N′-[1-(4-Amino­phen­yl)ethyl]pyrazine-2-carbohydrazide

Zhi-Yong Xing; De-Cheng Yu; Lai-Jun Li; Hai-Yan Liu; Jian-Fei Zhang

doi:10.1107/S1600536810004083

. 2010 Feb 6;66(Pt 3):o544. doi: 10.1107/S1600536810004083

N′-[1-(4-Aminophenyl)ethyl]pyrazine-2-carbohydrazide

Zhi-Yong Xing ^a,^b,^*, De-Cheng Yu ^a, Lai-Jun Li ^a, Hai-Yan Liu ^a, Jian-Fei Zhang ^c

PMCID: PMC2983521 PMID: 21580315

Abstract

The title compound, C₁₃H₁₃N₅O, crystallizes with two molecules in the asymmetric unit. The crystal structure is stabilized by intramolecular N—H⋯N and N—H⋯O hydrogen bonds. The dihedral angles between the pyrazine ring and the 4-aminolphenyl ring are 2.5 (1) and 6.5 (1)° in the two molecules.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009 ▶); Dubinina et al. (2006 ▶); Ellsworth et al. (2007 ▶); Mukaiyama et al. (2007 ▶).

Experimental

Crystal data

C₁₃H₁₃N₅O
M _r = 255.28
Triclinic,
a = 6.9783 (13) Å
b = 10.689 (3) Å
c = 17.061 (5) Å
α = 106.971 (10)°
β = 98.499 (4)°
γ = 90.174 (14)°
V = 1202.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.10 × 0.09 × 0.04 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.991, T _max = 0.996
9090 measured reflections
4150 independent reflections
2832 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.164
S = 1.05
4150 reflections
364 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810004083/hg2638sup1.cif

e-66-0o544-sup1.cif^{(24KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004083/hg2638Isup2.hkl

e-66-0o544-Isup2.hkl^{(203.3KB, 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—H1A⋯N10ⁱ	0.88 (3)	2.16 (3)	3.030 (4)	170 (3)
N1—H1B⋯O2ⁱⁱ	0.97 (3)	1.89 (3)	2.852 (3)	171 (3)
N6—H6A⋯N1ⁱⁱⁱ	0.91 (3)	2.38 (3)	3.162 (4)	145 (3)
N6—H6B⋯O1ⁱⁱ	0.95 (3)	2.07 (3)	3.015 (3)	169 (3)

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

Acknowledgments

The authors would like to thank the Scientific Research Fund of Heilongjiang Provincial Education Department (No. 1153 G043) and the Doctoral Foundation of Northeast Agricultural University (No. 2009RC22). We also thank Professor Hai-bin Song of Nankai University for his contribution to the crystal analysis for this paper.

supplementary crystallographic information

Comment

The pyrazine ring system is a useful structural element in medicinal chemistry and has found broad applications in drug development which can be used as antiproliferative agent (Dubinina et al., 2006), potent CXCR3 antagonists (Du et al., 2009), CB1 antagonists (Ellsworth et al., 2007) and c-Src inhibitory (Mukaiyama et al., 2007). In view of different applications of this class of compounds, we have undertaken a single-crystal structure determination of the title compound. The crystal structure has two independent molecules in the aysmmetric unit, and the dihedral angles between the pyrazine ring and the 4-aminolphenyl ring are 2.5 (1) and 6.5 (1)° in the two molecules (Fig. 1). The crystal structure is stabilized by N—H···O intermolecular hydrogen bonds (between molecules of the 'A' type), each of which are also by N—H···N intermolecular interactions (with molecules of 'B' type) between them (Fig. 2).

Experimental

For the synthesis of N'-(1-(4-aminophenyl)ethylidene) pyrazine-2-carbohydrazide, (I), a mixture of pyrazine-2-carboxylic acid hydrazide (0.01 mol, 1.38 g) and 1-(4-aminophenyl)ethanone (0.01 mol, 1.35 g) in methanol was refluxed for 2 h. The solid material obtained on cooling was filtered, washed with ethanol: ether =1:1, dried and crystallized from methanol (yield 62%). The compound (1.0 mmol, 0.268 g) was dissolved in 95% ethanol (30 ml) and kept at room temperature for one week, after which yellow platelet shaped single crystals formed and were collected and washed with ether for X-ray diffraction analysis.