organic compounds
4-Bromo-2-[(E)-(2-fluoro-5-nitrophenyl)iminomethyl]phenol
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, and ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al AzharUniversity, Egypt
*Correspondence e-mail: akkurt@erciyes.edu.tr
The molecular conformation of the title compound, C13H8BrFN2O3, is essentially planar, with maximum deviations of 0.076 (1) and −0.080 (2) Å for the O atoms of the NO2 group. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of molecules are linked via two pairs of C—H⋯O hydrogen bonds, forming inversion dimers that enclose R22(7)R22(10)R22(7) ring motifs.
Related literature
For the synthesis and biological activity of et al. (2009); Kalaivani et al. (2012); Blair et al. (2000). For the synthesis of fluorinated see: Mohamed et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For standard bond lengths, see: Allen et al. (1987).
see: PrzybylskiExperimental
Crystal data
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Refinement
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Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812050696/xu5665sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050696/xu5665Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050696/xu5665Isup3.cml
A mixture of 1 mmol (156 mg) 2-fluoro-5-nitroaniline and 1 mmol (201 mg) 5-bromo-2-hydroxybenzaldehyde in 50 ml e thanol was heated at 350 K and monitored by TLC till completion after 12 h. A mass solid product was deposited once the reaction mixture was allowed to cool at room temperature. The crude product was filtered dried under vacuum and washed by ethanol. Pure yellow rods (m.p. 465 K) suitable for X-ray diffraction were obtained in an excellent yield (92%) by crystallization of crude product from ethanol.
H atoms were positioned geometrically and refined using a riding model, with O—H = 0.84 Å, C—H = 0.95 Å, and with Uiso(H) = 1.5Ueq(O) for hydroxyl and Uiso(H) = 1.2 Ueq(C) for the other H atoms.
Schiff bases have been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral, and antipyretic properties (Przybylski et al., 2009; Kalaivani et al., 2012). Among such compounds, the fluorinated Schiff's bases were considered to possess a distingushed biological activity due to the dramatic affect of fluorine atom on the metabolism and distribution of drug molecules in the body (Blair et al., 2000). Further to our on going study on synthesis of bioactive fluorinated compounds (Mohamed et al., 2012) we herein report the synthesis and
of a new fluorinated azomethine derivative.In the title compound (I), (Fig. 1), the
is essentially planar, with maxium deviations of 0.076 (1) and -0.080 (2) Å, respectively, for O2 and O3. The C1–C7–N1–C8 torsion angle is 179.92 (16)°. The bond lengths and angles in (I) are within the normal range (Allen et al., 1987).Molecular conformation is stabilized by O—H···N hydrogen bond (Table 1), forming an S(6) ring motif. In the crystal, the pairs of molecules are linked by C—H···O interactions (Table 1, Fig. 2), generating R22(7)R22(10)R22(7) ring motifs (Bernstein et al., 1995) along the [001] direction.
For the synthesis and biological activity of
see: Przybylski et al. (2009); Kalaivani et al. (2012); Blair et al. (2000). For the synthesis of fluorinated see: Mohamed et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995). For standard bond lengths, see: Allen et al. (1987).Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell
CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C13H8BrFN2O3 | F(000) = 672 |
Mr = 339.11 | Dx = 1.829 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2yn | Cell parameters from 4566 reflections |
a = 4.5082 (9) Å | θ = 2.5–31.2° |
b = 19.815 (4) Å | µ = 3.36 mm−1 |
c = 13.853 (3) Å | T = 100 K |
β = 95.484 (5)° | Rod, yellow |
V = 1231.8 (4) Å3 | 0.24 × 0.04 × 0.03 mm |
Z = 4 |
Rigaku AFC12 (Right) diffractometer | 2811 independent reflections |
Radiation source: Rotating Anode | 2633 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.023 |
profile data from ω–scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012) | h = −5→5 |
Tmin = 0.500, Tmax = 0.906 | k = −25→24 |
8107 measured reflections | l = −17→14 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.059 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0255P)2 + 1.1447P] where P = (Fo2 + 2Fc2)/3 |
2811 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
C13H8BrFN2O3 | V = 1231.8 (4) Å3 |
Mr = 339.11 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.5082 (9) Å | µ = 3.36 mm−1 |
b = 19.815 (4) Å | T = 100 K |
c = 13.853 (3) Å | 0.24 × 0.04 × 0.03 mm |
β = 95.484 (5)° |
Rigaku AFC12 (Right) diffractometer | 2811 independent reflections |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012) | 2633 reflections with I > 2σ(I) |
Tmin = 0.500, Tmax = 0.906 | Rint = 0.023 |
8107 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.059 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.52 e Å−3 |
2811 reflections | Δρmin = −0.54 e Å−3 |
182 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | −0.15532 (4) | 0.22619 (1) | 0.43736 (1) | 0.0188 (1) | |
F1 | 0.7510 (2) | 0.50903 (6) | 0.05672 (7) | 0.0202 (3) | |
O1 | 0.2171 (3) | 0.37891 (7) | 0.09274 (9) | 0.0171 (4) | |
O2 | 1.5039 (3) | 0.63282 (8) | 0.41030 (11) | 0.0290 (4) | |
O3 | 1.2227 (5) | 0.56614 (11) | 0.48212 (12) | 0.0614 (8) | |
N1 | 0.5847 (3) | 0.44689 (7) | 0.21201 (11) | 0.0140 (4) | |
N2 | 1.3057 (4) | 0.59101 (9) | 0.40914 (12) | 0.0227 (5) | |
C1 | 0.2662 (4) | 0.36222 (8) | 0.26646 (12) | 0.0123 (5) | |
C2 | 0.1398 (4) | 0.34652 (9) | 0.17204 (12) | 0.0135 (5) | |
C3 | −0.0742 (4) | 0.29535 (9) | 0.15895 (13) | 0.0157 (5) | |
C4 | −0.1635 (4) | 0.26099 (9) | 0.23746 (13) | 0.0159 (5) | |
C5 | −0.0389 (4) | 0.27669 (9) | 0.33084 (12) | 0.0140 (5) | |
C6 | 0.1728 (4) | 0.32683 (9) | 0.34603 (12) | 0.0145 (5) | |
C7 | 0.4936 (4) | 0.41399 (9) | 0.28338 (13) | 0.0138 (5) | |
C8 | 0.8050 (4) | 0.49730 (9) | 0.22592 (13) | 0.0136 (5) | |
C9 | 0.8877 (4) | 0.52873 (9) | 0.14215 (12) | 0.0150 (5) | |
C10 | 1.0992 (4) | 0.57931 (9) | 0.14290 (13) | 0.0165 (5) | |
C11 | 1.2365 (4) | 0.60049 (9) | 0.23159 (13) | 0.0157 (5) | |
C12 | 1.1566 (4) | 0.56969 (9) | 0.31484 (13) | 0.0156 (5) | |
C13 | 0.9451 (4) | 0.51880 (9) | 0.31435 (13) | 0.0154 (5) | |
H1 | 0.34830 | 0.40790 | 0.10930 | 0.0260* | |
H3 | −0.15830 | 0.28430 | 0.09540 | 0.0190* | |
H4 | −0.31010 | 0.22660 | 0.22810 | 0.0190* | |
H6 | 0.25500 | 0.33730 | 0.41000 | 0.0170* | |
H7 | 0.57530 | 0.42350 | 0.34770 | 0.0170* | |
H10 | 1.14920 | 0.59910 | 0.08410 | 0.0200* | |
H11 | 1.38190 | 0.63530 | 0.23510 | 0.0190* | |
H13 | 0.89690 | 0.49900 | 0.37330 | 0.0180* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0189 (1) | 0.0213 (1) | 0.0161 (1) | −0.0045 (1) | 0.0003 (1) | 0.0053 (1) |
F1 | 0.0209 (6) | 0.0273 (6) | 0.0115 (5) | −0.0064 (5) | −0.0028 (4) | 0.0011 (4) |
O1 | 0.0208 (7) | 0.0184 (6) | 0.0119 (6) | −0.0042 (5) | 0.0007 (5) | 0.0008 (5) |
O2 | 0.0326 (8) | 0.0292 (8) | 0.0243 (7) | −0.0159 (7) | −0.0022 (6) | −0.0043 (6) |
O3 | 0.0880 (16) | 0.0804 (15) | 0.0135 (8) | −0.0628 (13) | −0.0074 (9) | 0.0082 (8) |
N1 | 0.0128 (7) | 0.0141 (7) | 0.0150 (7) | 0.0001 (6) | 0.0013 (6) | −0.0005 (5) |
N2 | 0.0290 (9) | 0.0228 (8) | 0.0156 (8) | −0.0085 (7) | −0.0011 (7) | −0.0008 (6) |
C1 | 0.0110 (8) | 0.0124 (8) | 0.0136 (8) | 0.0021 (6) | 0.0011 (6) | −0.0003 (6) |
C2 | 0.0137 (8) | 0.0135 (8) | 0.0133 (8) | 0.0026 (6) | 0.0015 (6) | 0.0004 (6) |
C3 | 0.0156 (9) | 0.0171 (8) | 0.0140 (8) | 0.0000 (7) | −0.0011 (6) | −0.0047 (7) |
C4 | 0.0145 (8) | 0.0144 (8) | 0.0186 (9) | −0.0005 (7) | 0.0001 (7) | −0.0018 (7) |
C5 | 0.0144 (8) | 0.0148 (8) | 0.0127 (8) | 0.0009 (7) | 0.0015 (6) | 0.0021 (6) |
C6 | 0.0147 (8) | 0.0160 (8) | 0.0125 (8) | 0.0014 (7) | 0.0000 (6) | 0.0002 (6) |
C7 | 0.0123 (8) | 0.0151 (8) | 0.0137 (8) | 0.0012 (7) | −0.0005 (6) | −0.0014 (6) |
C8 | 0.0129 (8) | 0.0129 (8) | 0.0151 (8) | 0.0007 (6) | 0.0016 (7) | −0.0003 (6) |
C9 | 0.0139 (8) | 0.0179 (8) | 0.0125 (8) | 0.0022 (7) | −0.0023 (6) | −0.0014 (6) |
C10 | 0.0164 (9) | 0.0166 (8) | 0.0167 (9) | 0.0011 (7) | 0.0022 (7) | 0.0036 (7) |
C11 | 0.0155 (8) | 0.0126 (8) | 0.0191 (9) | −0.0009 (7) | 0.0017 (7) | 0.0007 (7) |
C12 | 0.0163 (9) | 0.0155 (8) | 0.0145 (8) | −0.0004 (7) | −0.0010 (7) | −0.0021 (6) |
C13 | 0.0160 (9) | 0.0159 (8) | 0.0143 (8) | −0.0009 (7) | 0.0012 (7) | 0.0007 (6) |
Br1—C5 | 1.8980 (18) | C5—C6 | 1.380 (3) |
F1—C9 | 1.339 (2) | C8—C13 | 1.390 (3) |
O1—C2 | 1.347 (2) | C8—C9 | 1.399 (2) |
O2—N2 | 1.218 (2) | C9—C10 | 1.383 (3) |
O3—N2 | 1.215 (3) | C10—C11 | 1.387 (3) |
O1—H1 | 0.8400 | C11—C12 | 1.383 (3) |
N1—C7 | 1.284 (2) | C12—C13 | 1.387 (3) |
N1—C8 | 1.409 (2) | C3—H3 | 0.9500 |
N2—C12 | 1.473 (2) | C4—H4 | 0.9500 |
C1—C6 | 1.405 (2) | C6—H6 | 0.9500 |
C1—C7 | 1.453 (2) | C7—H7 | 0.9500 |
C1—C2 | 1.411 (2) | C10—H10 | 0.9500 |
C2—C3 | 1.399 (3) | C11—H11 | 0.9500 |
C3—C4 | 1.376 (3) | C13—H13 | 0.9500 |
C4—C5 | 1.395 (2) | ||
C2—O1—H1 | 109.00 | F1—C9—C10 | 118.47 (15) |
C7—N1—C8 | 121.86 (16) | C8—C9—C10 | 123.70 (16) |
O2—N2—C12 | 118.63 (16) | C9—C10—C11 | 118.36 (16) |
O3—N2—C12 | 118.09 (18) | C10—C11—C12 | 118.40 (17) |
O2—N2—O3 | 123.29 (18) | N2—C12—C11 | 118.69 (16) |
C2—C1—C7 | 121.43 (15) | C11—C12—C13 | 123.40 (17) |
C6—C1—C7 | 119.05 (15) | N2—C12—C13 | 117.91 (16) |
C2—C1—C6 | 119.52 (16) | C8—C13—C12 | 118.76 (16) |
O1—C2—C3 | 117.94 (15) | C2—C3—H3 | 120.00 |
C1—C2—C3 | 119.50 (16) | C4—C3—H3 | 120.00 |
O1—C2—C1 | 122.56 (16) | C3—C4—H4 | 120.00 |
C2—C3—C4 | 120.43 (16) | C5—C4—H4 | 120.00 |
C3—C4—C5 | 120.02 (17) | C1—C6—H6 | 120.00 |
Br1—C5—C4 | 119.11 (13) | C5—C6—H6 | 120.00 |
Br1—C5—C6 | 119.98 (13) | N1—C7—H7 | 120.00 |
C4—C5—C6 | 120.88 (16) | C1—C7—H7 | 120.00 |
C1—C6—C5 | 119.65 (15) | C9—C10—H10 | 121.00 |
N1—C7—C1 | 120.45 (16) | C11—C10—H10 | 121.00 |
N1—C8—C9 | 116.27 (16) | C10—C11—H11 | 121.00 |
N1—C8—C13 | 126.35 (16) | C12—C11—H11 | 121.00 |
C9—C8—C13 | 117.38 (16) | C8—C13—H13 | 121.00 |
F1—C9—C8 | 117.83 (16) | C12—C13—H13 | 121.00 |
C8—N1—C7—C1 | −179.92 (16) | C3—C4—C5—C6 | 0.4 (3) |
C7—N1—C8—C9 | 179.13 (17) | C3—C4—C5—Br1 | −177.66 (14) |
C7—N1—C8—C13 | −1.3 (3) | Br1—C5—C6—C1 | 177.55 (13) |
O3—N2—C12—C13 | −4.7 (3) | C4—C5—C6—C1 | −0.5 (3) |
O2—N2—C12—C11 | −3.3 (3) | N1—C8—C9—C10 | 179.72 (16) |
O2—N2—C12—C13 | 175.80 (17) | C13—C8—C9—F1 | −179.08 (16) |
O3—N2—C12—C11 | 176.20 (19) | C13—C8—C9—C10 | 0.1 (3) |
C7—C1—C2—C3 | 178.71 (17) | N1—C8—C9—F1 | 0.5 (2) |
C7—C1—C6—C5 | −178.80 (17) | N1—C8—C13—C12 | −179.49 (17) |
C2—C1—C7—N1 | 0.1 (3) | C9—C8—C13—C12 | 0.1 (3) |
C2—C1—C6—C5 | 0.7 (3) | F1—C9—C10—C11 | 178.83 (16) |
C6—C1—C2—C3 | −0.8 (3) | C8—C9—C10—C11 | −0.4 (3) |
C7—C1—C2—O1 | −1.2 (3) | C9—C10—C11—C12 | 0.4 (3) |
C6—C1—C7—N1 | 179.58 (16) | C10—C11—C12—N2 | 178.83 (16) |
C6—C1—C2—O1 | 179.35 (16) | C10—C11—C12—C13 | −0.3 (3) |
O1—C2—C3—C4 | −179.43 (16) | N2—C12—C13—C8 | −179.08 (16) |
C1—C2—C3—C4 | 0.7 (3) | C11—C12—C13—C8 | 0.0 (3) |
C2—C3—C4—C5 | −0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 | 1.86 | 2.601 (2) | 146 |
C7—H7···O3i | 0.95 | 2.45 | 3.399 (3) | 173 |
C13—H13···O3i | 0.95 | 2.48 | 3.430 (3) | 173 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H8BrFN2O3 |
Mr | 339.11 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 4.5082 (9), 19.815 (4), 13.853 (3) |
β (°) | 95.484 (5) |
V (Å3) | 1231.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.36 |
Crystal size (mm) | 0.24 × 0.04 × 0.03 |
Data collection | |
Diffractometer | Rigaku AFC12 (Right) |
Absorption correction | Multi-scan (CrystalClear-SM Expert; Rigaku, 2012) |
Tmin, Tmax | 0.500, 0.906 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8107, 2811, 2633 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.059, 1.05 |
No. of reflections | 2811 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.54 |
Computer programs: CrystalClear-SM Expert (Rigaku, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 | 1.86 | 2.601 (2) | 146 |
C7—H7···O3i | 0.95 | 2.45 | 3.399 (3) | 173 |
C13—H13···O3i | 0.95 | 2.48 | 3.430 (3) | 173 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Acknowledgements
The EPSRC National Crystallography Service is gratefully acknowledged for the X-ray diffraction data. AAA and SKM thank the Ministry of Higher Education of Egypt for financial support of this collaporative project. The authors are also thankful to Manchester Metropolitan University and Erciyes University for supporting this study.
References
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Schiff bases have been shown to exhibit a broad range of biological activities, including antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral, and antipyretic properties (Przybylski et al., 2009; Kalaivani et al., 2012). Among such compounds, the fluorinated Schiff's bases were considered to possess a distingushed biological activity due to the dramatic affect of fluorine atom on the metabolism and distribution of drug molecules in the body (Blair et al., 2000). Further to our on going study on synthesis of bioactive fluorinated compounds (Mohamed et al., 2012) we herein report the synthesis and crystal structure of a new fluorinated azomethine derivative.
In the title compound (I), (Fig. 1), the molecular conformation is essentially planar, with maxium deviations of 0.076 (1) and -0.080 (2) Å, respectively, for O2 and O3. The C1–C7–N1–C8 torsion angle is 179.92 (16)°. The bond lengths and angles in (I) are within the normal range (Allen et al., 1987).
Molecular conformation is stabilized by O—H···N hydrogen bond (Table 1), forming an S(6) ring motif. In the crystal, the pairs of molecules are linked by C—H···O interactions (Table 1, Fig. 2), generating R22(7)R22(10)R22(7) ring motifs (Bernstein et al., 1995) along the [001] direction.