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Volume 66 
Part 8 
Page o2131  
August 2010  

Received 20 July 2010
Accepted 22 July 2010
Online 31 July 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.113
Data-to-parameter ratio = 18.2
Details
Open access

N'-[(2-n-Butyl-4-chloro-1H-imidazol-5-yl)methylidene]adamantane-1-carbohydrazide sesquihydrate ethanol hemisolvate

aDepartment of Pharmaceutical Chemistry, College of Chemistry, King Saud University, Riyadh 11451, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the asymmetric unit of the title compound, C19H27ClN4O·0.5C2H6O·1.5H2O, there are two molecules of the Schiff base, which has a rigid adamantyl cage at one end of the C(= O)NH-N=CH- chain and an almost planar [torsion angles = 1.3 (1) and 7.9 (2)° imidazolyl ring at the other end, three molecules of water and one molecule of ethanol. In both independent molecules of the Schiff base, this chain displays an extended zigzag configuration. All their amino groups function as hydrogen-bond donors to water molecules; these are linked to other acceptor atoms, generating a layer structure. O-H...O and O-H...N interactions involving the water molecules also occur.

Related literature

For the cyclization of this class of Schiff bases to pharmaceutically useful chemicals, see: Kadi et al. (2007[Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.]).

[Scheme 1]

Experimental

Crystal data
  • C19H27ClN4O·0.5C2H6O·1.5H2O

  • Mr = 412.95

  • Triclinic, [P \overline 1]

  • a = 7.9867 (6) Å

  • b = 16.8478 (13) Å

  • c = 16.9656 (13) Å

  • [alpha] = 97.341 (1)°

  • [beta] = 100.376 (1)°

  • [gamma] = 97.505 (1)°

  • V = 2199.3 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 100 K

  • 0.40 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.924, Tmax = 0.980

  • 21291 measured reflections

  • 10050 independent reflections

  • 7547 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.113

  • S = 1.02

  • 10050 reflections

  • 552 parameters

  • 11 restraints

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

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.86 (1) 2.00 (1) 2.841 (2) 166 (2)
N3-H3...O1wii 0.86 (1) 1.95 (1) 2.806 (2) 170 (2)
N6-H6...O2w 0.88 (1) 1.95 (1) 2.829 (2) 174 (2)
N8-H8...O3wiii 0.86 (1) 1.94 (1) 2.778 (2) 164 (2)
O3-H3o...O1w 0.84 (1) 1.84 (1) 2.673 (2) 177 (2)
O1w-H11...O1ii 0.84 (1) 2.00 (1) 2.821 (2) 166 (2)
O1w-H12...N5 0.84 (1) 1.91 (1) 2.751 (2) 175 (3)
O2w-H21...O2 0.85 (1) 2.07 (1) 2.905 (2) 172 (2)
O2w-H22...O2iv 0.84 (1) 1.93 (1) 2.764 (2) 176 (2)
O3w-H31...N4 0.84 (1) 1.94 (1) 2.773 (2) 169 (2)
O3w-H32...O2w 0.85 (1) 1.92 (1) 2.766 (2) 174 (2)
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x+1, y, z; (iv) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); 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: BT5304 ).


Acknowledgements

We thank King Saud University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2010). E66, o2131  [ doi:10.1107/S1600536810029260 ]

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