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The title mol­ecule, C6H9NO6, exists in a zwitterionic form. The transfer of the H atom to the N atom involves two carboxyl groups and, as a result, their H atoms are disordered. The crystal structure is stabilized by O—H...O, N—H...O and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004117/ci6101sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004117/ci6101Isup2.hkl
Contains datablock I

CCDC reference: 183819

Key indicators

  • Powder X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.082
  • Data-to-parameter ratio = 10.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: KM-4 CCD System Software (Kuma, 1998); cell refinement: KM-4 CCD System Software; data reduction: KM-4 CCD System Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

N-carboxymethylaspartic acid top
Crystal data top
C6H9NO6F(000) = 400
Mr = 191.14Dx = 1.638 Mg m3
Monoclinic, P21/nMelting point: 470 K
Hall symbol: -p 2ynMo Kα radiation, λ = 0.71073 Å
a = 5.3430 (5) ÅCell parameters from 36 reflections
b = 16.033 (2) Åθ = 16.9–25.0°
c = 9.0895 (12) ŵ = 0.15 mm1
β = 95.384 (12)°T = 120 K
V = 775.2 (2) Å3Prism, colourless
Z = 40.60 × 0.40 × 0.30 mm
Data collection top
Kuma KM-4 four-circle κ-axis
diffractometer with Oxford Cryosystems Cryostream cooler (Cosier & Glazer, 1986)
Rint = 0.036
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 4.0°
Graphite monochromatorh = 60
ω scansk = 1919
2969 measured reflectionsl = 1010
1368 independent reflections3 standard reflections every 200 reflections
1179 reflections with I > 2σ(I) intensity decay: <2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.04P)2 + 0.2243P]
where P = (Fo2 + 2Fc2)/3
1368 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.24 e Å3
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*/UeqOcc. (<1)
O10.4767 (2)0.64415 (6)0.61666 (11)0.0170 (3)
O20.3125 (2)0.51825 (7)0.55872 (11)0.0166 (3)
O30.1324 (2)0.41892 (6)0.90873 (10)0.0163 (3)
O40.3500 (2)0.53653 (6)0.91396 (11)0.0149 (3)
O50.1229 (2)0.79036 (6)0.60638 (11)0.0181 (3)
O60.4103 (2)0.81542 (7)0.76614 (12)0.0198 (3)
N50.1317 (2)0.67990 (8)0.79540 (13)0.0139 (3)
H5A0.22230.65870.87660.022 (5)*
H5B0.23190.71710.75310.028 (5)*
C10.0714 (3)0.60976 (9)0.68777 (14)0.0128 (3)
H10.05210.62870.61330.010 (4)*
C20.3118 (3)0.59085 (9)0.61593 (14)0.0128 (3)
C30.0301 (3)0.53366 (9)0.76034 (15)0.0131 (3)
H3A0.16960.54970.81140.021 (4)*
H3B0.08860.49490.68580.009 (4)*
C40.1610 (3)0.49154 (9)0.86692 (14)0.0120 (3)
C60.0857 (3)0.72573 (9)0.84479 (15)0.0162 (3)
H6A0.03120.75930.92770.014 (4)*
H6B0.20550.68700.87470.020 (4)*
C70.2076 (3)0.78008 (9)0.72387 (15)0.0147 (3)
H20.459 (10)0.505 (4)0.520 (6)0.032 (13)*0.50
H40.452 (7)0.513 (2)0.975 (4)0.018 (11)*0.50
H60.476 (4)0.8558 (15)0.698 (3)0.049 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0154 (6)0.0192 (6)0.0168 (5)0.0016 (5)0.0033 (4)0.0019 (4)
O20.0141 (6)0.0203 (6)0.0160 (5)0.0001 (5)0.0040 (5)0.0052 (4)
O30.0183 (6)0.0157 (6)0.0142 (5)0.0029 (5)0.0013 (4)0.0020 (4)
O40.0133 (6)0.0165 (6)0.0140 (5)0.0008 (5)0.0035 (5)0.0015 (4)
O50.0192 (6)0.0194 (6)0.0157 (5)0.0000 (5)0.0020 (4)0.0023 (4)
O60.0213 (6)0.0208 (6)0.0176 (5)0.0087 (5)0.0033 (5)0.0016 (4)
N50.0145 (6)0.0158 (6)0.0111 (6)0.0019 (5)0.0002 (5)0.0001 (5)
C10.0130 (8)0.0161 (7)0.0089 (6)0.0021 (6)0.0007 (5)0.0011 (5)
C20.0131 (8)0.0174 (7)0.0075 (6)0.0020 (7)0.0010 (6)0.0034 (5)
C30.0114 (8)0.0176 (7)0.0104 (7)0.0000 (6)0.0014 (6)0.0019 (5)
C40.0129 (8)0.0153 (7)0.0082 (6)0.0005 (7)0.0033 (6)0.0029 (5)
C60.0186 (8)0.0181 (8)0.0120 (7)0.0054 (7)0.0015 (6)0.0025 (6)
C70.0161 (8)0.0138 (7)0.0138 (7)0.0003 (7)0.0006 (6)0.0026 (6)
Geometric parameters (Å, º) top
O1—C21.2268 (18)N5—H5A0.91
O2—C21.2750 (18)N5—H5B0.91
O2—H20.91 (5)C1—C31.512 (2)
O3—C41.2387 (18)C1—C21.525 (2)
O4—C41.2813 (18)C1—H10.95
O4—H40.83 (4)C3—C41.501 (2)
O5—C71.2097 (18)C3—H3A0.95
O6—C71.3115 (19)C3—H3B0.95
O6—H60.94 (3)C6—C71.502 (2)
N5—C61.4797 (19)C6—H6A0.95
N5—C11.5055 (18)C6—H6B0.95
C2—O2—H2113 (4)C4—C3—C1113.24 (12)
C4—O4—H4114 (3)C4—C3—H3A108.9
C7—O6—H6111.7 (14)C1—C3—H3A108.9
C6—N5—C1116.23 (12)C4—C3—H3B108.9
C6—N5—H5A108.2C1—C3—H3B108.9
C1—N5—H5A108.2H3A—C3—H3B107.7
C6—N5—H5B108.2O3—C4—O4122.88 (14)
C1—N5—H5B108.2O3—C4—C3121.66 (13)
H5A—N5—H5B107.4O4—C4—C3115.43 (13)
N5—C1—C3112.52 (11)N5—C6—C7111.40 (12)
N5—C1—C2106.82 (11)N5—C6—H6A109.3
C3—C1—C2112.18 (12)C7—C6—H6A109.3
N5—C1—H1108.4N5—C6—H6B109.3
C3—C1—H1108.4C7—C6—H6B109.3
C2—C1—H1108.4H6A—C6—H6B108.0
O1—C2—O2127.48 (14)O5—C7—O6125.98 (14)
O1—C2—C1119.49 (13)O5—C7—C6123.55 (14)
O2—C2—C1113.02 (13)O6—C7—C6110.45 (12)
C6—N5—C1—C374.25 (15)C2—C1—C3—C453.05 (15)
C6—N5—C1—C2162.23 (11)C1—C3—C4—O3162.31 (13)
N5—C1—C2—O121.35 (16)C1—C3—C4—O419.55 (17)
C3—C1—C2—O1145.08 (13)C1—N5—C6—C772.22 (16)
N5—C1—C2—O2159.50 (11)N5—C6—C7—O56.3 (2)
C3—C1—C2—O235.77 (16)N5—C6—C7—O6175.42 (12)
N5—C1—C3—C467.44 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O2i0.91 (5)1.52 (6)2.429 (2)174 (6)
O4—H4···O4ii0.83 (4)1.60 (4)2.433 (2)177 (4)
O6—H6···O3iii0.94 (3)1.58 (2)2.517 (2)170 (2)
N5—H5A···O40.912.092.751 (2)128
N5—H5A···O5iv0.912.323.040 (2)136
N5—H5B···O6v0.912.473.302 (2)152
C3—H3B···O2vi0.952.433.249 (2)144
C6—H6A···O1vii0.952.313.227 (2)162
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z+2; (iii) x1/2, y+1/2, z+3/2; (iv) x+1/2, y+3/2, z+1/2; (v) x+1, y, z; (vi) x, y+1, z+1; (vii) x1/2, y+3/2, z+1/2.
 

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