5-(4-Methyl­piperazin-1-yl)-2-nitro­aniline

Chang-jun Luan; Cheng Guo; Wei Wang; Jian-qiang Wang; Ren-jun Du

doi:10.1107/S1600536810015953

. 2010 May 8;66(Pt 6):o1268. doi: 10.1107/S1600536810015953

5-(4-Methylpiperazin-1-yl)-2-nitroaniline

Chang-jun Luan ^a, Cheng Guo ^a,^*, Wei Wang ^a, Jian-qiang Wang ^a, Ren-jun Du ^a

PMCID: PMC2979376 PMID: 21579369

Abstract

In the title compound, C₁₁H₁₆N₄O₂, the dihedral angle between the benzene ring and the plane of the four carbon atoms in the piperazine ring is 12.17 (3)°; the latter ring adopts a chair conformation. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, the molecules are linked by N—H⋯N hydrogen bonds, forming chains.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For the synthetic procedure and use of the title compound as an intermediate in the synthesis of tyrosine kinase inhibitors, see: Renhowe et al. (2009 ▶).

Experimental

Crystal data

C₁₁H₁₆N₄O₂
M _r = 236.28
Monoclinic,
a = 11.027 (2) Å
b = 6.121 (1) Å
c = 17.524 (4) Å
β = 103.79 (3)°
V = 1148.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.971, T _max = 0.995
2205 measured reflections
2090 independent reflections
1358 reflections with I > 2σ(I)
R _int = 0.042
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.192
S = 1.01
2090 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 I, global. DOI: 10.1107/S1600536810015953/im2192sup1.cif

e-66-o1268-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015953/im2192Isup2.hkl

e-66-o1268-Isup2.hkl^{(102.8KB, 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
N3—H3C⋯N1ⁱ	0.86	2.39	3.156 (4)	148
N3—H3D⋯O1	0.86	2.06	2.669 (4)	127

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Test and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound, (I), has been reported as an intermediate for the synthesis of novel tyrosine kinase inhibitors (Renhowe, P. A. et al., 2009). We herein report its crystal structure.

In the molecular structure of (I), (Fig.1), bond lengths (Allen et al., 1987) and angles are within normal ranges. N2, N3 and N4 atoms are almost coplanar with the benzene ring to which they are bonded [deviations of 0.078 (1), 0.052 (1) and 0.078 (1) Å]. The plane of C2—C3—C4—C5 is nearly parallel with the benzene ring plane (the torsion angle is 12.17 (3) °). By contrast, due to the piperazine moiety adopting a chair conformation N1—C2—C5 and N2—C3—C4 form two separate planes with torsion angle of 45.87 (2) ° and 25.92 (3) °, respectively, with respect to the benzene ring. The crystal structure of the title compound exhibits N—H···O, C—H···O, and N—H···N intra- and intermolecular hydrogen bonds to form a three dimensional network.

As can be seen from the packing diagram, (Fig. 2), the molecules are stacked along the b axis.

Experimental

The title compound, (I) was prepared by a literature method (Renhowe, P. A. et al., 2009). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in methanol (20 ml) and evaporating the solvent slowly at room temperature for about 7 d.