(E)-2-[3-(Trifluoro-meth-yl)phenyl-imino-meth-yl]benzene-1,4-diol.

In the title compound, C(14)H(10)F(3)NO(2), the two benzene rings are oriented at a dihedral angle of 31.94 (14)°. An intra-molecular O-H⋯N hydrogen bond helps to stabilize the mol-ecular structure. In the crystal, inter-molecular O-H⋯O hydrogen bonding links the mol-ecules, forming chains running along the crystallographic a axis. The F atoms of the trifluoro-methyl group are disordered over two positions with refined site occupancies of 0.488 (5) and 0.512 (5).

Related literature

For the biological properties of Schiff bases, see: Lozier et al. (1975 ▶). For Schiff base tautomerism, see: Şahin et al. (2005 ▶); Hadjoudis et al. (1987 ▶). For the structure of a similar compound, see: Temel et al. (2007 ▶). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶). For related structural studies of Schiff bases, see: (Gül et al., 2007 ▶; Şahin et al., 2009a ▶,b ▶,c ▶).

Experimental

Crystal data

C14H10F3NO2

M = 281.23

Triclinic,

a = 7.1019 (8) Å

b = 8.5910 (8) Å

c = 11.0412 (11) Å

α = 73.862 (8)°

β = 74.133 (7)°

γ = 87.431 (8)°

V = 622.10 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.49 × 0.32 × 0.02 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: multi-scan (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.934, T max = 0.995

6675 measured reflections

2548 independent reflections

1490 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.100

wR(F 2) = 0.293

S = 1.07

2548 reflections

183 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.56 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/S1600536809041610/xu2631sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041610/xu2631Isup2.hkl

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

C14H10F3NO2	Z = 2
Mr = 281.23	F(000) = 288
Triclinic, P1	Dx = 1.501 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1019 (8) Å	Cell parameters from 6675 reflections
b = 8.5910 (8) Å	θ = 2.0–27.4°
c = 11.0412 (11) Å	µ = 0.13 mm−1
α = 73.862 (8)°	T = 296 K
β = 74.133 (7)°	Plate, brown
γ = 87.431 (8)°	0.49 × 0.32 × 0.02 mm
V = 622.10 (11) Å3

Stoe IPDS II diffractometer	2548 independent reflections
Radiation source: fine-focus sealed tube	1490 reflections with I > 2σ(I)
graphite	Rint = 0.073
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.0°
ω scans	h = −8→8
Absorption correction: multi-scan (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.934, Tmax = 0.995	l = −13→13
6675 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)] = 0.100	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.293	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.131P)2 + 0.6957P] where P = (Fo2 + 2Fc2)/3
2548 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

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	Occ. (<1)
C1	0.8807 (6)	0.4507 (5)	0.3828 (4)	0.0464 (11)
H6	0.9747	0.5267	0.3765	0.056*
C2	0.9124 (6)	0.2884 (5)	0.4264 (4)	0.0463 (11)
C3	0.7727 (6)	0.1751 (5)	0.4348 (5)	0.0499 (11)
H3	0.7950	0.0650	0.4627	0.060*
C4	0.6009 (6)	0.2243 (5)	0.4020 (5)	0.0527 (12)
H4	0.5075	0.1474	0.4089	0.063*
C5	0.5675 (6)	0.3880 (5)	0.3588 (4)	0.0447 (10)
C6	0.7087 (6)	0.5034 (5)	0.3475 (4)	0.0429 (10)
C7	0.6778 (7)	0.6751 (5)	0.3017 (4)	0.0476 (11)
H7	0.7704	0.7493	0.3002	0.057*
C8	0.5029 (7)	0.8960 (5)	0.2113 (5)	0.0510 (11)
C9	0.3124 (7)	0.9517 (6)	0.2334 (5)	0.0589 (13)
H9	0.2073	0.8798	0.2822	0.071*
C10	0.2797 (8)	1.1122 (7)	0.1834 (5)	0.0677 (15)
H10	0.1525	1.1489	0.1997	0.081*
C11	0.4334 (8)	1.2195 (6)	0.1095 (5)	0.0650 (15)
H11	0.4104	1.3281	0.0747	0.078*
C12	0.6225 (7)	1.1646 (5)	0.0873 (5)	0.0558 (12)
C13	0.6580 (7)	1.0035 (5)	0.1379 (5)	0.0539 (12)
H13	0.7856	0.9676	0.1228	0.065*
C14	0.7854 (9)	1.2793 (6)	0.0089 (6)	0.0711 (16)
N1	0.5264 (5)	0.7276 (4)	0.2631 (4)	0.0506 (10)
O1	0.3968 (4)	0.4333 (4)	0.3267 (4)	0.0603 (10)
H1	0.405 (9)	0.543 (8)	0.297 (6)	0.09 (2)*
O2	1.0773 (4)	0.2313 (4)	0.4650 (4)	0.0630 (10)
H2	1.1482	0.3081	0.4575	0.094*
F1A	0.9366 (14)	1.2094 (11)	−0.0622 (10)	0.1040 (13)	0.488 (5)
F2A	0.8727 (14)	1.3390 (11)	0.0824 (9)	0.1040 (13)	0.488 (5)
F3A	0.7488 (14)	1.4075 (12)	−0.0793 (10)	0.1040 (13)	0.488 (5)
F1B	0.9660 (13)	1.2261 (10)	0.0118 (10)	0.1040 (13)	0.512 (5)
F2B	0.7781 (13)	1.4179 (10)	0.0474 (9)	0.1040 (13)	0.512 (5)
F3B	0.7846 (14)	1.3397 (11)	−0.1146 (10)	0.1040 (13)	0.512 (5)

	U11	U22	U33	U12	U13	U23
C1	0.042 (2)	0.038 (2)	0.055 (3)	−0.0027 (17)	−0.0144 (19)	−0.0047 (18)
C2	0.038 (2)	0.043 (2)	0.052 (2)	0.0029 (17)	−0.0122 (18)	−0.0050 (19)
C3	0.047 (2)	0.034 (2)	0.062 (3)	0.0019 (17)	−0.012 (2)	−0.0048 (19)
C4	0.045 (2)	0.042 (2)	0.068 (3)	−0.0042 (19)	−0.017 (2)	−0.009 (2)
C5	0.035 (2)	0.042 (2)	0.053 (2)	0.0005 (17)	−0.0104 (18)	−0.0088 (18)
C6	0.039 (2)	0.037 (2)	0.051 (2)	0.0042 (16)	−0.0117 (18)	−0.0098 (17)
C7	0.053 (2)	0.038 (2)	0.050 (2)	0.0008 (18)	−0.015 (2)	−0.0083 (18)
C8	0.055 (3)	0.044 (2)	0.054 (3)	0.013 (2)	−0.021 (2)	−0.009 (2)
C9	0.058 (3)	0.060 (3)	0.058 (3)	0.016 (2)	−0.020 (2)	−0.013 (2)
C10	0.059 (3)	0.070 (3)	0.072 (3)	0.027 (3)	−0.020 (3)	−0.019 (3)
C11	0.080 (4)	0.050 (3)	0.065 (3)	0.029 (3)	−0.026 (3)	−0.015 (2)
C12	0.071 (3)	0.041 (2)	0.057 (3)	0.013 (2)	−0.026 (2)	−0.010 (2)
C13	0.052 (2)	0.046 (2)	0.060 (3)	0.014 (2)	−0.014 (2)	−0.011 (2)
C14	0.084 (4)	0.045 (3)	0.076 (4)	0.015 (3)	−0.025 (3)	−0.001 (3)
N1	0.051 (2)	0.042 (2)	0.056 (2)	0.0084 (16)	−0.0164 (17)	−0.0072 (16)
O1	0.0447 (17)	0.0469 (19)	0.086 (2)	0.0006 (14)	−0.0290 (16)	−0.0024 (17)
O2	0.0441 (17)	0.0491 (19)	0.091 (3)	0.0037 (14)	−0.0281 (17)	−0.0018 (17)
F1A	0.109 (3)	0.078 (3)	0.103 (3)	−0.015 (2)	−0.019 (2)	0.002 (2)
F2A	0.109 (3)	0.078 (3)	0.103 (3)	−0.015 (2)	−0.019 (2)	0.002 (2)
F3A	0.109 (3)	0.078 (3)	0.103 (3)	−0.015 (2)	−0.019 (2)	0.002 (2)
F1B	0.109 (3)	0.078 (3)	0.103 (3)	−0.015 (2)	−0.019 (2)	0.002 (2)
F2B	0.109 (3)	0.078 (3)	0.103 (3)	−0.015 (2)	−0.019 (2)	0.002 (2)
F3B	0.109 (3)	0.078 (3)	0.103 (3)	−0.015 (2)	−0.019 (2)	0.002 (2)

C1—C2	1.374 (6)	C9—C10	1.370 (7)
C1—C6	1.400 (6)	C9—H9	0.9300
C1—H6	0.9300	C10—C11	1.376 (8)
C2—O2	1.378 (5)	C10—H10	0.9300
C2—C3	1.388 (6)	C11—C12	1.383 (7)
C3—C4	1.382 (6)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.381 (6)
C4—C5	1.386 (6)	C12—C14	1.463 (8)
C4—H4	0.9300	C13—H13	0.9300
C5—O1	1.365 (5)	C14—F3B	1.319 (11)
C5—C6	1.399 (6)	C14—F3A	1.321 (11)
C6—C7	1.448 (6)	C14—F1B	1.348 (11)
C7—N1	1.281 (6)	C14—F2A	1.357 (12)
C7—H7	0.9300	C14—F2B	1.365 (11)
C8—C13	1.382 (7)	C14—F1A	1.369 (11)
C8—C9	1.395 (6)	O1—H1	0.91 (7)
C8—N1	1.421 (5)	O2—H2	0.8200
C2—C1—C6	120.9 (4)	C10—C11—C12	119.4 (4)
C2—C1—H6	119.6	C10—C11—H11	120.3
C6—C1—H6	119.6	C12—C11—H11	120.3
C1—C2—O2	122.8 (4)	C13—C12—C11	120.7 (5)
C1—C2—C3	119.5 (4)	C13—C12—C14	120.1 (4)
O2—C2—C3	117.7 (4)	C11—C12—C14	119.2 (4)
C4—C3—C2	120.6 (4)	C12—C13—C8	119.7 (4)
C4—C3—H3	119.7	C12—C13—H13	120.2
C2—C3—H3	119.7	C8—C13—H13	120.2
C3—C4—C5	120.1 (4)	F3B—C14—F1B	108.3 (7)
C3—C4—H4	120.0	F3A—C14—F1B	124.5 (7)
C5—C4—H4	120.0	F3B—C14—F2A	129.6 (7)
O1—C5—C4	118.9 (4)	F3A—C14—F2A	105.4 (7)
O1—C5—C6	121.2 (4)	F1B—C14—F2A	64.3 (6)
C4—C5—C6	119.9 (4)	F3B—C14—F2B	100.7 (6)
C5—C6—C1	119.0 (4)	F3A—C14—F2B	67.7 (6)
C5—C6—C7	120.9 (4)	F1B—C14—F2B	103.3 (7)
C1—C6—C7	120.1 (4)	F3B—C14—F1A	74.1 (7)
N1—C7—C6	121.8 (4)	F3A—C14—F1A	103.5 (7)
N1—C7—H7	119.1	F2A—C14—F1A	102.9 (7)
C6—C7—H7	119.1	F2B—C14—F1A	131.6 (7)
C13—C8—C9	119.5 (4)	F3B—C14—C12	113.9 (7)
C13—C8—N1	123.1 (4)	F3A—C14—C12	117.6 (6)
C9—C8—N1	117.3 (4)	F1B—C14—C12	116.0 (5)
C10—C9—C8	120.1 (5)	F2A—C14—C12	113.3 (6)
C10—C9—H9	119.9	F2B—C14—C12	113.1 (6)
C8—C9—H9	119.9	F1A—C14—C12	112.7 (6)
C9—C10—C11	120.6 (5)	C7—N1—C8	121.3 (4)
C9—C10—H10	119.7	C5—O1—H1	106 (4)
C11—C10—H10	119.7	C2—O2—H2	109.5
C6—C1—C2—O2	−178.4 (4)	C10—C11—C12—C14	−179.8 (6)
C6—C1—C2—C3	0.5 (7)	C11—C12—C13—C8	0.2 (8)
C1—C2—C3—C4	−1.2 (7)	C14—C12—C13—C8	−179.7 (5)
O2—C2—C3—C4	177.7 (4)	C9—C8—C13—C12	−0.2 (7)
C2—C3—C4—C5	0.8 (7)	N1—C8—C13—C12	177.8 (5)
C3—C4—C5—O1	179.8 (4)	C13—C12—C14—F3B	114.4 (7)
C3—C4—C5—C6	0.4 (7)	C11—C12—C14—F3B	−65.5 (8)
O1—C5—C6—C1	179.5 (4)	C13—C12—C14—F3A	152.7 (7)
C4—C5—C6—C1	−1.2 (6)	C11—C12—C14—F3A	−27.2 (10)
O1—C5—C6—C7	0.2 (7)	C13—C12—C14—F1B	−12.3 (10)
C4—C5—C6—C7	179.5 (4)	C11—C12—C14—F1B	167.8 (7)
C2—C1—C6—C5	0.7 (6)	C13—C12—C14—F2A	−83.9 (8)
C2—C1—C6—C7	−180.0 (4)	C11—C12—C14—F2A	96.2 (7)
C5—C6—C7—N1	−3.9 (7)	C13—C12—C14—F2B	−131.4 (7)
C1—C6—C7—N1	176.8 (4)	C11—C12—C14—F2B	48.7 (8)
C13—C8—C9—C10	−0.4 (8)	C13—C12—C14—F1A	32.4 (9)
N1—C8—C9—C10	−178.5 (5)	C11—C12—C14—F1A	−147.5 (7)
C8—C9—C10—C11	1.0 (8)	C6—C7—N1—C8	−176.4 (4)
C9—C10—C11—C12	−0.9 (9)	C13—C8—N1—C7	34.0 (7)
C10—C11—C12—C13	0.3 (8)	C9—C8—N1—C7	−147.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.07	2.735 (5)	138
O1—H1···N1	0.91 (7)	1.74 (7)	2.569 (5)	151 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.07	2.735 (5)	138
O1—H1⋯N1	0.91 (7)	1.74 (7)	2.569 (5)	151 (6)

Symmetry code: (i) .