(E)-2-[(4-Iodo-phen-yl)imino-meth-yl]-6-methyl-phenol.

The title compound, C(14)H(12)INO, adopts the phenol-imine tautomeric form. The dihedral angle between the aromatic rings is 20.6 (3)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond while in the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a zigzag chain parallel to the b axis.

Related literature

For background to the properties and uses of Schiff bases, see: Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶); Cohen et al. (1964 ▶); Taggi et al. (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For comparative bond lengths, see: Şahin et al. (2009 ▶). For related structures, see: Özdemir et al. (2010 ▶); Tanak et al. (2009 ▶).

Experimental

Crystal data

C14H12INO

M = 337.15

Orthorhombic,

a = 4.6773 (4) Å

b = 11.6092 (12) Å

c = 23.6751 (4) Å

V = 1285.55 (17) Å3

Z = 4

Mo Kα radiation

μ = 2.47 mm−1

T = 293 K

0.48 × 0.24 × 0.09 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: numerical (X-AREA; Stoe & Cie, 2002 ▶) T min = 0.520, T max = 0.769

7548 measured reflections

2267 independent reflections

1541 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.078

S = 0.86

2267 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 901 Friedel pairs

Flack parameter: 0.10 (5)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001826X/dn2563sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001826X/dn2563Isup2.hkl

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

C14H12INO	F(000) = 656
Mr = 337.15	Dx = 1.742 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7912 reflections
a = 4.6773 (4) Å	θ = 1.7–27.8°
b = 11.6092 (12) Å	µ = 2.47 mm−1
c = 23.6751 (4) Å	T = 293 K
V = 1285.55 (17) Å3	Prism, yellow
Z = 4	0.48 × 0.24 × 0.09 mm

Stoe IPDS II diffractometer	2267 independent reflections
Radiation source: fine-focus sealed tube	1541 reflections with I > 2σ(I)
graphite	Rint = 0.086
Detector resolution: 6.67 pixels mm-1	θmax = 25.0°, θmin = 1.7°
rotation method scans	h = −5→5
Absorption correction: numerical (X-AREA; Stoe & Cie, 2002)	k = −13→13
Tmin = 0.520, Tmax = 0.769	l = −28→28
7548 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0321P)2] where P = (Fo2 + 2Fc2)/3
S = 0.86	(Δ/σ)max = 0.001
2267 reflections	Δρmax = 0.65 e Å−3
156 parameters	Δρmin = −0.29 e Å−3
0 restraints	Absolute structure: Flack (1983), 901 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (5)

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 > 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
I1	0.81565 (9)	0.49212 (4)	0.907466 (15)	0.07878 (18)
O1	−0.3098 (17)	0.6170 (3)	0.6324 (2)	0.0759 (15)
H1	−0.2028	0.6014	0.6588	0.114*
N1	0.0187 (10)	0.4895 (5)	0.69451 (16)	0.0621 (12)
C1	−0.0685 (14)	0.4026 (6)	0.6669 (2)	0.0596 (16)
H15	0.0064	0.3306	0.6757	0.071*
C2	−0.2788 (18)	0.4106 (5)	0.6224 (3)	0.0553 (19)
C3	−0.3704 (13)	0.3134 (5)	0.5941 (3)	0.0639 (16)
H3	−0.2933	0.2423	0.6037	0.077*
C4	−0.5711 (17)	0.3190 (6)	0.5522 (3)	0.071 (2)
H4	−0.6369	0.2523	0.5348	0.085*
C5	−0.6755 (18)	0.4266 (6)	0.5361 (3)	0.0680 (18)
H5	−0.8058	0.4307	0.5065	0.082*
C6	−0.5925 (14)	0.5272 (6)	0.5624 (3)	0.0660 (19)
C7	−0.3895 (13)	0.5201 (5)	0.6065 (2)	0.0568 (15)
C8	−0.699 (2)	0.6422 (6)	0.5449 (3)	0.091 (3)
H8A	−0.8417	0.6332	0.5161	0.137*
H8B	−0.5434	0.6872	0.5305	0.137*
H8C	−0.7818	0.6806	0.5769	0.137*
C9	0.2092 (13)	0.4822 (5)	0.7398 (2)	0.0582 (13)
C10	0.3469 (18)	0.5806 (5)	0.7557 (3)	0.068 (2)
H10	0.3162	0.6479	0.7353	0.082*
C11	0.5354 (18)	0.5827 (6)	0.8024 (3)	0.069 (2)
H11	0.6340	0.6496	0.8118	0.083*
C12	0.5693 (13)	0.4850 (7)	0.8333 (2)	0.0636 (15)
C13	0.4354 (17)	0.3826 (6)	0.8184 (3)	0.0658 (19)
H13	0.4652	0.3158	0.8392	0.079*
C14	0.2599 (16)	0.3824 (5)	0.7726 (3)	0.068 (2)
H14	0.1697	0.3141	0.7625	0.081*

	U11	U22	U33	U12	U13	U23
I1	0.0755 (3)	0.0930 (3)	0.0679 (2)	−0.0021 (4)	−0.0059 (2)	−0.0085 (3)
O1	0.099 (5)	0.053 (2)	0.076 (3)	−0.001 (3)	0.001 (3)	−0.001 (2)
N1	0.060 (3)	0.068 (3)	0.058 (2)	−0.011 (4)	0.002 (2)	−0.007 (3)
C1	0.058 (4)	0.056 (4)	0.064 (4)	0.008 (3)	0.009 (3)	0.002 (3)
C2	0.050 (5)	0.060 (4)	0.057 (3)	0.004 (3)	0.001 (3)	−0.001 (3)
C3	0.068 (5)	0.060 (3)	0.064 (3)	0.012 (3)	0.003 (4)	−0.003 (3)
C4	0.071 (5)	0.076 (5)	0.067 (4)	−0.004 (4)	0.000 (4)	−0.010 (3)
C5	0.060 (4)	0.086 (5)	0.058 (4)	0.005 (5)	0.006 (4)	0.010 (3)
C6	0.066 (4)	0.072 (5)	0.060 (3)	−0.007 (4)	0.011 (3)	0.012 (3)
C7	0.059 (4)	0.061 (4)	0.051 (3)	0.002 (4)	0.012 (2)	0.007 (3)
C8	0.109 (9)	0.080 (5)	0.085 (5)	0.012 (6)	−0.006 (5)	0.016 (4)
C9	0.058 (3)	0.052 (3)	0.066 (3)	0.003 (4)	0.003 (3)	−0.006 (3)
C10	0.078 (6)	0.054 (4)	0.073 (4)	0.005 (4)	0.007 (4)	0.014 (3)
C11	0.078 (5)	0.064 (4)	0.067 (4)	−0.017 (4)	0.001 (4)	−0.005 (3)
C12	0.063 (3)	0.076 (5)	0.052 (3)	0.000 (4)	0.004 (2)	0.001 (4)
C13	0.075 (5)	0.060 (4)	0.063 (4)	−0.001 (4)	−0.004 (4)	−0.002 (3)
C14	0.074 (7)	0.058 (4)	0.071 (4)	−0.006 (4)	−0.010 (4)	−0.007 (3)

I1—C12	2.102 (5)	C6—C7	1.415 (8)
O1—C7	1.334 (7)	C6—C8	1.484 (9)
O1—H1	0.8200	C8—H8A	0.9600
N1—C1	1.269 (8)	C8—H8B	0.9600
N1—C9	1.397 (7)	C8—H8C	0.9600
C1—C2	1.444 (10)	C9—C10	1.364 (9)
C1—H15	0.9300	C9—C14	1.414 (9)
C2—C3	1.381 (8)	C10—C11	1.415 (10)
C2—C7	1.423 (9)	C10—H10	0.9300
C3—C4	1.367 (9)	C11—C12	1.358 (9)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.394 (10)	C12—C13	1.389 (10)
C4—H4	0.9300	C13—C14	1.359 (9)
C5—C6	1.379 (9)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C7—O1—H1	109.5	C6—C8—H8B	109.5
C1—N1—C9	123.5 (6)	H8A—C8—H8B	109.5
N1—C1—C2	122.9 (6)	C6—C8—H8C	109.5
N1—C1—H15	118.5	H8A—C8—H8C	109.5
C2—C1—H15	118.5	H8B—C8—H8C	109.5
C3—C2—C7	119.2 (6)	C10—C9—N1	117.5 (6)
C3—C2—C1	120.9 (6)	C10—C9—C14	117.1 (5)
C7—C2—C1	119.9 (6)	N1—C9—C14	125.3 (6)
C4—C3—C2	121.8 (6)	C9—C10—C11	121.6 (6)
C4—C3—H3	119.1	C9—C10—H10	119.2
C2—C3—H3	119.1	C11—C10—H10	119.2
C3—C4—C5	118.8 (6)	C12—C11—C10	118.6 (6)
C3—C4—H4	120.6	C12—C11—H11	120.7
C5—C4—H4	120.6	C10—C11—H11	120.7
C6—C5—C4	122.4 (6)	C11—C12—C13	121.7 (5)
C6—C5—H5	118.8	C11—C12—I1	118.7 (5)
C4—C5—H5	118.8	C13—C12—I1	119.5 (5)
C5—C6—C7	118.3 (6)	C14—C13—C12	118.4 (6)
C5—C6—C8	122.8 (6)	C14—C13—H13	120.8
C7—C6—C8	118.9 (7)	C12—C13—H13	120.8
O1—C7—C6	118.6 (6)	C13—C14—C9	122.5 (6)
O1—C7—C2	122.0 (5)	C13—C14—H14	118.7
C6—C7—C2	119.4 (6)	C9—C14—H14	118.7
C6—C8—H8A	109.5
C9—N1—C1—C2	176.1 (5)	C3—C2—C7—C6	0.5 (9)
N1—C1—C2—C3	−179.1 (6)	C1—C2—C7—C6	179.1 (5)
N1—C1—C2—C7	2.3 (9)	C1—N1—C9—C10	162.2 (6)
C7—C2—C3—C4	−2.0 (10)	C1—N1—C9—C14	−21.4 (9)
C1—C2—C3—C4	179.4 (6)	N1—C9—C10—C11	177.6 (6)
C2—C3—C4—C5	3.1 (10)	C14—C9—C10—C11	0.8 (10)
C3—C4—C5—C6	−2.8 (11)	C9—C10—C11—C12	−2.7 (11)
C4—C5—C6—C7	1.3 (10)	C10—C11—C12—C13	3.3 (11)
C4—C5—C6—C8	179.1 (7)	C10—C11—C12—I1	−173.8 (5)
C5—C6—C7—O1	−179.6 (6)	C11—C12—C13—C14	−2.0 (11)
C8—C6—C7—O1	2.6 (9)	I1—C12—C13—C14	175.1 (5)
C5—C6—C7—C2	−0.2 (9)	C12—C13—C14—C9	0.1 (11)
C8—C6—C7—C2	−178.0 (6)	C10—C9—C14—C13	0.5 (10)
C3—C2—C7—O1	179.9 (7)	N1—C9—C14—C13	−176.0 (6)
C1—C2—C7—O1	−1.5 (9)	C2—C1—N1—C9	176.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.591 (8)	147
C13—H13···O1i	0.93	2.51	3.348 (8)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.591 (8)	147
C13—H13⋯O1i	0.93	2.51	3.348 (8)	150

Symmetry code: (i) .