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In the mol­ecule of the title compound, C7H10N4O2, the glyoxime group has an E configuration. In this configuration, both oxime groups are involved as donors in O—H...N inter­molecular hydrogen bonding, linking the mol­ecules to form a supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035490/xu2297sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035490/xu2297Isup2.hkl
Contains datablock I

CCDC reference: 657838

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.060
  • wR factor = 0.164
  • Data-to-parameter ratio = 21.1

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Comment top

Oxime and dioxime derivatives are very important compounds in the chemical industry and medicine (Sevagapandian et al., 2000). 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 hydrogen-bond systems in the crystals of oximes have been analysed and a correlation between a pattern of hydrogen bonding and N—O bond lengths has been suggested (Bertolasi et al., 1982). The configurational and/or conformational isomers of glyoxime derivatives (dioximes) have also been analysed (Chertanova et al., 1994).

The structures of oxime and dioxime derivatives have been the subject of much interest in our laboratory; examples are 2,3-dimethylquinoxaline-dimethyl- glyoxime (1/1), [(II) Hökelek, Batı et al., 2001], 1-(2,6-dimethylphenyl- amino)propane-1,2-dione dioxime, [(III) (Hökelek, Zülfikaroğlu et al., 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., 2004a], N-hydroxy-N'-(1-naphthyl)-2-phenylacetamidin-2-one [(VI) Hökelek et al., 2004b], N-(3-chloro-4-methylphenyl)-N'-hydroxy-2-oxo-2 -phenylacetamidine [(VII) Hökelek et al., 2004c] and 2-(1H-benzimidazol-1-yl) -1-phenylethanone oxime [(VIII) Özel Güven et al., 2007]. The structure determination of the title molecule was carried out in order to investigate the strength of the hydrogen bonding capability of the oxime groups and to compare the geometry of the oxime moieties with the previously reported ones.

In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987). It contains glyoxime and 3,5-dimethylpyrazole moieties. The dihedral angles between the glyoxime planes A (O1/N3/C7), B (O2/N4/C6) and pyrazole ring C (N1/N2/C2—C4) are A/B = 0.71 (15)°, A/C = 68.12 (8)° and B/C = 68.47 (9)°. In the glyoxime moiety, the N3—O1 [1.390 (2) Å] bond is slightly longer than N4—O2 [1.374 (2) Å], while C6—N4—O2 [113.0 (1)°] angle is larger than C7—N3—O1 [112.2 (2)°], reflecting the types and electron-withdrawing or -donating properties of the substituents bonded to C atoms of the glyoxime moiety.

Some significant changes in the geometry of the oxime moieties are evident when the bond lengths and angles are compared with the corresponding values in compounds (II)-(VIII) (Table 2). The glyoxime moiety has an E configuration [C6—C7—N3—O1 179.58 (15)° and C7—C6—N4—O2 - 179.53 (14)°; Chertanova et al., 1994]. In this configuration, both oxime groups are involved as donors in O—H···N intermolecular hydrogen bondings (Table 1).

In the crystal structure, the intermolecular O—H···N hydrogen bonds (Table 1) link the molecules to form a supramolecular structure (Fig. 2), in which they seem to be highly effective in the stabilization of the structure.

Related literature top

For general background, see: Sevagapandian et al. (2000); Marsman et al. (1999); Karle et al. (1996); Etter et al. (1990); Bertolasi et al. (1982); Chertanova et al. (1994). For related literatures, see: Hökelek, Batı et al. (2001); Hökelek, Zülfikaroğlu et al. (2001); Büyükgüngör et al. (2003); Hökelek et al. (2004a,b,c); Özel Güven et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 3,5-dimethyl-1H-pyrazole (0,9613 g, 10 mmol) was dissolved in ethanol (5 ml), and CH3COONa (1.36 g, 10 mmol) in water (3 ml) was added to this solution, and then solid anti-chloroglyoxime (1.225 g, 10 mmol) was added slowly with stirring. When almost half of the anti-chloroglyoxime was added, the ligand started to precipitate. When the addition was completed, stirring was continued for 2 h at room temperature. The precipitate was filtered, washed with water and dried at room temperature in a vacuum oven and recrystallized from an ethanol-water solution (yield 1.35 g, 68%).

Refinement top

Atoms H1, H2 and H7 were located in difference syntheses and refined isotropically [O1—H1 = 0.97 (4) Å, Uiso(H) = 0.169 (15) Å2; O2—H2 = 0.95 (3) Å, Uiso(H) = 0.097 (8) Å2 and C7—H7 = 1.00 (2) Å, Uiso(H) = 0.073 (6) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atom, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for aromatic H atoms.

Structure description top

Oxime and dioxime derivatives are very important compounds in the chemical industry and medicine (Sevagapandian et al., 2000). 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 hydrogen-bond systems in the crystals of oximes have been analysed and a correlation between a pattern of hydrogen bonding and N—O bond lengths has been suggested (Bertolasi et al., 1982). The configurational and/or conformational isomers of glyoxime derivatives (dioximes) have also been analysed (Chertanova et al., 1994).

The structures of oxime and dioxime derivatives have been the subject of much interest in our laboratory; examples are 2,3-dimethylquinoxaline-dimethyl- glyoxime (1/1), [(II) Hökelek, Batı et al., 2001], 1-(2,6-dimethylphenyl- amino)propane-1,2-dione dioxime, [(III) (Hökelek, Zülfikaroğlu et al., 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., 2004a], N-hydroxy-N'-(1-naphthyl)-2-phenylacetamidin-2-one [(VI) Hökelek et al., 2004b], N-(3-chloro-4-methylphenyl)-N'-hydroxy-2-oxo-2 -phenylacetamidine [(VII) Hökelek et al., 2004c] and 2-(1H-benzimidazol-1-yl) -1-phenylethanone oxime [(VIII) Özel Güven et al., 2007]. The structure determination of the title molecule was carried out in order to investigate the strength of the hydrogen bonding capability of the oxime groups and to compare the geometry of the oxime moieties with the previously reported ones.

In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987). It contains glyoxime and 3,5-dimethylpyrazole moieties. The dihedral angles between the glyoxime planes A (O1/N3/C7), B (O2/N4/C6) and pyrazole ring C (N1/N2/C2—C4) are A/B = 0.71 (15)°, A/C = 68.12 (8)° and B/C = 68.47 (9)°. In the glyoxime moiety, the N3—O1 [1.390 (2) Å] bond is slightly longer than N4—O2 [1.374 (2) Å], while C6—N4—O2 [113.0 (1)°] angle is larger than C7—N3—O1 [112.2 (2)°], reflecting the types and electron-withdrawing or -donating properties of the substituents bonded to C atoms of the glyoxime moiety.

Some significant changes in the geometry of the oxime moieties are evident when the bond lengths and angles are compared with the corresponding values in compounds (II)-(VIII) (Table 2). The glyoxime moiety has an E configuration [C6—C7—N3—O1 179.58 (15)° and C7—C6—N4—O2 - 179.53 (14)°; Chertanova et al., 1994]. In this configuration, both oxime groups are involved as donors in O—H···N intermolecular hydrogen bondings (Table 1).

In the crystal structure, the intermolecular O—H···N hydrogen bonds (Table 1) link the molecules to form a supramolecular structure (Fig. 2), in which they seem to be highly effective in the stabilization of the structure.

For general background, see: Sevagapandian et al. (2000); Marsman et al. (1999); Karle et al. (1996); Etter et al. (1990); Bertolasi et al. (1982); Chertanova et al. (1994). For related literatures, see: Hökelek, Batı et al. (2001); Hökelek, Zülfikaroğlu et al. (2001); Büyükgüngör et al. (2003); Hökelek et al. (2004a,b,c); Özel Güven et al. (2007). For bond-length data, see: Allen et al. (1987).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity [symmetry codes: (a) -x, y + 1/2, -z + 1/2; (b) -x, -y, -z; (c) x, -y + 1/2, z + 1/2].
(1Z,2E)-1-(3,5-Dimethyl-1H-pyrazol-1-yl)-1,2-ethanedione dioxime top
Crystal data top
C7H10N4O2F(000) = 384
Mr = 182.19Dx = 1.322 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3673 reflections
a = 9.7598 (5) Åθ = 2.0–30.5°
b = 9.8572 (6) ŵ = 0.10 mm1
c = 9.8140 (7) ÅT = 298 K
β = 104.254 (3)°Block, colourless
V = 915.08 (10) Å30.30 × 0.20 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
1879 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 30.6°, θmin = 2.9°
ω scansh = 1313
26614 measured reflectionsk = 1414
2785 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.072P)2 + 0.1814P]
where P = (Fo2 + 2Fc2)/3
2785 reflections(Δ/σ)max < 0.001
132 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C7H10N4O2V = 915.08 (10) Å3
Mr = 182.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.7598 (5) ŵ = 0.10 mm1
b = 9.8572 (6) ÅT = 298 K
c = 9.8140 (7) Å0.30 × 0.20 × 0.15 mm
β = 104.254 (3)°
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
1879 reflections with I > 2σ(I)
26614 measured reflectionsRint = 0.065
2785 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.19 e Å3
2785 reflectionsΔρmin = 0.24 e Å3
132 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
xyzUiso*/Ueq
O10.12971 (15)0.10253 (16)0.03495 (17)0.0774 (5)
H10.124 (4)0.034 (4)0.034 (4)0.169 (15)*
O20.29576 (13)0.24903 (13)0.53291 (13)0.0596 (4)
H20.293 (3)0.317 (3)0.601 (3)0.097 (8)*
N10.31551 (15)0.05600 (13)0.23301 (13)0.0479 (3)
N20.24604 (14)0.06268 (13)0.33862 (13)0.0449 (3)
N30.00111 (16)0.08524 (15)0.13275 (16)0.0586 (4)
N40.16951 (15)0.26301 (15)0.43425 (14)0.0534 (4)
C10.2119 (3)0.0631 (2)0.5483 (2)0.0714 (6)
H1A0.22150.01890.60260.107*
H1B0.25870.13600.60640.107*
H1C0.11340.08450.51390.107*
C20.27711 (19)0.04401 (17)0.42716 (17)0.0513 (4)
C30.3714 (2)0.12097 (18)0.37819 (19)0.0598 (5)
H30.41350.20130.41720.072*
C40.39228 (18)0.05630 (17)0.25889 (17)0.0508 (4)
C50.4841 (2)0.0981 (2)0.1644 (2)0.0705 (6)
H5A0.42990.09650.06840.106*
H5B0.51910.18830.18840.106*
H5C0.56230.03650.17570.106*
C60.14943 (18)0.17055 (16)0.33936 (16)0.0473 (4)
C70.01985 (19)0.17524 (18)0.22847 (18)0.0544 (4)
H70.048 (2)0.251 (2)0.233 (2)0.073 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0613 (8)0.0801 (10)0.0744 (10)0.0127 (7)0.0144 (7)0.0193 (8)
O20.0622 (8)0.0612 (8)0.0500 (7)0.0063 (6)0.0033 (6)0.0149 (6)
N10.0562 (8)0.0498 (7)0.0380 (6)0.0046 (6)0.0122 (6)0.0029 (5)
N20.0538 (8)0.0430 (7)0.0376 (6)0.0048 (5)0.0108 (5)0.0000 (5)
N30.0535 (8)0.0575 (8)0.0561 (8)0.0039 (6)0.0033 (6)0.0062 (7)
N40.0575 (8)0.0543 (8)0.0463 (7)0.0060 (6)0.0088 (6)0.0067 (6)
C10.0967 (16)0.0668 (12)0.0581 (11)0.0024 (10)0.0331 (11)0.0104 (9)
C20.0627 (10)0.0477 (9)0.0435 (8)0.0029 (7)0.0131 (7)0.0044 (6)
C30.0736 (12)0.0511 (10)0.0548 (10)0.0162 (8)0.0159 (8)0.0101 (8)
C40.0540 (9)0.0531 (9)0.0435 (8)0.0082 (7)0.0086 (7)0.0001 (7)
C50.0738 (13)0.0821 (14)0.0588 (11)0.0203 (10)0.0223 (9)0.0025 (10)
C60.0546 (9)0.0445 (8)0.0422 (8)0.0052 (7)0.0108 (6)0.0017 (6)
C70.0563 (10)0.0535 (9)0.0500 (9)0.0082 (8)0.0067 (7)0.0036 (7)
Geometric parameters (Å, º) top
O1—N31.3901 (19)C1—H1C0.9600
O1—H10.97 (4)C2—C31.368 (2)
O2—N41.3738 (18)C2—C11.492 (3)
O2—H20.95 (3)C3—H30.9300
N1—C41.326 (2)C4—C31.392 (2)
N2—C21.350 (2)C4—C51.498 (2)
N2—N11.3727 (18)C5—H5A0.9600
N2—C61.422 (2)C5—H5B0.9600
N3—C71.271 (2)C5—H5C0.9600
N4—C61.283 (2)C6—C71.452 (2)
C1—H1A0.9600C7—H71.00 (2)
C1—H1B0.9600
N3—O1—H1102 (2)C2—C3—H3126.5
N4—O2—H2104.5 (15)C4—C3—H3126.5
C4—N1—N2104.85 (13)N1—C4—C3110.52 (15)
C2—N2—N1111.97 (13)N1—C4—C5120.50 (16)
C2—N2—C6128.54 (14)C3—C4—C5128.99 (16)
N1—N2—C6119.41 (12)C4—C5—H5A109.5
C7—N3—O1112.23 (15)C4—C5—H5B109.5
C6—N4—O2112.99 (13)H5A—C5—H5B109.5
C2—C1—H1A109.5C4—C5—H5C109.5
C2—C1—H1B109.5H5A—C5—H5C109.5
H1A—C1—H1B109.5H5B—C5—H5C109.5
C2—C1—H1C109.5N4—C6—N2123.49 (15)
H1A—C1—H1C109.5N4—C6—C7118.07 (15)
H1B—C1—H1C109.5N2—C6—C7118.43 (14)
N2—C2—C3105.65 (15)N3—C7—C6118.92 (16)
N2—C2—C1122.60 (16)N3—C7—H7124.3 (12)
C3—C2—C1131.74 (16)C6—C7—H7116.8 (12)
C2—C3—C4107.00 (15)
N2—N1—C4—C30.52 (19)N1—N2—C6—C767.2 (2)
N2—N1—C4—C5179.96 (16)O1—N3—C7—C6179.58 (15)
C2—N2—N1—C40.89 (18)O2—N4—C6—N21.6 (2)
C6—N2—N1—C4177.87 (14)O2—N4—C6—C7179.53 (14)
N1—N2—C2—C30.90 (19)N2—C2—C3—C40.5 (2)
C6—N2—C2—C3177.53 (16)C1—C2—C3—C4178.3 (2)
N1—N2—C2—C1178.03 (16)N1—C4—C3—C20.0 (2)
C6—N2—C2—C11.4 (3)C5—C4—C3—C2179.47 (19)
C2—N2—C6—N469.6 (2)N4—C6—C7—N3179.27 (17)
N1—N2—C6—N4114.00 (18)N2—C6—C7—N31.8 (2)
C2—N2—C6—C7109.24 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.97 (4)2.51 (4)3.209 (3)129 (3)
O1—H1···N3i0.97 (4)2.10 (4)2.966 (3)149 (3)
O2—H2···N10.95 (3)1.78 (3)2.720 (2)172 (3)
Symmetry code: (i) x, y, z.

Experimental details

Crystal data
Chemical formulaC7H10N4O2
Mr182.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.7598 (5), 9.8572 (6), 9.8140 (7)
β (°) 104.254 (3)
V3)915.08 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.20 × 0.15
Data collection
DiffractometerRigaku R-AXIS RAPID-S
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
26614, 2785, 1879
Rint0.065
(sin θ/λ)max1)0.716
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.164, 1.02
No. of reflections2785
No. of parameters132
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.24

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.97 (4)2.51 (4)3.209 (3)129 (3)
O1—H1···N3i0.97 (4)2.10 (4)2.966 (3)149 (3)
O2—H2···N10.95 (3)1.78 (3)2.720 (2)172 (3)
Symmetry code: (i) x, y, z.
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)–(VIII). top
Bond/angle(I)(II)(III)(IV)(V)(VI)(VII)(VIII)
N3—O11.390 (2)1.403 (2)1.423 (3)1.417 (1)1.429 (4)1.424 (2)1.416 (3)1.383 (7)
N4—O21.374 (2)1.396 (2)1.396 (3)1.397 (3)
N3—C71.271 (2)1.281 (2)1.290 (3)1.290 (1)1.241 (6)1.289 (2)1.282 (3)1.300 (7)
N4—C61.283 (2)1.281 (2)1.282 (3)1.289 (3)
C6—C71.452 (2)1.477 (3)1.489 (3)1.510 (1)1.551 (7)1.513 (2)1.501 (4)1.491 (8)
1.473 (3)1.502 (4)
C6—C7—N3118.9 (2)115.2 (2)116.6 (2)114.3 (1)118.3 (5)113.2 (1)114.4 (2)115.3 (5)
C7—C6—N4118.1 (2)115.0 (2)115.0 (2)113.4 (2)
C7—N3—O1112.2 (2)112.4 (1)109.4 (2)110.7 (1)112.2 (4)110.6 (1)110.7 (2)111.4 (5)
C6—N4—O2113.0 (1)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'-di- phenylacetamidine (Büyükgüngör et al., 2003), (V): N-(3,4-dichloro- phenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine (Hökelek et al., 2004a), (VI): N-hydroxy-N'-(1-naphthyl)-2-phenylacetamidin-2-one (Hökelek et al., 2004b), (VII): N-(3-chloro-4-methylphenyl)-N'-hydroxy-2-oxo-2-phenylacetamidine-2,3- dimethylquinoxaline dimethylglyoxime (1/1) (Hökelek et al., 2004c) and (VIII): 2-(1H-benzimidazol-1-yl)-1-phenylethanone oxime (Özel Güven et al., 2007).
 

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