1,4-Bis{(+)-(S)-[1-(1-naphth­yl)eth­yl]imino­meth­yl}benzene

Espinosa Leija, A.; Bernès, S.; Hernández, G.; Sharma, P.; Peña, U.; Gutiérrez, R.

doi:10.1107/S1600536809033455

Volume 65
Part 10
Page o2317
October 2009

Received 30 July 2009
Accepted 21 August 2009
Online 5 September 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R = 0.052
wR = 0.163
Data-to-parameter ratio = 8.0
Details

1,4-Bis{(+)-(S)-[1-(1-naphthyl)ethyl]iminomethyl}benzene

Armando Espinosa Leija,^a Sylvain Bernès,^b ^* Guadalupe Hernández,^c Pankaj Sharma,^d Ulises Peña ^c and René Gutiérrez ^c

^aFacultad de Ciencias Químicas, UANL, Licenciatura en Química Industrial, Ciudad Universitaria, Monterrey, NL, Mexico,^bDEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, NL, Mexico,^cLab. Síntesis de Complejos, Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, PO Box 1067, 72001 Puebla, Pue., Mexico, and ^dInstituto de Química-UNAM, Circuito exterior, Cd. Universitaria, Coyoacán, CP 04510, México, DF, Mexico
Correspondence e-mail: sylvain_bernes@hotmail.com

The title compound, C₃₂H₂₈N₂, is a chiral bis-imine in which both imine groups display the common E configuration. The naphthyl groups present different orientations with respect to the central core, as reflected in the dihedral angles of 21.4 (2) and 78.83 (14)° between the benzene and naphthyl mean planes, thus the highest possible C₂ local molecular symmetry is not attained. This C₁ molecular conformation allows multiple C-H [pi] intermolecular contacts involving all aromatic rings, while no [pi] - [pi] interactions are available for the stabilization of the crystal structure. The resulting packing structure is based on molecules stacked along [100].

Related literature

For solvent-free synthesis in organic chemistry, see: Jeon et al. (2005); Noyori (2005); Tanaka & Toda (2000); Tovar et al. (2007). For related chiral Schiff bases constructed from a bis-substituted benzene core, see: Allouchi et al. (1994); Hamaker & Oberts (2006); Espinosa Leija et al. (2009). For the use of the enantiomer of the title compound as a chiral dopant for liquid crystals, see: Watanabe & Fukuda (2008).

Experimental

Crystal data

C₃₂H₂₈N₂
M_r = 440.56
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.391 (3) Å
b = 15.102 (5) Å
c = 19.569 (7) Å
V = 2479.6 (14) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 298 K
0.6 × 0.2 × 0.2 mm

Data collection

Siemens P4 diffractometer
Absorption correction: none
6140 measured reflections
2491 independent reflections
1445 reflections with I > 2(I)
R_int = 0.162
3 standard reflections every 97 reflections intensity decay: 2.5%

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.163
S = 1.10
2491 reflections
310 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12ACg3ⁱ	0.96	2.79	3.677 (6)	154
C18-H18ACg4ⁱ	0.93	2.62	3.520 (5)	163
C20-H20ACg5ⁱ	0.93	2.98	3.681 (5)	133
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ . Cg1 is the centroid of ring C27-C32, Cg2 is the centroid of ring C23-C27/C32, Cg3 is the centroid of ring C14-C19, Cg4 is the centroid of ring C1-C5/C10 and Cg5 is the centroid of ring C5-C10.

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2874 ).

Acknowledgements

Partial support from VIEP-UAP (GUPJ-NAT08-G) and SEP/PIFI-3 (CA-150 2006-22-08) is acknowledged.

References

Allouchi, H., Bideau, J. P., Cotrait, M., Destrade, Ch. & Nguyen, H. T. (1994). Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 239, 153-164.
Espinosa Leija, A., Hernández, G., Cruz, S., Bernès, S. & Gutiérrez, R. (2009). Acta Cryst. E65, o1316.
Hamaker, C. G. & Oberts, B. P. (2006). J. Chem. Crystallogr. 36, 735-742.
Jeon, S.-J., Li, H. & Walsh, P. J. (2005). J. Am. Chem. Soc. 127, 16416-16425.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Noyori, R. (2005). Chem. Commun. pp. 1807-1811.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Tanaka, K. & Toda, F. (2000). Chem. Rev. 100, 1025-1074.
Tovar, A., Penña, U., Hernández, G., Portillo, R. & Gutiérrez, R. (2007). Synthesis, pp. 22-24.
Watanabe, J. & Fukuda, K. (2008). Jpn. Kokai Tokkyo Koho Patent JP 2008106201.

organic compounds