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Volume 69 
Part 9 
Page o1428  
September 2013  

Received 17 July 2013
Accepted 2 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.008 Å
R = 0.052
wR = 0.155
Data-to-parameter ratio = 14.1
Details
Open access

2,5-Bis{[(-)-(S)-1-(4-methylphenyl)ethyl]iminomethyl}thiophene

aDEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, NL, Mexico,bLaboratorio de Síntesis de Complejos, Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, PO Box 156, 72001 Puebla, Pue., Mexico, and cIngeniería Bioquímica, Instituto Tecnológico Superior de Atlixco, 74218 Atlixco, Pue., Mexico
Correspondence e-mail: sylvain_bernes@Hotmail.com

The title chiral bis-aldimine, C24H26N2S, was synthesized using a solvent-free Schiff condensation. The molecule displays crystallographic C2 symmetry, with the S atom lying on the twofold axis parallel to [100]. As a consequence of the (S,S) stereochemistry, the tolyl groups are oriented towards opposite faces of the thiophene core, giving a twisted conformation for the whole molecule. Molecules are arranged in the crystal in a herringbone-like pattern, without any significant intermolecular contacts.

Related literature

For the solvent-free approach in organic synthesis, see: Tanaka & Toda (2000[Tanaka, K. & Toda, F. (2000). Chem. Rev. 100, 1025-1074.]). For the structure of a chiral bis-aldimine compound, see: Espinosa Leija et al. (2009[Espinosa Leija, A., Bernès, S., Hernández, G., Sharma, P., Peña, U. & Gutiérrez, R. (2009). Acta Cryst. E65, o2317.]). For structures of thiophenes substituted in positions 2 and 5 by imine functionalities, see: Skene & Dufresne (2006[Skene, W. G. & Dufresne, S. (2006). Acta Cryst. E62, o1116-o1117.]); Fridman & Kaftory (2007[Fridman, N. & Kaftory, M. (2007). Pol. J. Chem. 81, 825-832.]); de Lima et al. (2010[Lima, G. M. de, Harrison, W. T. A., Tiekink, E. R. T., Wardell, J. L. & Wardell, S. M. S. V. (2010). Acta Cryst. E66, o504-o505.]); Kudyakova et al. (2011[Kudyakova, Yu. S., Burgart, Ya. V. & Saloutin, V. I. (2011). Chem. Heterocycl. Compd, 47, 558-563.], 2012[Kudyakova, Y. S., Burgart, Y. V., Slepukhin, P. A. & Saloutin, V. I. (2012). Mendeleev Commun. 22, 284-286.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26N2S

  • Mr = 374.53

  • Orthorhombic, P 221 21

  • a = 6.278 (3) Å

  • b = 7.900 (3) Å

  • c = 21.500 (7) Å

  • V = 1066.4 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 298 K

  • 0.50 × 0.32 × 0.10 mm

Data collection
  • Bruker P4 diffractometer

  • Absorption correction: [psi] scan (XSCANS; Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.754, Tmax = 0.985

  • 3046 measured reflections

  • 1767 independent reflections

  • 1352 reflections with I > 2[sigma](I)

  • Rint = 0.066

  • 3 standard reflections every 97 reflections intensity decay: 2.5%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.155

  • S = 1.06

  • 1767 reflections

  • 125 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

  • Absolute structure: Flack x determined using 412 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.])

  • Absolute structure parameter: -0.08 (18)

Data collection: XSCANS (Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL2013.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2315 ).


Acknowledgements

Support from VIEP-UAP (GUPJ-NAT12-G) is acknowledged.

References

Espinosa Leija, A., Bernès, S., Hernández, G., Sharma, P., Peña, U. & Gutiérrez, R. (2009). Acta Cryst. E65, o2317.  [CSD] [CrossRef] [details]
Fridman, N. & Kaftory, M. (2007). Pol. J. Chem. 81, 825-832.  [ChemPort]
Kudyakova, Yu. S., Burgart, Ya. V. & Saloutin, V. I. (2011). Chem. Heterocycl. Compd, 47, 558-563.  [CrossRef] [ChemPort]
Kudyakova, Y. S., Burgart, Y. V., Slepukhin, P. A. & Saloutin, V. I. (2012). Mendeleev Commun. 22, 284-286.  [ISI] [CSD] [CrossRef] [ChemPort]
Lima, G. M. de, Harrison, W. T. A., Tiekink, E. R. T., Wardell, J. L. & Wardell, S. M. S. V. (2010). Acta Cryst. E66, o504-o505.  [CSD] [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Skene, W. G. & Dufresne, S. (2006). Acta Cryst. E62, o1116-o1117.  [CSD] [CrossRef] [ChemPort] [details]
Tanaka, K. & Toda, F. (2000). Chem. Rev. 100, 1025-1074.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1428  [ doi:10.1107/S1600536813021685 ]

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