Different packing motifs of isomeric (E)-N1-(halophenylmethylidene)-N-methyl-2-(thiophen-2-yl)-acetohydrazides controlled by C—HO interactions

Laura N. F. Cardoso, Thais C. M. Nogueira, James Wardell, Marcus V. N. de Souza, William T. A. Harrison

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Abstract

The crystal structures of three isomeric (E)-N0 -(chlorophenylmethylidene)-Nmethyl-2-(thiophen-2-yl)acetohydrazides (C14H13ClN2OS) are described, with
the Cl atom in ortho (I), meta (III) and para (IV) positions in the benzene ring.
The ortho-bromo derivative (II) (C14H13BrN2OS), which is isostructural with its
chloro congener (I), is also reported. Molecules (I)–(III) have similar conformations, which approximate to l-shapes, as indicated by their N—C—
C—Ct (t = thiophene) torsion angles of 90.1 (3), 91.44 (18) and 90.7 (9),
respectively. The conformation of (IV) is different, with an equivalent torsion
angle of 170.75 (11) corresponding to a more extended shape for the molecule. The thiophene ring in each structure features ‘flip’ rotational disorder.
The packing for (I) and (II) features inversion dimers, linked by pairs of C—HO interactions, which generate R22 (14) loops. In the crystal of (III), [010]C(8) chains arise, with adjacent molecules linked by pairs of C—HO hydrogen bonds. The packing for (IV) features unusually short C—HO interactions arising from an H atom attached to the benzene ring (HO = 2.18 A˚ ), which lead to C(9) [301] chains. Hirshfeld fingerprint percentage contact contributions are similar for the four title compounds.
Original languageEnglish
Pages (from-to)313-318
Number of pages6
JournalActa Crystallographica Section E: Structure Reports Online
Volume74
DOIs
Publication statusPublished - 2018

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Thiophenes
Thiophene
Benzene
thiophenes
Molecules
Conformations
rings
benzene
congeners
molecules
Atoms
interactions
Dimers
Torsional stress
torsion
atoms
Hydrogen bonds
Crystal structure
dimers
disorders

Keywords

  • crystal structure
  • carbohydrazide
  • methylation
  • weak hydrogen bonds

Cite this

@article{04e868b8375b4fac919c05b1145c0ff4,
title = "Different packing motifs of isomeric (E)-N1-(halophenylmethylidene)-N-methyl-2-(thiophen-2-yl)-acetohydrazides controlled by C—HO interactions",
abstract = "The crystal structures of three isomeric (E)-N0 -(chlorophenylmethylidene)-Nmethyl-2-(thiophen-2-yl)acetohydrazides (C14H13ClN2OS) are described, withthe Cl atom in ortho (I), meta (III) and para (IV) positions in the benzene ring.The ortho-bromo derivative (II) (C14H13BrN2OS), which is isostructural with itschloro congener (I), is also reported. Molecules (I)–(III) have similar conformations, which approximate to l-shapes, as indicated by their N—C—C—Ct (t = thiophene) torsion angles of 90.1 (3), 91.44 (18) and 90.7 (9),respectively. The conformation of (IV) is different, with an equivalent torsionangle of 170.75 (11) corresponding to a more extended shape for the molecule. The thiophene ring in each structure features ‘flip’ rotational disorder.The packing for (I) and (II) features inversion dimers, linked by pairs of C—HO interactions, which generate R22 (14) loops. In the crystal of (III), [010]C(8) chains arise, with adjacent molecules linked by pairs of C—HO hydrogen bonds. The packing for (IV) features unusually short C—HO interactions arising from an H atom attached to the benzene ring (HO = 2.18 A˚ ), which lead to C(9) [301] chains. Hirshfeld fingerprint percentage contact contributions are similar for the four title compounds.",
keywords = "crystal structure, carbohydrazide, methylation, weak hydrogen bonds",
author = "Cardoso, {Laura N. F.} and Nogueira, {Thais C. M.} and James Wardell and {de Souza}, {Marcus V. N.} and Harrison, {William T. A.}",
note = "We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections",
year = "2018",
doi = "10.1107/S2056989018001251",
language = "English",
volume = "74",
pages = "313--318",
journal = "Acta Crystallographica Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Different packing motifs of isomeric (E)-N1-(halophenylmethylidene)-N-methyl-2-(thiophen-2-yl)-acetohydrazides controlled by C—HO interactions

AU - Cardoso, Laura N. F.

AU - Nogueira, Thais C. M.

AU - Wardell, James

AU - de Souza, Marcus V. N.

AU - Harrison, William T. A.

N1 - We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections

PY - 2018

Y1 - 2018

N2 - The crystal structures of three isomeric (E)-N0 -(chlorophenylmethylidene)-Nmethyl-2-(thiophen-2-yl)acetohydrazides (C14H13ClN2OS) are described, withthe Cl atom in ortho (I), meta (III) and para (IV) positions in the benzene ring.The ortho-bromo derivative (II) (C14H13BrN2OS), which is isostructural with itschloro congener (I), is also reported. Molecules (I)–(III) have similar conformations, which approximate to l-shapes, as indicated by their N—C—C—Ct (t = thiophene) torsion angles of 90.1 (3), 91.44 (18) and 90.7 (9),respectively. The conformation of (IV) is different, with an equivalent torsionangle of 170.75 (11) corresponding to a more extended shape for the molecule. The thiophene ring in each structure features ‘flip’ rotational disorder.The packing for (I) and (II) features inversion dimers, linked by pairs of C—HO interactions, which generate R22 (14) loops. In the crystal of (III), [010]C(8) chains arise, with adjacent molecules linked by pairs of C—HO hydrogen bonds. The packing for (IV) features unusually short C—HO interactions arising from an H atom attached to the benzene ring (HO = 2.18 A˚ ), which lead to C(9) [301] chains. Hirshfeld fingerprint percentage contact contributions are similar for the four title compounds.

AB - The crystal structures of three isomeric (E)-N0 -(chlorophenylmethylidene)-Nmethyl-2-(thiophen-2-yl)acetohydrazides (C14H13ClN2OS) are described, withthe Cl atom in ortho (I), meta (III) and para (IV) positions in the benzene ring.The ortho-bromo derivative (II) (C14H13BrN2OS), which is isostructural with itschloro congener (I), is also reported. Molecules (I)–(III) have similar conformations, which approximate to l-shapes, as indicated by their N—C—C—Ct (t = thiophene) torsion angles of 90.1 (3), 91.44 (18) and 90.7 (9),respectively. The conformation of (IV) is different, with an equivalent torsionangle of 170.75 (11) corresponding to a more extended shape for the molecule. The thiophene ring in each structure features ‘flip’ rotational disorder.The packing for (I) and (II) features inversion dimers, linked by pairs of C—HO interactions, which generate R22 (14) loops. In the crystal of (III), [010]C(8) chains arise, with adjacent molecules linked by pairs of C—HO hydrogen bonds. The packing for (IV) features unusually short C—HO interactions arising from an H atom attached to the benzene ring (HO = 2.18 A˚ ), which lead to C(9) [301] chains. Hirshfeld fingerprint percentage contact contributions are similar for the four title compounds.

KW - crystal structure

KW - carbohydrazide

KW - methylation

KW - weak hydrogen bonds

U2 - 10.1107/S2056989018001251

DO - 10.1107/S2056989018001251

M3 - Article

VL - 74

SP - 313

EP - 318

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

ER -