![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
(S)-1-Hydroxypropan-2-aminium (2R,3R)-3-carboxy-2,3-dihydroxypropanoate monohydrate
aSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China, bTianjin Foreign Studies University, Tianjin 300204, People's Republic of China, and cTianjin EPC Petrochemical Engineering Co. Ltd, Tianjin 300000, People's Republic of China
*Correspondence e-mail: xinyutatala@yahoo.com.cn
The chiral title compound, C4H10NO+·C4H5O6−·H2O, is a hydrated molecular salt in which the tartaric acid has transferred one proton to the (S)-2-aminopropan-1-ol molecule. The is stabilized by a three-dimensional network of N—H⋯O and O—H⋯O hydrogen bonds. The was assigned on the basis of the starting materials.
Related literature
For the synthesis, see: Bai et al. (2004); For background, see: Humljan et al. (2006
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Bruker, 1997
); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808000391/hb2687sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808000391/hb2687Isup2.hkl
The title compound was prepared by the procedure of Bai et al. (2004). Colourless single crystals of (I) were grown by slow evaporation of a solution of methanol and water.
Anomalous dispersion was negligible and Friedel pairs were merged before refinement.
The N– and O-bound H atoms were located in difference maps and their positions were freely refined with Uiso(H) = 1.5Ueq(carrier).
The C-bound H atoms were positioned geometrically (C—H = 0.96–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell
SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).C3H10NO+·C4H5O6−·H2O | F(000) = 520 |
Mr = 243.22 | Dx = 1.444 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3930 reflections |
a = 7.533 (2) Å | θ = 2.9–26.4° |
b = 7.701 (2) Å | µ = 0.13 mm−1 |
c = 19.288 (5) Å | T = 294 K |
V = 1118.9 (5) Å3 | Block, colourless |
Z = 4 | 0.24 × 0.22 × 0.18 mm |
Bruker SMART CCD diffractometer | 1359 independent reflections |
Radiation source: fine-focus sealed tube | 1280 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −9→6 |
Tmin = 0.969, Tmax = 0.977 | k = −9→9 |
6331 measured reflections | l = −17→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difmap (N-H and O-H) and geom (C-H) |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0475P)2 + 0.1468P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1359 reflections | Δρmax = 0.25 e Å−3 |
174 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.067 (5) |
C3H10NO+·C4H5O6−·H2O | V = 1118.9 (5) Å3 |
Mr = 243.22 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.533 (2) Å | µ = 0.13 mm−1 |
b = 7.701 (2) Å | T = 294 K |
c = 19.288 (5) Å | 0.24 × 0.22 × 0.18 mm |
Bruker SMART CCD diffractometer | 1359 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1280 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.977 | Rint = 0.024 |
6331 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.25 e Å−3 |
1359 reflections | Δρmin = −0.17 e Å−3 |
174 parameters |
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 | ||
O1 | 0.5541 (2) | 0.9115 (2) | 0.77366 (8) | 0.0413 (4) | |
H1 | 0.611 (4) | 0.989 (4) | 0.7999 (16) | 0.062* | |
O2 | 0.14604 (17) | 0.39481 (16) | 0.92596 (8) | 0.0324 (3) | |
O3 | 0.42454 (16) | 0.30294 (16) | 0.92082 (7) | 0.0285 (3) | |
O4 | 0.01406 (16) | 0.07039 (17) | 0.94283 (7) | 0.0279 (3) | |
H4 | 0.002 (3) | 0.110 (3) | 0.9859 (13) | 0.042* | |
O5 | 0.30427 (18) | 0.05497 (16) | 1.04183 (6) | 0.0244 (3) | |
H5 | 0.406 (3) | 0.086 (3) | 1.0507 (12) | 0.037* | |
O6 | 0.2651 (2) | −0.28770 (17) | 0.91791 (7) | 0.0324 (3) | |
H6 | 0.218 (4) | −0.387 (4) | 0.9212 (13) | 0.049* | |
O7 | 0.1836 (2) | −0.27117 (18) | 1.02899 (7) | 0.0380 (4) | |
N1 | 0.6127 (2) | 0.5901 (2) | 0.84455 (8) | 0.0280 (4) | |
H1D | 0.561 (3) | 0.510 (3) | 0.8145 (13) | 0.042* | |
H1E | 0.665 (3) | 0.529 (3) | 0.8822 (13) | 0.042* | |
H1F | 0.521 (3) | 0.666 (3) | 0.8599 (12) | 0.042* | |
C1 | 0.8957 (3) | 0.5543 (4) | 0.78287 (12) | 0.0517 (6) | |
H1A | 0.8387 | 0.4739 | 0.7520 | 0.078* | |
H1B | 0.9459 | 0.4921 | 0.8213 | 0.078* | |
H1C | 0.9882 | 0.6146 | 0.7585 | 0.078* | |
C2 | 0.7608 (3) | 0.6838 (2) | 0.80928 (9) | 0.0288 (4) | |
H2 | 0.8185 | 0.7610 | 0.8428 | 0.035* | |
C3 | 0.6849 (3) | 0.7920 (3) | 0.75103 (10) | 0.0333 (4) | |
H3A | 0.7805 | 0.8555 | 0.7289 | 0.040* | |
H3B | 0.6330 | 0.7154 | 0.7167 | 0.040* | |
C4 | 0.2611 (2) | 0.2769 (2) | 0.92464 (8) | 0.0198 (3) | |
C5 | 0.1966 (2) | 0.0871 (2) | 0.92587 (8) | 0.0204 (3) | |
H5A | 0.2126 | 0.0400 | 0.8791 | 0.025* | |
C6 | 0.3130 (2) | −0.0200 (2) | 0.97483 (8) | 0.0202 (3) | |
H6A | 0.4360 | −0.0185 | 0.9583 | 0.024* | |
C7 | 0.2464 (2) | −0.2062 (2) | 0.97795 (9) | 0.0236 (4) | |
O8 | 0.7125 (2) | 0.1422 (2) | 0.85702 (9) | 0.0460 (4) | |
H8A | 0.633 (4) | 0.190 (4) | 0.8814 (15) | 0.055* | |
H8B | 0.802 (4) | 0.119 (4) | 0.8783 (15) | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0473 (9) | 0.0330 (7) | 0.0436 (8) | 0.0065 (7) | −0.0122 (7) | −0.0017 (7) |
O2 | 0.0262 (6) | 0.0181 (6) | 0.0529 (8) | 0.0018 (5) | 0.0047 (6) | −0.0008 (6) |
O3 | 0.0223 (6) | 0.0244 (6) | 0.0388 (7) | −0.0023 (5) | 0.0013 (5) | 0.0022 (6) |
O4 | 0.0199 (6) | 0.0271 (6) | 0.0368 (7) | −0.0029 (6) | −0.0025 (5) | 0.0002 (6) |
O5 | 0.0243 (6) | 0.0266 (6) | 0.0224 (6) | −0.0045 (5) | −0.0013 (5) | −0.0019 (5) |
O6 | 0.0449 (8) | 0.0189 (6) | 0.0333 (7) | −0.0063 (6) | 0.0090 (6) | −0.0044 (5) |
O7 | 0.0538 (9) | 0.0273 (6) | 0.0329 (7) | −0.0120 (7) | 0.0100 (7) | 0.0029 (6) |
N1 | 0.0337 (9) | 0.0260 (7) | 0.0244 (7) | −0.0005 (8) | 0.0006 (6) | 0.0017 (6) |
C1 | 0.0465 (13) | 0.0641 (15) | 0.0445 (12) | 0.0226 (13) | 0.0113 (10) | 0.0148 (11) |
C2 | 0.0276 (9) | 0.0329 (9) | 0.0259 (8) | −0.0018 (9) | −0.0010 (7) | 0.0022 (7) |
C3 | 0.0421 (11) | 0.0314 (9) | 0.0265 (8) | −0.0037 (9) | −0.0002 (8) | 0.0062 (7) |
C4 | 0.0244 (8) | 0.0181 (7) | 0.0169 (7) | −0.0002 (7) | −0.0004 (7) | 0.0006 (6) |
C5 | 0.0211 (7) | 0.0177 (7) | 0.0225 (7) | −0.0016 (6) | 0.0008 (7) | −0.0008 (7) |
C6 | 0.0195 (7) | 0.0184 (7) | 0.0228 (7) | −0.0003 (7) | 0.0012 (6) | 0.0000 (6) |
C7 | 0.0230 (8) | 0.0187 (8) | 0.0291 (8) | 0.0013 (7) | 0.0000 (7) | 0.0004 (7) |
O8 | 0.0416 (9) | 0.0528 (10) | 0.0435 (9) | 0.0115 (8) | −0.0096 (7) | −0.0171 (7) |
O1—C3 | 1.417 (3) | C1—C2 | 1.512 (3) |
O1—H1 | 0.89 (3) | C1—H1A | 0.9600 |
O2—C4 | 1.256 (2) | C1—H1B | 0.9600 |
O3—C4 | 1.249 (2) | C1—H1C | 0.9600 |
O4—C5 | 1.419 (2) | C2—C3 | 1.511 (3) |
O4—H4 | 0.89 (2) | C2—H2 | 0.9800 |
O5—C6 | 1.4166 (19) | C3—H3A | 0.9700 |
O5—H5 | 0.82 (3) | C3—H3B | 0.9700 |
O6—C7 | 1.325 (2) | C4—C5 | 1.540 (2) |
O6—H6 | 0.85 (3) | C5—C6 | 1.530 (2) |
O7—C7 | 1.202 (2) | C5—H5A | 0.9800 |
N1—C2 | 1.492 (2) | C6—C7 | 1.520 (2) |
N1—H1D | 0.93 (3) | C6—H6A | 0.9800 |
N1—H1E | 0.95 (3) | O8—H8A | 0.85 (3) |
N1—H1F | 0.95 (3) | O8—H8B | 0.81 (3) |
C3—O1—H1 | 106 (2) | C2—C3—H3A | 109.0 |
C5—O4—H4 | 106.3 (16) | O1—C3—H3B | 109.0 |
C6—O5—H5 | 105.4 (17) | C2—C3—H3B | 109.0 |
C7—O6—H6 | 108.7 (17) | H3A—C3—H3B | 107.8 |
C2—N1—H1D | 110.4 (16) | O3—C4—O2 | 124.44 (16) |
C2—N1—H1E | 106.4 (15) | O3—C4—C5 | 117.66 (15) |
H1D—N1—H1E | 108 (2) | O2—C4—C5 | 117.89 (14) |
C2—N1—H1F | 112.7 (15) | O4—C5—C6 | 111.34 (13) |
H1D—N1—H1F | 107 (2) | O4—C5—C4 | 113.31 (14) |
H1E—N1—H1F | 112 (2) | C6—C5—C4 | 109.88 (13) |
C2—C1—H1A | 109.5 | O4—C5—H5A | 107.3 |
C2—C1—H1B | 109.5 | C6—C5—H5A | 107.3 |
H1A—C1—H1B | 109.5 | C4—C5—H5A | 107.3 |
C2—C1—H1C | 109.5 | O5—C6—C7 | 109.44 (13) |
H1A—C1—H1C | 109.5 | O5—C6—C5 | 108.48 (13) |
H1B—C1—H1C | 109.5 | C7—C6—C5 | 110.12 (13) |
N1—C2—C3 | 108.85 (16) | O5—C6—H6A | 109.6 |
N1—C2—C1 | 109.68 (17) | C7—C6—H6A | 109.6 |
C3—C2—C1 | 111.56 (16) | C5—C6—H6A | 109.6 |
N1—C2—H2 | 108.9 | O7—C7—O6 | 124.11 (15) |
C3—C2—H2 | 108.9 | O7—C7—C6 | 123.73 (15) |
C1—C2—H2 | 108.9 | O6—C7—C6 | 112.17 (14) |
O1—C3—C2 | 113.08 (15) | H8A—O8—H8B | 114 (3) |
O1—C3—H3A | 109.0 | ||
N1—C2—C3—O1 | 57.1 (2) | C4—C5—C6—O5 | 58.54 (17) |
C1—C2—C3—O1 | 178.27 (18) | O4—C5—C6—C7 | 51.92 (18) |
O3—C4—C5—O4 | 169.20 (14) | C4—C5—C6—C7 | 178.28 (13) |
O2—C4—C5—O4 | −12.4 (2) | O5—C6—C7—O7 | 5.5 (2) |
O3—C4—C5—C6 | 44.0 (2) | C5—C6—C7—O7 | −113.67 (19) |
O2—C4—C5—C6 | −137.61 (15) | O5—C6—C7—O6 | −174.79 (15) |
O4—C5—C6—O5 | −67.82 (17) | C5—C6—C7—O6 | 66.06 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O8i | 0.89 (3) | 1.78 (3) | 2.677 (2) | 176 (3) |
O4—H4···O3ii | 0.89 (2) | 2.01 (3) | 2.885 (2) | 169 (2) |
O5—H5···O2iii | 0.82 (3) | 1.87 (3) | 2.676 (2) | 167 (3) |
O6—H6···O2iv | 0.85 (3) | 1.77 (3) | 2.6091 (19) | 173 (3) |
N1—H1D···O1v | 0.93 (3) | 2.05 (3) | 2.945 (2) | 159 (2) |
N1—H1E···O5iii | 0.95 (3) | 1.91 (3) | 2.852 (2) | 168 (2) |
N1—H1F···O6i | 0.95 (3) | 2.26 (3) | 3.121 (2) | 150 (2) |
O8—H8A···O3 | 0.85 (3) | 1.95 (3) | 2.784 (2) | 169 (3) |
O8—H8B···O4vi | 0.81 (3) | 2.06 (3) | 2.865 (2) | 173 (3) |
Symmetry codes: (i) x, y+1, z; (ii) x−1/2, −y+1/2, −z+2; (iii) x+1/2, −y+1/2, −z+2; (iv) x, y−1, z; (v) −x+1, y−1/2, −z+3/2; (vi) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C3H10NO+·C4H5O6−·H2O |
Mr | 243.22 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 7.533 (2), 7.701 (2), 19.288 (5) |
V (Å3) | 1118.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.969, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6331, 1359, 1280 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.074, 1.06 |
No. of reflections | 1359 |
No. of parameters | 174 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.17 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O8i | 0.89 (3) | 1.78 (3) | 2.677 (2) | 176 (3) |
O4—H4···O3ii | 0.89 (2) | 2.01 (3) | 2.885 (2) | 169 (2) |
O5—H5···O2iii | 0.82 (3) | 1.87 (3) | 2.676 (2) | 167 (3) |
O6—H6···O2iv | 0.85 (3) | 1.77 (3) | 2.6091 (19) | 173 (3) |
N1—H1D···O1v | 0.93 (3) | 2.05 (3) | 2.945 (2) | 159 (2) |
N1—H1E···O5iii | 0.95 (3) | 1.91 (3) | 2.852 (2) | 168 (2) |
N1—H1F···O6i | 0.95 (3) | 2.26 (3) | 3.121 (2) | 150 (2) |
O8—H8A···O3 | 0.85 (3) | 1.95 (3) | 2.784 (2) | 169 (3) |
O8—H8B···O4vi | 0.81 (3) | 2.06 (3) | 2.865 (2) | 173 (3) |
Symmetry codes: (i) x, y+1, z; (ii) x−1/2, −y+1/2, −z+2; (iii) x+1/2, −y+1/2, −z+2; (iv) x, y−1, z; (v) −x+1, y−1/2, −z+3/2; (vi) x+1, y, z. |
References
Bai, G. Y., Chen, L. G., Xing, P., Li, Y. & Yan, X. L. (2004). Fine Chem. 21, 943–945. CAS Google Scholar
Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Humljan, J., Kotnik, M., Boniface, A., Solmajer, T., Urleb, U., Blanot, D. & Gobec, S. (2006). Tetrahedron, 62, 10980–10988. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound, (I), (Fig. 1), is a hydrated (2R,3R)-tartrate salt of (S)-2-aminopropan-1-ol. (S)-2-aminopropan-1-ol is a key intermediate for the synthesis of potential inhibitors of the bacterial peptidoglycan biosynthesis enzymes MurD and MurE (Humljan et al., 2006).
In the crystal, the (S)-2-aminopropan-1-ol molecule is in a cationic form, and has a positively charged amino group. The tartaric acid molecule is a semi-tartrate ion, with a neutral carboxylic acid group at one end and a negatively charged carboxylate group at the other (Fig. 1). The bond distances and angles in the cation and the anion are normal. The chiralities of the carbon atoms (C2 S, C5 R, C6 R) were assigned according to the known absolute structures of the starting materials.
In the crystal structure of (I), an extensive hydrogen-bond network is built up (Table 1).