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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o706.
Published online 2008 March 12. doi:  10.1107/S1600536808005035
PMCID: PMC2961050

4-(Methyl­sulfan­yl)-2-(p-toluene­sulfonamido)butanoic acid

Abstract

In the title compound, C12H17NO4S2, the carboxyl groups link the mol­ecules into centrosymmetric dimers through O—H(...)O hydrogen bonds. An N—H(...)O hydrogen bond between the NH group of the l-methio­nine unit and a neighbouring carboxyl group, together with a complementary C—H(...)O contact to one O atom of the sulfonyl group, link the dimers into one-dimensional chains along the crystallographic b axis.

Related literature

The title compound is closely related to the previously reported N-tosyl-l-glutamic acid (Zachara et al., 2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o706-scheme1.jpg

Experimental

Crystal data

  • C12H17NO4S2
  • M r = 303.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o706-efi1.jpg
  • a = 33.121 (7) Å
  • b = 5.6531 (11) Å
  • c = 17.278 (4) Å
  • β = 116.62 (3)°
  • V = 2892.2 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.38 mm−1
  • T = 293 (2) K
  • 0.43 × 0.28 × 0.22 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.855, T max = 0.922
  • 6139 measured reflections
  • 2689 independent reflections
  • 2055 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.119
  • S = 1.00
  • 2689 reflections
  • 179 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005035/bi2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005035/bi2276Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support by the Key Laboratory of Non-ferrous Metal Materials and New Processing Technology, Ministry of Education, People’s Republic of China.

supplementary crystallographic information

Comment

The title compound (Fig. 1) was synthesized from 4-toluenesulfonyl chloride and L-methionine. It is closely related to the previously reported N-tosyl-L-glutamic acid (Zachara et al., 2005).

Experimental

A solution of L-methionine (0.005 mmol) and NaOH (0.015 mmol) in water (15 ml) was added to an ethanol solution of 4-toluenesulfonyl chloride (0.005 mmol). After stirring at 348 K for 40 min, crystals of the title compound were obtained by slow evaporation of the reaction mixture at room temperature.

Refinement

H atoms bound to C or O atoms were placed geometrically with C—H = 0.93–0.97 Å or O—H = 0.82 Å and refined as riding with Uiso(H) = 1.2 or 1.5Ueq(C/O). The H atom of the NH group was located in a difference Fourier map and refined with an isotropic displacement parameter, without restraint.

Figures

Fig. 1.
The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. H atoms bound to C and N are omitted.
Fig. 2.
Partial packing diagram showing a hydrogen-bonded chain running along the b axis.

Crystal data

C12H17NO4S2F000 = 1280
Mr = 303.39Dx = 1.394 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2689 reflections
a = 33.121 (7) Åθ = 2.8–25.5º
b = 5.6531 (11) ŵ = 0.38 mm1
c = 17.278 (4) ÅT = 293 (2) K
β = 116.62 (3)ºBlock, colorless
V = 2892.2 (10) Å30.43 × 0.28 × 0.22 mm
Z = 8

Data collection

Bruker APEXII CCD diffractometer2689 independent reflections
Radiation source: fine-focus sealed tube2055 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 293(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 2.8º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −40→30
Tmin = 0.855, Tmax = 0.922k = −5→6
6139 measured reflectionsl = −17→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119  w = 1/[σ2(Fo2) + (0.0619P)2 + 2.0643P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2689 reflectionsΔρmax = 0.30 e Å3
179 parametersΔρmin = −0.25 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
C10.05669 (12)0.1441 (6)−0.2992 (2)0.0798 (10)
H1A0.08140.0695−0.25160.120*
H1B0.05140.0655−0.35210.120*
H1C0.03000.1343−0.29060.120*
C20.09539 (9)0.5313 (5)−0.19259 (17)0.0532 (7)
H2A0.11860.4170−0.15960.064*
H2B0.10980.6843−0.18600.064*
C30.06194 (8)0.5443 (5)−0.15563 (16)0.0500 (7)
H3A0.04770.3909−0.16190.060*
H3B0.03850.6573−0.18900.060*
C40.08314 (7)0.6170 (4)−0.05971 (14)0.0386 (5)
H40.10990.5190−0.02730.046*
C50.04899 (8)0.5711 (4)−0.02597 (14)0.0392 (5)
C60.16839 (7)0.8595 (4)0.11546 (15)0.0405 (5)
C70.19182 (8)0.6522 (5)0.14801 (16)0.0480 (6)
H70.19670.54720.11170.058*
C80.16108 (9)1.0154 (5)0.17034 (18)0.0512 (7)
H80.14521.15540.14880.061*
C90.20788 (9)0.6019 (5)0.23483 (18)0.0538 (7)
H90.22350.46120.25630.065*
C100.17754 (9)0.9604 (5)0.25668 (18)0.0586 (7)
H100.17241.06440.29300.070*
C110.20148 (8)0.7549 (5)0.29100 (17)0.0526 (7)
C120.22040 (10)0.7014 (7)0.38595 (19)0.0769 (10)
H12A0.22420.53360.39480.115*
H12B0.20000.75800.40740.115*
H12C0.24910.77830.41640.115*
N10.09655 (7)0.8649 (4)−0.04861 (13)0.0429 (5)
H10.0819 (9)0.958 (5)−0.0360 (18)0.051 (8)*
O10.15126 (6)1.1856 (3)0.00061 (12)0.0545 (5)
O20.17393 (5)0.7911 (3)−0.02689 (11)0.0520 (5)
O30.02802 (6)0.7289 (3)−0.01265 (11)0.0479 (4)
O40.04342 (6)0.3447 (3)−0.01734 (12)0.0499 (5)
H4A0.02040.3249−0.01150.075*
S10.149864 (19)0.93464 (11)0.00597 (4)0.0414 (2)
S20.07010 (3)0.44879 (15)−0.30518 (4)0.0630 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.100 (3)0.073 (2)0.069 (2)0.007 (2)0.0400 (19)−0.0020 (17)
C20.0484 (14)0.072 (2)0.0443 (14)0.0011 (13)0.0249 (12)0.0054 (13)
C30.0437 (14)0.0659 (18)0.0441 (14)−0.0064 (12)0.0231 (11)−0.0046 (12)
C40.0380 (12)0.0417 (14)0.0382 (12)−0.0031 (10)0.0190 (10)0.0019 (10)
C50.0424 (13)0.0435 (15)0.0326 (12)−0.0045 (11)0.0175 (10)−0.0006 (10)
C60.0353 (12)0.0368 (13)0.0474 (13)−0.0032 (10)0.0167 (10)−0.0014 (11)
C70.0503 (14)0.0377 (14)0.0509 (15)0.0017 (12)0.0182 (12)−0.0033 (11)
C80.0529 (15)0.0439 (16)0.0607 (17)0.0093 (12)0.0290 (13)0.0011 (12)
C90.0474 (15)0.0459 (16)0.0599 (17)0.0045 (12)0.0168 (13)0.0079 (13)
C100.0564 (16)0.068 (2)0.0570 (17)0.0012 (14)0.0301 (14)−0.0105 (14)
C110.0374 (13)0.0666 (19)0.0518 (15)−0.0045 (13)0.0182 (11)0.0017 (13)
C120.0579 (18)0.116 (3)0.0528 (18)0.0025 (18)0.0210 (14)0.0104 (18)
N10.0386 (11)0.0409 (13)0.0508 (12)0.0019 (10)0.0214 (10)0.0059 (10)
O10.0543 (11)0.0385 (11)0.0688 (12)−0.0036 (8)0.0259 (9)0.0097 (8)
O20.0434 (9)0.0596 (12)0.0605 (11)−0.0002 (8)0.0300 (9)−0.0021 (9)
O30.0552 (10)0.0449 (11)0.0555 (11)−0.0038 (8)0.0353 (9)−0.0017 (8)
O40.0556 (11)0.0447 (11)0.0633 (11)−0.0053 (8)0.0391 (9)0.0012 (8)
S10.0362 (3)0.0394 (4)0.0498 (4)−0.0030 (2)0.0202 (3)0.0023 (3)
S20.0773 (5)0.0750 (6)0.0407 (4)0.0063 (4)0.0300 (4)0.0059 (3)

Geometric parameters (Å, °)

C1—S21.793 (4)C6—S11.760 (3)
C1—H1A0.960C7—C91.378 (4)
C1—H1B0.960C7—H70.930
C1—H1C0.960C8—C101.375 (4)
C2—C31.508 (3)C8—H80.930
C2—S21.801 (3)C9—C111.385 (4)
C2—H2A0.970C9—H90.930
C2—H2B0.970C10—C111.381 (4)
C3—C41.538 (3)C10—H100.930
C3—H3A0.970C11—C121.501 (4)
C3—H3B0.970C12—H12A0.960
C4—N11.457 (3)C12—H12B0.960
C4—C51.509 (3)C12—H12C0.960
C4—H40.980N1—S11.634 (2)
C5—O31.214 (3)N1—H10.81 (3)
C5—O41.311 (3)O1—S11.4238 (19)
C6—C71.378 (4)O2—S11.4216 (18)
C6—C81.393 (4)O4—H4A0.820
S2—C1—H1A109.5C9—C7—H7120.3
S2—C1—H1B109.5C6—C7—H7120.3
H1A—C1—H1B109.5C10—C8—C6119.3 (3)
S2—C1—H1C109.5C10—C8—H8120.3
H1A—C1—H1C109.5C6—C8—H8120.3
H1B—C1—H1C109.5C7—C9—C11121.9 (3)
C3—C2—S2113.29 (18)C7—C9—H9119.1
C3—C2—H2A108.9C11—C9—H9119.1
S2—C2—H2A108.9C8—C10—C11121.9 (3)
C3—C2—H2B108.9C8—C10—H10119.1
S2—C2—H2B108.9C11—C10—H10119.0
H2A—C2—H2B107.7C10—C11—C9117.6 (3)
C2—C3—C4113.7 (2)C10—C11—C12121.1 (3)
C2—C3—H3A108.8C9—C11—C12121.3 (3)
C4—C3—H3A108.8C11—C12—H12A109.5
C2—C3—H3B108.8C11—C12—H12B109.5
C4—C3—H3B108.8H12A—C12—H12B109.5
H3A—C3—H3B107.7C11—C12—H12C109.5
N1—C4—C5110.6 (2)H12A—C12—H12C109.5
N1—C4—C3111.3 (2)H12B—C12—H12C109.5
C5—C4—C3108.11 (18)C4—N1—S1119.67 (17)
N1—C4—H4108.9C4—N1—H1119 (2)
C5—C4—H4108.9S1—N1—H1108 (2)
C3—C4—H4108.9C5—O4—H4A109.5
O3—C5—O4125.0 (2)O2—S1—O1120.15 (11)
O3—C5—C4122.6 (2)O2—S1—N1106.62 (12)
O4—C5—C4112.3 (2)O1—S1—N1105.14 (11)
C7—C6—C8119.9 (2)O2—S1—C6107.68 (11)
C7—C6—S1120.36 (19)O1—S1—C6107.74 (12)
C8—C6—S1119.7 (2)N1—S1—C6109.16 (11)
C9—C7—C6119.5 (2)C1—S2—C2101.15 (15)
S2—C2—C3—C4−179.45 (19)C7—C9—C11—C101.1 (4)
C2—C3—C4—N170.7 (3)C7—C9—C11—C12−178.1 (3)
C2—C3—C4—C5−167.6 (2)C5—C4—N1—S1123.41 (19)
N1—C4—C5—O317.0 (3)C3—C4—N1—S1−116.39 (19)
C3—C4—C5—O3−105.1 (3)C4—N1—S1—O248.6 (2)
N1—C4—C5—O4−166.15 (18)C4—N1—S1—O1177.16 (17)
C3—C4—C5—O471.7 (3)C4—N1—S1—C6−67.5 (2)
C8—C6—C7—C9−0.1 (4)C7—C6—S1—O2−16.2 (2)
S1—C6—C7—C9176.96 (19)C8—C6—S1—O2160.89 (19)
C7—C6—C8—C100.2 (4)C7—C6—S1—O1−147.2 (2)
S1—C6—C8—C10−177.0 (2)C8—C6—S1—O129.9 (2)
C6—C7—C9—C11−0.5 (4)C7—C6—S1—N199.2 (2)
C6—C8—C10—C110.4 (4)C8—C6—S1—N1−83.7 (2)
C8—C10—C11—C9−1.0 (4)C3—C2—S2—C1−70.4 (3)
C8—C10—C11—C12178.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4A···O3i0.821.852.672 (3)174
N1—H1···O4ii0.81 (3)2.62 (3)3.405 (3)163 (2)
C4—H4···O1iii0.982.253.165 (3)155

Symmetry codes: (i) −x, −y+1, −z; (ii) x, y+1, z; (iii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2276).

References

  • Bruker (2001). SAINT-Plus and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zachara, J., Madura, I., Hajmowicz, H. & Synoradzki, L. (2005). Acta Cryst. C61, o181–o184. [PubMed]

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