Penta­decyl­ammonium methyl sulfate

Lijun Zhang; Youying Di; Wenyan Dan

doi:10.1107/S1600536811011226

. 2011 Apr 7;67(Pt 5):o1051. doi: 10.1107/S1600536811011226

Pentadecylammonium methyl sulfate

Lijun Zhang ^a, Youying Di ^a,^*, Wenyan Dan ^a

PMCID: PMC3089230 PMID: 21754378

Abstract

In the crystal of the title compound, C₁₅H₃₄N⁺·CH₃SO₄ ⁻, the cations and anions are joined together via strong N—H⋯O hydrogen bonds into layers parallel to (001).

Related literature

Long-chain n-alkylammonium halides are widely used as surfactants (Aratono et al., 1998 ▶; Tornblom et al., 2000 ▶) and as models for biological membranes (Ringsdorf et al., 1988 ▶). For solid-solid phase transitions in n-alkylammonium chlorides, see: Terreros et al. (2000 ▶).

Experimental

Crystal data

C₁₅H₃₄N⁺·CH₃O₄S⁻
M _r = 339.53
Monoclinic,
a = 5.4260 (5) Å
b = 7.4981 (6) Å
c = 24.376 (2) Å
β = 93.557 (1)°
V = 989.83 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 298 K
0.31 × 0.30 × 0.28 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.946, T _max = 0.951
5243 measured reflections
1880 independent reflections
1025 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.228
S = 1.06
1880 reflections
130 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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/S1600536811011226/ru2002sup1.cif

e-67-o1051-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011226/ru2002Isup2.hkl

e-67-o1051-Isup2.hkl^{(92.5KB, 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—H1A⋯O2ⁱ	0.89	2.03	2.857 (6)	155
N1—H1B⋯O3ⁱⁱ	0.89	2.03	2.911 (3)	169

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

Acknowledgments

We acknowledge the National Natural Science Foundation of China (20973089) for financial support.

supplementary crystallographic information

Comment

Long-chain n–alkylammonium halides are widely used as surfactants (Aratono et al., 1998; Tornblom et al., 2000) and as models for biological membranes (Ringsdorf et al., 1988). They exhibit polymorphism at room temperature; solid-solid phase transitions occurred in n–alkylammonium chlorides (Terreros et al., 2000). As a part of the studies on novel potential phase transition materials with the thermochemical properties such as n–alkylammonium chlorides, we report the crystal structure of the title compound (Fig. 1).

Atoms N1–C15 are coplanar in the title compound. The Space group of the title compound is P2(1)/m, however, the space group is P2(1)/c (Melanie Rademeyer,2009). The title compound has a symmetry plane, similarly, the n-pentadecylammonium bromide monohydrates has a symmetry axis. Furthermore, the S, O1, O2 and C16 are coplanar in the title compound.

The crystal packing (Fig. 2) is stabilized by one intermolecular N—H···O hydrogen bonds forming ionic pairs, and two other intramolecular N—H···O hydrogen bonds (Table 1).

Experimental

n–Pentadecylammonium methyl sulfate was prepared by the addition of sulfuric acid to an methanol solution of n–pentadecylamine. The mixture was heated and stirred under reflux for 6 h. Single crystals suitable for X–ray diffraction were prepared by evaporation of the resulting solutionat room temperature. Analysis, calculated for C₁₆H₃₇NSO₄ (Mr =339.53): C 56.60, H 10.98, N 4.13%; found: C 56.59, H 10.99, N 4.12%.