2,4-Diiodo-6-[(propyl-imino)-meth-yl]phenol.

The title compound, C(10)H(11)I(2)NO, was prepared by the reaction of 3,5-diiodo-salicyl-aldehyde with propyl-amine in ethanol. The mol-ecule adopts an E conformation with respect to the C=N bond and the aromatic ring. The aromatic ring and the imino unit are close to being coplanar, with a dihedral angle of 2.6 (3)° between their planes. This planarity is assisted by the formation of an intra-molecular O-H⋯O hydrogen bond.

Related literature

For the biological activity of Schiff base compounds, see: Chohan et al. (2012 ▶); Yan et al. (2011 ▶); Zhang et al. (2011 ▶). For their use as ligands in coordination chemistry, see: You et al. (2008 ▶); Xu et al. (2009 ▶); Chen et al. (2010 ▶); Cui et al. (2011 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H11I2NO

M = 415.00

Orthorhombic,

a = 10.7019 (14) Å

b = 7.1483 (9) Å

c = 32.404 (4) Å

V = 2478.9 (5) Å3

Z = 8

Mo Kα radiation

μ = 5.05 mm−1

T = 298 K

0.21 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.417, T max = 0.432

18976 measured reflections

2704 independent reflections

2224 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.104

S = 1.23

2704 reflections

131 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.96 e Å−3

Δρmin = −0.89 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005727/sj5194sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005727/sj5194Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005727/sj5194Isup3.cml

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

C10H11I2NO	F(000) = 1536
Mr = 415.00	Dx = 2.224 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1027 reflections
a = 10.7019 (14) Å	θ = 2.3–24.5°
b = 7.1483 (9) Å	µ = 5.05 mm−1
c = 32.404 (4) Å	T = 298 K
V = 2478.9 (5) Å3	Block, yellow
Z = 8	0.21 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2704 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.417, Tmax = 0.432	k = −9→8
18976 measured reflections	l = −41→41

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ2(Fo2) + (0.038P)2 + 7.4143P] where P = (Fo2 + 2Fc2)/3
2704 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.96 e Å−3
1 restraint	Δρmin = −0.89 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
I1	0.14060 (4)	0.18844 (7)	0.522554 (12)	0.05384 (15)
I2	−0.14147 (3)	0.44774 (7)	0.371421 (13)	0.05752 (16)
N1	0.3755 (4)	0.4405 (7)	0.34042 (16)	0.0449 (11)
O1	0.1359 (4)	0.4554 (7)	0.33939 (13)	0.0520 (10)
C1	0.2521 (5)	0.3571 (7)	0.39908 (16)	0.0378 (11)
C2	0.1382 (5)	0.3981 (8)	0.37824 (17)	0.0393 (11)
C3	0.0266 (5)	0.3772 (7)	0.40084 (16)	0.0396 (11)
C4	0.0250 (5)	0.3193 (8)	0.44167 (17)	0.0444 (12)
H4	−0.0501	0.3087	0.4559	0.053*
C5	0.1389 (5)	0.2770 (7)	0.46109 (17)	0.0397 (11)
C6	0.2501 (5)	0.2976 (7)	0.44023 (16)	0.0415 (11)
H6	0.3250	0.2716	0.4537	0.050*
C7	0.3699 (5)	0.3819 (8)	0.37775 (18)	0.0431 (12)
H7	0.4438	0.3544	0.3916	0.052*
C8	0.4981 (6)	0.4653 (9)	0.32071 (19)	0.0520 (14)
H8A	0.5636	0.4343	0.3402	0.062*
H8B	0.5085	0.5952	0.3127	0.062*
C9	0.5099 (6)	0.3412 (10)	0.28282 (19)	0.0572 (16)
H9A	0.4486	0.3791	0.2624	0.069*
H9B	0.4926	0.2126	0.2904	0.069*
C10	0.6403 (7)	0.3541 (14)	0.2642 (2)	0.077 (2)
H10A	0.6567	0.4809	0.2561	0.115*
H10B	0.6453	0.2740	0.2405	0.115*
H10C	0.7009	0.3154	0.2843	0.115*
H1	0.211 (3)	0.471 (11)	0.327 (2)	0.080*

	U11	U22	U33	U12	U13	U23
I1	0.0536 (2)	0.0651 (3)	0.0428 (2)	−0.0002 (2)	−0.00119 (15)	0.00945 (18)
I2	0.0393 (2)	0.0751 (3)	0.0582 (3)	0.00399 (19)	−0.01085 (16)	0.0073 (2)
N1	0.039 (2)	0.045 (3)	0.050 (3)	−0.002 (2)	0.0032 (19)	−0.001 (2)
O1	0.048 (2)	0.060 (3)	0.048 (2)	0.004 (2)	−0.0015 (17)	0.008 (2)
C1	0.037 (2)	0.032 (3)	0.045 (3)	0.003 (2)	−0.002 (2)	−0.005 (2)
C2	0.044 (3)	0.035 (3)	0.040 (3)	0.001 (2)	−0.004 (2)	−0.006 (2)
C3	0.039 (3)	0.035 (3)	0.045 (3)	0.004 (2)	−0.008 (2)	−0.002 (2)
C4	0.040 (3)	0.042 (3)	0.052 (3)	0.002 (2)	0.002 (2)	−0.002 (2)
C5	0.045 (3)	0.033 (3)	0.042 (3)	0.002 (2)	−0.003 (2)	0.001 (2)
C6	0.040 (3)	0.036 (3)	0.048 (3)	0.004 (2)	−0.005 (2)	−0.003 (2)
C7	0.041 (3)	0.043 (3)	0.045 (3)	0.002 (2)	−0.002 (2)	−0.009 (2)
C8	0.041 (3)	0.059 (4)	0.057 (3)	−0.006 (3)	0.005 (2)	0.000 (3)
C9	0.057 (4)	0.067 (4)	0.048 (3)	−0.006 (3)	0.005 (3)	−0.001 (3)
C10	0.070 (5)	0.099 (6)	0.061 (4)	−0.003 (4)	0.017 (3)	0.005 (4)

I1—C5	2.090 (5)	C5—C6	1.377 (7)
I2—C3	2.097 (5)	C6—H6	0.9300
N1—C7	1.282 (8)	C7—H7	0.9300
N1—C8	1.471 (7)	C8—C9	1.520 (9)
O1—C2	1.324 (7)	C8—H8A	0.9700
O1—H1	0.900 (10)	C8—H8B	0.9700
C1—C6	1.400 (7)	C9—C10	1.523 (9)
C1—C2	1.424 (7)	C9—H9A	0.9700
C1—C7	1.449 (7)	C9—H9B	0.9700
C2—C3	1.409 (7)	C10—H10A	0.9600
C3—C4	1.386 (8)	C10—H10B	0.9600
C4—C5	1.405 (7)	C10—H10C	0.9600
C4—H4	0.9300
C7—N1—C8	119.4 (5)	N1—C7—H7	119.0
C2—O1—H1	116 (5)	C1—C7—H7	119.0
C6—C1—C2	120.1 (5)	N1—C8—C9	110.7 (5)
C6—C1—C7	120.3 (5)	N1—C8—H8A	109.5
C2—C1—C7	119.6 (5)	C9—C8—H8A	109.5
O1—C2—C3	120.7 (5)	N1—C8—H8B	109.5
O1—C2—C1	122.1 (5)	C9—C8—H8B	109.5
C3—C2—C1	117.2 (5)	H8A—C8—H8B	108.1
C4—C3—C2	122.6 (5)	C8—C9—C10	111.1 (6)
C4—C3—I2	119.7 (4)	C8—C9—H9A	109.4
C2—C3—I2	117.7 (4)	C10—C9—H9A	109.4
C3—C4—C5	118.7 (5)	C8—C9—H9B	109.4
C3—C4—H4	120.6	C10—C9—H9B	109.4
C5—C4—H4	120.6	H9A—C9—H9B	108.0
C6—C5—C4	120.5 (5)	C9—C10—H10A	109.5
C6—C5—I1	119.5 (4)	C9—C10—H10B	109.5
C4—C5—I1	120.0 (4)	H10A—C10—H10B	109.5
C5—C6—C1	120.9 (5)	C9—C10—H10C	109.5
C5—C6—H6	119.6	H10A—C10—H10C	109.5
C1—C6—H6	119.6	H10B—C10—H10C	109.5
N1—C7—C1	122.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.90 (1)	1.82 (5)	2.567 (6)	138 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.90 (1)	1.82 (5)	2.567 (6)	138 (7)