Different packing motifs mediated by weak inter­actions and polymorphism in the crystal structures of five 2-(benzyl­­idene)benzosuberone derivatives

Lewis J. Seaman, Cristiane F. da Costa, Marcus V. N. de Souza, Solange M. S. V. Wardell, James L Wardell, William T A Harrison

Research output: Contribution to journalArticle

Abstract

The syntheses and crystal structures of five 2-benzyl­idene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetra­hydro-5H-benzo[7]annulen-5-one] derivatives, viz. 2-(4-meth­oxy­benzyl­idene)-1-benzosuberone, C19H18O2, (I), 2-(4-eth­oxy­benzyl­idene)-1-benzosuberone, C20H20O2, (II), 2-(4-benzyl­benzyl­idene)-1-benzosuberone, C25H22O2, (III), 2-(4-chloro­benzyl­idene)-1-benzosuberone, C18H15ClO, (IV) and 2-(4-cyano­benzyl­idene)-1-benzosuberone, C19H15NO, (V), are described. The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79 (3) for (I), 24.60 (4) for (II), 33.72 (4) for (III), 29.93 (8) for (IV) and 21.81 (7)° for (V). Key features of the packing include pairwise C—H⋯O hydrogen bonds for (II) and (IV), and pairwise C—H⋯N hydrogen bonds for (V), which generate inversion dimers in each case. The packing for (I) and (III) feature C—H⋯O hydrogen bonds, which lead to [010] and [100] chains, respectively. Weak C—H⋯π inter­actions consolidate the structures and weak aromatic π–π stacking is seen in (II) [centroid–centroid separation = 3.8414 (7) Å] and (III) [3.9475 (7) Å]. A polymorph of (I) crystallized from a different solvent has been reported previously [Dimmock et al. (1999[Dimmock, J. R., Kandepu, N. M., Nazarali, A. J., Kowalchuk, T. P., Motaganahalli, N., Quail, J. W., Mykytiuk, P., Audette, G. F., Prasad, L., Perjési, P., Allen, T. M., Santos, C. L., Szydlowski, J., De Clercq, E. & Balzarini, J. (1999). J. Med. Chem. 42, 1358-1366.]) J. Med. Chem. 42, 1358–1366] in the same space group but with a packing motif based on inversion dimers resembling that seen in (IV) in the present study. The Hirshfeld surfaces and fingerprint plots for (I) and its polymorph are com­pared and structural features of the 2-benzyl­idene-1-benzosuberone family of phases are surveyed.

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polymorphism
Polymorphism
Hydrogen bonds
Crystal structure
hydrogen bonds
Derivatives
Dimers
crystal structure
rings
Benzene
benzene
dimers
inversions
Dihedral angle
Conformations
dihedral angle
plots
fragments
methylidyne
synthesis

Keywords

  • crystal structure
  • suberone
  • polymorphism
  • Suberone
  • Crystal structure
  • Polymorphism

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Chemistry(all)
  • Materials Science(all)

Cite this

Different packing motifs mediated by weak inter­actions and polymorphism in the crystal structures of five 2-(benzyl­­idene)benzosuberone derivatives. / Seaman, Lewis J. ; da Costa, Cristiane F.; de Souza, Marcus V. N.; Wardell, Solange M. S. V.; Wardell, James L; Harrison, William T A.

In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 75, No. 11, 11.2019, p. 1741-1747.

Research output: Contribution to journalArticle

@article{ede99b93ec3a4fb0a50176ba55319b46,
title = "Different packing motifs mediated by weak inter­actions and polymorphism in the crystal structures of five 2-(benzyl­­idene)benzosuberone derivatives",
abstract = "The syntheses and crystal structures of five 2-benzyl­idene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetra­hydro-5H-benzo[7]annulen-5-one] derivatives, viz. 2-(4-meth­oxy­benzyl­idene)-1-benzosuberone, C19H18O2, (I), 2-(4-eth­oxy­benzyl­idene)-1-benzosuberone, C20H20O2, (II), 2-(4-benzyl­benzyl­idene)-1-benzosuberone, C25H22O2, (III), 2-(4-chloro­benzyl­idene)-1-benzosuberone, C18H15ClO, (IV) and 2-(4-cyano­benzyl­idene)-1-benzosuberone, C19H15NO, (V), are described. The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79 (3) for (I), 24.60 (4) for (II), 33.72 (4) for (III), 29.93 (8) for (IV) and 21.81 (7)° for (V). Key features of the packing include pairwise C—H⋯O hydrogen bonds for (II) and (IV), and pairwise C—H⋯N hydrogen bonds for (V), which generate inversion dimers in each case. The packing for (I) and (III) feature C—H⋯O hydrogen bonds, which lead to [010] and [100] chains, respectively. Weak C—H⋯π inter­actions consolidate the structures and weak aromatic π–π stacking is seen in (II) [centroid–centroid separation = 3.8414 (7) {\AA}] and (III) [3.9475 (7) {\AA}]. A polymorph of (I) crystallized from a different solvent has been reported previously [Dimmock et al. (1999[Dimmock, J. R., Kandepu, N. M., Nazarali, A. J., Kowalchuk, T. P., Motaganahalli, N., Quail, J. W., Mykytiuk, P., Audette, G. F., Prasad, L., Perj{\'e}si, P., Allen, T. M., Santos, C. L., Szydlowski, J., De Clercq, E. & Balzarini, J. (1999). J. Med. Chem. 42, 1358-1366.]) J. Med. Chem. 42, 1358–1366] in the same space group but with a packing motif based on inversion dimers resembling that seen in (IV) in the present study. The Hirshfeld surfaces and fingerprint plots for (I) and its polymorph are com­pared and structural features of the 2-benzyl­idene-1-benzosuberone family of phases are surveyed.",
keywords = "crystal structure, suberone, polymorphism, Suberone, Crystal structure, Polymorphism",
author = "Seaman, {Lewis J.} and {da Costa}, {Cristiane F.} and {de Souza}, {Marcus V. N.} and Wardell, {Solange M. S. V.} and Wardell, {James L} and Harrison, {William T A}",
year = "2019",
month = "11",
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language = "English",
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pages = "1741--1747",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "11",

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TY - JOUR

T1 - Different packing motifs mediated by weak inter­actions and polymorphism in the crystal structures of five 2-(benzyl­­idene)benzosuberone derivatives

AU - Seaman, Lewis J.

AU - da Costa, Cristiane F.

AU - de Souza, Marcus V. N.

AU - Wardell, Solange M. S. V.

AU - Wardell, James L

AU - Harrison, William T A

PY - 2019/11

Y1 - 2019/11

N2 - The syntheses and crystal structures of five 2-benzyl­idene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetra­hydro-5H-benzo[7]annulen-5-one] derivatives, viz. 2-(4-meth­oxy­benzyl­idene)-1-benzosuberone, C19H18O2, (I), 2-(4-eth­oxy­benzyl­idene)-1-benzosuberone, C20H20O2, (II), 2-(4-benzyl­benzyl­idene)-1-benzosuberone, C25H22O2, (III), 2-(4-chloro­benzyl­idene)-1-benzosuberone, C18H15ClO, (IV) and 2-(4-cyano­benzyl­idene)-1-benzosuberone, C19H15NO, (V), are described. The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79 (3) for (I), 24.60 (4) for (II), 33.72 (4) for (III), 29.93 (8) for (IV) and 21.81 (7)° for (V). Key features of the packing include pairwise C—H⋯O hydrogen bonds for (II) and (IV), and pairwise C—H⋯N hydrogen bonds for (V), which generate inversion dimers in each case. The packing for (I) and (III) feature C—H⋯O hydrogen bonds, which lead to [010] and [100] chains, respectively. Weak C—H⋯π inter­actions consolidate the structures and weak aromatic π–π stacking is seen in (II) [centroid–centroid separation = 3.8414 (7) Å] and (III) [3.9475 (7) Å]. A polymorph of (I) crystallized from a different solvent has been reported previously [Dimmock et al. (1999[Dimmock, J. R., Kandepu, N. M., Nazarali, A. J., Kowalchuk, T. P., Motaganahalli, N., Quail, J. W., Mykytiuk, P., Audette, G. F., Prasad, L., Perjési, P., Allen, T. M., Santos, C. L., Szydlowski, J., De Clercq, E. & Balzarini, J. (1999). J. Med. Chem. 42, 1358-1366.]) J. Med. Chem. 42, 1358–1366] in the same space group but with a packing motif based on inversion dimers resembling that seen in (IV) in the present study. The Hirshfeld surfaces and fingerprint plots for (I) and its polymorph are com­pared and structural features of the 2-benzyl­idene-1-benzosuberone family of phases are surveyed.

AB - The syntheses and crystal structures of five 2-benzyl­idene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetra­hydro-5H-benzo[7]annulen-5-one] derivatives, viz. 2-(4-meth­oxy­benzyl­idene)-1-benzosuberone, C19H18O2, (I), 2-(4-eth­oxy­benzyl­idene)-1-benzosuberone, C20H20O2, (II), 2-(4-benzyl­benzyl­idene)-1-benzosuberone, C25H22O2, (III), 2-(4-chloro­benzyl­idene)-1-benzosuberone, C18H15ClO, (IV) and 2-(4-cyano­benzyl­idene)-1-benzosuberone, C19H15NO, (V), are described. The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79 (3) for (I), 24.60 (4) for (II), 33.72 (4) for (III), 29.93 (8) for (IV) and 21.81 (7)° for (V). Key features of the packing include pairwise C—H⋯O hydrogen bonds for (II) and (IV), and pairwise C—H⋯N hydrogen bonds for (V), which generate inversion dimers in each case. The packing for (I) and (III) feature C—H⋯O hydrogen bonds, which lead to [010] and [100] chains, respectively. Weak C—H⋯π inter­actions consolidate the structures and weak aromatic π–π stacking is seen in (II) [centroid–centroid separation = 3.8414 (7) Å] and (III) [3.9475 (7) Å]. A polymorph of (I) crystallized from a different solvent has been reported previously [Dimmock et al. (1999[Dimmock, J. R., Kandepu, N. M., Nazarali, A. J., Kowalchuk, T. P., Motaganahalli, N., Quail, J. W., Mykytiuk, P., Audette, G. F., Prasad, L., Perjési, P., Allen, T. M., Santos, C. L., Szydlowski, J., De Clercq, E. & Balzarini, J. (1999). J. Med. Chem. 42, 1358-1366.]) J. Med. Chem. 42, 1358–1366] in the same space group but with a packing motif based on inversion dimers resembling that seen in (IV) in the present study. The Hirshfeld surfaces and fingerprint plots for (I) and its polymorph are com­pared and structural features of the 2-benzyl­idene-1-benzosuberone family of phases are surveyed.

KW - crystal structure

KW - suberone

KW - polymorphism

KW - Suberone

KW - Crystal structure

KW - Polymorphism

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U2 - 10.1107/S2056989019014245

DO - 10.1107/S2056989019014245

M3 - Article

VL - 75

SP - 1741

EP - 1747

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

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ER -