[2-Methyl-3-methyl­sulfanyl-1-(benzofuran-5-yl)]acetic acid

The title compound, C₁₂H₁₂O₃S, 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, H₂C—H...π inter­actions and inversion-related inter­molecular O—H...O hydrogen bonds between the carboxyl groups.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0316P)^2 + 0.3303P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.091 (6)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3^i	0.82	1.83	2.6470 (15)	179

Symmetry code: (i) −x+1, −y+2, −z+2.