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access4-Bromo-2-[(E)-(4-fluorophenyl)iminomethyl]phenol
aIslamic Azad University, Ardakan Branch, Iran, bX-ray Crystallography Laboratory, Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, cChemistry Department, Payame Noor University, Tehran 19395-4697, I. R. of Iran, and dDepartment of Physics, University of Sargodha, Punjab, Pakistan
*Correspondence e-mail: zsrkk@yahoo.com, rkia@srbiau.ac.ir, dmntahir_uos@yahoo.com
In the title compound, C13H9BrFNO, the dihedral angle between the substituted benzene rings is 9.00 (11)°. Strong intramolecular O—H⋯N hydrogen bonds generate S(6) ring motifs.
Related literature
For standard bond lengths, see: Allen et al. (1987![[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]](../../../../../../logos/arrows/e_arr.gif "Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.")
). For hydrogen-bond motifs, see: Bernstein et al. (1995).
![[Scheme 1]](jh2266scheme1.gif)
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536811004429/jh2266sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536811004429/jh2266Isup2.hkl
The title compound was synthesized by adding 5-bromo-salicylaldehyde (2 mmol) to a solution of p-fluoroaniline (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resulting light-yellow solution was filtered. Pale-yellow single crystals suitable for X-ray diffraction were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.
H atoms of the hydroxy groups were located by a rotating model and constrained to refine with the parent atoms with Uiso(H) = 1.5 Ueq(O), see Table 1. The remaining H atoms were positioned geometrically with C—H = 0.93 Å and included in a riding model approximation with Uiso (H) = 1.2 Ueq (C).
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
![[Figure 1]](./jh2266fig1thm.gif) | Fig. 1. The asymmetric unit of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bond is drawn as dashed lines. |
![[Figure 2]](./jh2266fig2thm.gif) | Fig. 2. The packing diagram of the title compound, viewed down the c-axis. |
| C13H9BrFNO | F(000) = 584 |
| Mr = 294.12 | Dx = 1.720 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 2520 reflections |
| a = 4.4820 (2) Å | θ = 2.5–28.5° |
| b = 20.8088 (9) Å | µ = 3.61 mm−1 |
| c = 12.2189 (5) Å | T = 296 K |
| β = 94.570 (2)° | Prism, pale-yellow |
| V = 1135.97 (8) Å3 | 0.35 × 0.17 × 0.11 mm |
| Z = 4 |
| Bruker SMART APEXII CCD area-detector diffractometer | 2792 independent reflections |
| Radiation source: fine-focus sealed tube | 1958 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.034 |
| ϕ and ω scans | θmax = 28.3°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −5→5 |
| Tmin = 0.365, Tmax = 0.692 | k = −27→27 |
| 10561 measured reflections | l = −16→16 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.083 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0413P)2 + 0.1115P] where P = (Fo2 + 2Fc2)/3 |
| 2792 reflections | (Δ/σ)max = 0.001 |
| 154 parameters | Δρmax = 0.44 e Å−3 |
| 0 restraints | Δρmin = −0.26 e Å−3 |
| C13H9BrFNO | V = 1135.97 (8) Å3 |
| Mr = 294.12 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 4.4820 (2) Å | µ = 3.61 mm−1 |
| b = 20.8088 (9) Å | T = 296 K |
| c = 12.2189 (5) Å | 0.35 × 0.17 × 0.11 mm |
| β = 94.570 (2)° |
| Bruker SMART APEXII CCD area-detector diffractometer | 2792 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1958 reflections with I > 2σ(I) |
| Tmin = 0.365, Tmax = 0.692 | Rint = 0.034 |
| 10561 measured reflections |
| R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
| wR(F2) = 0.083 | H-atom parameters constrained |
| S = 1.02 | Δρmax = 0.44 e Å−3 |
| 2792 reflections | Δρmin = −0.26 e Å−3 |
| 154 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
| x | y | z | Uiso*/Ueq | ||
| Br1 | 1.14491 (6) | 0.420695 (13) | 0.55664 (2) | 0.06007 (13) | |
| F1 | −0.3896 (4) | −0.01392 (7) | 0.62967 (14) | 0.0714 (5) | |
| O1 | 0.7822 (4) | 0.23124 (8) | 0.89264 (12) | 0.0502 (4) | |
| H1 | 0.6582 | 0.2057 | 0.8661 | 0.075* | |
| N1 | 0.4202 (4) | 0.17993 (8) | 0.73875 (14) | 0.0357 (4) | |
| C1 | 0.7310 (5) | 0.26970 (10) | 0.70681 (16) | 0.0322 (5) | |
| C2 | 0.8605 (5) | 0.27266 (11) | 0.81485 (16) | 0.0356 (5) | |
| C3 | 1.0742 (5) | 0.31885 (11) | 0.84342 (17) | 0.0415 (5) | |
| H3 | 1.1617 | 0.3204 | 0.9150 | 0.050* | |
| C4 | 1.1590 (5) | 0.36250 (11) | 0.76728 (18) | 0.0418 (5) | |
| H4 | 1.3019 | 0.3936 | 0.7873 | 0.050* | |
| C5 | 1.0300 (5) | 0.35970 (10) | 0.66087 (18) | 0.0377 (5) | |
| C6 | 0.8198 (5) | 0.31402 (10) | 0.63019 (17) | 0.0369 (5) | |
| H6 | 0.7360 | 0.3126 | 0.5581 | 0.044* | |
| C7 | 0.5052 (4) | 0.22206 (10) | 0.67230 (17) | 0.0343 (5) | |
| H7 | 0.4212 | 0.2224 | 0.6002 | 0.041* | |
| C8 | 0.2060 (4) | 0.13210 (10) | 0.70442 (17) | 0.0332 (5) | |
| C9 | 0.1021 (5) | 0.12019 (11) | 0.59655 (18) | 0.0418 (5) | |
| H9 | 0.1690 | 0.1454 | 0.5406 | 0.050* | |
| C10 | −0.0999 (5) | 0.07125 (11) | 0.57144 (19) | 0.0460 (6) | |
| H10 | −0.1702 | 0.0633 | 0.4990 | 0.055* | |
| C11 | −0.1946 (5) | 0.03478 (11) | 0.6549 (2) | 0.0445 (6) | |
| C12 | −0.0996 (5) | 0.04499 (12) | 0.7619 (2) | 0.0483 (6) | |
| H12 | −0.1684 | 0.0195 | 0.8171 | 0.058* | |
| C13 | 0.1021 (5) | 0.09426 (12) | 0.78670 (19) | 0.0443 (6) | |
| H13 | 0.1687 | 0.1021 | 0.8595 | 0.053* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.0733 (2) | 0.05159 (18) | 0.05448 (18) | −0.01654 (13) | −0.00037 (13) | 0.01097 (12) |
| F1 | 0.0782 (11) | 0.0552 (10) | 0.0788 (11) | −0.0331 (9) | −0.0069 (9) | 0.0023 (8) |
| O1 | 0.0592 (10) | 0.0587 (11) | 0.0313 (8) | −0.0167 (8) | −0.0051 (7) | 0.0033 (8) |
| N1 | 0.0310 (10) | 0.0401 (11) | 0.0354 (9) | 0.0009 (8) | −0.0014 (7) | −0.0038 (8) |
| C1 | 0.0303 (11) | 0.0348 (11) | 0.0312 (10) | 0.0019 (9) | 0.0005 (8) | −0.0036 (9) |
| C2 | 0.0348 (12) | 0.0405 (12) | 0.0315 (11) | 0.0018 (9) | 0.0023 (9) | −0.0039 (9) |
| C3 | 0.0422 (13) | 0.0505 (14) | 0.0305 (11) | −0.0031 (11) | −0.0043 (9) | −0.0084 (10) |
| C4 | 0.0393 (13) | 0.0388 (13) | 0.0467 (13) | −0.0048 (10) | −0.0005 (10) | −0.0125 (10) |
| C5 | 0.0418 (13) | 0.0314 (11) | 0.0402 (12) | 0.0017 (10) | 0.0045 (10) | 0.0001 (9) |
| C6 | 0.0382 (12) | 0.0387 (12) | 0.0327 (11) | 0.0021 (10) | −0.0036 (9) | −0.0026 (9) |
| C7 | 0.0326 (11) | 0.0372 (12) | 0.0322 (10) | 0.0025 (9) | −0.0028 (9) | −0.0055 (9) |
| C8 | 0.0275 (11) | 0.0361 (12) | 0.0357 (11) | 0.0019 (9) | −0.0004 (9) | −0.0001 (9) |
| C9 | 0.0495 (14) | 0.0409 (13) | 0.0344 (11) | −0.0059 (11) | −0.0005 (10) | 0.0009 (10) |
| C10 | 0.0517 (15) | 0.0451 (14) | 0.0397 (12) | −0.0089 (11) | −0.0066 (11) | −0.0024 (10) |
| C11 | 0.0407 (13) | 0.0364 (13) | 0.0554 (14) | −0.0050 (10) | −0.0027 (11) | 0.0008 (11) |
| C12 | 0.0501 (15) | 0.0462 (15) | 0.0492 (14) | −0.0058 (12) | 0.0068 (11) | 0.0128 (11) |
| C13 | 0.0425 (13) | 0.0523 (15) | 0.0370 (12) | −0.0029 (11) | −0.0035 (10) | 0.0038 (10) |
| Br1—C5 | 1.898 (2) | C5—C6 | 1.370 (3) |
| F1—C11 | 1.358 (3) | C6—H6 | 0.9300 |
| O1—C2 | 1.350 (2) | C7—H7 | 0.9300 |
| O1—H1 | 0.8176 | C8—C9 | 1.385 (3) |
| N1—C7 | 1.274 (3) | C8—C13 | 1.387 (3) |
| N1—C8 | 1.423 (3) | C9—C10 | 1.381 (3) |
| C1—C6 | 1.395 (3) | C9—H9 | 0.9300 |
| C1—C2 | 1.400 (3) | C10—C11 | 1.366 (3) |
| C1—C7 | 1.455 (3) | C10—H10 | 0.9300 |
| C2—C3 | 1.382 (3) | C11—C12 | 1.359 (3) |
| C3—C4 | 1.375 (3) | C12—C13 | 1.384 (3) |
| C3—H3 | 0.9300 | C12—H12 | 0.9300 |
| C4—C5 | 1.381 (3) | C13—H13 | 0.9300 |
| C4—H4 | 0.9300 | ||
| C2—O1—H1 | 110.1 | N1—C7—H7 | 119.3 |
| C7—N1—C8 | 121.51 (18) | C1—C7—H7 | 119.3 |
| C6—C1—C2 | 118.99 (19) | C9—C8—C13 | 118.8 (2) |
| C6—C1—C7 | 119.02 (19) | C9—C8—N1 | 125.01 (19) |
| C2—C1—C7 | 121.99 (19) | C13—C8—N1 | 116.18 (18) |
| O1—C2—C3 | 118.68 (18) | C10—C9—C8 | 120.5 (2) |
| O1—C2—C1 | 121.60 (19) | C10—C9—H9 | 119.7 |
| C3—C2—C1 | 119.7 (2) | C8—C9—H9 | 119.7 |
| C4—C3—C2 | 120.78 (19) | C11—C10—C9 | 118.8 (2) |
| C4—C3—H3 | 119.6 | C11—C10—H10 | 120.6 |
| C2—C3—H3 | 119.6 | C9—C10—H10 | 120.6 |
| C3—C4—C5 | 119.4 (2) | F1—C11—C12 | 118.8 (2) |
| C3—C4—H4 | 120.3 | F1—C11—C10 | 118.5 (2) |
| C5—C4—H4 | 120.3 | C12—C11—C10 | 122.7 (2) |
| C6—C5—C4 | 120.9 (2) | C11—C12—C13 | 118.4 (2) |
| C6—C5—Br1 | 119.87 (16) | C11—C12—H12 | 120.8 |
| C4—C5—Br1 | 119.20 (17) | C13—C12—H12 | 120.8 |
| C5—C6—C1 | 120.14 (19) | C12—C13—C8 | 120.9 (2) |
| C5—C6—H6 | 119.9 | C12—C13—H13 | 119.6 |
| C1—C6—H6 | 119.9 | C8—C13—H13 | 119.6 |
| N1—C7—C1 | 121.38 (19) | ||
| C6—C1—C2—O1 | 179.65 (18) | C6—C1—C7—N1 | 178.87 (18) |
| C7—C1—C2—O1 | 0.1 (3) | C2—C1—C7—N1 | −1.6 (3) |
| C6—C1—C2—C3 | −0.4 (3) | C7—N1—C8—C9 | 9.7 (3) |
| C7—C1—C2—C3 | 180.0 (2) | C7—N1—C8—C13 | −171.9 (2) |
| O1—C2—C3—C4 | −179.3 (2) | C13—C8—C9—C10 | −0.4 (3) |
| C1—C2—C3—C4 | 0.8 (3) | N1—C8—C9—C10 | 178.1 (2) |
| C2—C3—C4—C5 | −0.5 (3) | C8—C9—C10—C11 | −0.2 (4) |
| C3—C4—C5—C6 | −0.2 (3) | C9—C10—C11—F1 | −179.0 (2) |
| C3—C4—C5—Br1 | 179.31 (17) | C9—C10—C11—C12 | 0.5 (4) |
| C4—C5—C6—C1 | 0.5 (3) | F1—C11—C12—C13 | 179.2 (2) |
| Br1—C5—C6—C1 | −179.00 (15) | C10—C11—C12—C13 | −0.2 (4) |
| C2—C1—C6—C5 | −0.2 (3) | C11—C12—C13—C8 | −0.3 (4) |
| C7—C1—C6—C5 | 179.4 (2) | C9—C8—C13—C12 | 0.6 (4) |
| C8—N1—C7—C1 | −178.11 (18) | N1—C8—C13—C12 | −177.9 (2) |
Experimental details
| Crystal data | |
| Chemical formula | C13H9BrFNO |
| Mr | 294.12 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 296 |
| a, b, c (Å) | 4.4820 (2), 20.8088 (9), 12.2189 (5) |
| β (°) | 94.570 (2) |
| V (Å3) | 1135.97 (8) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 3.61 |
| Crystal size (mm) | 0.35 × 0.17 × 0.11 |
| Data collection | |
| Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
| Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
| Tmin, Tmax | 0.365, 0.692 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 10561, 2792, 1958 |
| Rint | 0.034 |
| (sin θ/λ)max (Å−1) | 0.667 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.083, 1.02 |
| No. of reflections | 2792 |
| No. of parameters | 154 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.44, −0.26 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Acknowledgements
AAA thanks the Islamic Azad University, Ardakan Branch for the research facilities (this paper was extracted from a research project supported by IAU). RK thanks the Science and Research Branch, Islamic Azad University, Tehran. HK thanks the PNU for financial support. MNT thanks Sargodha University for the research facilities.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of Schiff bases, we have determined the crystal structure of the title compound.
The asymmetric unit of the title compound, Fig. 1, comprises a potentially bidenate Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges. The dihedral angle between the substituted benzene rings is 9.00 (11)Å. Strong intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995).