Small Dihedral Angle Research Articles

Push‐Pull N‐Annulated Perylene‐Based Sensitizers for Dye‐Sensitized Solar Cells: Theoretical Property Tuning by DFT/TDDFT

AbstractWe evaluate the effects of donor and π‐linker moieties on power‐conversion efficiency for a series of push‐pull type, N‐annulated perylene dyes for dye‐sensitized solar cells. Triphenylamine and diphenylamine are used as electron donors. We investigate the structural, optical, and electronic properties of dyes by performing density functional theory (DFT) calculations at the B3LYP level, using the 6‐311G(d,p) basis set. Electronic absorption wavelengths were investigated using time dependent DFT (TD‐DFT) calculations on M062x/6‐311G(d,p) in THF. Our calculated results reveal that the diphenylamine (DPA) donor provides a small dihedral angle between diphenylamine and the perylene core, resulting in a red‐shifted absorption spectrum. Introduction of an O‐methoxy substituent into diphenylamine improves its donor properties, red‐shifts the absorption wavelength, and increases the dipole moment, indicating increased intramolecular charge transfer in the O‐methoxy substituted dye. Incorporation of a C‐C triple bond in linker extends the π‐conjugation system and decreases the dihedral angle between N‐annulated perylene and cyanoacrylic acid; the dye adopts a planar structure, causing a red‐shift in the absorption spectrum. Our results demonstrate that use of computational design can to help the experimentalist for out looking future developments to identify push‐pull perylene sensitizers for highly efficient solar cells.

Domain decomposition approach for parallel improvement of tetrahedral meshes

Presently, a tetrahedral mesher based on the Delaunay triangulation approach may outperform a tetrahedral improver based on local smoothing and flip operations by nearly one order in terms of computing time. Parallelization is a feasible way to speed up the improver and enable it to handle large-scale meshes. In this study, a novel domain decomposition approach is proposed for parallel mesh improvement. It analyses the dual graph of the input mesh to build an inter-domain boundary that avoids small dihedral angles and poorly shaped faces. Consequently, the parallel improver can fit this boundary without compromising the mesh quality. Meanwhile, the new method does not involve any inter-processor communications and therefore runs very efficiently. A parallel pre-processing pipeline that combines the proposed improver and existing parallel surface and volume meshers can prepare a quality mesh containing hundreds of millions of elements in minutes. Experiments are presented to show that the developed system is robust and applicable to models of a complication level experienced in industry.

A trilobal non-fullerene electron acceptor based on benzo[1,2-b:3,4-b′:5,6-b″] trithiophene and perylenediimide for polymer solar cells

A trilobal non-fullerene electron acceptor, BTT-3PDI, incorporating benzo[1,2-b:3,4-b′:5,6-b″]trithiophene (BTT) as the core and three bay-substituted perylenediimides (PDIs) as the arms, was designed and synthetized. It shows a high electron mobility of 3.69×10−3cm2V−1s−1 because it is a crystalline semiconductor for the partially conjugated structure between PDI units and BTT core. BTT-3PDI shows a matched energy levels and a complementary absorption spectrum with PTB7-Th. The conventional polymer solar cells were fabricated without any processing additive or posttreatment. It showed a power conversion efficiency (PCE) of 1.35% because the unconspicuous microphase separation of the blend film leads to low electron mobility (1.67×10−5cm2V−1s−1) and hole mobility (2.80×10−5cm2V−1s−1). The study provides a proof that the crystalline PDI derivative with small dihedral angles between a core and PDI units can also avoid serious molecular aggregation and large phase separation in the active layer.

Local partial melting of the lower crust triggered by hydration through melt–rock interaction: an example from Fiordland, New Zealand

ABSTRACTWe investigate a low‐strain outcrop of the lower crust, the Pembroke Granulite, exposed in northern Fiordland, New Zealand, which exhibits localized partial melting. Migmatite and associated tschermakite–clinozoisite (TC) gneiss form irregular, elongate bodies that cut a two‐pyroxene–pargasite (PP) gneiss. Gradational boundaries between rock types, and the progressive nature of changes in mineral assemblage, microstructure and chemistry are consistent with the TC gneiss and migmatite representing modified versions of the PP gneiss. Modification is essentially isochemical, where partial modification involves hydration of the assemblage and mineral chemistry changes, and complete modification involves additional recrystallization and in situ partial melt production. Microstructures of quartz and plagioclase, including small dihedral angles, string of beads textures and films surrounding amphibole and garnet grains are consistent with the former presence of melt in modified rock types. The documented rock modification is attributed to melt–rock interaction occurring during porous melt flow of a dominantly externally derived, hydrous silicate melt. Microstructures indicate melt flow occurred along grain boundaries and field relationships show it was focused into channels tens of metres wide, with preference for following the pre‐existing foliation. Melt–rock interaction at the grain scale resulted in hydration and modification of the host PP gneiss, which resulted in localized partial melting. These relationships indicate prograde hydration during localized melt–rock interaction drove migmatization of the lower crust.

Degenerate tetrahedra removal

Standard 3D mesh generation algorithms may produce a low quality tetrahedral mesh, i.e., a mesh where the tetrahedra have very small dihedral angles. In this paper, we propose a series of operations to recover these badly-shaped tetrahedra.In particular, we will focus on the shape of these undesired mesh elements by proposing a novel method to distinguish and classify them. For each of these configurations, we apply a suitable sequence of operations to get a higher mesh quality. Finally, we employ a random algorithm to avoid locks and loops in the procedure.The reliability of the proposed mesh optimization algorithm is numerically proved with several examples.

Synthesis and Sintering of LaCo<sub>1-X</sub>Fe<sub>x</sub>O<sub>3</sub> Ceramics: Microstructure Analysis

This work intends to show the effect of the iron ion doping in LaCoO3 perovskite, both in powders and in sintered samples obtained from combustion reaction route. The phase formation and particle morphology and particle size distribution of the powders were analysed by XRD, SEM and sedimentation techniques, respectively. Relative density, microstructure (secondary phases and grain size) and pore size distribution of LaCo1-xFexO3 sintered ceramics have been investigated by SEM/EDS and Hg porosimetry analysis. Although LaCo1-xFexO3 powders obtained from combustion reaction exhibited smaller grain sizes when sintered at high temperatures, they showed higher volume fraction of secondary phases. The presence of these crystalline phases in addition to the desired perovskite affected the microstructure acting as grain growth inhibitors by grain boundary pinning. It is believed by observing three grain junction pores that LaFeO3 phase has a smaller dihedral angle than LaCoO3. This fact would explain why LaFeO3 presented a smaller driving force for sintering with higher tendency of pore and inclusion coarsening at higher temperatures (1400°C).

Crystal Structures of 2-Phenyl-2H-1,2,3-Triazol-4-Carbaldehyde, an Active α-Glycosidase Inhibition Agent, and (1-Phenyl-1H-1,2,3-Triazol-4-yl)Methyl Benzoate and (2-(4-Fluorophenyl)-2H-1,2,3-Triazole-4-yl)Methanol, Two Moderately Active Compounds

The crystal structures of (1-phenyl-1H-1,2,3-triazol-4-yl)methyl benzoate, 1a, (2-(4-fluorophenyl)-2H-1,2,3-triazole-4-yl)methanol, 2a, and 2-phenyl-2H-1,2,3-triazol-4-carbaldehyde, 2b, are reported. Compounds 1a and 2a were recently reported to exhibit mild α-glycosidase inhibition activity, while compound 2b exhibited a much greater activity. Only small dihedral angles 6.52(4), 14.02(10) and 2.44(7)° are present between the triazolyl ring and the attached aryl rings in 1a, 2a and 2b, respectively. The relatively flat compounds 2a and 2b contrast with compound 1a, which is “V” shaped, with a dihedral angle between the near planar phenyltriazolyl-CH2 and phenyl-CO2CH2 moieties of 88.11(4)°. The intermolecular interactions in 1a are C–H···X (X = N or π(triazole) and π(triazole) ···π(phenyl): two different chains are formed, from (i) combinations of the C–H···N hydrogen bonds and (ii) combinations of the C–H···π and π···π interactions.. The intermolecular interactions in 2a are C–H···O and C–F···π(phenyl): the C–H···O interactions generate a sheet of molecules, containing a network of rings.·Classical O–H···O hydrogen bonds, and weaker C–H···π(triazolyl) and π(phenyl)···π(triazolyl) interactions are present in 2b: all three interactions together generate a chevron-type arrangement. Compound 1a crystallizes in the monoclinic space group P21 with a = 4.5661(5), b = 10.5573(14), c = 13.9694(19) A, β = 90.594(6)° and Z = 2. Compound 2a crystallizes in the monoclinic space group P21 with a = 3.7175(7), b = 10.428(2), c = 10.689(3) A, β = 90.521(6)° and Z = 2. Compound 2b crystallizes in the monoclinic space group P21/c with a = 11.4130(5), b = 4.80280(10), c = 15.5916(11) A, β = 103.373(7)° and Z = 4. The relatively flat compounds, (2-(4-fluorophenyl)-2H-1,2,3-triazole-4-yl)methanol and 2-phenyl-2H-1,2,3-triazol-4-carbaldehyde, contrast with compound (1-phenyl-1H-1,2,3-triazol-4-yl)methyl benzoate, which is “V” shaped, with a dihedral angle between the near planar phenyltriazolyl-CH2 and phenyl-CO2CH2 moieties of 88.11(4) o.

Impact of Aromatic Ring Count on the Ability to Participate in Attractive Interactions. Crystal Structure (X-ray) and Solid State Computational (DFT/QTAIM/RDS/Hirshfeld-surfaces) Study of 1,4-di(2-phenyl-1H-imidazol-4-yl)benzene. A Potential Nanotechnology Intrinsic Component

The crystal structure of 1,4-di(2-phenyl-1H-imidazol-4-yl)benzene (DPI4B) is determined by X-ray diffraction with a final R-factor of 6.42% at room temperature. It crystallizes with a space group P21/c, Z = 4, a = 5.01790(10), b = 28.8971(6), and c = 12.9362(3) A; β = 98.757(2)°. Two 4-phenyl-1H-imidazole (4PI) fragments are related by inversion symmetry and each makes a dihedral angle of 0° with the benzene rings. Despite the presence of a total number of five homo- and heterocyclic rings in the DPI4B molecule, similarly to 2-phenyl-1H-imidazole (2PI) but in contrast to 1,4-di(1H-imidazol-4-yl)benzene (DI4B) and 4-phenyl-1H-imidazole (4PI), it is almost planar. Each plane containing a terminal phenyl ring makes a small dihedral angle of about 3° with the central benzene ring plane. The average twisting angle of the whole molecule is equal to 7°. The ordering of compounds studied according to the decreasing twisting angle is 4PI > DI4B > DPI4B > 2PI and is the same as that according to hydrogen bond lengt...

Partial melting of deeply subducted continental crust during exhumation: insights from felsic veins and host UHP metamorphic rocks in North Qaidam, northern Tibet

ABSTRACTA combined petrological, geochronological and geochemical study was carried out on felsic veins and their host rocks from the North Qaidam ultrahigh‐pressure (UHP) metamorphic terrane in northern Tibet. The results provide insights into partial melting of deeply subducted continental crust during exhumation. Partial melting is petrograpically recognized in metagranite, metapelite and metabasite. Migmatized gneisses, including metagranite and metapelite, contain microstructures such as granitic aggregates with varying outlines, small dihedral angles at mineral junctions and feldspar with magmatic habits, indicating the former presence of felsic melts. Partial melts were also present in metabasite that occurs as retrograde eclogite. Felsic veins in both the eclogites and gneisses exhibit typical melt crystalline textures such as large euhedral feldspar grains with straight crystal faces, indicating vein crystallization from anatectic melts. The Sr–Nd isotope compositions of felsic veins inside gneisses suggest melt derivation from anatexis of host gneisses themselves, but those inside metabasites suggest melt derivation from hybrid sources. Felsic veins inside gneisses exhibit lithochemical compositions similar to experimental melts on the An–Ab–Or diagram. In trace element distribution diagrams, they exhibit parallel patterns to their host rocks, but with lower element contents and slightly positive Eu and Sr anomalies. The geochemistry of these felsic veins is controlled by minerals that would decompose and survive, respectively, during anatexis. Felsic veins inside metabasites are rich either in quartz or in plagioclase with low normative orthoclase. In either case, they have low trace element contents, with significantly positive Eu and Sr anomalies in plagioclase‐rich veins. Combined with cumulate structures in some veins, these felsic veins are interpreted to crystallize from anatectic melts of different origins with the effect of crystal fractionation. Nevertheless, felsic veins in different lithologies exhibit roughly consistent patterns of trace element distribution, with variable enrichment of LILE and LREE but depletion of HFSE and HREE. There are also higher contents of trace elements in veins hosted by gneisses than veins hosted by metabasites. Anatectic zircon domains from felsic veins and migmatized gneisses exhibit consistent U–Pb ages of c. 420 Ma, significantly younger than the peak UHP eclogite facies metamorphic event at c. 450–435 Ma. Combining the petrological observations with local P–T paths and experimentally constrained melting curves, it is inferred that anatexis of UHP gneisses was caused by muscovite breakdown while anatexis of UHP metabasites was caused by fluid influx. These UHP metagranite, metapelite and metabasite underwent simultaneous anatexis during the exhumation, giving rise to anatectic melts with different compositions in various elements but similar patterns in trace element distribution.

Effect of the Iron Ion Doping in LaCoO<sub>3</sub> Perovskite, Both in Powders and in Sintered Samples Obtained from Combustion Reaction and Solid State Route

The aim of this work is to show the effect of the iron ion doping in LaCoO3 perovskite, both in powders and in sintered samples obtained from combustion reaction and solid state route. The phase formation and particle morphology and particle size distribution of the powders were analysed by XRD, SEM and sedimentation techniques, respectively. Relative density, microstructure (secondary phases and grain size) and pore size distribution of LaCo1-xFexO3 sintered ceramics were investigated by SEM/EDS and Hg porosimetry analysis. Although LaCo1-xFexO3 powders obtained from the combustion reaction exhibited smaller grain sizes when sintered at high temperatures, they showed a higher volume fraction of secondary phases. The presence of these crystalline phases in addition to the desired perovskite affected the microstructure acting as grain growth inhibitors by grain boundary pinning. It is believed that by observing three grain junction pores that the LaFeO3 phase has a smaller dihedral angle than LaCoO3. This fact would explain why LaFeO3 presented a smaller driving force for sintering with a higher tendency of pore and inclusion coarsening at higher temperatures (1400°C).

Theoretical Modeling of Tunneling Barriers in Carbon-Based Molecular Electronic Junctions

Density functional theory (DFT) is applied to three models for carbon-based molecular junctions containing fragments of graphene with covalent edge-bonding to aromatic and aliphatic molecules, with the graphene representing a sp2 hybridized carbon electrode and the molecule representing a molecular layer between two electrodes. The DFT results agree well with experimental work functions and transport barriers, including the electronic coupling between molecular layers and graphitic contacts, and predict the compression of tunnel barriers observed for both ultraviolet photoelectron spectroscopy (UPS) and experimental tunneling currents. The results reveal the strong effect of the dihedral angle between the planes of the graphene electrode and the aromatic molecule and imply that the molecules with the smallest dihedral angle are responsible for the largest local current densities. In addition, the results are consistent with the proposal that the orbitals which mediate tunneling are those with significant electron density in the molecular layer. These conclusions should prove valuable for understanding the relationships between molecular structure and electronic transport as an important step toward rational design of carbon-based molecular electronic devices.

Speed of Conformational Change: Comparing Explicit and Implicit Solvent Molecular Dynamics Simulations

Adequate sampling of conformation space remains challenging in atomistic simulations, especially if the solvent is treated explicitly. Implicit-solvent simulations can speed up conformational sampling significantly. We compare the speed of conformational sampling between two commonly used methods of each class: the explicit-solvent particle mesh Ewald (PME) with TIP3P water model and a popular generalized Born (GB) implicit-solvent model, as implemented in the AMBER package. We systematically investigate small (dihedral angle flips in a protein), large (nucleosome tail collapse and DNA unwrapping), and mixed (folding of a miniprotein) conformational changes, with nominal simulation times ranging from nanoseconds to microseconds depending on system size. The speedups in conformational sampling for GB relative to PME simulations, are highly system- and problem-dependent. Where the simulation temperatures for PME and GB are the same, the corresponding speedups are approximately onefold (small conformational changes), between ∼1- and ∼100-fold (large changes), and approximately sevenfold (mixed case). The effects of temperature on speedup and free-energy landscapes, which may differ substantially between the solvent models, are discussed in detail for the case of miniprotein folding. In addition to speeding up conformational sampling, due to algorithmic differences, the implicit solvent model can be computationally faster for small systems or slower for large systems, depending on the number of solute and solvent atoms. For the conformational changes considered here, the combined speedups are approximately twofold, ∼1- to 60-fold, and ∼50-fold, respectively, in the low solvent viscosity regime afforded by the implicit solvent. For all the systems studied, 1) conformational sampling speedup increases as Langevin collision frequency (effective viscosity) decreases; and 2) conformational sampling speedup is mainly due to reduction in solvent viscosity rather than possible differences in free-energy landscapes between the solvent models.

5,20-Bis(α-oligothienyl)-substituted [26]hexaphyrins possessing electronic circuits strongly perturbed by meso-oligothienyl substituents.

A series of [26]hexaphyrins(1.1.1.1.1.1) bearing two α-oligothienyl substituents at 5,20-positions have been synthesised and are shown to have a dumbbell hexaphyrin conformation, to which the α-oligothienyl groups are linked with small dihedral angles to form an acyclic helix-like conjugated network. While their distinct diatropic ring currents and four reversible reduction waves characteristic of aromatic [26]hexaphyrins indicate that the [26]hexaphyrin aromatic circuits are viable, the absorption spectra and excited state dynamics are significantly perturbed, which becomes increasingly evident with elongation of the oligothienyl substituents. DFT calculations of these hexaphyrins indicated that the LUMO and LUMO + 1 are localised on the hexaphyrin circuit and the HOMO and HOMO - 1 are spread over the acyclic helix-like conjugation network, which can explain the perturbed absorption spectra.

Structure–Function Relationships of High-Electron Mobility Naphthalene Diimide Copolymers Prepared Via Direct Arylation

Direct arylation (DA) is emerging as a highly promising method to construct inexpensive conjugated materials for large-area electronics from simple and environmentally benign building blocks. Here, we show that exclusive α-C–H selectivity is feasible in the DA of π-extended monomers having unsubstituted thiophene or furan units, leading to fully linear materials. Two new naphthalene diimide-based conjugated copolymers—P(FuNDIFuF4) and P(ThNDIThF4), composed of naphthalene diimide (NDI), furan (Fu) or thiophene (Th), and tetrafluorobenzene (F4)—are synthesized. Insight into structure–function relationships is given by density functional theory (DFT) calculations and variety of experimental techniques, whereby the effect of the heteroatom on the optical, structural, and electronic properties is investigated. The use of furan (Fu) allows for enhanced solubilities, a smaller dihedral angle between NDI and Fu as a result of the smaller size of Fu, and a smaller π–π-stacking distance in the solid state. P(FuNDI...

Advantage of the N-alkylation strategy for retaining the molecular planarity for oligothiophene/imidazole/1,10-phenanthroline-based heterocyclic semiconducting and fluorescent compounds.

A family of planar oligothiophene/imidazole/1,10-phenanthroline (OTIP)-based heterocyclic, aromatic, semiconducting, and fluorescent compounds with N-substituted alkyl chains (allyl, n-butyl, n-octyl, n-dodecyl, and n-cetyl) have been designed and synthesized. They all have specific N-coordination sites, various donor-acceptor spacers, good molecular planarity, suitable solubility, and high thermal stability. In comparison with conventional double β-alkylation of the thiophene ring, our results reveal that the single imidazole N-alkylation strategy for OTIPs has the advantage of maintaining the planarity of the whole molecule, in addition to improving the solubility, which can be clearly verified by the small dihedral angles between adjacent thiophene/imidazole/1,10-phenanthroline (TIP) rings in eight X-ray single-crystal structures. In particular, n-dodecyl- and n-cetyl-substituted OTIPs (7 and 8) with the same molecular length of 2.37 nm (MW =939 and 1052), show good molecular planarity with the aforementioned dihedral angles of 8.9(5) and 10.4(5)°. Furthermore, special attention has been paid to the physicochemical properties of seven symmetrical OTIPs (6-8, 13-15, and 19), including two to six thiophene rings in the middle of their molecular structures. To the best of our knowledge, this is the first synthetic, structural, and spectral investigation into the N-alkylation of OTIP-based compounds.

Crystal structure of (E)-2-(2-{5-[(2-acetoxyethyl)(methyl)amino]thiophen-2-yl}vinyl)-3-methylbenzothiazolium iodide monohydrate

In the cation of the title hydrated salt, C19H21N2O2S2 +·I−·H2O, the benzo­thia­zolium ring system is approximately planar [maximum deviation = 0.0251 (15) Å], and it makes a small dihedral angle of 1.16 (18)° with the plane of the thio­phene ring. In the crystal, the cations, anions and crystalline water mol­ecules are linked by classical O—H⋯O, O—H⋯I and weak C—H⋯O hydrogn bonds, forming a three-dimensional supra­molecular network. π–π stacking is observed between parallel thia­zole rings of adjacent cations [centroid–centroid distance = 3.5945 (16) Å].

Crystal structure of [2-({4-[2,6-bis(pyri-din-2-yl)pyri-din-4-yl]phenyl}(methyl)amino)-ethanol-κ(3) N,N',N'']bis-(thio-cyan-ato-κN)zinc N,N-di-methyl-formamide monosolvate.

In the title compound, [Zn(NCS)2(C24H22N4O)]·C3H7NO, the ZnII cation is N,N′,N′′-chelated by one 2-({4-[2,6-bis­(pyridin-2-yl)pyridin-4-yl]phen­yl}(meth­yl)amino)­ethanol ligand and coordinated by two thio­cyanate anions in a distorted N5 trigonal–bipyramidal geometry. In the mol­ecule, the three pyridine rings are approximately coplanar [maximum deviation = 0.026 (5) Å], and the mean plane of the three pyridine rings is twisted to the benzene ring with a small dihedral angle of 5.9 (2)°. In the crystal, complex mol­ecules are linked by weak C—H⋯O hydrogen bonds into supra­molecular chains propagated along [110]; π–π stacking is observed between adjacent chains [centroid–centroid distance = 3.678 (4) Å]. The di­methyl­formamide solvent mol­ecules are linked with the complex chains via weak C—H⋯O hydrogen bonds.

The improvement of π-conjugation by the lateral benzene of anthracene and naphthalene

The 1,4-diarylnaphthalenes, 1,4-diarylanthracenes, and 9,10-diarylanthracenes containing the different side arenes, including phenyl, 2-thienyl, and 2-furyl groups, were synthesized to study the influence of structures on π-conjugation. According to photophysics and computation, the smaller dihedral angles and the lateral benzene of anthracene would increase the π-conjugation in some cases. Compared to 1,4-diarylnaphthalenes, 1,4-di(thien-2-yl)anthracene, 1,4-di(fur-2-yl)anthracene, and 9,10-di(fur-2-yl)anthracene displayed better π-conjugation in both of the ground and fluorescing excited states, but 9,10-di(thien-2-yl)anthracene only showed better π-conjugation in the fluorescing excited state.

Theoretical calculation on relationship between molecular structure and band gap of benzo[1,2-b:4,5-b $$'$$ ′ ]dithiophene based homopolymer

In order to guide the synthesis of new materials with low band gaps, quantum-chemical methods have been increasingly applied to predict the band gaps of conjugated polymers. Softwares such as Material Studio, Gauss View, Gauss 03 and Gauss 09 calculation program were used in this paper. Semi-empirical AM1 method was applied to calculate the optimal geometric structure of selected three benzo[1,2-b: 4,5-b']dithiophene homopolymers, namely PBDTV, H2 and H3. Using the generalized density function theory based on B3LYP/6-31G*, B3LYP/6-311G* and M062X/6-311G* level calculation of polymers' band gaps. The results indicate that whether there is enough interspace between adjacent subunits, long alkoxy side chain is advantageous to the band gap decrease, and otherwise it will bring steric hindrance to destroy the coplanarity of polymer chain which is disadvantageous to the band gap decrease. The band gaps of polymers mainly depends on the molecular structure, generally speaking, the more coplanarity of main chain, smaller dihedral angle, smaller difference between the bond length of single and double bonds in the main chain, resulting in narrower band gap.

3-(4-Bromo-phen-yl)cyclo-pent-2-en-1-one.

In the title compound, C11H9BrO, the cyclo­pentenone ring is almost planar with an r.m.s. deviation of 0.0097 Å. The largest inter-ring torsion angles [2.4 (3), 1.3 (3) and 3.53 (2)°] reveal only a very small twist between the rings, and suggest that the two rings are conjugated. The mol­ecule is slightly bowed, as shown by the small dihedral angle between the rings [5.3 (1)°]. The crystal packing pattern consists of parallel sheets that stack parallel to the ac plane. Each sheet consists of mol­ecules that pack side-to-side with the same relative orientation of phenyl and cyclo­pentenone rings along the a- and c-axis directions. Slipped side-to-side, face-to-face and edge-to-face inter­actions exist between pairs of sheets with edge-to-edge and edge-to-face O⋯H—C(sp 2) weak hydrogen-bond contacts. A relatively short edge-to-face contact (2.77 Å) also exists between pairs of sheets.