organic compounds
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—HO 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
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200990X/na6163sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680200990X/na6163Isup2.hkl |
CCDC reference: 189890
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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
C11H12O5S | Z = 2 |
Mr = 256.27 | F(000) = 268 |
Triclinic, P1 | Dx = 1.507 Mg m−3 |
a = 5.1851 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5030 (3) Å | Cell parameters from 3181 reflections |
c = 10.9550 (4) Å | θ = 2.9–27.5° |
α = 96.990 (1)° | µ = 0.29 mm−1 |
β = 101.135 (1)° | T = 120 K |
γ = 101.786 (3)° | Prism, colourless |
V = 564.90 (3) Å3 | 0.40 × 0.20 × 0.06 mm |
Data collection top
Bruker–Nonius KappaCCD area-detector diffractometer | 2484 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 2089 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.9° |
φ and ω scans | h = −6→6 |
Absorption correction: multi-scan SORTAV (Blessing, 1995) | k = −13→13 |
Tmin = 0.892, Tmax = 0.983 | l = −14→14 |
6362 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H 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 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.2139 (4) | 0.37910 (17) | 0.04390 (17) | 0.0180 (4) | |
O10 | 0.4157 (3) | 0.44149 (12) | 0.12343 (12) | 0.0225 (3) | |
O11 | 0.1782 (3) | 0.38926 (14) | −0.07673 (13) | 0.0250 (3) | |
H11 | 0.299 (5) | 0.441 (3) | −0.090 (3) | 0.047 (8)* | |
C2 | −0.0197 (4) | 0.29148 (18) | 0.07621 (18) | 0.0208 (4) | |
H21 | −0.1210 | 0.2269 | 0.0000 | 0.026* | |
H22 | −0.1429 | 0.3458 | 0.1004 | 0.026* | |
C3 | 0.0597 (4) | 0.21685 (17) | 0.18267 (17) | 0.0183 (4) | |
H31 | 0.1673 | 0.2807 | 0.2582 | 0.023* | |
H32 | −0.1057 | 0.1688 | 0.2045 | 0.023* | |
C4 | 0.2221 (4) | 0.12014 (17) | 0.14735 (17) | 0.0180 (4) | |
O41 | 0.3176 (3) | 0.12502 (14) | 0.05412 (13) | 0.0287 (4) | |
C5 | 0.2661 (3) | 0.01746 (17) | 0.22850 (16) | 0.0156 (4) | |
C6 | 0.4319 (4) | −0.06576 (17) | 0.20102 (17) | 0.0181 (4) | |
H6 | 0.5195 | −0.0555 | 0.1331 | 0.023* | |
C7 | 0.4698 (4) | −0.16350 (17) | 0.27228 (17) | 0.0186 (4) | |
H7 | 0.5843 | −0.2198 | 0.2541 | 0.023* | |
C8 | 0.3384 (4) | −0.17814 (17) | 0.37069 (16) | 0.0157 (4) | |
C9 | 0.1724 (4) | −0.09650 (19) | 0.39875 (18) | 0.0217 (4) | |
H9 | 0.0824 | −0.1080 | 0.4658 | 0.027* | |
C10 | 0.1382 (4) | 0.00224 (18) | 0.32835 (18) | 0.0213 (4) | |
H10 | 0.0271 | 0.0598 | 0.3482 | 0.027* | |
S1 | 0.37915 (9) | −0.30490 (4) | 0.46100 (4) | 0.01837 (18) | |
O1 | 0.3055 (3) | −0.27250 (13) | 0.57857 (12) | 0.0260 (3) | |
O2 | 0.6471 (3) | −0.32488 (14) | 0.46423 (14) | 0.0299 (4) | |
C11 | 0.1423 (4) | −0.44481 (18) | 0.37026 (18) | 0.0213 (4) | |
H111 | −0.0401 | −0.4294 | 0.3615 | 0.027* | |
H112 | 0.1536 | −0.5214 | 0.4122 | 0.027* | |
H113 | 0.1813 | −0.4616 | 0.2865 | 0.027* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0204 (9) | 0.0170 (9) | 0.0203 (9) | 0.0089 (7) | 0.0063 (7) | 0.0067 (7) |
O10 | 0.0233 (7) | 0.0234 (7) | 0.0193 (7) | 0.0018 (5) | 0.0038 (5) | 0.0059 (5) |
O11 | 0.0250 (8) | 0.0269 (8) | 0.0206 (7) | −0.0014 (6) | 0.0029 (6) | 0.0111 (6) |
C2 | 0.0201 (9) | 0.0199 (9) | 0.0251 (10) | 0.0061 (7) | 0.0058 (8) | 0.0106 (8) |
C3 | 0.0216 (9) | 0.0170 (9) | 0.0200 (9) | 0.0066 (7) | 0.0088 (7) | 0.0071 (7) |
C4 | 0.0196 (9) | 0.0156 (9) | 0.0187 (9) | 0.0013 (7) | 0.0064 (7) | 0.0042 (7) |
O41 | 0.0431 (9) | 0.0300 (8) | 0.0261 (8) | 0.0176 (7) | 0.0232 (7) | 0.0144 (6) |
C5 | 0.0169 (9) | 0.0135 (8) | 0.0158 (9) | 0.0006 (7) | 0.0053 (7) | 0.0027 (7) |
C6 | 0.0200 (9) | 0.0173 (9) | 0.0177 (9) | 0.0024 (7) | 0.0084 (7) | 0.0024 (7) |
C7 | 0.0192 (9) | 0.0165 (9) | 0.0232 (9) | 0.0066 (7) | 0.0092 (7) | 0.0041 (7) |
C8 | 0.0159 (9) | 0.0151 (8) | 0.0156 (9) | 0.0015 (7) | 0.0031 (7) | 0.0046 (7) |
C9 | 0.0279 (11) | 0.0232 (10) | 0.0195 (10) | 0.0089 (8) | 0.0123 (8) | 0.0080 (8) |
C10 | 0.0264 (10) | 0.0222 (10) | 0.0217 (10) | 0.0117 (8) | 0.0127 (8) | 0.0064 (8) |
S1 | 0.0180 (3) | 0.0179 (3) | 0.0202 (3) | 0.00448 (19) | 0.00343 (19) | 0.00750 (19) |
O1 | 0.0321 (8) | 0.0266 (7) | 0.0188 (7) | 0.0052 (6) | 0.0047 (6) | 0.0069 (6) |
O2 | 0.0189 (7) | 0.0332 (8) | 0.0439 (9) | 0.0107 (6) | 0.0085 (6) | 0.0202 (7) |
C11 | 0.0260 (10) | 0.0163 (9) | 0.0229 (10) | 0.0048 (7) | 0.0082 (8) | 0.0041 (7) |
Geometric parameters (Å, º) top
C1—O10 | 1.230 (2) | C6—H6 | 0.95 |
C1—O11 | 1.319 (2) | C7—C8 | 1.390 (3) |
C1—C2 | 1.493 (3) | C7—H7 | 0.95 |
O11—H11 | 0.79 (3) | C8—C9 | 1.382 (3) |
C2—C3 | 1.521 (2) | C8—S1 | 1.775 (2) |
C2—H21 | 0.99 | C9—C10 | 1.385 (3) |
C2—H22 | 0.99 | C9—H9 | 0.95 |
C3—C4 | 1.506 (2) | C10—H10 | 0.95 |
C3—H31 | 0.99 | S1—O1 | 1.434 (1) |
C3—H32 | 0.99 | S1—O2 | 1.441 (1) |
C4—O41 | 1.220 (2) | S1—C11 | 1.758 (2) |
C4—C5 | 1.504 (2) | C11—H111 | 0.98 |
C5—C6 | 1.392 (2) | C11—H112 | 0.98 |
C5—C10 | 1.393 (2) | C11—H113 | 0.98 |
C6—C7 | 1.386 (2) | ||
O10—C1—O11 | 122.9 (2) | C6—C7—C8 | 119.2 (2) |
O10—C1—C2 | 123.1 (2) | C6—C7—H7 | 120.4 |
O11—C1—C2 | 114.0 (2) | C8—C7—H7 | 120.4 |
C1—O11—H11 | 112 (2) | C9—C8—C7 | 121.1 (2) |
C1—C2—C3 | 114.1 (2) | C9—C8—S1 | 119.1 (1) |
C1—C2—H21 | 108.7 | C7—C8—S1 | 119.9 (1) |
C3—C2—H21 | 108.7 | C8—C9—C10 | 119.5 (2) |
C1—C2—H22 | 108.7 | C8—C9—H9 | 120.3 |
C3—C2—H22 | 108.7 | C10—C9—H9 | 120.3 |
H21—C2—H22 | 107.6 | C9—C10—C5 | 120.2 (2) |
C4—C3—C2 | 112.1 (2) | C9—C10—H10 | 119.9 |
C4—C3—H31 | 109.2 | C5—C10—H10 | 119.9 |
C2—C3—H31 | 109.2 | O1—S1—O2 | 118.32 (9) |
C4—C3—H32 | 109.2 | O1—S1—C11 | 109.39 (9) |
C2—C3—H32 | 109.2 | O2—S1—C11 | 108.71 (9) |
H31—C3—H32 | 107.9 | O1—S1—C8 | 108.56 (8) |
O41—C4—C5 | 120.2 (2) | O2—S1—C8 | 107.26 (8) |
O41—C4—C3 | 120.5 (2) | C11—S1—C8 | 103.60 (9) |
C5—C4—C3 | 119.3 (2) | S1—C11—H111 | 109.5 |
C6—C5—C10 | 119.7 (2) | S1—C11—H112 | 109.5 |
C6—C5—C4 | 119.2 (2) | H111—C11—H112 | 109.5 |
C10—C5—C4 | 121.1 (2) | S1—C11—H113 | 109.5 |
C7—C6—C5 | 120.3 (2) | H111—C11—H113 | 109.5 |
C7—C6—H6 | 119.8 | H112—C11—H113 | 109.5 |
C5—C6—H6 | 119.8 | ||
O10—C1—C2—C3 | −36.6 (2) | C6—C7—C8—S1 | 178.7 (1) |
O11—C1—C2—C3 | 146.9 (2) | C7—C8—C9—C10 | −0.6 (3) |
C1—C2—C3—C4 | −64.9 (2) | S1—C8—C9—C10 | −179.7 (1) |
C2—C3—C4—O41 | 13.5 (2) | C8—C9—C10—C5 | 1.2 (3) |
C2—C3—C4—C5 | −166.7 (1) | C6—C5—C10—C9 | −1.0 (3) |
O41—C4—C5—C6 | 4.4 (3) | C4—C5—C10—C9 | 177.3 (2) |
C3—C4—C5—C6 | −175.5 (2) | C9—C8—S1—O1 | −20.4 (2) |
O41—C4—C5—C10 | −173.9 (2) | C7—C8—S1—O1 | 160.5 (1) |
C3—C4—C5—C10 | 6.2 (3) | C9—C8—S1—O2 | −149.4 (2) |
C10—C5—C6—C7 | 0.1 (3) | C7—C8—S1—O2 | 31.5 (2) |
C4—C5—C6—C7 | −178.3 (2) | C9—C8—S1—C11 | 95.8 (2) |
C5—C6—C7—C8 | 0.6 (3) | C7—C8—S1—C11 | −83.4 (2) |
C6—C7—C8—C9 | −0.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O10i | 0.79 (3) | 1.85 (3) | 2.6388 (18) | 178 (3) |
C6—H6···O41ii | 0.95 | 2.45 | 3.346 (2) | 157 |
C9—H9···O1 | 0.95 | 2.58 | 2.942 (2) | 103 |
C11—H111···O2iii | 0.98 | 2.50 | 3.357 (2) | 146 |
C11—H113···O10iv | 0.98 | 2.57 | 3.483 (2) | 155 |
C11—H112···O2v | 0.98 | 2.49 | 3.423 (2) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z; (iii) x−1, y, z; (iv) x, y−1, z; (v) −x+1, −y−1, −z+1. |