Crystal structure of 4-(prop-2-yn-1-yl-oxy)benzonitrile

Mayu Kanagawa; Tsunehisa Okuno; William Thomas Alexander Harrison

doi:10.1107/S2056989014028035

Crystal structure of 4-(prop-2-yn-1-yl-oxy)benzonitrile

Mayu Kanagawa, Tsunehisa Okuno^*, William Thomas Alexander Harrison

^*Corresponding author for this work

Chemistry

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

2 Citations (Scopus)

Abstract

In the title compound, C₁₀H₇NO, the dihedral angle between the aromatic ring and the prop-2-yn-1-yloxy grouping is 9.47 (10)°. The bond lengths indicate electronic conjugation between the cyano group, the benzene ring and the propyn-yloxy oxygen atom. In the crystal, a hydrogen bond between the acetylenic C - H atom and the cyano nitrogen atom link the molecules into wave-like [301¯] C(11) chains. These chains are connected by Csp² - H⋯π_ac (π_ac is the acetylinic C - C triple bond) close contacts [2.794 (1) Å], resulting in a rolling sheet structure parallel to the ac plane and aromatic π-π stacking interactions between the sheets [centroid-centroid distance = 3.593 (2) Å] generate a three-dimensional network.

Original language	English
Pages (from-to)	o97-o98
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	2
DOIs	https://doi.org/10.1107/S2056989014028035
Publication status	Published - 1 Feb 2015

Keywords

C - H⋯n interactions
Crystal structure
Hydrogen bonding
Prop-2-yn-1-yloxy
π-πstacking interactions

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title = "Crystal structure of 4-(prop-2-yn-1-yl-oxy)benzonitrile",

abstract = "In the title compound, C10H7NO, the dihedral angle between the aromatic ring and the prop-2-yn-1-yloxy grouping is 9.47 (10)°. The bond lengths indicate electronic conjugation between the cyano group, the benzene ring and the propyn-yloxy oxygen atom. In the crystal, a hydrogen bond between the acetylenic C - H atom and the cyano nitrogen atom link the molecules into wave-like [301¯] C(11) chains. These chains are connected by Csp2 - H⋯πac (πac is the acetylinic C - C triple bond) close contacts [2.794 (1) {\AA}], resulting in a rolling sheet structure parallel to the ac plane and aromatic π-π stacking interactions between the sheets [centroid-centroid distance = 3.593 (2) {\AA}] generate a three-dimensional network.",

keywords = "C - H⋯n interactions, Crystal structure, Hydrogen bonding, Prop-2-yn-1-yloxy, π-πstacking interactions",

author = "Mayu Kanagawa and Tsunehisa Okuno and Harrison, {William Thomas Alexander}",

note = "Acknowledgements This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST)",

year = "2015",

month = feb,

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doi = "10.1107/S2056989014028035",

language = "English",

volume = "71",

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journal = "Acta Crystallographica Section E: Structure Reports Online",

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TY - JOUR

T1 - Crystal structure of 4-(prop-2-yn-1-yl-oxy)benzonitrile

AU - Kanagawa, Mayu

AU - Okuno, Tsunehisa

AU - Harrison, William Thomas Alexander

N1 - Acknowledgements This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST)

PY - 2015/2/1

Y1 - 2015/2/1

N2 - In the title compound, C10H7NO, the dihedral angle between the aromatic ring and the prop-2-yn-1-yloxy grouping is 9.47 (10)°. The bond lengths indicate electronic conjugation between the cyano group, the benzene ring and the propyn-yloxy oxygen atom. In the crystal, a hydrogen bond between the acetylenic C - H atom and the cyano nitrogen atom link the molecules into wave-like [301¯] C(11) chains. These chains are connected by Csp2 - H⋯πac (πac is the acetylinic C - C triple bond) close contacts [2.794 (1) Å], resulting in a rolling sheet structure parallel to the ac plane and aromatic π-π stacking interactions between the sheets [centroid-centroid distance = 3.593 (2) Å] generate a three-dimensional network.

AB - In the title compound, C10H7NO, the dihedral angle between the aromatic ring and the prop-2-yn-1-yloxy grouping is 9.47 (10)°. The bond lengths indicate electronic conjugation between the cyano group, the benzene ring and the propyn-yloxy oxygen atom. In the crystal, a hydrogen bond between the acetylenic C - H atom and the cyano nitrogen atom link the molecules into wave-like [301¯] C(11) chains. These chains are connected by Csp2 - H⋯πac (πac is the acetylinic C - C triple bond) close contacts [2.794 (1) Å], resulting in a rolling sheet structure parallel to the ac plane and aromatic π-π stacking interactions between the sheets [centroid-centroid distance = 3.593 (2) Å] generate a three-dimensional network.

KW - C - H⋯n interactions

KW - Crystal structure

KW - Hydrogen bonding

KW - Prop-2-yn-1-yloxy

KW - π-πstacking interactions

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DO - 10.1107/S2056989014028035

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AN - SCOPUS:84928155490

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SP - o97-o98

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

IS - 2

ER -

Crystal structure of 4-(prop-2-yn-1-yl-oxy)benzonitrile

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