(E)-1-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylidene] -2-phenylhydrazine: sheets built from π-stacked hydrogen-bonded chains

J. Trilleras; M. Utria; J. Cobo; C. Glidewell

doi:10.1107/S2053229614000680

(E)-1-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylidene] -2-phenylhydrazine: sheets built from π-stacked hydrogen-bonded chains

J. Trilleras, M. Utria, J. Cobo, C. Glidewell

School of Chemistry

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

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Abstract

The reaction between 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and phenylhydrazine proceeds via condensation to provide the title compound, C₁₇H₁₅ClN₄, (I), rather than via the alternative routes of simple nucleophilic substitution or cyclocondensation. With the exception of the phenyl group bonded directly to the pyrazole ring, the non-H atoms of (I) are nearly coplanar, with an r.m.s. deviation of 0.058Å. The molecules are linked into C(7) chains by a single N - H⋯N hydrogen bond, and the chains are linked by π-π stacking interactions to form sheets.

Original language	English
Pages (from-to)	216-219
Number of pages	4
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	70
Issue number	2
DOIs	https://doi.org/10.1107/S2053229614000680
Publication status	Published - 1 Feb 2014

Keywords

Crystal structure
pi-stacked hydrogen-bonded chains
Condensation reaction
Phenylhydrazine derivative

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10.1107/S2053229614000680

Glidewell_2014_OC_E15Chloro
© 2014 International Union of Crystallography.
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title = "(E)-1-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylidene] -2-phenylhydrazine: sheets built from π-stacked hydrogen-bonded chains",

abstract = "The reaction between 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and phenylhydrazine proceeds via condensation to provide the title compound, C17H15ClN4, (I), rather than via the alternative routes of simple nucleophilic substitution or cyclocondensation. With the exception of the phenyl group bonded directly to the pyrazole ring, the non-H atoms of (I) are nearly coplanar, with an r.m.s. deviation of 0.058{\AA}. The molecules are linked into C(7) chains by a single N - H⋯N hydrogen bond, and the chains are linked by π-π stacking interactions to form sheets.",

keywords = "Crystal structure, pi-stacked hydrogen-bonded chains, Condensation reaction, Phenylhydrazine derivative",

author = "J. Trilleras and M. Utria and J. Cobo and C. Glidewell",

note = "The authors thank `Centro de Instrumentaci{\'o}n Cient{\'i}fico-T{\'e}cnica of Universidad de Ja{\'e}n' and the staff for data collection. JT and MU thank UNIATLANTICO (Universidad del Atl{\'a}ntico, Colombia) for financial support. JC thanks the Consejer{\'i}a de Innovaci{\'o}n, Ciencia y Empresa (Junta de Andaluc{\'i}a, Spain) and the Universidad de Ja{\'e}n for financial support.",

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T2 - sheets built from π-stacked hydrogen-bonded chains

AU - Trilleras, J.

AU - Utria, M.

AU - Cobo, J.

AU - Glidewell, C.

N1 - The authors thank `Centro de Instrumentación Científico-Técnica of Universidad de Jaén' and the staff for data collection. JT and MU thank UNIATLANTICO (Universidad del Atlántico, Colombia) for financial support. JC thanks the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support.

PY - 2014/2/1

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N2 - The reaction between 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and phenylhydrazine proceeds via condensation to provide the title compound, C17H15ClN4, (I), rather than via the alternative routes of simple nucleophilic substitution or cyclocondensation. With the exception of the phenyl group bonded directly to the pyrazole ring, the non-H atoms of (I) are nearly coplanar, with an r.m.s. deviation of 0.058Å. The molecules are linked into C(7) chains by a single N - H⋯N hydrogen bond, and the chains are linked by π-π stacking interactions to form sheets.

AB - The reaction between 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and phenylhydrazine proceeds via condensation to provide the title compound, C17H15ClN4, (I), rather than via the alternative routes of simple nucleophilic substitution or cyclocondensation. With the exception of the phenyl group bonded directly to the pyrazole ring, the non-H atoms of (I) are nearly coplanar, with an r.m.s. deviation of 0.058Å. The molecules are linked into C(7) chains by a single N - H⋯N hydrogen bond, and the chains are linked by π-π stacking interactions to form sheets.

KW - Crystal structure

KW - pi-stacked hydrogen-bonded chains

KW - Condensation reaction

KW - Phenylhydrazine derivative

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(E)-1-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylidene] -2-phenylhydrazine: sheets built from π-stacked hydrogen-bonded chains

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