2,2′-{[(1E,1′E)-(Cyclo­hexane-1,4-diyl)­bis(aza­nylyl­idene)]bis­(ethan-1-yl-1-yl­idene)}diphenol

S H Anjana Lakshmi; M Kandaswamy; V Ramkumar

doi:10.1107/S1600536813026123

. 2013 Sep 28;69(Pt 10):o1593. doi: 10.1107/S1600536813026123

2,2′-{[(1E,1′E)-(Cyclohexane-1,4-diyl)bis(azanylylidene)]bis(ethan-1-yl-1-ylidene)}diphenol

S H Anjana Lakshmi ^a, M Kandaswamy ^a, V Ramkumar ^b,^*

PMCID: PMC3790448 PMID: 24098267

Abstract

The title compound, C₂₂H₂₆N₂O₂, crystallizes with three independent molecules, two of which are situated on inversion centers, so the asymmetric unit contains two independent half-molecules and one molecule in a general position. The two hydroxy groups in each molecule are involved in intramolecular O—H⋯N hydrogen bonds, which generate S(6) rings. In the crystal, weak intermolecular C—H⋯π interactions link the molecules into two crystallographically independent columns propagating along [001]; one column consists of molecules in general positions, while the other column is built from alternating independent centrosymmetric molecules.

Related literature

For applications of Schiff base ligands in coordination chemistry, see: Gao & Zheng (2002 ▶); Hamil et al. (2012 ▶); Chu et al. (2008 ▶); More et al. (2001 ▶); Vigato & Tamburini (2004 ▶). For details of the synthesis, see: Huang et al. (2008 ▶). graphic file with name e-69-o1593-scheme1.jpg

Experimental

Crystal data

C₂₂H₂₆N₂O₂
M _r = 350.45
Triclinic,
a = 9.0299 (6) Å
b = 11.4718 (8) Å
c = 17.9652 (13) Å
α = 92.946 (3)°
β = 95.521 (4)°
γ = 91.204 (3)°
V = 1849.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.980, T _max = 0.992
20050 measured reflections
6387 independent reflections
2646 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.239
S = 1.02
6387 reflections
477 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813026123/cv5426sup1.cif

e-69-o1593-sup1.cif^{(31.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026123/cv5426Isup2.hkl

e-69-o1593-Isup2.hkl^{(312.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2, Cg3 and Cg4 are the centroiods of the C17–C22, C1–C6, C34–C39 and C23–C28 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯N4	0.82	1.79	2.526 (5)	147
O5—H5⋯N3	0.82	1.80	2.523 (5)	147
O2—H2A⋯N2	0.82	1.80	2.516 (5)	145
O1—H1A⋯N1	0.82	1.79	2.520 (5)	147
C11—H11A⋯Cg1ⁱ	0.97	2.64	3.552 (3)	155
C14—H14A⋯Cg2ⁱⁱ	0.97	2.63	3.540 (1)	156
C33—H33B⋯Cg3ⁱⁱⁱ	0.97	2.62	3.510 (4)	151
C44—H44A⋯Cg4^iv	0.97	2.61	3.504 (4)	152

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors acknowledge the Department of Chemistry, IIT Madras, for the data collection.

supplementary crystallographic information

1. Comment

The research field dealing with Schiff base coordination chemistry has expanded enormously (Chu et al., 2008; Gao et al., 2002; Hamil et al., 2012); the presence of a lone pair of electrons in an sp² hybridized orbital of nitrogen atom of the azomethine group is of considerable chemical and biological importance (More et al., 2001). Because of the relative easiness of preparation, synthetic flexibility, and the special property of C=N group, Schiff bases are generally excellent chelating agents (Vigato et al., 2004). In azomethine derivatives, the C=N linkage is essential for biological activity, several azomethines were reported to possess remarkable antibacterial, antifungal, anticancer and diuretic activities. Herewith we present the crystal structure of the title compound.

The title compound crystallizes with two half-molecules situated on inversion centers and one molecule in general position (Fig. 1). Two hydroxy groups in each molecule are involved in intramolecular O—H···N hydrogen bonds (Table 1), which generate S(6) rings. In the crystal, weak intermolecular C—H···π interactions (Table 1) link the molecules into two crystallographically independent columns propagated in [001] - one column consists from the molecules in general positions, while another column is built from the alternating independent centrosymmetric molecules.

2. Experimental

The title compound was prepared by treating trans1, 4-diamino cyclohexane with 2-hydroxy acetophenone in the stoichiometric ratio in the ethanolic solution and refluxed for 5 h. The reaction mixture was then cooled slowly to room temperature; a yellow crystalline product was obtained and further washed with cold ethanol respectively (Huang et al., 2008). It was then recrystallized from chloroform. The yellow like single-crystal of the title compound used in X-ray diffraction studies were grown in a chloroform solution by slow evaporation of the solvent at room temperature.