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

ABSTRACT: The mol-ecule of the title chalcone derivative, C(19)H(15)NO, exists in a trans configuration with respect to the C=C double bond. The mol-ecule is slightly twisted with a dihedral angle of 6.12?(12)° between the benzene ring and the naphthalene ring system. The prop-2-en-1-one bridge is nearly planar, with an r.m.s. deviation of 0.0194?(2), and makes dihedral angles of 8.05?(19) and 11.47?(18)° with the benzene ring and the naphthalene ring system, respectively. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds into chains along the b axis. Weak N-H?? and C-H?? inter-actions and a short N?O contact [2.974?(4)?Å] are also observed.

SUBMITTER: Kobkeatthawin T

PROVIDER: S-EPMC3089117 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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

Kobkeatthawin Thawanrat T Chantrapromma Suchada S Saewan Nisakorn N Fun Hoong-Kun HK

Acta crystallographica. Section E, Structure reports online 20110422 Pt 5

The mol-ecule of the title chalcone derivative, C(19)H(15)NO, exists in a trans configuration with respect to the C=C double bond. The mol-ecule is slightly twisted with a dihedral angle of 6.12 (12)° between the benzene ring and the naphthalene ring system. The prop-2-en-1-one bridge is nearly planar, with an r.m.s. deviation of 0.0194 (2), and makes dihedral angles of 8.05 (19) and 11.47 (18)° with the benzene ring and the naphthalene ring system, respectively. In the crystal, mol-ecules are l ...[more]

PMID: 21754504

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3-[4-(Dimethyl-amino)-phen-yl]-1-(4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octa-hydro-naphthalen-2-yl)prop-2-en-1-one.

Project description:The title compound, C(23)H(31)NO, was semisynthesized from isocostic acid, isolated from the aerial part of Inula Viscosa- (L) Aiton [or Dittrichia Viscosa- (L) Greuter]. The cyclo-hexene ring has a half-chair conformation, whereas the cyclo-hexane ring displays a chair conformation. The dihedral angle between the latter ring and its substituent is 83.6?(7)°.

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1-(4-Amino-phen-yl)-3-[2-(trifluoro-meth-yl)phen-yl]prop-2-en-1-one.

Project description:The title compound, C(16)H(12)F(3)NO, a derivative of biologically active chalcones, comprises two benzene rings and a central -CH=CH-C(=O)- unit. The dihedral angle between the two rings is 10.9?(1)° and the mol-ecule adopts an E configuration about the central olefinic bond. The crystal structure is stabilized by inter-molecular N-H?O and N-H?N hydrogen bonds.

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

Project description:The title compound, C(15)H(11)Cl(2)NO, is approximately planar (r.m.s. deviation = 0.062?Å) and contains a single C=C double bond in a trans (E) configuration. The crystal packing is stabilized by intermolecular N-H?N and N-H?O inter-molecular hydrogen bonding.

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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.

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(E)-3-[4-(Dimethyl-amino)phen-yl]-1-(4-methyl-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(18)H(19)NO, the dihedral angle between 4-methyl-phenyl and 4-(dimethyl-amino)phenyl rings is 45.5?(3)°. The C-C=C-C torsion angle of 173.8?(3)° indicates that the mol-ecule adopts an E configuration. The dimethyl-amino group is nearly coplanar with the attached benzene ring, making a dihedral angle of 2.7?(3)°. Weak inter-molecular C-H?? inter-actions are observed in the crystal structure.

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

Project description:Mol-ecules of the title amino-chalcone, C(18)H(19)NO(4), are twisted, with a dihedral angle of 11.26?(6)° between the 4-amino-phenyl and 2,4,5-trimeth-oxy-phenyl rings. The conformations of the three meth-oxy groups with respect to the benzene ring are slightly different. Two meth-oxy groups are almost coplanar with the attached benzene ring [C-O-C-C torsion angles of -1.45?(19) and 1.5?(2)°], while the third is (-)-synclinal with the attached benzene ring [C-O-C-C = -81.36?(17)°]. In the crystal structure, mol-ecules are stacked into columns along the b axis and mol-ecules in adjacent columns are linked by N-H?O hydrogen bonds into V-shaped double columns. Weak ?-? inter-actions are also observed, with a centroid-centroid distance of 3.7532?(8)?Å.

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

Project description:In the asymmetric unit of the title chalcone derivative, C(18)H(19)NO(4), there are three crystallographically independent mol-ecules (mol-ecules A, B and C). In mol-ecule A, the dihedral angle between two benzene rings is 12.22 (10)° and the plane of the central prop-2-en-1-one unit makes dihedral angles of 11.02 (13) and 2.64 (12)° with the two adjacent benzene rings. The corresponding angles in mol-ecule B are 12.35 (10), 18.78 (12) and 7.29 (12)°, respectively, and those in mol-ecule C are 15.40 (10), 15.62 (3) and 3.19 (13)°. In each mol-ecule, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, the mol-ecules B are linked by inter-molecular N-H⋯O hydrogen bonds into a zigzag chain along the c axis, while the mol-ecules A and C are linked together via an N-H⋯O hydrogen bond into a dimer. Adjacent dimers are further connected by N-H⋯N hydrogen bonds into a three-dimensional network. Weak C-H⋯O and C-H⋯π inter-actions are also observed.

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(E)-1-(4-Chloro-phen-yl)-3-[4-(dimethyl-amino)phen-yl]prop-2-en-1-one.

Project description:The title compound, C(17)H(16)ClNO, was synthesized using a solvent-free method by reaction of 4-(dimethyl-amino)benzaldehyde with 4-chloro-acetophenone and NaOH. The chloro-phenyl ring makes a dihedral angle of 18.1 (3)° with the central propenone unit, while the (dimethyl-amino)phenyl group is disordered over two orientations of equal occupancies, which make dihedral angles with the central propenone unit of 32.9 (3) and 57.4 (3)°, respectively.

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(2E)-3-[4-(Dimethyl-amino)-phen-yl]-1-(4-fluoro-phen-yl)prop-2-en-1-one.

Project description:The mean planes of the two benzene rings in the title compound, C(17)H(16)FNO, are twisted slightly, making a dihedral angle of 7.8 (1)°. The prop-2-en-1-one group is also twisted slightly with a C-C-C-O torsion angle of -11.6 (3)°. In the crystal, weak inter-molecular C-H⋯O inter-actions link pairs of mol-ecules, forming centrosymmetric dimers.

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