Guanidinium 2-(myristoylsulfanyl)ethane­sulfonate

Elizabeth S Monillas; Wesley H Monillas; Eric R Sirianni; Glenn P A Yap; Klaus H Theopold

doi:10.1107/S1600536811046472

. 2011 Nov 12;67(Pt 12):o3257. doi: 10.1107/S1600536811046472

Guanidinium 2-(myristoylsulfanyl)ethanesulfonate

Elizabeth S Monillas ^a, Wesley H Monillas ^a, Eric R Sirianni ^a, Glenn P A Yap ^a,^*, Klaus H Theopold ^a

PMCID: PMC3238917 PMID: 22199766

Abstract

In the title compound, CH₆N₃ ⁺·C₁₆H₃₁O₄S₂ ⁻ [systematic name: guanidinium 2-(tetradecanoylsulfanyl)ethanesulfonate], each 2-(myristoylthio)ethanesulfonate ion displays hydrogen bonding to three guanidinium counter-ions, which themselves display hydrogen bonding to two symmetry-related 2-(myristoylthio)ethanesulfonate ions. Thus each cation forms six N—H⋯O bonds to neighboring anions, thereby self-assembling an extended ladder-type network. The average hydrogen-bond donor–acceptor distance is 2.931 (5) Å. The alkyl chains form the rungs of a ladder with hydrogen-bonding interactions forming the side rails.

Related literature

The synthesis of the title compound was adapted from Schramm et al. (1954 ▶) and Dalton et al. (1981 ▶). For extended networks via hydrogen-bonding in guanidinium organosulfonates, see: Horner et al. (2001 ▶, 2007 ▶); Russell & Ward (1996 ▶). For typical donor-acceptor distances in these compounds, see: Adams (1978 ▶); Ashiq et al. (2010 ▶). For studies of these structural motifs for use as electronic materials, see: Russell et al. (1994 ▶).

Experimental

Crystal data

CH₆N₃ ⁺·C₁₆H₃₁O₄S₂ ⁻
M _r = 411.62
Monoclinic,
a = 25.185 (13) Å
b = 7.370 (4) Å
c = 12.663 (7) Å
β = 101.851 (10)°
V = 2300 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 200 K
0.25 × 0.18 × 0.01 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.938, T _max = 0.997
18707 measured reflections
5688 independent reflections
2763 reflections with I > 2σ(I)
R _int = 0.085

Refinement

R[F ² > 2σ(F ²)] = 0.082
wR(F ²) = 0.247
S = 1.01
5688 reflections
292 parameters
83 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811046472/zj2033sup1.cif

e-67-o3257-sup1.cif^{(36.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046472/zj2033Isup3.hkl

e-67-o3257-Isup3.hkl^{(278.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811046472/zj2033Isup3.cml

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—H1⋯O1ⁱ	0.87 (4)	2.12 (4)	2.943 (4)	159 (4)
N1—H2⋯O3ⁱⁱ	0.80 (4)	2.11 (4)	2.900 (4)	171 (4)
N2—H3⋯O2ⁱⁱ	0.84 (4)	2.12 (4)	2.957 (4)	171 (4)
N2—H4⋯O1	0.84 (4)	2.13 (4)	2.960 (4)	172 (4)
N3—H5⋯O2	0.83 (5)	2.06 (5)	2.892 (4)	178 (5)
N3—H6⋯O3ⁱ	0.82 (5)	2.14 (5)	2.942 (4)	167 (5)

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

Acknowledgments

This work was supported by the National Science Foundation (grants CHE-0616375 and CHE-0911081) and the Department of Energy (grant DE—FG02–92ER14273).

supplementary crystallographic information

Comment

The title compound was prepared as a reagent in attempts to synthesized a myristoylate protein derivative in vitro. The synthesis was adapted from Schramm et al. (1954) and Dalton et al. (1981). During characterization by X-ray diffraction it was observed to display an interesting ladder-type lattice network. It has been previously reported that guanidinium organosulfonates are capable of extended networks via hydrogen-bonding (Russell & Ward 1996, Horner et al. 2001, 2007). As shown in Figure 2 the guanidinium counterions form near planar end caps, the side rails, with the inward facing myristoyl groups interlocking causing a bilayer stacking or the rungs of the extended ladder-type network. The average hydrogen bond donor-acceptor distance is 2.931 (5) Å which is in the typical range observed for these type of compounds (Adams 1978, Ashiq et al. 2010). These structural motifs have previously been studied for use as electronic materials (Russell et al. 1994).

Experimental

The compound synthesis was adapted from Schramm et al. (1954) and Dalton et al. (1981). Guanidinium 2-mercaptoethansulfonate, 1.0 g (5 mmol), and guanidinium carbonate, 0.9 g (9.9 mmol), were added to 20 mL 1:1 acetonitrile/water. The mixture was stirred and purged with dry nitrogen gas. When the guanidinium carbonate completely dissolved, 1.36 mL (5.01 mmol) of myristoyl chloride was added and the reaction was stirred under 1 atmosphere of nitrogen. After one hour, 4 mL 1:1 acetonitrile/water were added to the mixture. The mixture was stirred for an additional hour after which time the guanidinium 2-(myristoylthio)ethanesulfonate precipitate was filtered and collected yielding 1.09 g (2.65 mmol, 53% yield) of product. Crystals suitable for X-ray diffraction were obtained from slow evaporation of a saturated solution of the compound from a 9:1 acetonitrile/water mixed solvent.