Tetra­ethyl­ammonium l-tartarate dihydrate

Mohd Basyaruddin Abdul Rahman; Khairulazhar Jumbri; Kamaliah Sirat; Reza Kia; Hoong-Kun Fun

doi:10.1107/S1600536808036969

. 2008 Nov 13;64(Pt 12):o2343. doi: 10.1107/S1600536808036969

Tetraethylammonium l-tartarate dihydrate

Mohd Basyaruddin Abdul Rahman ^a,^‡, Khairulazhar Jumbri ^a, Kamaliah Sirat ^a, Reza Kia ^b, Hoong-Kun Fun ^b,^*

PMCID: PMC2960025 PMID: 21581318

Abstract

In the crystal structure of the title compound, C₈H₂₀N⁺·C₄H₅O₆ ⁻·2H₂O, the ions and water molecules are linked via O—H⋯O and C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (001).

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Allen et al. (2006 ▶); Jiang et al. (2008 ▶); Mei et al. (2002 ▶).

Experimental

Crystal data

C₈H₂₀N⁺·C₄H₅O₆ ⁻·2H₂O
M _r = 315.36
Monoclinic,
a = 7.4074 (1) Å
b = 13.8989 (2) Å
c = 8.0546 (1) Å
β = 106.553 (1)°
V = 794.89 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100.0 (1) K
0.47 × 0.45 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.861, T _max = 0.981
10518 measured reflections
3579 independent reflections
3240 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.092
S = 1.05
3579 reflections
218 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036969/ci2709sup1.cif

e-64-o2343-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036969/ci2709Isup2.hkl

e-64-o2343-Isup2.hkl^{(175.5KB, 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
O2—H1O2⋯O5ⁱ	1.00 (2)	1.52 (2)	2.5108 (13)	173 (2)
O3—H1O3⋯O1Wⁱⁱ	0.91 (2)	1.85 (2)	2.7191 (14)	162 (2)
O4—H1O4⋯O2Wⁱⁱⁱ	0.84 (2)	2.18 (2)	2.9780 (16)	160 (2)
O1W—H1W1⋯O2^iv	0.82 (2)	2.56 (2)	3.0668 (14)	122 (2)
O1W—H1W1⋯O2W^v	0.82 (2)	2.57 (2)	3.2155 (16)	137 (2)
O1W—H2W1⋯O6ⁱⁱⁱ	0.88 (3)	2.00 (3)	2.8672 (15)	171 (2)
O2W—H2W2⋯O1^vi	0.84 (2)	2.40 (2)	3.0082 (14)	129 (2)
C5—H5A⋯O3^vii	0.97	2.56	3.4344 (15)	151
C8—H8B⋯O4	0.96	2.38	3.3447 (16)	178
C10—H10B⋯O3^vii	0.96	2.47	3.4195 (16)	168
C11—H11A⋯O4	0.97	2.50	3.2693 (15)	136

Open in a new tab

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

Acknowledgments

MBAR, KJ and KS thank the Ministry of Higher Education of Malaysia for the research grant 05-10-07-377FR (Fundamental Research Grant Scheme-FRGS). HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund (grant No. 305/PFIZIK/613312). RK thanks Universiti Sains Malaysia for the award of a post-doctoral research fellowship.

supplementary crystallographic information

Comment

The crystal structures of chiral complexes of the plant acid (L-tartaric acid) with tetraethylammonium have been investigated in our laboratory in order to understand the nature of intramolecular and intermolecular interactions. The title compound was obtained by neutralization method at room temperature. Some other related compounds containing the same cation have been previously reported (Jiang et al., 2008; Allen et al., 2006). The crystal structure of bis(tetraethylammonium) tartrate bis(thiourea) dihydrate has also been reported (Mei et al., 2002).

The asymmetric unit of the title compound (Fig. 1) contains a tartarate anion, a tetraethylammonium cation and two water molecules of crystallization. Two intermolecular C—H···O hydrogen bonds involving O4 as a bifurcated acceptor link anion and cation in the asymmetric unit to form a seven-membered ring, with R¹₂(7) ring motif (Bernstein et al., 1995). In the crystal structure, the ionic units and water molecules are linked via O—H···O and C—H···O hydrogen bonds (Table 1) forming a two-dimensional network parallel to the (001) [Fig. 2].

Experimental

L-Tartaric acid (7.504 g, 0.05 mol) was first dissolved in 20 ml of distilled water in a 50 ml beaker. An aqueous solution (20% in water) of tetraethylammonium hydroxide (36.59 ml, 0.05 mol) was added slowly into an aqueous solution of L-tartaric acid and the mixture was stirred with a magnetic stirrer for 2 h at room temperature. A white solid product was obtained after being dried at 343 K under vacuum for 2 d. The product was dissolved in methanol and then covered by aluminium foil to allow slow evaporation at room temperature. Clear crystalline solid was obtained after 3 d. Decomposition temperature range (471.35–472.6 K). Analysis calculated (%): C 51.60, H 9.02, N 5.01%; found: C 50.53, H 9.09, N 3.28%.