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Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate

Year 2023, , 72 - 78, 31.12.2023
https://doi.org/10.47897/bilmes.1316337

Abstract

The title compound (1), C19H20N2O2, crystallized with single molecule in the asymmetric unit and is present in the zwitterionic form. The compound was synthesized from the condensation reaction of 8-hydroxyjulolidine-9-carbaldehyde and 3-aminophenol. In solid state compound adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N—H···O hydrogen bond with an S(6) ring motif. The conformation about the C=N bond is E. The aromatic ring of the julolidine moiety is inclined to the phenol ring by 13.00 (10)°. The fused non-aromatic rings of the julolidine moiety adopts a screw-boat conformations. In the crystal, the molecules are connected by N—H···O and O—H···O hydrogen bonds, with adjacent molecules related by a 21 screw axis, generating– A–B–A–B–zigzag chains extending along [010]. Furthermore, adjacent molecules are linked by pairs of C—H···O interactions, forming a ladder-like structure propagating along the a-axis direction. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

References

  • [1] Narayanaswamy, N. & Govindaraju, T. (2012). “Sens. Actuators B”, Chem. 161, 304–310.
  • [2] Maity, D., Manna, A. K., Karthigeyan, D., Kundu, T. K., Pati, S. K. & Govindaraju, T. (2011). “Chem. Eur. J”. 17, 11152–11161.
  • [3] Noh, J. Y., Kim, S., Hwang, I. H., Lee, G. Y., Kang, J., Kim, S. H., Min, J., Park, S., Kim, C. & Kim, J. (2013). “Dyes Pigments”, 99, 1016–1021.
  • [4] Nano, A., Gullo, M. P., Ventura, B., Armaroli, N., Barbieri, A. & Ziessel, R. (2015). “Chem. Commun”.51, 3351–3354.
  • [5] Jo, T. G., Na, Y. J., Lee, J. J., Lee, M. M., Lee, S. Y. & Kim, C. (2015). “New J. Chem”. 39, 2580–2587.
  • [6] Choi, Y. W., Lee, J. J., You, G. R., Lee, S. Y. & Kim, C. (2015). “RSC Adv”. 5, 86463–86472.
  • [7] Kim, Y. S., Lee, J. J., Choi, Y. W., You, G. R., Nguyen, L., Noh, I. & Kim, C. (2016). “Dyes Pigments”, 129, 43–53.
  • [8] Lee, S. A., You, G. R., Choi, Y. W., Jo, H. Y., Kim, A. R., Noh, I., Kim, S.-J., Kim, Y. & Kim, C. (2014). “Dalton Trans.” 43, 6650–6659.
  • [9] Mennucci, B., Cappelli, C., Guido, C. A., Cammi, R. & Tomasi, J. (2009). “J. Phys. Chem. A”, 113, 3009–3020.
  • [10] Park, G. J., Park, D. Y., Park, K.-M., Kim, Y., Kim, S.-J., Chang, P.-S. & Kim, C. (2014). “Tetrahedron”, 70, 7429–7438.
  • [11] Faizi, M. S. H., Ali, A. & Potaskalov, V. A. (2016). “Acta Cryst”. E72, 1366–1369.
  • [12] Faizi, M. S. H., Ahmad, M., Kapshuk, A. A. & Golenya, I. A. (2017a). “Acta Cryst”. E73,38–40
  • [13] Faizi, M. S. H., Dege, N. & Malysheva, M. L. (2017b). “Acta Cryst”. E73, 791–794.
  • [14] Na, Y. J., Hwang, I. H., Jo, H. Y., Lee, S. A., Park, G. J. & Kim, C. (2013). Inorg. “Chem. Commun”. 35, 342–345.
  • [15] Faizi, M. S. H., Iskenderov, T. S. & Sharkina, N. O. (2015). “Acta Cryst”. E71, 28–30.
  • [16] Kantar, E. N., Köysal, Y., Akdemir, N., Agăr, A. A. & Soylu, M. S. (2013). “Acta Cryst”. E69,0883
  • [17] Frisch, M. J., et al. (2009). GAUSSIAN09. Revision A. 02. Gaussian Inc., Wallingford, CT, USA.
  • [18] Becke, A. D. (1993). “J. Chem. Phys”. 98, 5648–5652.
  • [19] Groom (2016). “The cabricke structural data base”. Acta crystallographice B,72,171-179

Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate

Year 2023, , 72 - 78, 31.12.2023
https://doi.org/10.47897/bilmes.1316337

Abstract

The title compound (1), C19H20N2O2, crystallized with single molecule in the asymmetric unit and is present in the zwitterionic form. The compound was synthesized from the condensation reaction of 8-hydroxyjulolidine-9-carbaldehyde and 3-aminophenol. In solid state compound adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N—H···O hydrogen bond with an S(6) ring motif. The conformation about the C=N bond is E. The aromatic ring of the julolidine moiety is inclined to the phenol ring by 13.00 (10)°. The fused non-aromatic rings of the julolidine moiety adopts a screw-boat conformations. In the crystal, the molecules are connected by N—H···O and O—H···O hydrogen bonds, with adjacent molecules related by a 21 screw axis, generating– A–B–A–B–zigzag chains extending along [010]. Furthermore, adjacent molecules are linked by pairs of C—H···O interactions, forming a ladder-like structure propagating along the a-axis direction. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

References

  • [1] Narayanaswamy, N. & Govindaraju, T. (2012). “Sens. Actuators B”, Chem. 161, 304–310.
  • [2] Maity, D., Manna, A. K., Karthigeyan, D., Kundu, T. K., Pati, S. K. & Govindaraju, T. (2011). “Chem. Eur. J”. 17, 11152–11161.
  • [3] Noh, J. Y., Kim, S., Hwang, I. H., Lee, G. Y., Kang, J., Kim, S. H., Min, J., Park, S., Kim, C. & Kim, J. (2013). “Dyes Pigments”, 99, 1016–1021.
  • [4] Nano, A., Gullo, M. P., Ventura, B., Armaroli, N., Barbieri, A. & Ziessel, R. (2015). “Chem. Commun”.51, 3351–3354.
  • [5] Jo, T. G., Na, Y. J., Lee, J. J., Lee, M. M., Lee, S. Y. & Kim, C. (2015). “New J. Chem”. 39, 2580–2587.
  • [6] Choi, Y. W., Lee, J. J., You, G. R., Lee, S. Y. & Kim, C. (2015). “RSC Adv”. 5, 86463–86472.
  • [7] Kim, Y. S., Lee, J. J., Choi, Y. W., You, G. R., Nguyen, L., Noh, I. & Kim, C. (2016). “Dyes Pigments”, 129, 43–53.
  • [8] Lee, S. A., You, G. R., Choi, Y. W., Jo, H. Y., Kim, A. R., Noh, I., Kim, S.-J., Kim, Y. & Kim, C. (2014). “Dalton Trans.” 43, 6650–6659.
  • [9] Mennucci, B., Cappelli, C., Guido, C. A., Cammi, R. & Tomasi, J. (2009). “J. Phys. Chem. A”, 113, 3009–3020.
  • [10] Park, G. J., Park, D. Y., Park, K.-M., Kim, Y., Kim, S.-J., Chang, P.-S. & Kim, C. (2014). “Tetrahedron”, 70, 7429–7438.
  • [11] Faizi, M. S. H., Ali, A. & Potaskalov, V. A. (2016). “Acta Cryst”. E72, 1366–1369.
  • [12] Faizi, M. S. H., Ahmad, M., Kapshuk, A. A. & Golenya, I. A. (2017a). “Acta Cryst”. E73,38–40
  • [13] Faizi, M. S. H., Dege, N. & Malysheva, M. L. (2017b). “Acta Cryst”. E73, 791–794.
  • [14] Na, Y. J., Hwang, I. H., Jo, H. Y., Lee, S. A., Park, G. J. & Kim, C. (2013). Inorg. “Chem. Commun”. 35, 342–345.
  • [15] Faizi, M. S. H., Iskenderov, T. S. & Sharkina, N. O. (2015). “Acta Cryst”. E71, 28–30.
  • [16] Kantar, E. N., Köysal, Y., Akdemir, N., Agăr, A. A. & Soylu, M. S. (2013). “Acta Cryst”. E69,0883
  • [17] Frisch, M. J., et al. (2009). GAUSSIAN09. Revision A. 02. Gaussian Inc., Wallingford, CT, USA.
  • [18] Becke, A. D. (1993). “J. Chem. Phys”. 98, 5648–5652.
  • [19] Groom (2016). “The cabricke structural data base”. Acta crystallographice B,72,171-179
There are 19 citations in total.

Details

Primary Language English
Subjects Atomic and Molecular Physics, Material Physics
Journal Section Articles
Authors

Hasan İnaç 0000-0002-8870-5317

Publication Date December 31, 2023
Acceptance Date August 14, 2023
Published in Issue Year 2023

Cite

APA İnaç, H. (2023). Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. International Scientific and Vocational Studies Journal, 7(2), 72-78. https://doi.org/10.47897/bilmes.1316337
AMA İnaç H. Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. ISVOS. December 2023;7(2):72-78. doi:10.47897/bilmes.1316337
Chicago İnaç, Hasan. “Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate”. International Scientific and Vocational Studies Journal 7, no. 2 (December 2023): 72-78. https://doi.org/10.47897/bilmes.1316337.
EndNote İnaç H (December 1, 2023) Crystal Structure of Zwitterionic (E)-9-(3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. International Scientific and Vocational Studies Journal 7 2 72–78.
IEEE H. İnaç, “Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate”, ISVOS, vol. 7, no. 2, pp. 72–78, 2023, doi: 10.47897/bilmes.1316337.
ISNAD İnaç, Hasan. “Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate”. International Scientific and Vocational Studies Journal 7/2 (December 2023), 72-78. https://doi.org/10.47897/bilmes.1316337.
JAMA İnaç H. Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. ISVOS. 2023;7:72–78.
MLA İnaç, Hasan. “Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate”. International Scientific and Vocational Studies Journal, vol. 7, no. 2, 2023, pp. 72-78, doi:10.47897/bilmes.1316337.
Vancouver İnaç H. Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. ISVOS. 2023;7(2):72-8.


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