2-Hy­droxy-3-oct­yloxy-N,N,N-trimethyl­propan-1-aminium bromide

Jiuqiang Liu; Zengbin Wei; Xilian Wei; Chong Zhang

doi:10.1107/S1600536810040705

. 2010 Oct 20;66(Pt 11):o2865. doi: 10.1107/S1600536810040705

2-Hydroxy-3-octyloxy-N,N,N-trimethylpropan-1-aminium bromide

Jiuqiang Liu ^a, Zengbin Wei ^a,^*, Xilian Wei ^a, Chong Zhang ^a

PMCID: PMC3009037 PMID: 21589047

Abstract

In the title compound, C₁₄H₃₂NO₂ ⁺·Br⁻, organic cationsstacked parallel to the a axis andbromide anions placed between the head groups of the cations form ionic pairs via weak intermolecular O—H⋯Br hydrogen bonds. The octyl chain in the cation adopts an all-trans conformation. The O—CH₂—CH(—OH)—CH₂ portion of the molecule is disordered over two sets of sites with occupancy factors of 0.57 (3) and 0.47 (3).

Related literature

For uses of cationic surfactants, see: Zhao et al. (1997 ▶, 2010 ▶). For bond lengths and angles, see: Koh et al. (1993 ▶).

Experimental

Crystal data

C₁₄H₃₂NO₂ ⁺·Br⁻
M _r = 326.32
Monoclinic,
a = 5.9713 (11) Å
b = 7.4780 (12) Å
c = 19.992 (2) Å
β = 92.923 (1)°
V = 891.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 298 K
0.42 × 0.30 × 0.04 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.445, T _max = 0.914
4642 measured reflections
2827 independent reflections
1168 reflections with I > 2σ(I)
R _int = 0.135

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.199
S = 1.03
2827 reflections
211 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ▶), 1124 Friedel pairs
Flack parameter: 0.02 (7)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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/S1600536810040705/jj2054sup1.cif

e-66-o2865-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040705/jj2054Isup2.hkl

e-66-o2865-Isup2.hkl^{(138.8KB, 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
O2—H2⋯Br1ⁱ	0.82	2.50	3.32 (3)	171
O2′—H2′⋯Br1ⁱⁱ	0.82	2.27	3.05 (4)	160

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

Acknowledgments

We acknowledge the financial support of the National Natural Science Foundation of China (20673050) and the Shandong Province Science Foundation (2006B05).

supplementary crystallographic information

Comment

Cationic surfactants have attracted much attention due to their wide spread use in both household and industrial activities, such as in the production of cosmetics (Zhao et al., 1997) and polluted soil treatment (Zhao, et al., 2010). As a contribution to the chemistry of surfactants, we report here the synthesis and crystal structure of the title compound, C₁₄H₃₂Br₁N₁O₂.

The asymmetric unit of the title compound consists of a 3-octyloxy-2-hydroxypropyl-N,N,N- trimethylpropan-1-aminium cation, and a bromide anion, (Fig. 1). Atoms C1:C1', C2:C2', C3:C3', O1:O1' and O2:O2' are disordered with site occupancies of 0.47 (3):0.53 (3). The C—C bond distances in the octyl chain are alternately short and long, the average of the short distances being 1.46 (6)Å and the average of the long distances being 1.49 (8) Å. All N—C bond lengths and C—N—C angles are within the usual ranges (Koh et al., 1993). The bond distances of O1—C3 and O1—C7 are 1.4 (3)and 1.44 (18) Å, respectively. The octyl chains of the cations form monolayers parallel to the (010) plane. Adjacent anions are connected by weak intermolecular O—H···Br interactions and organic cations stacked parallel along the a axis (Table 1, Fig. 2).

Experimental

The reaction was carried out under nitrogen atmosphere. Trimethylammonium bromide (0.12 mol) and octyl glycidyl ether (0.1 mol) were added to a stirred solution of ethanol (100 ml) and stirred at 315 K for 24 h. The resulting clear solution was evaporated under vacuum. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution over a period of two weeks. (yield 82%, m.p.340k) Anal. Calcd (%) for C₁₄H₃₂Br₁N₁O₂ (Mr = 326.32): C, 51.48; H, 9.81; N, 4.29. Found (%): C, 51.52; H, 9.83; N, 4.26.