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

ABSTRACT: 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.

SUBMITTER: Zainuri DA

PROVIDER: S-EPMC5946975 | biostudies-literature |

REPOSITORIES: biostudies-literature

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

Project description: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.

| S-EPMC4644999 | biostudies-literature

The effect of the fused-ring substituent on anthracene chalcones: crystal structural and DFT studies of 1-(anthracen-9-yl)-3-(naphthalen-2-yl)prop-2-en-1-one and 1-(anthracen-9-yl)-3-(pyren-1-yl)prop-2-en-1-one.

Project description:The title chalcone compounds, C27H18O (I) and C33H20O (II), were synthesized using a Claisen-Schmidt condensation. Both compounds display an s-trans configuration of the enone moiety. The crystal structures feature inter-molecular C-H?O and C-H?? inter-actions. Quantum chemical analysis of density functional theory (DFT) with a B3LYP/6-311++G(d,p) basis set has been employed to study the structural properties of the compound. The effect of the inter-molecular inter-actions in the solid state are responsible for the differences between the experimental and theoretical optimized geometrical parameters. The small HOMO-LUMO energy gap in (I) (exp?: 3.18?eV and DFT: 3.15?eV) and (II) (exp?: 2.76?eV and DFT: 2.95?eV) indicates the suitability of these compounds for optoelectronic applications. The inter-molecular contacts and weak contributions to the supra-molecular stabilization are analysed using Hirshfeld surface analysis.

| S-EPMC5947480 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and DFT studies of 1,3-bis-[2-meth-oxy-4-(prop-2-en-1-yl)phen-oxy]propane.

Project description:The asymmetric unit of the title compound, C23H28O4, comprises two half-mol-ecules, with the other half of each mol-ecule being completed by the application of twofold rotation symmetry. The two completed mol-ecules both have a V-shaped appearance but differ in their conformations. In the crystal, each independent mol-ecule forms chains extending parallel to the b axis with its symmetry-related counterparts through C-H⋯π(ring) inter-actions. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (65.4%), H⋯C/C⋯H (21.8%) and H⋯O/O⋯H (12.3%) inter-actions. Optimized structures using density functional theory (DFT) at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structures in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

| S-EPMC7057369 | biostudies-literature

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.

| S-EPMC3007353 | biostudies-literature

(E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluoro-phen-yl)prop-2-en-1-one: crystal structure and Hirshfeld surface analysis.

Project description:In the title compound, C23H14ClFO, the enone moiety adopts an E conformation. The dihedral angle between the benzene and anthracene ring is 63.42?(8)° and an intra-molecular C-H?F hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are arranged into centrosymmetric dimers via pairs of C-H?F hydrogen bonds. The crystal structure also features C-H?? and ?-? inter-actions. Hirshfeld surface analysis was used to confirm the existence of inter-molecular inter-actions.

| S-EPMC4908534 | biostudies-literature

Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitro-phen-yl)prop-2-en-1-one.

Project description:The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethyl-ene C=C and carbonyl C=O double bonds in the enone unit. The mol-ecule is significantly twisted with a dihedral angle of 48.63?(14)° between the anthracene ring system and the benzene ring. In the crystal, mol-ecules are linked into inversion dimers with an R 2 2(10) graph-set motif via pairs of C-H?O hydrogen bonds. The inter-molecular inter-actions were analysed and qu-anti-fied by Hirshfeld surface analysis. The mol-ecular structure was optimized and a small HOMO-LUMO energy gap of 2.55?eV was obtained using the DFT method at the B3LYP/6-311?G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52?eV obtained from the UV-vis analysis. The crystal used was a two-component merohedral twin with a refined ratio of 0.1996?(16):0.8004?(16).

| S-EPMC6505597 | biostudies-literature

Mol-ecular structure, DFT studies and UV-Vis absorption of two new linear fused ring chalcones: (E)-1-(anthracen-9-yl)-3-(2-meth-oxy-phen-yl)prop-2-en-1-one and (E)-1-(anthracen-9-yl)-3-(3-fluoro-4-meth-oxy-phen-yl)prop-2-en-1-one.

Project description:The title compounds, C24H18O2 and C24H17FO2, were synthesized using the Claisen-Schmidt condensation method and characterized by UV-Vis spectroscopy. Weak inter-molecular C-H⋯O, C-H⋯π and π-π hydrogen-bonding inter-actions help to stabilize the crystal structures of both compounds. The geometrical parameters obtained from the mol-ecular structure were optimized using density functional theory (DFT) calculations at the B3LYP/6-311++G(d,p) level, showing a good correlation with the experimental results. The small HOMO-LUMO energy gaps of 3.11 and 3.07 eV enhances the non-linear responses of these mol-ecular systems.

| S-EPMC6072983 | biostudies-literature

(E)-3-(Anthracen-9-yl)-1-(4-bromo-phen-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C(23)H(15)BrO, the prop-2-en-1-one unit is planar and it makes dihedral angles of 20.9?(1) and 45.8?(1)°, respectively, with the 4-bromo-phenyl ring and the anthracene ring system. The interplanar angle between the 4-bromophenyl ring and the anthracene ring system is 35.52?(7)°. In the crystal structure, mol-ecules are linked into dimers by C-H?Br hydrogen bonds, and the dimers are linked into a zigzag network parallel to the bc plane by weak C-H?O hydrogen bonds and C-H?? inter-actions involving the central benzene ring of the anthracene ring system.

| S-EPMC2968141 | biostudies-literature

(E)-3-(Anthracen-9-yl)-1-(2-bromo-phen-yl)prop-2-en-1-one.

Project description:The mol-ecule of the title chalcone, C(23)H(15)BrO, is not planar and exists in the E configuration with respect to the central C=C bond. The dihedral angle between the benzene and anthracene rings is 83.58?(6)°. The prop-2-en-1-one bridge makes dihedral angles of 63.00?(7) and 42.62?(16)° with the benzene and anthracene rings, respectively. In the crystal, mol-ecules are linked into dimers by weak C-H?O inter-actions. These dimers are arranged parallel to the bc plane and are further stacked along the a axis by ?-? inter-actions with a centroid-centroid distance of 3.7561?(9)?Å. The crystal structure is further stabilized by C-H?? inter-actions.

| S-EPMC3011387 | biostudies-literature

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