(E)-4-Hy-droxy-N'-(2-hy-droxy-3,5-diiodo-benzyl-idene)-3-meth-oxy-benzohydrazide methanol monosolvate.

In the title compound, C(15)H(12)I(2)N(2)O(4)·CH(3)OH, the hydrazone mol-ecule exists in an E conformation with respect to the C=N bond. The dihedral angle between the rings is 11.9 (2)°. There is one intra-molecular O-H⋯N hydrogen bond in the hydrazone mol-ecule. In the crystal, the hydrazone and methanol mol-ecules are linked through O-H⋯O and N-H⋯O hydrogen bonds and C-H⋯O inter-actions to form two-dimensional networks lying parallel to (001).

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a ▶,b ▶).

Experimental

Crystal data

C15H12I2N2O4·CH4O

M = 570.11

Orthorhombic,

a = 19.467 (3) Å

b = 12.655 (2) Å

c = 16.138 (2) Å

V = 3975.5 (11) Å3

Z = 8

Mo Kα radiation

μ = 3.19 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.527, T max = 0.568

22354 measured reflections

4315 independent reflections

3198 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.091

S = 1.02

4315 reflections

239 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.12 e Å−3

Δρmin = −1.35 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004552/su2374sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004552/su2374Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004552/su2374Isup3.cml

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

C15H12I2N2O4·CH4O	F(000) = 2176
Mr = 570.11	Dx = 1.905 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6406 reflections
a = 19.467 (3) Å	θ = 2.3–26.0°
b = 12.655 (2) Å	µ = 3.19 mm−1
c = 16.138 (2) Å	T = 298 K
V = 3975.5 (11) Å3	Block, colourless
Z = 8	0.23 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	4315 independent reflections
Radiation source: fine-focus sealed tube	3198 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.527, Tmax = 0.568	k = −15→15
22354 measured reflections	l = −20→17

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.027P)2 + 9.4128P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4315 reflections	Δρmax = 1.12 e Å−3
239 parameters	Δρmin = −1.35 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00222 (10)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
I1	0.30599 (2)	0.65273 (4)	0.22384 (2)	0.0780 (2)
I2	0.44485 (3)	1.03076 (3)	0.37750 (3)	0.0875 (2)
O1	0.42798 (16)	0.5423 (2)	0.3180 (2)	0.0600 (11)
O2	0.53658 (14)	0.3091 (2)	0.40531 (19)	0.0511 (10)
O3	0.81379 (14)	0.1047 (2)	0.53841 (19)	0.0469 (10)
O4	0.72081 (16)	0.0227 (2)	0.4401 (2)	0.0579 (11)
N1	0.53819 (16)	0.5213 (3)	0.4091 (2)	0.0435 (11)
N2	0.59137 (17)	0.4611 (3)	0.4418 (2)	0.0430 (11)
C1	0.48852 (19)	0.6898 (3)	0.3790 (2)	0.0400 (12)
C2	0.4343 (2)	0.6470 (3)	0.3315 (3)	0.0430 (12)
C3	0.3854 (2)	0.7157 (4)	0.2971 (3)	0.0480 (14)
C4	0.3886 (2)	0.8237 (4)	0.3112 (3)	0.0550 (16)
C5	0.4420 (2)	0.8658 (3)	0.3584 (3)	0.0527 (16)
C6	0.4916 (2)	0.8002 (3)	0.3918 (3)	0.0480 (12)
C7	0.5422 (2)	0.6220 (3)	0.4159 (3)	0.0427 (12)
C8	0.58719 (19)	0.3537 (3)	0.4359 (2)	0.0378 (11)
C9	0.64765 (18)	0.2924 (3)	0.4669 (2)	0.0337 (11)
C10	0.65308 (19)	0.1866 (3)	0.4410 (2)	0.0393 (12)
C11	0.70893 (19)	0.1254 (3)	0.4644 (2)	0.0378 (11)
C12	0.76007 (18)	0.1695 (3)	0.5169 (2)	0.0349 (11)
C13	0.75389 (19)	0.2734 (3)	0.5434 (2)	0.0382 (11)
C14	0.69824 (19)	0.3345 (3)	0.5188 (2)	0.0383 (11)
C15	0.6690 (3)	−0.0275 (4)	0.3916 (4)	0.074 (2)
O5	0.40228 (15)	0.2948 (3)	0.3656 (2)	0.0545 (10)
C16	0.3918 (3)	0.2952 (5)	0.2788 (3)	0.072 (2)
H1	0.45980	0.51100	0.34060	0.0900*
H2	0.6291 (17)	0.493 (4)	0.463 (3)	0.0800*
H3	0.839 (2)	0.136 (4)	0.574 (3)	0.0800*
H4	0.35510	0.86800	0.28920	0.0660*
H6	0.52730	0.82890	0.42290	0.0570*
H7	0.57900	0.65240	0.44400	0.0510*
H10	0.61890	0.15740	0.40790	0.0470*
H13	0.78720	0.30230	0.57790	0.0460*
H14	0.69460	0.40400	0.53700	0.0460*
H15A	0.62660	−0.02830	0.42200	0.1110*
H15B	0.68270	−0.09870	0.37950	0.1110*
H15C	0.66280	0.01070	0.34080	0.1110*
H5	0.4435 (11)	0.311 (4)	0.376 (3)	0.0800*
H16A	0.39370	0.36660	0.25860	0.1080*
H16B	0.34770	0.26540	0.26630	0.1080*
H16C	0.42710	0.25410	0.25240	0.1080*

	U11	U22	U33	U12	U13	U23
I1	0.0504 (2)	0.1183 (4)	0.0653 (2)	0.0102 (2)	−0.0165 (2)	−0.0126 (2)
I2	0.1299 (4)	0.0430 (2)	0.0895 (3)	0.0164 (2)	0.0026 (3)	0.0088 (2)
O1	0.0545 (19)	0.0484 (18)	0.077 (2)	0.0036 (14)	−0.0186 (17)	−0.0037 (16)
O2	0.0344 (15)	0.0555 (18)	0.0634 (19)	0.0008 (13)	−0.0115 (14)	−0.0053 (15)
O3	0.0377 (16)	0.0410 (15)	0.0620 (19)	0.0103 (12)	−0.0107 (13)	−0.0080 (14)
O4	0.0627 (19)	0.0359 (16)	0.075 (2)	0.0051 (14)	−0.0197 (17)	−0.0150 (15)
N1	0.0366 (17)	0.046 (2)	0.0480 (19)	0.0088 (15)	−0.0006 (15)	0.0069 (16)
N2	0.0347 (17)	0.0403 (19)	0.054 (2)	0.0076 (14)	−0.0071 (16)	0.0050 (16)
C1	0.036 (2)	0.043 (2)	0.041 (2)	0.0050 (17)	0.0046 (17)	0.0060 (18)
C2	0.038 (2)	0.048 (2)	0.043 (2)	0.0048 (18)	0.0014 (17)	0.0007 (18)
C3	0.037 (2)	0.068 (3)	0.039 (2)	0.010 (2)	−0.0003 (17)	0.005 (2)
C4	0.058 (3)	0.059 (3)	0.048 (2)	0.023 (2)	0.001 (2)	0.014 (2)
C5	0.064 (3)	0.040 (2)	0.054 (3)	0.012 (2)	0.007 (2)	0.011 (2)
C6	0.047 (2)	0.047 (2)	0.050 (2)	−0.0020 (19)	0.002 (2)	0.002 (2)
C7	0.034 (2)	0.049 (2)	0.045 (2)	0.0057 (17)	−0.0022 (17)	0.0046 (18)
C8	0.0325 (19)	0.044 (2)	0.037 (2)	0.0020 (17)	0.0008 (16)	−0.0025 (17)
C9	0.0271 (17)	0.0349 (19)	0.039 (2)	−0.0009 (15)	0.0010 (15)	0.0005 (16)
C10	0.037 (2)	0.038 (2)	0.043 (2)	−0.0053 (16)	−0.0061 (17)	−0.0009 (17)
C11	0.039 (2)	0.0323 (19)	0.042 (2)	−0.0013 (15)	0.0000 (17)	−0.0040 (16)
C12	0.0302 (18)	0.0335 (19)	0.041 (2)	0.0017 (15)	0.0013 (15)	−0.0006 (16)
C13	0.0305 (18)	0.038 (2)	0.046 (2)	−0.0033 (16)	−0.0053 (17)	−0.0059 (17)
C14	0.0365 (19)	0.0314 (19)	0.047 (2)	0.0013 (16)	−0.0014 (17)	−0.0025 (17)
C15	0.087 (4)	0.045 (3)	0.090 (4)	−0.004 (3)	−0.028 (3)	−0.026 (3)
O5	0.0357 (15)	0.072 (2)	0.0557 (19)	−0.0057 (15)	0.0036 (14)	−0.0073 (16)
C16	0.082 (4)	0.075 (4)	0.060 (3)	−0.011 (3)	−0.007 (3)	−0.009 (3)

I1—C3	2.103 (4)	C5—C6	1.383 (6)
I2—C5	2.111 (4)	C8—C9	1.496 (5)
O1—C2	1.348 (5)	C9—C14	1.398 (5)
O2—C8	1.238 (5)	C9—C10	1.407 (5)
O3—C12	1.374 (4)	C10—C11	1.387 (5)
O4—C11	1.377 (5)	C11—C12	1.421 (5)
O4—C15	1.426 (7)	C12—C13	1.388 (5)
O1—H1	0.8200	C13—C14	1.389 (5)
O3—H3	0.85 (5)	C4—H4	0.9300
O5—C16	1.416 (6)	C6—H6	0.9300
O5—H5	0.85 (3)	C7—H7	0.9300
N1—C7	1.282 (5)	C10—H10	0.9300
N1—N2	1.390 (5)	C13—H13	0.9300
N2—C8	1.365 (5)	C14—H14	0.9300
N2—H2	0.91 (4)	C15—H15C	0.9600
C1—C6	1.414 (5)	C15—H15A	0.9600
C1—C7	1.477 (5)	C15—H15B	0.9600
C1—C2	1.413 (6)	C16—H16A	0.9600
C2—C3	1.404 (6)	C16—H16B	0.9600
C3—C4	1.387 (7)	C16—H16C	0.9600
C4—C5	1.395 (6)
C11—O4—C15	117.3 (3)	C10—C11—C12	119.5 (3)
C2—O1—H1	109.00	O4—C11—C10	125.5 (3)
C12—O3—H3	109 (3)	O3—C12—C11	116.7 (3)
C16—O5—H5	109 (3)	C11—C12—C13	119.7 (3)
N2—N1—C7	117.9 (3)	O3—C12—C13	123.6 (3)
N1—N2—C8	118.4 (3)	C12—C13—C14	120.5 (3)
C8—N2—H2	121 (3)	C9—C14—C13	120.6 (3)
N1—N2—H2	120 (3)	C5—C4—H4	120.00
C2—C1—C7	121.6 (3)	C3—C4—H4	120.00
C6—C1—C7	119.0 (3)	C1—C6—H6	120.00
C2—C1—C6	119.3 (3)	C5—C6—H6	120.00
O1—C2—C3	118.9 (4)	C1—C7—H7	120.00
C1—C2—C3	118.9 (4)	N1—C7—H7	120.00
O1—C2—C1	122.2 (4)	C9—C10—H10	120.00
I1—C3—C4	119.9 (3)	C11—C10—H10	120.00
C2—C3—C4	121.0 (4)	C14—C13—H13	120.00
I1—C3—C2	119.1 (3)	C12—C13—H13	120.00
C3—C4—C5	120.0 (4)	C9—C14—H14	120.00
C4—C5—C6	120.3 (4)	C13—C14—H14	120.00
I2—C5—C4	118.5 (3)	O4—C15—H15B	109.00
I2—C5—C6	121.2 (3)	O4—C15—H15C	109.00
C1—C6—C5	120.5 (4)	O4—C15—H15A	109.00
N1—C7—C1	120.0 (4)	H15A—C15—H15C	109.00
N2—C8—C9	116.5 (3)	H15B—C15—H15C	110.00
O2—C8—N2	122.0 (3)	H15A—C15—H15B	109.00
O2—C8—C9	121.5 (3)	O5—C16—H16A	109.00
C8—C9—C14	123.8 (3)	O5—C16—H16B	110.00
C10—C9—C14	119.2 (3)	O5—C16—H16C	109.00
C8—C9—C10	117.0 (3)	H16A—C16—H16B	109.00
C9—C10—C11	120.6 (3)	H16A—C16—H16C	109.00
O4—C11—C12	115.0 (3)	H16B—C16—H16C	110.00
C15—O4—C11—C10	−4.7 (6)	C3—C4—C5—C6	−0.5 (7)
C15—O4—C11—C12	176.2 (4)	I2—C5—C6—C1	179.4 (3)
C7—N1—N2—C8	179.1 (4)	C4—C5—C6—C1	−0.4 (7)
N2—N1—C7—C1	177.4 (3)	O2—C8—C9—C10	16.1 (5)
N1—N2—C8—O2	−2.8 (5)	O2—C8—C9—C14	−164.4 (3)
N1—N2—C8—C9	176.1 (3)	N2—C8—C9—C10	−162.8 (3)
C6—C1—C2—O1	−179.1 (4)	N2—C8—C9—C14	16.8 (5)
C6—C1—C2—C3	1.0 (6)	C8—C9—C10—C11	177.6 (3)
C7—C1—C2—O1	0.8 (6)	C14—C9—C10—C11	−2.0 (5)
C7—C1—C2—C3	−179.1 (4)	C8—C9—C14—C13	−178.4 (3)
C2—C1—C6—C5	0.2 (6)	C10—C9—C14—C13	1.2 (5)
C7—C1—C6—C5	−179.7 (4)	C9—C10—C11—O4	−177.3 (3)
C2—C1—C7—N1	−3.9 (6)	C9—C10—C11—C12	1.7 (5)
C6—C1—C7—N1	176.0 (4)	O4—C11—C12—O3	−1.4 (5)
O1—C2—C3—I1	−1.5 (6)	O4—C11—C12—C13	178.5 (3)
O1—C2—C3—C4	178.2 (4)	C10—C11—C12—O3	179.5 (3)
C1—C2—C3—I1	178.5 (3)	C10—C11—C12—C13	−0.7 (5)
C1—C2—C3—C4	−1.9 (7)	O3—C12—C13—C14	179.7 (3)
I1—C3—C4—C5	−178.7 (3)	C11—C12—C13—C14	−0.2 (5)
C2—C3—C4—C5	1.7 (7)	C12—C13—C14—C9	−0.1 (5)
C3—C4—C5—I2	179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.89	2.614 (4)	147
O5—H5···O2	0.85 (3)	1.87 (2)	2.698 (4)	165 (5)
N2—H2···O3i	0.91 (4)	2.17 (5)	3.024 (4)	157 (3)
O3—H3···O5ii	0.85 (5)	1.80 (4)	2.643 (4)	170 (4)
C14—H14···O3i	0.93	2.55	3.442 (5)	162
C16—H16A···O1	0.96	2.51	3.267 (7)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.89	2.614 (4)	147
O5—H5⋯O2	0.85 (3)	1.87 (2)	2.698 (4)	165 (5)
N2—H2⋯O3i	0.91 (4)	2.17 (5)	3.024 (4)	157 (3)
O3—H3⋯O5ii	0.85 (5)	1.80 (4)	2.643 (4)	170 (4)
C14—H14⋯O3i	0.93	2.55	3.442 (5)	162
C16—H16A⋯O1	0.96	2.51	3.267 (7)	135

Symmetry codes: (i) ; (ii) .