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1.  (±)-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
2.  1-(2,5-Dichloro-3-thien­yl)ethanone: infinite sheets mediated by O⋯Cl halogen bonds 
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.
doi:10.1107/S1600536810035154
PMCID: PMC2983218  PMID: 21587481
3.  3-(2-Chloro-6-fluoro­phen­yl)-1-(2-thien­yl)prop-2-en-1-one 
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.
doi:10.1107/S1600536808024872
PMCID: PMC2960501  PMID: 21201705
4.  trans-rac-[1-Oxo-2-phenethyl-3-(2-thien­yl)-1,2,3,4-tetra­hydro­isoquinolin-4-yl]methyl 4-methyl­benzene­sulfonate 
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.
doi:10.1107/S1600536808029309
PMCID: PMC2959401  PMID: 21201159
5.  (E)-1-(2,5-Dimethyl-3-thien­yl)-3-(2-hy­droxy­phen­yl)prop-2-en-1-one 
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.
doi:10.1107/S1600536810031284
PMCID: PMC3007990  PMID: 21588620
6.  (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
7.  (E)-1-(2-Thien­yl)-3-(3,4,5-trimethoxy­phen­yl)prop-2-en-1-one1  
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.
doi:10.1107/S1600536809021850
PMCID: PMC2969210  PMID: 21582853
8.  6-Chloro-2-methyl-4-phenyl-3-[1-phenyl-5-(2-thien­yl)-4,5-dihydro-1H-pyrazol-3-yl]quinoline 
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].
doi:10.1107/S1600536809040239
PMCID: PMC2971145  PMID: 21578307
9.  N′-[(3-Methyl-2-thien­yl)carbon­yl]isonicotinohydrazide 
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.
doi:10.1107/S1600536809033030
PMCID: PMC2969908  PMID: 21577634
10.  3-(4-{3,3,4,4,5,5-Hexafluoro-2-[5-(3-methoxy­phen­yl)-2-methyl-3-thien­yl]cyclo­pent-1-en­yl}-5-methyl-2-thien­yl)benzonitrile 
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).
doi:10.1107/S1600536809034771
PMCID: PMC2970449  PMID: 21577821
11.  2,6-Diphenyl-4-(2-thien­yl)-1,4-dihydro­pyridine-3,5-dicarbonitrile 
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).
doi:10.1107/S1600536809033339
PMCID: PMC2970109  PMID: 21577644
12.  2-Methyl-3-(5-methyl-2-thien­yl)-5-phenyl­perhydro­pyrrolo[3,4-d]isoxazole-4,6-dione 
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.
doi:10.1107/S1600536809009209
PMCID: PMC2968779  PMID: 21582577
13.  N′-[(E)-(4-Bromo-2-thien­yl)methyl­idene]benzohydrazide 0.06-hydrate 
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.
doi:10.1107/S1600536809037350
PMCID: PMC2970472  PMID: 21577950
14.  5-tert-Butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl)-2-thien­yl]-1,3-benzoxazole 
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.
doi:10.1107/S1600536808037665
PMCID: PMC2959973  PMID: 21581379
15.  3,6-Dimethyl-1-phenyl-4-(2-thien­yl)-8-(2-thienylmethyl­ene)-5,6,7,8-tetra­hydro-1H-pyrazolo[3,4-b][1,6]naphthyridine 
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.
doi:10.1107/S1600536809014810
PMCID: PMC2977787  PMID: 21583923
16.  (3R,3aS,6aR)-2,5-Dimethyl-3-(5-phenyl-2-thien­yl)perhydro­pyrrolo[3,4-d][1,2]oxazole-4,6-dione 
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 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)°.
doi:10.1107/S1600536808020102
PMCID: PMC2962057  PMID: 21203142
17.  5-tert-Butyl-2-hy­droxy-3-(2-thien­yl)benzaldehyde 
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.
doi:10.1107/S1600536810030382
PMCID: PMC3007824  PMID: 21588589
18.  (E)-1-(2,5-Dichloro-3-thien­yl)-3-[4-(dimethyl­amino)phen­yl]prop-2-en-1-one 
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.
doi:10.1107/S1600536810014364
PMCID: PMC2979294  PMID: 21579187
19.  1-(2-Chloro­phen­yl)-2-(2-methyl-5-phenyl-3-thien­yl)-3,3,4,4,5,5-hexa­fluoro­cyclo­pent-1-ene: a new photochromic diaryl­ethene 
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.
doi:10.1107/S1600536808013330
PMCID: PMC2961463  PMID: 21202552
20.  1-Methyl-4-[(E)-2-(2-thien­yl)­ethen­yl]­pyridinium 4-methyl­benzene­sulfonate1  
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.
doi:10.1107/S1600536808031401
PMCID: PMC2959609  PMID: 21580938
21.  6-(4-Amino­phen­yl)-2-eth­oxy-4-(2-thien­yl)nicotinonitrile 
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 [010]. These chains are stacked along the a axis. C—H⋯π weak inter­actions involving the thio­phene ring are observed.
doi:10.1107/S160053681002369X
PMCID: PMC3006713  PMID: 21588020
22.  1-Methyl-2-[(E)-2-(2-thien­yl)ethen­yl]quinolinium 4-bromo­benzene­sulfonate 
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.
doi:10.1107/S1600536810007488
PMCID: PMC2979024  PMID: 21579112
23.  (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
24.  3,3,4,4,5,5-Hexa­fluoro-1,2-bis­[5-(2-fluoro-4′-undecyl­oxybiphenyl-4-yl)-2-methyl-3-thien­yl]cyclo­pentene 
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.
doi:10.1107/S1600536808010635
PMCID: PMC2961548  PMID: 21202692
25.  (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

Results 1-25 (80931)