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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2474.
Published online 2010 September 4. doi:  10.1107/S1600536810034586
PMCID: PMC2983254

1-(4-{[(E)-5-Chloro-2-hy­droxy­benzyl­idene]amino}­phen­yl)ethanone oxime

Abstract

The title compound, C15H13ClN2O2, is an aromatic Schiff base having an aldoxime substituent; the two rings on the azomethine linkage are twisted by 44.4 (1)°. The phenolic H atom is intra­molecularly hydrogen bonded to the azomethine N atom, generating an S(6) ring. In the crystal, inversion dimers linked by pairs of O—H(...)N hydrogen bonds occur. The crystal studied was a non-merohedral twin with a 35% minor component.

Related literature

For background to oxime-type compounds, see: Dong et al. (2009 [triangle], 2010b [triangle]). For the synthesis, see: Rafiq et al. (2008 [triangle]); Dong et al. (2010a [triangle]). For the treatment of non-merohedrally twinned diffraction intensities, see: Spek (2009 [triangle]). We have reported the crystal structure of one of the first examples of a Schiff base bearing the oxime unit, see: Zhao et al. (2009 [triangle]).

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Object name is e-66-o2474-scheme1.jpg

Experimental

Crystal data

  • C15H13ClN2O2
  • M r = 288.72
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2474-efi1.jpg
  • a = 15.356 (2) Å
  • b = 14.035 (2) Å
  • c = 6.1124 (6) Å
  • β = 95.244 (1)°
  • V = 1311.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 293 K
  • 0.40 × 0.10 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.892, T max = 0.986
  • 3689 measured reflections
  • 2971 independent reflections
  • 1552 reflections with I > 2σ(I)
  • R int = 0.092

Refinement

  • R[F 2 > 2σ(F 2)] = 0.076
  • wR(F 2) = 0.239
  • S = 1.02
  • 2970 reflections
  • 192 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034586/hg2704sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034586/hg2704Isup2.hkl

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

Acknowledgments

We thank the Educational Department Foundation of Gansu Province (No. 20873) and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Oxime-type compounds are a very important ligands in coordination chemistry (Dong et al., 2010b; Dong et al., 2009). 4-Aminophenylethanone oxime is a amino compound having an oxime unit, a unit that can undergo a wide range of transformations. On the other hand, the amino unit lends itself to condensation with carbonyl compounds to yield Schiff bases, yet another class of compounds having an equally wide range of applications. We have reported the crystal structure of one of the first examples of a Schiff base bearing the oxime unit (Zhao et al., 2009). Here we report the synthesis and crystal structure of (E)-4-[(1-Hydroxyimino)ethyl]-N-(4'-methylbenzylidene)aniline (I), (Fig. 1).

The single-crystal structure of the title compound is built up by discrete C15H13ClN2O2 molecules, in which all bond lengths are in normal ranges. Within the molecule, the two rings on the azomethine linkage are twisted by 44.4 (1) °. In the crystal structure, adjacent molecules are connected by an O–H···Noxime hydrogen bond to generate a dimer (Table 1 and Fig. 2).

Experimental

4-Aminophenylethanone oxime was prepared by 1-(4-aminophenyl)ethanone, hydroxylamine sulfate and sodium acetate (Rafiq et al., 2008; Dong et al., 2010a). To an ethanol solution (6 ml) of 4-aminophenylethanone oxime (152.1 mg, 1.00 mmol) was added dropwise an ethanol solution (6 ml) of 5-chlorosalicylaldehyde (159.2 mg, 1.00 mmol). The mixture solution was stirred at 328 K for 5 h. After cooling to room temperature, the precipitate was filtered off, and washed successively three times with ethanol. The product was dried in vacuo and purified by recrystallization from ethanol to yield 266.5 mg (Yield, 92.3%) of solid; m.p. 484–486 K. Pale-yellow needle-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a mixed solution of ethyl acetate-chloroform (3:2) of (I) at room temperature for about four weeks. Anal. Calcd. for C15H13ClN2O2: C, 62.40; H, 4.54; N, 9.70; Found: C, 62.22; H, 4.50; N, 9.85.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

The hydroxy H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H of 0.85±0.01 Å; their temperature factors were freely refined.

The crystal is a non-merohedral twin; the diffraction intensities were separated into two domains by using PLATON (Spek, 2009); the minor twin component was 35%.

The somewhat large weighting scheme is probably the consequence of the twinning. Lowering the 2θ limit to 50 ° leads to a marginally better refinement but the weighting scheme is identical.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C15H13ClN2O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Hydrogen-bonded dimer.

Crystal data

C15H13ClN2O2F(000) = 600
Mr = 288.72Dx = 1.462 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1371 reflections
a = 15.356 (2) Åθ = 2.7–24.9°
b = 14.035 (2) ŵ = 0.29 mm1
c = 6.1124 (6) ÅT = 293 K
β = 95.244 (1)°Needle-like, yellow
V = 1311.8 (2) Å30.40 × 0.10 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer2971 independent reflections
Radiation source: fine-focus sealed tube1552 reflections with I > 2σ(I)
graphiteRint = 0.092
[var phi] and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −19→19
Tmin = 0.892, Tmax = 0.986k = −18→18
3689 measured reflectionsl = −2→7

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)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.1159P)2] where P = (Fo2 + 2Fc2)/3
2970 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.41 e Å3
2 restraintsΔρmin = −0.34 e Å3

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

xyzUiso*/Ueq
Cl10.26367 (8)0.34104 (10)0.2064 (3)0.0716 (5)
N10.6685 (2)0.3635 (2)0.1036 (6)0.0378 (9)
O10.5752 (2)0.4086 (3)−0.2569 (6)0.0543 (9)
N20.9958 (2)0.4344 (2)0.8002 (6)0.0444 (10)
O21.0777 (2)0.4341 (2)0.9205 (7)0.0565 (10)
C10.5046 (3)0.3912 (3)−0.1470 (8)0.0395 (11)
C20.4222 (3)0.4095 (3)−0.2484 (8)0.0454 (11)
H2A0.41640.4333−0.39100.054*
C30.3485 (3)0.3930 (3)−0.1418 (9)0.0481 (12)
H30.29330.4051−0.21240.058*
C40.3566 (3)0.3589 (3)0.0678 (9)0.0421 (11)
C50.4378 (3)0.3407 (3)0.1758 (8)0.0407 (10)
H50.44240.31780.31920.049*
C60.5131 (3)0.3569 (3)0.0687 (7)0.0353 (10)
C70.5974 (3)0.3471 (3)0.1921 (7)0.0359 (10)
H70.60020.32850.33860.043*
C80.7485 (2)0.3677 (3)0.2391 (7)0.0350 (10)
C90.8234 (3)0.3372 (3)0.1531 (7)0.0359 (10)
H90.82060.31240.01160.043*
C100.9030 (3)0.3438 (3)0.2787 (8)0.0368 (10)
H100.95310.32190.22010.044*
C110.9104 (2)0.3813 (3)0.4848 (7)0.0327 (10)
C120.8338 (2)0.4151 (3)0.5670 (7)0.0368 (10)
H120.83680.44270.70580.044*
C130.7546 (3)0.4079 (3)0.4454 (7)0.0374 (10)
H130.70440.43040.50270.045*
C140.9956 (3)0.3880 (3)0.6196 (8)0.0363 (10)
C151.0748 (3)0.3417 (3)0.5426 (9)0.0524 (13)
H15A1.12160.34360.65800.079*
H15B1.09210.37520.41650.079*
H15C1.06160.27670.50370.079*
H10.619 (3)0.395 (4)−0.166 (8)0.10 (2)*
H21.076 (4)0.471 (4)1.031 (8)0.12 (3)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0347 (6)0.0879 (10)0.0928 (13)0.0041 (6)0.0083 (7)0.0070 (9)
N10.0316 (19)0.0419 (19)0.039 (2)0.0017 (14)−0.0015 (17)−0.0003 (16)
O10.048 (2)0.075 (2)0.040 (2)0.0013 (17)0.0039 (18)0.0068 (18)
N20.0351 (19)0.050 (2)0.045 (3)−0.0027 (16)−0.0121 (18)0.0007 (19)
O20.0406 (17)0.061 (2)0.064 (3)0.0004 (15)−0.0211 (17)−0.004 (2)
C10.037 (2)0.038 (2)0.041 (3)0.0029 (18)−0.005 (2)−0.003 (2)
C20.050 (3)0.041 (2)0.043 (3)0.006 (2)−0.014 (2)−0.001 (2)
C30.037 (2)0.045 (3)0.059 (4)0.0054 (19)−0.011 (2)−0.005 (2)
C40.033 (2)0.039 (2)0.053 (3)0.0005 (17)−0.001 (2)−0.005 (2)
C50.040 (2)0.037 (2)0.044 (3)0.0021 (18)−0.004 (2)−0.002 (2)
C60.032 (2)0.036 (2)0.037 (3)−0.0014 (17)−0.0029 (19)−0.0036 (19)
C70.039 (2)0.034 (2)0.033 (2)0.0015 (17)−0.004 (2)−0.0011 (19)
C80.032 (2)0.035 (2)0.037 (3)−0.0023 (16)−0.0002 (19)0.0018 (19)
C90.039 (2)0.038 (2)0.030 (2)−0.0001 (17)0.0020 (19)−0.0032 (18)
C100.030 (2)0.039 (2)0.042 (3)0.0003 (17)0.005 (2)−0.002 (2)
C110.028 (2)0.030 (2)0.040 (3)−0.0040 (15)0.0033 (19)0.0008 (18)
C120.037 (2)0.043 (2)0.030 (2)−0.0021 (18)−0.0006 (19)−0.0060 (19)
C130.029 (2)0.046 (2)0.037 (3)0.0025 (17)0.0045 (19)−0.003 (2)
C140.032 (2)0.033 (2)0.042 (3)−0.0031 (17)−0.002 (2)0.005 (2)
C150.031 (2)0.066 (3)0.060 (3)0.003 (2)0.005 (2)−0.005 (3)

Geometric parameters (Å, °)

Cl1—C41.743 (5)C6—C71.444 (6)
N1—C71.282 (5)C7—H70.9300
N1—C81.419 (5)C8—C131.376 (6)
O1—C11.348 (5)C8—C91.375 (5)
O1—H10.85 (5)C9—C101.387 (6)
N2—C141.281 (6)C9—H90.9300
N2—O21.398 (4)C10—C111.360 (6)
O2—H20.86 (5)C10—H100.9300
C1—C21.382 (6)C11—C121.403 (5)
C1—C61.398 (6)C11—C141.484 (5)
C2—C31.376 (6)C12—C131.370 (5)
C2—H2A0.9300C12—H120.9300
C3—C41.363 (7)C13—H130.9300
C3—H30.9300C14—C151.492 (6)
C4—C51.379 (6)C15—H15A0.9600
C5—C61.400 (6)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C7—N1—C8119.1 (4)C13—C8—N1122.3 (4)
C1—O1—H1104 (4)C9—C8—N1118.3 (4)
C14—N2—O2112.6 (4)C8—C9—C10119.6 (4)
N2—O2—H2109 (5)C8—C9—H9120.2
O1—C1—C2119.2 (4)C10—C9—H9120.2
O1—C1—C6121.5 (4)C11—C10—C9122.2 (4)
C2—C1—C6119.3 (4)C11—C10—H10118.9
C3—C2—C1121.1 (5)C9—C10—H10118.9
C3—C2—H2A119.5C10—C11—C12117.4 (4)
C1—C2—H2A119.5C10—C11—C14122.2 (4)
C4—C3—C2119.7 (4)C12—C11—C14120.4 (4)
C4—C3—H3120.2C13—C12—C11120.9 (4)
C2—C3—H3120.2C13—C12—H12119.6
C3—C4—C5121.1 (4)C11—C12—H12119.6
C3—C4—Cl1119.9 (4)C12—C13—C8120.6 (4)
C5—C4—Cl1119.0 (4)C12—C13—H13119.7
C4—C5—C6119.7 (5)C8—C13—H13119.7
C4—C5—H5120.1N2—C14—C11116.3 (4)
C6—C5—H5120.1N2—C14—C15123.7 (4)
C1—C6—C5119.2 (4)C11—C14—C15120.0 (4)
C1—C6—C7121.8 (4)C14—C15—H15A109.5
C5—C6—C7118.7 (4)C14—C15—H15B109.5
N1—C7—C6121.3 (4)H15A—C15—H15B109.5
N1—C7—H7119.4C14—C15—H15C109.5
C6—C7—H7119.4H15A—C15—H15C109.5
C13—C8—C9119.2 (4)H15B—C15—H15C109.5
O1—C1—C2—C3−179.8 (4)C7—N1—C8—C9147.4 (4)
C6—C1—C2—C3−1.0 (6)C13—C8—C9—C102.7 (6)
C1—C2—C3—C40.5 (6)N1—C8—C9—C10177.6 (4)
C2—C3—C4—C50.2 (7)C8—C9—C10—C11−1.2 (6)
C2—C3—C4—Cl1178.2 (3)C9—C10—C11—C12−1.0 (6)
C3—C4—C5—C6−0.4 (6)C9—C10—C11—C14179.8 (4)
Cl1—C4—C5—C6−178.4 (3)C10—C11—C12—C131.7 (6)
O1—C1—C6—C5179.6 (4)C14—C11—C12—C13−179.0 (4)
C2—C1—C6—C50.8 (6)C11—C12—C13—C8−0.3 (7)
O1—C1—C6—C76.1 (6)C9—C8—C13—C12−1.9 (6)
C2—C1—C6—C7−172.6 (4)N1—C8—C13—C12−176.6 (4)
C4—C5—C6—C1−0.1 (6)O2—N2—C14—C11177.7 (3)
C4—C5—C6—C7173.6 (4)O2—N2—C14—C15−1.9 (6)
C8—N1—C7—C6170.1 (3)C10—C11—C14—N2172.3 (4)
C1—C6—C7—N1−4.7 (6)C12—C11—C14—N2−7.0 (6)
C5—C6—C7—N1−178.2 (3)C10—C11—C14—C15−8.1 (6)
C7—N1—C8—C13−37.9 (6)C12—C11—C14—C15172.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.85 (5)1.81 (3)2.594 (5)153 (6)
O2—H2···N2i0.86 (5)2.06 (4)2.819 (5)147 (6)

Symmetry codes: (i) −x+2, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2704).

References

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  • Zhao, L., Dong, W.-K., Wu, J.-C., Sun, Y.-X. & Xu, L. (2009). Acta Cryst. E65, o2462. [PMC free article] [PubMed]

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