(E)-4-Hy­droxy-N′-(2-hy­droxy-3,5-diiodo­benzyl­idene)-3-meth­oxy­benzohydrazide methanol monosolvate

Li, X.-Y.

doi:10.1107/S1600536812004552

organic compounds

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Volume 68| Part 3| March 2012| Page o654

doi:10.1107/S1600536812004552

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(E)-4-Hydroxy-N′-(2-hydroxy-3,5-diiodobenzylidene)-3-methoxybenzohydrazide methanol monosolvate

Xiao-Yan Li ^a ^*

^aZibo Vocational Institute, Zibo 255314, People's Republic of China
^*Correspondence e-mail: lixiaoyan_zb@126.com

(Received 2 February 2012; accepted 2 February 2012; online 10 February 2012)

In the title compound, C₁₅H₁₂I₂N₂O₄·CH₃OH, the hydrazone molecule 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 intramolecular O—H⋯N hydrogen bond in the hydrazone molecule. In the crystal, the hydrazone and methanol molecules are linked through O—H⋯O and N—H⋯O hydrogen bonds and C—H⋯O interactions 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_r = 570.11
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.091
S = 1.02
4315 reflections
239 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.12 e Å⁻³
Δρ_min = −1.35 e Å⁻³

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812004552/su2374sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812004552/su2374Isup3.cml

checkCIF report

Comment top

In recent years, hydrazone compounds have attracted much attention due to their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b), the author reports herein on the crystal structure of the new title hydrazone compound.

The title compound (Fig. 1), contains a N'-(2-hydroxy-3,5-diiodobenzylidene)-4-hydroxy-3-methoxybenzohydrazide molecule and a methanol solvent molecule. The hydrazone molecule exists in a trans or E conformation with respect to the C7═N1 bond. The dihedral angle between the (C1–C6) and (C9–C14) benzene rings of the hydrazone molecule is 11.9 (2)°. There is one O–H···N intramolecular hydrogen bond in the hydrazone molecule (Table 1).

In the crystal, the hydrazone and methanol molecules are linked through O–H···O and N–H···O hydrogen bonds and C-H···O interactions (Table 1), to form a two-dimensional network lieing parallel to the ab plane (Fig. 2).

Related literature top

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 on recently by the author, see: Li (2011a,b).

Experimental top

A mixture of 2-hydroxy-3,5-diiodobenzaldehyde (0.374 g, 1 mmol) and 4-hydroxy-3-methoxybenzohydrazide (0.182 g, 1 mmol) in 30 ml of ethanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Colourless crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a solution of the title compound in methanol.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level. The intramolecular O–H···N hydrogen bond, and the O-H···O hydrogen bond linking the hydrazone and methanol molecules are indicated by dashed lines (see Table 1 for details).
	Fig. 2. Crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are indicated by dashed lines (see Table 1 for details). The C-bound H-atoms have been omitted for clarity.

(E)-4-Hydroxy-N'-(2-hydroxy-3,5-diiodobenzylidene)- 3-methoxybenzohydrazide methanol monosolvate top

Crystal data top

C₁₅H₁₂I₂N₂O₄·CH₄O	F(000) = 2176
M_r = 570.11	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.027P)² + 9.4128P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4315 reflections	Δρ_max = 1.12 e Å⁻³
239 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₂I₂N₂O₄·CH₄O	V = 3975.5 (11) Å³
M_r = 570.11	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 19.467 (3) Å	µ = 3.19 mm⁻¹
b = 12.655 (2) Å	T = 298 K
c = 16.138 (2) Å	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4315 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3198 reflections with I > 2σ(I)
T_min = 0.527, T_max = 0.568	R_int = 0.040
22354 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 1.12 e Å⁻³
4315 reflections	Δρ_min = −1.35 e Å⁻³
239 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y+1/2, z; (ii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂I₂N₂O₄·CH₄O
M_r	570.11
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	19.467 (3), 12.655 (2), 16.138 (2)
V (Å³)	3975.5 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.19
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.527, 0.568
No. of measured, independent and observed [I > 2σ(I)] reflections	22354, 4315, 3198
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.091, 1.02
No. of reflections	4315
No. of parameters	239
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.12, −1.35

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond angles (º) top

C11—O4—C15	117.3 (3)	N1—C7—C1	120.0 (4)
N2—N1—C7	117.9 (3)	N2—C8—C9	116.5 (3)
N1—N2—C8	118.4 (3)	O2—C8—N2	122.0 (3)
O1—C2—C3	118.9 (4)	O2—C8—C9	121.5 (3)
O1—C2—C1	122.2 (4)	O4—C11—C12	115.0 (3)
I1—C3—C4	119.9 (3)	O4—C11—C10	125.5 (3)
I1—C3—C2	119.1 (3)	O3—C12—C11	116.7 (3)
I2—C5—C4	118.5 (3)	O3—C12—C13	123.6 (3)
I2—C5—C6	121.2 (3)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y+1/2, z; (ii) x+1/2, −y+1/2, −z+1.

Acknowledgements

The author is grateful to the Zibo Vocational Institute for supporting this work.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171. Web of Science CrossRef IUCr Journals Google Scholar
Lei, Y. (2011). Acta Cryst. E67, o162. Web of Science CrossRef IUCr Journals Google Scholar
Li, X.-Y. (2011a). Acta Cryst. E67, o1798. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, X.-Y. (2011b). Acta Cryst. E67, o2511. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126–o3127. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Page o654

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-4-Hy­dr­oxy-N′-(2-hy­dr­oxy-3,5-di­iodo­benzyl­­idene)-3-meth­­oxy­benzohydrazide methanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-4-Hydroxy-N′-(2-hydroxy-3,5-diiodobenzylidene)-3-methoxybenzohydrazide methanol monosolvate