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1.  (Z)-3-Meth­oxy-N-[(5-nitro­thio­phen-2-yl)methyl­idene]aniline 
In the title compound, C12H10N2O3S, the dihedral angle between the benzene and thio­phene rings is 43.17 (4)°. The crystal structure is devoid of any hydrogen-bonding inter­actions. However, π–π inter­actions between the benzene and thio­phene rings [distance between ring centroids = 3.6850 (11) Å] stack the mol­ecules along the a axis. The absolute structure could not be determined as the crystal studied was a racemic twin with a BASF parameter of 0.31 (6).
doi:10.1107/S1600536812033120
PMCID: PMC3435696  PMID: 22969567
2.  7-(4-Chloro­benzyl­idene)-3-[(4-chloro­phen­oxy)meth­yl]-6-(4-nitro­thio­phen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine 
In the title compound, C22H13Cl2N5O3S2, the thia­diazine ring adopts a half-chair conformation. The benzene rings of the chloro­phen­oxy and chloro­benzyl groups and the thio­phene ring form dihedral angles of 35.6 (1), 80.7 (1) and 14.2 (1)°, respectively, with the triazole ring. In the crystal, mol­ecules are connected into sheets parallel to (11) by inter­molecular C—H⋯N and C—H⋯Cl hydrogen bonds. In addition, π–π stacking inter­actions are observed between thio­phene and triazole rings, and between inversion-related triazole rings [centroid–centroid distances = 3.5975 (11) and 3.4324 (11) Å].
doi:10.1107/S1600536811015637
PMCID: PMC3089255  PMID: 21754553
3.  Methyl 3-[(1,1-dioxo-1λ6,2-benzothiazol-3-yl)amino]-5-nitrothiophene-2-carboxyl­ate 
The title nitro­thio­phene compound, C13H9N3O6S2, crystallizes with two independent mol­ecules in the asymmetric unit; the mol­ecular structure of each is stabilized by an intra­molecular N—H⋯O hydrogen bond. The two mol­ecules adopt flattened but slightly different conformations, viz. the dihedral angle between the thio­phene ring and the essentailly planar 1,2-benzisothia­zole fragment (r.m.s. deviations = 0.0227 and 0.0108 Å, respectively) is 15.62 (11)° in one mol­ecule and 5.46 (11)° in the other. In the crystal, mol­ecules are arranged into layers parallel to (-111) with weak Car—H⋯O inter­actions formed within the layer. N—H⋯O hydrogen bonds also occur. There are π–π stacking inter­actions between the mol­ecules in neighbouring layers, the distance between the centroids of the 1,2-benzisothia­zole benzene rings being 3.8660 (16) Å. Moreover, dipolar S=O⋯C=O inter­actions with an O⋯C distance of 2.893 (3) Å are observed between the symmetry-independent mol­ecules in different layers. The title compound showed weak inhibition of HLE (human leukocyte elastase).
doi:10.1107/S1600536812038378
PMCID: PMC3470323  PMID: 23125736
4.  2,3-Dibromo-3-(4-chloro­phen­yl)-1-(4-nitro­thio­phen-2-yl)propan-1-one 
The title compound, C13H8Br2ClNO3S, exhibits whole-mol­ecule disorder over two orientations in a 0.805 (6):0.195 (6) ratio. The dihedral angles between the thio­phene ring [maximum deviations = 0.017 (4) and 0.033 (9) Å for the major and minor components, respectively] and the chloro-substituted phenyl ring are 32.1 (5) (major component) and 26.3 (18)° (minor component). In the crystal, C—H⋯Cl and C—H⋯O hydrogen bonds link the mol­ecules into sheets lying parallel to the bc plane. Aromatic π–π stacking inter­actions [centroid–centroid distance = 3.550 (7) Å] are also observed.
doi:10.1107/S1600536812034551
PMCID: PMC3435703  PMID: 22969574
5.  (E)-1-(2-Thien­yl)-3-(2,4,5-trimethoxy­phen­yl)prop-2-en-1-one 
In the title mol­ecule, C16H16O4S, the enone fragment, thio­phene ring and benzene ring are individually essentially planar. The thio­phene ring is disordered over two sites, corresponding to a rotation of approximately 180° about the single C—C bond to which it is attached. The approximate ratio of occupancies for the major and minor components is 0.872 (2):0.128 (2). The major component of the thio­phene ring and the benzene ring are twisted from each other by 13.92 (19)°. An intra­molecular C—H⋯O hydrogen bond generates an S(5)S(5) ring motif. The crystal structure is stabilized by inter­molecular C—H⋯O hydrogen-bonding inter­actions. In addition, a π–π stacking inter­action, with a centroid–centroid distance of 3.852 (2) Å, and short S⋯O [2.9378 (12) Å] and O⋯O [2.5811 (16) Å] contacts are observed.
doi:10.1107/S1600536808021375
PMCID: PMC2962137  PMID: 21203219
6.  N-[(E)-Thio­phen-2-yl­methyl­idene]-1,3-benzothia­zol-2-amine 
In the title thio­phene-derived Schiff base compound, C12H8N2S2, the thio­phene ring is slighty rotated from the benzothia­zole group mean plane, giving a dihedral angle of 12.87 (6)°. The largest displacement of an atom in the mol­ecule from the nine-atom mean plane defined by the non-H atoms of the benzothia­zole ring system is 0.572 (1) Å, exhibited by the C atom at the 3-position of the thio­phene ring. In the crystal, weak C—H⋯S hydrogen bonds involving the thio­phene group S atom and the 4-position thio­phene C—H group of a symmetry-related mol­ecule lead to an infinite one-dimensional chain colinear with the c axis. The structure is further stabilized by π–π inter­actions; the distance between the thia­zole ring centroid and the centroid of an adjacent benzene ring is 3.686 (1) Å. The crystal studied was an inversion twin with the ratio of components 0.73 (3):0.27 (3).
doi:10.1107/S1600536812030498
PMCID: PMC3414944  PMID: 22904931
7.  2-Ethyl-N-[(5-nitro­thio­phen-2-yl)methyl­idene]aniline 
In the title compound, C13H12N2O2S, the dihedral angle between the benzene and thio­phene rings is 36.72 (8)°. An inter­molecular C—H⋯π inter­action contributes to the stability of the crystal structure.
doi:10.1107/S1600536811024615
PMCID: PMC3213459  PMID: 22091038
8.  (Z)-2-Meth­oxy-N-[(5-nitro­thio­phen-2-yl)methyl­idene]aniline 
The dihedral angle between the benzene and thio­phene rings in the title compound, C12H10N2O3S, is 27.94 (13)°. An inter­molecular C—H⋯π inter­action contributes to the stability of the crystal structure.
doi:10.1107/S160053681200044X
PMCID: PMC3275070  PMID: 22347015
9.  (E)-1-(2,5-Dimethyl-3-thien­yl)-3-(2,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one 
In the title compound, C18H20O4S, the thio­phene and benzene rings are oriented at a dihedral angle of 10.83 (11)°. The central chain makes dihedral angles of 1.86 (13) and 9.25 (12)° with the benzene and thio­phene rings, respectively. In the crystal, mol­ecules are linked through weak inter­molecular C—H⋯O inter­actions. π–π inter­actions are also observed between the benzene rings with a centroid–centroid distance of 3.6832 (12) Å. The slippage between the benzene rings is 0.956 Å.
doi:10.1107/S1600536810028709
PMCID: PMC3007317  PMID: 21588392
10.  2-(2-Nitro­anilino)-5,6,7,8-tetra­hydro-4H-cyclo­hepta­[b]thio­phene-3-carbonitrile 
The title compound, C16H15N3O2S, was synthesized by the reaction of 2-amino-5,6,7,8-tetra­hydro-4H-cyclo­hepta­[b]thio­phene-3-carbonitrile and o-fluoro­nitro­benzene. The thio­phene and nitro­phenyl rings and amino and carbonitrile groups are coplanar with a maximum deviation of 0.046 (2) Å and a dihedral angle of 0.92 (6)° between the rings. The cyclo­hepta ring adopts a chair conformation. Intra­molecular N—H⋯O and C—H⋯S inter­actions occur. In the crystal, the mol­ecules form layers that are linked by π–π stacking inter­actions between the thio­phene and benzene rings [centroid–centroid distances = 3.7089 (12) and 3.6170 (12) Å].
doi:10.1107/S1600536810017149
PMCID: PMC2979624  PMID: 21579437
11.  (E)-3-(3,4-Dimethoxy­phen­yl)-1-(2-thien­yl)prop-2-en-1-one 
The title compound, C15H14O3S, has two symmetry-independent mol­ecules in the asymmetric unit with almost identical geometry. The dihedral angle between the benzene and thio­phene rings is 1.61 (11)° in one mol­ecule and 7.21 (11)° in the other. In both mol­ecules, C—H⋯O hydrogen bonds generate rings of graph-set motif S(5). The crystal structure is stabilized by C—H⋯O hydrogen bonds, C—H⋯π inter­actions and π–π inter­actions involving the benzene and thio­phene rings, with centroid–centroid distances of 3.5249 (13) and 3.6057 (13) Å.
doi:10.1107/S1600536808020631
PMCID: PMC2962071  PMID: 21203155
12.  (±)-trans-6,7-Dimeth­oxy-1-oxo-3-(2-thien­yl)isochroman-4-carboxylic acid 
The title compound, C16H14O6S, was synthesized by the reaction of 6,7-dimethoxy­homophthalic anhydride with thio­phene-2-carbaldehyde in the presence of 4-(dimethyl­amino)pyridine (DMAP) as a basic catalyst. The thio­phene ring of the title mol­ecule is disordered over two sites with occupancies of 0.877 (3) and 0.123 (3). The disorder corresponds to an approximate 180° rotation of the thio­phene ring with respect to the C—C bond linking it to the rest of the mol­ecule. The six-membered ring of the 3,4-dihydro­isochromanone ring system is not planar [puckering parameters Q T = 0.571 (2) Å, θ = 115.2 (2)° and ϕ = 99.1 (2)°]. The benzene ring of the 3,4-dihydro­isochromanone ring system makes dihedral angles of 75.0 (2) and 77.2 (5)° with the disordered thio­phene rings. Inter­molecular O—H⋯O and C—H⋯O hydrogen bonds, as well as C—H⋯π inter­actions, lead to the observed supra­molecular structure.
doi:10.1107/S1600536809018844
PMCID: PMC2969835  PMID: 21583225
13.  (E)-3-(2,4-Dichloro­phen­yl)-1-(2-thien­yl)prop-2-en-1-one 
In the title chalcone derivative, C13H8Cl2OS, the prop-2-en-1-one unit and the thio­phene and 2,4-dichloro­phenyl rings are each essentially planar. The inter­planar angle between the thio­phene and 2,4-dichloro­phenyl rings is 19.87 (6)°. Weak intra­molecular C—H⋯O and C—H⋯Cl inter­actions involving the prop-2-en-1-one unit generate an S(5)S(5) ring motif. In the crystal structure, mol­ecules are linked into head-to-tail zigzag chains along the a axis and adjacent chains are cross-linked. These cross-linked chains are arranged into sheets parallel to the ab plane. The crystal structure is stabilized by weak C—H⋯O, C—H⋯Cl and C—H⋯π inter­actions. A π–π inter­action was also observed with a centroid–centroid distance of 3.6845 (6) Å.
doi:10.1107/S1600536808026524
PMCID: PMC2960483  PMID: 21201791
14.  N′-(3-Thienylmethyl­ene)pyridine-2-carbohydrazide 
The title compound, C11H9N3OS, was prepared to investigate the coordination chemistry of thio­phene-containing ligands as precursors to inter­esting metallopolymers. The mol­ecule is nearly planar. The angle between the thio­phene and pyridine rings is 8.63 (4)° and features the expected trans configuration about the imine bond. The structure is stabilized by a weak inter­molecular N—H⋯O hydrogen bond. The distance between centroids of adjacent thio­phene rings [3.67 (8) Å] suggests the presence of π–π inter­actions.
doi:10.1107/S1600536808004960
PMCID: PMC2961063  PMID: 21202109
15.  1,5-Bis(thio­phen-2-yl)-3-(2,4,5-trimeth­oxy­phen­yl)pentane-1,5-dione 
In the title 1,5-diketone compound, C22H22O5S2, the benzene ring makes dihedral angles of 41.51 (6) and 25.83 (6)° with the two thio­phene rings, while the dihedral angle between the thio­phene rings is 26.67 (7)°. An intra­molecular C—H⋯O inter­action generates an S(9) ring motif. In the crystal, mol­ecules are linked into a three-dimensional network by weak C—H⋯O and C—H⋯π inter­actions, and a π–π inter­action with a centroid–centroid distance of 3.6527 (8) Å.
doi:10.1107/S160053681104846X
PMCID: PMC3239053  PMID: 22199901
16.  3-Chloro-4-(4-chloro­phen­oxy)-N-[(Z)-(5-nitro­thio­phen-2-yl)methyl­idene]aniline 
In the title compound, C17H10Cl2N2O3S, the thio­phene ring and the central benzene ring are almost coplanar [dihedral angle = 8.44 (3)°], while the dihedral angle between the two benzene rings rings is 77.49 (9)°. The crystal packing is stabilized by inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812001316
PMCID: PMC3275174  PMID: 22347030
17.  (E)-1-(2,5-Dichloro­thio­phen-3-yl)ethan­one [8-(trifluoro­meth­yl)quinolin-4-yl]hydrazone 
In the title compound, C16H10Cl2F3N3S, the dihedral angle between the quinoline and thio­phene ring systems is 4.94 (10)°. The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thio­phene ring takes part in weak π–π stacking inter­actions with the pyridine ring [centroid-to-centroid separation = 3.7553 (19) Å and inter­planar angle = 5.48 (12)°] and the benzene ring [3.7927 (19) Å and 4.58 (12)°]. Together, these lead to [100] stacks of mol­ecules in an alternating head-to-tail arrangement, with two π–π stacking contacts between each adjacent pair.
doi:10.1107/S1600536812005673
PMCID: PMC3297859  PMID: 22412662
18.  {2-[(1H-Indol-3-yl­methyl­idene)amino]-4,5,6,7-tetra­hydro­benzo[b]thio­phen-3-yl}(phen­yl)methanone 
The title compound, C24H20N2OS, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit, in each of which the cyclo­hexene rings adopt half-chair conformations. The mean plane of the indole ring is twisted from those of the phenyl and thio­phene rings by 69.0 (7) and 8.3 (5)°, respectively, in mol­ecule A and by 65.4 (9) and 6.7 (5)°, respectively, in mol­ecule B. The dihedral angles between the mean planes of the phenyl and thio­phene rings are 63.0 (4) and 58.8 (9)° in mol­ecules A and B, respectively. In the crystal, N—H⋯O hydrogen bonds lead to the formation of an infinite chain along [101]. In addition, π–π stacking inter­actions are observed involving the thio­phene and pyrrole rings of the two mol­ecules, with a shortest inter­centroid distance of 3.468 (2) Å.
doi:10.1107/S1600536814006345
PMCID: PMC3998588  PMID: 24826189
19.  2-(Naphthalen-1-yl)-4-(thio­phen-2-yl­methyl­idene)-1,3-oxazol-5(4H)-one 
The asymmetric unit of the title compound, C18H11NO2S, contains two crystallographically independent mol­ecules. In one mol­ecule, the oxazole and thio­phene rings are oriented at dihedral angles of 17.40 (9) and 18.18 (7)° with respect to the naphthalene ring system, while the oxazole and thio­phene rings are oriented to each other at a dihedral angle of 0.86 (9)°. In the other mol­ecule, the corresponding angles are 3.05 (8), 9.62 (6) and 7.02 (8)°, respectively. In each mol­ecule, a weak intra­molecular C—H⋯N hydrogen bond links the oxazole N atom to the naphthalene group. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure. π–π stacking between the oxazole and thio­phene rings, between the thio­phene and naphthalene rings, and between the oxaozole and naphthalene rings, [centroid–centroid distances = 3.811 (2), 3.889 (2), 3.697 (2) and 3.525 (2) Å] may further stabilize the crystal structure.
doi:10.1107/S1600536811016151
PMCID: PMC3120366  PMID: 21754719
20.  2,3,5,6-Tetra­fluoro-1,4-bis­({[(5-methyl­thio­phen-2-yl)methyl­idene]amino}­meth­yl)benzene 
The title compound, C20H16F4N2S2, is a flexible bis­thio­phene-type Schiff base ligand with a perfluorinated backbone. The terminal thio­phene rings are almost normal to one another with a dihedral angle of 83.8 (2)°, and they are tilted to the central tetra­fluorinated benzene ring with dihedral angles of 61.2 (2) and 77.7 (1)°. In the crystal, there are π–π inter­actions involving the benzene ring and the thiophene ring of a symmetry-related molecule with a centroid–centroid separation of 3.699 (3) Å.
doi:10.1107/S1600536814011398
PMCID: PMC4051115  PMID: 24940272
21.  2-Iodo-5-nitro­thio­phene 
The title compound, C4H2INO2S, was synthesized by nitration of iodo­thio­phene with acetyl nitrate. The molecule is essentially planar, withthe nitro group tilted by 1.78 (19)° and the iodine atom displaced by 0.0233 (2) Å with respect to the thiophene ring. In the crystal structure, adjacent mol­ecules are linked through weak I⋯O inter­actions [3.039 (2)Å], forming chains extending along the b axis.
doi:10.1107/S1600536810017356
PMCID: PMC2979622  PMID: 21579486
22.  3-Amino-4,6-dimethyl­thieno[2,3-b]pyridine-2-carbonitrile 
The mol­ecule of the title compound, C10H9N3S, is almost planar, with a dihedral angle of 1.38 (4)° between the thio­phene and pyridine rings. In the crystal packing, mol­ecules are linked into layers parallel to the ab plane by inter­molecular N—H⋯N hydrogen bonds and by π⋯π stacking inter­actions involving adjacent pyridine and thio­phene rings with a centroid–centroid distance of 3.537 (3) Å.
doi:10.1107/S1600536809048132
PMCID: PMC2971991  PMID: 21578859
23.  3-[(N-Methyl­anilino)meth­yl]-5-(thio­phen-2-yl)-1,3,4-oxadiazole-2(3H)-thione 
In the title compound, C14H13N3OS2, the thio­phene ring is disordered over two orientations by ca 180° about the C—C bond axis linking the ring to the rest of the mol­ecule, with a site-occupancy ratio of 0.651 (5):0.349 (5). The central 1,3,4-oxadiazole-2(3H)-thione ring forms dihedral angles of 9.2 (5), 4.6 (11) and 47.70 (7)° with the major and minor parts of the disordered thio­phene ring and the terminal phenyl ring, respectively. In the crystal, no significant inter­molecular hydrogen bonds are observed. The crystal packing is stabilized by π–π inter­actions [centroid–centroid distance = 3.589 (2) Å].
doi:10.1107/S1600536812014419
PMCID: PMC3344480  PMID: 22590242
24.  Methyl trans-(±)-1-oxo-2-phenethyl-3-(thio­phen-2-yl)-1,2,3,4-tetra­hydro­isoquinoline-4-carboxyl­ate 
In the title compound, C23H21NO3S, the piperidine ring of the tetra­hydro­isoquinolinone unit adopts a screw-boat conformation. The thio­phene ring is disordered in a 0.700 (3):0.300 (3) ratio by an approximate 180° rotation of the ring around the C—C bond linking the ring to the tetra­hydro­isoquinolinone unit. The benzene ring of the tetra­hydro­isoquinolinone unit makes dihedral angles of 83.1 (2) and 62.38 (11)° with the major occupancy thio­phene ring and the phenyl ring, respectively. The dihedral angle between the phenyl ring and the thio­phene ring is 71.0 (2)°. In the crystal structure, mol­ecules are linked together by inter­molecular C—H⋯O and C—H⋯π inter­actions.
doi:10.1107/S1600536809017383
PMCID: PMC2969771  PMID: 21583149
25.  (2E,7E)-2,7-Bis[(thio­phen-2-yl)methyl­idene]cyclo­hepta­none 
The whole molecule of the title compound, C17H16OS2, is generated by two-fold rotational symmetry. The carbonyl C and O atoms of the cycloheptanone ring lie on the twofold rotation axis which bisects the opposite –CH2–CH2– bond of the ring. The mol­ecule exists in an E,E conformation with respect to the C=C double bond. The cyclo­hepta­none ring exhibits a twisted chair conformation and its mean plane makes a dihedral angle of 50.12 (19)° with the planes of the thio­phene rings. The two S atoms are in an anti arrangement with respect the carbonyl O atom and the dihedral angle between the two thio­phene ring planes is 69.38 (7)°. In the molecule, there are two intramolecular C—H⋯S hydrogen bond, forming S(6) ring motifs. In the crystal, inversion dimers are generated via pairs of C—H⋯O hydrogen bonds. These dimers are inter­connected by another inter­action of the same kind with a neighbouring mol­ecule, forming a mol­ecular chain along the c-axis direction.
doi:10.1107/S1600536814011866
PMCID: PMC4051043  PMID: 24940291

Results 1-25 (348557)