(IUCr) 2-Hydroxyimino-1-phenylethanone thiosemicarbazone monohydrate

Volume 64
Part 3
Pages o623-o624
March 2008

Received 14 February 2008
Accepted 20 February 2008
Online 22 February 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R = 0.062
wR = 0.155
Data-to-parameter ratio = 18.7
Details

2-Hydroxyimino-1-phenylethanone thiosemicarbazone monohydrate

Nursabah Sarikavakli,^a knur Babahan,^a Ertan Sahin ^b and Tuncer Hökelek ^c ^*

^aAdnan Menderes University, Department of Chemistry, 09010 Aydin, Turkey,^bAtatürk University, Department of Chemistry, 22240 Erzurum, Turkey, and ^cHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title thiosemicarbazone derivative, C₉H₁₀N₄OS·H₂O, intramolecular N-HN hydrogen bonds result in the formation of two nearly coplanar five- and six-membered rings, which are also almost coplanar with the adjacent phenyl ring. The oxime group has an E configuration and is involved in intermolecular O-HO hydrogen bonding as a donor. In the crystal structure, intramolecular O-HS and N-HN and intermolecular O-HO and N-HS hydrogen bonds generate edge-fused R₂²(8) and R₄¹(11) ring motifs. The hydrogen-bonded motifs are linked to each other to form a three-dimensional supramolecular network.

Related literature

For general backgroud, see: Lukevics et al. (1995); Liberta & West (1992); Hagenbach & Gysin (1952); Jones et al. (1965); Brockman & Thomson (1956); Klayman et al. (1979); Petering & van Giesen (1966); Sevagapandian et al. (2000); Forman (1964); Holan et al. (1984); Balsamo et al. (1990); Marsman et al. (1999); Karle et al. (1996); Etter et al. (1990); Chertanova et al. (1994); Bernstein et al. (1995). For related structures, see: Sarikavakli et al. (2007); Özel Güven et al. (2007); Hökelek, Bati et al. (2001); Hökelek, Zülfikaroglu & Bati (2001); Büyükgüngör et al. (2003); Hökelek et al. (2004a,b); Hökelek et al. (2004). For the synthesis, see: El-Shazly et al. (2005). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₉H₁₀N₄OS·H₂O
M_r = 240.29
Monoclinic, C 2/c
a = 28.5615 (3) Å
b = 4.6805 (3) Å
c = 22.0977 (4) Å
= 127.24 (2)°
V = 2351.8 (6) Å³
Z = 8
Mo K radiation
= 0.27 mm^-1
T = 294 (2) K
0.30 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (Blessing, 1995) T_min = 0.940, T_max = 0.960
31269 measured reflections
3607 independent reflections
2146 reflections with I > 2(I)
R_int = 0.090

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.154
S = 1.04
3607 reflections
193 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.14 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO2ⁱ	0.90 (3)	1.83 (3)	2.728 (3)	174 (3)
O2-H21S1	0.94 (3)	2.32 (3)	3.250 (3)	171 (3)
O2-H22O2ⁱ	0.91 (3)	1.98 (3)	2.886 (3)	172 (4)
N3-H3AN1	0.92 (3)	1.91 (2)	2.604 (3)	130 (2)
N4-H41S1ⁱⁱ	0.92 (2)	2.53 (2)	3.434 (2)	169 (3)
N4-H42N2	0.93 (3)	2.24 (3)	2.643 (3)	105 (2)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2403 ).

Acknowledgements

The authors are indebted to the Department of Chemistry, Atatürk University, Erzurum, Turkey, for the use of the X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund.

References

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organic compounds