organic compounds
(E)-4-Fluoro-2-[(phenylimino)methyl]phenol
aPostgraduate Research Department of Physics, Government Arts College (Autonomous), Kumbakonam 612 001, Tamilnadu, India, bPostgraduate Department of Physics, Dharmapuram Gnanambigai College for Women, Mayiladuthurai 609 001, Tamilnadu, India, cPrincipal, Kunthavai Naacchiyaar Government Arts College for Women (Autonomous), Thanjavur 613 007, Tamilnadu, India, and dPostgraduate Department of Physics, A.D.M. College for Women (Autonomous), Nagapattinam 611 001, Tamilnadu, India
*Correspondence e-mail: thiruvalluvar.a@gmail.com
The title compound, C13H10FNO, is essentially planar (r.m.s. deviation = 0.022 Å) and the dihedral angle between the planes of the two aryl rings is 0.69 (15)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring. The features C—H⋯O hydrogen bonds.
Keywords: crystal structure; salicylaldehyde derivative; O—H⋯N hydrogen bonding; C—H⋯O hydrogen bonding.
CCDC reference: 1586558
Structure description
We report here, as part of our ongoing research (Ida Malarselvi et al., 2016), the synthesis and (Fig. 1), of the title fluorinated Schiff base compound, synthesized from the condensation reaction of equimolar amounts of 5-fluorosalicylaldehyde and aniline in DMSO. In this structure, the benzene and phenyl rings subtend a dihedral angle of 0.69 (15)°. The molecule has an E conformation about the C=N bond, and the C1—C7=N1—C8 torsion angle is 180.0 (2)°. There is a strong intramolecular O1—H1⋯N1 hydrogen bond [H⋯N = 1.70 (5) Å], which generates an S(6) ring. The features C7—H7⋯O1 hydrogen bonds (see Table 1, Fig. 2).
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Yan et al., (2014) have reported the of 4-bromo-2-[(phenylimino)methyl]phenol, in which the molecule is essentially planar (r.m.s. deviation = 0.026 Å), similar to our present study (r.m.s. deviation = 0.022 Å).
Synthesis and crystallization
0.35 g (0.0025 mol) of 5-fluorosalicylaldehyde were dissolved in 10 ml of DMSO. To this solution, 0.23 g (0.0025 mol) of aniline were added drop wise with constant stirring for 1 h. During this time, the solution turned deep yellow. On standing for two weeks with slow evaporation of the solvent, orange crystals of the title compound, suitable for X-ray study were obtained.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1586558
https://doi.org/10.1107/S2414314617016716/hg4032sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617016716/hg4032Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617016716/hg4032Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617016716/hg4032Isup4.cml
Data collection: APEX3 (Bruker, 2016); cell
APEX3 and SAINT (Bruker, 2016); data reduction: SAINT and XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C13H10FNO | F(000) = 448 |
Mr = 215.22 | Dx = 1.371 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 18.965 (2) Å | Cell parameters from 2681 reflections |
b = 4.7214 (5) Å | θ = 4.9–70.9° |
c = 12.2399 (13) Å | µ = 0.83 mm−1 |
β = 107.881 (7)° | T = 296 K |
V = 1043.0 (2) Å3 | Plate, orange |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
Bruker Kappa APEX3 CMOS diffractometer | 1069 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed tube | Rint = 0.097 |
ω and φ scan | θmax = 71.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −23→21 |
Tmin = 0.536, Tmax = 0.754 | k = −4→5 |
10586 measured reflections | l = −14→15 |
1997 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.0689P)2 + 0.2085P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.173 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.16 e Å−3 |
1997 reflections | Δρmin = −0.16 e Å−3 |
150 parameters | Extinction correction: SHELXL2017 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0042 (11) |
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. H atoms attached to C of (I) were placed in geometrically idealized positions with Csp2—H = 0.93 Å. The hydroxy H atom, H1, is located in a difference Fourier map and freely refined. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.31946 (14) | 0.1990 (6) | 0.8556 (2) | 0.0569 (7) | |
C2 | 0.32137 (16) | 0.1370 (6) | 0.9681 (2) | 0.0642 (8) | |
C3 | 0.37148 (17) | −0.0616 (7) | 1.0310 (3) | 0.0742 (9) | |
H3 | 0.373294 | −0.100204 | 1.106307 | 0.089* | |
C4 | 0.41831 (17) | −0.2017 (7) | 0.9837 (3) | 0.0752 (9) | |
H4 | 0.451482 | −0.336124 | 1.025813 | 0.090* | |
C5 | 0.41512 (16) | −0.1390 (7) | 0.8726 (3) | 0.0711 (8) | |
C6 | 0.36730 (16) | 0.0553 (6) | 0.8083 (2) | 0.0664 (8) | |
H6 | 0.366494 | 0.092055 | 0.733234 | 0.080* | |
C7 | 0.26800 (16) | 0.4054 (6) | 0.7872 (2) | 0.0612 (7) | |
H7 | 0.267062 | 0.436748 | 0.711738 | 0.073* | |
C8 | 0.17332 (15) | 0.7488 (6) | 0.7606 (2) | 0.0592 (7) | |
C9 | 0.16766 (17) | 0.8212 (7) | 0.6485 (2) | 0.0777 (9) | |
H9 | 0.198385 | 0.735704 | 0.611808 | 0.093* | |
C10 | 0.11625 (19) | 1.0209 (7) | 0.5914 (3) | 0.0869 (10) | |
H10 | 0.112828 | 1.069505 | 0.516307 | 0.104* | |
C11 | 0.07008 (17) | 1.1487 (7) | 0.6439 (3) | 0.0806 (9) | |
H11 | 0.035174 | 1.280954 | 0.604422 | 0.097* | |
C12 | 0.07608 (18) | 1.0791 (7) | 0.7551 (3) | 0.0796 (9) | |
H12 | 0.045277 | 1.164804 | 0.791596 | 0.096* | |
C13 | 0.12772 (16) | 0.8821 (7) | 0.8129 (3) | 0.0711 (8) | |
H13 | 0.131820 | 0.838381 | 0.888667 | 0.085* | |
N1 | 0.22382 (12) | 0.5460 (5) | 0.82746 (17) | 0.0611 (6) | |
O1 | 0.27583 (12) | 0.2678 (5) | 1.01816 (17) | 0.0817 (7) | |
F5 | 0.46145 (10) | −0.2803 (4) | 0.82560 (15) | 0.0977 (7) | |
H1 | 0.245 (2) | 0.405 (9) | 0.961 (4) | 0.142 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0652 (16) | 0.0505 (17) | 0.0541 (14) | −0.0028 (13) | 0.0168 (13) | −0.0012 (12) |
C2 | 0.0727 (18) | 0.0631 (19) | 0.0565 (15) | 0.0010 (15) | 0.0195 (14) | 0.0033 (14) |
C3 | 0.083 (2) | 0.076 (2) | 0.0601 (17) | 0.0034 (17) | 0.0173 (16) | 0.0073 (15) |
C4 | 0.078 (2) | 0.065 (2) | 0.0738 (19) | 0.0056 (16) | 0.0101 (16) | 0.0035 (16) |
C5 | 0.0707 (19) | 0.066 (2) | 0.0771 (19) | 0.0069 (16) | 0.0242 (16) | −0.0088 (16) |
C6 | 0.0742 (18) | 0.065 (2) | 0.0595 (15) | 0.0016 (15) | 0.0201 (14) | −0.0020 (14) |
C7 | 0.0741 (18) | 0.0568 (18) | 0.0554 (15) | −0.0031 (14) | 0.0238 (14) | 0.0010 (13) |
C8 | 0.0658 (16) | 0.0495 (17) | 0.0594 (15) | −0.0036 (13) | 0.0151 (14) | 0.0007 (13) |
C9 | 0.090 (2) | 0.080 (2) | 0.0631 (17) | 0.0172 (18) | 0.0228 (16) | 0.0054 (16) |
C10 | 0.101 (3) | 0.084 (3) | 0.0687 (19) | 0.016 (2) | 0.0156 (18) | 0.0096 (18) |
C11 | 0.076 (2) | 0.068 (2) | 0.088 (2) | 0.0054 (17) | 0.0117 (18) | 0.0079 (18) |
C12 | 0.074 (2) | 0.070 (2) | 0.098 (2) | 0.0075 (16) | 0.0313 (18) | 0.0044 (18) |
C13 | 0.078 (2) | 0.067 (2) | 0.0732 (18) | 0.0026 (16) | 0.0313 (16) | 0.0048 (15) |
N1 | 0.0709 (15) | 0.0551 (15) | 0.0573 (13) | 0.0004 (11) | 0.0195 (11) | 0.0024 (10) |
O1 | 0.0998 (16) | 0.0907 (17) | 0.0631 (12) | 0.0191 (13) | 0.0374 (12) | 0.0105 (11) |
F5 | 0.0988 (13) | 0.0962 (15) | 0.0989 (13) | 0.0253 (11) | 0.0317 (11) | −0.0080 (11) |
C1—C6 | 1.394 (4) | C8—C13 | 1.376 (4) |
C1—C2 | 1.397 (4) | C8—C9 | 1.386 (4) |
C1—C7 | 1.450 (4) | C8—N1 | 1.422 (3) |
C2—O1 | 1.352 (3) | C9—C10 | 1.382 (4) |
C2—C3 | 1.388 (4) | C9—H9 | 0.9300 |
C3—C4 | 1.370 (4) | C10—C11 | 1.375 (4) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C5 | 1.375 (4) | C11—C12 | 1.371 (4) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.358 (4) | C12—C13 | 1.378 (4) |
C5—F5 | 1.364 (3) | C12—H12 | 0.9300 |
C6—H6 | 0.9300 | C13—H13 | 0.9300 |
C7—N1 | 1.280 (3) | O1—H1 | 0.99 (4) |
C7—H7 | 0.9300 | ||
C6—C1—C2 | 119.0 (3) | C13—C8—C9 | 118.6 (3) |
C6—C1—C7 | 119.7 (2) | C13—C8—N1 | 116.7 (2) |
C2—C1—C7 | 121.3 (3) | C9—C8—N1 | 124.7 (3) |
O1—C2—C3 | 118.8 (2) | C10—C9—C8 | 119.8 (3) |
O1—C2—C1 | 121.6 (3) | C10—C9—H9 | 120.1 |
C3—C2—C1 | 119.6 (3) | C8—C9—H9 | 120.1 |
C4—C3—C2 | 121.0 (3) | C11—C10—C9 | 121.0 (3) |
C4—C3—H3 | 119.5 | C11—C10—H10 | 119.5 |
C2—C3—H3 | 119.5 | C9—C10—H10 | 119.5 |
C3—C4—C5 | 118.4 (3) | C12—C11—C10 | 119.2 (3) |
C3—C4—H4 | 120.8 | C12—C11—H11 | 120.4 |
C5—C4—H4 | 120.8 | C10—C11—H11 | 120.4 |
C6—C5—F5 | 119.2 (3) | C11—C12—C13 | 120.1 (3) |
C6—C5—C4 | 122.5 (3) | C11—C12—H12 | 120.0 |
F5—C5—C4 | 118.3 (3) | C13—C12—H12 | 120.0 |
C5—C6—C1 | 119.4 (3) | C8—C13—C12 | 121.3 (3) |
C5—C6—H6 | 120.3 | C8—C13—H13 | 119.4 |
C1—C6—H6 | 120.3 | C12—C13—H13 | 119.4 |
N1—C7—C1 | 122.0 (2) | C7—N1—C8 | 122.2 (2) |
N1—C7—H7 | 119.0 | C2—O1—H1 | 107 (2) |
C1—C7—H7 | 119.0 | ||
C6—C1—C2—O1 | −179.4 (3) | C6—C1—C7—N1 | −178.9 (3) |
C7—C1—C2—O1 | −0.5 (4) | C2—C1—C7—N1 | 2.2 (4) |
C6—C1—C2—C3 | 1.2 (4) | C13—C8—C9—C10 | −0.8 (5) |
C7—C1—C2—C3 | −179.9 (3) | N1—C8—C9—C10 | 179.7 (3) |
O1—C2—C3—C4 | 179.4 (3) | C8—C9—C10—C11 | −0.3 (5) |
C1—C2—C3—C4 | −1.2 (4) | C9—C10—C11—C12 | 0.9 (5) |
C2—C3—C4—C5 | 0.7 (5) | C10—C11—C12—C13 | −0.3 (5) |
C3—C4—C5—C6 | −0.2 (5) | C9—C8—C13—C12 | 1.5 (4) |
C3—C4—C5—F5 | −179.5 (3) | N1—C8—C13—C12 | −179.1 (3) |
F5—C5—C6—C1 | 179.6 (2) | C11—C12—C13—C8 | −0.9 (5) |
C4—C5—C6—C1 | 0.2 (5) | C1—C7—N1—C8 | 180.0 (2) |
C2—C1—C6—C5 | −0.7 (4) | C13—C8—N1—C7 | 178.8 (3) |
C7—C1—C6—C5 | −179.7 (3) | C9—C8—N1—C7 | −1.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.93 | 2.61 | 3.440 (3) | 149 |
O1—H1···N1 | 0.99 (4) | 1.70 (5) | 2.595 (3) | 148 (4) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Acknowledgements
The authors are grateful to the Sophisticated Analytical Instrument Facility (SAIF), IITM, Chennai, Tamilnadu, India, for the single-crystal X-ray diffraction data.
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