2-[(E)-2-Hy-droxy-5-(trifluoro-meth-oxy)benzyl-idene-amino]-4-methyl-phenol.

The title compound, C(15)H(12)F(3)NO(3), is a Schiff base which adopts the cis-quinoid form in the solid state. The dihedral angle between the least-squares planes of the benzene rings being 3.6 (1)°. The F atoms of the -CF(3) group are disordered over two sets of sites with refined occupancies of 0.61 (5) and 0.39 (5). An intra-molecular N-H⋯O hydrogen bond occurs. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds.

Related literature

Schiff base compounds can be classified by their photochromic and thermochromic characteristics, see: Calligaris et al. (1972 ▶); Cohen et al. (1964 ▶); Hadjoudis et al. (1987 ▶). For Schiff base tautomerism, see: Karabıyık et al. (2008 ▶).

Experimental

Crystal data

C15H12F3NO3

M = 311.26

Triclinic,

a = 6.4730 (5) Å

b = 8.4435 (6) Å

c = 13.0369 (9) Å

α = 82.171 (6)°

β = 88.034 (6)°

γ = 85.622 (6)°

V = 703.62 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.58 × 0.27 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.953, T max = 0.995

11152 measured reflections

2762 independent reflections

1328 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.077

S = 0.89

2762 reflections

236 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.10 e Å−3

Δρmin = −0.14 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050579/zq2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050579/zq2072Isup2.hkl

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

C15H12F3NO3	Z = 2
Mr = 311.26	F(000) = 320
Triclinic, P1	Dx = 1.469 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4730 (5) Å	Cell parameters from 7349 reflections
b = 8.4435 (6) Å	θ = 1.6–27.9°
c = 13.0369 (9) Å	µ = 0.13 mm−1
α = 82.171 (6)°	T = 293 K
β = 88.034 (6)°	Prism, yellow
γ = 85.622 (6)°	0.58 × 0.27 × 0.03 mm
V = 703.62 (9) Å3

Stoe IPDS 2 diffractometer	2762 independent reflections
Radiation source: fine-focus sealed tube	1328 reflections with I > 2σ(I)
graphite	Rint = 0.078
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.6°
rotation method scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.953, Tmax = 0.995	l = −16→16
11152 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ2(Fo2) + (0.0202P)2] where P = (Fo2 + 2Fc2)/3
2762 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.10 e Å−3
3 restraints	Δρmin = −0.14 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)
C16	0.9623 (6)	0.7727 (5)	0.9480 (2)	0.0728 (9)
H1A	−0.054 (5)	0.899 (4)	0.399 (2)	0.114 (12)*
H111	0.303 (4)	0.857 (3)	0.540 (2)	0.097 (10)*
C1	0.7674 (4)	0.9053 (3)	0.81076 (18)	0.0484 (6)
C2	0.5942 (4)	0.9960 (3)	0.84348 (18)	0.0561 (7)
H2	0.5980	1.0412	0.9045	0.067*
C3	0.4201 (4)	1.0184 (3)	0.78629 (18)	0.0544 (7)
H3	0.3059	1.0792	0.8089	0.065*
C4	0.4088 (4)	0.9514 (3)	0.69342 (17)	0.0462 (6)
C5	0.5886 (4)	0.8589 (3)	0.66153 (16)	0.0427 (6)
C6	0.7678 (4)	0.8403 (3)	0.72199 (18)	0.0486 (6)
H6	0.8861	0.7830	0.7005	0.058*
C7	0.3895 (4)	0.7180 (3)	0.42719 (17)	0.0424 (6)
C8	0.1917 (4)	0.7462 (3)	0.38710 (18)	0.0477 (6)
C9	0.1518 (4)	0.6878 (3)	0.29666 (19)	0.0592 (7)
H9	0.0212	0.7074	0.2680	0.071*
C10	0.3056 (4)	0.6007 (3)	0.2487 (2)	0.0602 (8)
H10	0.2760	0.5618	0.1879	0.072*
C11	0.5026 (4)	0.5689 (3)	0.28793 (18)	0.0500 (6)
C12	0.5427 (4)	0.6285 (3)	0.37817 (17)	0.0464 (6)
H12	0.6736	0.6087	0.4065	0.056*
C13	0.6709 (4)	0.4766 (3)	0.2318 (2)	0.0702 (8)
H13A	0.7443	0.5501	0.1838	0.105*
H13B	0.6093	0.4019	0.1950	0.105*
H13C	0.7657	0.4194	0.2812	0.105*
C14	0.5861 (4)	0.7821 (3)	0.57199 (17)	0.0442 (6)
H14	0.7059	0.7253	0.5516	0.053*
F1A	0.8285 (13)	0.808 (3)	1.0198 (5)	0.120 (4)	0.61 (5)
F2B	0.952 (2)	0.6343 (7)	0.9169 (9)	0.106 (3)	0.61 (5)
F3A	1.1534 (11)	0.7647 (17)	0.9796 (12)	0.103 (3)	0.61 (5)
F1B	0.819 (2)	0.769 (3)	1.0204 (10)	0.141 (7)	0.39 (5)
F2A	0.916 (4)	0.6340 (8)	0.9273 (14)	0.110 (6)	0.39 (5)
F3B	1.122 (4)	0.771 (3)	1.007 (3)	0.154 (8)	0.39 (5)
N1	0.4201 (3)	0.7886 (2)	0.51702 (14)	0.0433 (5)
O1	0.0485 (3)	0.8293 (2)	0.44187 (13)	0.0619 (5)
O2	0.2431 (2)	0.9701 (2)	0.63948 (12)	0.0576 (5)
O33	0.9507 (3)	0.8897 (2)	0.86952 (14)	0.0682 (6)

	U11	U22	U33	U12	U13	U23
C16	0.093 (3)	0.080 (3)	0.0477 (19)	0.007 (2)	−0.0135 (18)	−0.0181 (19)
C1	0.0470 (17)	0.0509 (17)	0.0475 (14)	−0.0074 (14)	−0.0058 (12)	−0.0040 (13)
C2	0.0695 (19)	0.0587 (18)	0.0424 (14)	−0.0121 (15)	0.0007 (13)	−0.0112 (13)
C3	0.0542 (17)	0.0556 (18)	0.0531 (15)	0.0019 (14)	0.0066 (13)	−0.0113 (13)
C4	0.0469 (16)	0.0454 (16)	0.0456 (14)	−0.0011 (13)	−0.0006 (12)	−0.0048 (12)
C5	0.0419 (16)	0.0447 (16)	0.0411 (13)	−0.0005 (13)	0.0000 (12)	−0.0060 (12)
C6	0.0441 (16)	0.0467 (16)	0.0540 (15)	−0.0001 (12)	−0.0006 (12)	−0.0049 (13)
C7	0.0465 (17)	0.0377 (15)	0.0430 (14)	−0.0025 (13)	0.0011 (12)	−0.0060 (11)
C8	0.0465 (16)	0.0452 (17)	0.0508 (14)	−0.0001 (13)	−0.0013 (12)	−0.0054 (13)
C9	0.0595 (19)	0.0566 (18)	0.0634 (17)	−0.0042 (15)	−0.0145 (14)	−0.0108 (14)
C10	0.072 (2)	0.0552 (19)	0.0583 (16)	−0.0090 (16)	−0.0038 (15)	−0.0207 (14)
C11	0.0616 (18)	0.0391 (16)	0.0499 (14)	−0.0065 (13)	0.0073 (12)	−0.0089 (12)
C12	0.0453 (16)	0.0418 (16)	0.0510 (15)	0.0005 (13)	0.0001 (12)	−0.0042 (12)
C13	0.080 (2)	0.0564 (18)	0.0773 (19)	−0.0037 (16)	0.0181 (16)	−0.0256 (15)
C14	0.0404 (16)	0.0428 (16)	0.0470 (14)	0.0040 (12)	0.0026 (12)	−0.0023 (12)
F1A	0.153 (7)	0.149 (9)	0.046 (4)	0.051 (4)	0.002 (4)	−0.007 (4)
F2B	0.127 (5)	0.085 (7)	0.106 (5)	0.031 (5)	−0.024 (4)	−0.030 (5)
F3A	0.069 (6)	0.158 (5)	0.078 (5)	0.007 (3)	−0.048 (3)	−0.003 (4)
F1B	0.190 (14)	0.108 (9)	0.098 (10)	0.030 (6)	0.077 (11)	0.037 (7)
F2A	0.189 (14)	0.045 (7)	0.094 (8)	−0.013 (7)	−0.087 (9)	0.019 (6)
F3B	0.22 (2)	0.165 (10)	0.082 (11)	−0.021 (10)	−0.082 (9)	−0.007 (7)
N1	0.0387 (13)	0.0436 (14)	0.0467 (12)	0.0048 (10)	−0.0011 (10)	−0.0063 (10)
O1	0.0488 (11)	0.0748 (14)	0.0604 (11)	0.0158 (10)	−0.0036 (9)	−0.0138 (10)
O2	0.0461 (11)	0.0673 (13)	0.0592 (10)	0.0141 (9)	−0.0051 (9)	−0.0173 (9)
O33	0.0648 (14)	0.0784 (14)	0.0620 (12)	−0.0158 (11)	−0.0203 (10)	−0.0008 (11)

C16—F2B	1.294 (5)	C7—C8	1.391 (3)
C16—F2A	1.295 (5)	C7—C12	1.392 (3)
C16—F1B	1.302 (6)	C7—N1	1.411 (3)
C16—F1A	1.303 (5)	C8—O1	1.362 (3)
C16—F3A	1.312 (5)	C8—C9	1.378 (3)
C16—F3B	1.312 (6)	C9—C10	1.376 (3)
C16—O33	1.322 (3)	C9—H9	0.9300
C1—C6	1.347 (3)	C10—C11	1.383 (3)
C1—C2	1.396 (3)	C10—H10	0.9300
C1—O33	1.422 (3)	C11—C12	1.381 (3)
C2—C3	1.360 (3)	C11—C13	1.517 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.411 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—O2	1.291 (3)	C13—H13C	0.9600
C4—C5	1.433 (3)	C14—N1	1.305 (3)
C5—C6	1.411 (3)	C14—H14	0.9300
C5—C14	1.412 (3)	N1—H111	0.98 (3)
C6—H6	0.9300	O1—H1A	0.99 (3)
F2B—C16—F1B	101.8 (16)	C8—C7—N1	115.3 (2)
F2A—C16—F1A	105 (2)	C12—C7—N1	124.3 (2)
F2A—C16—F3A	110.3 (14)	O1—C8—C9	124.3 (2)
F1A—C16—F3A	111.9 (7)	O1—C8—C7	116.8 (2)
F2B—C16—F3B	110.6 (14)	C9—C8—C7	118.9 (2)
F1B—C16—F3B	97.7 (19)	C10—C9—C8	119.9 (2)
F2B—C16—O33	111.3 (5)	C10—C9—H9	120.1
F2A—C16—O33	115.5 (7)	C8—C9—H9	120.1
F1B—C16—O33	119.0 (11)	C9—C10—C11	122.3 (2)
F1A—C16—O33	108.7 (9)	C9—C10—H10	118.8
F3A—C16—O33	105.6 (7)	C11—C10—H10	118.8
F3B—C16—O33	115.1 (14)	C12—C11—C10	117.7 (2)
C6—C1—C2	121.3 (2)	C12—C11—C13	121.1 (2)
C6—C1—O33	119.5 (2)	C10—C11—C13	121.2 (2)
C2—C1—O33	119.0 (2)	C11—C12—C7	120.7 (2)
C3—C2—C1	120.1 (2)	C11—C12—H12	119.6
C3—C2—H2	119.9	C7—C12—H12	119.6
C1—C2—H2	119.9	C11—C13—H13A	109.5
C2—C3—C4	121.4 (2)	C11—C13—H13B	109.5
C2—C3—H3	119.3	H13A—C13—H13B	109.5
C4—C3—H3	119.3	C11—C13—H13C	109.5
O2—C4—C3	121.8 (2)	H13A—C13—H13C	109.5
O2—C4—C5	120.8 (2)	H13B—C13—H13C	109.5
C3—C4—C5	117.3 (2)	N1—C14—C5	121.7 (2)
C6—C5—C14	119.7 (2)	N1—C14—H14	119.1
C6—C5—C4	119.7 (2)	C5—C14—H14	119.1
C14—C5—C4	120.6 (2)	C14—N1—C7	129.2 (2)
C1—C6—C5	120.1 (2)	C14—N1—H111	114.7 (17)
C1—C6—H6	120.0	C7—N1—H111	116.0 (17)
C5—C6—H6	120.0	C8—O1—H1A	114.9 (17)
C8—C7—C12	120.4 (2)	C16—O33—C1	116.4 (2)
C6—C1—C2—C3	0.9 (4)	C9—C10—C11—C12	−0.3 (4)
O33—C1—C2—C3	177.2 (2)	C9—C10—C11—C13	−178.2 (3)
C1—C2—C3—C4	0.1 (4)	C10—C11—C12—C7	−0.3 (3)
C2—C3—C4—O2	179.0 (3)	C13—C11—C12—C7	177.7 (3)
C2—C3—C4—C5	−0.1 (4)	C8—C7—C12—C11	1.3 (4)
O2—C4—C5—C6	−180.0 (2)	N1—C7—C12—C11	−177.3 (2)
C3—C4—C5—C6	−0.9 (3)	C6—C5—C14—N1	176.1 (2)
O2—C4—C5—C14	−1.9 (4)	C4—C5—C14—N1	−1.9 (3)
C3—C4—C5—C14	177.2 (2)	C5—C14—N1—C7	−179.0 (2)
C2—C1—C6—C5	−2.0 (4)	C8—C7—N1—C14	179.2 (3)
O33—C1—C6—C5	−178.2 (2)	C12—C7—N1—C14	−2.1 (4)
C14—C5—C6—C1	−176.1 (2)	F2B—C16—O33—C1	60.1 (7)
C4—C5—C6—C1	1.9 (4)	F2A—C16—O33—C1	48.0 (16)
C12—C7—C8—O1	177.5 (2)	F1B—C16—O33—C1	−57.8 (14)
N1—C7—C8—O1	−3.8 (3)	F1A—C16—O33—C1	−69.6 (9)
C12—C7—C8—C9	−1.8 (4)	F3A—C16—O33—C1	170.2 (7)
N1—C7—C8—C9	176.9 (2)	F3B—C16—O33—C1	−173.1 (19)
O1—C8—C9—C10	−177.9 (3)	C6—C1—O33—C16	−97.4 (3)
C7—C8—C9—C10	1.3 (4)	C2—C1—O33—C16	86.3 (3)
C8—C9—C10—C11	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H111···O1	0.99 (3)	2.16 (3)	2.610 (3)	106 (2)
N1—H111···O2	0.99 (3)	1.72 (3)	2.546 (2)	138 (2)
O1—H1A···O2i	0.99 (3)	1.63 (3)	2.591 (2)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H111⋯O2	0.99 (3)	1.72 (3)	2.546 (2)	138 (2)
O1—H1A⋯O2i	0.99 (3)	1.63 (3)	2.591 (2)	164 (3)

Symmetry code: (i) .