PMCC PMCC

Search tips
Search criteria

Advanced
Results 1-25 (571013)

Clipboard (0)
None

Related Articles

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.
doi:10.1107/S1600536810052505
PMCID: PMC3050181  PMID: 21522706
2.  5-[(4-Meth­oxy­benz­yl)sulfan­yl]-2-methyl-1,3,4-thia­diazole 
The title mol­ecule, C11H12N2OS2, is twisted with a dihedral angle of 83.63 (12)° between the 1,3,4-thia­diazole and benzene rings. The meth­oxy group deviates slightly from the attached benzene ring, with a C—C—O—C torsion angle of 4.2 (4)°. In the crystal, mol­ecules are linked by weak C—H⋯N inter­actions and stacked along the c axis.
doi:10.1107/S1600536810051858
PMCID: PMC3050388  PMID: 21522670
3.  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.
doi:10.1107/S1600536812012639
PMCID: PMC3344160  PMID: 22606163
4.  1-Methyl-4-({5-[(4-methyl­phen­yl)sulfan­yl]pent­yl}sulfan­yl)benzene 
There are two independent mol­ecules in the asymmetric unit of the title compound, C19H24S2. In both mol­ecules, the aliphatic segment of the ligand is in an all-trans conformation: the –S–(CH2)5–S–bridging chain is almost planar (r.m.s. deviation for all non-H atoms = 0.0393 and 0.0796 Å in the two mol­ecules) and maximally extended. Their mean planes form dihedral angles of 4.08 (6)/20.47 (6) and 2.22 (6)/58.19 (6)° with the aromatic rings in the two mol­ecules. The crystal packing is purely governed by weak inter­molecular forces.
doi:10.1107/S1600536809044870
PMCID: PMC2972162  PMID: 21578720
5.  5-({3-[(5-Amino-1,3,4-thia­diazol-2-yl)sulfanylmeth­yl]benz­yl}sulfan­yl)-1,3,4-thia­diazol-2-amine 
In the title compound, C12H12N6S4, the two terminal thia­diazole rings are twisted with respect to the central benzene ring, making dihedral angles of 54.28 (4) and 76.56 (3)°. The dihedral angle between the two thia­diazole rings is 27.77 (4)°. Inter­molecular N—H⋯N hydrogen bonds stabilize the crystal packing, linking the mol­ecules into a tape along the b axis.
doi:10.1107/S1600536812013116
PMCID: PMC3344171  PMID: 22606174
6.  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.
doi:10.1107/S1600536812019150
PMCID: PMC3379226  PMID: 22719424
7.  2-(2,4-Dichloro­phen­oxy­meth­yl)-5-(4-methyl­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole1  
In the title compound, C18H13Cl2N3OS, the eight atoms comprising the central imidazo/thia­diazo­lethia­diazole residue are coplanar (r.m.s. deviation = 0.009 Å). The dihedral angle of 8.72 (13)° between the dichloro­benzene and tolyl rings reflects a twist about the O—C(benzene) bond; the Cm—O—Cb—Cb torsion angle = −168.5 (2)° (m = methyl­ene C and b is benzene C). Supra­molecular tapes along the b axis are found in the crystal structure which are mediated by π–π inter­actions occurring between centrosymmetrically related thia­diazole rings [inter-ring centroid distance = 3.6907 (16) Å] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å].
doi:10.1107/S160053681300384X
PMCID: PMC3588533  PMID: 23476564
8.  (E)-[({[(3-Methyl­phen­yl)meth­yl]sulfan­yl}methane­thio­yl)amino](1-phenyl­pentyl­idene)amine 
In the structure of the title compound, C20H24N2S2, the central CN2S2 atoms are planar (r.m.s. deviation = 0.0205 Å) but both benzene rings are twisted out of this plane forming dihedral angles of 23.03 (6) and 84.75 (4)° (tol­yl); the n-butyl group occupies a position normal to the plane [N—C—C—C torsion angle = −84.33 (16)°]. The conformation of the imine bond [1.2888 (18) Å] is E. The syn arrangement of the thione S and amino H atoms enables the formation of N—H⋯S hydrogen bonds between centrosymmetrically related mol­ecules. These lead to eight-membered {⋯HNC=S}2 synthons which are further stabilized by proximate C—H⋯S interactions. The resulting dimeric aggregates are connected into a supra­molecular chain along the c axis by C—H⋯π(tol­yl) inter­actions.
doi:10.1107/S1600536811016965
PMCID: PMC3120291  PMID: 21754762
9.  Diethyl {(4-methoxy­phen­yl)[5-(4-nitro­phen­yl)-1,3,4-thia­diazol-2-ylamino]meth­yl}phospho­nate 
The title compound, C20H23N4O6PS, was synthesized by the reaction of N-(4-methoxy­benzyl­idene)-5-(4-nitro­phen­yl)-1,3,4-thia­diazol-2-amine and diethyl phosphite. The thia­diazole and nitro-substituted phenyl rings in the mol­ecule are approximately coplanar, the dihedral angle being 5.3 (2)°. The dihedral angle formed by the mean plane through all non-H atoms of both the thia­diazole and the nitro-substituted phenyl ring with the plane of the meth­oxy-substituted phenyl ring is 48.9 (2)°. In the crystal structure, mol­ecules form centrosymmetric dimers as a result of N—H⋯O bonds involving amine H and phosphine oxide O atoms.
doi:10.1107/S1600536808017364
PMCID: PMC2962010  PMID: 21203097
10.  3,5-Dimethyl-1-{2-[(5-methyl-1,3,4-thia­diazol-2-yl)sulfan­yl]acet­yl}-2,6-diphenylpiperidin-4-one 
In the title compound, C24H25N3O2S2, the piperidine ring adopts a distorted boat conformation. The phenyl rings subtend angles of 75.6 (1)° and 86.3 (1)° with the mean plane of the piperidine ring. In the crystal, mol­ecules are linked through a network C—H⋯N hydrogen bonds, forming zigzag chains along [100]. The thia­diazol ring methyl group is disordered over two positions with an occupancy ratio of 0.69 (4):0.31 (4).
doi:10.1107/S1600536813012014
PMCID: PMC3684930  PMID: 23795032
11.  6-(2-Methyl­phen­yl)-3-(3,4,5-trimethoxy­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole 
In the mol­ecule of the title compound, C19H18N4O3S, the planar central heterocylic ring system is oriented with respect to the trimethoxy­phenyl and 2-methyl­phenyl rings at dihedral angles of 4.43 (3) and 4.32 (3)°, respectively. The dihedral angle between the two benzene rings is 7.65 (4)°. In the crystal structure, inter­molecular C—H⋯N hydrogen bonds link the mol­ecules into centrosymmetric R 2 2(18) dimers. These dimers are connected via a C—H⋯π contact between the 2-methyl­phenyl and trimethoxy­phenyl rings, and a π–π contact between the thia­diazole and trimethoxy­phenyl rings [interplanar distance 3.51 Å, dihedral angles 4.17(4)°]. An intramolecular C—H⋯N hydrogen bond is also present.
doi:10.1107/S160053680802062X
PMCID: PMC2962111  PMID: 21203193
12.  Crystal structure of 2-meth­oxy-2-[(4-methyl­phen­yl)sulfan­yl]-1-phenyl­ethan-1-one 
In the title β-thio­carbonyl compound, C16H16O2S, the carbonyl and meth­oxy O atoms are approximately coplanar [O—C—C—O torsion angle = −18.2 (5)°] and syn to each other, and the tolyl ring is orientated to lie over them. The dihedral angle between the planes of the two rings is 44.03 (16)°. In the crystal, supra­molecular chains are formed along the c axis mediated by C—H⋯O inter­actions involving methine and methyl H atoms as donors, with the carbonyl O atom accepting both bonds; these pack with no specific inter­molecular inter­actions between them.
doi:10.1107/S205698901402550X
PMCID: PMC4331849
crystal structure; β-thio­carbon­yl; C—H⋯O inter­actions
13.  3-[5-(4-Fluoro­phen­yl)-1,3,4-thia­diazol-2-yl]-2-(4-methoxy­phen­yl)-1,3-thia­zolidin-4-one 
The title compound, C18H14FN3O2S2, was synthesized by the reaction of 5-(4-fluoro­phen­yl)-N-(4-methoxy­benzyl­idene)-1,3,4-thia­diazol-2-amine and mercaptoacetic acid. The thia­zolidinone ring adopts a twist conformation. The 4-methoxy­phenyl ring is almost perpendicular to the thia­diazole ring, making a dihedral angle of 88.4 (3)°. The 4-fluoro­phenyl ring is nearly coplanar with the thia­diazole ring, the dihedral angle being 6.8 (3)°. The crystal structure involves C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds.
doi:10.1107/S1600536808019089
PMCID: PMC2961680  PMID: 21202977
14.  2-(2,4-Dichloro­phen­yl)-3-[5-(3,5-dimethyl­phen­yl)-1,3,4-thia­diazol-2-yl]thia­zolidin-4-one 
The title compound, C19H15Cl2N3OS2, was synthesized by the reaction of N-(2,4-dichloro­phen­yl)-5-(3,5-dimethyl­phen­yl)-1,3,4-thia­diazol-2-amine and mercaptoacetic acid. The thia­zolidinone ring adopts a twist conformation. The 2,4-dichloro­phenyl ring is almost perpendicular to the thia­diazole ring, the dihedral angle being 82.8 (2)°. The 3,5-dimethyl­phenyl ring is nearly coplanar with the thia­diazole ring, the dihedral angle being 2.7 (2)°. An intramolecular C—H⋯N hydrogen bond is present.
doi:10.1107/S1600536807066068
PMCID: PMC2924216  PMID: 21200825
15.  5-(2-Methyl­phen­yl)-1,3,4-thia­diazol-2-amine 
The asymmetric unit of the title compound, C9H9N3S, contains two crystallographically independent mol­ecules, in which the thia­diazole and tolyl rings are oriented at dihedral angles of 32.25 (3) and 74.50 (3)°. An intra­molecular C—H⋯S inter­action results in the formation of a five-membered ring. In the crystal structure, inter­molecular N—H⋯N hydrogen bonds link the mol­ecules into chains along the a axis. A π–π contact between the thia­diazole rings [centroid–centroid distance = 3.910 (3) Å] may further stabilize the structure. There is also a weak C—H⋯π inter­action.
doi:10.1107/S1600536809011234
PMCID: PMC2977661  PMID: 21584004
16.  5-(4-Bromo­phen­oxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde-O-[(5-meth­oxy-1,3,4-thia­diazol-2-yl)-meth­yl]oxime 
In the title mol­ecule, C16H16BrN5O3S, the 1,3,4-thia­diazole ring is situated under the benzene ring, forming a dihedral angle of 86.6 (2)°, and with an S⋯Cg (where Cg is the centroid of the benzene ring) distance of 3.312 (3) Å. The benzene and 1,3,4-thia­diazole rings form dihedral angles of 83.8 (3) and 57.7 (2)°, respectively, with the central pyrazole ring. In the absence of classical hydrogen bonds, the crystal packing is stabilized by a C—H⋯π inter­action..
doi:10.1107/S1600536812042274
PMCID: PMC3515227  PMID: 23284447
17.  2-Benzyl­sulfanyl-4-[(4-methyl­phen­yl)sulfan­yl]-6-pentyl­pyrimidine-5-carbonitrile 
In the title compound, C24H25N3S2, the S-bound benzene rings have orthogonal [dihedral angle = 85.31 (9)°] and splayed [67.92 (11)°] orientations with respect to the pyrimidine ring; the dihedral angle between the benzene rings is 48.18 (12)°. The pentyl group has an extended all-trans conformation and lies to one side of the pyrimidine ring [the Npy—Cpy—Cp—Cp torsion angle = −85.7 (2)°; py = pyrimidine and p = pent­yl].
doi:10.1107/S1600536812025275
PMCID: PMC3393321  PMID: 22807878
18.  N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)benzene­sulfonamide 
The title compound, C22H23BrN4O3S2, crystallizes with two mol­ecules, A and B, in the asymmetric unit. In one of these, the meth­oxy group is disordered over two sets of sites in a 0.565 (9):0.435 (9) ratio. The benzene rings bridged by the sulfonamide group are tilted relative to each other by 37.4 (1) and 56.1 (1)° in mol­ecules A and B, respectively, while the dihedral angles between the sulfur-bridged pyrimidine and benzene rings are 72.4 (1) and 70.2 (1)° for A and B, respectively. The piperidine ring adopts a chair conformation in both mol­ecules. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds occur for both A and B; the dimers are linked into [010] chains by C—H⋯O hydrogen bonds. The crystal structure also features inversion-generated aromatic π–π stacking inter­actions between the pyrimidine rings for both mol­ecules [centroid–centroid distances = 3.412 (2) (mol­ecule A) and 3.396 (2) Å (mol­ecule B)].
doi:10.1107/S1600536812043668
PMCID: PMC3515297  PMID: 23284517
19.  N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-4-methyl­benzene­sulfonamide 
In the title compound, C23H25BrN4O3S2, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 69.7 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 70.4 (1)°. The mol­ecular conformation is stabilized by a weak intra­molecular π–π stacking inter­action between the pyrimidine and the 4-methyl benzene rings [centroid–centroid distance = 3.633 (2) Å]. The piperidine ring adopts a chair conformation. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds.
doi:10.1107/S1600536812037257
PMCID: PMC3470193  PMID: 23125637
20.  2-Meth­oxy-N-[5-(2-methoxy­phen­yl)-1,3,4-thia­diazol-2-yl]benzamide hemi­hydrate 
In the mol­ecule of the title compound, C17H15N3O3S·0.5H2O, the thia­diazole ring is oriented with respect to the two 2-methoxy­phenyl rings at dihedral angles of 3.70 (3) and 1.74 (2)°. An intra­molecular N—H⋯O hydrogen bond results in the formation of a planar six-membered ring, which is oriented with respect to the thia­diazole ring at a dihedral angle of 1.33 (3)°. Thus, all of the rings are nearly coplanar. In the crystal structure, inter­molecular O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules.
doi:10.1107/S1600536808019934
PMCID: PMC2962244  PMID: 21203326
21.  2-[(4,6-Di­amino­pyrimidin-2-yl)sulfan­yl]-N-(2-methyl­phen­yl)acetamide 
In the title compound, C13H15NOS, the plane of the pyrimidine ring makes a dihedral angle of 54.73 (9)° with that of the o-tolyl ring. The mol­ecule adopts an extended conformation, which is evident from the C—C(=O)—N—Car (ar = aromatic) torsion angle of 178.42 (15)°. In the crystal, mol­ecules are linked via pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are linked by N—H⋯O and C—H⋯O hydrogen bonds, with the O atom accepting three such interactions, forming sheets parallel to (100).
doi:10.1107/S1600536814015256
PMCID: PMC4158502  PMID: 25249901
crystal structure
22.  3-(3-Methyl­phen­yl)-5-(quinolin-8-yl­meth­oxy)-1,2,4-oxa­diazole monohydrate 
In the title compound, C19H15N3O2·H2O, the oxa­diazole ring and the quinoline unit are almost coplanar, making a dihedral angle of 7.66 (8)°. The dihedral angle between the benzene ring and the quinoline system is 25.95 (8)° while that between the benzene and the oxa­diazole rings is 18.88 (9)°. The water mol­ecule is hydrogen bonded to an oxa­diazole N atom and to the quinoline N atom. In the crystal, these units are linked via C—H⋯O hydrogen bonds, forming two-dimensional net­works lying parallel to the ab plane.
doi:10.1107/S160053681302477X
PMCID: PMC3790408  PMID: 24098227
23.  N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-4-methyl­benzene­sulfonamide 
In the title compound, C22H23BrN4O4S2, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 68.9 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 69.7 (1)°. The mol­ecular conformation is stabilized by a weak intra­molecular π–π stacking inter­action between the pyrimidine and the 4-methylbenzene rings [centroid–centroid distance = 3.934 (2) Å]. The morpholine ring adopts a chair conformation and is disordered over two positions with an occupancy ratio of 0.853 (6):0.147 (6). In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into chains extending along the a axis and further, through C—H⋯N and C—H⋯O inter­actions, into a three-dimensional supramolecular structure.
doi:10.1107/S1600536812033375
PMCID: PMC3415028  PMID: 22905015
24.  1-Methyl-3,3-bis­[(4-methyl­phen­yl)sulfan­yl]piperidin-2-one 
The piperidone ring in the title compound, C20H23NOS2, has a half-chair distorted to a twisted-boat conformation [Q T = 0.5200 (17) Å]. One of the S-bound benzene rings is almost perpendicular to the least-squares plane through the piperidone ring, whereas the other is not [dihedral angles = 75.28 (5) and 46.41 (5) Å, respectively]. In the crystal, the presence of C—H⋯O and C—H⋯π inter­actions leads to the formation of supra­molecular layers in the ab plane.
doi:10.1107/S1600536811037111
PMCID: PMC3201309  PMID: 22065241
25.  Crystal structures of the co-crystalline adduct 5-(4-bromo­phen­yl)-1,3,4-thia­diazol-2-amine–4-nitro­benzoic acid (1/1) and the salt 2-amino-5-(4-bromo­phen­yl)-1,3,4-thia­diazol-3-ium 2-carb­oxy-4,6-di­nitro­phenolate 
The hydrogen-bonded structures of both a (1:1) mol­ecular adduct and a salt of 5-(4-bromo­phen­yl)-1,3,4-thia­diazol-2-amine with 4-nitro­benzoic acid and 3,5-di­nitro­salicylic acid, respectively, have been determined.
The structures of the 1:1 co-crystalline adduct C8H6BrN3S·C7H5NO4, (I), and the salt C8H7BrN3S+·C7H3N2O7 −, (II), obtained from the inter­action of 5-(4-bromo­phen­yl)-1,3,4-thia­diazol-2-amine with 4-nitro­benzoic acid and 3,5-di­nitro­salicylic acid, respectively, have been determined. The primary inter-species association in both (I) and (II) is through duplex R 2 2(8) (N—H⋯O/O—H⋯O) or (N—H⋯O/N—H⋯O) hydrogen bonds, respectively, giving heterodimers. In (II), these are close to planar [the dihedral angles between the thia­diazole ring and the two phenyl rings are 2.1 (3) (intra) and 9.8 (2)° (inter)], while in (I) these angles are 22.11 (15) and 26.08 (18)°, respectively. In the crystal of (I), the heterodimers are extended into a chain along b through an amine N—H⋯Nthia­diazole hydrogen bond but in (II), a centrosymmetric cyclic hetero­tetra­mer structure is generated through N—H⋯O hydrogen bonds to phenol and nitro O-atom acceptors and features, together with the primary R 2 2(8) inter­action, conjoined R 4 6(12), R 2 1(6) and S(6) ring motifs. Also present in (I) are π–π inter­actions between thia­diazole rings [minimum ring-centroid separation = 3.4624 (16) Å], as well as short Br⋯Onitro inter­actions in both (I) and (II) [3.296 (3) and 3.104 (3) Å, respectively].
doi:10.1107/S1600536814021138
PMCID: PMC4257302  PMID: 25484726
5-substituted-2-amino-1,3,4-thia­diazo­les; 4-nitro­benzoic acid; 3,5-di­nitro­salicylic acid; proton transfer; mol­ecular adducts; co-crystals; hydrogen bonding; π–π inter­actions; crystal structure

Results 1-25 (571013)