(E)-2-(2-Hy­droxy-5-iodo­benzyl­idene)hydrazinecarboxamide

Rahman Bikas; Samra Nikbakht Sardari; Seyed Sajjad Hosseini; Gholam Hossein Shahverdizadeh; Behrouz Notash

doi:10.1107/S1600536812010197

. 2012 Mar 17;68(Pt 4):o1090. doi: 10.1107/S1600536812010197

(E)-2-(2-Hydroxy-5-iodobenzylidene)hydrazinecarboxamide

Rahman Bikas ^a,^*, Samra Nikbakht Sardari ^b, Seyed Sajjad Hosseini ^b, Gholam Hossein Shahverdizadeh ^c, Behrouz Notash ^d

PMCID: PMC3344044 PMID: 22589953

Abstract

In the title molecule, C₈H₈IN₃O₂, there is an intramolecular O—H⋯N hydrogen bond between the hydroxy group and the imine N atom, which generates an S(6) ring. In the crystal, the carbonyl O atom accepts two different N—H⋯O hydrogen bonds, which connect molecules with two R ₂ ²(8) motifs.

Related literature

For historical background to semicarbazones, see: Arapov et al. (1987 ▶); Pickart et al. (1983 ▶). For related structures see: Bikas et al. (2010 ▶, 2012a ▶,b ▶); Monfared et al. (2010a ▶). For background to the development of hydrazide derivatives for biological evaluation, see: Carvalho et al. (2008 ▶). For catalytic applications of aroylhydrazones, see: Monfared et al. (2010b ▶). For a similiar structure, see: Abboud et al. (1995 ▶).

Experimental

Crystal data

C₈H₈IN₃O₂
M _r = 305.07
Monoclinic,
a = 9.1066 (18) Å
b = 7.6277 (15) Å
c = 14.375 (3) Å
β = 95.31 (3)°
V = 994.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.20 mm⁻¹
T = 120 K
0.25 × 0.13 × 0.12 mm

Data collection

Stoe IPDS 2T diffractometer
Absorption correction: numerical (shape of crystal determined optically; X-RED32 and X-SHAPE, Stoe & Cie, 2005 ▶) T _min = 0.502, T _max = 0.700
10438 measured reflections
2686 independent reflections
2362 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.056
S = 1.13
2686 reflections
143 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010197/vm2154sup1.cif

e-68-o1090-sup1.cif^{(15KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010197/vm2154Isup2.hkl

e-68-o1090-Isup2.hkl^{(131.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010197/vm2154Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O2ⁱ	0.81 (4)	2.13 (4)	2.920 (3)	163 (3)
N2—H2⋯O2ⁱⁱ	0.80 (4)	2.00 (4)	2.800 (3)	176 (3)
O1—H1⋯N1	0.84 (2)	1.88 (3)	2.628 (3)	147 (4)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors are grateful to the Islamic Azad University (Tabriz Branch) and the Islamic Azad University (Ardabil Branch) for financial support.

supplementary crystallographic information

Comment

Semicarbazone compounds are derived from the condensation of carbonyl compounds and semicarbazides. This class are important tridentate O, N, O-donor ligands. As biologically active compounds, semicarbazones find application in the treatment of diseases such as anti-tumor, tuberculosis, leprosy and mental disorder. Furthermore, semicarbazone have wide spread applications in fields such as coordination chemistry, bioinorganic chemistry, and in magnetic, electronic, nonlinear optically active and fluorescent compounds. Also semicarbazone metal complexes seem to be a good candidate for catalytic oxidation studies because of their resist to oxidation (Monfared et al., 2010b).

As part of our studies on the synthesis and characterization of hydrazone derivatives (Bikas et al., 2010; Bikas et al., 2012a,b), we report here the crystal structure of (E)-2-(2-hydroxy-5-iodobenzylidene)hydrazinecarboxamide (Fig.1). Bond distances are in the normal range for similar hydrazone compounds (Abboud et al., 1995). The molecule is approximately planar, with an r.m.s. deviation from the mean plane through all 14 non-H atoms of 0.181 (2) Å. The dihedral angle between the phenyl ring plane and the least-squares plane through the N3—C8—O2—N2 unit is 14.00 (13)°. In the crystal structure of the title compound, the molecule adopts an E configuration with respect to the C7=N1 bond. In the crystal structure of the title compound, there is an intramolecular O—H···N hydrogen bonding between the hydroxyl group and imine nitrogen atom. The carbonyl group forms two different intermolecular N—H···O hydrogen bonds parallel to ac- plane which connects molecules with two R₂²(8) motifs (Table 1, Fig. 2).

Experimental

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 semicarbazide (1.5 mmol), and the mixture was refluxed for 3 h. The solution was then evaporated on a steam bath to 5 ml and cooled to room temperature. The light-yellow precipitates of the title compound were separated and filtered off, washed with 3 ml of cooled methanol and then dried in air. Colorless crystals were obtained from its methanol solution by slow solvent evaporation. Yield: 92%. IR (cm^-1): 3464 (m, O—H), 3176 (m, broad, N—H), 1699 (vs, C=O), 1594 (s, C=N), 1463 (s), 1340 (m), 1259 (vs), 1187 (s), 1072 (m), 942 (vs), 893 (m), 818 (m), 769 (vs), 682 (m), 613 (m), 572 (vs), 517 (s), 522 (m), 472 (vs), 427 (vs).