Crystal structure of (S)-5,7-diphenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Ivy K. Price; Celine Rougeot; Jason E. Hein; W. T A Harrison

doi:10.1107/S2056989015002996

Crystal structure of (S)-5,7-diphenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Ivy K. Price, Celine Rougeot, Jason E. Hein^*, W. T A Harrison (Editor)

^*Corresponding author for this work

Chemistry

University of California Merced

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

3 Citations (Scopus)

7 Downloads (Pure)

Abstract

The title compound, C₁₆H₁₃N₅, was synthesized by coupling aminotetrazole with chalcone in the presence of an amine organocatalyst derived from chincona alkaloid. There are two molecules, A and B, in the asymmetric unit. In molecule A, the dihedral angles between the partly hydrogenated pyrimidine ring system (r.m.s. deviation = 0.056 Å) and the sp²- and sp³-bonded phenyl groups are 33.32 (11) and 86.53 (11)°, respectively. The equivalent data for molecule B are 0.049 Å, and 27.05 (10) and 85.27 (11)°, respectively. In the crystal, A+B dimers linked by pairs of N - H⋯N hydrogen bonds generate R ²₂(8) loops. The dimers are linked by aromatic π-π stacking interactions [shortest centroid-centroid separation = 3.5367 (15) Å], which results in a three-dimensional network.

Original language	English
Pages (from-to)	o220-o221
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	4
Early online date	4 Mar 2015
DOIs	https://doi.org/10.1107/S2056989015002996
Publication status	Published - 1 Apr 2015

Bibliographical note

Acknowledgements
The authors thank Christopher Daley, A. Rheingold and C. Moore (UCSD) for the data collection. Funding for this work was provided by the University of California, Merced and the National Science Foundation (CHE-1300686)

Keywords

Crystal structure
Hydrogen bonding
Tetrazolo[1,5-a]pyrimidine
π-π stacking

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10.1107/S2056989015002996Licence: CC BY

Crystal structure of (S)-5,7-diphenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine
© 2015 Price et al. Licence: Creative Commons Attribution (CC-BY) https://creativecommons.org/licenses/by/4.0/
Final published version, 298 KBLicence: CC BY

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title = "Crystal structure of (S)-5,7-diphenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine",

abstract = "The title compound, C16H13N5, was synthesized by coupling aminotetrazole with chalcone in the presence of an amine organocatalyst derived from chincona alkaloid. There are two molecules, A and B, in the asymmetric unit. In molecule A, the dihedral angles between the partly hydrogenated pyrimidine ring system (r.m.s. deviation = 0.056 {\AA}) and the sp2- and sp3-bonded phenyl groups are 33.32 (11) and 86.53 (11)°, respectively. The equivalent data for molecule B are 0.049 {\AA}, and 27.05 (10) and 85.27 (11)°, respectively. In the crystal, A+B dimers linked by pairs of N - H⋯N hydrogen bonds generate R 22(8) loops. The dimers are linked by aromatic π-π stacking interactions [shortest centroid-centroid separation = 3.5367 (15) {\AA}], which results in a three-dimensional network.",

keywords = "Crystal structure, Hydrogen bonding, Tetrazolo[1,5-a]pyrimidine, π-π stacking",

author = "Price, {Ivy K.} and Celine Rougeot and Hein, {Jason E.} and Harrison, {W. T A}",

note = "Acknowledgements The authors thank Christopher Daley, A. Rheingold and C. Moore (UCSD) for the data collection. Funding for this work was provided by the University of California, Merced and the National Science Foundation (CHE-1300686)",

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AU - Price, Ivy K.

AU - Rougeot, Celine

AU - Hein, Jason E.

A2 - Harrison, W. T A

N1 - Acknowledgements The authors thank Christopher Daley, A. Rheingold and C. Moore (UCSD) for the data collection. Funding for this work was provided by the University of California, Merced and the National Science Foundation (CHE-1300686)

PY - 2015/4/1

Y1 - 2015/4/1

N2 - The title compound, C16H13N5, was synthesized by coupling aminotetrazole with chalcone in the presence of an amine organocatalyst derived from chincona alkaloid. There are two molecules, A and B, in the asymmetric unit. In molecule A, the dihedral angles between the partly hydrogenated pyrimidine ring system (r.m.s. deviation = 0.056 Å) and the sp2- and sp3-bonded phenyl groups are 33.32 (11) and 86.53 (11)°, respectively. The equivalent data for molecule B are 0.049 Å, and 27.05 (10) and 85.27 (11)°, respectively. In the crystal, A+B dimers linked by pairs of N - H⋯N hydrogen bonds generate R 22(8) loops. The dimers are linked by aromatic π-π stacking interactions [shortest centroid-centroid separation = 3.5367 (15) Å], which results in a three-dimensional network.

AB - The title compound, C16H13N5, was synthesized by coupling aminotetrazole with chalcone in the presence of an amine organocatalyst derived from chincona alkaloid. There are two molecules, A and B, in the asymmetric unit. In molecule A, the dihedral angles between the partly hydrogenated pyrimidine ring system (r.m.s. deviation = 0.056 Å) and the sp2- and sp3-bonded phenyl groups are 33.32 (11) and 86.53 (11)°, respectively. The equivalent data for molecule B are 0.049 Å, and 27.05 (10) and 85.27 (11)°, respectively. In the crystal, A+B dimers linked by pairs of N - H⋯N hydrogen bonds generate R 22(8) loops. The dimers are linked by aromatic π-π stacking interactions [shortest centroid-centroid separation = 3.5367 (15) Å], which results in a three-dimensional network.

KW - Crystal structure

KW - Hydrogen bonding

KW - Tetrazolo[1,5-a]pyrimidine

KW - π-π stacking

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Crystal structure of (S)-5,7-diphenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine

Abstract

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Keywords

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