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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
CCDC reference: 262472
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (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
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
C5H14NO4P | F(000) = 392 |
Mr = 183.14 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/c | Melting point: 378 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.525 (3) Å | Cell parameters from 22 reflections |
b = 5.992 (3) Å | θ = 19.9–21.1° |
c = 14.817 (2) Å | µ = 0.30 mm−1 |
β = 94.77 (2)° | T = 290 K |
V = 842.7 (5) Å3 | Prism, colourless |
Z = 4 | 0.28 × 0.28 × 0.20 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | θmax = 26.0°, θmin = 2.2° |
Radiation source: fine-focus sealed tube | h = 0→11 |
non–profiled ω/2θ scans | k = 0→7 |
1757 measured reflections | l = −18→18 |
1654 independent reflections | 3 standard reflections every 120 min |
1305 reflections with I > 2σ(I) | intensity decay: none |
Rint = 0.021 | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-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 reflections | Δρmax = 0.33 e Å−3 |
102 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.1577 (3) | 0.6950 (5) | 0.33790 (18) | 0.0314 (6) | |
H1A | 0.1595 | 0.8584 | 0.3363 | 0.038* | |
C2 | 0.2755 (3) | 0.6217 (7) | 0.4087 (2) | 0.0501 (9) | |
H2A | 0.3584 | 0.7109 | 0.4003 | 0.060* | |
H2B | 0.2462 | 0.6560 | 0.4682 | 0.060* | |
C3 | 0.3173 (4) | 0.3778 (7) | 0.4074 (3) | 0.0620 (11) | |
H3A | 0.2348 | 0.2864 | 0.4090 | 0.093* | |
H3B | 0.3814 | 0.3458 | 0.4593 | 0.093* | |
H3C | 0.3624 | 0.3468 | 0.3532 | 0.093* | |
C4 | 0.3184 (3) | 0.6749 (5) | 0.2088 (2) | 0.0378 (7) | |
H4A | 0.3932 | 0.6577 | 0.2569 | 0.045* | |
H4B | 0.3168 | 0.8296 | 0.1895 | 0.045* | |
C5 | 0.3469 (3) | 0.5262 (6) | 0.1303 (2) | 0.0448 (8) | |
H5A | 0.2639 | 0.5226 | 0.0877 | 0.054* | |
H5B | 0.4236 | 0.5888 | 0.0994 | 0.054* | |
O4 | 0.3820 (2) | 0.3057 (4) | 0.15780 (18) | 0.0550 (7) | |
H4C | 0.3167 | 0.2510 | 0.1829 | 0.083* | |
N1 | 0.1795 (2) | 0.6157 (4) | 0.24387 (14) | 0.0285 (5) | |
H1B | 0.1704 | 0.4662 | 0.2426 | 0.034* | |
H1C | 0.1102 | 0.6725 | 0.2056 | 0.034* | |
O1 | −0.0441 (2) | 0.7733 (3) | 0.44645 (12) | 0.0366 (5) | |
H1D | 0.0108 | 0.7423 | 0.4902 | 0.055* | |
O2 | −0.11980 (19) | 0.6732 (3) | 0.28695 (12) | 0.0305 (5) | |
O3 | −0.02139 (19) | 0.3719 (3) | 0.39345 (12) | 0.0307 (5) | |
P | −0.01846 (7) | 0.61372 (11) | 0.36636 (4) | 0.0258 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0359 (14) | 0.0255 (13) | 0.0322 (14) | −0.0025 (11) | −0.0002 (11) | −0.0032 (11) |
C2 | 0.0387 (17) | 0.070 (2) | 0.0403 (17) | 0.0001 (17) | −0.0072 (13) | −0.0063 (17) |
C3 | 0.0470 (19) | 0.083 (3) | 0.055 (2) | 0.026 (2) | −0.0037 (16) | 0.015 (2) |
C4 | 0.0291 (14) | 0.0350 (17) | 0.0495 (17) | −0.0062 (12) | 0.0050 (12) | 0.0043 (13) |
C5 | 0.0364 (16) | 0.053 (2) | 0.0458 (18) | −0.0055 (15) | 0.0113 (14) | 0.0049 (15) |
O4 | 0.0390 (12) | 0.0450 (14) | 0.0822 (18) | 0.0081 (11) | 0.0115 (12) | −0.0051 (13) |
N1 | 0.0268 (11) | 0.0247 (11) | 0.0340 (12) | −0.0008 (9) | 0.0017 (9) | 0.0023 (10) |
O1 | 0.0559 (13) | 0.0267 (10) | 0.0265 (10) | 0.0091 (9) | −0.0005 (9) | −0.0036 (8) |
O2 | 0.0346 (10) | 0.0278 (10) | 0.0283 (10) | 0.0020 (8) | −0.0015 (8) | 0.0017 (8) |
O3 | 0.0426 (11) | 0.0226 (10) | 0.0265 (9) | 0.0016 (8) | 0.0001 (8) | 0.0025 (8) |
P | 0.0327 (4) | 0.0207 (4) | 0.0237 (4) | 0.0018 (3) | 0.0006 (2) | −0.0003 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.503 (3) | C4—H4A | 0.9700 |
C1—C2 | 1.534 (4) | C4—H4B | 0.9700 |
C1—P | 1.830 (3) | C5—O4 | 1.415 (4) |
C1—H1A | 0.9800 | C5—H5A | 0.9700 |
C2—C3 | 1.515 (5) | C5—H5B | 0.9700 |
C2—H2A | 0.9700 | O4—H4C | 0.8200 |
C2—H2B | 0.9700 | N1—H1B | 0.9000 |
C3—H3A | 0.9600 | N1—H1C | 0.9000 |
C3—H3B | 0.9600 | O1—P | 1.5590 (19) |
C3—H3C | 0.9600 | O1—H1D | 0.8200 |
C4—N1 | 1.503 (3) | O2—P | 1.5013 (19) |
C4—C5 | 1.508 (4) | O3—P | 1.5046 (19) |
| | | |
N1—C1—C2 | 113.2 (2) | C5—C4—H4B | 109.6 |
N1—C1—P | 109.23 (17) | H4A—C4—H4B | 108.1 |
C2—C1—P | 113.5 (2) | O4—C5—C4 | 112.5 (3) |
N1—C1—H1A | 106.8 | O4—C5—H5A | 109.1 |
C2—C1—H1A | 106.8 | C4—C5—H5A | 109.1 |
P—C1—H1A | 106.8 | O4—C5—H5B | 109.1 |
C3—C2—C1 | 116.5 (3) | C4—C5—H5B | 109.1 |
C3—C2—H2A | 108.2 | H5A—C5—H5B | 107.8 |
C1—C2—H2A | 108.2 | C5—O4—H4C | 109.5 |
C3—C2—H2B | 108.2 | C4—N1—C1 | 116.0 (2) |
C1—C2—H2B | 108.2 | C4—N1—H1B | 108.3 |
H2A—C2—H2B | 107.3 | C1—N1—H1B | 108.3 |
C2—C3—H3A | 109.5 | C4—N1—H1C | 108.3 |
C2—C3—H3B | 109.5 | C1—N1—H1C | 108.3 |
H3A—C3—H3B | 109.5 | H1B—N1—H1C | 107.4 |
C2—C3—H3C | 109.5 | P—O1—H1D | 109.5 |
H3A—C3—H3C | 109.5 | O2—P—O3 | 114.37 (11) |
H3B—C3—H3C | 109.5 | O2—P—O1 | 108.66 (11) |
N1—C4—C5 | 110.3 (2) | O3—P—O1 | 112.34 (11) |
N1—C4—H4A | 109.6 | O2—P—C1 | 107.37 (12) |
C5—C4—H4A | 109.6 | O3—P—C1 | 110.82 (12) |
N1—C4—H4B | 109.6 | O1—P—C1 | 102.53 (12) |
| | | |
O1—P—C1—N1 | −160.84 (17) | P—C1—C2—C3 | 77.0 (3) |
P—C1—N1—C4 | 178.3 (2) | O2—P—C1—N1 | −46.5 (2) |
C1—N1—C4—C5 | 161.2 (2) | O3—P—C1—N1 | 79.1 (2) |
N1—C4—C5—O4 | −72.6 (3) | O2—P—C1—C2 | −173.8 (2) |
O1—P—C1—C2 | 71.8 (2) | O3—P—C1—C2 | −48.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4C···O2i | 0.82 | 2.02 | 2.807 (3) | 161 |
N1—H1B···O2i | 0.90 | 1.86 | 2.742 (3) | 165 |
N1—H1C···O3ii | 0.90 | 2.02 | 2.873 (3) | 157 |
O1—H1D···O3iii | 0.82 | 1.85 | 2.555 (3) | 143 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, −y+1, −z+1. |
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