Crystal structure and Hirshfeld analysis of 2-(5-bromothiophen-2-yl)acetonitrile

Ted M. Pappenfus; Tiana L. Wood; Joseph L. Morey; Wyatt D. Wilcox; Daron E. Janzen

doi:10.1107/S2056989018000968

Crystal structure and Hirshfeld analysis of 2-(5-bromothiophen-2-yl)acetonitrile

Ted M. Pappenfus, Tiana L. Wood, Joseph L. Morey, Wyatt D. Wilcox, Daron E. Janzen

Chemistry (Morris)

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

2 Scopus citations

Abstract

The title compound, C₆H₄BrNS, crystallizes in the space group P2₁/n with one complete molecule in the asymmetric unit. The non-H atoms are nearly planar (r.m.s for non-H atoms = 0.071 Å), with the nitrile group oriented antiperiplanar with respect to the thiophene S atom. Intermolecular Type I centrosymmetric Br Br halogen interactions are present at a distance of 3.582 (1) Å and with a C-Br Br angle of 140.7 (1). Additional weaker C-H N, C-H S, and S interactions are also present. A Hirshfeld analysis indicates Br Br interactions comprise only 1.9% of all the interatomic contacts.

Original language	English (US)
Pages (from-to)	189-192
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	74
DOIs	https://doi.org/10.1107/S2056989018000968
State	Published - Feb 2018

Bibliographical note

Funding Information:
The authors acknowledge St. Catherine University and NSF– MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. TMP acknowledges the following: (i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research and the UMM Division of Science and Mathematics for financial assistance, and (ii) The Supercomputing Institute of the University of Minnesota. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University.

Funding Information:
The authors acknowledge St. Catherine University and NSF-MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. TMP acknowledges the following: (i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research and the UMM Division of Science and Mathematics for financial assistance, and (ii) The Supercomputing Institute of the University of Minnesota. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University.

Publisher Copyright:
© 2018 IUCr. All rights reserved.

Keywords

Crystal structure
Halogen interactions
Hirshfeld analysis
Nitrile
Thiophene

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10.1107/S2056989018000968

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title = "Crystal structure and Hirshfeld analysis of 2-(5-bromothiophen-2-yl)acetonitrile",

abstract = "The title compound, C6H4BrNS, crystallizes in the space group P21/n with one complete molecule in the asymmetric unit. The non-H atoms are nearly planar (r.m.s for non-H atoms = 0.071 {\AA}), with the nitrile group oriented antiperiplanar with respect to the thiophene S atom. Intermolecular Type I centrosymmetric Br Br halogen interactions are present at a distance of 3.582 (1) {\AA} and with a C-Br Br angle of 140.7 (1). Additional weaker C-H N, C-H S, and S interactions are also present. A Hirshfeld analysis indicates Br Br interactions comprise only 1.9% of all the interatomic contacts.",

keywords = "Crystal structure, Halogen interactions, Hirshfeld analysis, Nitrile, Thiophene",

author = "Pappenfus, {Ted M.} and Wood, {Tiana L.} and Morey, {Joseph L.} and Wilcox, {Wyatt D.} and Janzen, {Daron E.}",

note = "Funding Information: The authors acknowledge St. Catherine University and NSF– MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. TMP acknowledges the following: (i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research and the UMM Division of Science and Mathematics for financial assistance, and (ii) The Supercomputing Institute of the University of Minnesota. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University. Funding Information: The authors acknowledge St. Catherine University and NSF-MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. TMP acknowledges the following: (i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research and the UMM Division of Science and Mathematics for financial assistance, and (ii) The Supercomputing Institute of the University of Minnesota. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University. Publisher Copyright: {\textcopyright} 2018 IUCr. All rights reserved.",

year = "2018",

month = feb,

doi = "10.1107/S2056989018000968",

language = "English (US)",

volume = "74",

pages = "189--192",

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

issn = "2056-9890",

publisher = "International Union of Crystallography",

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T1 - Crystal structure and Hirshfeld analysis of 2-(5-bromothiophen-2-yl)acetonitrile

AU - Pappenfus, Ted M.

AU - Wood, Tiana L.

AU - Morey, Joseph L.

AU - Wilcox, Wyatt D.

AU - Janzen, Daron E.

N1 - Funding Information: The authors acknowledge St. Catherine University and NSF– MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. TMP acknowledges the following: (i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research and the UMM Division of Science and Mathematics for financial assistance, and (ii) The Supercomputing Institute of the University of Minnesota. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University. Funding Information: The authors acknowledge St. Catherine University and NSF-MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. TMP acknowledges the following: (i) University of Minnesota, Morris (UMM) Faculty Research Enhancement Funds supported by the University of Minnesota Office of the Vice President for Research and the UMM Division of Science and Mathematics for financial assistance, and (ii) The Supercomputing Institute of the University of Minnesota. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University. Publisher Copyright: © 2018 IUCr. All rights reserved.

PY - 2018/2

Y1 - 2018/2

N2 - The title compound, C6H4BrNS, crystallizes in the space group P21/n with one complete molecule in the asymmetric unit. The non-H atoms are nearly planar (r.m.s for non-H atoms = 0.071 Å), with the nitrile group oriented antiperiplanar with respect to the thiophene S atom. Intermolecular Type I centrosymmetric Br Br halogen interactions are present at a distance of 3.582 (1) Å and with a C-Br Br angle of 140.7 (1). Additional weaker C-H N, C-H S, and S interactions are also present. A Hirshfeld analysis indicates Br Br interactions comprise only 1.9% of all the interatomic contacts.

AB - The title compound, C6H4BrNS, crystallizes in the space group P21/n with one complete molecule in the asymmetric unit. The non-H atoms are nearly planar (r.m.s for non-H atoms = 0.071 Å), with the nitrile group oriented antiperiplanar with respect to the thiophene S atom. Intermolecular Type I centrosymmetric Br Br halogen interactions are present at a distance of 3.582 (1) Å and with a C-Br Br angle of 140.7 (1). Additional weaker C-H N, C-H S, and S interactions are also present. A Hirshfeld analysis indicates Br Br interactions comprise only 1.9% of all the interatomic contacts.

KW - Crystal structure

KW - Halogen interactions

KW - Hirshfeld analysis

KW - Nitrile

KW - Thiophene

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ER -

Crystal structure and Hirshfeld analysis of 2-(5-bromothiophen-2-yl)acetonitrile

Abstract

Bibliographical note

Keywords

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