2-(4-Meth­oxy­phenyl)-2-oxoethan­aminium chloride

Hoong-Kun Fun; Wan-Sin Loh; S Viveka; Dinesha; G K Nagaraja

doi:10.1107/S1600536812039645

. 2012 Sep 22;68(Pt 10):o2987. doi: 10.1107/S1600536812039645

2-(4-Methoxyphenyl)-2-oxoethanaminium chloride

Hoong-Kun Fun ^a,^b,^*,^‡, Wan-Sin Loh ^a,^§, S Viveka ^c, Dinesha ^c, G K Nagaraja ^c

PMCID: PMC3470349 PMID: 23125762

Abstract

In the cation of the title compound, C₉H₁₂NO₂ ⁺·Cl⁻, the dihedral angle between the 2-oxoethanaminium N—C—C(=O)– plane [maximum deviation = 0.0148 (12) Å] and the benzene ring is 7.98 (8)°. The methoxy group is approximately in-plane with the benzene ring, with a C—O—C—C torsion angle of −2.91 (18)°. In the crystal, the cations and chloride anions are connected by N—H⋯Cl and C—H⋯Cl hydrogen bonds, forming a layer parallel to the bc plane. A C—H⋯π interaction further links the layers.

Related literature

For syntheses and applications of nitrogen-containing heterocyclic compounds, see: Alvarez-Builla et al. (2011 ▶); Katritzky et al. (2010 ▶); Chen et al. (2011 ▶). For a related structure, see: Zhang et al. (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₉H₁₂NO₂ ⁺·Cl⁻
M _r = 201.65
Monoclinic,
a = 12.2822 (8) Å
b = 7.1605 (4) Å
c = 11.1226 (7) Å
β = 92.435 (1)°
V = 977.31 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 100 K
0.40 × 0.24 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.870, T _max = 0.942
10764 measured reflections
2871 independent reflections
2622 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.099
S = 1.08
2871 reflections
132 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039645/is5194sup1.cif

e-68-o2987-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039645/is5194Isup2.hkl

e-68-o2987-Isup2.hkl^{(141KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812039645/is5194Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N1⋯Cl1ⁱ	0.95 (2)	2.26 (2)	3.2061 (14)	173.6 (15)
N1—H3N1⋯Cl1	0.99 (2)	2.19 (2)	3.1496 (12)	162.6 (19)
N1—H1N1⋯Cl1ⁱⁱ	0.97 (2)	2.27 (2)	3.2240 (12)	168.4 (19)
C9—H9B⋯Cl1ⁱⁱⁱ	0.99	2.69	3.6135 (13)	156
C3—H3A⋯Cg1^iv	0.95	2.53	3.3909 (14)	150

Open in a new tab

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for a Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian government and USM for the position of Research Officer under the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

The synthesis of nitrogen-containing heterocycles has long been a topic of intense research (Alvarez-Builla et al., 2011; Katritzky et al., 2010). This is due, in large part, to the importance of these compounds as drug candidates. The vast majority of new molecular entities (NMEs) contain at least one nitrogen atom in the chemical structure. A subcategory of these compounds are imidazoles, which are notable pharmacophores in a number of areas of discovery chemistry research (Chen et al., 2011). Appropriately, numerous synthetic approaches to these compounds have been published in the literature (Alvarez-Builla et al., 2011). Phenacyl amines are the key intermediate in the synthesis of various ketoamides and also provides a robust synthetic route toward 1H-4-substituted imidazole developed using phenacyl amines. Herein we report the synthesis and crystal structure of 2-(4-methoxyphenyl)-2-oxoethanaminium chloride.

The asymmetric unit of the title compound as shown in Fig. 1 consists of one 2-(4-methoxyphenyl)-2-oxoethanaminium cation and one chloride anion. One proton is transferred from the hydrochloric acid to the N atom. The ketone side chain and the methoxy group are coplanar with the benzene ring (C2–C7) with the torsion angles of C6—C5—C8—C9 = 173.82 (11)° and C1—O1—C2—C7 = -2.91 (18)°, respectively. The bond lengths and angles are similar to a related structure (Zhang et al., 2009).

The crystal structure (Fig. 2) is mainly stabilized by N—H···Cl and C—H···Cl hydrogen bonds (Table 1). In the crystal structure, the amine N atom acts as donor whereas the chloride anion acts as acceptor, linking them into a layer parallel to the bc plane. A C—H···π interaction (Table 1), involving the benzene ring, further consolidates the crystal structure.

Experimental

A 40 ml ethanolic solution of 5 mmol 4-methoxy phenacyl bromide was stirred with 5 mmol of HMTA for 10 h. The solid precipitated was filtered and the precipitate was dissolved in HCl and evaporated to dryness to get the crystals. M.p.: 433 K.