1,5-Bis[(E)-1-(2-hydroxyphenyl)ethyl­idene]thiocarbonohydrazide mono­hydrate

Affan, M.A.; Chee, D.N.A.; Ahmad, F.B.; Tiekink, E.R.T.

doi:10.1107/S1600536810004241

Volume 66
Part 3
Page o555
March 2010

Received 2 February 2010
Accepted 2 February 2010
Online 6 February 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.102
Data-to-parameter ratio = 16.1
Details

1,5-Bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide monohydrate

Md. Abu Affan,^a ⁺ Dayang N. A. Chee,^a Fasihuddin B. Ahmad ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: Edward.Tiekink@gmail.com

In the title compound, C₁₇H₁₈N₄O₂S·H₂O, the thiourea derivative is almost planar, with an r.m.s. deviation for the non-H atoms of 0.057 Å. The hydroxyl groups lie to the same side of the molecule as the thione S atom, a conformation that allows the formation of intramolecular O-HS and O-HN hydrogen bonds. In the crystal structure, the thiourea and water molecules self-assemble into a two-dimensional array by a combination of O_water-HO_hydroxyl, N-HO_water and O_water-HS hydrogen bonds and C-H [pi] interactions.

Related literature

For background and recent studies of the biological activity of organotin compounds, see: Gielen & Tiekink (2005); Affan et al. (2009). For the structure of the ketone analogue of the title compound, see: Zukerman-Schpector et al. (2009).

Experimental

Crystal data

C₁₇H₁₈N₄O₂S·H₂O
M_r = 360.43
Monoclinic, P 2₁ /n
a = 15.8654 (3) Å
b = 7.3938 (1) Å
c = 16.3697 (3) Å
= 115.922 (1)°
V = 1727.06 (5) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 100 K
0.44 × 0.13 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.905, T_max = 1
15464 measured reflections
3968 independent reflections
3136 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.102
S = 1.03
3968 reflections
246 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4-C9 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1ON2	0.83 (2)	1.79 (2)	2.5191 (17)	147 (2)
O1-H1OS1	0.83 (2)	2.86 (2)	3.5126 (13)	138 (2)
O2-H2ON4	0.82 (2)	1.81 (2)	2.542 (2)	148 (2)
O2-H2OS1	0.82 (2)	2.96 (2)	3.6220 (15)	139 (2)
O3-H3OO1	0.84 (2)	1.91 (2)	2.7525 (18)	174 (2)
O3-H4OS1ⁱ	0.82 (2)	2.76 (2)	3.5089 (14)	154 (2)
N1-H1NO3ⁱⁱ	0.87 (2)	2.04 (2)	2.8169 (19)	150 (2)
N3-H3NO3ⁱⁱ	0.88 (2)	2.04 (2)	2.854 (2)	154 (2)
C11-H11CCg1ⁱⁱⁱ	0.98	2.61	3.4497 (17)	144
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5327 ).

Acknowledgements

The authors express their gratitude to the Ministry of Science, Technology and Innovation (MOSTI) for a research grant (No. 06-01-09-SF0046), and to Universiti Malaysia Sarawak (UNIMAS) for financial support.

References

Affan, M. A., Foo, S. W., Jusoh, I., Hanapi, S. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 5031-5037.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gielen, M. & Tiekink, E. R. T. (2005). Editors. Metallotherapeutic Drugs and Metal-Based Diagnostic Agents: The Use of Metals in Medicine, pp. 421-439. Chichester: John Wiley & Sons.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951.

organic compounds