2-(Tri-methyl-aza-nium-yl)ethyl hydrogen phosphate (phospho-choline) mono-hydrate.

In the crystal structure of the title compound, C5H14NO4P·H2O, the zwitterionic phospho-choline mol-ecules 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 mol-ecules, forming a layer parallel to (101). Three and one C-H⋯O inter-actions 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)°

Related literature

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

Experimental

Crystal data

C5H14NO4P·H2O

M = 201.16

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.101

S = 1.13

1715 reflections

121 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.50 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400779X/is5344sup1.cif

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

Click here for additional data file.

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

CCDC reference: 996006

Additional supporting information: crystallographic information; 3D view; checkCIF report

C5H14NO4P·H2O	F(000) = 432
Mr = 201.16	Dx = 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

Rigaku R-AXIS RAPID diffractometer	1715 independent reflections
Radiation source: rotating anode	1632 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 4.8°
ω scans	h = −12→12
Absorption correction: numerical (NUMABS; Rigaku, 1999)	k = −8→8
Tmin = 0.306, Tmax = 0.424	l = −15→16
16036 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)] = 0.038	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(Fo2) + (0.0594P)2 + 0.4329P] where P = (Fo2 + 2Fc2)/3
1715 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.50 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	0.19372 (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)*

	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)

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)

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···O3iv	0.99	2.47	3.440 (2)	167
C3—H3B···O5v	0.98	2.52	3.479 (3)	167
C3—H3C···O3vi	0.98	2.51	3.388 (2)	149
C5—H5C···O4vii	0.98	2.36	3.219 (3)	146

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⋯O3iv	0.99	2.47	3.440 (2)	167
C3—H3B⋯O5v	0.98	2.52	3.479 (3)	167
C3—H3C⋯O3vi	0.98	2.51	3.388 (2)	149
C5—H5C⋯O4vii	0.98	2.36	3.219 (3)	146

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