Crystal structure of (E)-9-({[4-(diethylamino)phenyl]imino}methyl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol

Faizi, Md. Serajul Haque; Ahmad, Musheer; Kapshuk, Anatoly A.; Golenya, Irina A.

doi:10.1107/s2056989016019733

Cited by 8 publications

(3 citation statements)

References 25 publications

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“…These features are similar to those observed in related 4-dimethylamino-N-salicylideneanilines (Wozniak et al, 1995;Pizzala et al, 2000). The C-N, C=N and C-C bond lengths are normal and close to the values observed in related structures (Faizi et al, 2017).…”

Section: Structural Commentarysupporting

confidence: 84%

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

Faizi

Çınar

Aydin

et al. 2020

Acta Crystallogr E Cryst Commun

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The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 3-chloro-4-methylaniline, and crystallizes in the monoclinic space group P21/c. The 3-chlorobenzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intramolecular O—H...N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H...H (43.8%) and C...H/H...C (26.7%) interactions. The density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is provided.

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Section: Structural Commentarysupporting

confidence: 84%

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

Faizi

Çınar

Aydin

et al. 2020

Acta Crystallogr E Cryst Commun

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“…Table gives a summary of the conditions employed to obtain compounds 367–371 . With the exception of the reactions using 2‐amino‐3‐(1 H ‐indol‐3‐yl)propanoic acid (Table , Entry 2) and furan‐2‐ylmethanamine (Table , Entry 3), which resulted in low yield and took long reaction times, all other conditions generated the desired Schiff bases with good to excelent yields (61–93 %) , , , …”

Section: Reactions From Julolidinesmentioning

confidence: 99%

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Varejão

Fernandes

2019

Eur J Org Chem

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Julolidines constitute a class of N‐heterocycle compounds which have in common the 2,3,6,7‐tetrahydro‐1H,5H‐benzo[1,2]quinolizine ring. Due mainly to its fluorescence properties, such structures have shown potential application in a range of scientific and technological areas and have attracted attention of a great variety of research groups. For example, julolidines have been used for detection of ions and volatile compounds in environmental and biological samples, to the construction of dye‐sensitized solar cells, photoconductive materials and as fluorescent sensors for bioimaging. This review summarizes the strategies reported to the synthesis of the julolidine ring and the principal modifications for obtaining more complex julolidine derivatives with improved fluorescence properties of these compounds. In this context, aldol condensation, olefination, imine synthesis, and cross‐coupling reactions have been extensively explored and discussed. Examples of applications, which illustrate the great potential of such structures, will also be briefly presented.

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“…There are many reports in the literature on julolidine-based Schiff bases and their applications as sensors for metal ions (Park et al, 2014;Lee et al, 2014;Kim et al, 2016). The present work is a part of an ongoing structural study of Schiff bases based on the julolidine ring system (Faizi et al, 2016(Faizi et al, , 2017. We report here the crystal structure and DFT computational calculation of the title julolidine compound (I).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure and DFT study of 8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline-9-carbaldehyde

2017

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Supporting information: this article has supporting information at journals.iucr.org/eCrystal structure and DFT study of 8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij] In the title compound, C 13 H 15 NO 2 , the fused non-aromatic rings of the julolidine moiety adopt envelope conformations. The hydroxy group forms an intramolecular hydrogen bond to the aldehyde O atom, generating an S(6) ring motif. Weak intermolecular C-HÁ Á ÁO hydrogen bonds help to stabilize the crystal structure. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state.

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Crystal structure of (E)-9-({[4-(diethylamino)phenyl]imino}methyl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol

Abstract: In the title compound, the hydroxy group forms a intramolecular hydrogen bond to the imine N atom and generates an S(6) ring motif. The conformation about the C=N bond is E, and the aromatic ring of the julolidine moiety is inclined to the benzene ring by 3.74 (14)°.

Cited by 8 publications

References 25 publications

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Crystal structure and DFT study of 8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline-9-carbaldehyde

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Crystal structure of (E)-9-({[4-(diethylamino)phenyl]imino}methyl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol

Abstract: In the title compound, the hy­droxy group forms a intra­molecular hydrogen bond to the imine N atom and generates an S(6) ring motif. The conformation about the C=N bond is E, and the aromatic ring of the julolidine moiety is inclined to the benzene ring by 3.74 (14)°.

Cited by 8 publications

References 25 publications

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Crystal structure and DFT study of 8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline-9-carbaldehyde

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Abstract: In the title compound, the hydroxy group forms a intramolecular hydrogen bond to the imine N atom and generates an S(6) ring motif. The conformation about the C=N bond is E, and the aromatic ring of the julolidine moiety is inclined to the benzene ring by 3.74 (14)°.