N′-[(E)-3-Indol-3-ylmethyl­ene]isonicotino­hydrazide monohydrate

Liang-You Xia; Wen-Long Wang; Shan-Heng Wang; Yan-Lan Huang; Shang Shan

doi:10.1107/S1600536809027329

. 2009 Jul 18;65(Pt 8):o1900. doi: 10.1107/S1600536809027329

N′-[(E)-3-Indol-3-ylmethylene]isonicotinohydrazide monohydrate

Liang-You Xia ^a, Wen-Long Wang ^b, Shan-Heng Wang ^b, Yan-Lan Huang ^b, Shang Shan ^b,^*

PMCID: PMC2977231 PMID: 21583590

Abstract

Crystals of the title compound, C₁₅H₁₂N₄O·H₂O, were obtained from a condensation reaction of isonicotinylhydrazine and 3-indolylformaldehyde. The molecule assumes an E configuration, with the isonicotinoylhydrazine and indole units located on the opposite sites of the C=N double bond. In the molecular structure the pyridine ring is twisted with respect to the indole ring system, forming a dihedral angle of 44.72 (7)°. Extensive classical N—H⋯N, N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonding and weak C—H⋯O interactions are present in the crystal structure.

Related literature

For the applications of hydrazone derivatives in biology, see: Okabe et al. (1993 ▶). For general background to this work, see: Shan et al. (2003 ▶); Qiang et al. (2007 ▶). For the corresponding (E)-3-indolylformaldehyde isonicotinoylhydrazone methanol solvate, see: Tai et al. (2003 ▶), and (E)-3-indolylformaldehyde isonicotinoylhydrazone ethanol solvate, see: Jing et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₂N₄O·H₂O
M _r = 282.30
Monoclinic,
a = 7.1984 (11) Å
b = 25.327 (4) Å
c = 7.9811 (16) Å
β = 104.062 (12)°
V = 1411.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 K
0.40 × 0.32 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: none
9235 measured reflections
2504 independent reflections
1575 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.161
S = 1.07
2504 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536809027329/xu2554sup1.cif

e-65-o1900-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027329/xu2554Isup2.hkl

e-65-o1900-Isup2.hkl^{(120.5KB, 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
N1—H1N⋯N4ⁱ	0.91	2.06	2.961 (3)	171
N3—H3N⋯O1Wⁱⁱ	0.89	2.11	2.939 (3)	155
O1W—H1A⋯O1ⁱⁱⁱ	0.91	1.90	2.800 (3)	168
O1W—H2A⋯N2	0.89	2.40	3.223 (3)	152
C12—H12⋯O1Wⁱⁱ	0.93	2.58	3.466 (3)	159

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

Acknowledgments

The work was supported by the Natural Science Foundation of Zhejiang Province, China (No. M203027).

supplementary crystallographic information

Comment

The hydrazone derivatives has attracted our much attention because they have shown to be potential DNA damaging and mutagenic agents (Okabe et al., 1993). As part of the ongoing investigation on the relationship between structure and property of hydrazone derivatives (Shan et al., 2003; Qiang et al., 2007) the title compound has recently been prepared in our laboratory and its crystal structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. The pyridine ring is twisted with respect to the indole ring system by a dihedral angle of 44.72 (7)°. The N2—C9 bond distance of 1.293 (3) Å shows a typical C═N double bond. The isonicotinoylhydrazine and indole moieties are located on the opposite sites of the CN bond, thus the molecule assumes an E configuration, which agrees with those found in ethanol solvate compound (Jing et al., 2006) and methanol solvate compound (Tai et al., 2003).

The extensive classic hydrogen bonding and weak C—H···O hydrogen bonding are present in the crystal structure (Table 1).

Experimental

Isonicotinylhydrazine (1.37 g, 0.01 mol) was dissolved in ethanol (50 ml), the solution was heated at about 333 K for several minutes until the solution cleared. An ethanol solution (20 ml) containing 3-indolylformaldehyde (1.45 g, 0.01 mol) was dropped slowly into the above solution with continuous stirring, and the mixture solution was refluxed for 1.5 h. When the solution had cooled to room temperature, colorless powder crystals appeared. The powder crystals were separated from the solution and washed with cold water three times. Recrystallization was performed twice with a mixture solvent of 2-propanol-water (1:1 v/v), to obtain single crystals of the title compound.