N-(Quinoxalin-2-yl)-4-toluidine

Wan Ainna Mardhiah Wan Saffiee; Azila Idris; Zaharah Aiyub; Zanariah Abdullah; Seik Weng Ng

doi:10.1107/S1600536808041160

. 2008 Dec 10;65(Pt 1):o93. doi: 10.1107/S1600536808041160

N-(Quinoxalin-2-yl)-4-toluidine

Wan Ainna Mardhiah Wan Saffiee ^a, Azila Idris ^a, Zaharah Aiyub ^a, Zanariah Abdullah ^a, Seik Weng Ng ^a,^*

PMCID: PMC2968000 PMID: 21581731

Abstract

The aromatic and the aromatic fused-rings in the title compound, C₁₅H₁₃N₃, open the angle at the planar N atom to 130.07 (13) and 129.98 (13)° in the two independent molecules in the asymmetric unit. The amino N atom of one molecule forms a hydrogen bond to the 4-N atom of an adjacent quinoxalinyl ring, generating a supramolecular chain.

Related literature

For the structure of N-(2-pyridyl)-4-toluidine, see: Fairuz et al. (2008 ▶); for that of N-(pyrazin-2-yl)-4-toluidine, see: Wan Saffiee et al. (2008 ▶). The title compound is isostructural with N-(quinoxalin-2-yl)-4-chloroaniline; see: Idris et al. (2008 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃
M _r = 235.28
Orthorhombic,
a = 12.2081 (9) Å
b = 11.3720 (9) Å
c = 35.097 (3) Å
V = 4872.5 (6) Å³
Z = 16
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 (2) K
0.40 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
26747 measured reflections
5592 independent reflections
4089 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.112
S = 1.03
5592 reflections
335 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041160/tk2339sup1.cif

e-65-00o93-sup1.cif^{(23KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041160/tk2339Isup2.hkl

e-65-00o93-Isup2.hkl^{(273.9KB, 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—H1⋯N5	0.89 (1)	2.26 (1)	3.114 (2)	163 (2)
N4—H4⋯N2ⁱ	0.87 (1)	2.19 (1)	3.017 (2)	157 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the University of Malaya for supporting this study (FS358/2008 A).

supplementary crystallographic information

Experimental

2-Chloroquinoxaline (1.64 g, 10 mmol) and 4-toluidine (1.07 g, 10 mmol) were mixed with ethanol (2 ml) and the mixture was heated at 423–433 K for 3 h. The product was dissolved in water and the solution extracted with ether. The ether phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped crystals along with some unidentified brown material.