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In the title compound, 2C5H12NO2S+·SO42−, the sulfate anion forms a strong O—H...O hydrogen bond with a me­thio­ninium residue. The S atom (Sδ) of the methioninium residue is disordered. The packing reveals aggregation of the me­thioninium cations as a cylindrical cage along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021324/ci6427sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021324/ci6427Isup2.hkl
Contains datablock I

CCDC reference: 252969

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.061
  • wR factor = 0.178
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.02 Ratio PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors for C5 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors for S1' PLAT432_ALERT_2_B Short Inter X...Y Contact O22 .. C1 .. 2.81 Ang.
Alert level C WEIGH01_ALERT_1_C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+13.3806P Weighting scheme identified as calc PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.55 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for S1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for S2 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for S3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.27 Ratio
1 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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.

Bis(DL-methioninium) sulfate top
Crystal data top
2C5H12NO2S+·SO42Dx = 1.467 Mg m3
Dm = 1.465 Mg m3
Dm measured by Flotation technique using mixture of carbon tetrachloride and xylene
Mr = 396.49Mo Kα radiation, λ = 0.71069 Å
Trigonal, R3Cell parameters from 25 reflections
Hall symbol: -R 3θ = 9.7–15.5°
a = 10.233 (5) ŵ = 0.45 mm1
c = 44.494 (5) ÅT = 293 K
V = 4035 (3) Å3Block, colourless
Z = 90.3 × 0.2 × 0.15 mm
F(000) = 1890
Data collection top
MACH3-Nonius sealed tube
diffractometer
1332 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ω–2θ scansh = 1210
Absorption correction: ψ scan
(North et al., 1968)
k = 112
Tmin = 0.897, Tmax = 0.935l = 5252
5569 measured reflections3 standard reflections every 60 min
1584 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)] = 0.061H-atom parameters constrained
wR(F2) = 0.178Calculated w = 1/[σ2(Fo2) + (0.085P)2 + 13.3806P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.003
1576 reflectionsΔρmax = 0.66 e Å3
124 parametersΔρmin = 0.35 e Å3
16 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: none
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*/UeqOcc. (<1)
S10.5952 (5)0.0821 (5)0.19158 (8)0.1213 (17)0.556 (5)
S1'0.6555 (5)0.1059 (5)0.20543 (8)0.1037 (18)0.444 (5)
O10.3105 (3)0.0777 (3)0.30396 (7)0.0528 (8)
O20.3511 (3)0.0639 (4)0.26343 (7)0.0585 (9)
H2A0.27380.06240.26890.070*
N10.5857 (3)0.0387 (4)0.30463 (7)0.0436 (8)
H1A0.50900.12270.31210.065*
H1B0.61450.03590.31790.065*
H1C0.66250.05380.30080.065*
C10.3868 (4)0.0080 (4)0.28296 (9)0.0404 (9)
C20.5376 (4)0.0022 (5)0.27645 (9)0.0460 (10)
H20.61110.10770.27190.055*
C30.5367 (6)0.0921 (7)0.25088 (10)0.0656 (13)
H3A0.45380.19430.25360.079*
H3B0.62960.09570.25130.079*
C40.5214 (9)0.0366 (11)0.22050 (13)0.114 (3)
H4A0.56890.07250.22130.137*0.556 (5)
H4B0.41490.07610.21650.137*0.556 (5)
H4C0.43860.01800.22180.137*0.444 (5)
H4D0.49190.11880.20680.137*0.444 (5)
C50.7907 (10)0.0228 (14)0.1990 (2)0.162 (4)
H5A0.84470.00500.18340.195*0.556 (5)
H5B0.81120.00800.21800.195*0.556 (5)
H5C0.82240.12830.19970.195*0.556 (5)
H5D0.88240.09810.18970.195*0.444 (5)
H5E0.74220.06410.18630.195*0.444 (5)
H5F0.81320.00510.21810.195*0.444 (5)
S20.66670.33330.33330.0364 (6)
O210.66670.33330.3665 (2)0.057 (3)0.50
O220.5118 (6)0.2406 (7)0.32223 (14)0.0591 (16)0.50
S31.00000.00000.29659 (3)0.0332 (5)
O311.00000.00000.32923 (11)0.0555 (13)
O320.8842 (3)0.0329 (3)0.28512 (7)0.0468 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.154 (4)0.135 (3)0.091 (2)0.085 (3)0.014 (2)0.032 (2)
S1'0.105 (3)0.111 (3)0.074 (2)0.037 (3)0.002 (2)0.020 (2)
O10.0344 (14)0.0509 (17)0.0727 (19)0.0209 (13)0.0087 (13)0.0169 (14)
O20.0535 (18)0.078 (2)0.0657 (18)0.0495 (17)0.0121 (14)0.0200 (16)
N10.0331 (16)0.0401 (17)0.062 (2)0.0217 (14)0.0071 (14)0.0111 (14)
C10.0342 (19)0.0344 (18)0.055 (2)0.0191 (16)0.0017 (17)0.0011 (16)
C20.040 (2)0.045 (2)0.062 (2)0.0273 (18)0.0059 (17)0.0075 (18)
C30.064 (3)0.085 (4)0.064 (3)0.050 (3)0.000 (2)0.007 (2)
C40.115 (5)0.196 (7)0.076 (4)0.111 (5)0.003 (4)0.006 (4)
C50.124 (6)0.218 (9)0.136 (6)0.079 (6)0.037 (5)0.004 (6)
S20.0216 (7)0.0216 (7)0.0660 (15)0.0108 (3)0.0000.000
O210.056 (4)0.056 (4)0.059 (6)0.0281 (19)0.0000.000
O220.024 (3)0.050 (3)0.087 (4)0.006 (2)0.007 (3)0.003 (3)
S30.0217 (5)0.0217 (5)0.0563 (10)0.0109 (3)0.0000.000
O310.0538 (19)0.0538 (19)0.059 (3)0.0269 (9)0.0000.000
O320.0280 (13)0.0321 (13)0.084 (2)0.0176 (11)0.0034 (12)0.0057 (12)
Geometric parameters (Å, º) top
S1—C41.672 (7)C5—H5C0.96
S1—C51.765 (10)C5—H5D0.96
S1'—C41.568 (9)C5—H5E0.96
S1'—C51.974 (11)C5—H5F0.96
O1—C11.198 (5)S2—O22i1.467 (5)
O2—C11.303 (5)S2—O221.467 (5)
O2—H2A0.82S2—O22ii1.467 (5)
N1—C21.482 (5)S2—O22iii1.467 (5)
N1—H1A0.89S2—O22iv1.467 (5)
N1—H1B0.89S2—O22v1.467 (5)
N1—H1C0.89S2—O21iii1.476 (10)
C1—C21.522 (5)S2—O211.475 (10)
C2—C31.489 (6)O21—O22iv1.694 (8)
C2—H20.98O21—O22iii1.694 (8)
C3—C41.504 (8)O21—O22v1.694 (8)
C3—H3A0.97O22—O21iii1.694 (8)
C3—H3B0.97O22—O22v1.699 (8)
C4—H4A0.97O22—O22iv1.699 (8)
C4—H4B0.97S3—O311.452 (5)
C4—H4C0.96S3—O32vi1.475 (2)
C4—H4D0.96S3—O321.475 (2)
C5—H5A0.96S3—O32vii1.475 (2)
C5—H5B0.96
C4—S1—C5102.6 (5)H5A—C5—H5F109.7
C4—S1'—C597.9 (5)H5C—C5—H5F108.0
C1—O2—H2A109.5H5D—C5—H5F109.6
C2—N1—H1A109.5H5E—C5—H5F109.7
C2—N1—H1B109.5O22i—S2—O22109.3 (3)
H1A—N1—H1B109.5O22i—S2—O22ii109.3 (3)
C2—N1—H1C109.5O22—S2—O22ii109.3 (3)
H1A—N1—H1C109.5O22i—S2—O22iii70.7 (3)
H1B—N1—H1C109.5O22—S2—O22iii179.995 (2)
O1—C1—O2124.9 (3)O22ii—S2—O22iii70.7 (3)
O1—C1—C2121.8 (3)O22i—S2—O22iv70.7 (3)
O2—C1—C2113.3 (3)O22—S2—O22iv70.7 (3)
N1—C2—C3111.1 (3)O22ii—S2—O22iv180.0 (5)
N1—C2—C1106.7 (3)O22iii—S2—O22iv109.3 (3)
C3—C2—C1115.0 (4)O22i—S2—O22v179.996 (5)
N1—C2—H2107.9O22—S2—O22v70.7 (3)
C3—C2—H2107.9O22ii—S2—O22v70.7 (3)
C1—C2—H2107.9O22iii—S2—O22v109.3 (3)
C2—C3—C4114.2 (5)O22iv—S2—O22v109.3 (3)
C2—C3—H3A108.7O22i—S2—O21iii70.3 (2)
C4—C3—H3A108.7O22—S2—O21iii70.3 (2)
C2—C3—H3B108.7O22ii—S2—O21iii70.3 (2)
C4—C3—H3B108.7O22iii—S2—O21iii109.7 (2)
H3A—C3—H3B107.6O22iv—S2—O21iii109.7 (2)
C3—C4—S1'121.8 (6)O22v—S2—O21iii109.7 (2)
C3—C4—S1116.1 (5)O22i—S2—O21109.7 (2)
C3—C4—H4A108.3O22—S2—O21109.7 (2)
S1—C4—H4A108.3O22ii—S2—O21109.7 (2)
C3—C4—H4B108.3O22iii—S2—O2170.3 (2)
S1'—C4—H4B126.0O22iv—S2—O2170.3 (2)
S1—C4—H4B108.3O22v—S2—O2170.3 (2)
H4A—C4—H4B107.4O21iii—S2—O21179.998 (1)
C3—C4—H4C106.8S2—O21—O22iv54.6 (3)
S1'—C4—H4C106.9S2—O21—O22iii54.6 (3)
S1—C4—H4C132.1O22iv—O21—O22iii89.8 (5)
C3—C4—H4D106.8S2—O21—O22v54.6 (3)
S1'—C4—H4D106.7O22iv—O21—O22v89.8 (5)
H4C—C4—H4D107.0O22iii—O21—O22v89.8 (5)
S1—C5—H5A109.5S2—O22—O21iii55.1 (3)
S1—C5—H5B109.5S2—O22—O22v54.63 (13)
S1'—C5—H5B109.3O21iii—O22—O22v90.3 (3)
H5A—C5—H5B109.5S2—O22—O22iv54.63 (13)
S1—C5—H5C109.5O21iii—O22—O22iv90.3 (3)
H5A—C5—H5C109.5O22v—O22—O22iv89.5 (5)
H5B—C5—H5C109.5O31—S3—O32vi110.24 (13)
S1'—C5—H5D109.3O31—S3—O32110.24 (13)
H5B—C5—H5D110.7O32vi—S3—O32108.69 (13)
S1'—C5—H5E109.6O31—S3—O32vii110.24 (13)
H5B—C5—H5E108.3O32vi—S3—O32vii108.69 (13)
H5D—C5—H5E109.6O32—S3—O32vii108.69 (13)
S1'—C5—H5F109.0
O1—C1—C2—N118.9 (5)O22—S2—O21—O22iii179.998 (1)
O2—C1—C2—N1161.9 (3)O22ii—S2—O21—O22iii60.002 (1)
O1—C1—C2—C3104.8 (5)O22i—S2—O21—O22v180.000 (6)
O2—C1—C2—C374.4 (5)O22—S2—O21—O22v60.000 (6)
N1—C2—C3—C4167.7 (5)O22ii—S2—O21—O22v60.000 (6)
C1—C2—C3—C470.9 (6)O22iv—S2—O21—O22v120.000 (6)
C2—C3—C4—S1'74.1 (7)O22i—S2—O22—O21iii59.7 (3)
C2—C3—C4—S1153.2 (5)O22ii—S2—O22—O21iii59.7 (3)
C5—S1'—C4—C366.7 (7)O22iv—S2—O22—O21iii120.3 (3)
C5—S1'—C4—S141.1 (4)O22v—S2—O22—O21iii120.3 (3)
C5—S1—C4—C367.5 (8)O21—S2—O22—O21iii180.002 (2)
C5—S1—C4—S1'48.3 (5)O22i—S2—O22—O22v180.003 (2)
C4—S1—C5—S1'40.6 (4)O22ii—S2—O22—O22v60.5 (6)
C4—S1'—C5—S143.1 (4)O22iv—S2—O22—O22v119.5 (6)
O22i—S2—O21—O22iv60.000 (2)O21—S2—O22—O22v59.7 (3)
O22—S2—O21—O22iv60.000 (2)O22i—S2—O22—O22iv60.5 (6)
O22ii—S2—O21—O22iv180.000 (2)O22ii—S2—O22—O22iv180.0
O22iii—S2—O21—O22iv119.998 (2)O22v—S2—O22—O22iv119.5 (6)
O22v—S2—O21—O22iv120.000 (2)O21iii—S2—O22—O22iv120.3 (3)
O22i—S2—O21—O22iii59.998 (1)O21—S2—O22—O22iv59.7 (3)
Symmetry codes: (i) y+1, xy, z; (ii) x+y+1, x+1, z; (iii) x+4/3, y+2/3, z+2/3; (iv) xy+1/3, x1/3, z+2/3; (v) y+1/3, x+y+2/3, z+2/3; (vi) y+1, xy1, z; (vii) x+y+2, x+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O32ii0.821.782.570 (4)162
N1—H1A···O31viii0.892.303.179 (4)172
N1—H1B···O22iv0.891.922.772 (7)160
N1—H1B···O22i0.892.112.862 (7)141
N1—H1C···O320.892.102.895 (4)148
N1—H1C···O1ix0.892.412.924 (4)117
Symmetry codes: (i) y+1, xy, z; (ii) x+y+1, x+1, z; (iv) xy+1/3, x1/3, z+2/3; (viii) x+4/3, y1/3, z+2/3; (ix) x+y+1, x, z.
 

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