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Acta Cryst. (2008). E64, o422    [ doi:10.1107/S1600536808000391 ]

(S)-1-Hydroxypropan-2-aminium (2R,3R)-3-carboxy-2,3-dihydroxypropanoate monohydrate

X.-Y. Tang, X.-L. Yan, P. Zhang, L. Qin and Y. Yin

Abstract top

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 crystal structure is stabilized by a three-dimensional network of N-H...O and O-H...O hydrogen bonds. The absolute configuration was assigned on the basis of the starting materials.

Comment top

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).

Related literature top

For the synthesis, see: Bai et al. (2004); For backgrond, see: Humljan et al. (2006).

Experimental top

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.

Refinement top

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).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I). Displacement ellopsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radius. The hydrogen bond is indicated by a double dashed line.
(S)-1-hydroxypropan-2-aminium (2R,3R)-3-carboxy -2,3-dihydroxypropanoate monohydrate top
Crystal data top
C3H10NO1+·C4H5O61–·H2OF000 = 520
Mr = 243.22Dx = 1.444 Mg m−3
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3930 reflections
a = 7.533 (2) Åθ = 2.9–26.4º
b = 7.701 (2) ŵ = 0.13 mm−1
c = 19.288 (5) ÅT = 294 (2) K
V = 1118.9 (5) Å3Block, colourless
Z = 40.24 × 0.22 × 0.18 mm
Data collection top
Bruker SMART CCD
diffractometer		1359 independent reflections
Radiation source: fine-focus sealed tube1280 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 294(2) Kθmax = 26.4º
ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −9→6
Tmin = 0.969, Tmax = 0.977k = −9→9
6331 measured reflectionsl = −17→24
Refinement top
Refinement on F2Hydrogen site location: difmap (N-H and O-H) and geom (C-H)
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.028  w = 1/[σ2(Fo2) + (0.0475P)2 + 0.1468P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.25 e Å−3
1359 reflectionsΔρmin = −0.17 e Å−3
174 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.067 (5)
Secondary atom site location: difference Fourier map
Crystal data top
C3H10NO1+·C4H5O61–·H2OV = 1118.9 (5) Å3
Mr = 243.22Z = 4
Orthorhombic, P212121Mo Kα
a = 7.533 (2) ŵ = 0.13 mm−1
b = 7.701 (2) ÅT = 294 (2) K
c = 19.288 (5) Å0.24 × 0.22 × 0.18 mm
Data collection top
Bruker SMART CCD
diffractometer		1359 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		1280 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.977Rint = 0.024
6331 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028174 parameters
wR(F2) = 0.074H atoms treated by a mixture of
independent and constrained refinement
S = 1.06Δρmax = 0.25 e Å−3
1359 reflectionsΔρmin = −0.17 e Å−3
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
xyzUiso*/Ueq
O10.5541 (2)0.9115 (2)0.77366 (8)0.0413 (4)
H10.611 (4)0.989 (4)0.7999 (16)0.062*
O20.14604 (17)0.39481 (16)0.92596 (8)0.0324 (3)
O30.42454 (16)0.30294 (16)0.92082 (7)0.0285 (3)
O40.01406 (16)0.07039 (17)0.94283 (7)0.0279 (3)
H40.002 (3)0.110 (3)0.9859 (13)0.042*
O50.30427 (18)0.05497 (16)1.04183 (6)0.0244 (3)
H50.406 (3)0.086 (3)1.0507 (12)0.037*
O60.2651 (2)−0.28770 (17)0.91791 (7)0.0324 (3)
H60.218 (4)−0.387 (4)0.9212 (13)0.049*
O70.1836 (2)−0.27117 (18)1.02899 (7)0.0380 (4)
N10.6127 (2)0.5901 (2)0.84455 (8)0.0280 (4)
H1D0.561 (3)0.510 (3)0.8145 (13)0.042*
H1E0.665 (3)0.529 (3)0.8822 (13)0.042*
H1F0.521 (3)0.666 (3)0.8599 (12)0.042*
C10.8957 (3)0.5543 (4)0.78287 (12)0.0517 (6)
H1A0.83870.47390.75200.078*
H1B0.94590.49210.82130.078*
H1C0.98820.61460.75850.078*
C20.7608 (3)0.6838 (2)0.80928 (9)0.0288 (4)
H20.81850.76100.84280.035*
C30.6849 (3)0.7920 (3)0.75103 (10)0.0333 (4)
H3A0.78050.85550.72890.040*
H3B0.63300.71540.71670.040*
C40.2611 (2)0.2769 (2)0.92464 (8)0.0198 (3)
C50.1966 (2)0.0871 (2)0.92587 (8)0.0204 (3)
H5A0.21260.04000.87910.025*
C60.3130 (2)−0.0200 (2)0.97483 (8)0.0202 (3)
H6A0.4360−0.01850.95830.024*
C70.2464 (2)−0.2062 (2)0.97795 (9)0.0236 (4)
O80.7125 (2)0.1422 (2)0.85702 (9)0.0460 (4)
H8A0.633 (4)0.190 (4)0.8814 (15)0.055*
H8B0.802 (4)0.119 (4)0.8783 (15)0.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0473 (9)0.0330 (7)0.0436 (8)0.0065 (7)−0.0122 (7)−0.0017 (7)
O20.0262 (6)0.0181 (6)0.0529 (8)0.0018 (5)0.0047 (6)−0.0008 (6)
O30.0223 (6)0.0244 (6)0.0388 (7)−0.0023 (5)0.0013 (5)0.0022 (6)
O40.0199 (6)0.0271 (6)0.0368 (7)−0.0029 (6)−0.0025 (5)0.0002 (6)
O50.0243 (6)0.0266 (6)0.0224 (6)−0.0045 (5)−0.0013 (5)−0.0019 (5)
O60.0449 (8)0.0189 (6)0.0333 (7)−0.0063 (6)0.0090 (6)−0.0044 (5)
O70.0538 (9)0.0273 (6)0.0329 (7)−0.0120 (7)0.0100 (7)0.0029 (6)
N10.0337 (9)0.0260 (7)0.0244 (7)−0.0005 (8)0.0006 (6)0.0017 (6)
C10.0465 (13)0.0641 (15)0.0445 (12)0.0226 (13)0.0113 (10)0.0148 (11)
C20.0276 (9)0.0329 (9)0.0259 (8)−0.0018 (9)−0.0010 (7)0.0022 (7)
C30.0421 (11)0.0314 (9)0.0265 (8)−0.0037 (9)−0.0002 (8)0.0062 (7)
C40.0244 (8)0.0181 (7)0.0169 (7)−0.0002 (7)−0.0004 (7)0.0006 (6)
C50.0211 (7)0.0177 (7)0.0225 (7)−0.0016 (6)0.0008 (7)−0.0008 (7)
C60.0195 (7)0.0184 (7)0.0228 (7)−0.0003 (7)0.0012 (6)0.0000 (6)
C70.0230 (8)0.0187 (8)0.0291 (8)0.0013 (7)0.0000 (7)0.0004 (7)
O80.0416 (9)0.0528 (10)0.0435 (9)0.0115 (8)−0.0096 (7)−0.0171 (7)
Geometric parameters (Å, °) top
O1—C31.417 (3)C1—C21.512 (3)
O1—H10.89 (3)C1—H1A0.9600
O2—C41.256 (2)C1—H1B0.9600
O3—C41.249 (2)C1—H1C0.9600
O4—C51.419 (2)C2—C31.511 (3)
O4—H40.89 (2)C2—H20.9800
O5—C61.4166 (19)C3—H3A0.9700
O5—H50.82 (3)C3—H3B0.9700
O6—C71.325 (2)C4—C51.540 (2)
O6—H60.85 (3)C5—C61.530 (2)
O7—C71.202 (2)C5—H5A0.9800
N1—C21.492 (2)C6—C71.520 (2)
N1—H1D0.93 (3)C6—H6A0.9800
N1—H1E0.95 (3)O8—H8A0.85 (3)
N1—H1F0.95 (3)O8—H8B0.81 (3)
C3—O1—H1106 (2)C2—C3—H3A109.0
C5—O4—H4106.3 (16)O1—C3—H3B109.0
C6—O5—H5105.4 (17)C2—C3—H3B109.0
C7—O6—H6108.7 (17)H3A—C3—H3B107.8
C2—N1—H1D110.4 (16)O3—C4—O2124.44 (16)
C2—N1—H1E106.4 (15)O3—C4—C5117.66 (15)
H1D—N1—H1E108 (2)O2—C4—C5117.89 (14)
C2—N1—H1F112.7 (15)O4—C5—C6111.34 (13)
H1D—N1—H1F107 (2)O4—C5—C4113.31 (14)
H1E—N1—H1F112 (2)C6—C5—C4109.88 (13)
C2—C1—H1A109.5O4—C5—H5A107.3
C2—C1—H1B109.5C6—C5—H5A107.3
H1A—C1—H1B109.5C4—C5—H5A107.3
C2—C1—H1C109.5O5—C6—C7109.44 (13)
H1A—C1—H1C109.5O5—C6—C5108.48 (13)
H1B—C1—H1C109.5C7—C6—C5110.12 (13)
N1—C2—C3108.85 (16)O5—C6—H6A109.6
N1—C2—C1109.68 (17)C7—C6—H6A109.6
C3—C2—C1111.56 (16)C5—C6—H6A109.6
N1—C2—H2108.9O7—C7—O6124.11 (15)
C3—C2—H2108.9O7—C7—C6123.73 (15)
C1—C2—H2108.9O6—C7—C6112.17 (14)
O1—C3—C2113.08 (15)H8A—O8—H8B114 (3)
O1—C3—H3A109.0
N1—C2—C3—O157.1 (2)C4—C5—C6—O558.54 (17)
C1—C2—C3—O1178.27 (18)O4—C5—C6—C751.92 (18)
O3—C4—C5—O4169.20 (14)C4—C5—C6—C7178.28 (13)
O2—C4—C5—O4−12.4 (2)O5—C6—C7—O75.5 (2)
O3—C4—C5—C644.0 (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—O666.06 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O8i0.89 (3)1.78 (3)2.677 (2)176 (3)
O4—H4···O3ii0.89 (2)2.01 (3)2.885 (2)169 (2)
O5—H5···O2iii0.82 (3)1.87 (3)2.676 (2)167 (3)
O6—H6···O2iv0.85 (3)1.77 (3)2.6091 (19)173 (3)
N1—H1D···O1v0.93 (3)2.05 (3)2.945 (2)159 (2)
N1—H1E···O5iii0.95 (3)1.91 (3)2.852 (2)168 (2)
N1—H1F···O6i0.95 (3)2.26 (3)3.121 (2)150 (2)
O8—H8A···O30.85 (3)1.95 (3)2.784 (2)169 (3)
O8—H8B···O4vi0.81 (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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O8i0.89 (3)1.78 (3)2.677 (2)176 (3)
O4—H4···O3ii0.89 (2)2.01 (3)2.885 (2)169 (2)
O5—H5···O2iii0.82 (3)1.87 (3)2.676 (2)167 (3)
O6—H6···O2iv0.85 (3)1.77 (3)2.6091 (19)173 (3)
N1—H1D···O1v0.93 (3)2.05 (3)2.945 (2)159 (2)
N1—H1E···O5iii0.95 (3)1.91 (3)2.852 (2)168 (2)
N1—H1F···O6i0.95 (3)2.26 (3)3.121 (2)150 (2)
O8—H8A···O30.85 (3)1.95 (3)2.784 (2)169 (3)
O8—H8B···O4vi0.81 (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
References top

Bai, G. Y., Chen, L. G., Xing, P., Li, Y. & Yan, X. L. (2004). Fine Chem. , 21, 943–945.

Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Humljan, J., Kotnik, M., Boniface, A., Solmajer, T., Urleb, U., Blanot, D. & Gobec, S. (2006). Tetrahedron, 62, 10980–10988.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.