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Volume 69 
Part 10 
Page o1593  
October 2013  

Received 19 August 2013
Accepted 21 September 2013
Online 28 September 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.008 Å
R = 0.060
wR = 0.239
Data-to-parameter ratio = 13.4
Details
Open access

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

aDepartment of Inorganic Chemistry, University of Madras, Maraimalai Campus (Guindy), Chennai-25, India, and bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
Correspondence e-mail: shanjanalakshmi@gmail.com

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...[pi] 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[Gao, W. T. & Zheng, Z. (2002). Molecules, 7, 511-516.]); Hamil et al. (2012[Hamil, A. M., Abdelkarem, M., Hemmet, M. & El-ajaily, M. M. (2012). Int. J. ChemTech Res. 4, 682-685.]); Chu et al. (2008[Chu, Z., Huang, W., Wang, L. & Gou, S. (2008). Polyhedron, 27, 1079-1092.]); More et al. (2001[More, P. G., Bhalvankar, R. B. & Pattar, S. C. (2001). J. Indian Chem. Soc. 78, 474-475.]); Vigato & Tamburini (2004[Vigato, P. A. & Tamburini, S. (2004). Coord. Chem. Rev. 248, 1717-2128.]). For details of the synthesis, see: Huang et al. (2008[Huang, W., Chu, Z. & Jiang, J. (2008). Polyhedron, 27, 2705-2709.]).

[Scheme 1]

Experimental

Crystal data
  • C22H26N2O2

  • Mr = 350.45

  • Triclinic, [P \overline 1]

  • a = 9.0299 (6) Å

  • b = 11.4718 (8) Å

  • c = 17.9652 (13) Å

  • [alpha] = 92.946 (3)°

  • [beta] = 95.521 (4)°

  • [gamma] = 91.204 (3)°

  • V = 1849.3 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.992

  • 20050 measured reflections

  • 6387 independent reflections

  • 2646 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.239

  • S = 1.02

  • 6387 reflections

  • 477 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

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...Cg4iv 0.97 2.61 3.504 (4) 152
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y, -z+1; (iii) x-1, y, z; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5426 ).


Acknowledgements

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

References

Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chu, Z., Huang, W., Wang, L. & Gou, S. (2008). Polyhedron, 27, 1079-1092.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gao, W. T. & Zheng, Z. (2002). Molecules, 7, 511-516.  [CrossRef] [ChemPort]
Hamil, A. M., Abdelkarem, M., Hemmet, M. & El-ajaily, M. M. (2012). Int. J. ChemTech Res. 4, 682-685.  [ChemPort]
Huang, W., Chu, Z. & Jiang, J. (2008). Polyhedron, 27, 2705-2709.  [Web of Science] [CSD] [CrossRef] [ChemPort]
More, P. G., Bhalvankar, R. B. & Pattar, S. C. (2001). J. Indian Chem. Soc. 78, 474-475.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vigato, P. A. & Tamburini, S. (2004). Coord. Chem. Rev. 248, 1717-2128.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1593  [ doi:10.1107/S1600536813026123 ]

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