Critical role of weak [C–H⋯O] hydrogen bonds in the assembly of benzo[1,2-d:4,5-d′]bisoxazole cruciforms into supramolecular sheets

Lim, Jaebum; Osowska, Karolina; Armitage, Jacob; Martin, Benjamin; Miljanić, Ognjen Š.

doi:10.1039/c2ce25485a

Cited by 9 publications

(2 citation statements)

References 109 publications

(8 reference statements)

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“…A search of the Cambridge Structural Database (CSD, version of November 2020; Groom et al, 2016) found only twelve benzoxazoles substituted by a carbonyl group on the 2-position. In almost half of the cases, the benzoxazole derivative is used as a ligand to complex an Ni, Co or Cu atom (CAYSIG and CAYSOM;Iasco et al, 2012;LAJNAN;Zhang et al, 2010), or incorporated in a macromolecule (NESPUY; Lim et al, 2012;LUYJUL;Osowska & Miljanic ´, 2010), resulting in a geometry quite far from that of a small entity. Among the remaining examples, the benzoxazolylcarbonyl moiety may be linked to an aromatic group.…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure of methyl 1,3-benzoxazole-2-carboxylate

Poirot¹,

Saffon‐Merceron²,

Leygue³

et al. 2021

Acta Cryst E

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The title compound, C9H7NO3, crystallizes in the monoclinic (P21) space group. In the crystal, the almost planar molecules display a flattened herringbone arrangement. Stacking molecules are slipped in the lengthwise and widthwise directions and are linked by π–π interactions [d(Cg...Cg = 3.6640 (11) Å]. The structure is characterized by strong C—H...N and weak C—H...O hydrogen bonds, and further stabilized by C–O...π interactions.

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Section: Database Surveymentioning

confidence: 99%

Crystal structure of methyl 1,3-benzoxazole-2-carboxylate

Poirot¹,

Saffon‐Merceron²,

Leygue³

et al. 2021

Acta Cryst E

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“…Studies on role and importance of the weak interactions have been received much attentions. [8][9][10][11] On the other hand, investigation with the intense to understand and estimate the relative contribution to a whole of molecular aggregation has gradually progressed. [12][13][14] One reason why is that a series of model compounds suitable for systematic investigations on weak interactions is difficult to obtain.…”

Section: Introductionmentioning

confidence: 99%

Dimeric Molecular Aggregation Motif in Crystal of 2,7-Diethoxy-1-(4-Nitrobenzoyl)naphthalene: Correlation of Single Molecular Structure, Molecular Accumulation Structure and Non-Covalent-Bonding Interactions

Ohisa

Saeki

Shiomichi

et al. 2018

ECB

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Crystal structure of 2,7-diethoxy-1-(4-nitrobenzoyl)naphthalene C21H19NO5, is reported and discussed on the characteristics of the spatial organization of single molecule and molecular aggregation as contrasted with a homologous compound. The molecular structures of these compounds differ only in the kind of alkoxy group of 2,7-positions of the naphthalene rings, i.e., ethoxy groups for title compound and methoxy groups for homologue. In single molecular crystal structures of these compounds, 4-nitrobenzoyl group is non-coplanarly attached to the naphthalene ring. The molecules exhibit axial chirality, with either R or S stereogenic axis. The two pairs of the enantiomeric molecules are related by twofold helical axis in the asymmetric unit of P21/n space group for title compound and P21/c one for homologue, showing the number of molecules (Z) is four for both compounds. In their molecular packing structures, (R)-and (S)enantiomers are connected to each other by … stacking interactions, forming centrosymmetric dimeric molecular aggregates. However, the aggregation structures of the dimers are apparently different between title compound and homologue. The dimeric units of title compound are stacked into columnar structure with (sp 2)C-H…O=C non-classical hydrogen bonds between identical enantiomers along aaxis. The columns are connected by (sp 2)C-H…OEt non-classical hydrogen bonds between identical enantiomers along c-axis to give sheet-like aggregation spreading on ac-plane. The sheets are piled up through (sp 3)C-H… non-classical hydrogen bonds between opposite enantiomeric molecules of next dimeric aggregates along b-axis giving layers. On the other hand, the dimeric molecular aggregates of homologue are connected into flattish column by (sp 3)C-H…O=C non-classical hydrogen bonds and (sp 3)C-H… nonclassical hydrogen bonds between identical enantiomers. The columns are linked into waving plate through weak (sp 2)C-H… nonclassical hydrogen bonds. In title compound, difference between … stacking interactions and non-classical hydrogen bonds is smaller than homologue in contribution to the whole of molecular packing structure.

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Synthesis, characterization, spectral property, Hirshfeld surface analysis and TD/DFT calculations of 2, 6-disubstituted benzobisoxazoles

Yue

Chai

et al. 2019

Journal of Molecular Structure

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Critical role of weak [C–H⋯O] hydrogen bonds in the assembly of benzo[1,2-d:4,5-d′]bisoxazole cruciforms into supramolecular sheets

Cited by 9 publications

References 109 publications

Crystal structure of methyl 1,3-benzoxazole-2-carboxylate

Crystal structure of methyl 1,3-benzoxazole-2-carboxylate

Dimeric Molecular Aggregation Motif in Crystal of 2,7-Diethoxy-1-(4-Nitrobenzoyl)naphthalene: Correlation of Single Molecular Structure, Molecular Accumulation Structure and Non-Covalent-Bonding Interactions

Synthesis, characterization, spectral property, Hirshfeld surface analysis and TD/DFT calculations of 2, 6-disubstituted benzobisoxazoles

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