2-Chloro-N'-(2-hy-droxy-3,5-diiodo-benzyl-idene)benzohydrazide.

In the title compound, C(14)H(9)ClI(2)N(2)O(2), the dihedral angle between the benzene rings is 65.9 (2)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. The mol-ecule has an E conformation about the C=N bond. In the crystal, mol-ecules are linked into C(4) chains propagating in [001] by N-H⋯O hydrogen bonds.

Related literature

For background to hydrazone compounds and their biological properties, see: Kucukguzel et al. (2006 ▶); Khattab (2005 ▶); Karthikeyan et al. (2006 ▶); Okabe et al. (1993 ▶). For reference bond-length values, see: Allen et al. (1987 ▶). For related structures, see: Shan et al. (2008 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Ma et al. (2008 ▶); Diao et al. (2008a ▶,b ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C14H9ClI2N2O2

M = 526.48

Monoclinic,

a = 14.311 (3) Å

b = 11.469 (2) Å

c = 9.736 (2) Å

β = 90.032 (2)°

V = 1598.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.11 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.525, T max = 0.542

7381 measured reflections

3383 independent reflections

1747 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.112

S = 0.95

3383 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.93 e Å−3

Δρmin = −0.80 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007653/hb5809sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007653/hb5809Isup2.hkl

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

C14H9ClI2N2O2	F(000) = 984
Mr = 526.48	Dx = 2.188 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 989 reflections
a = 14.311 (3) Å	θ = 2.5–24.5°
b = 11.469 (2) Å	µ = 4.11 mm−1
c = 9.736 (2) Å	T = 298 K
β = 90.032 (2)°	Block, colourless
V = 1598.0 (5) Å3	0.18 × 0.17 × 0.17 mm
Z = 4

Bruker SMART CCD diffractometer	3383 independent reflections
Radiation source: fine-focus sealed tube	1747 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→13
Tmin = 0.525, Tmax = 0.542	k = −14→9
7381 measured reflections	l = −12→12

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0353P)2] where P = (Fo2 + 2Fc2)/3
3383 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.93 e Å−3
1 restraint	Δρmin = −0.80 e Å−3

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 > 2sigma(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	−0.22657 (4)	0.87447 (6)	−0.18612 (7)	0.0664 (2)
I2	−0.12679 (4)	0.97420 (6)	0.39763 (7)	0.0689 (2)
Cl1	0.39839 (19)	0.5079 (3)	0.3068 (3)	0.0908 (9)
N1	0.1820 (4)	0.8044 (6)	0.1129 (6)	0.0385 (16)
N2	0.2702 (4)	0.7650 (6)	0.0825 (6)	0.0402 (17)
O1	0.0634 (3)	0.8886 (5)	0.2821 (5)	0.0482 (14)
H1	0.1148	0.8671	0.2551	0.072*
O2	0.3053 (4)	0.7548 (6)	0.3039 (6)	0.077 (2)
C1	0.0291 (5)	0.8487 (6)	0.0472 (8)	0.0343 (19)
C2	0.0025 (5)	0.8833 (6)	0.1793 (8)	0.0367 (19)
C3	−0.0897 (5)	0.9172 (7)	0.2027 (8)	0.043 (2)
C4	−0.1538 (5)	0.9133 (7)	0.0998 (10)	0.050 (2)
H4	−0.2153	0.9350	0.1168	0.060*
C5	−0.1283 (5)	0.8778 (8)	−0.0279 (9)	0.051 (2)
C6	−0.0383 (5)	0.8446 (6)	−0.0562 (8)	0.044 (2)
H6	−0.0222	0.8196	−0.1439	0.053*
C7	0.1229 (5)	0.8119 (7)	0.0171 (8)	0.0378 (19)
H7	0.1400	0.7937	−0.0725	0.045*
C8	0.3274 (5)	0.7392 (8)	0.1856 (8)	0.046 (2)
C9	0.4215 (5)	0.6948 (8)	0.1424 (8)	0.044 (2)
C10	0.4584 (6)	0.5931 (8)	0.1939 (9)	0.055 (2)
C11	0.5447 (7)	0.5530 (10)	0.1535 (11)	0.074 (3)
H11	0.5699	0.4843	0.1882	0.088*
C12	0.5921 (7)	0.6211 (15)	0.0577 (14)	0.102 (6)
H12	0.6510	0.5968	0.0293	0.122*
C13	0.5576 (8)	0.7187 (12)	0.0048 (12)	0.090 (4)
H13	0.5915	0.7607	−0.0599	0.108*
C14	0.4710 (6)	0.7572 (9)	0.0471 (9)	0.068 (3)
H14	0.4462	0.8255	0.0109	0.082*
H2	0.290 (5)	0.755 (8)	−0.005 (3)	0.080*

	U11	U22	U33	U12	U13	U23
I1	0.0465 (4)	0.0791 (5)	0.0737 (5)	−0.0086 (3)	−0.0190 (3)	0.0115 (4)
I2	0.0617 (4)	0.0786 (5)	0.0663 (5)	0.0136 (3)	0.0127 (3)	−0.0186 (4)
Cl1	0.0839 (19)	0.089 (2)	0.099 (2)	−0.0011 (15)	−0.0081 (16)	0.0317 (18)
N1	0.028 (4)	0.052 (5)	0.036 (4)	0.004 (3)	−0.002 (3)	−0.002 (3)
N2	0.034 (4)	0.063 (5)	0.024 (4)	0.008 (3)	0.004 (3)	−0.005 (4)
O1	0.051 (3)	0.058 (4)	0.036 (3)	0.008 (3)	0.000 (3)	−0.002 (3)
O2	0.068 (4)	0.143 (7)	0.020 (3)	0.042 (4)	0.003 (3)	0.003 (4)
C1	0.041 (5)	0.031 (5)	0.031 (5)	−0.001 (3)	0.002 (3)	0.008 (4)
C2	0.035 (4)	0.035 (5)	0.040 (5)	−0.011 (4)	0.004 (3)	0.008 (4)
C3	0.051 (5)	0.034 (5)	0.044 (6)	−0.007 (4)	0.010 (4)	0.002 (4)
C4	0.034 (5)	0.048 (6)	0.067 (7)	0.000 (4)	0.004 (4)	0.006 (5)
C5	0.037 (5)	0.061 (6)	0.055 (6)	0.000 (4)	−0.011 (4)	0.014 (5)
C6	0.049 (5)	0.038 (5)	0.045 (5)	−0.003 (4)	−0.006 (4)	−0.008 (4)
C7	0.051 (5)	0.038 (5)	0.025 (5)	0.002 (4)	0.003 (4)	0.009 (4)
C8	0.047 (5)	0.070 (7)	0.020 (5)	0.007 (4)	0.002 (4)	0.000 (4)
C9	0.030 (4)	0.072 (7)	0.029 (5)	0.000 (4)	−0.002 (3)	−0.008 (5)
C10	0.048 (6)	0.066 (7)	0.052 (6)	−0.001 (5)	−0.007 (4)	−0.003 (5)
C11	0.054 (7)	0.100 (10)	0.067 (8)	0.026 (6)	−0.018 (5)	−0.025 (7)
C12	0.039 (6)	0.182 (16)	0.083 (10)	0.015 (8)	−0.013 (6)	−0.079 (11)
C13	0.066 (8)	0.141 (13)	0.063 (8)	−0.034 (8)	0.029 (6)	−0.016 (8)
C14	0.050 (6)	0.112 (9)	0.043 (6)	−0.006 (6)	0.010 (4)	0.007 (6)

I1—C5	2.086 (7)	C4—H4	0.9300
I2—C3	2.076 (8)	C5—C6	1.372 (10)
Cl1—C10	1.703 (9)	C6—H6	0.9300
N1—C7	1.261 (8)	C7—H7	0.9300
N1—N2	1.373 (7)	C8—C9	1.501 (10)
N2—C8	1.328 (9)	C9—C14	1.369 (11)
N2—H2	0.91 (4)	C9—C10	1.374 (12)
O1—C2	1.328 (8)	C10—C11	1.376 (11)
O1—H1	0.8200	C11—C12	1.393 (16)
O2—C8	1.208 (9)	C11—H11	0.9300
C1—C6	1.395 (10)	C12—C13	1.328 (16)
C1—C2	1.398 (10)	C12—H12	0.9300
C1—C7	1.438 (9)	C13—C14	1.379 (13)
C2—C3	1.396 (10)	C13—H13	0.9300
C3—C4	1.358 (10)	C14—H14	0.9300
C4—C5	1.358 (11)
C7—N1—N2	118.6 (6)	N1—C7—H7	120.2
C8—N2—N1	118.5 (6)	C1—C7—H7	120.2
C8—N2—H2	119 (5)	O2—C8—N2	121.8 (7)
N1—N2—H2	122 (5)	O2—C8—C9	123.5 (7)
C2—O1—H1	109.5	N2—C8—C9	114.6 (7)
C6—C1—C2	119.0 (7)	C14—C9—C10	119.5 (8)
C6—C1—C7	119.2 (7)	C14—C9—C8	118.5 (8)
C2—C1—C7	121.7 (6)	C10—C9—C8	122.0 (8)
O1—C2—C3	118.9 (7)	C9—C10—C11	121.6 (9)
O1—C2—C1	121.8 (7)	C9—C10—Cl1	121.9 (7)
C3—C2—C1	119.2 (7)	C11—C10—Cl1	116.5 (8)
C4—C3—C2	120.5 (8)	C10—C11—C12	116.2 (10)
C4—C3—I2	120.8 (6)	C10—C11—H11	121.9
C2—C3—I2	118.6 (6)	C12—C11—H11	121.9
C5—C4—C3	120.3 (8)	C13—C12—C11	123.5 (12)
C5—C4—H4	119.9	C13—C12—H12	118.3
C3—C4—H4	119.9	C11—C12—H12	118.3
C4—C5—C6	121.3 (7)	C12—C13—C14	119.2 (12)
C4—C5—I1	120.0 (6)	C12—C13—H13	120.4
C6—C5—I1	118.7 (7)	C14—C13—H13	120.4
C5—C6—C1	119.7 (8)	C9—C14—C13	120.0 (10)
C5—C6—H6	120.2	C9—C14—H14	120.0
C1—C6—H6	120.2	C13—C14—H14	120.0
N1—C7—C1	119.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.556 (8)	146
N2—H2···O2i	0.91 (4)	1.88 (2)	2.768 (8)	168 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.556 (8)	146
N2—H2⋯O2i	0.91 (4)	1.88 (2)	2.768 (8)	168 (8)

Symmetry code: (i) .