(E)-2,4-Dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone–4,4′-bipyridine–water (4/7/2)

Ng, S.W.

doi:10.1107/S1600536809030852

Volume 65
Part 9
Page o2129
September 2009

Received 22 July 2009
Accepted 3 August 2009
Online 12 August 2009

Key indicators
Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.061
wR = 0.179
Data-to-parameter ratio = 14.6
Details

(E)-2,4-Dihydroxybenzaldehyde 4-ethylthiosemicarbazone-4,4'-bipyridine-water (4/7/2)

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The asymmetric unit of the title compound, 7C₁₀H₈N₂·4C₁₀H₁₃N₃O₂S·2H₂O, contains two independent 2,4-hydroxybenzaldehyde 4-ethylthiosemicarbazone molecules, three and a half 4,4'-bipyridine molecules and one water molecule. Two of the 4,4'-bipyridine molecules lie on general positions and the other three on centers of inversion. The two 4,4'-bipyridine molecules on general positions and one of the three on special positions are disordered over two positions each with an occupancy of 0.50. The -NH-C(=S)-NH-NC fragment is close to planar in the two 2,4-hydroxybenzaldehyde 4-ethylthiosemicarbazone molecules (r.m.s. deviations = 0.04 and 0.05 Å). In the crystal, the Schiff base, N-heterocycle and water molecules engage in O-HO, O-HN and N-HO hydrogen-bonding interactions, generating a layer structure.

Related literature

4,4'-Bipyridine forms a number of clathrates with diphenols; for the quinol clathrate, see: Oswald et al. (2005) and for the 2,2'-biphenol clathrate, see: Lavender et al. (1999). For the crystal structure of 2,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone, see: Tan et al. (2008).

Experimental

Crystal data

7C₁₀H₈N₂·4C₁₀H₁₃N₃O₂S·2H₂O
M_r = 2086.50
Triclinic, $[P \overline 1]$
a = 11.7683 (3) Å
b = 15.2531 (4) Å
c = 16.0612 (4) Å
= 74.639 (2)°
= 86.561 (2)°
= 70.252 (1)°
V = 2615.2 (1) Å³
Z = 1
Mo K radiation
= 0.16 mm^-1
T = 153 K
0.20 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.968, T_max = 0.992
18419 measured reflections
10042 independent reflections
6419 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.179
S = 1.02
10042 reflections
686 parameters
170 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.66 e Å^-3
_min = -0.56 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1oN8ⁱ	0.84 (4)	1.92 (1)	2.755 (5)	171 (5)
O1-H1oN8'ⁱ	0.84 (4)	1.97 (1)	2.798 (5)	171 (5)
O2-H2oN7	0.84 (4)	1.93 (1)	2.768 (5)	172 (4)
O2-H2oN7'	0.84 (4)	1.93 (1)	2.766 (5)	178 (4)
O3-H3oN10ⁱⁱ	0.84 (4)	1.91 (1)	2.751 (5)	178 (5)
O3-H3oN10'ⁱⁱ	0.84 (4)	1.90 (1)	2.736 (5)	172 (5)
O4-H4oN11	0.84 (4)	1.90 (1)	2.735 (4)	174 (4)
O1w-H1w1O4	0.84 (3)	2.04 (2)	2.843 (4)	160 (5)
O1w-H1w2N9	0.84 (3)	1.94 (1)	2.782 (5)	175 (7)
O1w-H1w2N9'	0.84 (3)	1.91 (3)	2.722 (5)	160 (7)
N2-H2nO1w	0.88 (3)	1.88 (1)	2.757 (4)	175 (4)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2864 ).

Acknowledgements

The author thanks the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Lavender, E. S., Ferguson, G. & Glidewell, C. (1999). Acta Cryst. C55, 430-432.
Oswald, I. D. H., Motherwell, W. D. S. & Parsons, S. (2005). Acta Cryst. B61, 46-57.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tan, K. W., Ng, C. H., Maah, M. J. & Ng, S. W. (2008). Acta Cryst. E64, o2123.
Westrip, S. P. (2009). publCIF. In preparation.

organic compounds