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

ABSTRACT: 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.

SUBMITTER: Fun HK

PROVIDER: S-EPMC2961505 | biostudies-literature | 2008 May

REPOSITORIES: biostudies-literature

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

Fun Hoong-Kun HK Jebas Samuel Robinson SR Razak Ibrahim Abdul IA Patil P S PS Dharmaprakash S M SM Deepak D'Silva E E

Acta crystallographica. Section E, Structure reports online 20080530 Pt 6

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. ...[more]

PMID: 21202683

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(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??-ring inter-actions are observed, which contribute to the stability of crystal packing.

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

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

Project description:In the title chalcone derivative, C(15)H(9)Cl(3)O, the dihedral angle between the 2-chloro-phenyl and 2,4-dichloro-phenyl rings is 41.79?(14)°. Weak C-H?O and C-H?Cl intra-molecular inter-actions involving the enone unit generate S(5) ring motifs. In the crystal structure, the mol-ecules are arranged in a head-to-tail manner along the a axis. These chains are stacked along the b axis.

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

Project description:In the title compound, C(15)H(10)BrClO, the dihedral angle between mean planes of the bromo- and chloro-substituted benzene rings is 46.2?(2)° compared to 45.20?(9)° in the structure with the Cl substituent in the meta position of the aromatic ring. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-bromo-phenyl and 3-chloro-phenyl rings are 28.7?(5) and 24.2?(4)°, respectively. In the crystal, weak inter-molecular C-H?? inter-actions occur.

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

Project description:The title compound, C(16)H(13)ClO, adopts an E configuration with respect to the C=C double bond of the propenone unit. The dihedral angle between the two benzene rings is 45.9?(2)°. In the crystal structure, mol-ecules are arranged into sheets parallel to the ac plane and the sheets are stacked along the b axis. This arrangement is stabilized by weak inter-molecular C-H?? inter-actions involving both aromatic rings.

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

Project description:The title mol-ecule, C(16)H(13)ClO(2), is trans with respect to the C=C double bond. The dihedral angles between the mean plane of the prop-2-en-1-one unit and those of the 3-chloro- and 4-meth-oxy-substituted benzene rings are 20.93?(9) and 20.42?(10)°, respectively, and the dihedral angle between the mean planes of the two benzene rings is 40.96?(5)°. The crystal structure is stabilized by weak inter-molecular C-H?O hydrogen bonds, forming chains along the b axis.

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

Project description:In the title chalcone derivative, C(15)H(8)Cl(4)O, the C=C double bond exists in an E configuration and the dihedral angle between the two benzene rings is 48.13 (11)°. In the crystal, mol-ecules are arranged into columns and stacked down the a axis featuring possible weak aromatic π-π stacking inter-actions [centroid-centroid separation = 3.888 (2) Å].

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

Project description:In the title compound, C(15)H(10)BrClO, the dihedral angle between the mean planes of the benzene rings in the ortho-bromo- and para-chloro-substituted rings is 70.5 (6)°. The dihedral angles between the mean plane of the prop-2-en-1-one group and the mean planes of the benzene rings in the 4-chloro-phenyl and 2-bromo-phenyl rings are 14.9 (3) and 63.3 (8)°, respectively. In the crystal, inversion dimers linked by pairs of weak C-H⋯O interactions are observed as well as aromatic π-π stacking inter-actions.

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

Project description:In the title compound, C(15)H(10)ClNO(3), a substituted chalcone, the 2-chloro-phenyl and 4-nitro-phenyl rings make a dihedral angle of 26.48 (6)°. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Weak intra-molecular C-H⋯O and C-H⋯Cl inter-actions involving the enone groups generate S(5) ring motifs, which help to stabilize the planarity of the 3-(2-chloro-phen-yl)prop-2-en-1-one segment of the mol-ecule. In the crystal structure, adjacent mol-ecules are stacked in a head-to-tail fashion into columns along the a axis by π-π inter-actions [centroid-centroid distance = 3.6955 (8) Å]. Neighbouring columns are linked by weak C-H⋯O inter-actions.

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

Project description:The title compound, C(15)H(12)ClNO, a substituted chalcone, adopts an E configuration with respect to the C=C bond of the enone unit. The mol-ecule is not planar, as can be seen from the dihedral angle of 28.9 (2)° between the two rings which are twisted from each other. The enone segment of the mol-ecule is not coplanar with the chloro-phenyl ring, making a dihedral angle of 23.4 (3)° with it. The amino group is also not coplanar with the ring to which it is bound, making a dihedral angle of 35 (4)°. In the crystal structure, adjacent mol-ecules are linked by N-H⋯O inter-actions into one-dimensional infinite chains along the c axis, and are further stacked as one-dimensional zigzag chains down the b axis, forming two-dimensional extended networks parallel to the bc plane.

| S-EPMC2959457 | biostudies-literature

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