Dimethyl Sulfoxide Solvent Molecules Research Articles

Crystal structure of the nucleoside 2'-de-oxy-guanosine dimethyl sulfoxide disolvate.

The title com-pound, C10H13N5O4·2C2H6OS, which is of inter-est with respect to its biological activity, at 183 K has ortho-rhom-bic (P212121) crystal symmetry. The structure displays a network of inter-molecular N-H⋯N, N-H⋯O and O-H⋯O hydrogen bonds. 2'-De-oxy-guanosine mol-ecules are linked to each other and to the two dimethyl sulfoxide solvent mol-ecules by hydrogen bonding.

Crystal structure and Hirshfeld surface analysis of 5-oxo-7-phenyl-2-(phenyl-amino)-1H-[1,2,4]triazolo[1,5-a]pyridine-6,8-dicarbo-nitrile dimethyl sulfoxide monosolvate.

In the title compound, C20H12N6O·C2H6OS, the [1,2,4]triazolo[1,5-a]pyridine ring system is almost planar and makes dihedral angles of 16.33 (7) and 46.80 (7)°, respectively, with the phenyl-amino and phenyl rings. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds into chains along the b-axis direction through the dimethyl sulfoxide solvent mol-ecule, forming C(10)R 2 1(6) motifs. These chains are connected via S-O⋯π inter-actions, π-π stacking inter-actions between the pyridine rings [centroid-to-centroid distance = 3.6662 (9) Å] and van der Waals inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (28.1%), C⋯H/H⋯C (27.2%), N⋯H/H⋯N (19.4%) and O⋯H/H⋯O (9.8%) inter-actions.

Preferential solvation and solvation shell composition of sunitinib malate, an anti-tumor compound, in some binary mixed solvents at 298.15 K

Preferential solvation of sunitinib malate (STM) was investigated in the binary mixtures of water, ethanol, ethylene glycol (EG), and propylene carbonate (PC) solvents at 298.15 K. Similar to its pharmaceutical formulation steps, dimethyl sulfoxide (DMSO) was used as the base solvent during our experiments. Bosch–Rose model was utilized to estimate the electronic transition energies, ET, and other preferential solvation parameters, demonstrating solute–solvent and solute–solute interactions. Shifting λmax situation with respect to the dielectric constant of the pure solvents was carefully monitored indicating that STM had the lowest λmax in water and PC among HBD and HBA solvents, respectively. Moreover, ET showed positive deviation with respect to ideality for ethanol–EG, ethanol–PC, and ethanol–DMSO binary systems while negative deviation was obtained for the others which was explainable based on the model assumptions. According to the results, STM molecules preferred to be solvated by PC, ethanol, EG, and DMSO solvent molecules rather than water in the binary mixtures of the aforementioned solvents, meaning that the presence of water in the cybotactic region is least probable compared to the others. Based on the local mole fractions, the abundance of pure solvents and/or complex solvent molecules in the cybotactic region around the solute was discussed in detail, illustrating the specific and non-specific interactions between solute and solvent molecules.

Solvent-assisted planar structure of a stilbene-based salicylhydrazone compound: crystal structure, solvent- and aggregation-induced emission, and switchable luminescence colouration.

A novel stilbene-based salicylhydrazone compound {systematic name: (E)-4,4'-(ethene-1,2-diyl)bis[(N'E)-N'-(2-hydroxybenzylidene)benzohydrazide] dimethyl sulfoxide disolvate, C30H24N4O4·2C2H6OS or L·2DMSO} was synthesized and characterized by single-crystal X-ray diffraction, powder X-ray diffraction and luminescence spectroscopy. The title compound crystallizes in the monoclinic space group P21/c, with half a symmetry-independent L molecule and one dimethyl sulfoxide (DMSO) solvent molecule in the asymmetric unit. The L molecule adopts an almost planar structure, with a small dihedral angle between the planes of the stilbene and salicylhydrazone groups. There are multiple π-π stacking interactions between adjacent L molecules. The DMSO solvent molecules act as proton donors and acceptors, forming hydrogen bonds of various strengths with the L molecules. In addition, the geometry optimization of a single molecule of L and its luminescence properties either in solution, as a solvated solid or as a desolvated solid were studied. The compound shows an aggregation-induced emission (AIE) effect and exhibits switchable luminescence colouration in the solid state by the simple removal or re-addition of the DMSO solvent.

Paramagnetic iron-containing ionic liquid crystals

Iron-containing ionic liquid crystals of N,N′-dialkylimidazolium salts ([(CnH2n+1)2IM]3[Fe(CN)6], with n = 12 (1), 14 (2), 16 (3), 18 (4), IM = imidazolium) were prepared and their structures and properties were characterized. Differential scanning calorimetry (DSC), polarizing optical microscopy (POM) as well as powder X-ray diffraction (PXRD) analysis reveal for all compounds thermotropic liquid crystalline behavior. The observed textures point to smectic A and smectic X phases. The crystal structure of the solvate [C12C12IM]3[Fe(CN)6]·2 DMSO (DMSO = dimethylsulfoxide) was examined by single crystal X-ray diffraction analysis which reveals two crystallographically independent [C12C12IM]+ cations with different conformation, U-shape and rod-shape, together with a nearly ideal octahedral [Fe(CN)6]3− anion and two DMSO solvent molecules. The crystal packing is characterized by alternating bilayers of almost linearly arranged imidazolium cations with the U-shaped cations being arranged in a head-to-head fashion and the cations' hydrophobic dodecyl chains being interdigitated. Magnetic measurements for compounds 1–4 show paramagnetic moments, μeff, of ~1.7 μB, which are close to the theoretically expected value for a d5 low-spin Fe3+ spin-only S = 1/2 system (μeffs.o. = 1.73 μB). It was possible to obtain an Fe3+ containing ILC material that combines liquid crystalline behavior over a large mesophase window (from 33 °C to 170 °C) with high magnetic susceptibility by mixing compound 3 with [C16C16IM][FeCl4] (5), which contains the d5 high-spin Fe3+ ion (S = 5/2). All compounds are highly hydrophobic and stable in the atmosphere indicating a great potential of applications as functional materials.

Cytotoxicity of photoactivatable bromo tricarbonyl manganese(i) compounds against human liver carcinoma cells.

Two series of photoinduced tricarbonyl manganese(i) compounds were prepared from the reaction of [MnBr(CO)3(2-C(H)[double bond, length as m-dash]O)] (2-C(H)[double bond, length as m-dash]O: quinoline-2-carboxaldehyde and pyridine-2-carboxaldehyde) and para-substituted aniline derivatives (X = OH, OCH3, Cl and NO2). Different electron-donating and electron-withdrawing substituents were introduced in the para-position of the phenyl ring to investigate their influence on the stability of the compounds in the dark and the photophysical properties upon illumination at 525 nm. When kept in the dark, the aerated solutions of the complexes in dimethyl sulfoxide (DMSO) and CH2Cl2 were stable. In the solution, the complexes bearing electron-withdrawing substituents, exchange their bromo ligands with DMSO solvent molecules, as evidenced from infrared and UV/Vis studies as well as time-dependent density functional theory (TDDFT) calculations. The complexes were assessed for their cytotoxicity, both in the dark and upon exposure to a 525 nm LED, against the human hepatocarcinoma cell line (HepG2). A marked reduction in the viability of HepG2 cells treated with the complex functionalized with quinoline and methoxy substituent was observed after illumination in a dose-dependent manner, with an IC50 value of 7.1 μM, making it the most phototoxic compound in our study.

Synthesis and crystal structures of some bis(3-methyl-1H-indol-2-yl)(salicyl)methanes.

Four 2,2'-bisindolylmethanes (BIMs), a useful class of polyindolyl species joined to a central carbon, were synthesized using salicylaldehyde derivatives and simple acid catalysis; these are 2-[bis(3-methyl-1H-indol-2-yl)methyl]-6-methylphenol, (IIa), 2-[bis(3-methyl-1H-indol-2-yl)methyl]-4,6-dichlorophenol, (IIb), 2-[bis(3-methyl-1H-indol-2-yl)methyl]-4-nitrophenol, (IIc), and 2-[bis(3-methyl-1H-indol-2-yl)methyl]-4,6-di-tert-butylphenol, (IId). BIMs (IIa) and (IIb) were characterized crystallographically as the dimethyl sulfoxide (DMSO) disolvates, i.e. C26H24N2O·2C2H6OS and C25H20Cl2N2O·2C2H6OS, respectively. Both form strikingly similar one-dimensional hydrogen-bonding chain motifs with the DMSO solvent molecules. BIM (IIa) packs into double layers of chains whose orientations alternate every double layer, while (IIb) forms more simply packed chains along the a axis. BIM (IIa) has a remarkably long c axis.

Effects of Dual Solvents on the Electrolyte Properties of LiNO3/G4-Based Electrolyte for Li-Air Batteries

Lithium (Li)-air (O2) batteries (LABs) have been expected to be used for electric vehicles because of the high theoretical energy density of ca. 3500 Wh kg-1. However, there are some problems in the practical use, i.e. Li dendrite growth at Li metal negative electrode (NE), high overpotential during discharge process, etc. Recently, to solve these problems, LiNO3/ tetraglyme (G4)-based electrolytes were studied because of the bi-functional effects of surface oxidation for Li metal NE [1] and Li2O2 decomposition mediator at air electrode [2] by the NO3 -. However, the LiNO3 salt is quite low dissociation degree in G4 solvent, which causes to low ionic conductivity. In this study, we mixed dimethyl sulfoxide (DMSO) or acetonitrile (AN) with high dielectric constant e and low viscosity h as binary solvent to 1.0 M LiNO3/G4 electrolyte and investigated the effects on the electrolyte properties and LAB cell performance. G4 (< 30 ppm H2O) and AN or DMSO were mixed at the volume ratio of 9:1, 7:3 and 5:5, and 1.0 M LiNO3/G4+X (X =DMSO, AN) was prepared by dissolution of LiNO3 as supporting salt in an Ar filled dry box. The viscosity η and ionic conductivity σ were measured. The self-diffusion coefficient D of ions and solvents were evaluated by a PGSE-NMR [3]. The dissociation degree of Li salt was evaluated by using a Raman spectroscopy and Walden plot. Discharge/charge properties were also tested by using LAB cells using the electrolytes to discuss the effect of dual solvent. The η values of 1.0 M LiNO3/G4+X (DMSO, AN) decreased with increase in the content of dual solvents especially for AN because of the lower viscosity (0.37 mPa s) than that of DMSO (2.0 mPa s). However, DMSO-mixed electrolytes exhibited a similar increase in the σ value as well as AN mixed ones. Namely, the Li salt dissociation was assumed to be enhanced by the high e value (47) of DMSO. Fig. 1 shows the Raman spectra for the dual solvent electrolytes. In fact, the peak corresponding [Li+-(G4)] complex, i.e. Li+ solvation structure of G4, at 870 cm-1 disappeared for the DMSO-mixed electrolyte, indicating the strong interaction with DMSO solvent molecules compared with G4 ones. Walden plots exhibited and supported the enhancement of Li salt dissociation. Therefore, the DMSO and AN mixing as binary solvent was effective to increase in the number and mobility of carrier ions, respectively. Fig. 2 shows the discharge/charge properties of LAB cells using the 1.0 M LiNO3/G4+X (X = DMSO, AN, vol. ratio = 5:5). The both dual electrolytes successfully reduced the overpotential during discharge process. Especially for the DMSO-mixing a significant effect was achieved owing to the good supplying rate of NO3 - as mediator to the air-electrode. The effects for the dual solvent system in more detail, e.g. stability of the DMSO and AN in the dual electrolytes will be also reported at the meeting. This study was supported by JST Project “ALCA-SPRING”, Japan. [1] J. Uddin et al., J. Phys. Chem., 4, 3760 (2013). [2] D. Sharon et al., ACS Appl. Mater. Interfaces, 7, 16590, (2015). [3] M. Saito et al., RSC Adv., 7, 49031-49040 ,(2017). Figure 1

Electronic structure, pore size distribution, and sorption characterization of an unusual MOF, {[Ni(dpbz)][Ni(CN)4]}n, dpbz = 1,4-bis(4-pyridyl)benzene

The monoclinic (Ni(L)[Ni(CN)4] (L= 1,4-Bis(4-pyridyl) benzene) compound (defined as Ni-dpbz) is a flexible metal organic framework which assumes a pillared structure with layers defined by 2D Ni[Ni(CN)4]n nets and dpbz ligands as pillars. The structure features an entrapped dpbz ligand that links between the open ends of four-fold Ni sites from two neighboring chains. This arrangement results in an unusual 5-fold pseudo square-pyramid environment for Ni and a significantly long Ni-N distance of 2.369(4) Å. Using Density Functional Theory calculations, the different bonding characteristics between the 5-fold and 6-fold Ni's were determined. We found that there is weak covalent bonding between the 5-fold Ni and N in the entrapped ligand, and the 6-fold Ni-N bonds provide effective electronic conduction. The disordered dimethyl sulfoxide (DMSO) solvent molecules are not bonded to the framework. The material has a single pore with a diameter of 4.1 Å. This pore includes approximately 55% of the total free volume (based on a zero-diameter probe). The accessible pore surface area and pore volume were calculated to be 507 m2/g and 6.99 cm3/kg, respectively. The maximum amount of CO2 that can be accommodated in the pores after DMSO is removed was found to be 204 mg/g, agreeing with the results of adsorption/desorption experiments of about 220 mg/g.

(E)-7-[(4-Nitro-phen-yl)diazen-yl]-3a-(p-tol-yl)-2,3,3a,4-tetra-hydro-1H-benzo[d]pyrrolo-[1,2-a]imidazol-1-one 0.58-dimethyl sulfoxide 0.42-aceto-nitrile solvate: crystal structure, Hirshfeld analysis and DFT estimation of the energy of inter-molecular inter-actions.

In the crystal structure of the title compound, C23H19N5O3·0.58C2H6OS·0.42C2H3N, prepared by the azo coupling of the 4-nitro-phenyl-diazo-nium salt with 3a-(p-tol-yl)-2,3,3a,4-tetra-hydro-1H-benzo[d]pyrrolo-[1,2-a]imidazol-1-one, the azo mol-ecules are linked by N-H⋯O hydrogen bonds into chains along the a-axis direction, and by the π-π inter-action into [101] chains. The dimethyl sulfoxide and aceto-nitrile solvent mol-ecules occupy the same positions, with populations of 0.585 (3) and 0.415 (3), respectively. These mol-ecules take part in C-H⋯O(N) and C-H⋯π contacts. The energy of the π-π inter-actions was estimated using DFT calculations. The Hirshfeld mol-ecular surface analysis revealed the positions of the most important inter-molecular contacts, such as hydrogen bonds and π-π inter-actions.

Lithium‐Oxygen Batteries: Stabilization of Li Metal Anode in DMSO‐Based Electrolytes via Optimization of Salt–Solvent Coordination for Li–O2 Batteries (Adv. Energy Mater. 14/2017)

In article number 1602605, a new approach to enhance the cycling stability of Li-O2 batteries with dimethyl sulfoxide (DMSO) based electrolyte is developed by Wu Xu, Ji-Guang Zhang, and co-workers. It is found that the LiTFSI-3DMSO electrolyte exhibits an optimal concentration in which only most stable TFSI−–Li+–(DMSO)3 complexes exist but Li+–(DMSO)4 solvates and free DMSO solvent molecules are absent. This electrolyte significantly enhances the stability of both Li metal anodes and carbon-based airelectrode. The finding on the fundamental stability of the electrolyte in the absence of free-solvent against the chemical and electrochemical reactions can also be used to enhance the stability of other electrochemical systems.

Crystal structure, spectral property, antimicrobial activity and DFT calculation of N-(coumarin-3-yl)-N′-(2-amino-5-phenyl-1,3,4-thiadiazol-2-yl) urea

N-(coumarin-3-yl)-N′-(2-amino-5-phenyl-1,3,4-thiadiazol-2-yl) urea was synthesized and characterized by elemental analysis, IR, 1H NMR, 13C NMR, UV–Vis and emission spectroscopy, as well as by single-crystal X-ray diffraction. X-ray crystallographic analyses have indicated that the crystal structure consists of two dimethyl sulfoxide (DMSO) solvent molecules and the structural geometry of DMSO is a trigonal pyramid in shape. In the crystal structure, a self-assembling two-dimensional (2-D) layer supramolecular architecture is formed through intermolecular hydrogen bonds, CO···π (thiadiazole ring) and π···π stacking interactions. The geometry of the compound has been optimized by the DFT method and the results are compared with the X-ray diffraction data. The electronic transitions and spectral features of the compound were carried out by using DFT/B3LYP method. In addition, the antimicrobial activity was also studied, and the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), and HOMO-LUMO gap were also calculated.

Stabilization of Li Metal Anode in DMSO‐Based Electrolytes via Optimization of Salt–Solvent Coordination for Li–O2 Batteries

The conventional electrolyte of 1 m lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) in dimethyl sulfoxide (DMSO) is unstable against the Li metal anode and therefore cannot be used directly in practical Li–O2 batteries. Here, we demonstrate that a highly concentrated electrolyte based on LiTFSI in DMSO (with a molar ratio of 1:3) can greatly improve the stability of the Li metal anode against DMSO and significantly improve the cycling stability of Li–O2 batteries. This highly concentrated electrolyte contains no free DMSO solvent molecules, but only complexes of (TFSI−)aLi+(DMSO)b (where a + b = 4), and thus enhances their stability with Li metal anodes. In addition, such salt–solvent complexes have higher Gibbs activation energy barriers than the free DMSO solvent molecules, indicating improved stability of the electrolyte against the attack of superoxide radical anions. Therefore, the stability of this highly concentrated electrolyte at both Li metal anodes and carbon‐based air electrodes has been greatly enhanced, resulting in improved cycling performance of Li–O2 batteries. The fundamental stability of the electrolyte in the absence of free‐solvent against the chemical and electrochemical reactions can also be used to enhance the stability of other electrochemical systems.

4-Amino-3-[2-(9H-carbazol-9-yl)ethyl]-1H-1,2,4-triazole-5(4H)-thione dimethyl sulfoxide monosolvate

In the crystal of the title compound, C16H15N5S·C2H6OS, both the 1,2,4-triazole derivative molecules and the disordered [refined occupancy ratio = 0.604 (1):0.396 (1)] dimethyl sulfoxide solvent molecules form centrosymmetric dimers, by way of pairwise N—H...S and C—H...O hydrogen bonds, respectively. In the crystal, the two types of dimer are connected by N—H...O hydrogen bonds, forming infinite chains parallel to [101]. The packing is assisted by π–π stacking and C—H...π(ring) and N—H...π(ring) interactions.

2-(5-Bromo-1H-indol-3-yl)-4-(4-bromophenyl)-5-(4-chlorobenzoyl)-1H-pyrrole-3-carbonitrile dimethyl sulfoxide monosolvate

In the title solvated compound, C26H14Br2ClN3O·C2H6OS, the indole ring is inclined to the central pyrrole ring by 25.7 (2)°. The chlorobenzene ring and the bromobenzene rings subtend dihedral angles of 56.5 (2) and 53.4 (2)°, respectively, with the central pyrrole ring. In the crystal, molecules are bridged by N—H...O hydrogen bonds, involving the dimethyl sulfoxide solvent molecule, forming chains along [010]. There are no other significant intermolecular interactions present.

Solvent-molecule-mediated manipulation of crystalline grains for efficient planar binary lead and tin triiodide perovskite solar cells.

Binary lead and tin perovskites offer the benefits of narrower band gaps for broader adsorption of solar spectrum and better charge transport for higher photocurrent density. Here, we report the growth of large, smooth crystalline grains of bianry lead and tin triiodide perovskite films via a two-step solution process with thermal plus solvent vapor-assisted thermal annealing. The crystalline SnxPb1-xI2 films formed in the first step served as the templates for the formation of crystalline CH3NH3SnxPb1-xI3 films during the second step interdiffusion of methylammonium iodide (MAI). Followed by dimethylsulfoxide (DMSO) vapor-assisted thermal annealing, small, faceted perovskite grains grew into large, smooth grains via the possible mechanism involving bond breaking and reforming mediated by DMSO solvent molecules. The absorption onset was extended to 950 and 1010 nm for the CH3NH3SnxPb1-xI3 perovskites with x = 0.1 and 0.25, respectively. The highest PCE of 10.25% was achieved from the planar perovskite solar cell with the CH3NH3Sn0.1Pb0.9I3 layer prepared via the thermal plus DMSO vapor-assisted thermal annealing. This research provides a way to control and manipulate film morphology, grain size, and especially the distribution of metal cations in binary metal perovskite layers, which opens an avenue to grow perovskite materials with desired properties to enhance device performance.

Synthesis and structural characterization of a flexible metal organic framework {[Ni(dpbz)][Ni(CN)4]}n, dpbz = 1,4-bis(4-pyridyl)benzene) with an unusual Ni–N bond

The chartreuse monoclinic Ni-dpbz (Ni(L)[Ni(CN)4], (L = 1,4-Bis(4-pyridyl)benzene, or dpbz) crystal assumes a pillared structure with layers defined by 2-D Ni[Ni(CN)4]n nets and dpbz ligands as pillars, linking between coordinated Ni sites. In addition to the hysteretic adsorption/desorption feature of Ni-dpbz, in half of the parallelepiped-shape space enclosed by the pillars and nets, an additional dpbz ligand was found to link between the open ends of two four-fold Ni sites. This arrangement results in an unusual 5-fold pseudo square-pyramid environment for Ni and a significantly long Ni–N distance of 2.369(4) Å. The presence of disordered dimethyl sulfoxide (DMSO) solvent molecules give rise to the formula of Ni(dpbz)[Ni(CN)4]·½dpbz·0.44DMSO. Sorption isotherms showed flexible behavior during the adsorption and desorption of CO2.

Atomistic Modeling of the Charge Process in Lithium/Air Batteries

We present a combined classical and density functional theory (DFT) based Molecular Dynamics (MD) study of the mechanisms underlying the oxygen evolution reactions during the charging of lithium/air batteries. As models for the Li2O2 material at the cathode we employ small amorphous clusters with a 2:2 Li:O stoichiometry, whose energetically most stable atomic configurations comprise both O atoms and O–O pairs with mixed peroxide/superoxide character, as revealed by their bond lengths, charges, spin moments, and densities of states. The oxidation of Li8O8 clusters is studied in unbiased DFT-based MD simulations upon removal of either one or two electrons, either in vacuo or immersed in dimethyl sulfoxide solvent molecules with a structure previously optimized by means of classical MD. Whereas removal of one electron leads only to an enhancement of the superoxide character of O–O bonds, removal of two electrons leads to the spontaneous dissolution of either an O2 or a LiO2+ molecule. These results are inte...

Density Functional Theory (DFT) Study for Role of Ion-Conducting Lithium Salts Regarding the Oxygen Reduction Reaction (ORR) Kinetics in Li-air (O2) Batteries

Density functional theory calculations are performed to investigate the role of lithium salts regarding the oxygen reduction reaction (ORR) occurred in non-aqueous electrolyte in Li-air batteries. This study is useful to elucidate the influence of ion-conducting lithium salts on ORR kinetics. The Li+-O bonding, binding energy, Gibb's free energy, heat of formation energy, and IR spectra with increase in dimethyl sulfoxide (DMSO) solvent molecules in the primary solvation shell reveal that lithium trifluoromethanesulfonate (LiCF3SO3) is the most stable in dimethyl sulfoxide (DMSO) as compared to lithium hexafluorophosphate (LiPF6) and lithium bis(trifluoromethanesulfonimide (LiN(CF3SO2)2). Infrared spectroscopic (IR) data confirm the formation of lithium peroxide (Li2O2), lithium oxide (Li2O), and lithium carbonate (Li2CO3) as discharge products on the micro-electrode surface in non-aqueous electrolyte containing lithium salts. The infrared (IR) analysis reveals that the lithium trifluoromethanesulfonate/dimethyl sulfoxide (LiCF3SO3/DMSO) electrolyte is primarily assumed to be the most favorable for ORR kinetics. In order to study the kinetics of oxygen reduction reaction at the oxygen cathode of non-aqueous Li-air battery with three Li salts in dimethyl sulfoxide (DMSO), we calculate thermodynamic properties of the reactions held during the formation of lithium peroxide (Li2O2) and lithium oxide (Li2O). The Gibb's energy and heat of formation of these reactions indicate that lithium trifluoromethanesulfonate/dimethyl sulfoxide (LiCF3SO3/DMSO) electrolyte plays a key role in oxygen reduction reaction mechanism compared to other two.

Crystal structure of (2Z)-2-{(5Z)-5-[3-fluoro-2-(4-phenyl-piperidin-1-yl)benzyl-idene]-4-oxo-3-(p-tol-yl)-1,3-thia-zolidin-2-yl-idene}-N-(p-tol-yl)ethane-thio-amide dimethyl sulfoxide monosolvate.

The title compound, C37H34FN3OS2·C2H6OS, was obtained by the Knoevenagel condensation. The thia­zolidine ring is essentially planar (r.m.s. deviation = 0.025 Å) and forms dihedral angles of 4.2 (3), 68.60 (14) and 39.57 (15)° with the attached thio­amide group, p-tolyl group benzene ring and fluoro-substituted benzene ring, respectively. The exocyclic double bonds are in a Z configuration. In the crystal, the dimethyl sulfoxide solvent mol­ecule is connected to the main mol­ecule via an N—H⋯O hydrogen bond. Weak C—H⋯O hydrogen bonds link the components of the structure into a two-dimensional network parallel to (10-1). Weak intra­molecular C—H⋯S hydrogen bonds are also observed. The crystal is an inversion twin with a ratio of twin components 0.78 (2):0.22 (6).