4-Ethoxyanilinium chloride

The title compound, C8H12NO+·Cl−, consists of an almost planar protonated 4-ethoxyanilinium cation with the N atom showing the biggest deviation from the plane formed by all non-H atoms of the cation [0.066 (1) Å]. In the crystal, N—H⋯Cl hydrogen bonds link cations and anions into chains along the a axis. Additional C—H⋯π and π–π interactions [centroid–centroid distance = 4.873 (2) Å] stabilize the crystal structure.

The title compound, C 8 H 12 NO + ÁCl À , consists of an almost planar protonated 4-ethoxyanilinium cation with the N atom showing the biggest deviation from the plane formed by all non-H atoms of the cation [0.066 (1) Å ]. In the crystal, N-HÁ Á ÁCl hydrogen bonds link cations and anions into chains along the a axis. Additional C-HÁ Á Á andinteractions [centroid-centroid distance = 4.873 (2) Å ] stabilize the crystal structure.
The author is grateful to the Starter Fund of Southeast University for financial support to buy the X-ray diffractometer.

Comment
The crystal structure of 4-ethoxyanilinium perchlorate as well as those of 2-and 4-methoxyanilinium chloride are known (Fu, 2009;Zhao, 2009;Jiang et al., 1996). In this article, the crystal structure of (I) is presented.

Experimental
Single crystals suitable for X-ray diffraction were obtained by slow evaporation at room temperature of an ethanolic solution of equimolar amounts of 4-ethoxyaniline and 6M hydrochloric acid.
Dielectric studies (capacitance and dielectric loss measurements) were performed using an automatic impedance TongHui2828 Analyzer on powder samples that were pressed into tablets on the surfaces of which a conducting carbon glue was deposited. Dielectric permittivity of the compound was tested to systematically to investigate the possibility of ferroelectric phase transitions (Li et al., 2008, Ye et al., 2009Zhang et al., 2009). Unfortunately, the temperature dependence of the relative permittivity at 1 MHz varied smoothly from 4.0 to 4.3 and there was no distinct anomaly observed from 93 K to 350 K (sublimation higher than 378 K) in the title compound, suggesting that this compound should not be a real ferroelectric or that no distinct phase transition occurred within the measured temperature range.

Refinement
Positional parameters of all the H atoms for C atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, with U iso (H) = 1.2U eq (C). H atoms bonded to nitrogen atom were found in the difference maps and refined freely.  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.