Adjacent Phenyl Research Articles

Activating Photodynamic Therapy in vitro with Cerenkov Radiation Generated from Yttrium-90.

The translation of photodynamic therapy (PDT) to the clinical setting has primarily been limited to easily accessible and/or superficial diseases, for which traditional light delivery can be performed noninvasively. Cerenkov radiation, as generated from medically relevant radionuclides, has been suggested as a means to deliver light to deeper tissues noninvasively to overcome this depth limitation. This article investigates the utility of Cerenkov radiation, as generated from the radionuclide yttrium-90, for activating the PDT process using clinically approved aminolevulinic acid at 1.0 mm and also the more efficient porphyrin-based photosensitizer mesotetraphenylporphine with two sulfonate groups on adjacent phenyl rings (TPPS2a) at 1.2 µm. Experiments were conducted with monolayer cultured glioma and breast tumor cell lines. Although aminolevulinic acid proved to be ineffective for generating a therapeutic effect at all but the highest activity levels, TPPS2a produced at least a 20% therapeutic effect at activities ranging from 6 to 60 µCi/well for the C6 glioma cell line. Importantly, these results demonstrate for the first time, to our knowledge, that Cerenkov radiation generated from a radionuclide can be used to activate PDT using clinically relevant photosensitizers. These results therefore provide evidence that it may be possible to generate a phototherapeutic effect in vivo using Cerenkov radiation and clinically relevant photosensitizers.

Interaction of carboxylic acids with rutile TiO2(110): IR-investigations of terephthalic and benzoic acid adsorbed on a single crystal substrate

The adsorption of two carboxylic acids, benzoic acid (BA) and terephthalic acid (TPA), on a single crystal rutile TiO2(110) substrate was studied using infrared reflection–absorption spectroscopy (IRRAS) in conjunction with DFT calculations. On the basis of the high-quality IR data (in particular for the OH bands), various adsorbate species with different geometries could be identified. The adsorption of both, BA and TPA, on TiO2(110) leads to deprotonation of carboxylic acids and protonation of substrate O-atoms. At low coverage, the deprotonated BA molecule adsorbs on TiO2(110) in an upright, bidentate configuration, while the TPA molecule adopts a flat-lying geometry with both carboxylates bound to the surface in a monodentate geometry. At higher coverages, a transition from flat-lying to upright-oriented TPA molecules occurs. At saturation coverage, both BA and TPA molecules undergo dimerization indicating the presence of pronounced attractive intermolecular interactions. We propose that the BA dimers are stabilized by the interaction between adjacent phenyl rings, while the TPA dimerization is attributed to the formation of double hydrogen bonds between adjacent apical carboxylic groups.

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the CO and CS adopting a pseudo-antiperiplanar conformation. An intramolecular NH⋯OC hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular NH⋯SC and NH⋯OC hydrogen-bonding interactions involving the acylthiourea moiety. Compound 2 is further stabilized by π-stacking between adjacent naphthalene and phenyl rings. The thermal behavior, as well as the vibrational properties, studied by infrared and Raman spectroscopy data complemented by quantum chemical calculations at the B3PW91/6-311++G(d,p) support the formation of these intra- and intermolecular hydrogen bonds. Furthermore, the UV–Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations with the shapes of the simulated absorption spectra in good accordance with the experimental data.

Crystal structure of (E)-2-[(2-hy-droxy-4-meth-oxy-phen-yl)(phen-yl)methyl-idene]-N-phenyl-hydrazine-1-carboxamide.

The title compound, C21H19N3O3, has an E conformation about the azomethine double bond. The central moiety of the hydrazinecarboxamide moiety [-N-N-C(=O)-N-] has an almost coplanar arrangement [maximum deviation for the C atom = 0.010 (2) Å]. This central moiety is flanked by three aromatic rings and its mean plane makes dihedral angles of 24.7 (1), 72.91 (12) and 34.26 (11) Å, respectively, with the phenolic ring, the phenyl ring attached to the same C atom as the phenolic ring, and the phenyl-hydrazine ring. The adjacent phenolic and phenyl rings are twisted away from each other to reduce steric hindrance and make a dihedral angle of 80.59 (12)°. The phenolic and phenyl-hydrazine rings are inclined to one another by 28.89 (11)°. The rigidity of the mol-ecule is increased by an intra-molecular O-H⋯N hydrogen bond involving the phenolic hydrogen and the azomethine N atom. In the crystal, the carbonyl O atom forms bifurcated hydrogen bonds with the two NH atoms of the hydrazinic group, leading to the formation of chains propagating along [001]. Within the chains there are also C-H⋯O hydrogen bonds present. The chains are linked via C=O⋯π [3.4316 (18) Å] and parallel slipped π-π inter-actions, involving inversion-related benzene rings [centroid-centroid distance = 3.8850 (14) Å; inter-planar distance = 3.3895 (10) Å; slippage = 1.899 Å], forming sheets lying parallel to (100).

Gas-phase Smiles rearrangement reactions of deprotonated N-phenylbenzamides studied by electrospray ionization tandem mass spectrometry.

Electrospray ionization tandem mass spectrometry (ESI-MS(n)) is an invaluable tool for the study of gas-phase reactions. When N-phenylbenzamide is analyzed in negative ion mode, the nucleophilic deprotonated site of nitrogen or oxygen, together with the adjacent electrophilic phenyl carbon in the same molecule, provides a useful opportunity to study the intramolecular nucleophilic reaction in the gas phase. All MS(n) experiments of deprotonated N-phenylbenzamides were conducted on an ion trap mass spectrometer using ESI in negative ion mode. The accurate masses of fragments were measured on an ESI quadrupole time-of-flight mass spectrometer in negative ion mode. Theoretical calculations were conducted at the B3LYP/6-31++G(d,p) level of density functional theory using the Gaussian 03 program. When the polarity of the substituent on the aniline ring was changed, gas-phase Smiles rearrangement reactions could be initiated by different atoms in the anionic center. Upon collisional activation, loss of CO from deprotonated N-phenylbenzamides could be observed, which can be interpreted as a nitrogen anion triggering the Smiles rearrangement reaction through a three-membered ring transition state. As the aniline ring was substituted by a strong electron-withdrawing group (e.g., NO(2), COCH(3), or CF(3)) at the para position, a characteristic phenolate anion was obtained, which was derived from the Smiles rearrangement reaction initiated by the oxygen anion through a four-membered ring transition state. In the fragmentation of deprotonated N-phenylbenzamides, the gas-phase Smiles rearrangement reaction initiated by either the nitrogen or the oxygen atom can proceed. The findings in this study have not only enriched knowledge on the gas-phase Smiles rearrangement reactions, but also provided valuable information for understanding the rearrangements of deprotonated aromatic amides in gas phase.

Crystal structure of 7-[(2E)-2-benzyl-idene-3-oxobut-oxy]-4-methyl-2H-chromen-2-one.

Two independent mol­ecules (A and B) comprise the asymmetric unit of the title compound, C21H18O4. There are significant conformational differences between the mol­ecules relating in particular to the relative orientation of the 3-oxo-2-(phenyl­methyl­idene)but­oxy substituent with respect to the superimposable chromen-2-one residues. To a first approximation, the substituents are mirror images; both are approximately perpendicular to the chromen-2-one fused ring system with dihedral angles of 88.50 (7) (A) and 81.96 (7)° (B). Another difference between the independent mol­ecules is noted in the dihedral angles between the adjacent phenyl and but-3-en-2-one groups of 8.72 (12) (A) and 27.70 (10)° (B). The conformation about the ethene bond in both mol­ecules is E. The crystal packing features C—H⋯O, C—H⋯π(ar­yl) and π–π [Cg⋯Cg = 3.6657 (8) and 3.7778 (8) Å] stacking inter­actions, which generate a three-dimensional network.

Electronic and magnetic properties of silicon supported organometallic molecular wires: a density functional theory (DFT) study.

The electronic and magnetic properties of transition metal (TM = Sc, Ti, V, Cr and Mn) atom incorporated single and double one-dimensional (1D) styrene molecular wires confined on the hydrogen-terminated Si(100) surface are explored for the first time by means of spin-polarized density functional theory, denoted as Si-[TM(styrene)]. It is unveiled that TM atoms bind asymmetrically to the adjacent phenyl rings, which leads to novel electronic and magnetic properties in stark contrast to the well-studied gas phase TM-benzene molecular wires. Si-[Mn(styrene)]∞ and Si-[Cr(styrene)]∞ single molecular wires (SMWs) are a ferromagnetic semiconductor and half metal, respectively. Creation of H-atom defects on the silicon surface can introduce an impurity metallic band, which leads to novel half-metallic magnetism of a Si-[Mn(styrene)]∞ system. Moreover, double molecular wires (DMWs) containing two identical or hetero SMWs are theoretically designed. The [Mn(styrene)]∞-[Cr(styrene)]∞ DMW exhibits half-metallic magnetism where the spin-up and spin-down channels are contributed by two single molecular wires. Finally, we demonstrate that introducing a TM-defect may significantly affect the electronic structure and magnetic properties of molecular wires. These studies provide new insights into the structure and properties of surface supported 1-D sandwiched molecular wires and may inspire the future experimental synthesis of substrate confined organometallic sandwiched molecular wires.

1,8‐Disubstituted Xanthylidene‐Based Remote Carbenes: Photolytic Generation and Isolation of Low‐Coordinate Palladium(II) Complex

The isolation and study of carbenes with σ-donating and π-accepting properties stronger than those of N-heterocyclic carbenes (NHCs) have been regarded as one of the big challenges in carbene chemistry. We have investigated the properties of 1,8-disubstituted xanthylidene-based compounds by using two different approaches: The photolysis-induced formation of free carbenes and the synthesis of the corresponding metal–carbene complexes by oxidative addition. The former study revealed that the carbene unsubstituted at the 1- and 8-positions is kinetically more reactive than the parent xanthylidene and that the substituents at the 1- and 8-positions are less effective in generating carbenes by photolysis. However, oxidative addition of palladium(0) to the 1,8-diphenyl-substituted precursor successfully afforded a low-coordinate 14-electron palladium(II)–carbene complex. This unusual complex is stabilized by agnostic interactions involving an adjacent phenyl group. This complex is the second example of a stable cationic 14-electron palladium(II)–carbene complex to have been reported so far.

Construction of a ytterbium supramolecular compound from 5,5′-(buta-diyne-1,4-diyl)diisophthalic acid

A novel 3D ytterbium supramolecular compound, [Yb(HBDDC)(H2O)4]·2H2O(1), was synthesized via 5,5′-(buta-diyne-1,4-diyl)diisophthalic acid ligand(H4BDDC) under solvothermal conditions. Single-crystal X-ray diffraction analysis reveals that compound 1 crystallizes in triclinic system, $P\bar 1$ space group with a=0.71372(14) nm, b=1.0566(2) nm, c=1.7969(4) nm, α=101.01(3)°, β=98.15(3)°, γ=99.17(3)° and V=1.2922(4) nm3. Compound 1 exhibits a special infinite 1D chain, which stacks parallel each other in an ABAB sequence, leading to the formation of a 3D supramolecular structure owing to the strong π-π interactions between adjacent phenyl ring groups. Moreover, compound 1 manifests excellent luminescent property.

C2-Symmetric Benzene-Based Hydrogel Modified Electrode for the Determination of Copper Ion by Stripping Voltammetry

In the last few years, low molecular organogels (LMWG) have attracted much interest due to their unique properties, including high adsorption capacity, high specific surface area, high porosity and rich functional groups binding with other guest species. LMWG based materials have wide applications in various field, such as separation technologies, tissue engineering, sensors, catalysis [1-4]. LMWGs are usually obtained by self-assembly of low molecular(typically with a molecular weight < 1000 Da)weight gelators in organic solvents or in water, to form fibrous structure through non-covalent interactions such as hydrogen bonding, π-π stacking, metal coordination, coulomb forces, and van der Waals interactions[5] .C2-symmetric benzene-based hydrogel (C2-BHG) is a new type of LMWGs with a 1,4-dimine benzene as the symmetric structure which can provide strong parallel interactions between hydrogen-bonding amide moieties. The C2-BHG has been used as an adsorbent to remove the toxic materials due to its strong adsorption ability [5]. The C2-BNG can self-assemble on many surfaces to form fibrous network structure through the π–π stacking between the adjacent phenyl groups or hydrogen bonding.In this report, the C2-BHG modified glassy carbon electrode (C2-BHG/GCE) was fabricated by self assembly at a suitable assembly temperature. The gelation and self-assembly of C2-GHB can occur simultaneously on the carbon surface with a uniform film thickness. The film properties were studied by cyclic voltammetry (CV) and electrochemical impedance spectroscopy (EIS) in the presence of redox probes. The morphology of C2-GHB-modified layer was characterized by atomic force microscopy (AFM). The porous membrane structure with a high surface area could provide rich active sites to interact with the target substance. In addition, the C2-GHB-modified layer contains a large amount of hydroxyl group on the hydrophilic chain. The sensing properties of the C2-BHG/GCE to Cu(II) ions were investigated with sensitive response. Under the optimized conditions (such as preconcentration time, preconcentration potential and electrolyte type), the linear range of Cu(II) ions was determined between 1ppt-800ppt and 1ppb-100ppb, with a detection limit down to 0.5 ppt. The complex interaction of C2-BHG with Cu2+ was confirmed by UV-Vis characterization.As a new kind of low molecular organogel modifier, C2-GHB is a promising material in the development of a new type of chemical modified electrode for sensor application.

Chain folding in main-chain liquid crystalline polyesters: from π–π stacking toward shape memory

A series of main-chain thermotropic liquid crystalline polyesters were synthesized by polycondensation from mesogenic dial such as 4,4′-bis(6-hydroxyhexyloxy)biphenyl (BHHBP) and various diacids with different substituents such as succinic acid (no side group), 2-methylsuccinic acid (aliphatic side group) and 2-phenylsuccinic acid (aromatic side group), named poly(4,4′-bis(6-hydroxyhexyloxy)biphenyl succinate) (PBDS), poly(4,4′-bis(6-hydroxyhexyloxy)biphenyl methylsuccinate) (PBDMS), and poly(4,4′-bis(6-hydroxyhexyloxy)biphenyl phenylsuccinate) (PBDPS), respectively. Liquid crystalline behaviours were investigated through differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and small angle X-ray scattering (SAXS) and the thermal stability of the polyesters was determined via thermogravimetric analysis (TGA). PBDS, PBDMS and PBDPS showed a SmF, SmB and SmA phase, respectively. On enlarging the side group, the d-spacing of the smectic layer increased, indicating folding packing of the polymer chains. Therefore, the adjacent phenyl rings in side groups stacked well together and formed strong π–π interactions even when the temperature was higher than Ti. The special structure of PBDPS could provide good mechanical properties. Thus, PBDPS exhibited the maximum tensile stress (28.6 MPa) and the highest elongation at break (1060%). Furthermore, the strong π–π interaction can act as netpoints; therefore, PBDPS exhibited excellent shape fixing (>99%) and shape recovery ratio (>99%) with large strain (>220%).

N,N'-(Propane-1,3-di-yl)dibenzo-thio-amide.

The title compound, C17H18N2S2, exhibits a trans–trans–trans–gauche+ (tttg +) conformation with regard to the NH–CH2–CH2–CH2–NH bond sequence. In the crystal, mol­ecules are connected by N—H⋯S=C and C—H⋯S=C hydrogen bonds, forming a herringbone arrangement along the c-axis direction. The two thioamide groups make dihedral angles of 43.0 (2) and 33.1 (2)° with the adjacent phenyl rings.

Phase Behavior and Molecular Packing of Octadecyl Phenols and their Methyl Ethers at the Air/Water Interface

Noncovalent molecular interactions, such as hydrogen bonding and van der Waals forces, play an important role in self-assembling to supramolecular structures. To study these forces, we chose monolayers at the air/water interface to limit the possible arrangements of the interacting molecules. Furthermore, monolayers provide useful tools to understand and study interactions between molecules in a controlled and fundamental way. The phase behavior and molecular packing of the phenols 1-(4-hydroxyphenyl)-octadecane (5a), 1-(3,4-dihydroxyphenyl)-octadecane (6), and 1-(2,3,4-trihydroxyphenyl)-octadecane (3) and their methyl ethers in monolayers at the air/water interface have been examined by π/A isotherms, Brewster angle microscopy (BAM), grazing incidence X-ray diffraction (GIXD) measurements, and density functional theory (DFT) calculations. The phenols are synthesized by Friedel-Crafts acylation of methoxybenzenes, hydrogenation of the resulting aryl ketones, and cleavage of the aryl methyl ethers. In the π/A isotherms and in BAM, the phenols show patches of the solid condensed phase at large molecular areas and the monolayers collapse at high pressures. Furthermore, the dimensions of the unit cell obtained by GIXD measurements are compatible with an arrangement of the phenyl rings that allows one aryl ring to interact with four adjacent phenyl rings in an edge-to-face arrangement, which leads to a significant binding energy. The experimental data are in good agreement with DFT calculations of 2D crystalline benzene and p-cresol arrangements. The enhanced monolayer stability of phenol 5a can be explained by hydrogen bonds of the hydroxyl group with water and van der Waals forces between the alkyl chains and aryl-aryl interactions.

Structure and optical properties of fullerene C60 complex with dipyridinated iron(II) phthalocyanine [Fe(II)Pc(C5H5N)2]·C60·4C6H4Cl2: First structure of bisaxially coordinated iron(II) phthalocyanine complex with acetonitrile Fe(II)Pc(CH3CN)2

The complex of fullerene C 60 with dipyridinated iron(II) phthalocyanine [ Fe ( II ) Pc ( C 5 H 5 N )2]· C 60·4 C 6 H 4 Cl 2 (1) has been obtained as single crystals. According to the IR- and UV-visible-NIR spectra, 1 is molecular solid with no charge transfer from Fe ( II ) Pc ( C 5 H 5 N )2 to C 60· C 60 molecules form closely packed linear columns in 1 along the b axis with a uniform interfullerene center-to center distance of 9.99 Å and multiple short van der Waals (vdW) C … C contacts between fullerenes of 3.10–3.18 Å. Totally each Fe ( II ) Pc ( C 5 H 5 N )2 unit is surrounded by four C 60 molecules two of which form short vdW C … C contacts with the phthalocyanine plane locating near two adjacent phenylene substituents of Fe ( II ) Pc . The Fe ( II ) Pc ( C 5 H 5 N )2 geometry remains almost unchanged as compared with that of fullerene free Fe ( II ) Pc ( C 5 H 5 N )2. The iron(II) atoms are located exactly in the Pc plane, the Fe - N ( C 5 H 5 N ) bond length is 2.038(3) Å and the averaged of the Fe - N ( Pc ) bond length is 1.935(3) Å. Bisaxially coordinated iron(II) phthalocyanine complex with acetonitrile Fe ( II ) Pc ( CH 3 CN )2 does not cocrystallize with C 60. Nevertheless, good quality crystals of [ Fe ( II ) Pc ( CH 3 CN )2]·2 C 6 H 4 Cl 2 (2) were isolated in this synthesis. That is the first structure of bisaxially coordinated metal phthalocyanine complex with nitrile containing solvent. Acetonitrile unusually strongly coordinates to Fe ( II ) Pc with the Fe – N ( CH 3 CN ) bond length of 1.938(1) Å. The iron(II) atoms are located in the Pc plane and the averaged length of the Fe - N ( Pc ) bonds is 1.934(1) Å.

A tetrahydropyrene-based organic dye for solar cell application

A novel tetrahydropyrene-based D–π–A organic dye D2 was designed and synthesized for the first time, featuring 4,5,9,10-tetrahydropyrene as a π conjugation linker to bridge the diphenylamine unit and the thienyl acrylic acid moiety. Its counterpart D1 was prepared for comparison, where biphenyl was used as the linker. Both dyes were characterized by photophysical, electrochemical, and theoretical computational methods. It was found that the introduction of two ethylene groups on the C2, C2′ and C6, C6′ of the biphenyl in D2 can prevent the rotation of the adjacent phenyl rings, and ensure the coplanarity of the bridge. As a result, the maximum absorption peak (λmax) of D2 was 29 nm red shifted as compared with D1. Nanocrystalline TiO2-based dye-sensitized solar cells were fabricated using the dyes as light harvesting sensitizers, and exhibited power conversion efficiencies of 6.75% for D2 and 4.73% for D1 under AM 1.5 conditions.

Synthesis and optoelectronic properties of phenylenevinylenequinoline macromolecules

A series of 3, 5 and 7 quinoline terminated arylenevinylene oligomers was selectively synthesized by applying two repetitive reactions at each cycle of oligomerization: a Wittig and Pd Heck cross-coupling. Oligomers were characterized by 1H and homo-J-resolved, DEPT-135, APT, 13C NMR and MALDI-TOF spectrometry. A detailed characterization of the oligomers was performed by UV-Vis, static-dynamic fluorescence and Z-scan spectroscopy. The HOMO and LUMO levels were determined by cyclic voltammetry and compared with the theoretical ones. Effective conjugation is attained for the pentamer, whilst the molecular structure of the heptamer shows a pronounced torsion of the phenylenevinylene segment disrupting the degree of conjugation as revealed by theoretical simulation of the oligomer geometry. Furthermore, the theoretical simulation shows that the HOMO–LUMO frontier orbitals are mainly localized in the phenylenevinylene structure, while in the quinolines the spatial distribution is only located at the CN– group without any appreciable contribution of the adjacent phenyl group. The pentamer is the most fluorescent oligomer with a quantum yield in solution of ϕ = 0.62–0.68 depending on the solvent and a fluorescence lifetime of 1.07–1.28 ns, making this oligomer suitable for optoelectronic devices.

Synthesis and crystal structure of α,β-unsaturated ketone: 3,3′-[1,2-ethanediylbis(oxy-2,1-phenylene)]bis[1-(2-pyridyl)-2-propen-1-one

The title compound, C30H24N2O4, 3,3′-[1,2-ethanediyl-bis(oxy-2,1-phenylene)]bis[1-(2-pyridyl)-2-propen-1-one] was synthesized and characterized by elemental analysis, FT-IR spectra, 1H NMR, and X-ray single-crystal diffraction. In the molecule, the pyridine plane and the adjacent phenyl plane are almost coplanar with the dihedral angle of 3.07°, while the dihedral angle between the mean planes of the two asymmetric units is 67.56°. The crystal packing is stabilized by weak intermolecular C-H...N and C-H...O hydrogen bonds, C-H...π and π...π stacking interactions.

N'-Benzoyl-5-methyl-1,3-diphenyl-1H-pyrazole-4-carbohydrazide.

In the title compound, C24H20N4O2, the pyrazole ring makes dihedral angles of 47.57 (10)° and 30.56 (11)° with its N-bound and C-bound phenyl groups, respectively. The C—N—N—C group that links the two carbonyls has a torsion angle of 81.5 (2)°. The torsion angles between the carbonyl groups and their adjacent pyrazole and phenyl rings are 125.89 (19) and 164.22 (17)°, respectively. In the crystal, pairs of mol­ecules are linked by N—H⋯O hydrogen bonds into R 2 2(10) ring motifs, which in turn link to form chains that propagate parallel to the c-axis direction.

Quantized Water Transport: Ideal Desalination through Graphyne-4 Membrane

Graphyne sheet exhibits promising potential for nanoscale desalination to achieve both high water permeability and salt rejection rate. Extensive molecular dynamics simulations on pore-size effects suggest that γ-graphyne-4, with 4 acetylene bonds between two adjacent phenyl rings, has the best performance with 100% salt rejection and an unprecedented water permeability, to our knowledge, of ~13 L/cm2/day/MPa, 3 orders of magnitude higher than prevailing commercial membranes based on reverse osmosis, and ~10 times higher than the state-of-the-art nanoporous graphene. Strikingly, water permeability across graphyne exhibits unexpected nonlinear dependence on the pore size. This counter-intuitive behavior is attributed to the quantized nature of water flow at the nanoscale, which has wide implications in controlling nanoscale water transport and designing highly effective membranes.

8-Bromo-3-(4-ethyl-phen-yl)-1-phenyl-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c]isoxazole-3a-carbo-nitrile.

In the title compound, C25H21BrN2O2, the fused isoxazolidine ring adopts an envelope conformation with the N atom at the flap and the mean plane of the ring makes dihedral angles of 54.37 (12) and 87.32 (13)°, respectively, with the adjacent phenyl and benzene rings. The tetra­hydro­pyran ring has a half-chair conformation. In the crystal, mol­ecules are linked into a double-column structure along the b-axis direction through weak C—H⋯O and C—H⋯π inter­actions.