2-Methyl-6-[2-(trifluoro-meth-yl)phenyl-imino-meth-yl]phenol.

The title compound, C(15)H(12)F(3)NO, is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The dihedral angle between the aromatic rings is 38.79 (5)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring. In addition, there is an intra-molecular short C-H⋯F contact.

Related literature

For the biological properties of Schiff bases, see: Barton et al. (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶) Taggi et al. (2002 ▶); Aydoğan et al. (2001 ▶). Schiff base compounds can be classified by their photochromic and thermochromic characteristics, see: Cohen et al. (1964 ▶); Moustakali-Mavridis et al. (1978 ▶). For the graph-set description of hydrogen bonds, see: Bernstein et al. (1995 ▶. For a related structure, see: Temel et al. (2007 ▶).

Experimental

Crystal data

C15H12F3NO

M = 279.26

Orthorhombic,

a = 8.1634 (3) Å

b = 11.8810 (6) Å

c = 13.4469 (7) Å

V = 1304.21 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.73 × 0.51 × 0.37 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.943, T max = 0.970

14752 measured reflections

1565 independent reflections

1396 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.07

1565 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.09 e Å−3

Δρmin = −0.15 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044560/bt5114sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044560/bt5114Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12F3NO	F(000) = 576
Mr = 279.26	Dx = 1.422 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 19471 reflections
a = 8.1634 (3) Å	θ = 1.5–28.0°
b = 11.8810 (6) Å	µ = 0.12 mm−1
c = 13.4469 (7) Å	T = 293 K
V = 1304.21 (11) Å3	Prism, light yellow
Z = 4	0.73 × 0.51 × 0.37 mm

Stoe IPDS II diffractometer	1565 independent reflections
Radiation source: fine-focus sealed tube	1396 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.3°
rotation method scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.943, Tmax = 0.970	l = −16→16
14752 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.0179P] where P = (Fo2 + 2Fc2)/3
1565 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.09 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. 270 frames, detector distance = 100 mm

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.

	x	y	z	Uiso*/Ueq
C1	0.5950 (2)	0.12366 (13)	0.48589 (13)	0.0521 (4)
C2	0.7604 (2)	0.09829 (14)	0.46506 (13)	0.0521 (4)
C3	0.8634 (3)	0.05379 (15)	0.53818 (15)	0.0589 (5)
C4	0.7966 (3)	0.03487 (16)	0.63136 (16)	0.0669 (5)
H4	0.8626	0.0039	0.6806	0.080*
C5	0.6363 (3)	0.06007 (18)	0.65389 (16)	0.0725 (6)
H5	0.5960	0.0471	0.7176	0.087*
C6	0.5366 (3)	0.10426 (16)	0.58227 (15)	0.0653 (5)
H6	0.4285	0.1217	0.5977	0.078*
C7	1.0381 (3)	0.0287 (2)	0.51468 (19)	0.0804 (6)
H7A	1.0972	0.0979	0.5064	0.121*
H7B	1.0440	−0.0144	0.4544	0.121*
H7C	1.0857	−0.0137	0.5682	0.121*
C8	0.4855 (2)	0.16517 (13)	0.41041 (14)	0.0536 (4)
H8	0.3783	0.1826	0.4280	0.064*
C9	0.4144 (2)	0.21161 (13)	0.24725 (14)	0.0525 (4)
C10	0.2558 (3)	0.16864 (15)	0.24564 (17)	0.0638 (5)
H10	0.2227	0.1181	0.2945	0.077*
C11	0.1481 (3)	0.20022 (18)	0.1726 (2)	0.0757 (6)
H11	0.0427	0.1705	0.1720	0.091*
C12	0.1946 (3)	0.27551 (18)	0.10000 (19)	0.0747 (6)
H12	0.1202	0.2976	0.0514	0.090*
C13	0.3510 (3)	0.31792 (17)	0.09962 (16)	0.0661 (5)
H13	0.3827	0.3681	0.0502	0.079*
C14	0.4618 (2)	0.28640 (13)	0.17241 (14)	0.0541 (4)
C15	0.6310 (3)	0.33225 (16)	0.17122 (15)	0.0625 (5)
N1	0.53021 (19)	0.17904 (11)	0.31975 (11)	0.0530 (3)
O1	0.82427 (18)	0.11539 (13)	0.37360 (11)	0.0671 (4)
F1	0.67184 (18)	0.38548 (12)	0.25515 (11)	0.0888 (4)
F2	0.74444 (17)	0.25364 (12)	0.15746 (12)	0.0872 (4)
F3	0.65390 (18)	0.40802 (13)	0.09842 (12)	0.0930 (5)
H1	0.738 (4)	0.141 (2)	0.335 (2)	0.097 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0552 (10)	0.0460 (7)	0.0550 (9)	−0.0031 (7)	0.0000 (8)	−0.0035 (7)
C2	0.0568 (10)	0.0468 (7)	0.0528 (9)	−0.0038 (7)	−0.0010 (8)	−0.0033 (7)
C3	0.0606 (11)	0.0518 (8)	0.0644 (11)	−0.0035 (8)	−0.0118 (9)	−0.0052 (8)
C4	0.0800 (15)	0.0577 (9)	0.0631 (11)	−0.0075 (9)	−0.0180 (11)	0.0033 (8)
C5	0.0891 (16)	0.0757 (11)	0.0528 (11)	−0.0107 (11)	0.0015 (11)	0.0036 (9)
C6	0.0685 (12)	0.0689 (10)	0.0584 (10)	−0.0042 (10)	0.0059 (10)	−0.0013 (9)
C7	0.0621 (13)	0.0903 (14)	0.0889 (16)	0.0081 (11)	−0.0139 (13)	−0.0037 (13)
C8	0.0492 (10)	0.0487 (7)	0.0630 (10)	0.0005 (7)	0.0041 (8)	−0.0018 (7)
C9	0.0490 (9)	0.0471 (7)	0.0613 (10)	0.0058 (7)	−0.0018 (8)	−0.0009 (7)
C10	0.0527 (11)	0.0570 (9)	0.0816 (13)	0.0005 (8)	−0.0025 (10)	0.0039 (10)
C11	0.0528 (11)	0.0695 (11)	0.1048 (17)	0.0025 (9)	−0.0140 (12)	−0.0067 (12)
C12	0.0711 (14)	0.0692 (11)	0.0837 (14)	0.0144 (11)	−0.0227 (12)	−0.0005 (11)
C13	0.0706 (13)	0.0599 (10)	0.0678 (12)	0.0109 (9)	−0.0078 (10)	0.0059 (9)
C14	0.0559 (10)	0.0478 (7)	0.0586 (10)	0.0070 (7)	−0.0011 (8)	−0.0010 (7)
C15	0.0604 (11)	0.0620 (10)	0.0652 (11)	0.0010 (8)	0.0044 (9)	0.0072 (9)
N1	0.0483 (8)	0.0525 (7)	0.0583 (8)	0.0029 (6)	−0.0018 (7)	0.0025 (6)
O1	0.0530 (8)	0.0886 (9)	0.0596 (8)	0.0050 (7)	0.0044 (7)	0.0051 (7)
F1	0.0835 (10)	0.0967 (9)	0.0861 (9)	−0.0323 (8)	0.0002 (8)	−0.0127 (7)
F2	0.0565 (7)	0.0926 (8)	0.1124 (11)	0.0123 (7)	0.0131 (7)	0.0079 (8)
F3	0.0857 (9)	0.0928 (8)	0.1004 (10)	−0.0116 (8)	0.0083 (8)	0.0376 (8)

C1—C6	1.400 (3)	C9—C10	1.392 (3)
C1—C2	1.411 (3)	C9—C14	1.397 (2)
C1—C8	1.440 (3)	C9—N1	1.412 (2)
C2—O1	1.351 (2)	C10—C11	1.371 (3)
C2—C3	1.398 (3)	C10—H10	0.9300
C3—C4	1.385 (3)	C11—C12	1.377 (3)
C3—C7	1.491 (3)	C11—H11	0.9300
C4—C5	1.376 (3)	C12—C13	1.373 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.366 (3)	C13—C14	1.385 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.484 (3)
C7—H7A	0.9600	C15—F2	1.328 (2)
C7—H7B	0.9600	C15—F1	1.336 (2)
C7—H7C	0.9600	C15—F3	1.343 (2)
C8—N1	1.283 (2)	O1—H1	0.93 (3)
C8—H8	0.9300
C6—C1—C2	118.34 (18)	C10—C9—C14	118.66 (18)
C6—C1—C8	119.82 (18)	C10—C9—N1	122.19 (17)
C2—C1—C8	121.82 (16)	C14—C9—N1	119.10 (17)
O1—C2—C3	117.71 (18)	C11—C10—C9	120.5 (2)
O1—C2—C1	121.19 (17)	C11—C10—H10	119.8
C3—C2—C1	121.10 (18)	C9—C10—H10	119.8
C4—C3—C2	117.4 (2)	C10—C11—C12	120.6 (2)
C4—C3—C7	122.4 (2)	C10—C11—H11	119.7
C2—C3—C7	120.1 (2)	C12—C11—H11	119.7
C5—C4—C3	122.6 (2)	C13—C12—C11	119.8 (2)
C5—C4—H4	118.7	C13—C12—H12	120.1
C3—C4—H4	118.7	C11—C12—H12	120.1
C6—C5—C4	119.7 (2)	C12—C13—C14	120.4 (2)
C6—C5—H5	120.2	C12—C13—H13	119.8
C4—C5—H5	120.2	C14—C13—H13	119.8
C5—C6—C1	120.9 (2)	C13—C14—C9	120.02 (19)
C5—C6—H6	119.6	C13—C14—C15	120.06 (17)
C1—C6—H6	119.6	C9—C14—C15	119.91 (16)
C3—C7—H7A	109.5	F2—C15—F1	106.04 (18)
C3—C7—H7B	109.5	F2—C15—F3	105.81 (17)
H7A—C7—H7B	109.5	F1—C15—F3	105.28 (16)
C3—C7—H7C	109.5	F2—C15—C14	113.09 (15)
H7A—C7—H7C	109.5	F1—C15—C14	113.39 (17)
H7B—C7—H7C	109.5	F3—C15—C14	112.55 (17)
N1—C8—C1	122.48 (18)	C8—N1—C9	120.06 (16)
N1—C8—H8	118.8	C2—O1—H1	105.5 (18)
C1—C8—H8	118.8
C6—C1—C2—O1	−179.82 (16)	C9—C10—C11—C12	−0.5 (3)
C8—C1—C2—O1	2.1 (2)	C10—C11—C12—C13	1.2 (3)
C6—C1—C2—C3	0.7 (2)	C11—C12—C13—C14	−0.7 (3)
C8—C1—C2—C3	−177.39 (15)	C12—C13—C14—C9	−0.4 (3)
O1—C2—C3—C4	−179.06 (16)	C12—C13—C14—C15	179.73 (18)
C1—C2—C3—C4	0.5 (2)	C10—C9—C14—C13	1.1 (2)
O1—C2—C3—C7	1.1 (3)	N1—C9—C14—C13	178.90 (16)
C1—C2—C3—C7	−179.41 (17)	C10—C9—C14—C15	−179.04 (17)
C2—C3—C4—C5	−1.2 (3)	N1—C9—C14—C15	−1.3 (2)
C7—C3—C4—C5	178.6 (2)	C13—C14—C15—F2	−116.15 (19)
C3—C4—C5—C6	0.8 (3)	C9—C14—C15—F2	64.0 (2)
C4—C5—C6—C1	0.4 (3)	C13—C14—C15—F1	123.08 (19)
C2—C1—C6—C5	−1.1 (3)	C9—C14—C15—F1	−56.8 (2)
C8—C1—C6—C5	176.98 (17)	C13—C14—C15—F3	3.7 (3)
C6—C1—C8—N1	−176.38 (16)	C9—C14—C15—F3	−176.13 (16)
C2—C1—C8—N1	1.6 (3)	C1—C8—N1—C9	175.06 (14)
C14—C9—C10—C11	−0.7 (3)	C10—C9—N1—C8	−39.7 (2)
N1—C9—C10—C11	−178.38 (17)	C14—C9—N1—C8	142.65 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.93 (3)	1.77 (3)	2.619 (2)	151 (3)
C13—H13···F3	0.93	2.36	2.694 (3)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.93 (3)	1.77 (3)	2.619 (2)	151 (3)
C13—H13⋯F3	0.93	2.36	2.694 (3)	101