2,2′-[(E,E)-cis-(Cyclo­hexane-1,4-di­yl)bis­(nitrilo­methanylyl­idene)]diphenol

Shaaban K Mohamed; Mehmet Akkurt; Muhammad N Tahir; Antar A Abdelhamid

doi:10.1107/S1600536812023367

. 2012 May 26;68(Pt 6):o1905. doi: 10.1107/S1600536812023367

2,2′-[(E,E)-cis-(Cyclohexane-1,4-diyl)bis(nitrilomethanylylidene)]diphenol

Shaaban K Mohamed ^a, Mehmet Akkurt ^b,^*, Muhammad N Tahir ^c, Antar A Abdelhamid ^a

PMCID: PMC3379462 PMID: 22719660

Abstract

In the title compound, C₂₀H₂₂N₂O₂, the asymmetric unit contains two independent half-molecules, which are both completed by crystallographic inversion symmetry. The cyclohexane rings of both molecules adopt chair conformations; the N atoms are in equatorial orientations in one molecule and in axial orientations in the other. Both molecules feature two intramolecular O—H⋯N hydrogen bonds, which generate S(6) rings.

Related literature

For background to Schiff bases as ligands, see: Li & Zhang (2004 ▶). graphic file with name e-68-o1905-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₂N₂O₂
M _r = 322.40
Monoclinic,
a = 16.2979 (11) Å
b = 6.1103 (4) Å
c = 18.2336 (12) Å
β = 104.975 (4)°
V = 1754.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.32 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.975, T _max = 0.980
12904 measured reflections
3428 independent reflections
1641 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.140
S = 1.01
3428 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023367/hb6813sup1.cif

e-68-o1905-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023367/hb6813Isup2.hkl

e-68-o1905-Isup2.hkl^{(168.2KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.579 (2)	148
O2—H2A⋯N2	0.82	1.86	2.593 (3)	148

Open in a new tab

Acknowledgments

This project was sponsored by the General Association of Scholarships in Egypt. The University of Sargodha is gratefully acknowledged for The X-ray difraction measurements and the data collection.

supplementary crystallographic information

Comment

Schiff base compounds have been reported as excelent substrates in the development of coordination chemistry (e.g. Li & Zhang, 2004), In this study we report the synthesis and crystal structure of the title compound (I).

As shown in Fig. 1, there are two independent half molecules A (with C1) and B (with C11) in the asymmetric unit of the title compound. They are centrosymmetric and the centres of symmetry are lied on the centroids of their cyclohexane rings. The cyclohexane rings of them adopt chair conformations Molecular conformation of the title compound is stabilized by intramolecular O—H···N hydrogen bonds, generating an S(6) ring motif (Table 1, Fig. 2).

Experimental

The title compound arose as a bi-product from heating a reaction mixture of 114 mg (1 mmol) cyclohexane-1,4-diamine, 112 mg (1 mmol) cyclohexane-1,3-dione and 122 mg (1 mmol) salicylaldehyde in 50 ml e thanol under reflux for 6 h. The reaction mixture was concentrated under vacuum then left to cool at ambient temperature. The obtained solid was collected by Buckner funnel, washed with water then ethanol, dried in desiccator and crystallized from ethanol (m.p. 451 K). Yellow prisms were grown from ethanol solution by slow evaporation over two days.