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

The title mol-ecule, C(16)H(15)I(2)N(3)O(2), adopts an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 6.4 (2)°. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains propagating in the c-axis direction.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Su et al. (2011a ▶,b ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For similar compounds that we have reported recently, see: Dai & Mao (2010a ▶,b ▶).

Experimental

Crystal data

C16H15I2N3O2

M = 535.11

Monoclinic,

a = 20.387 (4) Å

b = 9.0000 (16) Å

c = 9.8355 (17) Å

β = 94.320 (2)°

V = 1799.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.51 mm−1

T = 298 K

0.17 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.587, T max = 0.621

9471 measured reflections

3892 independent reflections

2551 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.094

S = 1.04

3892 reflections

214 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −1.06 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: 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/S1600536811035070/su2309sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035070/su2309Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035070/su2309Isup3.cml

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

C16H15I2N3O2	F(000) = 1016
Mr = 535.11	Dx = 1.975 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2040 reflections
a = 20.387 (4) Å	θ = 2.4–24.5°
b = 9.0000 (16) Å	µ = 3.51 mm−1
c = 9.8355 (17) Å	T = 298 K
β = 94.320 (2)°	Block, colourless
V = 1799.5 (5) Å3	0.17 × 0.17 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3892 independent reflections
Radiation source: fine-focus sealed tube	2551 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −25→18
Tmin = 0.587, Tmax = 0.621	k = −11→11
9471 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.036P)2 + 0.0912P] where P = (Fo2 + 2Fc2)/3
3892 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.70 e Å−3
1 restraint	Δρmin = −1.06 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	0.430896 (19)	0.68628 (4)	0.37673 (4)	0.06296 (15)
I2	0.41396 (2)	0.29856 (5)	−0.12108 (4)	0.07864 (18)
N1	0.17425 (19)	0.6984 (4)	0.1129 (4)	0.0460 (10)
N2	0.1097 (2)	0.7279 (5)	0.0734 (4)	0.0486 (11)
N3	−0.1967 (2)	0.8856 (6)	−0.0186 (5)	0.0745 (15)
O1	0.28501 (17)	0.7467 (4)	0.2597 (3)	0.0556 (9)
H1	0.2449	0.7485	0.2442	0.083*
O2	0.09491 (16)	0.8441 (4)	0.2731 (3)	0.0528 (9)
C1	0.2749 (2)	0.5829 (5)	0.0659 (4)	0.0411 (12)
C2	0.3110 (2)	0.6455 (5)	0.1782 (5)	0.0423 (12)
C3	0.3763 (2)	0.6018 (5)	0.2055 (5)	0.0400 (11)
C4	0.4057 (2)	0.5002 (5)	0.1236 (4)	0.0407 (11)
H4	0.4491	0.4712	0.1439	0.049*
C5	0.3697 (2)	0.4431 (5)	0.0118 (5)	0.0408 (11)
C6	0.3058 (2)	0.4842 (5)	−0.0169 (5)	0.0459 (12)
H6	0.2824	0.4452	−0.0936	0.055*
C7	0.2062 (2)	0.6198 (6)	0.0322 (5)	0.0481 (13)
H7	0.1853	0.5858	−0.0492	0.058*
C8	0.0719 (2)	0.8033 (5)	0.1611 (5)	0.0427 (12)
C9	0.0026 (2)	0.8230 (5)	0.1103 (5)	0.0406 (11)
C10	−0.0353 (2)	0.9280 (5)	0.1713 (5)	0.0457 (13)
H10	−0.0161	0.9855	0.2423	0.055*
C11	−0.1005 (2)	0.9493 (6)	0.1295 (5)	0.0480 (13)
H11	−0.1245	1.0206	0.1731	0.058*
C12	−0.1311 (2)	0.8675 (6)	0.0245 (5)	0.0500 (13)
C13	−0.0930 (3)	0.7631 (7)	−0.0376 (6)	0.0675 (17)
H13	−0.1121	0.7059	−0.1088	0.081*
C14	−0.0279 (3)	0.7425 (6)	0.0035 (5)	0.0563 (14)
H14	−0.0037	0.6728	−0.0414	0.068*
C15	−0.2392 (3)	0.9775 (7)	0.0537 (6)	0.0759 (19)
H15A	−0.2365	0.9488	0.1480	0.114*
H15B	−0.2837	0.9659	0.0155	0.114*
H15C	−0.2261	1.0794	0.0464	0.114*
C16	−0.2223 (3)	0.8274 (7)	−0.1472 (6)	0.083 (2)
H16A	−0.1876	0.8203	−0.2076	0.124*
H16B	−0.2561	0.8922	−0.1862	0.124*
H16C	−0.2405	0.7305	−0.1341	0.124*
H2	0.095 (3)	0.714 (6)	−0.014 (2)	0.080*

	U11	U22	U33	U12	U13	U23
I1	0.0550 (3)	0.0776 (3)	0.0542 (3)	−0.0025 (2)	−0.00991 (18)	−0.02124 (19)
I2	0.0613 (3)	0.0960 (4)	0.0767 (3)	0.0256 (2)	−0.0072 (2)	−0.0429 (2)
N1	0.034 (2)	0.068 (3)	0.036 (2)	0.010 (2)	0.0000 (18)	0.004 (2)
N2	0.036 (2)	0.075 (3)	0.034 (2)	0.015 (2)	0.0013 (19)	0.003 (2)
N3	0.041 (3)	0.121 (4)	0.060 (3)	0.024 (3)	−0.007 (2)	−0.013 (3)
O1	0.049 (2)	0.071 (2)	0.046 (2)	0.011 (2)	0.0005 (19)	−0.0170 (18)
O2	0.044 (2)	0.083 (3)	0.0309 (19)	0.0048 (18)	−0.0020 (16)	−0.0016 (18)
C1	0.040 (3)	0.055 (3)	0.028 (3)	0.004 (2)	0.000 (2)	0.002 (2)
C2	0.051 (3)	0.045 (3)	0.032 (3)	0.002 (2)	0.006 (2)	−0.002 (2)
C3	0.036 (3)	0.047 (3)	0.036 (3)	−0.003 (2)	−0.004 (2)	−0.003 (2)
C4	0.034 (3)	0.045 (3)	0.042 (3)	0.006 (2)	−0.003 (2)	0.007 (2)
C5	0.041 (3)	0.046 (3)	0.036 (3)	0.007 (2)	0.004 (2)	−0.004 (2)
C6	0.049 (3)	0.054 (3)	0.034 (3)	−0.002 (3)	−0.003 (2)	−0.009 (2)
C7	0.040 (3)	0.065 (3)	0.038 (3)	0.004 (3)	−0.006 (2)	0.002 (3)
C8	0.044 (3)	0.050 (3)	0.035 (3)	0.007 (2)	0.007 (2)	0.011 (2)
C9	0.036 (3)	0.051 (3)	0.034 (3)	0.006 (2)	0.002 (2)	0.005 (2)
C10	0.043 (3)	0.057 (3)	0.036 (3)	0.004 (3)	−0.002 (2)	−0.004 (2)
C11	0.050 (3)	0.056 (3)	0.039 (3)	0.014 (3)	0.008 (2)	−0.001 (2)
C12	0.037 (3)	0.068 (4)	0.045 (3)	0.008 (3)	0.004 (2)	0.006 (3)
C13	0.051 (4)	0.099 (5)	0.051 (4)	0.008 (3)	−0.008 (3)	−0.025 (3)
C14	0.040 (3)	0.074 (4)	0.054 (3)	0.012 (3)	0.000 (3)	−0.022 (3)
C15	0.043 (3)	0.099 (5)	0.085 (5)	0.023 (3)	0.004 (3)	0.008 (4)
C16	0.046 (4)	0.139 (6)	0.060 (4)	−0.001 (4)	−0.014 (3)	0.001 (4)

I1—C3	2.091 (4)	C6—H6	0.9300
I2—C5	2.096 (4)	C7—H7	0.9300
N1—C7	1.278 (6)	C8—C9	1.474 (6)
N1—N2	1.371 (5)	C9—C14	1.385 (6)
N2—C8	1.378 (6)	C9—C10	1.385 (6)
N2—H2	0.898 (10)	C10—C11	1.375 (6)
N3—C12	1.380 (6)	C10—H10	0.9300
N3—C15	1.427 (7)	C11—C12	1.380 (7)
N3—C16	1.431 (7)	C11—H11	0.9300
O1—C2	1.348 (5)	C12—C13	1.390 (7)
O1—H1	0.8200	C13—C14	1.370 (7)
O2—C8	1.221 (5)	C13—H13	0.9300
C1—C6	1.389 (6)	C14—H14	0.9300
C1—C2	1.400 (6)	C15—H15A	0.9600
C1—C7	1.452 (6)	C15—H15B	0.9600
C2—C3	1.393 (6)	C15—H15C	0.9600
C3—C4	1.385 (6)	C16—H16A	0.9600
C4—C5	1.375 (6)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.363 (6)
C7—N1—N2	117.1 (4)	N2—C8—C9	114.4 (4)
N1—N2—C8	119.2 (4)	C14—C9—C10	117.0 (4)
N1—N2—H2	120 (4)	C14—C9—C8	123.9 (4)
C8—N2—H2	120 (4)	C10—C9—C8	119.1 (4)
C12—N3—C15	121.7 (5)	C11—C10—C9	121.5 (5)
C12—N3—C16	120.6 (5)	C11—C10—H10	119.2
C15—N3—C16	117.2 (5)	C9—C10—H10	119.2
C2—O1—H1	109.5	C10—C11—C12	121.5 (5)
C6—C1—C2	119.0 (4)	C10—C11—H11	119.2
C6—C1—C7	119.0 (4)	C12—C11—H11	119.2
C2—C1—C7	122.0 (4)	C11—C12—N3	122.7 (5)
O1—C2—C3	119.3 (4)	C11—C12—C13	117.0 (5)
O1—C2—C1	122.3 (4)	N3—C12—C13	120.3 (5)
C3—C2—C1	118.5 (4)	C14—C13—C12	121.5 (5)
C4—C3—C2	121.6 (4)	C14—C13—H13	119.2
C4—C3—I1	118.7 (3)	C12—C13—H13	119.2
C2—C3—I1	119.7 (3)	C13—C14—C9	121.5 (5)
C5—C4—C3	118.9 (4)	C13—C14—H14	119.3
C5—C4—H4	120.6	C9—C14—H14	119.3
C3—C4—H4	120.6	N3—C15—H15A	109.5
C6—C5—C4	120.6 (4)	N3—C15—H15B	109.5
C6—C5—I2	119.2 (3)	H15A—C15—H15B	109.5
C4—C5—I2	120.1 (3)	N3—C15—H15C	109.5
C5—C6—C1	121.4 (4)	H15A—C15—H15C	109.5
C5—C6—H6	119.3	H15B—C15—H15C	109.5
C1—C6—H6	119.3	N3—C16—H16A	109.5
N1—C7—C1	120.8 (4)	N3—C16—H16B	109.5
N1—C7—H7	119.6	H16A—C16—H16B	109.5
C1—C7—H7	119.6	N3—C16—H16C	109.5
O2—C8—N2	121.2 (4)	H16A—C16—H16C	109.5
O2—C8—C9	124.3 (4)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.91	2.623 (5)	144.
N2—H2···O2i	0.90 (1)	2.16 (2)	3.016 (5)	159 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.91	2.623 (5)	144
N2—H2⋯O2i	0.90 (1)	2.16 (2)	3.016 (5)	159 (5)

Symmetry code: (i) .