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Este estudo descreve a síntese e a estrutura de (1E,4E)-1-(3-clorofenil)-5-(2,6,6-trimetilciclohex-1-eno)penta-1,4-dien-3-ona (BC I) pela difração de raios X por monocristal e pela análise da Superfície de Hirshfeld (SH). Cálculos teóricos, tais como a Teoria Quântica de Átomos em Moléculas (QTAIM), orbitais moleculares de fronteira, Mapa de Potencial Eletrostático (MPE) e atribuições do espectro no infravermelho, foram calculados com o nível de teoria B3LYP/6-311++G(d,p). Também, este trabalho investigou o docking molecular contra o DNA e a atividade citotóxica contra duas linhagens de células tumorais. A molécula BC I tem uma conformação do tipo meia cadeira para o anel ciclohexeno e os arranjos supramoleculares são estabilizados pelas interações C6–H6…O1 e C7–H7…O1. Análises do MPE e de docking indicam um ataque eletrofílico que é passível de ocorrer sobre o grupo carbonil. Além disso, três estruturas cristalinas (2E,6E)-2,6-bis(4-etilbenzilideno) ciclohexanona (BH I), (2E,6E)-2,6-bis(2,4 diclorobenzilideno) ciclohexanona (BH II) e (2E,6E)-2,6-bis(4-clorobenzilideno ciclohexanona (BH III) de chalconas baseadas no núcleo ciclohexanona foram sintetizadas e descritas pela cristalografia de raios X e pela análise da SH. Cálculos teóricos usando orbitais moleculares de fronteira, MPE, energias das interações de hiperconjugação, correções de counterpoise, QTAIM e atribuições do espectro no infravermelho foram calculados com o nível de teoria ωB97X-D/6-311++G(d,p). Também, este trabalho determinou o poder calorífico por meio da bomba calorimétrica. O empacotamento cristalino para BH I é determinado pela interação C3–H3B…O1 e pelo contato de dihidrogênio C13–H13B…H13B–C13. Da mesma forma, o empacotamento cristalino para BH II é determinado pelas interações C10–H10A…O1, C20–H20…O1, C17–H17…Cl3 e pelo empilhamento π…π. Também para BH III o empacotamento cristalino é determinado pelas interações C6–H6…π, C10–H10B…Cl1 e pelo contato halogênio C1–Cl1…Cl2. O procedimento de counterpoise foi calculado para elucidar as forças de interação que conduzem os arranjos moleculares no estado sólido. Também as energias das interações de hiperconjugação e a análise de QTAIM foram calculados para provar a existência de interações intermoleculares e para classificar suas naturezas. Ademais, orbitais moleculares de fronteira e MPE foram calculados para estudar suas propriedades eletrônicas e a análise do valor calorífico revelou que os três compostos possuem capacidades caloríficas semelhantes a alguns combustíveis. his study describes the synthesis and structure of (1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one (BC I) by X-ray single-crystal diffraction and Hirshfeld Surface (HS) analysis. Theoretical calculations, such as Quantum Theory of Atoms in Molecules (QTAIM), frontier molecular orbital, Molecular Electrostatic Potential (MEP) map and infrared spectra assignments, were performed at the B3LYP/6-311++G(d,p) level of theory. Also, this work evaluates molecular docking against DNA and cytotoxic activity against two tumor cell lines. The BC I molecule has a half chair conformation of the cyclohexene ring, and the supramolecular arrangements are stabilized by C6–H6…O1 and C7–H7…O1 interactions. MEP and docking analyses indicate an electrophilic attack that is likely to occur on the carbonyl group. Besides, three crystal structures (2E,6E)-2,6-bis(4-ethylbenzylidene)cyclohexanone (BH I), (2E,6E)-2,6-bis(2,4-dichlorobenzylidene)cyclohexanone (BH II) and (2E,6E)-2,6-bis(4-chlorobenzylidene)cyclohexanone (BH III) of chalcone based on the cyclohexanone core were synthesized and described by X-ray crystallography and HS analysis. Theoretical calculations using frontier molecular orbital, MEP, hyperconjugative interaction energies, counterpoise procedure, QTAIM and infrared spectra assignments were calculated at ωB97X-D/6-311++G(d,p) level of theory. Besides, the calorific value is determined by the calorimetric pump. The crystal packing for BH I is determined by C3–H3B…O1 interaction and C13–H13B…H13B–C13 dihydrogen contact. Likewise, the crystal packing for BH II is determined by C10–H10A…O1, C20–H20…O1, C17–H17…Cl3 interactions and π…π stacking. Also, for BH III the crystal packing is determined by C6–H6…π, C10–H10B…Cl1 interactions and halogen C1–Cl1…Cl2 contact. The counterpoise procedure was calculated to elucidate the interaction forces that drive the molecular arrangements in the solid-state. Also, hyperconjugative interaction energies and QTAIM analysis were calculated to prove the existence of intermolecular interactions and to classify their nature. Additionally, frontier molecular orbital and MEP were calculated to study their electronic properties and the calorific value analysis revealed that the three compounds have similar calorific capabilities to some fuels. Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES Fundação de Apoio à pesquisa do Estado de Goiás - FAPEG

The title bis­chalcone shows s-trans and s-cis conformations for its C=C—C=O bonds., In the title bis­chalcone, C17H12Br2O, the olefinic double bonds are almost coplanar with their attached 4-bromo­phenyl rings [torsion angles = −10.2 (4) and −6.2 (4)°], while the carbonyl double bond is in an s-trans conformation with with respect to one of the C=C bonds and an s-cis conformation with respect to the other [C=C—C=O = 160.7 (3) and −15.2 (4)°, respectively]. The dihedral angle between the 4-bromo­phenyl rings is 51.56 (2)°. In the crystal, mol­ecules are linked into a zigzag chain propagating along [001] by weak C—H⋯π inter­actions. The conformations of related bis­chalcones are surveyed and a Hirshfeld surface analysis is used to investigate and qu­antify the inter­molecular contacts.

In the bis­chalcone mol­ecule, the central benzene and terminal hy­droxy­phenyl rings form a dihedral angle of 14.28 (11)° and the central C=C double bond adopts a trans conformation. In the crystal, the title mol­ecule and solvate are linked by O—H⋯O hydrogen bonds., In the bis­chalcone mol­ecule of the title compound, C24H18O4·2C3H7NO, the central benzene and terminal hy­droxy­phenyl rings form a dihedral angle of 14.28 (11)° and the central C=C double bond adopts a trans configuration. In the crystal, the bis­chalcone and solvate mol­ecules are inter­connected via O—H⋯O hydrogen bonds, which were investigated by Hirshfeld surface analysis. Solid-state fluorescence was measured at λex = 4400 Å. The emission wavelength appeared at 5510 Å, which corresponds to yellow light and the solid-state fluorescence quantum yield (F f) is 0.18.

The three title compounds are centrosymmetric. Their packing features chains linked by either pairwise C—H⋯O or C—H⋯π inter­actions., In the title compounds, (2E,2′E)-3,3′-(1,4-phenyl­ene)bis­[1-(2-meth­oxy­phen­yl)prop-2-en-1-one], C26H22O4 (I), (2E,2′E)-3,3′-(1,4-phenyl­ene)bis­[1-(3-meth­oxy­phen­yl)prop-2-en-1-one], C26H22O4 (II) and (2E,2′E)-3,3′-(1,4-phenyl­ene)bis­[1-(3,4-di­meth­oxy­phen­yl)prop-2-en-1-one], C28H26O6 (III), the asymmetric unit consists of a half-mol­ecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98 (8), 7.74 (7) and 7.73 (7)° for (I), (II) and (III), respectively. In the crystal of (I), mol­ecules are linked by pairs of C—H⋯π inter­actions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C—H⋯O hydrogen bonds, forming R 2 2(16) and R 2 2(14) ring motifs, respectively, as parts of [201] and [101] chains, respectively.

In this paper, new (2E, 2'E)-3, 3'-(((3- hydroxypropane-1, 2-diyl) bis (oxy)) bis (2, 1-phenylene)) bis (1-phenylprop-2-en-1-one) (2a) was prepared in good yield by condensation reaction of acetophenone with bisaldehyde (1a) in ethanolic NaOH solutions at room temperature. The (2E, 2'E)-3, 3'-(((3- hydroxypropane-1, 2-diyl) bis (oxy)) bis (2, 1-phenylene)) bis (1-phenylprop-2-en-1-one) (2a) was immediately reacted with phenyl hydrazine under refluxing conditions in the presence of potassium hydroxide to obtain the corresponding 2, 3-bis (2-(1, 3-diphenyl-4, 5-dihydro-1H-pyrazol-5-yl) phenoxy) propan-1-ol (3a). The newly synthesized compounds confirmed by melting point and TLC and their structure were established by various analytical techniques such as IR, 1H-NMR, 13C-NMR and elemental analysis.

WOS: 000470072800002 A series of 12 novel methyl- and halogen-substituted bischalcones containing an azo linkage was synthesized by a Claisen-Schmidt condensation between (E)-1-{4-[(4-acetyl-2-hydroxyphenyl)diazenyl]phenyl}ethanone and various araldehydes using microwave irradiation and conventional procedures and the results were compared. Karadeniz Technical University (BAP)Karadeniz Teknik University [2012/9181] The author(s) disclosed receipt of the following financial support for the research, authorship and/or publication of this article: This work received financial support from The Research Fund of Karadeniz Technical University (BAP, Project No. 2012/9181).