2-(Tri­methyl­aza­nium­yl)ethyl hydrogen phosphate (phospho­choline) mono­hydrate

Nikawa, Y.; Fujita, K.; Noguchi, K.; Ohno, H.

doi:10.1107/S160053681400779X

organic compounds

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Volume 70| Part 5| May 2014| Page o549

doi:10.1107/S160053681400779X

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2-(Trimethylazaniumyl)ethyl hydrogen phosphate (phosphocholine) monohydrate

Yohsuke Nikawa,^a,^b Kyoko Fujita,^a,^b,^c Keiichi Noguchi ^d and Hiroyuki Ohno ^a,^b,^c ^*

^aDepartment of Biotechnology, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan, ^bFunctional Ionic liquid Laboratories, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei, Japan, ^cJapan Science and Technology Agency (JST), Core Research for Evolutional Science and Technology (CREST), Chiyoda, Japan, and ^dInstrumentation Analysis Center, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: ohnoh@cc.tuat.ac.jp

(Received 22 February 2014; accepted 8 April 2014; online 12 April 2014)

In the crystal structure of the title compound, C₅H₁₄NO₄P·H₂O, the zwitterionic phosphocholine molecules are connected by an O—H⋯O hydrogen bond between the phosphate groups, forming a zigzag chain along the b-axis direction. The chains are further connected through O—H⋯O hydrogen bonds involving water molecules, forming a layer parallel to (101). Three and one C—H⋯O interactions are also observed in the layer and between the layers, respectively. The conformation of the N—C—C—O backbone is gauche with a torsion angle of −75.8 (2)°

CCDC reference: 996006

Related literature

For related structures, see: Fujita et al. (2009 ); Pearson & Pascher (1979 ); McAlister et al. (1979 ).

Experimental

Crystal data

C₅H₁₄NO₄P·H₂O
M_r = 201.16
Monoclinic, P 2₁ /n
a = 10.4304 (2) Å
b = 6.8873 (1) Å
c = 13.4992 (3) Å
β = 105.800 (1)°
V = 933.11 (3) Å³
Z = 4
Cu Kα radiation
μ = 2.59 mm⁻¹
T = 193 K
0.60 × 0.40 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Rigaku, 1999 ) T_min = 0.306, T_max = 0.424
16036 measured reflections
1715 independent reflections
1632 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.13
1715 reflections
121 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O4ⁱ	0.80 (3)	1.74 (3)	2.525 (2)	167 (3)
O5—H5OA⋯O3ⁱⁱ	0.77 (3)	1.99 (3)	2.764 (2)	175 (3)
O5—H5OB⋯O3ⁱⁱⁱ	0.75 (3)	2.04 (3)	2.784 (2)	172 (3)
C2—H2A⋯O3^iv	0.99	2.47	3.440 (2)	167
C3—H3B⋯O5^v	0.98	2.52	3.479 (3)	167
C3—H3C⋯O3^vi	0.98	2.51	3.388 (2)	149
C5—H5C⋯O4^vii	0.98	2.36	3.219 (3)	146
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z; (v) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) -x, -y, -z+1; (vii) -x+1, -y, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 2004 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010 ); program(s) used to solve structure: Il Milione (Burla et al., 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 996006

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681400779X/is5344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400779X/is5344Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681400779X/is5344Isup3.cml

checkCIF report

Comment top

Phosphocholine is similar to head groups of the phospholipid which is a major component of cell membranes. In past study, crystal structures of the compounds which have the phospholipid head group, such as 1,2-dimyristoyl-sn-glycero-3-phosphorylcholine dihydrate (Pearson & Pascher, 1979), choline phosphate calcium chloride tetrahydrate (McAlister et al., 1979) and choline dihydrogen phosphate (Fujita et al., 2009), were observed. We report herein the crystal structure of phosphocholine monohydrate.

The molecular structures of the title compound are shown in Fig. 1. The phosphate groups form the hydrogen bonds of O2···H—O4 linked to two neighboring phosphate groups (Fig. 2). These hydrogen bonds create a hydrogen bonding chain of phosphate groups along the b axis. In addition, phosphate groups are connected to the other neighboring phosphate group via two hydrogen bonds of O3···H—O5, with two water molecules (Fig. 3). Due to these hydrogen bonding network, molecules are arranged in layers parallel to the (101) plane. Four C—H···O interactions also occur in these layered structure (Table 1).

Related literature top

For related structures, see: Fujita et al. (2009); Pearson & Pascher (1979); McAlister et al. (1979).

Experimental top

Phosphorylcholine calcium chloride tetrahydrate was dissolved in water. The aqueous solution was treated on an anion exchange resin (Amberlite IRN77) and a cation exchange resin (TULSION-93). The solvent evaporated and the product was dried in vacuo. White powder was crystallized from a methanol solution. Acetonitrile was used as the antisolvent. This crystallization was repeated twice. Final purification was achieved by recrystallization from a saturated aqueous solution at room temperature for X-ray measurements.

The title compound was identified using ¹H NMR, electrospray mass spectrometry, and elementary analysis. Spectroscopic analysis: ¹H NMR (D₂O, δ, p.p.m.): 3.214(s, 9H), 3.653(t, 2H), 4.286(m, 2H), HRMS(ESI) (m/z) calcd for C₅H₁₄NO₄P [M+H]⁺ 184.0739, found 184.0849. Elementary analysis calculated for C₅H₁₄NO₄P: C 32.79, H 7.71, N 7.65% found: C 32.22, H 7.383, N 8.017%.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2004); cell refinement: PROCESS-AUTO (Rigaku, 2004); data reduction: CrystalStructure (Rigaku, 2010); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Displacement ellipsoid plot and atomic numbering scheme of the title compound. Ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) x - 1/2, -y + 1/2, z + 1/2.]
	Fig. 2. A packing diagram of the title compound, viewed along the a axis. Dashed lines indicate intermolecular O—H···O and C—H···O hydrogen bonds. [Symmetry codes: (i) x - 1/2, -y + 1/2, z + 1/2; (ii) -x + 1/2, y + 1/2, -z + 1/2; (iii) -x + 1/2, y - 3/2, -z + 1/2; (vi) x, 1 + y, z.]
	Fig. 3. A packing diagram of the title compound, viewed along the b axis. Dashed lines indicate intermolecular O—H···O and C—H···O hydrogen bonds. [Symmetry codes: (i) x - 1/2, -y + 1/2, z + 1/2; (ii) -x + 1/2, y + 1/2, -z + 1/2; (iii) -x + 1/2, y - 3/2, -z + 1/2; (iv) 1 - x, -y, 1 - z; (v) -x, -y, 1 - z.]

2-(Trimethylazaniumyl)ethyl hydrogen phosphate monohydrate top

Crystal data top

C₅H₁₄NO₄P·H₂O	F(000) = 432
M_r = 201.16	D_x = 1.432 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 15511 reflections
a = 10.4304 (2) Å	θ = 3.4–68.2°
b = 6.8873 (1) Å	µ = 2.59 mm⁻¹
c = 13.4992 (3) Å	T = 193 K
β = 105.800 (1)°	Block, colorless
V = 933.11 (3) Å³	0.60 × 0.40 × 0.40 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	1715 independent reflections
Radiation source: rotating anode	1632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 4.8°
ω scans	h = −12→12
Absorption correction: numerical (NUMABS; Rigaku, 1999)	k = −8→8
T_min = 0.306, T_max = 0.424	l = −15→16
16036 measured reflections

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0594P)² + 0.4329P] where P = (F_o² + 2F_c²)/3
1715 reflections	(Δ/σ)_max < 0.001
121 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₅H₁₄NO₄P·H₂O	V = 933.11 (3) Å³
M_r = 201.16	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 10.4304 (2) Å	µ = 2.59 mm⁻¹
b = 6.8873 (1) Å	T = 193 K
c = 13.4992 (3) Å	0.60 × 0.40 × 0.40 mm
β = 105.800 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	1715 independent reflections
Absorption correction: numerical (NUMABS; Rigaku, 1999)	1632 reflections with I > 2σ(I)
T_min = 0.306, T_max = 0.424	R_int = 0.037
16036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.21 e Å⁻³
1715 reflections	Δρ_min = −0.50 e Å⁻³
121 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. 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.

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

	x	y	z	U_iso*/U_eq
P1	0.19372 (4)	−0.29328 (6)	0.34891 (3)	0.02017 (18)
O1	0.26794 (11)	−0.11051 (17)	0.41531 (9)	0.0250 (3)
O2	0.11276 (14)	−0.2045 (2)	0.24371 (10)	0.0340 (4)
H2O	0.149 (3)	−0.124 (4)	0.219 (2)	0.058 (8)*
O3	0.09520 (13)	−0.3768 (2)	0.39911 (10)	0.0316 (3)
O4	0.30448 (13)	−0.4207 (2)	0.34008 (11)	0.0341 (3)
N1	0.31816 (14)	0.1794 (2)	0.60363 (11)	0.0216 (3)
C1	0.18974 (19)	0.0567 (3)	0.42416 (14)	0.0304 (4)
H1A	0.1186	0.0186	0.4561	0.036*
H1B	0.1469	0.1091	0.3547	0.036*
C2	0.27544 (19)	0.2105 (2)	0.48844 (13)	0.0264 (4)
H2A	0.2266	0.3353	0.4746	0.032*
H2B	0.3567	0.2245	0.4646	0.032*
C3	0.20152 (19)	0.1449 (3)	0.64541 (15)	0.0340 (4)
H3A	0.2310	0.1464	0.7208	0.041*
H3B	0.1619	0.0184	0.6217	0.041*
H3C	0.1351	0.2473	0.6211	0.041*
C4	0.4142 (2)	0.0135 (3)	0.63344 (15)	0.0367 (5)
H4A	0.3717	−0.1062	0.6013	0.044*
H4B	0.4401	−0.0015	0.7085	0.044*
H4C	0.4936	0.0399	0.6100	0.044*
C5	0.3865 (2)	0.3617 (3)	0.65134 (16)	0.0355 (5)
H5A	0.4193	0.3447	0.7261	0.043*
H5B	0.3232	0.4701	0.6361	0.043*
H5C	0.4616	0.3896	0.6230	0.043*
O5	0.58971 (16)	0.8315 (2)	0.10139 (12)	0.0367 (4)
H5OA	0.593 (3)	0.838 (4)	0.045 (2)	0.043 (7)*
H5OB	0.539 (3)	0.905 (4)	0.106 (2)	0.046 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0221 (3)	0.0191 (3)	0.0200 (3)	−0.00203 (15)	0.00695 (18)	−0.00011 (15)
O1	0.0229 (6)	0.0223 (6)	0.0273 (6)	0.0025 (5)	0.0025 (5)	−0.0048 (5)
O2	0.0380 (8)	0.0316 (8)	0.0263 (7)	−0.0155 (6)	−0.0015 (6)	0.0066 (5)
O3	0.0314 (7)	0.0330 (7)	0.0341 (7)	−0.0039 (6)	0.0151 (6)	0.0046 (6)
O4	0.0311 (7)	0.0313 (7)	0.0423 (8)	−0.0002 (6)	0.0141 (6)	−0.0127 (6)
N1	0.0195 (7)	0.0220 (7)	0.0227 (7)	0.0027 (5)	0.0046 (6)	−0.0014 (5)
C1	0.0308 (9)	0.0274 (10)	0.0276 (9)	0.0099 (8)	−0.0012 (7)	−0.0058 (7)
C2	0.0348 (10)	0.0208 (9)	0.0230 (9)	0.0030 (7)	0.0067 (7)	0.0025 (6)
C3	0.0297 (10)	0.0397 (11)	0.0357 (10)	−0.0025 (8)	0.0144 (8)	0.0026 (9)
C4	0.0380 (10)	0.0382 (11)	0.0292 (10)	0.0194 (9)	0.0013 (8)	−0.0007 (8)
C5	0.0308 (10)	0.0356 (11)	0.0397 (11)	−0.0083 (8)	0.0087 (8)	−0.0147 (9)
O5	0.0415 (9)	0.0374 (8)	0.0321 (8)	0.0114 (7)	0.0115 (7)	0.0050 (6)

Geometric parameters (Å, º) top

P1—O4	1.4812 (13)	C2—H2A	0.9900
P1—O3	1.4918 (13)	C2—H2B	0.9900
P1—O2	1.5655 (13)	C3—H3A	0.9800
P1—O1	1.6154 (12)	C3—H3B	0.9800
O1—C1	1.435 (2)	C3—H3C	0.9800
O2—H2O	0.79 (3)	C4—H4A	0.9800
N1—C3	1.493 (2)	C4—H4B	0.9800
N1—C5	1.500 (2)	C4—H4C	0.9800
N1—C4	1.501 (2)	C5—H5A	0.9800
N1—C2	1.512 (2)	C5—H5B	0.9800
C1—C2	1.501 (2)	C5—H5C	0.9800
C1—H1A	0.9900	O5—H5OA	0.77 (3)
C1—H1B	0.9900	O5—H5OB	0.74 (3)

O4—P1—O3	117.19 (8)	C1—C2—H2B	108.0
O4—P1—O2	113.47 (8)	N1—C2—H2B	108.0
O3—P1—O2	107.13 (8)	H2A—C2—H2B	107.2
O4—P1—O1	103.88 (7)	N1—C3—H3A	109.5
O3—P1—O1	109.49 (7)	N1—C3—H3B	109.5
O2—P1—O1	104.93 (7)	H3A—C3—H3B	109.5
C1—O1—P1	118.31 (10)	N1—C3—H3C	109.5
P1—O2—H2O	117 (2)	H3A—C3—H3C	109.5
C3—N1—C5	108.18 (14)	H3B—C3—H3C	109.5
C3—N1—C4	109.31 (15)	N1—C4—H4A	109.5
C5—N1—C4	108.53 (15)	N1—C4—H4B	109.5
C3—N1—C2	111.65 (13)	H4A—C4—H4B	109.5
C5—N1—C2	107.20 (14)	N1—C4—H4C	109.5
C4—N1—C2	111.84 (14)	H4A—C4—H4C	109.5
O1—C1—C2	110.62 (14)	H4B—C4—H4C	109.5
O1—C1—H1A	109.5	N1—C5—H5A	109.5
C2—C1—H1A	109.5	N1—C5—H5B	109.5
O1—C1—H1B	109.5	H5A—C5—H5B	109.5
C2—C1—H1B	109.5	N1—C5—H5C	109.5
H1A—C1—H1B	108.1	H5A—C5—H5C	109.5
C1—C2—N1	117.20 (15)	H5B—C5—H5C	109.5
C1—C2—H2A	108.0	H5OA—O5—H5OB	105 (3)
N1—C2—H2A	108.0

O4—P1—O1—C1	170.10 (13)	O1—C1—C2—N1	−75.8 (2)
O3—P1—O1—C1	−63.97 (14)	C3—N1—C2—C1	−54.4 (2)
O2—P1—O1—C1	50.72 (15)	C5—N1—C2—C1	−172.72 (15)
P1—O1—C1—C2	179.94 (12)	C4—N1—C2—C1	68.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O4ⁱ	0.80 (3)	1.74 (3)	2.525 (2)	167 (3)
O5—H5OA···O3ⁱⁱ	0.77 (3)	1.99 (3)	2.764 (2)	175 (3)
O5—H5OB···O3ⁱⁱⁱ	0.75 (3)	2.04 (3)	2.784 (2)	172 (3)
C2—H2A···O3^iv	0.99	2.47	3.440 (2)	167
C3—H3B···O5^v	0.98	2.52	3.479 (3)	167
C3—H3C···O3^vi	0.98	2.51	3.388 (2)	149
C5—H5C···O4^vii	0.98	2.36	3.219 (3)	146

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1/2, y+3/2, −z+1/2; (iv) x, y+1, z; (v) x−1/2, −y+1/2, z+1/2; (vi) −x, −y, −z+1; (vii) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O4ⁱ	0.80 (3)	1.74 (3)	2.525 (2)	167 (3)
O5—H5OA···O3ⁱⁱ	0.77 (3)	1.99 (3)	2.764 (2)	175 (3)
O5—H5OB···O3ⁱⁱⁱ	0.75 (3)	2.04 (3)	2.784 (2)	172 (3)
C2—H2A···O3^iv	0.99	2.47	3.440 (2)	167
C3—H3B···O5^v	0.98	2.52	3.479 (3)	167
C3—H3C···O3^vi	0.98	2.51	3.388 (2)	149
C5—H5C···O4^vii	0.98	2.36	3.219 (3)	146

Acknowledgements

This research was supported by a Grant-in-Aid for Scientific Research to HO (No. 21225007) and KF (No. 23750120) from the Japan Society for the Promotion of Science. KF is grateful to the Funds for Development of Human Resources in Science and Technology "Supporting positive activities for female researchers", the Ministry of Education, Culture, Sports, Science and Technology, Japan.

References

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

2-(Tri­methyl­aza­nium­yl)ethyl hydrogen phosphate (phospho­choline) mono­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(Trimethylazaniumyl)ethyl hydrogen phosphate (phosphocholine) monohydrate