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

ABSTRACT: 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.

SUBMITTER: Suwunwong T

PROVIDER: S-EPMC2969210 | biostudies-other | 2009

REPOSITORIES: biostudies-other

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

Suwunwong Thitipone T Chantrapromma Suchada S Pakdeevanich Paradorn P Fun Hoong-Kun HK

Acta crystallographica. Section E, Structure reports online 20090613 Pt 7

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 structu ...[more]

PMID: 21582853

Similar Datasets

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

Project description:In the title compound, C(18)H(17)BrO(4), the dihedral angle between the 4-bromo-phenyl and 3,4,5-trimethoxy-phenyl rings is 44.18?(6)°. In the crystal structure, the mol-ecules are linked by C-H?O and C-H?? inter-actions.

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1-Phenyl-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(18)H(18)O(4), a derivative of biologically active chalcones, the dihedral angle between the two rings is 7.43?(7)°. The molecule adopts an E configuration about the central olefinic bonds. In the crystal, there are no strong inter-actions between the mol-ecules.

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1-Phenyl-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(18)H(18)O(4), the dihedral angle between the mean planes of the aromatic rings is 7.39 (6)°. The dihedral angles between the linking C-C=C-C plane and the phenyl and benzene rings are 11.27 (5) and 4.20 (5)°, respectively.

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(E)-1-(4-Bromo-phen-yl)-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

Project description:The mol-ecule of the title chalcone derivative, C(18)H(17)BrO(4), is twisted, the dihedral angle between the 4-bromo-phenyl and 2,4,6-trimethoxy-phenyl rings being 39.17?(6)°. The three meth-oxy groups are oriented in two different conformations whereby two meth-oxy groups are coplanar, whereas the third is twisted with respect to the attached benzene ring [C-O-C-C torsion angles of -2.84?(18), -2.80?(18) and -9.31?(18)°]. Weak intra-molecular C-H?O inter-actions generate two S(5) and one S(6) ring motifs. In the crystal structure, mol-ecules are linked into supra-molecular sheets parallel to the bc plane by weak C-H?O inter-actions. These sheets are stacked along the a axis. The crystal structure is further stabilized by weak C-H?? inter-actions.

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A second polymorph of (2E)-1-(4-fluoro-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

Project description:The crystal structure of the title compound, C(18)H(17)FO(4), reported here is a polymorph of the structure first reported by Patil et al. [Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A (2007), 461, 123-130]. It is a chalcone analog and consists of substituted phenyl rings bonded at the opposite ends of a propenone group, the biologically active region. The dihedral angle between the mean planes of the aromatic rings within the 4-fluoro-phenyl and trimethoxy-phenyl groups is 28.7?(1)° compared to 20.8?(6)° in the published structure. The angles between the mean plane of the prop-2-ene-1-one group and the mean plane of aromatic rings within the 4-fluoro-phenyl and trimethoxy-phenyl groups are 30.3?(4) and 7.4?(7)°, respectively, in contast to 10.7?(3) and 12.36° for the polymorph. While the two 3-meth-oxy groups are in the plane of the trimeth-oxy-substituted ring, the 4-meth-oxy group is in a synclinical [-sc = -78.1?(2)°] or anti-clinical [+ac = 104.0?(4)°] position, compared to a +sc [53.0?(4)°] or -ac [-132.4?(7)°] position. While no classical hydrogen bonds are present, weak inter-molecular C-H??-ring inter-actions are observed which contribute to the stability of the crystal packing. The two polymorphs crystallize in the same space group, P2(1)/c, but have different cell parameters for the a, b and c axes and the ? angle. A comparison of the mol-ecular geometries of both polymorphs to a geometry optimized density functional theory (DFT) calculation at the B3-LYP/6-311+G(d,p) level for each structure provides additional support to these observations.

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(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.

| S-EPMC2960483 | biostudies-literature

(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.

| S-EPMC2962071 | biostudies-literature

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

Project description: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.

| S-EPMC2962207 | biostudies-literature

(2E)-1-(2-Bromo-phen-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

Project description:In the chalcone title compound, C(18)H(17)BrO(4), the dihedral angle between the mean planes of the 2-bromo- and 3,4,5-trimethoxy-substituted benzene rings is 89.3?(1)°. The angles between the mean plane of the prop-2-en-1-one group and the 2-bromo-phenyl and 3,4,5-trimeth-oxy-phenyl ring planes are 59.7?(1) and 40.5?(8)°, respectively. While no classical hydrogen bonds are present, three weak inter-molecular C-H?O inter-actions and weak C-H?Br and C-H?Cg ?-ring stacking inter-actions [C-H?Cg distance = 3.377?(2)?Å] are observed, which contribute to the stability of crystal packing.

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