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In the title compound, C
4H
10NO
3+·C
4H
3O
4−, the threonine molecule exists as a cation and the maleic acid molecule exists in the mono-ionized state. In the semi-maleate ion, there is an intramolecular O—H
O hydrogen bond. The molecules aggregate into infinite parallel layers which extend in the (0
2) plane. These layers have no hydrogen-bonded interactions between them, only van der Waals interactions. The semi-maleate ion is essentially planar. The structure is stabilized by O—H
O and N—H
O hydrogen bonds, in addition to weak C—H
O interactions. No classical head-to-tail hydrogen bonds are observed.
Supporting information
CCDC reference: 236084
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.001 Å
- R factor = 0.034
- wR factor = 0.093
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
DL-Threoninium maleate
top
Crystal data top
C4H10NO3+·C4H3O4− | Z = 2 |
Mr = 235.19 | F(000) = 248 |
Triclinic, P1 | Dx = 1.563 Mg m−3 Dm = 1.57 Mg m−3 Dm measured by flotation in a mixture of xylene and bromoform |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8050 (12) Å | Cell parameters from 1024 reflections |
b = 8.4310 (17) Å | θ = 2.0–28.3° |
c = 10.740 (2) Å | µ = 0.14 mm−1 |
α = 98.88 (3)° | T = 150 K |
β = 105.17 (3)° | Prismatic, colorless |
γ = 91.68 (3)° | 0.5 × 0.5 × 0.3 mm |
V = 499.90 (19) Å3 | |
Data collection top
Bruker/SMART diffractometer | 2366 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 28.4°, θmin = 2.0° |
Detector resolution: 8 pixels mm-1 | h = −7→7 |
ω scans | k = −11→11 |
7459 measured reflections | l = −14→14 |
2468 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1504P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2468 reflections | Δρmax = 0.42 e Å−3 |
195 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.061 (9) |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.59462 (13) | 1.10303 (9) | 0.39309 (7) | 0.02098 (18) | |
H1 | 0.751 (4) | 1.133 (2) | 0.4185 (19) | 0.044 (5)* | |
O2 | 0.71631 (13) | 0.91813 (9) | 0.25623 (7) | 0.02208 (18) | |
O3 | 0.26663 (13) | 0.91897 (8) | 0.00676 (7) | 0.01706 (17) | |
H3O | 0.356 (3) | 0.871 (2) | −0.0395 (18) | 0.035 (4)* | |
O4 | 0.50780 (13) | 0.27172 (9) | 0.15272 (7) | 0.02067 (18) | |
O5 | 0.86638 (13) | 0.39959 (9) | 0.23023 (7) | 0.02148 (18) | |
H5 | 0.9319 | 0.4800 | 0.2863 | 0.032* | |
O6 | 1.05186 (13) | 0.62906 (9) | 0.39118 (7) | 0.02034 (18) | |
O7 | 0.95305 (13) | 0.80330 (9) | 0.53993 (7) | 0.02113 (18) | |
N1 | 0.15812 (15) | 1.08093 (10) | 0.21839 (8) | 0.01611 (18) | |
H1N | 0.244 (3) | 1.1560 (19) | 0.1922 (15) | 0.027 (4)* | |
H2N | 0.021 (3) | 1.061 (2) | 0.1603 (17) | 0.033 (4)* | |
H3N | 0.135 (3) | 1.1270 (19) | 0.2970 (17) | 0.030 (4)* | |
C1 | 0.55898 (17) | 0.98338 (11) | 0.29452 (9) | 0.0162 (2) | |
C2 | 0.29267 (16) | 0.93239 (11) | 0.23408 (9) | 0.01524 (19) | |
H2 | 0.234 (3) | 0.8798 (18) | 0.2947 (15) | 0.023 (3)* | |
C3 | 0.24743 (17) | 0.82100 (11) | 0.10294 (9) | 0.0161 (2) | |
H3 | 0.376 (2) | 0.7448 (16) | 0.1142 (13) | 0.018 (3)* | |
C4 | 0.00459 (19) | 0.72765 (12) | 0.06432 (10) | 0.0198 (2) | |
H4A | −0.005 (3) | 0.6600 (19) | 0.1290 (16) | 0.029 (4)* | |
H4B | −0.122 (3) | 0.7986 (18) | 0.0552 (14) | 0.022 (3)* | |
H4C | −0.018 (3) | 0.6581 (18) | −0.0187 (15) | 0.025 (3)* | |
C5 | 0.64327 (17) | 0.38206 (11) | 0.22697 (9) | 0.0164 (2) | |
C6 | 0.53977 (17) | 0.49631 (12) | 0.31459 (10) | 0.0179 (2) | |
H6 | 0.372 (3) | 0.4733 (18) | 0.3039 (14) | 0.023 (3)* | |
C7 | 0.64343 (17) | 0.62212 (12) | 0.40533 (9) | 0.0172 (2) | |
H7 | 0.548 (3) | 0.6800 (18) | 0.4528 (15) | 0.024 (3)* | |
C8 | 0.89873 (17) | 0.68859 (11) | 0.44769 (9) | 0.0160 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0162 (3) | 0.0267 (4) | 0.0162 (3) | −0.0016 (3) | 0.0036 (3) | −0.0062 (3) |
O2 | 0.0181 (3) | 0.0251 (4) | 0.0217 (4) | 0.0020 (3) | 0.0065 (3) | −0.0024 (3) |
O3 | 0.0205 (3) | 0.0186 (3) | 0.0133 (3) | −0.0001 (3) | 0.0082 (3) | 0.0003 (2) |
O4 | 0.0215 (4) | 0.0203 (4) | 0.0188 (4) | −0.0039 (3) | 0.0078 (3) | −0.0042 (3) |
O5 | 0.0181 (3) | 0.0220 (4) | 0.0230 (4) | −0.0024 (3) | 0.0098 (3) | −0.0067 (3) |
O6 | 0.0151 (3) | 0.0246 (4) | 0.0195 (3) | −0.0010 (3) | 0.0064 (3) | −0.0043 (3) |
O7 | 0.0190 (3) | 0.0256 (4) | 0.0156 (3) | −0.0026 (3) | 0.0049 (3) | −0.0058 (3) |
N1 | 0.0145 (4) | 0.0184 (4) | 0.0140 (4) | −0.0004 (3) | 0.0046 (3) | −0.0025 (3) |
C1 | 0.0172 (4) | 0.0187 (4) | 0.0121 (4) | −0.0003 (3) | 0.0039 (3) | 0.0015 (3) |
C2 | 0.0160 (4) | 0.0169 (4) | 0.0124 (4) | −0.0008 (3) | 0.0049 (3) | −0.0003 (3) |
C3 | 0.0190 (4) | 0.0155 (4) | 0.0130 (4) | −0.0005 (3) | 0.0053 (3) | −0.0006 (3) |
C4 | 0.0231 (5) | 0.0184 (4) | 0.0164 (4) | −0.0054 (4) | 0.0057 (4) | −0.0012 (3) |
C5 | 0.0191 (4) | 0.0165 (4) | 0.0145 (4) | 0.0001 (3) | 0.0065 (3) | 0.0015 (3) |
C6 | 0.0150 (4) | 0.0199 (4) | 0.0188 (4) | −0.0001 (3) | 0.0066 (3) | −0.0008 (4) |
C7 | 0.0155 (4) | 0.0199 (4) | 0.0167 (4) | 0.0012 (3) | 0.0070 (3) | −0.0003 (3) |
C8 | 0.0158 (4) | 0.0191 (4) | 0.0124 (4) | 0.0002 (3) | 0.0035 (3) | 0.0014 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.3133 (12) | C1—C2 | 1.5316 (14) |
O1—H1 | 0.89 (2) | C2—C3 | 1.5226 (13) |
O2—C1 | 1.2091 (13) | C2—H2 | 0.965 (15) |
O3—C3 | 1.4421 (12) | C3—C4 | 1.5189 (14) |
O3—H3O | 0.874 (19) | C3—H3 | 0.992 (14) |
O4—C5 | 1.2327 (13) | C4—H4A | 0.975 (16) |
O5—C5 | 1.2899 (12) | C4—H4B | 0.956 (15) |
O5—H5 | 0.8400 | C4—H4C | 0.964 (16) |
O6—C8 | 1.2747 (12) | C5—C6 | 1.4914 (14) |
O7—C8 | 1.2406 (13) | C6—C7 | 1.3317 (14) |
N1—C2 | 1.5035 (13) | C6—H6 | 0.962 (15) |
N1—H1N | 0.916 (16) | C7—C8 | 1.4957 (14) |
N1—H2N | 0.866 (19) | C7—H7 | 0.946 (16) |
N1—H3N | 0.919 (17) | | |
| | | |
C1—O1—H1 | 107.3 (12) | O3—C3—H3 | 110.8 (8) |
C3—O3—H3O | 107.7 (11) | C4—C3—H3 | 109.5 (8) |
C5—O5—H5 | 109.5 | C2—C3—H3 | 105.9 (8) |
C2—N1—H1N | 110.5 (10) | C3—C4—H4A | 110.3 (9) |
C2—N1—H2N | 112.4 (11) | C3—C4—H4B | 111.2 (9) |
H1N—N1—H2N | 107.1 (14) | H4A—C4—H4B | 110.1 (13) |
C2—N1—H3N | 110.2 (10) | C3—C4—H4C | 110.1 (9) |
H1N—N1—H3N | 107.2 (14) | H4A—C4—H4C | 107.7 (13) |
H2N—N1—H3N | 109.3 (15) | H4B—C4—H4C | 107.5 (12) |
O2—C1—O1 | 124.61 (9) | O4—C5—O5 | 122.08 (9) |
O2—C1—C2 | 123.26 (9) | O4—C5—C6 | 117.40 (9) |
O1—C1—C2 | 112.13 (9) | O5—C5—C6 | 120.52 (9) |
N1—C2—C3 | 110.38 (8) | C7—C6—C5 | 130.31 (9) |
N1—C2—C1 | 108.71 (8) | C7—C6—H6 | 115.7 (9) |
C3—C2—C1 | 112.07 (8) | C5—C6—H6 | 114.0 (9) |
N1—C2—H2 | 106.8 (9) | C6—C7—C8 | 129.43 (9) |
C3—C2—H2 | 110.2 (9) | C6—C7—H7 | 118.1 (9) |
C1—C2—H2 | 108.6 (9) | C8—C7—H7 | 112.4 (9) |
O3—C3—C4 | 110.96 (8) | O7—C8—O6 | 122.08 (9) |
O3—C3—C2 | 107.47 (7) | O7—C8—C7 | 116.83 (9) |
C4—C3—C2 | 112.08 (8) | O6—C8—C7 | 121.09 (9) |
| | | |
O2—C1—C2—N1 | −136.12 (10) | C1—C2—C3—C4 | 161.21 (8) |
O1—C1—C2—N1 | 45.02 (10) | O4—C5—C6—C7 | 178.22 (10) |
O2—C1—C2—C3 | −13.84 (13) | O5—C5—C6—C7 | −1.63 (17) |
O1—C1—C2—C3 | 167.29 (8) | C5—C6—C7—C8 | 0.11 (19) |
N1—C2—C3—O3 | 44.71 (10) | C6—C7—C8—O7 | −176.44 (10) |
C1—C2—C3—O3 | −76.62 (10) | C6—C7—C8—O6 | 3.42 (16) |
N1—C2—C3—C4 | −77.46 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O7i | 0.89 (2) | 1.70 (2) | 2.598 (1) | 177 (2) |
O3—H3O···O4ii | 0.87 (2) | 1.91 (2) | 2.771 (1) | 166 (2) |
O5—H5···O6 | 0.84 | 1.56 | 2.400 (1) | 180 |
N1—H1N···O4iii | 0.92 (2) | 1.96 (2) | 2.848 (1) | 162 (1) |
N1—H2N···O3iv | 0.87 (2) | 2.14 (2) | 2.968 (1) | 160 (2) |
N1—H3N···O7v | 0.92 (2) | 1.96 (2) | 2.870 (1) | 171 (2) |
C6—H6···O6vi | 0.96 (2) | 2.59 (2) | 3.328 (2) | 133 (1) |
C7—H7···O1v | 0.95 (2) | 2.58 (2) | 3.489 (2) | 162 (1) |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+1, −z; (iii) x, y+1, z; (iv) −x, −y+2, −z; (v) −x+1, −y+2, −z+1; (vi) x−1, y, z. |
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