top
Kappa-CCD
diffractometer
2960 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
2327 reflections with I > 2σ(I)
Tmin = 0.882, Tmax = 0.987Rint = 0.036
6846 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.05Δρmax = 0.40 e Å3
2960 reflectionsΔρmin = 0.42 e Å3
163 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.14074 (7)0.39829 (6)0.17396 (4)0.02787 (16)
S20.21248 (7)0.46708 (6)0.32690 (4)0.02647 (16)
C110.3636 (3)0.3184 (2)0.09132 (17)0.0242 (4)
C120.5407 (3)0.2980 (3)0.13321 (19)0.0287 (5)
C130.7061 (3)0.2329 (3)0.06260 (19)0.0294 (5)
C140.6923 (3)0.1898 (2)0.04922 (17)0.0257 (4)
Cl140.90005 (8)0.11244 (7)0.14014 (5)0.03490 (17)
C150.5176 (3)0.2095 (3)0.09223 (18)0.0306 (5)
C160.3525 (3)0.2743 (3)0.02186 (18)0.0293 (5)
C210.2325 (3)0.2669 (2)0.42179 (17)0.0235 (4)
C220.2571 (3)0.2587 (2)0.54267 (17)0.0236 (4)
N220.2733 (2)0.4162 (2)0.59494 (15)0.0268 (4)
O2210.2768 (2)0.55227 (18)0.52754 (13)0.0376 (4)
O2220.2815 (2)0.40748 (19)0.70217 (13)0.0375 (4)
C230.2692 (3)0.1042 (3)0.61713 (18)0.0273 (4)
C240.2599 (3)0.0492 (3)0.57190 (18)0.0286 (5)
C250.2389 (3)0.0456 (3)0.45267 (18)0.0285 (5)
C260.2253 (3)0.1084 (2)0.37904 (18)0.0265 (4)
H120.54840.32880.21030.034*
H130.82740.21820.09100.035*
H150.51090.17880.16950.037*
H160.23170.28860.05080.035*
H230.28370.10400.69880.033*
H240.26790.15590.62190.034*
H250.23370.15110.42100.034*
H260.21070.10680.29760.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0271 (3)0.0306 (3)0.0251 (3)0.0001 (2)0.0043 (2)0.0021 (2)
S20.0318 (3)0.0214 (3)0.0249 (3)0.00147 (19)0.0023 (2)0.0014 (2)
C110.0289 (11)0.0214 (9)0.0216 (9)0.0052 (8)0.0027 (8)0.0008 (8)
C120.0311 (11)0.0311 (11)0.0247 (10)0.0034 (9)0.0049 (9)0.0051 (9)
C130.0268 (11)0.0302 (11)0.0319 (11)0.0017 (8)0.0072 (9)0.0036 (9)
C140.0294 (11)0.0226 (10)0.0239 (10)0.0033 (8)0.0005 (8)0.0030 (8)
Cl140.0327 (3)0.0379 (3)0.0333 (3)0.0003 (2)0.0009 (2)0.0114 (2)
C150.0367 (12)0.0329 (11)0.0239 (10)0.0044 (9)0.0066 (9)0.0059 (9)
C160.0294 (11)0.0330 (11)0.0264 (10)0.0044 (9)0.0079 (9)0.0005 (9)
C210.0191 (10)0.0238 (9)0.0257 (10)0.0024 (7)0.0014 (8)0.0015 (8)
C220.0209 (10)0.0235 (10)0.0255 (10)0.0025 (7)0.0008 (8)0.0042 (8)
N220.0248 (9)0.0270 (9)0.0285 (9)0.0020 (7)0.0027 (7)0.0047 (8)
O2210.0544 (10)0.0233 (8)0.0349 (9)0.0054 (7)0.0055 (8)0.0032 (7)
O2220.0497 (10)0.0380 (9)0.0283 (8)0.0027 (7)0.0143 (7)0.0075 (7)
C230.0215 (10)0.0321 (11)0.0269 (10)0.0018 (8)0.0015 (8)0.0011 (9)
C240.0251 (11)0.0246 (10)0.0336 (12)0.0020 (8)0.0031 (9)0.0038 (9)
C250.0287 (11)0.0220 (10)0.0348 (11)0.0036 (8)0.0014 (9)0.0060 (9)
C260.0267 (11)0.0271 (10)0.0254 (10)0.0032 (8)0.0012 (8)0.0042 (8)
Geometric parameters (Å, º) top
S1—S22.0398 (7)C15—H150.9500
S1—C111.784 (2)C16—H160.9500
S2—C211.7889 (19)C21—C261.400 (3)
N22—O2211.230 (2)C21—C221.405 (3)
N22—O2221.223 (2)C22—C231.387 (3)
C11—C121.390 (3)C22—N221.460 (2)
C11—C161.391 (3)C23—C241.379 (3)
C12—C131.387 (3)C23—H230.9500
C12—H120.9500C24—C251.384 (3)
C13—C141.378 (3)C24—H240.9500
C13—H130.9500C25—C261.379 (3)
C14—C151.381 (3)C25—H250.9500
C14—Cl141.7433 (19)C26—H260.9500
C15—C161.384 (3)
C11—S1—S2105.25 (7)C15—C16—H16120.1
C21—S2—S1103.78 (7)C11—C16—H16120.1
O221—N22—O222123.32 (16)C26—C21—C22116.04 (17)
O221—N22—C22117.44 (16)C26—C21—S2121.50 (15)
O222—N22—C22119.24 (16)C22—C21—S2122.46 (15)
C12—C11—C16119.96 (18)C23—C22—C21122.65 (17)
C12—C11—S1124.37 (15)C23—C22—N22116.95 (17)
C16—C11—S1115.67 (16)C21—C22—N22120.39 (17)
C13—C12—C11120.10 (19)C24—C23—C22119.55 (18)
C13—C12—H12119.9C24—C23—H23120.2
C11—C12—H12119.9C22—C23—H23120.2
C14—C13—C12119.13 (19)C23—C24—C25119.15 (19)
C14—C13—H13120.4C23—C24—H24120.4
C12—C13—H13120.4C25—C24—H24120.4
C13—C14—C15121.49 (18)C26—C25—C24121.21 (19)
C13—C14—Cl14119.55 (16)C26—C25—H25119.4
C15—C14—Cl14118.95 (15)C24—C25—H25119.4
C14—C15—C16119.45 (18)C25—C26—C21121.38 (19)
C14—C15—H15120.3C25—C26—H26119.3
C16—C15—H15120.3C21—C26—H26119.3
C15—C16—C11119.9 (2)
C11—S1—S2—C2181.50 (9)C13—C14—C15—C160.1 (3)
S1—S2—C21—C22172.01 (15)Cl14—C14—C15—C16178.62 (15)
S1—S2—C21—C268.28 (17)C14—C15—C16—C110.2 (3)
S2—S1—C11—C124.67 (18)C12—C11—C16—C150.3 (3)
S2—S1—C11—C16175.64 (13)S1—C11—C16—C15179.38 (15)
S2—C21—C22—N221.9 (3)C26—C21—C22—C231.5 (3)
C21—C22—N22—O2214.5 (3)S2—C21—C22—C23178.80 (15)
C21—C22—N22—O222175.11 (18)C26—C21—C22—N22177.85 (16)
C23—C22—N22—O221174.86 (17)C21—C22—C23—C241.0 (3)
C23—C22—N22—O2225.5 (3)N22—C22—C23—C24178.31 (17)
C16—C11—C12—C130.4 (3)C22—C23—C24—C250.0 (3)
S1—C11—C12—C13179.28 (15)C23—C24—C25—C260.6 (3)
C11—C12—C13—C140.3 (3)C24—C25—C26—C210.1 (3)
C12—C13—C14—C150.2 (3)C22—C21—C26—C250.9 (3)
C12—C13—C14—Cl14178.55 (14)S2—C21—C26—C25179.37 (15)
(3) 2,4-Dinitro-4'-methyldiphenyl disulfide top
Crystal data top
C13H10N2O4S2F(000) = 332
Mr = 322.35Dx = 1.564 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.1301 (2) ÅCell parameters from 1695 reflections
b = 6.3474 (1) Åθ = 2.1–27.5°
c = 11.1133 (2) ŵ = 0.41 mm1
β = 106.644 (8)°T = 150 K
V = 684.64 (2) Å3Needle, yellow
Z = 20.55 × 0.10 × 0.08 mm
Data collection top
Kappa-CCD
diffractometer
1695 independent reflections
Radiation source: fine-focus sealed X-ray tube1615 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
ϕ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 1313
Tmin = 0.808, Tmax = 0.970k = 78
7452 measured reflectionsl = 1214
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 = 1.04w = 1/[σ2(Fo2) + (0.0742P)2 + 0.0709P]
where P = (Fo2 + 2Fc2)/3
1695 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.40 e Å3
1 restraintΔρmin = 0.51 e Å3
Crystal data top
C13H10N2O4S2V = 684.64 (2) Å3
Mr = 322.35Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.1301 (2) ŵ = 0.41 mm1
b = 6.3474 (1) ÅT = 150 K
c = 11.1133 (2) Å0.55 × 0.10 × 0.08 mm
β = 106.644 (8)°
Data collection top
Kappa-CCD
diffractometer
1695 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
1615 reflections with I > 2σ(I)
Tmin = 0.808, Tmax = 0.970Rint = 0.072
7452 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.107H-atom parameters constrained
S = 1.04Δρmax = 0.40 e Å3
1695 reflectionsΔρmin = 0.51 e Å3
191 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.17395 (7)0.83986 (13)0.00092 (6)0.0270 (2)
S20.02483 (6)0.88284 (11)0.11272 (7)0.0262 (2)
C110.2715 (3)0.9965 (5)0.0780 (2)0.0217 (6)
C120.3138 (3)1.1968 (5)0.0322 (3)0.0251 (6)
C130.3917 (2)1.3193 (5)0.0890 (3)0.0253 (6)
C140.4285 (3)1.2454 (5)0.1929 (3)0.0264 (6)
C1410.5103 (3)1.3803 (6)0.2570 (3)0.0319 (7)
C150.3868 (3)1.0437 (6)0.2372 (3)0.0289 (7)
C160.3090 (3)0.9186 (5)0.1815 (3)0.0267 (6)
C210.0558 (3)0.6666 (5)0.2182 (3)0.0238 (6)
C220.1821 (3)0.6415 (5)0.3137 (3)0.0254 (6)
N220.2914 (3)0.7983 (5)0.3299 (2)0.0306 (6)
O2210.2723 (2)0.9471 (5)0.2579 (2)0.0426 (6)
O2220.3974 (2)0.7749 (5)0.4180 (2)0.0443 (7)
C230.2082 (3)0.4715 (6)0.3937 (3)0.0280 (6)
C240.1076 (3)0.3215 (5)0.3809 (3)0.0262 (6)
N240.1328 (3)0.1385 (5)0.4646 (2)0.0342 (6)
O2410.2393 (3)0.1373 (5)0.5530 (2)0.0514 (7)
O2420.0492 (3)0.0050 (5)0.4416 (2)0.0453 (6)
C250.0192 (3)0.3390 (5)0.2909 (3)0.0271 (6)
C260.0423 (3)0.5102 (5)0.2113 (3)0.0252 (6)
H120.28921.24960.03840.030*
H130.42041.45570.05680.030*
H14A0.50131.52860.23620.048*0.50
H14B0.47541.36100.34810.048*0.50
H14C0.60761.33900.22850.048*0.50
H14D0.55491.29050.30570.048*0.50
H14E0.58081.45810.19370.048*0.50
H14F0.44861.48010.31340.048*0.50
H150.41240.99080.30740.035*
H160.28140.78150.21310.032*
H230.29400.45810.45650.034*
H250.08850.23530.28430.032*
H260.12870.52190.14910.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0248 (3)0.0320 (4)0.0238 (3)0.0044 (3)0.0061 (3)0.0008 (3)
S20.0205 (3)0.0270 (4)0.0330 (4)0.0009 (3)0.0106 (3)0.0033 (3)
C110.0159 (11)0.0282 (14)0.0200 (12)0.0003 (11)0.0036 (10)0.0013 (11)
C120.0163 (12)0.0303 (15)0.0255 (13)0.0036 (12)0.0009 (10)0.0022 (12)
C130.0183 (11)0.0264 (13)0.0284 (13)0.0008 (12)0.0022 (10)0.0019 (12)
C140.0160 (11)0.0330 (15)0.0273 (14)0.0041 (13)0.0013 (10)0.0057 (13)
C1410.0242 (12)0.0410 (18)0.0301 (14)0.0008 (15)0.0071 (11)0.0063 (15)
C150.0224 (13)0.0354 (16)0.0281 (15)0.0018 (13)0.0057 (11)0.0034 (13)
C160.0232 (12)0.0316 (16)0.0249 (13)0.0008 (12)0.0063 (10)0.0022 (12)
C210.0218 (13)0.0233 (13)0.0269 (14)0.0017 (12)0.0079 (10)0.0042 (12)
C220.0190 (12)0.0304 (15)0.0263 (14)0.0013 (13)0.0055 (11)0.0058 (12)
N220.0216 (11)0.0370 (15)0.0334 (13)0.0026 (11)0.0081 (10)0.0087 (12)
O2210.0298 (11)0.0425 (16)0.0546 (15)0.0082 (12)0.0105 (11)0.0063 (13)
O2220.0262 (11)0.0591 (18)0.0398 (12)0.0071 (12)0.0029 (10)0.0079 (13)
C230.0280 (14)0.0349 (15)0.0213 (12)0.0051 (14)0.0076 (11)0.0032 (12)
C240.0325 (14)0.0262 (14)0.0223 (12)0.0028 (13)0.0116 (11)0.0018 (12)
N240.0470 (16)0.0334 (15)0.0266 (13)0.0105 (15)0.0174 (12)0.0037 (12)
O2410.0547 (15)0.0546 (18)0.0384 (14)0.0134 (16)0.0029 (11)0.0120 (14)
O2420.0686 (17)0.0339 (13)0.0395 (13)0.0020 (15)0.0249 (12)0.0059 (12)
C250.0298 (13)0.0256 (14)0.0273 (13)0.0008 (13)0.0106 (11)0.0012 (13)
C260.0220 (13)0.0286 (15)0.0242 (13)0.0024 (12)0.0054 (11)0.0015 (12)
Geometric parameters (Å, º) top
S1—C111.784 (3)C15—H150.9500
S1—S22.0591 (9)C16—H160.9500
S2—C211.774 (3)C21—C261.391 (4)
C11—C121.391 (4)C21—C221.418 (4)
C11—C161.401 (4)C22—C231.375 (5)
C12—C131.382 (4)C22—N221.461 (4)
C12—H120.9500N22—O2211.217 (4)
C13—C141.393 (4)N22—O2221.238 (3)
C13—H130.9500C23—C241.372 (5)
C14—C151.394 (5)C23—H230.9500
C14—C1411.506 (4)C24—C251.388 (4)
C141—H14A0.9800C24—N241.464 (4)
C141—H14B0.9800N24—O2421.220 (4)
C141—H14C0.9800N24—O2411.233 (4)
C141—H14D0.9800C25—C261.378 (4)
C141—H14E0.9800C25—H250.9500
C141—H14F0.9800C26—H260.9500
C15—C161.383 (4)
C11—S1—S2102.51 (9)H14D—C141—H14F109.5
C21—S2—S1104.69 (10)H14E—C141—H14F109.5
C12—C11—C16119.7 (3)C16—C15—C14121.5 (3)
C12—C11—S1119.2 (2)C16—C15—H15119.2
C16—C11—S1121.1 (2)C14—C15—H15119.2
C13—C12—C11120.2 (3)C15—C16—C11119.2 (3)
C13—C12—H12119.9C15—C16—H16120.4
C11—C12—H12119.9C11—C16—H16120.4
C12—C13—C14120.8 (3)C26—C21—C22116.0 (3)
C12—C13—H13119.6C26—C21—S2121.8 (2)
C14—C13—H13119.6C22—C21—S2122.2 (2)
C15—C14—C13118.5 (3)C23—C22—C21122.5 (3)
C15—C14—C141120.5 (3)C23—C22—N22117.2 (2)
C13—C14—C141121.0 (3)C21—C22—N22120.4 (3)
C14—C141—H14A109.5O221—N22—O222123.5 (3)
C14—C141—H14B109.5O221—N22—C22118.4 (2)
H14A—C141—H14B109.5O222—N22—C22118.1 (3)
C14—C141—H14C109.5C24—C23—C22118.6 (3)
H14A—C141—H14C109.5C24—C23—H23120.7
H14B—C141—H14C109.5C22—C23—H23120.7
C14—C141—H14D109.5C23—C24—C25121.7 (3)
H14A—C141—H14D141.1C23—C24—N24119.7 (3)
H14B—C141—H14D56.3C25—C24—N24118.6 (3)
H14C—C141—H14D56.3O242—N24—O241123.9 (3)
C14—C141—H14E109.5O242—N24—C24118.3 (3)
H14A—C141—H14E56.3O241—N24—C24117.7 (3)
H14B—C141—H14E141.1C26—C25—C24118.6 (3)
H14C—C141—H14E56.3C26—C25—H25120.7
H14D—C141—H14E109.5C24—C25—H25120.7
C14—C141—H14F109.5C25—C26—C21122.7 (3)
H14A—C141—H14F56.3C25—C26—H26118.7
H14B—C141—H14F56.3C21—C26—H26118.7
H14C—C141—H14F141.1
C11—S1—S2—C2194.61 (14)S2—C21—C22—N221.3 (4)
S2—S1—C11—C1299.4 (2)C23—C22—N22—O221177.9 (3)
S2—S1—C11—C1682.3 (2)C21—C22—N22—O2211.7 (4)
C16—C11—C12—C130.5 (4)C23—C22—N22—O2223.7 (4)
S1—C11—C12—C13178.8 (2)C21—C22—N22—O222176.7 (3)
C11—C12—C13—C140.2 (4)C21—C22—C23—C240.4 (4)
C12—C13—C14—C150.9 (4)N22—C22—C23—C24180.0 (3)
C12—C13—C14—C141178.5 (2)C22—C23—C24—C250.8 (4)
C13—C14—C15—C160.8 (4)C22—C23—C24—N24179.8 (3)
C141—C14—C15—C16178.6 (3)C23—C24—N24—O242171.0 (3)
C14—C15—C16—C110.1 (4)C25—C24—N24—O2429.6 (4)
C12—C11—C16—C150.6 (4)C23—C24—N24—O2417.5 (4)
S1—C11—C16—C15178.8 (2)C25—C24—N24—O241171.8 (3)
S1—S2—C21—C262.2 (3)C23—C24—C25—C261.3 (4)
S1—S2—C21—C22178.5 (2)N24—C24—C25—C26179.3 (2)
C26—C21—C22—C231.1 (4)C24—C25—C26—C210.5 (4)
S2—C21—C22—C23178.2 (2)C22—C21—C26—C250.6 (4)
C26—C21—C22—N22179.3 (2)S2—C21—C26—C25178.7 (2)
(4) 2,4-Dinitrophenyl-2'-methoxycarbonylmethyl disulfide top
Crystal data top
C9H8N2O6S2Z = 2
Mr = 304.30F(000) = 312
Triclinic, P1Dx = 1.709 Mg m3
a = 8.1655 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.2415 (3) ÅCell parameters from 2629 reflections
c = 9.3887 (4) Åθ = 2.9–29.3°
α = 72.1417 (15)°µ = 0.48 mm1
β = 83.3965 (14)°T = 150 K
γ = 80.332 (3)°Needle, yellow
V = 591.48 (4) Å30.35 × 0.05 × 0.03 mm
Data collection top
Kappa-CCD
diffractometer
2629 independent reflections
Radiation source: fine-focus sealed X-ray tube1969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ϕ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 1010
Tmin = 0.851, Tmax = 0.988k = 910
6105 measured reflectionsl = 1111
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0536P)2]
where P = (Fo2 + 2Fc2)/3
2629 reflections(Δ/σ)max = 0.008
173 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C9H8N2O6S2γ = 80.332 (3)°
Mr = 304.30V = 591.48 (4) Å3
Triclinic, P1Z = 2
a = 8.1655 (3) ÅMo Kα radiation
b = 8.2415 (3) ŵ = 0.48 mm1
c = 9.3887 (4) ÅT = 150 K
α = 72.1417 (15)°0.35 × 0.05 × 0.03 mm
β = 83.3965 (14)°
Data collection top
Kappa-CCD
diffractometer
2629 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
1969 reflections with I > 2σ(I)
Tmin = 0.851, Tmax = 0.988Rint = 0.050
6105 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.04Δρmax = 0.36 e Å3
2629 reflectionsΔρmin = 0.38 e Å3
173 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.31637 (7)0.86272 (8)0.91373 (7)0.02245 (18)
S20.09158 (7)0.89766 (8)0.82419 (7)0.02167 (18)
C10.4109 (3)1.0481 (3)0.7967 (3)0.0205 (5)
C20.3239 (3)1.2169 (3)0.8142 (3)0.0201 (5)
O30.2542 (2)1.3296 (2)0.7165 (2)0.0309 (4)
O40.3370 (2)1.2272 (2)0.95141 (18)0.0254 (4)
C50.2645 (3)1.3890 (3)0.9787 (3)0.0344 (6)
C210.1368 (3)0.8092 (3)0.6714 (3)0.0180 (5)
C220.0110 (2)0.7859 (3)0.5912 (3)0.0179 (5)
N220.1648 (2)0.8353 (3)0.6329 (2)0.0212 (5)
O2210.19512 (18)0.9202 (2)0.7223 (2)0.0281 (4)
O2220.27220 (19)0.7932 (2)0.5763 (2)0.0330 (5)
C230.0430 (3)0.7170 (3)0.4719 (3)0.0191 (5)
C240.2073 (3)0.6735 (3)0.4288 (3)0.0177 (5)
N240.2445 (2)0.6046 (3)0.3001 (2)0.0232 (5)
O2410.1278 (2)0.5881 (3)0.2372 (2)0.0362 (5)
O2420.39156 (19)0.5679 (2)0.2617 (2)0.0305 (4)
C250.3360 (3)0.6936 (3)0.5019 (3)0.0194 (5)
C260.3011 (3)0.7597 (3)0.6213 (3)0.0190 (5)
H1A0.52801.03370.82150.025*
H1B0.41161.05120.69040.025*
H5A0.28001.38311.08220.052*0.50
H5B0.14531.41050.96280.052*0.50
H5C0.31931.48270.90940.052*0.50
H5D0.21651.46780.88740.052*0.50
H5E0.35111.44031.00680.052*0.50
H5F0.17711.36821.06020.052*0.50
H230.04490.70050.42190.023*
H250.44820.66190.46980.023*
H260.39060.77240.67150.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0278 (3)0.0206 (3)0.0201 (3)0.0042 (2)0.0066 (2)0.0055 (3)
S20.0221 (3)0.0239 (4)0.0210 (4)0.0034 (2)0.0008 (2)0.0095 (3)
C10.0206 (11)0.0229 (13)0.0208 (13)0.0038 (9)0.0001 (9)0.0105 (11)
C20.0166 (11)0.0223 (13)0.0227 (14)0.0054 (9)0.0016 (9)0.0070 (11)
O30.0348 (10)0.0244 (10)0.0335 (11)0.0015 (7)0.0181 (8)0.0041 (9)
O40.0380 (9)0.0184 (9)0.0200 (10)0.0002 (7)0.0022 (7)0.0081 (8)
C50.0484 (16)0.0199 (14)0.0367 (17)0.0043 (11)0.0080 (12)0.0149 (13)
C210.0211 (11)0.0148 (12)0.0177 (12)0.0032 (8)0.0020 (9)0.0034 (10)
C220.0160 (11)0.0156 (12)0.0200 (13)0.0009 (8)0.0011 (8)0.0029 (10)
N220.0175 (10)0.0220 (11)0.0215 (11)0.0033 (7)0.0009 (8)0.0025 (9)
O2210.0236 (9)0.0316 (11)0.0308 (11)0.0002 (7)0.0013 (7)0.0150 (9)
O2220.0189 (9)0.0468 (12)0.0395 (12)0.0058 (7)0.0048 (7)0.0203 (10)
C230.0204 (11)0.0164 (12)0.0204 (13)0.0037 (8)0.0045 (9)0.0036 (10)
C240.0205 (11)0.0151 (12)0.0173 (13)0.0028 (8)0.0000 (9)0.0050 (10)
N240.0219 (11)0.0254 (12)0.0234 (12)0.0043 (8)0.0007 (8)0.0085 (9)
O2410.0252 (9)0.0556 (14)0.0401 (12)0.0047 (8)0.0068 (8)0.0309 (10)
O2420.0221 (9)0.0413 (12)0.0313 (11)0.0007 (7)0.0029 (7)0.0192 (9)
C250.0193 (11)0.0155 (12)0.0209 (13)0.0007 (8)0.0018 (9)0.0026 (10)
C260.0198 (11)0.0184 (13)0.0189 (13)0.0024 (8)0.0045 (8)0.0046 (10)
Geometric parameters (Å, º) top
S1—S22.0464 (8)C5—H5C0.9800
S1—C11.819 (2)C5—H5D0.9800
S2—C211.777 (2)C5—H5E0.9800
N22—O2211.229 (3)C5—H5F0.9800
N22—O2221.222 (2)C21—C261.405 (3)
N24—O2411.224 (3)C21—C221.411 (3)
N24—O2421.228 (2)C22—C231.384 (3)
C1—C21.499 (3)C22—N221.467 (3)
C1—H1A0.9900C23—C241.377 (3)
C1—H1B0.9900C23—H230.9500
C2—O31.202 (3)C24—C251.377 (3)
C2—O41.335 (3)C24—N241.468 (3)
O4—C51.450 (3)C25—C261.373 (3)
C5—H5A0.9800C25—H250.9500
C5—H5B0.9800C26—H260.9500
C1—S1—S2102.72 (8)H5A—C5—H5E56.3
C21—S2—S1104.16 (7)H5B—C5—H5E141.1
C2—C1—S1113.96 (15)H5C—C5—H5E56.3
O221—N22—O222123.66 (18)H5D—C5—H5E109.5
O221—N22—C22117.16 (18)O4—C5—H5F109.5
O222—N22—C22119.17 (19)H5A—C5—H5F56.3
O241—N24—O242124.0 (2)H5B—C5—H5F56.3
O241—N24—C24118.23 (18)H5C—C5—H5F141.1
O242—N24—C24117.72 (18)H5D—C5—H5F109.5
C2—C1—H1A108.8H5E—C5—H5F109.5
S1—C1—H1A108.8C26—C21—C22115.6 (2)
C2—C1—H1B108.8C26—C21—S2121.94 (17)
S1—C1—H1B108.8C22—C21—S2122.43 (16)
H1A—C1—H1B107.7C23—C22—C21123.56 (19)
O3—C2—O4124.4 (2)C23—C22—N22116.32 (19)
O3—C2—C1124.5 (2)C21—C22—N22120.1 (2)
O4—C2—C1111.07 (19)C24—C23—C22117.2 (2)
C2—O4—C5115.87 (19)C24—C23—H23121.4
O4—C5—H5A109.5C22—C23—H23121.4
O4—C5—H5B109.5C23—C24—C25122.1 (2)
H5A—C5—H5B109.5C23—C24—N24118.29 (19)
O4—C5—H5C109.5C25—C24—N24119.56 (18)
H5A—C5—H5C109.5C26—C25—C24119.5 (2)
H5B—C5—H5C109.5C26—C25—H25120.2
O4—C5—H5D109.5C24—C25—H25120.2
H5A—C5—H5D141.1C25—C26—C21121.9 (2)
H5B—C5—H5D56.3C25—C26—H26119.0
H5C—C5—H5D56.3C21—C26—H26119.0
O4—C5—H5E109.5
C1—S1—S2—C2183.97 (11)C1—C2—O4—C5176.97 (19)
S1—S2—C21—C22171.14 (18)C26—C21—C22—C230.9 (3)
S1—S2—C21—C269.7 (2)S2—C21—C22—C23179.88 (18)
C21—C22—N22—O22111.0 (3)C26—C21—C22—N22179.26 (19)
C21—C22—N22—O222170.2 (2)S2—C21—C22—N220.0 (3)
C23—C22—N22—O221169.1 (2)C21—C22—C23—C241.6 (3)
C23—C22—N22—O2229.7 (3)N22—C22—C23—C24178.57 (19)
C23—C24—N24—O2410.4 (3)C22—C23—C24—C251.3 (3)
C23—C24—N24—O242179.3 (2)C22—C23—C24—N24178.3 (2)
C25—C24—N24—O241180.0 (2)C23—C24—C25—C260.3 (3)
C25—C24—N24—O2420.3 (3)N24—C24—C25—C26179.3 (2)
S2—S1—C1—C267.02 (17)C24—C25—C26—C210.4 (3)
S1—C1—C2—O3115.4 (2)C22—C21—C26—C250.2 (3)
S1—C1—C2—O466.0 (2)S2—C21—C26—C25179.07 (18)
O3—C2—O4—C51.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O3i0.952.353.299 (3)176
Symmetry code: (i) x, y+2, z+1.
(5) Bis-(2-nitrophenyl) disulfide top
Crystal data top
C12H8N2O4S2F(000) = 632
Mr = 308.32Dx = 1.625 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.1028 (11) ÅCell parameters from 1862 reflections
b = 22.925 (4) Åθ = 3.0–28.5°
c = 7.7769 (14) ŵ = 0.44 mm1
β = 95.536 (12)°T = 150 K
V = 1260.4 (4) Å3Needle, yellow
Z = 40.40 × 0.07 × 0.07 mm
Data collection top
Kappa-CCD
diffractometer
1862 independent reflections
Radiation source: fine-focus sealed X-ray tube1135 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ϕ scans and ω scans with κ offsetsθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 87
Tmin = 0.845, Tmax = 0.970k = 2728
3982 measured reflectionsl = 710
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0528P)2]
where P = (Fo2 + 2Fc2)/3
1862 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C12H8N2O4S2V = 1260.4 (4) Å3
Mr = 308.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.1028 (11) ŵ = 0.44 mm1
b = 22.925 (4) ÅT = 150 K
c = 7.7769 (14) Å0.40 × 0.07 × 0.07 mm
β = 95.536 (12)°
Data collection top
Kappa-CCD
diffractometer
1862 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
1135 reflections with I > 2σ(I)
Tmin = 0.845, Tmax = 0.970Rint = 0.059
3982 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.03Δρmax = 0.33 e Å3
1862 reflectionsΔρmin = 0.29 e Å3
181 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.29771 (18)0.41853 (5)0.46148 (13)0.0341 (4)
S20.40937 (18)0.34184 (5)0.37879 (14)0.0340 (4)
C110.2744 (7)0.46456 (18)0.2756 (5)0.0304 (12)
C120.2372 (6)0.52434 (18)0.2864 (5)0.0277 (12)
N120.2115 (6)0.55123 (16)0.4526 (5)0.0344 (10)
O1220.1984 (5)0.60403 (13)0.4631 (4)0.0404 (9)
O1210.2035 (5)0.51862 (13)0.5782 (4)0.0493 (10)
C130.2205 (6)0.56018 (19)0.1441 (5)0.0331 (12)
C140.2377 (7)0.5376 (2)0.0167 (6)0.0382 (14)
C150.2743 (6)0.47882 (19)0.0328 (5)0.0346 (13)
C160.2950 (7)0.44307 (19)0.1129 (5)0.0346 (12)
C210.2079 (7)0.30143 (18)0.2867 (5)0.0253 (11)
C220.2159 (7)0.24112 (17)0.2660 (5)0.0246 (11)
N220.3850 (6)0.20841 (16)0.3224 (4)0.0334 (11)
O2210.5343 (5)0.23556 (14)0.3516 (4)0.0459 (10)
O2220.3759 (5)0.15520 (13)0.3377 (4)0.0455 (9)
C230.0617 (7)0.20969 (19)0.1951 (5)0.0313 (12)
C240.1040 (7)0.23808 (19)0.1391 (5)0.0347 (13)
C250.1174 (7)0.29733 (19)0.1603 (5)0.0333 (13)
C260.0371 (7)0.32882 (18)0.2340 (5)0.0306 (13)
H130.19700.60070.15740.040*
H140.22460.56210.11580.046*
H150.28540.46260.14380.042*
H160.32400.40300.09970.041*
H230.06980.16850.18490.038*
H240.20860.21670.08610.042*
H250.23250.31690.12450.040*
H260.02590.36980.24860.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0493 (10)0.0221 (6)0.0303 (7)0.0004 (6)0.0015 (7)0.0001 (4)
S20.0373 (9)0.0235 (6)0.0401 (8)0.0002 (6)0.0023 (6)0.0006 (4)
C110.034 (4)0.030 (3)0.027 (3)0.004 (2)0.003 (2)0.0008 (17)
C120.031 (4)0.027 (3)0.025 (3)0.001 (2)0.000 (2)0.0054 (16)
N120.042 (3)0.023 (2)0.037 (2)0.0035 (19)0.000 (2)0.0009 (17)
O1220.050 (2)0.0242 (19)0.047 (2)0.0071 (17)0.0043 (17)0.0026 (13)
O1210.083 (3)0.036 (2)0.028 (2)0.0068 (19)0.005 (2)0.0018 (14)
C130.034 (3)0.030 (3)0.035 (3)0.003 (2)0.003 (2)0.0033 (19)
C140.045 (4)0.036 (3)0.034 (3)0.002 (2)0.007 (3)0.0098 (19)
C150.042 (4)0.034 (3)0.028 (3)0.005 (2)0.007 (3)0.0021 (18)
C160.037 (4)0.025 (3)0.042 (3)0.004 (2)0.007 (3)0.0035 (19)
C210.027 (3)0.028 (3)0.021 (2)0.003 (2)0.001 (2)0.0015 (16)
C220.029 (4)0.023 (2)0.022 (2)0.001 (2)0.001 (2)0.0005 (17)
N220.041 (4)0.031 (3)0.028 (2)0.007 (2)0.002 (2)0.0016 (15)
O2210.029 (3)0.036 (2)0.071 (3)0.0011 (18)0.0047 (19)0.0021 (16)
O2220.060 (3)0.0195 (18)0.056 (2)0.0072 (17)0.0041 (19)0.0090 (13)
C230.038 (4)0.026 (3)0.032 (3)0.003 (2)0.009 (3)0.0003 (18)
C240.034 (4)0.036 (3)0.034 (3)0.011 (3)0.003 (2)0.0035 (19)
C250.032 (4)0.033 (3)0.035 (3)0.000 (2)0.002 (3)0.0008 (19)
C260.036 (4)0.023 (2)0.033 (3)0.003 (2)0.003 (3)0.0000 (17)
Geometric parameters (Å, º) top
S1—S22.0572 (15)C15—C161.395 (5)
S1—C111.784 (4)C15—H150.9500
S2—C211.795 (5)C16—H160.9500
N12—O1211.236 (4)C21—C261.392 (6)
N12—O1221.217 (4)C21—C221.394 (6)
N22—O2211.232 (5)C22—C231.381 (6)
N22—O2221.228 (4)C22—N221.448 (5)
C11—C161.379 (5)C23—C241.378 (6)
C11—C121.400 (6)C23—H230.9500
C12—C131.374 (5)C24—C251.373 (6)
C12—N121.460 (5)C24—H240.9500
C13—C141.370 (5)C25—C261.390 (6)
C13—H130.9500C25—H250.9500
C14—C151.381 (6)C26—H260.9500
C14—H140.9500
C11—S1—S2105.11 (14)C16—C15—H15119.8
C21—S2—S1104.43 (15)C11—C16—C15121.6 (4)
O121—N12—O122122.6 (4)C11—C16—H16119.2
O121—N12—C12117.6 (4)C15—C16—H16119.2
O122—N12—C12119.7 (3)C26—C21—C22117.2 (4)
O221—N22—O222122.4 (4)C26—C21—S2121.6 (3)
O221—N22—C22117.9 (4)C22—C21—S2121.2 (4)
O222—N22—C22119.6 (4)C23—C22—C21121.6 (4)
C16—C11—C12116.2 (4)C23—C22—N22117.0 (4)
C16—C11—S1121.5 (3)C21—C22—N22121.4 (4)
C12—C11—S1122.3 (3)C24—C23—C22120.0 (4)
C13—C12—C11122.7 (4)C24—C23—H23120.0
C13—C12—N12116.9 (4)C22—C23—H23120.0
C11—C12—N12120.4 (3)C25—C24—C23119.8 (5)
C14—C13—C12120.1 (4)C25—C24—H24120.1
C14—C13—H13120.0C23—C24—H24120.1
C12—C13—H13120.0C24—C25—C26120.2 (5)
C13—C14—C15119.0 (4)C24—C25—H25119.9
C13—C14—H14120.5C26—C25—H25119.9
C15—C14—H14120.5C25—C26—C21121.2 (4)
C14—C15—C16120.4 (4)C25—C26—H26119.4
C14—C15—H15119.8C21—C26—H26119.4
C11—S1—S2—C2184.4 (2)N12—C12—C13—C14178.2 (4)
S1—S2—C21—C22159.6 (3)C12—C13—C14—C150.8 (7)
S1—S2—C21—C2620.1 (3)C13—C14—C15—C160.5 (7)
S2—S1—C11—C1611.5 (4)C12—C11—C16—C151.8 (7)
S2—S1—C11—C12167.5 (4)S1—C11—C16—C15179.1 (4)
C11—C12—N12—O1217.6 (7)C14—C15—C16—C111.9 (7)
C13—C12—N12—O121171.5 (4)C26—C21—C22—C230.4 (6)
C11—C12—N12—O122172.6 (5)S2—C21—C22—C23179.9 (3)
C13—C12—N12—O1228.3 (7)C26—C21—C22—N22177.8 (3)
C21—C22—N22—O22116.7 (5)S2—C21—C22—N221.9 (5)
C23—C22—N22—O221165.0 (4)C21—C22—C23—C241.5 (6)
C21—C22—N22—O222164.1 (4)N22—C22—C23—C24179.8 (3)
C23—C22—N22—O22214.2 (5)C22—C23—C24—C252.5 (6)
C16—C11—C12—C130.4 (7)C23—C24—C25—C261.6 (6)
S1—C11—C12—C13179.5 (4)C24—C25—C26—C210.4 (6)
C16—C11—C12—N12179.5 (4)C22—C21—C26—C251.4 (6)
S1—C11—C12—N121.5 (7)S2—C21—C26—C25179.0 (3)
C11—C12—C13—C140.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O222i0.952.493.197 (5)131
Symmetry code: (i) x, y+1/2, z1/2.
(6) Bis-(2-nitro-4-trifluoromethylphenyl) disulfide top
Crystal data top
C14H6F6N2O4S2F(000) = 888
Mr = 444.33Dx = 1.727 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.1617 (5) ÅCell parameters from 3812 reflections
b = 5.3367 (2) Åθ = 2.3–27.5°
c = 22.6233 (10) ŵ = 0.40 mm1
β = 91.7376 (13)°T = 150 K
V = 1709.01 (12) Å3Needle, yellow
Z = 40.35 × 0.10 × 0.05 mm
Data collection top
Kappa-CCD
diffractometer
3812 independent reflections
Radiation source: fine-focus sealed X-ray tube1646 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
ϕ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 1818
Tmin = 0.873, Tmax = 0.980k = 66
14106 measured reflectionsl = 2829
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 0.94w = 1/[σ2(Fo2) + (0.0668P)2]
where P = (Fo2 + 2Fc2)/3
3812 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C14H6F6N2O4S2V = 1709.01 (12) Å3
Mr = 444.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.1617 (5) ŵ = 0.40 mm1
b = 5.3367 (2) ÅT = 150 K
c = 22.6233 (10) Å0.35 × 0.10 × 0.05 mm
β = 91.7376 (13)°
Data collection top
Kappa-CCD
diffractometer
3812 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
1646 reflections with I > 2σ(I)
Tmin = 0.873, Tmax = 0.980Rint = 0.081
14106 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 0.94Δρmax = 0.37 e Å3
3812 reflectionsΔρmin = 0.25 e Å3
253 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.22533 (7)0.85099 (16)0.26136 (4)0.0621 (3)
S20.36334 (7)0.75071 (18)0.27725 (4)0.0655 (3)
C110.1863 (2)0.6570 (5)0.20162 (13)0.0472 (8)
C120.0974 (2)0.6873 (6)0.17393 (15)0.0499 (8)
N120.0328 (3)0.8793 (6)0.19395 (15)0.0650 (8)
O1210.0592 (2)1.0148 (5)0.23493 (14)0.0809 (8)
O1220.0445 (2)0.8981 (6)0.16933 (14)0.0952 (10)
C130.0671 (3)0.5438 (6)0.12645 (15)0.0571 (9)
C140.1258 (3)0.3619 (6)0.10481 (14)0.0544 (9)
C1410.0949 (4)0.2153 (8)0.05198 (19)0.0764 (12)
F1410.1023 (2)0.3360 (5)0.00274 (11)0.1177 (11)
F1420.1400 (3)0.0050 (5)0.04609 (13)0.1450 (13)
F1430.0052 (3)0.1512 (7)0.05305 (13)0.1541 (15)
C150.2126 (3)0.3236 (6)0.13188 (16)0.0594 (10)
C160.2422 (2)0.4667 (6)0.17987 (14)0.0540 (9)
C210.3579 (3)0.5036 (6)0.33034 (14)0.0543 (9)
C220.4390 (3)0.4100 (7)0.35920 (16)0.0572 (9)
N220.5332 (3)0.5069 (8)0.34643 (17)0.0775 (10)
O2210.5381 (2)0.6731 (6)0.30981 (15)0.0935 (9)
O2220.6013 (2)0.4158 (8)0.37199 (17)0.1210 (13)
C230.4357 (3)0.2279 (7)0.40201 (16)0.0629 (10)
C240.3500 (3)0.1328 (6)0.41772 (15)0.0598 (9)
C2410.3456 (4)0.0516 (8)0.46645 (19)0.0799 (12)
F2410.3469 (2)0.0509 (5)0.51923 (11)0.1215 (11)
F2420.4182 (2)0.2098 (5)0.46767 (12)0.1100 (9)
F2430.2693 (2)0.1963 (5)0.46249 (14)0.1293 (11)
C250.2687 (3)0.2202 (7)0.38939 (16)0.0650 (10)
C260.2726 (3)0.3999 (7)0.34613 (16)0.0602 (9)
H130.00750.56940.10910.069*
H150.25210.19960.11770.071*
H160.30080.43470.19800.065*
H230.49120.16950.42020.075*
H250.21040.15630.39980.078*
H260.21700.45290.32710.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0662 (7)0.0613 (6)0.0586 (6)0.0014 (5)0.0008 (5)0.0079 (4)
S20.0577 (7)0.0799 (6)0.0589 (6)0.0190 (5)0.0005 (5)0.0003 (5)
C110.046 (2)0.0530 (18)0.0424 (19)0.0026 (16)0.0032 (16)0.0036 (14)
C120.048 (2)0.0499 (19)0.052 (2)0.0061 (16)0.0078 (18)0.0083 (15)
N120.054 (2)0.068 (2)0.074 (2)0.0126 (17)0.0088 (19)0.0140 (18)
O1210.076 (2)0.0710 (18)0.097 (2)0.0117 (14)0.0189 (17)0.0144 (16)
O1220.062 (2)0.121 (2)0.103 (2)0.0381 (17)0.0032 (18)0.0064 (18)
C130.048 (2)0.068 (2)0.054 (2)0.0011 (18)0.0041 (18)0.0107 (18)
C140.057 (3)0.059 (2)0.047 (2)0.0062 (18)0.0054 (18)0.0037 (16)
C1410.081 (4)0.083 (3)0.065 (3)0.007 (2)0.010 (2)0.005 (2)
F1410.180 (3)0.119 (2)0.0528 (16)0.0310 (19)0.0129 (17)0.0032 (14)
F1420.217 (4)0.098 (2)0.116 (2)0.040 (2)0.059 (2)0.0466 (17)
F1430.132 (3)0.225 (4)0.105 (2)0.088 (3)0.011 (2)0.065 (2)
C150.063 (3)0.060 (2)0.056 (2)0.0047 (18)0.007 (2)0.0035 (17)
C160.040 (2)0.061 (2)0.060 (2)0.0085 (16)0.0079 (18)0.0001 (17)
C210.052 (3)0.068 (2)0.043 (2)0.0115 (18)0.0002 (18)0.0112 (16)
C220.036 (2)0.082 (2)0.053 (2)0.0128 (18)0.0006 (18)0.0130 (19)
N220.053 (3)0.105 (3)0.074 (3)0.010 (2)0.001 (2)0.011 (2)
O2210.058 (2)0.118 (2)0.104 (2)0.0259 (17)0.0075 (17)0.009 (2)
O2220.048 (2)0.175 (3)0.139 (3)0.010 (2)0.016 (2)0.030 (3)
C230.051 (3)0.082 (3)0.055 (2)0.0017 (19)0.0084 (19)0.0124 (19)
C240.058 (3)0.071 (2)0.050 (2)0.002 (2)0.0022 (19)0.0087 (18)
C2410.089 (4)0.083 (3)0.068 (3)0.005 (3)0.003 (3)0.005 (2)
F2410.193 (3)0.115 (2)0.0566 (16)0.0197 (19)0.0159 (17)0.0041 (14)
F2420.131 (3)0.0999 (18)0.099 (2)0.0315 (17)0.0021 (17)0.0117 (14)
F2430.123 (3)0.130 (2)0.134 (3)0.039 (2)0.012 (2)0.0536 (19)
C250.050 (3)0.082 (3)0.063 (3)0.0112 (19)0.005 (2)0.001 (2)
C260.044 (2)0.077 (2)0.059 (2)0.0084 (18)0.0050 (18)0.0012 (19)
Geometric parameters (Å, º) top
S1—S22.0476 (14)C16—H160.9300
S1—C111.777 (3)C21—C261.385 (5)
S2—C211.787 (3)C21—C221.396 (5)
N12—O1221.217 (4)C22—C231.374 (5)
N12—O1211.225 (4)C22—N221.467 (5)
C11—C161.387 (4)N22—O2221.211 (4)
C11—C121.399 (4)N22—O2211.217 (4)
C12—C131.377 (5)C23—C241.373 (5)
C12—N121.455 (4)C23—H230.9300
C13—C141.377 (5)C24—C251.382 (5)
C13—H130.9300C24—C2411.480 (5)
C14—C151.372 (5)C241—F2411.313 (5)
C14—C1411.483 (5)C241—F2431.329 (5)
C141—F1411.294 (5)C241—F2421.330 (5)
C141—F1421.300 (5)C25—C261.372 (5)
C141—F1431.317 (5)C25—H250.9300
C15—C161.382 (5)C26—H260.9300
C15—H150.9300
C11—S1—S2104.74 (12)C16—C15—H15119.5
C21—S2—S1104.52 (13)C15—C16—C11121.4 (3)
O121—N12—O122123.2 (3)C15—C16—H16119.3
O122—N12—C12118.7 (4)C11—C16—H16119.3
O121—N12—C12118.1 (3)C26—C21—C22116.6 (3)
O221—N22—O222123.8 (4)C26—C21—S2121.6 (3)
O221—N22—C22117.5 (4)C22—C21—S2121.8 (3)
O222—N22—C22118.7 (4)C23—C22—C21122.5 (3)
C16—C11—C12116.2 (3)C23—C22—N22116.0 (4)
C16—C11—S1121.9 (3)C21—C22—N22121.4 (4)
C12—C11—S1121.9 (2)C24—C23—C22119.6 (4)
C13—C12—C11122.7 (3)C24—C23—H23120.2
C13—C12—N12116.8 (3)C22—C23—H23120.2
C11—C12—N12120.5 (3)C23—C24—C25119.1 (3)
C14—C13—C12119.5 (3)C23—C24—C241119.7 (4)
C14—C13—H13120.3C25—C24—C241121.1 (4)
C12—C13—H13120.3F241—C241—F243107.0 (4)
C15—C14—C13119.3 (3)F241—C241—F242104.8 (4)
C15—C14—C141121.3 (4)F243—C241—F242105.0 (4)
C13—C14—C141119.5 (4)F241—C241—C24113.6 (4)
F141—C141—F142106.8 (4)F243—C241—C24112.9 (4)
F141—C141—F143104.4 (4)F242—C241—C24112.8 (4)
F142—C141—F143104.8 (4)C26—C25—C24121.0 (4)
F141—C141—C14113.7 (4)C26—C25—H25119.5
F142—C141—C14113.8 (4)C24—C25—H25119.5
F143—C141—C14112.5 (4)C25—C26—C21121.2 (4)
C14—C15—C16120.9 (3)C25—C26—H26119.4
C14—C15—H15119.5C21—C26—H26119.4
C11—S1—S2—C2189.93 (15)C13—C14—C141—F14341.2 (5)
S1—S2—C21—C22170.2 (2)C13—C14—C15—C160.8 (5)
S1—S2—C21—C268.0 (3)C141—C14—C15—C16177.8 (3)
S2—S1—C11—C12173.6 (2)C14—C15—C16—C111.4 (5)
S2—S1—C11—C166.6 (3)C12—C11—C16—C152.8 (5)
C21—C22—N22—O2210.3 (5)S1—C11—C16—C15177.4 (3)
C21—C22—N22—O222178.7 (4)C26—C21—C22—C231.3 (5)
C23—C22—N22—O221178.1 (3)S2—C21—C22—C23177.0 (3)
C23—C22—N22—O2222.9 (5)C26—C21—C22—N22179.5 (3)
C16—C11—C12—C132.1 (5)S2—C21—C22—N221.2 (5)
S1—C11—C12—C13178.0 (2)C21—C22—C23—C240.2 (5)
C16—C11—C12—N12179.1 (3)N22—C22—C23—C24178.1 (3)
S1—C11—C12—N120.8 (4)C22—C23—C24—C250.9 (5)
C13—C12—N12—O1222.1 (4)C22—C23—C24—C241176.1 (3)
C11—C12—N12—O122179.0 (3)C23—C24—C241—F24182.4 (5)
C13—C12—N12—O121177.8 (3)C25—C24—C241—F24194.6 (5)
C11—C12—N12—O1211.1 (5)C23—C24—C241—F243155.6 (4)
C11—C12—C13—C140.0 (5)C25—C24—C241—F24327.4 (5)
N12—C12—C13—C14178.9 (3)C23—C24—C241—F24236.8 (5)
C12—C13—C14—C151.5 (5)C25—C24—C241—F242146.3 (4)
C12—C13—C14—C141177.2 (3)C23—C24—C25—C260.1 (5)
C15—C14—C141—F141101.4 (5)C241—C24—C25—C26176.9 (3)
C13—C14—C141—F14177.2 (5)C24—C25—C26—C211.5 (6)
C15—C14—C141—F14221.2 (6)C22—C21—C26—C252.1 (5)
C13—C14—C141—F142160.2 (4)S2—C21—C26—C25176.2 (3)
C15—C14—C141—F143140.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O222i0.932.573.421 (5)152
C26—H26···O122ii0.932.463.239 (5)141
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y1/2, z+1/2.
(7) S-(2-Nitrophenyl) 2-nitrobenzene thiosulfonate top
Crystal data top
C12H8N2O6S2Z = 6
Mr = 340.32F(000) = 1044
Triclinic, P1Dx = 1.670 Mg m3
a = 8.8211 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.042 (2) ÅCell parameters from 8996 reflections
c = 21.258 (4) Åθ = 2.9–29.7°
α = 101.06 (3)°µ = 0.43 mm1
β = 91.97 (3)°T = 150 K
γ = 91.07 (3)°Plate, yellow
V = 2030.3 (7) Å30.05 × 0.05 × 0.01 mm
Data collection top
Kappa-CCD
diffractometer
8996 independent reflections
Radiation source: fine-focus sealed X-ray tube3364 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ϕ scans and ω scans with κ offsetsθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
h = 1110
Tmin = 0.979, Tmax = 0.996k = 1114
19285 measured reflectionsl = 2927
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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 0.92w = 1/[σ2(Fo2) + (0.0515P)2]
where P = (Fo2 + 2Fc2)/3
8996 reflections(Δ/σ)max = 0.001
595 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C12H8N2O6S2γ = 91.07 (3)°
Mr = 340.32V = 2030.3 (7) Å3
Triclinic, P1Z = 6
a = 8.8211 (18) ÅMo Kα radiation
b = 11.042 (2) ŵ = 0.43 mm1
c = 21.258 (4) ÅT = 150 K
α = 101.06 (3)°0.05 × 0.05 × 0.01 mm
β = 91.97 (3)°
Data collection top
Kappa-CCD
diffractometer
8996 independent reflections
Absorption correction: multi-scan
SORTAV (Blessing, 1995 & 1997)
3364 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.996Rint = 0.075
19285 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0790 restraints
wR(F2) = 0.189H-atom parameters constrained
S = 0.92Δρmax = 0.73 e Å3
8996 reflectionsΔρmin = 0.43 e Å3
595 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.75190 (18)0.42884 (16)0.26121 (8)0.0306 (4)
O10.8710 (4)0.5209 (4)0.27188 (19)0.0344 (12)
O20.7558 (5)0.3298 (4)0.20682 (19)0.0414 (12)
S20.54838 (18)0.51519 (17)0.25096 (8)0.0354 (5)
C110.7460 (6)0.3694 (6)0.3325 (3)0.0239 (15)
C120.6805 (6)0.2537 (6)0.3367 (3)0.0263 (15)
N120.5993 (6)0.1748 (6)0.2814 (3)0.0372 (15)
O1210.5014 (5)0.2206 (5)0.2526 (2)0.0533 (15)
O1220.6362 (5)0.0650 (5)0.2698 (2)0.0476 (13)
C130.6856 (6)0.2100 (6)0.3935 (3)0.0304 (16)
C140.7540 (7)0.2845 (7)0.4476 (3)0.0389 (18)
C150.8185 (6)0.3966 (6)0.4445 (3)0.0294 (16)
C160.8124 (6)0.4391 (6)0.3876 (3)0.0300 (16)
C210.5814 (6)0.6440 (6)0.3139 (3)0.0253 (15)
C220.6622 (6)0.7530 (6)0.3086 (3)0.0284 (16)
N220.7217 (6)0.7675 (5)0.2458 (3)0.0368 (14)
O2210.6408 (5)0.7366 (5)0.1976 (2)0.0450 (13)
O2220.8488 (5)0.8154 (5)0.2480 (2)0.0541 (15)
C230.6910 (7)0.8459 (7)0.3595 (3)0.0378 (18)
C240.6359 (7)0.8353 (8)0.4187 (3)0.043 (2)
C250.5565 (7)0.7337 (8)0.4263 (3)0.042 (2)
C260.5297 (6)0.6380 (7)0.3742 (3)0.0344 (17)
S30.74925 (17)0.02210 (16)0.59309 (8)0.0279 (4)
O30.6293 (4)0.0641 (4)0.5977 (2)0.0346 (11)
O40.7447 (5)0.0879 (4)0.54078 (18)0.0340 (11)
S40.95184 (17)0.07031 (16)0.58652 (8)0.0305 (4)
C310.7565 (6)0.1294 (6)0.6668 (3)0.0230 (14)
C320.8166 (6)0.2514 (6)0.6751 (3)0.0231 (15)
N320.8927 (6)0.2955 (5)0.6230 (2)0.0300 (13)
O3210.9950 (5)0.2346 (5)0.5970 (2)0.0447 (13)
O3220.8485 (5)0.3941 (4)0.6103 (2)0.0404 (12)
C330.8071 (6)0.3324 (6)0.7328 (3)0.0282 (16)
C340.7435 (7)0.2910 (7)0.7842 (3)0.0354 (17)
C350.6889 (6)0.1732 (7)0.7768 (3)0.0327 (17)
C360.6929 (6)0.0916 (6)0.7192 (3)0.0288 (16)
C410.9207 (6)0.1563 (6)0.6480 (3)0.0245 (15)
C420.8318 (6)0.2656 (6)0.6402 (3)0.0256 (15)
N420.7644 (6)0.3236 (5)0.5765 (3)0.0352 (14)
O4210.8377 (5)0.3218 (4)0.5287 (2)0.0396 (12)
O4220.6369 (5)0.3725 (5)0.5760 (2)0.0487 (14)
C430.8037 (7)0.3227 (6)0.6903 (3)0.0351 (17)
C440.8663 (7)0.2726 (7)0.7505 (3)0.0415 (19)
C450.9544 (7)0.1676 (7)0.7590 (3)0.0421 (19)
C460.9808 (6)0.1063 (6)0.7086 (3)0.0316 (16)
S50.79527 (17)0.66439 (16)0.92199 (7)0.0274 (4)
O50.9146 (4)0.7526 (4)0.92025 (18)0.0309 (11)
O60.7757 (4)0.5613 (4)0.86949 (18)0.0326 (11)
S60.59025 (17)0.75433 (16)0.92699 (8)0.0314 (4)
C510.8210 (6)0.6124 (6)0.9953 (3)0.0209 (15)
C520.7670 (6)0.5001 (6)1.0076 (3)0.0257 (15)
N520.6727 (6)0.4142 (5)0.9605 (3)0.0337 (14)
O5210.5619 (5)0.4529 (4)0.9351 (2)0.0422 (13)
O5220.7089 (5)0.3050 (5)0.9497 (2)0.0471 (13)
C530.8001 (7)0.4654 (7)1.0657 (3)0.0350 (17)
C540.8802 (7)0.5486 (8)1.1127 (3)0.045 (2)
C550.9332 (7)0.6562 (8)1.1020 (3)0.041 (2)
C560.9031 (6)0.6904 (6)1.0434 (3)0.0296 (16)
C610.6476 (6)0.8832 (6)0.9877 (3)0.0259 (15)
C620.7323 (6)0.9852 (6)0.9774 (3)0.0273 (15)
N620.7791 (7)0.9978 (5)0.9135 (3)0.0338 (14)
O6210.6899 (5)0.9626 (4)0.8678 (2)0.0412 (12)
O6220.9037 (5)1.0450 (4)0.9091 (2)0.0442 (13)
C630.7805 (6)1.0787 (6)1.0280 (3)0.0315 (16)
C640.7370 (7)1.0734 (7)1.0886 (3)0.0394 (19)
C650.6511 (7)0.9735 (7)1.1004 (3)0.0375 (18)
C660.6098 (6)0.8782 (7)1.0507 (3)0.0336 (17)
H130.64340.13110.39560.037*
H140.75590.25710.48730.047*
H150.86750.44530.48160.035*
H160.85500.51820.38640.036*
H230.74800.91720.35480.045*
H240.65430.90070.45450.052*
H250.51930.72780.46700.050*
H260.47460.56640.37990.041*
H330.84340.41530.73740.034*
H340.73840.34530.82450.043*
H350.64650.14640.81240.039*
H360.65270.00990.71520.035*
H430.74200.39580.68400.042*
H440.84800.31130.78580.050*
H450.99890.13520.80020.050*
H461.03920.03140.71580.038*
H530.76870.38671.07310.042*
H540.89790.52841.15380.054*
H550.99190.70971.13450.049*
H560.93940.76811.03640.035*
H630.84281.14541.02060.038*
H640.76571.13881.12320.047*
H650.62120.97121.14270.045*
H660.55520.80851.05910.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0378 (10)0.0227 (11)0.0317 (10)0.0043 (8)0.0024 (8)0.0058 (8)
O10.025 (2)0.046 (3)0.036 (3)0.004 (2)0.0004 (19)0.020 (2)
O20.068 (3)0.031 (3)0.023 (2)0.013 (2)0.001 (2)0.001 (2)
S20.0399 (10)0.0254 (11)0.0396 (10)0.0023 (8)0.0081 (8)0.0041 (9)
C110.024 (3)0.018 (4)0.030 (4)0.003 (3)0.002 (3)0.004 (3)
C120.022 (3)0.021 (4)0.033 (4)0.003 (3)0.001 (3)0.003 (3)
N120.034 (3)0.030 (4)0.047 (4)0.004 (3)0.004 (3)0.006 (3)
O1210.045 (3)0.045 (4)0.065 (4)0.005 (3)0.019 (3)0.001 (3)
O1220.063 (3)0.024 (3)0.054 (3)0.002 (3)0.007 (2)0.002 (3)
C130.032 (4)0.013 (4)0.049 (4)0.000 (3)0.008 (3)0.014 (3)
C140.043 (4)0.042 (5)0.038 (4)0.008 (4)0.014 (3)0.021 (4)
C150.034 (4)0.035 (5)0.020 (4)0.003 (3)0.006 (3)0.005 (3)
C160.031 (3)0.023 (4)0.037 (4)0.001 (3)0.004 (3)0.010 (3)
C210.027 (3)0.020 (4)0.028 (4)0.002 (3)0.004 (3)0.002 (3)
C220.020 (3)0.028 (4)0.038 (4)0.005 (3)0.002 (3)0.008 (3)
N220.042 (4)0.022 (4)0.045 (4)0.008 (3)0.005 (3)0.002 (3)
O2210.050 (3)0.050 (4)0.035 (3)0.006 (3)0.005 (2)0.007 (3)
O2220.046 (3)0.051 (4)0.060 (4)0.017 (3)0.017 (3)0.003 (3)
C230.032 (4)0.028 (5)0.050 (5)0.004 (3)0.004 (3)0.000 (4)
C240.045 (4)0.048 (6)0.031 (4)0.014 (4)0.000 (4)0.009 (4)
C250.035 (4)0.063 (6)0.029 (4)0.014 (4)0.004 (3)0.012 (4)
C260.026 (3)0.041 (5)0.042 (4)0.004 (3)0.001 (3)0.023 (4)
S30.0330 (9)0.0208 (11)0.0289 (9)0.0010 (8)0.0028 (7)0.0029 (8)
O30.029 (2)0.022 (3)0.051 (3)0.009 (2)0.006 (2)0.004 (2)
O40.058 (3)0.018 (3)0.027 (3)0.002 (2)0.007 (2)0.007 (2)
S40.0353 (9)0.0227 (11)0.0359 (10)0.0049 (8)0.0107 (8)0.0096 (8)
C310.022 (3)0.019 (4)0.030 (4)0.002 (3)0.003 (3)0.006 (3)
C320.019 (3)0.027 (4)0.025 (4)0.001 (3)0.003 (3)0.009 (3)
N320.029 (3)0.025 (4)0.036 (3)0.012 (3)0.005 (3)0.009 (3)
O3210.041 (3)0.048 (4)0.050 (3)0.001 (3)0.017 (2)0.019 (3)
O3220.054 (3)0.024 (3)0.048 (3)0.000 (2)0.001 (2)0.019 (2)
C330.031 (4)0.017 (4)0.034 (4)0.001 (3)0.006 (3)0.001 (3)
C340.043 (4)0.038 (5)0.024 (4)0.006 (4)0.001 (3)0.003 (3)
C350.029 (4)0.045 (5)0.025 (4)0.002 (3)0.001 (3)0.009 (4)
C360.037 (4)0.017 (4)0.033 (4)0.004 (3)0.002 (3)0.005 (3)
C410.023 (3)0.025 (4)0.029 (4)0.005 (3)0.006 (3)0.015 (3)
C420.023 (3)0.031 (4)0.024 (4)0.007 (3)0.005 (3)0.008 (3)
N420.043 (4)0.020 (4)0.042 (4)0.004 (3)0.002 (3)0.008 (3)
O4210.053 (3)0.037 (3)0.026 (3)0.001 (2)0.002 (2)0.001 (2)
O4220.043 (3)0.039 (4)0.065 (4)0.016 (3)0.007 (3)0.016 (3)
C430.039 (4)0.026 (4)0.046 (5)0.000 (3)0.006 (3)0.019 (4)
C440.049 (4)0.052 (6)0.027 (4)0.014 (4)0.005 (3)0.014 (4)
C450.039 (4)0.049 (6)0.041 (5)0.011 (4)0.005 (3)0.013 (4)
C460.032 (4)0.024 (4)0.036 (4)0.002 (3)0.002 (3)0.002 (3)
S50.0344 (9)0.0219 (11)0.0261 (9)0.0004 (8)0.0001 (7)0.0057 (8)
O50.029 (2)0.032 (3)0.033 (3)0.001 (2)0.0003 (19)0.008 (2)
O60.047 (3)0.022 (3)0.025 (2)0.001 (2)0.001 (2)0.002 (2)
S60.0330 (9)0.0214 (11)0.0373 (10)0.0001 (8)0.0062 (8)0.0009 (8)
C510.017 (3)0.027 (4)0.018 (3)0.003 (3)0.002 (3)0.005 (3)
C520.032 (3)0.012 (4)0.031 (4)0.003 (3)0.001 (3)0.001 (3)
N520.038 (3)0.025 (4)0.039 (4)0.003 (3)0.005 (3)0.009 (3)
O5210.039 (3)0.038 (3)0.047 (3)0.003 (2)0.007 (2)0.004 (3)
O5220.053 (3)0.022 (3)0.064 (4)0.004 (2)0.001 (3)0.003 (3)
C530.036 (4)0.033 (5)0.043 (4)0.014 (3)0.015 (3)0.021 (4)
C540.044 (4)0.065 (7)0.028 (4)0.020 (4)0.000 (4)0.013 (4)
C550.021 (3)0.071 (7)0.029 (4)0.000 (4)0.005 (3)0.010 (4)
C560.030 (3)0.024 (4)0.035 (4)0.001 (3)0.001 (3)0.005 (3)
C610.024 (3)0.020 (4)0.032 (4)0.003 (3)0.001 (3)0.001 (3)
C620.026 (3)0.024 (4)0.032 (4)0.004 (3)0.001 (3)0.005 (3)
N620.045 (4)0.018 (4)0.039 (4)0.001 (3)0.008 (3)0.006 (3)
O6210.053 (3)0.035 (3)0.037 (3)0.000 (2)0.002 (2)0.010 (2)
O6220.042 (3)0.036 (3)0.054 (3)0.009 (3)0.010 (2)0.006 (3)
C630.026 (3)0.024 (4)0.043 (4)0.001 (3)0.010 (3)0.005 (3)
C640.039 (4)0.027 (5)0.045 (5)0.008 (3)0.011 (4)0.010 (4)
C650.045 (4)0.034 (5)0.031 (4)0.010 (4)0.010 (3)0.004 (4)
C660.027 (3)0.035 (5)0.042 (4)0.004 (3)0.013 (3)0.012 (4)
Geometric parameters (Å, º) top
S1—O11.430 (4)C35—H350.9500
S1—O21.433 (4)C36—H360.9500
S1—C111.764 (6)C41—C461.384 (8)
S1—S22.073 (2)C41—C421.406 (8)
S2—C211.768 (6)C42—C431.365 (8)
C11—C161.379 (8)C42—N421.483 (7)
C11—C121.412 (8)N42—O4211.226 (6)
C12—C131.384 (8)N42—O4221.237 (6)
C12—N121.477 (7)C43—C441.384 (8)
N12—O1211.214 (6)C43—H430.9500
N12—O1221.242 (7)C44—C451.363 (10)
C13—C141.390 (9)C44—H440.9500
C13—H130.9500C45—C461.396 (9)
C14—C151.366 (9)C45—H450.9500
C14—H140.9500C46—H460.9500
C15—C161.377 (8)S5—O51.427 (4)
C15—H150.9500S5—O61.437 (4)
C16—H160.9500S5—C511.771 (6)
C21—C261.387 (8)S5—S62.076 (2)
C21—C221.412 (9)S6—C611.781 (6)
C22—C231.354 (9)C51—C561.378 (8)
C22—N221.486 (8)C51—C521.394 (8)
N22—O2211.219 (6)C52—C531.387 (8)
N22—O2221.226 (6)C52—N521.464 (7)
C23—C241.390 (9)N52—O5211.223 (6)
C23—H230.9500N52—O5221.233 (7)
C24—C251.349 (10)C53—C541.385 (9)
C24—H240.9500C53—H530.9500
C25—C261.387 (9)C54—C551.331 (10)
C25—H250.9500C54—H540.9500
C26—H260.9500C55—C561.387 (8)
S3—O31.428 (4)C55—H550.9500
S3—O41.440 (4)C56—H560.9500
S3—C311.773 (6)C61—C621.396 (9)
S3—S42.070 (2)C61—C661.401 (8)
S4—C411.782 (6)C62—C631.389 (8)
C31—C361.394 (8)C62—N621.466 (8)
C31—C321.415 (8)N62—O6221.221 (6)
C32—C331.377 (8)N62—O6211.226 (6)
C32—N321.471 (7)C63—C641.369 (9)
N32—O3211.219 (6)C63—H630.9500
N32—O3221.237 (6)C64—C651.393 (9)
C33—C341.393 (8)C64—H640.9500
C33—H330.9500C65—C661.374 (9)
C34—C351.357 (9)C65—H650.9500
C34—H340.9500C66—H660.9500
C35—C361.375 (8)
O1—S1—O2119.3 (3)C35—C36—C31119.6 (6)
O1—S1—C11105.8 (3)C35—C36—H36120.2
O2—S1—C11110.1 (3)C31—C36—H36120.2
O1—S1—S2108.3 (2)C46—C41—C42118.2 (6)
O2—S1—S2105.5 (2)C46—C41—S4116.8 (5)
C11—S1—S2107.4 (2)C42—C41—S4124.9 (5)
C21—S2—S197.6 (2)C43—C42—C41122.1 (6)
C16—C11—C12117.5 (6)C43—C42—N42117.2 (6)
C16—C11—S1118.1 (5)C41—C42—N42120.7 (5)
C12—C11—S1124.4 (4)O421—N42—O422124.7 (6)
C13—C12—C11121.6 (6)O421—N42—C42118.8 (5)
C13—C12—N12116.6 (6)O422—N42—C42116.4 (5)
C11—C12—N12121.8 (6)C42—C43—C44119.0 (7)
O121—N12—O122125.9 (6)C42—C43—H43120.5
O121—N12—C12118.4 (6)C44—C43—H43120.5
O122—N12—C12115.7 (5)C45—C44—C43119.9 (7)
C12—C13—C14118.3 (6)C45—C44—H44120.0
C12—C13—H13120.8C43—C44—H44120.0
C14—C13—H13120.8C44—C45—C46121.7 (7)
C15—C14—C13121.1 (6)C44—C45—H45119.2
C15—C14—H14119.5C46—C45—H45119.2
C13—C14—H14119.5C41—C46—C45119.0 (7)
C14—C15—C16120.0 (6)C41—C46—H46120.5
C14—C15—H15120.0C45—C46—H46120.5
C16—C15—H15120.0O5—S5—O6118.7 (3)
C15—C16—C11121.5 (6)O5—S5—C51106.6 (3)
C15—C16—H16119.2O6—S5—C51110.4 (3)
C11—C16—H16119.2O5—S5—S6108.6 (2)
C26—C21—C22116.3 (6)O6—S5—S6105.65 (19)
C26—C21—S2118.6 (5)C51—S5—S6106.2 (2)
C22—C21—S2125.0 (5)C61—S6—S597.4 (2)
C23—C22—C21122.3 (6)C56—C51—C52118.3 (5)
C23—C22—N22117.7 (6)C56—C51—S5116.2 (5)
C21—C22—N22120.0 (6)C52—C51—S5125.5 (4)
O221—N22—O222125.4 (6)C53—C52—C51120.9 (6)
O221—N22—C22118.9 (5)C53—C52—N52117.0 (6)
O222—N22—C22115.6 (5)C51—C52—N52122.1 (5)
C22—C23—C24119.0 (7)O521—N52—O522123.7 (5)
C22—C23—H23120.5O521—N52—C52119.1 (6)
C24—C23—H23120.5O522—N52—C52117.2 (5)
C25—C24—C23121.1 (7)C54—C53—C52118.1 (7)
C25—C24—H24119.5C54—C53—H53120.9
C23—C24—H24119.5C52—C53—H53120.9
C24—C25—C26119.6 (7)C55—C54—C53121.8 (6)
C24—C25—H25120.2C55—C54—H54119.1
C26—C25—H25120.2C53—C54—H54119.1
C25—C26—C21121.7 (7)C54—C55—C56120.2 (7)
C25—C26—H26119.2C54—C55—H55119.9
C21—C26—H26119.2C56—C55—H55119.9
O3—S3—O4119.1 (3)C51—C56—C55120.4 (7)
O3—S3—C31106.0 (3)C51—C56—H56119.8
O4—S3—C31109.4 (3)C55—C56—H56119.8
O3—S3—S4108.5 (2)C62—C61—C66118.2 (6)
O4—S3—S4105.8 (2)C62—C61—S6124.8 (5)
C31—S3—S4107.58 (19)C66—C61—S6117.0 (5)
C41—S4—S397.33 (19)C63—C62—C61121.4 (6)
C36—C31—C32118.3 (6)C63—C62—N62116.4 (6)
C36—C31—S3117.2 (5)C61—C62—N62122.2 (6)
C32—C31—S3124.5 (5)O622—N62—O621124.0 (5)
C33—C32—C31120.9 (6)O622—N62—C62117.8 (5)
C33—C32—N32117.8 (6)O621—N62—C62118.1 (5)
C31—C32—N32121.3 (6)C64—C63—C62118.9 (7)
O321—N32—O322125.5 (6)C64—C63—H63120.5
O321—N32—C32118.2 (5)C62—C63—H63120.5
O322—N32—C32116.2 (5)C63—C64—C65121.0 (6)
C32—C33—C34119.1 (6)C63—C64—H64119.5
C32—C33—H33120.5C65—C64—H64119.5
C34—C33—H33120.5C66—C65—C64119.8 (6)
C35—C34—C33120.1 (6)C66—C65—H65120.1
C35—C34—H34119.9C64—C65—H65120.1
C33—C34—H34119.9C65—C66—C61120.5 (7)
C34—C35—C36122.0 (7)C65—C66—H66119.7
C34—C35—H35119.0C61—C66—H66119.7
C36—C35—H35119.0
O1—S1—S2—C2142.5 (3)C34—C35—C36—C310.8 (9)
O2—S1—S2—C21171.3 (3)C32—C31—C36—C350.7 (8)
C11—S1—S2—C2171.3 (3)S3—C31—C36—C35176.8 (4)
O1—S1—C11—C1619.2 (5)S3—S4—C41—C4695.0 (4)
O2—S1—C11—C16149.4 (4)S3—S4—C41—C4280.5 (5)
S2—S1—C11—C1696.2 (5)C46—C41—C42—C430.1 (9)
O1—S1—C11—C12159.4 (5)S4—C41—C42—C43175.4 (5)
O2—S1—C11—C1229.3 (6)C46—C41—C42—N42180.0 (5)
S2—S1—C11—C1285.2 (5)S4—C41—C42—N424.6 (8)
C16—C11—C12—C131.5 (8)C43—C42—N42—O421142.7 (6)
S1—C11—C12—C13177.1 (4)C41—C42—N42—O42137.3 (8)
C16—C11—C12—N12176.6 (5)C43—C42—N42—O42236.2 (8)
S1—C11—C12—N124.7 (8)C41—C42—N42—O422143.8 (6)
C13—C12—N12—O121127.8 (6)C41—C42—C43—C441.0 (9)
C11—C12—N12—O12150.5 (8)N42—C42—C43—C44179.1 (5)
C13—C12—N12—O12250.4 (7)C42—C43—C44—C450.1 (10)
C11—C12—N12—O122131.3 (6)C43—C44—C45—C461.6 (10)
C11—C12—C13—C141.6 (9)C42—C41—C46—C451.6 (9)
N12—C12—C13—C14176.6 (5)S4—C41—C46—C45177.5 (5)
C12—C13—C14—C151.8 (9)C44—C45—C46—C412.5 (10)
C13—C14—C15—C161.9 (10)O5—S5—S6—C6145.9 (3)
C14—C15—C16—C111.9 (9)O6—S5—S6—C61174.3 (3)
C12—C11—C16—C151.6 (8)C51—S5—S6—C6168.4 (3)
S1—C11—C16—C15177.1 (5)O5—S5—C51—C5622.7 (5)
S1—S2—C21—C2693.1 (5)O6—S5—C51—C56152.9 (4)
S1—S2—C21—C2284.3 (5)S6—S5—C51—C5693.0 (4)
C26—C21—C22—C231.3 (9)O5—S5—C51—C52156.5 (5)
S2—C21—C22—C23176.2 (5)O6—S5—C51—C5226.3 (6)
C26—C21—C22—N22180.0 (5)S6—S5—C51—C5287.8 (5)
S2—C21—C22—N222.5 (8)C56—C51—C52—C532.5 (9)
C23—C22—N22—O221137.8 (6)S5—C51—C52—C53176.7 (4)
C21—C22—N22—O22143.4 (8)C56—C51—C52—N52177.0 (5)
C23—C22—N22—O22239.3 (8)S5—C51—C52—N523.8 (8)
C21—C22—N22—O222139.5 (6)C53—C52—N52—O521129.8 (6)
C21—C22—C23—C241.7 (9)C51—C52—N52—O52149.8 (8)
N22—C22—C23—C24179.6 (5)C53—C52—N52—O52248.8 (8)
C22—C23—C24—C250.9 (10)C51—C52—N52—O522131.7 (6)
C23—C24—C25—C260.2 (10)C51—C52—C53—C543.9 (9)
C24—C25—C26—C210.6 (10)N52—C52—C53—C54175.6 (5)
C22—C21—C26—C250.1 (9)C52—C53—C54—C554.2 (10)
S2—C21—C26—C25177.6 (5)C53—C54—C55—C562.9 (10)
O3—S3—S4—C4144.5 (3)C52—C51—C56—C551.2 (9)
O4—S3—S4—C41173.4 (3)S5—C51—C56—C55178.1 (5)
C31—S3—S4—C4169.7 (3)C54—C55—C56—C511.4 (10)
O3—S3—C31—C3621.3 (5)S5—S6—C61—C6279.2 (5)
O4—S3—C31—C36150.9 (4)S5—S6—C61—C6698.0 (4)
S4—S3—C31—C3694.6 (4)C66—C61—C62—C631.1 (9)
O3—S3—C31—C32156.0 (5)S6—C61—C62—C63176.0 (4)
O4—S3—C31—C3226.4 (6)C66—C61—C62—N62179.1 (5)
S4—S3—C31—C3288.1 (5)S6—C61—C62—N622.0 (8)
C36—C31—C32—C332.6 (8)C63—C62—N62—O62234.6 (8)
S3—C31—C32—C33174.7 (4)C61—C62—N62—O622143.5 (6)
C36—C31—C32—N32176.7 (5)C63—C62—N62—O621144.0 (6)
S3—C31—C32—N326.0 (8)C61—C62—N62—O62137.9 (8)
C33—C32—N32—O321127.0 (6)C61—C62—C63—C643.5 (9)
C31—C32—N32—O32152.3 (7)N62—C62—C63—C64178.4 (5)
C33—C32—N32—O32251.4 (7)C62—C63—C64—C652.8 (9)
C31—C32—N32—O322129.3 (6)C63—C64—C65—C660.4 (10)
C31—C32—C33—C343.0 (8)C64—C65—C66—C612.8 (9)
N32—C32—C33—C34176.3 (5)C62—C61—C66—C652.1 (9)
C32—C33—C34—C351.5 (9)S6—C61—C66—C65179.5 (5)
C33—C34—C35—C360.4 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O40.952.373.209 (8)147
C34—H34···O60.952.413.183 (9)139
C35—H35···O621i0.952.563.298 (9)134
C44—H44···O6i0.952.563.502 (8)172
C54—H54···O1ii0.952.553.459 (8)161
C64—H64···O2iii0.952.493.403 (8)161
C13—H13···O3iv0.952.523.214 (7)130
C46—H46···O222v0.952.533.466 (8)168
C56—H56···O622vi0.952.533.320 (8)141
C63—H63···O5vi0.952.573.277 (7)131
Symmetry codes: (i) x, y1, z; (ii) x, y, z+1; (iii) x, y+1, z+1; (iv) x+1, y, z+1; (v) x+2, y+1, z+1; (vi) x+2, y+2, z+2.

Experimental details

(1)(2)(3)(4)
Crystal data
Chemical formulaC13H11NO2S2C12H8ClNO2S2C13H10N2O4S2C9H8N2O6S2
Mr277.35297.76322.35304.30
Crystal system, space groupMonoclinic, P21/cTriclinic, P1Monoclinic, P21Triclinic, P1
Temperature (K)150150150150
a, b, c (Å)6.6384 (2), 24.4389 (7), 7.9478 (3)7.0434 (5), 7.8315 (5), 11.3709 (8)10.1301 (2), 6.3474 (1), 11.1133 (2)8.1655 (3), 8.2415 (3), 9.3887 (4)
α, β, γ (°)90, 93.6346 (10), 9082.576 (4), 80.690 (3), 83.189 (3)90, 106.644 (8), 9072.1417 (15), 83.3965 (14), 80.332 (3)
V3)1286.82 (7)610.71 (7)684.64 (2)591.48 (4)
Z4222
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.410.650.410.48
Crystal size (mm)0.25 × 0.20 × 0.100.20 × 0.15 × 0.020.55 × 0.10 × 0.080.35 × 0.05 × 0.03
Data collection
DiffractometerKappa-CCD
diffractometer
Kappa-CCD
diffractometer
Kappa-CCD
diffractometer
Kappa-CCD
diffractometer
Absorption correctionMulti-scan
SORTAV (Blessing, 1995 & 1997)
Multi-scan
SORTAV (Blessing, 1995 & 1997)
Multi-scan
SORTAV (Blessing, 1995 & 1997)
Multi-scan
SORTAV (Blessing, 1995 & 1997)
Tmin, Tmax0.905, 0.9610.882, 0.9870.808, 0.9700.851, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
13605, 2935, 1639 6846, 2960, 2327 7452, 1695, 1615 6105, 2629, 1969
Rint0.0720.0360.0720.050
(sin θ/λ)max1)0.6470.6710.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.147, 1.03 0.044, 0.116, 1.05 0.039, 0.107, 1.04 0.044, 0.111, 1.04
No. of reflections2935296016952629
No. of parameters164163191173
No. of restraints0010
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.250.40, 0.420.40, 0.510.36, 0.38


(5)(6)(7)
Crystal data
Chemical formulaC12H8N2O4S2C14H6F6N2O4S2C12H8N2O6S2
Mr308.32444.33340.32
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cTriclinic, P1
Temperature (K)150150150
a, b, c (Å)7.1028 (11), 22.925 (4), 7.7769 (14)14.1617 (5), 5.3367 (2), 22.6233 (10)8.8211 (18), 11.042 (2), 21.258 (4)
α, β, γ (°)90, 95.536 (12), 9090, 91.7376 (13), 90101.06 (3), 91.97 (3), 91.07 (3)
V3)1260.4 (4)1709.01 (12)2030.3 (7)
Z446
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.440.400.43
Crystal size (mm)0.40 × 0.07 × 0.070.35 × 0.10 × 0.050.05 × 0.05 × 0.01
Data collection
DiffractometerKappa-CCD
diffractometer
Kappa-CCD
diffractometer
Kappa-CCD
diffractometer
Absorption correctionMulti-scan
SORTAV (Blessing, 1995 & 1997)
Multi-scan
SORTAV (Blessing, 1995 & 1997)
Multi-scan
SORTAV (Blessing, 1995 & 1997)
Tmin, Tmax0.845, 0.9700.873, 0.9800.979, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
3982, 1862, 1135 14106, 3812, 1646 19285, 8996, 3364
Rint0.0590.0810.075
(sin θ/λ)max1)0.5950.6490.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.135, 1.03 0.053, 0.149, 0.94 0.079, 0.189, 0.92
No. of reflections186238128996
No. of parameters181253595
No. of restraints000
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.290.37, 0.250.73, 0.43

Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b), ORTEP (Johnson, 1976), PLATON (Spek, 1999), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (4) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O3i0.952.353.299 (3)176
Symmetry code: (i) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) for (5) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O222i0.952.493.197 (5)131
Symmetry code: (i) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) for (6) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O222i0.932.573.421 (5)152
C26—H26···O122ii0.932.463.239 (5)141
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (7) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O40.952.373.209 (8)147
C34—H34···O60.952.413.183 (9)139
C35—H35···O621i0.952.563.298 (9)134
C44—H44···O6i0.952.563.502 (8)172
C54—H54···O1ii0.952.553.459 (8)161
C64—H64···O2iii0.952.493.403 (8)161
C13—H13···O3iv0.952.523.214 (7)130
C46—H46···O222v0.952.533.466 (8)168
C56—H56···O622vi0.952.533.320 (8)141
C63—H63···O5vi0.952.573.277 (7)131
Symmetry codes: (i) x, y1, z; (ii) x, y, z+1; (iii) x, y+1, z+1; (iv) x+1, y, z+1; (v) x+2, y+1, z+1; (vi) x+2, y+2, z+2.
 

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