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(E)-3-(4-Chloro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

ABSTRACT: The title compound, C(13)H(9)ClOS, adopts an E configuration with respect to the C=C double bond of the propenone unit. The thienyl and benzene rings are slightly twisted from each other, making a dihedral angle of 6.38 (3)°. An intra-molecular C-H⋯O hydrogen bond generates an S(5) ring motif. A weak inter-molecular C-H⋯O inter-action, a short intra-molecular S⋯O contact [2.932 (2) Å] and two π-π inter-actions between the thienyl and benzene rings are observed. The centroid-centroid distances of the π-π inter-actions are 3.7899 (16) and 3.7891 (16) Å.

SUBMITTER: Fun HK

PROVIDER: S-EPMC2962207 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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(E)-3-(4-Chloro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

Fun Hoong-Kun HK Jebas Samuel Robinson SR Patil P S PS Dharmaprakash S M SM

Acta crystallographica. Section E, Structure reports online 20080726 Pt 8

The title compound, C(13)H(9)ClOS, adopts an E configuration with respect to the C=C double bond of the propenone unit. The thienyl and benzene rings are slightly twisted from each other, making a dihedral angle of 6.38 (3)°. An intra-molecular C-H⋯O hydrogen bond generates an S(5) ring motif. A weak inter-molecular C-H⋯O inter-action, a short intra-molecular S⋯O contact [2.932 (2) Å] and two π-π inter-actions between the thienyl and benzene rings are observed. The centroid-centroid distances of ...[more]

PMID: 21203288

Similar Datasets

3-(2-Chloro-6-fluoro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

Project description:The title chalcone derivative, C(13)H(8)ClFOS, crystallized as an inversion twin with two independent mol-ecules in the asymmetric unit. The thio-phene rings in both mol-ecules are disordered over two sites: the ratios of occupancies for the major and minor components in the two mol-ecules 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 thio-phene and benzene rings are 1.13 (18) and 2.2 (6)°, respectively, in one mol-ecule, with corresponding values 6.09 (17) and 1.3 (6)° in the other. Weak intra-molecular C-H⋯O and C-H⋯F inter-actions involving the prop-2-en-1-one group generate an S(5)S(5) ring motif, whereas a weak intra-molecular C-H⋯Cl contact generates an S(6) ring motif. In the crystal structure, mol-ecules 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 inter-actions.

| S-EPMC2960501 | biostudies-literature

(2E)-1-(3-Chloro-phen-yl)-3-(4-chloro-phen-yl)prop-2-en-1-one.

Project description:The title compound, C(15)H(10)Cl(2)O, is a chalcone with 3-chloro-phenyl and 4-chloro-phenyl substituents bonded at the opposite ends of a propenone group, the biologically active region. The dihedral angle between mean planes of these two chloro-substituted benzene rings is 46.7 (7)° compared to 46.0 (1) and 32.4 (1)° in similar published sructures. The angles between the mean plane of the prop-2-en-1-one group and the mean planes of the 3-chloro-phenyl and 4-chloro-phenyl rings are 24.1 (2) and 29.63°, respectively. While no classical hydrogen bonds are present, weak inter-molecular C-H⋯π-ring inter-actions are observed, which contribute to the stability of crystal packing.

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(E)-3-(2-Chloro-phen-yl)-1-(4-chloro-phen-yl)prop-2-en-1-one.

Project description:The title compound, C(15)H(10)Cl(2)O, adopts an E configuration with respect to the C=C bond of the propenone unit. The dihedral angle between the two benzene rings is 32.4 (1)°. Intra-molecular C-H⋯O and C-H⋯Cl hydrogen bonds generate an S(5)S(5)S(5) motif. In addition, the crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

| S-EPMC2961505 | biostudies-literature

(E)-3-(2,4-Dichloro-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

Project description:In the title chalcone derivative, C(13)H(8)Cl(2)OS, the prop-2-en-1-one unit and the thio-phene and 2,4-dichloro-phenyl rings are each essentially planar. The inter-planar angle between the thio-phene and 2,4-dichloro-phenyl rings is 19.87 (6)°. Weak intra-molecular C-H⋯O and C-H⋯Cl inter-actions involving the prop-2-en-1-one unit generate an S(5)S(5) ring motif. In the crystal structure, mol-ecules 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 inter-actions. A π-π inter-action was also observed with a centroid-centroid distance of 3.6845 (6) Å.

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(E)-3-(3,4-Dimethoxy-phen-yl)-1-(2-thien-yl)prop-2-en-1-one.

Project description:The title compound, C(15)H(14)O(3)S, has two symmetry-independent mol-ecules in the asymmetric unit with almost identical geometry. The dihedral angle between the benzene and thio-phene rings is 1.61 (11)° in one mol-ecule and 7.21 (11)° in the other. In both mol-ecules, 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 inter-actions and π-π inter-actions involving the benzene and thio-phene rings, with centroid-centroid distances of 3.5249 (13) and 3.6057 (13) Å.

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(E)-1-(2-Thien-yl)-3-(2,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C(16)H(16)O(4)S, the enone fragment, thio-phene ring and benzene ring are individually essentially planar. The thio-phene 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 thio-phene ring and the benzene ring are twisted from each other by 13.92 (19)°. An intra-molecular C-H⋯O hydrogen bond generates an S(5)S(5) ring motif. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen-bonding inter-actions. In addition, a π-π stacking inter-action, 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.

| S-EPMC2962137 | biostudies-literature

(E)-1-(2-Thien-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Project description:The mol-ecule of the title heteroaryl chalcone, C(16)H(16)O(4)S, which consists of substituted thio-phene and benzene rings bridged by the prop-2-en-1-one group, is slightly twisted. The dihedral angle between the thio-phene and 3,4,5-trimethoxy-phenyl rings is 12.18 (4)°. The three meth-oxy groups have two different conformations; two meth-oxy 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 mol-ecules are linked in a face-to-side manner into chains along the c axis by weak C-H⋯O(enone) inter-actions. These chains are stacked along the b axis by weak C-H⋯O(meth-oxy) inter-actions.

| S-EPMC2969210 | biostudies-literature

1-(4-Chloro-phen-yl)-3-(3,4-dimethyl-phen-yl)prop-2-en-1-one.

Project description:The title compound, C(17)H(15)ClO, was prepared from 3,4-dimethyl-benzaldehyde and 4-chloro-hypnone by Aldol condensation. The dihedral angle formed by the two benzene rings is 48.91 (8)°. Only van der Waals forces affect the packing.

| S-EPMC3008096 | biostudies-literature

(2E)-1-(2,5-Dimethyl-3-thien-yl)-3-(2-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(16)H(16)O(2)S, 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-meth-oxy-phenyl and 2,5-dimethyl-thio-phene residues, respectively. The dihedral angle between the ring systems is 23.47?(5)°. In the crystal, mol-ecules are linked by weak C-H?? inter-actions and aromatic ?-? stacking [phenyl ring centroid-centroid separation = 3.6418?(11)?Å; thio-phene-thio-phene ring separation = 3.8727?(9)?Å].

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(2E)-1-(4-Amino-phen-yl)-3-(2-thien-yl)prop-2-en-1-one ethanol hemisolvate.

Project description:In the title compound, C(13)H(11)NOS·0.5C(2)H(6)O, the chalcone derivative is close to planar, the dihedral angle between the thio-phene and 4-amino-phenyl rings being 3.1 (2)°. The thio-phene ring is disordered over two orientations with occupancies of 0.842 (3) and 0.158 (3). In the crystal structure, mol-ecules are linked into chains along the b axis by N-H⋯O hydrogen bonds. The chains are crosslinked via N-H⋯π inter-actions involving the thio-phene ring. The ethanol solvent mol-ecule is also disordered over two positions, each with an occupancy of 0.25.

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