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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o92
https://doi.org/10.1107/S1600536807058618

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

Şehriman Atalay,a* Talip Kaya Erdem,a Ferda Erşahinb and Nihat Tınkılıçb

aDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and bDepartment of Chemistry, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
*Correspondence e-mail: atalays@omu.edu.tr

(Received 5 November 2007; accepted 13 November 2007; online 6 December 2007)

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[Akkaya, A., Erşahin, F., Şenel, I., Ağar, E. & Büyükgüngör, O. (2007). Acta Cryst. E63, o2383-o2385.]); Atalay et al. (2005[Atalay, S., Ocak Ískeleli, N., Ağar, E. & Akdemir, N (2005). Acta Cryst. E61, o2654-o2655.], 2006[Atalay, Ş., Petek, H., Ocak Ískeleli, N., Albayrak, Ç. & Ağar, E. (2006). Acta Cryst. E62, o3092-o3093.]); Calligaris & Randaccio (1987[Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, edited by G. Wilkinson, pp. 715-738. London: Pergamon.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14BrNO

  • Mr = 304.18

  • Orthorhombic, P n a 21

  • 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[Stoe & Cie (2002). X-AREA (Version 1.118) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.521, Tmax = 0.809

  • 7324 measured reflections

  • 1318 independent reflections

  • 819 reflections with I > 2σ(I)

  • Rint = 0.102
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 1231 Friedel pairs

  • Flack parameter: 0.10 (3)

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

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.118) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA (Version 1.118) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807058618/wn2219Isup2.hkl

checkCIF report


Comment top

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).

Related literature top

For related literature, see: Atalay et al. (2005, 2006); Calligaris & Randaccio (1987).

For related literature, see: Akkaya et al. (2007).

Experimental top

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 top

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.

Structure description top

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).

For related literature, see: Atalay et al. (2005, 2006); Calligaris & Randaccio (1987).

For related literature, see: Akkaya et al. (2007).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

Figures top
[Figure 1] 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.
(E)-4-Bromo-2-[(4-ethylphenyl)iminomethyl]phenol top
Crystal data top
C15H14BrNODx = 1.526 Mg m−3
Mr = 304.18Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 9683 reflections
a = 6.2280 (6) Åθ = 1.4–26.1°
b = 7.0292 (7) ŵ = 3.09 mm−1
c = 30.237 (4) ÅT = 293 K
V = 1323.7 (3) Å3Plate, yellow
Z = 40.48 × 0.31 × 0.05 mm
F(000) = 616
Data collection top
STOE IPDS 2
diffractometer		1318 independent reflections
Radiation source: fine-focus sealed tube819 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.102
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.4°
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 top
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 Å−3
1318 reflectionsΔρmin = −0.41 e Å−3
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 mapAbsolute structure parameter: 0.10 (3)
Crystal data top
C15H14BrNOV = 1323.7 (3) Å3
Mr = 304.18Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 6.2280 (6) ŵ = 3.09 mm−1
b = 7.0292 (7) ÅT = 293 K
c = 30.237 (4) Å0.48 × 0.31 × 0.05 mm
Data collection top
STOE IPDS 2
diffractometer		1318 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		819 reflections with I > 2σ(I)
Tmin = 0.521, Tmax = 0.809Rint = 0.102
7324 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.41 e Å−3
S = 0.92Δρmin = −0.41 e Å−3
1318 reflectionsAbsolute structure: Flack (1983), 1231 Friedel pairs
165 parametersAbsolute structure parameter: 0.10 (3)
1 restraint
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.

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

Experimental details

Crystal data
Chemical formulaC15H14BrNO
Mr304.18
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)293
a, b, c (Å)6.2280 (6), 7.0292 (7), 30.237 (4)
V (Å3)1323.7 (3)
Z4
Radiation typeMo Kα
µ (mm−1)3.09
Crystal size (mm)0.48 × 0.31 × 0.05
Data collection
DiffractometerSTOE IPDS 2
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.521, 0.809
No. of measured, independent and
observed [I > 2σ(I)] reflections		7324, 1318, 819
Rint0.102
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.109, 0.92
No. of reflections1318
No. of parameters165
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.41
Absolute structureFlack (1983), 1231 Friedel pairs
Absolute structure parameter0.10 (3)

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-III (Burnett & Johnson, 1996), WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.892.609 (10)145.8
 

Acknowledgements

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

References

First citationAkkaya, A., Erşahin, F., Şenel, I., Ağar, E. & Büyükgüngör, O. (2007). Acta Cryst. E63, o2383–o2385.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationAtalay, S., Ocak Ískeleli, N., Ağar, E. & Akdemir, N (2005). Acta Cryst. E61, o2654–o2655.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationAtalay, Ş., Petek, H., Ocak Ískeleli, N., Albayrak, Ç. & Ağar, E. (2006). Acta Cryst. E62, o3092–o3093.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
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 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationNardelli, M. (1995). J. Appl. Cryst. 28, 659.  CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationStoe & Cie (2002). X-AREA (Version 1.118) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.  Google Scholar

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o92
https://doi.org/10.1107/S1600536807058618
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