Synthesis and crystal structure of tetramethyl (E)-4,40-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate)

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

Authors

  • Artjom Businski
  • Thuy C. Ta
  • Niklas Gindullis
  • Christian Näther
  • Rainer Herges

Research Organisations

External Research Organisations

  • Kiel University
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Details

Original languageEnglish
Pages (from-to)435-438
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume80
Issue numberPt 4
Publication statusPublished - Apr 2024

Abstract

The title compound, C22H18N2O12, was obtained as a by-product during the planned synthesis of 1,2-bis(2-nitro-4,5-dimethyl phthalate)ethane by oxidative dimerization starting from dimethyl-4-methyl-5-nitro phthalate. To identify this compound unambiguously, a single-crystal structure analysis was performed. The asymmetric unit consists of half a molecule that is located at a centre of inversion. As a result of symmetry restrictions, the molecule shows an E configuration around the double bond. Both phenyl rings are coplanar, whereas the nitro and the two methyl ester groups are rotated out of the ring plane by 32.6 (1), 56.5 (2) and 49.5 (2), respectively. In the crystal, molecules are connected into chains extending parallel to the a axis by pairs of C—H O hydrogen bonds that are connected into a tri-periodic network by additional C—H O hydrogen-bonding interactions.

Keywords

    crystal structure, diazocine, stilbene derivative, synthesis

ASJC Scopus subject areas

Cite this

Synthesis and crystal structure of tetramethyl (E)-4,40-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate). / Businski, Artjom; Ta, Thuy C.; Gindullis, Niklas et al.
In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 80, No. Pt 4, 04.2024, p. 435-438.

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

Businski, A, Ta, TC, Gindullis, N, Näther, C & Herges, R 2024, 'Synthesis and crystal structure of tetramethyl (E)-4,40-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate)', Acta Crystallographica Section E: Crystallographic Communications, vol. 80, no. Pt 4, pp. 435-438. https://doi.org/10.1107/S2056989024002676
Businski, A., Ta, T. C., Gindullis, N., Näther, C., & Herges, R. (2024). Synthesis and crystal structure of tetramethyl (E)-4,40-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate). Acta Crystallographica Section E: Crystallographic Communications, 80(Pt 4), 435-438. https://doi.org/10.1107/S2056989024002676
Businski A, Ta TC, Gindullis N, Näther C, Herges R. Synthesis and crystal structure of tetramethyl (E)-4,40-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate). Acta Crystallographica Section E: Crystallographic Communications. 2024 Apr;80(Pt 4):435-438. doi: 10.1107/S2056989024002676
Businski, Artjom ; Ta, Thuy C. ; Gindullis, Niklas et al. / Synthesis and crystal structure of tetramethyl (E)-4,40-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate). In: Acta Crystallographica Section E: Crystallographic Communications. 2024 ; Vol. 80, No. Pt 4. pp. 435-438.
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title = "Synthesis and crystal structure of tetramethyl (E)-4,40-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate)",
abstract = "The title compound, C22H18N2O12, was obtained as a by-product during the planned synthesis of 1,2-bis(2-nitro-4,5-dimethyl phthalate)ethane by oxidative dimerization starting from dimethyl-4-methyl-5-nitro phthalate. To identify this compound unambiguously, a single-crystal structure analysis was performed. The asymmetric unit consists of half a molecule that is located at a centre of inversion. As a result of symmetry restrictions, the molecule shows an E configuration around the double bond. Both phenyl rings are coplanar, whereas the nitro and the two methyl ester groups are rotated out of the ring plane by 32.6 (1), 56.5 (2) and 49.5 (2), respectively. In the crystal, molecules are connected into chains extending parallel to the a axis by pairs of C—H O hydrogen bonds that are connected into a tri-periodic network by additional C—H O hydrogen-bonding interactions.",
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AU - Businski, Artjom

AU - Ta, Thuy C.

AU - Gindullis, Niklas

AU - Näther, Christian

AU - Herges, Rainer

N1 - Funding Information: This work was supported by the State of Schleswig-Holstein.

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N2 - The title compound, C22H18N2O12, was obtained as a by-product during the planned synthesis of 1,2-bis(2-nitro-4,5-dimethyl phthalate)ethane by oxidative dimerization starting from dimethyl-4-methyl-5-nitro phthalate. To identify this compound unambiguously, a single-crystal structure analysis was performed. The asymmetric unit consists of half a molecule that is located at a centre of inversion. As a result of symmetry restrictions, the molecule shows an E configuration around the double bond. Both phenyl rings are coplanar, whereas the nitro and the two methyl ester groups are rotated out of the ring plane by 32.6 (1), 56.5 (2) and 49.5 (2), respectively. In the crystal, molecules are connected into chains extending parallel to the a axis by pairs of C—H O hydrogen bonds that are connected into a tri-periodic network by additional C—H O hydrogen-bonding interactions.

AB - The title compound, C22H18N2O12, was obtained as a by-product during the planned synthesis of 1,2-bis(2-nitro-4,5-dimethyl phthalate)ethane by oxidative dimerization starting from dimethyl-4-methyl-5-nitro phthalate. To identify this compound unambiguously, a single-crystal structure analysis was performed. The asymmetric unit consists of half a molecule that is located at a centre of inversion. As a result of symmetry restrictions, the molecule shows an E configuration around the double bond. Both phenyl rings are coplanar, whereas the nitro and the two methyl ester groups are rotated out of the ring plane by 32.6 (1), 56.5 (2) and 49.5 (2), respectively. In the crystal, molecules are connected into chains extending parallel to the a axis by pairs of C—H O hydrogen bonds that are connected into a tri-periodic network by additional C—H O hydrogen-bonding interactions.

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KW - synthesis

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