organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-(4-{[(E)-4-Methyl­benzyl­­idene]amino}­phen­yl)ethanone oxime

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: zhaoli_72@163.com

(Received 21 August 2010; accepted 27 August 2010; online 4 September 2010)

In the title compound, C16H16N2O, the dihedral angle formed by the two benzene rings is 50.3 (1)°. In the crystal structure, mol­ecules are linked into an infinite one-dimensional supra­molecular structure by inter­molecular O—H⋯N hydrogen-bond inter­actions.

Related literature

For background to oxime-type compounds, see: Dong et al. (2009a[Dong, W.-K., Lv, Z.-W., Sun, Y.-X., Xu, L., Wang, L. & Dong, X.-Y. (2009a). Chin. J. Inorg. Chem. 25, 1627-1634.],b[Dong, W.-K., Sun, Y.-X., Zhang, Y.-P., Li, L., He, X.-N. & Tang, X.-L. (2009b). Inorg. Chim. Acta, 362, 117-124.]). For the synthesis, see: Rafiq et al. (2008[Rafiq, M., Hanif, M., Qadeer, G., Vuoti, S. & Autio, J. (2008). Acta Cryst. E64, o2173.]); Dong et al. (2009c[Dong, W.-K., Duan, J.-G., Guan, Y.-H., Shi, J.-Y. & Zhao, C.-Y. (2009c). Inorg. Chim. Acta, 362, 1129-1134.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O

  • Mr = 252.31

  • Monoclinic, P 21 /n

  • a = 5.7785 (6) Å

  • b = 14.581 (2) Å

  • c = 16.226 (2) Å

  • β = 94.285 (1)°

  • V = 1363.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.45 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.966, Tmax = 0.992

  • 6860 measured reflections

  • 2396 independent reflections

  • 1480 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.136

  • S = 0.95

  • 2396 reflections

  • 178 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N2i 0.86 (1) 2.06 (1) 2.919 (2) 175 (3)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1996[Bruker (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1996[Bruker (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Oxime-type compounds are a great important ligands in modern coordination chemistry (Dong et al., 2009a; Dong et al., 2009b). Structures of oxime-type compounds derived from substituted benzaldehydes and 1-(4-aminophenyl)ethanone haven't been reported so far (Rafiq et al., 2008). 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 C16H16N2O molecules, in which all bond lengths are in normal ranges. Within the molecule, the dihedral angle formed by the two benzene rings is 50.3 (1)°. In the crystal structure, the molecules are linked into infinite one-dimensional supramolecular structure by intermolecular O—H···N hydrogen bond interaction (Table 1 and Fig. 2).

Related literature top

For background to oxime-type compounds, see: Dong et al. (2009a,b). For the synthesis, see: Rafiq et al. (2008); Dong et al. (2009c).

Experimental top

4-Aminophenylethanone oxime was prepared by 1-(4-aminophenyl)ethanone, hydroxylamine sulfate and sodium acetate (Rafiq et al., 2008; Dong et al., 2009c). To an ethanol solution (7 ml) of 4-aminophenylethanone oxime (151.0 mg, 1.00 mmol) was added dropwise an ethanol solution (8 ml) of 4-methylbenzaldehyde (121.6 mg, 1.00 mmol). The mixture solution was stirred at 330 K for 4 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 220.3 mg (Yield, 80.8%) of solid; m.p. 471–472 K. Pale-yellow block-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of acetone of (I) at room temperature for about two weeks. Anal. Calcd. for C16H16N2O: C, 76.16; H, 6.39; N, 11.10; Found: C, 76.08; H, 6.45; N, 11.02.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 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-atom was located in a difference Fourier map, and was refined with a distance restraint of O–H of 0.85±0.01 Å; its temperature factor was freely refined.

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C16H16N2O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Part of one-dimensional supramolecular structure is formed by O—H···N intermolecular interaction with H bonds drawn as dotted lines.
1-(4-{[(E)-4-Methylbenzylidene]amino}phenyl)ethanone oxime top
Crystal data top
C16H16N2OF(000) = 536
Mr = 252.31Dx = 1.229 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1735 reflections
a = 5.7785 (6) Åθ = 2.5–25.3°
b = 14.581 (2) ŵ = 0.08 mm1
c = 16.226 (2) ÅT = 293 K
β = 94.285 (1)°Block, yellow
V = 1363.4 (2) Å30.45 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker SMART
diffractometer
2396 independent reflections
Radiation source: fine-focus sealed tube1480 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.966, Tmax = 0.992k = 1714
6860 measured reflectionsl = 1819
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0748P)2]
where P = (Fo2 + 2Fc2)/3
2396 reflections(Δ/σ)max = 0.001
178 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.17 e Å3
Crystal data top
C16H16N2OV = 1363.4 (2) Å3
Mr = 252.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.7785 (6) ŵ = 0.08 mm1
b = 14.581 (2) ÅT = 293 K
c = 16.226 (2) Å0.45 × 0.15 × 0.10 mm
β = 94.285 (1)°
Data collection top
Bruker SMART
diffractometer
2396 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1480 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.992Rint = 0.054
6860 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0471 restraint
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.15 e Å3
2396 reflectionsΔρmin = 0.17 e Å3
178 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7517 (3)0.26556 (12)0.05236 (8)0.0674 (5)
H10.861 (4)0.2274 (16)0.0445 (16)0.107 (11)*
N10.7670 (3)0.27459 (12)0.13916 (9)0.0529 (5)
N20.6350 (3)0.35564 (11)0.51824 (10)0.0512 (5)
C10.4032 (4)0.36066 (17)0.11219 (13)0.0710 (7)
H1A0.43130.35130.05520.106*
H1B0.39340.42520.12310.106*
H1C0.25990.33160.12360.106*
C20.5974 (4)0.32006 (13)0.16606 (11)0.0457 (5)
C30.6050 (3)0.32942 (12)0.25745 (11)0.0419 (5)
C40.4248 (4)0.36780 (14)0.29717 (12)0.0515 (5)
H40.29430.38900.26590.062*
C50.4343 (4)0.37537 (14)0.38259 (12)0.0531 (6)
H50.30910.40010.40780.064*
C60.6290 (4)0.34636 (13)0.43064 (11)0.0451 (5)
C70.8106 (4)0.30705 (14)0.39156 (11)0.0508 (5)
H70.94150.28610.42280.061*
C80.7974 (4)0.29896 (13)0.30692 (12)0.0506 (5)
H80.92060.27240.28190.061*
C90.8175 (4)0.39055 (13)0.55448 (12)0.0502 (5)
H90.93160.41040.52110.060*
C100.8639 (4)0.40224 (12)0.64333 (12)0.0470 (5)
C110.7108 (4)0.37421 (14)0.70052 (12)0.0554 (6)
H110.56940.34810.68230.066*
C120.7675 (4)0.38494 (14)0.78433 (12)0.0605 (6)
H120.66300.36580.82170.073*
C130.9766 (4)0.42353 (14)0.81375 (13)0.0555 (6)
C141.1268 (4)0.45209 (14)0.75684 (13)0.0624 (6)
H141.26770.47860.77520.075*
C151.0720 (4)0.44209 (14)0.67304 (13)0.0593 (6)
H151.17590.46230.63590.071*
C161.0399 (5)0.43398 (18)0.90515 (13)0.0821 (8)
H16A1.17100.39580.92100.123*
H16B0.91060.41600.93540.123*
H16C1.07830.49680.91730.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0689 (12)0.0968 (13)0.0364 (9)0.0112 (10)0.0044 (7)0.0072 (8)
N10.0546 (12)0.0723 (12)0.0319 (9)0.0032 (9)0.0043 (8)0.0032 (8)
N20.0532 (11)0.0621 (11)0.0388 (10)0.0012 (9)0.0078 (8)0.0002 (8)
C10.0772 (18)0.0874 (17)0.0466 (13)0.0216 (14)0.0075 (12)0.0056 (11)
C20.0468 (13)0.0492 (12)0.0411 (11)0.0013 (10)0.0027 (9)0.0008 (9)
C30.0436 (12)0.0441 (11)0.0383 (10)0.0009 (9)0.0034 (9)0.0033 (8)
C40.0461 (13)0.0631 (13)0.0449 (12)0.0082 (10)0.0015 (10)0.0029 (9)
C50.0472 (13)0.0670 (14)0.0462 (12)0.0069 (11)0.0110 (10)0.0012 (9)
C60.0503 (13)0.0503 (11)0.0356 (11)0.0028 (9)0.0078 (9)0.0025 (8)
C70.0469 (13)0.0632 (13)0.0422 (12)0.0074 (10)0.0016 (10)0.0018 (9)
C80.0481 (13)0.0610 (13)0.0430 (12)0.0088 (10)0.0065 (10)0.0019 (9)
C90.0543 (14)0.0529 (12)0.0447 (12)0.0008 (10)0.0122 (10)0.0012 (9)
C100.0556 (14)0.0451 (11)0.0406 (11)0.0013 (10)0.0050 (10)0.0027 (8)
C110.0566 (14)0.0648 (13)0.0448 (12)0.0067 (11)0.0048 (10)0.0059 (10)
C120.0717 (16)0.0685 (15)0.0419 (12)0.0052 (12)0.0078 (11)0.0055 (10)
C130.0699 (16)0.0499 (12)0.0459 (12)0.0042 (11)0.0017 (11)0.0061 (9)
C140.0628 (16)0.0594 (13)0.0629 (15)0.0095 (11)0.0096 (12)0.0083 (11)
C150.0609 (15)0.0594 (14)0.0582 (14)0.0098 (11)0.0084 (12)0.0013 (10)
C160.101 (2)0.0889 (18)0.0538 (15)0.0072 (15)0.0125 (14)0.0117 (12)
Geometric parameters (Å, º) top
O1—N11.4107 (19)C7—H70.9300
O1—H10.860 (10)C8—H80.9300
N1—C21.286 (2)C9—C101.457 (3)
N2—C91.275 (2)C9—H90.9300
N2—C61.426 (2)C10—C151.389 (3)
C1—C21.492 (3)C10—C111.390 (3)
C1—H1A0.9600C11—C121.384 (3)
C1—H1B0.9600C11—H110.9300
C1—H1C0.9600C12—C131.385 (3)
C2—C31.487 (2)C12—H120.9300
C3—C41.383 (3)C13—C141.378 (3)
C3—C81.394 (3)C13—C161.509 (3)
C4—C51.387 (3)C14—C151.381 (3)
C4—H40.9300C14—H140.9300
C5—C61.386 (3)C15—H150.9300
C5—H50.9300C16—H16A0.9600
C6—C71.389 (3)C16—H16B0.9600
C7—C81.375 (3)C16—H16C0.9600
N1—O1—H1102.5 (18)C3—C8—H8119.0
C2—N1—O1113.22 (16)N2—C9—C10126.0 (2)
C9—N2—C6117.10 (18)N2—C9—H9117.0
C2—C1—H1A109.5C10—C9—H9117.0
C2—C1—H1B109.5C15—C10—C11117.95 (19)
H1A—C1—H1B109.5C15—C10—C9118.88 (19)
C2—C1—H1C109.5C11—C10—C9123.16 (19)
H1A—C1—H1C109.5C12—C11—C10120.5 (2)
H1B—C1—H1C109.5C12—C11—H11119.8
N1—C2—C3114.78 (17)C10—C11—H11119.8
N1—C2—C1124.35 (18)C11—C12—C13121.4 (2)
C3—C2—C1120.87 (19)C11—C12—H12119.3
C4—C3—C8117.15 (17)C13—C12—H12119.3
C4—C3—C2122.31 (17)C14—C13—C12118.0 (2)
C8—C3—C2120.54 (18)C14—C13—C16120.6 (2)
C3—C4—C5121.51 (18)C12—C13—C16121.4 (2)
C3—C4—H4119.2C13—C14—C15121.2 (2)
C5—C4—H4119.2C13—C14—H14119.4
C6—C5—C4120.5 (2)C15—C14—H14119.4
C6—C5—H5119.8C14—C15—C10121.0 (2)
C4—C5—H5119.8C14—C15—H15119.5
C5—C6—C7118.56 (18)C10—C15—H15119.5
C5—C6—N2119.34 (18)C13—C16—H16A109.5
C7—C6—N2122.08 (18)C13—C16—H16B109.5
C8—C7—C6120.26 (19)H16A—C16—H16B109.5
C8—C7—H7119.9C13—C16—H16C109.5
C6—C7—H7119.9H16A—C16—H16C109.5
C7—C8—C3122.00 (19)H16B—C16—H16C109.5
C7—C8—H8119.0
O1—N1—C2—C3178.84 (15)C4—C3—C8—C70.6 (3)
O1—N1—C2—C10.6 (3)C2—C3—C8—C7179.64 (18)
N1—C2—C3—C4173.15 (18)C6—N2—C9—C10176.97 (17)
C1—C2—C3—C46.3 (3)N2—C9—C10—C15179.7 (2)
N1—C2—C3—C86.6 (3)N2—C9—C10—C111.2 (3)
C1—C2—C3—C8173.93 (19)C15—C10—C11—C120.9 (3)
C8—C3—C4—C50.3 (3)C9—C10—C11—C12178.23 (18)
C2—C3—C4—C5179.52 (18)C10—C11—C12—C130.0 (3)
C3—C4—C5—C61.6 (3)C11—C12—C13—C140.7 (3)
C4—C5—C6—C72.0 (3)C11—C12—C13—C16179.1 (2)
C4—C5—C6—N2179.47 (18)C12—C13—C14—C150.4 (3)
C9—N2—C6—C5132.4 (2)C16—C13—C14—C15179.4 (2)
C9—N2—C6—C749.1 (3)C13—C14—C15—C100.5 (3)
C5—C6—C7—C81.2 (3)C11—C10—C15—C141.1 (3)
N2—C6—C7—C8179.67 (18)C9—C10—C15—C14178.03 (18)
C6—C7—C8—C30.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.86 (1)2.06 (1)2.919 (2)175 (3)
Symmetry code: (i) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H16N2O
Mr252.31
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)5.7785 (6), 14.581 (2), 16.226 (2)
β (°) 94.285 (1)
V3)1363.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.45 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.966, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
6860, 2396, 1480
Rint0.054
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.136, 0.95
No. of reflections2396
No. of parameters178
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.17

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.86 (1)2.06 (1)2.919 (2)175 (3)
Symmetry code: (i) x+1/2, y+1/2, z1/2.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDong, W.-K., Duan, J.-G., Guan, Y.-H., Shi, J.-Y. & Zhao, C.-Y. (2009c). Inorg. Chim. Acta, 362, 1129–1134.  Web of Science CSD CrossRef CAS Google Scholar
First citationDong, W.-K., Lv, Z.-W., Sun, Y.-X., Xu, L., Wang, L. & Dong, X.-Y. (2009a). Chin. J. Inorg. Chem. 25, 1627–1634.  CAS Google Scholar
First citationDong, W.-K., Sun, Y.-X., Zhang, Y.-P., Li, L., He, X.-N. & Tang, X.-L. (2009b). Inorg. Chim. Acta, 362, 117–124.  Web of Science CSD CrossRef CAS Google Scholar
First citationRafiq, M., Hanif, M., Qadeer, G., Vuoti, S. & Autio, J. (2008). Acta Cryst. E64, o2173.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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