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

Akerman, K.J.

doi:10.1107/S1600536812046193

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 (C-C) = 0.003 Å
R = 0.050
wR = 0.131
Data-to-parameter ratio = 15.5
Details

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

Kate J. Akerman ^a ^*

^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 Zn^II, Cu^II and Ni^II chelates in the solid state, see: Wang et al. (2007). For the solid-state synthesis and X-ray structure of the anhydrous trans racemate of the ligand, see: van den Ancker et al. (2006). For the Ti^IV chelate of the trans racemic complex, see: Zhang et al. (2008). For the intermolecular interaction-controlled self-assembly and a study of the photophysics of the Pt^II chelate of the R,R and S,S enantiomers as well as the trans racemic complex, see: Shan et al. (2008). For the X-ray structure and applications of the trans racemate of the Pd^II chelate as a hydrogenation catalyst, see: Bacchi et al. (2003).

Experimental

Crystal data

C₁₆H₂₀N₄·H₂O
M_r = 286.38
Monoclinic, P 2₁ /n
a = 9.7207 (7) Å
b = 18.4183 (13) Å
c = 18.2460 (12) Å
= 92.721 (7)°
V = 3263.1 (4) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.956, T_max = 0.989
23848 measured reflections
6428 independent reflections
3290 reflections with I > 2(I)
R_int = 0.067

Refinement

R[F² > 2(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
_max = 0.15 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H1WN3A	0.82 (3)	2.28 (3)	3.014 (2)	149 (3)
O1W-H2WN3B	0.92 (3)	1.96 (3)	2.857 (2)	166 (3)
O2W-H3WN2B	0.80 (3)	2.16 (3)	2.927 (2)	159 (3)
O2W-H4WN2A	0.98 (3)	1.88 (3)	2.819 (2)	159 (2)
N1A-H01AO2W	0.93 (2)	2.03 (2)	2.896 (2)	154 (2)
N1B-H01BO2W	0.95 (2)	1.96 (2)	2.899 (2)	169 (2)
N4A-H04AO1W	0.88 (2)	2.02 (2)	2.882 (3)	166 (2)
N4B-H04BO1W	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

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

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