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Volume 68 
Part 12 
Pages o3354-o3355  
December 2012  

Received 7 November 2012
Accepted 8 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.131
Data-to-parameter ratio = 15.5
Details
Open access

(1R*,2S*)-N,N'-Bis[(E)-1H-pyrrol-2-ylmethylidene]cyclohexane-1,2-diamine monohydrate

aSchool of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X01, Scottsville, Pietermaritzburg, 3209, South Africa
Correspondence e-mail: 205503190@stu.ukzn.ac.za

The title compound, C16H20N4·H2O, was synthesized from cis-1,2-diaminocyclohexane (a racemic mixture of the (1R,2S) and (1S,2R) enantiomers). The compound crystallized with two molecules (A and B) in the asymmetric unit with a single water solvent molecule per Schiff base molecule. Molecules A and B have similar conformations as illustrated by the least-squares-fit with an r.m.s. deviation of 0.242 Å. The molecules within the asymmetric unit are bridged by hydrogen bonds to the two water molecules, resulting in a heterotetramer. The water molecule acts as both a hydrogen-bond donor and acceptor. The pyrrole-imine units are not co-planar, making an angle of 73.9 (3)° and 76.9 (3)° in molecules A and B, respectively.

Related literature

For a study of the helical structures formed by both the S,S and R,R bis(pyrrolide-imine) ligands as well as the ZnII, CuII and NiII chelates in the solid state, see: Wang et al. (2007[Wang, Y., Fu, H., Shen, F., Sheng, X., Peng, A., Gu, Z., Ma, H., Ma, J. S. & Yao, J. (2007). Inorg. Chem. 46, 3548-3556.]). For the solid-state synthesis and X-ray structure of the anhydrous trans racemate of the ligand, see: van den Ancker et al. (2006[Ancker, T. R. van den, Cave, G. W. V. & Raston, C. L. (2006). Green Chem. 8, 50-53.]). For the TiIV chelate of the trans racemic complex, see: Zhang et al. (2008[Zhang, X.-Q., Xu, B., Li, Y.-H. & Li, W. (2008). Acta Cryst. E64, m437.]). For the intermolecular interaction-controlled self-assembly and a study of the photophysics of the PtII chelate of the R,R and S,S enantiomers as well as the trans racemic complex, see: Shan et al. (2008[Shan, X.-F., Wang, D.-H., Tung, C.-H. & Wu, L.-Z. (2008). Tetrahedron, 64, 5577-5582.]). For the X-ray structure and applications of the trans racemate of the PdII chelate as a hydrogenation catalyst, see: Bacchi et al. (2003[Bacchi, A., Carcelli, M., Gabba, L., Ianelli, S., Pelagatti, P., Pelizzi, G. & Rogolino, D. (2003). Inorg. Chim. Acta, 342, 229-235.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20N4·H2O

  • Mr = 286.38

  • Monoclinic, P 21 /n

  • a = 9.7207 (7) Å

  • b = 18.4183 (13) Å

  • c = 18.2460 (12) Å

  • [beta] = 92.721 (7)°

  • V = 3263.1 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.60 × 0.30 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur 2 CCD diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.956, Tmax = 0.989

  • 23848 measured reflections

  • 6428 independent reflections

  • 3290 reflections with I > 2[sigma](I)

  • Rint = 0.067

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.131

  • S = 0.85

  • 6428 reflections

  • 414 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1W...N3A 0.82 (3) 2.28 (3) 3.014 (2) 149 (3)
O1W-H2W...N3B 0.92 (3) 1.96 (3) 2.857 (2) 166 (3)
O2W-H3W...N2B 0.80 (3) 2.16 (3) 2.927 (2) 159 (3)
O2W-H4W...N2A 0.98 (3) 1.88 (3) 2.819 (2) 159 (2)
N1A-H01A...O2W 0.93 (2) 2.03 (2) 2.896 (2) 154 (2)
N1B-H01B...O2W 0.95 (2) 1.96 (2) 2.899 (2) 169 (2)
N4A-H04A...O1W 0.88 (2) 2.02 (2) 2.882 (3) 166 (2)
N4B-H04B...O1W 0.86 (3) 2.09 (3) 2.896 (3) 155 (2)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2181 ).


Acknowledgements

I would like to thank the University of KwaZulu-Natal for the use of their facilities and the National Research Foundation (South Africa) for funding.

References

Ancker, T. R. van den, Cave, G. W. V. & Raston, C. L. (2006). Green Chem. 8, 50-53.
Bacchi, A., Carcelli, M., Gabba, L., Ianelli, S., Pelagatti, P., Pelizzi, G. & Rogolino, D. (2003). Inorg. Chim. Acta, 342, 229-235.  [ISI] [CSD] [CrossRef] [ChemPort]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Shan, X.-F., Wang, D.-H., Tung, C.-H. & Wu, L.-Z. (2008). Tetrahedron, 64, 5577-5582.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, Y., Fu, H., Shen, F., Sheng, X., Peng, A., Gu, Z., Ma, H., Ma, J. S. & Yao, J. (2007). Inorg. Chem. 46, 3548-3556.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhang, X.-Q., Xu, B., Li, Y.-H. & Li, W. (2008). Acta Cryst. E64, m437.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3354-o3355   [ doi:10.1107/S1600536812046193 ]

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