The title compound, C
12H
12O
3S, was prepared by the Lewis acid-catalyzed reaction of 4-hydroxyphenylacetic acid with α-chloro-α-(methylsulfanyl)acetone. The 1-benzofuran ring system is nearly planar. The structure is stabilized by intermolecular aromatic π–π interactions between the furan rings of the benzofuran group, H
2C—H
π interactions and inversion-related intermolecular O—H
O hydrogen bonds between the carboxyl groups.
Supporting information
CCDC reference: 628404
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.083
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm
| Author Response: The Beam size is 0.8 mm.
|
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
[2-Methyl-3-methylsulfanyl-1-(benzofuran-5-yl)]acetic acid
top
Crystal data top
C12H12O3S | Z = 2 |
Mr = 236.28 | F(000) = 248 |
Triclinic, P1 | Dx = 1.384 Mg m−3 |
Hall symbol: -p_1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1751 (5) Å | Cell parameters from 4078 reflections |
b = 8.1457 (6) Å | θ = 2.5–28.3° |
c = 9.8533 (7) Å | µ = 0.27 mm−1 |
α = 81.998 (1)° | T = 120 K |
β = 85.120 (1)° | Block, colorless |
γ = 85.800 (1)° | 0.62 × 0.54 × 0.45 mm |
V = 567.11 (7) Å3 | |
Data collection top
Bruker SMART CCD diffractometer | 2172 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 26.5°, θmin = 2.1° |
Detector resolution: 10.00 pixels mm-1 | h = −8→8 |
φ and ω scans | k = −10→10 |
4717 measured reflections | l = −12→12 |
2309 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0316P)2 + 0.3303P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2309 reflections | Δρmax = 0.29 e Å−3 |
147 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.091 (6) |
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 | x | y | z | Uiso*/Ueq | |
S | 0.16363 (6) | 0.83927 (5) | 0.32168 (4) | 0.03713 (15) | |
O1 | 0.27862 (14) | 0.38847 (11) | 0.51229 (10) | 0.0256 (2) | |
O2 | 0.44771 (14) | 0.78857 (12) | 0.97583 (12) | 0.0320 (3) | |
H2 | 0.5303 | 0.8439 | 0.9950 | 0.048* | |
O3 | 0.28381 (14) | 1.03263 (12) | 0.96519 (11) | 0.0311 (3) | |
C1 | 0.1274 (2) | 0.79345 (18) | 0.93203 (15) | 0.0281 (3) | |
H1A | 0.0272 | 0.8747 | 0.9048 | 0.034* | |
H1B | 0.0834 | 0.7279 | 1.0170 | 0.034* | |
C2 | 0.16784 (18) | 0.68002 (17) | 0.82208 (14) | 0.0240 (3) | |
C3 | 0.16429 (19) | 0.74652 (16) | 0.68406 (14) | 0.0238 (3) | |
H3 | 0.1366 | 0.8595 | 0.6591 | 0.029* | |
C4 | 0.20302 (18) | 0.64071 (16) | 0.58395 (14) | 0.0221 (3) | |
C5 | 0.24318 (19) | 0.47162 (16) | 0.62488 (14) | 0.0232 (3) | |
C6 | 0.2443 (2) | 0.40112 (17) | 0.76057 (15) | 0.0276 (3) | |
H6 | 0.2686 | 0.2876 | 0.7850 | 0.033* | |
C7 | 0.2073 (2) | 0.50856 (18) | 0.85872 (14) | 0.0272 (3) | |
H7 | 0.2086 | 0.4660 | 0.9513 | 0.033* | |
C8 | 0.21442 (19) | 0.65981 (16) | 0.43527 (14) | 0.0240 (3) | |
C9 | 0.26180 (19) | 0.50729 (17) | 0.39797 (14) | 0.0238 (3) | |
C10 | 0.2983 (2) | 0.44629 (18) | 0.26315 (15) | 0.0293 (3) | |
H10A | 0.1957 | 0.3840 | 0.2469 | 0.044* | |
H10B | 0.4118 | 0.3762 | 0.2629 | 0.044* | |
H10C | 0.3110 | 0.5390 | 0.1921 | 0.044* | |
C11 | 0.29339 (19) | 0.88359 (17) | 0.95866 (13) | 0.0234 (3) | |
C12 | 0.3485 (3) | 0.9673 (2) | 0.3500 (2) | 0.0567 (5) | |
H12A | 0.3366 | 1.0721 | 0.2923 | 0.068* | |
H12B | 0.4680 | 0.9123 | 0.3282 | 0.068* | |
H12C | 0.3390 | 0.9856 | 0.4446 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0572 (3) | 0.0260 (2) | 0.0261 (2) | 0.00491 (17) | −0.00774 (17) | 0.00273 (14) |
O1 | 0.0319 (5) | 0.0202 (5) | 0.0250 (5) | −0.0009 (4) | −0.0043 (4) | −0.0035 (4) |
O2 | 0.0274 (5) | 0.0255 (5) | 0.0451 (6) | 0.0010 (4) | −0.0090 (4) | −0.0099 (4) |
O3 | 0.0279 (5) | 0.0231 (5) | 0.0420 (6) | −0.0001 (4) | −0.0055 (4) | −0.0028 (4) |
C1 | 0.0247 (7) | 0.0343 (7) | 0.0263 (7) | −0.0039 (6) | 0.0024 (5) | −0.0088 (6) |
C2 | 0.0194 (6) | 0.0279 (7) | 0.0254 (7) | −0.0046 (5) | −0.0008 (5) | −0.0053 (5) |
C3 | 0.0237 (6) | 0.0209 (6) | 0.0268 (7) | −0.0014 (5) | −0.0018 (5) | −0.0029 (5) |
C4 | 0.0210 (6) | 0.0219 (6) | 0.0230 (6) | −0.0023 (5) | −0.0031 (5) | −0.0002 (5) |
C5 | 0.0238 (7) | 0.0214 (6) | 0.0252 (7) | −0.0025 (5) | −0.0033 (5) | −0.0047 (5) |
C6 | 0.0328 (7) | 0.0213 (6) | 0.0279 (7) | −0.0026 (5) | −0.0054 (6) | 0.0021 (5) |
C7 | 0.0292 (7) | 0.0296 (7) | 0.0223 (7) | −0.0059 (5) | −0.0034 (5) | 0.0016 (5) |
C8 | 0.0267 (7) | 0.0229 (6) | 0.0220 (6) | −0.0014 (5) | −0.0037 (5) | −0.0004 (5) |
C9 | 0.0231 (7) | 0.0250 (6) | 0.0234 (7) | −0.0025 (5) | −0.0037 (5) | −0.0016 (5) |
C10 | 0.0322 (8) | 0.0301 (7) | 0.0273 (7) | −0.0046 (6) | −0.0025 (6) | −0.0082 (6) |
C11 | 0.0256 (7) | 0.0269 (7) | 0.0171 (6) | −0.0012 (5) | 0.0013 (5) | −0.0026 (5) |
C12 | 0.0802 (15) | 0.0317 (9) | 0.0559 (12) | −0.0187 (9) | 0.0060 (11) | 0.0037 (8) |
Geometric parameters (Å, º) top
S—C8 | 1.7487 (13) | C4—C5 | 1.3963 (18) |
S—C12 | 1.809 (2) | C4—C8 | 1.4475 (19) |
O1—C5 | 1.3748 (16) | C5—C6 | 1.3801 (19) |
O1—C9 | 1.3866 (16) | C6—C7 | 1.389 (2) |
O2—C11 | 1.3129 (17) | C6—H6 | 0.9300 |
O2—H2 | 0.8200 | C7—H7 | 0.9300 |
O3—C11 | 1.2213 (17) | C8—C9 | 1.3558 (19) |
C1—C11 | 1.504 (2) | C9—C10 | 1.4784 (19) |
C1—C2 | 1.5158 (18) | C10—H10A | 0.9600 |
C1—H1A | 0.9700 | C10—H10B | 0.9600 |
C1—H1B | 0.9700 | C10—H10C | 0.9600 |
C2—C3 | 1.3936 (19) | C12—H12A | 0.9600 |
C2—C7 | 1.407 (2) | C12—H12B | 0.9600 |
C3—C4 | 1.3958 (19) | C12—H12C | 0.9600 |
C3—H3 | 0.9300 | | |
| | | |
C8—S—C12 | 100.98 (8) | C6—C7—C2 | 121.87 (13) |
C5—O1—C9 | 106.18 (10) | C6—C7—H7 | 119.1 |
C11—O2—H2 | 109.5 | C2—C7—H7 | 119.1 |
C11—C1—C2 | 114.09 (11) | C9—C8—C4 | 106.88 (12) |
C11—C1—H1A | 108.7 | C9—C8—S | 125.04 (11) |
C2—C1—H1A | 108.7 | C4—C8—S | 127.97 (10) |
C11—C1—H1B | 108.7 | C8—C9—O1 | 111.14 (12) |
C2—C1—H1B | 108.7 | C8—C9—C10 | 132.99 (13) |
H1A—C1—H1B | 107.6 | O1—C9—C10 | 115.87 (12) |
C3—C2—C7 | 120.07 (13) | C9—C10—H10A | 109.5 |
C3—C2—C1 | 119.52 (12) | C9—C10—H10B | 109.5 |
C7—C2—C1 | 120.41 (13) | H10A—C10—H10B | 109.5 |
C2—C3—C4 | 118.86 (12) | C9—C10—H10C | 109.5 |
C2—C3—H3 | 120.6 | H10A—C10—H10C | 109.5 |
C4—C3—H3 | 120.6 | H10B—C10—H10C | 109.5 |
C3—C4—C5 | 119.15 (12) | O3—C11—O2 | 123.11 (13) |
C3—C4—C8 | 135.65 (12) | O3—C11—C1 | 122.42 (13) |
C5—C4—C8 | 105.21 (12) | O2—C11—C1 | 114.46 (12) |
O1—C5—C6 | 125.90 (12) | S—C12—H12A | 109.5 |
O1—C5—C4 | 110.59 (11) | S—C12—H12B | 109.5 |
C6—C5—C4 | 123.52 (13) | H12A—C12—H12B | 109.5 |
C5—C6—C7 | 116.52 (12) | S—C12—H12C | 109.5 |
C5—C6—H6 | 121.7 | H12A—C12—H12C | 109.5 |
C7—C6—H6 | 121.7 | H12B—C12—H12C | 109.5 |
| | | |
C11—C1—C2—C3 | −82.39 (16) | C1—C2—C7—C6 | 179.79 (13) |
C11—C1—C2—C7 | 98.09 (15) | C3—C4—C8—C9 | 178.95 (15) |
C7—C2—C3—C4 | −0.9 (2) | C5—C4—C8—C9 | −0.93 (15) |
C1—C2—C3—C4 | 179.57 (12) | C3—C4—C8—S | −4.8 (2) |
C2—C3—C4—C5 | 0.32 (19) | C5—C4—C8—S | 175.31 (11) |
C2—C3—C4—C8 | −179.55 (14) | C12—S—C8—C9 | −117.47 (14) |
C9—O1—C5—C6 | 179.81 (13) | C12—S—C8—C4 | 66.94 (15) |
C9—O1—C5—C4 | 0.39 (14) | C4—C8—C9—O1 | 1.22 (16) |
C3—C4—C5—O1 | −179.58 (11) | S—C8—C9—O1 | −175.15 (10) |
C8—C4—C5—O1 | 0.32 (15) | C4—C8—C9—C10 | −178.51 (14) |
C3—C4—C5—C6 | 1.0 (2) | S—C8—C9—C10 | 5.1 (2) |
C8—C4—C5—C6 | −179.12 (13) | C5—O1—C9—C8 | −1.02 (15) |
O1—C5—C6—C7 | 179.06 (13) | C5—O1—C9—C10 | 178.76 (11) |
C4—C5—C6—C7 | −1.6 (2) | C2—C1—C11—O3 | 132.25 (14) |
C5—C6—C7—C2 | 0.9 (2) | C2—C1—C11—O2 | −48.53 (17) |
C3—C2—C7—C6 | 0.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.82 | 1.83 | 2.6470 (15) | 179 |
Symmetry code: (i) −x+1, −y+2, −z+2. |