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Volume 69 
Part 7 
Page o1075  
July 2013  

Received 9 May 2013
Accepted 27 May 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.106
Data-to-parameter ratio = 15.1
Details
Open access

rac-(E,E)-N,N'-Bis(2-chlorobenzylidene)cyclohexane-1,2-diamine

aDepartment of Chemistry, An-Najah National University, Nablus, State of Palestine,bDepartment of Chemistry, Hashemite University, Zarqa 13115, Jordan,cDepartment of Chemistry, University of Jordan, Amman 11942, Jordan, and dLCAE-URAC18, Faculté des Sciences, Université Mohammed Ier, Oujda 60000, Morocco
Correspondence e-mail: i.kh.warad@gmail.com, manoaimi@hu.edu.jo

In the title racemic Schiff base ligand, C20H20Cl2N2, which was prepared by the condensation of 2-chlorobenzaldehyde and cyclohexane-1,2-diamine, the cyclohexane ring adopts a chair conformation and the dihedral angle between the aromatic rings of the 2-chlorophenyl substituent groups is 62.52 (8)°. In the structure, there are two short intramolecular methine C-H...Cl interactions [C...Cl = 3.066 (2) and 3.076 (3) Å], and in the crystal there are also weak intermolecular aromatic C-H...Cl [3.464 (3), 3.553 (3) and 3.600 (3) Å] and Cl...Cl [3.557 (3) and 3.891 (3) Å] contacts.

Related literature

For the crystal structures of some Schiff bases derived from cyclohexane-1,2-diamine, see: Arvinnezhad et al. (2012[Arvinnezhad, H., Jadidi, K. & Notash, B. (2012). Acta Cryst. E68, o407-o408.]); Fan et al. (2011[Fan, P., Ge, C., Zhang, X., Zhang, R. & Li, S. (2011). Acta Cryst. E67, o3399.]); Saleh Salga et al. (2010[Saleh Salga, M., Khaledi, H., Mohd Ali, H. & Puteh, R. (2010). Acta Cryst. E66, o1095.]). For applications of chiral Schiff base ligands, see: Da Silva et al. (2011[Da Silva, C. M., Da Silva, D. L., Modolo, L. V., Alves, R. B., De Resende, M. A., Martins, C. V. B. & De Faetima, A. (2011). J. Adv. Res. 2, 1-8.]); Dhar & Taploo (1982[Dhar, D. N. & Taploo, C. L. (1982). J. Sci. Ind. Res. 41, 501-506.]); Przybylski et al. (2009[Przybylski, P., Huczynski, A., Pyta, K., Brzezinski, B. & Bartl, F. (2009). Curr. Org. Chem. 13, 124-148.]); Gupta & Sutar (2008[Gupta, K. C. & Sutar, A. K. (2008). Coord. Chem. Rev. 252, 1420-1450.]). For the synthesis of the title compound, see: Larrow & Jacobsen (1998[Larrow, J. F. & Jacobsen, E. N. (1998). Org. Synth. 75, 1-11.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20Cl2N2

  • Mr = 359.28

  • Monoclinic, P 21 /n

  • a = 5.9029 (5) Å

  • b = 19.5613 (13) Å

  • c = 16.1662 (11) Å

  • [beta] = 93.493 (7)°

  • V = 1863.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.15 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.902, Tmax = 0.949

  • 7483 measured reflections

  • 3273 independent reflections

  • 2252 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.106

  • S = 1.02

  • 3273 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2261 ).


Acknowledgements

This project was supported by An-Najah National University and Hashemite University. The X-ray structural work was carried out at the Hamdi Mango Center for Scientific Research at the University of Jordan.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Arvinnezhad, H., Jadidi, K. & Notash, B. (2012). Acta Cryst. E68, o407-o408.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Da Silva, C. M., Da Silva, D. L., Modolo, L. V., Alves, R. B., De Resende, M. A., Martins, C. V. B. & De Faetima, A. (2011). J. Adv. Res. 2, 1-8.
Dhar, D. N. & Taploo, C. L. (1982). J. Sci. Ind. Res. 41, 501-506.  [ChemPort]
Fan, P., Ge, C., Zhang, X., Zhang, R. & Li, S. (2011). Acta Cryst. E67, o3399.  [CSD] [CrossRef] [IUCr Journals]
Gupta, K. C. & Sutar, A. K. (2008). Coord. Chem. Rev. 252, 1420-1450.  [Web of Science] [CrossRef] [ChemPort]
Larrow, J. F. & Jacobsen, E. N. (1998). Org. Synth. 75, 1-11.  [ChemPort]
Przybylski, P., Huczynski, A., Pyta, K., Brzezinski, B. & Bartl, F. (2009). Curr. Org. Chem. 13, 124-148.  [Web of Science] [CrossRef] [ChemPort]
Saleh Salga, M., Khaledi, H., Mohd Ali, H. & Puteh, R. (2010). Acta Cryst. E66, o1095.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1075  [ doi:10.1107/S1600536813014554 ]

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