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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o92.
Published online 2007 December 6. doi:  10.1107/S1600536807058618
PMCID: PMC2915047

(E)-4-Bromo-2-[(4-ethyl­phen­yl)imino­meth­yl]phenol

Abstract

In the title compound, C15H14BrNO, the dihedral angle between the two benzene rings is 43.99 (2)°. The mol­ecular conformation is influenced by an intra­molecular O—H(...)N hydrogen bond.

Related literature

For related literature, see: Akkaya et al. (2007 [triangle]); Atalay et al. (2005 [triangle], 2006 [triangle]); Calligaris & Randaccio (1987 [triangle]).

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Object name is e-64-00o92-scheme1.jpg

Experimental

Crystal data

  • C15H14BrNO
  • M r = 304.18
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o92-efi1.jpg
  • a = 6.2280 (6) Å
  • b = 7.0292 (7) Å
  • c = 30.237 (4) Å
  • V = 1323.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.09 mm−1
  • T = 293 (2) K
  • 0.48 × 0.31 × 0.05 mm

Data collection

  • Stoe IPDS 2 diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.521, T max = 0.809
  • 7324 measured reflections
  • 1318 independent reflections
  • 819 reflections with I > 2σ(I)
  • R int = 0.102

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.109
  • S = 0.92
  • 1318 reflections
  • 165 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.41 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 1231 Friedel pairs
  • Flack parameter: 0.10 (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, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PARST (Nardelli, 1995 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807058618/wn2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807058618/wn2219Isup2.hkl

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

Acknowledgments

The authors thank the Turkish Goverment and the University of Ondokuz Mayıs for research grant F443.

supplementary crystallographic information

Comment

Schiff bases exhibit biological activity and they are widely used as ligands in metal complexes (Calligaris & Randaccio 1987).

In the title compound the dihedral angle between the benzene rings rings is 43.99 (2)°. The N?C and N—C bond lengths, 1.264 (10) Å and 1.417 (10) Å, respectively, agree with literature values (Akkaya et al., 2007; Atalay et al., 2006). The Br1—C4 and C1—O1 bond lengths are 1.878 (9) Å and 1.371 (12) Å, respectively, in good agreement with the literature (Atalay et al., 2005). The molecular conformation is influenced by an O—H···N hydrogen bond (Table 1, Fig. 1).

Experimental

The title compound, (E)-2-[(4-ethylphenylimino)methyl]-4-bromophenol, was prepared by refluxing a mixture of a solution containing 5-bromosalicylaldehyde (0.05 ml, 0.25 mmol) in 20 ml e thanol and a solution containing 4-ethylaniline (0.03 g, 0.25 mmol) in 20 ml e thanol. The reaction mixture was stirred for 1 h under reflux. Crystals of the title compound suitable for X-ray analysis were obtained from an acetonitrile solution by slow evaporation (yield 84%; m.p. 385–386 K).

Refinement

All H atoms were placed in calculated positions and refined using a riding model, with aromatic C—H = 0.93 Å for Csp2, 0.97 Å for methylene and 0.96 Å for methyl; O—H = 0.82 Å. Uiso(H) = xUeq(carrier atom), where x = 1.5 for O and 1.2 for all C atoms. The value of Rint is rather high because of the poor data quality.

Figures

Fig. 1.
The molecular structure of the title compound, with the atom-numbering scheme and 50% probability displacement ellipsoids. The hydrogen bond is shown as a double-dashed line.

Crystal data

C15H14BrNODx = 1.526 Mg m3
Mr = 304.18Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 9683 reflections
a = 6.2280 (6) Åθ = 1.4–26.1º
b = 7.0292 (7) ŵ = 3.09 mm1
c = 30.237 (4) ÅT = 293 (2) K
V = 1323.7 (3) Å3Plate, yellow
Z = 40.48 × 0.31 × 0.05 mm
F000 = 616

Data collection

STOE IPDS 2 diffractometer1318 independent reflections
Radiation source: fine-focus sealed tube819 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.102
Detector resolution: 6.67 pixels mm-1θmax = 26.0º
T = 293(2) Kθmin = 1.4º
w scansh = −7→7
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)k = −8→8
Tmin = 0.521, Tmax = 0.809l = −36→36
7324 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041  w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109(Δ/σ)max < 0.001
S = 0.92Δρmax = 0.41 e Å3
1318 reflectionsΔρmin = −0.41 e Å3
165 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0011 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1231 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.10 (3)

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
C70.6103 (14)0.4481 (11)0.6165 (3)0.0602 (19)
H70.75420.41320.61520.072*
C50.6251 (12)0.4361 (11)0.6979 (3)0.0562 (18)
H50.76520.39070.69640.067*
C30.3255 (13)0.5382 (12)0.7420 (3)0.063 (2)
H30.26630.56280.76970.076*
C120.9101 (13)0.5783 (11)0.4937 (3)0.063 (2)
H121.04550.63230.49040.075*
C10.2969 (13)0.5335 (10)0.6631 (3)0.0576 (18)
C40.5322 (13)0.4707 (12)0.7385 (3)0.0582 (19)
C110.8254 (11)0.5622 (12)0.5348 (3)0.0578 (19)
H110.90240.60240.55940.069*
C60.5101 (12)0.4686 (10)0.6591 (2)0.0512 (16)
C90.5119 (15)0.4235 (12)0.5023 (3)0.061 (2)
H90.37410.37370.50480.073*
C80.6088 (16)0.4367 (13)0.4610 (3)0.066 (2)
H80.53800.38890.43630.079*
C130.8010 (18)0.5166 (17)0.4562 (4)0.067 (3)
C140.9191 (18)0.5424 (16)0.4110 (4)0.092 (3)
H14A0.93040.67750.40490.111*
H14B1.06390.49320.41400.111*
C20.2089 (15)0.5685 (12)0.7048 (5)0.057 (3)
H20.06880.61310.70700.069*
C100.6197 (12)0.4841 (10)0.5396 (2)0.0523 (18)
C150.819 (3)0.451 (3)0.3735 (8)0.141 (9)
H15A0.81260.31640.37840.169*
H15B0.90210.47630.34730.169*
H15C0.67650.50020.36970.169*
N10.5106 (11)0.4758 (10)0.5806 (2)0.0553 (18)
O10.1708 (9)0.5649 (9)0.6266 (3)0.067 (2)
H10.23890.53950.60420.100*
Br10.70006 (13)0.43768 (13)0.78954 (7)0.0838 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C70.063 (4)0.051 (5)0.067 (5)−0.009 (4)0.004 (4)−0.001 (4)
C50.047 (4)0.051 (5)0.070 (5)−0.007 (3)−0.004 (4)0.003 (4)
C30.054 (5)0.063 (5)0.073 (5)0.001 (4)0.013 (4)0.002 (4)
C120.056 (4)0.048 (5)0.084 (6)−0.005 (4)0.003 (4)0.004 (4)
C10.057 (4)0.049 (4)0.067 (4)−0.002 (4)−0.005 (4)−0.002 (4)
C40.054 (4)0.045 (5)0.076 (5)−0.007 (3)−0.007 (4)−0.001 (4)
C110.051 (5)0.054 (5)0.069 (5)−0.005 (4)−0.010 (4)0.003 (4)
C60.044 (4)0.052 (4)0.058 (4)0.001 (3)0.001 (3)0.001 (4)
C90.050 (5)0.057 (6)0.075 (5)0.000 (4)−0.004 (4)−0.008 (4)
C80.071 (5)0.061 (6)0.066 (5)−0.007 (5)−0.008 (4)−0.007 (4)
C130.073 (6)0.061 (6)0.066 (6)0.009 (5)0.005 (5)−0.001 (5)
C140.090 (7)0.102 (8)0.086 (6)−0.015 (6)0.017 (6)−0.001 (7)
C20.053 (5)0.049 (5)0.070 (7)0.002 (4)0.001 (5)0.001 (5)
C100.050 (4)0.044 (5)0.063 (4)0.008 (3)−0.002 (4)−0.004 (4)
C150.112 (13)0.22 (2)0.094 (15)−0.025 (11)0.020 (10)−0.015 (12)
N10.056 (4)0.054 (5)0.056 (4)0.004 (4)−0.003 (3)−0.003 (4)
O10.040 (3)0.089 (5)0.073 (4)0.009 (3)−0.005 (3)−0.002 (4)
Br10.0808 (5)0.1063 (7)0.0642 (4)0.0050 (5)−0.0098 (8)−0.0008 (10)

Geometric parameters (Å, °)

C7—N11.264 (10)C11—H110.9300
C7—C61.440 (11)C9—C101.378 (11)
C7—H70.9300C9—C81.391 (12)
C5—C41.379 (12)C9—H90.9300
C5—C61.394 (11)C8—C131.330 (14)
C5—H50.9300C8—H80.9300
C3—C21.357 (18)C13—C141.562 (15)
C3—C41.376 (12)C14—C151.45 (2)
C3—H30.9300C14—H14A0.9700
C12—C111.356 (11)C14—H14B0.9700
C12—C131.390 (14)C2—H20.9300
C12—H120.9300C10—N11.417 (10)
C1—O11.371 (12)C15—H15A0.9600
C1—C21.397 (17)C15—H15B0.9600
C1—C61.409 (10)C15—H15C0.9600
C4—Br11.878 (9)O1—H10.8200
C11—C101.401 (10)
N1—C7—C6122.6 (8)C13—C8—C9121.1 (8)
N1—C7—H7118.7C13—C8—H8119.4
C6—C7—H7118.7C9—C8—H8119.4
C4—C5—C6120.4 (7)C8—C13—C12118.8 (9)
C4—C5—H5119.8C8—C13—C14124.6 (10)
C6—C5—H5119.8C12—C13—C14116.5 (9)
C2—C3—C4119.4 (9)C15—C14—C13115.7 (11)
C2—C3—H3120.3C15—C14—H14A108.4
C4—C3—H3120.3C13—C14—H14A108.4
C11—C12—C13122.1 (8)C15—C14—H14B108.4
C11—C12—H12119.0C13—C14—H14B108.4
C13—C12—H12119.0H14A—C14—H14B107.4
O1—C1—C2118.2 (8)C3—C2—C1120.8 (8)
O1—C1—C6121.6 (7)C3—C2—H2119.6
C2—C1—C6120.2 (8)C1—C2—H2119.6
C3—C4—C5121.5 (8)C9—C10—C11118.9 (7)
C3—C4—Br1120.0 (7)C9—C10—N1118.0 (7)
C5—C4—Br1118.4 (6)C11—C10—N1123.0 (7)
C12—C11—C10118.8 (7)C14—C15—H15A109.5
C12—C11—H11120.6C14—C15—H15B109.5
C10—C11—H11120.6H15A—C15—H15B109.5
C5—C6—C1117.8 (7)C14—C15—H15C109.5
C5—C6—C7121.0 (7)H15A—C15—H15C109.5
C1—C6—C7121.1 (7)H15B—C15—H15C109.5
C10—C9—C8120.1 (8)C7—N1—C10121.5 (7)
C10—C9—H9119.9C1—O1—H1109.5
C8—C9—H9119.9
C2—C3—C4—C51.1 (12)C9—C8—C13—C14−178.3 (9)
C2—C3—C4—Br1177.4 (6)C11—C12—C13—C8−1.0 (15)
C6—C5—C4—C3−0.1 (12)C11—C12—C13—C14−179.5 (9)
C6—C5—C4—Br1−176.5 (6)C8—C13—C14—C15−7.7 (18)
C13—C12—C11—C10−1.2 (13)C12—C13—C14—C15170.7 (12)
C4—C5—C6—C1−1.3 (10)C4—C3—C2—C1−0.5 (13)
C4—C5—C6—C7174.8 (8)O1—C1—C2—C3179.3 (8)
O1—C1—C6—C5−178.5 (7)C6—C1—C2—C3−0.9 (13)
C2—C1—C6—C51.8 (11)C8—C9—C10—C111.3 (12)
O1—C1—C6—C75.4 (11)C8—C9—C10—N1177.2 (8)
C2—C1—C6—C7−174.3 (8)C12—C11—C10—C91.0 (11)
N1—C7—C6—C5179.7 (8)C12—C11—C10—N1−174.7 (7)
N1—C7—C6—C1−4.3 (12)C6—C7—N1—C10170.0 (7)
C10—C9—C8—C13−3.6 (14)C9—C10—N1—C7149.2 (8)
C9—C8—C13—C123.4 (15)C11—C10—N1—C7−35.1 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.892.609 (10)146

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2219).

References

  • Akkaya, A., Erşahin, F., Şenel, I., Ağar, E. & Büyükgüngör, O. (2007). Acta Cryst. E63, o2383–o2385.
  • Atalay, S., Ocak Ískeleli, N., Ağar, E. & Akdemir, N (2005). Acta Cryst. E61, o2654–o2655.
  • Atalay, Ş., Petek, H., Ocak Ískeleli, N., Albayrak, Ç. & Ağar, E. (2006). Acta Cryst. E62, o3092–o3093.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, edited by G. Wilkinson, pp. 715–738. London: Pergamon.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Nardelli, M. (1995). J. Appl. Cryst.28, 659.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Stoe & Cie (2002). X-AREA (Version 1.118) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.

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