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

Karadayı, N.; Şahin, S.; Köysal, Y.; Coşkun, E.; Büyükgüngör, O.

doi:10.1107/S2056989015010129

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o466-o467

doi:10.1107/S2056989015010129

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

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

^aYeşilyurt Demir Celik Higher Vocational School, Ondokuz Mayıs University, TR-55330 Tekkeköy-Samsun, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
^*Correspondence e-mail: nevzatk@omu.edu.tr

Edited by H. Ishida, Okayama University, Japan (Received 16 April 2015; accepted 25 May 2015; online 13 June 2015)

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.

CCDC reference: 1402674

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₁F₃N₂O₄
M_r = 340.26
Trigonal, $[R \overline 3]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.84	2.571 (4)	148
O1—H1⋯O4	0.82	2.76	3.468 (4)	146
C7—H7⋯O2ⁱ	0.93	2.55	3.476 (7)	176
C9—H9⋯O2ⁱ	0.93	2.46	3.378 (6)	169
Symmetry code: (i) $[-y+{\script{4\over 3}}, x-y-{\script{1\over 3}}, z-{\script{1\over 3}}]$ .

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).

Supporting information

CCDC reference: 1402674

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

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

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

checkCIF report

Comment top

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).

Related literature top

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).

Experimental top

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).

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, 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).

Figures top

Fig. 1. 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.

2-{[2-Methoxy-5-(trifluoromethyl)phenyl]iminomethyl}-4-nitrophenol top

Crystal data top

C₁₅H₁₁F₃N₂O₄	D_x = 1.505 Mg m⁻³
M_r = 340.26	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 10608 reflections
Hall symbol: -R 3	θ = 2.1–28.0°
a = 33.0327 (16) Å	µ = 0.13 mm⁻¹
c = 7.1523 (3) Å	T = 296 K
V = 6758.7 (5) Å³	Needle, light brown
Z = 18	0.67 × 0.25 × 0.04 mm
F(000) = 3132

Data collection top

Stoe IPDS 2 diffractometer	2958 independent reflections
Radiation source: fine-focus sealed tube	1380 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.140
ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −40→40
T_min = 0.951, T_max = 0.994	k = −39→40
16356 measured reflections	l = −8→8

Refinement top

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0292P)²] where P = (F_o² + 2F_c²)/3
2958 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₁F₃N₂O₄	Z = 18
M_r = 340.26	Mo Kα radiation
Trigonal, R3	µ = 0.13 mm⁻¹
a = 33.0327 (16) Å	T = 296 K
c = 7.1523 (3) Å	0.67 × 0.25 × 0.04 mm
V = 6758.7 (5) Å³

Data collection top

Stoe IPDS 2 diffractometer	2958 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1380 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.994	R_int = 0.140
16356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	Δρ_max = 0.15 e Å⁻³
2958 reflections	Δρ_min = −0.19 e Å⁻³
246 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O4	0.76299 (10)	0.04667 (9)	0.2585 (4)	0.0569 (8)
O1	0.76808 (9)	0.14868 (10)	0.4121 (5)	0.0647 (9)
H1	0.7798	0.1330	0.3798	0.097*
N1	0.83251 (11)	0.12822 (11)	0.3519 (4)	0.0443 (8)
N2	0.90475 (14)	0.32508 (12)	0.6373 (5)	0.0538 (9)
C7	0.86313 (14)	0.17045 (14)	0.4002 (5)	0.0473 (10)
H7	0.8947	0.1797	0.3969	0.057*
C1	0.84911 (13)	0.20297 (13)	0.4583 (5)	0.0417 (10)
O3	0.94606 (11)	0.33571 (11)	0.6341 (5)	0.0724 (10)
C6	0.80087 (14)	0.18987 (14)	0.4640 (6)	0.0488 (11)
C4	0.82253 (15)	0.26645 (15)	0.5825 (6)	0.0529 (11)
H4	0.8141	0.2879	0.6241	0.063*
C2	0.88280 (14)	0.24797 (13)	0.5163 (6)	0.0452 (10)
H2	0.9143	0.2568	0.5131	0.054*
C3	0.86965 (13)	0.27894 (13)	0.5775 (6)	0.0429 (10)
C13	0.80545 (15)	0.04950 (14)	0.2514 (6)	0.0463 (10)
C10	0.89519 (15)	0.06269 (15)	0.2580 (6)	0.0549 (12)
O2	0.89212 (12)	0.35192 (11)	0.6969 (5)	0.0788 (10)
C11	0.85770 (17)	0.01995 (16)	0.2083 (6)	0.0614 (13)
H11	0.8627	−0.0045	0.1772	0.074*
C5	0.78900 (15)	0.22311 (14)	0.5269 (6)	0.0544 (11)
H5	0.7578	0.2152	0.5303	0.065*
C9	0.88791 (15)	0.09902 (15)	0.3038 (6)	0.0532 (11)
H9	0.9132	0.1278	0.3373	0.064*
C8	0.84359 (13)	0.09318 (13)	0.3005 (5)	0.0424 (10)
C12	0.81262 (16)	0.01297 (14)	0.2039 (6)	0.0568 (12)
H12	0.7876	−0.0159	0.1695	0.068*
C15	0.72262 (15)	0.00229 (14)	0.2147 (6)	0.0630 (13)
H15A	0.6950	0.0048	0.2240	0.094*
H15B	0.7205	−0.0209	0.3011	0.094*
H15C	0.7254	−0.0066	0.0897	0.094*
C14	0.9427 (2)	0.0689 (2)	0.2677 (12)	0.0853 (18)
F1A	0.9456 (8)	0.0369 (9)	0.340 (5)	0.142 (14)	0.39 (2)
F2A	0.9748 (7)	0.1072 (7)	0.317 (7)	0.158 (16)	0.39 (2)
F3A	0.9570 (6)	0.0665 (12)	0.074 (2)	0.152 (9)	0.39 (2)
F1B	0.9474 (5)	0.0345 (4)	0.221 (3)	0.136 (9)	0.61 (2)
F2B	0.9590 (5)	0.0783 (9)	0.4489 (18)	0.156 (7)	0.61 (2)
F3B	0.9727 (4)	0.1064 (6)	0.181 (2)	0.128 (7)	0.61 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0435 (17)	0.0424 (17)	0.077 (2)	0.0155 (15)	0.0007 (15)	−0.0058 (15)
O1	0.0437 (17)	0.048 (2)	0.097 (3)	0.0190 (16)	0.0001 (17)	−0.0140 (17)
N1	0.045 (2)	0.0307 (18)	0.050 (2)	0.0140 (17)	−0.0002 (17)	−0.0023 (15)
N2	0.057 (3)	0.040 (2)	0.059 (2)	0.021 (2)	−0.0016 (19)	−0.0045 (18)
C7	0.040 (2)	0.051 (3)	0.051 (3)	0.024 (2)	0.005 (2)	0.006 (2)
C1	0.036 (2)	0.040 (2)	0.046 (2)	0.017 (2)	0.0036 (18)	0.0010 (19)
O3	0.047 (2)	0.058 (2)	0.100 (3)	0.0173 (17)	−0.0097 (18)	−0.0190 (18)
C6	0.046 (3)	0.035 (2)	0.058 (3)	0.014 (2)	0.005 (2)	−0.002 (2)
C4	0.058 (3)	0.049 (3)	0.061 (3)	0.034 (2)	0.004 (2)	0.001 (2)
C2	0.039 (2)	0.044 (3)	0.051 (3)	0.019 (2)	−0.0017 (19)	−0.0007 (19)
C3	0.043 (3)	0.035 (2)	0.051 (3)	0.020 (2)	−0.0026 (19)	0.0000 (19)
C13	0.047 (3)	0.043 (3)	0.048 (3)	0.021 (2)	0.008 (2)	0.008 (2)
C10	0.051 (3)	0.048 (3)	0.069 (3)	0.027 (2)	0.006 (2)	0.001 (2)
O2	0.081 (2)	0.0451 (19)	0.111 (3)	0.032 (2)	0.003 (2)	−0.0172 (19)
C11	0.065 (3)	0.047 (3)	0.079 (4)	0.033 (3)	0.006 (3)	0.000 (2)
C5	0.041 (3)	0.051 (3)	0.070 (3)	0.022 (2)	0.005 (2)	0.000 (2)
C9	0.049 (3)	0.044 (3)	0.062 (3)	0.020 (2)	0.002 (2)	0.002 (2)
C8	0.044 (3)	0.031 (2)	0.046 (2)	0.014 (2)	0.0038 (19)	0.0014 (18)
C12	0.058 (3)	0.035 (2)	0.071 (3)	0.019 (2)	0.001 (2)	−0.003 (2)
C15	0.046 (3)	0.045 (3)	0.081 (3)	0.010 (2)	−0.008 (2)	−0.009 (2)
C14	0.060 (4)	0.059 (4)	0.135 (7)	0.028 (3)	0.014 (4)	0.006 (4)
F1A	0.095 (10)	0.15 (2)	0.23 (3)	0.094 (15)	0.062 (17)	0.12 (2)
F2A	0.069 (11)	0.075 (12)	0.33 (5)	0.041 (9)	−0.09 (2)	−0.032 (18)
F3A	0.137 (12)	0.20 (2)	0.152 (13)	0.107 (15)	0.075 (9)	0.028 (14)
F1B	0.078 (6)	0.094 (10)	0.26 (2)	0.058 (7)	−0.002 (10)	−0.056 (12)
F2B	0.132 (9)	0.257 (19)	0.150 (9)	0.149 (12)	−0.068 (7)	−0.062 (10)
F3B	0.060 (7)	0.130 (11)	0.194 (15)	0.047 (7)	0.047 (8)	0.054 (12)

Geometric parameters (Å, º) top

O4—C13	1.359 (5)	C13—C8	1.405 (5)
O4—C15	1.439 (4)	C10—C9	1.376 (5)
O1—C6	1.299 (4)	C10—C11	1.380 (6)
O1—H1	0.8200	C10—C14	1.478 (7)
N1—C7	1.295 (5)	C11—C12	1.389 (6)
N1—C8	1.426 (5)	C11—H11	0.9300
N2—O3	1.227 (4)	C5—H5	0.9300
N2—O2	1.230 (4)	C9—C8	1.378 (5)
N2—C3	1.443 (5)	C9—H9	0.9300
C7—C1	1.428 (5)	C12—H12	0.9300
C7—H7	0.9300	C15—H15A	0.9600
C1—C2	1.402 (5)	C15—H15B	0.9600
C1—C6	1.428 (5)	C15—H15C	0.9600
C6—C5	1.411 (5)	C14—F1A	1.225 (17)
C4—C5	1.360 (6)	C14—F2A	1.228 (19)
C4—C3	1.397 (5)	C14—F3A	1.481 (17)
C4—H4	0.9300	C14—F1B	1.267 (12)
C2—C3	1.368 (5)	C14—F3B	1.295 (13)
C2—H2	0.9300	C14—F2B	1.379 (12)
C13—C12	1.383 (5)

C13—O4—C15	117.4 (3)	C12—C11—H11	119.5
C6—O1—H1	109.5	C4—C5—C6	121.0 (4)
C7—N1—C8	124.3 (4)	C4—C5—H5	119.5
O3—N2—O2	122.0 (4)	C6—C5—H5	119.5
O3—N2—C3	119.2 (4)	C10—C9—C8	120.7 (4)
O2—N2—C3	118.8 (4)	C10—C9—H9	119.6
N1—C7—C1	121.0 (4)	C8—C9—H9	119.6
N1—C7—H7	119.5	C9—C8—C13	119.5 (4)
C1—C7—H7	119.5	C9—C8—N1	124.6 (4)
C2—C1—C6	119.1 (4)	C13—C8—N1	115.8 (4)
C2—C1—C7	120.0 (4)	C13—C12—C11	119.1 (4)
C6—C1—C7	120.9 (4)	C13—C12—H12	120.4
O1—C6—C5	119.7 (4)	C11—C12—H12	120.4
O1—C6—C1	121.9 (4)	O4—C15—H15A	109.5
C5—C6—C1	118.4 (4)	O4—C15—H15B	109.5
C5—C4—C3	120.3 (4)	H15A—C15—H15B	109.5
C5—C4—H4	119.9	O4—C15—H15C	109.5
C3—C4—H4	119.9	H15A—C15—H15C	109.5
C3—C2—C1	120.5 (4)	H15B—C15—H15C	109.5
C3—C2—H2	119.8	F1A—C14—F2A	111.5 (16)
C1—C2—H2	119.8	F1A—C14—F3A	100.7 (13)
C2—C3—C4	120.7 (4)	F2A—C14—F3A	100.8 (18)
C2—C3—N2	119.8 (4)	F1B—C14—F3B	110.7 (11)
C4—C3—N2	119.5 (4)	F1B—C14—F2B	103.7 (10)
O4—C13—C12	124.8 (4)	F3B—C14—F2B	102.1 (10)
O4—C13—C8	115.2 (4)	F1A—C14—C10	115.9 (11)
C12—C13—C8	120.0 (4)	F2A—C14—C10	117.9 (11)
C9—C10—C11	119.6 (4)	C10—C14—F3A	107.1 (8)
C9—C10—C14	120.3 (5)	F1B—C14—C10	117.5 (8)
C11—C10—C14	120.1 (5)	F3B—C14—C10	111.3 (8)
C10—C11—C12	121.0 (4)	F2B—C14—C10	110.2 (6)
C10—C11—H11	119.5

C8—N1—C7—C1	−177.0 (3)	C14—C10—C9—C8	−178.1 (5)
N1—C7—C1—C2	177.7 (4)	C10—C9—C8—C13	0.6 (6)
N1—C7—C1—C6	−0.3 (6)	C10—C9—C8—N1	177.7 (4)
C2—C1—C6—O1	180.0 (4)	O4—C13—C8—C9	177.8 (4)
C7—C1—C6—O1	−1.9 (6)	C12—C13—C8—C9	−1.0 (6)
C2—C1—C6—C5	0.5 (6)	O4—C13—C8—N1	0.4 (5)
C7—C1—C6—C5	178.5 (4)	C12—C13—C8—N1	−178.4 (3)
C6—C1—C2—C3	0.0 (6)	C7—N1—C8—C9	3.1 (6)
C7—C1—C2—C3	−178.1 (4)	C7—N1—C8—C13	−179.6 (4)
C1—C2—C3—C4	−0.3 (6)	O4—C13—C12—C11	−177.7 (4)
C1—C2—C3—N2	179.8 (4)	C8—C13—C12—C11	0.9 (6)
C5—C4—C3—C2	0.2 (6)	C10—C11—C12—C13	−0.4 (7)
C5—C4—C3—N2	−179.9 (4)	C9—C10—C14—F1A	136 (2)
O3—N2—C3—C2	−0.7 (6)	C11—C10—C14—F1A	−42 (2)
O2—N2—C3—C2	−177.9 (4)	C9—C10—C14—F2A	0 (3)
O3—N2—C3—C4	179.4 (4)	C11—C10—C14—F2A	−178 (3)
O2—N2—C3—C4	2.2 (6)	C9—C10—C14—F1B	−179.0 (14)
C15—O4—C13—C12	0.5 (6)	C11—C10—C14—F1B	2.9 (16)
C15—O4—C13—C8	−178.3 (4)	C9—C10—C14—F3B	−49.9 (13)
C9—C10—C11—C12	−0.1 (7)	C11—C10—C14—F3B	132.0 (12)
C14—C10—C11—C12	178.0 (5)	C9—C10—C14—F2B	62.5 (13)
C3—C4—C5—C6	0.3 (6)	C11—C10—C14—F2B	−115.5 (12)
O1—C6—C5—C4	179.8 (4)	C9—C10—C14—F3A	−112.9 (16)
C1—C6—C5—C4	−0.6 (6)	C11—C10—C14—F3A	69.1 (16)
C11—C10—C9—C8	0.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.571 (4)	148
O1—H1···O4	0.82	2.76	3.468 (4)	146
C7—H7···O2ⁱ	0.93	2.55	3.476 (7)	176
C9—H9···O2ⁱ	0.93	2.46	3.378 (6)	169

Symmetry code: (i) −y+4/3, x−y−1/3, z−1/3.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.84	2.571 (4)	148
O1—H1···O4	0.82	2.76	3.468 (4)	146
C7—H7···O2ⁱ	0.93	2.55	3.476 (7)	176
C9—H9···O2ⁱ	0.93	2.46	3.378 (6)	169

Symmetry code: (i) −y+4/3, x−y−1/3, z−1/3.

Acknowledgements

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).

References

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Volume 71| Part 7| July 2015| Pages o466-o467

doi:10.1107/S2056989015010129

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

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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