(E)-N'-(2-Hy-droxy-3,5-diiodo-benzyl-idene)-3-methyl-benzohydrazide.

In the title compound, C(15)H(12)I(2)N(2)O(2), the dihedral angle between the benzene rings is 26.5 (3)° and the mol-ecule has an E configuration about the C=N bond. An intra-molecular O-H⋯N hydrogen bond is observed in the mol-ecule. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12I2N2O2

M = 506.07

Monoclinic,

a = 14.778 (3) Å

b = 11.764 (3) Å

c = 9.8480 (19) Å

β = 102.191 (2)°

V = 1673.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 3.76 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 = 0.567, T max = 0.602

11923 measured reflections

3430 independent reflections

2072 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.175

S = 1.02

3430 reflections

196 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.01 e Å−3

Δρmin = −1.21 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200387X/su2373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200387X/su2373Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200387X/su2373Isup3.cml

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

C15H12I2N2O2	F(000) = 952
Mr = 506.07	Dx = 2.009 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2661 reflections
a = 14.778 (3) Å	θ = 2.2–24.4°
b = 11.764 (3) Å	µ = 3.76 mm−1
c = 9.8480 (19) Å	T = 298 K
β = 102.191 (2)°	Cut from needle, colourless
V = 1673.4 (6) Å3	0.17 × 0.15 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3430 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→18
Tmin = 0.567, Tmax = 0.602	k = −14→14
11923 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.058P)2 + 13.9544P] where P = (Fo2 + 2Fc2)/3
3430 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 2.01 e Å−3
1 restraint	Δρmin = −1.21 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	0.35741 (6)	0.46000 (8)	0.09441 (9)	0.0923 (4)
I2	0.26264 (6)	0.40585 (9)	0.65569 (12)	0.0979 (4)
N1	0.6613 (5)	0.2920 (6)	0.4785 (7)	0.0399 (17)
N2	0.7486 (5)	0.2539 (6)	0.5352 (7)	0.0410 (17)
O1	0.5439 (5)	0.3715 (6)	0.2693 (6)	0.0589 (18)
H1	0.5930	0.3439	0.3106	0.088*
O2	0.7851 (4)	0.2492 (7)	0.3260 (6)	0.0599 (19)
C1	0.5105 (6)	0.3476 (7)	0.4956 (10)	0.044 (2)
C2	0.4846 (6)	0.3768 (7)	0.3551 (9)	0.045 (2)
C3	0.3942 (7)	0.4123 (9)	0.3033 (11)	0.059 (3)
C4	0.3331 (7)	0.4219 (8)	0.3891 (13)	0.066 (3)
H4	0.2733	0.4478	0.3532	0.080*
C5	0.3581 (6)	0.3939 (9)	0.5277 (13)	0.061 (3)
C6	0.4465 (6)	0.3558 (8)	0.5815 (11)	0.055 (2)
H6	0.4636	0.3355	0.6747	0.066*
C7	0.6045 (6)	0.3093 (7)	0.5559 (9)	0.043 (2)
H7	0.6225	0.2976	0.6512	0.052*
C8	0.8065 (6)	0.2322 (7)	0.4513 (8)	0.039 (2)
C9	0.8987 (6)	0.1848 (7)	0.5190 (8)	0.0377 (19)
C10	0.9737 (7)	0.2119 (9)	0.4621 (11)	0.059 (3)
H10	0.9661	0.2599	0.3855	0.070*
C11	1.0589 (8)	0.1685 (11)	0.5179 (14)	0.075 (3)
H11	1.1091	0.1863	0.4787	0.090*
C12	1.0708 (7)	0.0988 (11)	0.6311 (12)	0.072 (3)
H12	1.1297	0.0711	0.6691	0.086*
C13	0.9977 (8)	0.0684 (10)	0.6908 (10)	0.067 (3)
C14	0.9116 (7)	0.1147 (8)	0.6307 (9)	0.049 (2)
H14	0.8610	0.0968	0.6689	0.059*
C15	1.0119 (11)	−0.0117 (13)	0.8132 (13)	0.108 (5)
H15A	1.0718	0.0011	0.8714	0.162*
H15B	1.0078	−0.0888	0.7805	0.162*
H15C	0.9650	0.0015	0.8656	0.162*
H2	0.767 (4)	0.239 (6)	0.626 (2)	0.018 (17)*

	U11	U22	U33	U12	U13	U23
I1	0.0839 (6)	0.0968 (7)	0.0776 (6)	0.0291 (5)	−0.0248 (4)	0.0073 (5)
I2	0.0542 (5)	0.1061 (8)	0.1439 (9)	−0.0029 (5)	0.0449 (5)	−0.0132 (6)
N1	0.037 (4)	0.044 (4)	0.036 (4)	0.009 (3)	0.001 (3)	0.002 (3)
N2	0.041 (4)	0.056 (5)	0.024 (3)	0.010 (3)	0.002 (3)	0.001 (3)
O1	0.054 (4)	0.072 (5)	0.044 (4)	0.016 (4)	−0.005 (3)	0.002 (3)
O2	0.058 (4)	0.101 (5)	0.023 (3)	0.011 (4)	0.014 (3)	0.005 (3)
C1	0.039 (5)	0.033 (4)	0.058 (6)	−0.001 (4)	0.003 (4)	−0.008 (4)
C2	0.044 (5)	0.040 (5)	0.046 (5)	0.006 (4)	−0.002 (4)	−0.013 (4)
C3	0.061 (6)	0.053 (6)	0.056 (6)	0.008 (5)	−0.007 (5)	−0.012 (5)
C4	0.043 (6)	0.045 (6)	0.101 (9)	0.005 (5)	−0.008 (6)	−0.015 (6)
C5	0.035 (5)	0.053 (6)	0.093 (8)	−0.007 (5)	0.008 (5)	−0.013 (6)
C6	0.044 (5)	0.049 (6)	0.071 (7)	0.000 (5)	0.012 (5)	−0.007 (5)
C7	0.044 (5)	0.044 (5)	0.041 (5)	0.006 (4)	0.007 (4)	−0.004 (4)
C8	0.045 (5)	0.049 (5)	0.020 (4)	−0.001 (4)	0.006 (3)	−0.002 (3)
C9	0.040 (5)	0.045 (5)	0.027 (4)	0.003 (4)	0.006 (3)	−0.006 (4)
C10	0.052 (6)	0.058 (6)	0.064 (6)	0.002 (5)	0.007 (5)	0.000 (5)
C11	0.049 (7)	0.090 (9)	0.091 (9)	−0.008 (6)	0.028 (6)	−0.011 (7)
C12	0.039 (6)	0.101 (9)	0.070 (8)	0.017 (6)	0.000 (5)	−0.025 (7)
C13	0.074 (8)	0.078 (8)	0.042 (5)	0.027 (6)	−0.008 (5)	−0.002 (5)
C14	0.051 (5)	0.065 (6)	0.032 (5)	0.015 (5)	0.009 (4)	−0.008 (4)
C15	0.114 (11)	0.133 (13)	0.069 (8)	0.070 (10)	0.001 (8)	0.016 (8)

I1—C3	2.090 (10)	C6—H6	0.9300
I2—C5	2.085 (11)	C7—H7	0.9300
N1—C7	1.264 (10)	C8—C9	1.493 (11)
N1—N2	1.368 (9)	C9—C14	1.356 (12)
N2—C8	1.334 (10)	C9—C10	1.381 (13)
N2—H2	0.897 (10)	C10—C11	1.362 (15)
O1—C2	1.341 (11)	C10—H10	0.9300
O1—H1	0.8200	C11—C12	1.365 (17)
O2—C8	1.224 (9)	C11—H11	0.9300
C1—C2	1.399 (12)	C12—C13	1.381 (16)
C1—C6	1.399 (13)	C12—H12	0.9300
C1—C7	1.461 (12)	C13—C14	1.395 (13)
C2—C3	1.390 (13)	C13—C15	1.510 (16)
C3—C4	1.365 (15)	C14—H14	0.9300
C4—C5	1.377 (16)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.377 (13)	C15—H15C	0.9600
C7—N1—N2	119.7 (7)	O2—C8—C9	121.9 (8)
C8—N2—N1	118.8 (6)	N2—C8—C9	116.1 (6)
C8—N2—H2	119 (4)	C14—C9—C10	118.9 (8)
N1—N2—H2	123 (4)	C14—C9—C8	123.2 (8)
C2—O1—H1	109.5	C10—C9—C8	117.9 (8)
C2—C1—C6	120.2 (8)	C11—C10—C9	120.1 (10)
C2—C1—C7	121.0 (8)	C11—C10—H10	119.9
C6—C1—C7	118.8 (8)	C9—C10—H10	119.9
O1—C2—C3	119.2 (8)	C10—C11—C12	120.3 (11)
O1—C2—C1	122.2 (8)	C10—C11—H11	119.9
C3—C2—C1	118.5 (9)	C12—C11—H11	119.9
C4—C3—C2	120.5 (10)	C11—C12—C13	121.7 (10)
C4—C3—I1	121.2 (8)	C11—C12—H12	119.2
C2—C3—I1	118.1 (8)	C13—C12—H12	119.2
C3—C4—C5	121.3 (10)	C12—C13—C14	116.4 (10)
C3—C4—H4	119.3	C12—C13—C15	120.8 (11)
C5—C4—H4	119.3	C14—C13—C15	122.8 (11)
C6—C5—C4	119.6 (10)	C9—C14—C13	122.7 (10)
C6—C5—I2	119.8 (9)	C9—C14—H14	118.6
C4—C5—I2	120.6 (8)	C13—C14—H14	118.6
C5—C6—C1	119.8 (10)	C13—C15—H15A	109.5
C5—C6—H6	120.1	C13—C15—H15B	109.5
C1—C6—H6	120.1	H15A—C15—H15B	109.5
N1—C7—C1	120.0 (8)	C13—C15—H15C	109.5
N1—C7—H7	120.0	H15A—C15—H15C	109.5
C1—C7—H7	120.0	H15B—C15—H15C	109.5
O2—C8—N2	122.1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.572 (8)	146
N2—H2···O2i	0.90 (1)	1.93 (2)	2.800 (9)	162 (6)

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	2.572 (8)	146
N2—H2⋯O2i	0.90 (1)	1.93 (2)	2.800 (9)	162 (6)

Symmetry code: (i) .