5,5′-[1,4-Phenyl­enebis(methyl­enesulfanedi­yl)]bis­[1,3,4-thia­diazol-2(3H)-one] dimethyl sulfoxide disolvate

Kang, S.K.; Cho, N.S.; Jang, S.

doi:10.1107/S1600536812006289

organic compounds

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doi:10.1107/S1600536812006289

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5,5′-[1,4-Phenylenebis(methylenesulfanediyl)]bis[1,3,4-thiadiazol-2(3H)-one] dimethyl sulfoxide disolvate

Sung Kwon Kang,^a ^* Nam Sook Cho ^a and Siyoung Jang ^a

^aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

(Received 9 February 2012; accepted 13 February 2012; online 17 February 2012)

The asymmetric unit of the title compound, C₁₂H₁₀N₄O₂S₄·2C₂H₆OS, contains one half of the p-xylene molecule and one dimethyl sulfoxide molecule. The p-xylene molecule is located about a crystallographic inversion centre. In the molecule, the thiadiazole and benzene rings are almost perpendicular to one another, with a dihedral angle of 88.95 (6)°. In the crystal, an N—H⋯O hydrogen bond is observed between the two components. The dimethyl sulfoxide molecule is disordered over two orientations with an occupancy ratio of 0.879 (1):0.121 (1).

Related literature

For general background to polydentate macrocyclic compounds, see: Dietrich et al. (1993 ); Vogle (1991 ). For the synthesis and reactivity of thiadiazole derivatives, see: Cho et al. (1998 , 1999 , 2001 ).

Experimental

Crystal data

C₁₂H₁₀N₄O₂S₄·2C₂H₆OS
M_r = 526.74
Triclinic, $[P \overline 1]$
a = 7.5723 (15) Å
b = 8.3258 (17) Å
c = 10.346 (2) Å
α = 109.70 (4)°
β = 95.74 (3)°
γ = 91.15 (3)°
V = 610.0 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 296 K
0.18 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.895, T_max = 0.923
21342 measured reflections
3039 independent reflections
2124 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.100
S = 1.02
3039 reflections
162 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O13	0.91 (2)	1.83 (2)	2.742 (3)	175.6 (19)

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006289/is5071sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006289/is5071Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006289/is5071Isup3.cml

checkCIF report

Comment top

Polydentate macrocyclic compounds containing heterocyclic rings as subunits possess a variety of interesting properties. Heterocyclic units contain oxygen, nitrogen or sulfur, which provide the coordination sites allowing the heterocycles to form complexes with metals and act as effective hosts for different kinds of molecules (Dietrich et al., 1993; Vogle, 1991). We studied on macrocyclic compounds composed of two 5-mercapto-2,3-dihydro-1,3,4-thiadizol-2-ones and two p-xylenes (Cho et al., 1998, 1999, 2001). The NH of the title compound, α,α'-bis[(4,5-dihydro-5-oxo-1,3,4-thiazol-2-yl)thio]-p-xylene (I) is acidic enough to be alkylated in triethylamine with alkyl halide. The two NH functional groups can afford ring formation through an [2 + 2] alkylation.

The 5-oxo-1,3,4-thiadiazol-2-yl unit is planar, with an r.m.s. deviation of 0.004 Å from the corresponding squares plane defined by the seven constituent atoms. There is a crystallographic inversion center located in the middle of benzene ring. The bond distance of N4—C5 [1.281 (2) Å] is shorter than that of C2—N3 [1.337 (2) Å], which is consistent with double bond character. The thiadiazole and benzene rings are almost perpendicular to each other, with a dihedral angle 88.95 (6)°. The crystal structure is stabilized by the intermolecular N—H···O hydrogen bonds between the p-xylene compound and the dimethyl sulfoxide molecules (Fig. 1 and Table 1).

Related literature top

For general background to polydentate macrocyclic compounds, see: Dietrich et al. (1993); Vogle (1991). For the synthesis and reactivity of thiadiazole derivatives, see: Cho et al. (1998, 1999, 2001).

Experimental top

To a solution of α,α'-bis[(5-ethoxy-1,3,4-thiadiazol-2-yl)thio]-p-xylene (Cho et al., 1999, 2001) (2.56 g, 6 mmol) in ethanol (20 ml), was added HBr (47%, 3.5 ml, 30 mmol), in one portion. The mixture was heated under reflux until the above p-xylene compound was disappeared on TLC. The solvent evaporated under reduced pressure to leave a solid residue, which was washed with water. The crude product was recrystallized from EtOH:THF = 3:1. Colorless crystals of (I) were obtained from its DMSO solution by slow evaporation of the solvent at room temperature. Yield 92%, m.p. 208–210°C; R_f: 0.63 (n-hexane: EA = 5: 5); IR (KBr pellet, cm^-1): 3120 (NH), 3062, 2950 (CH), 1656 (C═O), 1500, 1200; ¹H NMR (DMSO-d₆, p.p.m.): 12.95(2H, s, NH), 7.35(4H, s, C₆H₄), 4.32(4H, s, SCH₂); ¹³C NMR (DMSO-d₆, p.p.m.): 171.4 (C=O), 147.8 (C—S), 135.9, 129.2, (C₆H₄), 36.2 (SCH₂).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids. Intermolecular N—H···O hydrogen bonds are indicated by dashed lines. Only major components of the disordered dimethyl sulfoxide molecule are shown.
	Fig. 2. Part of the crystal structure of the title compound, showing molecules linked by intermolecular N—H···O hydrogen bonds (dashed lines).

5-({4-[(5-oxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)methyl]phenyl}methyl)- 2,3-dihydro-1,3,4-thiadiazol-2-one dimethyl sulfoxide disolvate top

Crystal data top

C₁₂H₁₀N₄O₂S₄·2C₂H₆OS	Z = 1
M_r = 526.74	F(000) = 274
Triclinic, P1	D_x = 1.434 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5723 (15) Å	Cell parameters from 5678 reflections
b = 8.3258 (17) Å	θ = 2.6–25.2°
c = 10.346 (2) Å	µ = 0.59 mm⁻¹
α = 109.70 (4)°	T = 296 K
β = 95.74 (3)°	Block, colourless
γ = 91.15 (3)°	0.18 × 0.17 × 0.12 mm
V = 610.0 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	2124 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
T_min = 0.895, T_max = 0.923	k = −11→11
21342 measured reflections	l = −13→13
3039 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0506P)²] where P = (F_o² + 2F_c²)/3
3039 reflections	(Δ/σ)_max < 0.001
162 parameters	Δρ_max = 0.16 e Å⁻³
3 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₂H₁₀N₄O₂S₄·2C₂H₆OS	γ = 91.15 (3)°
M_r = 526.74	V = 610.0 (2) Å³
Triclinic, P1	Z = 1
a = 7.5723 (15) Å	Mo Kα radiation
b = 8.3258 (17) Å	µ = 0.59 mm⁻¹
c = 10.346 (2) Å	T = 296 K
α = 109.70 (4)°	0.18 × 0.17 × 0.12 mm
β = 95.74 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3039 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2124 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.923	R_int = 0.083
21342 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	3 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.16 e Å⁻³
3039 reflections	Δρ_min = −0.22 e Å⁻³
162 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.76776 (6)	0.37928 (6)	0.42321 (5)	0.07516 (18)
C2	0.7758 (2)	0.3744 (2)	0.59474 (19)	0.0668 (4)
N3	0.62432 (19)	0.2937 (2)	0.60130 (16)	0.0688 (4)
H3	0.589 (3)	0.282 (3)	0.679 (2)	0.090 (7)*
N4	0.50062 (17)	0.23800 (17)	0.48623 (14)	0.0611 (3)
C5	0.55873 (19)	0.27358 (19)	0.38640 (17)	0.0549 (4)
O6	0.89774 (16)	0.43193 (18)	0.68683 (15)	0.0946 (5)
S7	0.44211 (6)	0.22149 (6)	0.22259 (5)	0.06970 (16)
C8	0.2421 (2)	0.1210 (2)	0.25284 (16)	0.0598 (4)
H8A	0.2729	0.0257	0.283	0.072*
H8B	0.1848	0.2027	0.3249	0.072*
C9	0.11735 (19)	0.05870 (19)	0.12143 (15)	0.0516 (3)
C10	−0.0134 (2)	0.1597 (2)	0.09349 (16)	0.0610 (4)
H10	−0.0228	0.2687	0.1563	0.073*
C11	0.1302 (2)	−0.1018 (2)	0.02588 (16)	0.0603 (4)
H11	0.2181	−0.1713	0.0421	0.072*
S12	0.32235 (7)	0.21416 (7)	0.85488 (5)	0.0693 (2)	0.8786 (14)
O13	0.5091 (2)	0.2414 (3)	0.8277 (2)	0.0771 (6)	0.8786 (14)
C14	0.1951 (5)	0.1372 (4)	0.6870 (4)	0.0807 (9)	0.8786 (14)
H14A	0.2232	0.0218	0.639	0.121*	0.8786 (14)
H14B	0.2238	0.2084	0.635	0.121*	0.8786 (14)
H14C	0.0706	0.1402	0.6975	0.121*	0.8786 (14)
C15	0.2328 (6)	0.4158 (6)	0.9137 (4)	0.0964 (12)	0.8786 (14)
H15A	0.2907	0.4803	1.0039	0.145*	0.8786 (14)
H15B	0.1078	0.4017	0.9183	0.145*	0.8786 (14)
H15C	0.2511	0.4757	0.8509	0.145*	0.8786 (14)
S12A	0.3220 (5)	0.3284 (5)	0.7826 (4)	0.0717 (14)	0.1214 (14)
O13A	0.5108 (17)	0.3036 (17)	0.8234 (16)	0.057 (4)*	0.1214 (14)
C14A	0.209 (5)	0.126 (3)	0.729 (3)	0.093 (11)*	0.1214 (14)
H14D	0.29	0.0394	0.6939	0.14*	0.1214 (14)
H14E	0.1146	0.1194	0.6573	0.14*	0.1214 (14)
H14F	0.1595	0.1102	0.8058	0.14*	0.1214 (14)
C15A	0.250 (5)	0.410 (5)	0.952 (2)	0.087 (10)*	0.1214 (14)
H15D	0.3501	0.4642	1.0183	0.13*	0.1214 (14)
H15E	0.1998	0.3176	0.9746	0.13*	0.1214 (14)
H15F	0.1623	0.4918	0.953	0.13*	0.1214 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0514 (3)	0.0787 (3)	0.0898 (4)	−0.0150 (2)	−0.0004 (2)	0.0249 (2)
C2	0.0489 (9)	0.0614 (10)	0.0737 (11)	−0.0010 (7)	−0.0108 (8)	0.0069 (8)
N3	0.0541 (8)	0.0853 (10)	0.0560 (8)	−0.0119 (7)	−0.0137 (7)	0.0162 (7)
N4	0.0495 (7)	0.0731 (9)	0.0527 (7)	−0.0090 (6)	−0.0092 (6)	0.0159 (6)
C5	0.0436 (8)	0.0553 (8)	0.0607 (9)	−0.0018 (6)	−0.0025 (7)	0.0156 (7)
O6	0.0600 (8)	0.0931 (10)	0.0981 (10)	−0.0088 (7)	−0.0304 (7)	0.0017 (8)
S7	0.0588 (3)	0.0926 (3)	0.0573 (3)	−0.0129 (2)	−0.00617 (19)	0.0296 (2)
C8	0.0500 (9)	0.0749 (10)	0.0494 (8)	−0.0074 (7)	−0.0062 (7)	0.0184 (7)
C9	0.0442 (8)	0.0595 (9)	0.0460 (8)	−0.0028 (6)	−0.0026 (6)	0.0139 (7)
C10	0.0565 (9)	0.0579 (9)	0.0562 (9)	0.0060 (7)	−0.0038 (7)	0.0062 (7)
C11	0.0512 (9)	0.0627 (10)	0.0600 (9)	0.0109 (7)	−0.0066 (7)	0.0149 (7)
S12	0.0666 (3)	0.0796 (4)	0.0724 (4)	0.0135 (2)	0.0099 (2)	0.0388 (3)
O13	0.0570 (9)	0.1063 (17)	0.0751 (10)	0.0135 (10)	0.0017 (7)	0.0413 (12)
C14	0.0665 (16)	0.0774 (18)	0.085 (2)	−0.0001 (11)	−0.0046 (15)	0.0146 (15)
C15	0.0810 (19)	0.098 (2)	0.088 (2)	0.0245 (14)	−0.0073 (19)	0.007 (2)
S12A	0.064 (2)	0.092 (3)	0.070 (2)	0.0013 (18)	−0.0017 (17)	0.045 (2)

Geometric parameters (Å, º) top

S1—C5	1.7385 (16)	S12—O13	1.4964 (19)
S1—C2	1.784 (2)	S12—C15	1.757 (4)
C2—O6	1.220 (2)	S12—C14	1.802 (4)
C2—N3	1.337 (2)	C14—H14A	0.96
N3—N4	1.3772 (18)	C14—H14B	0.96
N3—H3	0.91 (2)	C14—H14C	0.96
N4—C5	1.281 (2)	C15—H15A	0.96
C5—S7	1.7406 (17)	C15—H15B	0.96
S7—C8	1.8202 (17)	C15—H15C	0.96
C8—C9	1.502 (2)	S12A—O13A	1.488 (13)
C8—H8A	0.97	S12A—C14A	1.758 (18)
C8—H8B	0.97	S12A—C15A	1.796 (18)
C9—C11	1.380 (2)	C14A—H14D	0.96
C9—C10	1.382 (2)	C14A—H14E	0.96
C10—C11ⁱ	1.379 (2)	C14A—H14F	0.96
C10—H10	0.93	C15A—H15D	0.96
C11—C10ⁱ	1.379 (2)	C15A—H15E	0.96
C11—H11	0.93	C15A—H15F	0.96

C5—S1—C2	88.75 (8)	C15—S12—C14	97.27 (19)
O6—C2—N3	127.16 (19)	S12—C14—H14A	109.5
O6—C2—S1	126.18 (16)	S12—C14—H14B	109.5
N3—C2—S1	106.66 (12)	H14A—C14—H14B	109.5
C2—N3—N4	119.02 (16)	S12—C14—H14C	109.5
C2—N3—H3	125.3 (14)	H14A—C14—H14C	109.5
N4—N3—H3	115.3 (14)	H14B—C14—H14C	109.5
C5—N4—N3	109.97 (14)	S12—C15—H15A	109.5
N4—C5—S1	115.59 (12)	S12—C15—H15B	109.5
N4—C5—S7	123.92 (12)	H15A—C15—H15B	109.5
S1—C5—S7	120.48 (10)	S12—C15—H15C	109.5
C5—S7—C8	98.72 (8)	H15A—C15—H15C	109.5
C9—C8—S7	109.26 (12)	H15B—C15—H15C	109.5
C9—C8—H8A	109.8	O13A—S12A—C14A	106.7 (13)
S7—C8—H8A	109.8	O13A—S12A—C15A	98.7 (13)
C9—C8—H8B	109.8	C14A—S12A—C15A	97.6 (18)
S7—C8—H8B	109.8	S12A—C14A—H14D	109.5
H8A—C8—H8B	108.3	S12A—C14A—H14E	109.5
C11—C9—C10	118.39 (13)	H14D—C14A—H14E	109.5
C11—C9—C8	120.59 (14)	S12A—C14A—H14F	109.5
C10—C9—C8	121.02 (14)	H14D—C14A—H14F	109.5
C11ⁱ—C10—C9	121.18 (14)	H14E—C14A—H14F	109.5
C11ⁱ—C10—H10	119.4	S12A—C15A—H15D	109.5
C9—C10—H10	119.4	S12A—C15A—H15E	109.5
C10ⁱ—C11—C9	120.43 (14)	H15D—C15A—H15E	109.5
C10ⁱ—C11—H11	119.8	S12A—C15A—H15F	109.5
C9—C11—H11	119.8	H15D—C15A—H15F	109.5
O13—S12—C15	107.4 (2)	H15E—C15A—H15F	109.5
O13—S12—C14	105.18 (15)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O13	0.91 (2)	1.83 (2)	2.742 (3)	175.6 (19)

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₄O₂S₄·2C₂H₆OS
M_r	526.74
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5723 (15), 8.3258 (17), 10.346 (2)
α, β, γ (°)	109.70 (4), 95.74 (3), 91.15 (3)
V (Å³)	610.0 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.18 × 0.17 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.895, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	21342, 3039, 2124
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.100, 1.02
No. of reflections	3039
No. of parameters	162
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.22

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O13	0.91 (2)	1.83 (2)	2.742 (3)	175.6 (19)

References

Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cho, N. S., Hong, S. I., Park, Y. S. & Suh, I. H. (2001). Bull. Korean Chem. Soc. 22, 1280–1282. CAS Google Scholar
Cho, N. S., Park, C. K., Kim, H. S., Choi, E. S. & Kang, S. K. (1998). Bull. Korean Chem. Soc. 19, 103–106. CAS Google Scholar
Cho, N. S., Park, C. K., Kim, H. S., Oh, J. G., Suh, I. H. & Oh, M. R. (1999). Heterocycles, 51, 2739–2746. CAS Google Scholar
Dietrich, B., Viout, P. & Lehn, J. M. (1993). In Macrocyclic Chemistry: Aspects of Organic and Inorganic Supramolecular Chemistry. Weinheim: VCH. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5,5′-[1,4-Phenyl­enebis(methyl­enesulfanedi­yl)]bis­­[1,3,4-thia­diazol-2(3H)-one] di­methyl sulfoxide disolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

5,5′-[1,4-Phenylenebis(methylenesulfanediyl)]bis[1,3,4-thiadiazol-2(3H)-one] dimethyl sulfoxide disolvate