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1.  4-Meth­oxy-N-[(E)-(5-nitro­thio­phen-2-yl)methyl­idene]aniline 
The title mol­ecule, C12H10N2O3S, is nonplanar with an inter­planar angle of 33.44 (7)° between the benzene and thio­phene rings. In the crystal there exist only weak inter­molecular C—H⋯O inter­actions, π–π inter­actions between the benzene rings [centroid–centroid distance = 3.7465 (14) Å] and X—Y⋯π inter­actions to the thio­phene and benzene rings [N⋯centroid distances = 3.718 (3) and 3.355 (3) Å, respectively]. Inter­molecular C—H⋯O inter­actions link the mol­ecules into chains parallel to the a axis.
doi:10.1107/S1600536812034344
PMCID: PMC3470380  PMID: 23125793
2.  (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
3.  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
4.  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
5.  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
6.  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
7.  4-Methyl-N-[(5-nitro­thio­phen-2-yl)methyl­idene]aniline 
The title compound, C12H10N2O2S, is a Schiff base formed from p-toluidine and 5-nitro­thio­phene-2-carbaldehyde. The C=N bond adopts an E configuration. The benzene and thio­phene rings form a dihedral angle of 9.2 (1)°.
doi:10.1107/S1600536811030297
PMCID: PMC3200857  PMID: 22064527
8.  (E)-4-Methyl-N-[(5-nitro­thio­phen-2-yl)methyl­idene]aniline 
In the crystal structure of the title compound, C12H10N2O2S, the benzene and the 2-nitro­thio­phene rings make a dihedral angle of 7.47 (12)°. The dihedral angle between the nitro group and the attached ring is 1.9 (6)°.
doi:10.1107/S1600536812026062
PMCID: PMC3393928  PMID: 22798793
9.  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
10.  Diethyl 2-{[3-(2-meth­oxy­benz­yl)thio­phen-2-yl]methyl­idene}malonate 
In the title compound, C20H22O5S, the dihedral angle between the mean planes through the thio­phene and benzene rings is 75.2 (1)°. The meth­oxy group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.019 (2) Å for the O atom. The malonate group assumes an extended conformation.
doi:10.1107/S1600536811022525
PMCID: PMC3151827  PMID: 21837085
11.  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
12.  (E)-1-(3-Nitro­phen­yl)-2-({5-[(1E)-2-(3-nitro­phen­yl)hydrazin-1-ylidenemeth­yl]-2-thien­yl}methyl­idene)hydrazine 
The title mol­ecule, C18H14N6O4S, adopts a U-shape with the aromatic groups lying syn and oriented in the same direction as the thio­phene S atom. Twists away from planarity are evident with the maximum deviation being found for a terminal nitro group: C/C/N/O = 19.0 (3)°. The conformation about each of the C=N bonds is E. In the crystal, centrosymmetrically related mol­ecules are connected via N—H⋯Onitro hydrogen bonds, forming 14-membered {⋯HNC3NO}2 synthons. These are linked into layers via C—H⋯Onitro inter­actions with the primary inter­actions between layers being of the type C—H⋯π, where the π-system is the thio­phene ring.
doi:10.1107/S1600536810002771
PMCID: PMC2979791  PMID: 21579872
13.  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
14.  (E)-1-Phenyl-2-({5-[(1E)-(2-phenyl­hydrazin-1-yl­idene)meth­yl]-2-thien­yl}methyl­idene)hydrazine 
The title mol­ecule, C18H16N4S, adopts a U-shape with the aromatic groups lying syn and orientated in the same direction as the thio­phene S atom. The conformation about each of the C=N bonds is E. Overall, the mol­ecule is curved as seen in the dihedral angle of 30.26 (19)° formed between the terminal benzene rings. In the crystal, supra­molecular chains along the c axis are formed by a combination of N—H⋯N hydrogen bonds and N—H⋯π inter­actions.
doi:10.1107/S1600536810003302
PMCID: PMC2983505  PMID: 21580281
15.  (2E)-1-(2,5-Dimethyl-3-thien­yl)-3-(2-meth­oxy­phen­yl)prop-2-en-1-one 
In the title compound, C16H16O2S, the central propenone group is almost planar (r.m.s. deviation = 0.009 Å) and subtends dihedral angles of 8.55 (8) and 16.22 (8)° to the 2-meth­oxy­phenyl and 2,5-dimethyl­thio­phene residues, respectively. The dihedral angle between the ring systems is 23.47 (5)°. In the crystal, mol­ecules are linked by weak C—H⋯π inter­actions and aromatic π–π stacking [phenyl ring centroid–centroid separation = 3.6418 (11) Å; thio­phene–thio­phene ring separation = 3.8727 (9) Å].
doi:10.1107/S1600536810032769
PMCID: PMC3008090  PMID: 21588700
16.  (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
17.  Crystal structure of 3-({[(thio­phen-2-yl)methyl­idene]hydrazin­yl}carbon­yl)pyridinium chloride dihydrate 
In the title compound, C11H10N3OS+·Cl−·2H2O, the organic cation exhibits a dihedral angle of 21.26 (8)° between the mean planes of the pyridine and thio­phene rings, and dihedral angles of 15.11 (9) and 6.49 (9)° between the mean planes of the hydrazide moiety and the pyridine and thio­phene rings, respectively. In the crystal, the organic cation, the chloride counter-anion and the two water mol­ecules of crystallization are linked through an intricate hydrogen-bonding network consisting of O—H⋯O, O—H⋯N, N—H⋯Cl, C—H⋯Cl, C—H⋯O, N—H⋯O, O—H⋯Cl and C—H⋯S inter­actions that consolidate a three-dimensional network.
doi:10.1107/S1600536814017565
PMCID: PMC4186149  PMID: 25309289
crystal structure; pyridinium chloride salt; hydrogen bonding; hydrazone derivatives
18.  (E)-2-(2,3-Dimethyl­anilino)-N′-(thio­phen-2-yl­methyl­idene)benzohydrazide 
In the title compound, C20H19N3OS, the central benzene ring makes dihedral angles of 45.36 (9) and 55.33 (9)° with the thio­phene ring and the dimethyl-substituted benzene ring, respectively. The dihedral angle between the thio­phene ring and dimethyl-substituted benzene ring is 83.60 (9)°. The thio­phene ring and the benzene ring are twisted from the mean plane of the C(=O)—N—N=C bridge [maximum deviation = 0.0860 (13) Å], with dihedral angles of 23.86 (9) and 24.77 (8)°, respectively. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds to the same acceptor atom, forming sheets lying parallel to the bc plane. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S160053681203259X
PMCID: PMC3414973  PMID: 22904960
19.  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
20.  (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
21.  {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
22.  Crystal structure of [4-(2-meth­oxy­phen­yl)-3-methyl-1-phenyl-6-tri­fluoro­methyl-1H-pyrazolo­[3,4-b]pyridin-5-yl](thio­phen-2-yl)methanone 
The title compound, C26H18F3N3O2S, a 2-meth­oxy-substituted derivative, is closely related to its 4-methyl- and 4-chloro-substituted analogues and yet displays no structural relationships with them. The thio­phene ring is disorder free and the –CF3 group exhibits disorder, respectively, in contrast and similar to that observed in the 4-methyl- and 4-chloro-substituted derivatives. The torsion angle which defines the twist of the thio­phene ring is −69.6 (2)° (gauche) in the title compound, whereas it is anti­clinal in the 4-methyl- and 4-chloro-substituted derivatives, with respective values of 99.9 (2) and 99.3 (2)°. The absence of disorder in the thio­phene ring facilitates one of its ring C atoms to participate in the lone inter­molecular C—H⋯O hydrogen bond present in the crystal, leading to a characteristic C(5) chain graph-set motif linking mol­ecules related through glides along [010]. An intra­moleculr C—H⋯N hydrogen bond also occurs.
doi:10.1107/S1600536814017437
PMCID: PMC4186079  PMID: 25309288
crystal structure; 1H-pyrazolo­[3,4-b]pyridine; hydrogen bonding graph-set analysis
23.  2,3,5,6-Tetra­fluoro-1,4-bis­({[(thio­phen-2-yl)methyl­idene]amino}­meth­yl)benzene 
In the title compound, C18H12F4N2S2, a bis-thio­phenyl Schiff base ligand with a perifluorinated aromatic core, the complete molecule is generated by crystallographic inversion symmetry. The thio­phene and tetra­fluorinated benzene rings are oriented at a dihedral angle of 77.38 (4)°. The crystal structure exhibits C—H⋯F hydrogen bonds, resulting in supra­molecular chains along the c-axis direction.
doi:10.1107/S1600536814012434
PMCID: PMC4120615  PMID: 25161544
24.  (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
25.  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

Results 1-25 (614492)