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Hernández-Téllez G, Bernès S, Mendoza A, et al. Crystal structures of four chiral imine-substituted thio-phene derivatives. Acta Crystallogr E Crystallogr Commun. 2016;72:350-4doi: 10.1107/S2056989016002516.
Hernández-Téllez, G., Bernès, S., Mendoza, A., Ríos-Merino, F. J., Moreno, G. E., Portillo, O., & Gutiérrez, R. (2016). Crystal structures of four chiral imine-substituted thio-phene derivatives. Acta crystallographica. Section E, Crystallographic communications, 72350-4. https://doi.org/10.1107/S2056989016002516
Hernández-Téllez, Guadalupe, et al. "Crystal structures of four chiral imine-substituted thio-phene derivatives." Acta crystallographica. Section E, Crystallographic communications vol. 72 (2016): 350-4. doi: https://doi.org/10.1107/S2056989016002516
Hernández-Téllez G, Bernès S, Mendoza A, Ríos-Merino FJ, Moreno GE, Portillo O, Gutiérrez R. Crystal structures of four chiral imine-substituted thio-phene derivatives. Acta Crystallogr E Crystallogr Commun. 2016 Feb 17;72:350-4. doi: 10.1107/S2056989016002516. eCollection 2016 Mar 01. PMID: 27006806; PMCID: PMC4778840.
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Acta Crystallogr E Crystallogr Commun. 2016 Feb 17;72:350-4. doi: 10.1107/S2056989016002516. eCollection 2016 Mar 01.

Crystal structures of four chiral imine-substituted thio-phene derivatives.

Acta crystallographica. Section E, Crystallographic communications

Guadalupe Hernández-Téllez, Sylvain Bernès, Angel Mendoza, Francisco Javier Ríos-Merino, Gloria E Moreno, Oscar Portillo, René Gutiérrez

Affiliations

  1. Laboratorio de Síntesis de Complejos, Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, A.P. 1067, 72001 Puebla, Pue., Mexico.
  2. Instituto de Física, Universidad Autónoma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico.
  3. Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, 72570 Puebla, Pue., Mexico.

PMID: 27006806 PMCID: PMC4778840 DOI: 10.1107/S2056989016002516

Abstract

A series of thio-phenes substituted in positions 2 and 5 by imine groups have been synthesized using a solvent-free approach, and their crystal structures determined. The substituents are chiral groups, and the expected absolute configuration for each mol-ecule was confirmed by refinement of the Flack parameter. The compounds are 2,5-bis-[(S)-(+)-(1,2,3,4-tetra-hydro-naphthalen-1-yl)imino]-thio-phene, C26H26N2S, (I), 2,5-bis-{[(R)-(-)-1-(4-meth-oxy-phen-yl)eth-yl]imino-meth-yl}thio-phene, C24H26N2O2S, (II), 2,5-bis-{[(R)-(-)-1-(4-fluoro-phen-yl)eth-yl]imino-meth-yl}thio-phene, C22H20F2N2S, (III), and 2,5-bis-{[(S)-(+)-1-(4-chloro-phen-yl)eth-yl]imino-meth-yl}thio-phene, C22H20Cl2N2S, (IV). A common feature of all four mol-ecules is the presence of twofold symmetry. For (I), which crystallizes in the triclinic space group P1, this symmetry is non-crystallographic, but for (II) in C2 and the isomorphous structures (III) and (IV) that crystallize in P21212, the twofold symmetry is crystallographically imposed with one half of each mol-ecule in the asymmetric unit. The comparable mol-ecular symmetry in the four structures is also reflected in similar packing, with mol-ecules aggregated to form chains through weak C-H⋯S inter-actions.

Keywords: Schiff base; bis-imine; crystal structure; thio­phene

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