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Crystal structure of (E)-1,3-bis-(6-methoxy-naphthalen-2-yl)prop-2-en-1-one.

ABSTRACT: In the title compound, C25H20O3, the central -C(=O)-C=C- chain is disordered over two positions about the central C atom, with an occupancy ratio of 0.848 (6):0.152 (6). The mol-ecule is twisted with the two naphthalene ring systems being inclined to one another by 52.91 (9)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming a three-dimensional structure. The structure was refined as a two-component twin with a 180 ° rotation about the c* axis.

SUBMITTER: Patel PN

PROVIDER: S-EPMC4644999 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(E)-1,3-Bis(anthracen-9-yl)prop-2-en-1-one: crystal structure and DFT study.

Project description:The title compound, C31H20O, was synthesized using a Claisen-Schmidt condensation. The enone group adopts an s-trans conformation and the anthracene ring systems are twisted at angles of 85.21 (19) and 83.98 (19)° from the enone plane. In the crystal, mol-ecules are connected into chains along [100] via weak C-H⋯π inter-actions. The observed band gap of 3.03 eV is in excellent agreement with that (3.07 eV) calculated using density functional theory (DFT) at the B3LYP/6-311++G(d,p) level. The Hirshfeld surface analysis indicates a high percentage of C⋯H/H⋯C (41.2%) contacts in the crystal.

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

Project description:In the title compound, C(15)H(9)BrCl(2)O, the two benzene rings are twisted from each other with a dihedral angle of 47.33?(8)°. The crystal structure is stabilized by aromatic ?-? inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.680?(2)?Å], and by weak inter-molecular C-H?O and C-H?Cl inter-actions. Additionally, the crystal structure exhibits a short intra-molecular C-H?Br contact (H?Br = 2.69?Å).

| S-EPMC2971337 | biostudies-literature

(E)-1,3-Bis(2,3,4,5,6-penta-fluoro-phen-yl)prop-2-en-1-one.

Project description:In the title compound, C(15)H(2)F(10)O, the two perfluorinated arene rings are tilted at an angle of 66.08?(5)° with respect to each other. The olefinic double bond adopts an E configuration and the single bond between the olefinic and carbonyl double bonds has an s-trans conformation. The carbonyl group is not in a coplanar alignment with respect to the neighbouring arene ring (0.963?Å from aryl plane) while being coplanar with regard to the olefinic double bond (0.0805?Å from olefinic bond). The crystal packing does not feature significant hydrogen-bond-type or stacking inter-actions.

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Crystal structure of (E)-1-(1-hy-droxy-naphthalen-2-yl)-3-(2,3,4-tri-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:The title compound, C22H20O5, is composed of a hy-droxy-naphthyl ring and a tri-meth-oxy-phenyl ring [the planes of which are inclined to one another by 21.61?(10)°] bridged by an unsaturated prop-2-en-1-one group. The mean plane of the prop-2-en-1-one group [-C(=O)-C=C-] is inclined to that of the naphthyl system and benzene rings by 3.77?(14) and 18.01?(16)°, respectively. There is an intra-molecular O-H?O hydrogen bond present forming an S(6) ring motif. In the crystal, inversion-related mol-ecules are linked by a slipped-parallel ?-? inter-action [inter-centroid distance = 3.8942?(13)?Å, inter-planar distance = 3.478?(9)?Å and slippage = 1.751?Å], and stack along the [101] direction. There are no other significant inter-molecular inter-actions present.

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(Z)-1,3-Bis(4-chloro-phen-yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C(17)H(11)Cl(2)N(3)O, the C=C bond connecting the triazole and 4-chloro-phenyl groups adopts a Z geometry. The dihedral angles formed by the triazole ring and the 4-chloro substituted benzene rings are 67.3?(1) and 59.1?(1)°. The dihedral angle between the two benzene rings is 73.5?(1)°.

| S-EPMC3344571 | biostudies-literature

Crystal structure of 3-[4-(1-methyl-eth-yl)phen-yl]-1-(naphthalen-2-yl)prop-2-en-1-one.

Project description:The title compound, C22H20O, was synthesized by reacting 4-iso-propyl-benzaldehyde with 2-acetonaphtone by aldolic condensation under Claisen-Schmidt conditions. The mol-ecule consists of a naphthalene group and a benzene ring with a pendant isopropyl moiety, both rings bound by a propenone linker. The naphthalene ring system is almost planar [maximum deviation from the least-squares plane = 0.026?(10)?Å] and subtends a dihedral angle of 52.31?(4)° with the benzene ring. The propenone linker, in turn, deviates slightly more from planarity [maximum deviation = 0.125?(18)?Å] and has its least-squares plane oriented midway the former two, at 25.62?(6) and 28.02?(5)° from the naphthalene ring system and the benzene ring, respectively. Finally, the isopropyl group presents its CC2 plane almost perpendicular to the benzene ring, at 85.30?(4)°. No significant hydrogen bonding or ?-? stacking inter-actions are found in the crystal structure.

| S-EPMC4186083 | biostudies-other

3-(4-Methoxy-phen-yl)-1-(2-pyrrol-yl)prop-2-en-1-one.

Project description:The title mol-ecule, C(14)H(13)NO(2), is almost flat with a dihedral angle of 8.0?(1)° between the pyrrole and benzene rings. The central C(3)O ketone unit has an s-cis conformation and is also coplanar with a torsion angle of -0.6?(3) °. An intra-molecular C-H?O hydrogen bond generates an S(5) ring motif. In addition, the meth-oxy group is coplanar with the attached benzene ring. In the crystal structure, neighboring mol-ecules are paired through N-H?O hydrogen bonds into centrosymmetric dimers with an R(2) (2)(10) motif.

| S-EPMC2959486 | biostudies-literature

3-(4-Methoxy-phen-yl)-1-(2-nitrophen-yl)prop-2-en-1-one.

Project description:The title compound, C(16)H(13)NO(4), was prepared from 2-nitrylhypnone [systematic name: 1-(2-nitrophenyl)ethanone] and 4-methoxy-benzophenone by a Claisen-Schmidt condensation. The dihedral angle formed by the two benzene rings is 80.73 (2). The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds.

| S-EPMC2971945 | biostudies-literature

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

Project description: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.

| S-EPMC3089117 | biostudies-literature

(Z)-3-(9-Anthr-yl)-1-(4-methoxy-phen-yl)prop-2-en-1-one.

Project description:The title chalcone derivative, C(24)H(18)O(2), which consists of the substituted 4-methoxy-phenyl and anthracene rings bridged by the prop-2-en-1-one unit, exists in a cis configuration. The mol-ecule is twisted, the inter-planar angle between the benzene and anthracene rings being 69.50?(10)°. The meth-oxy group is coplanar with the attached benzene ring [C-O-C-C angle = 2.9?(3)°]. In the crystal structure, mol-ecules are linked into chains along the a axis by a weak C-H?O(enone) inter-action. The chains are stacked along the c axis. A C-H?? inter-action involving the benzene ring is observed.

| S-EPMC2971453 | biostudies-literature

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