Download citation
Download citation
link to html
The title compound, C13H14O3S, was prepared by alkaline hydrolysis of ethyl 2-(5-ethyl-3-methyl­sulfanyl-1-benzofuran-2-yl)acetate. The crystal structure is stabilized by aromatic π–π stacking inter­actions and inversion-related inter­molecular O—H...O hydrogen bonds between adjacent carboxyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013165/sj2260sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013165/sj2260Isup2.hkl
Contains datablock I

CCDC reference: 647332

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.096
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
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 1 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 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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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-(5-Ethyl-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid top
Crystal data top
C13H14O3SZ = 2
Mr = 250.30F(000) = 264
Triclinic, P1Dx = 1.356 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.0746 (4) ÅCell parameters from 2838 reflections
b = 8.0636 (6) Åθ = 2.7–28.2°
c = 15.058 (1) ŵ = 0.26 mm1
α = 94.711 (1)°T = 173 K
β = 93.153 (1)°Block, colorless
γ = 90.538 (1)°0.32 × 0.25 × 0.20 mm
V = 613.10 (8) Å3
Data collection top
Bruker SMART CCD
diffractometer
2145 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 26.0°, θmin = 2.7°
Detector resolution: 10.00 pixels mm-1h = 66
φ and ω scansk = 99
3461 measured reflectionsl = 1218
2368 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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.2398P]
where P = (Fo2 + 2Fc2)/3
2368 reflections(Δ/σ)max < 0.001
159 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (CDCl3): δ 1.29 (t, J = 8.0 Hz, 3H), 2.33 (s, 3H), 2.76 (q, J = 8.60 Hz, 2H), 4.03 (s, 2H), 7.15 (d, J = 8.20 Hz, 1H), 7.36 (d, J = 8.20 Hz, 1H), 7.45 (s, 1H), 12.04 (s, 1H); 13C NMR (CDCl3): δ 16.3, 18.7, 28.9, 32.5, 111.2, 112.1, 118.4, 125.1, 129.1, 139.5, 152.6, 153.0, 174.9; MS: 250 [M+].

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
S1.08378 (8)0.78807 (5)0.81251 (3)0.03092 (15)
O10.8825 (2)0.44245 (13)0.61842 (7)0.0277 (3)
O20.8617 (2)0.81886 (18)0.54991 (9)0.0393 (3)
H140.815 (6)0.899 (4)0.523 (2)0.082 (9)*
O31.2713 (2)0.90818 (15)0.53205 (9)0.0371 (3)
C10.9524 (3)0.62195 (18)0.74081 (10)0.0241 (3)
C20.7485 (3)0.50541 (18)0.75908 (10)0.0238 (3)
C30.5943 (3)0.48356 (19)0.83136 (11)0.0250 (3)
H30.61560.55590.88440.030*
C40.4098 (3)0.35468 (19)0.82460 (11)0.0262 (3)
C50.3813 (3)0.2495 (2)0.74545 (12)0.0297 (4)
H50.25390.16180.74160.036*
C60.5316 (3)0.2685 (2)0.67270 (11)0.0298 (4)
H60.51100.19650.61950.036*
C70.7137 (3)0.39881 (19)0.68219 (10)0.0250 (3)
C81.0241 (3)0.57953 (19)0.65727 (11)0.0254 (3)
C91.2173 (3)0.6552 (2)0.60094 (11)0.0284 (4)
H9A1.26560.57050.55340.034*
H9B1.37960.68640.63830.034*
C101.1165 (3)0.80757 (19)0.55796 (10)0.0252 (3)
C110.2428 (3)0.3262 (2)0.90246 (12)0.0317 (4)
H11A0.06070.29600.87950.038*
H11B0.23510.43120.94120.038*
C120.3500 (4)0.1895 (2)0.95786 (12)0.0376 (4)
H12A0.52880.21990.98200.045*
H12B0.35480.08470.92010.045*
H12C0.23540.17581.00710.045*
C130.8183 (4)0.9339 (2)0.80137 (16)0.0433 (5)
H13A0.80520.96750.74020.065*
H13B0.85381.03220.84320.065*
H13C0.65180.88120.81470.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0261 (2)0.0262 (2)0.0394 (3)0.00554 (15)0.00043 (17)0.00182 (17)
O10.0337 (6)0.0242 (6)0.0253 (6)0.0038 (5)0.0016 (4)0.0035 (4)
O20.0249 (6)0.0440 (8)0.0527 (8)0.0017 (5)0.0020 (5)0.0271 (6)
O30.0283 (6)0.0347 (7)0.0510 (8)0.0040 (5)0.0024 (5)0.0205 (6)
C10.0242 (7)0.0201 (7)0.0282 (8)0.0008 (6)0.0018 (6)0.0057 (6)
C20.0244 (7)0.0202 (7)0.0274 (8)0.0012 (6)0.0022 (6)0.0070 (6)
C30.0261 (8)0.0227 (7)0.0266 (8)0.0016 (6)0.0002 (6)0.0047 (6)
C40.0253 (8)0.0224 (8)0.0322 (8)0.0030 (6)0.0012 (6)0.0090 (6)
C50.0286 (8)0.0216 (8)0.0390 (9)0.0050 (6)0.0005 (7)0.0057 (7)
C60.0355 (9)0.0232 (8)0.0301 (8)0.0038 (7)0.0014 (7)0.0011 (6)
C70.0274 (8)0.0235 (7)0.0250 (8)0.0010 (6)0.0011 (6)0.0070 (6)
C80.0257 (8)0.0212 (7)0.0298 (8)0.0006 (6)0.0012 (6)0.0073 (6)
C90.0244 (8)0.0299 (8)0.0325 (9)0.0018 (6)0.0029 (6)0.0113 (7)
C100.0252 (8)0.0263 (8)0.0248 (8)0.0013 (6)0.0024 (6)0.0057 (6)
C110.0302 (8)0.0283 (8)0.0379 (9)0.0003 (7)0.0076 (7)0.0074 (7)
C120.0479 (11)0.0331 (9)0.0336 (9)0.0006 (8)0.0072 (8)0.0096 (7)
C130.0337 (10)0.0265 (9)0.0689 (13)0.0002 (7)0.0070 (9)0.0032 (8)
Geometric parameters (Å, º) top
S—C11.752 (2)C5—H50.9500
S—C131.807 (2)C6—C71.386 (2)
O1—C81.383 (2)C6—H60.9500
O1—C71.386 (2)C8—C91.489 (2)
O2—C101.297 (2)C9—C101.516 (2)
O2—H140.82 (3)C9—H9A0.9900
O3—C101.225 (2)C9—H9B0.9900
C1—C81.347 (2)C11—C121.523 (2)
C1—C21.444 (2)C11—H11A0.9900
C2—C71.386 (2)C11—H11B0.9900
C2—C31.397 (2)C12—H12A0.9800
C3—C41.386 (2)C12—H12B0.9800
C3—H30.9500C12—H12C0.9800
C4—C51.405 (2)C13—H13A0.9800
C4—C111.515 (2)C13—H13B0.9800
C5—C61.387 (2)C13—H13C0.9800
C1—S—C1399.20 (8)C8—C9—C10113.98 (13)
C8—O1—C7105.51 (12)C8—C9—H9A108.8
C10—O2—H14112 (2)C10—C9—H9A108.8
C8—C1—C2106.98 (14)C8—C9—H9B108.8
C8—C1—S125.87 (12)C10—C9—H9B108.8
C2—C1—S127.15 (12)H9A—C9—H9B107.7
C7—C2—C3119.59 (14)O3—C10—O2124.37 (15)
C7—C2—C1105.33 (14)O3—C10—C9120.48 (14)
C3—C2—C1135.07 (15)O2—C10—C9115.14 (13)
C4—C3—C2119.01 (15)C4—C11—C12112.63 (14)
C4—C3—H3120.5C4—C11—H11A109.1
C2—C3—H3120.5C12—C11—H11A109.1
C3—C4—C5119.47 (15)C4—C11—H11B109.1
C3—C4—C11120.19 (15)C12—C11—H11B109.1
C5—C4—C11120.33 (14)H11A—C11—H11B107.8
C6—C5—C4122.69 (14)C11—C12—H12A109.5
C6—C5—H5118.7C11—C12—H12B109.5
C4—C5—H5118.7H12A—C12—H12B109.5
C7—C6—C5116.01 (15)C11—C12—H12C109.5
C7—C6—H6122.0H12A—C12—H12C109.5
C5—C6—H6122.0H12B—C12—H12C109.5
C6—C7—O1126.16 (15)S—C13—H13A109.5
C6—C7—C2123.22 (15)S—C13—H13B109.5
O1—C7—C2110.61 (13)H13A—C13—H13B109.5
C1—C8—O1111.57 (13)S—C13—H13C109.5
C1—C8—C9131.94 (15)H13A—C13—H13C109.5
O1—C8—C9116.47 (14)H13B—C13—H13C109.5
C13—S—C1—C8102.92 (16)C3—C2—C7—C60.3 (2)
C13—S—C1—C276.89 (15)C1—C2—C7—C6179.56 (15)
C8—C1—C2—C70.04 (17)C3—C2—C7—O1179.32 (13)
S—C1—C2—C7179.88 (12)C1—C2—C7—O10.02 (17)
C8—C1—C2—C3179.09 (16)C2—C1—C8—O10.08 (17)
S—C1—C2—C30.7 (3)S—C1—C8—O1179.93 (11)
C7—C2—C3—C40.2 (2)C2—C1—C8—C9178.01 (16)
C1—C2—C3—C4179.27 (16)S—C1—C8—C91.8 (3)
C2—C3—C4—C50.2 (2)C7—O1—C8—C10.09 (17)
C2—C3—C4—C11179.02 (14)C7—O1—C8—C9178.32 (13)
C3—C4—C5—C60.1 (2)C1—C8—C9—C1078.9 (2)
C11—C4—C5—C6179.07 (15)O1—C8—C9—C1099.09 (16)
C4—C5—C6—C70.1 (2)C8—C9—C10—O3159.01 (16)
C5—C6—C7—O1179.30 (14)C8—C9—C10—O222.3 (2)
C5—C6—C7—C20.2 (2)C3—C4—C11—C1298.42 (18)
C8—O1—C7—C6179.49 (16)C5—C4—C11—C1280.8 (2)
C8—O1—C7—C20.07 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H14···O3i0.82 (3)1.87 (3)2.684 (2)175 (3)
Symmetry code: (i) x+2, y+2, z+1.
 

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