Conformational preferences and supramolecular aggregation in 2-nitrophenylthiolates: disulfides and thiosulfonates

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.

S1. Comment

Comment in full text version

S2. Experimental

Synthesis in full text version

S3. Refinement

See full text version

Computing details

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

In full text version

(1) 2-Nitro-4'-methyldiphenyl disulfide

Crystal data

C13H11NO2S2	F(000) = 576
Mr = 277.35	Dx = 1.432 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6384 (2) Å	Cell parameters from 2935 reflections
b = 24.4389 (7) Å	θ = 1.7–27.4°
c = 7.9478 (3) Å	µ = 0.41 mm^−1
β = 93.6346 (10)°	T = 150 K
V = 1286.82 (7) Å^3	Block, yellow
Z = 4	0.25 × 0.20 × 0.10 mm

Data collection

Kappa-CCD diffractometer	2935 independent reflections
Radiation source: fine-focus sealed X-ray tube	1639 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
ϕ scans and ω scans with κ offsets	θmax = 27.4°, θmin = 1.7°
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997)	h = −8→8
Tmin = 0.905, Tmax = 0.961	k = −31→31
13605 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0738P)^2] where P = (Fo^2 + 2Fc^2)/3
2935 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.20408 (10)	0.56546 (3)	0.30150 (9)	0.0696 (3)
S2	0.05205 (9)	0.63845 (3)	0.31321 (9)	0.0659 (3)
C11	0.3654 (3)	0.56755 (9)	0.4884 (3)	0.0545 (6)
C12	0.2964 (4)	0.55147 (11)	0.6414 (4)	0.0681 (7)
C13	0.4224 (4)	0.55274 (11)	0.7852 (4)	0.0716 (8)
C14	0.6219 (4)	0.56912 (10)	0.7816 (3)	0.0610 (7)
C15	0.6889 (4)	0.58499 (12)	0.6283 (4)	0.0659 (7)
C16	0.5642 (3)	0.58387 (11)	0.4836 (3)	0.0631 (7)
C141	0.7634 (4)	0.56926 (12)	0.9382 (4)	0.0809 (9)
C21	0.2108 (3)	0.68762 (10)	0.2224 (3)	0.0524 (6)
C22	0.1752 (4)	0.74342 (12)	0.2309 (3)	0.0623 (7)
C23	0.3051 (5)	0.78207 (12)	0.1674 (4)	0.0784 (9)
C24	0.4735 (5)	0.76482 (14)	0.0911 (4)	0.0803 (9)
C25	0.5092 (4)	0.71019 (13)	0.0762 (3)	0.0704 (8)
C26	0.3817 (4)	0.67193 (12)	0.1400 (3)	0.0610 (7)
N22	−0.0005 (5)	0.76411 (14)	0.3107 (3)	0.0846 (8)
O221	−0.1195 (3)	0.73069 (12)	0.3618 (3)	0.1044 (8)
O222	−0.0218 (4)	0.81352 (12)	0.3256 (3)	0.1313 (10)
H12	0.1637	0.5397	0.6469	0.082*
H13	0.3727	0.5424	0.8873	0.086*
H15	0.8216	0.5967	0.6227	0.079*
H16	0.6140	0.5942	0.3816	0.076*
H14A	0.8942	0.5818	0.9101	0.121*	0.50
H14B	0.7745	0.5328	0.9832	0.121*	0.50
H14C	0.7116	0.5932	1.0208	0.121*	0.50
H14D	0.6926	0.5568	1.0326	0.121*	0.50
H14E	0.8124	0.6057	0.9596	0.121*	0.50
H14F	0.8753	0.5453	0.9220	0.121*	0.50
H23	0.2778	0.8192	0.1768	0.094*
H24	0.5625	0.7902	0.0500	0.096*
H25	0.6216	0.6985	0.0219	0.084*
H26	0.4100	0.6349	0.1281	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0775 (5)	0.0550 (5)	0.0750 (5)	−0.0089 (3)	−0.0060 (4)	−0.0064 (4)
S2	0.0507 (4)	0.0754 (6)	0.0712 (5)	−0.0005 (3)	0.0007 (3)	−0.0013 (4)
C11	0.0611 (14)	0.0408 (15)	0.0617 (16)	−0.0012 (11)	0.0054 (12)	−0.0020 (12)
C12	0.0622 (15)	0.0628 (19)	0.080 (2)	−0.0066 (13)	0.0085 (14)	0.0105 (15)
C13	0.0848 (19)	0.063 (2)	0.0685 (19)	−0.0036 (15)	0.0154 (15)	0.0097 (15)
C14	0.0782 (17)	0.0417 (16)	0.0629 (18)	0.0030 (12)	0.0025 (14)	−0.0005 (13)
C15	0.0601 (14)	0.0641 (19)	0.073 (2)	−0.0050 (13)	0.0022 (13)	0.0056 (15)
C16	0.0623 (15)	0.0669 (19)	0.0611 (17)	−0.0042 (13)	0.0103 (13)	0.0066 (14)
C141	0.105 (2)	0.062 (2)	0.073 (2)	−0.0040 (15)	−0.0112 (17)	0.0021 (15)
C21	0.0510 (13)	0.0577 (17)	0.0473 (14)	0.0057 (12)	−0.0076 (10)	−0.0019 (12)
C22	0.0722 (16)	0.0615 (19)	0.0509 (16)	0.0180 (14)	−0.0138 (13)	−0.0041 (14)
C23	0.123 (3)	0.0494 (19)	0.0589 (18)	0.0121 (18)	−0.0224 (17)	0.0051 (14)
C24	0.098 (2)	0.077 (2)	0.065 (2)	−0.0104 (18)	−0.0089 (17)	0.0191 (17)
C25	0.0724 (17)	0.075 (2)	0.0630 (18)	0.0039 (15)	0.0032 (13)	0.0146 (16)
C26	0.0663 (15)	0.0539 (17)	0.0626 (17)	0.0062 (13)	0.0034 (13)	0.0024 (13)
N22	0.101 (2)	0.089 (2)	0.0613 (16)	0.0453 (17)	−0.0129 (14)	−0.0099 (15)
O221	0.0760 (15)	0.125 (2)	0.113 (2)	0.0366 (14)	0.0112 (13)	−0.0130 (16)
O222	0.178 (2)	0.091 (2)	0.125 (2)	0.0727 (19)	0.0115 (17)	−0.0178 (15)

Geometric parameters (Å, º)

S1—S2	2.0544 (10)	C141—H14B	0.9600
S1—C11	1.776 (3)	C141—H14C	0.9600
S2—C21	1.781 (2)	C141—H14D	0.9600
N22—O221	1.224 (4)	C141—H14E	0.9600
N22—O222	1.222 (4)	C141—H14F	0.9600
C11—C16	1.381 (3)	C21—C22	1.386 (4)
C11—C12	1.384 (4)	C21—C26	1.399 (3)
C12—C13	1.373 (4)	C22—C23	1.395 (4)
C12—H12	0.9300	C22—N22	1.453 (4)
C13—C14	1.386 (3)	C23—C24	1.371 (4)
C13—H13	0.9300	C23—H23	0.9300
C14—C15	1.379 (4)	C24—C25	1.363 (4)
C14—C141	1.511 (4)	C24—H24	0.9300
C15—C16	1.374 (3)	C25—C26	1.379 (4)
C15—H15	0.9300	C25—H25	0.9300
C16—H16	0.9300	C26—H26	0.9300
C141—H14A	0.9600
C11—S1—S2	102.07 (8)	H14B—C141—H14D	56.3
C21—S2—S1	105.22 (8)	H14C—C141—H14D	56.3
O221—N22—O222	123.1 (3)	C14—C141—H14E	109.5
O221—N22—C22	117.7 (3)	H14A—C141—H14E	56.3
O222—N22—C22	119.1 (3)	H14B—C141—H14E	141.1
C16—C11—C12	118.5 (2)	H14C—C141—H14E	56.3
C16—C11—S1	120.8 (2)	H14D—C141—H14E	109.5
C12—C11—S1	120.73 (19)	C14—C141—H14F	109.5
C13—C12—C11	120.4 (2)	H14A—C141—H14F	56.3
C13—C12—H12	119.8	H14B—C141—H14F	56.3
C11—C12—H12	119.8	H14C—C141—H14F	141.1
C12—C13—C14	121.5 (3)	H14D—C141—H14F	109.5
C12—C13—H13	119.3	H14E—C141—H14F	109.5
C14—C13—H13	119.3	C22—C21—C26	116.0 (2)
C15—C14—C13	117.5 (2)	C22—C21—S2	122.5 (2)
C15—C14—C141	120.6 (3)	C26—C21—S2	121.5 (2)
C13—C14—C141	121.9 (2)	C21—C22—C23	122.5 (3)
C16—C15—C14	121.5 (2)	C21—C22—N22	120.5 (3)
C16—C15—H15	119.2	C23—C22—N22	117.0 (3)
C14—C15—H15	119.2	C24—C23—C22	119.5 (3)
C15—C16—C11	120.6 (2)	C24—C23—H23	120.3
C15—C16—H16	119.7	C22—C23—H23	120.3
C11—C16—H16	119.7	C25—C24—C23	119.4 (3)
C14—C141—H14A	109.5	C25—C24—H24	120.3
C14—C141—H14B	109.5	C23—C24—H24	120.3
H14A—C141—H14B	109.5	C24—C25—C26	121.2 (3)
C14—C141—H14C	109.5	C24—C25—H25	119.4
H14A—C141—H14C	109.5	C26—C25—H25	119.4
H14B—C141—H14C	109.5	C25—C26—C21	121.4 (3)
C14—C141—H14D	109.5	C25—C26—H26	119.3
H14A—C141—H14D	141.1	C21—C26—H26	119.3
C11—S1—S2—C21	85.36 (12)	C141—C14—C15—C16	178.4 (2)
S2—S1—C11—C16	−98.0 (2)	C14—C15—C16—C11	1.1 (4)
S2—S1—C11—C12	83.8 (2)	C12—C11—C16—C15	−1.2 (4)
S1—S2—C21—C22	−169.75 (17)	S1—C11—C16—C15	−179.5 (2)
S1—S2—C21—C26	9.3 (2)	C26—C21—C22—C23	−2.4 (3)
C21—C22—N22—O221	−3.6 (4)	S2—C21—C22—C23	176.62 (19)
C23—C22—N22—O221	177.6 (2)	C26—C21—C22—N22	178.8 (2)
C21—C22—N22—O222	175.6 (2)	S2—C21—C22—N22	−2.2 (3)
C23—C22—N22—O222	−3.3 (4)	C21—C22—C23—C24	1.0 (4)
C16—C11—C12—C13	1.1 (4)	N22—C22—C23—C24	179.9 (2)
S1—C11—C12—C13	179.4 (2)	C22—C23—C24—C25	1.1 (4)
C11—C12—C13—C14	−1.1 (4)	C23—C24—C25—C26	−1.6 (4)
C12—C13—C14—C15	1.0 (4)	C24—C25—C26—C21	0.1 (4)
C12—C13—C14—C141	−178.4 (2)	C22—C21—C26—C25	1.9 (3)
C13—C14—C15—C16	−1.0 (4)	S2—C21—C26—C25	−177.17 (19)

(2) 2-Nitro-4'-chlorodiphenyl disulfide

Crystal data

C12H8ClNO2S2	Z = 2
Mr = 297.76	F(000) = 304
Triclinic, P1	Dx = 1.619 Mg m^−3
a = 7.0434 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8315 (5) Å	Cell parameters from 2960 reflections
c = 11.3709 (8) Å	θ = 2.9–30.2°
α = 82.576 (4)°	µ = 0.65 mm^−1
β = 80.690 (3)°	T = 150 K
γ = 83.189 (3)°	Plate, yellow
V = 610.71 (7) Å^3	0.20 × 0.15 × 0.02 mm

Data collection

Kappa-CCD diffractometer	2960 independent reflections
Radiation source: fine-focus sealed X-ray tube	2327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ϕ scans and ω scans with κ offsets	θmax = 28.5°, θmin = 2.9°
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997)	h = −9→9
Tmin = 0.882, Tmax = 0.987	k = −10→10
6846 measured reflections	l = −13→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0627P)^2] where P = (Fo^2 + 2Fc^2)/3
2960 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.14074 (7)	0.39829 (6)	0.17396 (4)	0.02787 (16)
S2	0.21248 (7)	0.46708 (6)	0.32690 (4)	0.02647 (16)
C11	0.3636 (3)	0.3184 (2)	0.09132 (17)	0.0242 (4)
C12	0.5407 (3)	0.2980 (3)	0.13321 (19)	0.0287 (5)
C13	0.7061 (3)	0.2329 (3)	0.06260 (19)	0.0294 (5)
C14	0.6923 (3)	0.1898 (2)	−0.04922 (17)	0.0257 (4)
Cl14	0.90005 (8)	0.11244 (7)	−0.14014 (5)	0.03490 (17)
C15	0.5176 (3)	0.2095 (3)	−0.09223 (18)	0.0306 (5)
C16	0.3525 (3)	0.2743 (3)	−0.02186 (18)	0.0293 (5)
C21	0.2325 (3)	0.2669 (2)	0.42179 (17)	0.0235 (4)
C22	0.2571 (3)	0.2587 (2)	0.54267 (17)	0.0236 (4)
N22	0.2733 (2)	0.4162 (2)	0.59494 (15)	0.0268 (4)
O221	0.2768 (2)	0.55227 (18)	0.52754 (13)	0.0376 (4)
O222	0.2815 (2)	0.40748 (19)	0.70217 (13)	0.0375 (4)
C23	0.2692 (3)	0.1042 (3)	0.61713 (18)	0.0273 (4)
C24	0.2599 (3)	−0.0492 (3)	0.57190 (18)	0.0286 (5)
C25	0.2389 (3)	−0.0456 (3)	0.45267 (18)	0.0285 (5)
C26	0.2253 (3)	0.1084 (2)	0.37904 (18)	0.0265 (4)
H12	0.5484	0.3288	0.2103	0.034*
H13	0.8274	0.2182	0.0910	0.035*
H15	0.5109	0.1788	−0.1695	0.037*
H16	0.2317	0.2886	−0.0508	0.035*
H23	0.2837	0.1040	0.6988	0.033*
H24	0.2679	−0.1559	0.6219	0.034*
H25	0.2337	−0.1511	0.4210	0.034*
H26	0.2107	0.1068	0.2976	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0271 (3)	0.0306 (3)	0.0251 (3)	−0.0001 (2)	−0.0043 (2)	−0.0021 (2)
S2	0.0318 (3)	0.0214 (3)	0.0249 (3)	−0.00147 (19)	−0.0023 (2)	−0.0014 (2)
C11	0.0289 (11)	0.0214 (9)	0.0216 (9)	−0.0052 (8)	−0.0027 (8)	0.0008 (8)
C12	0.0311 (11)	0.0311 (11)	0.0247 (10)	−0.0034 (9)	−0.0049 (9)	−0.0051 (9)
C13	0.0268 (11)	0.0302 (11)	0.0319 (11)	−0.0017 (8)	−0.0072 (9)	−0.0036 (9)
C14	0.0294 (11)	0.0226 (10)	0.0239 (10)	−0.0033 (8)	0.0005 (8)	−0.0030 (8)
Cl14	0.0327 (3)	0.0379 (3)	0.0333 (3)	−0.0003 (2)	0.0009 (2)	−0.0114 (2)
C15	0.0367 (12)	0.0329 (11)	0.0239 (10)	−0.0044 (9)	−0.0066 (9)	−0.0059 (9)
C16	0.0294 (11)	0.0330 (11)	0.0264 (10)	−0.0044 (9)	−0.0079 (9)	−0.0005 (9)
C21	0.0191 (10)	0.0238 (9)	0.0257 (10)	−0.0024 (7)	0.0014 (8)	−0.0015 (8)
C22	0.0209 (10)	0.0235 (10)	0.0255 (10)	−0.0025 (7)	0.0008 (8)	−0.0042 (8)
N22	0.0248 (9)	0.0270 (9)	0.0285 (9)	−0.0020 (7)	−0.0027 (7)	−0.0047 (8)
O221	0.0544 (10)	0.0233 (8)	0.0349 (9)	−0.0054 (7)	−0.0055 (8)	−0.0032 (7)
O222	0.0497 (10)	0.0380 (9)	0.0283 (8)	−0.0027 (7)	−0.0143 (7)	−0.0075 (7)
C23	0.0215 (10)	0.0321 (11)	0.0269 (10)	−0.0018 (8)	−0.0015 (8)	−0.0011 (9)
C24	0.0251 (11)	0.0246 (10)	0.0336 (12)	−0.0020 (8)	−0.0031 (9)	0.0038 (9)
C25	0.0287 (11)	0.0220 (10)	0.0348 (11)	−0.0036 (8)	−0.0014 (9)	−0.0060 (9)
C26	0.0267 (11)	0.0271 (10)	0.0254 (10)	−0.0032 (8)	−0.0012 (8)	−0.0042 (8)

Geometric parameters (Å, º)

S1—S2	2.0398 (7)	C15—H15	0.9500
S1—C11	1.784 (2)	C16—H16	0.9500
S2—C21	1.7889 (19)	C21—C26	1.400 (3)
N22—O221	1.230 (2)	C21—C22	1.405 (3)
N22—O222	1.223 (2)	C22—C23	1.387 (3)
C11—C12	1.390 (3)	C22—N22	1.460 (2)
C11—C16	1.391 (3)	C23—C24	1.379 (3)
C12—C13	1.387 (3)	C23—H23	0.9500
C12—H12	0.9500	C24—C25	1.384 (3)
C13—C14	1.378 (3)	C24—H24	0.9500
C13—H13	0.9500	C25—C26	1.379 (3)
C14—C15	1.381 (3)	C25—H25	0.9500
C14—Cl14	1.7433 (19)	C26—H26	0.9500
C15—C16	1.384 (3)
C11—S1—S2	105.25 (7)	C15—C16—H16	120.1
C21—S2—S1	103.78 (7)	C11—C16—H16	120.1
O221—N22—O222	123.32 (16)	C26—C21—C22	116.04 (17)
O221—N22—C22	117.44 (16)	C26—C21—S2	121.50 (15)
O222—N22—C22	119.24 (16)	C22—C21—S2	122.46 (15)
C12—C11—C16	119.96 (18)	C23—C22—C21	122.65 (17)
C12—C11—S1	124.37 (15)	C23—C22—N22	116.95 (17)
C16—C11—S1	115.67 (16)	C21—C22—N22	120.39 (17)
C13—C12—C11	120.10 (19)	C24—C23—C22	119.55 (18)
C13—C12—H12	119.9	C24—C23—H23	120.2
C11—C12—H12	119.9	C22—C23—H23	120.2
C14—C13—C12	119.13 (19)	C23—C24—C25	119.15 (19)
C14—C13—H13	120.4	C23—C24—H24	120.4
C12—C13—H13	120.4	C25—C24—H24	120.4
C13—C14—C15	121.49 (18)	C26—C25—C24	121.21 (19)
C13—C14—Cl14	119.55 (16)	C26—C25—H25	119.4
C15—C14—Cl14	118.95 (15)	C24—C25—H25	119.4
C14—C15—C16	119.45 (18)	C25—C26—C21	121.38 (19)
C14—C15—H15	120.3	C25—C26—H26	119.3
C16—C15—H15	120.3	C21—C26—H26	119.3
C15—C16—C11	119.9 (2)
C11—S1—S2—C21	−81.50 (9)	C13—C14—C15—C16	0.1 (3)
S1—S2—C21—C22	−172.01 (15)	Cl14—C14—C15—C16	−178.62 (15)
S1—S2—C21—C26	8.28 (17)	C14—C15—C16—C11	−0.2 (3)
S2—S1—C11—C12	4.67 (18)	C12—C11—C16—C15	0.3 (3)
S2—S1—C11—C16	−175.64 (13)	S1—C11—C16—C15	−179.38 (15)
S2—C21—C22—N22	−1.9 (3)	C26—C21—C22—C23	−1.5 (3)
C21—C22—N22—O221	−4.5 (3)	S2—C21—C22—C23	178.80 (15)
C21—C22—N22—O222	175.11 (18)	C26—C21—C22—N22	177.85 (16)
C23—C22—N22—O221	174.86 (17)	C21—C22—C23—C24	1.0 (3)
C23—C22—N22—O222	−5.5 (3)	N22—C22—C23—C24	−178.31 (17)
C16—C11—C12—C13	−0.4 (3)	C22—C23—C24—C25	0.0 (3)
S1—C11—C12—C13	179.28 (15)	C23—C24—C25—C26	−0.6 (3)
C11—C12—C13—C14	0.3 (3)	C24—C25—C26—C21	0.1 (3)
C12—C13—C14—C15	−0.2 (3)	C22—C21—C26—C25	0.9 (3)
C12—C13—C14—Cl14	178.55 (14)	S2—C21—C26—C25	−179.37 (15)

(3) 2,4-Dinitro-4'-methyldiphenyl disulfide

Crystal data

C13H10N2O4S2	F(000) = 332
Mr = 322.35	Dx = 1.564 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.1301 (2) Å	Cell parameters from 1695 reflections
b = 6.3474 (1) Å	θ = 2.1–27.5°
c = 11.1133 (2) Å	µ = 0.41 mm^−1
β = 106.644 (8)°	T = 150 K
V = 684.64 (2) Å^3	Needle, yellow
Z = 2	0.55 × 0.10 × 0.08 mm

Data collection

Kappa-CCD diffractometer	1695 independent reflections
Radiation source: fine-focus sealed X-ray tube	1615 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997)	h = −13→13
Tmin = 0.808, Tmax = 0.970	k = −7→8
7452 measured reflections	l = −12→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0742P)^2 + 0.0709P] where P = (Fo^2 + 2Fc^2)/3
1695 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.40 e Å^−3
1 restraint	Δρmin = −0.51 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	−0.17395 (7)	0.83986 (13)	0.00092 (6)	0.0270 (2)
S2	0.02483 (6)	0.88284 (11)	0.11272 (7)	0.0262 (2)
C11	−0.2715 (3)	0.9965 (5)	0.0780 (2)	0.0217 (6)
C12	−0.3138 (3)	1.1968 (5)	0.0322 (3)	0.0251 (6)
C13	−0.3917 (2)	1.3193 (5)	0.0890 (3)	0.0253 (6)
C14	−0.4285 (3)	1.2454 (5)	0.1929 (3)	0.0264 (6)
C141	−0.5103 (3)	1.3803 (6)	0.2570 (3)	0.0319 (7)
C15	−0.3868 (3)	1.0437 (6)	0.2372 (3)	0.0289 (7)
C16	−0.3090 (3)	0.9186 (5)	0.1815 (3)	0.0267 (6)
C21	0.0558 (3)	0.6666 (5)	0.2182 (3)	0.0238 (6)
C22	0.1821 (3)	0.6415 (5)	0.3137 (3)	0.0254 (6)
N22	0.2914 (3)	0.7983 (5)	0.3299 (2)	0.0306 (6)
O221	0.2723 (2)	0.9471 (5)	0.2579 (2)	0.0426 (6)
O222	0.3974 (2)	0.7749 (5)	0.4180 (2)	0.0443 (7)
C23	0.2082 (3)	0.4715 (6)	0.3937 (3)	0.0280 (6)
C24	0.1076 (3)	0.3215 (5)	0.3809 (3)	0.0262 (6)
N24	0.1328 (3)	0.1385 (5)	0.4646 (2)	0.0342 (6)
O241	0.2393 (3)	0.1373 (5)	0.5530 (2)	0.0514 (7)
O242	0.0492 (3)	−0.0050 (5)	0.4416 (2)	0.0453 (6)
C25	−0.0192 (3)	0.3390 (5)	0.2909 (3)	0.0271 (6)
C26	−0.0423 (3)	0.5102 (5)	0.2113 (3)	0.0252 (6)
H12	−0.2892	1.2496	−0.0384	0.030*
H13	−0.4204	1.4557	0.0568	0.030*
H14A	−0.5013	1.5286	0.2362	0.048*	0.50
H14B	−0.4754	1.3610	0.3481	0.048*	0.50
H14C	−0.6076	1.3390	0.2285	0.048*	0.50
H14D	−0.5549	1.2905	0.3057	0.048*	0.50
H14E	−0.5808	1.4581	0.1937	0.048*	0.50
H14F	−0.4486	1.4801	0.3134	0.048*	0.50
H15	−0.4124	0.9908	0.3074	0.035*
H16	−0.2814	0.7815	0.2131	0.032*
H23	0.2940	0.4581	0.4565	0.034*
H25	−0.0885	0.2353	0.2843	0.032*
H26	−0.1287	0.5219	0.1491	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0248 (3)	0.0320 (4)	0.0238 (3)	0.0044 (3)	0.0061 (3)	−0.0008 (3)
S2	0.0205 (3)	0.0270 (4)	0.0330 (4)	0.0009 (3)	0.0106 (3)	0.0033 (3)
C11	0.0159 (11)	0.0282 (14)	0.0200 (12)	0.0003 (11)	0.0036 (10)	−0.0013 (11)
C12	0.0163 (12)	0.0303 (15)	0.0255 (13)	−0.0036 (12)	0.0009 (10)	0.0022 (12)
C13	0.0183 (11)	0.0264 (13)	0.0284 (13)	−0.0008 (12)	0.0022 (10)	0.0019 (12)
C14	0.0160 (11)	0.0330 (15)	0.0273 (14)	−0.0041 (13)	0.0013 (10)	−0.0057 (13)
C141	0.0242 (12)	0.0410 (18)	0.0301 (14)	0.0008 (15)	0.0071 (11)	−0.0063 (15)
C15	0.0224 (13)	0.0354 (16)	0.0281 (15)	−0.0018 (13)	0.0057 (11)	0.0034 (13)
C16	0.0232 (12)	0.0316 (16)	0.0249 (13)	0.0008 (12)	0.0063 (10)	0.0022 (12)
C21	0.0218 (13)	0.0233 (13)	0.0269 (14)	0.0017 (12)	0.0079 (10)	−0.0042 (12)
C22	0.0190 (12)	0.0304 (15)	0.0263 (14)	0.0013 (13)	0.0055 (11)	−0.0058 (12)
N22	0.0216 (11)	0.0370 (15)	0.0334 (13)	−0.0026 (11)	0.0081 (10)	−0.0087 (12)
O221	0.0298 (11)	0.0425 (16)	0.0546 (15)	−0.0082 (12)	0.0105 (11)	0.0063 (13)
O222	0.0262 (11)	0.0591 (18)	0.0398 (12)	−0.0071 (12)	−0.0029 (10)	−0.0079 (13)
C23	0.0280 (14)	0.0349 (15)	0.0213 (12)	0.0051 (14)	0.0076 (11)	−0.0032 (12)
C24	0.0325 (14)	0.0262 (14)	0.0223 (12)	0.0028 (13)	0.0116 (11)	−0.0018 (12)
N24	0.0470 (16)	0.0334 (15)	0.0266 (13)	0.0105 (15)	0.0174 (12)	0.0037 (12)
O241	0.0547 (15)	0.0546 (18)	0.0384 (14)	0.0134 (16)	0.0029 (11)	0.0120 (14)
O242	0.0686 (17)	0.0339 (13)	0.0395 (13)	−0.0020 (15)	0.0249 (12)	0.0059 (12)
C25	0.0298 (13)	0.0256 (14)	0.0273 (13)	−0.0008 (13)	0.0106 (11)	−0.0012 (13)
C26	0.0220 (13)	0.0286 (15)	0.0242 (13)	−0.0024 (12)	0.0054 (11)	−0.0015 (12)

Geometric parameters (Å, º)

S1—C11	1.784 (3)	C15—H15	0.9500
S1—S2	2.0591 (9)	C16—H16	0.9500
S2—C21	1.774 (3)	C21—C26	1.391 (4)
C11—C12	1.391 (4)	C21—C22	1.418 (4)
C11—C16	1.401 (4)	C22—C23	1.375 (5)
C12—C13	1.382 (4)	C22—N22	1.461 (4)
C12—H12	0.9500	N22—O221	1.217 (4)
C13—C14	1.393 (4)	N22—O222	1.238 (3)
C13—H13	0.9500	C23—C24	1.372 (5)
C14—C15	1.394 (5)	C23—H23	0.9500
C14—C141	1.506 (4)	C24—C25	1.388 (4)
C141—H14A	0.9800	C24—N24	1.464 (4)
C141—H14B	0.9800	N24—O242	1.220 (4)
C141—H14C	0.9800	N24—O241	1.233 (4)
C141—H14D	0.9800	C25—C26	1.378 (4)
C141—H14E	0.9800	C25—H25	0.9500
C141—H14F	0.9800	C26—H26	0.9500
C15—C16	1.383 (4)
C11—S1—S2	102.51 (9)	H14D—C141—H14F	109.5
C21—S2—S1	104.69 (10)	H14E—C141—H14F	109.5
C12—C11—C16	119.7 (3)	C16—C15—C14	121.5 (3)
C12—C11—S1	119.2 (2)	C16—C15—H15	119.2
C16—C11—S1	121.1 (2)	C14—C15—H15	119.2
C13—C12—C11	120.2 (3)	C15—C16—C11	119.2 (3)
C13—C12—H12	119.9	C15—C16—H16	120.4
C11—C12—H12	119.9	C11—C16—H16	120.4
C12—C13—C14	120.8 (3)	C26—C21—C22	116.0 (3)
C12—C13—H13	119.6	C26—C21—S2	121.8 (2)
C14—C13—H13	119.6	C22—C21—S2	122.2 (2)
C15—C14—C13	118.5 (3)	C23—C22—C21	122.5 (3)
C15—C14—C141	120.5 (3)	C23—C22—N22	117.2 (2)
C13—C14—C141	121.0 (3)	C21—C22—N22	120.4 (3)
C14—C141—H14A	109.5	O221—N22—O222	123.5 (3)
C14—C141—H14B	109.5	O221—N22—C22	118.4 (2)
H14A—C141—H14B	109.5	O222—N22—C22	118.1 (3)
C14—C141—H14C	109.5	C24—C23—C22	118.6 (3)
H14A—C141—H14C	109.5	C24—C23—H23	120.7
H14B—C141—H14C	109.5	C22—C23—H23	120.7
C14—C141—H14D	109.5	C23—C24—C25	121.7 (3)
H14A—C141—H14D	141.1	C23—C24—N24	119.7 (3)
H14B—C141—H14D	56.3	C25—C24—N24	118.6 (3)
H14C—C141—H14D	56.3	O242—N24—O241	123.9 (3)
C14—C141—H14E	109.5	O242—N24—C24	118.3 (3)
H14A—C141—H14E	56.3	O241—N24—C24	117.7 (3)
H14B—C141—H14E	141.1	C26—C25—C24	118.6 (3)
H14C—C141—H14E	56.3	C26—C25—H25	120.7
H14D—C141—H14E	109.5	C24—C25—H25	120.7
C14—C141—H14F	109.5	C25—C26—C21	122.7 (3)
H14A—C141—H14F	56.3	C25—C26—H26	118.7
H14B—C141—H14F	56.3	C21—C26—H26	118.7
H14C—C141—H14F	141.1
C11—S1—S2—C21	94.61 (14)	S2—C21—C22—N22	1.3 (4)
S2—S1—C11—C12	99.4 (2)	C23—C22—N22—O221	177.9 (3)
S2—S1—C11—C16	−82.3 (2)	C21—C22—N22—O221	−1.7 (4)
C16—C11—C12—C13	0.5 (4)	C23—C22—N22—O222	−3.7 (4)
S1—C11—C12—C13	178.8 (2)	C21—C22—N22—O222	176.7 (3)
C11—C12—C13—C14	0.2 (4)	C21—C22—C23—C24	−0.4 (4)
C12—C13—C14—C15	−0.9 (4)	N22—C22—C23—C24	−180.0 (3)
C12—C13—C14—C141	178.5 (2)	C22—C23—C24—C25	−0.8 (4)
C13—C14—C15—C16	0.8 (4)	C22—C23—C24—N24	179.8 (3)
C141—C14—C15—C16	−178.6 (3)	C23—C24—N24—O242	−171.0 (3)
C14—C15—C16—C11	−0.1 (4)	C25—C24—N24—O242	9.6 (4)
C12—C11—C16—C15	−0.6 (4)	C23—C24—N24—O241	7.5 (4)
S1—C11—C16—C15	−178.8 (2)	C25—C24—N24—O241	−171.8 (3)
S1—S2—C21—C26	2.2 (3)	C23—C24—C25—C26	1.3 (4)
S1—S2—C21—C22	−178.5 (2)	N24—C24—C25—C26	−179.3 (2)
C26—C21—C22—C23	1.1 (4)	C24—C25—C26—C21	−0.5 (4)
S2—C21—C22—C23	−178.2 (2)	C22—C21—C26—C25	−0.6 (4)
C26—C21—C22—N22	−179.3 (2)	S2—C21—C26—C25	178.7 (2)

(4) 2,4-Dinitrophenyl-2'-methoxycarbonylmethyl disulfide

Crystal data

C9H8N2O6S2	Z = 2
Mr = 304.30	F(000) = 312
Triclinic, P1	Dx = 1.709 Mg m^−3
a = 8.1655 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2415 (3) Å	Cell parameters from 2629 reflections
c = 9.3887 (4) Å	θ = 2.9–29.3°
α = 72.1417 (15)°	µ = 0.48 mm^−1
β = 83.3965 (14)°	T = 150 K
γ = 80.332 (3)°	Needle, yellow
V = 591.48 (4) Å^3	0.35 × 0.05 × 0.03 mm

Data collection

Kappa-CCD diffractometer	2629 independent reflections
Radiation source: fine-focus sealed X-ray tube	1969 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997)	h = −10→10
Tmin = 0.851, Tmax = 0.988	k = −9→10
6105 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0536P)^2] where P = (Fo^2 + 2Fc^2)/3
2629 reflections	(Δ/σ)max = 0.008
173 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.31637 (7)	0.86272 (8)	0.91373 (7)	0.02245 (18)
S2	0.09158 (7)	0.89766 (8)	0.82419 (7)	0.02167 (18)
C1	0.4109 (3)	1.0481 (3)	0.7967 (3)	0.0205 (5)
C2	0.3239 (3)	1.2169 (3)	0.8142 (3)	0.0201 (5)
O3	0.2542 (2)	1.3296 (2)	0.7165 (2)	0.0309 (4)
O4	0.3370 (2)	1.2272 (2)	0.95141 (18)	0.0254 (4)
C5	0.2645 (3)	1.3890 (3)	0.9787 (3)	0.0344 (6)
C21	0.1368 (3)	0.8092 (3)	0.6714 (3)	0.0180 (5)
C22	0.0110 (2)	0.7859 (3)	0.5912 (3)	0.0179 (5)
N22	−0.1648 (2)	0.8353 (3)	0.6329 (2)	0.0212 (5)
O221	−0.19512 (18)	0.9202 (2)	0.7223 (2)	0.0281 (4)
O222	−0.27220 (19)	0.7932 (2)	0.5763 (2)	0.0330 (5)
C23	0.0430 (3)	0.7170 (3)	0.4719 (3)	0.0191 (5)
C24	0.2073 (3)	0.6735 (3)	0.4288 (3)	0.0177 (5)
N24	0.2445 (2)	0.6046 (3)	0.3001 (2)	0.0232 (5)
O241	0.1278 (2)	0.5881 (3)	0.2372 (2)	0.0362 (5)
O242	0.39156 (19)	0.5679 (2)	0.2617 (2)	0.0305 (4)
C25	0.3360 (3)	0.6936 (3)	0.5019 (3)	0.0194 (5)
C26	0.3011 (3)	0.7597 (3)	0.6213 (3)	0.0190 (5)
H1A	0.5280	1.0337	0.8215	0.025*
H1B	0.4116	1.0512	0.6904	0.025*
H5A	0.2800	1.3831	1.0822	0.052*	0.50
H5B	0.1453	1.4105	0.9628	0.052*	0.50
H5C	0.3193	1.4827	0.9094	0.052*	0.50
H5D	0.2165	1.4678	0.8874	0.052*	0.50
H5E	0.3511	1.4403	1.0068	0.052*	0.50
H5F	0.1771	1.3682	1.0602	0.052*	0.50
H23	−0.0449	0.7005	0.4219	0.023*
H25	0.4482	0.6619	0.4698	0.023*
H26	0.3906	0.7724	0.6715	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0278 (3)	0.0206 (3)	0.0201 (3)	−0.0042 (2)	−0.0066 (2)	−0.0055 (3)
S2	0.0221 (3)	0.0239 (4)	0.0210 (4)	−0.0034 (2)	−0.0008 (2)	−0.0095 (3)
C1	0.0206 (11)	0.0229 (13)	0.0208 (13)	−0.0038 (9)	−0.0001 (9)	−0.0105 (11)
C2	0.0166 (11)	0.0223 (13)	0.0227 (14)	−0.0054 (9)	−0.0016 (9)	−0.0070 (11)
O3	0.0348 (10)	0.0244 (10)	0.0335 (11)	−0.0015 (7)	−0.0181 (8)	−0.0041 (9)
O4	0.0380 (9)	0.0184 (9)	0.0200 (10)	0.0002 (7)	−0.0022 (7)	−0.0081 (8)
C5	0.0484 (16)	0.0199 (14)	0.0367 (17)	−0.0043 (11)	0.0080 (12)	−0.0149 (13)
C21	0.0211 (11)	0.0148 (12)	0.0177 (12)	−0.0032 (8)	−0.0020 (9)	−0.0034 (10)
C22	0.0160 (11)	0.0156 (12)	0.0200 (13)	−0.0009 (8)	−0.0011 (8)	−0.0029 (10)
N22	0.0175 (10)	0.0220 (11)	0.0215 (11)	−0.0033 (7)	−0.0009 (8)	−0.0025 (9)
O221	0.0236 (9)	0.0316 (11)	0.0308 (11)	0.0002 (7)	0.0013 (7)	−0.0150 (9)
O222	0.0189 (9)	0.0468 (12)	0.0395 (12)	−0.0058 (7)	−0.0048 (7)	−0.0203 (10)
C23	0.0204 (11)	0.0164 (12)	0.0204 (13)	−0.0037 (8)	−0.0045 (9)	−0.0036 (10)
C24	0.0205 (11)	0.0151 (12)	0.0173 (13)	−0.0028 (8)	0.0000 (9)	−0.0050 (10)
N24	0.0219 (11)	0.0254 (12)	0.0234 (12)	−0.0043 (8)	−0.0007 (8)	−0.0085 (9)
O241	0.0252 (9)	0.0556 (14)	0.0401 (12)	−0.0047 (8)	−0.0068 (8)	−0.0309 (10)
O242	0.0221 (9)	0.0413 (12)	0.0313 (11)	−0.0007 (7)	0.0029 (7)	−0.0192 (9)
C25	0.0193 (11)	0.0155 (12)	0.0209 (13)	−0.0007 (8)	−0.0018 (9)	−0.0026 (10)
C26	0.0198 (11)	0.0184 (13)	0.0189 (13)	−0.0024 (8)	−0.0045 (8)	−0.0046 (10)

Geometric parameters (Å, º)

S1—S2	2.0464 (8)	C5—H5C	0.9800
S1—C1	1.819 (2)	C5—H5D	0.9800
S2—C21	1.777 (2)	C5—H5E	0.9800
N22—O221	1.229 (3)	C5—H5F	0.9800
N22—O222	1.222 (2)	C21—C26	1.405 (3)
N24—O241	1.224 (3)	C21—C22	1.411 (3)
N24—O242	1.228 (2)	C22—C23	1.384 (3)
C1—C2	1.499 (3)	C22—N22	1.467 (3)
C1—H1A	0.9900	C23—C24	1.377 (3)
C1—H1B	0.9900	C23—H23	0.9500
C2—O3	1.202 (3)	C24—C25	1.377 (3)
C2—O4	1.335 (3)	C24—N24	1.468 (3)
O4—C5	1.450 (3)	C25—C26	1.373 (3)
C5—H5A	0.9800	C25—H25	0.9500
C5—H5B	0.9800	C26—H26	0.9500
C1—S1—S2	102.72 (8)	H5A—C5—H5E	56.3
C21—S2—S1	104.16 (7)	H5B—C5—H5E	141.1
C2—C1—S1	113.96 (15)	H5C—C5—H5E	56.3
O221—N22—O222	123.66 (18)	H5D—C5—H5E	109.5
O221—N22—C22	117.16 (18)	O4—C5—H5F	109.5
O222—N22—C22	119.17 (19)	H5A—C5—H5F	56.3
O241—N24—O242	124.0 (2)	H5B—C5—H5F	56.3
O241—N24—C24	118.23 (18)	H5C—C5—H5F	141.1
O242—N24—C24	117.72 (18)	H5D—C5—H5F	109.5
C2—C1—H1A	108.8	H5E—C5—H5F	109.5
S1—C1—H1A	108.8	C26—C21—C22	115.6 (2)
C2—C1—H1B	108.8	C26—C21—S2	121.94 (17)
S1—C1—H1B	108.8	C22—C21—S2	122.43 (16)
H1A—C1—H1B	107.7	C23—C22—C21	123.56 (19)
O3—C2—O4	124.4 (2)	C23—C22—N22	116.32 (19)
O3—C2—C1	124.5 (2)	C21—C22—N22	120.1 (2)
O4—C2—C1	111.07 (19)	C24—C23—C22	117.2 (2)
C2—O4—C5	115.87 (19)	C24—C23—H23	121.4
O4—C5—H5A	109.5	C22—C23—H23	121.4
O4—C5—H5B	109.5	C23—C24—C25	122.1 (2)
H5A—C5—H5B	109.5	C23—C24—N24	118.29 (19)
O4—C5—H5C	109.5	C25—C24—N24	119.56 (18)
H5A—C5—H5C	109.5	C26—C25—C24	119.5 (2)
H5B—C5—H5C	109.5	C26—C25—H25	120.2
O4—C5—H5D	109.5	C24—C25—H25	120.2
H5A—C5—H5D	141.1	C25—C26—C21	121.9 (2)
H5B—C5—H5D	56.3	C25—C26—H26	119.0
H5C—C5—H5D	56.3	C21—C26—H26	119.0
O4—C5—H5E	109.5
C1—S1—S2—C21	83.97 (11)	C1—C2—O4—C5	176.97 (19)
S1—S2—C21—C22	171.14 (18)	C26—C21—C22—C23	0.9 (3)
S1—S2—C21—C26	−9.7 (2)	S2—C21—C22—C23	−179.88 (18)
C21—C22—N22—O221	11.0 (3)	C26—C21—C22—N22	−179.26 (19)
C21—C22—N22—O222	−170.2 (2)	S2—C21—C22—N22	0.0 (3)
C23—C22—N22—O221	−169.1 (2)	C21—C22—C23—C24	−1.6 (3)
C23—C22—N22—O222	9.7 (3)	N22—C22—C23—C24	178.57 (19)
C23—C24—N24—O241	−0.4 (3)	C22—C23—C24—C25	1.3 (3)
C23—C24—N24—O242	179.3 (2)	C22—C23—C24—N24	−178.3 (2)
C25—C24—N24—O241	−180.0 (2)	C23—C24—C25—C26	−0.3 (3)
C25—C24—N24—O242	−0.3 (3)	N24—C24—C25—C26	179.3 (2)
S2—S1—C1—C2	67.02 (17)	C24—C25—C26—C21	−0.4 (3)
S1—C1—C2—O3	−115.4 (2)	C22—C21—C26—C25	0.2 (3)
S1—C1—C2—O4	66.0 (2)	S2—C21—C26—C25	−179.07 (18)
O3—C2—O4—C5	−1.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O3^i	0.95	2.35	3.299 (3)	176

Symmetry code: (i) −x, −y+2, −z+1.

(5) Bis-(2-nitrophenyl) disulfide

Crystal data

C12H8N2O4S2	F(000) = 632
Mr = 308.32	Dx = 1.625 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.1028 (11) Å	Cell parameters from 1862 reflections
b = 22.925 (4) Å	θ = 3.0–28.5°
c = 7.7769 (14) Å	µ = 0.44 mm^−1
β = 95.536 (12)°	T = 150 K
V = 1260.4 (4) Å^3	Needle, yellow
Z = 4	0.40 × 0.07 × 0.07 mm

Data collection

Kappa-CCD diffractometer	1862 independent reflections
Radiation source: fine-focus sealed X-ray tube	1135 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ϕ scans and ω scans with κ offsets	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997)	h = −8→7
Tmin = 0.845, Tmax = 0.970	k = −27→28
3982 measured reflections	l = −7→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0528P)^2] where P = (Fo^2 + 2Fc^2)/3
1862 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.29771 (18)	0.41853 (5)	0.46148 (13)	0.0341 (4)
S2	0.40937 (18)	0.34184 (5)	0.37879 (14)	0.0340 (4)
C11	0.2744 (7)	0.46456 (18)	0.2756 (5)	0.0304 (12)
C12	0.2372 (6)	0.52434 (18)	0.2864 (5)	0.0277 (12)
N12	0.2115 (6)	0.55123 (16)	0.4526 (5)	0.0344 (10)
O122	0.1984 (5)	0.60403 (13)	0.4631 (4)	0.0404 (9)
O121	0.2035 (5)	0.51862 (13)	0.5782 (4)	0.0493 (10)
C13	0.2205 (6)	0.56018 (19)	0.1441 (5)	0.0331 (12)
C14	0.2377 (7)	0.5376 (2)	−0.0167 (6)	0.0382 (14)
C15	0.2743 (6)	0.47882 (19)	−0.0328 (5)	0.0346 (13)
C16	0.2950 (7)	0.44307 (19)	0.1129 (5)	0.0346 (12)
C21	0.2079 (7)	0.30143 (18)	0.2867 (5)	0.0253 (11)
C22	0.2159 (7)	0.24112 (17)	0.2660 (5)	0.0246 (11)
N22	0.3850 (6)	0.20841 (16)	0.3224 (4)	0.0334 (11)
O221	0.5343 (5)	0.23556 (14)	0.3516 (4)	0.0459 (10)
O222	0.3759 (5)	0.15520 (13)	0.3377 (4)	0.0455 (9)
C23	0.0617 (7)	0.20969 (19)	0.1951 (5)	0.0313 (12)
C24	−0.1040 (7)	0.23808 (19)	0.1391 (5)	0.0347 (13)
C25	−0.1174 (7)	0.29733 (19)	0.1603 (5)	0.0333 (13)
C26	0.0371 (7)	0.32882 (18)	0.2340 (5)	0.0306 (13)
H13	0.1970	0.6007	0.1574	0.040*
H14	0.2246	0.5621	−0.1158	0.046*
H15	0.2854	0.4626	−0.1438	0.042*
H16	0.3240	0.4030	0.0997	0.041*
H23	0.0698	0.1685	0.1849	0.038*
H24	−0.2086	0.2167	0.0861	0.042*
H25	−0.2325	0.3169	0.1245	0.040*
H26	0.0259	0.3698	0.2486	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0493 (10)	0.0221 (6)	0.0303 (7)	−0.0004 (6)	0.0015 (7)	0.0001 (4)
S2	0.0373 (9)	0.0235 (6)	0.0401 (8)	−0.0002 (6)	−0.0023 (6)	−0.0006 (4)
C11	0.034 (4)	0.030 (3)	0.027 (3)	−0.004 (2)	0.003 (2)	−0.0008 (17)
C12	0.031 (4)	0.027 (3)	0.025 (3)	−0.001 (2)	0.000 (2)	−0.0054 (16)
N12	0.042 (3)	0.023 (2)	0.037 (2)	0.0035 (19)	0.000 (2)	−0.0009 (17)
O122	0.050 (2)	0.0242 (19)	0.047 (2)	0.0071 (17)	0.0043 (17)	−0.0026 (13)
O121	0.083 (3)	0.036 (2)	0.028 (2)	0.0068 (19)	0.005 (2)	0.0018 (14)
C13	0.034 (3)	0.030 (3)	0.035 (3)	0.003 (2)	0.003 (2)	0.0033 (19)
C14	0.045 (4)	0.036 (3)	0.034 (3)	0.002 (2)	0.007 (3)	0.0098 (19)
C15	0.042 (4)	0.034 (3)	0.028 (3)	−0.005 (2)	0.007 (3)	−0.0021 (18)
C16	0.037 (4)	0.025 (3)	0.042 (3)	−0.004 (2)	0.007 (3)	−0.0035 (19)
C21	0.027 (3)	0.028 (3)	0.021 (2)	−0.003 (2)	0.001 (2)	−0.0015 (16)
C22	0.029 (4)	0.023 (2)	0.022 (2)	−0.001 (2)	0.001 (2)	−0.0005 (17)
N22	0.041 (4)	0.031 (3)	0.028 (2)	0.007 (2)	0.002 (2)	−0.0016 (15)
O221	0.029 (3)	0.036 (2)	0.071 (3)	−0.0011 (18)	−0.0047 (19)	−0.0021 (16)
O222	0.060 (3)	0.0195 (18)	0.056 (2)	0.0072 (17)	0.0041 (19)	0.0090 (13)
C23	0.038 (4)	0.026 (3)	0.032 (3)	0.003 (2)	0.009 (3)	0.0003 (18)
C24	0.034 (4)	0.036 (3)	0.034 (3)	−0.011 (3)	0.003 (2)	−0.0035 (19)
C25	0.032 (4)	0.033 (3)	0.035 (3)	0.000 (2)	0.002 (3)	−0.0008 (19)
C26	0.036 (4)	0.023 (2)	0.033 (3)	0.003 (2)	0.003 (3)	0.0000 (17)

Geometric parameters (Å, º)

S1—S2	2.0572 (15)	C15—C16	1.395 (5)
S1—C11	1.784 (4)	C15—H15	0.9500
S2—C21	1.795 (5)	C16—H16	0.9500
N12—O121	1.236 (4)	C21—C26	1.392 (6)
N12—O122	1.217 (4)	C21—C22	1.394 (6)
N22—O221	1.232 (5)	C22—C23	1.381 (6)
N22—O222	1.228 (4)	C22—N22	1.448 (5)
C11—C16	1.379 (5)	C23—C24	1.378 (6)
C11—C12	1.400 (6)	C23—H23	0.9500
C12—C13	1.374 (5)	C24—C25	1.373 (6)
C12—N12	1.460 (5)	C24—H24	0.9500
C13—C14	1.370 (5)	C25—C26	1.390 (6)
C13—H13	0.9500	C25—H25	0.9500
C14—C15	1.381 (6)	C26—H26	0.9500
C14—H14	0.9500
C11—S1—S2	105.11 (14)	C16—C15—H15	119.8
C21—S2—S1	104.43 (15)	C11—C16—C15	121.6 (4)
O121—N12—O122	122.6 (4)	C11—C16—H16	119.2
O121—N12—C12	117.6 (4)	C15—C16—H16	119.2
O122—N12—C12	119.7 (3)	C26—C21—C22	117.2 (4)
O221—N22—O222	122.4 (4)	C26—C21—S2	121.6 (3)
O221—N22—C22	117.9 (4)	C22—C21—S2	121.2 (4)
O222—N22—C22	119.6 (4)	C23—C22—C21	121.6 (4)
C16—C11—C12	116.2 (4)	C23—C22—N22	117.0 (4)
C16—C11—S1	121.5 (3)	C21—C22—N22	121.4 (4)
C12—C11—S1	122.3 (3)	C24—C23—C22	120.0 (4)
C13—C12—C11	122.7 (4)	C24—C23—H23	120.0
C13—C12—N12	116.9 (4)	C22—C23—H23	120.0
C11—C12—N12	120.4 (3)	C25—C24—C23	119.8 (5)
C14—C13—C12	120.1 (4)	C25—C24—H24	120.1
C14—C13—H13	120.0	C23—C24—H24	120.1
C12—C13—H13	120.0	C24—C25—C26	120.2 (5)
C13—C14—C15	119.0 (4)	C24—C25—H25	119.9
C13—C14—H14	120.5	C26—C25—H25	119.9
C15—C14—H14	120.5	C25—C26—C21	121.2 (4)
C14—C15—C16	120.4 (4)	C25—C26—H26	119.4
C14—C15—H15	119.8	C21—C26—H26	119.4
C11—S1—S2—C21	−84.4 (2)	N12—C12—C13—C14	−178.2 (4)
S1—S2—C21—C22	−159.6 (3)	C12—C13—C14—C15	−0.8 (7)
S1—S2—C21—C26	20.1 (3)	C13—C14—C15—C16	−0.5 (7)
S2—S1—C11—C16	11.5 (4)	C12—C11—C16—C15	−1.8 (7)
S2—S1—C11—C12	−167.5 (4)	S1—C11—C16—C15	179.1 (4)
C11—C12—N12—O121	−7.6 (7)	C14—C15—C16—C11	1.9 (7)
C13—C12—N12—O121	171.5 (4)	C26—C21—C22—C23	0.4 (6)
C11—C12—N12—O122	172.6 (5)	S2—C21—C22—C23	−179.9 (3)
C13—C12—N12—O122	−8.3 (7)	C26—C21—C22—N22	−177.8 (3)
C21—C22—N22—O221	−16.7 (5)	S2—C21—C22—N22	1.9 (5)
C23—C22—N22—O221	165.0 (4)	C21—C22—C23—C24	1.5 (6)
C21—C22—N22—O222	164.1 (4)	N22—C22—C23—C24	179.8 (3)
C23—C22—N22—O222	−14.2 (5)	C22—C23—C24—C25	−2.5 (6)
C16—C11—C12—C13	0.4 (7)	C23—C24—C25—C26	1.6 (6)
S1—C11—C12—C13	179.5 (4)	C24—C25—C26—C21	0.4 (6)
C16—C11—C12—N12	179.5 (4)	C22—C21—C26—C25	−1.4 (6)
S1—C11—C12—N12	−1.5 (7)	S2—C21—C26—C25	179.0 (3)
C11—C12—C13—C14	0.9 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O222^i	0.95	2.49	3.197 (5)	131

Symmetry code: (i) x, −y+1/2, z−1/2.

(6) Bis-(2-nitro-4-trifluoromethylphenyl) disulfide

Crystal data

C14H6F6N2O4S2	F(000) = 888
Mr = 444.33	Dx = 1.727 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.1617 (5) Å	Cell parameters from 3812 reflections
b = 5.3367 (2) Å	θ = 2.3–27.5°
c = 22.6233 (10) Å	µ = 0.40 mm^−1
β = 91.7376 (13)°	T = 150 K
V = 1709.01 (12) Å^3	Needle, yellow
Z = 4	0.35 × 0.10 × 0.05 mm

Data collection

Kappa-CCD diffractometer	3812 independent reflections
Radiation source: fine-focus sealed X-ray tube	1646 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997)	h = −18→18
Tmin = 0.873, Tmax = 0.980	k = −6→6
14106 measured reflections	l = −28→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0668P)^2] where P = (Fo^2 + 2Fc^2)/3
3812 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.22533 (7)	0.85099 (16)	0.26136 (4)	0.0621 (3)
S2	0.36334 (7)	0.75071 (18)	0.27725 (4)	0.0655 (3)
C11	0.1863 (2)	0.6570 (5)	0.20162 (13)	0.0472 (8)
C12	0.0974 (2)	0.6873 (6)	0.17393 (15)	0.0499 (8)
N12	0.0328 (3)	0.8793 (6)	0.19395 (15)	0.0650 (8)
O121	0.0592 (2)	1.0148 (5)	0.23493 (14)	0.0809 (8)
O122	−0.0445 (2)	0.8981 (6)	0.16933 (14)	0.0952 (10)
C13	0.0671 (3)	0.5438 (6)	0.12645 (15)	0.0571 (9)
C14	0.1258 (3)	0.3619 (6)	0.10481 (14)	0.0544 (9)
C141	0.0949 (4)	0.2153 (8)	0.05198 (19)	0.0764 (12)
F141	0.1023 (2)	0.3360 (5)	0.00274 (11)	0.1177 (11)
F142	0.1400 (3)	0.0050 (5)	0.04609 (13)	0.1450 (13)
F143	0.0052 (3)	0.1512 (7)	0.05305 (13)	0.1541 (15)
C15	0.2126 (3)	0.3236 (6)	0.13188 (16)	0.0594 (10)
C16	0.2422 (2)	0.4667 (6)	0.17987 (14)	0.0540 (9)
C21	0.3579 (3)	0.5036 (6)	0.33034 (14)	0.0543 (9)
C22	0.4390 (3)	0.4100 (7)	0.35920 (16)	0.0572 (9)
N22	0.5332 (3)	0.5069 (8)	0.34643 (17)	0.0775 (10)
O221	0.5381 (2)	0.6731 (6)	0.30981 (15)	0.0935 (9)
O222	0.6013 (2)	0.4158 (8)	0.37199 (17)	0.1210 (13)
C23	0.4357 (3)	0.2279 (7)	0.40201 (16)	0.0629 (10)
C24	0.3500 (3)	0.1328 (6)	0.41772 (15)	0.0598 (9)
C241	0.3456 (4)	−0.0516 (8)	0.46645 (19)	0.0799 (12)
F241	0.3469 (2)	0.0509 (5)	0.51923 (11)	0.1215 (11)
F242	0.4182 (2)	−0.2098 (5)	0.46767 (12)	0.1100 (9)
F243	0.2693 (2)	−0.1963 (5)	0.46249 (14)	0.1293 (11)
C25	0.2687 (3)	0.2202 (7)	0.38939 (16)	0.0650 (10)
C26	0.2726 (3)	0.3999 (7)	0.34613 (16)	0.0602 (9)
H13	0.0075	0.5694	0.1091	0.069*
H15	0.2521	0.1996	0.1177	0.071*
H16	0.3008	0.4347	0.1980	0.065*
H23	0.4912	0.1695	0.4202	0.075*
H25	0.2104	0.1563	0.3998	0.078*
H26	0.2170	0.4529	0.3271	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0662 (7)	0.0613 (6)	0.0586 (6)	−0.0014 (5)	0.0008 (5)	−0.0079 (4)
S2	0.0577 (7)	0.0799 (6)	0.0589 (6)	−0.0190 (5)	−0.0005 (5)	0.0003 (5)
C11	0.046 (2)	0.0530 (18)	0.0424 (19)	−0.0026 (16)	0.0032 (16)	0.0036 (14)
C12	0.048 (2)	0.0499 (19)	0.052 (2)	0.0061 (16)	0.0078 (18)	0.0083 (15)
N12	0.054 (2)	0.068 (2)	0.074 (2)	0.0126 (17)	0.0088 (19)	0.0140 (18)
O121	0.076 (2)	0.0710 (18)	0.097 (2)	0.0117 (14)	0.0189 (17)	−0.0144 (16)
O122	0.062 (2)	0.121 (2)	0.103 (2)	0.0381 (17)	0.0032 (18)	0.0064 (18)
C13	0.048 (2)	0.068 (2)	0.054 (2)	−0.0011 (18)	−0.0041 (18)	0.0107 (18)
C14	0.057 (3)	0.059 (2)	0.047 (2)	−0.0062 (18)	−0.0054 (18)	0.0037 (16)
C141	0.081 (4)	0.083 (3)	0.065 (3)	−0.007 (2)	−0.010 (2)	−0.005 (2)
F141	0.180 (3)	0.119 (2)	0.0528 (16)	−0.0310 (19)	−0.0129 (17)	0.0032 (14)
F142	0.217 (4)	0.098 (2)	0.116 (2)	0.040 (2)	−0.059 (2)	−0.0466 (17)
F143	0.132 (3)	0.225 (4)	0.105 (2)	−0.088 (3)	0.011 (2)	−0.065 (2)
C15	0.063 (3)	0.060 (2)	0.056 (2)	0.0047 (18)	0.007 (2)	−0.0035 (17)
C16	0.040 (2)	0.061 (2)	0.060 (2)	0.0085 (16)	−0.0079 (18)	0.0001 (17)
C21	0.052 (3)	0.068 (2)	0.043 (2)	−0.0115 (18)	−0.0002 (18)	−0.0112 (16)
C22	0.036 (2)	0.082 (2)	0.053 (2)	−0.0128 (18)	0.0006 (18)	−0.0130 (19)
N22	0.053 (3)	0.105 (3)	0.074 (3)	−0.010 (2)	−0.001 (2)	−0.011 (2)
O221	0.058 (2)	0.118 (2)	0.104 (2)	−0.0259 (17)	0.0075 (17)	0.009 (2)
O222	0.048 (2)	0.175 (3)	0.139 (3)	−0.010 (2)	−0.016 (2)	0.030 (3)
C23	0.051 (3)	0.082 (3)	0.055 (2)	0.0017 (19)	−0.0084 (19)	−0.0124 (19)
C24	0.058 (3)	0.071 (2)	0.050 (2)	−0.002 (2)	−0.0022 (19)	−0.0087 (18)
C241	0.089 (4)	0.083 (3)	0.068 (3)	0.005 (3)	0.003 (3)	0.005 (2)
F241	0.193 (3)	0.115 (2)	0.0566 (16)	0.0197 (19)	0.0159 (17)	0.0041 (14)
F242	0.131 (3)	0.0999 (18)	0.099 (2)	0.0315 (17)	0.0021 (17)	0.0117 (14)
F243	0.123 (3)	0.130 (2)	0.134 (3)	−0.039 (2)	−0.012 (2)	0.0536 (19)
C25	0.050 (3)	0.082 (3)	0.063 (3)	−0.0112 (19)	0.005 (2)	−0.001 (2)
C26	0.044 (2)	0.077 (2)	0.059 (2)	−0.0084 (18)	−0.0050 (18)	0.0012 (19)

Geometric parameters (Å, º)

S1—S2	2.0476 (14)	C16—H16	0.9300
S1—C11	1.777 (3)	C21—C26	1.385 (5)
S2—C21	1.787 (3)	C21—C22	1.396 (5)
N12—O122	1.217 (4)	C22—C23	1.374 (5)
N12—O121	1.225 (4)	C22—N22	1.467 (5)
C11—C16	1.387 (4)	N22—O222	1.211 (4)
C11—C12	1.399 (4)	N22—O221	1.217 (4)
C12—C13	1.377 (5)	C23—C24	1.373 (5)
C12—N12	1.455 (4)	C23—H23	0.9300
C13—C14	1.377 (5)	C24—C25	1.382 (5)
C13—H13	0.9300	C24—C241	1.480 (5)
C14—C15	1.372 (5)	C241—F241	1.313 (5)
C14—C141	1.483 (5)	C241—F243	1.329 (5)
C141—F141	1.294 (5)	C241—F242	1.330 (5)
C141—F142	1.300 (5)	C25—C26	1.372 (5)
C141—F143	1.317 (5)	C25—H25	0.9300
C15—C16	1.382 (5)	C26—H26	0.9300
C15—H15	0.9300
C11—S1—S2	104.74 (12)	C16—C15—H15	119.5
C21—S2—S1	104.52 (13)	C15—C16—C11	121.4 (3)
O121—N12—O122	123.2 (3)	C15—C16—H16	119.3
O122—N12—C12	118.7 (4)	C11—C16—H16	119.3
O121—N12—C12	118.1 (3)	C26—C21—C22	116.6 (3)
O221—N22—O222	123.8 (4)	C26—C21—S2	121.6 (3)
O221—N22—C22	117.5 (4)	C22—C21—S2	121.8 (3)
O222—N22—C22	118.7 (4)	C23—C22—C21	122.5 (3)
C16—C11—C12	116.2 (3)	C23—C22—N22	116.0 (4)
C16—C11—S1	121.9 (3)	C21—C22—N22	121.4 (4)
C12—C11—S1	121.9 (2)	C24—C23—C22	119.6 (4)
C13—C12—C11	122.7 (3)	C24—C23—H23	120.2
C13—C12—N12	116.8 (3)	C22—C23—H23	120.2
C11—C12—N12	120.5 (3)	C23—C24—C25	119.1 (3)
C14—C13—C12	119.5 (3)	C23—C24—C241	119.7 (4)
C14—C13—H13	120.3	C25—C24—C241	121.1 (4)
C12—C13—H13	120.3	F241—C241—F243	107.0 (4)
C15—C14—C13	119.3 (3)	F241—C241—F242	104.8 (4)
C15—C14—C141	121.3 (4)	F243—C241—F242	105.0 (4)
C13—C14—C141	119.5 (4)	F241—C241—C24	113.6 (4)
F141—C141—F142	106.8 (4)	F243—C241—C24	112.9 (4)
F141—C141—F143	104.4 (4)	F242—C241—C24	112.8 (4)
F142—C141—F143	104.8 (4)	C26—C25—C24	121.0 (4)
F141—C141—C14	113.7 (4)	C26—C25—H25	119.5
F142—C141—C14	113.8 (4)	C24—C25—H25	119.5
F143—C141—C14	112.5 (4)	C25—C26—C21	121.2 (4)
C14—C15—C16	120.9 (3)	C25—C26—H26	119.4
C14—C15—H15	119.5	C21—C26—H26	119.4
C11—S1—S2—C21	−89.93 (15)	C13—C14—C141—F143	−41.2 (5)
S1—S2—C21—C22	−170.2 (2)	C13—C14—C15—C16	−0.8 (5)
S1—S2—C21—C26	8.0 (3)	C141—C14—C15—C16	177.8 (3)
S2—S1—C11—C12	−173.6 (2)	C14—C15—C16—C11	−1.4 (5)
S2—S1—C11—C16	6.6 (3)	C12—C11—C16—C15	2.8 (5)
C21—C22—N22—O221	0.3 (5)	S1—C11—C16—C15	−177.4 (3)
C21—C22—N22—O222	−178.7 (4)	C26—C21—C22—C23	−1.3 (5)
C23—C22—N22—O221	−178.1 (3)	S2—C21—C22—C23	177.0 (3)
C23—C22—N22—O222	2.9 (5)	C26—C21—C22—N22	−179.5 (3)
C16—C11—C12—C13	−2.1 (5)	S2—C21—C22—N22	−1.2 (5)
S1—C11—C12—C13	178.0 (2)	C21—C22—C23—C24	−0.2 (5)
C16—C11—C12—N12	179.1 (3)	N22—C22—C23—C24	178.1 (3)
S1—C11—C12—N12	−0.8 (4)	C22—C23—C24—C25	0.9 (5)
C13—C12—N12—O122	2.1 (4)	C22—C23—C24—C241	−176.1 (3)
C11—C12—N12—O122	−179.0 (3)	C23—C24—C241—F241	82.4 (5)
C13—C12—N12—O121	−177.8 (3)	C25—C24—C241—F241	−94.6 (5)
C11—C12—N12—O121	1.1 (5)	C23—C24—C241—F243	−155.6 (4)
C11—C12—C13—C14	0.0 (5)	C25—C24—C241—F243	27.4 (5)
N12—C12—C13—C14	178.9 (3)	C23—C24—C241—F242	−36.8 (5)
C12—C13—C14—C15	1.5 (5)	C25—C24—C241—F242	146.3 (4)
C12—C13—C14—C141	−177.2 (3)	C23—C24—C25—C26	−0.1 (5)
C15—C14—C141—F141	−101.4 (5)	C241—C24—C25—C26	176.9 (3)
C13—C14—C141—F141	77.2 (5)	C24—C25—C26—C21	−1.5 (6)
C15—C14—C141—F142	21.2 (6)	C22—C21—C26—C25	2.1 (5)
C13—C14—C141—F142	−160.2 (4)	S2—C21—C26—C25	−176.2 (3)
C15—C14—C141—F143	140.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O222^i	0.93	2.57	3.421 (5)	152
C26—H26···O122^ii	0.93	2.46	3.239 (5)	141

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

(7) S-(2-Nitrophenyl) 2-nitrobenzene thiosulfonate

Crystal data

C12H8N2O6S2	Z = 6
Mr = 340.32	F(000) = 1044
Triclinic, P1	Dx = 1.670 Mg m^−3
a = 8.8211 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.042 (2) Å	Cell parameters from 8996 reflections
c = 21.258 (4) Å	θ = 2.9–29.7°
α = 101.06 (3)°	µ = 0.43 mm^−1
β = 91.97 (3)°	T = 150 K
γ = 91.07 (3)°	Plate, yellow
V = 2030.3 (7) Å^3	0.05 × 0.05 × 0.01 mm

Data collection

Kappa-CCD diffractometer	8996 independent reflections
Radiation source: fine-focus sealed X-ray tube	3364 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ϕ scans and ω scans with κ offsets	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan SORTAV (Blessing, 1995 & 1997)	h = −11→10
Tmin = 0.979, Tmax = 0.996	k = −11→14
19285 measured reflections	l = −29→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.189	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0515P)^2] where P = (Fo^2 + 2Fc^2)/3
8996 reflections	(Δ/σ)max = 0.001
595 parameters	Δρmax = 0.73 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.75190 (18)	0.42884 (16)	0.26121 (8)	0.0306 (4)
O1	0.8710 (4)	0.5209 (4)	0.27188 (19)	0.0344 (12)
O2	0.7558 (5)	0.3298 (4)	0.20682 (19)	0.0414 (12)
S2	0.54838 (18)	0.51519 (17)	0.25096 (8)	0.0354 (5)
C11	0.7460 (6)	0.3694 (6)	0.3325 (3)	0.0239 (15)
C12	0.6805 (6)	0.2537 (6)	0.3367 (3)	0.0263 (15)
N12	0.5993 (6)	0.1748 (6)	0.2814 (3)	0.0372 (15)
O121	0.5014 (5)	0.2206 (5)	0.2526 (2)	0.0533 (15)
O122	0.6362 (5)	0.0650 (5)	0.2698 (2)	0.0476 (13)
C13	0.6856 (6)	0.2100 (6)	0.3935 (3)	0.0304 (16)
C14	0.7540 (7)	0.2845 (7)	0.4476 (3)	0.0389 (18)
C15	0.8185 (6)	0.3966 (6)	0.4445 (3)	0.0294 (16)
C16	0.8124 (6)	0.4391 (6)	0.3876 (3)	0.0300 (16)
C21	0.5814 (6)	0.6440 (6)	0.3139 (3)	0.0253 (15)
C22	0.6622 (6)	0.7530 (6)	0.3086 (3)	0.0284 (16)
N22	0.7217 (6)	0.7675 (5)	0.2458 (3)	0.0368 (14)
O221	0.6408 (5)	0.7366 (5)	0.1976 (2)	0.0450 (13)
O222	0.8488 (5)	0.8154 (5)	0.2480 (2)	0.0541 (15)
C23	0.6910 (7)	0.8459 (7)	0.3595 (3)	0.0378 (18)
C24	0.6359 (7)	0.8353 (8)	0.4187 (3)	0.043 (2)
C25	0.5565 (7)	0.7337 (8)	0.4263 (3)	0.042 (2)
C26	0.5297 (6)	0.6380 (7)	0.3742 (3)	0.0344 (17)
S3	0.74925 (17)	0.02210 (16)	0.59309 (8)	0.0279 (4)
O3	0.6293 (4)	−0.0641 (4)	0.5977 (2)	0.0346 (11)
O4	0.7447 (5)	0.0879 (4)	0.54078 (18)	0.0340 (11)
S4	0.95184 (17)	−0.07031 (16)	0.58652 (8)	0.0305 (4)
C31	0.7565 (6)	0.1294 (6)	0.6668 (3)	0.0230 (14)
C32	0.8166 (6)	0.2514 (6)	0.6751 (3)	0.0231 (15)
N32	0.8927 (6)	0.2955 (5)	0.6230 (2)	0.0300 (13)
O321	0.9950 (5)	0.2346 (5)	0.5970 (2)	0.0447 (13)
O322	0.8485 (5)	0.3941 (4)	0.6103 (2)	0.0404 (12)
C33	0.8071 (6)	0.3324 (6)	0.7328 (3)	0.0282 (16)
C34	0.7435 (7)	0.2910 (7)	0.7842 (3)	0.0354 (17)
C35	0.6889 (6)	0.1732 (7)	0.7768 (3)	0.0327 (17)
C36	0.6929 (6)	0.0916 (6)	0.7192 (3)	0.0288 (16)
C41	0.9207 (6)	−0.1563 (6)	0.6480 (3)	0.0245 (15)
C42	0.8318 (6)	−0.2656 (6)	0.6402 (3)	0.0256 (15)
N42	0.7644 (6)	−0.3236 (5)	0.5765 (3)	0.0352 (14)
O421	0.8377 (5)	−0.3218 (4)	0.5287 (2)	0.0396 (12)
O422	0.6369 (5)	−0.3725 (5)	0.5760 (2)	0.0487 (14)
C43	0.8037 (7)	−0.3227 (6)	0.6903 (3)	0.0351 (17)
C44	0.8663 (7)	−0.2726 (7)	0.7505 (3)	0.0415 (19)
C45	0.9544 (7)	−0.1676 (7)	0.7590 (3)	0.0421 (19)
C46	0.9808 (6)	−0.1063 (6)	0.7086 (3)	0.0316 (16)
S5	0.79527 (17)	0.66439 (16)	0.92199 (7)	0.0274 (4)
O5	0.9146 (4)	0.7526 (4)	0.92025 (18)	0.0309 (11)
O6	0.7757 (4)	0.5613 (4)	0.86949 (18)	0.0326 (11)
S6	0.59025 (17)	0.75433 (16)	0.92699 (8)	0.0314 (4)
C51	0.8210 (6)	0.6124 (6)	0.9953 (3)	0.0209 (15)
C52	0.7670 (6)	0.5001 (6)	1.0076 (3)	0.0257 (15)
N52	0.6727 (6)	0.4142 (5)	0.9605 (3)	0.0337 (14)
O521	0.5619 (5)	0.4529 (4)	0.9351 (2)	0.0422 (13)
O522	0.7089 (5)	0.3050 (5)	0.9497 (2)	0.0471 (13)
C53	0.8001 (7)	0.4654 (7)	1.0657 (3)	0.0350 (17)
C54	0.8802 (7)	0.5486 (8)	1.1127 (3)	0.045 (2)
C55	0.9332 (7)	0.6562 (8)	1.1020 (3)	0.041 (2)
C56	0.9031 (6)	0.6904 (6)	1.0434 (3)	0.0296 (16)
C61	0.6476 (6)	0.8832 (6)	0.9877 (3)	0.0259 (15)
C62	0.7323 (6)	0.9852 (6)	0.9774 (3)	0.0273 (15)
N62	0.7791 (7)	0.9978 (5)	0.9135 (3)	0.0338 (14)
O621	0.6899 (5)	0.9626 (4)	0.8678 (2)	0.0412 (12)
O622	0.9037 (5)	1.0450 (4)	0.9091 (2)	0.0442 (13)
C63	0.7805 (6)	1.0787 (6)	1.0280 (3)	0.0315 (16)
C64	0.7370 (7)	1.0734 (7)	1.0886 (3)	0.0394 (19)
C65	0.6511 (7)	0.9735 (7)	1.1004 (3)	0.0375 (18)
C66	0.6098 (6)	0.8782 (7)	1.0507 (3)	0.0336 (17)
H13	0.6434	0.1311	0.3956	0.037*
H14	0.7559	0.2571	0.4873	0.047*
H15	0.8675	0.4453	0.4816	0.035*
H16	0.8550	0.5182	0.3864	0.036*
H23	0.7480	0.9172	0.3548	0.045*
H24	0.6543	0.9007	0.4545	0.052*
H25	0.5193	0.7278	0.4670	0.050*
H26	0.4746	0.5664	0.3799	0.041*
H33	0.8434	0.4153	0.7374	0.034*
H34	0.7384	0.3453	0.8245	0.043*
H35	0.6465	0.1464	0.8124	0.039*
H36	0.6527	0.0099	0.7152	0.035*
H43	0.7420	−0.3958	0.6840	0.042*
H44	0.8480	−0.3113	0.7858	0.050*
H45	0.9989	−0.1352	0.8002	0.050*
H46	1.0392	−0.0314	0.7158	0.038*
H53	0.7687	0.3867	1.0731	0.042*
H54	0.8979	0.5284	1.1538	0.054*
H55	0.9919	0.7097	1.1345	0.049*
H56	0.9394	0.7681	1.0364	0.035*
H63	0.8428	1.1454	1.0206	0.038*
H64	0.7657	1.1388	1.1232	0.047*
H65	0.6212	0.9712	1.1427	0.045*
H66	0.5552	0.8085	1.0591	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0378 (10)	0.0227 (11)	0.0317 (10)	0.0043 (8)	0.0024 (8)	0.0058 (8)
O1	0.025 (2)	0.046 (3)	0.036 (3)	−0.004 (2)	−0.0004 (19)	0.020 (2)
O2	0.068 (3)	0.031 (3)	0.023 (2)	0.013 (2)	0.001 (2)	−0.001 (2)
S2	0.0399 (10)	0.0254 (11)	0.0396 (10)	0.0023 (8)	−0.0081 (8)	0.0041 (9)
C11	0.024 (3)	0.018 (4)	0.030 (4)	0.003 (3)	−0.002 (3)	0.004 (3)
C12	0.022 (3)	0.021 (4)	0.033 (4)	0.003 (3)	−0.001 (3)	−0.003 (3)
N12	0.034 (3)	0.030 (4)	0.047 (4)	−0.004 (3)	0.004 (3)	0.006 (3)
O121	0.045 (3)	0.045 (4)	0.065 (4)	0.005 (3)	−0.019 (3)	0.001 (3)
O122	0.063 (3)	0.024 (3)	0.054 (3)	−0.002 (3)	0.007 (2)	0.002 (3)
C13	0.032 (4)	0.013 (4)	0.049 (4)	0.000 (3)	0.008 (3)	0.014 (3)
C14	0.043 (4)	0.042 (5)	0.038 (4)	0.008 (4)	0.014 (3)	0.021 (4)
C15	0.034 (4)	0.035 (5)	0.020 (4)	−0.003 (3)	0.006 (3)	0.005 (3)
C16	0.031 (3)	0.023 (4)	0.037 (4)	−0.001 (3)	−0.004 (3)	0.010 (3)
C21	0.027 (3)	0.020 (4)	0.028 (4)	0.002 (3)	−0.004 (3)	0.002 (3)
C22	0.020 (3)	0.028 (4)	0.038 (4)	0.005 (3)	−0.002 (3)	0.008 (3)
N22	0.042 (4)	0.022 (4)	0.045 (4)	0.008 (3)	0.005 (3)	0.002 (3)
O221	0.050 (3)	0.050 (4)	0.035 (3)	0.006 (3)	0.005 (2)	0.007 (3)
O222	0.046 (3)	0.051 (4)	0.060 (4)	−0.017 (3)	0.017 (3)	−0.003 (3)
C23	0.032 (4)	0.028 (5)	0.050 (5)	0.004 (3)	−0.004 (3)	0.000 (4)
C24	0.045 (4)	0.048 (6)	0.031 (4)	0.014 (4)	0.000 (4)	−0.009 (4)
C25	0.035 (4)	0.063 (6)	0.029 (4)	0.014 (4)	0.004 (3)	0.012 (4)
C26	0.026 (3)	0.041 (5)	0.042 (4)	0.004 (3)	−0.001 (3)	0.023 (4)
S3	0.0330 (9)	0.0208 (11)	0.0289 (9)	0.0010 (8)	−0.0028 (7)	0.0029 (8)
O3	0.029 (2)	0.022 (3)	0.051 (3)	−0.009 (2)	−0.006 (2)	0.004 (2)
O4	0.058 (3)	0.018 (3)	0.027 (3)	0.002 (2)	−0.007 (2)	0.007 (2)
S4	0.0353 (9)	0.0227 (11)	0.0359 (10)	0.0049 (8)	0.0107 (8)	0.0096 (8)
C31	0.022 (3)	0.019 (4)	0.030 (4)	0.002 (3)	0.003 (3)	0.006 (3)
C32	0.019 (3)	0.027 (4)	0.025 (4)	−0.001 (3)	0.003 (3)	0.009 (3)
N32	0.029 (3)	0.025 (4)	0.036 (3)	−0.012 (3)	−0.005 (3)	0.009 (3)
O321	0.041 (3)	0.048 (4)	0.050 (3)	0.001 (3)	0.017 (2)	0.019 (3)
O322	0.054 (3)	0.024 (3)	0.048 (3)	0.000 (2)	0.001 (2)	0.019 (2)
C33	0.031 (4)	0.017 (4)	0.034 (4)	−0.001 (3)	−0.006 (3)	0.001 (3)
C34	0.043 (4)	0.038 (5)	0.024 (4)	0.006 (4)	−0.001 (3)	0.003 (3)
C35	0.029 (4)	0.045 (5)	0.025 (4)	0.002 (3)	0.001 (3)	0.009 (4)
C36	0.037 (4)	0.017 (4)	0.033 (4)	0.004 (3)	0.002 (3)	0.005 (3)
C41	0.023 (3)	0.025 (4)	0.029 (4)	0.005 (3)	0.006 (3)	0.015 (3)
C42	0.023 (3)	0.031 (4)	0.024 (4)	0.007 (3)	0.005 (3)	0.008 (3)
N42	0.043 (4)	0.020 (4)	0.042 (4)	0.004 (3)	−0.002 (3)	0.008 (3)
O421	0.053 (3)	0.037 (3)	0.026 (3)	0.001 (2)	−0.002 (2)	0.001 (2)
O422	0.043 (3)	0.039 (4)	0.065 (4)	−0.016 (3)	−0.007 (3)	0.016 (3)
C43	0.039 (4)	0.026 (4)	0.046 (5)	0.000 (3)	0.006 (3)	0.019 (4)
C44	0.049 (4)	0.052 (6)	0.027 (4)	0.014 (4)	0.005 (3)	0.014 (4)
C45	0.039 (4)	0.049 (6)	0.041 (5)	0.011 (4)	−0.005 (3)	0.013 (4)
C46	0.032 (4)	0.024 (4)	0.036 (4)	0.002 (3)	−0.002 (3)	−0.002 (3)
S5	0.0344 (9)	0.0219 (11)	0.0261 (9)	−0.0004 (8)	0.0001 (7)	0.0057 (8)
O5	0.029 (2)	0.032 (3)	0.033 (3)	0.001 (2)	−0.0003 (19)	0.008 (2)
O6	0.047 (3)	0.022 (3)	0.025 (2)	−0.001 (2)	0.001 (2)	−0.002 (2)
S6	0.0330 (9)	0.0214 (11)	0.0373 (10)	0.0001 (8)	−0.0062 (8)	0.0009 (8)
C51	0.017 (3)	0.027 (4)	0.018 (3)	−0.003 (3)	−0.002 (3)	0.005 (3)
C52	0.032 (3)	0.012 (4)	0.031 (4)	0.003 (3)	−0.001 (3)	−0.001 (3)
N52	0.038 (3)	0.025 (4)	0.039 (4)	−0.003 (3)	0.005 (3)	0.009 (3)
O521	0.039 (3)	0.038 (3)	0.047 (3)	−0.003 (2)	−0.007 (2)	0.004 (3)
O522	0.053 (3)	0.022 (3)	0.064 (4)	−0.004 (2)	0.001 (3)	0.003 (3)
C53	0.036 (4)	0.033 (5)	0.043 (4)	0.014 (3)	0.015 (3)	0.021 (4)
C54	0.044 (4)	0.065 (7)	0.028 (4)	0.020 (4)	0.000 (4)	0.013 (4)
C55	0.021 (3)	0.071 (7)	0.029 (4)	0.000 (4)	−0.005 (3)	0.010 (4)
C56	0.030 (3)	0.024 (4)	0.035 (4)	0.001 (3)	−0.001 (3)	0.005 (3)
C61	0.024 (3)	0.020 (4)	0.032 (4)	0.003 (3)	−0.001 (3)	−0.001 (3)
C62	0.026 (3)	0.024 (4)	0.032 (4)	0.004 (3)	0.001 (3)	0.005 (3)
N62	0.045 (4)	0.018 (4)	0.039 (4)	−0.001 (3)	0.008 (3)	0.006 (3)
O621	0.053 (3)	0.035 (3)	0.037 (3)	0.000 (2)	−0.002 (2)	0.010 (2)
O622	0.042 (3)	0.036 (3)	0.054 (3)	−0.009 (3)	0.010 (2)	0.006 (3)
C63	0.026 (3)	0.024 (4)	0.043 (4)	0.001 (3)	−0.010 (3)	0.005 (3)
C64	0.039 (4)	0.027 (5)	0.045 (5)	0.008 (3)	−0.011 (4)	−0.010 (4)
C65	0.045 (4)	0.034 (5)	0.031 (4)	0.010 (4)	0.010 (3)	−0.004 (4)
C66	0.027 (3)	0.035 (5)	0.042 (4)	0.004 (3)	0.013 (3)	0.012 (4)

Geometric parameters (Å, º)

S1—O1	1.430 (4)	C35—H35	0.9500
S1—O2	1.433 (4)	C36—H36	0.9500
S1—C11	1.764 (6)	C41—C46	1.384 (8)
S1—S2	2.073 (2)	C41—C42	1.406 (8)
S2—C21	1.768 (6)	C42—C43	1.365 (8)
C11—C16	1.379 (8)	C42—N42	1.483 (7)
C11—C12	1.412 (8)	N42—O421	1.226 (6)
C12—C13	1.384 (8)	N42—O422	1.237 (6)
C12—N12	1.477 (7)	C43—C44	1.384 (8)
N12—O121	1.214 (6)	C43—H43	0.9500
N12—O122	1.242 (7)	C44—C45	1.363 (10)
C13—C14	1.390 (9)	C44—H44	0.9500
C13—H13	0.9500	C45—C46	1.396 (9)
C14—C15	1.366 (9)	C45—H45	0.9500
C14—H14	0.9500	C46—H46	0.9500
C15—C16	1.377 (8)	S5—O5	1.427 (4)
C15—H15	0.9500	S5—O6	1.437 (4)
C16—H16	0.9500	S5—C51	1.771 (6)
C21—C26	1.387 (8)	S5—S6	2.076 (2)
C21—C22	1.412 (9)	S6—C61	1.781 (6)
C22—C23	1.354 (9)	C51—C56	1.378 (8)
C22—N22	1.486 (8)	C51—C52	1.394 (8)
N22—O221	1.219 (6)	C52—C53	1.387 (8)
N22—O222	1.226 (6)	C52—N52	1.464 (7)
C23—C24	1.390 (9)	N52—O521	1.223 (6)
C23—H23	0.9500	N52—O522	1.233 (7)
C24—C25	1.349 (10)	C53—C54	1.385 (9)
C24—H24	0.9500	C53—H53	0.9500
C25—C26	1.387 (9)	C54—C55	1.331 (10)
C25—H25	0.9500	C54—H54	0.9500
C26—H26	0.9500	C55—C56	1.387 (8)
S3—O3	1.428 (4)	C55—H55	0.9500
S3—O4	1.440 (4)	C56—H56	0.9500
S3—C31	1.773 (6)	C61—C62	1.396 (9)
S3—S4	2.070 (2)	C61—C66	1.401 (8)
S4—C41	1.782 (6)	C62—C63	1.389 (8)
C31—C36	1.394 (8)	C62—N62	1.466 (8)
C31—C32	1.415 (8)	N62—O622	1.221 (6)
C32—C33	1.377 (8)	N62—O621	1.226 (6)
C32—N32	1.471 (7)	C63—C64	1.369 (9)
N32—O321	1.219 (6)	C63—H63	0.9500
N32—O322	1.237 (6)	C64—C65	1.393 (9)
C33—C34	1.393 (8)	C64—H64	0.9500
C33—H33	0.9500	C65—C66	1.374 (9)
C34—C35	1.357 (9)	C65—H65	0.9500
C34—H34	0.9500	C66—H66	0.9500
C35—C36	1.375 (8)
O1—S1—O2	119.3 (3)	C35—C36—C31	119.6 (6)
O1—S1—C11	105.8 (3)	C35—C36—H36	120.2
O2—S1—C11	110.1 (3)	C31—C36—H36	120.2
O1—S1—S2	108.3 (2)	C46—C41—C42	118.2 (6)
O2—S1—S2	105.5 (2)	C46—C41—S4	116.8 (5)
C11—S1—S2	107.4 (2)	C42—C41—S4	124.9 (5)
C21—S2—S1	97.6 (2)	C43—C42—C41	122.1 (6)
C16—C11—C12	117.5 (6)	C43—C42—N42	117.2 (6)
C16—C11—S1	118.1 (5)	C41—C42—N42	120.7 (5)
C12—C11—S1	124.4 (4)	O421—N42—O422	124.7 (6)
C13—C12—C11	121.6 (6)	O421—N42—C42	118.8 (5)
C13—C12—N12	116.6 (6)	O422—N42—C42	116.4 (5)
C11—C12—N12	121.8 (6)	C42—C43—C44	119.0 (7)
O121—N12—O122	125.9 (6)	C42—C43—H43	120.5
O121—N12—C12	118.4 (6)	C44—C43—H43	120.5
O122—N12—C12	115.7 (5)	C45—C44—C43	119.9 (7)
C12—C13—C14	118.3 (6)	C45—C44—H44	120.0
C12—C13—H13	120.8	C43—C44—H44	120.0
C14—C13—H13	120.8	C44—C45—C46	121.7 (7)
C15—C14—C13	121.1 (6)	C44—C45—H45	119.2
C15—C14—H14	119.5	C46—C45—H45	119.2
C13—C14—H14	119.5	C41—C46—C45	119.0 (7)
C14—C15—C16	120.0 (6)	C41—C46—H46	120.5
C14—C15—H15	120.0	C45—C46—H46	120.5
C16—C15—H15	120.0	O5—S5—O6	118.7 (3)
C15—C16—C11	121.5 (6)	O5—S5—C51	106.6 (3)
C15—C16—H16	119.2	O6—S5—C51	110.4 (3)
C11—C16—H16	119.2	O5—S5—S6	108.6 (2)
C26—C21—C22	116.3 (6)	O6—S5—S6	105.65 (19)
C26—C21—S2	118.6 (5)	C51—S5—S6	106.2 (2)
C22—C21—S2	125.0 (5)	C61—S6—S5	97.4 (2)
C23—C22—C21	122.3 (6)	C56—C51—C52	118.3 (5)
C23—C22—N22	117.7 (6)	C56—C51—S5	116.2 (5)
C21—C22—N22	120.0 (6)	C52—C51—S5	125.5 (4)
O221—N22—O222	125.4 (6)	C53—C52—C51	120.9 (6)
O221—N22—C22	118.9 (5)	C53—C52—N52	117.0 (6)
O222—N22—C22	115.6 (5)	C51—C52—N52	122.1 (5)
C22—C23—C24	119.0 (7)	O521—N52—O522	123.7 (5)
C22—C23—H23	120.5	O521—N52—C52	119.1 (6)
C24—C23—H23	120.5	O522—N52—C52	117.2 (5)
C25—C24—C23	121.1 (7)	C54—C53—C52	118.1 (7)
C25—C24—H24	119.5	C54—C53—H53	120.9
C23—C24—H24	119.5	C52—C53—H53	120.9
C24—C25—C26	119.6 (7)	C55—C54—C53	121.8 (6)
C24—C25—H25	120.2	C55—C54—H54	119.1
C26—C25—H25	120.2	C53—C54—H54	119.1
C25—C26—C21	121.7 (7)	C54—C55—C56	120.2 (7)
C25—C26—H26	119.2	C54—C55—H55	119.9
C21—C26—H26	119.2	C56—C55—H55	119.9
O3—S3—O4	119.1 (3)	C51—C56—C55	120.4 (7)
O3—S3—C31	106.0 (3)	C51—C56—H56	119.8
O4—S3—C31	109.4 (3)	C55—C56—H56	119.8
O3—S3—S4	108.5 (2)	C62—C61—C66	118.2 (6)
O4—S3—S4	105.8 (2)	C62—C61—S6	124.8 (5)
C31—S3—S4	107.58 (19)	C66—C61—S6	117.0 (5)
C41—S4—S3	97.33 (19)	C63—C62—C61	121.4 (6)
C36—C31—C32	118.3 (6)	C63—C62—N62	116.4 (6)
C36—C31—S3	117.2 (5)	C61—C62—N62	122.2 (6)
C32—C31—S3	124.5 (5)	O622—N62—O621	124.0 (5)
C33—C32—C31	120.9 (6)	O622—N62—C62	117.8 (5)
C33—C32—N32	117.8 (6)	O621—N62—C62	118.1 (5)
C31—C32—N32	121.3 (6)	C64—C63—C62	118.9 (7)
O321—N32—O322	125.5 (6)	C64—C63—H63	120.5
O321—N32—C32	118.2 (5)	C62—C63—H63	120.5
O322—N32—C32	116.2 (5)	C63—C64—C65	121.0 (6)
C32—C33—C34	119.1 (6)	C63—C64—H64	119.5
C32—C33—H33	120.5	C65—C64—H64	119.5
C34—C33—H33	120.5	C66—C65—C64	119.8 (6)
C35—C34—C33	120.1 (6)	C66—C65—H65	120.1
C35—C34—H34	119.9	C64—C65—H65	120.1
C33—C34—H34	119.9	C65—C66—C61	120.5 (7)
C34—C35—C36	122.0 (7)	C65—C66—H66	119.7
C34—C35—H35	119.0	C61—C66—H66	119.7
C36—C35—H35	119.0
O1—S1—S2—C21	−42.5 (3)	C34—C35—C36—C31	0.8 (9)
O2—S1—S2—C21	−171.3 (3)	C32—C31—C36—C35	0.7 (8)
C11—S1—S2—C21	71.3 (3)	S3—C31—C36—C35	−176.8 (4)
O1—S1—C11—C16	19.2 (5)	S3—S4—C41—C46	−95.0 (4)
O2—S1—C11—C16	149.4 (4)	S3—S4—C41—C42	80.5 (5)
S2—S1—C11—C16	−96.2 (5)	C46—C41—C42—C43	0.1 (9)
O1—S1—C11—C12	−159.4 (5)	S4—C41—C42—C43	−175.4 (5)
O2—S1—C11—C12	−29.3 (6)	C46—C41—C42—N42	−180.0 (5)
S2—S1—C11—C12	85.2 (5)	S4—C41—C42—N42	4.6 (8)
C16—C11—C12—C13	−1.5 (8)	C43—C42—N42—O421	−142.7 (6)
S1—C11—C12—C13	177.1 (4)	C41—C42—N42—O421	37.3 (8)
C16—C11—C12—N12	176.6 (5)	C43—C42—N42—O422	36.2 (8)
S1—C11—C12—N12	−4.7 (8)	C41—C42—N42—O422	−143.8 (6)
C13—C12—N12—O121	127.8 (6)	C41—C42—C43—C44	−1.0 (9)
C11—C12—N12—O121	−50.5 (8)	N42—C42—C43—C44	179.1 (5)
C13—C12—N12—O122	−50.4 (7)	C42—C43—C44—C45	0.1 (10)
C11—C12—N12—O122	131.3 (6)	C43—C44—C45—C46	1.6 (10)
C11—C12—C13—C14	1.6 (9)	C42—C41—C46—C45	1.6 (9)
N12—C12—C13—C14	−176.6 (5)	S4—C41—C46—C45	177.5 (5)
C12—C13—C14—C15	−1.8 (9)	C44—C45—C46—C41	−2.5 (10)
C13—C14—C15—C16	1.9 (10)	O5—S5—S6—C61	−45.9 (3)
C14—C15—C16—C11	−1.9 (9)	O6—S5—S6—C61	−174.3 (3)
C12—C11—C16—C15	1.6 (8)	C51—S5—S6—C61	68.4 (3)
S1—C11—C16—C15	−177.1 (5)	O5—S5—C51—C56	22.7 (5)
S1—S2—C21—C26	−93.1 (5)	O6—S5—C51—C56	152.9 (4)
S1—S2—C21—C22	84.3 (5)	S6—S5—C51—C56	−93.0 (4)
C26—C21—C22—C23	1.3 (9)	O5—S5—C51—C52	−156.5 (5)
S2—C21—C22—C23	−176.2 (5)	O6—S5—C51—C52	−26.3 (6)
C26—C21—C22—N22	180.0 (5)	S6—S5—C51—C52	87.8 (5)
S2—C21—C22—N22	2.5 (8)	C56—C51—C52—C53	−2.5 (9)
C23—C22—N22—O221	−137.8 (6)	S5—C51—C52—C53	176.7 (4)
C21—C22—N22—O221	43.4 (8)	C56—C51—C52—N52	177.0 (5)
C23—C22—N22—O222	39.3 (8)	S5—C51—C52—N52	−3.8 (8)
C21—C22—N22—O222	−139.5 (6)	C53—C52—N52—O521	129.8 (6)
C21—C22—C23—C24	−1.7 (9)	C51—C52—N52—O521	−49.8 (8)
N22—C22—C23—C24	179.6 (5)	C53—C52—N52—O522	−48.8 (8)
C22—C23—C24—C25	0.9 (10)	C51—C52—N52—O522	131.7 (6)
C23—C24—C25—C26	0.2 (10)	C51—C52—C53—C54	3.9 (9)
C24—C25—C26—C21	−0.6 (10)	N52—C52—C53—C54	−175.6 (5)
C22—C21—C26—C25	−0.1 (9)	C52—C53—C54—C55	−4.2 (10)
S2—C21—C26—C25	177.6 (5)	C53—C54—C55—C56	2.9 (10)
O3—S3—S4—C41	−44.5 (3)	C52—C51—C56—C55	1.2 (9)
O4—S3—S4—C41	−173.4 (3)	S5—C51—C56—C55	−178.1 (5)
C31—S3—S4—C41	69.7 (3)	C54—C55—C56—C51	−1.4 (10)
O3—S3—C31—C36	21.3 (5)	S5—S6—C61—C62	79.2 (5)
O4—S3—C31—C36	150.9 (4)	S5—S6—C61—C66	−98.0 (4)
S4—S3—C31—C36	−94.6 (4)	C66—C61—C62—C63	1.1 (9)
O3—S3—C31—C32	−156.0 (5)	S6—C61—C62—C63	−176.0 (4)
O4—S3—C31—C32	−26.4 (6)	C66—C61—C62—N62	179.1 (5)
S4—S3—C31—C32	88.1 (5)	S6—C61—C62—N62	2.0 (8)
C36—C31—C32—C33	−2.6 (8)	C63—C62—N62—O622	34.6 (8)
S3—C31—C32—C33	174.7 (4)	C61—C62—N62—O622	−143.5 (6)
C36—C31—C32—N32	176.7 (5)	C63—C62—N62—O621	−144.0 (6)
S3—C31—C32—N32	−6.0 (8)	C61—C62—N62—O621	37.9 (8)
C33—C32—N32—O321	127.0 (6)	C61—C62—C63—C64	−3.5 (9)
C31—C32—N32—O321	−52.3 (7)	N62—C62—C63—C64	178.4 (5)
C33—C32—N32—O322	−51.4 (7)	C62—C63—C64—C65	2.8 (9)
C31—C32—N32—O322	129.3 (6)	C63—C64—C65—C66	0.4 (10)
C31—C32—C33—C34	3.0 (8)	C64—C65—C66—C61	−2.8 (9)
N32—C32—C33—C34	−176.3 (5)	C62—C61—C66—C65	2.1 (9)
C32—C33—C34—C35	−1.5 (9)	S6—C61—C66—C65	179.5 (5)
C33—C34—C35—C36	−0.4 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O4	0.95	2.37	3.209 (8)	147
C34—H34···O6	0.95	2.41	3.183 (9)	139
C35—H35···O621^i	0.95	2.56	3.298 (9)	134
C44—H44···O6^i	0.95	2.56	3.502 (8)	172
C54—H54···O1^ii	0.95	2.55	3.459 (8)	161
C64—H64···O2^iii	0.95	2.49	3.403 (8)	161
C13—H13···O3^iv	0.95	2.52	3.214 (7)	130
C46—H46···O222^v	0.95	2.53	3.466 (8)	168
C56—H56···O622^vi	0.95	2.53	3.320 (8)	141
C63—H63···O5^vi	0.95	2.57	3.277 (7)	131

Symmetry codes: (i) x, y−1, 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.