Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C13H18O4S, displays a CPh-S-C-Cacid torsion angle of 33.23 (8)°; it has been suggested that this angle should be approximately 60° for the mol­ecule to act as an artificial sweetener. Mol­ecules are connected by classical carboxylic acid hydrogen-bond dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017879/bt2083sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017879/bt2083Isup2.hkl
Contains datablock I

CCDC reference: 610720

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.105
  • Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.103 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

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: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

2,3-Dimethyl-2-(p-tolylsulfonyl)butyric acid top
Crystal data top
C13H18O4SDx = 1.349 Mg m3
Mr = 270.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 7042 reflections
a = 10.6198 (11) Åθ = 2.7–30.5°
b = 12.4497 (12) ŵ = 0.25 mm1
c = 20.141 (2) ÅT = 133 K
V = 2662.9 (5) Å3Tablet, colourless
Z = 80.27 × 0.24 × 0.22 mm
F(000) = 1152
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3280 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.103
Graphite monochromatorθmax = 30.5°, θmin = 2.0°
Detector resolution: 8.192 pixels mm-1h = 1515
φ and ω scansk = 1717
36385 measured reflectionsl = 2828
4064 independent 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.5795P]
where P = (Fo2 + 2Fc2)/3
4064 reflections(Δ/σ)max = 0.001
171 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

Experimental. 1H NMR (CDCl3, 400 MHz): δ 7.75 (d, 2H), 7.3 (d, 2H), 2.80 (m, 1H), 1.60 (s, 3H), 1.40 (s, 3H), 1.25 (d, 3H), 1.00 (d, 3H); ESI MS (m/z) for C13H18O4S: 271 (M + H)+.

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
S0.71994 (2)0.61810 (2)0.661423 (13)0.01669 (9)
O10.71786 (8)0.68551 (7)0.71968 (4)0.02406 (19)
O20.82694 (8)0.54865 (7)0.65063 (4)0.02217 (18)
O30.44357 (8)0.55535 (7)0.56664 (4)0.02235 (19)
O40.61754 (8)0.45422 (7)0.55849 (4)0.02235 (18)
H040.5981 (19)0.4500 (16)0.5150 (11)0.053 (6)*
C10.57492 (10)0.53498 (8)0.66302 (5)0.0151 (2)
C20.47162 (11)0.59863 (10)0.69806 (6)0.0204 (2)
H2A0.45680.66600.67420.025*
H2B0.49790.61450.74370.025*
H2C0.39390.55620.69880.025*
C30.53853 (10)0.51603 (8)0.59075 (5)0.0162 (2)
C40.60493 (11)0.42479 (9)0.69631 (6)0.0193 (2)
H40.68160.39450.67440.023*
C50.63208 (12)0.43461 (11)0.77071 (6)0.0260 (3)
H5A0.55530.45670.79400.031*
H5B0.69810.48840.77790.031*
H5C0.66030.36500.78790.031*
C60.49643 (14)0.34585 (10)0.68557 (7)0.0317 (3)
H6A0.52010.27520.70300.038*
H6B0.47840.34000.63800.038*
H6C0.42130.37180.70880.038*
C110.70149 (10)0.70019 (9)0.59057 (6)0.0184 (2)
C120.75800 (12)0.66995 (10)0.53112 (6)0.0241 (2)
H120.81020.60810.52930.029*
C130.73739 (12)0.73109 (11)0.47452 (7)0.0274 (3)
H130.77640.71080.43400.033*
C140.66009 (11)0.82206 (10)0.47625 (7)0.0245 (2)
C150.60624 (11)0.85126 (10)0.53673 (7)0.0250 (2)
H150.55430.91330.53870.030*
C160.62660 (11)0.79217 (9)0.59392 (6)0.0220 (2)
H160.59020.81390.63480.026*
C170.63827 (13)0.88764 (11)0.41445 (7)0.0322 (3)
H17A0.54760.89440.40650.039*
H17B0.67790.85200.37650.039*
H17C0.67510.95920.42020.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.01545 (14)0.01863 (14)0.01598 (14)0.00136 (9)0.00161 (9)0.00072 (9)
O10.0278 (5)0.0243 (4)0.0201 (4)0.0044 (3)0.0041 (3)0.0054 (3)
O20.0156 (4)0.0271 (4)0.0238 (4)0.0024 (3)0.0009 (3)0.0025 (3)
O30.0186 (4)0.0309 (4)0.0176 (4)0.0062 (3)0.0030 (3)0.0051 (3)
O40.0226 (4)0.0283 (4)0.0161 (4)0.0088 (3)0.0026 (3)0.0070 (3)
C10.0149 (4)0.0170 (4)0.0135 (5)0.0003 (4)0.0004 (3)0.0024 (4)
C20.0190 (5)0.0238 (5)0.0184 (5)0.0016 (4)0.0026 (4)0.0042 (4)
C30.0165 (5)0.0166 (4)0.0156 (5)0.0010 (4)0.0000 (4)0.0025 (4)
C40.0210 (5)0.0182 (5)0.0187 (5)0.0005 (4)0.0014 (4)0.0012 (4)
C50.0286 (6)0.0292 (6)0.0203 (6)0.0024 (5)0.0040 (5)0.0041 (5)
C60.0377 (7)0.0227 (6)0.0346 (7)0.0099 (5)0.0097 (6)0.0064 (5)
C110.0173 (5)0.0188 (5)0.0192 (5)0.0031 (4)0.0012 (4)0.0016 (4)
C120.0224 (5)0.0266 (6)0.0234 (6)0.0038 (4)0.0037 (4)0.0038 (5)
C130.0270 (6)0.0330 (6)0.0222 (6)0.0003 (5)0.0031 (5)0.0047 (5)
C140.0204 (5)0.0260 (6)0.0273 (6)0.0065 (4)0.0052 (5)0.0065 (5)
C150.0230 (6)0.0195 (5)0.0325 (7)0.0011 (4)0.0034 (5)0.0032 (5)
C160.0224 (5)0.0184 (5)0.0252 (6)0.0019 (4)0.0006 (4)0.0018 (4)
C170.0294 (6)0.0347 (7)0.0326 (7)0.0051 (5)0.0070 (5)0.0132 (6)
Geometric parameters (Å, º) top
S—O11.4427 (9)O4—H040.90 (2)
S—O21.4443 (9)C2—H2A0.9800
S—C111.7661 (12)C2—H2B0.9800
S—C11.8557 (11)C2—H2C0.9800
O3—C31.2215 (13)C4—H41.0000
O4—C31.3108 (13)C5—H5A0.9800
C1—C31.5245 (15)C5—H5B0.9800
C1—C21.5263 (15)C5—H5C0.9800
C1—C41.5598 (15)C6—H6A0.9800
C4—C61.5298 (17)C6—H6B0.9800
C4—C51.5310 (17)C6—H6C0.9800
C11—C121.3913 (17)C12—H120.9500
C11—C161.3958 (16)C13—H130.9500
C12—C131.3881 (18)C15—H150.9500
C13—C141.3992 (18)C16—H160.9500
C14—C151.3939 (19)C17—H17A0.9800
C14—C171.5065 (18)C17—H17B0.9800
C15—C161.3837 (17)C17—H17C0.9800
O1—S—O2118.86 (5)C1—C2—H2C109.5
O1—S—C11108.59 (6)H2A—C2—H2C109.5
O2—S—C11108.19 (5)H2B—C2—H2C109.5
O1—S—C1107.31 (5)C6—C4—H4108.0
O2—S—C1108.77 (5)C5—C4—H4108.0
C11—S—C1104.16 (5)C1—C4—H4108.0
C3—C1—C2109.86 (9)C4—C5—H5A109.5
C3—C1—C4109.03 (9)C4—C5—H5B109.5
C2—C1—C4113.88 (9)H5A—C5—H5B109.5
C3—C1—S106.27 (7)C4—C5—H5C109.5
C2—C1—S108.36 (7)H5A—C5—H5C109.5
C4—C1—S109.17 (7)H5B—C5—H5C109.5
O3—C3—O4124.52 (10)C4—C6—H6A109.5
O3—C3—C1121.79 (10)C4—C6—H6B109.5
O4—C3—C1113.69 (9)H6A—C6—H6B109.5
C6—C4—C5109.37 (10)C4—C6—H6C109.5
C6—C4—C1110.51 (9)H6A—C6—H6C109.5
C5—C4—C1112.89 (10)H6B—C6—H6C109.5
C12—C11—C16120.62 (11)C13—C12—H12120.3
C12—C11—S119.40 (9)C11—C12—H12120.3
C16—C11—S119.93 (9)C12—C13—H13119.5
C13—C12—C11119.37 (11)C14—C13—H13119.5
C12—C13—C14121.06 (12)C16—C15—H15119.2
C15—C14—C13118.26 (11)C14—C15—H15119.2
C15—C14—C17121.17 (12)C15—C16—H16120.5
C13—C14—C17120.56 (12)C11—C16—H16120.5
C16—C15—C14121.65 (11)C14—C17—H17A109.5
C15—C16—C11119.02 (11)C14—C17—H17B109.5
C3—O4—H04111.7 (13)H17A—C17—H17B109.5
C1—C2—H2A109.5C14—C17—H17C109.5
C1—C2—H2B109.5H17A—C17—H17C109.5
H2A—C2—H2B109.5H17B—C17—H17C109.5
O1—S—C1—C3148.25 (7)C2—C1—C4—C552.21 (13)
O2—S—C1—C381.96 (8)S—C1—C4—C569.02 (11)
C11—S—C1—C333.23 (8)O1—S—C11—C12148.95 (10)
O1—S—C1—C230.24 (9)O2—S—C11—C1218.67 (11)
O2—S—C1—C2160.02 (7)C1—S—C11—C1296.94 (10)
C11—S—C1—C284.79 (8)O1—S—C11—C1633.59 (10)
O1—S—C1—C494.30 (8)O2—S—C11—C16163.87 (9)
O2—S—C1—C435.49 (8)C1—S—C11—C1680.53 (10)
C11—S—C1—C4150.68 (8)C16—C11—C12—C131.21 (18)
C2—C1—C3—O34.90 (14)S—C11—C12—C13176.23 (10)
C4—C1—C3—O3130.34 (11)C11—C12—C13—C140.4 (2)
S—C1—C3—O3112.12 (10)C12—C13—C14—C151.36 (19)
C2—C1—C3—O4174.68 (9)C12—C13—C14—C17179.89 (12)
C4—C1—C3—O449.25 (12)C13—C14—C15—C160.66 (18)
S—C1—C3—O468.29 (10)C17—C14—C15—C16179.40 (11)
C3—C1—C4—C652.45 (13)C14—C15—C16—C110.95 (18)
C2—C1—C4—C670.62 (12)C12—C11—C16—C151.90 (17)
S—C1—C4—C6168.14 (9)S—C11—C16—C15175.54 (9)
C3—C1—C4—C5175.28 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H04···O3i0.90 (2)1.70 (2)2.6051 (12)178 (2)
Symmetry code: (i) x+1, y+1, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds