Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-ethoxyquinoline-4-carboxylate

Younos Bouzian; Khalid Karrouchi; El Hassane Anouar; Rachid Bouhfid; Suhana Arshad; El Mokhtar Essassi

doi:10.1107/S2056989019007473

Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-ethoxyquinoline-4-carboxylate

Younos Bouzian, Khalid Karrouchi, El Hassane Anouar, Rachid Bouhfid, Suhana Arshad, El Mokhtar Essassi

Chemistry

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8 Scopus citations

Abstract

In the title quinoline derivative, C₁₄ H 14 ClNO₃, there is an intramolecular C - H...O hydrogen bond forming an S(6) graph-set motif. The molecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-ethoxyquinoline mean plane. In the crystal, offset π-π interactions with a centroid-to-centroid distance oF₃.4731 (14) Å link inversion-related molecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H...H contacts make the largest contribution (50.8%) to the Hirshfeld surface.

Original language	English
Pages (from-to)	912-916
Number of pages	5
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	75
DOIs	https://doi.org/10.1107/S2056989019007473
State	Published - 2019

Keywords

crystal structure
DFT
Hirshfeld surface analysis
offset π-π interactions
quinoline

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10.1107/S2056989019007473

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title = "Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-ethoxyquinoline-4-carboxylate",

abstract = "In the title quinoline derivative, C14 H 14 ClNO3, there is an intramolecular C - H...O hydrogen bond forming an S(6) graph-set motif. The molecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-ethoxyquinoline mean plane. In the crystal, offset π-π interactions with a centroid-to-centroid distance oF3.4731 (14) {\AA} link inversion-related molecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H...H contacts make the largest contribution (50.8\%) to the Hirshfeld surface.",

keywords = "crystal structure, DFT, Hirshfeld surface analysis, offset π-π interactions, quinoline",

author = "Younos Bouzian and Khalid Karrouchi and Anouar, \{El Hassane\} and Rachid Bouhfid and Suhana Arshad and Essassi, \{El Mokhtar\}",

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year = "2019",

doi = "10.1107/S2056989019007473",

language = "English",

volume = "75",

pages = "912--916",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

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TY - JOUR

T1 - Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-ethoxyquinoline-4-carboxylate

AU - Bouzian, Younos

AU - Karrouchi, Khalid

AU - Anouar, El Hassane

AU - Bouhfid, Rachid

AU - Arshad, Suhana

AU - Essassi, El Mokhtar

PY - 2019

Y1 - 2019

N2 - In the title quinoline derivative, C14 H 14 ClNO3, there is an intramolecular C - H...O hydrogen bond forming an S(6) graph-set motif. The molecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-ethoxyquinoline mean plane. In the crystal, offset π-π interactions with a centroid-to-centroid distance oF3.4731 (14) Å link inversion-related molecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H...H contacts make the largest contribution (50.8%) to the Hirshfeld surface.

AB - In the title quinoline derivative, C14 H 14 ClNO3, there is an intramolecular C - H...O hydrogen bond forming an S(6) graph-set motif. The molecule is essentially planar with the mean plane of the ethyl acetate group making a dihedral angle of 5.02 (3)° with the ethyl 6-chloro-2-ethoxyquinoline mean plane. In the crystal, offset π-π interactions with a centroid-to-centroid distance oF3.4731 (14) Å link inversion-related molecules into columns along the c-axis direction. Hirshfeld surface analysis indicates that H...H contacts make the largest contribution (50.8%) to the Hirshfeld surface.

KW - crystal structure

KW - DFT

KW - Hirshfeld surface analysis

KW - offset π-π interactions

KW - quinoline

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U2 - 10.1107/S2056989019007473

DO - 10.1107/S2056989019007473

M3 - Article

AN - SCOPUS:85069854385

SN - 2056-9890

VL - 75

SP - 912

EP - 916

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -

Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-ethoxyquinoline-4-carboxylate

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Keywords

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