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In the title compound, C5H12NO2S+·ClO4·C5H11NO2S·H2O, the L-me­thionine and L-me­thioninium residues are linked by a strong O...O hydrogen bond [2.500 (1) Å]. The me­thionine residue adopts a transgauche I–gauche I conformation, while the me­thioninium residue has a gauche II–transgauche I conformation. The me­thioninium residues in the crystal are engaged in straight (S1) head-to-tail hydrogen bonding, thus forming infinite chains along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010656/ya6110sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010656/ya6110Isup2.hkl
Contains datablock I

CCDC reference: 189911

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.086
  • Data-to-parameter ratio = 40.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 37.60 From the CIF: _reflns_number_total 9018 Count of symmetry unique reflns 5304 Completeness (_total/calc) 170.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3714 Fraction of Friedel pairs measured 0.700 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

L-methionine L-methioninium perchlorate monohydrate top
Crystal data top
C5H12NO2S+·ClO4·C5H11NO2S·H2OF(000) = 440
Mr = 416.89Dx = 1.493 Mg m3
Dm = 1.472 Mg m3
Dm measured by flotation in carbon tetrachloride and xylene
Monoclinic, P21Mo Kα radiation, λ = 0.71070 Å
a = 11.3720 (15) ÅCell parameters from 7529 reflections
b = 5.5876 (8) Åθ = 2.7–37.6°
c = 15.323 (2) ŵ = 0.48 mm1
β = 107.782 (5)°T = 105 K
V = 927.1 (2) Å3Plate, colorless
Z = 20.8 × 0.4 × 0.2 mm
Data collection top
Bruker SMART CCD
diffractometer
9018 independent reflections
Radiation source: fine-focus sealed tube8635 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.33 pixels mm-1θmax = 37.6°, θmin = 1.4°
ω scansh = 1918
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 99
Tmin = 0.677, Tmax = 0.913l = 2626
17119 measured reflections
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)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0501P)2 + 0.1368P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
9018 reflectionsΔρmax = 0.62 e Å3
225 parametersΔρmin = 0.60 e Å3
1 restraintAbsolute structure: Flack (1983), 3692 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (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
xyzUiso*/Ueq
Cl0.521360 (19)0.65794 (4)0.605643 (14)0.01177 (4)
O10.56965 (9)0.6632 (2)0.52947 (6)0.02188 (15)
O20.57325 (8)0.45792 (17)0.66442 (6)0.01972 (15)
O30.55157 (8)0.87874 (17)0.65699 (6)0.02051 (15)
O40.38773 (7)0.63508 (16)0.57392 (6)0.01849 (14)
O1A0.11741 (7)1.42468 (17)0.59291 (6)0.01835 (14)
O1B0.12625 (8)1.41499 (17)0.74137 (6)0.01938 (14)
C110.16270 (9)1.35608 (17)0.67458 (7)0.01322 (14)
C120.27300 (8)1.18507 (17)0.69587 (6)0.01156 (14)
H120.24781.03030.71440.014*
N110.30826 (7)1.15005 (18)0.61010 (5)0.01364 (12)
H11A0.24351.09550.56570.020*
H11B0.36971.04480.62060.020*
H11C0.33251.28910.59300.020*
C130.38321 (9)1.27857 (19)0.77340 (7)0.01450 (15)
H13A0.45871.21320.76620.017*
H13B0.38701.45140.76870.017*
C140.37581 (11)1.2128 (2)0.86843 (7)0.01780 (18)
H14A0.29831.27140.87430.021*
H14B0.44211.29320.91430.021*
S110.38650 (3)0.89384 (6)0.891692 (18)0.01910 (5)
C150.54450 (12)0.8390 (3)0.89445 (9)0.0247 (2)
H15A0.56360.67250.90630.037*
H15B0.59920.93360.94210.037*
H15C0.55450.88190.83650.037*
O2A0.84774 (9)0.28937 (18)0.63593 (8)0.0265 (2)
O2B1.02666 (8)0.18599 (18)0.74094 (7)0.02335 (17)
H2B1.04840.32050.73100.035*
C210.91375 (9)0.14753 (19)0.68887 (7)0.01533 (16)
C220.86929 (9)0.10138 (18)0.70495 (7)0.01375 (15)
H220.93590.21670.70990.016*
N210.76185 (8)0.1652 (2)0.62420 (6)0.01641 (14)
H21A0.73450.31010.63240.025*
H21B0.70180.05840.61820.025*
H21C0.78520.16500.57380.025*
C230.83376 (10)0.1067 (2)0.79420 (7)0.01655 (17)
H23A0.74990.04870.78200.020*
H23B0.88800.00090.83890.020*
C240.84328 (11)0.3598 (2)0.83367 (8)0.01893 (18)
H24A0.79900.46850.78550.023*
H24B0.92940.40780.85320.023*
S210.78281 (3)0.39046 (6)0.92960 (2)0.02403 (6)
C250.87637 (14)0.1791 (3)1.00959 (9)0.0299 (3)
H25A0.85270.17871.06460.045*
H25B0.96170.22361.02400.045*
H25C0.86470.02210.98290.045*
OW0.12675 (8)1.83730 (16)0.50284 (6)0.01686 (13)
H1W0.115 (2)1.718 (4)0.5277 (16)0.027 (5)*
H2W0.058 (2)1.875 (5)0.4691 (15)0.032 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.01113 (8)0.01132 (8)0.01329 (8)0.00050 (6)0.00437 (6)0.00080 (7)
O10.0263 (4)0.0247 (4)0.0196 (3)0.0015 (3)0.0143 (3)0.0023 (3)
O20.0186 (3)0.0191 (4)0.0226 (4)0.0075 (3)0.0079 (3)0.0091 (3)
O30.0206 (3)0.0160 (4)0.0227 (4)0.0016 (3)0.0032 (3)0.0062 (3)
O40.0095 (3)0.0165 (4)0.0276 (4)0.0004 (2)0.0029 (2)0.0002 (3)
O1A0.0151 (3)0.0201 (4)0.0179 (3)0.0041 (3)0.0020 (2)0.0041 (3)
O1B0.0188 (3)0.0205 (4)0.0212 (3)0.0073 (3)0.0095 (3)0.0009 (3)
C110.0108 (3)0.0114 (4)0.0175 (4)0.0008 (2)0.0043 (3)0.0008 (3)
C120.0117 (3)0.0111 (4)0.0122 (3)0.0010 (2)0.0041 (2)0.0001 (3)
N110.0141 (3)0.0138 (3)0.0138 (3)0.0017 (3)0.0054 (2)0.0007 (3)
C130.0140 (4)0.0147 (4)0.0135 (3)0.0004 (3)0.0023 (3)0.0007 (3)
C140.0211 (4)0.0188 (5)0.0131 (4)0.0034 (3)0.0047 (3)0.0000 (3)
S110.01965 (11)0.02054 (12)0.01728 (10)0.00042 (9)0.00588 (8)0.00526 (9)
C150.0231 (5)0.0283 (6)0.0230 (5)0.0080 (4)0.0073 (4)0.0064 (4)
O2A0.0213 (4)0.0207 (4)0.0327 (5)0.0017 (3)0.0009 (3)0.0102 (3)
O2B0.0169 (3)0.0203 (4)0.0280 (4)0.0074 (3)0.0003 (3)0.0056 (3)
C210.0140 (4)0.0156 (4)0.0169 (4)0.0018 (3)0.0054 (3)0.0017 (3)
C220.0124 (3)0.0138 (4)0.0151 (4)0.0014 (3)0.0043 (3)0.0003 (3)
N210.0144 (3)0.0186 (4)0.0163 (3)0.0032 (3)0.0049 (2)0.0030 (3)
C230.0196 (4)0.0158 (4)0.0149 (4)0.0016 (3)0.0064 (3)0.0006 (3)
C240.0215 (4)0.0176 (5)0.0181 (4)0.0013 (3)0.0066 (3)0.0035 (3)
S210.02551 (13)0.02760 (15)0.01996 (11)0.00908 (11)0.00839 (9)0.00393 (10)
C250.0317 (6)0.0393 (8)0.0181 (4)0.0092 (5)0.0066 (4)0.0022 (5)
OW0.0155 (3)0.0173 (3)0.0165 (3)0.0003 (2)0.0029 (2)0.0017 (2)
Geometric parameters (Å, º) top
Cl—O11.4339 (8)O2A—C211.2156 (14)
Cl—O21.4435 (9)O2B—C211.3060 (14)
Cl—O31.4471 (9)O2B—H2B0.8200
Cl—O41.4529 (8)C21—C221.5254 (15)
O1A—C111.2587 (13)C22—N211.4925 (13)
O1B—C111.2596 (13)C22—C231.5400 (14)
C11—C121.5306 (13)C22—H220.9800
C12—N111.4994 (12)N21—H21A0.8900
C12—C131.5316 (14)N21—H21B0.8900
C12—H120.9800N21—H21C0.8900
N11—H11A0.8900C23—C241.5290 (16)
N11—H11B0.8900C23—H23A0.9700
N11—H11C0.8900C23—H23B0.9700
C13—C141.5289 (15)C24—S211.8112 (11)
C13—H13A0.9700C24—H24A0.9700
C13—H13B0.9700C24—H24B0.9700
C14—S111.8140 (12)S21—C251.7979 (15)
C14—H14A0.9700C25—H25A0.9600
C14—H14B0.9700C25—H25B0.9600
S11—C151.8105 (14)C25—H25C0.9600
C15—H15A0.9600OW—H1W0.80 (2)
C15—H15B0.9600OW—H2W0.82 (2)
C15—H15C0.9600
O1—Cl—O2109.79 (6)H15A—C15—H15C109.5
O1—Cl—O3109.80 (6)H15B—C15—H15C109.5
O2—Cl—O3109.69 (6)C21—O2B—H2B109.5
O1—Cl—O4110.55 (5)O2A—C21—O2B126.30 (11)
O2—Cl—O4109.10 (5)O2A—C21—C22122.32 (10)
O3—Cl—O4107.89 (5)O2B—C21—C22111.34 (9)
O1B—C11—O1A126.29 (9)N21—C22—C21108.16 (9)
O1B—C11—C12116.20 (9)N21—C22—C23111.17 (8)
O1A—C11—C12117.51 (9)C21—C22—C23110.54 (8)
N11—C12—C11108.41 (7)N21—C22—H22109.0
N11—C12—C13110.47 (8)C21—C22—H22109.0
C11—C12—C13112.06 (8)C23—C22—H22109.0
N11—C12—H12108.6C22—N21—H21A109.5
C11—C12—H12108.6C22—N21—H21B109.5
C13—C12—H12108.6H21A—N21—H21B109.5
C12—N11—H11A109.5C22—N21—H21C109.5
C12—N11—H11B109.5H21A—N21—H21C109.5
H11A—N11—H11B109.5H21B—N21—H21C109.5
C12—N11—H11C109.5C24—C23—C22111.28 (9)
H11A—N11—H11C109.5C24—C23—H23A109.4
H11B—N11—H11C109.5C22—C23—H23A109.4
C14—C13—C12112.74 (9)C24—C23—H23B109.4
C14—C13—H13A109.0C22—C23—H23B109.4
C12—C13—H13A109.0H23A—C23—H23B108.0
C14—C13—H13B109.0C23—C24—S21114.20 (8)
C12—C13—H13B109.0C23—C24—H24A108.7
H13A—C13—H13B107.8S21—C24—H24A108.7
C13—C14—S11113.80 (8)C23—C24—H24B108.7
C13—C14—H14A108.8S21—C24—H24B108.7
S11—C14—H14A108.8H24A—C24—H24B107.6
C13—C14—H14B108.8C25—S21—C24101.47 (6)
S11—C14—H14B108.8S21—C25—H25A109.5
H14A—C14—H14B107.7S21—C25—H25B109.5
C15—S11—C14100.21 (6)H25A—C25—H25B109.5
S11—C15—H15A109.5S21—C25—H25C109.5
S11—C15—H15B109.5H25A—C25—H25C109.5
H15A—C15—H15B109.5H25B—C25—H25C109.5
S11—C15—H15C109.5H1W—OW—H2W104 (2)
O1A—C11—C12—N113.82 (12)O2A—C21—C22—N2121.62 (15)
O1B—C11—C12—N11176.01 (9)O2B—C21—C22—N21160.75 (10)
O1B—C11—C12—C1353.83 (12)O2A—C21—C22—C23100.30 (13)
O1A—C11—C12—C13126.01 (10)O2B—C21—C22—C2377.33 (12)
N11—C12—C13—C14153.83 (9)N21—C22—C23—C2484.52 (11)
C11—C12—C13—C1485.17 (11)C21—C22—C23—C24155.34 (9)
C12—C13—C14—S1165.58 (11)C22—C23—C24—S21171.84 (7)
C13—C14—S11—C1567.02 (9)C23—C24—S21—C2558.75 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···OWi0.892.002.818 (1)153
N11—H11B···O30.892.183.042 (1)164
N11—H11C···O4ii0.892.082.962 (1)171
O2B—H2B···O1Biii0.821.712.500 (1)163
N21—H21A···O20.892.202.909 (1)137
N21—H21A···O2Aii0.892.573.189 (2)127
N21—H21B···O3i0.892.213.044 (1)155
N21—H21C···OWiv0.892.012.798 (1)147
OW—H1W···O1A0.80 (2)1.92 (3)2.706 (1)169 (2)
OW—H2W···O1Av0.82 (2)1.95 (2)2.759 (1)168 (2)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x+1, y2, z; (iv) x+1, y3/2, z+1; (v) x, y+1/2, z+1.
 

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