Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035490/xu2297sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035490/xu2297Isup2.hkl |
CCDC reference: 657838
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C)= 0.003 Å
- R factor = 0.060
- wR factor = 0.164
- Data-to-parameter ratio = 21.1
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
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).
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%).
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.
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).
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).
C7H10N4O2 | F(000) = 384 |
Mr = 182.19 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3673 reflections |
a = 9.7598 (5) Å | θ = 2.0–30.5° |
b = 9.8572 (6) Å | µ = 0.10 mm−1 |
c = 9.8140 (7) Å | T = 298 K |
β = 104.254 (3)° | Block, colourless |
V = 915.08 (10) Å3 | 0.30 × 0.20 × 0.15 mm |
Z = 4 |
Rigaku R-AXIS RAPID-S diffractometer | 1879 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.065 |
Graphite monochromator | θmax = 30.6°, θmin = 2.9° |
ω scans | h = −13→13 |
26614 measured reflections | k = −14→14 |
2785 independent reflections | l = −13→13 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H 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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C7H10N4O2 | V = 915.08 (10) Å3 |
Mr = 182.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.7598 (5) Å | µ = 0.10 mm−1 |
b = 9.8572 (6) Å | T = 298 K |
c = 9.8140 (7) Å | 0.30 × 0.20 × 0.15 mm |
β = 104.254 (3)° |
Rigaku R-AXIS RAPID-S diffractometer | 1879 reflections with I > 2σ(I) |
26614 measured reflections | Rint = 0.065 |
2785 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.19 e Å−3 |
2785 reflections | Δρmin = −0.24 e Å−3 |
132 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.12971 (15) | 0.10253 (16) | 0.03495 (17) | 0.0774 (5) | |
H1 | −0.124 (4) | 0.034 (4) | −0.034 (4) | 0.169 (15)* | |
O2 | 0.29576 (13) | 0.24903 (13) | 0.53291 (13) | 0.0596 (4) | |
H2 | 0.293 (3) | 0.317 (3) | 0.601 (3) | 0.097 (8)* | |
N1 | 0.31551 (15) | 0.05600 (13) | 0.23301 (13) | 0.0479 (3) | |
N2 | 0.24604 (14) | 0.06268 (13) | 0.33862 (13) | 0.0449 (3) | |
N3 | −0.00111 (16) | 0.08524 (15) | 0.13275 (16) | 0.0586 (4) | |
N4 | 0.16951 (15) | 0.26301 (15) | 0.43425 (14) | 0.0534 (4) | |
C1 | 0.2119 (3) | −0.0631 (2) | 0.5483 (2) | 0.0714 (6) | |
H1A | 0.2215 | 0.0189 | 0.6026 | 0.107* | |
H1B | 0.2587 | −0.1360 | 0.6064 | 0.107* | |
H1C | 0.1134 | −0.0845 | 0.5139 | 0.107* | |
C2 | 0.27711 (19) | −0.04401 (17) | 0.42716 (17) | 0.0513 (4) | |
C3 | 0.3714 (2) | −0.12097 (18) | 0.37819 (19) | 0.0598 (5) | |
H3 | 0.4135 | −0.2013 | 0.4172 | 0.072* | |
C4 | 0.39228 (18) | −0.05630 (17) | 0.25889 (17) | 0.0508 (4) | |
C5 | 0.4841 (2) | −0.0981 (2) | 0.1644 (2) | 0.0705 (6) | |
H5A | 0.4299 | −0.0965 | 0.0684 | 0.106* | |
H5B | 0.5191 | −0.1883 | 0.1884 | 0.106* | |
H5C | 0.5623 | −0.0365 | 0.1757 | 0.106* | |
C6 | 0.14943 (18) | 0.17055 (16) | 0.33936 (16) | 0.0473 (4) | |
C7 | 0.01985 (19) | 0.17524 (18) | 0.22847 (18) | 0.0544 (4) | |
H7 | −0.048 (2) | 0.251 (2) | 0.233 (2) | 0.073 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0613 (8) | 0.0801 (10) | 0.0744 (10) | 0.0127 (7) | −0.0144 (7) | −0.0193 (8) |
O2 | 0.0622 (8) | 0.0612 (8) | 0.0500 (7) | 0.0063 (6) | 0.0033 (6) | −0.0149 (6) |
N1 | 0.0562 (8) | 0.0498 (7) | 0.0380 (6) | 0.0046 (6) | 0.0122 (6) | 0.0029 (5) |
N2 | 0.0538 (8) | 0.0430 (7) | 0.0376 (6) | 0.0048 (5) | 0.0108 (5) | 0.0000 (5) |
N3 | 0.0535 (8) | 0.0575 (8) | 0.0561 (8) | 0.0039 (6) | −0.0033 (6) | −0.0062 (7) |
N4 | 0.0575 (8) | 0.0543 (8) | 0.0463 (7) | 0.0060 (6) | 0.0088 (6) | −0.0067 (6) |
C1 | 0.0967 (16) | 0.0668 (12) | 0.0581 (11) | 0.0024 (10) | 0.0331 (11) | 0.0104 (9) |
C2 | 0.0627 (10) | 0.0477 (9) | 0.0435 (8) | 0.0029 (7) | 0.0131 (7) | 0.0044 (6) |
C3 | 0.0736 (12) | 0.0511 (10) | 0.0548 (10) | 0.0162 (8) | 0.0159 (8) | 0.0101 (8) |
C4 | 0.0540 (9) | 0.0531 (9) | 0.0435 (8) | 0.0082 (7) | 0.0086 (7) | 0.0001 (7) |
C5 | 0.0738 (13) | 0.0821 (14) | 0.0588 (11) | 0.0203 (10) | 0.0223 (9) | −0.0025 (10) |
C6 | 0.0546 (9) | 0.0445 (8) | 0.0422 (8) | 0.0052 (7) | 0.0108 (6) | −0.0017 (6) |
C7 | 0.0563 (10) | 0.0535 (9) | 0.0500 (9) | 0.0082 (8) | 0.0067 (7) | −0.0036 (7) |
O1—N3 | 1.3901 (19) | C1—H1C | 0.9600 |
O1—H1 | 0.97 (4) | C2—C3 | 1.368 (2) |
O2—N4 | 1.3738 (18) | C2—C1 | 1.492 (3) |
O2—H2 | 0.95 (3) | C3—H3 | 0.9300 |
N1—C4 | 1.326 (2) | C4—C3 | 1.392 (2) |
N2—C2 | 1.350 (2) | C4—C5 | 1.498 (2) |
N2—N1 | 1.3727 (18) | C5—H5A | 0.9600 |
N2—C6 | 1.422 (2) | C5—H5B | 0.9600 |
N3—C7 | 1.271 (2) | C5—H5C | 0.9600 |
N4—C6 | 1.283 (2) | C6—C7 | 1.452 (2) |
C1—H1A | 0.9600 | C7—H7 | 1.00 (2) |
C1—H1B | 0.9600 | ||
N3—O1—H1 | 102 (2) | C2—C3—H3 | 126.5 |
N4—O2—H2 | 104.5 (15) | C4—C3—H3 | 126.5 |
C4—N1—N2 | 104.85 (13) | N1—C4—C3 | 110.52 (15) |
C2—N2—N1 | 111.97 (13) | N1—C4—C5 | 120.50 (16) |
C2—N2—C6 | 128.54 (14) | C3—C4—C5 | 128.99 (16) |
N1—N2—C6 | 119.41 (12) | C4—C5—H5A | 109.5 |
C7—N3—O1 | 112.23 (15) | C4—C5—H5B | 109.5 |
C6—N4—O2 | 112.99 (13) | H5A—C5—H5B | 109.5 |
C2—C1—H1A | 109.5 | C4—C5—H5C | 109.5 |
C2—C1—H1B | 109.5 | H5A—C5—H5C | 109.5 |
H1A—C1—H1B | 109.5 | H5B—C5—H5C | 109.5 |
C2—C1—H1C | 109.5 | N4—C6—N2 | 123.49 (15) |
H1A—C1—H1C | 109.5 | N4—C6—C7 | 118.07 (15) |
H1B—C1—H1C | 109.5 | N2—C6—C7 | 118.43 (14) |
N2—C2—C3 | 105.65 (15) | N3—C7—C6 | 118.92 (16) |
N2—C2—C1 | 122.60 (16) | N3—C7—H7 | 124.3 (12) |
C3—C2—C1 | 131.74 (16) | C6—C7—H7 | 116.8 (12) |
C2—C3—C4 | 107.00 (15) | ||
N2—N1—C4—C3 | 0.52 (19) | N1—N2—C6—C7 | 67.2 (2) |
N2—N1—C4—C5 | −179.96 (16) | O1—N3—C7—C6 | 179.58 (15) |
C2—N2—N1—C4 | −0.89 (18) | O2—N4—C6—N2 | 1.6 (2) |
C6—N2—N1—C4 | −177.87 (14) | O2—N4—C6—C7 | −179.53 (14) |
N1—N2—C2—C3 | 0.90 (19) | N2—C2—C3—C4 | −0.5 (2) |
C6—N2—C2—C3 | 177.53 (16) | C1—C2—C3—C4 | 178.3 (2) |
N1—N2—C2—C1 | −178.03 (16) | N1—C4—C3—C2 | 0.0 (2) |
C6—N2—C2—C1 | −1.4 (3) | C5—C4—C3—C2 | −179.47 (19) |
C2—N2—C6—N4 | 69.6 (2) | N4—C6—C7—N3 | 179.27 (17) |
N1—N2—C6—N4 | −114.00 (18) | N2—C6—C7—N3 | −1.8 (2) |
C2—N2—C6—C7 | −109.24 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.97 (4) | 2.51 (4) | 3.209 (3) | 129 (3) |
O1—H1···N3i | 0.97 (4) | 2.10 (4) | 2.966 (3) | 149 (3) |
O2—H2···N1 | 0.95 (3) | 1.78 (3) | 2.720 (2) | 172 (3) |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C7H10N4O2 |
Mr | 182.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 9.7598 (5), 9.8572 (6), 9.8140 (7) |
β (°) | 104.254 (3) |
V (Å3) | 915.08 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID-S |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26614, 2785, 1879 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.716 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.164, 1.02 |
No. of reflections | 2785 |
No. of parameters | 132 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.97 (4) | 2.51 (4) | 3.209 (3) | 129 (3) |
O1—H1···N3i | 0.97 (4) | 2.10 (4) | 2.966 (3) | 149 (3) |
O2—H2···N1 | 0.95 (3) | 1.78 (3) | 2.720 (2) | 172 (3) |
Symmetry code: (i) −x, −y, −z. |
Bond/angle | (I) | (II) | (III) | (IV) | (V) | (VI) | (VII) | (VIII) |
N3—O1 | 1.390 (2) | 1.403 (2) | 1.423 (3) | 1.417 (1) | 1.429 (4) | 1.424 (2) | 1.416 (3) | 1.383 (7) |
N4—O2 | 1.374 (2) | 1.396 (2) | 1.396 (3) | 1.397 (3) | ||||
N3—C7 | 1.271 (2) | 1.281 (2) | 1.290 (3) | 1.290 (1) | 1.241 (6) | 1.289 (2) | 1.282 (3) | 1.300 (7) |
N4—C6 | 1.283 (2) | 1.281 (2) | 1.282 (3) | 1.289 (3) | ||||
C6—C7 | 1.452 (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—N3 | 118.9 (2) | 115.2 (2) | 116.6 (2) | 114.3 (1) | 118.3 (5) | 113.2 (1) | 114.4 (2) | 115.3 (5) |
C7—C6—N4 | 118.1 (2) | 115.0 (2) | 115.0 (2) | 113.4 (2) | ||||
C7—N3—O1 | 112.2 (2) | 112.4 (1) | 109.4 (2) | 110.7 (1) | 112.2 (4) | 110.6 (1) | 110.7 (2) | 111.4 (5) |
C6—N4—O2 | 113.0 (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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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.