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

Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review

Autoren

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

Organisationseinheiten

Externe Organisationen

  • Christian-Albrechts-Universität zu Kiel (CAU)
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Details

OriginalspracheEnglisch
Seiten (von - bis)435-438
Seitenumfang4
FachzeitschriftActa Crystallographica Section E: Crystallographic Communications
Jahrgang80
AusgabenummerPt 4
PublikationsstatusVeröffentlicht - 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.

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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, Jahrgang 80, Nr. Pt 4, 04.2024, S. 435-438.

Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › 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, Jg. 80, Nr. Pt 4, S. 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 ; Jahrgang 80, Nr. Pt 4. S. 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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author = "Artjom Businski and Ta, {Thuy C.} and Niklas Gindullis and Christian N{\"a}ther and Rainer Herges",
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TY - JOUR

T1 - Synthesis and crystal structure of tetramethyl (E)-4,40-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate)

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.

PY - 2024/4

Y1 - 2024/4

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.

KW - crystal structure

KW - diazocine

KW - stilbene derivative

KW - synthesis

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U2 - 10.1107/S2056989024002676

DO - 10.1107/S2056989024002676

M3 - Article

AN - SCOPUS:85189703238

VL - 80

SP - 435

EP - 438

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - Pt 4

ER -