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In the title compound, C
5H
12NO
2S
+·C
2Cl
3O
2−, the methionine molecule exists as a cation with a protonated amino group and an uncharged carboxylic acid group, while the trichloroacetic acid molecule exists as an anion. The assembly of methioninium and trichloroacetate ions, leading to layers parallel to the
ab plane, is characterized by a strong O—H
O-type hydrogen bond between the carboxylic acid and carboxylate groups of the respective ions. A head-to-tail hydrogen bond is also observed between the methioninium cations, in addition to S
Cl, Cl
Cl and Cl
O short contacts.
Supporting information
CCDC reference: 202990
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.092
- Data-to-parameter ratio = 20.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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-methiononium trichloroacetate at 123 K
top
Crystal data top
C5H12NO2S+·C2Cl3O2− | Z = 2 |
Mr = 312.60 | F(000) = 320 |
Triclinic, P1 | Dx = 1.578 Mg m−3 Dm = 1.58 Mg m−3 Dm measured by floatation in a mixture of xylene and bromoform |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1359 (12) Å | Cell parameters from 1024 reflections |
b = 8.9746 (18) Å | θ = 1.7–27.5° |
c = 12.731 (3) Å | µ = 0.85 mm−1 |
α = 70.54 (3)° | T = 123 K |
β = 85.95 (3)° | Prism, colourless |
γ = 85.08 (3)° | 0.5 × 0.3 × 0.2 mm |
V = 657.9 (3) Å3 | |
Data collection top
Bruker SMART diffractometer | 2999 independent reflections |
Radiation source: fine-focus sealed tube | 2628 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 8 pixels mm-1 | θmax = 27.5°, θmin = 1.7° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −11→11 |
Tmin = 0.743, Tmax = 0.843 | l = −14→16 |
7442 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0385P)2 + 0.4522P] where P = (Fo2 + 2Fc2)/3 |
2999 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
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 | 0.28221 (9) | 0.36780 (6) | 0.40975 (4) | 0.03244 (14) | |
Cl1 | 1.04062 (9) | 0.74883 (6) | 0.31890 (4) | 0.03306 (13) | |
Cl2 | 1.02444 (11) | 1.04591 (7) | 0.35800 (4) | 0.04089 (16) | |
Cl3 | 0.72973 (8) | 1.00052 (7) | 0.20404 (5) | 0.04054 (15) | |
N1 | 0.5430 (3) | 0.70793 (18) | 0.05645 (13) | 0.0215 (3) | |
H1A | 0.4798 | 0.7889 | 0.0754 | 0.032* | |
H1B | 0.4407 | 0.6467 | 0.0508 | 0.032* | |
H1C | 0.6166 | 0.7445 | −0.0088 | 0.032* | |
O1 | 0.9458 (2) | 0.39321 (17) | 0.17917 (12) | 0.0275 (3) | |
H1 | 1.0022 | 0.3211 | 0.1583 | 0.041* | |
O2 | 0.7537 (2) | 0.45138 (16) | 0.02522 (12) | 0.0252 (3) | |
O3 | 1.1650 (2) | 1.17240 (17) | 0.11985 (13) | 0.0330 (3) | |
O4 | 1.2738 (3) | 0.93047 (19) | 0.11946 (14) | 0.0400 (4) | |
C1 | 0.8018 (3) | 0.4764 (2) | 0.10851 (15) | 0.0202 (3) | |
C2 | 0.6973 (3) | 0.6134 (2) | 0.14354 (15) | 0.0203 (3) | |
H2 | 0.8130 | 0.6811 | 0.1455 | 0.024* | |
C3 | 0.5836 (3) | 0.5559 (2) | 0.26014 (15) | 0.0233 (4) | |
H3A | 0.6939 | 0.5079 | 0.3146 | 0.028* | |
H3B | 0.5129 | 0.6466 | 0.2770 | 0.028* | |
C4 | 0.4132 (3) | 0.4363 (3) | 0.27201 (17) | 0.0284 (4) | |
H4A | 0.4835 | 0.3458 | 0.2545 | 0.034* | |
H4B | 0.3020 | 0.4845 | 0.2181 | 0.034* | |
C5 | 0.5048 (5) | 0.2502 (4) | 0.4873 (2) | 0.0549 (7) | |
H5A | 0.4575 | 0.2050 | 0.5641 | 0.082* | |
H5B | 0.6239 | 0.3156 | 0.4816 | 0.082* | |
H5C | 0.5524 | 0.1669 | 0.4576 | 0.082* | |
C6 | 1.1631 (3) | 1.0240 (2) | 0.15541 (15) | 0.0223 (4) | |
C7 | 0.9984 (3) | 0.9557 (2) | 0.25646 (15) | 0.0225 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0326 (3) | 0.0329 (3) | 0.0279 (3) | −0.0051 (2) | 0.0084 (2) | −0.0059 (2) |
Cl1 | 0.0390 (3) | 0.0213 (2) | 0.0343 (3) | −0.00138 (18) | −0.0036 (2) | −0.00284 (18) |
Cl2 | 0.0672 (4) | 0.0349 (3) | 0.0223 (2) | 0.0050 (2) | −0.0010 (2) | −0.0141 (2) |
Cl3 | 0.0209 (2) | 0.0428 (3) | 0.0470 (3) | −0.0003 (2) | −0.0038 (2) | −0.0003 (2) |
N1 | 0.0219 (7) | 0.0193 (7) | 0.0232 (8) | 0.0019 (6) | 0.0026 (6) | −0.0083 (6) |
O1 | 0.0263 (7) | 0.0270 (7) | 0.0290 (7) | 0.0086 (5) | −0.0034 (5) | −0.0109 (6) |
O2 | 0.0225 (7) | 0.0272 (7) | 0.0298 (7) | 0.0012 (5) | 0.0001 (5) | −0.0157 (6) |
O3 | 0.0332 (8) | 0.0227 (7) | 0.0372 (8) | 0.0016 (6) | 0.0138 (6) | −0.0059 (6) |
O4 | 0.0450 (9) | 0.0328 (8) | 0.0401 (9) | 0.0115 (7) | 0.0124 (7) | −0.0153 (7) |
C1 | 0.0165 (8) | 0.0192 (8) | 0.0245 (9) | −0.0019 (6) | 0.0038 (6) | −0.0073 (7) |
C2 | 0.0199 (8) | 0.0195 (8) | 0.0226 (9) | −0.0008 (6) | 0.0009 (6) | −0.0089 (7) |
C3 | 0.0241 (9) | 0.0248 (9) | 0.0222 (9) | −0.0017 (7) | 0.0027 (7) | −0.0101 (7) |
C4 | 0.0281 (10) | 0.0331 (10) | 0.0241 (9) | −0.0075 (8) | 0.0026 (7) | −0.0093 (8) |
C5 | 0.0535 (16) | 0.0614 (17) | 0.0328 (13) | 0.0020 (13) | −0.0009 (11) | 0.0053 (12) |
C6 | 0.0200 (8) | 0.0239 (9) | 0.0219 (8) | 0.0031 (7) | 0.0008 (7) | −0.0077 (7) |
C7 | 0.0219 (9) | 0.0216 (8) | 0.0227 (9) | 0.0024 (7) | −0.0008 (7) | −0.0068 (7) |
Geometric parameters (Å, º) top
S1—C5 | 1.789 (3) | O4—C6 | 1.220 (2) |
S1—C4 | 1.807 (2) | C1—C2 | 1.521 (2) |
Cl1—C7 | 1.7634 (19) | C2—C3 | 1.537 (2) |
Cl2—C7 | 1.761 (2) | C2—H2 | 0.98 |
Cl3—C7 | 1.786 (2) | C3—C4 | 1.527 (3) |
N1—C2 | 1.493 (2) | C3—H3A | 0.97 |
N1—H1A | 0.89 | C3—H3B | 0.97 |
N1—H1B | 0.89 | C4—H4A | 0.97 |
N1—H1C | 0.89 | C4—H4B | 0.97 |
O1—C1 | 1.304 (2) | C5—H5A | 0.96 |
O1—H1 | 0.82 | C5—H5B | 0.96 |
O2—C1 | 1.215 (2) | C5—H5C | 0.96 |
O3—C6 | 1.257 (2) | C6—C7 | 1.565 (3) |
| | | |
C5—S1—C4 | 100.28 (12) | H3A—C3—H3B | 107.7 |
C2—N1—H1A | 109.5 | C3—C4—S1 | 113.45 (14) |
C2—N1—H1B | 109.5 | C3—C4—H4A | 108.9 |
H1A—N1—H1B | 109.5 | S1—C4—H4A | 108.9 |
C2—N1—H1C | 109.5 | C3—C4—H4B | 108.9 |
H1A—N1—H1C | 109.5 | S1—C4—H4B | 108.9 |
H1B—N1—H1C | 109.5 | H4A—C4—H4B | 107.7 |
C1—O1—H1 | 109.5 | S1—C5—H5A | 109.5 |
O2—C1—O1 | 126.14 (17) | S1—C5—H5B | 109.5 |
O2—C1—C2 | 123.04 (17) | H5A—C5—H5B | 109.5 |
O1—C1—C2 | 110.82 (16) | S1—C5—H5C | 109.5 |
N1—C2—C1 | 107.99 (14) | H5A—C5—H5C | 109.5 |
N1—C2—C3 | 112.22 (15) | H5B—C5—H5C | 109.5 |
C1—C2—C3 | 111.87 (15) | O4—C6—O3 | 127.07 (18) |
N1—C2—H2 | 108.2 | O4—C6—C7 | 117.98 (17) |
C1—C2—H2 | 108.2 | O3—C6—C7 | 114.94 (16) |
C3—C2—H2 | 108.2 | C6—C7—Cl2 | 109.80 (13) |
C4—C3—C2 | 113.75 (15) | C6—C7—Cl1 | 112.47 (13) |
C4—C3—H3A | 108.8 | Cl2—C7—Cl1 | 108.67 (10) |
C2—C3—H3A | 108.8 | C6—C7—Cl3 | 107.04 (12) |
C4—C3—H3B | 108.8 | Cl2—C7—Cl3 | 109.97 (10) |
C2—C3—H3B | 108.8 | Cl1—C7—Cl3 | 108.86 (11) |
| | | |
O2—C1—C2—N1 | −2.7 (2) | C5—S1—C4—C3 | −70.20 (19) |
O1—C1—C2—N1 | 177.21 (14) | O4—C6—C7—Cl2 | 132.81 (18) |
O2—C1—C2—C3 | 121.28 (19) | O3—C6—C7—Cl2 | −47.4 (2) |
O1—C1—C2—C3 | −58.8 (2) | O4—C6—C7—Cl1 | 11.7 (2) |
N1—C2—C3—C4 | 66.1 (2) | O3—C6—C7—Cl1 | −168.56 (14) |
C1—C2—C3—C4 | −55.4 (2) | O4—C6—C7—Cl3 | −107.84 (19) |
C2—C3—C4—S1 | 179.46 (13) | O3—C6—C7—Cl3 | 71.92 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 1.78 | 2.589 (2) | 171 |
N1—H1A···O4ii | 0.89 | 1.90 | 2.771 (2) | 164 |
N1—H1B···O2iii | 0.89 | 2.01 | 2.854 (2) | 157 |
N1—H1C···O3iv | 0.89 | 1.89 | 2.749 (2) | 163 |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+2, −z. |
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