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

Al-Tamimi, A.-M.S.; Bari, A.; Al-Omar, M.A.; El-Emam, A.A.; Ng, S.W.

doi:10.1107/S1600536810029260

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 (C-C) = 0.002 Å
R = 0.043
wR = 0.113
Data-to-parameter ratio = 18.2
Details

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

Abdul-Malek S. Al-Tamimi,^a Ahmed Bari,^a Mohamed A. Al-Omar,^a Ali A. El-Emam ^a and Seik Weng Ng ^b ^*

^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-HO and O-HN 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).

Experimental

Crystal data

C₁₉H₂₇ClN₄O·0.5C₂H₆O·1.5H₂O
M_r = 412.95
Triclinic, $[P \overline 1]$
a = 7.9867 (6) Å
b = 16.8478 (13) Å
c = 16.9656 (13) Å
= 97.341 (1)°
= 100.376 (1)°
= 97.505 (1)°
V = 2199.3 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.924, T_max = 0.980
21291 measured reflections
10050 independent reflections
7547 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(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
_max = 0.37 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O3ⁱ	0.86 (1)	2.00 (1)	2.841 (2)	166 (2)
N3-H3O1wⁱⁱ	0.86 (1)	1.95 (1)	2.806 (2)	170 (2)
N6-H6O2w	0.88 (1)	1.95 (1)	2.829 (2)	174 (2)
N8-H8O3wⁱⁱⁱ	0.86 (1)	1.94 (1)	2.778 (2)	164 (2)
O3-H3oO1w	0.84 (1)	1.84 (1)	2.673 (2)	177 (2)
O1w-H11O1ⁱⁱ	0.84 (1)	2.00 (1)	2.821 (2)	166 (2)
O1w-H12N5	0.84 (1)	1.91 (1)	2.751 (2)	175 (3)
O2w-H21O2	0.85 (1)	2.07 (1)	2.905 (2)	172 (2)
O2w-H22O2^iv	0.84 (1)	1.93 (1)	2.764 (2)	176 (2)
O3w-H31N4	0.84 (1)	1.94 (1)	2.773 (2)	169 (2)
O3w-H32O2w	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); 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: 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.
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.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds