n-Tridecyl­amine chloride monohydrate

Lijun Zhang; Youying Di; Wenyan Dan

doi:10.1107/S1600536811006246

. 2011 Feb 26;67(Pt 3):o717. doi: 10.1107/S1600536811006246

n-Tridecylamine chloride monohydrate

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

PMCID: PMC3052102 PMID: 21522459

Abstract

In the title compound, C₁₃H₃₀N⁺·Cl⁻·H₂O, the C₁₃H₂₇ alkyl chain is in an all-trans conformation. In the crystal, intermolecular N—H⋯Cl, N—H⋯O and O—H⋯Cl hydrogen bonds connect the components into layers parallel to (010), with the alkyl chains oriented approximately perpendicular to these layers.

Related literature

For applications of long-chain n-alkylammonium halides, see: Aratono et al. (1998 ▶); Tornblom et al. (2000 ▶); Ringsdorf et al. (1988 ▶). For details of phase transitions in n-alkylammonium chlorides, see: Terreros et al. (2000 ▶). For related structures, see: Rademeyer et al. (2009 ▶); Lundén (1974 ▶); Clark & Hudgens (1950 ▶).

Experimental

Crystal data

C₁₃H₃₀N⁺·Cl⁻·H₂O
M _r = 253.85
Monoclinic,
a = 4.7420 (5) Å
b = 45.250 (3) Å
c = 7.8191 (9) Å
β = 106.332 (2)°
V = 1610.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 K
0.34 × 0.33 × 0.03 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.928, T _max = 0.993
8230 measured reflections
2845 independent reflections
1379 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.124
S = 1.03
2845 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 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/S1600536811006246/lh5197sup1.cif

e-67-0o717-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006246/lh5197Isup2.hkl

e-67-0o717-Isup2.hkl^{(139.7KB, 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⋯Cl1	0.89	2.44	3.303 (3)	162
N1—H1B⋯Cl1ⁱ	0.89	2.36	3.236 (2)	170
N1—H1C⋯O1ⁱⁱ	0.89	2.05	2.901 (4)	159
O1—H1H⋯Cl1	0.85	2.45	3.290 (3)	170
O1—H1I⋯Cl1ⁱⁱⁱ	0.85	2.39	3.228 (2)	170

Open in a new tab

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

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). It has been shown that phase transitions occur in n-alkylammonium chlorides (Terreros et al., 2000). As a part of our studies on novel potential phase transition materials with thermochemical properties, we report herein the crystal structure of the title compound (Fig. 1).

Atoms C2–C13 are essentially co-planar with a maximum deviation of 0.048 (3)Å for atom C2. The alkyl chain in related compounds is typically in the extended conformation e.g. in the isostructural n-tridecylamine bromide monohydrate compound (Rademeyer et al., 2009), n–dodecylammonium bromide (Lundén, 1974) and n–tridecylamine chloride (Clark & Hudgens, 1950). Although the methylene chain has the extended all–trans conformation, it is slightly bent in the vicinity of the ammonium group possibly to accommodate the hydrogen–bonding interactions. Only the C1–C2–C3–C4 torsion angle deviates significantly from 180 °, with a value of 169.84 (3)°. The crystal packing (Fig. 2) is stabilized by intermolecular N—H···Cl, N—H···O and O—H···Cl hydrogen bonds (Table 1 and Fig.2).

Experimental

n–Tridecylamine chloride monohydrate was prepared by the addition of hydrochloric acid to an ethanolic solution of n–tridecylamine. 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 solution at room temperature. Analysis, calculated for C₁₃H₃₂ClNO (Mr =253.85): C 61.51, H 12.71, N 5.52, Cl 13.96%; found: C 61.50, H 12.72, N 5.51, Cl 13.95%.