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1.  2-Methyl-5-[(3-methyl-4-nitro­benz­yl)sulfan­yl]-1,3,4-thia­diazole 
The mol­ecule of the title thia­diazole derivative, C11H11N3O2S2, has a butterfly-like structure and the whole mol­ecule is disordered with a site-occupancy ratio of 0.629 (4):0.371 (4). The mol­ecule is disordered in such a way that the 3-methyl-4-nitro­phenyl units of the major and minor components are approximately related by 180° rotation around the C—N bond axis. The dihedral angle between the 1,3,4-thia­diazole and benzene rings is 70.8 (4)° in the major component and 74.9 (6)° in the minor component. In the crystal, mol­ecules are arranged into screw chains along the c axis. These chains are stacked along the b axis. Weak inter­molecular C—H⋯O and C—H⋯π inter­actions and a short C⋯O contact [3.005 (7) Å] are present.
PMCID: PMC3050181  PMID: 21522706
2.  5-(4-Bromo­phen­yl)-2-(3,4-methyl­ene­dioxy­phen­yl)-3-methyl­sulfanyl-1-benzofuran 
The title compound, C22H15BrO3S, crystallizes with four mol­ecules in the asymmetric unit. The 4-bromo­phenyl rings are rotated out of the benzofuran planes, with dihedral angles for the four mol­ecules of 20.8 (2), 17.8 (2), 23.5 (4) and 23.9 (4)°. The dihedral angles between the 3,4-methyl­ene­dioxy­phenyl ring and the benzofuran plane are 13.5 (2), 7.1 (2), 18.6 (3) and 14.2 (3)° in the four mol­ecules. The crystal structure is stabilized by weak nonclassical inter­molecular C—H⋯O hydrogen bonds. The crystal structure also exhibits inter­molecular aromatic π–π inter­actions between the benzene and furan rings and between the 4-bromo­phenyl and 3,4-methyl­enedioxy­phenyl rings from mol­ecules of the same type; the centroid–centroid distances are 3.92 (1) and 3.79 (1), 3.91 (1), 3.77 (1) and 3.77 (1), and 3.79 (1) and 3.75 (1)Å in the four mol­ecules.
PMCID: PMC2970320  PMID: 21577975
3.  Crystal structure of 1-methyl-4-methyl­sulfanyl-1H-pyrazolo­[3,4-d]pyrimidine 
In the title compound, C7H8N4S, the non-H atoms of the pyrazolo­[3,4-d]pyrimidine ring system and the methyl­sulfanyl group lie on a crystallographic mirror plane. In the crystal, mol­ecules are linked via a number of π–π inter­actions [centroid–centroid distances vary from 3.452 (7) to 3.6062 (8) Å], forming a three-dimensional structure.
PMCID: PMC4257437  PMID: 25553046
crystal structure; 1H-pyrazolo­[3,4-d]pyrimidine; pharmacol­ogical and biochemical properties; π–π inter­actions
4.  (E)-5-(3,5-Dimethyl­phen­yl)-N-[4-(methyl­sulfan­yl)benzyl­idene]-1,3,4-thia­diazol-2-amine 
The title compound, C18H17N3S2, was synthesized by the reaction of 5-(3,5-dimethyl­phen­yl)-1,3,4-thia­diazol-2-amine and 4-(methyl­sulfan­yl)benzaldehyde. An intra­molecular C—H⋯S hydrogen bond results in the formation of a planar (r.m.s. deviation = 0.003 Å) five-membered ring. In the crystal structure, inter­molecular C—H⋯N hydrogen bonds link the mol­ecules to form layers parallel to (011).
PMCID: PMC2979762  PMID: 21579829
5.  2-Methyl­sulfanyl-9H-1,3,4-thia­diazolo[2,3-b]quinazolin-9-one 
In the title compound, C10H7N3OS2, the 16 non-H atoms are almost planar (r.m.s. deviation = 0.037 Å) and the S-bound methyl group is syn to the ketone O atom. In the crystal, centrosymmetrically related mol­ecules are connected by pairs of C—H⋯O inter­actions between the ketone O and methyl H atoms. The dimeric aggregates are connected into a linear supra­molecular chain along the b axis via π–π inter­actions occurring between the five-membered and benzene rings [centroid–centroid distance = 3.6123 (9) Å]. The chains assemble into layers in the bc plane via S⋯S inter­actions involving the endocyclic S atoms [S⋯S = 3.4607 (6) and 3.4792 (6) Å].
PMCID: PMC3393945  PMID: 22798810
6.  7-[4-(4-Fluoro­phen­yl)-2-methyl­sulfanyl-1H-imidazol-5-yl]tetra­zolo[1,5-a]pyridine 
The crystal structure of the title compound, C15H11FN6S, forms a three-dimensional network stabilized by π–π inter­actions between the imidazole core and the tetra­zole ring of the tetra­zolopyridine­unit; the centroid–centroid distance is 3.627 (1) Å. The crystal structure also displays bifurcated N—H⋯(N,N) hydrogen bonding and C—H⋯F inter­actions. The former involve the NH H atom of the imidazole core and the tetra­zolopyridine N atoms, while the latter involve a methyl H atom, of the methyl­sulfanyl group, and the 4-fluoro­phenyl F atom. In the mol­ecule, the imidazole ring makes dihedral angles of 40.45 (9) and 17.09 (8)°, respectively, with the 4-fluoro­phenyl ring and the tetra­zolopyridine ring mean plane.
PMCID: PMC2979910  PMID: 21579866
7.  2-Methyl­sulfanyl-1,2,4-triazolo[1,5-a]quinazoline-5(4H)-thione 
In the title compound, C10H8N4S2, comprising fused six-, six- and five-membered rings, the mol­ecule is close to being planar (r.m.s. deviation of the non-H atoms = 0.041 Å). The S-bound methyl group is folded away from the single N atom of the triazole ring and the NH group of the six-membered ring, allowing for the formation of centrosymmetric eight-membered {⋯HNCN}2 synthons in the crystal. The resulting inversion dimers are connected into supra­molecular stacks aligned along the b-axis direction by π–π inter­actions [centroid–centroid distances = 3.6531 (12) and 3.7182 (12) Å].
PMCID: PMC3588520  PMID: 23476605
8.  (OC-6-33)-(2,2′-Bipyridine-κ2 N,N′)trimeth­yl(2-methyl­sulfanyl-2-thia­zoline-κN)platinum(IV) tetra­fluoridoborate 
The asymmetric unit of the title complex, [Pt(CH3)3(C10H8N2)(C4H7NS2)]BF4, contains two crystallographically independent mol­ecules. The PtIV atom in each complex cation exhibits a distorted octa­hedral coordination geometry, built up by three methyl ligands in a facial binding fashion, a bipyridine ligand and a monodentately N-bound 2-methyl­sulfanyl-2-thia­zoline ligand (configuration index: OC-6–33). In the crystal structure, weak inter­molecular C—H⋯F hydrogen bonds are found between the complex cations and BF4 − anions.
PMCID: PMC3007407  PMID: 21588173
9.  2-(5-Isopropyl-3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid 
There are two mol­ecules in the asymmetric unit of the title compound, C14H16O3S. In the crystal structure, the carboxyl groups are involved in inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further packed into stacks along the a axis by aromatic π–π inter­actions between the furan rings of adjacent mol­ecules [centroid–centroid distance = 3.430 (4) Å] and by additional C—H⋯π and C—H⋯O inter­actions.
PMCID: PMC2969340  PMID: 21582817
10.  1,2-Bis[1-(3-methyl­sulfanyl-1,2,4-triazin-5-yl)ethyl­idene]diazane 
The mol­ecule of the title compound, C12H14N8S2, has an N—N gauche conformation. The triazine rings are nearly coplanar with respect to the imide bonds [C—C—C—N torsion angles = −15.3 (3) and −15.8 (3)°] and they are twisted by 77.88 (7)°. The overall conformation of the mol­ecule is stabilized by intra­molecular C—H⋯N hydrogen bonding. The mol­ecular packing is influenced by π–π inter­actions of the triazine systems with a shortest centroid–centroid separation of 3.5242 (12) Å.
PMCID: PMC2977495  PMID: 21583480
11.  6-Methyl­sulfanyl-4H-pyrimido[1,6-a]pyrimidin-4-one 
Reaction of 2-(methyl­sulfan­yl)pyrimidin-4-amine with the 5-(methoxy­vinyl­idene) derivative of Meldrum’s acid and subsequent heating of the product in Dowtherm fluid yielded the title compound, C8H7N3OS, which was proven to contain a bicyclic 4H-pyrimido[1,6-a]pyrimidine system. All non-H atoms of the mol­ecule are coplanar within 0.15 Å. The bond-length distribution in the bicyclic core shows localization of the double bonds. The geometry of the intra­molecular S⋯O 1,5-contact [2.534 (2) Å] is consistent with the existence of an attractive inter­action.
PMCID: PMC2970259  PMID: 21578009
12.  (2Z)-2-Fluoro-N-{4-[5-(4-fluoro­phen­yl)-2-methyl­sulfanyl-1H-imidazol-4-yl]-2-pyrid­yl}-3-phenyl­acrylamide 
The asymmetric unit of the title compound, C24H18F2N4OS, contains two crystallographically independent mol­ecules, A and B, which are linked into two chains of A and B mol­ecules by inter­molecular N—H⋯O hydrogen bonds. The three-dimensional network is stabilized by π–π inter­actions between the pyridine rings and phenyl rings of different residues, with centroid–centroid distances of 3.793 (1) and 3.666 (2) Å. The mol­ecular conformation is stabilized by intra­molecular N—H⋯F hydrogen bonds (2.15/2.15Å). The imidazole rings make dihedral angles of 39.5 (2)/38.5 (2) and 31.8 (2)/33.2 (2)° with the 4-fluoro­phenyl rings and the pyridine rings, respectively. The methyl group of molecule A is disorderd in a 0.60:0.40 ratio.
PMCID: PMC2971986  PMID: 21578977
13.  N-(5-Benzyl­sulfanyl-1,3,4-thia­diazol-2-yl)-2-(piperidin-1-yl)acetamide 
The title compound, C16H20N4OS2, was synthesized by the reaction of 2-benzyl­sulfanyl-5-chloro­acetamido-1,3,4-thia­diazole and piperidine in a 1:2 ratio. The planes of the acetamide and 1,3,4-thia­diazole units are twisted by 10.8 (4)°. The thia­diazole S atom and the acetamide O atom are syn-oriented due to a hypervalent S⋯O inter­action of 2.628 (4) Å. In the crystal, mol­ecules form centrosymmetric dimers via N—H⋯N hydrogen bonds. These dimers are further connected by C—H⋯O inter­actions into (100) layers.
PMCID: PMC3998473  PMID: 24764962
14.  2-(5-Cyclo­hexyl-3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid 
In the title compound, C17H20O3S, the cyclo­hexyl ring adopts a chair conformation. In the crystal, the carboxyl groups are involved in inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further stabilized by weak inter­molecular C—H⋯O hydrogen bonds. In addition, the crystal structure also exhibits aromatic π–π inter­actions between the furan rings of adjacent mol­ecules [centroid–centroid distance = 3.505 (2) Å, inter­planar distance = 3.385 (2) Å and slippage = 0.909 (2) Å], and inter­molecular C—H⋯π inter­actions.
PMCID: PMC3212340  PMID: 22090997
15.  1-(5-Benzyl­sulfanyl-2,2-dimethyl-2,3-dihydro-1,3,4-thia­diazol-3-yl)-2,2-dimethyl­propan-1-one 
In the title compound, C16H22N2OS2, the S atom of the thia­diazole ring and the attached methyl groups are disordered over two orientations with a refined site-occupancy ratio of 0.641 (11):0.359 (11). The thia­diazole ring is in a twist conformation in both disorder components. The mean plane through the thia­diazole ring makes dihedral angles of 77.39 (8) (major component) and 67.45 (11)° (minor component) with the benzene ring. Intra­molecular C—H⋯N inter­actions generate two S(6) ring motifs. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into zigzag chains parallel to the b axis.
PMCID: PMC3344160  PMID: 22606163
16.  1-Methyl-2-methyl­sulfanyl-6-nitro-1H-benzimidazole 
The mol­ecule of the title compound, C9H9N3O2S, is built up from fused five- and six-membered rings connected to methyl­sulfanyl and nitro groups, respectively. The mean plane through the fused ring system is inclined slightly relative to the plane passing through the nitro group [dihedral angle = 3.6 (2)°]. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds and π–π inter­actions between imidazole rings [inter-centroid distance = 3.667 (3) Å], forming a three-dimensional network.
PMCID: PMC3998622  PMID: 24826123
17.  Crystal structure of 2-amino-5-methyl­sulfanyl-1,3,4-thia­diazol-3-ium chloride monohydrate 
The title salt, C3H6N3S2 +·Cl−·H2O, crystallized with two organic cations, two chloride anions and two water mol­ecules in the asymmetric unit. The methyl C atoms deviate from their respective bound ring planes by 0.081 and 0.002 Å. In the crystal, the components are connected via N—H⋯O, N—H⋯Cl and O—H⋯Cl hydrogen bonds, forming sheets lying parallel to (100). The sheets are linked into bilayers by O—H⋯Cl hydrogen bonds involving the chloride ions and water mol­ecules. Within the bilayers there are π–π inter­actions [inter-centroid distances = 3.4654 (4) and 3.4789 (4) Å] involving inversion-related cations.
PMCID: PMC4186122  PMID: 25309249
crystal structure; 1,3,4-thia­diazole; biological activity; organic-inorganic hybrid
18.  1-Tosyl-2-[(1-tosyl-1H-benzimidazol-2-yl)methyl­sulfanyl]-1H-benzimidazole 
In the title compound, C29H24N4O4S3, the two N-tosyl­benzimidazolyl unit are connected through a —S—CH2— fragment, the dihedral angle between the benzimidazole rings being 76.09 (5)°. The methyl­thio group is disordered with respect to exchange of the S and C atoms in a 0.547 (4):0.453 (4) ratio. In the crystal, C—H⋯O and C—H⋯π inter­actions connect adjacent mol­ecules into infinite layers parallel to the ab plane. The crystal packing is further stabilized by a π–π inter­action [centroid–centroid separation = 3.5187 (4) Å].
PMCID: PMC3089064  PMID: 21754370
19.  2-(4-Methyl­phen­yl)-5-[({[5-(4-methyl­phen­yl)-1,3,4-thia­diazol-2-yl]sulfan­yl}meth­yl)sulfan­yl]-1,3,4-thia­diazole 
In the title compound, C19H16N4S4, the mol­ecules exhibit a butterfly conformation, where the thia­diazole and attached benzene rings in two wings are almost coplanar, with dihedral angles of 0.8 (3) and 0.9 (3)°, respectively, while the two thia­diazole rings form a dihedral angle of 46.3 (3)°.
PMCID: PMC3297906  PMID: 22412709
20.  2-(5-Bromo-3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid 
The title compound, C11H9BrO3S, was prepared by alkaline hydrolysis of ethyl 2-(5-bromo-3-methyl­sulfanyl-1-benzofuran-2-yl)acetate. In the crystal structure, the carboxyl groups are involved in inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further packed into stacks along the c axis by weak C—H⋯π inter­actions. In addition, the stacked mol­ecules exhibit a Br⋯S inter­action of 3.4787 (7) Å.
PMCID: PMC2968485  PMID: 21582220
21.  (3aR*,8bR*)-3a,8b-Dihy­droxy-1-(4-methyl­phen­yl)-2-methyl­sulfanyl-3-nitro-1,8b-di­hydro­indeno­[1,2-b]pyrrol-4(3aH)-one 
The asymmetric unit of the title compound, C19H16N2O5S, contains four independent mol­ecules (A, B, C and D), with two mol­ecules (B and D) displaying disorder in their methyl­sulfanyl groups [occupancy ratios of 0.797 (11):0.203 (11) and 0.85 (2):0.15 (2)]. The nitro groups are twisted slightly out of the planes of the 2-pyrroline rings to which they are bonded with dihedral angles of 10.17 (1), 8.01 (1), 9.44 (1) and 8.87 (1)° in mol­ecules A, B, C and D, respectively. The 2-pyrroline rings are almost orthogonal to the attached tolyl rings, forming dihedral angles of 73.44 (1), 81.21 (1), 88.18 (8) and 73.94 (1)° for mol­ecules A, B, C and D, respectively. A weak intra­molecular O—H⋯O inter­action is observed in mol­ecules B and C. The two hy­droxy groups in each mol­ecule are involved in inter­molecular O—H⋯O hydrogen bonding. In the crystal, mol­ecules are connected via O—H⋯O and C—H⋯O hydrogen bonds, forming a complex three-dimensional network.
PMCID: PMC3998437  PMID: 24764991
22.  (R)-4-[2-(Methyl­sulfanyl)pyrimidin-4-yl]-1-(tetra­hydro­furan-3-yl)-1H-pyrazol-5-amine 
The title compound, C12H15N5OS, was obtained by reaction of 2-(2-(methyl­thio)pyrimidin-4-yl)-3-oxopropane­nitrile with (tetra­hydro­furan-3-yl)hydrazine dihydro­chloride, and the racemic product was subsequently separated by chiral chromatography (first peak; [α]D 20 = +51.3°). The chiral center at the substituted atom of the tetra­hydro­furanyl group has an R-configuration. The pyrimidine and pyrazolyl rings are almost coplanar, their mean planes forming a dihedral angle of 6.4 (1)°. One of the H atoms of the amino group participates in an intra­molecular hydrogen bond with the pyrimidine N atom in position 3. The second H atom is involved in an inter­molecular hydrogen bond, which links the mol­ecules into an infinite chain.
PMCID: PMC2968870  PMID: 21582437
23.  6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazen­yl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione–1-methyl­pyrrolidin-2-one–water (1/1/1) 
In the title compound, C13H16N10O2S·C5H9NO·H2O, the entire 1-methylpyrrolidin-2-one (NMP) mol­ecule is disordered over two sites with occupancies of 0.488 (5) and 0.512 (5). The six-membered triazine ring and the two five-membered pyrazole and thiadia­zole rings, together with the diazene (–N=N–) linkage are almost coplanar (r.m.s. deviation for the non-H atoms = 0.0256 Å) with methyl groups from the tert-butyl substituent on the pyrazole ring located above and below the plane. Three intra­molecular N—H⋯N hydrogen bonds contribute to the planarity of the system. The O atom of the NMP mol­ecule is hydrogen bonded to an O—H group of water. In turn, the water mol­ecule is hydrogen bonded to the mono-azo skeleton through inter­molecular N—H⋯O and O—H⋯N hydrogen bonds. At both ends of the long mol­ecular axis of the main mol­ecule there are inter­molecular N—H⋯N hydrogen bonds, arranged in a head-to-tail fashion, between the N—H group of the triazine ring of one mol­ecule and the N atom of the thia­diazole ring of a neighboring mol­ecule. These form a polymeric chain along [110] or [10]. The main mol­ecules are stacked alternately along the b axis, which effectively cancels their dipole moments. In addition, pairs of alternate molecules are dimerized via inter­molecular hydrogen bonds involving the solvent mol­ecules.
PMCID: PMC2983887  PMID: 21580749
24.  2,5-Bis[(3-chloro­benz­yl)sulfan­yl]-1,3,4-thia­diazole 
The complete mol­ecule of the title compound, C16H12Cl2N2S3, is generated by crystallographic twofold symmetry, with the S atom of the thiadiazole ring lying on the rotation axis. The dihedral angle between the mean planes of the 1,3,4-thia­diazole and benzene rings is 87.19 (7)°. In the crystal, mol­ecules are linked by C—H⋯N inter­actions and short S⋯S contacts [3.3389 (9) Å] occur.
PMCID: PMC3379226  PMID: 22719424
25.  2-(5-Fluoro-3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid 
The title compound, C11H9FO3S, was prepared by alkaline hydrolysis of ethyl 2-(5-fluoro-3-methyl­sulfanyl-1-benzofuran-2-yl)acetate. In the crystal structure, the carboxyl groups are involved in inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by inter­molecular C—H⋯O and C—H⋯F inter­actions.
PMCID: PMC2977173  PMID: 21583516

Results 1-25 (565387)