2-{(E)-[(3-Iodo-4-methyl-phen-yl)imino]-meth-yl}-4-(trifluoro-meth-oxy)phenol.

The title compound, C(15)H(11)F(3)INO(2), adopts the enol-imine tautomeric form. The mol-ecule displays an E conformation with respect to the imine C=N double bond. The dihedral angle between the two benzene rings is 12.4 (2)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. The trifluoro-meth-oxy-phenyl group is disordered over two sites with an occupancy ratio of 0.621 (6):0.379 (6). The crystal structure features C-H⋯π inter-actions.

Related literature

For generic history to the use of Schiff bases and their biological activity, see: Tarafder et al. (2002 ▶); Cukurovali et al. (2002 ▶); Ali et al. (2002 ▶). Schiff base compounds can be classified by their photochromic and thermochromic characteristics, see: Alarcon et al. (1999 ▶); Cohen et al. (1964 ▶); Gül et al. (2007 ▶); Hadjoudis et al. (1987 ▶); Şahin et al. (2005 ▶); Xu et al. (1994 ▶). For related structures, see: Ağar et al. 2010 ▶); Ceylan et al. (2011 ▶); Demirtaş et al. (2009) ▶; Tecer et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11F3INO2

M = 421.15

Triclinic,

a = 4.6733 (3) Å

b = 6.6441 (5) Å

c = 25.2825 (19) Å

α = 86.970 (6)°

β = 86.386 (6)°

γ = 78.087 (5)°

V = 765.95 (10) Å3

Z = 2

Mo Kα radiation

μ = 2.13 mm−1

T = 296 K

0.80 × 0.38 × 0.10 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.389, T max = 0.833

9671 measured reflections

3237 independent reflections

2806 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.04

3237 reflections

198 parameters

38 restraints

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.58 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 datablock(s) I, global. DOI: 10.1107/S1600536812026876/lr2067sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026876/lr2067Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026876/lr2067Isup3.cml

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

C15H11F3INO2	Z = 2
Mr = 421.15	F(000) = 408
Triclinic, P1	Dx = 1.826 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6733 (3) Å	Cell parameters from 18957 reflections
b = 6.6441 (5) Å	θ = 1.6–27.3°
c = 25.2825 (19) Å	µ = 2.13 mm−1
α = 86.970 (6)°	T = 296 K
β = 86.386 (6)°	PLATE, yellow
γ = 78.087 (5)°	0.80 × 0.38 × 0.10 mm
V = 765.95 (10) Å3

Stoe IPDS 2 diffractometer	3237 independent reflections
Radiation source: fine-focus sealed tube	2806 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.066
Detector resolution: 6.67 pixels mm-1	θmax = 26.8°, θmin = 1.6°
rotation method scans	h = −5→5
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
Tmin = 0.389, Tmax = 0.833	l = −31→31
9671 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0721P)2 + 0.1093P] where P = (Fo2 + 2Fc2)/3
3237 reflections	(Δ/σ)max = 0.002
198 parameters	Δρmax = 0.71 e Å−3
38 restraints	Δρmin = −0.58 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)
C15	0.9104 (9)	0.8097 (7)	0.57659 (18)	0.0655 (10)
H15A	0.9969	0.6685	0.5849	0.098*
H15B	1.0566	0.8921	0.5770	0.098*
H15C	0.8333	0.8211	0.5420	0.098*
C14	−0.6844 (15)	0.7327 (12)	0.9450 (2)	0.0967 (18)
I1	0.59478 (6)	1.29948 (4)	0.557019 (11)	0.06978 (14)
O1	−0.3927 (8)	1.3987 (4)	0.77435 (14)	0.0774 (9)
H1	−0.2581	1.3429	0.7544	0.116*
N1	−0.0211 (6)	1.0922 (4)	0.73088 (12)	0.0511 (6)
C1	0.5067 (7)	1.0843 (5)	0.61658 (13)	0.0487 (7)
C5	0.2116 (7)	1.0139 (5)	0.69393 (13)	0.0491 (7)
C6	0.2828 (7)	1.1499 (5)	0.65460 (14)	0.0498 (7)
H6	0.1808	1.2858	0.6535	0.060*
O2	−0.8277 (7)	0.8215 (5)	0.90303 (13)	0.0752 (8)
C3	0.5939 (8)	0.7512 (5)	0.65756 (16)	0.0578 (8)
H3	0.6984	0.6160	0.6593	0.069*
C13	−0.1359 (8)	0.9712 (5)	0.76217 (14)	0.0528 (7)
H13	−0.0655	0.8301	0.7601	0.063*
C7	−0.3726 (7)	1.0436 (5)	0.80106 (14)	0.0501 (7)
C4	0.3711 (8)	0.8124 (6)	0.69536 (15)	0.0566 (8)
H4	0.3276	0.7190	0.7218	0.068*
C12	−0.4914 (8)	1.2548 (6)	0.80557 (15)	0.0575 (8)
C8	−0.4832 (8)	0.9026 (6)	0.83407 (16)	0.0563 (8)
H8	−0.4079	0.7626	0.8309	0.068*
C2	0.6688 (7)	0.8836 (5)	0.61677 (15)	0.0520 (7)
C10	−0.8238 (10)	1.1762 (8)	0.87578 (19)	0.0725 (11)
H10	−0.9750	1.2198	0.9009	0.087*
C9	−0.7043 (8)	0.9682 (6)	0.87166 (15)	0.0602 (9)
C11	−0.7204 (10)	1.3145 (7)	0.8433 (2)	0.0716 (11)
H11	−0.8034	1.4536	0.8461	0.086*
F1A	−0.830 (2)	0.6351 (14)	0.9751 (3)	0.1137 (11)	0.621 (6)
F2A	−0.4368 (18)	0.5983 (14)	0.9256 (3)	0.1137 (11)	0.621 (6)
F3A	−0.5481 (19)	0.8352 (13)	0.9714 (3)	0.1137 (11)	0.621 (6)
F1B	−0.818 (4)	0.571 (2)	0.9597 (5)	0.1137 (11)	0.379 (6)
F2B	−0.428 (3)	0.704 (2)	0.9445 (5)	0.1137 (11)	0.379 (6)
F3B	−0.758 (3)	0.8901 (18)	0.9804 (4)	0.1137 (11)	0.379 (6)

	U11	U22	U33	U12	U13	U23
C15	0.057 (2)	0.064 (2)	0.072 (2)	−0.0052 (17)	0.0091 (18)	−0.0137 (19)
C14	0.102 (4)	0.128 (5)	0.074 (3)	−0.062 (4)	−0.007 (3)	0.026 (3)
I1	0.0703 (2)	0.0657 (2)	0.0686 (2)	−0.01119 (13)	0.01306 (13)	0.00966 (13)
O1	0.088 (2)	0.0503 (14)	0.083 (2)	0.0003 (13)	0.0198 (16)	0.0101 (14)
N1	0.0505 (14)	0.0500 (14)	0.0493 (14)	−0.0040 (12)	0.0000 (12)	0.0015 (12)
C1	0.0473 (16)	0.0482 (15)	0.0500 (16)	−0.0087 (13)	−0.0021 (13)	−0.0008 (13)
C5	0.0475 (16)	0.0483 (16)	0.0497 (17)	−0.0050 (13)	−0.0039 (13)	−0.0014 (13)
C6	0.0476 (16)	0.0457 (15)	0.0530 (17)	−0.0029 (13)	−0.0019 (13)	−0.0002 (13)
O2	0.0662 (16)	0.091 (2)	0.0705 (18)	−0.0272 (15)	−0.0008 (14)	0.0153 (16)
C3	0.0545 (19)	0.0446 (16)	0.068 (2)	0.0029 (14)	−0.0012 (16)	−0.0029 (15)
C13	0.0545 (18)	0.0483 (16)	0.0541 (18)	−0.0072 (14)	−0.0030 (14)	−0.0010 (14)
C7	0.0473 (16)	0.0506 (16)	0.0507 (17)	−0.0072 (13)	−0.0030 (13)	0.0020 (13)
C4	0.0569 (19)	0.0497 (17)	0.058 (2)	−0.0016 (15)	0.0014 (15)	0.0063 (15)
C12	0.061 (2)	0.0515 (17)	0.0570 (19)	−0.0071 (15)	0.0012 (16)	0.0032 (15)
C8	0.0537 (18)	0.0540 (18)	0.060 (2)	−0.0086 (15)	−0.0038 (15)	0.0040 (15)
C2	0.0444 (16)	0.0538 (17)	0.0559 (18)	−0.0045 (14)	−0.0021 (14)	−0.0085 (15)
C10	0.064 (2)	0.082 (3)	0.067 (2)	−0.008 (2)	0.0115 (19)	−0.009 (2)
C9	0.0553 (19)	0.072 (2)	0.0546 (19)	−0.0175 (17)	−0.0003 (15)	0.0035 (17)
C11	0.068 (2)	0.061 (2)	0.079 (3)	0.0028 (18)	0.010 (2)	−0.009 (2)
F1A	0.1195 (19)	0.136 (3)	0.090 (2)	−0.043 (2)	−0.010 (2)	0.0223 (18)
F2A	0.1195 (19)	0.136 (3)	0.090 (2)	−0.043 (2)	−0.010 (2)	0.0223 (18)
F3A	0.1195 (19)	0.136 (3)	0.090 (2)	−0.043 (2)	−0.010 (2)	0.0223 (18)
F1B	0.1195 (19)	0.136 (3)	0.090 (2)	−0.043 (2)	−0.010 (2)	0.0223 (18)
F2B	0.1195 (19)	0.136 (3)	0.090 (2)	−0.043 (2)	−0.010 (2)	0.0223 (18)
F3B	0.1195 (19)	0.136 (3)	0.090 (2)	−0.043 (2)	−0.010 (2)	0.0223 (18)

C15—C2	1.492 (5)	C5—C4	1.391 (5)
C15—H15A	0.9600	C6—H6	0.9300
C15—H15B	0.9600	O2—C9	1.415 (5)
C15—H15C	0.9600	C3—C4	1.380 (5)
C14—F2B	1.174 (16)	C3—C2	1.395 (6)
C14—F1A	1.236 (10)	C3—H3	0.9300
C14—F3A	1.263 (10)	C13—C7	1.454 (5)
C14—O2	1.336 (7)	C13—H13	0.9300
C14—F1B	1.371 (16)	C7—C8	1.380 (5)
C14—F3B	1.387 (12)	C7—C12	1.406 (5)
C14—F2A	1.387 (10)	C4—H4	0.9300
I1—C1	2.102 (3)	C12—C11	1.396 (6)
O1—C12	1.344 (5)	C8—C9	1.377 (6)
O1—H1	0.8200	C8—H8	0.9300
N1—C13	1.272 (5)	C10—C11	1.343 (7)
N1—C5	1.420 (4)	C10—C9	1.386 (6)
C1—C2	1.391 (5)	C10—H10	0.9300
C1—C6	1.392 (5)	C11—H11	0.9300
C5—C6	1.379 (5)
C2—C15—H15A	109.5	C5—C6—C1	120.2 (3)
C2—C15—H15B	109.5	C5—C6—H6	119.9
H15A—C15—H15B	109.5	C1—C6—H6	119.9
C2—C15—H15C	109.5	C14—O2—C9	117.8 (4)
H15A—C15—H15C	109.5	C4—C3—C2	122.7 (3)
H15B—C15—H15C	109.5	C4—C3—H3	118.6
F2B—C14—F1A	122.8 (10)	C2—C3—H3	118.6
F2B—C14—F3A	56.8 (8)	N1—C13—C7	122.9 (3)
F1A—C14—F3A	110.3 (7)	N1—C13—H13	118.6
F2B—C14—O2	120.6 (8)	C7—C13—H13	118.6
F1A—C14—O2	113.4 (6)	C8—C7—C12	119.4 (3)
F3A—C14—O2	119.7 (6)	C8—C7—C13	119.4 (3)
F2B—C14—F1B	118.3 (11)	C12—C7—C13	121.2 (3)
F1A—C14—F1B	25.2 (7)	C3—C4—C5	120.0 (3)
F3A—C14—F1B	131.3 (8)	C3—C4—H4	120.0
O2—C14—F1B	103.9 (7)	C5—C4—H4	120.0
F2B—C14—F3B	100.5 (10)	O1—C12—C11	119.7 (4)
F1A—C14—F3B	86.9 (7)	O1—C12—C7	121.9 (3)
F3A—C14—F3B	43.6 (6)	C11—C12—C7	118.4 (4)
O2—C14—F3B	100.3 (7)	C9—C8—C7	120.3 (4)
F1B—C14—F3B	111.8 (9)	C9—C8—H8	119.8
F2B—C14—F2A	39.0 (8)	C7—C8—H8	119.8
F1A—C14—F2A	108.9 (8)	C1—C2—C3	115.9 (3)
F3A—C14—F2A	95.7 (7)	C1—C2—C15	123.3 (4)
O2—C14—F2A	106.9 (6)	C3—C2—C15	120.7 (3)
F1B—C14—F2A	90.9 (9)	C11—C10—C9	119.7 (4)
F3B—C14—F2A	139.0 (8)	C11—C10—H10	120.1
C12—O1—H1	109.5	C9—C10—H10	120.1
C13—N1—C5	120.7 (3)	C8—C9—C10	120.4 (4)
C2—C1—C6	122.3 (3)	C8—C9—O2	119.7 (4)
C2—C1—I1	119.9 (3)	C10—C9—O2	119.7 (4)
C6—C1—I1	117.8 (2)	C10—C11—C12	121.7 (4)
C6—C5—C4	118.8 (3)	C10—C11—H11	119.1
C6—C5—N1	116.8 (3)	C12—C11—H11	119.1
C4—C5—N1	124.4 (3)
C13—N1—C5—C6	167.1 (3)	C8—C7—C12—C11	−0.5 (6)
C13—N1—C5—C4	−13.6 (5)	C13—C7—C12—C11	179.3 (4)
C4—C5—C6—C1	1.2 (5)	C12—C7—C8—C9	−1.1 (6)
N1—C5—C6—C1	−179.4 (3)	C13—C7—C8—C9	179.1 (3)
C2—C1—C6—C5	−0.9 (5)	C6—C1—C2—C3	−0.1 (5)
I1—C1—C6—C5	178.6 (2)	I1—C1—C2—C3	−179.6 (3)
F2B—C14—O2—C9	−31.7 (14)	C6—C1—C2—C15	−179.8 (3)
F1A—C14—O2—C9	168.1 (7)	I1—C1—C2—C15	0.7 (5)
F3A—C14—O2—C9	35.1 (10)	C4—C3—C2—C1	0.7 (6)
F1B—C14—O2—C9	−167.2 (8)	C4—C3—C2—C15	−179.6 (4)
F3B—C14—O2—C9	77.1 (7)	C7—C8—C9—C10	1.8 (6)
F2A—C14—O2—C9	−71.9 (7)	C7—C8—C9—O2	176.2 (3)
C5—N1—C13—C7	179.4 (3)	C11—C10—C9—C8	−0.9 (7)
N1—C13—C7—C8	−179.2 (3)	C11—C10—C9—O2	−175.2 (4)
N1—C13—C7—C12	1.0 (5)	C14—O2—C9—C8	81.3 (6)
C2—C3—C4—C5	−0.3 (6)	C14—O2—C9—C10	−104.3 (6)
C6—C5—C4—C3	−0.7 (5)	C9—C10—C11—C12	−0.7 (8)
N1—C5—C4—C3	−180.0 (3)	O1—C12—C11—C10	−179.3 (4)
C8—C7—C12—O1	−179.8 (4)	C7—C12—C11—C10	1.4 (7)
C13—C7—C12—O1	0.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.628 (4)	147
C15—H15B···Cgi	0.96	2.85	3.570 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.628 (4)	147
C15—H15B⋯Cg i	0.96	2.85	3.570 (5)	133

Symmetry code: (i) .