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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2007 Dec 6;64(Pt 1):o92. doi: 10.1107/S1600536807058618

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

Şehriman Atalay a,*, Talip Kaya Erdem a, Ferda Erşahin b, Nihat Tınkılıç b
PMCID: PMC2915047  PMID: 21200969

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 ▶); Atalay et al. (2005 ▶, 2006 ▶); Calligaris & Randaccio (1987 ▶).graphic file with name e-64-00o92-scheme1.jpg

Experimental

Crystal data

  • C15H14BrNO

  • M r = 304.18

  • Orthorhombic, Inline graphic

  • 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 ▶) 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 ▶), with 1231 Friedel pairs

  • Flack parameter: 0.10 (3)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶).

Supplementary Material

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

e-64-00o92-sup1.cif (16.5KB, cif)

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

e-64-00o92-Isup2.hkl (63.8KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.82 1.89 2.609 (10) 146
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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.

Fig. 1.

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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

C15H14BrNO Dx = 1.526 Mg m−3
Mr = 304.18 Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pna21 Cell parameters from 9683 reflections
a = 6.2280 (6) Å θ = 1.4–26.1º
b = 7.0292 (7) Å µ = 3.09 mm−1
c = 30.237 (4) Å T = 293 (2) K
V = 1323.7 (3) Å3 Plate, yellow
Z = 4 0.48 × 0.31 × 0.05 mm
F000 = 616
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Data collection

STOE IPDS 2 diffractometer 1318 independent reflections
Radiation source: fine-focus sealed tube 819 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.102
Detector resolution: 6.67 pixels mm-1 θmax = 26.0º
T = 293(2) K θmin = 1.4º
w scans h = −7→7
Absorption correction: integration(X-RED32; Stoe & Cie, 2002) k = −8→8
Tmin = 0.521, Tmax = 0.809 l = −36→36
7324 measured reflections
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Refinement

Refinement on F2 Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full H-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 = 0.92 Δρmax = 0.41 e Å−3
1318 reflections Δρmin = −0.41 e Å−3
165 parameters Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint Extinction coefficient: 0.0011 (7)
Primary atom site location: structure-invariant direct methods Absolute structure: Flack (1983), 1231 Friedel pairs
Secondary atom site location: difference Fourier map Flack parameter: 0.10 (3)
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C7 0.6103 (14) 0.4481 (11) 0.6165 (3) 0.0602 (19)
H7 0.7542 0.4132 0.6152 0.072*
C5 0.6251 (12) 0.4361 (11) 0.6979 (3) 0.0562 (18)
H5 0.7652 0.3907 0.6964 0.067*
C3 0.3255 (13) 0.5382 (12) 0.7420 (3) 0.063 (2)
H3 0.2663 0.5628 0.7697 0.076*
C12 0.9101 (13) 0.5783 (11) 0.4937 (3) 0.063 (2)
H12 1.0455 0.6323 0.4904 0.075*
C1 0.2969 (13) 0.5335 (10) 0.6631 (3) 0.0576 (18)
C4 0.5322 (13) 0.4707 (12) 0.7385 (3) 0.0582 (19)
C11 0.8254 (11) 0.5622 (12) 0.5348 (3) 0.0578 (19)
H11 0.9024 0.6024 0.5594 0.069*
C6 0.5101 (12) 0.4686 (10) 0.6591 (2) 0.0512 (16)
C9 0.5119 (15) 0.4235 (12) 0.5023 (3) 0.061 (2)
H9 0.3741 0.3737 0.5048 0.073*
C8 0.6088 (16) 0.4367 (13) 0.4610 (3) 0.066 (2)
H8 0.5380 0.3889 0.4363 0.079*
C13 0.8010 (18) 0.5166 (17) 0.4562 (4) 0.067 (3)
C14 0.9191 (18) 0.5424 (16) 0.4110 (4) 0.092 (3)
H14A 0.9304 0.6775 0.4049 0.111*
H14B 1.0639 0.4932 0.4140 0.111*
C2 0.2089 (15) 0.5685 (12) 0.7048 (5) 0.057 (3)
H2 0.0688 0.6131 0.7070 0.069*
C10 0.6197 (12) 0.4841 (10) 0.5396 (2) 0.0523 (18)
C15 0.819 (3) 0.451 (3) 0.3735 (8) 0.141 (9)
H15A 0.8126 0.3164 0.3784 0.169*
H15B 0.9021 0.4763 0.3473 0.169*
H15C 0.6765 0.5002 0.3697 0.169*
N1 0.5106 (11) 0.4758 (10) 0.5806 (2) 0.0553 (18)
O1 0.1708 (9) 0.5649 (9) 0.6266 (3) 0.067 (2)
H1 0.2389 0.5395 0.6042 0.100*
Br1 0.70006 (13) 0.43768 (13) 0.78954 (7) 0.0838 (4)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C7 0.063 (4) 0.051 (5) 0.067 (5) −0.009 (4) 0.004 (4) −0.001 (4)
C5 0.047 (4) 0.051 (5) 0.070 (5) −0.007 (3) −0.004 (4) 0.003 (4)
C3 0.054 (5) 0.063 (5) 0.073 (5) 0.001 (4) 0.013 (4) 0.002 (4)
C12 0.056 (4) 0.048 (5) 0.084 (6) −0.005 (4) 0.003 (4) 0.004 (4)
C1 0.057 (4) 0.049 (4) 0.067 (4) −0.002 (4) −0.005 (4) −0.002 (4)
C4 0.054 (4) 0.045 (5) 0.076 (5) −0.007 (3) −0.007 (4) −0.001 (4)
C11 0.051 (5) 0.054 (5) 0.069 (5) −0.005 (4) −0.010 (4) 0.003 (4)
C6 0.044 (4) 0.052 (4) 0.058 (4) 0.001 (3) 0.001 (3) 0.001 (4)
C9 0.050 (5) 0.057 (6) 0.075 (5) 0.000 (4) −0.004 (4) −0.008 (4)
C8 0.071 (5) 0.061 (6) 0.066 (5) −0.007 (5) −0.008 (4) −0.007 (4)
C13 0.073 (6) 0.061 (6) 0.066 (6) 0.009 (5) 0.005 (5) −0.001 (5)
C14 0.090 (7) 0.102 (8) 0.086 (6) −0.015 (6) 0.017 (6) −0.001 (7)
C2 0.053 (5) 0.049 (5) 0.070 (7) 0.002 (4) 0.001 (5) 0.001 (5)
C10 0.050 (4) 0.044 (5) 0.063 (4) 0.008 (3) −0.002 (4) −0.004 (4)
C15 0.112 (13) 0.22 (2) 0.094 (15) −0.025 (11) 0.020 (10) −0.015 (12)
N1 0.056 (4) 0.054 (5) 0.056 (4) 0.004 (4) −0.003 (3) −0.003 (4)
O1 0.040 (3) 0.089 (5) 0.073 (4) 0.009 (3) −0.005 (3) −0.002 (4)
Br1 0.0808 (5) 0.1063 (7) 0.0642 (4) 0.0050 (5) −0.0098 (8) −0.0008 (10)
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Geometric parameters (Å, °)

C7—N1 1.264 (10) C11—H11 0.9300
C7—C6 1.440 (11) C9—C10 1.378 (11)
C7—H7 0.9300 C9—C8 1.391 (12)
C5—C4 1.379 (12) C9—H9 0.9300
C5—C6 1.394 (11) C8—C13 1.330 (14)
C5—H5 0.9300 C8—H8 0.9300
C3—C2 1.357 (18) C13—C14 1.562 (15)
C3—C4 1.376 (12) C14—C15 1.45 (2)
C3—H3 0.9300 C14—H14A 0.9700
C12—C11 1.356 (11) C14—H14B 0.9700
C12—C13 1.390 (14) C2—H2 0.9300
C12—H12 0.9300 C10—N1 1.417 (10)
C1—O1 1.371 (12) C15—H15A 0.9600
C1—C2 1.397 (17) C15—H15B 0.9600
C1—C6 1.409 (10) C15—H15C 0.9600
C4—Br1 1.878 (9) O1—H1 0.8200
C11—C10 1.401 (10)
N1—C7—C6 122.6 (8) C13—C8—C9 121.1 (8)
N1—C7—H7 118.7 C13—C8—H8 119.4
C6—C7—H7 118.7 C9—C8—H8 119.4
C4—C5—C6 120.4 (7) C8—C13—C12 118.8 (9)
C4—C5—H5 119.8 C8—C13—C14 124.6 (10)
C6—C5—H5 119.8 C12—C13—C14 116.5 (9)
C2—C3—C4 119.4 (9) C15—C14—C13 115.7 (11)
C2—C3—H3 120.3 C15—C14—H14A 108.4
C4—C3—H3 120.3 C13—C14—H14A 108.4
C11—C12—C13 122.1 (8) C15—C14—H14B 108.4
C11—C12—H12 119.0 C13—C14—H14B 108.4
C13—C12—H12 119.0 H14A—C14—H14B 107.4
O1—C1—C2 118.2 (8) C3—C2—C1 120.8 (8)
O1—C1—C6 121.6 (7) C3—C2—H2 119.6
C2—C1—C6 120.2 (8) C1—C2—H2 119.6
C3—C4—C5 121.5 (8) C9—C10—C11 118.9 (7)
C3—C4—Br1 120.0 (7) C9—C10—N1 118.0 (7)
C5—C4—Br1 118.4 (6) C11—C10—N1 123.0 (7)
C12—C11—C10 118.8 (7) C14—C15—H15A 109.5
C12—C11—H11 120.6 C14—C15—H15B 109.5
C10—C11—H11 120.6 H15A—C15—H15B 109.5
C5—C6—C1 117.8 (7) C14—C15—H15C 109.5
C5—C6—C7 121.0 (7) H15A—C15—H15C 109.5
C1—C6—C7 121.1 (7) H15B—C15—H15C 109.5
C10—C9—C8 120.1 (8) C7—N1—C10 121.5 (7)
C10—C9—H9 119.9 C1—O1—H1 109.5
C8—C9—H9 119.9
C2—C3—C4—C5 1.1 (12) C9—C8—C13—C14 −178.3 (9)
C2—C3—C4—Br1 177.4 (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—C15 170.7 (12)
C4—C5—C6—C1 −1.3 (10) C4—C3—C2—C1 −0.5 (13)
C4—C5—C6—C7 174.8 (8) O1—C1—C2—C3 179.3 (8)
O1—C1—C6—C5 −178.5 (7) C6—C1—C2—C3 −0.9 (13)
C2—C1—C6—C5 1.8 (11) C8—C9—C10—C11 1.3 (12)
O1—C1—C6—C7 5.4 (11) C8—C9—C10—N1 177.2 (8)
C2—C1—C6—C7 −174.3 (8) C12—C11—C10—C9 1.0 (11)
N1—C7—C6—C5 179.7 (8) C12—C11—C10—N1 −174.7 (7)
N1—C7—C6—C1 −4.3 (12) C6—C7—N1—C10 170.0 (7)
C10—C9—C8—C13 −3.6 (14) C9—C10—N1—C7 149.2 (8)
C9—C8—C13—C12 3.4 (15) C11—C10—N1—C7 −35.1 (12)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O1—H1···N1 0.82 1.89 2.609 (10) 146
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Footnotes

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

References

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

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-64-00o92-sup1.cif (16.5KB, cif)

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

e-64-00o92-Isup2.hkl (63.8KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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