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.
In the title compound, C6H4Cl2OS, the acetyl group is almost coplanar with the thiophene ring [dihedral angle = 4.01 (2)°]. In the crystal, short intermolecular O⋯Cl contacts [2.9494 (14) and 3.1191 (14) Å] link the molecules into infinite (100) sheets and aromatic π–π stacking [centroid–centroid separation = 3.5422 (10) Å] consolidates the packing.
The title chalcone derivative, C13H8ClFOS, crystallized as an inversion twin with two independent molecules in the asymmetric unit. The thiophene rings in both molecules are disordered over two sites: the ratios of occupancies for the major and minor components in the two molecules are 0.820 (2):0.180 (2) and 0.853 (2):0.147 (2). The dihedral angles between the major and minor components of the thiophene and benzene rings are 1.13 (18) and 2.2 (6)°, respectively, in one molecule, with corresponding values 6.09 (17) and 1.3 (6)° in the other. Weak intramolecular C—H⋯O and C—H⋯F interactions involving the prop-2-en-1-one group generate an S(5)S(5) ring motif, whereas a weak intramolecular C—H⋯Cl contact generates an S(6) ring motif. In the crystal structure, molecules of both the major and minor components are linked into infinite one-dimensional chains along the b axis. The crystal structure is stabilized by weak C—H⋯O, C—H⋯F, C—H⋯Cl and C—H⋯π interactions.
The title compound, C29H27NO4S2, was synthesized by reaction of trans-rac-4-(hydroxymethyl)-2-phenethyl-3-(thiophen-2-yl)-3,4-dihydroisoquinolin-1(2H)-one and 4-methylbenzene-1-sulfonyl chloride in the presence of Et3N in CH2Cl2. The relative orientations of the benzene ring (A) of the 3,4-dihydroisoquinolinone ring system, the thiophene ring (B), the benzene ring (C) of the methylbenzene group and the phenyl ring (D) result in the following dihedral angles: A/B = 80.91 (16), A/C = 22.79 (18), A/D = 9.9 (2), B/C = 80.73 (19), B/D = 88.9 (2) and C/D = 29.9 (2)°. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.
In the title compound, C15H14O2S, the dihedral angle between the aromatic rings is 8.46 –(8)°. The central enone group is planar (r.m.s. deviation = 0.0267 Å) and is oriented at a dihedral angle of 1.20 (9)° with respect to the benzene ring and at 8.27 (9)° with respect to the thiophene group. In the crystal, the molecules are linked into polymeric chains extending along the b axis due to intermolecular O—H⋯O hydrogen bonding. An S(6) ring motif is formed due to a short intramolecular C—H⋯O contact. C—H⋯π interactions involving a methyl group of the 2,5-dimethylthienyl group and the benzene ring are present. π–π interactions between the centroids of the benzene and heterocyclic rings [3.7691 (9) Å] also occur.
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.
The molecule of the title heteroaryl chalcone, C16H16O4S, which consists of substituted thiophene and benzene rings bridged by the prop-2-en-1-one group, is slightly twisted. The dihedral angle between the thiophene and 3,4,5-trimethoxyphenyl rings is 12.18 (4)°. The three methoxy groups have two different conformations; two methoxy groups are coplanar [C—O—C—C torsion angles = −1.38 (12) and 0.47 (12)°] whereas the third is (-)-synclinal with the benzene ring. In the crystal structure, adjacent molecules are linked in a face-to-side manner into chains along the c axis by weak C—H⋯O(enone) interactions. These chains are stacked along the b axis by weak C—H⋯O(methoxy) interactions.
In the title molecule, C29H22ClN3S, the quinoline ring system, thiophene ring and phenyl ring substituents are inclined at angles of 71.70 (7), 59.26 (9) and 81.61 (9)°, respectively, to the 4,5-dihydropyrazole ring. In the 4-phenylquinoline ring system, the phenyl ring makes a dihedral angle of 62.49 (7)° with mean plane of quinoline ring system. In the crystal structure, molecules are linked via weak intermolecular C—H⋯N hydrogen bonds, forming an extended one-dimensional chain along the b axis and are further consolidated by C—H⋯π and π–π stacking interactions [centroid–centroid distances = 3.7022 (10) Å].
In the title compound, C12H11N3O2S, the pyridine ring is inclined to the thiophene ring, forming a dihedral angle of 34.96 (7)°. The mean plane through the hydrazide unit forms dihedral angles of 21.57 (8) and 53.08 (8)°, respectively, with the pyridine and thiophene rings. The two O atoms are twisted away from each other, as indicated by the C—N—N—C torsion angle of −81.27 (15)°. In the crystal structure, molecules are linked into an extended three-dimensional network by intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds. The crystal structure also features a short S⋯O [3.2686 (10) Å] interaction and a weak intermolecular C—H⋯π interaction.
The title compound, C29H19F6NOS2, is a new unsymmetrical photochromic diarylethene derivative with different meta-phenyl substituents. The distance between the two reactive (i.e. can be irradiated to form a new chemical bond) C atoms is 3.501 (4) Å; the dihedral angles between the mean plane of the main central cyclopentene ring and the thiophene rings are 47.7 (5) and 45.1 (2)°, and those between the thiophene rings and the adjacent benzene rings are 29.4 (2) and 28.4 (3)°. The three C atoms and the F atoms of hexafuorocyclopentene ring are disordered over two positions, with site-occupancy factors of 0.751 (4) and 0.249 (4).
The asymmetric unit of the title compound, C23H15N3S, contains two crystallographically independent molecules. The pyridine rings adopt envelope conformations. The thiophene rings are oriented at dihedral angles of 77.97 (4)/53.53 (4) and 78.44 (4)/57.11 (4)° with respect to the phenyl rings, while the dihedral angles between the phenyl rings are 48.51 (4) and 44.49 (4)°. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link the molecules into chains along the c axis. The S, C and H atoms of one of the thiophene rings are disordered over two orientations, with occupancy ratios of 0.314 (15):0.686 (15).
In the molecule of the title compound, C17H16N2O3S, the phenyl ring is oriented with respect to the thiophene and succinimide rings at dihedral angles of 88.08 (3) and 57.81 (3)°, respectively; the dihedral angle between the thiophene and succinimide rings is 35.69 (3)°. The isoxazole ring adopts an envelope conformation with the N atom at the flap position. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into infinite chains along the b axis. Weak C—H⋯π interactions may further stabilize the structure.
The title compound, C12H9BrN2OS·0.06H2O, is a hydrated Schiff base derived from benzoic hydrazide and 4-bromothiophene-2-carboxaldehide. The two Schiff base molecules in the asymmetric unit differ crystallographically: in one molecule the dihedral angle between the benzene ring and thiophene ring is 49.88 (11)°, whereas the other molecule the rings are almost coplanar with an r.m.s. deviation for the non-H atoms of 0.025 Å. In the crystal, molecules form polymeric sheets linked by N—H⋯O and C—H⋯O hydrogen bonds. The water molecule of crystallization is partially occupied and its H atoms could not be located.
The title compound, C26H26N2O2S, was prepared by the reaction of thiophene-2,5-dicarboxylic acid and 2-amino-4-tert-butylphenol. One of the tert-butyl groups is disordered over two conformations, with occupancies of 0.539 (1) and 0.461 (2). The two 1,3-benzoxazole rings are almost planar, with dihedral angles of 0.83 (18) and 1.64 (17)° between the five- and six-membered rings. The thiophene ring makes dihedral angles of 21.54 (19) and 4.49 (18)° with the planes of the five-membered oxazole rings. The crystal packing is controlled by π–π stacking interactions involving the thiophene and benzene rings, with a centroid–centroid distance of 3.748 (2) Å.
In the molecule of the title compound, C26H22N4S2, the pyrazole ring is oriented at a dihedral angle of 0.85 (3)° with respect to the adjacent naphthyridine ring, while the other ring of naphthyridine adopts an envelope conformation. The dihedral angle between phenyl and pyrazole rings is 87.65 (3)°. In the crystal structure, weak intermolecular C—H⋯N interactions link the molecules into chains. The π–π contacts between the naphthyridine rings and the naphthyridine and thiophene rings [centroid–centroid distances = 3.766 (3) and 3.878 (3) Å] may further stabilize the structure. A weak C—H⋯π interaction is also present.
The crystal structure of the title compound, C17H16N2O3S, exhibits intramolecular C—H⋯S and intermolecular C—H⋯S and C—H⋯O hydrogen bonds, C—S⋯N [S⋯N = 3.033 (2) Å and C—S⋯N = 142.76 (9)°] interactions, and C—H⋯π interactions; these interactions generate S(4), S(6) and R
2(14) ring motifs. The isoxazole ring adopts an envelope conformation, with the N atom displaced by 0.672 (2) Å from the plane of the other ring atoms. The thiophene ring is oriented with respect to the succinimide and phenyl rings at dihedral angles of 40.03 (12) and 5.21 (13)°, respectively. The dihedral angle between the succinimide and phenyl rings is 39.38 (12)°.
In the crystal structure of the title compound, C15H16O2S, the thiophene ring is essentially planar (r.m.s. deviation = 0.006 Å for all non-H atoms) and roughly coplanar with the benzene ring, the dihedral angle between the mean planes of the rings being 4.35 (8)°. An intramolecular O—H⋯O hydrogen bond is observed between the OH group and the aldehyde O atom.
In the title compound, C15H13Cl2NOS, the benzene and thiophene rings make a dihedral angle of 10.8 (1)°. The dimethylamino substituent and the α,β-unsaturated carbonyl group are almost coplanar with respect to the aromatic ring, forming dihedral angles of 4.73 (3)° and 5.0 (2)°, respectively. In the crystal structure, molecules are connected into two-dimensional layers by weak C—H⋯Cl hydrogen bonds and C—Cl⋯O [Cl⋯O = 3.073 (2) Å] interactions. These layers are stacked with short C(methyl)–H⋯π contacts betweeen the layers.
The title compound, C22H13ClF6S, is a hybrid diarylethene derivative with one 3-thienyl substituent, and a Cl-substituted six-membered aryl unit bonded to the double bond of a hexafluorocyclopentene ring. In the crystal structure, the molecule adopts a photo-active antiparallel conformation that can undergo effective photocyclization reactions. The distance between the two reactive C atoms is 3.848 (3) Å. The dihedral angles between the least-squares cyclopentene plane and those of the adjacent thiophene and chlorophenyl rings are 49.39 (8) and 59.88 (8)°, respectively. The F atoms are disordered over two positions, with site occupancy factors of 0.6 and 0.4.
In the title compound, C12H12NS+·C7H7O3S−, the cation exists in an E configuration with respect to the ethenyl C=C bond. The cation is essentially planar with a dihedral angle of 1.94 (10)° between the pyridinium and thiophene rings. The benzene ring of the anion makes dihedral angles of 75.23 (10) and 76.83 (10)°, respectively, with the pyridinium and thiophene rings. In the crystal structure, cations and anions form alternate layers parallel to the bc plane. Within each layer, both cations and anions are arranged into chains directed along the b axis. The cation chain and the anion chain are interconnected by weak C—H⋯O interactions into a three-dimensional network. The crystal structure is further stabilized by C—H⋯π interactions.
In the title nicotinonitrile derivative, C18H15N3OS, the central pyridyl ring makes dihedral angles of 25.22 (10) and 24.80 (16)° with the 4-aminophenyl and thiophene rings, respectively. The thiophene ring is disordered over two orientations by rotation around the C(thiophene)—C(pyridine) bond; the occupancies are 0.858 (2) and 0.142 (2). The ethoxy group is slightly twisted from the attached pyridyl ring [C—O—C—C torsion angle = 171.13 (16)°]. In the crystal structure, molecules are linked by N—H⋯N hydrogen bonds into chains along . These chains are stacked along the a axis. C—H⋯π weak interactions involving the thiophene ring are observed.
In the title compound, C16H14NS+·C6H4BrO3S−, the cation exists in an E configuration and is essentially planar, the dihedral angle between the quinolinium and thiophene rings being 3.45 (9)°. The anion is inclined to the cation with dihedral angles of 75.43 (8) and 72.03 (11)°, respectively between the benzene ring and the quinolinium and thiophene rings. In the crystal, the cations and anions are arranged individually into separate chains along the c axis. The cation chains are stacked in an antiparallel manner along the a axis by π⋯π interactions with centroid–centroid distances of 3.7257 (13) and 3.7262 (14) Å. Weak C—H⋯O and C—H⋯π interactions link the cations and anions into a three-dimensional network. Short Br⋯S [3.7224 (5) Å] and Br⋯O [3.4267 (16) Å] contacts are also observed.
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.
The title compound, C61H68F8O2S2, is a photochromic liquid crystal based on diarylethene as photoswitchable unit. The F atoms connected to the benzene rings are disordered over two positions; the site-occupation factors refined to 0.830 (3)/0.170 (3). The molecule adopts a photo-active antiparallel conformation and the distance between the two reactive C atoms of the thiophene rings is 3.448 (3) Å. The dihedral angles between the central cyclopentene ring and the adjacent thiophene rings are 43.56 (3) and 48.58 (3)°. These structural elements exhibit a suitable geometry for photochromic behaviour in the crystalline state.
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.