(E)-2-{[(2-(Trifluoro-meth-yl)phen-yl]imino-meth-yl}phenol.

In the crystal of the title compound, C(14)H(10)F(3)NO, intra-molecular O-H⋯N and O-H⋯F hydrogen bonds generate S(6) and S(10) intramolecular hydrogen-bonded rings. The dihedral angle between the planes of the aromatic rings is 13.00 (14)°.

Related literature

For related structures, see: Odabaşoǧlu et al. (2003 ▶, 2005 ▶); Albayrak et al. (2012 ▶); Temel et al. (2006 ▶). For ring motifs, see: Bernstein et al. (1995 ▶). For azomethine dye applications, see: Williams (1972 ▶); Elizbarashvili et al. (2007 ▶); Taggi et al. (2002 ▶); Ichijima & Kobayashi (2005 ▶); Calligaris et al. (1972 ▶); Hadjoudis et al. (1987 ▶). For the synthesis of the title mol­ecule, see: Odabaşoǧlu et al. (2003 ▶).

Experimental

Crystal data

C14H10F3NO

M = 265.23

Orthorhombic,

a = 17.9907 (18) Å

b = 5.0898 (4) Å

c = 13.2564 (10) Å

V = 1213.88 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.73 × 0.48 × 0.27 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.932, T max = 0.966

9185 measured reflections

2519 independent reflections

1827 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.084

S = 1.07

1318 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: 1201 measured Friedel pairs were merged, because the compound is a weak anomalous scatterer

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812003212/bh2411sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003212/bh2411Isup2.hkl

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

C14H10F3NO	Dx = 1.451 Mg m−3
Mr = 265.23	Melting point: 338 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 15262 reflections
a = 17.9907 (18) Å	θ = 1.5–28.0°
b = 5.0898 (4) Å	µ = 0.12 mm−1
c = 13.2564 (10) Å	T = 296 K
V = 1213.88 (18) Å3	Prism, yellow
Z = 4	0.73 × 0.48 × 0.27 mm
F(000) = 544

Stoe IPDS II diffractometer	2519 independent reflections
Radiation source: fine-focus sealed tube	1827 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 0 pixels mm-1	θmax = 26.5°, θmin = 2.3°
rotation method scans	h = −22→22
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −6→6
Tmin = 0.932, Tmax = 0.966	l = −16→16
9185 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3
1318 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.15 e Å−3
0 constraints	Absolute structure: 1201 measured Friedel pairs were merged, because the compound is a weak anomalous scatterer

	x	y	z	Uiso*/Ueq
C1	0.45358 (12)	1.0002 (5)	0.7729 (2)	0.0617 (6)
C2	0.43472 (14)	1.0230 (5)	0.6716 (2)	0.0698 (7)
C3	0.38195 (19)	1.2075 (6)	0.6431 (3)	0.0864 (9)
H3	0.3689	1.2237	0.5755	0.104*
C4	0.34888 (18)	1.3658 (6)	0.7134 (4)	0.0915 (11)
H4	0.3140	1.4894	0.6928	0.110*
C5	0.36636 (17)	1.3453 (6)	0.8136 (3)	0.0868 (10)
H5	0.3433	1.4530	0.8608	0.104*
C6	0.41827 (16)	1.1637 (6)	0.8435 (3)	0.0793 (8)
H6	0.4302	1.1486	0.9115	0.095*
C7	0.50948 (15)	0.8157 (5)	0.8071 (2)	0.0648 (6)
H7	0.5213	0.8108	0.8753	0.078*
C8	0.59564 (12)	0.4792 (5)	0.7836 (2)	0.0612 (6)
C9	0.60401 (16)	0.4129 (6)	0.8843 (3)	0.0780 (8)
H9	0.5728	0.4895	0.9319	0.094*
C10	0.65715 (18)	0.2370 (7)	0.9161 (3)	0.0885 (9)
H10	0.6627	0.2004	0.9844	0.106*
C11	0.70208 (16)	0.1155 (6)	0.8462 (3)	0.0891 (10)
H11	0.7380	−0.0038	0.8672	0.107*
C12	0.69381 (17)	0.1702 (5)	0.7458 (3)	0.0811 (9)
H12	0.7235	0.0845	0.6987	0.097*
C13	0.64133 (14)	0.3532 (5)	0.7135 (2)	0.0644 (7)
C14	0.63575 (17)	0.4148 (6)	0.6040 (2)	0.0769 (8)
N1	0.54272 (12)	0.6611 (4)	0.74774 (15)	0.0622 (5)
O1	0.46592 (15)	0.8714 (5)	0.60028 (16)	0.0918 (7)
F1	0.68225 (14)	0.2715 (5)	0.54915 (16)	0.1234 (8)
F2	0.65111 (13)	0.6642 (4)	0.58376 (16)	0.1042 (7)
F3	0.56880 (12)	0.3721 (4)	0.56487 (15)	0.1069 (7)
H13	0.496 (3)	0.776 (8)	0.628 (4)	0.107 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0553 (12)	0.0619 (14)	0.0680 (16)	−0.0060 (11)	0.0034 (13)	0.0022 (13)
C2	0.0679 (15)	0.0666 (15)	0.0750 (18)	−0.0014 (13)	−0.0018 (15)	0.0004 (15)
C3	0.087 (2)	0.0808 (19)	0.091 (2)	0.0044 (16)	−0.0121 (18)	0.0104 (18)
C4	0.0713 (18)	0.0710 (16)	0.132 (4)	0.0094 (15)	−0.001 (2)	0.005 (2)
C5	0.0714 (18)	0.0773 (19)	0.112 (3)	0.0054 (15)	0.0153 (18)	−0.0065 (18)
C6	0.0755 (17)	0.0786 (17)	0.084 (2)	0.0003 (15)	0.0129 (16)	−0.0033 (17)
C7	0.0632 (14)	0.0720 (15)	0.0593 (14)	−0.0052 (13)	0.0005 (12)	−0.0027 (13)
C8	0.0525 (12)	0.0627 (14)	0.0683 (16)	−0.0069 (11)	−0.0001 (13)	−0.0031 (13)
C9	0.0711 (16)	0.090 (2)	0.0725 (18)	0.0070 (15)	0.0017 (14)	0.0019 (17)
C10	0.085 (2)	0.092 (2)	0.088 (2)	0.0053 (18)	−0.0119 (19)	0.0170 (18)
C11	0.0669 (17)	0.0803 (19)	0.120 (3)	0.0050 (14)	−0.008 (2)	0.016 (2)
C12	0.0658 (16)	0.0713 (16)	0.106 (3)	−0.0003 (15)	0.0126 (16)	−0.0036 (18)
C13	0.0545 (13)	0.0611 (13)	0.0774 (17)	−0.0084 (12)	0.0061 (12)	−0.0056 (14)
C14	0.0745 (17)	0.0743 (18)	0.082 (2)	−0.0008 (14)	0.0190 (16)	−0.0080 (16)
N1	0.0569 (11)	0.0677 (11)	0.0618 (13)	0.0011 (10)	0.0009 (9)	−0.0008 (11)
O1	0.1086 (16)	0.0980 (16)	0.0688 (14)	0.0250 (14)	−0.0129 (12)	−0.0076 (12)
F1	0.1361 (18)	0.1374 (17)	0.0967 (15)	0.0357 (14)	0.0433 (14)	−0.0107 (13)
F2	0.1301 (16)	0.0950 (13)	0.0874 (13)	−0.0185 (11)	0.0113 (11)	0.0147 (10)
F3	0.0988 (13)	0.1415 (18)	0.0803 (12)	−0.0191 (11)	−0.0043 (10)	−0.0233 (14)

C1—C2	1.390 (4)	C8—C13	1.397 (4)
C1—C6	1.404 (4)	C8—N1	1.411 (3)
C1—C7	1.449 (4)	C9—C10	1.376 (4)
C2—O1	1.343 (4)	C9—H9	0.9300
C2—C3	1.388 (4)	C10—C11	1.376 (5)
C3—C4	1.369 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.368 (5)
C4—C5	1.368 (6)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.394 (4)
C5—C6	1.372 (5)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.488 (5)
C6—H6	0.9300	C14—F2	1.326 (3)
C7—N1	1.263 (3)	C14—F1	1.327 (4)
C7—H7	0.9300	C14—F3	1.329 (4)
C8—C9	1.385 (4)	O1—H13	0.82 (5)
C2—C1—C6	119.0 (2)	C10—C9—C8	121.9 (3)
C2—C1—C7	121.7 (2)	C10—C9—H9	119.0
C6—C1—C7	119.3 (3)	C8—C9—H9	119.0
O1—C2—C3	118.9 (3)	C9—C10—C11	119.7 (3)
O1—C2—C1	122.0 (2)	C9—C10—H10	120.2
C3—C2—C1	119.1 (3)	C11—C10—H10	120.2
C4—C3—C2	120.7 (4)	C12—C11—C10	120.0 (3)
C4—C3—H3	119.7	C12—C11—H11	120.0
C2—C3—H3	119.7	C10—C11—H11	120.0
C5—C4—C3	121.1 (3)	C11—C12—C13	120.6 (3)
C5—C4—H4	119.5	C11—C12—H12	119.7
C3—C4—H4	119.5	C13—C12—H12	119.7
C4—C5—C6	119.2 (3)	C12—C13—C8	120.1 (3)
C4—C5—H5	120.4	C12—C13—C14	119.1 (3)
C6—C5—H5	120.4	C8—C13—C14	120.8 (2)
C5—C6—C1	121.0 (3)	F2—C14—F1	106.5 (2)
C5—C6—H6	119.5	F2—C14—F3	105.4 (3)
C1—C6—H6	119.5	F1—C14—F3	105.5 (3)
N1—C7—C1	122.5 (2)	F2—C14—C13	112.6 (3)
N1—C7—H7	118.7	F1—C14—C13	112.1 (3)
C1—C7—H7	118.7	F3—C14—C13	114.0 (2)
C9—C8—C13	117.7 (2)	C7—N1—C8	121.2 (2)
C9—C8—N1	123.9 (2)	C2—O1—H13	107 (3)
C13—C8—N1	118.3 (2)
C6—C1—C2—O1	−179.5 (2)	C10—C11—C12—C13	1.5 (5)
C7—C1—C2—O1	1.6 (4)	C11—C12—C13—C8	−1.2 (4)
C6—C1—C2—C3	0.4 (4)	C11—C12—C13—C14	177.8 (3)
C7—C1—C2—C3	−178.6 (3)	C9—C8—C13—C12	−0.8 (3)
O1—C2—C3—C4	−180.0 (3)	N1—C8—C13—C12	−179.4 (2)
C1—C2—C3—C4	0.2 (5)	C9—C8—C13—C14	−179.8 (3)
C2—C3—C4—C5	−0.6 (5)	N1—C8—C13—C14	1.7 (3)
C3—C4—C5—C6	0.4 (5)	C12—C13—C14—F2	−117.6 (3)
C4—C5—C6—C1	0.2 (4)	C8—C13—C14—F2	61.4 (3)
C2—C1—C6—C5	−0.6 (4)	C12—C13—C14—F1	2.5 (4)
C7—C1—C6—C5	178.4 (2)	C8—C13—C14—F1	−178.5 (2)
C2—C1—C7—N1	−1.9 (4)	C12—C13—C14—F3	122.3 (3)
C6—C1—C7—N1	179.2 (2)	C8—C13—C14—F3	−58.7 (3)
C13—C8—C9—C10	2.5 (4)	C1—C7—N1—C8	−178.5 (2)
N1—C8—C9—C10	−179.0 (3)	C9—C8—N1—C7	14.7 (4)
C8—C9—C10—C11	−2.2 (5)	C13—C8—N1—C7	−166.9 (2)
C9—C10—C11—C12	0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H13···N1	0.82 (5)	1.88 (5)	2.622 (3)	149 (4)
O1—H13···F3	0.82 (5)	2.58 (4)	3.179 (3)	131 (4)
C10—H10···O1i	0.93	2.80	3.342 (5)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H13⋯N1	0.82 (5)	1.88 (5)	2.622 (3)	149 (4)
O1—H13⋯F3	0.82 (5)	2.58 (4)	3.179 (3)	131 (4)