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In the title compound, C5H11NO2S, the conformation of the terminal meth­yl C atom with respect to the β-C atom is trans. The crystal structure is stabilized by a network of characteristic head-to-tail DL1 and DL2 sequences.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009141/wn6339sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009141/wn6339Isup2.hkl
Contains datablock I

CCDC reference: 270574

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.100
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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: SMART (Bruker 1999); cell refinement: SMART; data reduction: SAINT (Bruker 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

DL-methionine top
Crystal data top
C5H11NO2SF(000) = 640
Mr = 149.21Dx = 1.367 Mg m3
Dm = 1.36 Mg m3
Dm measured by flotation in a mixture of xylene and bromoform
Monoclinic, I2/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2yaCell parameters from 1012 reflections
a = 9.877 (2) Åθ = 2.6–26.1°
b = 4.6915 (10) ŵ = 0.38 mm1
c = 32.603 (6) ÅT = 105 K
β = 106.25 (1)°Block, colourless
V = 1450.4 (5) Å30.32 × 0.24 × 0.22 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
1436 independent reflections
Radiation source: fine-focus sealed tube1373 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8 pixels mm-1θmax = 26.3°, θmin = 2.6°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 55
Tmin = 0.85, Tmax = 0.92l = 4040
6469 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.23 w = 1/[σ2(Fo2) + (0.028P)2 + 3.0328P]
where P = (Fo2 + 2Fc2)/3
1436 reflections(Δ/σ)max = 0.001
82 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.34 e Å3
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
S10.39654 (6)0.15678 (13)0.442915 (17)0.0328 (2)
O10.14522 (14)0.2025 (3)0.31402 (5)0.0239 (3)
O20.01845 (14)0.0810 (3)0.28409 (4)0.0216 (3)
N10.19303 (17)0.3001 (3)0.29735 (5)0.0193 (4)
H1A0.14780.37300.27200.029*
H1B0.21690.12030.29410.029*
H1C0.27040.40180.30880.029*
C10.0329 (2)0.1302 (4)0.30560 (6)0.0184 (4)
C20.09968 (19)0.3086 (4)0.32589 (6)0.0181 (4)
H20.07250.50610.32930.022*
C30.1764 (2)0.1830 (4)0.36982 (6)0.0214 (4)
H3A0.11610.20310.38850.026*
H3B0.19090.01920.36650.026*
C40.3196 (2)0.3214 (4)0.39142 (6)0.0246 (4)
H4A0.30700.52390.39510.030*
H4B0.38230.29800.37350.030*
C50.5659 (2)0.3325 (6)0.45831 (7)0.0349 (5)
H5A0.61960.26390.48580.052*
H5B0.55240.53450.45970.052*
H5C0.61580.29240.43760.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0350 (3)0.0336 (3)0.0230 (3)0.0067 (2)0.0031 (2)0.0074 (2)
O10.0223 (7)0.0168 (7)0.0334 (8)0.0011 (5)0.0090 (6)0.0004 (6)
O20.0254 (7)0.0155 (7)0.0220 (7)0.0011 (5)0.0037 (5)0.0028 (5)
N10.0212 (8)0.0164 (8)0.0191 (8)0.0009 (6)0.0036 (6)0.0007 (6)
C10.0213 (9)0.0136 (9)0.0182 (9)0.0007 (7)0.0020 (7)0.0034 (7)
C20.0211 (9)0.0125 (8)0.0208 (9)0.0007 (7)0.0058 (7)0.0008 (7)
C30.0248 (10)0.0188 (9)0.0195 (9)0.0006 (8)0.0045 (8)0.0002 (7)
C40.0276 (10)0.0214 (10)0.0213 (9)0.0014 (8)0.0010 (8)0.0015 (8)
C50.0307 (11)0.0415 (14)0.0268 (11)0.0024 (10)0.0011 (9)0.0012 (10)
Geometric parameters (Å, º) top
S1—C51.806 (2)C2—H20.9800
S1—C41.811 (2)C3—C41.536 (3)
O1—C11.261 (2)C3—H3A0.9700
O2—C11.245 (2)C3—H3B0.9700
N1—C21.483 (2)C4—H4A0.9700
N1—H1A0.8900C4—H4B0.9700
N1—H1B0.8900C5—H5A0.9600
N1—H1C0.8900C5—H5B0.9600
C1—C21.539 (3)C5—H5C0.9600
C2—C31.538 (3)
C5—S1—C4100.30 (10)C4—C3—H3A108.6
C2—N1—H1A109.5C2—C3—H3A108.6
C2—N1—H1B109.5C4—C3—H3B108.6
H1A—N1—H1B109.5C2—C3—H3B108.6
C2—N1—H1C109.5H3A—C3—H3B107.6
H1A—N1—H1C109.5C3—C4—S1109.79 (14)
H1B—N1—H1C109.5C3—C4—H4A109.7
O2—C1—O1125.64 (18)S1—C4—H4A109.7
O2—C1—C2117.20 (16)C3—C4—H4B109.7
O1—C1—C2117.06 (17)S1—C4—H4B109.7
N1—C2—C3110.07 (15)H4A—C4—H4B108.2
N1—C2—C1108.62 (15)S1—C5—H5A109.5
C3—C2—C1109.29 (15)S1—C5—H5B109.5
N1—C2—H2109.6H5A—C5—H5B109.5
C3—C2—H2109.6S1—C5—H5C109.5
C1—C2—H2109.6H5A—C5—H5C109.5
C4—C3—C2114.56 (16)H5B—C5—H5C109.5
O2—C1—C2—N132.6 (2)N1—C2—C3—C454.4 (2)
O1—C1—C2—N1150.95 (16)C1—C2—C3—C4173.58 (16)
O2—C1—C2—C387.6 (2)C2—C3—C4—S1179.23 (13)
O1—C1—C2—C388.9 (2)C5—S1—C4—C3174.99 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.891.932.788 (2)162
N1—H1B···O1ii0.892.022.814 (2)148
N1—H1C···O1iii0.892.022.794 (2)144
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1/2, y, z; (iii) x+1/2, y+1, z.
 

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