(E)-3-{4-[(7-Chloroquinolin-4-yl)oxy]-3-methoxyphenyl}-1-(4-methylphenyl) prop-2-en-1-one: a ladder-like structure resulting solely from π-π stacking interactions

A. Montoya; B. Insuasty; J. Cobo; C. Glidewell

doi:10.1107/S2053229614013588

(E)-3-{4-[(7-Chloroquinolin-4-yl)oxy]-3-methoxyphenyl}-1-(4-methylphenyl) prop-2-en-1-one: a ladder-like structure resulting solely from π-π stacking interactions

A. Montoya, B. Insuasty, J. Cobo, C. Glidewell

School of Chemistry

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Abstract

In the title compound, C₂₆H₂₀0ClNO₃, the quinoline fragment is nearly orthogonal to the adjacent aryl ring, while the rest of the molecular skeleton is close to being planar. The crystal structure contains no hydrogen bonds of any sort, but there are two π-π stacking interactions present. One, involving the quinoline ring, links molecules related by inversion, while the other, involving the two nonfused aryl rings, links molecules related by translation, so together forming a ladder-type arrangement.

Original language	English
Pages (from-to)	677-680
Number of pages	4
Journal	Acta Crystallographica Section C Structural Chemistry
Volume	70
Issue number	7
DOIs	https://doi.org/10.1107/S2053229614013588
Publication status	Published - 1 Jul 2014

Keywords

Crystal structure
pi-pi stacking interactions
Ladder-like structure
Prop-2-en-1-one
(7-chloroquinolin-4-yl)oxy
Nucleophilic aromatic substitution
Claisen-Schmidt condensation
Chalcone

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10.1107/S2053229614013588

Glidewell_2014_SC_E347Chloroquinolin
© 2014 International Union of Crystallography.
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title = "(E)-3-{4-[(7-Chloroquinolin-4-yl)oxy]-3-methoxyphenyl}-1-(4-methylphenyl) prop-2-en-1-one: a ladder-like structure resulting solely from π-π stacking interactions",

abstract = "In the title compound, C26H200ClNO3, the quinoline fragment is nearly orthogonal to the adjacent aryl ring, while the rest of the molecular skeleton is close to being planar. The crystal structure contains no hydrogen bonds of any sort, but there are two π-π stacking interactions present. One, involving the quinoline ring, links molecules related by inversion, while the other, involving the two nonfused aryl rings, links molecules related by translation, so together forming a ladder-type arrangement.",

keywords = "Crystal structure, pi-pi stacking interactions, Ladder-like structure, Prop-2-en-1-one, (7-chloroquinolin-4-yl)oxy, Nucleophilic aromatic substitution, Claisen-Schmidt condensation, Chalcone",

author = "A. Montoya and B. Insuasty and J. Cobo and C. Glidewell",

note = "The authors thank the Centro de Instrumentaci{\'o}n Cient{\'i}fico-T{\'e}cnica of the Universidad de Ja{\'e}n and the staff for the data collection. AM and BI thank COLCIENCIAS and the Universidad del Valle for financial support. JC thanks the Consejer{\'i}a de Innovaci{\'o}n, Ciencia y Empresa (Junta de Andaluc{\'i}a, Spain) and the Universidad de Ja{\'e}n for financial support.",

year = "2014",

month = jul,

day = "1",

doi = "10.1107/S2053229614013588",

language = "English",

volume = "70",

pages = "677--680",

journal = "Acta Crystallographica Section C Structural Chemistry",

issn = "2053-2296",

publisher = "International Union of Crystallography",

number = "7",

}

(E)-3-{4-[(7-Chloroquinolin-4-yl)oxy]-3-methoxyphenyl}-1-(4-methylphenyl) prop-2-en-1-one: a ladder-like structure resulting solely from π-π stacking interactions. / Montoya, A.; Insuasty, B.; Cobo, J. et al.
In: Acta Crystallographica Section C Structural Chemistry, Vol. 70, No. 7, 01.07.2014, p. 677-680.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - (E)-3-{4-[(7-Chloroquinolin-4-yl)oxy]-3-methoxyphenyl}-1-(4-methylphenyl) prop-2-en-1-one

T2 - a ladder-like structure resulting solely from π-π stacking interactions

AU - Montoya, A.

AU - Insuasty, B.

AU - Cobo, J.

AU - Glidewell, C.

N1 - The authors thank the Centro de Instrumentación Científico-Técnica of the Universidad de Jaén and the staff for the data collection. AM and BI thank COLCIENCIAS and the Universidad del Valle for financial support. JC thanks the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support.

PY - 2014/7/1

Y1 - 2014/7/1

N2 - In the title compound, C26H200ClNO3, the quinoline fragment is nearly orthogonal to the adjacent aryl ring, while the rest of the molecular skeleton is close to being planar. The crystal structure contains no hydrogen bonds of any sort, but there are two π-π stacking interactions present. One, involving the quinoline ring, links molecules related by inversion, while the other, involving the two nonfused aryl rings, links molecules related by translation, so together forming a ladder-type arrangement.

AB - In the title compound, C26H200ClNO3, the quinoline fragment is nearly orthogonal to the adjacent aryl ring, while the rest of the molecular skeleton is close to being planar. The crystal structure contains no hydrogen bonds of any sort, but there are two π-π stacking interactions present. One, involving the quinoline ring, links molecules related by inversion, while the other, involving the two nonfused aryl rings, links molecules related by translation, so together forming a ladder-type arrangement.

KW - Crystal structure

KW - pi-pi stacking interactions

KW - Ladder-like structure

KW - Prop-2-en-1-one

KW - (7-chloroquinolin-4-yl)oxy

KW - Nucleophilic aromatic substitution

KW - Claisen-Schmidt condensation

KW - Chalcone

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M3 - Article

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SP - 677

EP - 680

JO - Acta Crystallographica Section C Structural Chemistry

JF - Acta Crystallographica Section C Structural Chemistry

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(E)-3-{4-[(7-Chloroquinolin-4-yl)oxy]-3-methoxyphenyl}-1-(4-methylphenyl) prop-2-en-1-one: a ladder-like structure resulting solely from π-π stacking interactions

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