Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801012016/bt6061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801012016/bt6061Isup2.hkl |
CCDC reference: 170914
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- Disorder in solvent or counterion
- R factor = 0.051
- wR factor = 0.147
- Data-to-parameter ratio = 7.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
REFI_021 Alert A _refine_ls_abs_structure_details is missing Absolute structure method and Friedel-pair number. This should be present as the _refine_ls_abs_structure_Flack or Roger field has been filled out.
Alert Level B:
STRDE_01 Alert B A value for _refine_ls_abs_structure_flack has been given, without an explanantion in the _refine_ls_abs_structure_details field.
Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 6.00 Perc. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 69.99 From the CIF: _reflns_number_total 1786 Count of symmetry unique reflns 1722 Completeness (_total/calc) 103.72% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 64 Fraction of Friedel pairs measured 0.037 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
1 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound crystallized in aqueous solution of methionine and sulfuric acid in stoichiometric ratio of 2:1. The density of the sample was measured by flotation technique using a liquid mixture of carbon tetrachloride and xylene.
In molecule B, the atoms C24, S21 are disordered; the site-occupation factor for C24 and S21 is 0.58 (1), and for C24' and S21' is 0.42 (1). Since the geometry of these disordered atoms differs significantly from expected values, the distances were fixed by DFIX and the disordered group of atoms (with the associated H atoms) was treated using a split model. All H atoms were fixed by geometric restraints using HFIX, and allowed to ride on the preceding atom.
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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
2C5H12NO2S+·SO42− | Dx = 1.459 Mg m−3 Dm = 1.454 Mg m−3 Dm measured by flotation |
Mr = 396.49 | Cu Kα radiation, λ = 1.5418 Å |
Trigonal, P3 | Cell parameters from 25 reflections |
a = 10.281 (3) Å | θ = 14.5–23.4° |
c = 14.788 (6) Å | µ = 4.12 mm−1 |
V = 1353.5 (8) Å3 | T = 293 K |
Z = 3 | Needle, colourless |
F(000) = 630 | 0.5 × 0.35 × 0.2 mm |
Enraf-Nonius sealed tube diffractometer | 1690 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 70.0°, θmin = 5.0° |
ω–2θ scans | h = 0→12 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→10 |
Tmin = 0.221, Tmax = 0.438 | l = 0→17 |
2818 measured reflections | 25 standard reflections every 3 reflections |
1786 independent reflections | intensity decay: none |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters not refined |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1004P)2 + 0.3922P] where P = (Fo2 + 2Fc2)/3 |
1786 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.60 e Å−3 |
7 restraints | Δρmin = −0.51 e Å−3 |
2C5H12NO2S+·SO42− | Z = 3 |
Mr = 396.49 | Cu Kα radiation |
Trigonal, P3 | µ = 4.12 mm−1 |
a = 10.281 (3) Å | T = 293 K |
c = 14.788 (6) Å | 0.5 × 0.35 × 0.2 mm |
V = 1353.5 (8) Å3 |
Enraf-Nonius sealed tube diffractometer | 1690 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.066 |
Tmin = 0.221, Tmax = 0.438 | 25 standard reflections every 3 reflections |
2818 measured reflections | intensity decay: none |
1786 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 7 restraints |
wR(F2) = 0.147 | H-atom parameters not refined |
S = 1.09 | Δρmax = 0.60 e Å−3 |
1786 reflections | Δρmin = −0.51 e Å−3 |
229 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.3333 | 0.6667 | 0.77391 (13) | 0.0310 (4) | |
O1 | 0.3333 | 0.6667 | 0.8717 (5) | 0.0434 (14) | |
O2 | 0.4427 (4) | 0.8170 (4) | 0.7397 (3) | 0.0438 (9) | |
S2 | 1.0000 | 1.0000 | 0.98814 (13) | 0.0305 (4) | |
O3 | 1.0000 | 1.0000 | 0.8912 (5) | 0.062 (2) | |
O4 | 0.8825 (4) | 0.8538 (4) | 1.0219 (3) | 0.0452 (9) | |
S3 | 0.6667 | 0.3333 | 0.86420 (13) | 0.0314 (4) | |
O5 | 0.6667 | 0.3333 | 0.9608 (5) | 0.0534 (17) | |
O6 | 0.5636 (6) | 0.1826 (5) | 0.8286 (4) | 0.0715 (14) | |
O11 | 1.0169 (5) | 0.3728 (5) | 0.6607 (3) | 0.0501 (9) | |
H11 | 1.0871 | 0.4506 | 0.6810 | 0.075* | |
O12 | 1.0378 (5) | 0.2760 (5) | 0.7908 (3) | 0.0515 (10) | |
N11 | 0.7559 (5) | 0.0500 (5) | 0.7821 (3) | 0.0437 (10) | |
H11A | 0.8198 | 0.0413 | 0.8188 | 0.066* | |
H11B | 0.6772 | −0.0406 | 0.7715 | 0.066* | |
H11C | 0.7249 | 0.1078 | 0.8080 | 0.066* | |
C11 | 0.9748 (6) | 0.2651 (6) | 0.7207 (4) | 0.0399 (11) | |
C12 | 0.8326 (6) | 0.1193 (5) | 0.6949 (4) | 0.0400 (10) | |
H12 | 0.8634 | 0.0524 | 0.6669 | 0.048* | |
C13 | 0.7291 (7) | 0.1375 (7) | 0.6291 (4) | 0.0532 (14) | |
H13A | 0.7296 | 0.2301 | 0.6428 | 0.064* | |
H13B | 0.6273 | 0.0550 | 0.6375 | 0.064* | |
C14 | 0.7749 (9) | 0.1408 (9) | 0.5302 (5) | 0.0708 (19) | |
H14A | 0.8768 | 0.2231 | 0.5224 | 0.085* | |
H14B | 0.7100 | 0.1609 | 0.4923 | 0.085* | |
S11 | 0.7659 (3) | −0.0287 (3) | 0.49214 (15) | 0.0864 (7) | |
C15 | 0.5623 (13) | −0.1487 (12) | 0.4901 (8) | 0.109 (4) | |
H15A | 0.5370 | −0.2475 | 0.4702 | 0.164* | |
H15B | 0.5198 | −0.1074 | 0.4493 | 0.164* | |
H15C | 0.5228 | −0.1545 | 0.5497 | 0.164* | |
O21 | 0.7156 (4) | 0.0723 (5) | 0.0797 (3) | 0.0503 (10) | |
H21 | 0.7936 | 0.0769 | 0.0624 | 0.075* | |
O22 | 0.6232 (5) | −0.0585 (5) | −0.0462 (3) | 0.0535 (10) | |
C21 | 0.6119 (6) | 0.0030 (6) | 0.0200 (4) | 0.0366 (10) | |
C22 | 0.4706 (5) | 0.0103 (5) | 0.0384 (3) | 0.0375 (10) | |
H22 | 0.4987 | 0.1148 | 0.0509 | 0.045* | |
N21 | 0.3763 (5) | −0.0402 (5) | −0.0446 (3) | 0.0411 (10) | |
H21A | 0.2925 | −0.0367 | −0.0353 | 0.062* | |
H21B | 0.3528 | −0.1339 | −0.0576 | 0.062* | |
H21C | 0.4270 | 0.0199 | −0.0905 | 0.062* | |
C23 | 0.3778 (7) | −0.0877 (9) | 0.1178 (4) | 0.0641 (18) | |
H23A | 0.3766 | −0.1826 | 0.1179 | 0.077* | 0.576 (10) |
H23B | 0.2753 | −0.1074 | 0.1146 | 0.077* | 0.576 (10) |
H23C | 0.2941 | −0.0698 | 0.1240 | 0.077* | 0.424 (10) |
H23D | 0.3353 | −0.1905 | 0.0970 | 0.077* | 0.424 (10) |
C24 | 0.4590 (16) | 0.007 (3) | 0.2046 (6) | 0.093 (7) | 0.576 (10) |
H24A | 0.4908 | 0.1114 | 0.1938 | 0.112* | 0.576 (10) |
H24B | 0.5479 | −0.0006 | 0.2165 | 0.112* | 0.576 (10) |
C24' | 0.432 (3) | −0.086 (2) | 0.2133 (11) | 0.079 (7) | 0.424 (10) |
H24C | 0.5274 | −0.0844 | 0.2126 | 0.095* | 0.424 (10) |
H24D | 0.3595 | −0.1749 | 0.2462 | 0.095* | 0.424 (10) |
S21 | 0.3392 (7) | −0.0573 (9) | 0.3016 (3) | 0.121 (3) | 0.576 (10) |
S21' | 0.4523 (12) | 0.0817 (10) | 0.2647 (5) | 0.126 (4) | 0.424 (10) |
C25 | 0.2501 (18) | 0.038 (2) | 0.2777 (9) | 0.166 (8) | |
H25A | 0.1459 | −0.0318 | 0.2665 | 0.250* | 0.576 (10) |
H25B | 0.2943 | 0.0988 | 0.2250 | 0.250* | 0.576 (10) |
H25C | 0.2593 | 0.1009 | 0.3280 | 0.250* | 0.576 (10) |
H25D | 0.1994 | −0.0416 | 0.3210 | 0.250* | 0.424 (10) |
H25E | 0.1998 | 0.0070 | 0.2204 | 0.250* | 0.424 (10) |
H25F | 0.2492 | 0.1259 | 0.2983 | 0.250* | 0.424 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0239 (5) | 0.0239 (5) | 0.0451 (10) | 0.0119 (3) | 0.000 | 0.000 |
O1 | 0.042 (2) | 0.042 (2) | 0.047 (3) | 0.0208 (10) | 0.000 | 0.000 |
O2 | 0.0301 (17) | 0.0283 (17) | 0.067 (2) | 0.0100 (14) | 0.0006 (15) | 0.0090 (16) |
S2 | 0.0256 (5) | 0.0256 (5) | 0.0403 (9) | 0.0128 (3) | 0.000 | 0.000 |
O3 | 0.071 (3) | 0.071 (3) | 0.043 (4) | 0.0353 (15) | 0.000 | 0.000 |
O4 | 0.0293 (16) | 0.0269 (17) | 0.079 (3) | 0.0136 (14) | 0.0040 (16) | 0.0077 (17) |
S3 | 0.0262 (5) | 0.0262 (5) | 0.0419 (10) | 0.0131 (3) | 0.000 | 0.000 |
O5 | 0.059 (3) | 0.059 (3) | 0.042 (3) | 0.0295 (13) | 0.000 | 0.000 |
O6 | 0.072 (3) | 0.035 (2) | 0.070 (3) | −0.002 (2) | −0.008 (2) | −0.003 (2) |
O11 | 0.045 (2) | 0.038 (2) | 0.050 (2) | 0.0078 (16) | −0.0025 (17) | 0.0016 (17) |
O12 | 0.044 (2) | 0.053 (2) | 0.059 (2) | 0.0254 (18) | −0.0045 (17) | 0.0022 (18) |
N11 | 0.048 (3) | 0.031 (2) | 0.051 (3) | 0.0185 (19) | 0.0105 (19) | −0.0022 (18) |
C11 | 0.042 (3) | 0.034 (2) | 0.047 (3) | 0.022 (2) | 0.006 (2) | 0.000 (2) |
C12 | 0.040 (3) | 0.036 (2) | 0.044 (2) | 0.019 (2) | 0.008 (2) | 0.001 (2) |
C13 | 0.042 (3) | 0.052 (3) | 0.058 (4) | 0.018 (2) | −0.005 (2) | −0.003 (3) |
C14 | 0.070 (5) | 0.068 (4) | 0.060 (4) | 0.023 (4) | −0.007 (3) | 0.007 (3) |
S11 | 0.0890 (15) | 0.0899 (15) | 0.0657 (11) | 0.0337 (12) | 0.0030 (10) | −0.0215 (11) |
C15 | 0.104 (8) | 0.079 (6) | 0.099 (7) | 0.011 (6) | −0.015 (6) | −0.024 (5) |
O21 | 0.0334 (19) | 0.066 (3) | 0.056 (2) | 0.0283 (19) | −0.0085 (16) | −0.021 (2) |
O22 | 0.042 (2) | 0.073 (3) | 0.054 (2) | 0.035 (2) | −0.0054 (17) | −0.021 (2) |
C21 | 0.030 (2) | 0.030 (2) | 0.045 (3) | 0.0121 (18) | 0.0041 (19) | 0.0045 (18) |
C22 | 0.033 (2) | 0.037 (2) | 0.043 (2) | 0.019 (2) | 0.003 (2) | −0.003 (2) |
N21 | 0.032 (2) | 0.049 (2) | 0.045 (2) | 0.0219 (19) | 0.0037 (17) | 0.0101 (18) |
C23 | 0.053 (3) | 0.104 (5) | 0.043 (3) | 0.045 (4) | 0.017 (3) | 0.016 (3) |
C24 | 0.078 (10) | 0.20 (2) | 0.018 (5) | 0.081 (14) | 0.005 (5) | −0.004 (8) |
C24' | 0.098 (16) | 0.098 (16) | 0.066 (13) | 0.067 (14) | 0.017 (10) | 0.031 (11) |
S21 | 0.143 (5) | 0.211 (7) | 0.0429 (18) | 0.114 (5) | 0.034 (2) | 0.043 (3) |
S21' | 0.199 (10) | 0.139 (7) | 0.065 (4) | 0.103 (7) | −0.014 (4) | −0.021 (4) |
C25 | 0.27 (2) | 0.225 (19) | 0.088 (8) | 0.19 (2) | 0.050 (11) | 0.015 (10) |
S1—O1 | 1.446 (7) | C15—H15C | 0.9600 |
S1—O2i | 1.474 (3) | O21—C21 | 1.289 (7) |
S1—O2 | 1.474 (3) | O21—H21 | 0.8200 |
S1—O2ii | 1.474 (3) | O22—C21 | 1.202 (7) |
S2—O3 | 1.433 (8) | C21—C22 | 1.517 (7) |
S2—O4iii | 1.466 (3) | C22—N21 | 1.486 (7) |
S2—O4iv | 1.466 (3) | C22—C23 | 1.530 (8) |
S2—O4 | 1.466 (3) | C22—H22 | 0.9800 |
S3—O5 | 1.429 (8) | N21—H21A | 0.8900 |
S3—O6v | 1.469 (4) | N21—H21B | 0.8900 |
S3—O6 | 1.469 (4) | N21—H21C | 0.8900 |
S3—O6vi | 1.469 (4) | C23—C24' | 1.517 (16) |
O11—C11 | 1.312 (7) | C23—C24 | 1.574 (14) |
O11—H11 | 0.8200 | C23—H23A | 0.9700 |
O12—C11 | 1.198 (7) | C23—H23B | 0.9700 |
N11—C12 | 1.494 (7) | C23—H23C | 0.9700 |
N11—H11A | 0.8900 | C23—H23D | 0.9700 |
N11—H11B | 0.8900 | C24—S21 | 1.787 (12) |
N11—H11C | 0.8900 | C24—H24A | 0.9700 |
C11—C12 | 1.529 (7) | C24—H24B | 0.9700 |
C12—C13 | 1.521 (8) | C24'—S21' | 1.803 (17) |
C12—H12 | 0.9800 | C24'—H24C | 0.9700 |
C13—C14 | 1.532 (10) | C24'—H24D | 0.9700 |
C13—H13A | 0.9700 | S21—C25 | 1.678 (13) |
C13—H13B | 0.9700 | S21'—C25 | 1.903 (15) |
C14—S11 | 1.789 (9) | C25—H25A | 0.9600 |
C14—H14A | 0.9700 | C25—H25B | 0.9600 |
C14—H14B | 0.9700 | C25—H25C | 0.9600 |
S11—C15 | 1.823 (12) | C25—H25D | 0.9600 |
C15—H15A | 0.9600 | C25—H25E | 0.9600 |
C15—H15B | 0.9600 | C25—H25F | 0.9600 |
O1—S1—O2i | 110.08 (18) | C22—N21—H21C | 109.5 |
O1—S1—O2 | 110.08 (19) | H21A—N21—H21C | 109.5 |
O2i—S1—O2 | 108.85 (19) | H21B—N21—H21C | 109.5 |
O1—S1—O2ii | 110.08 (18) | C24'—C23—C22 | 127.2 (12) |
O2i—S1—O2ii | 108.85 (19) | C24'—C23—C24 | 32.4 (9) |
O2—S1—O2ii | 108.85 (19) | C22—C23—C24 | 104.9 (8) |
O3—S2—O4iii | 109.9 (2) | C24'—C23—H23A | 80.0 |
O3—S2—O4iv | 109.9 (2) | C22—C23—H23A | 110.8 |
O4iii—S2—O4iv | 109.1 (2) | C24—C23—H23A | 110.8 |
O3—S2—O4 | 109.9 (2) | C24'—C23—H23B | 113.8 |
O4iii—S2—O4 | 109.1 (2) | C22—C23—H23B | 110.8 |
O4iv—S2—O4 | 109.1 (2) | C24—C23—H23B | 110.8 |
O5—S3—O6v | 111.0 (2) | H23A—C23—H23B | 108.8 |
O5—S3—O6 | 111.0 (2) | C24'—C23—H23C | 105.5 |
O6v—S3—O6 | 107.9 (2) | C22—C23—H23C | 105.5 |
O5—S3—O6vi | 111.0 (2) | C24—C23—H23C | 93.0 |
O6v—S3—O6vi | 107.9 (2) | H23A—C23—H23C | 128.6 |
O6—S3—O6vi | 107.9 (2) | H23B—C23—H23C | 21.6 |
C11—O11—H11 | 109.5 | C24'—C23—H23D | 105.5 |
C12—N11—H11A | 109.5 | C22—C23—H23D | 105.5 |
C12—N11—H11B | 109.5 | C24—C23—H23D | 137.8 |
H11A—N11—H11B | 109.5 | H23A—C23—H23D | 29.8 |
C12—N11—H11C | 109.5 | H23B—C23—H23D | 84.6 |
H11A—N11—H11C | 109.5 | H23C—C23—H23D | 106.1 |
H11B—N11—H11C | 109.5 | C23—C24—S21 | 111.9 (10) |
O12—C11—O11 | 124.9 (5) | C23—C24—H24A | 109.2 |
O12—C11—C12 | 121.0 (5) | S21—C24—H24A | 109.2 |
O11—C11—C12 | 114.1 (5) | C23—C24—H24B | 109.2 |
N11—C12—C13 | 112.0 (5) | S21—C24—H24B | 109.2 |
N11—C12—C11 | 105.7 (4) | H24A—C24—H24B | 107.9 |
C13—C12—C11 | 115.1 (4) | C23—C24'—S21' | 105.4 (10) |
N11—C12—H12 | 107.9 | C23—C24'—H24C | 110.7 |
C13—C12—H12 | 107.9 | S21'—C24'—H24C | 110.7 |
C11—C12—H12 | 107.9 | C23—C24'—H24D | 110.7 |
C12—C13—C14 | 112.7 (5) | S21'—C24'—H24D | 110.7 |
C12—C13—H13A | 109.0 | H24C—C24'—H24D | 108.8 |
C14—C13—H13A | 109.0 | C25—S21—C24 | 95.3 (9) |
C12—C13—H13B | 109.0 | C24'—S21'—C25 | 103.1 (11) |
C14—C13—H13B | 109.0 | S21—C25—S21' | 46.4 (5) |
H13A—C13—H13B | 107.8 | S21—C25—H25A | 109.5 |
C13—C14—S11 | 114.5 (5) | S21'—C25—H25A | 147.1 |
C13—C14—H14A | 108.6 | S21—C25—H25B | 109.5 |
S11—C14—H14A | 108.6 | S21'—C25—H25B | 70.1 |
C13—C14—H14B | 108.6 | H25A—C25—H25B | 109.5 |
S11—C14—H14B | 108.6 | S21—C25—H25C | 109.5 |
H14A—C14—H14B | 107.6 | S21'—C25—H25C | 101.0 |
C14—S11—C15 | 98.5 (5) | H25A—C25—H25C | 109.5 |
S11—C15—H15A | 109.5 | H25B—C25—H25C | 109.5 |
S11—C15—H15B | 109.5 | S21—C25—H25D | 65.6 |
H15A—C15—H15B | 109.5 | S21'—C25—H25D | 109.5 |
S11—C15—H15C | 109.5 | H25A—C25—H25D | 63.4 |
H15A—C15—H15C | 109.5 | H25B—C25—H25D | 167.0 |
H15B—C15—H15C | 109.5 | H25C—C25—H25D | 83.5 |
C21—O21—H21 | 109.5 | S21—C25—H25E | 110.7 |
O22—C21—O21 | 125.3 (5) | S21'—C25—H25E | 109.5 |
O22—C21—C22 | 121.2 (5) | H25A—C25—H25E | 52.0 |
O21—C21—C22 | 113.4 (4) | H25B—C25—H25E | 60.0 |
N21—C22—C21 | 108.0 (4) | H25C—C25—H25E | 139.6 |
N21—C22—C23 | 108.7 (4) | H25D—C25—H25E | 109.5 |
C21—C22—C23 | 113.7 (5) | S21—C25—H25F | 138.5 |
N21—C22—H22 | 108.8 | S21'—C25—H25F | 109.5 |
C21—C22—H22 | 108.8 | H25A—C25—H25F | 102.9 |
C23—C22—H22 | 108.8 | H25B—C25—H25F | 82.3 |
C22—N21—H21A | 109.5 | H25C—C25—H25F | 32.9 |
C22—N21—H21B | 109.5 | H25D—C25—H25F | 109.5 |
H21A—N21—H21B | 109.5 | H25E—C25—H25F | 109.5 |
O12—C11—C12—N11 | 30.7 (6) | N21—C22—C23—C24' | 173.9 (10) |
O11—C11—C12—N11 | −148.4 (5) | C21—C22—C23—C24' | 53.6 (12) |
O12—C11—C12—C13 | 154.8 (5) | N21—C22—C23—C24 | −159.6 (9) |
O11—C11—C12—C13 | −24.3 (6) | C21—C22—C23—C24 | 80.1 (10) |
N11—C12—C13—C14 | −154.7 (5) | C24'—C23—C24—S21 | −60 (2) |
C11—C12—C13—C14 | 84.5 (6) | C22—C23—C24—S21 | 161.4 (10) |
C12—C13—C14—S11 | 63.1 (7) | C22—C23—C24'—S21' | 74.6 (17) |
C13—C14—S11—C15 | 70.8 (7) | C24—C23—C24'—S21' | 21.0 (12) |
O22—C21—C22—N21 | −11.1 (7) | C23—C24—S21—C25 | −82.4 (15) |
O21—C21—C22—N21 | 166.7 (4) | C23—C24'—S21'—C25 | 70.0 (15) |
O22—C21—C22—C23 | 109.5 (6) | C24—S21—C25—S21' | −37.2 (7) |
O21—C21—C22—C23 | −72.6 (6) | C24'—S21'—C25—S21 | 47.2 (8) |
Symmetry codes: (i) −y+1, x−y+1, z; (ii) −x+y, −x+1, z; (iii) −x+y+1, −x+2, z; (iv) −y+2, x−y+1, z; (v) −y+1, x−y, z; (vi) −x+y+1, −x+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O2iv | 0.82 | 1.79 | 2.569 (6) | 159 |
N11—H11A···O3vii | 0.89 | 2.36 | 3.233 (7) | 169 |
N11—H11B···O2vii | 0.89 | 2.16 | 2.964 (6) | 151 |
N11—H11B···O12viii | 0.89 | 2.33 | 2.816 (6) | 115 |
N11—H11C···O6 | 0.89 | 2.17 | 2.989 (8) | 153 |
N11—H11C···O6v | 0.89 | 2.49 | 3.209 (8) | 138 |
O21—H21···O4ix | 0.82 | 1.76 | 2.576 (5) | 171 |
N21—H21A···O4x | 0.89 | 2.11 | 2.956 (6) | 159 |
N21—H21B···O1xi | 0.89 | 2.22 | 3.079 (6) | 162 |
N21—H21B···O22xii | 0.89 | 2.65 | 3.083 (7) | 111 |
N21—H21C···O6xiii | 0.89 | 1.96 | 2.839 (7) | 168 |
Symmetry codes: (iv) −y+2, x−y+1, z; (v) −y+1, x−y, z; (vii) x, y−1, z; (viii) −y+1, x−y−1, z; (ix) −x+y+1, −x+1, z−1; (x) −y+1, x−y, z−1; (xi) x, y−1, z−1; (xii) −y, x−y−1, z; (xiii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | 2C5H12NO2S+·SO42− |
Mr | 396.49 |
Crystal system, space group | Trigonal, P3 |
Temperature (K) | 293 |
a, c (Å) | 10.281 (3), 14.788 (6) |
V (Å3) | 1353.5 (8) |
Z | 3 |
Radiation type | Cu Kα |
µ (mm−1) | 4.12 |
Crystal size (mm) | 0.5 × 0.35 × 0.2 |
Data collection | |
Diffractometer | Enraf-Nonius sealed tube diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.221, 0.438 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2818, 1786, 1690 |
Rint | 0.066 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.147, 1.09 |
No. of reflections | 1786 |
No. of parameters | 229 |
No. of restraints | 7 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.60, −0.51 |
Absolute structure parameter | −0.01 (3) |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999), SHELXL97.
O11—C11 | 1.312 (7) | O21—C21 | 1.289 (7) |
O12—C11 | 1.198 (7) | O22—C21 | 1.202 (7) |
O11—C11—C12—N11 | −148.4 (5) | C21—C22—C23—C24' | 53.6 (12) |
N11—C12—C13—C14 | −154.7 (5) | N21—C22—C23—C24 | −159.6 (9) |
C11—C12—C13—C14 | 84.5 (6) | C21—C22—C23—C24 | 80.1 (10) |
C12—C13—C14—S11 | 63.1 (7) | C22—C23—C24—S21 | 161.4 (10) |
C13—C14—S11—C15 | 70.8 (7) | C22—C23—C24'—S21' | 74.6 (17) |
O21—C21—C22—N21 | 166.7 (4) | C23—C24—S21—C25 | −82.4 (15) |
N21—C22—C23—C24' | 173.9 (10) | C23—C24'—S21'—C25 | 70.0 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O2i | 0.82 | 1.79 | 2.569 (6) | 158.9 |
N11—H11A···O3ii | 0.89 | 2.36 | 3.233 (7) | 169.0 |
N11—H11B···O2ii | 0.89 | 2.16 | 2.964 (6) | 150.6 |
N11—H11B···O12iii | 0.89 | 2.33 | 2.816 (6) | 114.5 |
N11—H11C···O6 | 0.89 | 2.17 | 2.989 (8) | 152.8 |
N11—H11C···O6iv | 0.89 | 2.49 | 3.209 (8) | 138.0 |
O21—H21···O4v | 0.82 | 1.76 | 2.576 (5) | 170.8 |
N21—H21A···O4vi | 0.89 | 2.11 | 2.956 (6) | 159.1 |
N21—H21B···O1vii | 0.89 | 2.22 | 3.079 (6) | 162.4 |
N21—H21B···O22viii | 0.89 | 2.65 | 3.083 (7) | 110.8 |
N21—H21C···O6ix | 0.89 | 1.96 | 2.839 (7) | 167.8 |
Symmetry codes: (i) −y+2, x−y+1, z; (ii) x, y−1, z; (iii) −y+1, x−y−1, z; (iv) −y+1, x−y, z; (v) −x+y+1, −x+1, z−1; (vi) −y+1, x−y, z−1; (vii) x, y−1, z−1; (viii) −y, x−y−1, z; (ix) x, y, z−1. |
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Methionine is one of the few amino acids having sulfur; it also has straight-chain aliphatic α-amino acids. The crystal structure of DL-methionine (Mathieson, 1952), L-methionine (Torii & Iitaka, 1973), DL-methionine hydrochloride (Di Blasio et al., 1977), DL-methionine nitrate (Mostad & Natarajan, 1985) and bis(DL-methionine dihydrogen phosphate) (Asath Bahadur, 1992) have already been reported. In the present study, the structure of bis(DL-methioninium)sulfate (I) was determined.
The two crystallographically independent methionine cations (A and B) have similar geometries (Fig. 1). The Cγ and Sδ atoms of molecule B are disordered. The minor contributing disordered atoms are denoted as primed atoms. The conformation angle ψ2 is -148.5 (5) and 166.7 (4) for molecules A and B, respectively, which agrees well with bis(DL-methionine dihydrogen phosphate). The χ1 straight-chain conformation is in trans form [-154.7 (5) & -159.6 (9)] for both the A and B molecules. The χ2 conformation is in gauche I form [63.1 (7)°] for molecule A, and in trans [161.4 (10)°] and gauche I [75 (2)°] forms for the unprimed and primed atoms of molecule B. The χ3 conformation is in gauche I form [70.8 (7)°] for molecule A, and in gauche II [-82 (2)°] and gauche I [70 (2)°] forms for the unprimed and primed atoms of molecule B (Lakshminarayanan et al., 1967).
The carboxyl groups of the methionine cations A and B (Fig. 2 and Table 2) form strong hydrogen bonds with the sulfate anions. The three sulfate anions sitting on the threefold axis link the amino N atom of both the molecules (A and B) and stabilize the structure. Bifurcated hydrogen bonds are observed in the case of the amino N atom and the sulfate- and carboxyl-O atoms of both the A and B molecules (Jeffrey & Saenger, 1991). Both the A and B molecules are engaged in a head-to-tail sequence since the hydrogen bonds N11—H11B···O12(-y + 1, x-y - 1, z) and N21—H21B···O22(-y, x-y - 1,z), connect the amino acids along xy plane (Vijayan, 1988).