N′-(2-Hy­droxy-3,5-diiodo­benzyl­idene)-2-methyl­benzohydrazide

Chun-Bao Tang

doi:10.1107/S1600536810052050

. 2010 Dec 18;67(Pt 1):o166. doi: 10.1107/S1600536810052050

N′-(2-Hydroxy-3,5-diiodobenzylidene)-2-methylbenzohydrazide

Chun-Bao Tang ^a,^*

PMCID: PMC3050158 PMID: 21522673

Abstract

The asymmetric unit of the title compound, C₁₅H₁₂I₂N₂O₂, contains two independent molecules in which the dihedral angles between the two benzene rings are 62.4 (7) and 41.1 (7)°. Intramolecular O—H⋯N hydrogen bonds generate S(6) ring motifs in each molecule. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶). For reference bond-length data, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₂I₂N₂O₂
M _r = 506.07
Monoclinic,
a = 9.658 (2) Å
b = 11.723 (2) Å
c = 14.732 (3) Å
β = 93.216 (2)°
V = 1665.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.78 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.549, T _max = 0.601
12106 measured reflections
5976 independent reflections
4443 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.089
S = 1.01
5976 reflections
389 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.88 e Å⁻³
Absolute structure: Flack (1983 ▶), 2163 Friedel pairs
Flack parameter: 0.10 (3)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052050/sj5075sup1.cif

e-67-0o166-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052050/sj5075Isup2.hkl

e-67-0o166-Isup2.hkl^{(292.5KB, hkl)}

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
O1—H1⋯N1	0.82	1.87	2.570 (9)	143
O3—H3⋯N3	0.82	1.85	2.560 (10)	144
N4—H4⋯O2	0.90 (5)	1.94 (4)	2.786 (8)	155 (8)
N2—H2⋯O4ⁱ	0.90 (6)	1.91 (3)	2.788 (9)	164 (10)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Jiaying University research fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Hydrazone compounds have received much attention in biological and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). In the present paper, the author reports the crystal structure of the new title hydrazone compound (Fig. 1).

The asymmetric unit of the title compound contains two independent molecules. The dihedral angles between the two benzene rings in the two molecules are 62.4 (7) and 41.1 (7)°, respectively. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8, N1—N2—C8—C9, C16—C22—N3—N4, C22—N3—N4—C23, and N3—N4—C23—C24 are 1.5 (6), 7.2 (6), 4.9 (6), 3.4 (6), 4.8 (6), and 4.3 (6)°, respectively. Bond lengths in the molecules are normal (Allen et al., 1987) and comparable to those in the similar compound the author reported recently (Tang, 2010). Intramolecular O1—H1···N1 and O3—H3···N3 hydrogen bonds generate S(6) ring motifs in each molecule (Bernstein et al., 1995). In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis (Fig. 2).

Experimental

2-Hydroxy-3,5-diiodobenzaldehyde (0.1 mmol, 37.4 mg) and 2-methylbenzohydrazide (0.1 mmol, 15.0 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless block-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.