(E)-1-[(3-Iodo-phen-yl)imino-meth-yl]naphthalen-2-ol.

In the title mol-ecule, C(17)H(12)INO, the dihedral angle between the naphthaldeyde plane and the 3-iodo-aniline plane is20.07 (13)°. It exists in the solid state as an enol-imine tautomer with a strong intra-molecular O-H⋯N hydrogen bond.

Related literature

For the applications of iodoaromatic compounds in synthetic organic chemistry, medicine and biochemistry, see; Merkushev (1988 ▶); Olah et al. (1993 ▶). Schiff base complexes have been used in catalytic reactions and are used as models for biological systems, see: Hamilton et al. (1987 ▶); Pyrz et al. (1985 ▶); Costamagna et al. (1992 ▶). For related structures, see: Ünver et al. (2000 ▶); Manvizhi et al. (2011 ▶).

Experimental

Crystal data

C17H12INO

M = 373.18

Monoclinic,

a = 32.059 (3) Å

b = 4.8392 (3) Å

c = 19.2682 (16) Å

β = 107.269 (6)°

V = 2854.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 2.24 mm−1

T = 296 K

0.80 × 0.30 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.793, T max = 0.925

9569 measured reflections

2781 independent reflections

1607 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.094

S = 0.93

2781 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.57 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: WinGX (Farrugia, 1997 ▶) and 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 ▶) and PLATON (Spek, 2009).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036793/zj2093sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036793/zj2093Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036793/zj2093Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812036793/zj2093Isup4.cml

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

C17H12INO	F(000) = 1456
Mr = 373.18	Dx = 1.737 Mg m−3
Monoclinic, C2/c	Melting point = 410–412 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 32.059 (3) Å	Cell parameters from 9569 reflections
b = 4.8392 (3) Å	θ = 1.3–26.0°
c = 19.2682 (16) Å	µ = 2.24 mm−1
β = 107.269 (6)°	T = 296 K
V = 2854.5 (4) Å3	Needle, yellow
Z = 8	0.80 × 0.30 × 0.03 mm

Stoe IPDS 2 diffractometer	2781 independent reflections
Radiation source: fine-focus sealed tube	1607 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
w–scan rotation	θmax = 26.0°, θmin = 1.3°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −38→38
Tmin = 0.793, Tmax = 0.925	k = −5→5
9569 measured reflections	l = −23→23

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0405P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max = 0.001
2781 reflections	Δρmax = 0.87 e Å−3
181 parameters	Δρmin = −0.57 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0

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
I1	0.052729 (12)	0.52255 (9)	0.33319 (2)	0.08465 (19)
C5	0.16216 (15)	0.0503 (9)	0.4653 (2)	0.0490 (11)
C8	0.15014 (14)	−0.4836 (10)	0.5955 (2)	0.0498 (11)
O1	0.22667 (12)	−0.3804 (8)	0.6294 (2)	0.0784 (11)
H1	0.2177	−0.2766	0.5946	0.118*
C9	0.19336 (16)	−0.5200 (11)	0.6398 (3)	0.0593 (13)
C11	0.1710 (2)	−0.8587 (12)	0.7108 (3)	0.0712 (16)
H11	0.1781	−0.9838	0.7491	0.085*
N1	0.17155 (13)	−0.1458 (9)	0.5220 (2)	0.0546 (10)
C4	0.19651 (17)	0.1402 (12)	0.4410 (3)	0.0620 (13)
H4	0.2243	0.0672	0.4616	0.074*
C6	0.12123 (16)	0.1594 (10)	0.4331 (2)	0.0514 (12)
H6	0.0976	0.1010	0.4481	0.062*
C7	0.14134 (16)	−0.2876 (10)	0.5375 (2)	0.0508 (12)
H7	0.1125	−0.2607	0.5096	0.061*
C3	0.19005 (19)	0.3351 (13)	0.3873 (3)	0.0721 (16)
H3	0.2135	0.3935	0.3720	0.087*
C2	0.14946 (18)	0.4450 (11)	0.3557 (3)	0.0655 (14)
H2	0.1451	0.5779	0.3194	0.079*
C1	0.11518 (16)	0.3532 (11)	0.3793 (2)	0.0544 (12)
C13	0.11570 (16)	−0.6479 (10)	0.6093 (2)	0.0510 (12)
C17	0.0936 (2)	−0.9958 (12)	0.6815 (3)	0.0797 (16)
H17	0.1007	−1.1192	0.7203	0.096*
C14	0.07180 (17)	−0.6311 (12)	0.5668 (3)	0.0651 (14)
H14	0.0638	−0.5092	0.5277	0.078*
C16	0.0511 (2)	−0.9750 (14)	0.6391 (4)	0.0868 (18)
H16	0.0296	−1.0836	0.6488	0.104*
C10	0.20262 (19)	−0.7080 (12)	0.6980 (3)	0.0693 (15)
H10	0.2312	−0.7273	0.7279	0.083*
C12	0.1268 (2)	−0.8351 (11)	0.6679 (3)	0.0613 (14)
C15	0.0407 (2)	−0.7938 (14)	0.5825 (4)	0.0810 (17)
H15	0.0118	−0.7799	0.5538	0.097*

	U11	U22	U33	U12	U13	U23
I1	0.0709 (2)	0.0937 (3)	0.0771 (3)	0.0026 (2)	0.00310 (19)	0.0215 (2)
C5	0.053 (3)	0.047 (3)	0.047 (3)	−0.006 (2)	0.014 (2)	−0.009 (2)
C8	0.058 (3)	0.048 (3)	0.045 (2)	0.007 (2)	0.017 (2)	−0.005 (2)
O1	0.054 (2)	0.094 (3)	0.079 (3)	0.005 (2)	0.007 (2)	0.005 (2)
C9	0.058 (3)	0.060 (3)	0.058 (3)	0.010 (3)	0.015 (2)	−0.010 (3)
C11	0.104 (5)	0.060 (4)	0.045 (3)	0.021 (3)	0.014 (3)	0.006 (3)
N1	0.053 (2)	0.055 (3)	0.056 (2)	0.001 (2)	0.016 (2)	−0.005 (2)
C4	0.053 (3)	0.067 (4)	0.067 (3)	−0.011 (3)	0.019 (3)	−0.009 (3)
C6	0.054 (3)	0.056 (3)	0.045 (3)	−0.010 (2)	0.015 (2)	−0.005 (2)
C7	0.050 (3)	0.053 (3)	0.046 (3)	0.004 (2)	0.010 (2)	−0.007 (2)
C3	0.069 (4)	0.085 (4)	0.070 (4)	−0.027 (3)	0.032 (3)	−0.004 (3)
C2	0.073 (3)	0.073 (4)	0.051 (3)	−0.012 (3)	0.018 (3)	0.004 (3)
C1	0.058 (3)	0.060 (3)	0.043 (3)	−0.009 (2)	0.011 (2)	−0.007 (2)
C13	0.060 (3)	0.045 (3)	0.052 (3)	0.005 (2)	0.022 (2)	−0.007 (2)
C17	0.114 (5)	0.059 (4)	0.080 (4)	0.007 (4)	0.049 (4)	0.005 (3)
C14	0.059 (3)	0.068 (4)	0.070 (3)	−0.002 (3)	0.022 (3)	0.001 (3)
C16	0.099 (5)	0.073 (4)	0.107 (5)	−0.017 (4)	0.059 (4)	−0.005 (4)
C10	0.067 (4)	0.071 (4)	0.060 (3)	0.014 (3)	0.004 (3)	0.001 (3)
C12	0.090 (4)	0.048 (3)	0.053 (3)	0.008 (3)	0.032 (3)	−0.001 (2)
C15	0.069 (4)	0.082 (5)	0.097 (5)	−0.006 (3)	0.032 (4)	−0.013 (4)

I1—C1	2.101 (5)	C6—H6	0.9300
C5—C6	1.379 (6)	C7—H7	0.9300
C5—C4	1.387 (6)	C3—C2	1.370 (7)
C5—N1	1.411 (6)	C3—H3	0.9300
C8—C9	1.406 (6)	C2—C1	1.381 (7)
C8—C7	1.428 (6)	C2—H2	0.9300
C8—C13	1.448 (7)	C13—C14	1.406 (7)
O1—C9	1.328 (6)	C13—C12	1.408 (7)
O1—H1	0.8200	C17—C16	1.368 (9)
C9—C10	1.405 (7)	C17—C12	1.404 (8)
C11—C10	1.331 (8)	C17—H17	0.9300
C11—C12	1.416 (7)	C14—C15	1.373 (8)
C11—H11	0.9300	C14—H14	0.9300
N1—C7	1.292 (6)	C16—C15	1.361 (9)
C4—C3	1.370 (8)	C16—H16	0.9300
C4—H4	0.9300	C10—H10	0.9300
C6—C1	1.369 (7)	C15—H15	0.9300
C6—C5—C4	118.3 (5)	C3—C2—H2	120.9
C6—C5—N1	124.1 (4)	C1—C2—H2	120.9
C4—C5—N1	117.6 (4)	C6—C1—C2	121.4 (5)
C9—C8—C7	119.3 (4)	C6—C1—I1	119.4 (4)
C9—C8—C13	119.1 (4)	C2—C1—I1	119.2 (4)
C7—C8—C13	121.6 (4)	C14—C13—C12	118.4 (5)
C9—O1—H1	109.5	C14—C13—C8	123.1 (4)
O1—C9—C10	117.4 (5)	C12—C13—C8	118.4 (5)
O1—C9—C8	122.4 (5)	C16—C17—C12	121.5 (6)
C10—C9—C8	120.2 (5)	C16—C17—H17	119.2
C10—C11—C12	122.2 (5)	C12—C17—H17	119.2
C10—C11—H11	118.9	C15—C14—C13	120.3 (5)
C12—C11—H11	118.9	C15—C14—H14	119.9
C7—N1—C5	122.3 (4)	C13—C14—H14	119.9
C3—C4—C5	120.9 (5)	C15—C16—C17	119.3 (6)
C3—C4—H4	119.6	C15—C16—H16	120.4
C5—C4—H4	119.6	C17—C16—H16	120.4
C1—C6—C5	120.3 (4)	C11—C10—C9	120.7 (5)
C1—C6—H6	119.8	C11—C10—H10	119.7
C5—C6—H6	119.8	C9—C10—H10	119.7
N1—C7—C8	123.1 (4)	C17—C12—C13	118.8 (6)
N1—C7—H7	118.5	C17—C12—C11	121.9 (5)
C8—C7—H7	118.5	C13—C12—C11	119.4 (5)
C2—C3—C4	120.9 (5)	C16—C15—C14	121.7 (6)
C2—C3—H3	119.6	C16—C15—H15	119.1
C4—C3—H3	119.6	C14—C15—H15	119.1
C3—C2—C1	118.3 (5)
C7—C8—C9—O1	−0.8 (7)	C7—C8—C13—C14	1.2 (7)
C13—C8—C9—O1	178.7 (4)	C9—C8—C13—C12	1.1 (6)
C7—C8—C9—C10	178.8 (4)	C7—C8—C13—C12	−179.4 (4)
C13—C8—C9—C10	−1.7 (7)	C12—C13—C14—C15	0.2 (8)
C6—C5—N1—C7	16.5 (7)	C8—C13—C14—C15	179.6 (5)
C4—C5—N1—C7	−164.2 (4)	C12—C17—C16—C15	−0.2 (9)
C6—C5—C4—C3	0.9 (7)	C12—C11—C10—C9	−1.1 (9)
N1—C5—C4—C3	−178.5 (4)	O1—C9—C10—C11	−178.7 (5)
C4—C5—C6—C1	−0.6 (7)	C8—C9—C10—C11	1.7 (8)
N1—C5—C6—C1	178.7 (4)	C16—C17—C12—C13	0.3 (8)
C5—N1—C7—C8	−179.0 (4)	C16—C17—C12—C11	−178.9 (5)
C9—C8—C7—N1	2.2 (7)	C14—C13—C12—C17	−0.3 (7)
C13—C8—C7—N1	−177.2 (4)	C8—C13—C12—C17	−179.8 (4)
C5—C4—C3—C2	−0.4 (8)	C14—C13—C12—C11	179.0 (5)
C4—C3—C2—C1	−0.3 (8)	C8—C13—C12—C11	−0.5 (7)
C5—C6—C1—C2	−0.1 (7)	C10—C11—C12—C17	179.7 (5)
C5—C6—C1—I1	−178.5 (3)	C10—C11—C12—C13	0.5 (8)
C3—C2—C1—C6	0.6 (8)	C17—C16—C15—C14	0.1 (9)
C3—C2—C1—I1	179.0 (4)	C13—C14—C15—C16	−0.1 (9)
C9—C8—C13—C14	−178.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.555 (6)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.555 (6)	148