N'-(2-Hydr-oxy-3,5-diiodo-benzyl-idene)-2-methoxy-benzohydrazide.

The title compound, C(15)H(12)I(2)N(2)O(3), was synthesized by the condensation of equimolar amounts of 3,5-diiodo-salicylaldehyde and 2-methoxy-benzohydrazide in a methanol solution. There are two independent mol-ecules, A and B, in the asymmetric unit. The dihedral angle between the two benzene rings is 30.2 (2)° for mol-ecule A and 21.7 (2)° for mol-ecule B. There are intra-molecular O-H⋯N and N-H⋯O hydrogen bonds in each mol-ecule. The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio.

Related literature

For background to Schiff bases and their complexes, see: Ali et al. (2005 ▶). For related structures, see: Yehye et al. (2008a ▶,b ▶); Jing et al. (2006 ▶); Ling et al. (2008 ▶).

Experimental

Crystal data

C15H12I2N2O3

M = 522.07

Orthorhombic,

a = 16.073 (2) Å

b = 15.628 (2) Å

c = 13.284 (1) Å

V = 3336.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 3.78 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.432, T max = 0.469

26178 measured reflections

7237 independent reflections

4902 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.101

S = 1.00

7237 reflections

407 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.78 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 3436 Friedel pairs

Flack parameter: 0.59 (3)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S160053680901914X/sj2624sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901914X/sj2624Isup2.hkl

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

C15H12I2N2O3	F(000) = 1968
Mr = 522.07	Dx = 2.078 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4242 reflections
a = 16.073 (2) Å	θ = 2.3–24.5°
b = 15.628 (2) Å	µ = 3.78 mm−1
c = 13.284 (1) Å	T = 298 K
V = 3336.8 (6) Å3	Block, colorless
Z = 8	0.23 × 0.20 × 0.20 mm

Bruker SMART 1000 CCD area-detector diffractometer	7237 independent reflections
Radiation source: fine-focus sealed tube	4902 reflections with I > 2σ(I)
graphite	Rint = 0.053
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→20
Tmin = 0.432, Tmax = 0.469	k = −19→19
26178 measured reflections	l = −16→16

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
7237 reflections	Δρmax = 0.78 e Å−3
407 parameters	Δρmin = −0.56 e Å−3
3 restraints	Absolute structure: Flack (1983), 3436 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.59 (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
I3	0.40540 (3)	0.37109 (4)	0.59648 (6)	0.0789 (2)
I4	0.75672 (4)	0.29448 (4)	0.71249 (6)	0.0744 (2)
O4	0.4652 (3)	0.5530 (4)	0.6664 (5)	0.0592 (16)
H4	0.4752	0.5974	0.6971	0.071*
O5	0.4563 (4)	0.7984 (3)	0.7103 (6)	0.0738 (18)
O6	0.7003 (4)	0.8732 (4)	0.7109 (6)	0.0745 (19)
N3	0.5663 (4)	0.6711 (4)	0.7246 (6)	0.0492 (17)
N4	0.5871 (4)	0.7542 (4)	0.7391 (6)	0.0552 (19)
C16	0.6078 (4)	0.5270 (5)	0.7135 (7)	0.0428 (18)
C17	0.5299 (5)	0.4972 (5)	0.6787 (6)	0.0430 (19)
C18	0.5183 (5)	0.4121 (5)	0.6577 (7)	0.052 (2)
C19	0.5820 (5)	0.3546 (5)	0.6660 (6)	0.048 (2)
H19	0.5740	0.2974	0.6493	0.057*
C20	0.6582 (5)	0.3831 (5)	0.6994 (6)	0.047 (2)
C21	0.6718 (5)	0.4676 (5)	0.7198 (7)	0.053 (2)
H21	0.7248	0.4856	0.7381	0.064*
C22	0.6248 (5)	0.6155 (5)	0.7341 (6)	0.047 (2)
H22	0.6777	0.6325	0.7541	0.057*
C23	0.5297 (5)	0.8171 (5)	0.7244 (6)	0.0452 (19)
C24	0.5589 (5)	0.9062 (5)	0.7306 (6)	0.0455 (19)
C25	0.6422 (5)	0.9340 (5)	0.7234 (7)	0.053 (2)
C26	0.6607 (7)	1.0209 (6)	0.7251 (8)	0.074 (3)
H26	0.7154	1.0391	0.7171	0.089*
C27	0.6000 (9)	1.0786 (6)	0.7381 (7)	0.085 (4)
H27	0.6137	1.1362	0.7431	0.102*
C28	0.5176 (8)	1.0543 (7)	0.7445 (7)	0.083 (3)
H28	0.4758	1.0950	0.7518	0.100*
C29	0.4986 (6)	0.9687 (6)	0.7397 (6)	0.061 (2)
H29	0.4430	0.9522	0.7428	0.073*
C30	0.7849 (5)	0.8953 (7)	0.6937 (8)	0.080 (3)
H30A	0.8055	0.9276	0.7499	0.119*
H30B	0.7890	0.9292	0.6336	0.119*
H30C	0.8173	0.8441	0.6860	0.119*
I1	0.81885 (3)	0.63308 (4)	0.55553 (6)	0.0747 (2)
I2	0.46921 (4)	0.71070 (4)	0.43332 (6)	0.0793 (2)
O1	0.7606 (3)	0.4525 (4)	0.4793 (5)	0.0549 (16)
H1	0.7425	0.4041	0.4890	0.082*
O2	0.7669 (3)	0.2033 (4)	0.4301 (7)	0.076 (2)
O3	0.5224 (3)	0.1360 (3)	0.4748 (5)	0.0639 (16)
N1	0.6578 (4)	0.3339 (4)	0.4300 (5)	0.0465 (16)
N2	0.6348 (4)	0.2499 (4)	0.4275 (6)	0.0540 (17)
C1	0.6177 (4)	0.4794 (5)	0.4342 (6)	0.0407 (18)
C2	0.6962 (5)	0.5073 (5)	0.4661 (6)	0.046 (2)
C3	0.7075 (4)	0.5914 (5)	0.4888 (6)	0.048 (2)
C4	0.6443 (5)	0.6517 (5)	0.4757 (6)	0.052 (2)
H4A	0.6537	0.7094	0.4883	0.063*
C5	0.5680 (5)	0.6235 (5)	0.4438 (7)	0.053 (2)
C6	0.5548 (5)	0.5392 (5)	0.4207 (6)	0.0451 (19)
H6	0.5035	0.5219	0.3958	0.054*
C7	0.6016 (5)	0.3892 (5)	0.4185 (7)	0.048 (2)
H7	0.5486	0.3717	0.3996	0.057*
C8	0.6933 (5)	0.1877 (5)	0.4350 (7)	0.0462 (19)
C9	0.6631 (5)	0.0984 (5)	0.4467 (6)	0.044 (2)
C10	0.5797 (5)	0.0735 (5)	0.4667 (6)	0.047 (2)
C11	0.5616 (6)	−0.0131 (6)	0.4790 (7)	0.063 (2)
H11	0.5075	−0.0300	0.4938	0.075*
C12	0.6220 (8)	−0.0729 (6)	0.4696 (8)	0.077 (3)
H12	0.6084	−0.1304	0.4766	0.093*
C13	0.7045 (7)	−0.0501 (6)	0.4495 (7)	0.074 (3)
H13	0.7460	−0.0913	0.4437	0.089*
C14	0.7219 (6)	0.0346 (5)	0.4387 (6)	0.052 (2)
H14	0.7766	0.0503	0.4252	0.062*
C15	0.4365 (5)	0.1115 (6)	0.4888 (7)	0.066 (3)
H15A	0.4293	0.0880	0.5550	0.099*
H15B	0.4215	0.0694	0.4394	0.099*
H15C	0.4015	0.1609	0.4813	0.099*
H2	0.5807 (15)	0.237 (5)	0.435 (7)	0.080*
H4B	0.639 (2)	0.770 (5)	0.754 (7)	0.080*

	U11	U22	U33	U12	U13	U23
I3	0.0459 (3)	0.0612 (4)	0.1295 (6)	−0.0160 (3)	−0.0114 (4)	−0.0033 (4)
I4	0.0618 (4)	0.0584 (4)	0.1029 (5)	0.0198 (3)	−0.0071 (4)	−0.0048 (4)
O4	0.034 (3)	0.054 (3)	0.089 (5)	−0.002 (3)	0.003 (3)	−0.001 (3)
O5	0.056 (4)	0.053 (4)	0.112 (5)	0.002 (3)	0.003 (4)	0.002 (4)
O6	0.048 (4)	0.067 (4)	0.108 (6)	−0.011 (3)	0.003 (4)	0.010 (4)
N3	0.041 (4)	0.044 (4)	0.063 (5)	−0.004 (3)	0.002 (4)	−0.006 (4)
N4	0.045 (4)	0.038 (4)	0.083 (6)	−0.001 (3)	−0.012 (4)	−0.012 (4)
C16	0.029 (4)	0.043 (4)	0.056 (5)	0.008 (3)	−0.007 (4)	0.006 (4)
C17	0.045 (5)	0.042 (4)	0.042 (5)	−0.003 (4)	0.009 (4)	−0.003 (4)
C18	0.038 (4)	0.056 (5)	0.060 (6)	−0.006 (4)	0.001 (4)	0.016 (5)
C19	0.057 (5)	0.040 (4)	0.047 (5)	−0.009 (4)	0.009 (4)	0.008 (4)
C20	0.046 (4)	0.045 (5)	0.051 (5)	0.009 (4)	0.003 (4)	−0.002 (4)
C21	0.039 (4)	0.056 (5)	0.064 (6)	−0.009 (4)	0.013 (4)	−0.005 (5)
C22	0.046 (5)	0.043 (5)	0.053 (6)	−0.009 (4)	−0.005 (4)	−0.009 (4)
C23	0.042 (5)	0.053 (5)	0.041 (5)	−0.006 (4)	0.004 (4)	−0.003 (4)
C24	0.047 (4)	0.050 (5)	0.039 (5)	−0.001 (4)	0.007 (4)	0.006 (4)
C25	0.056 (5)	0.054 (5)	0.048 (5)	−0.002 (4)	−0.005 (4)	0.006 (4)
C26	0.093 (7)	0.053 (6)	0.076 (7)	−0.026 (6)	−0.015 (6)	0.008 (6)
C27	0.152 (12)	0.038 (5)	0.065 (7)	−0.015 (7)	0.019 (7)	0.002 (5)
C28	0.111 (9)	0.064 (7)	0.075 (8)	0.026 (6)	0.023 (7)	0.003 (5)
C29	0.079 (6)	0.056 (6)	0.047 (6)	−0.003 (5)	0.005 (5)	0.003 (4)
C30	0.055 (6)	0.115 (8)	0.069 (7)	−0.009 (6)	0.000 (5)	0.016 (6)
I1	0.0441 (3)	0.0585 (4)	0.1215 (6)	−0.0146 (3)	−0.0043 (3)	−0.0101 (4)
I2	0.0761 (4)	0.0635 (4)	0.0985 (5)	0.0285 (3)	−0.0265 (4)	−0.0121 (4)
O1	0.031 (3)	0.045 (3)	0.088 (5)	0.004 (2)	−0.002 (3)	0.000 (3)
O2	0.033 (3)	0.058 (4)	0.137 (6)	0.003 (3)	0.002 (4)	−0.004 (4)
O3	0.045 (3)	0.051 (3)	0.096 (5)	−0.003 (3)	0.005 (3)	0.000 (3)
N1	0.039 (4)	0.042 (4)	0.058 (4)	0.001 (3)	−0.001 (3)	−0.007 (4)
N2	0.041 (4)	0.039 (4)	0.082 (5)	−0.007 (3)	−0.004 (4)	−0.003 (4)
C1	0.039 (4)	0.037 (4)	0.047 (5)	−0.002 (3)	0.003 (4)	−0.007 (4)
C2	0.035 (4)	0.050 (5)	0.052 (5)	0.002 (4)	0.007 (4)	0.005 (4)
C3	0.038 (4)	0.051 (5)	0.053 (5)	−0.006 (4)	0.001 (4)	−0.005 (4)
C4	0.059 (6)	0.033 (4)	0.065 (6)	0.001 (4)	−0.004 (5)	−0.009 (4)
C5	0.055 (5)	0.048 (5)	0.057 (6)	0.003 (4)	−0.004 (4)	0.008 (5)
C6	0.040 (4)	0.061 (5)	0.035 (5)	0.008 (4)	−0.013 (4)	−0.004 (4)
C7	0.035 (4)	0.056 (5)	0.053 (5)	−0.012 (4)	−0.005 (4)	0.007 (4)
C8	0.043 (5)	0.037 (4)	0.058 (5)	0.002 (4)	0.007 (4)	−0.008 (4)
C9	0.052 (5)	0.045 (4)	0.034 (5)	0.008 (4)	0.005 (4)	0.000 (4)
C10	0.062 (5)	0.043 (5)	0.035 (5)	−0.013 (4)	−0.007 (4)	0.003 (4)
C11	0.070 (6)	0.053 (6)	0.064 (6)	−0.014 (5)	−0.014 (5)	0.001 (5)
C12	0.127 (10)	0.038 (5)	0.068 (7)	−0.007 (6)	−0.009 (6)	−0.002 (5)
C13	0.112 (9)	0.043 (5)	0.068 (7)	0.002 (6)	−0.018 (6)	0.001 (5)
C14	0.061 (5)	0.043 (5)	0.051 (5)	0.004 (4)	−0.001 (5)	−0.008 (4)
C15	0.054 (5)	0.080 (6)	0.065 (6)	−0.029 (5)	−0.002 (5)	−0.002 (5)

I3—C18	2.090 (8)	I1—C3	2.101 (7)
I4—C20	2.111 (7)	I2—C5	2.098 (8)
O4—C17	1.367 (9)	O1—C2	1.355 (8)
O4—H4	0.8200	O1—H1	0.8200
O5—C23	1.229 (9)	O2—C8	1.210 (9)
O6—C25	1.342 (10)	O3—C10	1.348 (10)
O6—C30	1.421 (10)	O3—C15	1.445 (9)
N3—C22	1.287 (10)	N1—C7	1.259 (10)
N3—N4	1.354 (8)	N1—N2	1.364 (8)
N4—C23	1.362 (10)	N2—C8	1.356 (9)
N4—H4B	0.89 (5)	N2—H2	0.90 (3)
C16—C21	1.389 (10)	C1—C6	1.389 (10)
C16—C17	1.414 (10)	C1—C2	1.400 (10)
C16—C22	1.437 (10)	C1—C7	1.448 (10)
C17—C18	1.371 (11)	C2—C3	1.360 (10)
C18—C19	1.366 (11)	C3—C4	1.396 (11)
C19—C20	1.377 (11)	C4—C5	1.370 (11)
C19—H19	0.9300	C4—H4A	0.9300
C20—C21	1.365 (10)	C5—C6	1.369 (10)
C21—H21	0.9300	C6—H6	0.9300
C22—H22	0.9300	C7—H7	0.9300
C23—C24	1.472 (11)	C8—C9	1.485 (11)
C24—C29	1.382 (12)	C9—C14	1.379 (10)
C24—C25	1.412 (11)	C9—C10	1.421 (11)
C25—C26	1.390 (12)	C10—C11	1.393 (11)
C26—C27	1.339 (15)	C11—C12	1.353 (13)
C26—H26	0.9300	C11—H11	0.9300
C27—C28	1.381 (15)	C12—C13	1.399 (14)
C27—H27	0.9300	C12—H12	0.9300
C28—C29	1.374 (12)	C13—C14	1.360 (12)
C28—H28	0.9300	C13—H13	0.9300
C29—H29	0.9300	C14—H14	0.9300
C30—H30A	0.9600	C15—H15A	0.9600
C30—H30B	0.9600	C15—H15B	0.9600
C30—H30C	0.9600	C15—H15C	0.9600
C17—O4—H4	109.4	C2—O1—H1	109.5
C25—O6—C30	120.9 (7)	C10—O3—C15	118.1 (6)
C22—N3—N4	116.9 (7)	C7—N1—N2	117.7 (7)
N3—N4—C23	120.3 (7)	C8—N2—N1	120.1 (6)
N3—N4—H4B	121 (6)	C8—N2—H2	120 (6)
C23—N4—H4B	118 (6)	N1—N2—H2	118 (6)
C21—C16—C17	117.1 (7)	C6—C1—C2	119.0 (7)
C21—C16—C22	119.4 (7)	C6—C1—C7	120.5 (7)
C17—C16—C22	123.3 (7)	C2—C1—C7	120.5 (7)
O4—C17—C18	119.5 (7)	O1—C2—C3	118.7 (7)
O4—C17—C16	120.1 (7)	O1—C2—C1	122.0 (7)
C18—C17—C16	120.4 (7)	C3—C2—C1	119.2 (7)
C19—C18—C17	121.3 (8)	C2—C3—C4	121.8 (7)
C19—C18—I3	118.7 (7)	C2—C3—I1	120.4 (6)
C17—C18—I3	119.6 (6)	C4—C3—I1	117.6 (6)
C18—C19—C20	118.7 (8)	C5—C4—C3	118.2 (8)
C18—C19—H19	120.7	C5—C4—H4A	120.9
C20—C19—H19	120.7	C3—C4—H4A	120.9
C21—C20—C19	121.3 (8)	C6—C5—C4	121.2 (8)
C21—C20—I4	119.9 (6)	C6—C5—I2	119.5 (6)
C19—C20—I4	118.8 (6)	C4—C5—I2	119.3 (6)
C20—C21—C16	121.0 (8)	C5—C6—C1	120.4 (7)
C20—C21—H21	119.5	C5—C6—H6	119.8
C16—C21—H21	119.5	C1—C6—H6	119.8
N3—C22—C16	119.5 (7)	N1—C7—C1	121.5 (8)
N3—C22—H22	120.3	N1—C7—H7	119.2
C16—C22—H22	120.3	C1—C7—H7	119.2
O5—C23—N4	120.1 (7)	O2—C8—N2	121.9 (7)
O5—C23—C24	122.6 (7)	O2—C8—C9	121.0 (7)
N4—C23—C24	117.3 (7)	N2—C8—C9	117.1 (7)
C29—C24—C25	117.0 (8)	C14—C9—C10	117.6 (8)
C29—C24—C23	116.7 (7)	C14—C9—C8	116.6 (7)
C25—C24—C23	126.2 (7)	C10—C9—C8	125.9 (7)
O6—C25—C26	123.0 (8)	O3—C10—C11	123.5 (8)
O6—C25—C24	116.7 (7)	O3—C10—C9	117.4 (7)
C26—C25—C24	120.2 (9)	C11—C10—C9	119.0 (8)
C27—C26—C25	120.3 (10)	C12—C11—C10	120.7 (9)
C27—C26—H26	119.9	C12—C11—H11	119.7
C25—C26—H26	119.9	C10—C11—H11	119.7
C26—C27—C28	121.5 (9)	C11—C12—C13	121.5 (9)
C26—C27—H27	119.3	C11—C12—H12	119.3
C28—C27—H27	119.3	C13—C12—H12	119.3
C29—C28—C27	118.6 (10)	C14—C13—C12	117.5 (10)
C29—C28—H28	120.7	C14—C13—H13	121.2
C27—C28—H28	120.7	C12—C13—H13	121.2
C28—C29—C24	122.4 (9)	C13—C14—C9	123.7 (9)
C28—C29—H29	118.8	C13—C14—H14	118.1
C24—C29—H29	118.8	C9—C14—H14	118.1
O6—C30—H30A	109.5	O3—C15—H15A	109.5
O6—C30—H30B	109.5	O3—C15—H15B	109.5
H30A—C30—H30B	109.5	H15A—C15—H15B	109.5
O6—C30—H30C	109.5	O3—C15—H15C	109.5
H30A—C30—H30C	109.5	H15A—C15—H15C	109.5
H30B—C30—H30C	109.5	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3	0.82	1.90	2.577 (8)	139
O1—H1···N1	0.82	1.92	2.568 (8)	136
N2—H2···O3	0.90 (3)	1.91 (6)	2.613 (8)	134 (8)
N4—H4B···O6	0.89 (5)	1.98 (7)	2.629 (9)	128 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N3	0.82	1.90	2.577 (8)	139
O1—H1⋯N1	0.82	1.92	2.568 (8)	136
N2—H2⋯O3	0.90 (3)	1.91 (6)	2.613 (8)	134 (8)
N4—H4B⋯O6	0.89 (5)	1.98 (7)	2.629 (9)	128 (7)