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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2173.
Published online 2008 October 22. doi:  10.1107/S1600536808034120
PMCID: PMC2959509

(E)-1-(4-Amino­phen­yl)ethanone oxime

Abstract

In the mol­ecule of the title compound, C8H10N2O, the oxime group is oriented at a dihedral angle of 5.58 (3)° with respect to the benzene ring. In the crystal structure, inter­molecular O—H(...)N and N—H(...)O hydrogen bonds link the mol­ecules, forming a three-dimensional network.

Related literature

For general background, see: Bertolasi et al. (1982 [triangle]); Degorre et al. (1998 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-o2173-scheme1.jpg

Experimental

Crystal data

  • C8H10N2O
  • M r = 150.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2173-efi1.jpg
  • a = 4.8641 (2) Å
  • b = 9.2016 (3) Å
  • c = 17.1447 (7) Å
  • β = 95.535 (2)°
  • V = 763.78 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 (2) K
  • 0.34 × 0.28 × 0.26 mm

Data collection

  • Enraf–Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997 [triangle]) T min = 0.972, T max = 0.979
  • 6132 measured reflections
  • 1761 independent reflections
  • 1483 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.107
  • S = 1.04
  • 1761 reflections
  • 113 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: COLLECT (Hooft, 1998 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2007 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034120/hk2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034120/hk2552Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

supplementary crystallographic information

Comment

One of the richest sources of diversity for the medicinal chemist is small heterocyclic rings, which in addition to often exhibiting biological activity, may serve as rigid scaffolds for a further display of functionalities. Oximes are among those, that have been reported to posses a wide range of biological activities including anti-oxidants, anti-inflammatory and as reactivators of organophosphate inhibited acetylcholine esterases (Degorre et al., 1998). The oxime moiety can both donate and accept hydrogen bonds, which makes it a very interesting building block in supramolecular chemistry (Bertolasi et al., 1982). It is also a key intermediate, which undergoes the 1,3-dipolar cycloaddition reaction with mono substituted alkenes to form isoxazolines.Due to importance of these compounds, we decided to synthesize the title compound and report herein its crystal structure.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges . The phenyl ring A (C1-C6) is oriented with respect to the planar (O1/N1/C1/C7/C8) moiety at a dihedral angle of 5.46 (3)°. N2 atom is -0.014 (3) Å away from the phenyl plane.

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

Experimental

For the preparation of the title compound, a solution of 1-(4-aminophenyl)- ethanone (1.35 g, 10 mmol) in methanol (15 ml) was added to a mixture of hydroxylamine sulfate (1.31 g, 10 mmol) and sodium acetate (2.0 g, 25 mmol). The reaction mass was refluxed for 4-5 h, until the reaction completed. The solvent was evaporated under vacuo and demineralized water (40 ml) was added, cooled to 268-265 K and filtered to obtain crystalline solid (yield; 1.11 g, 75%; m.p. 401-402 K).

Refinement

H atoms (for OH and NH2) were located in difference syntheses and refined isotropically [O-H = 0.92 (2) Å; Uiso(H) = 0.049 (5) Å2 and N-H = 0.916 (18) and 0.929 (19) Å; Uiso(H) = 0.035 (4) and 0.039 (4) Å2]. The remaining H atoms were positioned geometrically, with C-H = 0.95 and 0.98 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Figures

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 partial packing diagram. Hydrogen bonds are shown as dashed lines.

Crystal data

C8H10N2OF(000) = 320
Mr = 150.18Dx = 1.306 Mg m3
Monoclinic, P21/nMelting point: 401(1) K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 4.8641 (2) ÅCell parameters from 3781 reflections
b = 9.2016 (3) Åθ = 1.0–30.0°
c = 17.1447 (7) ŵ = 0.09 mm1
β = 95.535 (2)°T = 100 K
V = 763.78 (5) Å3Block, pale yellow
Z = 40.34 × 0.28 × 0.26 mm

Data collection

Enraf–Nonius KappaCCD diffractometer1761 independent reflections
Radiation source: fine-focus sealed tube1483 reflections with I > 2σ(I)
horizontally mounted graphite crystalRint = 0.026
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 4.2°
[var phi] and ω scansh = −6→6
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997)k = −11→11
Tmin = 0.972, Tmax = 0.979l = −22→22
6132 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: mixed
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2855P] where P = (Fo2 + 2Fc2)/3
1761 reflections(Δ/σ)max < 0.001
113 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

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)

xyzUiso*/Ueq
O10.42570 (18)0.21270 (10)0.47528 (5)0.0203 (2)
H1O0.273 (4)0.158 (2)0.4589 (11)0.049 (5)*
N10.38949 (19)0.23108 (10)0.55574 (5)0.0168 (2)
N20.4407 (2)0.42572 (11)0.91465 (6)0.0186 (2)
H2N0.288 (4)0.3807 (18)0.9308 (10)0.035 (4)*
H2M0.440 (4)0.525 (2)0.9257 (10)0.039 (4)*
C10.5281 (2)0.34967 (12)0.67458 (6)0.0147 (2)
C20.3462 (2)0.26638 (12)0.71490 (7)0.0179 (3)
H20.24210.19140.68780.021*
C30.3148 (2)0.29074 (13)0.79324 (7)0.0177 (3)
H30.19030.23270.81920.021*
C40.4655 (2)0.40050 (12)0.83408 (6)0.0156 (2)
C50.6512 (2)0.48187 (13)0.79535 (7)0.0187 (3)
H50.75880.55500.82300.022*
C60.6810 (2)0.45726 (13)0.71660 (7)0.0178 (3)
H60.80750.51460.69100.021*
C70.5571 (2)0.32441 (12)0.59009 (6)0.0149 (2)
C80.7713 (2)0.40782 (13)0.55104 (7)0.0195 (3)
H8A0.76060.38150.49540.029*
H8B0.95530.38410.57620.029*
H8C0.73770.51230.55600.029*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0222 (5)0.0272 (5)0.0121 (4)−0.0020 (4)0.0043 (3)−0.0033 (3)
N10.0190 (5)0.0200 (5)0.0118 (5)0.0020 (4)0.0038 (4)−0.0010 (4)
N20.0230 (5)0.0190 (5)0.0141 (5)0.0005 (4)0.0032 (4)−0.0012 (4)
C10.0144 (5)0.0144 (5)0.0156 (5)0.0029 (4)0.0024 (4)0.0005 (4)
C20.0191 (6)0.0168 (5)0.0178 (5)−0.0026 (4)0.0018 (4)−0.0015 (4)
C30.0172 (5)0.0182 (6)0.0181 (6)−0.0017 (4)0.0042 (4)0.0018 (4)
C40.0168 (5)0.0160 (5)0.0138 (5)0.0042 (4)0.0012 (4)0.0003 (4)
C50.0200 (6)0.0173 (6)0.0187 (6)−0.0025 (4)0.0017 (4)−0.0036 (4)
C60.0179 (5)0.0176 (5)0.0185 (6)−0.0017 (4)0.0041 (4)0.0006 (4)
C70.0139 (5)0.0158 (5)0.0153 (5)0.0039 (4)0.0027 (4)0.0019 (4)
C80.0177 (5)0.0231 (6)0.0182 (5)−0.0019 (4)0.0045 (4)0.0010 (4)

Geometric parameters (Å, °)

O1—N11.4175 (11)C3—C41.3961 (16)
O1—H1O0.92 (2)C3—H30.9500
N1—C71.2869 (15)C4—C51.3905 (16)
N2—C41.4173 (14)C5—C61.3903 (15)
N2—H2N0.916 (18)C5—H50.9500
N2—H2M0.929 (19)C6—H60.9500
C1—C61.3961 (16)C7—C81.5026 (15)
C1—C21.4020 (16)C8—H8A0.9800
C1—C71.4872 (14)C8—H8B0.9800
C2—C31.3846 (15)C8—H8C0.9800
C2—H20.9500
N1—O1—H1O100.9 (11)C3—C4—N2121.15 (10)
C7—N1—O1113.10 (9)C6—C5—C4120.63 (10)
C4—N2—H2N111.6 (10)C6—C5—H5119.7
C4—N2—H2M111.1 (11)C4—C5—H5119.7
H2N—N2—H2M111.2 (15)C5—C6—C1121.09 (10)
C6—C1—C2117.60 (10)C5—C6—H6119.5
C6—C1—C7121.17 (10)C1—C6—H6119.5
C2—C1—C7121.23 (10)N1—C7—C1115.76 (9)
C3—C2—C1121.59 (11)N1—C7—C8124.95 (10)
C3—C2—H2119.2C1—C7—C8119.29 (10)
C1—C2—H2119.2C7—C8—H8A109.5
C2—C3—C4120.12 (10)C7—C8—H8B109.5
C2—C3—H3119.9H8A—C8—H8B109.5
C4—C3—H3119.9C7—C8—H8C109.5
C5—C4—C3118.94 (10)H8A—C8—H8C109.5
C5—C4—N2119.85 (10)H8B—C8—H8C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···N2i0.92 (2)1.88 (2)2.7919 (14)169.8 (18)
N2—H2N···O1ii0.916 (18)2.165 (18)3.0790 (13)175.7 (15)
N2—H2M···N1iii0.929 (19)2.525 (19)3.3000 (14)141.0 (14)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2552).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bertolasi, V., Gilli, G. & Veronese, A. C. (1982). Acta Cryst. B38, 502–511.
  • Brandenburg, K. (2007). DIAMOND Crystal Impact Gbr, Bonn, Germany.
  • Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst.38, 381–388.
  • Degorre, F., Kiffer, D. & Terrie, F. (1998). J. Med. Chem 31, 757-761. [PubMed]
  • Hooft, R. W. W. (1998). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzimology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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