Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides

Laura N. F. Cardoso, Thais C. M. Noguiera, Carlos R. Kaiser, James L Wardell, Marcus V. N. de Souza, William T A Harrison (Corresponding Author)

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Abstract

The syntheses and crystal structures of (E)-N′-(3-cyano­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C15H13N3OS, (I), and (E)-N′-(4-meth­oxy­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C15H16N2O2S, (II), with different substituents in the meta and para position of the benzene ring are described. Compounds (I) and (II) both crystallize with two mol­ecules in the asymmetric unit, with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280 Å, respectively] that approximate to L-shapes. The thio­phene rings in (I) are well ordered, whereas those in (II) exhibit `flip' rotational disorder [occupancies 0.662 (2) and 0.338 (2) for mol­ecule 1, and 0.549 (3) and 0.451 (3) for mol­ecule 2]. The packing for (I) features short C—H...O inter­actions arising from the C—H grouping adjacent to the cyanide group and C—H...Nc (c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C—H...π inter­actions inter­link the chains into a three-dimensional network. The packing for (II) features numerous C—H...O and C—H...π inter­actions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II).
Original languageEnglish
Pages (from-to)1636-1641
Number of pages6
JournalActa Crystallographica Section E: Crystallographic Communications
Volume73
Issue number11
DOIs
Publication statusPublished - Nov 2017

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Crystal structure
Cyanides
methylidyne
crystal structure
Molecules
Thiophenes
cyanides
Thiophene
Benzene
Conformations
molecules
rings
interactions
thiophenes
plots
benzene
disorders
synthesis

Keywords

  • crystal structure
  • carbohydrazide
  • methylation
  • weak hydrogen bonds

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Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides. / Cardoso, Laura N. F. ; Noguiera, Thais C. M.; Kaiser, Carlos R. ; Wardell, James L; de Souza, Marcus V. N.; Harrison, William T A (Corresponding Author).

In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 73, No. 11, 11.2017, p. 1636-1641.

Research output: Contribution to journalArticle

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title = "Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides",
abstract = "The syntheses and crystal structures of (E)-N′-(3-cyano­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C15H13N3OS, (I), and (E)-N′-(4-meth­oxy­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C15H16N2O2S, (II), with different substituents in the meta and para position of the benzene ring are described. Compounds (I) and (II) both crystallize with two mol­ecules in the asymmetric unit, with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280 {\AA}, respectively] that approximate to L-shapes. The thio­phene rings in (I) are well ordered, whereas those in (II) exhibit `flip' rotational disorder [occupancies 0.662 (2) and 0.338 (2) for mol­ecule 1, and 0.549 (3) and 0.451 (3) for mol­ecule 2]. The packing for (I) features short C—H...O inter­actions arising from the C—H grouping adjacent to the cyanide group and C—H...Nc (c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C—H...π inter­actions inter­link the chains into a three-dimensional network. The packing for (II) features numerous C—H...O and C—H...π inter­actions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II).",
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T1 - Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides

AU - Cardoso, Laura N. F.

AU - Noguiera, Thais C. M.

AU - Kaiser, Carlos R.

AU - Wardell, James L

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 - 2017/11

Y1 - 2017/11

N2 - The syntheses and crystal structures of (E)-N′-(3-cyano­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C15H13N3OS, (I), and (E)-N′-(4-meth­oxy­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C15H16N2O2S, (II), with different substituents in the meta and para position of the benzene ring are described. Compounds (I) and (II) both crystallize with two mol­ecules in the asymmetric unit, with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280 Å, respectively] that approximate to L-shapes. The thio­phene rings in (I) are well ordered, whereas those in (II) exhibit `flip' rotational disorder [occupancies 0.662 (2) and 0.338 (2) for mol­ecule 1, and 0.549 (3) and 0.451 (3) for mol­ecule 2]. The packing for (I) features short C—H...O inter­actions arising from the C—H grouping adjacent to the cyanide group and C—H...Nc (c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C—H...π inter­actions inter­link the chains into a three-dimensional network. The packing for (II) features numerous C—H...O and C—H...π inter­actions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II).

AB - The syntheses and crystal structures of (E)-N′-(3-cyano­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C15H13N3OS, (I), and (E)-N′-(4-meth­oxy­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C15H16N2O2S, (II), with different substituents in the meta and para position of the benzene ring are described. Compounds (I) and (II) both crystallize with two mol­ecules in the asymmetric unit, with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280 Å, respectively] that approximate to L-shapes. The thio­phene rings in (I) are well ordered, whereas those in (II) exhibit `flip' rotational disorder [occupancies 0.662 (2) and 0.338 (2) for mol­ecule 1, and 0.549 (3) and 0.451 (3) for mol­ecule 2]. The packing for (I) features short C—H...O inter­actions arising from the C—H grouping adjacent to the cyanide group and C—H...Nc (c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C—H...π inter­actions inter­link the chains into a three-dimensional network. The packing for (II) features numerous C—H...O and C—H...π inter­actions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II).

KW - crystal structure

KW - carbohydrazide

KW - methylation

KW - weak hydrogen bonds

U2 - 10.1107/S2056989017014384

DO - 10.1107/S2056989017014384

M3 - Article

VL - 73

SP - 1636

EP - 1641

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

IS - 11

ER -