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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004324/ww6012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004324/ww6012Isup2.hkl
Contains datablock I

CCDC reference: 183789

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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








Computing details top

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+·C4H3O4F(000) = 560
Mr = 265.28Dx = 1.440 Mg m3
Dm = 1.44 Mg m3
Dm measured by flotation in a xylene/bromoform mixture
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.070 (2) Åθ = 16–24°
b = 5.746 (5) ŵ = 2.55 mm1
c = 19.697 (14) ÅT = 293 K
β = 102.34 (3)°Needle, colorless
V = 1223.9 (14) Å30.30 × 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 tubeRint = 0.013
Graphite monochromatorθmax = 68.0°, θmin = 4.1°
ω–2θ scansh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 06
Tmin = 0.52, Tmax = 0.77l = 2323
2298 measured reflections3 standard reflections every 60 min
2192 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-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 reflectionsΔρmax = 0.41 e Å3
157 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
S10.92165 (7)0.45582 (15)0.08362 (4)0.0714 (3)
O10.76509 (13)0.1339 (3)0.25590 (8)0.0501 (4)
H10.74300.03340.28020.075*
O20.56744 (15)0.2239 (3)0.23299 (11)0.0690 (6)
N10.60262 (13)0.6312 (3)0.17681 (7)0.0337 (4)
H1A0.61650.74820.14990.051*
H1B0.60400.68430.21940.051*
H1C0.52900.56880.15930.051*
C10.67023 (17)0.2584 (3)0.22658 (9)0.0356 (4)
C20.70017 (16)0.4516 (3)0.17996 (9)0.0328 (4)
H2A0.69230.38730.13310.039*
C30.82999 (18)0.5536 (4)0.20232 (10)0.0404 (5)
H3A0.82920.71290.18590.048*
H3B0.85280.55660.25270.048*
C40.9266 (2)0.4177 (5)0.17485 (13)0.0530 (6)
H4A0.91630.25360.18370.064*
H4B1.00780.46350.20070.064*
C50.9835 (4)0.7435 (7)0.08380 (19)0.0922 (11)
H5A0.98620.78780.03720.138*
H5B1.06550.74680.11220.138*
H5C0.93190.85030.10210.138*
O30.40000 (15)0.3128 (3)0.01795 (7)0.0492 (4)
H30.39170.35590.02050.074*
O40.34345 (16)0.0188 (3)0.08797 (7)0.0523 (4)
O50.37431 (15)0.4261 (3)0.09854 (7)0.0469 (4)
O60.28360 (14)0.2746 (3)0.17866 (7)0.0455 (4)
C60.35539 (18)0.1060 (3)0.02994 (9)0.0370 (4)
C70.3211 (2)0.0342 (4)0.02625 (10)0.0435 (5)
H70.30580.19060.01570.052*
C80.3089 (2)0.0286 (4)0.08944 (10)0.0428 (5)
H80.28790.09150.11640.051*
C90.32351 (17)0.2606 (3)0.12396 (9)0.0359 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0704 (5)0.0930 (6)0.0621 (4)0.0109 (4)0.0389 (3)0.0187 (3)
O10.0414 (8)0.0522 (9)0.0585 (9)0.0035 (7)0.0150 (6)0.0198 (7)
O20.0436 (9)0.0777 (13)0.0926 (13)0.0053 (8)0.0301 (8)0.0461 (10)
N10.0374 (8)0.0356 (8)0.0308 (7)0.0023 (6)0.0132 (6)0.0005 (6)
C10.0382 (10)0.0376 (10)0.0339 (9)0.0034 (7)0.0141 (7)0.0002 (7)
C20.0362 (9)0.0348 (10)0.0308 (8)0.0025 (7)0.0148 (7)0.0020 (7)
C30.0385 (10)0.0450 (11)0.0408 (10)0.0086 (8)0.0156 (8)0.0025 (8)
C40.0425 (11)0.0591 (14)0.0630 (14)0.0012 (10)0.0234 (10)0.0050 (11)
C50.095 (2)0.111 (3)0.082 (2)0.020 (2)0.0430 (18)0.0191 (19)
O30.0753 (10)0.0447 (9)0.0309 (7)0.0209 (7)0.0187 (7)0.0027 (6)
O40.0863 (12)0.0441 (9)0.0310 (7)0.0086 (7)0.0224 (7)0.0053 (6)
O50.0706 (10)0.0398 (8)0.0318 (7)0.0169 (7)0.0140 (6)0.0035 (6)
O60.0577 (9)0.0492 (9)0.0343 (7)0.0067 (7)0.0199 (6)0.0072 (6)
C60.0466 (10)0.0373 (10)0.0290 (9)0.0016 (8)0.0120 (7)0.0003 (7)
C70.0663 (13)0.0318 (10)0.0360 (10)0.0095 (9)0.0192 (9)0.0025 (8)
C80.0615 (12)0.0369 (11)0.0335 (9)0.0123 (9)0.0184 (9)0.0011 (8)
C90.0410 (10)0.0399 (10)0.0267 (8)0.0049 (8)0.0074 (7)0.0014 (7)
Geometric parameters (Å, º) top
S1—C51.789 (4)C4—H4A0.9700
S1—C41.800 (3)C4—H4B0.9700
O1—C11.299 (3)C5—H5A0.9600
O1—H10.8200C5—H5B0.9600
O2—C11.188 (2)C5—H5C0.9600
N1—C21.485 (2)O3—C61.289 (3)
N1—H1A0.8900O3—H30.8200
N1—H1B0.8900O4—C61.229 (2)
N1—H1C0.8900O5—C91.261 (2)
C1—C21.522 (3)O6—C91.251 (2)
C2—C31.527 (3)C6—C71.482 (3)
C2—H2A0.9800C7—C81.330 (3)
C3—C41.515 (3)C7—H70.9300
C3—H3A0.9700C8—C91.489 (3)
C3—H3B0.9700C8—H80.9300
C5—S1—C4100.40 (16)C3—C4—H4A108.5
C1—O1—H1109.5S1—C4—H4A108.5
C2—N1—H1A109.5C3—C4—H4B108.5
C2—N1—H1B109.5S1—C4—H4B108.5
H1A—N1—H1B109.5H4A—C4—H4B107.5
C2—N1—H1C109.5S1—C5—H5A109.5
H1A—N1—H1C109.5S1—C5—H5B109.5
H1B—N1—H1C109.5H5A—C5—H5B109.5
O2—C1—O1124.22 (19)S1—C5—H5C109.5
O2—C1—C2121.52 (18)H5A—C5—H5C109.5
O1—C1—C2114.22 (16)H5B—C5—H5C109.5
N1—C2—C1106.38 (14)C6—O3—H3109.5
N1—C2—C3112.10 (16)O4—C6—O3120.45 (18)
C1—C2—C3114.77 (16)O4—C6—C7118.64 (19)
N1—C2—H2A107.8O3—C6—C7120.88 (17)
C1—C2—H2A107.8C8—C7—C6130.13 (19)
C3—C2—H2A107.8C8—C7—H7114.9
C4—C3—C2113.06 (18)C6—C7—H7114.9
C4—C3—H3A109.0C7—C8—C9130.34 (18)
C2—C3—H3A109.0C7—C8—H8114.8
C4—C3—H3B109.0C9—C8—H8114.8
C2—C3—H3B109.0O6—C9—O5124.26 (19)
H3A—C3—H3B107.8O6—C9—C8115.25 (18)
C3—C4—S1114.88 (17)O5—C9—C8120.48 (17)
O2—C1—C2—N126.6 (3)C5—S1—C4—C373.4 (2)
O1—C1—C2—N1155.56 (16)O4—C6—C7—C8169.5 (2)
O2—C1—C2—C3151.2 (2)O3—C6—C7—C812.4 (4)
O1—C1—C2—C331.0 (2)C6—C7—C8—C91.2 (4)
N1—C2—C3—C4152.86 (17)C7—C8—C9—O6167.1 (2)
C1—C2—C3—C485.6 (2)C7—C8—C9—O513.7 (4)
C2—C3—C4—S173.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O6i0.821.752.552 (3)166
O3—H3···O50.821.642.459 (3)177
N1—H1A···O4ii0.891.922.812 (3)175
N1—H1B···O6iii0.892.192.973 (3)147
N1—H1B···O2iii0.892.302.900 (2)125
N1—H1C···O50.892.042.914 (3)167
C2—H2A···O4iv0.982.503.233 (4)132
Symmetry codes: (i) x+1, y1/2, 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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