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The structure of the title compound, C11H12O5S, (I), comprises a simple mol­ecule that associates via carboxyl­ic acid dimers in the solid state. Other associated dimers are formed from C—H...O intermolecular close contacts to the two carbonyl and one sulfonyl O atoms. All three SO2CH3 H atoms and one phenyl H atom are also involved in these close-contact associations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200990X/na6163sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680200990X/na6163Isup2.hkl
Contains datablock I

CCDC reference: 189890

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.138
  • Data-to-parameter ratio = 15.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

3-(4-(Methylsulfonyl)benzoyl)propionic acid top
Crystal data top
C11H12O5SZ = 2
Mr = 256.27F(000) = 268
Triclinic, P1Dx = 1.507 Mg m3
a = 5.1851 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.5030 (3) ÅCell parameters from 3181 reflections
c = 10.9550 (4) Åθ = 2.9–27.5°
α = 96.990 (1)°µ = 0.29 mm1
β = 101.135 (1)°T = 120 K
γ = 101.786 (3)°Prism, colourless
V = 564.90 (3) Å30.40 × 0.20 × 0.06 mm
Data collection top
Bruker–Nonius KappaCCD area-detector
diffractometer
2484 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode2089 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.9°
φ and ω scansh = 66
Absorption correction: multi-scan
SORTAV (Blessing, 1995)
k = 1313
Tmin = 0.892, Tmax = 0.983l = 1414
6362 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
2484 reflections(Δ/σ)max < 0.001
159 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.66 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2139 (4)0.37910 (17)0.04390 (17)0.0180 (4)
O100.4157 (3)0.44149 (12)0.12343 (12)0.0225 (3)
O110.1782 (3)0.38926 (14)0.07673 (13)0.0250 (3)
H110.299 (5)0.441 (3)0.090 (3)0.047 (8)*
C20.0197 (4)0.29148 (18)0.07621 (18)0.0208 (4)
H210.12100.22690.00000.026*
H220.14290.34580.10040.026*
C30.0597 (4)0.21685 (17)0.18267 (17)0.0183 (4)
H310.16730.28070.25820.023*
H320.10570.16880.20450.023*
C40.2221 (4)0.12014 (17)0.14735 (17)0.0180 (4)
O410.3176 (3)0.12502 (14)0.05412 (13)0.0287 (4)
C50.2661 (3)0.01746 (17)0.22850 (16)0.0156 (4)
C60.4319 (4)0.06576 (17)0.20102 (17)0.0181 (4)
H60.51950.05550.13310.023*
C70.4698 (4)0.16350 (17)0.27228 (17)0.0186 (4)
H70.58430.21980.25410.023*
C80.3384 (4)0.17814 (17)0.37069 (16)0.0157 (4)
C90.1724 (4)0.09650 (19)0.39875 (18)0.0217 (4)
H90.08240.10800.46580.027*
C100.1382 (4)0.00224 (18)0.32835 (18)0.0213 (4)
H100.02710.05980.34820.027*
S10.37915 (9)0.30490 (4)0.46100 (4)0.01837 (18)
O10.3055 (3)0.27250 (13)0.57857 (12)0.0260 (3)
O20.6471 (3)0.32488 (14)0.46423 (14)0.0299 (4)
C110.1423 (4)0.44481 (18)0.37026 (18)0.0213 (4)
H1110.04010.42940.36150.027*
H1120.15360.52140.41220.027*
H1130.18130.46160.28650.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0204 (9)0.0170 (9)0.0203 (9)0.0089 (7)0.0063 (7)0.0067 (7)
O100.0233 (7)0.0234 (7)0.0193 (7)0.0018 (5)0.0038 (5)0.0059 (5)
O110.0250 (8)0.0269 (8)0.0206 (7)0.0014 (6)0.0029 (6)0.0111 (6)
C20.0201 (9)0.0199 (9)0.0251 (10)0.0061 (7)0.0058 (8)0.0106 (8)
C30.0216 (9)0.0170 (9)0.0200 (9)0.0066 (7)0.0088 (7)0.0071 (7)
C40.0196 (9)0.0156 (9)0.0187 (9)0.0013 (7)0.0064 (7)0.0042 (7)
O410.0431 (9)0.0300 (8)0.0261 (8)0.0176 (7)0.0232 (7)0.0144 (6)
C50.0169 (9)0.0135 (8)0.0158 (9)0.0006 (7)0.0053 (7)0.0027 (7)
C60.0200 (9)0.0173 (9)0.0177 (9)0.0024 (7)0.0084 (7)0.0024 (7)
C70.0192 (9)0.0165 (9)0.0232 (9)0.0066 (7)0.0092 (7)0.0041 (7)
C80.0159 (9)0.0151 (8)0.0156 (9)0.0015 (7)0.0031 (7)0.0046 (7)
C90.0279 (11)0.0232 (10)0.0195 (10)0.0089 (8)0.0123 (8)0.0080 (8)
C100.0264 (10)0.0222 (10)0.0217 (10)0.0117 (8)0.0127 (8)0.0064 (8)
S10.0180 (3)0.0179 (3)0.0202 (3)0.00448 (19)0.00343 (19)0.00750 (19)
O10.0321 (8)0.0266 (7)0.0188 (7)0.0052 (6)0.0047 (6)0.0069 (6)
O20.0189 (7)0.0332 (8)0.0439 (9)0.0107 (6)0.0085 (6)0.0202 (7)
C110.0260 (10)0.0163 (9)0.0229 (10)0.0048 (7)0.0082 (8)0.0041 (7)
Geometric parameters (Å, º) top
C1—O101.230 (2)C6—H60.95
C1—O111.319 (2)C7—C81.390 (3)
C1—C21.493 (3)C7—H70.95
O11—H110.79 (3)C8—C91.382 (3)
C2—C31.521 (2)C8—S11.775 (2)
C2—H210.99C9—C101.385 (3)
C2—H220.99C9—H90.95
C3—C41.506 (2)C10—H100.95
C3—H310.99S1—O11.434 (1)
C3—H320.99S1—O21.441 (1)
C4—O411.220 (2)S1—C111.758 (2)
C4—C51.504 (2)C11—H1110.98
C5—C61.392 (2)C11—H1120.98
C5—C101.393 (2)C11—H1130.98
C6—C71.386 (2)
O10—C1—O11122.9 (2)C6—C7—C8119.2 (2)
O10—C1—C2123.1 (2)C6—C7—H7120.4
O11—C1—C2114.0 (2)C8—C7—H7120.4
C1—O11—H11112 (2)C9—C8—C7121.1 (2)
C1—C2—C3114.1 (2)C9—C8—S1119.1 (1)
C1—C2—H21108.7C7—C8—S1119.9 (1)
C3—C2—H21108.7C8—C9—C10119.5 (2)
C1—C2—H22108.7C8—C9—H9120.3
C3—C2—H22108.7C10—C9—H9120.3
H21—C2—H22107.6C9—C10—C5120.2 (2)
C4—C3—C2112.1 (2)C9—C10—H10119.9
C4—C3—H31109.2C5—C10—H10119.9
C2—C3—H31109.2O1—S1—O2118.32 (9)
C4—C3—H32109.2O1—S1—C11109.39 (9)
C2—C3—H32109.2O2—S1—C11108.71 (9)
H31—C3—H32107.9O1—S1—C8108.56 (8)
O41—C4—C5120.2 (2)O2—S1—C8107.26 (8)
O41—C4—C3120.5 (2)C11—S1—C8103.60 (9)
C5—C4—C3119.3 (2)S1—C11—H111109.5
C6—C5—C10119.7 (2)S1—C11—H112109.5
C6—C5—C4119.2 (2)H111—C11—H112109.5
C10—C5—C4121.1 (2)S1—C11—H113109.5
C7—C6—C5120.3 (2)H111—C11—H113109.5
C7—C6—H6119.8H112—C11—H113109.5
C5—C6—H6119.8
O10—C1—C2—C336.6 (2)C6—C7—C8—S1178.7 (1)
O11—C1—C2—C3146.9 (2)C7—C8—C9—C100.6 (3)
C1—C2—C3—C464.9 (2)S1—C8—C9—C10179.7 (1)
C2—C3—C4—O4113.5 (2)C8—C9—C10—C51.2 (3)
C2—C3—C4—C5166.7 (1)C6—C5—C10—C91.0 (3)
O41—C4—C5—C64.4 (3)C4—C5—C10—C9177.3 (2)
C3—C4—C5—C6175.5 (2)C9—C8—S1—O120.4 (2)
O41—C4—C5—C10173.9 (2)C7—C8—S1—O1160.5 (1)
C3—C4—C5—C106.2 (3)C9—C8—S1—O2149.4 (2)
C10—C5—C6—C70.1 (3)C7—C8—S1—O231.5 (2)
C4—C5—C6—C7178.3 (2)C9—C8—S1—C1195.8 (2)
C5—C6—C7—C80.6 (3)C7—C8—S1—C1183.4 (2)
C6—C7—C8—C90.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H11···O10i0.79 (3)1.85 (3)2.6388 (18)178 (3)
C6—H6···O41ii0.952.453.346 (2)157
C9—H9···O10.952.582.942 (2)103
C11—H111···O2iii0.982.503.357 (2)146
C11—H113···O10iv0.982.573.483 (2)155
C11—H112···O2v0.982.493.423 (2)160
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x1, y, z; (iv) x, y1, z; (v) x+1, y1, z+1.
 

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