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The molecule of the title compound, C5H14NO4P, exists as a zwitterion rather than as [1-(hydroxyethyl­amino)propyl]­phospho­nic acid, with the N atom of the amino group protonated and the phospho­nic acid group negatively charged. In the crystal structure, the molecules are linked via extensive hydrogen bonding, forming layers parallel to (100).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032623/ob6454sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032623/ob6454Isup2.hkl
Contains datablock I

CCDC reference: 262472

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.123
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

[1-(hydroxyethylammonio)propyl]phosphonate top
Crystal data top
C5H14NO4PF(000) = 392
Mr = 183.14Dx = 1.444 Mg m3
Monoclinic, P21/cMelting point: 378 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.525 (3) ÅCell parameters from 22 reflections
b = 5.992 (3) Åθ = 19.9–21.1°
c = 14.817 (2) ŵ = 0.30 mm1
β = 94.77 (2)°T = 290 K
V = 842.7 (5) Å3Prism, colourless
Z = 40.28 × 0.28 × 0.20 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
θmax = 26.0°, θmin = 2.2°
Radiation source: fine-focus sealed tubeh = 011
non–profiled ω/2θ scansk = 07
1757 measured reflectionsl = 1818
1654 independent reflections3 standard reflections every 120 min
1305 reflections with I > 2σ(I) intensity decay: none
Rint = 0.021
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0699P)2 + 1.1953P]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max < 0.001
1654 reflectionsΔρmax = 0.33 e Å3
102 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.007 (2)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1577 (3)0.6950 (5)0.33790 (18)0.0314 (6)
H1A0.15950.85840.33630.038*
C20.2755 (3)0.6217 (7)0.4087 (2)0.0501 (9)
H2A0.35840.71090.40030.060*
H2B0.24620.65600.46820.060*
C30.3173 (4)0.3778 (7)0.4074 (3)0.0620 (11)
H3A0.23480.28640.40900.093*
H3B0.38140.34580.45930.093*
H3C0.36240.34680.35320.093*
C40.3184 (3)0.6749 (5)0.2088 (2)0.0378 (7)
H4A0.39320.65770.25690.045*
H4B0.31680.82960.18950.045*
C50.3469 (3)0.5262 (6)0.1303 (2)0.0448 (8)
H5A0.26390.52260.08770.054*
H5B0.42360.58880.09940.054*
O40.3820 (2)0.3057 (4)0.15780 (18)0.0550 (7)
H4C0.31670.25100.18290.083*
N10.1795 (2)0.6157 (4)0.24387 (14)0.0285 (5)
H1B0.17040.46620.24260.034*
H1C0.11020.67250.20560.034*
O10.0441 (2)0.7733 (3)0.44645 (12)0.0366 (5)
H1D0.01080.74230.49020.055*
O20.11980 (19)0.6732 (3)0.28695 (12)0.0305 (5)
O30.02139 (19)0.3719 (3)0.39345 (12)0.0307 (5)
P0.01846 (7)0.61372 (11)0.36636 (4)0.0258 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0359 (14)0.0255 (13)0.0322 (14)0.0025 (11)0.0002 (11)0.0032 (11)
C20.0387 (17)0.070 (2)0.0403 (17)0.0001 (17)0.0072 (13)0.0063 (17)
C30.0470 (19)0.083 (3)0.055 (2)0.026 (2)0.0037 (16)0.015 (2)
C40.0291 (14)0.0350 (17)0.0495 (17)0.0062 (12)0.0050 (12)0.0043 (13)
C50.0364 (16)0.053 (2)0.0458 (18)0.0055 (15)0.0113 (14)0.0049 (15)
O40.0390 (12)0.0450 (14)0.0822 (18)0.0081 (11)0.0115 (12)0.0051 (13)
N10.0268 (11)0.0247 (11)0.0340 (12)0.0008 (9)0.0017 (9)0.0023 (10)
O10.0559 (13)0.0267 (10)0.0265 (10)0.0091 (9)0.0005 (9)0.0036 (8)
O20.0346 (10)0.0278 (10)0.0283 (10)0.0020 (8)0.0015 (8)0.0017 (8)
O30.0426 (11)0.0226 (10)0.0265 (9)0.0016 (8)0.0001 (8)0.0025 (8)
P0.0327 (4)0.0207 (4)0.0237 (4)0.0018 (3)0.0006 (2)0.0003 (3)
Geometric parameters (Å, º) top
C1—N11.503 (3)C4—H4A0.9700
C1—C21.534 (4)C4—H4B0.9700
C1—P1.830 (3)C5—O41.415 (4)
C1—H1A0.9800C5—H5A0.9700
C2—C31.515 (5)C5—H5B0.9700
C2—H2A0.9700O4—H4C0.8200
C2—H2B0.9700N1—H1B0.9000
C3—H3A0.9600N1—H1C0.9000
C3—H3B0.9600O1—P1.5590 (19)
C3—H3C0.9600O1—H1D0.8200
C4—N11.503 (3)O2—P1.5013 (19)
C4—C51.508 (4)O3—P1.5046 (19)
N1—C1—C2113.2 (2)C5—C4—H4B109.6
N1—C1—P109.23 (17)H4A—C4—H4B108.1
C2—C1—P113.5 (2)O4—C5—C4112.5 (3)
N1—C1—H1A106.8O4—C5—H5A109.1
C2—C1—H1A106.8C4—C5—H5A109.1
P—C1—H1A106.8O4—C5—H5B109.1
C3—C2—C1116.5 (3)C4—C5—H5B109.1
C3—C2—H2A108.2H5A—C5—H5B107.8
C1—C2—H2A108.2C5—O4—H4C109.5
C3—C2—H2B108.2C4—N1—C1116.0 (2)
C1—C2—H2B108.2C4—N1—H1B108.3
H2A—C2—H2B107.3C1—N1—H1B108.3
C2—C3—H3A109.5C4—N1—H1C108.3
C2—C3—H3B109.5C1—N1—H1C108.3
H3A—C3—H3B109.5H1B—N1—H1C107.4
C2—C3—H3C109.5P—O1—H1D109.5
H3A—C3—H3C109.5O2—P—O3114.37 (11)
H3B—C3—H3C109.5O2—P—O1108.66 (11)
N1—C4—C5110.3 (2)O3—P—O1112.34 (11)
N1—C4—H4A109.6O2—P—C1107.37 (12)
C5—C4—H4A109.6O3—P—C1110.82 (12)
N1—C4—H4B109.6O1—P—C1102.53 (12)
O1—P—C1—N1160.84 (17)P—C1—C2—C377.0 (3)
P—C1—N1—C4178.3 (2)O2—P—C1—N146.5 (2)
C1—N1—C4—C5161.2 (2)O3—P—C1—N179.1 (2)
N1—C4—C5—O472.6 (3)O2—P—C1—C2173.8 (2)
O1—P—C1—C271.8 (2)O3—P—C1—C248.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4C···O2i0.822.022.807 (3)161
N1—H1B···O2i0.901.862.742 (3)165
N1—H1C···O3ii0.902.022.873 (3)157
O1—H1D···O3iii0.821.852.555 (3)143
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x, y+1, z+1.
 

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