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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 2| February 2008| Page o422
doi:10.1107/S1600536808000391

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

Xin-Yu Tang,a Xi-Long Yan,a* Ping Zhang,b Ling Qina and Yueguang Yinc

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

(Received 4 January 2008; accepted 6 January 2008; online 11 January 2008)

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.

Related literature

For the synthesis, see: Bai et al. (2004[Bai, G. Y., Chen, L. G., Xing, P., Li, Y. & Yan, X. L. (2004). Fine Chem. 21, 943-945.]); For background, see: Humljan et al. (2006[Humljan, J., Kotnik, M., Boniface, A., Solmajer, T., Urleb, U., Blanot, D. & Gobec, S. (2006). Tetrahedron, 62, 10980-10988.]).

[Scheme 1]

Experimental

Crystal data

  • C4H10NO+·C4H5O6−·H2O

  • Mr = 243.22

  • Orthorhombic, P 21 21 21

  • a = 7.533 (2) Å

  • b = 7.701 (2) Å

  • c = 19.288 (5) Å

  • V = 1118.9 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 294 (2) K

  • 0.24 × 0.22 × 0.18 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.977

  • 6331 measured reflections

  • 1359 independent reflections

  • 1280 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.074

  • S = 1.06

  • 1359 reflections

  • 174 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]; (iv) x, y-1, z; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (vi) x+1, y, z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Bruker, 1997[Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000391/hb2687sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000391/hb2687Isup2.hkl

checkCIF report


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
C3H10NO+·C4H5O6−·H2OF(000) = 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 = 2.9–26.4°
b = 7.701 (2) ŵ = 0.13 mm−1
c = 19.288 (5) ÅT = 294 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)
Graphite monochromatorRint = 0.024
ω scansθmax = 26.4°, θmin = 2.1°
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 F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap (N-H and O-H) and geom (C-H)
R[F2 > 2σ(F2)] = 0.028H 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 reflectionsΔρmax = 0.25 e Å−3
174 parametersΔρmin = −0.17 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.067 (5)
Crystal data top
C3H10NO+·C4H5O6−·H2OV = 1118.9 (5) Å3
Mr = 243.22Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.533 (2) ŵ = 0.13 mm−1
b = 7.701 (2) ÅT = 294 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)] = 0.0280 restraints
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
174 parameters
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, º) 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, º) 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.

Experimental details

Crystal data
Chemical formulaC3H10NO+·C4H5O6−·H2O
Mr243.22
Crystal system, space groupOrthorhombic, P212121
Temperature (K)294
a, b, c (Å)7.533 (2), 7.701 (2), 19.288 (5)
V (Å3)1118.9 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.13
Crystal size (mm)0.24 × 0.22 × 0.18
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.969, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections		6331, 1359, 1280
Rint0.024
(sin θ/λ)max (Å−1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.074, 1.06
No. of reflections1359
No. of parameters174
H-atom treatmentH 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).

Hydrogen-bond geometry (Å, º) 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

First citationBai, G. Y., Chen, L. G., Xing, P., Li, Y. & Yan, X. L. (2004). Fine Chem. 21, 943–945.  CAS Google Scholar
 First citationBruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHumljan, 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
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 2| February 2008| Page o422
doi:10.1107/S1600536808000391
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