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The title compound, C5H9NO4·H2O, has been synthesized and crystallized. It crystallizes in Cc with one mol­ecule in the asymmetric unit. The compound is found in its zwitterionic form. D and L forms of the compound are linked in the crystal via O—H...O and N—H...O hydrogen bonds, both directly between the aspartic acid-derivative entities and to the crystal water mol­ecule. A weak intramolecular N—H...O interaction is found. The carbon skeleton is slightly twisted with C—C—C—C = 166.83 (11)°. A comparison with other derivatives of aspartic acid shows only two rotamers – one with a near planar carbon skeleton and one with a significantly twisted carbon skeleton.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008593/av1045sup1.cif
Contains datablocks I, NMDLASP

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008593/av1045Isup2.hkl
Contains datablock I

CCDC reference: 150861

Computing details top

Data collection: MAR; cell refinement: DENZO (Otwinoski & Minor, 1993); data reduction: DENZO (Otwinoski & Minor, 1993) and CCP4 (Evans, 1994)); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

N-Methyl-DL-Aspartic Acid top
Crystal data top
C5H9NO4·H2OF(000) = 352
Mr = 165.15Dx = 1.490 Mg m3
Monoclinic, CcSynchrotron radiation, λ = 0.70000 Å
a = 9.282 ÅCell parameters from 6678 reflections
b = 10.803 Åθ = 3.0–28.0°
c = 7.887 ŵ = 0.13 mm1
β = 111.45°T = 122 K
V = 736.1 Å3Multi-faceted, colourless
Z = 40.2 × 0.15 × 0.15 mm
Data collection top
MAR Image Plate
diffractometer
891 reflections with I > 2σ(I)
Radiation source: European Synchrotron Radiation FacilityRint = 0.029
Si(111) monochromatorθmax = 28.0°, θmin = 3.0°
Detector resolution: 6.66 pixels mm-1h = 1211
φ scansk = 1414
6678 measured reflectionsl = 99
893 independent reflections
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.048P)2 + 0.1021P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max = 0.042
S = 1.31Δρmax = 0.39 e Å3
893 reflectionsΔρmin = 0.22 e Å3
145 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.048 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.2 (9)
Special details top

Experimental. Two data sets were collected. One low resolution data set to up to 0.9 Å and one medium resolution from 1.7 Å to 0.7 Å. Scan range 5°.

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
O10.38612 (13)0.09177 (10)0.08917 (15)0.0135 (3)
O20.20517 (14)0.23216 (11)0.23859 (16)0.0145 (3)
C10.29997 (16)0.18271 (14)0.09703 (18)0.0088 (3)
C20.30871 (15)0.23675 (12)0.0865 (2)0.0078 (3)
H10.412 (3)0.2411 (19)0.166 (4)0.005 (4)*
N10.24935 (15)0.36751 (11)0.05886 (18)0.0092 (3)
H20.189 (3)0.379 (2)0.058 (5)0.018 (6)*
H30.195 (3)0.383 (2)0.121 (3)0.004 (4)*
C50.37574 (19)0.46106 (14)0.0977 (2)0.0172 (3)
H40.330 (3)0.542 (3)0.079 (4)0.028 (8)*
H50.437 (3)0.443 (3)0.026 (4)0.025 (7)*
H60.446 (3)0.450 (3)0.223 (4)0.020 (6)*
C30.21565 (16)0.15826 (13)0.1710 (2)0.0087 (3)
H70.104 (3)0.169 (3)0.109 (4)0.015 (5)*
H80.245 (3)0.069 (3)0.165 (5)0.020 (6)*
C40.25388 (16)0.19328 (12)0.36860 (19)0.0093 (3)
O30.36350 (17)0.25899 (13)0.4512 (2)0.0220 (3)
O40.15812 (13)0.14691 (11)0.44050 (16)0.0152 (3)
H90.183 (4)0.176 (3)0.543 (5)0.022 (6)*
OW0.57309 (13)0.01479 (11)0.73230 (17)0.0125 (3)
H1W0.509 (4)0.046 (4)0.778 (6)0.040 (8)*
H2W0.515 (3)0.021 (3)0.639 (5)0.023 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0193 (5)0.0131 (5)0.0113 (6)0.0039 (4)0.0094 (4)0.0004 (4)
O20.0175 (5)0.0200 (5)0.0061 (6)0.0051 (4)0.0044 (4)0.0003 (4)
C10.0111 (5)0.0116 (6)0.0056 (6)0.0008 (4)0.0054 (5)0.0009 (4)
C20.0097 (6)0.0081 (6)0.0060 (6)0.0012 (4)0.0035 (5)0.0003 (4)
N10.0134 (5)0.0090 (5)0.0070 (6)0.0019 (4)0.0058 (4)0.0002 (4)
C50.0198 (7)0.0108 (7)0.0226 (9)0.0031 (5)0.0098 (6)0.0003 (5)
C30.0104 (6)0.0110 (6)0.0059 (6)0.0008 (4)0.0044 (5)0.0012 (4)
C40.0132 (6)0.0091 (6)0.0066 (6)0.0010 (5)0.0048 (5)0.0001 (5)
O30.0242 (6)0.0319 (7)0.0104 (6)0.0158 (5)0.0071 (5)0.0081 (5)
O40.0182 (5)0.0223 (6)0.0087 (6)0.0055 (4)0.0091 (4)0.0039 (4)
OW0.0138 (4)0.0151 (5)0.0111 (6)0.0006 (4)0.0074 (4)0.0020 (4)
Geometric parameters (Å, º) top
O1—C11.2539 (19)C5—H50.96 (3)
O2—C11.2600 (18)C5—H60.97 (3)
C1—C21.535 (2)C3—C41.5145 (14)
C2—N11.5029 (17)C3—H70.98 (3)
C2—C31.5268 (19)C3—H81.00 (3)
C2—H10.93 (2)C4—O31.2161 (19)
N1—C51.4927 (19)C4—O41.3157 (18)
N1—H20.89 (3)O4—H90.82 (4)
N1—H30.84 (3)OW—H1W0.87 (4)
C5—H40.96 (3)OW—H2W0.83 (3)
O1—C1—O2127.02 (14)N1—C5—H5109.5 (17)
O1—C1—C2116.01 (12)H4—C5—H5115 (2)
O2—C1—C2116.95 (13)N1—C5—H6108.4 (16)
N1—C2—C3110.45 (11)H4—C5—H6111 (3)
N1—C2—C1109.32 (12)H5—C5—H6105 (2)
C3—C2—C1110.93 (11)C4—C3—C2110.71 (11)
N1—C2—H1106.3 (13)C4—C3—H7106.9 (16)
C3—C2—H1110.0 (16)C2—C3—H7112.7 (16)
C1—C2—H1109.7 (16)C4—C3—H8108.9 (19)
C5—N1—C2112.81 (11)C2—C3—H8107.8 (17)
C5—N1—H2105.1 (16)H7—C3—H8110 (2)
C2—N1—H2110.0 (16)O3—C4—O4123.78 (14)
C5—N1—H3109.8 (15)O3—C4—C3122.17 (14)
C2—N1—H3112.0 (15)O4—C4—C3114.05 (12)
H2—N1—H3107 (2)C4—O4—H9107 (2)
N1—C5—H4108.5 (17)H1W—OW—H2W103 (3)
O1—C1—C2—N1159.02 (12)C1—C2—N1—C595.90 (14)
O2—C1—C2—N122.54 (17)N1—C2—C3—C471.80 (14)
O1—C1—C2—C378.94 (15)C1—C2—C3—C4166.83 (11)
O2—C1—C2—C399.49 (15)C2—C3—C4—O311.94 (19)
C3—C2—N1—C5141.77 (13)C2—C3—C4—O4167.77 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
OW—H1W···O1i0.87 (4)1.87 (5)2.7337 (15)169 (4)
OW—H2W···O1ii0.83 (3)1.92 (3)2.7472 (17)175 (3)
O4—H9···O2i0.82 (4)1.77 (4)2.5761 (18)171 (3)
N1—H2···O20.89 (3)2.18 (3)2.6658 (18)114 (2)
N1—H2···OWiii0.89 (3)2.18 (3)2.9596 (18)146 (2)
N1—H3···OWiv0.84 (3)2.00 (2)2.7931 (17)158 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z+1/2; (iii) x1/2, y+1/2, z1; (iv) x1/2, y+1/2, z1/2.
 

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