2-Hydroxy­imino-1-phenyl­ethanone thio­semicarbazone monohydrate

Sarıkavaklı, N.; Babahan, İ.; Şahin, E.; Hökelek, T.

doi:10.1107/S1600536808004947

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages o623-o624

doi:10.1107/S1600536808004947

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2-Hydroxyimino-1-phenylethanone thiosemicarbazone monohydrate

Nursabah Sarıkavaklı,^a İknur Babahan,^a Ertan Şahin ^b and Tuncer Hökelek ^c ^*

^aAdnan Menderes University, Department of Chemistry, 09010 Aydın, 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

(Received 14 February 2008; accepted 20 February 2008; online 22 February 2008)

In the title thiosemicarbazone derivative, C₉H₁₀N₄OS·H₂O, intramolecular N—H⋯N 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—H⋯O hydrogen bonding as a donor. In the crystal structure, intramolecular O—H⋯S and N—H⋯N and intermolecular O—H⋯O and N—H⋯S 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: Sarıkavaklı et al. (2007 ); Özel Güven et al. (2007 ); Hökelek, Batı et al. (2001 ); Hökelek, Zülfikaroğlu & Batı (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
β = 127.24 (2)°
V = 2351.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(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
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2ⁱ	0.90 (3)	1.83 (3)	2.728 (3)	174 (3)
O2—H21⋯S1	0.94 (3)	2.32 (3)	3.250 (3)	171 (3)
O2—H22⋯O2ⁱ	0.91 (3)	1.98 (3)	2.886 (3)	172 (4)
N3—H3A⋯N1	0.92 (3)	1.91 (2)	2.604 (3)	130 (2)
N4—H41⋯S1ⁱⁱ	0.92 (2)	2.53 (2)	3.434 (2)	169 (3)
N4—H42⋯N2	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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004947/xu2403sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004947/xu2403Isup2.hkl

checkCIF report

Comment top

Thiosemicarbazones are derivatives of carbonyl compounds and they have a wide range of biological activities, depending on the parent aldehyde or ketone (Lukevics et al., 1995; Liberta & West, 1992). Some of the thiosemicarbazone derivatives have antitumour (Hagenbach & Gysin, 1952), antiviral (Jones et al., 1965), antileukaemic (Brockman & Thomson, 1956) and antimalarial (Klayman et al., 1979) activities. Thus, some of them have been used as drugs and have the ability to form complexes (Petering & van Giesen, 1966).

Oxime and dioxime derivatives are very important compounds in the chemical industry and medicine (Sevagapandian et al., 2000). They have a broad pharmacological activity spectrum, encompassing antibacterial, antidepressant and antifungal activities (Forman, 1964; Holan et al., 1984; Balsamo et al., 1990). The oxime (–C=N—OH) moiety is potentially ambidentate, with possibilities of coordination through nitrogen and/or oxygen atoms. It is a functional group that has not been extensively explored in crystal engineering. In the solid state, oximes are usually associated via O—H···N hydrogen bonds of length 2.8 Å.

Oxime groups possess stronger hydrogen-bonding capabilities than alcohols, phenols, and carboxylic acids (Marsman et al., 1999), in which intermolecular hydrogen bonding combines moderate strength and directionality (Karle et al., 1996) in linking molecules to form supramolecular structures; this has received considerable attention with respect to directional noncovalent intermolecular interactions (Etter et al., 1990).

The structures of some oxime and dioxime derivatives have been determined in our laboratory, including those of 2,3-dimethylquinoxaline-dimethyl-glyoxime (1/1), [(II) Hökelek, Batı et al., 2001], 1-(2,6-dimethylphenylamino)- propane-1,2-dione dioxime, [(III) (Hökelek, Zülfikaroğlu & Batı, 2001), N-hydroxy-2-oxo-2,N'-diphenylacetamidine, [(IV) (Büyükgüngör et al., 2003], N-(3,4-dichlorophenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine, [(V) Hökelek et al., 2004], N-hydroxy-N'-(1-naphthyl)-2-phenylacetamidin-2-one [(VI) Hökelek et al., 2004a], N-(3-chloro-4-methylphenyl)-N'-hydroxy-2 -oxo-2-phenylacetamidine [(VII) Hökelek et al., 2004b], 2-(1H-benzimidazol -1-yl)-1-phenylethanone oxime [(VIII) Özel Güven et al., 2007] and (1Z,2E)-1-(3,5-dimethyl-1H-pyrazole-1-yl)ethane-1,2-dione dioxime [(IX) Sarıkavaklı et al., 2007]. The structure determination of the title compound, (I), a thiosemicarbazone derivative with one 2-hydroxyimino -1-phenyl-ethanone, one thiosemicarbazone moieties and one uncoordinated water molecule, was carried out in order to investigate the strength of the hydrogen bonding capability of the oxime and thiosemicarbazone groups and to compare the geometry of the oxime moiety with the previously reported ones.

In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Ring A (C1—C6) is, of course, planar. The intramolecular N—H···N hydrogen bonds (Table 1) result in the formation of two more planar five- and six-membered rings B (C9/N2—N4/H42) and C (C7/C8/N1—N3/H3A). The rings A, B and C are also nearly coplanar with dihedral angles of A/B = 3.47 (10)°, A/C = 2.84 (10) and B/C = 5.94 (10)°.

Some significant changes in the geometry of the oxime moiety are evident when the bond lengths and angles are compared with the corresponding values in compounds (II)-(VII) (Table 2). The oxime moiety has an E configuration [C7—C8—N1—O1 177.1 (2)°; Chertanova et al., 1994]. In this configuration, the oxime groups are involved as donors in O—H···O intermolecular hydrogen bondings (Table 1).

In the crystal structure, intramolecular O—H···S and N—H···N and intermolecular O—H···O and N—H···S hydrogen bonds (Table 1) generate edge-fused R₂²(8) and R₄¹(11) ring motifs (Fig. 2) (Bernstein et al., 1995). The hydrogen bonded motifs are linked to each other to form a three dimensional network (Fig. 3). The intra- and intermolecular hydrogen bonds seem to be effective in the stabilization of the crystal structure.

Related literature top

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: Sarıkavaklı et al. (2007); Özel Güven et al. (2007); Hökelek, Batı et al. (2001); Hökelek, Zülfikaroğlu & Batı (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 top

The title compound was prepared according to the literature method (El-Shazly et al., 2005). 2-Isonitrosoacetophenone (149 mg, 1 mmol) was reacted with thiosemicarbazide (91 mg, 1 mmol) in ethanol-water mixture (1:1) by refluxing for 24 h. Then, a few drops of glacial acetic acid were added. The formed precipitate was filtered and recrystallized from ethanol to obtain yellow crystals (yield: 155 mg, 70%).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A part of the crystal structure of (I), showing the formation of R₂²(8) and R₄¹(11) ring motifs. Hydrogen bonds are shown as dashed lines.
	Fig. 3. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2-Hydroxyimino-1-phenylethanone thiosemicarbazone monohydrate top

Crystal data top

C₉H₁₀N₄OS·H₂O	F(000) = 1008
M_r = 240.29	D_x = 1.357 Mg m⁻³
Monoclinic, C2/c	Melting point: 443 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 28.5615 (3) Å	Cell parameters from 2893 reflections
b = 4.6805 (3) Å	θ = 2.3–30.5°
c = 22.0977 (4) Å	µ = 0.27 mm⁻¹
β = 127.24 (2)°	T = 294 K
V = 2351.8 (6) Å³	Prism, yellow
Z = 8	0.30 × 0.20 × 0.15 mm

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3607 independent reflections
Radiation source: fine-focus sealed tube	2146 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ω scans	θ_max = 30.5°, θ_min = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −40→40
T_min = 0.940, T_max = 0.960	k = −6→5
31269 measured reflections	l = −31→31

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0474P)² + 0.9027P] where P = (F_o² + 2F_c²)/3
3607 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.14 e Å⁻³
8 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₉H₁₀N₄OS·H₂O	V = 2351.8 (6) Å³
M_r = 240.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.5615 (3) Å	µ = 0.27 mm⁻¹
b = 4.6805 (3) Å	T = 294 K
c = 22.0977 (4) Å	0.30 × 0.20 × 0.15 mm
β = 127.24 (2)°

Data collection top

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

Refinement top

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

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.08587 (3)	0.69943 (16)	0.58554 (3)	0.0693 (2)
O1	0.24428 (8)	0.9359 (4)	0.88734 (10)	0.0740 (5)
H1A	0.2527 (12)	1.022 (6)	0.8584 (15)	0.100 (10)*
O2	0.22848 (8)	0.6577 (4)	0.70204 (11)	0.0720 (5)
H21	0.1878 (8)	0.692 (7)	0.6673 (16)	0.133 (14)*
H22	0.2445 (13)	0.817 (5)	0.7313 (16)	0.113 (12)*
N1	0.19953 (8)	0.7460 (4)	0.83853 (10)	0.0576 (5)
N2	0.09978 (8)	0.3607 (4)	0.75639 (10)	0.0577 (5)
N3	0.10929 (9)	0.5206 (5)	0.71329 (10)	0.0619 (5)
H3A	0.1412 (9)	0.641 (5)	0.7347 (14)	0.077 (8)*
N4	0.02448 (9)	0.3422 (5)	0.60650 (11)	0.0654 (6)
H41	−0.0011 (10)	0.316 (5)	0.5550 (10)	0.076 (8)*
H42	0.0210 (12)	0.238 (5)	0.6394 (14)	0.084 (9)*
C1	0.07415 (11)	0.0295 (6)	0.83508 (14)	0.0644 (6)
H1	0.0517 (11)	0.012 (5)	0.7826 (15)	0.074 (8)*
C2	0.06113 (12)	−0.1405 (6)	0.87378 (17)	0.0721 (7)
H2	0.0280 (11)	−0.257 (5)	0.8455 (15)	0.071 (8)*
C3	0.09577 (13)	−0.1362 (6)	0.95201 (17)	0.0724 (7)
H3	0.0859 (12)	−0.245 (6)	0.9780 (16)	0.083 (9)*
C4	0.14393 (14)	0.0388 (6)	0.99041 (16)	0.0742 (7)
H4	0.1666 (12)	0.036 (6)	1.0426 (16)	0.092 (9)*
C5	0.15737 (13)	0.2112 (6)	0.95211 (14)	0.0639 (6)
H5	0.1913 (13)	0.330 (6)	0.9810 (17)	0.089 (9)*
C6	0.12248 (9)	0.2111 (5)	0.87338 (12)	0.0521 (5)
C7	0.13487 (9)	0.3927 (5)	0.82959 (11)	0.0516 (5)
C8	0.18351 (10)	0.5985 (5)	0.87101 (13)	0.0580 (6)
H8	0.2005 (11)	0.621 (5)	0.9241 (15)	0.080 (8)*
C9	0.07134 (10)	0.5057 (5)	0.63645 (11)	0.0556 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0632 (4)	0.0943 (5)	0.0452 (3)	−0.0096 (3)	0.0301 (3)	0.0036 (3)
O1	0.0703 (11)	0.0827 (12)	0.0573 (10)	−0.0268 (9)	0.0324 (9)	−0.0116 (9)
O2	0.0630 (11)	0.0814 (13)	0.0698 (12)	0.0040 (10)	0.0393 (10)	−0.0022 (10)
N1	0.0518 (10)	0.0649 (12)	0.0491 (10)	−0.0074 (9)	0.0269 (9)	−0.0074 (8)
N2	0.0588 (11)	0.0704 (12)	0.0439 (10)	−0.0070 (9)	0.0311 (9)	−0.0025 (8)
N3	0.0611 (12)	0.0780 (14)	0.0419 (9)	−0.0147 (10)	0.0287 (9)	−0.0037 (9)
N4	0.0628 (12)	0.0832 (15)	0.0449 (11)	−0.0118 (11)	0.0299 (10)	−0.0060 (10)
C1	0.0567 (13)	0.0777 (17)	0.0544 (14)	−0.0031 (12)	0.0313 (12)	0.0037 (12)
C2	0.0633 (15)	0.0771 (18)	0.0776 (18)	−0.0037 (14)	0.0436 (15)	0.0078 (14)
C3	0.0841 (19)	0.0761 (18)	0.0785 (19)	0.0119 (15)	0.0603 (17)	0.0164 (14)
C4	0.093 (2)	0.0816 (18)	0.0567 (15)	0.0102 (16)	0.0496 (15)	0.0081 (14)
C5	0.0737 (16)	0.0693 (15)	0.0500 (13)	−0.0021 (13)	0.0381 (12)	−0.0023 (11)
C6	0.0534 (12)	0.0566 (12)	0.0491 (11)	0.0061 (10)	0.0325 (10)	0.0012 (9)
C7	0.0503 (11)	0.0596 (13)	0.0429 (11)	0.0026 (10)	0.0272 (9)	−0.0009 (9)
C8	0.0563 (13)	0.0668 (14)	0.0435 (11)	−0.0018 (11)	0.0263 (10)	−0.0028 (10)
C9	0.0549 (12)	0.0657 (14)	0.0438 (11)	−0.0008 (11)	0.0286 (10)	−0.0044 (10)

Geometric parameters (Å, º) top

S1—C9	1.681 (2)	C2—H2	0.93 (3)
O1—H1A	0.903 (18)	C3—C2	1.378 (4)
O2—H21	0.940 (17)	C3—C4	1.368 (4)
O2—H22	0.907 (18)	C3—H3	0.93 (3)
N1—O1	1.385 (2)	C4—H4	0.92 (3)
N1—C8	1.264 (3)	C5—C4	1.381 (4)
N2—N3	1.362 (3)	C5—H5	0.95 (3)
N2—C7	1.297 (3)	C6—C1	1.389 (3)
N3—H3A	0.923 (17)	C6—C5	1.386 (3)
N4—C9	1.320 (3)	C6—C7	1.483 (3)
N4—H41	0.915 (17)	C7—C8	1.469 (3)
N4—H42	0.930 (17)	C8—H8	0.97 (3)
C1—C2	1.374 (3)	C9—N3	1.355 (3)
C1—H1	0.93 (2)

N1—O1—H1A	104.6 (19)	C3—C4—C5	121.2 (3)
H21—O2—H22	106 (3)	C3—C4—H4	116.6 (19)
C8—N1—O1	112.88 (19)	C5—C4—H4	122.2 (19)
C7—N2—N3	118.58 (19)	C4—C5—C6	120.9 (3)
C9—N3—N2	120.1 (2)	C4—C5—H5	118.5 (18)
C9—N3—H3A	117.9 (16)	C6—C5—H5	120.6 (18)
N2—N3—H3A	122.0 (17)	C1—C6—C7	119.6 (2)
C9—N4—H41	120.3 (17)	C5—C6—C1	117.3 (2)
C9—N4—H42	117.9 (17)	C5—C6—C7	123.0 (2)
H41—N4—H42	121 (2)	N2—C7—C8	125.4 (2)
C2—C1—C6	121.2 (2)	N2—C7—C6	116.00 (19)
C2—C1—H1	118.9 (16)	C8—C7—C6	118.60 (18)
C6—C1—H1	119.7 (16)	N1—C8—C7	122.4 (2)
C1—C2—C3	120.9 (3)	N1—C8—H8	122.8 (16)
C1—C2—H2	118.0 (16)	C7—C8—H8	114.7 (16)
C3—C2—H2	121.1 (16)	N4—C9—N3	117.2 (2)
C4—C3—C2	118.4 (3)	N4—C9—S1	124.28 (17)
C4—C3—H3	120.7 (18)	N3—C9—S1	118.46 (18)
C2—C3—H3	120.8 (18)

O1—N1—C8—C7	177.1 (2)	C1—C6—C5—C4	−0.6 (4)
C7—N2—N3—C9	−175.9 (2)	C7—C6—C5—C4	179.8 (2)
N3—N2—C7—C8	2.8 (3)	C5—C6—C7—N2	177.2 (2)
N3—N2—C7—C6	−179.56 (19)	C1—C6—C7—N2	−2.4 (3)
C6—C1—C2—C3	−0.1 (4)	C5—C6—C7—C8	−5.0 (3)
C4—C3—C2—C1	−0.8 (4)	C1—C6—C7—C8	175.4 (2)
C2—C3—C4—C5	1.0 (4)	N2—C7—C8—N1	−7.6 (4)
C6—C5—C4—C3	−0.3 (4)	C6—C7—C8—N1	174.8 (2)
C5—C6—C1—C2	0.8 (4)	S1—C9—N3—N2	−178.23 (16)
C7—C6—C1—C2	−179.6 (2)	N4—C9—N3—N2	3.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.90 (3)	1.83 (3)	2.728 (3)	174 (3)
O2—H21···S1	0.94 (3)	2.32 (3)	3.250 (3)	171 (3)
O2—H22···O2ⁱ	0.91 (3)	1.98 (3)	2.886 (3)	172 (4)
N3—H3A···N1	0.92 (3)	1.91 (2)	2.604 (3)	130 (2)
N4—H41···S1ⁱⁱ	0.92 (2)	2.53 (2)	3.434 (2)	169 (3)
N4—H42···N2	0.93 (3)	2.24 (3)	2.643 (3)	105 (2)

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₄OS·H₂O
M_r	240.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	28.5615 (3), 4.6805 (3), 22.0977 (4)
β (°)	127.24 (2)
V (Å³)	2351.8 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.940, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	31269, 3607, 2146
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.154, 1.04
No. of reflections	3607
No. of parameters	193
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.31

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.90 (3)	1.83 (3)	2.728 (3)	174 (3)
O2—H21···S1	0.94 (3)	2.32 (3)	3.250 (3)	171 (3)
O2—H22···O2ⁱ	0.91 (3)	1.98 (3)	2.886 (3)	172 (4)
N3—H3A···N1	0.92 (3)	1.91 (2)	2.604 (3)	130 (2)
N4—H41···S1ⁱⁱ	0.92 (2)	2.53 (2)	3.434 (2)	169 (3)
N4—H42···N2	0.93 (3)	2.24 (3)	2.643 (3)	105 (2)

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x, −y+1, −z+1.

Table 2. Comparison of the bond lengths and angles (Å, °) in the oxime moieties of the title compound,(I), with the corresponding values in the related compounds (II)–(VII) top

Bond/Angle	(I)	(II)	(III)	(IV)	(V)	(VI)	(VII)
N1-O1	1.385 (2)	1.403 (2)	1.423 (3)	1.417 (1)	1.429 (4)	1.424 (2)	1.416 (3)
		1.396 (2)	1.396 (3)				1.397 (3)
N1-C8	1.264 (3)	1.281 (2)	1.290 (3)	1.290 (1)	1.241 (6)	1.289 (2)	1.282 (3)
		1.281 (2)	1.282 (3)				1.289 (3)
C7-C8	1.469 (3)	1.477 (3)	1.489 (3)	1.510 (1)	1.551 (7)	1.513 (2)	1.501 (4)
		1.473 (3)					1.502 (4)
C7-C8-N1	122.4 (2)	115.2 (2)	116.6 (2)	114.3 (1)	118.3 (5)	113.2 (1)	114.4 (2)
		115.0 (2)	115.0 (2)				113.4 (2)
C8-N1-O1	112.9 (2)	112.4 (1)	109.4 (2)	110.7 (1)	112.2 (4)	110.6 (1)	110.7 (2)
		112.2 (1)	111.5 (2)				111.1 (2)

Notes: (II): 2,3-dimethylquinoxaline-dimethylglyoxime (1/1) (Hökelek, Batı et al., 2001), (III): 1-(2,6-dimethylphenylamino)propane-1,2-dione dioxime (Hökelek, Zülfikaroğlu & Batı, 2001), (IV): N-hydroxy-2-oxo-2,N'-diphenylacetamidine (Büyükgüngör et al., 2003), (V): N-(3,4-dichlorophenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine (Hökelek et al., 2004), (VI): N-hydroxy-N'-(1-naphthyl)-2-phenylacetamidin-2-one (Hökelek et al., 2004a), (VII): N-(3-chloro-4-methylphenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine-2,3- dimethylquinoxaline-dimethyl-glyoxime (1/1) (Hökelek et al., 2004b).

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.

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