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

The title compound, C(14)H(9)ClF(3)NO(2), crystallizes in a phenol-imine tautomeric form, with a strong intra-molecular O-H⋯N hydrogen bond. The dihedral angle between the two benzene rings is 47.62 (9)°. In the crystal, mol-ecules are linked into chains along the c axis by C-H⋯O hydrogen bonds, and weak C-H⋯π inter-actions involving both benzene rings are also observed.

Related literature

For general background to Schiff bases, see: Calligaris et al. (1972 ▶); Cohen et al. (1964 ▶); Hadjoudis et al. (1987 ▶); Karadayı et al. (2003 ▶); Hökelek et al.(2000 ▶); Dey et al. (2001 ▶); Ünver et al. (2002 ▶). For a related structure, see: Gül et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H9ClF3NO2

M = 315.67

Monoclinic,

a = 29.612 (5) Å

b = 7.195 (5) Å

c = 6.375 (5) Å

β = 96.012 (5)°

V = 1350.8 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.72 × 0.44 × 0.10 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.844, T max = 0.966

11226 measured reflections

2579 independent reflections

1539 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.201

S = 1.04

2579 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.33 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/S1600536809040690/ci2934sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040690/ci2934Isup2.hkl

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

C14H9ClF3NO2	F(000) = 640
Mr = 315.67	Dx = 1.552 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 13303 reflections
a = 29.612 (5) Å	θ = 2.1–26.7°
b = 7.195 (5) Å	µ = 0.32 mm−1
c = 6.375 (5) Å	T = 296 K
β = 96.012 (5)°	Plate, light brown
V = 1350.8 (14) Å3	0.72 × 0.44 × 0.10 mm
Z = 4

Stoe IPDS-II diffractometer	2579 independent reflections
Radiation source: fine-focus sealed tube	1539 reflections with I > 2σ(I)
graphite	Rint = 0.059
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.8°
ω scans	h = −36→32
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
Tmin = 0.844, Tmax = 0.966	l = −7→7
11226 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1139P)2] where P = (Fo2 + 2Fc2)/3
2579 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.33 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
C1	0.79069 (11)	0.5332 (4)	0.8304 (4)	0.0561 (7)
C2	0.83127 (11)	0.5846 (4)	0.7543 (5)	0.0595 (8)
H2	0.8309	0.6345	0.6196	0.071*
C3	0.87134 (11)	0.5624 (4)	0.8759 (5)	0.0612 (8)
C4	0.87339 (12)	0.4841 (4)	1.0761 (5)	0.0651 (8)
H4	0.9012	0.4679	1.1566	0.078*
C5	0.83396 (12)	0.4317 (4)	1.1521 (5)	0.0662 (9)
H5	0.8351	0.3769	1.2847	0.079*
C6	0.79214 (11)	0.4581 (4)	1.0363 (5)	0.0607 (8)
C8	0.74786 (12)	0.5520 (4)	0.6986 (5)	0.0616 (8)
H8	0.7481	0.5908	0.5596	0.074*
C9	0.66929 (11)	0.5123 (4)	0.6311 (5)	0.0598 (7)
C10	0.62906 (12)	0.5708 (4)	0.7062 (5)	0.0674 (8)
H10	0.6298	0.6195	0.8417	0.081*
C11	0.58855 (13)	0.5576 (5)	0.5832 (6)	0.0778 (10)
H11	0.5619	0.5972	0.6350	0.093*
C12	0.58717 (12)	0.4860 (5)	0.3835 (6)	0.0716 (9)
C13	0.62616 (13)	0.4247 (5)	0.3058 (5)	0.0707 (9)
H13	0.6248	0.3734	0.1713	0.085*
C14	0.66709 (12)	0.4392 (4)	0.4268 (5)	0.0637 (8)
H14	0.6935	0.4003	0.3729	0.076*
C15	0.94016 (13)	0.5208 (5)	0.7263 (6)	0.0748 (9)
N1	0.70971 (9)	0.5168 (3)	0.7683 (4)	0.0618 (7)
O1	0.75423 (9)	0.4102 (3)	1.1218 (4)	0.0773 (7)
H1	0.7320	0.4327	1.0380	0.116*
O2	0.91140 (8)	0.6360 (3)	0.8050 (4)	0.0756 (7)
F1	0.91975 (12)	0.4373 (4)	0.5572 (5)	0.1403 (12)
F2	0.97374 (9)	0.6120 (4)	0.6655 (5)	0.1174 (9)
F3	0.95437 (12)	0.3876 (5)	0.8491 (6)	0.1558 (15)
Cl1	0.53598 (4)	0.46496 (19)	0.22578 (19)	0.1103 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0635 (19)	0.0520 (15)	0.0530 (16)	−0.0008 (13)	0.0076 (13)	−0.0016 (12)
C2	0.068 (2)	0.0537 (15)	0.0575 (16)	−0.0002 (13)	0.0091 (15)	0.0024 (13)
C3	0.0584 (19)	0.0548 (16)	0.0713 (19)	−0.0048 (13)	0.0118 (15)	−0.0032 (13)
C4	0.067 (2)	0.0586 (17)	0.0674 (18)	0.0012 (14)	−0.0043 (15)	−0.0038 (14)
C5	0.081 (3)	0.0627 (18)	0.0551 (17)	0.0009 (15)	0.0063 (16)	−0.0006 (13)
C6	0.067 (2)	0.0583 (17)	0.0576 (17)	−0.0009 (14)	0.0121 (15)	−0.0030 (13)
C8	0.069 (2)	0.0602 (17)	0.0557 (16)	−0.0005 (14)	0.0073 (15)	0.0022 (13)
C9	0.063 (2)	0.0565 (15)	0.0609 (17)	−0.0012 (13)	0.0101 (15)	0.0027 (13)
C10	0.067 (2)	0.076 (2)	0.0608 (18)	0.0042 (16)	0.0156 (16)	−0.0032 (15)
C11	0.059 (2)	0.089 (2)	0.087 (2)	0.0072 (17)	0.0131 (18)	0.0024 (19)
C12	0.066 (2)	0.0692 (19)	0.077 (2)	−0.0015 (16)	−0.0024 (17)	0.0100 (17)
C13	0.076 (3)	0.074 (2)	0.0614 (18)	0.0006 (16)	0.0042 (17)	0.0013 (15)
C14	0.062 (2)	0.0690 (19)	0.0614 (18)	0.0028 (14)	0.0144 (15)	0.0015 (14)
C15	0.070 (2)	0.079 (2)	0.075 (2)	−0.0030 (19)	0.0089 (18)	0.0058 (19)
N1	0.0598 (17)	0.0655 (15)	0.0608 (15)	0.0022 (12)	0.0094 (13)	0.0018 (11)
O1	0.0702 (16)	0.1015 (17)	0.0622 (13)	−0.0015 (12)	0.0164 (11)	0.0150 (12)
O2	0.0702 (16)	0.0633 (13)	0.0952 (16)	−0.0058 (11)	0.0180 (13)	−0.0014 (11)
F1	0.137 (3)	0.158 (3)	0.130 (2)	−0.025 (2)	0.032 (2)	−0.063 (2)
F2	0.0774 (17)	0.126 (2)	0.154 (2)	−0.0122 (14)	0.0383 (16)	0.0144 (17)
F3	0.129 (3)	0.169 (3)	0.181 (3)	0.081 (2)	0.066 (2)	0.091 (2)
Cl1	0.0737 (8)	0.1402 (10)	0.1111 (9)	−0.0048 (6)	−0.0188 (6)	0.0037 (7)

C1—C2	1.392 (4)	C9—N1	1.407 (4)
C1—C6	1.416 (4)	C10—C11	1.366 (5)
C1—C8	1.453 (4)	C10—H10	0.93
C2—C3	1.357 (5)	C11—C12	1.370 (5)
C2—H2	0.93	C11—H11	0.93
C3—C4	1.391 (5)	C12—C13	1.376 (5)
C3—O2	1.416 (4)	C12—Cl1	1.736 (4)
C4—C5	1.363 (5)	C13—C14	1.371 (5)
C4—H4	0.93	C13—H13	0.93
C5—C6	1.387 (5)	C14—H14	0.93
C5—H5	0.93	C15—F3	1.280 (4)
C6—O1	1.343 (4)	C15—F2	1.285 (4)
C8—N1	1.282 (4)	C15—F1	1.323 (5)
C8—H8	0.93	C15—O2	1.324 (4)
C9—C10	1.394 (5)	O1—H1	0.82
C9—C14	1.400 (4)
C2—C1—C6	118.7 (3)	C11—C10—C9	120.8 (3)
C2—C1—C8	120.4 (3)	C11—C10—H10	119.6
C6—C1—C8	120.8 (3)	C9—C10—H10	119.6
C3—C2—C1	120.3 (3)	C10—C11—C12	119.9 (3)
C3—C2—H2	119.8	C10—C11—H11	120.1
C1—C2—H2	119.8	C12—C11—H11	120.1
C2—C3—C4	121.6 (3)	C11—C12—C13	120.7 (3)
C2—C3—O2	119.1 (3)	C11—C12—Cl1	120.7 (3)
C4—C3—O2	119.1 (3)	C13—C12—Cl1	118.6 (3)
C5—C4—C3	118.8 (3)	C14—C13—C12	119.9 (3)
C5—C4—H4	120.6	C14—C13—H13	120.0
C3—C4—H4	120.6	C12—C13—H13	120.0
C4—C5—C6	121.5 (3)	C13—C14—C9	120.3 (3)
C4—C5—H5	119.2	C13—C14—H14	119.8
C6—C5—H5	119.2	C9—C14—H14	119.8
O1—C6—C5	119.1 (3)	F3—C15—F2	110.6 (4)
O1—C6—C1	121.9 (3)	F3—C15—F1	104.5 (4)
C5—C6—C1	119.0 (3)	F2—C15—F1	106.8 (3)
N1—C8—C1	121.9 (3)	F3—C15—O2	114.8 (3)
N1—C8—H8	119.0	F2—C15—O2	110.1 (3)
C1—C8—H8	119.0	F1—C15—O2	109.6 (3)
C10—C9—C14	118.3 (3)	C8—N1—C9	120.8 (3)
C10—C9—N1	118.8 (3)	C6—O1—H1	109.5
C14—C9—N1	122.7 (3)	C15—O2—C3	118.7 (3)
C6—C1—C2—C3	0.1 (4)	C9—C10—C11—C12	0.0 (5)
C8—C1—C2—C3	−178.3 (3)	C10—C11—C12—C13	0.8 (5)
C1—C2—C3—C4	1.7 (4)	C10—C11—C12—Cl1	179.1 (3)
C1—C2—C3—O2	−172.5 (2)	C11—C12—C13—C14	−1.6 (5)
C2—C3—C4—C5	−1.1 (5)	Cl1—C12—C13—C14	−179.9 (2)
O2—C3—C4—C5	173.1 (3)	C12—C13—C14—C9	1.5 (5)
C3—C4—C5—C6	−1.3 (5)	C10—C9—C14—C13	−0.6 (4)
C4—C5—C6—O1	−177.5 (3)	N1—C9—C14—C13	174.8 (3)
C4—C5—C6—C1	3.0 (4)	C1—C8—N1—C9	−171.6 (3)
C2—C1—C6—O1	178.2 (3)	C10—C9—N1—C8	−146.5 (3)
C8—C1—C6—O1	−3.4 (4)	C14—C9—N1—C8	38.1 (4)
C2—C1—C6—C5	−2.4 (4)	F3—C15—O2—C3	−56.1 (5)
C8—C1—C6—C5	176.0 (3)	F2—C15—O2—C3	178.3 (3)
C2—C1—C8—N1	−175.6 (3)	F1—C15—O2—C3	61.2 (4)
C6—C1—C8—N1	6.0 (4)	C2—C3—O2—C15	−103.8 (4)
C14—C9—C10—C11	−0.2 (5)	C4—C3—O2—C15	81.9 (4)
N1—C9—C10—C11	−175.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.604 (4)	147
C14—H14···O1i	0.93	2.53	3.396 (5)	155
C2—H2···Cg1ii	0.93	2.77	3.496 (4)	135
C5—H5···Cg1iii	0.93	2.98	3.713 (4)	136
C10—H10···Cg2iv	0.93	2.94	3.644 (4)	133
C13—H13···Cg2v	0.93	2.88	3.597 (4)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.604 (4)	147
C14—H14⋯O1i	0.93	2.53	3.396 (5)	155
C2—H2⋯Cg1ii	0.93	2.77	3.496 (4)	135
C5—H5⋯Cg1iii	0.93	2.98	3.713 (4)	136
C10—H10⋯Cg2iv	0.93	2.94	3.644 (4)	133
C13—H13⋯Cg2v	0.93	2.88	3.597 (4)	135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.