Tetra-ethyl-ammonium l-tartarate dihydrate.

In the crystal structure of the title compound, C(8)H(20)N(+)·C(4)H(5)O(6) (-)·2H(2)O, the ions and water mol-ecules 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 = 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

Δρmax = 0.29 e Å−3

Δρmin = −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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H20N+·C4H5O6–·2H2O	F000 = 344
Mr = 315.36	Dx = 1.318 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4555 reflections
a = 7.4074 (1) Å	θ = 2.6–33.5º
b = 13.8989 (2) Å	µ = 0.11 mm−1
c = 8.0546 (1) Å	T = 100.0 (1) K
β = 106.553 (1)º	Block, colourless
V = 794.891 (19) Å3	0.47 × 0.45 × 0.17 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	3579 independent reflections
Radiation source: fine-focus sealed tube	3240 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 100.0(1) K	θmax = 35.0º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→11
Tmin = 0.861, Tmax = 0.981	k = −22→17
10518 measured reflections	l = −12→12

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.0426P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3579 reflections	Δρmax = 0.29 e Å−3
218 parameters	Δρmin = −0.23 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.71436 (14)	0.19227 (7)	−0.03566 (13)	0.01818 (18)
O2	1.02013 (14)	0.23261 (7)	0.04449 (14)	0.0201 (2)
O3	0.61932 (14)	0.36818 (7)	−0.18764 (12)	0.01677 (18)
O4	0.68458 (16)	0.39108 (7)	0.17930 (13)	0.0190 (2)
C1	0.83853 (18)	0.25107 (9)	−0.01824 (15)	0.0138 (2)
C2	0.79871 (18)	0.35668 (9)	−0.06869 (15)	0.0134 (2)
H2A	0.8929	0.3785	−0.1246	0.016*
C3	0.81928 (18)	0.41837 (9)	0.09447 (16)	0.0144 (2)
H3A	0.9446	0.4064	0.1739	0.017*
C4	0.80699 (19)	0.52553 (9)	0.04614 (16)	0.0156 (2)
N1	0.61784 (16)	0.13577 (8)	0.44527 (13)	0.01415 (19)
C5	0.68066 (19)	0.05680 (10)	0.34333 (17)	0.0169 (2)
H5A	0.5698	0.0232	0.2745	0.020*
H5B	0.7406	0.0866	0.2638	0.020*
C6	0.8153 (2)	−0.01643 (11)	0.4516 (2)	0.0249 (3)
H6A	0.8474	−0.0632	0.3769	0.037*
H6B	0.7563	−0.0481	0.5285	0.037*
H6C	0.9275	0.0156	0.5181	0.037*
C7	0.78506 (19)	0.18803 (10)	0.56438 (16)	0.0174 (2)
H7A	0.7381	0.2382	0.6249	0.021*
H7B	0.8550	0.1428	0.6507	0.021*
C8	0.9195 (2)	0.23319 (12)	0.47596 (19)	0.0227 (3)
H8A	1.0203	0.2644	0.5609	0.034*
H8B	0.8532	0.2797	0.3926	0.034*
H8C	0.9703	0.1841	0.4183	0.034*
C9	0.50734 (19)	0.09482 (11)	0.56176 (16)	0.0186 (2)
H9A	0.5880	0.0505	0.6428	0.022*
H9B	0.4763	0.1471	0.6286	0.022*
C10	0.3270 (2)	0.04279 (11)	0.46895 (19)	0.0218 (3)
H10A	0.2674	0.0194	0.5523	0.033*
H10B	0.3558	−0.0104	0.4047	0.033*
H10C	0.2437	0.0864	0.3910	0.033*
C11	0.49727 (18)	0.20335 (10)	0.31067 (15)	0.0157 (2)
H11A	0.5737	0.2288	0.2411	0.019*
H11B	0.3959	0.1665	0.2344	0.019*
C12	0.4121 (2)	0.28706 (11)	0.38285 (18)	0.0205 (3)
H12A	0.3389	0.3259	0.2891	0.031*
H12B	0.5110	0.3253	0.4562	0.031*
H12C	0.3325	0.2630	0.4489	0.031*
O1W	0.30848 (16)	0.27561 (10)	0.84652 (15)	0.0243 (2)
O2W	0.69834 (18)	0.97603 (9)	0.95574 (16)	0.0252 (2)
O5	0.93673 (14)	0.55475 (7)	−0.01728 (15)	0.0218 (2)
O6	0.67739 (15)	0.57466 (8)	0.07043 (14)	0.0226 (2)
H1O2	1.043 (4)	0.161 (2)	0.045 (3)	0.045 (7)*
H1O3	0.534 (3)	0.3304 (19)	−0.159 (3)	0.036 (6)*
H1O4	0.590 (3)	0.422 (2)	0.122 (3)	0.033 (6)*
H1W1	0.260 (4)	0.306 (2)	0.911 (4)	0.055 (8)*
H2W1	0.316 (4)	0.216 (2)	0.884 (3)	0.043 (7)*
H1W2	0.818 (4)	0.9985 (19)	0.980 (3)	0.037 (6)*
H2W2	0.630 (4)	1.025 (2)	0.962 (3)	0.039 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0174 (4)	0.0115 (4)	0.0261 (4)	−0.0015 (3)	0.0070 (4)	0.0010 (4)
O2	0.0150 (4)	0.0121 (4)	0.0307 (5)	0.0009 (4)	0.0027 (4)	−0.0024 (4)
O3	0.0174 (4)	0.0135 (4)	0.0167 (4)	−0.0013 (3)	0.0006 (3)	0.0020 (3)
O4	0.0242 (5)	0.0155 (4)	0.0191 (4)	0.0013 (4)	0.0091 (4)	0.0022 (3)
C1	0.0164 (5)	0.0107 (5)	0.0146 (4)	0.0011 (4)	0.0050 (4)	−0.0005 (4)
C2	0.0151 (5)	0.0095 (5)	0.0156 (4)	−0.0007 (4)	0.0040 (4)	0.0005 (4)
C3	0.0161 (5)	0.0096 (5)	0.0162 (5)	0.0001 (4)	0.0024 (4)	−0.0005 (4)
C4	0.0164 (5)	0.0104 (5)	0.0180 (5)	−0.0001 (4)	0.0013 (4)	−0.0010 (4)
N1	0.0153 (5)	0.0138 (5)	0.0131 (4)	−0.0007 (4)	0.0037 (3)	0.0003 (3)
C5	0.0185 (5)	0.0134 (5)	0.0191 (5)	−0.0001 (5)	0.0057 (4)	−0.0026 (4)
C6	0.0232 (7)	0.0160 (6)	0.0349 (7)	0.0027 (5)	0.0071 (6)	0.0032 (5)
C7	0.0168 (5)	0.0175 (6)	0.0156 (5)	−0.0016 (5)	0.0007 (4)	−0.0013 (4)
C8	0.0191 (6)	0.0217 (7)	0.0256 (6)	−0.0052 (5)	0.0036 (5)	0.0012 (5)
C9	0.0200 (6)	0.0209 (6)	0.0162 (5)	−0.0018 (5)	0.0073 (4)	0.0025 (4)
C10	0.0196 (6)	0.0221 (7)	0.0254 (6)	−0.0029 (5)	0.0089 (5)	0.0024 (5)
C11	0.0171 (5)	0.0147 (5)	0.0140 (4)	0.0012 (4)	0.0024 (4)	0.0012 (4)
C12	0.0213 (6)	0.0161 (6)	0.0235 (6)	0.0025 (5)	0.0055 (5)	−0.0020 (5)
O1W	0.0200 (5)	0.0272 (6)	0.0262 (5)	−0.0003 (4)	0.0076 (4)	0.0019 (4)
O2W	0.0250 (6)	0.0191 (5)	0.0321 (5)	−0.0048 (4)	0.0094 (4)	−0.0044 (4)
O5	0.0187 (4)	0.0118 (4)	0.0361 (5)	−0.0022 (4)	0.0096 (4)	0.0006 (4)
O6	0.0245 (5)	0.0164 (5)	0.0286 (5)	0.0071 (4)	0.0102 (4)	0.0021 (4)

O1—C1	1.2084 (16)	C6—H6C	0.96
O2—C1	1.3203 (15)	C7—C8	1.516 (2)
O2—H1O2	1.01 (3)	C7—H7A	0.97
O3—C2	1.4085 (16)	C7—H7B	0.97
O3—H1O3	0.90 (3)	C8—H8A	0.96
O4—C3	1.4124 (17)	C8—H8B	0.96
O4—H1O4	0.84 (3)	C8—H8C	0.96
C1—C2	1.5292 (17)	C9—C10	1.516 (2)
C2—C3	1.5400 (17)	C9—H9A	0.97
C2—H2A	0.98	C9—H9B	0.97
C3—C4	1.5356 (18)	C10—H10A	0.96
C3—H3A	0.98	C10—H10B	0.96
C4—O6	1.2382 (17)	C10—H10C	0.96
C4—O5	1.2763 (17)	C11—C12	1.516 (2)
N1—C11	1.5178 (16)	C11—H11A	0.97
N1—C7	1.5183 (17)	C11—H11B	0.97
N1—C9	1.5205 (16)	C12—H12A	0.96
N1—C5	1.5209 (17)	C12—H12B	0.96
C5—C6	1.515 (2)	C12—H12C	0.96
C5—H5A	0.97	O1W—H1W1	0.83 (3)
C5—H5B	0.97	O1W—H2W1	0.88 (3)
C6—H6A	0.96	O2W—H1W2	0.91 (3)
C6—H6B	0.96	O2W—H2W2	0.85 (3)
C1—O2—H1O2	110.3 (15)	C8—C7—N1	115.36 (10)
C2—O3—H1O3	110.7 (16)	C8—C7—H7A	108.4
C3—O4—H1O4	101.3 (17)	N1—C7—H7A	108.4
O1—C1—O2	124.88 (12)	C8—C7—H7B	108.4
O1—C1—C2	122.38 (11)	N1—C7—H7B	108.4
O2—C1—C2	112.74 (11)	H7A—C7—H7B	107.5
O3—C2—C1	111.28 (10)	C7—C8—H8A	109.5
O3—C2—C3	111.23 (10)	C7—C8—H8B	109.5
C1—C2—C3	110.06 (10)	H8A—C8—H8B	109.5
O3—C2—H2A	108.0	C7—C8—H8C	109.5
C1—C2—H2A	108.0	H8A—C8—H8C	109.5
C3—C2—H2A	108.0	H8B—C8—H8C	109.5
O4—C3—C4	112.59 (11)	C10—C9—N1	115.34 (10)
O4—C3—C2	110.58 (10)	C10—C9—H9A	108.4
C4—C3—C2	109.84 (10)	N1—C9—H9A	108.4
O4—C3—H3A	107.9	C10—C9—H9B	108.4
C4—C3—H3A	107.9	N1—C9—H9B	108.4
C2—C3—H3A	107.9	H9A—C9—H9B	107.5
O6—C4—O5	126.43 (13)	C9—C10—H10A	109.5
O6—C4—C3	119.17 (12)	C9—C10—H10B	109.5
O5—C4—C3	114.40 (11)	H10A—C10—H10B	109.5
C11—N1—C7	111.31 (10)	C9—C10—H10C	109.5
C11—N1—C9	111.21 (10)	H10A—C10—H10C	109.5
C7—N1—C9	105.96 (9)	H10B—C10—H10C	109.5
C11—N1—C5	105.62 (9)	C12—C11—N1	115.18 (10)
C7—N1—C5	111.49 (10)	C12—C11—H11A	108.5
C9—N1—C5	111.36 (10)	N1—C11—H11A	108.5
C6—C5—N1	115.24 (11)	C12—C11—H11B	108.5
C6—C5—H5A	108.5	N1—C11—H11B	108.5
N1—C5—H5A	108.5	H11A—C11—H11B	107.5
C6—C5—H5B	108.5	C11—C12—H12A	109.5
N1—C5—H5B	108.5	C11—C12—H12B	109.5
H5A—C5—H5B	107.5	H12A—C12—H12B	109.5
C5—C6—H6A	109.5	C11—C12—H12C	109.5
C5—C6—H6B	109.5	H12A—C12—H12C	109.5
H6A—C6—H6B	109.5	H12B—C12—H12C	109.5
C5—C6—H6C	109.5	H1W1—O1W—H2W1	106 (3)
H6A—C6—H6C	109.5	H1W2—O2W—H2W2	106 (2)
H6B—C6—H6C	109.5
O1—C1—C2—O3	−20.73 (16)	C11—N1—C5—C6	175.99 (11)
O2—C1—C2—O3	159.12 (10)	C7—N1—C5—C6	54.95 (15)
O1—C1—C2—C3	103.04 (13)	C9—N1—C5—C6	−63.16 (15)
O2—C1—C2—C3	−77.11 (13)	C11—N1—C7—C8	−60.40 (15)
O3—C2—C3—O4	60.68 (13)	C9—N1—C7—C8	178.57 (12)
C1—C2—C3—O4	−63.12 (13)	C5—N1—C7—C8	57.25 (15)
O3—C2—C3—C4	−64.19 (13)	C11—N1—C9—C10	56.22 (15)
C1—C2—C3—C4	172.01 (10)	C7—N1—C9—C10	177.31 (12)
O4—C3—C4—O6	−5.84 (16)	C5—N1—C9—C10	−61.29 (15)
C2—C3—C4—O6	117.86 (13)	C7—N1—C11—C12	−60.88 (14)
O4—C3—C4—O5	174.27 (11)	C9—N1—C11—C12	57.02 (14)
C2—C3—C4—O5	−62.03 (14)	C5—N1—C11—C12	177.97 (12)

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···O2iv	0.82 (2)	2.56 (2)	3.0668 (14)	122 (2)
O1W—H1W1···O2Wv	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···O1vi	0.84 (2)	2.40 (2)	3.0082 (14)	129 (2)
C5—H5A···O3vii	0.97	2.56	3.4344 (15)	151
C8—H8B···O4	0.96	2.38	3.3447 (16)	178
C10—H10B···O3vii	0.96	2.47	3.4195 (16)	168
C11—H11A···O4	0.97	2.50	3.2693 (15)	136

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⋯O2iv	0.82 (2)	2.56 (2)	3.0668 (14)	122 (2)
O1W—H1W1⋯O2Wv	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⋯O1vi	0.84 (2)	2.40 (2)	3.0082 (14)	129 (2)
C5—H5A⋯O3vii	0.97	2.56	3.4344 (15)	151
C8—H8B⋯O4	0.96	2.38	3.3447 (16)	178
C10—H10B⋯O3vii	0.96	2.47	3.4195 (16)	168
C11—H11A⋯O4	0.97	2.50	3.2693 (15)	136

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