Crystal structures of 2,4,6-triiodobenzonitrile and 2,4,6-triiodophenyl isocyanide

Wayland E. Noland; Doyle Britton; Gregory K. Sutton; Andrew K. Schneerer; Kenneth J Tritch

doi:10.1107/S2056989017018217

Crystal structures of 2,4,6-triiodobenzonitrile and 2,4,6-triiodophenyl isocyanide

Wayland E. Noland, Doyle Britton, Gregory K. Sutton, Andrew K. Schneerer, Kenneth J Tritch

Chemistry (Twin Cities)

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

4 Scopus citations

Abstract

The title crystals, C₇H₂I₃N, are isomorphous. Both molecules lie across two crystallographic mirror planes and a twofold axis. The principal supramolecular interaction is centric R²₂(10) CN/NC I short contacts involving both ortho I atoms, with two contacts bisecting each cyano and isocyano group. These form ribbons along [010] and give rise to a planar sheet structure parallel to (100). All pairs of adjacent sheets have centric stacking, a mode not previously reported for sheets of this type. This study completes the series of homo-2,4,6trihalobenzonitriles, in which I atoms give the strongest CN X and NC X interactions (X = F, Cl, Br, I).

Original language	English (US)
Pages (from-to)	98-102
Number of pages	5
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	74
DOIs	https://doi.org/10.1107/S2056989017018217
State	Published - 2018

Bibliographical note

Funding Information:
The authors thank Victor G. Young, Jr. (X-Ray Crystallographic Laboratory, University of Minnesota) for assistance with the crystallographic determination, and the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for generous financial support of this project. This work was taken in large part from the PhD thesis of KJT (Tritch, 2017).

Keywords

C I contacts
Crystal structure
Isocyanide
N I contacts
Nitrile

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10.1107/S2056989017018217

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@article{7b3ea61637c14826b7d85a1c1773daab,

title = "Crystal structures of 2,4,6-triiodobenzonitrile and 2,4,6-triiodophenyl isocyanide",

abstract = "The title crystals, C7H2I3N, are isomorphous. Both molecules lie across two crystallographic mirror planes and a twofold axis. The principal supramolecular interaction is centric R22(10) CN/NC I short contacts involving both ortho I atoms, with two contacts bisecting each cyano and isocyano group. These form ribbons along [010] and give rise to a planar sheet structure parallel to (100). All pairs of adjacent sheets have centric stacking, a mode not previously reported for sheets of this type. This study completes the series of homo-2,4,6trihalobenzonitriles, in which I atoms give the strongest CN X and NC X interactions (X = F, Cl, Br, I).",

keywords = "C I contacts, Crystal structure, Isocyanide, N I contacts, Nitrile",

author = "Noland, {Wayland E.} and Doyle Britton and Sutton, {Gregory K.} and Schneerer, {Andrew K.} and Tritch, {Kenneth J}",

note = "Funding Information: The authors thank Victor G. Young, Jr. (X-Ray Crystallographic Laboratory, University of Minnesota) for assistance with the crystallographic determination, and the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for generous financial support of this project. This work was taken in large part from the PhD thesis of KJT (Tritch, 2017).",

year = "2018",

doi = "10.1107/S2056989017018217",

language = "English (US)",

volume = "74",

pages = "98--102",

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

issn = "2056-9890",

publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structures of 2,4,6-triiodobenzonitrile and 2,4,6-triiodophenyl isocyanide

AU - Noland, Wayland E.

AU - Britton, Doyle

AU - Sutton, Gregory K.

AU - Schneerer, Andrew K.

AU - Tritch, Kenneth J

N1 - Funding Information: The authors thank Victor G. Young, Jr. (X-Ray Crystallographic Laboratory, University of Minnesota) for assistance with the crystallographic determination, and the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for generous financial support of this project. This work was taken in large part from the PhD thesis of KJT (Tritch, 2017).

PY - 2018

Y1 - 2018

N2 - The title crystals, C7H2I3N, are isomorphous. Both molecules lie across two crystallographic mirror planes and a twofold axis. The principal supramolecular interaction is centric R22(10) CN/NC I short contacts involving both ortho I atoms, with two contacts bisecting each cyano and isocyano group. These form ribbons along [010] and give rise to a planar sheet structure parallel to (100). All pairs of adjacent sheets have centric stacking, a mode not previously reported for sheets of this type. This study completes the series of homo-2,4,6trihalobenzonitriles, in which I atoms give the strongest CN X and NC X interactions (X = F, Cl, Br, I).

AB - The title crystals, C7H2I3N, are isomorphous. Both molecules lie across two crystallographic mirror planes and a twofold axis. The principal supramolecular interaction is centric R22(10) CN/NC I short contacts involving both ortho I atoms, with two contacts bisecting each cyano and isocyano group. These form ribbons along [010] and give rise to a planar sheet structure parallel to (100). All pairs of adjacent sheets have centric stacking, a mode not previously reported for sheets of this type. This study completes the series of homo-2,4,6trihalobenzonitriles, in which I atoms give the strongest CN X and NC X interactions (X = F, Cl, Br, I).

KW - C I contacts

KW - Crystal structure

KW - Isocyanide

KW - N I contacts

KW - Nitrile

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U2 - 10.1107/S2056989017018217

DO - 10.1107/S2056989017018217

M3 - Article

C2 - 29850032

AN - SCOPUS:85043232460

SN - 2056-9890

VL - 74

SP - 98

EP - 102

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -

Crystal structures of 2,4,6-triiodobenzonitrile and 2,4,6-triiodophenyl isocyanide

Abstract

Bibliographical note

Keywords

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