Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl 3,5-dibromo-4-isocyano-benzoate

Wayland E. Noland; Ryan J. Herzig; Abigail J. Engwall; Renee C. Jensen; Kenneth J Tritch

doi:10.1107/S2056989018002256

Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl 3,5-dibromo-4-isocyano-benzoate

Wayland E. Noland, Ryan J. Herzig, Abigail J. Engwall, Renee C. Jensen, Kenneth J Tritch

Chemistry (Twin Cities)

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

Abstract

The title crystals, C9H5Br2NO2, are the first reported 2,6-dihalophenyl cyanide-isocyanide pair that have neither three- nor two-dimensional isomorphism. Both crystals contain contacts between the carbonyl O atom and a Br atom. In the crystal of the cyanide, R 2 ²(10) inversion dimers form based on C≡N. . .Br contacts, a common packing feature in this series of crystals. In the isocyanide, the corresponding N≡C. . .Br contacts are not observed. Instead, the isocyano C atom forms contacts with the methoxy C atom. RNC was refined as a two-component pseudo-merohedral twin.

Original language	English (US)
Pages (from-to)	345-348
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	74
DOIs	https://doi.org/10.1107/S2056989018002256
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).

Publisher Copyright:
© 2018 International Union of Crystallography. All rights reserved.

Keywords

C=O. . .Br contacts
C≡N. . .Br contacts
N≡C. . .C contacts
crystal structure
isocyanide
nitrile

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10.1107/S2056989018002256

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title = "Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl 3,5-dibromo-4-isocyano-benzoate",

abstract = "The title crystals, C9H5Br2NO2, are the first reported 2,6-dihalophenyl cyanide-isocyanide pair that have neither three- nor two-dimensional isomorphism. Both crystals contain contacts between the carbonyl O atom and a Br atom. In the crystal of the cyanide, R 2 2(10) inversion dimers form based on C≡N. . .Br contacts, a common packing feature in this series of crystals. In the isocyanide, the corresponding N≡C. . .Br contacts are not observed. Instead, the isocyano C atom forms contacts with the methoxy C atom. RNC was refined as a two-component pseudo-merohedral twin.",

keywords = "C=O. . .Br contacts, C≡N. . .Br contacts, N≡C. . .C contacts, crystal structure, isocyanide, nitrile",

author = "Noland, {Wayland E.} and Herzig, {Ryan J.} and Engwall, {Abigail J.} and Jensen, {Renee C.} 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). Publisher Copyright: {\textcopyright} 2018 International Union of Crystallography. All rights reserved.",

year = "2018",

doi = "10.1107/S2056989018002256",

language = "English (US)",

volume = "74",

pages = "345--348",

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

issn = "2056-9890",

publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl 3,5-dibromo-4-isocyano-benzoate

AU - Noland, Wayland E.

AU - Herzig, Ryan J.

AU - Engwall, Abigail J.

AU - Jensen, Renee C.

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). Publisher Copyright: © 2018 International Union of Crystallography. All rights reserved.

PY - 2018

Y1 - 2018

N2 - The title crystals, C9H5Br2NO2, are the first reported 2,6-dihalophenyl cyanide-isocyanide pair that have neither three- nor two-dimensional isomorphism. Both crystals contain contacts between the carbonyl O atom and a Br atom. In the crystal of the cyanide, R 2 2(10) inversion dimers form based on C≡N. . .Br contacts, a common packing feature in this series of crystals. In the isocyanide, the corresponding N≡C. . .Br contacts are not observed. Instead, the isocyano C atom forms contacts with the methoxy C atom. RNC was refined as a two-component pseudo-merohedral twin.

AB - The title crystals, C9H5Br2NO2, are the first reported 2,6-dihalophenyl cyanide-isocyanide pair that have neither three- nor two-dimensional isomorphism. Both crystals contain contacts between the carbonyl O atom and a Br atom. In the crystal of the cyanide, R 2 2(10) inversion dimers form based on C≡N. . .Br contacts, a common packing feature in this series of crystals. In the isocyanide, the corresponding N≡C. . .Br contacts are not observed. Instead, the isocyano C atom forms contacts with the methoxy C atom. RNC was refined as a two-component pseudo-merohedral twin.

KW - C=O. . .Br contacts

KW - C≡N. . .Br contacts

KW - N≡C. . .C contacts

KW - crystal structure

KW - isocyanide

KW - nitrile

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U2 - 10.1107/S2056989018002256

DO - 10.1107/S2056989018002256

M3 - Article

C2 - 29765720

AN - SCOPUS:85043301220

SN - 2056-9890

VL - 74

SP - 345

EP - 348

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -

Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl 3,5-dibromo-4-isocyano-benzoate

Abstract

Bibliographical note

Keywords

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