(E)-4-Hy­droxy-N′-(2-hy­droxy-5-iodo­benzyl­idene)benzohydrazide methanol monosolvate

Mahboubi Anarjan, P.; Monfared, H.H.; Arslan, N.B.; Kazak, C.; Bikas, R.

doi:10.1107/S1600536812034848

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2698

doi:10.1107/S1600536812034848

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(E)-4-Hydroxy-N′-(2-hydroxy-5-iodobenzylidene)benzohydrazide methanol monosolvate

Parisa Mahboubi Anarjan,^a ‡ Hassan Hosseini Monfared,^b N. Burcu Arslan,^c Canan Kazak ^c and Rahman Bikas ^b ^*

^aSama Technical and Vocational Training College, Islamic Azad University, Mamaghan Branch, Mamaghan, Iran, ^bDepartment of Chemistry, Faculty of Science, University of Zanjan, 45195-313 Zanjan, Iran, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55019 Kurupelit, Samsun, Turkey
^*Correspondence e-mail: bikas_r@yahoo.com

(Received 5 August 2012; accepted 7 August 2012; online 11 August 2012)

In the title compound, C₁₄H₁₁IN₂O₃·CH₄O, the dihedral angle between the benzene rings is 33.2 (3)°. The molecule displays trans and anti conformations about the C=N and N—N bonds, respectively. There is an intramolecular O—H⋯N(azomethine) hydrogen bond. Intermolecular N—H⋯O and O—H⋯O hydrogen bonds consolidate molecules into a three-dimensional architecture.

Related literature

For the structures of related carbohydrazides, see: Monfared et al. (2010a ); Bikas et al. (2010a ,b , 2012a ,b ). For catalytic applications of aroylhydrazones, see: Monfared et al. (2010b ).

Experimental

Crystal data

C₁₄H₁₁IN₂O₃·CH₄O
M_r = 414.19
Monoclinic, C c
a = 10.1077 (7) Å
b = 12.5703 (11) Å
c = 13.1586 (17) Å
β = 102.886 (10)°
V = 1629.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.98 mm⁻¹
T = 293 K
0.3 × 0.3 × 0.3 mm

Data collection

Agilent SuperNova (Single source at offset), Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.864, T_max = 1.000
3370 measured reflections
2094 independent reflections
1981 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.04
2094 reflections
201 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ), 419 Friedel pairs
Flack parameter: −0.01 (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	2.607 (8)	146
N2—H2⋯O4	0.86	2.06	2.897 (7)	164
O3—H3⋯O2ⁱ	0.82	1.90	2.712 (6)	171
O4—H4⋯O2ⁱⁱ	0.82	2.05	2.868 (7)	177
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812034848/tk5140sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034848/tk5140Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034848/tk5140Isup3.cml

checkCIF report

Comment top

Hydrazones are a special group of compounds in the Schiff base family that are characterized by the presence of RR'C=N–N=C(O)R'' which two inter-linked nitrogen atoms (–N—N–) separate them into a different class from imines, oximes, etc. Hydrazone ligands derived from the condensation of acid hydrazides (R–CO–NH–NH₂) with aromatic carbonyl compounds are important O, N-donor ligands. Hydrazone derivatives have widespread applications in fields such as coordination chemistry, bioinorganic chemistry, magnetics, electronics, nonlinear optics and fluorescent materials. Aroylhydrazone complexes also seem to be good candidates for catalytic oxidation studies because of their resistance to oxidation (Monfared et al., 2010b).

As part of our studies on the synthesis and characterization of hydrazone derivatives (Bikas et al., 2010a,b; Bikas et al., 2012a,b), we report here the crystal structure of [(E)-4-hydroxy-N'-(2-hydroxy-5-iodobenzylidene)benzohydrazide] methanol solvate. The asymmetric unit of C₁₄H₁₁IN₂O₃.CH₄O contains one molecule of hydrazone and a molecule of methanol, as shown in Fig. 1. In the title compound, the bond distances are in the normal range for similar hydrazone compounds (Monfared et al., 2010a; Bikas et al., 2012a,b). The dihedral angle between the mean planes of the phenol ring and the salcylidine ring is 33.2 (3)°. Molecule adopts an E configuration with respect to the C7=N1 bond. There is an intramolecular O—H···N hydrogen bond between the hydroxyl group and imine nitrogen atom, Table 1. In the crystal structure, the O atom of methanol molecule accepts a hydrogen bond from an amine H atom (NH), and forms another intermolecular O—H···O(carbonyl) hydrogen bond, thereby linking two carbohydrazide molecules. The result is a supramolecular layer parallel to (010). The carbonyl O atom accepts another O—H···O hydrogen bond which the O—H phenol is a donor group (Table 1, Fig. 2).

Related literature top

For the structures of related carbohydrazides, see: Monfared et al. (2010a); Bikas et al. (2010a,b, 2012a,b). For catalytic applications of aroylhydrazones, see: Monfared et al. (2010b).

Experimental top

For preparing the title compound, a methanol (10 ml) solution of 2-hydroxy-5-iodobenzaldehyde (1.5 mmol) was added drop-wise to a methanol solution (10 ml) of 4-hydroxybenzoic acid hydrazide (1.5 mmol). The mixture was refluxed for 5 h. The solution was evaporated on a steam-bath to 5 ml and cooled to room temperature. White precipitates of the title compound were separated and filtered off, washed with 3 ml of cooled methanol and then dried in air. Colourless crystals of the title compound were obtained from its methanol solution by slow solvent evaporation. Yield 94%. Selected IR (cm^-1): 3446 (s, broad, O—H), 3224 (s, N—H), 1626 (vs), 1577 (m), 1509 (s), 1278 (vs), 1013 (s), 850 (m), 690 (m).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. The blue dashed lines indicate intra- and inter-molecular hydrogen bonds.

(E)-4-Hydroxy-N'-(2-hydroxy-5-iodobenzylidene)benzohydrazide methanol monosolvate top

Crystal data top

C₁₄H₁₁IN₂O₃·CH₄O	F(000) = 816
M_r = 414.19	D_x = 1.688 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1140 reflections
a = 10.1077 (7) Å	θ = 3.3–32.3°
b = 12.5703 (11) Å	µ = 1.98 mm⁻¹
c = 13.1586 (17) Å	T = 293 K
β = 102.886 (10)°	Block, colourless
V = 1629.8 (3) Å³	0.3 × 0.3 × 0.3 mm
Z = 4

Data collection top

Agilent SuperNova (Single source at offset), Eos diffractometer	2094 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1981 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.034
Detector resolution: 16.0454 pixels mm^-1	θ_max = 26.4°, θ_min = 3.3°
ω scans	h = −12→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→15
T_min = 0.864, T_max = 1.000	l = −16→14
3370 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0466P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2094 reflections	Δρ_max = 0.32 e Å⁻³
201 parameters	Δρ_min = −0.56 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 419 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (3)

Crystal data top

C₁₄H₁₁IN₂O₃·CH₄O	V = 1629.8 (3) Å³
M_r = 414.19	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 10.1077 (7) Å	µ = 1.98 mm⁻¹
b = 12.5703 (11) Å	T = 293 K
c = 13.1586 (17) Å	0.3 × 0.3 × 0.3 mm
β = 102.886 (10)°

Data collection top

Agilent SuperNova (Single source at offset), Eos diffractometer	2094 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	1981 reflections with I > 2σ(I)
T_min = 0.864, T_max = 1.000	R_int = 0.034
3370 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 0.32 e Å⁻³
S = 1.04	Δρ_min = −0.56 e Å⁻³
2094 reflections	Absolute structure: Flack (1983), 419 Friedel pairs
201 parameters	Absolute structure parameter: −0.01 (3)
2 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
I1	0.71478 (4)	0.35952 (3)	0.30013 (4)	0.05205 (16)
O1	0.3254 (6)	0.5311 (5)	0.5685 (4)	0.0672 (17)
H1	0.2521	0.5492	0.5321	0.101*
O2	−0.0512 (5)	0.6112 (4)	0.4916 (3)	0.0450 (11)
O3	−0.5681 (5)	0.7936 (4)	0.1732 (3)	0.0548 (13)
H3	−0.5634	0.8156	0.1155	0.082*
O4	0.0029 (7)	0.5759 (4)	0.1189 (4)	0.0613 (15)
H4	−0.0129	0.5213	0.0842	0.092*
N1	0.1430 (6)	0.5574 (5)	0.3960 (4)	0.0412 (12)
N2	0.0194 (5)	0.5934 (4)	0.3409 (4)	0.0379 (11)
H2	0.0008	0.5958	0.2739	0.045*
C1	0.4061 (7)	0.4922 (6)	0.5066 (5)	0.0469 (16)
C2	0.5354 (8)	0.4584 (7)	0.5544 (5)	0.0553 (19)
H2A	0.5635	0.4611	0.6266	0.066*
C3	0.6226 (7)	0.4209 (6)	0.4960 (5)	0.0472 (16)
H3A	0.7102	0.4002	0.5285	0.057*
C4	0.5793 (6)	0.4142 (5)	0.3886 (4)	0.0376 (13)
C5	0.4500 (6)	0.4478 (5)	0.3393 (4)	0.0369 (13)
H5	0.4225	0.4441	0.2671	0.044*
C6	0.3614 (6)	0.4868 (5)	0.3973 (4)	0.0359 (13)
C7	0.2277 (6)	0.5220 (5)	0.3436 (5)	0.0395 (14)
H7	0.2027	0.5190	0.2712	0.047*
C8	−0.0721 (7)	0.6251 (4)	0.3958 (4)	0.0336 (13)
C9	−0.1990 (6)	0.6748 (5)	0.3356 (4)	0.0318 (12)
C10	−0.3134 (7)	0.6734 (6)	0.3778 (5)	0.0407 (14)
H10	−0.3078	0.6452	0.4439	0.049*
C11	−0.4344 (7)	0.7135 (6)	0.3224 (5)	0.0426 (15)
H11	−0.5112	0.7094	0.3502	0.051*
C12	−0.4438 (6)	0.7604 (5)	0.2252 (4)	0.0371 (13)
C13	−0.3289 (6)	0.7659 (5)	0.1848 (4)	0.0374 (13)
H13	−0.3338	0.7982	0.1204	0.045*
C14	−0.2068 (7)	0.7242 (5)	0.2388 (5)	0.0369 (14)
H14	−0.1301	0.7288	0.2110	0.044*
C15	0.0531 (14)	0.6548 (7)	0.0605 (7)	0.075 (3)
H15A	−0.0125	0.7109	0.0429	0.112*
H15B	0.0696	0.6238	−0.0022	0.112*
H15C	0.1363	0.6833	0.1013	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0380 (2)	0.0592 (3)	0.0620 (3)	0.0113 (3)	0.01773 (16)	−0.0025 (2)
O1	0.054 (3)	0.108 (5)	0.039 (2)	0.030 (4)	0.010 (2)	−0.005 (2)
O2	0.043 (3)	0.057 (3)	0.035 (2)	0.009 (2)	0.0088 (19)	0.0027 (18)
O3	0.036 (3)	0.080 (4)	0.052 (3)	0.020 (3)	0.016 (2)	0.019 (2)
O4	0.083 (4)	0.062 (3)	0.040 (2)	−0.015 (3)	0.015 (2)	−0.007 (2)
N1	0.031 (3)	0.053 (3)	0.038 (2)	0.006 (3)	0.005 (2)	0.002 (2)
N2	0.030 (3)	0.048 (3)	0.035 (2)	0.009 (3)	0.006 (2)	−0.002 (2)
C1	0.041 (4)	0.060 (4)	0.040 (3)	0.011 (3)	0.007 (3)	0.004 (3)
C2	0.042 (4)	0.079 (5)	0.041 (3)	0.015 (4)	0.000 (3)	0.005 (3)
C3	0.032 (3)	0.059 (4)	0.048 (3)	0.008 (3)	0.003 (3)	0.004 (3)
C4	0.032 (3)	0.038 (3)	0.045 (3)	0.002 (3)	0.012 (3)	0.000 (2)
C5	0.034 (3)	0.043 (3)	0.032 (3)	0.003 (3)	0.005 (2)	−0.002 (2)
C6	0.030 (3)	0.039 (3)	0.036 (3)	0.003 (3)	0.004 (2)	−0.001 (2)
C7	0.032 (3)	0.053 (4)	0.034 (3)	0.002 (3)	0.007 (2)	−0.001 (2)
C8	0.031 (3)	0.034 (3)	0.035 (3)	0.001 (2)	0.006 (2)	−0.001 (2)
C9	0.032 (3)	0.031 (3)	0.032 (3)	0.005 (2)	0.007 (2)	−0.003 (2)
C10	0.040 (4)	0.051 (4)	0.035 (3)	0.004 (3)	0.016 (3)	0.005 (3)
C11	0.035 (3)	0.057 (4)	0.041 (3)	0.012 (3)	0.019 (3)	0.010 (3)
C12	0.030 (3)	0.041 (3)	0.043 (3)	0.009 (3)	0.012 (2)	0.004 (2)
C13	0.034 (3)	0.044 (3)	0.036 (3)	0.004 (3)	0.012 (2)	0.009 (2)
C14	0.032 (3)	0.047 (4)	0.034 (3)	−0.001 (3)	0.012 (3)	0.001 (2)
C15	0.099 (9)	0.066 (5)	0.061 (5)	−0.003 (5)	0.021 (5)	−0.003 (4)

Geometric parameters (Å, º) top

I1—C4	2.101 (6)	C5—C6	1.389 (9)
O1—C1	1.365 (9)	C5—H5	0.9300
O1—H1	0.8200	C6—C7	1.447 (8)
O2—C8	1.243 (7)	C7—H7	0.9300
O3—C12	1.355 (7)	C8—C9	1.486 (8)
O3—H3	0.8200	C9—C10	1.390 (9)
O4—C15	1.416 (12)	C9—C14	1.403 (8)
O4—H4	0.8200	C10—C11	1.373 (9)
N1—C7	1.292 (9)	C10—H10	0.9300
N1—N2	1.374 (7)	C11—C12	1.392 (9)
N2—C8	1.355 (8)	C11—H11	0.9300
N2—H2	0.8600	C12—C13	1.383 (9)
C1—C2	1.385 (10)	C13—C14	1.383 (9)
C1—C6	1.409 (8)	C13—H13	0.9300
C2—C3	1.375 (10)	C14—H14	0.9300
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.387 (9)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.388 (8)

C1—O1—H1	109.5	O2—C8—N2	121.2 (6)
C12—O3—H3	109.5	O2—C8—C9	122.1 (6)
C15—O4—H4	109.5	N2—C8—C9	116.7 (5)
C7—N1—N2	117.7 (5)	C10—C9—C14	119.0 (6)
C8—N2—N1	117.7 (5)	C10—C9—C8	118.5 (5)
C8—N2—H2	121.2	C14—C9—C8	122.5 (6)
N1—N2—H2	121.2	C11—C10—C9	120.4 (6)
O1—C1—C2	117.9 (6)	C11—C10—H10	119.8
O1—C1—C6	121.9 (6)	C9—C10—H10	119.8
C2—C1—C6	120.3 (7)	C10—C11—C12	120.9 (6)
C3—C2—C1	120.6 (6)	C10—C11—H11	119.6
C3—C2—H2A	119.7	C12—C11—H11	119.6
C1—C2—H2A	119.7	O3—C12—C13	123.6 (5)
C2—C3—C4	119.6 (6)	O3—C12—C11	117.3 (6)
C2—C3—H3A	120.2	C13—C12—C11	118.9 (6)
C4—C3—H3A	120.2	C12—C13—C14	120.9 (5)
C3—C4—C5	120.5 (6)	C12—C13—H13	119.6
C3—C4—I1	119.2 (5)	C14—C13—H13	119.6
C5—C4—I1	120.2 (4)	C13—C14—C9	119.9 (6)
C4—C5—C6	120.4 (5)	C13—C14—H14	120.1
C4—C5—H5	119.8	C9—C14—H14	120.1
C6—C5—H5	119.8	O4—C15—H15A	109.5
C5—C6—C1	118.6 (5)	O4—C15—H15B	109.5
C5—C6—C7	119.0 (5)	H15A—C15—H15B	109.5
C1—C6—C7	122.4 (6)	O4—C15—H15C	109.5
N1—C7—C6	120.1 (5)	H15A—C15—H15C	109.5
N1—C7—H7	119.9	H15B—C15—H15C	109.5
C6—C7—H7	119.9

C7—N1—N2—C8	176.5 (6)	N1—N2—C8—O2	−7.8 (9)
O1—C1—C2—C3	−178.4 (7)	N1—N2—C8—C9	173.5 (5)
C6—C1—C2—C3	1.1 (12)	O2—C8—C9—C10	−21.6 (9)
C1—C2—C3—C4	−1.8 (12)	N2—C8—C9—C10	157.1 (6)
C2—C3—C4—C5	1.8 (10)	O2—C8—C9—C14	157.4 (6)
C2—C3—C4—I1	178.9 (6)	N2—C8—C9—C14	−23.9 (8)
C3—C4—C5—C6	−1.2 (10)	C14—C9—C10—C11	4.3 (10)
I1—C4—C5—C6	−178.2 (5)	C8—C9—C10—C11	−176.6 (6)
C4—C5—C6—C1	0.5 (10)	C9—C10—C11—C12	−2.8 (11)
C4—C5—C6—C7	179.5 (6)	C10—C11—C12—O3	177.0 (7)
O1—C1—C6—C5	179.0 (7)	C10—C11—C12—C13	0.1 (10)
C2—C1—C6—C5	−0.4 (11)	O3—C12—C13—C14	−175.6 (6)
O1—C1—C6—C7	0.0 (11)	C11—C12—C13—C14	1.1 (10)
C2—C1—C6—C7	−179.5 (7)	C12—C13—C14—C9	0.4 (10)
N2—N1—C7—C6	177.6 (6)	C10—C9—C14—C13	−3.1 (10)
C5—C6—C7—N1	179.2 (6)	C8—C9—C14—C13	177.9 (6)
C1—C6—C7—N1	−1.8 (10)

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	2.607 (8)	146
N2—H2···O4	0.86	2.06	2.897 (7)	164
O3—H3···O2ⁱ	0.82	1.90	2.712 (6)	171
O4—H4···O2ⁱⁱ	0.82	2.05	2.868 (7)	177

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁IN₂O₃·CH₄O
M_r	414.19
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	10.1077 (7), 12.5703 (11), 13.1586 (17)
β (°)	102.886 (10)
V (Å³)	1629.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.98
Crystal size (mm)	0.3 × 0.3 × 0.3

Data collection
Diffractometer	Agilent SuperNova (Single source at offset), Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.864, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3370, 2094, 1981
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.04
No. of reflections	2094
No. of parameters	201
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.56
Absolute structure	Flack (1983), 419 Friedel pairs
Absolute structure parameter	−0.01 (3)

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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	2.607 (8)	146
N2—H2···O4	0.86	2.06	2.897 (7)	164
O3—H3···O2ⁱ	0.82	1.90	2.712 (6)	171
O4—H4···O2ⁱⁱ	0.82	2.05	2.868 (7)	177

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, −y+1, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: mahboubi_p@yahoo.com.

Acknowledgements

The authors are grateful to the Islamic Azad University, the University of Zanjan and Ondokuz Mayis University.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Bikas, R., Anarjan, P. M., Ng, S. W. & Tiekink, E. R. T. (2012a). Acta Cryst. E68, o413–o414. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Monfared, H. H., Bikas, R. & Mayer, P. (2010a). Acta Cryst. E66, o236–o237. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 68| Part 9| September 2012| Page o2698

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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-5-iodo­benzyl­­idene)benzohydrazide methanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(E)-4-Hydroxy-N′-(2-hydroxy-5-iodobenzylidene)benzohydrazide methanol monosolvate