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Volume 69 
Part 9 
Page o1480  
September 2013  

Received 14 August 2013
Accepted 21 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.006 Å
R = 0.040
wR = 0.092
Data-to-parameter ratio = 13.7
Details
Open access

(+)-(S)-N-[(1-Benzothiophen-2-yl)methylidene]-1-(naphthalen-1-yl)ethylamine

aLab. Síntesis de Complejos, Facultad de Ciencias Químicas, Benemérita, Universidad Autónoma de Puebla, PO Box 1067, 72001 Puebla, Pue., Mexico, and bCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570 Puebla, Pue., Mexico
Correspondence e-mail: angel.mendoza@correo.buap.mx

In the title compound, C21H17NS, the C=N double bond shows an E conformation. The dihedral angle between the mean planes of the naphthyl residue and the benzothiophene residue is 89.14 (6)°. The crystal packing is stabilized by intermolecular C-H...[pi] interactions, building a ribbon structure along the a axis.

Related literature

For Schiff bases, see: García et al. (2011[García, T., Bernès, S., Flores-Alamo, M., Hernández, G. & Gutiérrez, R. (2011). Acta Cryst. E67, o1648-o1649.]); Bernès et al. (2010[Bernès, S., Hernández, G., Portillo, R., Cruz, S. & Gutiérrez, R. (2010). Acta Cryst. E66, o1322-o1323.]); Jeon et al. (2005[Jeon, S.-J., Li, H. & Walsh, P. J. (2005). J. Am. Chem. Soc. 127, 16416-16425.]); Noyori (2005[Noyori, R. (2005). Chem. Commun. pp. 1807-1811.]); Tanaka & Toda (2000[Tanaka, K. & Toda, F. (2000). Chem. Rev. 100, 1025-1074.]).

[Scheme 1]

Experimental

Crystal data
  • C21H17NS

  • Mr = 315.42

  • Orthorhombic, P 21 21 21

  • a = 5.6423 (3) Å

  • b = 8.0808 (4) Å

  • c = 36.3864 (19) Å

  • V = 1659.01 (15) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.70 mm-1

  • T = 298 K

  • 0.93 × 0.17 × 0.06 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.665, Tmax = 1

  • 8690 measured reflections

  • 2844 independent reflections

  • 2417 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.092

  • S = 1.01

  • 2844 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack parameter determined using 839 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack (2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.])

  • Absolute structure parameter: 0.021 (17)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1/C2/C3/C4/C9, C12/C13/C18/C19/C20/C21 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C8-H8...Cg1i 0.93 2.73 3.491 (4) 139
C11-H11B...Cg2ii 0.96 2.59 3.724 (5) 149
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (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: SHELXL2013; software used to prepare material for publication: SHELXL2013.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6929 ).


Acknowledgements

Support from VIEP-UAP (GUPJ-NAT10-G) is acknowledged.

References

Bernès, S., Hernández, G., Portillo, R., Cruz, S. & Gutiérrez, R. (2010). Acta Cryst. E66, o1322-o1323.  [CSD] [CrossRef] [details]
García, T., Bernès, S., Flores-Alamo, M., Hernández, G. & Gutiérrez, R. (2011). Acta Cryst. E67, o1648-o1649.  [CrossRef] [details]
Jeon, S.-J., Li, H. & Walsh, P. J. (2005). J. Am. Chem. Soc. 127, 16416-16425.  [ISI] [CrossRef] [PubMed] [ChemPort]
Noyori, R. (2005). Chem. Commun. pp. 1807-1811.  [CrossRef]
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Tanaka, K. & Toda, F. (2000). Chem. Rev. 100, 1025-1074.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1480  [ doi:10.1107/S1600536813023611 ]

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