2-[(4-Bromo-phenyl-imino)-meth-yl]-4,6-di-iodo-phenol.

The title compound, C(13)H(8)BrI(2)NO, was prepared by the reaction of 3,5-diiodo-salicyl-aldehyde with 4-bromo-phenyl-amine in ethanol. There is an intra-molecular O-H⋯N hydrogen bond in the mol-ecule, which generates an S(6) ring. The dihedral angle between the benzene rings is 2.6 (3)°.

Related literature

For the biological activities of Schiff bases, see: Chohan et al. (2012 ▶); Yan et al. (2011 ▶); Zhang et al. (2011 ▶). For the coordination of Schiff bases, see: You et al. (2008 ▶); Xu et al. (2009 ▶); Chen et al. (2010 ▶); Cui et al. (2011 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H8BrI2NO

M = 527.91

Triclinic,

a = 7.9870 (13) Å

b = 8.9811 (14) Å

c = 11.3907 (18) Å

α = 91.093 (2)°

β = 99.873 (2)°

γ = 114.570 (2)°

V = 728.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 7.05 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.380, T max = 0.418

6174 measured reflections

3125 independent reflections

2425 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.094

S = 1.07

3125 reflections

164 parameters

H-atom parameters constrained

Δρmax = 1.26 e Å−3

Δρmin = −0.76 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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/S160053681200551X/qm2053sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200551X/qm2053Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200551X/qm2053Isup3.cml

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

C13H8BrI2NO	Z = 2
Mr = 527.91	F(000) = 484
Triclinic, P1	Dx = 2.407 Mg m−3
a = 7.9870 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9811 (14) Å	Cell parameters from 1027 reflections
c = 11.3907 (18) Å	θ = 2.5–25.1°
α = 91.093 (2)°	µ = 7.05 mm−1
β = 99.873 (2)°	T = 298 K
γ = 114.570 (2)°	Block, yellow
V = 728.4 (2) Å3	0.17 × 0.15 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	3125 independent reflections
Radiation source: fine-focus sealed tube	2425 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.380, Tmax = 0.418	k = −10→11
6174 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0399P)2 + 1.2928P] where P = (Fo2 + 2Fc2)/3
3125 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 1.26 e Å−3
0 restraints	Δρmin = −0.76 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	0.87298 (7)	0.30448 (5)	−0.38474 (3)	0.06516 (15)
Br1	0.27660 (10)	0.16630 (8)	0.47166 (5)	0.0712 (2)
I2	1.20768 (6)	1.02378 (4)	−0.20734 (4)	0.06502 (15)
N1	0.6508 (5)	0.3888 (5)	0.0440 (3)	0.0403 (9)
O1	0.7124 (6)	0.2911 (4)	−0.1515 (3)	0.0532 (9)
H1	0.6635	0.2839	−0.0929	0.080*
C1	0.8487 (7)	0.5748 (6)	−0.0729 (4)	0.0390 (10)
C2	0.8205 (6)	0.4496 (6)	−0.1604 (4)	0.0380 (10)
C3	0.9082 (7)	0.4926 (6)	−0.2583 (4)	0.0421 (11)
C4	1.0185 (7)	0.6550 (6)	−0.2713 (4)	0.0444 (11)
H4	1.0764	0.6820	−0.3371	0.053*
C5	1.0422 (7)	0.7773 (6)	−0.1854 (4)	0.0418 (11)
C6	0.9621 (7)	0.7389 (6)	−0.0865 (4)	0.0416 (11)
H6	0.9830	0.8220	−0.0282	0.050*
C7	0.7600 (7)	0.5360 (6)	0.0313 (4)	0.0419 (11)
H7	0.7836	0.6202	0.0894	0.050*
C8	0.5660 (6)	0.3466 (6)	0.1464 (4)	0.0397 (10)
C9	0.5782 (8)	0.4581 (7)	0.2364 (5)	0.0554 (14)
H9	0.6453	0.5703	0.2325	0.066*
C10	0.4912 (8)	0.4041 (7)	0.3323 (5)	0.0548 (14)
H10	0.4986	0.4796	0.3922	0.066*
C11	0.3947 (7)	0.2400 (7)	0.3386 (4)	0.0469 (12)
C12	0.3773 (8)	0.1262 (7)	0.2497 (5)	0.0547 (14)
H12	0.3098	0.0143	0.2545	0.066*
C13	0.4618 (8)	0.1808 (7)	0.1527 (5)	0.0517 (13)
H13	0.4484	0.1048	0.0910	0.062*

	U11	U22	U33	U12	U13	U23
I1	0.0980 (3)	0.0439 (2)	0.0485 (2)	0.0182 (2)	0.0335 (2)	0.00210 (15)
Br1	0.0904 (5)	0.0621 (4)	0.0500 (3)	0.0110 (3)	0.0415 (3)	0.0074 (3)
I2	0.0833 (3)	0.0366 (2)	0.0657 (3)	0.01060 (18)	0.0292 (2)	0.01196 (16)
N1	0.041 (2)	0.044 (2)	0.039 (2)	0.0172 (18)	0.0162 (17)	0.0086 (17)
O1	0.067 (2)	0.0355 (18)	0.047 (2)	0.0065 (16)	0.0266 (18)	0.0060 (15)
C1	0.041 (3)	0.042 (3)	0.037 (2)	0.018 (2)	0.0134 (19)	0.0135 (19)
C2	0.039 (2)	0.036 (2)	0.038 (2)	0.0129 (19)	0.0105 (19)	0.0054 (18)
C3	0.049 (3)	0.044 (3)	0.036 (2)	0.020 (2)	0.013 (2)	0.007 (2)
C4	0.053 (3)	0.043 (3)	0.040 (2)	0.019 (2)	0.018 (2)	0.013 (2)
C5	0.047 (3)	0.032 (2)	0.046 (3)	0.013 (2)	0.018 (2)	0.012 (2)
C6	0.044 (3)	0.040 (3)	0.043 (2)	0.019 (2)	0.010 (2)	0.004 (2)
C7	0.049 (3)	0.043 (3)	0.040 (2)	0.022 (2)	0.017 (2)	0.008 (2)
C8	0.037 (2)	0.047 (3)	0.038 (2)	0.017 (2)	0.0153 (19)	0.010 (2)
C9	0.070 (4)	0.041 (3)	0.049 (3)	0.012 (3)	0.028 (3)	0.005 (2)
C10	0.070 (4)	0.047 (3)	0.042 (3)	0.016 (3)	0.022 (3)	−0.002 (2)
C11	0.049 (3)	0.051 (3)	0.038 (2)	0.015 (2)	0.019 (2)	0.007 (2)
C12	0.063 (3)	0.043 (3)	0.053 (3)	0.011 (2)	0.027 (3)	0.007 (2)
C13	0.063 (3)	0.045 (3)	0.049 (3)	0.020 (3)	0.026 (3)	0.005 (2)

I1—C3	2.093 (5)	C5—C6	1.369 (7)
Br1—C11	1.907 (5)	C6—H6	0.9300
I2—C5	2.101 (5)	C7—H7	0.9300
N1—C7	1.273 (6)	C8—C9	1.382 (7)
N1—C8	1.427 (6)	C8—C13	1.382 (7)
O1—C2	1.340 (6)	C9—C10	1.382 (7)
O1—H1	0.8200	C9—H9	0.9300
C1—C6	1.401 (7)	C10—C11	1.360 (8)
C1—C2	1.406 (7)	C10—H10	0.9300
C1—C7	1.460 (6)	C11—C12	1.373 (7)
C2—C3	1.394 (6)	C12—C13	1.385 (7)
C3—C4	1.382 (7)	C12—H12	0.9300
C4—C5	1.387 (7)	C13—H13	0.9300
C4—H4	0.9300
C7—N1—C8	122.4 (4)	N1—C7—H7	119.4
C2—O1—H1	109.5	C1—C7—H7	119.4
C6—C1—C2	119.6 (4)	C9—C8—C13	118.8 (4)
C6—C1—C7	119.6 (4)	C9—C8—N1	125.0 (5)
C2—C1—C7	120.8 (4)	C13—C8—N1	116.1 (4)
O1—C2—C3	119.6 (4)	C8—C9—C10	120.4 (5)
O1—C2—C1	121.7 (4)	C8—C9—H9	119.8
C3—C2—C1	118.7 (4)	C10—C9—H9	119.8
C4—C3—C2	121.2 (4)	C11—C10—C9	119.7 (5)
C4—C3—I1	120.4 (3)	C11—C10—H10	120.1
C2—C3—I1	118.4 (4)	C9—C10—H10	120.1
C3—C4—C5	119.3 (4)	C10—C11—C12	121.3 (5)
C3—C4—H4	120.3	C10—C11—Br1	119.5 (4)
C5—C4—H4	120.3	C12—C11—Br1	119.2 (4)
C6—C5—C4	121.0 (4)	C11—C12—C13	118.9 (5)
C6—C5—I2	120.1 (4)	C11—C12—H12	120.6
C4—C5—I2	118.9 (3)	C13—C12—H12	120.6
C5—C6—C1	120.2 (4)	C8—C13—C12	120.8 (5)
C5—C6—H6	119.9	C8—C13—H13	119.6
C1—C6—H6	119.9	C12—C13—H13	119.6
N1—C7—C1	121.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.576 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.576 (5)	148