Tetra-ethyl-ammonium bicarbonate trihydrate.

In the title compound, C(8)H(20)N(+)·CHO(3) (-)·3H(2)O, the bicarbon-ate anion, which has a small mean deviation from the plane of 0.0014 Å, fully utilises its three O and one H atom to form various O-H⋯O hydrogen bonds with the three water mol-ecules in the asymmetric unit, generating a hydrogen-bonded layer, which extends along (10[Formula: see text]). The tetra-ethyl-ammonium cations, as the guest species, are accommodated between every two neighboring layers, constructing a sandwich-like structure with an inter-layer distance of 7.28 Å.

Related literature

For the crystal structure of tetra­ethyl­ammonium bicarbonate monohydrate clathrate, see: Li et al. (2003 ▶). For O—H⋯O hydrogen bonds, see: Steiner (2002 ▶). For polymorphism see Kumar et al. (2002 ▶).

Experimental

Crystal data

C8H20N+·CHO3 −·3H2O

M = 245.32

Monoclinic,

a = 7.6633 (1) Å

b = 12.9627 (3) Å

c = 14.2683 (3) Å

β = 99.932 (1)°

V = 1396.13 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.61 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.854, T max = 1.000

8465 measured reflections

3480 independent reflections

2466 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.138

S = 1.02

3480 reflections

166 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026080/nr2008sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026080/nr2008Isup2.hkl

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

C8H20N+·CHO3−·3H2O	F(000) = 544
Mr = 245.32	Dx = 1.167 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2627 reflections
a = 7.6633 (1) Å	θ = 3.1–26.7°
b = 12.9627 (3) Å	µ = 0.10 mm−1
c = 14.2683 (3) Å	T = 296 K
β = 99.932 (1)°	Block, colourless
V = 1396.13 (5) Å3	0.61 × 0.29 × 0.18 mm
Z = 4

Bruker SMART APEX diffractometer	3480 independent reflections
Radiation source: fine-focus sealed tube	2466 reflections with I > 2σ(I)
graphite	Rint = 0.018
phi and ω scans	θmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
Tmin = 0.854, Tmax = 1.000	k = −17→15
8465 measured reflections	l = −12→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0697P)2 + 0.1916P] where P = (Fo2 + 2Fc2)/3
3480 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.16 e Å−3
10 restraints	Δρmin = −0.17 e Å−3

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
N1	0.23247 (12)	0.27367 (8)	0.83104 (6)	0.0337 (2)
O1	0.02644 (15)	0.87654 (8)	0.97489 (8)	0.0608 (3)
O1W	0.24867 (16)	0.07251 (10)	0.33750 (8)	0.0642 (3)
H1WA	0.218 (3)	0.0994 (16)	0.2845 (10)	0.096*
H1WB	0.308 (3)	0.0199 (12)	0.3364 (16)	0.096*
C1	−0.08821 (18)	0.89307 (11)	0.90217 (9)	0.0453 (3)
O2	−0.14805 (14)	0.82902 (9)	0.84014 (8)	0.0594 (3)
O2W	0.21273 (15)	0.68993 (10)	0.99356 (9)	0.0641 (3)
H2WA	0.165 (3)	0.7475 (10)	0.9923 (15)	0.096*
H2WB	0.212 (3)	0.6570 (14)	1.0426 (11)	0.096*
C2	0.40040 (16)	0.21074 (11)	0.86043 (9)	0.0443 (3)
H2A	0.4158	0.1663	0.8077	0.053*
H2B	0.5004	0.2577	0.8714	0.053*
O3	−0.15534 (16)	0.98874 (8)	0.88939 (8)	0.0632 (3)
H3	−0.109 (3)	1.0260 (15)	0.9338 (12)	0.095*
O3W	−0.05481 (19)	0.61659 (11)	0.84914 (10)	0.0767 (4)
H3WA	−0.110 (3)	0.6718 (13)	0.8393 (18)	0.115*
H3WB	0.017 (3)	0.6182 (19)	0.8983 (12)	0.115*
C3	0.4058 (3)	0.14500 (13)	0.94748 (12)	0.0654 (4)
H3A	0.5164	0.1086	0.9602	0.098*
H3B	0.3099	0.0964	0.9370	0.098*
H3C	0.3945	0.1880	1.0009	0.098*
C4	0.26289 (17)	0.33841 (11)	0.74702 (9)	0.0428 (3)
H4A	0.3656	0.3819	0.7671	0.051*
H4B	0.2907	0.2926	0.6979	0.051*
C5	0.1098 (2)	0.40604 (13)	0.70431 (11)	0.0599 (4)
H5A	0.1407	0.4439	0.6517	0.090*
H5B	0.0832	0.4535	0.7516	0.090*
H5C	0.0079	0.3639	0.6825	0.090*
C6	0.19457 (17)	0.34029 (10)	0.91255 (9)	0.0418 (3)
H6A	0.0877	0.3797	0.8907	0.050*
H6B	0.1710	0.2954	0.9633	0.050*
C7	0.3400 (2)	0.41413 (12)	0.95290 (11)	0.0542 (4)
H7A	0.3047	0.4526	1.0040	0.081*
H7B	0.3621	0.4607	0.9040	0.081*
H7C	0.4460	0.3761	0.9765	0.081*
C8	0.07102 (17)	0.20495 (11)	0.80381 (10)	0.0460 (3)
H8A	0.0591	0.1620	0.8580	0.055*
H8B	−0.0334	0.2484	0.7905	0.055*
C9	0.0748 (2)	0.13609 (13)	0.71913 (13)	0.0655 (4)
H9A	−0.0319	0.0958	0.7070	0.098*
H9B	0.1754	0.0909	0.7321	0.098*
H9C	0.0834	0.1776	0.6644	0.098*

	U11	U22	U33	U12	U13	U23
N1	0.0328 (5)	0.0355 (5)	0.0333 (5)	−0.0040 (4)	0.0068 (4)	−0.0037 (4)
O1	0.0708 (7)	0.0493 (6)	0.0566 (6)	0.0134 (5)	−0.0049 (5)	0.0020 (5)
O1W	0.0656 (7)	0.0716 (8)	0.0541 (6)	−0.0014 (6)	0.0067 (5)	−0.0011 (6)
C1	0.0479 (7)	0.0450 (8)	0.0446 (7)	0.0014 (6)	0.0123 (6)	0.0060 (6)
O2	0.0651 (6)	0.0528 (6)	0.0577 (6)	0.0023 (5)	0.0035 (5)	−0.0053 (5)
O2W	0.0592 (6)	0.0610 (7)	0.0716 (7)	0.0131 (5)	0.0106 (5)	0.0068 (6)
C2	0.0401 (6)	0.0455 (8)	0.0464 (7)	0.0048 (5)	0.0052 (5)	−0.0046 (6)
O3	0.0769 (8)	0.0459 (6)	0.0593 (7)	0.0090 (5)	−0.0094 (5)	0.0057 (5)
O3W	0.0932 (10)	0.0618 (8)	0.0705 (8)	0.0027 (7)	0.0013 (7)	−0.0066 (6)
C3	0.0826 (11)	0.0567 (10)	0.0540 (9)	0.0176 (8)	0.0034 (8)	0.0062 (7)
C4	0.0467 (7)	0.0460 (7)	0.0373 (6)	−0.0067 (6)	0.0116 (5)	0.0010 (5)
C5	0.0662 (9)	0.0568 (9)	0.0532 (8)	−0.0010 (7)	0.0005 (7)	0.0136 (7)
C6	0.0430 (6)	0.0458 (7)	0.0383 (6)	0.0007 (5)	0.0117 (5)	−0.0073 (5)
C7	0.0627 (8)	0.0503 (8)	0.0483 (8)	−0.0063 (7)	0.0054 (6)	−0.0153 (6)
C8	0.0411 (6)	0.0475 (8)	0.0488 (7)	−0.0141 (6)	0.0060 (5)	−0.0028 (6)
C9	0.0682 (10)	0.0556 (10)	0.0685 (10)	−0.0155 (8)	−0.0001 (8)	−0.0204 (8)

N1—C4	1.5141 (15)	C3—H3C	0.9600
N1—C6	1.5162 (15)	C4—C5	1.507 (2)
N1—C8	1.5197 (15)	C4—H4A	0.9700
N1—C2	1.5203 (16)	C4—H4B	0.9700
O1—C1	1.2569 (17)	C5—H5A	0.9600
O1W—H1WA	0.829 (9)	C5—H5B	0.9600
O1W—H1WB	0.823 (9)	C5—H5C	0.9600
C1—O2	1.2422 (17)	C6—C7	1.5064 (19)
C1—O3	1.3429 (18)	C6—H6A	0.9700
O2W—H2WA	0.830 (9)	C6—H6B	0.9700
O2W—H2WB	0.820 (9)	C7—H7A	0.9600
C2—C3	1.501 (2)	C7—H7B	0.9600
C2—H2A	0.9700	C7—H7C	0.9600
C2—H2B	0.9700	C8—C9	1.506 (2)
O3—H3	0.827 (10)	C8—H8A	0.9700
O3W—H3WA	0.831 (9)	C8—H8B	0.9700
O3W—H3WB	0.812 (9)	C9—H9A	0.9600
C3—H3A	0.9600	C9—H9B	0.9600
C3—H3B	0.9600	C9—H9C	0.9600
C4—N1—C6	111.57 (10)	C4—C5—H5A	109.5
C4—N1—C8	110.62 (9)	C4—C5—H5B	109.5
C6—N1—C8	105.95 (9)	H5A—C5—H5B	109.5
C4—N1—C2	106.09 (9)	C4—C5—H5C	109.5
C6—N1—C2	111.05 (9)	H5A—C5—H5C	109.5
C8—N1—C2	111.66 (10)	H5B—C5—H5C	109.5
H1WA—O1W—H1WB	113.7 (19)	C7—C6—N1	115.34 (10)
O2—C1—O1	126.42 (14)	C7—C6—H6A	108.4
O2—C1—O3	115.77 (12)	N1—C6—H6A	108.4
O1—C1—O3	117.81 (13)	C7—C6—H6B	108.4
H2WA—O2W—H2WB	114.8 (19)	N1—C6—H6B	108.4
C3—C2—N1	115.72 (12)	H6A—C6—H6B	107.5
C3—C2—H2A	108.4	C6—C7—H7A	109.5
N1—C2—H2A	108.4	C6—C7—H7B	109.5
C3—C2—H2B	108.4	H7A—C7—H7B	109.5
N1—C2—H2B	108.4	C6—C7—H7C	109.5
H2A—C2—H2B	107.4	H7A—C7—H7C	109.5
C1—O3—H3	109.4 (16)	H7B—C7—H7C	109.5
H3WA—O3W—H3WB	112 (2)	C9—C8—N1	115.14 (11)
C2—C3—H3A	109.5	C9—C8—H8A	108.5
C2—C3—H3B	109.5	N1—C8—H8A	108.5
H3A—C3—H3B	109.5	C9—C8—H8B	108.5
C2—C3—H3C	109.5	N1—C8—H8B	108.5
H3A—C3—H3C	109.5	H8A—C8—H8B	107.5
H3B—C3—H3C	109.5	C8—C9—H9A	109.5
C5—C4—N1	115.30 (11)	C8—C9—H9B	109.5
C5—C4—H4A	108.4	H9A—C9—H9B	109.5
N1—C4—H4A	108.4	C8—C9—H9C	109.5
C5—C4—H4B	108.4	H9A—C9—H9C	109.5
N1—C4—H4B	108.4	H9B—C9—H9C	109.5
H4A—C4—H4B	107.5

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2i	0.83 (1)	2.00 (1)	2.8239 (16)	177 (2)
O1W—H1WB···O3Wii	0.82 (1)	2.05 (1)	2.8666 (19)	173 (2)
O2W—H2WA···O1	0.83 (1)	1.97 (1)	2.7980 (15)	172 (2)
O2W—H2WB···O1Wiii	0.82 (1)	2.01 (1)	2.8229 (16)	171 (2)
O3—H3···O1iv	0.83 (1)	1.85 (1)	2.6676 (15)	172 (2)
O3W—H3WA···O2	0.83 (1)	2.06 (1)	2.8422 (18)	157 (2)
O3W—H3WB···O2W	0.81 (1)	2.07 (2)	2.8099 (19)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2i	0.83 (1)	2.00 (1)	2.8239 (16)	177 (2)
O1W—H1WB⋯O3Wii	0.82 (1)	2.05 (1)	2.8666 (19)	173 (2)
O2W—H2WA⋯O1	0.83 (1)	1.97 (1)	2.7980 (15)	172 (2)
O2W—H2WB⋯O1Wiii	0.82 (1)	2.01 (1)	2.8229 (16)	171 (2)
O3—H3⋯O1iv	0.83 (1)	1.85 (1)	2.6676 (15)	172 (2)
O3W—H3WA⋯O2	0.83 (1)	2.06 (1)	2.8422 (18)	157 (2)
O3W—H3WB⋯O2W	0.81 (1)	2.07 (2)	2.8099 (19)	152 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .