Crystal structure of 2-{[2-meth­oxy-5-(tri­fluoro­meth­yl)phen­yl]iminomethyl}-4-nitro­phenol

Nevzat Karadayı; Songül Şahin; Yavuz Köysal; Emine Coşkun; Orhan Büyükgüngör

doi:10.1107/S2056989015010129

. 2015 Jun 13;71(Pt 7):o466–o467. doi: 10.1107/S2056989015010129

Crystal structure of 2-{[2-methoxy-5-(trifluoromethyl)phenyl]iminomethyl}-4-nitrophenol

Nevzat Karadayı ^a,^*, Songül Şahin ^b, Yavuz Köysal ^a, Emine Coşkun ^b, Orhan Büyükgüngör ^c

PMCID: PMC4518952 PMID: 26279911

Abstract

In the title compound, C₁₅H₁₁F₃N₂O₄, the N=C bond of the central imine group adopts an E conformation. The dihedral angle between two benzene rings is 6.2 (2)°. There is an intramolecular bifurcated O—H⋯(N,O) hydrogen bond with S(6) and S(9) ring motifs. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into a helical chain along the 3₁ screw axis parallel to c. The –CF₃ group shows rotational disorder over two sites, with occupancies of 0.39 (2) and 0.61 (2).

Keywords: crystal structure, Schiff base, hydrogen bonding

Related literature

For photochromic, thermochromic and biological applications of related Schiff base compounds, see: Hadjoudis et al. (1987 ▸); Santos et al. (2001 ▸); Tarafder et al. (2002 ▸). For related structures, see: Faridbod et al. (2008 ▸); Karadayı et al. (2003 ▸, 2006 ▸, 2013 ▸); Raja et al. (2008 ▸). graphic file with name e-71-0o466-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₁F₃N₂O₄
M _r = 340.26
Trigonal,
a = 33.0327 (16) Å
c = 7.1523 (3) Å
V = 6758.7 (5) Å³
Z = 18
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.67 × 0.25 × 0.04 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▸) T _min = 0.951, T _max = 0.994
16356 measured reflections
2958 independent reflections
1380 reflections with I > 2σ(I)
R _int = 0.140

Refinement

R[F ² > 2σ(F ²)] = 0.084
wR(F ²) = 0.126
S = 1.07
2958 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 e Å⁻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, 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 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015010129/is5398sup1.cif

e-71-0o466-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010129/is5398Isup2.hkl

e-71-0o466-Isup2.hkl^{(142.5KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015010129/is5398Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

ORTEP . DOI: 10.1107/S2056989015010129/is5398fig1.tif

An ORTEP drawing of the title compound showing the atomic numbering scheme. Displacement ellipsoids of non-H atoms are shown at the 20% probability level. Hydrogen bonds are indicated by dashed lines.

CCDC reference: 1402674

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.84	2.571(4)	148
O1H1O4	0.82	2.76	3.468(4)	146
C7H7O2ⁱ	0.93	2.55	3.476(7)	176
C9H9O2ⁱ	0.93	2.46	3.378(6)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

S1. Comment

Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Hadjoudis et al., 1987). Schiff bases are potentially biologically active compounds and the antifungal, anticancer, anticonvulsant, diuretic and cytotoxic activities have been reported. For the development of bacteriostatic activity, it is believed that the presence of a nitro group in the p-position is an important condition (Tarafder et al., 2002; Santos et al., 2001). In this study we report the structure of the title compound (I).

The N1═C7 bond length is 1.295 (5) Å, approximately equal to previously reported C═N bond lengths (Karadayı et al., 2003; Faridbod et al., 2008; Karadayı et al., 2013). The geometric parameters in (I) are comparable with the similar reported structures (Raja et al., 2008; Karadayı et al., 2006). The dihedral angle between the aromatic rings (C1–C6) and (C8–C13) is 6.2 (2)°. The CF₃ group showed rotational disorder. The site occupancy factors are 0.39 (2) and 0.61 (2) for F1A–F3A and F1B–F3B, respectively. An intramolecular bifurcated O—H···(N, O) hydrogen bond is observed (Table 1 and Fig. 1).

S2. Experimental

The title compound was prepared by refluxing a mixture of a solution containing 2-hydroxy-5-nitrobenzaldehyde (0.014 g, 0.082 mmol) and a solution containing 2-methoxy-5-(trifluoromethyl)aniline (0,016 g, 0.082 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1 h under reflux. Single crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation (yield 54%, m.p. 475–477 K).