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

The asymmetric unit of the title compound, C(15)H(12)I(2)N(2)O(2), contains two independent mol-ecules in which the dihedral angles between the two benzene rings are 62.4 (7) and 41.1 (7)°. Intra-molecular O-H⋯N hydrogen bonds generate S(6) ring motifs in each mol-ecule. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the a 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 ▶). For reference bond-length data, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H12I2N2O2

M = 506.07

Monoclinic,

a = 9.658 (2) Å

b = 11.723 (2) Å

c = 14.732 (3) Å

β = 93.216 (2)°

V = 1665.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 3.78 mm−1

T = 298 K

0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.549, T max = 0.601

12106 measured reflections

5976 independent reflections

4443 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.089

S = 1.01

5976 reflections

389 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.88 e Å−3

Absolute structure: Flack (1983 ▶), 2163 Friedel pairs

Flack parameter: 0.10 (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 datablocks global, I. DOI: 10.1107/S1600536810052050/sj5075sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052050/sj5075Isup2.hkl

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

C15H12I2N2O2	F(000) = 952
Mr = 506.07	Dx = 2.018 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3095 reflections
a = 9.658 (2) Å	θ = 2.5–24.5°
b = 11.723 (2) Å	µ = 3.78 mm−1
c = 14.732 (3) Å	T = 298 K
β = 93.216 (2)°	Block, colourless
V = 1665.4 (6) Å3	0.18 × 0.17 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5976 independent reflections
Radiation source: fine-focus sealed tube	4443 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.549, Tmax = 0.601	k = −9→14
12106 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0325P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
5976 reflections	Δρmax = 0.53 e Å−3
389 parameters	Δρmin = −0.88 e Å−3
3 restraints	Absolute structure: Flack (1983), 2163 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (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	0.63728 (6)	−0.05063 (8)	0.65864 (5)	0.0703 (3)
I2	0.04006 (6)	0.04601 (6)	0.72932 (4)	0.0560 (2)
I3	1.16416 (8)	0.40275 (8)	0.64944 (6)	0.0777 (3)
I4	0.57051 (8)	0.30877 (7)	0.73109 (5)	0.0722 (3)
N1	0.3538 (7)	0.1082 (8)	0.3438 (4)	0.040 (2)
N2	0.3260 (6)	0.1360 (8)	0.2538 (5)	0.039 (2)
N3	0.8691 (7)	0.2375 (8)	0.3398 (5)	0.037 (2)
N4	0.8323 (6)	0.2070 (7)	0.2514 (5)	0.038 (2)
O1	0.5262 (5)	0.0329 (7)	0.4690 (4)	0.0500 (18)
H1	0.4996	0.0449	0.4160	0.075*
O2	0.5548 (5)	0.1423 (9)	0.2297 (4)	0.065 (3)
O3	1.0418 (5)	0.3199 (8)	0.4607 (4)	0.055 (2)
H3	1.0188	0.2846	0.4142	0.082*
O4	1.0562 (5)	0.2148 (8)	0.2173 (4)	0.062 (3)
C1	0.2840 (8)	0.0766 (8)	0.4902 (6)	0.035 (2)
C2	0.4176 (7)	0.0386 (10)	0.5221 (6)	0.038 (2)
C3	0.4385 (7)	0.0046 (8)	0.6126 (6)	0.038 (2)
C4	0.3328 (8)	0.0075 (8)	0.6722 (5)	0.041 (3)
H4A	0.3488	−0.0147	0.7325	0.050*
C5	0.2011 (7)	0.0447 (10)	0.6398 (6)	0.041 (2)
C6	0.1778 (8)	0.0739 (8)	0.5498 (5)	0.036 (2)
H6	0.0883	0.0925	0.5283	0.044*
C7	0.2561 (8)	0.1083 (9)	0.3969 (6)	0.037 (2)
H7	0.1670	0.1288	0.3759	0.044*
C8	0.4346 (7)	0.1479 (9)	0.1991 (5)	0.034 (2)
C9	0.3917 (8)	0.1684 (10)	0.1014 (6)	0.043 (3)
C10	0.4529 (9)	0.2538 (8)	0.0538 (6)	0.048 (2)
C11	0.4131 (11)	0.2638 (10)	−0.0406 (6)	0.070 (3)
H11	0.4512	0.3210	−0.0751	0.084*
C12	0.3196 (13)	0.1896 (14)	−0.0802 (8)	0.086 (5)
H12	0.2945	0.1972	−0.1417	0.103*
C13	0.2618 (11)	0.1041 (11)	−0.0316 (7)	0.079 (3)
H13	0.1987	0.0541	−0.0604	0.095*
C14	0.2961 (9)	0.0924 (9)	0.0577 (6)	0.058 (3)
H14	0.2568	0.0343	0.0906	0.070*
C15	0.5496 (10)	0.3374 (10)	0.0925 (7)	0.075 (3)
H15A	0.5197	0.3620	0.1504	0.113*
H15B	0.5531	0.4018	0.0524	0.113*
H15C	0.6402	0.3039	0.1004	0.113*
C16	0.8046 (8)	0.2772 (9)	0.4902 (5)	0.041 (3)
C17	0.9381 (8)	0.3161 (10)	0.5183 (5)	0.037 (2)
C18	0.9635 (8)	0.3486 (9)	0.6068 (6)	0.045 (3)
C19	0.8592 (10)	0.3491 (9)	0.6676 (6)	0.052 (3)
H19	0.8777	0.3739	0.7270	0.063*
C20	0.7290 (9)	0.3129 (10)	0.6401 (6)	0.046 (2)
C21	0.7013 (9)	0.2749 (9)	0.5519 (6)	0.050 (3)
H21	0.6135	0.2477	0.5340	0.060*
C22	0.7737 (9)	0.2397 (10)	0.3971 (6)	0.043 (3)
H22	0.6841	0.2171	0.3789	0.051*
C23	0.9330 (8)	0.1963 (10)	0.1929 (6)	0.048 (3)
C24	0.8872 (8)	0.1720 (9)	0.0985 (6)	0.039 (2)
C25	0.9316 (9)	0.2342 (8)	0.0260 (6)	0.054 (2)
C26	0.8796 (12)	0.2072 (11)	−0.0621 (7)	0.068 (3)
H26	0.9075	0.2497	−0.1112	0.082*
C27	0.7902 (12)	0.1207 (15)	−0.0763 (8)	0.085 (4)
H27	0.7588	0.1041	−0.1357	0.102*
C28	0.7430 (10)	0.0558 (11)	−0.0069 (8)	0.079 (3)
H28	0.6805	−0.0035	−0.0187	0.094*
C29	0.7919 (9)	0.0814 (9)	0.0826 (6)	0.057 (3)
H29	0.7617	0.0391	0.1311	0.069*
C30	1.0280 (11)	0.3345 (9)	0.0403 (7)	0.076 (3)
H30A	1.0004	0.3786	0.0911	0.114*
H30B	1.0239	0.3812	−0.0133	0.114*
H30C	1.1211	0.3075	0.0522	0.114*
H2	0.239 (4)	0.153 (10)	0.233 (6)	0.080*
H4	0.748 (4)	0.188 (10)	0.227 (6)	0.080*

	U11	U22	U33	U12	U13	U23
I1	0.0474 (4)	0.0872 (8)	0.0748 (5)	0.0162 (4)	−0.0098 (3)	0.0093 (4)
I2	0.0566 (4)	0.0726 (6)	0.0403 (3)	0.0013 (4)	0.0168 (2)	0.0029 (4)
I3	0.0673 (5)	0.0831 (8)	0.0806 (6)	−0.0164 (4)	−0.0136 (4)	−0.0137 (5)
I4	0.0870 (5)	0.0812 (7)	0.0519 (5)	0.0016 (5)	0.0343 (4)	0.0025 (4)
N1	0.045 (4)	0.051 (7)	0.024 (4)	−0.004 (3)	0.007 (3)	0.004 (3)
N2	0.029 (3)	0.053 (6)	0.035 (4)	0.000 (3)	0.006 (3)	−0.002 (4)
N3	0.034 (4)	0.037 (6)	0.040 (5)	−0.004 (3)	0.002 (3)	0.004 (4)
N4	0.031 (4)	0.054 (6)	0.031 (4)	−0.002 (3)	0.006 (3)	0.001 (4)
O1	0.042 (3)	0.064 (6)	0.045 (4)	−0.001 (3)	0.010 (2)	0.004 (4)
O2	0.026 (3)	0.121 (8)	0.048 (4)	−0.007 (3)	−0.002 (3)	0.007 (4)
O3	0.037 (3)	0.071 (6)	0.058 (4)	−0.002 (4)	0.012 (3)	−0.005 (4)
O4	0.032 (3)	0.101 (8)	0.054 (4)	0.010 (3)	0.004 (3)	−0.010 (4)
C1	0.035 (4)	0.029 (7)	0.042 (5)	−0.004 (4)	0.007 (3)	−0.003 (4)
C2	0.033 (4)	0.031 (7)	0.051 (5)	−0.007 (4)	0.006 (3)	0.000 (5)
C3	0.038 (4)	0.040 (7)	0.036 (5)	0.001 (4)	−0.004 (3)	0.007 (4)
C4	0.062 (5)	0.037 (7)	0.024 (5)	0.001 (4)	−0.005 (4)	0.003 (4)
C5	0.036 (4)	0.042 (7)	0.043 (5)	0.002 (5)	0.002 (3)	0.005 (5)
C6	0.039 (4)	0.042 (8)	0.027 (4)	0.007 (4)	0.000 (3)	0.000 (4)
C7	0.040 (5)	0.036 (7)	0.035 (5)	−0.007 (4)	0.007 (4)	−0.002 (4)
C8	0.030 (4)	0.044 (7)	0.028 (4)	−0.002 (4)	0.003 (3)	−0.001 (4)
C9	0.028 (4)	0.061 (8)	0.040 (5)	0.003 (4)	0.012 (4)	−0.001 (5)
C10	0.044 (5)	0.052 (7)	0.050 (5)	0.009 (4)	0.017 (4)	−0.003 (4)
C11	0.087 (8)	0.080 (9)	0.047 (6)	0.013 (6)	0.035 (5)	0.006 (5)
C12	0.108 (10)	0.118 (15)	0.032 (6)	0.005 (9)	0.014 (6)	−0.004 (7)
C13	0.084 (8)	0.103 (10)	0.048 (6)	−0.004 (7)	−0.015 (5)	−0.020 (6)
C14	0.059 (6)	0.077 (8)	0.037 (5)	−0.007 (5)	−0.001 (4)	−0.010 (5)
C15	0.076 (7)	0.080 (9)	0.070 (7)	−0.014 (6)	0.001 (5)	0.017 (6)
C16	0.044 (5)	0.052 (9)	0.026 (5)	0.003 (4)	−0.001 (3)	−0.001 (4)
C17	0.050 (5)	0.029 (6)	0.032 (5)	0.002 (4)	−0.001 (3)	0.007 (5)
C18	0.044 (5)	0.044 (8)	0.047 (6)	0.009 (4)	0.004 (4)	0.005 (5)
C19	0.081 (7)	0.034 (8)	0.039 (6)	0.001 (5)	−0.014 (5)	−0.002 (5)
C20	0.062 (6)	0.045 (7)	0.031 (5)	−0.002 (5)	0.010 (4)	0.000 (5)
C21	0.050 (5)	0.046 (8)	0.055 (7)	0.006 (5)	0.014 (4)	0.003 (5)
C22	0.047 (5)	0.050 (8)	0.032 (5)	−0.004 (5)	0.006 (4)	−0.001 (5)
C23	0.033 (5)	0.063 (9)	0.049 (6)	0.010 (5)	0.006 (4)	−0.004 (5)
C24	0.040 (5)	0.043 (7)	0.034 (5)	0.015 (4)	0.005 (3)	−0.005 (5)
C25	0.069 (6)	0.051 (7)	0.043 (5)	0.011 (5)	0.014 (4)	−0.006 (4)
C26	0.084 (8)	0.077 (10)	0.045 (6)	0.020 (7)	0.019 (5)	0.007 (6)
C27	0.075 (8)	0.133 (14)	0.047 (7)	0.030 (8)	−0.004 (6)	−0.013 (7)
C28	0.067 (7)	0.076 (9)	0.092 (9)	−0.002 (6)	−0.002 (6)	−0.033 (7)
C29	0.050 (5)	0.069 (8)	0.054 (6)	0.005 (5)	0.010 (4)	−0.010 (5)
C30	0.089 (8)	0.069 (8)	0.073 (7)	−0.008 (6)	0.028 (6)	−0.009 (6)

I1—C3	2.102 (8)	C11—H11	0.9300
I2—C5	2.095 (8)	C12—C13	1.369 (17)
I3—C18	2.101 (9)	C12—H12	0.9300
I4—C20	2.091 (8)	C13—C14	1.346 (12)
N1—C7	1.259 (9)	C13—H13	0.9300
N1—N2	1.378 (9)	C14—H14	0.9300
N2—C8	1.365 (9)	C15—H15A	0.9600
N2—H2	0.90 (6)	C15—H15B	0.9600
N3—C22	1.284 (9)	C15—H15C	0.9600
N3—N4	1.377 (9)	C16—C21	1.386 (11)
N4—C23	1.341 (10)	C16—C17	1.408 (12)
N4—H4	0.90 (5)	C16—C22	1.456 (11)
O1—C2	1.345 (8)	C17—C18	1.367 (12)
O1—H1	0.8200	C18—C19	1.386 (12)
O2—C8	1.224 (9)	C19—C20	1.367 (12)
O3—C17	1.349 (8)	C19—H19	0.9300
O3—H3	0.8200	C20—C21	1.386 (12)
O4—C23	1.243 (10)	C21—H21	0.9300
C1—C6	1.387 (10)	C22—H22	0.9300
C1—C2	1.420 (11)	C23—C24	1.464 (11)
C1—C7	1.435 (11)	C24—C25	1.381 (12)
C2—C3	1.395 (11)	C24—C29	1.416 (13)
C3—C4	1.383 (10)	C25—C26	1.401 (13)
C4—C5	1.403 (11)	C25—C30	1.507 (13)
C4—H4A	0.9300	C26—C27	1.341 (18)
C5—C6	1.376 (11)	C26—H26	0.9300
C6—H6	0.9300	C27—C28	1.373 (17)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.495 (11)	C28—C29	1.409 (12)
C9—C10	1.374 (13)	C28—H28	0.9300
C9—C14	1.412 (12)	C29—H29	0.9300
C10—C11	1.426 (12)	C30—H30A	0.9600
C10—C15	1.450 (13)	C30—H30B	0.9600
C11—C12	1.361 (16)	C30—H30C	0.9600
C7—N1—N2	119.1 (7)	C10—C15—H15B	109.5
C8—N2—N1	118.6 (6)	H15A—C15—H15B	109.5
C8—N2—H2	120 (6)	C10—C15—H15C	109.5
N1—N2—H2	121 (6)	H15A—C15—H15C	109.5
C22—N3—N4	118.1 (7)	H15B—C15—H15C	109.5
C23—N4—N3	118.3 (7)	C21—C16—C17	119.7 (8)
C23—N4—H4	113 (6)	C21—C16—C22	119.7 (9)
N3—N4—H4	128 (6)	C17—C16—C22	120.7 (7)
C2—O1—H1	109.5	O3—C17—C18	119.4 (8)
C17—O3—H3	109.5	O3—C17—C16	121.7 (8)
C6—C1—C2	118.3 (8)	C18—C17—C16	118.9 (7)
C6—C1—C7	120.4 (8)	C17—C18—C19	121.3 (9)
C2—C1—C7	121.1 (7)	C17—C18—I3	118.9 (6)
O1—C2—C3	117.8 (7)	C19—C18—I3	119.8 (7)
O1—C2—C1	123.1 (8)	C20—C19—C18	119.8 (9)
C3—C2—C1	119.1 (7)	C20—C19—H19	120.1
C4—C3—C2	121.8 (7)	C18—C19—H19	120.1
C4—C3—I1	119.7 (6)	C19—C20—C21	120.3 (8)
C2—C3—I1	118.4 (6)	C19—C20—I4	120.8 (7)
C3—C4—C5	118.6 (8)	C21—C20—I4	118.9 (7)
C3—C4—H4A	120.7	C16—C21—C20	120.0 (9)
C5—C4—H4A	120.7	C16—C21—H21	120.0
C6—C5—C4	120.1 (7)	C20—C21—H21	120.0
C6—C5—I2	121.2 (6)	N3—C22—C16	120.6 (9)
C4—C5—I2	118.6 (6)	N3—C22—H22	119.7
C5—C6—C1	121.9 (8)	C16—C22—H22	119.7
C5—C6—H6	119.0	O4—C23—N4	121.0 (9)
C1—C6—H6	119.0	O4—C23—C24	122.9 (7)
N1—C7—C1	119.2 (8)	N4—C23—C24	115.9 (7)
N1—C7—H7	120.4	C25—C24—C29	119.7 (8)
C1—C7—H7	120.4	C25—C24—C23	122.8 (9)
O2—C8—N2	121.4 (8)	C29—C24—C23	117.5 (8)
O2—C8—C9	124.7 (7)	C24—C25—C26	119.1 (10)
N2—C8—C9	113.9 (6)	C24—C25—C30	121.3 (8)
C10—C9—C14	121.1 (8)	C26—C25—C30	119.5 (9)
C10—C9—C8	120.3 (8)	C27—C26—C25	120.7 (11)
C14—C9—C8	118.5 (9)	C27—C26—H26	119.7
C9—C10—C11	117.2 (9)	C25—C26—H26	119.7
C9—C10—C15	125.3 (8)	C26—C27—C28	122.7 (11)
C11—C10—C15	117.4 (9)	C26—C27—H27	118.6
C12—C11—C10	120.1 (10)	C28—C27—H27	118.6
C12—C11—H11	120.0	C27—C28—C29	118.1 (11)
C10—C11—H11	120.0	C27—C28—H28	120.9
C11—C12—C13	121.6 (11)	C29—C28—H28	120.9
C11—C12—H12	119.2	C28—C29—C24	119.7 (9)
C13—C12—H12	119.2	C28—C29—H29	120.2
C14—C13—C12	120.0 (11)	C24—C29—H29	120.2
C14—C13—H13	120.0	C25—C30—H30A	109.5
C12—C13—H13	120.0	C25—C30—H30B	109.5
C13—C14—C9	120.0 (10)	H30A—C30—H30B	109.5
C13—C14—H14	120.0	C25—C30—H30C	109.5
C9—C14—H14	120.0	H30A—C30—H30C	109.5
C10—C15—H15A	109.5	H30B—C30—H30C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.570 (9)	143
O3—H3···N3	0.82	1.85	2.560 (10)	144
N4—H4···O2	0.90 (5)	1.94 (4)	2.786 (8)	155 (8)
N2—H2···O4i	0.90 (6)	1.91 (3)	2.788 (9)	164 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.570 (9)	143
O3—H3⋯N3	0.82	1.85	2.560 (10)	144
N4—H4⋯O2	0.90 (5)	1.94 (4)	2.786 (8)	155 (8)
N2—H2⋯O4i	0.90 (6)	1.91 (3)	2.788 (9)	164 (10)

Symmetry code: (i) .