Choline dihydrogen phosphate.

In the cystal structure of the title compound, (2-hy-droxy-ethyl)trimethylammonium dihydrogen phosphate, C(5)H(14)NO(+)·H(2)PO(4) (-), two anions create dimeric structures via two O-H⋯O hydrogen bonds. The hydrogen-bonded dimers are connected by another O-H⋯O hydrogen bond with the hydroxyl groups of the cations, constructing a columner structure along the a axis. A number of C-H⋯O interactions are also present.

Related literature

For background to ionic liquids, see: Byrne et al. (2007 ▶); Fujita et al. (2005 ▶); Ohno (2005 ▶); van Rantwijk et al. (2003 ▶); Seddon (1997 ▶); Wasserscheid & Welton (2002 ▶); Welton (1999 ▶); Zhao et al. (2008 ▶).

Experimental

Crystal data

C5H14NO+·H2PO4 −

M = 201.16

Triclinic,

a = 6.9232 (3) Å

b = 8.2807 (4) Å

c = 9.2333 (3) Å

α = 84.458 (3)°

β = 71.414 (3)°

γ = 70.758 (3)°

V = 473.68 (4) Å3

Z = 2

Cu Kα radiation

μ = 2.55 mm−1

T = 193 K

0.60 × 0.10 × 0.02 mm

Data collection

Rigaku RAXIS-RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.429, T max = 0.950

8717 measured reflections

1714 independent reflections

1344 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.121

S = 1.12

1714 reflections

124 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.38 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson (1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007259/at2730sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007259/at2730Isup2.hkl

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

C5H14NO+·H2PO4−	Z = 2
Mr = 201.16	F(000) = 216
Triclinic, P1	Dx = 1.410 Mg m−3
Hall symbol: -P 1	Melting point: 392 K
a = 6.9232 (3) Å	Cu Kα radiation, λ = 1.54187 Å
b = 8.2807 (4) Å	Cell parameters from 6930 reflections
c = 9.2333 (3) Å	θ = 5.1–68.3°
α = 84.458 (3)°	µ = 2.55 mm−1
β = 71.414 (3)°	T = 193 K
γ = 70.758 (3)°	Platelet, colourless
V = 473.68 (4) Å3	0.60 × 0.10 × 0.02 mm

Rigaku RAXIS-RAPID diffractometer	1714 independent reflections
Radiation source: rotating anode	1344 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 10.00 pixels mm-1	θmax = 68.3°, θmin = 5.1°
ω scans	h = −8→8
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→9
Tmin = 0.429, Tmax = 0.950	l = −11→11
8717 measured reflections

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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.050P] where P = (Fo2 + 2Fc2)/3
1714 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.38 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 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
P1	0.81645 (9)	0.68990 (7)	0.17447 (6)	0.0335 (2)
O1	0.5777 (2)	0.7534 (2)	0.24514 (18)	0.0430 (5)
O2	0.9220 (3)	0.50241 (19)	0.19693 (17)	0.0439 (5)
O3	0.9039 (3)	0.8007 (2)	0.25187 (19)	0.0390 (4)
O4	0.8798 (3)	0.7343 (2)	0.00080 (18)	0.0406 (4)
O5	0.7017 (3)	0.2172 (2)	−0.10979 (19)	0.0452 (5)
N1	0.4405 (3)	0.2917 (2)	0.3125 (2)	0.0340 (5)
C1	0.5122 (4)	0.3227 (3)	0.1424 (2)	0.0342 (5)
H1A	0.5978	0.4020	0.1227	0.041*
H1B	0.3832	0.3801	0.1096	0.041*
C2	0.6444 (4)	0.1635 (3)	0.0453 (2)	0.0391 (6)
H2A	0.7750	0.1035	0.0755	0.047*
H2B	0.5596	0.0844	0.0584	0.047*
C3	0.3093 (4)	0.4616 (3)	0.3894 (3)	0.0417 (6)
H3A	0.1821	0.5104	0.3547	0.050*
H3B	0.3958	0.5391	0.3633	0.050*
H3C	0.2640	0.4464	0.5003	0.050*
C4	0.3029 (4)	0.1774 (3)	0.3487 (3)	0.0458 (7)
H4A	0.1836	0.2257	0.3057	0.055*
H4B	0.2458	0.1681	0.4597	0.055*
H4C	0.3893	0.0636	0.3042	0.055*
C5	0.6299 (4)	0.2169 (3)	0.3699 (3)	0.0435 (6)
H5A	0.7117	0.1024	0.3255	0.052*
H5B	0.5805	0.2089	0.4815	0.052*
H5C	0.7219	0.2902	0.3403	0.052*
H3O	1.025 (5)	0.793 (4)	0.209 (3)	0.058 (9)*
H4O	0.959 (6)	0.643 (5)	−0.067 (4)	0.096 (12)*
H5O	0.597 (5)	0.232 (4)	−0.158 (4)	0.090 (12)*

	U11	U22	U33	U12	U13	U23
P1	0.0331 (4)	0.0388 (4)	0.0280 (4)	−0.0104 (3)	−0.0088 (3)	−0.0016 (2)
O1	0.0311 (9)	0.0607 (12)	0.0372 (9)	−0.0139 (8)	−0.0102 (7)	−0.0032 (8)
O2	0.0622 (11)	0.0359 (10)	0.0292 (9)	−0.0108 (8)	−0.0130 (8)	0.0003 (7)
O3	0.0323 (9)	0.0490 (10)	0.0363 (9)	−0.0148 (8)	−0.0066 (7)	−0.0093 (7)
O4	0.0474 (10)	0.0392 (10)	0.0298 (9)	−0.0082 (8)	−0.0099 (7)	−0.0009 (7)
O5	0.0372 (9)	0.0728 (13)	0.0290 (9)	−0.0221 (9)	−0.0102 (7)	0.0022 (8)
N1	0.0408 (11)	0.0326 (10)	0.0299 (10)	−0.0123 (8)	−0.0125 (8)	0.0028 (8)
C1	0.0372 (12)	0.0396 (13)	0.0284 (12)	−0.0143 (10)	−0.0124 (10)	0.0042 (9)
C2	0.0421 (13)	0.0476 (14)	0.0282 (12)	−0.0154 (11)	−0.0103 (10)	0.0001 (10)
C3	0.0476 (14)	0.0366 (13)	0.0340 (12)	−0.0063 (11)	−0.0097 (11)	−0.0028 (10)
C4	0.0574 (16)	0.0469 (15)	0.0356 (13)	−0.0284 (13)	−0.0064 (11)	0.0038 (11)
C5	0.0506 (15)	0.0435 (14)	0.0352 (13)	−0.0045 (12)	−0.0223 (11)	0.0006 (11)

P1—O1	1.4969 (16)	C1—H1A	0.9900
P1—O2	1.5080 (16)	C1—H1B	0.9900
P1—O4	1.5629 (16)	C2—H2A	0.9900
P1—O3	1.5771 (17)	C2—H2B	0.9900
O3—H3O	0.79 (3)	C3—H3A	0.9800
O4—H4O	0.93 (4)	C3—H3B	0.9800
O5—C2	1.427 (3)	C3—H3C	0.9800
O5—H5O	0.93 (4)	C4—H4A	0.9800
N1—C5	1.493 (3)	C4—H4B	0.9800
N1—C4	1.499 (3)	C4—H4C	0.9800
N1—C3	1.499 (3)	C5—H5A	0.9800
N1—C1	1.513 (3)	C5—H5B	0.9800
C1—C2	1.513 (3)	C5—H5C	0.9800
O1—P1—O2	115.19 (10)	C1—C2—H2A	110.3
O1—P1—O4	110.63 (9)	O5—C2—H2B	110.3
O2—P1—O4	110.24 (9)	C1—C2—H2B	110.3
O1—P1—O3	104.81 (9)	H2A—C2—H2B	108.6
O2—P1—O3	109.78 (10)	N1—C3—H3A	109.5
O4—P1—O3	105.63 (10)	N1—C3—H3B	109.5
P1—O3—H3O	113 (2)	H3A—C3—H3B	109.5
P1—O4—H4O	117 (2)	N1—C3—H3C	109.5
C2—O5—H5O	114 (2)	H3A—C3—H3C	109.5
C5—N1—C4	110.68 (19)	H3B—C3—H3C	109.5
C5—N1—C3	108.80 (19)	N1—C4—H4A	109.5
C4—N1—C3	108.66 (19)	N1—C4—H4B	109.5
C5—N1—C1	110.65 (17)	H4A—C4—H4B	109.5
C4—N1—C1	110.51 (18)	N1—C4—H4C	109.5
C3—N1—C1	107.44 (16)	H4A—C4—H4C	109.5
N1—C1—C2	114.88 (18)	H4B—C4—H4C	109.5
N1—C1—H1A	108.5	N1—C5—H5A	109.5
C2—C1—H1A	108.5	N1—C5—H5B	109.5
N1—C1—H1B	108.5	H5A—C5—H5B	109.5
C2—C1—H1B	108.5	N1—C5—H5C	109.5
H1A—C1—H1B	107.5	H5A—C5—H5C	109.5
O5—C2—C1	107.09 (19)	H5B—C5—H5C	109.5
O5—C2—H2A	110.3
C5—N1—C1—C2	62.5 (3)	C3—N1—C1—C2	−178.9 (2)
C4—N1—C1—C2	−60.5 (3)	N1—C1—C2—O5	−178.51 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5i	0.80 (4)	1.79 (4)	2.586 (3)	178 (3)
O4—H4O···O2i	0.93 (4)	1.60 (4)	2.526 (2)	173 (3)
O5—H5O···O1ii	0.93 (4)	1.63 (4)	2.556 (3)	176 (4)
C3—H3B···O1	0.98	2.48	3.439 (3)	166
C4—H4B···O3iii	0.98	2.54	3.504 (3)	170
C4—H4C···O1iv	0.98	2.49	3.457 (3)	168
C5—H5A···O3iv	0.98	2.46	3.430 (3)	172
C5—H5B···O1iii	0.98	2.42	3.382 (3)	169
C5—H5C···O2	0.98	2.60	3.549 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O5i	0.80 (4)	1.79 (4)	2.586 (3)	178 (3)
O4—H4O⋯O2i	0.93 (4)	1.60 (4)	2.526 (2)	173 (3)
O5—H5O⋯O1ii	0.93 (4)	1.63 (4)	2.556 (3)	176 (4)
C3—H3B⋯O1	0.98	2.48	3.439 (3)	166
C4—H4B⋯O3iii	0.98	2.54	3.504 (3)	170
C4—H4C⋯O1iv	0.98	2.49	3.457 (3)	168
C5—H5A⋯O3iv	0.98	2.46	3.430 (3)	172
C5—H5B⋯O1iii	0.98	2.42	3.382 (3)	169
C5—H5C⋯O2	0.98	2.60	3.549 (3)	164

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