Crystal structure of (Z)-methyl N'-(5,7-dibromo-1-(2-morpholinoethyl)-2- oxoindolin-3-ylidene)hydrazinecarbodithioate, C16H18Br2N4O2S2

Ma, Lei; Li, Aimin; Wan, Chong‐Qing; Cao, Sheng‐Li

doi:10.1515/ncrs-2014-0020

Zeitschrift Für Kristallographie - New Crystal Structures

2014

DOI: 10.1515/ncrs-2014-0020

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Crystal structure of (Z)-methyl N'-(5,7-dibromo-1-(2-morpholinoethyl)-2- oxoindolin-3-ylidene)hydrazinecarbodithioate, C16H18Br2N4O2S2

Lei Ma¹,

Aimin Li²,

Chong‐Qing Wan³

et al.

Abstract: Abstract

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Cited by 3 publications

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“…Searching the Cambridge Structural Database, one can find a small number of larger, relatively bulky building blocks that are halogen bonded via either the morpholine oxygen or piperazine nitrogen atoms. Most numerous are polyfunctional organic compounds, − followed by metal–organic complexes ,− and clathrates. , Only a few of these studies ,,,− have been systematically focused on halogen bonding. Therefore, we set out to further investigate the possibility of halogen bond formation and the possible diversity of halogen bond motifs in bulkier molecules containing peripherally located morpholine and piperazine fragments as potential building blocks in the design of novel halogen-bonded multicomponent solids …”

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confidence: 99%

Halogen Bond Motifs in Cocrystals of N,N,O and N,O,O Acceptors Derived from Diketones and Containing a Morpholine or Piperazine Moiety

Sušanj

Nemec

Bedeković

et al. 2022

Crystal Growth & Design

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In this study, we investigate the halogen bond acceptor potential of oxygen and nitrogen atoms of morpholine and piperazine fragments when they are peripherally located on N,O,O or N,N,O acceptor molecules. We synthesized four acceptor molecules derived from either acetylacetone or benzoylacetone and cocrystallized them with 1,4-diiodotetrafluorobenzene and 1,3,5triiodotrifluorobenzene. This resulted in eight cocrystals featuring different topicities and geometric dispositions of donor atoms. In all cocrystals, halogen bonds are formed with either the morpholinyl oxygen atom or the terminal piperazine nitrogen atom. The I•••O morpholine halogen bonds feature lower relative shortening values than I•••N terminal , I•••O carbonyl , and I•••N proximal halogen bonds. The N and O halogen bond acceptor sites were evaluated through calculations of molecular electrostatic potential values.

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mentioning

confidence: 99%

Halogen Bond Motifs in Cocrystals of N,N,O and N,O,O Acceptors Derived from Diketones and Containing a Morpholine or Piperazine Moiety

Sušanj

Nemec

Bedeković

et al. 2022

Crystal Growth & Design

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Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Qin

Cao

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 10 H 8 FN 3 OS 2 , monoclinic, P2 1 /c (no. 14), a = 6.2909(2) Å, CCDC no.: 1557525The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was obtained via condensation of 5-fluoroindoline-2,3-dione (0.3 g, 2 mmol) with methyl hydrazinecarbodithioate (0.2 g, 2 mmol) in 8 mL methanol at room temperature for 12 h. The mixture was isolated by column chromatography on silica gel with dichloromethane/methanol = 98:2 (v/v) as eluent to give the title compound methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate (yield 65%; m.p.

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Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C₂₂H₃₁N₅O₄S₂

Qin

Cao

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1557526The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was synthesized via a three-step synthetic protocol. The reaction of 5-methoxyindoline-2,3-dione (0.9 g, 5 mmol) with 1,2-dibromoethane (2.8 g,15 mmol) in 15 mL of N,N-dimethylformamide (DMF) in the presence of potassium carbonate (1.0 g, 7.2 mmol) at 40-50°C gave 1-(2-bromoethyl)indoline-2,3-dione [4]. Next, 1-(2-bromoethyl) indoline-2,3-dione (0.6 g, 2.0 mmol) was reacted with tertbutyl piperazine-1-carboxylate (1.1 g, 0.6 mmol) in DMF (5 mL) for 12 h at room temperature to yield 1-((4-(tertbutyloxycarbonyl)piperazin-1-yl)ethyl)-5-methoxyindolin-2,3-dione. Finally, condensation of 1-((4-(tert-butyloxycarbonyl) piperazin-1-yl)-5-methoxyindolin-2,3-dione (0.4 g, 1 mmol) with methyl hydrazinecarbodithioate (0.1 g, 1 mmol) in 5 mL methanol at room temperature for 12 h gave a solid, which was collected by filtration and dried in air. The crude product was purified by recrystallization from methanol (yield 60%; m.p. 421-423 K). Crystals of the title compound were obtained by slow evaporation of the mixed solvent dichloromethane and methanol (5:1, v/v). Experimental detailsH atoms were placed in calculated positions. The U iso values of the hydrogen atoms of methyl groups were set to 1.5U eq (C) and the U iso values of all other hydrogen atoms were set to 1.2U eq (C, N). DiscussionIndolin-2-one derivatives exhibit promising antitumor activity by targeting different biomacromolecules [5,6], of which 3-hydrazinoindolin-2-one derivatives have particularly attracted intensive attention [7,8]. In our previous work, methyl hydrazinecarbodithioate derivatives of 5-fluoro-1-(2-morpholinoethyl)indolin-2-one and 5-methoxy-1-(2-morpholinoethyl)indolin-2-one were used as ligands to achieve two new Pt(II) complexes, which exhibited cytotoxicity against cancer cells by inducing apoptosis [9]. As a continuous work, herein we report a new methyl hydrazinecarbodithioate derivative. X-ray single-crystal diffraction analysis revealed that the hydrazinecarbodithioate and

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Crystal structure of (Z)-methyl N'-(5,7-dibromo-1-(2-morpholinoethyl)-2- oxoindolin-3-ylidene)hydrazinecarbodithioate, C16H18Br2N4O2S2

Abstract: Abstract

Cited by 3 publications

References 7 publications

Halogen Bond Motifs in Cocrystals of N,N,O and N,O,O Acceptors Derived from Diketones and Containing a Morpholine or Piperazine Moiety

Halogen Bond Motifs in Cocrystals of N,N,O and N,O,O Acceptors Derived from Diketones and Containing a Morpholine or Piperazine Moiety

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C₂₂H₃₁N₅O₄S₂

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Crystal structure of (Z)-methyl N'-(5,7-dibromo-1-(2-morpholinoethyl)-2- oxoindolin-3-ylidene)hydrazinecarbodithioate, C16H18Br2N4O2S2

Abstract: Abstract

Cited by 3 publications

References 7 publications

Halogen Bond Motifs in Cocrystals of N,N,O and N,O,O Acceptors Derived from Diketones and Containing a Morpholine or Piperazine Moiety

Halogen Bond Motifs in Cocrystals of N,N,O and N,O,O Acceptors Derived from Diketones and Containing a Morpholine or Piperazine Moiety

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C10H8FN3OS2

Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C22H31N5O4S2

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Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C₂₂H₃₁N₅O₄S₂