Bis(tetra­ethyl­ammonium) oxalate dihydrate

McNeese, T.J.; Pike, R.D.

doi:10.1107/S160053681203022X

Volume 68
Part 8
Pages o2382-o2383
August 2012

Received 1 June 2012
Accepted 2 July 2012
Online 7 July 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 7.9
Details

Bis(tetraethylammonium) oxalate dihydrate

Timothy J. McNeese ^a ^* and Robert D. Pike ^b

^aDepartment of Chemistry, Loyola University Maryland, 4501 North Charles Street, Baltimore, MD 21210-2699, USA, and ^bDepartment of Chemistry, College of William and Mary, PO Box 8795, Williamsburg, VA 23187-8795, USA
Correspondence e-mail: tmcneese@loyola.edu

The title compound, 2C₈H₂₀N⁺·C₂O₄^2-·2H₂O, synthesized by neutralizing H₂C₂O₄·2H₂O with (C₂H₅)₄NOH in a 1:2 molar ratio, is a deliquescent solid. The oxalate ion is nonplanar, with a dihedral angle between carboxylate groups of 64.37 (2)°. O-HO hydrogen bonds of moderate strength link the O atoms of the water molecules and the oxalate ions into rings parallel to the c axis. The rings exhibit the graph-set motif R₄⁴(12). In addition, there are weak C-HO interactions in the crystal structure.

Related literature

For related compounds containing planar and nonplanar oxalate ions, see: Beagley & Small (1964); Robertson (1965); Jeffrey & Parry (1954). For general syntheses of tetraalkylammonium salts and their uses, see: Barthel & Kunz (1988); Heck (1982); Markowitz (1957); McNeese et al. (1984); Starks (1971). For uses of [(C₂H₅)₄N)₂(C₂O₄)]·2H₂O, see: Darensbourg et al. (1992); Demadis & Coucouvanis (1995); Diop et al. (1997); Engels et al. (1983). For classification of the graph-set motifs, see: Etter et al. (1990). For classification of the hydrogen bonds, see: Gilli & Gilli (2009). Oxalate was confirmed by the blue ring resorcinol test (Chernoff, 1920).

Experimental

Crystal data

2C₈H₂₀N⁺·C₂O₄^2-·2H₂O
M_r = 384.55
Orthorhombic, P c a 2₁
a = 19.9302 (4) Å
b = 7.6627 (1) Å
c = 14.3253 (3) Å
V = 2187.75 (7) Å³
Z = 4
Cu K radiation
= 0.70 mm^-1
T = 100 K
0.32 × 0.25 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.808, T_max = 0.966
17374 measured reflections
2026 independent reflections
1953 reflections with I > 2(I)
R_int = 0.067

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.081
S = 1.07
2026 reflections
256 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O6-H1WO1ⁱ	0.82 (4)	1.96 (4)	2.749 (2)	161 (3)
O6-H2WO3ⁱⁱ	0.87 (4)	2.00 (4)	2.842 (2)	162 (3)
O5-H3WO2ⁱⁱⁱ	0.86 (4)	1.88 (4)	2.720 (2)	166 (4)
O5-H4WO4^iv	0.85 (4)	1.89 (4)	2.732 (2)	167 (3)
C3-H3BO2ⁱ	0.99	2.40	3.300 (3)	151
C5-H5AO1	0.99	2.43	3.324 (3)	149
C5-H5BO4ⁱⁱⁱ	0.99	2.34	3.270 (3)	157
C7-H7AO3ⁱⁱ	0.99	2.44	3.332 (3)	150
C8-H8BO4ⁱⁱⁱ	0.98	2.57	3.497 (3)	158
C10-H10AO2ⁱ	0.98	2.50	3.450 (3)	162
C11-H11BO5^v	0.99	2.41	3.384 (3)	167
C13-H13AO1^vi	0.99	2.37	3.334 (3)	165
C15-H15BO4^vi	0.99	2.51	3.166 (3)	124
C16-H16CO6^vii	0.98	2.59	3.559 (3)	170
C18-H18AO3ⁱ	0.98	2.59	3.296 (2)	129
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, -y+2, z-{\script{1\over 2}}]$ ; (iv) x, y, z-1; (v) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (vi) $[x+{\script{1\over 2}}, -y+1, z]$ ; (vii) $[-x+1, -y, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXLE (Hübschle et al., 2011); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2256 ).

Acknowledgements

TJM acknowledges Daniel M. Perrine and Daniel R. Gorbaty for technical assistance and Loyola University Maryland for financial support. RDP thanks the NSF (grant No. CHE-0443345) and the College of William and Mary for the purchase of the X-ray equipment.

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organic compounds