2-[(1Z)-(9-Ethyl-9H-carbazol-3-yl)methyl­eneamino]-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carbonitrile–benzene (2/1)

Fun, H.-K.; Goh, J.H.; Asiri, A.M.; Khan, S.A.; Khan, K.A.

doi:10.1107/S1600536810014947

Volume 66
Part 5
Pages o1200-o1201
May 2010

Received 22 March 2010
Accepted 23 April 2010
Online 28 April 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.070
wR = 0.167
Data-to-parameter ratio = 22.7
Details

2-[(1Z)-(9-Ethyl-9H-carbazol-3-yl)methyleneamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile-benzene (2/1)

Hoong-Kun Fun,^a ^*⁺ Jia Hao Goh,^a ⁺⁺ Abdullah M. Asiri,^b ⁺⁺⁺ Salman A. Khan ^b and Khalid A. Khan ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia
Correspondence e-mail: hkfun@usm.my

In the title compound, 2C₂₄H₂₁N₃S·C₆H₆, the two independent Schiff base molecules (A and B) in the asymmetric unit differ in the orientation of the tetrahydrobenzothiophene ring system with respect to the carbazole ring system by 180° rotation about the C-C bond in the C-C=N-C linkage. The two molecules also differ in the orientation of the ethyl groups [C-N-C-C torsion angle of 90.7 (3)° in molecule A, and -79.4 (3)° in molecule B]. In molecule B, two methylene C atoms of the cyclohexene ring are disordered over two sites with occupancies of 0.58 (1) and 0.42 (1). The cyclohexene rings in both molecules adopt half-chair conformations. The dihedral angle between the thiophene ring and the carbazole ring system is 8.07 (9)° in molecule A [3.10 (9)° in molecule B]. In the crystal structure, the independent molecules are linked into dimers by intermolecular C-HN hydrogen bonds. In addition, C-H [pi] interactions are observed.

Related literature

For biological and other applications of Schiff base compounds, see: Abu-Hussen (2006); Elerman et al. (2002); Panneerselvam et al. (2005); Walsh et al. (1996). For ring puckering parameters, see: Cremer & Pople (1975). For a related structure, see: Elerman & Elmali (1998).

Experimental

Crystal data

2C₂₄H₂₁N₃S·C₆H₆
M_r = 845.10
Triclinic, $[P \overline 1]$
a = 11.4816 (1) Å
b = 13.7322 (2) Å
c = 14.8358 (2) Å
= 81.841 (1)°
= 77.083 (1)°
= 83.864 (1)°
V = 2250.00 (5) Å³
Z = 2
Mo K radiation
= 0.16 mm^-1
T = 293 K
0.45 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.931, T_max = 0.989
48693 measured reflections
13169 independent reflections
6227 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.070
wR(F²) = 0.167
S = 1.01
13169 reflections
580 parameters
63 restraints
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1B-C6B, C7A-C12A and C14A-C16A/C21A/S1A rings, respectively.

D-HA	D-H	HA	DA	D-HA
C22A-H22AN3Bⁱ	0.97	2.59	3.487 (3)	155
C11A-H11ACg1ⁱⁱ	0.93	2.65	3.499 (3)	153
C11B-H11BCg2ⁱ	0.93	2.82	3.725 (3)	166
C27-H27ACg3ⁱⁱⁱ	0.93	2.71	3.625 (6)	169
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y, z; (iii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5065 ).

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. The authors thank the Department of Chemistry, King Abdulaziz University, for providing research facilities.

References

Abu-Hussen, A. A. A. (2006). J. Coord. Chem. 59, 157-176.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Elerman, Y. & Elmali, A. (1998). Acta Cryst. C54, 529-531.
Elerman, Y., Kabak, M. & Elmali, A. (2002). Z. Naturforsch. Teil B, 57, 651-656.
Panneerselvam, P., Nair, R. P., Vijayalakshmi, G., Subramanian, E. H. & Sridhar, S. K. (2005). Eur. J. Med. Chem. 40, 225-229.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Walsh, O. M., Meegan, M. J., Prendergast, R. M. & Nakib, T. A. (1996). Eur. J. Med. Chem. 31, 989-1000.

organic compounds