(E)-2-[(3-Fluoro-phen-yl)imino-meth-yl]-4-(trifluoro-meth-oxy)phenol.

The title compound, C(14)H(9)F(4)NO(2), is a Schiff base which adopts the phenol-imine tautomeric form in the solid state. The H atom is located on the hydr-oxy O atom rather than on the N atom. This H atom is involved in a strong intra-molecular O-H⋯N hydrogen bond. The mol-ecule is almost planar, the angle between the benzene rings being 2.14 (13)°.

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: Şahin et al. (2005 ▶).

Experimental

Crystal data

C14H9F4NO2

M = 299.22

Monoclinic,

a = 14.223 (2) Å

b = 7.0894 (6) Å

c = 13.2479 (19) Å

β = 100.910 (11)°

V = 1311.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.72 × 0.34 × 0.07 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.929, T max = 0.985

8512 measured reflections

2581 independent reflections

1261 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.133

S = 1.01

2581 reflections

222 parameters

66 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002989/si2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002989/si2237Isup2.hkl

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

C14H9F4NO2	F(000) = 608
Mr = 299.22	Dx = 1.515 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8512 reflections
a = 14.223 (2) Å	θ = 1.6–28.5°
b = 7.0894 (6) Å	µ = 0.14 mm−1
c = 13.2479 (19) Å	T = 296 K
β = 100.910 (11)°	Prism., yellow
V = 1311.7 (3) Å3	0.72 × 0.34 × 0.07 mm
Z = 4

Stoe IPDS-II diffractometer	2581 independent reflections
Radiation source: fine-focus sealed tube	1261 reflections with I > 2σ(I)
graphite	Rint = 0.063
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.9°
ω scans	h = −17→17
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
Tmin = 0.929, Tmax = 0.985	l = −16→16
8512 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0516P)2] where P = (Fo2 + 2Fc2)/3
2581 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.12 e Å−3
66 restraints	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6817 (2)	0.1145 (4)	0.8494 (2)	0.0532 (7)
C2	0.7714 (2)	0.1111 (4)	0.8217 (2)	0.0590 (8)
H2	0.7757	0.1033	0.7526	0.071*
C3	0.8530 (2)	0.1190 (4)	0.8947 (2)	0.0609 (8)
C4	0.8492 (2)	0.1262 (5)	0.9975 (2)	0.0713 (9)
H4	0.9054	0.1308	1.0465	0.086*
C5	0.7622 (2)	0.1265 (5)	1.0275 (2)	0.0720 (9)
H5	0.7595	0.1308	1.0971	0.086*
C6	0.6781 (2)	0.1207 (4)	0.9551 (2)	0.0578 (7)
C7	0.5955 (2)	0.1111 (4)	0.7713 (2)	0.0564 (7)
H7	0.6011	0.1079	0.7025	0.068*
C8	0.42736 (18)	0.1115 (4)	0.7176 (2)	0.0488 (7)
C9	0.3428 (2)	0.1172 (4)	0.7535 (2)	0.0626 (8)
H9	0.3441	0.1207	0.8239	0.075*
C10	0.2558 (2)	0.1176 (4)	0.6859 (3)	0.0734 (9)
H10	0.1992	0.1217	0.7114	0.088*
C11	0.2521 (2)	0.1121 (5)	0.5813 (3)	0.0707 (9)
H11	0.1941	0.1132	0.5351	0.085*
C12	0.3369 (2)	0.1050 (5)	0.5484 (2)	0.0666 (8)
C13	0.4241 (2)	0.1054 (4)	0.6120 (2)	0.0647 (8)
H13	0.4801	0.1017	0.5855	0.078*
C15	0.9817 (2)	0.2629 (7)	0.8394 (3)	0.0769 (10)
N1	0.51254 (17)	0.1122 (3)	0.79347 (16)	0.0539 (6)
O1	0.59429 (17)	0.1222 (4)	0.98783 (16)	0.0776 (7)
O2	0.94418 (15)	0.1066 (3)	0.86652 (18)	0.0787 (7)
F1A	0.9358 (12)	0.389 (2)	0.7861 (18)	0.117 (5)	0.288 (17)
F2A	1.0127 (14)	0.332 (3)	0.9365 (12)	0.132 (6)	0.288 (17)
F3A	1.0594 (14)	0.243 (4)	0.7992 (19)	0.129 (8)	0.288 (17)
F1B	0.9331 (4)	0.3107 (14)	0.7446 (5)	0.115 (2)	0.712 (17)
F2B	0.9765 (5)	0.4159 (9)	0.8941 (7)	0.110 (2)	0.712 (17)
F3B	1.0706 (4)	0.2329 (14)	0.8333 (7)	0.0968 (19)	0.712 (17)
F4	0.33425 (15)	0.0950 (4)	0.44555 (14)	0.1095 (8)
H1	0.546 (3)	0.113 (6)	0.932 (4)	0.144 (18)*

	U11	U22	U33	U12	U13	U23
C1	0.0594 (18)	0.0479 (17)	0.0537 (16)	−0.0005 (15)	0.0148 (14)	0.0009 (15)
C2	0.066 (2)	0.061 (2)	0.0517 (16)	0.0087 (16)	0.0163 (15)	−0.0009 (16)
C3	0.0532 (18)	0.0606 (19)	0.070 (2)	0.0119 (16)	0.0140 (15)	0.0046 (17)
C4	0.067 (2)	0.081 (2)	0.062 (2)	0.0048 (18)	0.0026 (16)	0.0132 (19)
C5	0.074 (2)	0.092 (2)	0.0498 (17)	−0.0028 (19)	0.0107 (16)	0.0077 (18)
C6	0.0584 (19)	0.0612 (19)	0.0551 (18)	−0.0008 (16)	0.0139 (14)	0.0080 (16)
C7	0.068 (2)	0.0540 (19)	0.0500 (17)	−0.0041 (16)	0.0180 (15)	−0.0042 (15)
C8	0.0541 (17)	0.0393 (15)	0.0546 (16)	−0.0024 (14)	0.0145 (14)	0.0010 (14)
C9	0.070 (2)	0.061 (2)	0.0605 (18)	−0.0078 (17)	0.0220 (16)	−0.0063 (16)
C10	0.064 (2)	0.074 (2)	0.086 (3)	0.0009 (18)	0.0242 (18)	−0.006 (2)
C11	0.060 (2)	0.064 (2)	0.083 (2)	−0.0019 (17)	0.0011 (17)	0.0037 (18)
C12	0.076 (2)	0.072 (2)	0.0500 (18)	−0.0008 (18)	0.0055 (16)	0.0092 (17)
C13	0.066 (2)	0.079 (2)	0.0520 (17)	0.0000 (17)	0.0191 (15)	0.0068 (17)
C15	0.055 (2)	0.096 (3)	0.082 (3)	0.006 (2)	0.018 (2)	0.001 (3)
N1	0.0594 (15)	0.0536 (15)	0.0496 (13)	−0.0024 (13)	0.0127 (11)	0.0003 (12)
O1	0.0673 (15)	0.116 (2)	0.0532 (13)	−0.0080 (14)	0.0212 (11)	0.0009 (13)
O2	0.0605 (14)	0.0801 (17)	0.0998 (17)	0.0159 (13)	0.0264 (12)	0.0094 (14)
F1A	0.103 (7)	0.096 (7)	0.160 (10)	0.020 (6)	0.044 (8)	0.026 (7)
F2A	0.128 (9)	0.128 (10)	0.141 (8)	−0.039 (7)	0.030 (6)	−0.039 (7)
F3A	0.115 (10)	0.153 (11)	0.136 (12)	0.006 (7)	0.068 (8)	−0.001 (8)
F1B	0.094 (3)	0.164 (5)	0.083 (3)	−0.015 (3)	0.008 (2)	0.044 (3)
F2B	0.113 (4)	0.086 (3)	0.143 (5)	−0.019 (3)	0.053 (3)	−0.034 (3)
F3B	0.048 (2)	0.137 (4)	0.110 (4)	0.008 (2)	0.025 (2)	0.011 (3)
F4	0.1097 (16)	0.162 (2)	0.0533 (11)	−0.0061 (15)	0.0052 (10)	0.0172 (12)

C1—C2	1.393 (4)	C9—C10	1.383 (4)
C1—C6	1.411 (4)	C9—H9	0.9300
C1—C7	1.447 (4)	C10—C11	1.378 (4)
C2—C3	1.365 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.358 (4)
C3—C4	1.374 (4)	C11—H11	0.9300
C3—O2	1.418 (3)	C12—F4	1.358 (3)
C4—C5	1.369 (4)	C12—C13	1.361 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.385 (4)	C15—F1A	1.246 (12)
C5—H5	0.9300	C15—F3B	1.299 (6)
C6—O1	1.343 (3)	C15—O2	1.310 (4)
C7—N1	1.268 (3)	C15—F2B	1.315 (5)
C7—H7	0.9300	C15—F3A	1.321 (13)
C8—C9	1.376 (4)	C15—F1B	1.357 (6)
C8—C13	1.392 (4)	C15—F2A	1.369 (11)
C8—N1	1.420 (3)	O1—H1	0.91 (5)
C2—C1—C6	118.0 (3)	C10—C11—H11	121.4
C2—C1—C7	120.4 (3)	C11—C12—F4	117.8 (3)
C6—C1—C7	121.7 (3)	C11—C12—C13	124.2 (3)
C3—C2—C1	120.7 (3)	F4—C12—C13	118.0 (3)
C3—C2—H2	119.6	C12—C13—C8	118.4 (3)
C1—C2—H2	119.6	C12—C13—H13	120.8
C2—C3—C4	121.0 (3)	C8—C13—H13	120.8
C2—C3—O2	120.5 (3)	F1A—C15—F3B	119.6 (9)
C4—C3—O2	118.3 (3)	F1A—C15—O2	124.6 (9)
C5—C4—C3	119.7 (3)	F3B—C15—O2	109.3 (6)
C5—C4—H4	120.1	F1A—C15—F2B	69.0 (9)
C3—C4—H4	120.1	F3B—C15—F2B	109.1 (6)
C4—C5—C6	120.6 (3)	O2—C15—F2B	118.6 (4)
C4—C5—H5	119.7	F1A—C15—F3A	103.6 (14)
C6—C5—H5	119.7	F3B—C15—F3A	20.0 (12)
O1—C6—C5	118.6 (3)	O2—C15—F3A	115.9 (14)
O1—C6—C1	121.5 (3)	F2B—C15—F3A	116.6 (14)
C5—C6—C1	120.0 (3)	F1A—C15—F1B	34.5 (8)
N1—C7—C1	122.3 (3)	F3B—C15—F1B	108.4 (5)
N1—C7—H7	118.9	O2—C15—F1B	107.6 (4)
C1—C7—H7	118.9	F2B—C15—F1B	103.5 (5)
C9—C8—C13	118.9 (3)	F3A—C15—F1B	88.4 (11)
C9—C8—N1	116.1 (3)	F1A—C15—F2A	108.5 (10)
C13—C8—N1	125.0 (2)	F3B—C15—F2A	88.4 (8)
C8—C9—C10	120.7 (3)	O2—C15—F2A	96.8 (9)
C8—C9—H9	119.7	F2B—C15—F2A	39.6 (9)
C10—C9—H9	119.7	F3A—C15—F2A	105.7 (12)
C11—C10—C9	120.7 (3)	F1B—C15—F2A	143.0 (10)
C11—C10—H10	119.7	C7—N1—C8	122.9 (2)
C9—C10—H10	119.7	C6—O1—H1	109 (3)
C12—C11—C10	117.2 (3)	C15—O2—C3	117.4 (3)
C12—C11—H11	121.4
C6—C1—C2—C3	−1.8 (4)	C9—C10—C11—C12	0.4 (5)
C7—C1—C2—C3	178.4 (3)	C10—C11—C12—F4	178.5 (3)
C1—C2—C3—C4	1.5 (5)	C10—C11—C12—C13	−0.9 (5)
C1—C2—C3—O2	177.0 (3)	C11—C12—C13—C8	0.7 (5)
C2—C3—C4—C5	−0.4 (5)	F4—C12—C13—C8	−178.6 (3)
O2—C3—C4—C5	−176.0 (3)	C9—C8—C13—C12	−0.1 (5)
C3—C4—C5—C6	−0.3 (5)	N1—C8—C13—C12	179.8 (3)
C4—C5—C6—O1	−179.7 (3)	C1—C7—N1—C8	179.1 (2)
C4—C5—C6—C1	−0.1 (5)	C9—C8—N1—C7	−178.6 (3)
C2—C1—C6—O1	−179.3 (3)	C13—C8—N1—C7	1.4 (4)
C7—C1—C6—O1	0.5 (5)	F1A—C15—O2—C3	−39.7 (14)
C2—C1—C6—C5	1.1 (4)	F3B—C15—O2—C3	169.1 (5)
C7—C1—C6—C5	−179.1 (3)	F2B—C15—O2—C3	43.4 (7)
C2—C1—C7—N1	179.3 (3)	F3A—C15—O2—C3	−170.4 (13)
C6—C1—C7—N1	−0.5 (4)	F1B—C15—O2—C3	−73.4 (6)
C13—C8—C9—C10	−0.3 (5)	F2A—C15—O2—C3	78.4 (11)
N1—C8—C9—C10	179.8 (3)	C2—C3—O2—C15	85.7 (4)
C8—C9—C10—C11	0.1 (5)	C4—C3—O2—C15	−98.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (5)	1.81 (5)	2.618 (3)	146 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.91 (5)	1.81 (5)	2.618 (3)	146 (4)