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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o547.
Published online 2009 February 18. doi:  10.1107/S1600536809004784
PMCID: PMC2968664

2-[(4-Ethyl­phen­yl)imino­meth­yl]-3,5-dimethoxy­phenol

Abstract

The title compound, C17H19NO3, adopts the phenol–imine tautomeric form, with a resonance-assisted O—H(...)N intra­molecular hydrogen bond [O(...)N = 2.551 (3) Å]. The dihedral angle between the two benzene rings is 45.42 (7)°. The two meth­oxy groups are coplanar with the attached benzene ring [C—O—C—C torsion angles = −1.1 (5) and 3.2 (4)°].

Related literature

For the photochromic and thermochromic characteristics of Schiff base compounds, see: Hadjoudis et al. (1987 [triangle]); Lozier et al. (1975 [triangle]). For the notation of hydrogen-bonding motifs, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-0o547-scheme1.jpg

Experimental

Crystal data

  • C17H19NO3
  • M r = 285.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o547-efi1.jpg
  • a = 7.5026 (5) Å
  • b = 9.4540 (8) Å
  • c = 21.4408 (13) Å
  • V = 1520.79 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.46 × 0.35 × 0.11 mm

Data collection

  • Stoe IPDS II diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.991, T max = 0.998
  • 10094 measured reflections
  • 1831 independent reflections
  • 1036 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.077
  • S = 0.92
  • 1831 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.09 e Å−3
  • Δρmin = −0.11 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004784/ci2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004784/ci2762Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

supplementary crystallographic information

Comment

Most Schiff base compounds have antibacterial, anticancer, anti-inflammatory and antioxic properties. In addition Schiff bases are important in diverse fields of chemistry and biochemistry owing to their biological activites (Lozier et al., 1975). There are two types of intramolecular hydrogen bonds in Schiff bases which may stabilize them in keto–amine (N—H···O hydrogen bond) or phenol–imine (N···H—O hydrogen bond) tautomeric forms (Hadjoudis et al., 1987). Our investigations show that the title compound adopts the phenol–imine tautomeric form (Fig. 1).

The N1—C7 bond length of 1.281 (3) Å is typical of a double bond. The dihedral angle between the C1–C6 and C8–C13 benzene rings is 45.4 (2)°. The C4—C7—N1—C8 torsion angle is -179.5 (3)°. The strong intramolecular O3—H3···N1 hydrogen bond forms an S(6) motif (Bernstein et al., 1995).

Experimental

2-Hydroxy-4,6-dimethoxybenzaldehyde (0.0327 g, 0.18 mmol) in ethanol (20 ml) was added to a solution of 4-ethylaniline (0.0219 g, 0.18 mmol) in ethanol (20 ml) and the reaction mixture was stirred for 1 h under reflux, to obtain the title compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 61%; m.p.351–353 K).

Refinement

All H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å, O—H = 0.82 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl,O). In the absence of significant anomalous dispersion effects, Friedel pairs were merged before the final refinement.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability.

Crystal data

C17H19NO3F(000) = 608
Mr = 285.33Dx = 1.246 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 10094 reflections
a = 7.5026 (5) Åθ = 1.9–27.7°
b = 9.4540 (8) ŵ = 0.09 mm1
c = 21.4408 (13) ÅT = 296 K
V = 1520.79 (19) Å3Prism, yellow
Z = 40.46 × 0.35 × 0.11 mm

Data collection

Stoe IPDS II diffractometer1831 independent reflections
Radiation source: fine-focus sealed tube1036 reflections with I > 2σ(I)
graphiteRint = 0.049
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 1.9°
ω scansh = −9→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −11→10
Tmin = 0.991, Tmax = 0.998l = −26→26
10094 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: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 0.92w = 1/[σ2(Fo2) + (0.0332P)2] where P = (Fo2 + 2Fc2)/3
1831 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.09 e Å3
0 restraintsΔρmin = −0.11 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
C10.2906 (4)0.3417 (3)0.70797 (12)0.0630 (8)
C20.2290 (5)0.3445 (3)0.76807 (12)0.0692 (9)
H20.19880.42950.78710.083*
C30.2128 (4)0.2174 (3)0.79972 (12)0.0635 (8)
C40.2526 (4)0.0871 (3)0.77182 (11)0.0566 (7)
C50.3141 (4)0.0911 (3)0.70914 (12)0.0610 (8)
C60.3354 (4)0.2165 (3)0.67808 (12)0.0630 (8)
H60.37940.21780.63750.076*
C70.2409 (4)−0.0436 (3)0.80628 (12)0.0601 (7)
H70.2663−0.12840.78620.072*
C80.1874 (4)−0.1759 (3)0.89708 (11)0.0559 (7)
C90.2513 (4)−0.1775 (3)0.95769 (12)0.0679 (8)
H90.2991−0.09560.97490.081*
C100.2447 (5)−0.3000 (3)0.99269 (12)0.0699 (8)
H100.2930−0.30041.03260.084*
C110.1679 (4)−0.4216 (3)0.96967 (12)0.0625 (8)
C120.1013 (4)−0.4181 (3)0.90983 (12)0.0634 (8)
H120.0481−0.49880.89340.076*
C130.1118 (4)−0.2971 (3)0.87352 (11)0.0604 (8)
H130.0675−0.29800.83300.072*
C140.2705 (5)0.5932 (3)0.69842 (14)0.0878 (10)
H14A0.29390.66630.66850.132*
H14B0.34120.60910.73500.132*
H14C0.14640.59440.70940.132*
C150.4190 (5)−0.0439 (4)0.62229 (12)0.0884 (11)
H15A0.4361−0.14070.61020.133*
H15B0.53110.00490.62120.133*
H15C0.33720.00070.59400.133*
C160.1567 (5)−0.5544 (3)1.00901 (14)0.0857 (10)
H16A0.1075−0.52991.04940.103*
H16B0.0747−0.61980.98920.103*
C170.3298 (6)−0.6273 (4)1.01865 (17)0.1268 (16)
H17A0.3789−0.65380.97900.190*
H17B0.3116−0.71051.04350.190*
H17C0.4108−0.56481.03970.190*
N10.1964 (3)−0.0451 (2)0.86397 (10)0.0629 (7)
O10.3148 (3)0.4591 (2)0.67216 (8)0.0834 (7)
O20.3479 (3)−0.0388 (2)0.68417 (8)0.0781 (6)
O30.1587 (4)0.2229 (2)0.85970 (8)0.0879 (7)
H30.15260.14250.87380.132*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.063 (2)0.060 (2)0.0665 (18)−0.0127 (18)−0.0040 (17)0.0093 (15)
C20.082 (2)0.0589 (19)0.0672 (18)−0.0111 (18)0.0035 (17)−0.0034 (15)
C30.070 (2)0.0659 (18)0.0548 (15)−0.0106 (19)0.0023 (15)−0.0011 (15)
C40.0569 (19)0.0566 (18)0.0563 (15)−0.0072 (17)−0.0013 (14)0.0015 (14)
C50.059 (2)0.0607 (19)0.0630 (17)0.0015 (17)−0.0005 (14)−0.0030 (15)
C60.062 (2)0.0680 (19)0.0586 (15)−0.0035 (19)0.0001 (14)0.0062 (16)
C70.0531 (18)0.0607 (18)0.0665 (17)0.0020 (17)0.0004 (15)0.0003 (14)
C80.0524 (19)0.062 (2)0.0534 (15)0.0002 (17)0.0044 (14)0.0009 (14)
C90.074 (2)0.067 (2)0.0621 (16)−0.0129 (18)−0.0080 (16)−0.0051 (15)
C100.075 (2)0.078 (2)0.0569 (15)−0.0050 (19)−0.0071 (15)0.0078 (16)
C110.061 (2)0.062 (2)0.0642 (17)0.0031 (18)0.0066 (14)0.0035 (15)
C120.067 (2)0.0563 (19)0.0664 (18)−0.0047 (17)0.0065 (16)−0.0045 (15)
C130.059 (2)0.068 (2)0.0541 (15)−0.0018 (17)0.0005 (14)−0.0004 (16)
C140.104 (3)0.062 (2)0.097 (2)−0.006 (2)−0.009 (2)0.0148 (18)
C150.110 (3)0.092 (2)0.0636 (18)0.001 (2)0.0264 (18)−0.0078 (17)
C160.100 (3)0.076 (2)0.081 (2)0.003 (2)0.0076 (19)0.0194 (18)
C170.125 (4)0.119 (3)0.137 (3)0.047 (3)0.038 (3)0.058 (3)
N10.0689 (18)0.0643 (15)0.0554 (14)−0.0059 (15)0.0017 (12)0.0050 (11)
O10.1059 (19)0.0655 (13)0.0788 (14)−0.0060 (14)0.0029 (12)0.0146 (12)
O20.0968 (17)0.0701 (14)0.0674 (12)0.0057 (13)0.0197 (12)0.0004 (11)
O30.136 (2)0.0651 (13)0.0621 (11)−0.0094 (16)0.0212 (12)−0.0037 (9)

Geometric parameters (Å, °)

C1—O11.362 (3)C11—C121.377 (3)
C1—C21.369 (3)C11—C161.515 (4)
C1—C61.387 (4)C12—C131.386 (4)
C2—C31.385 (4)C12—H120.93
C2—H20.93C13—H130.93
C3—O31.350 (3)C14—O11.426 (3)
C3—C41.401 (3)C14—H14A0.96
C4—C51.421 (3)C14—H14B0.96
C4—C71.442 (3)C14—H14C0.96
C5—O21.364 (3)C15—O21.430 (3)
C5—C61.370 (4)C15—H15A0.96
C6—H60.93C15—H15B0.96
C7—N11.281 (3)C15—H15C0.96
C7—H70.93C16—C171.485 (5)
C8—C131.375 (4)C16—H16A0.97
C8—C91.385 (3)C16—H16B0.97
C8—N11.428 (3)C17—H17A0.96
C9—C101.381 (4)C17—H17B0.96
C9—H90.93C17—H17C0.96
C10—C111.377 (4)O3—H30.82
C10—H100.93
O1—C1—C2124.0 (3)C11—C12—H12119.2
O1—C1—C6113.7 (2)C13—C12—H12119.2
C2—C1—C6122.2 (3)C8—C13—C12120.3 (2)
C1—C2—C3118.3 (3)C8—C13—H13119.8
C1—C2—H2120.9C12—C13—H13119.8
C3—C2—H2120.9O1—C14—H14A109.5
O3—C3—C2117.4 (3)O1—C14—H14B109.5
O3—C3—C4120.3 (3)H14A—C14—H14B109.5
C2—C3—C4122.3 (2)O1—C14—H14C109.5
C3—C4—C5116.7 (3)H14A—C14—H14C109.5
C3—C4—C7121.4 (2)H14B—C14—H14C109.5
C5—C4—C7121.8 (3)O2—C15—H15A109.5
O2—C5—C6124.5 (2)O2—C15—H15B109.5
O2—C5—C4114.1 (2)H15A—C15—H15B109.5
C6—C5—C4121.4 (3)O2—C15—H15C109.5
C5—C6—C1119.0 (3)H15A—C15—H15C109.5
C5—C6—H6120.5H15B—C15—H15C109.5
C1—C6—H6120.5C17—C16—C11114.4 (3)
N1—C7—C4121.3 (3)C17—C16—H16A108.7
N1—C7—H7119.3C11—C16—H16A108.7
C4—C7—H7119.3C17—C16—H16B108.7
C13—C8—C9118.6 (3)C11—C16—H16B108.7
C13—C8—N1124.0 (2)H16A—C16—H16B107.6
C9—C8—N1117.3 (3)C16—C17—H17A109.5
C10—C9—C8120.4 (3)C16—C17—H17B109.5
C10—C9—H9119.8H17A—C17—H17B109.5
C8—C9—H9119.8C16—C17—H17C109.5
C11—C10—C9121.4 (3)H17A—C17—H17C109.5
C11—C10—H10119.3H17B—C17—H17C109.5
C9—C10—H10119.3C7—N1—C8120.1 (2)
C10—C11—C12117.8 (3)C1—O1—C14118.1 (2)
C10—C11—C16121.0 (3)C5—O2—C15117.6 (2)
C12—C11—C16121.2 (3)C3—O3—H3109.5
C11—C12—C13121.5 (3)
O1—C1—C2—C3−179.1 (3)N1—C8—C9—C10179.2 (3)
C6—C1—C2—C30.5 (5)C8—C9—C10—C11−2.9 (5)
C1—C2—C3—O3177.4 (3)C9—C10—C11—C121.5 (5)
C1—C2—C3—C4−1.8 (5)C9—C10—C11—C16−178.3 (3)
O3—C3—C4—C5−178.1 (3)C10—C11—C12—C130.4 (4)
C2—C3—C4—C51.1 (4)C16—C11—C12—C13−179.7 (3)
O3—C3—C4—C7−1.4 (4)C9—C8—C13—C12−0.4 (4)
C2—C3—C4—C7177.8 (3)N1—C8—C13—C12−177.1 (3)
C3—C4—C5—O2−179.0 (3)C11—C12—C13—C8−1.0 (4)
C7—C4—C5—O24.3 (4)C10—C11—C16—C17−71.9 (4)
C3—C4—C5—C60.8 (4)C12—C11—C16—C17108.2 (4)
C7—C4—C5—C6−175.8 (3)C4—C7—N1—C8−179.5 (3)
O2—C5—C6—C1177.8 (3)C13—C8—N1—C7−43.7 (4)
C4—C5—C6—C1−2.1 (4)C9—C8—N1—C7139.6 (3)
O1—C1—C6—C5−179.0 (3)C2—C1—O1—C14−1.1 (5)
C2—C1—C6—C51.4 (5)C6—C1—O1—C14179.3 (3)
C3—C4—C7—N1−1.1 (4)C6—C5—O2—C153.2 (4)
C5—C4—C7—N1175.4 (3)C4—C5—O2—C15−176.9 (3)
C13—C8—C9—C102.3 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N10.821.822.551 (3)149

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2762).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Hadjoudis, E., Vitterakis, M., Moustakali, I. & Mavridis, I. (1987). Tetrahedron, 43, 1345–1360.
  • Lozier, R., Bogomolni, R. A. & Stoekenius, W. (1975). Biophys. J.15, 955–962. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (2002). X-RED and X-AREA Stoe & Cie, Darmstadt, Germany.

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