(E)-N′-(5-Bromo-2-hy­droxy-3-meth­oxy­benzyl­idene)-1H-indole-3-carbo­hydrazide

Xiao-Yan Li

doi:10.1107/S1600536811039195

. 2011 Sep 30;67(Pt 10):o2815. doi: 10.1107/S1600536811039195

(E)-N′-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-1H-indole-3-carbohydrazide

Xiao-Yan Li ^a,^*

PMCID: PMC3201537 PMID: 22065413

Abstract

There are three independent moleculesi n the asymmetric unit of the title compound, C₁₈H₁₆BrN₃O₃, in which the dihedral angles between the indole and benzene rings are 76.9 (2), 4.9 (2), and 70.9 (2)°. All three molecules exist in a trans configuration with respect to the methylidene units. In each molecule, there is one intramolecular O—H⋯N hydrogen bond. In the crystal, N—H⋯O hydrogen bonds occur.

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

C₁₈H₁₆BrN₃O₃
M _r = 402.25
Monoclinic,
a = 15.023 (3) Å
b = 13.860 (3) Å
c = 24.856 (4) Å
β = 102.192 (2)°
V = 5058.8 (17) Å³
Z = 12
Mo Kα radiation
μ = 2.46 mm⁻¹
T = 298 K
0.13 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.740, T _max = 0.847
23383 measured reflections
8466 independent reflections
3662 reflections with I > 2σ(I)
R _int = 0.089

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.125
S = 0.97
8466 reflections
700 parameters
24 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.40 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039195/qm2030sup1.cif

e-67-o2815-sup1.cif^{(34.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039195/qm2030Isup2.hkl

e-67-o2815-Isup2.hkl^{(422.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039195/qm2030Isup3.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—H3⋯O8ⁱ	0.90 (1)	2.73 (4)	3.453 (8)	138 (5)
N9—H9⋯O2	0.89 (1)	2.16 (2)	3.048 (6)	171 (6)
N6—H6⋯O5ⁱⁱ	0.90 (1)	2.28 (2)	3.159 (6)	165 (5)
N2—H2⋯O9ⁱⁱⁱ	0.90 (1)	2.01 (2)	2.893 (6)	168 (6)
N5—H5⋯O6^iv	0.90 (1)	1.99 (1)	2.885 (6)	174 (5)
N8—H8⋯O3^v	0.90 (1)	1.89 (1)	2.795 (6)	179 (6)
O7—H7⋯N7	0.82	1.90	2.615 (6)	146
O4—H4⋯N4	0.82	1.92	2.634 (6)	145
O1—H1⋯N1	0.82	1.91	2.610 (6)	143

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

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

supplementary crystallographic information

Comment

In the last few years, hydrazones have attracted much attention for 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.

In the asymmetric unit of the title compound there are three (A, B and C) independent molecules (Fig. 1). The bond distances and angles are comparable to those observed in similar compounds (Li, 2011a,b). The dihedral angles between the indole ring and the benzene ring in the three molecules are 76.9 (2), 175.1 (2), and 70.9 (2)° for molecules A, B and C, respectively. All the molecules exist in the trans configuration with respect to the methylidene units. In each molecule there is an O—H···N intramolecular hydrogen bond (Table 1).

Experimental

A mixture of 1H-indole-3-carbohydrazide (0.189 g, 1 mmol) and 5-bromo-2-hydroxy-3-methoxybenzaldehyde (0.231 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.