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In the title compound, C5H12NO2S+·C4H3O4-, the methionine molecule exists in the cationic form and the maleic acid molecule in the mono-ionized state. In the semi-maleate ion, there is an asymmetric intramolecular hydrogen bond between the carboxy OH group and an O atom of the other carboxylate group. There are no direct hydrogen-bonded interactions among the semi-maleate anions.
Supporting information
CCDC reference: 183789
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.129
- Data-to-parameter ratio = 14.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; 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-methioninium maleate
top
Crystal data top
C5H12NO2S+·C4H3O4− | F(000) = 560 |
Mr = 265.28 | Dx = 1.440 Mg m−3 Dm = 1.44 Mg m−3 Dm measured by flotation in a xylene/bromoform mixture |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 11.070 (2) Å | θ = 16–24° |
b = 5.746 (5) Å | µ = 2.55 mm−1 |
c = 19.697 (14) Å | T = 293 K |
β = 102.34 (3)° | Needle, colorless |
V = 1223.9 (14) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 2029 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 68.0°, θmin = 4.1° |
ω–2θ scans | h = 0→13 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→6 |
Tmin = 0.52, Tmax = 0.77 | l = −23→23 |
2298 measured reflections | 3 standard reflections every 60 min |
2192 independent reflections | intensity decay: none |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0859P)2 + 0.8155P] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max < 0.001 |
2192 reflections | Δρmax = 0.41 e Å−3 |
157 parameters | Δρmin = −0.23 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: 0.0036 (6) |
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 | |
S1 | 0.92165 (7) | 0.45582 (15) | 0.08362 (4) | 0.0714 (3) | |
O1 | 0.76509 (13) | 0.1339 (3) | 0.25590 (8) | 0.0501 (4) | |
H1 | 0.7430 | 0.0334 | 0.2802 | 0.075* | |
O2 | 0.56744 (15) | 0.2239 (3) | 0.23299 (11) | 0.0690 (6) | |
N1 | 0.60262 (13) | 0.6312 (3) | 0.17681 (7) | 0.0337 (4) | |
H1A | 0.6165 | 0.7482 | 0.1499 | 0.051* | |
H1B | 0.6040 | 0.6843 | 0.2194 | 0.051* | |
H1C | 0.5290 | 0.5688 | 0.1593 | 0.051* | |
C1 | 0.67023 (17) | 0.2584 (3) | 0.22658 (9) | 0.0356 (4) | |
C2 | 0.70017 (16) | 0.4516 (3) | 0.17996 (9) | 0.0328 (4) | |
H2A | 0.6923 | 0.3873 | 0.1331 | 0.039* | |
C3 | 0.82999 (18) | 0.5536 (4) | 0.20232 (10) | 0.0404 (5) | |
H3A | 0.8292 | 0.7129 | 0.1859 | 0.048* | |
H3B | 0.8528 | 0.5566 | 0.2527 | 0.048* | |
C4 | 0.9266 (2) | 0.4177 (5) | 0.17485 (13) | 0.0530 (6) | |
H4A | 0.9163 | 0.2536 | 0.1837 | 0.064* | |
H4B | 1.0078 | 0.4635 | 0.2007 | 0.064* | |
C5 | 0.9835 (4) | 0.7435 (7) | 0.08380 (19) | 0.0922 (11) | |
H5A | 0.9862 | 0.7878 | 0.0372 | 0.138* | |
H5B | 1.0655 | 0.7468 | 0.1122 | 0.138* | |
H5C | 0.9319 | 0.8503 | 0.1021 | 0.138* | |
O3 | 0.40000 (15) | 0.3128 (3) | −0.01795 (7) | 0.0492 (4) | |
H3 | 0.3917 | 0.3559 | 0.0205 | 0.074* | |
O4 | 0.34345 (16) | 0.0188 (3) | −0.08797 (7) | 0.0523 (4) | |
O5 | 0.37431 (15) | 0.4261 (3) | 0.09854 (7) | 0.0469 (4) | |
O6 | 0.28360 (14) | 0.2746 (3) | 0.17866 (7) | 0.0455 (4) | |
C6 | 0.35539 (18) | 0.1060 (3) | −0.02994 (9) | 0.0370 (4) | |
C7 | 0.3211 (2) | −0.0342 (4) | 0.02625 (10) | 0.0435 (5) | |
H7 | 0.3058 | −0.1906 | 0.0157 | 0.052* | |
C8 | 0.3089 (2) | 0.0286 (4) | 0.08944 (10) | 0.0428 (5) | |
H8 | 0.2879 | −0.0915 | 0.1164 | 0.051* | |
C9 | 0.32351 (17) | 0.2606 (3) | 0.12396 (9) | 0.0359 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0704 (5) | 0.0930 (6) | 0.0621 (4) | −0.0109 (4) | 0.0389 (3) | −0.0187 (3) |
O1 | 0.0414 (8) | 0.0522 (9) | 0.0585 (9) | 0.0035 (7) | 0.0150 (6) | 0.0198 (7) |
O2 | 0.0436 (9) | 0.0777 (13) | 0.0926 (13) | 0.0053 (8) | 0.0301 (8) | 0.0461 (10) |
N1 | 0.0374 (8) | 0.0356 (8) | 0.0308 (7) | −0.0023 (6) | 0.0132 (6) | −0.0005 (6) |
C1 | 0.0382 (10) | 0.0376 (10) | 0.0339 (9) | −0.0034 (7) | 0.0141 (7) | 0.0002 (7) |
C2 | 0.0362 (9) | 0.0348 (10) | 0.0308 (8) | −0.0025 (7) | 0.0148 (7) | −0.0020 (7) |
C3 | 0.0385 (10) | 0.0450 (11) | 0.0408 (10) | −0.0086 (8) | 0.0156 (8) | −0.0025 (8) |
C4 | 0.0425 (11) | 0.0591 (14) | 0.0630 (14) | 0.0012 (10) | 0.0234 (10) | 0.0050 (11) |
C5 | 0.095 (2) | 0.111 (3) | 0.082 (2) | −0.020 (2) | 0.0430 (18) | 0.0191 (19) |
O3 | 0.0753 (10) | 0.0447 (9) | 0.0309 (7) | −0.0209 (7) | 0.0187 (7) | −0.0027 (6) |
O4 | 0.0863 (12) | 0.0441 (9) | 0.0310 (7) | −0.0086 (7) | 0.0224 (7) | −0.0053 (6) |
O5 | 0.0706 (10) | 0.0398 (8) | 0.0318 (7) | −0.0169 (7) | 0.0140 (6) | −0.0035 (6) |
O6 | 0.0577 (9) | 0.0492 (9) | 0.0343 (7) | −0.0067 (7) | 0.0199 (6) | −0.0072 (6) |
C6 | 0.0466 (10) | 0.0373 (10) | 0.0290 (9) | −0.0016 (8) | 0.0120 (7) | 0.0003 (7) |
C7 | 0.0663 (13) | 0.0318 (10) | 0.0360 (10) | −0.0095 (9) | 0.0192 (9) | −0.0025 (8) |
C8 | 0.0615 (12) | 0.0369 (11) | 0.0335 (9) | −0.0123 (9) | 0.0184 (9) | 0.0011 (8) |
C9 | 0.0410 (10) | 0.0399 (10) | 0.0267 (8) | −0.0049 (8) | 0.0074 (7) | −0.0014 (7) |
Geometric parameters (Å, º) top
S1—C5 | 1.789 (4) | C4—H4A | 0.9700 |
S1—C4 | 1.800 (3) | C4—H4B | 0.9700 |
O1—C1 | 1.299 (3) | C5—H5A | 0.9600 |
O1—H1 | 0.8200 | C5—H5B | 0.9600 |
O2—C1 | 1.188 (2) | C5—H5C | 0.9600 |
N1—C2 | 1.485 (2) | O3—C6 | 1.289 (3) |
N1—H1A | 0.8900 | O3—H3 | 0.8200 |
N1—H1B | 0.8900 | O4—C6 | 1.229 (2) |
N1—H1C | 0.8900 | O5—C9 | 1.261 (2) |
C1—C2 | 1.522 (3) | O6—C9 | 1.251 (2) |
C2—C3 | 1.527 (3) | C6—C7 | 1.482 (3) |
C2—H2A | 0.9800 | C7—C8 | 1.330 (3) |
C3—C4 | 1.515 (3) | C7—H7 | 0.9300 |
C3—H3A | 0.9700 | C8—C9 | 1.489 (3) |
C3—H3B | 0.9700 | C8—H8 | 0.9300 |
| | | |
C5—S1—C4 | 100.40 (16) | C3—C4—H4A | 108.5 |
C1—O1—H1 | 109.5 | S1—C4—H4A | 108.5 |
C2—N1—H1A | 109.5 | C3—C4—H4B | 108.5 |
C2—N1—H1B | 109.5 | S1—C4—H4B | 108.5 |
H1A—N1—H1B | 109.5 | H4A—C4—H4B | 107.5 |
C2—N1—H1C | 109.5 | S1—C5—H5A | 109.5 |
H1A—N1—H1C | 109.5 | S1—C5—H5B | 109.5 |
H1B—N1—H1C | 109.5 | H5A—C5—H5B | 109.5 |
O2—C1—O1 | 124.22 (19) | S1—C5—H5C | 109.5 |
O2—C1—C2 | 121.52 (18) | H5A—C5—H5C | 109.5 |
O1—C1—C2 | 114.22 (16) | H5B—C5—H5C | 109.5 |
N1—C2—C1 | 106.38 (14) | C6—O3—H3 | 109.5 |
N1—C2—C3 | 112.10 (16) | O4—C6—O3 | 120.45 (18) |
C1—C2—C3 | 114.77 (16) | O4—C6—C7 | 118.64 (19) |
N1—C2—H2A | 107.8 | O3—C6—C7 | 120.88 (17) |
C1—C2—H2A | 107.8 | C8—C7—C6 | 130.13 (19) |
C3—C2—H2A | 107.8 | C8—C7—H7 | 114.9 |
C4—C3—C2 | 113.06 (18) | C6—C7—H7 | 114.9 |
C4—C3—H3A | 109.0 | C7—C8—C9 | 130.34 (18) |
C2—C3—H3A | 109.0 | C7—C8—H8 | 114.8 |
C4—C3—H3B | 109.0 | C9—C8—H8 | 114.8 |
C2—C3—H3B | 109.0 | O6—C9—O5 | 124.26 (19) |
H3A—C3—H3B | 107.8 | O6—C9—C8 | 115.25 (18) |
C3—C4—S1 | 114.88 (17) | O5—C9—C8 | 120.48 (17) |
| | | |
O2—C1—C2—N1 | 26.6 (3) | C5—S1—C4—C3 | 73.4 (2) |
O1—C1—C2—N1 | −155.56 (16) | O4—C6—C7—C8 | −169.5 (2) |
O2—C1—C2—C3 | 151.2 (2) | O3—C6—C7—C8 | 12.4 (4) |
O1—C1—C2—C3 | −31.0 (2) | C6—C7—C8—C9 | 1.2 (4) |
N1—C2—C3—C4 | −152.86 (17) | C7—C8—C9—O6 | 167.1 (2) |
C1—C2—C3—C4 | 85.6 (2) | C7—C8—C9—O5 | −13.7 (4) |
C2—C3—C4—S1 | 73.9 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O6i | 0.82 | 1.75 | 2.552 (3) | 166 |
O3—H3···O5 | 0.82 | 1.64 | 2.459 (3) | 177 |
N1—H1A···O4ii | 0.89 | 1.92 | 2.812 (3) | 175 |
N1—H1B···O6iii | 0.89 | 2.19 | 2.973 (3) | 147 |
N1—H1B···O2iii | 0.89 | 2.30 | 2.900 (2) | 125 |
N1—H1C···O5 | 0.89 | 2.04 | 2.914 (3) | 167 |
C2—H2A···O4iv | 0.98 | 2.50 | 3.233 (4) | 132 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) −x+1, y+1/2, −z+1/2; (iv) −x+1, −y, −z. |
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