Bis(tetra­ethyl­ammonium) bis­(hydrogen l-tartrate) l-tartaric acid monohydrate

Rajalakshmi, M.; Indirajith, R.; Gopalakrishnan, R.; Ramamurthi, K.; Stoeckli-Evans, H.

doi:10.1107/S1600536811015479

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1315-o1316

doi:10.1107/S1600536811015479

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Bis(tetraethylammonium) bis(hydrogen L-tartrate) L-tartaric acid monohydrate

M. Rajalakshmi,^a R. Indirajith,^a R. Gopalakrishnan,^a K. Ramamurthi ^b and Helen Stoeckli-Evans ^c ^*

^aDepartment of Physics, Anna University, Chennai 600 025, India, ^bCrystal Growth and Thin Film Laboratory, School of Physics, Bharathidasan University, Tiruchirappalli 620 024, India, and ^cInstitute of Physics, University of Neuchâtel, CH-2000 Neuchâtel, Switzerland
^*Correspondence e-mail: krgkrishnan@yahoo.com

(Received 10 March 2011; accepted 24 April 2011; online 7 May 2011)

In the title compound, 2C₈H₂₀N⁺·2C₄H₅O₆⁻·C₄H₆O₆·H₂O, the presence of the two tetraethylammonium cations is balanced by two hydrogen L-tartrate anions. Also present in the asymmetric unit are a molecule of L-tartaric acid and a water molecule. The various components are linked by O—H⋯O hydrogen bonds. In the crystal, two-dimensional networks are formed via O—H⋯O hydrogen bonds and C—H⋯O interactions involving the water molecule, the hydrogen L-tartrate anions and the L-tartaric acid molecules. These layers, which stack along [001], are separated by tetraethylammonium cations. The latter are also involved in C—H⋯O interactions with the anions and the L-tartaric acid and water molecules participating in the two-dimensional network.

Related literature

For potential industrial applications of non-linear optical (NLO) materials, see: Dega-Szafran et al. (2008 ); Bosshard et al. (1995 ). For an example of a structure showing bulk quadratic NLO effects, see: Coe et al. (2005 ). For the crystal structure of tetraethylammonium hydrogen L-tartrate dihydrate, see: Rahman et al. (2008 ).

Experimental

Crystal data

2C₈H₂₀N⁺·2C₄H₅O₆⁻·C₄H₆O₆·H₂O
M_r = 726.76
Monoclinic, P 2₁
a = 7.5725 (4) Å
b = 27.7907 (13) Å
c = 8.7620 (6) Å
β = 99.884 (5)°
V = 1816.55 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 173 K
0.45 × 0.32 × 0.25 mm

Data collection

Stoe IPDS 2 diffractometer
20250 measured reflections
3502 independent reflections
3116 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.064
S = 1.03
3502 reflections
469 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O2	0.89 (5)	2.56 (4)	2.995 (3)	111 (3)
O1W—H1WB⋯O5ⁱ	0.89 (5)	2.19 (5)	3.015 (3)	155 (4)
O3—H3O⋯O1W	0.84	2.04	2.868 (3)	167
O4—H4O⋯O11	0.84	1.99	2.790 (2)	160
O6—H6O⋯O2ⁱⁱ	0.84	1.65	2.485 (2)	175
O9—H9O⋯O1Wⁱⁱ	0.84	2.25	3.077 (3)	169
O10—H10O⋯O5	0.84	2.05	2.848 (2)	158
O14—H14O⋯O7ⁱⁱⁱ	0.84	1.73	2.552 (2)	164
O15—H15O⋯O1	0.84	2.05	2.869 (2)	166
O16—H16O⋯O12ⁱⁱⁱ	0.84	2.27	3.054 (3)	156
O18—H18O⋯O1ⁱⁱ	0.84	1.77	2.588 (2)	165
C3—H3⋯O15	1.00	2.55	3.503 (3)	158
C7—H7⋯O13^iv	1.00	2.52	3.396 (3)	146
C13—H13A⋯O1W^v	0.99	2.51	3.419 (4)	152
C16—H16B⋯O3^vi	0.98	2.46	3.378 (3)	155
C19—H19A⋯O3^vi	0.99	2.38	3.275 (3)	150
C19—H19B⋯O9^vi	0.99	2.37	3.294 (3)	155
C23—H23A⋯O17^vii	0.99	2.47	3.420 (3)	161
C25—H25A⋯O13	0.99	2.46	3.419 (3)	164
C26—H26A⋯O9^viii	0.98	2.56	3.482 (4)	157
C27—H27B⋯O18ⁱ	0.99	2.49	3.180 (3)	126
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (v) x-1, y, z+1; (vi) x, y, z+1; (vii) x+1, y, z-1; (viii) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Data collection: X-AREA (Stoe & Cie, 2009 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97 and PLATON .

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015479/nr2003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015479/nr2003Isup2.hkl

checkCIF report

Comment top

Our interest in the determination of the structure of the title compound is due to recent advances in organic non-linear optical (NLO) materials on account of their widespread potential industrial applications (Dega-Szafran et al., 2008; Bosshard et al., 1995). The majority of promising compounds constitute dipolar donor-π-acceptor molecules and these must be arranged non-centrosymmetrically to afford macroscopic structures capable of showing bulk quadratic NLO effects, such as frequency doubling [second-harmonic generation, SHG] (Coe et al., 2005). In particular, molecule-based NLO materials offer ultrafast response times, lower dielectric constants, better processability characteristics and enhanced nonresonant NLO responses relative to the traditional inorganic crystals. Previous work has shown that an inherent relationship exists between the structure of title material and its observed properties, although the SHG output was found to be rather weak when compared to KDP or urea.

The molecular structure of the title compound is illustrated in Fig. 1. The asymmetric unit is composed of two tetraethylammonium cations, two hydrogen L-tartrate anions, a molecule of L-tartaric acid and a water molecule. The various moieties are linked by O—H···O hydrogen bonds (Table 1).

In the crystal two-dimensional networks (Fig. 2) are formed via O—H···O hydrogen bonds and C—H···O interactions (Table 1) involving the water molecule, the hydrogen L-tartrate anions and the L-tartaric acid molecules. These layers stack along [001] are separated by tetraethylammonium cations, which are also involved in C—H···O interactions with the anions and the L-tartaric acid and water molecules (Fig. 3 and Table 1). This arrangement is similar to that in the crystal structure of Tetra-ethylammonium hydrogen L-tartrate dihydrate, which has been reported on previously (Rahman et al., 2008).

Related literature top

For potential industrial applications of non-linear optical (NLO) materials, see: Dega-Szafran et al. (2008); Bosshard et al. (1995). For an example of a structure showing bulk quadratic NLO effects, see: Coe et al. (2005). For the crystal structure of tetraethylammonium hydrogen L-tartrate dihydrate, see: Rahman et al. (2008).

Experimental top

The title compound was synthesized using tetraethyl ammonium and L-tartaric acid in an equimolar ratio. The measured quantity of L-tartaric was dissolved in double distilled water until a saturated solution was obtained. Tetraethylammonium hydroxide (20% water) was then added slowly drop wise to the aqueous solution of L-tartaric acid. The mixture was stirred well at RT until a homogeneous solution was obtained. It was then stirred for 4 hrs at 350 K (oil bath) and then cooled to RT. The cooled solution was then filtered and the filtrate covered using a thick parafilm sheet, in order to control the evaporation rate at RT in a constant temperature bath. Good quality single crystals of title compound were obtained after 1 month.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view along the c axis of the crystal packing of the title compound, with the O—H···O hydrogen bonds shown as dashed cyan lines (see Table 1 for details; C-bound H-atoms and the Tetra-ethylammonium cations have been omitted for clarity).
	Fig. 3. A view along the a axis of the crystal packing of the title compound, showing both the O—H···O hydrogen bonds and the C—H···O interactions as dashed cyan lines (see Table 1 for details; C-bound H-atoms not involved in the C—H···O interactions have been omitted for clarity).

Bis(tetraethylammonium) bis(hydrogen L-tartrate) L-tartaric acid monohydrate top

Crystal data top

2C₈H₂₀N⁺·2C₄H₅O₆⁻·C₄H₆O₆·H₂O	F(000) = 784
M_r = 726.76	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 16128 reflections
a = 7.5725 (4) Å	θ = 1.5–25.7°
b = 27.7907 (13) Å	µ = 0.11 mm⁻¹
c = 8.7620 (6) Å	T = 173 K
β = 99.884 (5)°	Rod, colourless
V = 1816.55 (18) Å³	0.45 × 0.32 × 0.25 mm
Z = 2

Data collection top

Stoe IPDS 2 diffractometer	3116 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.072
Graphite monochromator	θ_max = 25.7°, θ_min = 1.5°
ϕ and ω scans	h = −9→9
20250 measured reflections	k = −33→33
3502 independent reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0336P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3502 reflections	Δρ_max = 0.17 e Å⁻³
469 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (10)

Crystal data top

2C₈H₂₀N⁺·2C₄H₅O₆⁻·C₄H₆O₆·H₂O	V = 1816.55 (18) Å³
M_r = 726.76	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.5725 (4) Å	µ = 0.11 mm⁻¹
b = 27.7907 (13) Å	T = 173 K
c = 8.7620 (6) Å	0.45 × 0.32 × 0.25 mm
β = 99.884 (5)°

Data collection top

Stoe IPDS 2 diffractometer	3116 reflections with I > 2σ(I)
20250 measured reflections	R_int = 0.072
3502 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
3502 reflections	Δρ_min = −0.20 e Å⁻³
469 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. The water H-atoms were located in difference electron-density maps and refined with O—H distance restraints of 0.84 (2) Å, and U_iso(H) = 1.5 × U_eq(O). The OH and C-bound H-atoms were included in calculated positions and treated as riding atoms: O—H = 0.84 Å, C—H = 1.0, 0.99 and 0.98Å for CH, CH₂, and CH₃ H-atoms, respectively, with U_iso(H) = k × U_eq(C or O), where k = 1.5 for OH and CH₃ H-atoms, and k = 1.2 for all other H-atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.8300 (2)	0.28144 (6)	0.5505 (2)	0.0269 (4)
O2	0.9206 (2)	0.23806 (7)	0.3631 (2)	0.0337 (5)
O3	0.6051 (2)	0.19685 (6)	0.27276 (19)	0.0251 (4)
H3O	0.7027	0.1818	0.2838	0.038*
O4	0.6211 (2)	0.17495 (6)	0.5971 (2)	0.0255 (4)
H4O	0.5879	0.1502	0.5453	0.038*
O5	0.2590 (2)	0.16831 (6)	0.4724 (2)	0.0267 (4)
O6	0.2518 (2)	0.24709 (6)	0.4224 (2)	0.0314 (4)
H6O	0.1406	0.2424	0.4023	0.047*
C1	0.8051 (3)	0.25215 (8)	0.4390 (3)	0.0199 (5)
C2	0.6153 (3)	0.23299 (9)	0.3861 (3)	0.0194 (5)
H2	0.5407	0.2606	0.3384	0.023*
C3	0.5318 (3)	0.21533 (8)	0.5243 (3)	0.0188 (5)
H3	0.5441	0.2419	0.6022	0.023*
C4	0.3328 (3)	0.20709 (9)	0.4694 (3)	0.0199 (5)
O7	0.0108 (2)	−0.03787 (6)	0.4425 (2)	0.0231 (4)
O8	−0.1122 (2)	0.02964 (6)	0.3374 (2)	0.0342 (5)
O9	0.1768 (2)	0.05712 (6)	0.2309 (2)	0.0256 (4)
H9O	0.0916	0.0746	0.2475	0.038*
O10	0.2592 (2)	0.07004 (6)	0.5647 (2)	0.0267 (4)
H10O	0.2803	0.0963	0.5242	0.040*
O11	0.5811 (3)	0.08248 (6)	0.4720 (3)	0.0391 (5)
O12	0.5832 (2)	0.00705 (6)	0.3876 (3)	0.0342 (5)
H12O	0.6874	0.0144	0.3751	0.051*
C5	0.0186 (3)	0.00157 (8)	0.3764 (3)	0.0182 (5)
C6	0.1979 (3)	0.01833 (8)	0.3365 (3)	0.0187 (5)
H6	0.2516	−0.0092	0.2870	0.022*
C7	0.3276 (3)	0.03191 (8)	0.4858 (3)	0.0204 (5)
H7	0.3407	0.0032	0.5556	0.025*
C8	0.5108 (3)	0.04356 (9)	0.4477 (3)	0.0239 (6)
O13	0.5634 (2)	0.41652 (7)	0.4106 (2)	0.0291 (4)
O14	0.7719 (2)	0.39729 (6)	0.6164 (2)	0.0266 (4)
H14O	0.8314	0.4188	0.5809	0.040*
O15	0.5743 (2)	0.32771 (6)	0.70813 (19)	0.0222 (4)
H15O	0.6599	0.3135	0.6779	0.033*
O16	0.4137 (3)	0.41234 (7)	0.7886 (2)	0.0358 (5)
H16O	0.4190	0.4418	0.7683	0.054*
O17	0.1584 (2)	0.34469 (7)	0.80706 (19)	0.0307 (4)
O18	0.1062 (2)	0.33623 (6)	0.54942 (19)	0.0244 (4)
H18O	0.0235	0.3180	0.5672	0.037*
C9	0.6136 (3)	0.39366 (8)	0.5289 (3)	0.0203 (5)
C10	0.4884 (3)	0.35829 (8)	0.5892 (3)	0.0189 (5)
H10	0.4295	0.3379	0.5009	0.023*
C11	0.3428 (3)	0.38693 (8)	0.6524 (3)	0.0199 (5)
H11	0.2910	0.4109	0.5719	0.024*
C12	0.1928 (3)	0.35356 (8)	0.6810 (3)	0.0178 (5)
N1	0.1498 (3)	0.18045 (7)	0.9192 (2)	0.0216 (4)
C13	0.0283 (4)	0.20263 (11)	1.0211 (3)	0.0311 (6)
H13A	−0.0298	0.1763	1.0704	0.037*
H13B	0.1034	0.2210	1.1049	0.037*
C14	−0.1157 (4)	0.23552 (13)	0.9396 (4)	0.0462 (8)
H14C	−0.1862	0.2482	1.0146	0.069*
H14B	−0.1944	0.2175	0.8589	0.069*
H14A	−0.0603	0.2623	0.8923	0.069*
C15	0.2489 (4)	0.21890 (9)	0.8449 (3)	0.0262 (6)
H15A	0.3226	0.2030	0.7765	0.031*
H15B	0.1597	0.2393	0.7788	0.031*
C16	0.3694 (4)	0.25100 (10)	0.9570 (3)	0.0343 (6)
H16C	0.4319	0.2736	0.8991	0.052*
H16B	0.4574	0.2312	1.0245	0.052*
H16A	0.2969	0.2689	1.0202	0.052*
C17	0.0424 (4)	0.15163 (10)	0.7866 (3)	0.0304 (6)
H17A	−0.0401	0.1739	0.7209	0.036*
H17B	0.1265	0.1386	0.7221	0.036*
C18	−0.0661 (4)	0.11051 (11)	0.8345 (4)	0.0457 (8)
H18C	−0.1327	0.0949	0.7419	0.069*
H18B	−0.1505	0.1228	0.8982	0.069*
H18A	0.0144	0.0871	0.8944	0.069*
C19	0.2818 (4)	0.14840 (10)	1.0239 (3)	0.0301 (6)
H19A	0.3407	0.1679	1.1129	0.036*
H19B	0.2134	0.1226	1.0655	0.036*
C20	0.4256 (4)	0.12536 (12)	0.9483 (4)	0.0461 (8)
H20A	0.5018	0.1505	0.9153	0.069*
H20B	0.3695	0.1067	0.8579	0.069*
H20C	0.4987	0.1040	1.0226	0.069*
N2	0.9558 (3)	0.42249 (8)	0.1066 (2)	0.0252 (5)
C21	0.8261 (4)	0.38890 (10)	0.0071 (3)	0.0318 (6)
H21A	0.7490	0.4082	−0.0730	0.038*
H21B	0.8958	0.3664	−0.0470	0.038*
C22	0.7068 (5)	0.35979 (12)	0.0949 (4)	0.0492 (8)
H22C	0.6219	0.3409	0.0214	0.074*
H22B	0.6407	0.3816	0.1526	0.074*
H22A	0.7809	0.3380	0.1673	0.074*
C23	1.0666 (4)	0.44630 (11)	−0.0008 (3)	0.0335 (6)
H23A	1.1215	0.4208	−0.0562	0.040*
H23B	0.9852	0.4651	−0.0793	0.040*
C24	1.2140 (5)	0.47937 (12)	0.0767 (5)	0.0510 (9)
H24C	1.2734	0.4943	−0.0022	0.076*
H24B	1.3017	0.4607	0.1484	0.076*
H24A	1.1622	0.5044	0.1342	0.076*
C25	0.8563 (4)	0.45954 (9)	0.1868 (3)	0.0282 (6)
H25A	0.7907	0.4426	0.2591	0.034*
H25B	0.9455	0.4808	0.2494	0.034*
C26	0.7250 (4)	0.49045 (10)	0.0805 (4)	0.0374 (7)
H26C	0.6702	0.5138	0.1421	0.056*
H26B	0.6315	0.4700	0.0222	0.056*
H26A	0.7881	0.5076	0.0083	0.056*
C27	1.0750 (4)	0.39489 (11)	0.2343 (3)	0.0377 (7)
H27A	1.1613	0.4176	0.2936	0.045*
H27B	0.9995	0.3818	0.3062	0.045*
C28	1.1785 (5)	0.35398 (12)	0.1782 (3)	0.0440 (8)
H28C	1.2500	0.3378	0.2673	0.066*
H28B	1.2580	0.3666	0.1106	0.066*
H28A	1.0945	0.3309	0.1204	0.066*
O1W	0.9034 (3)	0.13191 (8)	0.3037 (3)	0.0361 (5)
H1WA	0.873 (5)	0.1078 (16)	0.348 (5)	0.060 (12)*
H1WB	0.985 (6)	0.1475 (16)	0.370 (5)	0.069 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0211 (9)	0.0305 (9)	0.0308 (10)	−0.0086 (8)	0.0089 (8)	−0.0131 (8)
O2	0.0154 (9)	0.0414 (11)	0.0452 (12)	−0.0024 (8)	0.0077 (8)	−0.0189 (9)
O3	0.0180 (9)	0.0331 (10)	0.0232 (9)	−0.0021 (7)	0.0009 (7)	−0.0088 (8)
O4	0.0278 (10)	0.0189 (8)	0.0260 (9)	−0.0017 (8)	−0.0057 (8)	0.0017 (7)
O5	0.0242 (10)	0.0206 (9)	0.0354 (10)	−0.0068 (8)	0.0060 (8)	−0.0020 (8)
O6	0.0118 (9)	0.0243 (9)	0.0581 (13)	−0.0007 (8)	0.0065 (9)	0.0040 (9)
C1	0.0165 (12)	0.0195 (11)	0.0235 (12)	0.0017 (10)	0.0029 (10)	0.0003 (10)
C2	0.0140 (12)	0.0211 (12)	0.0222 (12)	0.0026 (10)	0.0004 (10)	−0.0013 (10)
C3	0.0174 (12)	0.0149 (11)	0.0238 (12)	−0.0002 (10)	0.0025 (10)	−0.0017 (10)
C4	0.0205 (12)	0.0186 (12)	0.0219 (12)	−0.0012 (11)	0.0074 (10)	−0.0040 (10)
O7	0.0187 (9)	0.0225 (9)	0.0298 (9)	0.0009 (7)	0.0090 (7)	0.0041 (7)
O8	0.0159 (9)	0.0255 (9)	0.0626 (14)	0.0045 (8)	0.0109 (9)	0.0130 (9)
O9	0.0228 (10)	0.0293 (9)	0.0260 (9)	0.0013 (8)	0.0082 (8)	0.0094 (7)
O10	0.0301 (10)	0.0242 (9)	0.0279 (9)	0.0003 (8)	0.0115 (8)	−0.0056 (8)
O11	0.0245 (10)	0.0228 (10)	0.0701 (15)	−0.0060 (8)	0.0082 (10)	−0.0118 (9)
O12	0.0177 (10)	0.0198 (9)	0.0682 (14)	−0.0026 (8)	0.0163 (9)	−0.0094 (9)
C5	0.0158 (12)	0.0180 (12)	0.0207 (12)	−0.0014 (10)	0.0030 (9)	−0.0023 (10)
C6	0.0169 (13)	0.0173 (11)	0.0229 (12)	0.0022 (10)	0.0065 (10)	−0.0003 (10)
C7	0.0191 (13)	0.0185 (11)	0.0234 (13)	0.0022 (9)	0.0027 (10)	−0.0011 (9)
C8	0.0158 (12)	0.0194 (13)	0.0347 (15)	−0.0002 (10)	−0.0009 (11)	−0.0013 (11)
O13	0.0290 (10)	0.0348 (10)	0.0243 (10)	−0.0056 (8)	0.0066 (8)	0.0061 (8)
O14	0.0192 (9)	0.0259 (9)	0.0342 (10)	−0.0075 (7)	0.0032 (8)	0.0052 (8)
O15	0.0215 (9)	0.0196 (8)	0.0266 (9)	0.0038 (7)	0.0076 (7)	0.0033 (7)
O16	0.0255 (10)	0.0365 (10)	0.0443 (11)	−0.0035 (9)	0.0033 (9)	−0.0258 (9)
O17	0.0320 (10)	0.0435 (11)	0.0180 (9)	−0.0012 (9)	0.0083 (7)	0.0029 (8)
O18	0.0211 (9)	0.0311 (9)	0.0218 (9)	−0.0121 (7)	0.0063 (7)	−0.0029 (7)
C9	0.0201 (13)	0.0194 (11)	0.0221 (13)	−0.0008 (10)	0.0056 (10)	−0.0045 (10)
C10	0.0175 (12)	0.0181 (11)	0.0209 (12)	−0.0016 (10)	0.0026 (10)	−0.0042 (9)
C11	0.0205 (13)	0.0163 (11)	0.0224 (12)	−0.0006 (10)	0.0024 (10)	−0.0031 (9)
C12	0.0155 (12)	0.0197 (11)	0.0182 (12)	0.0048 (10)	0.0031 (9)	−0.0012 (9)
N1	0.0229 (11)	0.0232 (10)	0.0184 (10)	−0.0039 (9)	0.0031 (8)	0.0020 (8)
C13	0.0299 (14)	0.0409 (15)	0.0245 (13)	−0.0037 (13)	0.0102 (11)	−0.0016 (12)
C14	0.0382 (18)	0.0535 (19)	0.0481 (19)	0.0074 (16)	0.0106 (15)	−0.0084 (16)
C15	0.0286 (14)	0.0263 (13)	0.0241 (13)	−0.0029 (11)	0.0056 (11)	0.0057 (10)
C16	0.0345 (16)	0.0290 (14)	0.0396 (16)	−0.0059 (12)	0.0062 (13)	0.0088 (12)
C17	0.0288 (15)	0.0314 (13)	0.0280 (14)	−0.0014 (12)	−0.0036 (11)	−0.0045 (11)
C18	0.0387 (19)	0.0378 (17)	0.055 (2)	−0.0119 (14)	−0.0069 (16)	0.0025 (15)
C19	0.0285 (15)	0.0287 (13)	0.0297 (14)	−0.0048 (12)	−0.0043 (11)	0.0093 (11)
C20	0.0393 (18)	0.0340 (16)	0.062 (2)	0.0103 (14)	0.0003 (16)	0.0008 (15)
N2	0.0307 (12)	0.0308 (11)	0.0137 (9)	0.0042 (10)	0.0030 (9)	0.0012 (9)
C21	0.0364 (16)	0.0384 (15)	0.0208 (13)	0.0009 (13)	0.0051 (12)	−0.0062 (12)
C22	0.061 (2)	0.0441 (17)	0.0474 (19)	−0.0139 (16)	0.0234 (17)	−0.0142 (15)
C23	0.0292 (16)	0.0456 (16)	0.0279 (14)	0.0083 (13)	0.0110 (12)	0.0082 (12)
C24	0.042 (2)	0.0465 (18)	0.069 (2)	−0.0022 (16)	0.0227 (18)	−0.0028 (17)
C25	0.0346 (16)	0.0313 (14)	0.0204 (13)	0.0024 (12)	0.0096 (11)	−0.0024 (11)
C26	0.0419 (18)	0.0365 (15)	0.0369 (16)	0.0082 (13)	0.0154 (14)	0.0008 (13)
C27	0.0509 (19)	0.0422 (15)	0.0169 (13)	0.0139 (14)	−0.0031 (12)	0.0046 (12)
C28	0.054 (2)	0.0522 (19)	0.0235 (14)	0.0226 (17)	0.0008 (13)	0.0018 (14)
O1W	0.0376 (13)	0.0253 (10)	0.0444 (13)	−0.0045 (9)	0.0041 (10)	0.0029 (10)

Geometric parameters (Å, º) top

O1—C1	1.261 (3)	C14—H14B	0.9800
O2—C1	1.249 (3)	C14—H14A	0.9800
O3—C2	1.405 (3)	C15—C16	1.512 (4)
O3—H3O	0.8400	C15—H15A	0.9900
O4—C3	1.406 (3)	C15—H15B	0.9900
O4—H4O	0.8400	C16—H16C	0.9800
O5—C4	1.216 (3)	C16—H16B	0.9800
O6—C4	1.302 (3)	C16—H16A	0.9800
O6—H6O	0.8400	C17—C18	1.508 (4)
C1—C2	1.528 (3)	C17—H17A	0.9900
C2—C3	1.539 (3)	C17—H17B	0.9900
C2—H2	1.0000	C18—H18C	0.9800
C3—C4	1.519 (3)	C18—H18B	0.9800
C3—H3	1.0000	C18—H18A	0.9800
O7—C5	1.246 (3)	C19—C20	1.511 (4)
O8—C5	1.261 (3)	C19—H19A	0.9900
O9—C6	1.411 (3)	C19—H19B	0.9900
O9—H9O	0.8400	C20—H20A	0.9800
O10—C7	1.412 (3)	C20—H20B	0.9800
O10—H10O	0.8400	C20—H20C	0.9800
O11—C8	1.208 (3)	N2—C23	1.516 (3)
O12—C8	1.306 (3)	N2—C25	1.517 (3)
O12—H12O	0.8400	N2—C21	1.517 (3)
C5—C6	1.531 (3)	N2—C27	1.519 (3)
C6—C7	1.541 (3)	C21—C22	1.517 (4)
C6—H6	1.0000	C21—H21A	0.9900
C7—C8	1.517 (4)	C21—H21B	0.9900
C7—H7	1.0000	C22—H22C	0.9800
O13—C9	1.219 (3)	C22—H22B	0.9800
O14—C9	1.311 (3)	C22—H22A	0.9800
O14—H14O	0.8400	C23—C24	1.513 (5)
O15—C10	1.413 (3)	C23—H23A	0.9900
O15—H15O	0.8400	C23—H23B	0.9900
O16—C11	1.411 (3)	C24—H24C	0.9800
O16—H16O	0.8400	C24—H24B	0.9800
O17—C12	1.204 (3)	C24—H24A	0.9800
O18—C12	1.316 (3)	C25—C26	1.508 (4)
O18—H18O	0.8400	C25—H25A	0.9900
C9—C10	1.522 (3)	C25—H25B	0.9900
C10—C11	1.538 (3)	C26—H26C	0.9800
C10—H10	1.0000	C26—H26B	0.9800
C11—C12	1.520 (3)	C26—H26A	0.9800
C11—H11	1.0000	C27—C28	1.510 (4)
N1—C15	1.515 (3)	C27—H27A	0.9900
N1—C13	1.519 (3)	C27—H27B	0.9900
N1—C19	1.523 (3)	C28—H28C	0.9800
N1—C17	1.526 (3)	C28—H28B	0.9800
C13—C14	1.506 (4)	C28—H28A	0.9800
C13—H13A	0.9900	O1W—H1WA	0.83 (4)
C13—H13B	0.9900	O1W—H1WB	0.88 (5)
C14—H14C	0.9800

C2—O3—H3O	109.5	H15A—C15—H15B	107.5
C3—O4—H4O	109.5	C15—C16—H16C	109.5
C4—O6—H6O	109.5	C15—C16—H16B	109.5
O2—C1—O1	126.1 (2)	H16C—C16—H16B	109.5
O2—C1—C2	115.9 (2)	C15—C16—H16A	109.5
O1—C1—C2	117.9 (2)	H16C—C16—H16A	109.5
O3—C2—C1	113.48 (19)	H16B—C16—H16A	109.5
O3—C2—C3	110.34 (19)	C18—C17—N1	115.5 (2)
C1—C2—C3	111.38 (19)	C18—C17—H17A	108.4
O3—C2—H2	107.1	N1—C17—H17A	108.4
C1—C2—H2	107.1	C18—C17—H17B	108.4
C3—C2—H2	107.1	N1—C17—H17B	108.4
O4—C3—C4	113.41 (19)	H17A—C17—H17B	107.5
O4—C3—C2	112.41 (19)	C17—C18—H18C	109.5
C4—C3—C2	108.57 (19)	C17—C18—H18B	109.5
O4—C3—H3	107.4	H18C—C18—H18B	109.5
C4—C3—H3	107.4	C17—C18—H18A	109.5
C2—C3—H3	107.4	H18C—C18—H18A	109.5
O5—C4—O6	124.8 (2)	H18B—C18—H18A	109.5
O5—C4—C3	124.2 (2)	C20—C19—N1	115.5 (2)
O6—C4—C3	111.1 (2)	C20—C19—H19A	108.4
C6—O9—H9O	109.5	N1—C19—H19A	108.4
C7—O10—H10O	109.5	C20—C19—H19B	108.4
C8—O12—H12O	109.5	N1—C19—H19B	108.4
O7—C5—O8	124.9 (2)	H19A—C19—H19B	107.5
O7—C5—C6	119.2 (2)	C19—C20—H20A	109.5
O8—C5—C6	115.8 (2)	C19—C20—H20B	109.5
O9—C6—C5	112.13 (19)	H20A—C20—H20B	109.5
O9—C6—C7	110.67 (19)	C19—C20—H20C	109.5
C5—C6—C7	109.97 (19)	H20A—C20—H20C	109.5
O9—C6—H6	108.0	H20B—C20—H20C	109.5
C5—C6—H6	108.0	C23—N2—C25	111.3 (2)
C7—C6—H6	108.0	C23—N2—C21	106.50 (19)
O10—C7—C8	111.96 (19)	C25—N2—C21	111.1 (2)
O10—C7—C6	111.45 (19)	C23—N2—C27	110.8 (2)
C8—C7—C6	109.8 (2)	C25—N2—C27	106.34 (19)
O10—C7—H7	107.8	C21—N2—C27	110.9 (2)
C8—C7—H7	107.8	C22—C21—N2	114.8 (2)
C6—C7—H7	107.8	C22—C21—H21A	108.6
O11—C8—O12	124.3 (2)	N2—C21—H21A	108.6
O11—C8—C7	123.0 (2)	C22—C21—H21B	108.6
O12—C8—C7	112.7 (2)	N2—C21—H21B	108.6
C9—O14—H14O	109.5	H21A—C21—H21B	107.5
C10—O15—H15O	109.5	C21—C22—H22C	109.5
C11—O16—H16O	109.5	C21—C22—H22B	109.5
C12—O18—H18O	109.5	H22C—C22—H22B	109.5
O13—C9—O14	125.2 (2)	C21—C22—H22A	109.5
O13—C9—C10	120.7 (2)	H22C—C22—H22A	109.5
O14—C9—C10	114.1 (2)	H22B—C22—H22A	109.5
O15—C10—C9	114.16 (19)	C24—C23—N2	115.5 (2)
O15—C10—C11	108.28 (18)	C24—C23—H23A	108.4
C9—C10—C11	108.58 (18)	N2—C23—H23A	108.4
O15—C10—H10	108.6	C24—C23—H23B	108.4
C9—C10—H10	108.6	N2—C23—H23B	108.4
C11—C10—H10	108.6	H23A—C23—H23B	107.5
O16—C11—C12	110.6 (2)	C23—C24—H24C	109.5
O16—C11—C10	111.75 (19)	C23—C24—H24B	109.5
C12—C11—C10	110.23 (18)	H24C—C24—H24B	109.5
O16—C11—H11	108.0	C23—C24—H24A	109.5
C12—C11—H11	108.0	H24C—C24—H24A	109.5
C10—C11—H11	108.0	H24B—C24—H24A	109.5
O17—C12—O18	125.1 (2)	C26—C25—N2	115.3 (2)
O17—C12—C11	124.2 (2)	C26—C25—H25A	108.4
O18—C12—C11	110.68 (19)	N2—C25—H25A	108.4
C15—N1—C13	111.18 (19)	C26—C25—H25B	108.4
C15—N1—C19	110.43 (19)	N2—C25—H25B	108.4
C13—N1—C19	106.50 (19)	H25A—C25—H25B	107.5
C15—N1—C17	106.36 (18)	C25—C26—H26C	109.5
C13—N1—C17	111.3 (2)	C25—C26—H26B	109.5
C19—N1—C17	111.15 (19)	H26C—C26—H26B	109.5
C14—C13—N1	115.5 (2)	C25—C26—H26A	109.5
C14—C13—H13A	108.4	H26C—C26—H26A	109.5
N1—C13—H13A	108.4	H26B—C26—H26A	109.5
C14—C13—H13B	108.4	C28—C27—N2	114.6 (2)
N1—C13—H13B	108.4	C28—C27—H27A	108.6
H13A—C13—H13B	107.5	N2—C27—H27A	108.6
C13—C14—H14C	109.5	C28—C27—H27B	108.6
C13—C14—H14B	109.5	N2—C27—H27B	108.6
H14C—C14—H14B	109.5	H27A—C27—H27B	107.6
C13—C14—H14A	109.5	C27—C28—H28C	109.5
H14C—C14—H14A	109.5	C27—C28—H28B	109.5
H14B—C14—H14A	109.5	H28C—C28—H28B	109.5
C16—C15—N1	115.1 (2)	C27—C28—H28A	109.5
C16—C15—H15A	108.5	H28C—C28—H28A	109.5
N1—C15—H15A	108.5	H28B—C28—H28A	109.5
C16—C15—H15B	108.5	H1WA—O1W—H1WB	108 (4)
N1—C15—H15B	108.5

O2—C1—C2—O3	8.5 (3)	O15—C10—C11—C12	−67.9 (2)
O1—C1—C2—O3	−173.5 (2)	C9—C10—C11—C12	167.62 (19)
O2—C1—C2—C3	133.7 (2)	O16—C11—C12—O17	−10.4 (3)
O1—C1—C2—C3	−48.3 (3)	C10—C11—C12—O17	113.7 (3)
O3—C2—C3—O4	61.1 (2)	O16—C11—C12—O18	169.10 (19)
C1—C2—C3—O4	−65.8 (2)	C10—C11—C12—O18	−66.8 (2)
O3—C2—C3—C4	−65.2 (2)	C15—N1—C13—C14	60.4 (3)
C1—C2—C3—C4	167.88 (18)	C19—N1—C13—C14	−179.2 (2)
O4—C3—C4—O5	−7.3 (3)	C17—N1—C13—C14	−57.9 (3)
C2—C3—C4—O5	118.4 (2)	C13—N1—C15—C16	60.4 (3)
O4—C3—C4—O6	171.3 (2)	C19—N1—C15—C16	−57.6 (3)
C2—C3—C4—O6	−63.0 (2)	C17—N1—C15—C16	−178.3 (2)
O7—C5—C6—O9	165.8 (2)	C15—N1—C17—C18	179.2 (2)
O8—C5—C6—O9	−13.8 (3)	C13—N1—C17—C18	−59.5 (3)
O7—C5—C6—C7	−70.6 (3)	C19—N1—C17—C18	59.0 (3)
O8—C5—C6—C7	109.8 (2)	C15—N1—C19—C20	−54.8 (3)
O9—C6—C7—O10	63.3 (2)	C13—N1—C19—C20	−175.6 (2)
C5—C6—C7—O10	−61.1 (2)	C17—N1—C19—C20	63.0 (3)
O9—C6—C7—C8	−61.4 (2)	C23—N2—C21—C22	177.6 (3)
C5—C6—C7—C8	174.21 (18)	C25—N2—C21—C22	−61.1 (3)
O10—C7—C8—O11	−5.5 (4)	C27—N2—C21—C22	57.0 (3)
C6—C7—C8—O11	118.9 (3)	C25—N2—C23—C24	62.4 (3)
O10—C7—C8—O12	174.0 (2)	C21—N2—C23—C24	−176.4 (2)
C6—C7—C8—O12	−61.6 (3)	C27—N2—C23—C24	−55.7 (3)
O13—C9—C10—O15	168.0 (2)	C23—N2—C25—C26	60.9 (3)
O14—C9—C10—O15	−13.4 (3)	C21—N2—C25—C26	−57.6 (3)
O13—C9—C10—C11	−71.1 (3)	C27—N2—C25—C26	−178.4 (2)
O14—C9—C10—C11	107.5 (2)	C23—N2—C27—C28	−62.3 (3)
O15—C10—C11—O16	55.6 (2)	C25—N2—C27—C28	176.6 (3)
C9—C10—C11—O16	−68.9 (2)	C21—N2—C27—C28	55.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O2	0.89 (5)	2.56 (4)	2.995 (3)	111 (3)
O1W—H1WB···O5ⁱ	0.89 (5)	2.19 (5)	3.015 (3)	155 (4)
O3—H3O···O1W	0.84	2.04	2.868 (3)	167
O3—H3O···O2	0.84	2.29	2.645 (2)	106
O4—H4O···O5	0.84	2.51	2.778 (2)	100
O4—H4O···O11	0.84	1.99	2.790 (2)	160
O6—H6O···O2ⁱⁱ	0.84	1.65	2.485 (2)	175
O9—H9O···O1Wⁱⁱ	0.84	2.25	3.077 (3)	169
O9—H9O···O8	0.84	2.23	2.635 (2)	110
O10—H10O···O5	0.84	2.05	2.848 (2)	158
O10—H10O···O11	0.84	2.43	2.720 (3)	101
O14—H14O···O7ⁱⁱⁱ	0.84	1.73	2.552 (2)	164
O15—H15O···O1	0.84	2.05	2.869 (2)	166
O16—H16O···O12ⁱⁱⁱ	0.84	2.27	3.054 (3)	156
O18—H18O···O1ⁱⁱ	0.84	1.77	2.588 (2)	165
C2—H2···O6	1.00	2.45	2.852 (3)	103
C3—H3···O1	1.00	2.54	2.890 (3)	100
C3—H3···O15	1.00	2.55	3.503 (3)	158
C7—H7···O13^iv	1.00	2.52	3.396 (3)	146
C10—H10···O18	1.00	2.56	2.920 (3)	101
C13—H13A···O1W^v	0.99	2.51	3.419 (4)	152
C16—H16B···O3^vi	0.98	2.46	3.378 (3)	155
C19—H19A···O3^vi	0.99	2.38	3.275 (3)	150
C19—H19B···O9^vi	0.99	2.37	3.294 (3)	155
C23—H23A···O17^vii	0.99	2.47	3.420 (3)	161
C25—H25A···O13	0.99	2.46	3.419 (3)	164
C26—H26A···O9^viii	0.98	2.56	3.482 (4)	157
C27—H27B···O18ⁱ	0.99	2.49	3.180 (3)	126

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z+1; (v) x−1, y, z+1; (vi) x, y, z+1; (vii) x+1, y, z−1; (viii) −x+1, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	2C₈H₂₀N⁺·2C₄H₅O₆⁻·C₄H₆O₆·H₂O
M_r	726.76
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	7.5725 (4), 27.7907 (13), 8.7620 (6)
β (°)	99.884 (5)
V (Å³)	1816.55 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.32 × 0.25

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20250, 3502, 3116
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.064, 1.03
No. of reflections	3502
No. of parameters	469
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: X-AREA (Stoe & Cie, 2009), X-RED32 (Stoe & Cie, 2009), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O2	0.89 (5)	2.56 (4)	2.995 (3)	111 (3)
O1W—H1WB···O5ⁱ	0.89 (5)	2.19 (5)	3.015 (3)	155 (4)
O3—H3O···O1W	0.84	2.04	2.868 (3)	167
O4—H4O···O11	0.84	1.99	2.790 (2)	160
O6—H6O···O2ⁱⁱ	0.84	1.65	2.485 (2)	175
O9—H9O···O1Wⁱⁱ	0.84	2.25	3.077 (3)	169
O10—H10O···O5	0.84	2.05	2.848 (2)	158
O14—H14O···O7ⁱⁱⁱ	0.84	1.73	2.552 (2)	164
O15—H15O···O1	0.84	2.05	2.869 (2)	166
O16—H16O···O12ⁱⁱⁱ	0.84	2.27	3.054 (3)	156
O18—H18O···O1ⁱⁱ	0.84	1.77	2.588 (2)	165
C3—H3···O15	1.00	2.55	3.503 (3)	158
C7—H7···O13^iv	1.00	2.52	3.396 (3)	146
C13—H13A···O1W^v	0.99	2.51	3.419 (4)	152
C16—H16B···O3^vi	0.98	2.46	3.378 (3)	155
C19—H19A···O3^vi	0.99	2.38	3.275 (3)	150
C19—H19B···O9^vi	0.99	2.37	3.294 (3)	155
C23—H23A···O17^vii	0.99	2.47	3.420 (3)	161
C25—H25A···O13	0.99	2.46	3.419 (3)	164
C26—H26A···O9^viii	0.98	2.56	3.482 (4)	157
C27—H27B···O18ⁱ	0.99	2.49	3.180 (3)	126

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z+1; (v) x−1, y, z+1; (vi) x, y, z+1; (vii) x+1, y, z−1; (viii) −x+1, y+1/2, −z.

Acknowledgements

HSE thanks the staff of the XRD Application LAB., CSEM, Neuchâtel, for access to the X-ray diffraction equipment.

References

Bosshard, Ch., Sutter, K., Preâtre, Ph., Hulliger, J., Floérsheimer, M., Kaatz, P. & Guénter, P. (1995). Organic Nonlinear Optical Materials, Advances in Nonlinear Optics, Vol. 1. Amsterdam: Gordon and Breach. Google Scholar
Coe, B. J., Hall, J. J., Harris, J. A., Brunschwig, B. S., Coles, S. J. & Hursthouse, M. B. (2005). Acta Cryst. E61, o464–o467. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Dega-Szafran, Z., Dutkiewicz, G., Kosturkiewicz, Z. & Szafran, M. (2008). J. Mol. Struct. 889, 286–296. CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rahman, M. B. A., Jumbri, K., Sirat, K., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o2343. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie. (2009). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar

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Volume 67| Part 6| June 2011| Pages o1315-o1316

doi:10.1107/S1600536811015479

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(tetra­ethyl­ammonium) bis­­(hydrogen L-tartrate) L-tartaric acid monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Bis(tetraethylammonium) bis(hydrogen L-tartrate) L-tartaric acid monohydrate