![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
Propyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate
aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr
In the title compound, C14H15BrO4S, the S atom has a distorted trigonal–pyramidal coordination. The O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The molecules form slightly slipped π-stacked inversion-symmetric dimers by intermolecular aromatic π–π interactions, with a centroid-to-centroid distance of 3.695 (4) Å between the benzene rings of neighbouring molecules. The crystal packing is further stabilized by intermolecular C—H⋯π interactions between the methylene H atoms of the propyl group towards the benzene and furan rings of neighbouring molecules, respectively. Additionally, the exhibits weak intermolecular C—H⋯O hydrogen bonds.
Related literature
For the crystal structures of similar alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008a,b
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 (Farrugia, 1997
) and DIAMOND (Brandenburg, 1998
); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S160053680900453X/zl2167sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680900453X/zl2167Isup2.hkl
77% 3-chloroperoxybenzoic acid (179 mg, 0.8 mmol) was added in small portions to a stirred solution of propyl 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (629 mg, 0.75 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 3 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by δ 0.94 (t, J = 7.32 Hz, 3H), 1.63–1.72 (m, 2H), 3.07 (s, 3H), 4.05 (s, 2H), 4.11 (t, J = 6.96 Hz, 2H), 7.40 (d, J = 8.76 Hz, 1H), 7.48 (dd, J = 8.76 Hz and J = 1.84 Hz, 1H), 8.09 (d, J = 1.84 Hz, 1H); EI-MS 360 [M+2], 358 [M+].
(hexane–ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 81%, m.p. 413–413.5 K; Rf = 0.55 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature. Spectroscopic analysis: 1H NMR (CDCl3, 400 MHz)All H atoms were geometrically positioned and refined using a riding model, with C—H = 0.93 Å for the aryl, 0.97 Å for the methylene, and 0.96 Å for the methyl H atoms. Uiso(H) = 1.2Ueq(C) for the ary and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C14H15BrO4S | Z = 2 |
Mr = 359.23 | F(000) = 364 |
Triclinic, P1 | Dx = 1.597 Mg m−3 |
Hall symbol: -p_1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4538 (6) Å | Cell parameters from 2872 reflections |
b = 9.8823 (7) Å | θ = 2.7–28.0° |
c = 10.3231 (7) Å | µ = 2.90 mm−1 |
α = 72.358 (1)° | T = 298 K |
β = 81.200 (1)° | Block, colourless |
γ = 65.443 (1)° | 0.60 × 0.50 × 0.20 mm |
V = 747.16 (9) Å3 |
Bruker SMART CCD diffractometer | 2593 independent reflections |
Radiation source: fine-focus sealed tube | 2359 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Detector resolution: 10.0 pixels mm-1 | θmax = 25.0°, θmin = 2.4° |
ϕ and ω scans | h = −9→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | k = −10→11 |
Tmin = 0.187, Tmax = 0.556 | l = −12→10 |
3932 measured reflections |
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)] = 0.034 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0598P)2 + 0.3564P] where P = (Fo2 + 2Fc2)/3 |
2593 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.62 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C14H15BrO4S | γ = 65.443 (1)° |
Mr = 359.23 | V = 747.16 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.4538 (6) Å | Mo Kα radiation |
b = 9.8823 (7) Å | µ = 2.90 mm−1 |
c = 10.3231 (7) Å | T = 298 K |
α = 72.358 (1)° | 0.60 × 0.50 × 0.20 mm |
β = 81.200 (1)° |
Bruker SMART CCD diffractometer | 2593 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 2359 reflections with I > 2σ(I) |
Tmin = 0.187, Tmax = 0.556 | Rint = 0.014 |
3932 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.62 e Å−3 |
2593 reflections | Δρmin = −0.38 e Å−3 |
182 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
Br | 0.68856 (4) | 0.78591 (4) | 0.61232 (4) | 0.06138 (16) | |
S | 0.26099 (9) | 0.40306 (8) | 0.96326 (6) | 0.04277 (19) | |
O1 | 0.1656 (2) | 0.5416 (2) | 0.57292 (17) | 0.0389 (4) | |
O2 | 0.0410 (3) | 0.1435 (2) | 0.7276 (3) | 0.0651 (6) | |
O3 | 0.2856 (3) | 0.1366 (3) | 0.7909 (3) | 0.0628 (6) | |
O4 | 0.2583 (3) | 0.5257 (3) | 1.0205 (2) | 0.0565 (5) | |
C1 | 0.2557 (3) | 0.4773 (3) | 0.7850 (2) | 0.0355 (5) | |
C2 | 0.3457 (3) | 0.5694 (3) | 0.6968 (2) | 0.0345 (5) | |
C3 | 0.4701 (3) | 0.6215 (3) | 0.7124 (3) | 0.0390 (6) | |
H3 | 0.5166 | 0.5970 | 0.7965 | 0.047* | |
C4 | 0.5206 (3) | 0.7106 (3) | 0.5974 (3) | 0.0411 (6) | |
C5 | 0.4525 (4) | 0.7510 (3) | 0.4691 (3) | 0.0448 (6) | |
H5 | 0.4882 | 0.8144 | 0.3949 | 0.054* | |
C6 | 0.3327 (3) | 0.6968 (3) | 0.4533 (3) | 0.0421 (6) | |
H6 | 0.2877 | 0.7199 | 0.3689 | 0.051* | |
C7 | 0.2826 (3) | 0.6069 (3) | 0.5677 (3) | 0.0367 (5) | |
C8 | 0.1513 (3) | 0.4645 (3) | 0.7068 (3) | 0.0368 (5) | |
C9 | 0.0363 (3) | 0.3784 (3) | 0.7351 (3) | 0.0408 (6) | |
H9A | −0.0412 | 0.4178 | 0.6600 | 0.049* | |
H9B | −0.0347 | 0.3956 | 0.8164 | 0.049* | |
C10 | 0.1380 (4) | 0.2072 (3) | 0.7546 (3) | 0.0448 (6) | |
C11 | 0.1221 (5) | −0.0227 (4) | 0.7402 (6) | 0.0860 (14) | |
H11A | 0.1843 | −0.0769 | 0.8242 | 0.103* | |
H11B | 0.2040 | −0.0434 | 0.6648 | 0.103* | |
C12 | −0.0195 (6) | −0.0757 (5) | 0.7394 (6) | 0.0900 (14) | |
H12A | −0.0800 | −0.0196 | 0.6548 | 0.108* | |
H12B | 0.0329 | −0.1842 | 0.7418 | 0.108* | |
C13 | −0.1468 (9) | −0.0548 (7) | 0.8527 (6) | 0.122 (2) | |
H13A | −0.2019 | 0.0527 | 0.8501 | 0.147* | |
H13B | −0.0889 | −0.1122 | 0.9372 | 0.147* | |
H13C | −0.2332 | −0.0913 | 0.8452 | 0.147* | |
C14 | 0.4798 (4) | 0.2618 (4) | 0.9755 (3) | 0.0575 (8) | |
H14A | 0.5592 | 0.3128 | 0.9465 | 0.086* | |
H14B | 0.4965 | 0.1959 | 0.9185 | 0.086* | |
H14C | 0.5011 | 0.2010 | 1.0681 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.0581 (2) | 0.0617 (2) | 0.0766 (3) | −0.03898 (17) | −0.00471 (16) | −0.01173 (17) |
S | 0.0443 (4) | 0.0525 (4) | 0.0332 (3) | −0.0238 (3) | −0.0022 (3) | −0.0064 (3) |
O1 | 0.0385 (9) | 0.0443 (10) | 0.0356 (9) | −0.0182 (8) | −0.0059 (7) | −0.0078 (8) |
O2 | 0.0436 (11) | 0.0429 (11) | 0.114 (2) | −0.0170 (9) | −0.0113 (12) | −0.0243 (12) |
O3 | 0.0443 (12) | 0.0509 (12) | 0.0865 (16) | −0.0157 (10) | −0.0153 (11) | −0.0066 (11) |
O4 | 0.0607 (13) | 0.0705 (14) | 0.0457 (11) | −0.0259 (11) | 0.0001 (10) | −0.0262 (10) |
C1 | 0.0360 (12) | 0.0366 (12) | 0.0339 (12) | −0.0145 (10) | −0.0016 (10) | −0.0087 (10) |
C2 | 0.0341 (12) | 0.0333 (12) | 0.0356 (12) | −0.0117 (10) | −0.0021 (10) | −0.0102 (10) |
C3 | 0.0394 (13) | 0.0395 (13) | 0.0412 (14) | −0.0160 (11) | −0.0047 (10) | −0.0123 (11) |
C4 | 0.0376 (13) | 0.0365 (13) | 0.0513 (16) | −0.0157 (11) | −0.0002 (11) | −0.0137 (11) |
C5 | 0.0430 (14) | 0.0394 (14) | 0.0465 (15) | −0.0165 (12) | 0.0019 (12) | −0.0049 (12) |
C6 | 0.0429 (14) | 0.0438 (14) | 0.0348 (13) | −0.0143 (12) | −0.0048 (11) | −0.0060 (11) |
C7 | 0.0335 (12) | 0.0342 (12) | 0.0409 (14) | −0.0108 (10) | −0.0047 (10) | −0.0097 (10) |
C8 | 0.0340 (12) | 0.0382 (13) | 0.0373 (13) | −0.0142 (10) | −0.0016 (10) | −0.0084 (10) |
C9 | 0.0366 (13) | 0.0446 (14) | 0.0449 (14) | −0.0186 (11) | −0.0029 (11) | −0.0123 (11) |
C10 | 0.0401 (14) | 0.0463 (15) | 0.0491 (15) | −0.0210 (12) | −0.0001 (12) | −0.0089 (12) |
C11 | 0.055 (2) | 0.0450 (19) | 0.158 (4) | −0.0120 (16) | −0.004 (2) | −0.039 (2) |
C12 | 0.075 (3) | 0.047 (2) | 0.151 (4) | −0.0233 (18) | −0.005 (3) | −0.032 (2) |
C13 | 0.138 (5) | 0.095 (4) | 0.140 (5) | −0.073 (4) | 0.050 (4) | −0.026 (3) |
C14 | 0.0550 (18) | 0.0543 (18) | 0.0555 (18) | −0.0142 (15) | −0.0160 (14) | −0.0075 (14) |
Br—C4 | 1.899 (3) | C6—C7 | 1.374 (4) |
S—O4 | 1.492 (2) | C6—H6 | 0.9300 |
S—C1 | 1.763 (3) | C8—C9 | 1.486 (4) |
S—C14 | 1.790 (3) | C9—C10 | 1.509 (4) |
O1—C8 | 1.375 (3) | C9—H9A | 0.9700 |
O1—C7 | 1.375 (3) | C9—H9B | 0.9700 |
O2—C10 | 1.323 (4) | C11—C12 | 1.494 (6) |
O2—C11 | 1.465 (4) | C11—H11A | 0.9700 |
O3—C10 | 1.202 (4) | C11—H11B | 0.9700 |
C1—C8 | 1.349 (4) | C12—C13 | 1.465 (7) |
C1—C2 | 1.448 (4) | C12—H12A | 0.9700 |
C2—C3 | 1.396 (4) | C12—H12B | 0.9700 |
C2—C7 | 1.397 (3) | C13—H13A | 0.9600 |
C3—C4 | 1.376 (4) | C13—H13B | 0.9600 |
C3—H3 | 0.9300 | C13—H13C | 0.9600 |
C4—C5 | 1.402 (4) | C14—H14A | 0.9600 |
C5—C6 | 1.377 (4) | C14—H14B | 0.9600 |
C5—H5 | 0.9300 | C14—H14C | 0.9600 |
O4—S—C1 | 107.01 (13) | C10—C9—H9A | 109.2 |
O4—S—C14 | 106.32 (14) | C8—C9—H9B | 109.2 |
C1—S—C14 | 98.46 (14) | C10—C9—H9B | 109.2 |
C8—O1—C7 | 106.53 (19) | H9A—C9—H9B | 107.9 |
C10—O2—C11 | 117.2 (2) | O3—C10—O2 | 124.0 (3) |
C8—C1—C2 | 107.4 (2) | O3—C10—C9 | 125.6 (3) |
C8—C1—S | 123.4 (2) | O2—C10—C9 | 110.4 (2) |
C2—C1—S | 129.00 (19) | O2—C11—C12 | 107.7 (3) |
C3—C2—C7 | 119.3 (2) | O2—C11—H11A | 110.2 |
C3—C2—C1 | 136.1 (2) | C12—C11—H11A | 110.2 |
C7—C2—C1 | 104.6 (2) | O2—C11—H11B | 110.2 |
C4—C3—C2 | 116.8 (2) | C12—C11—H11B | 110.2 |
C4—C3—H3 | 121.6 | H11A—C11—H11B | 108.5 |
C2—C3—H3 | 121.6 | C13—C12—C11 | 114.4 (5) |
C3—C4—C5 | 123.3 (3) | C13—C12—H12A | 108.7 |
C3—C4—Br | 118.7 (2) | C11—C12—H12A | 108.7 |
C5—C4—Br | 117.9 (2) | C13—C12—H12B | 108.7 |
C6—C5—C4 | 119.8 (3) | C11—C12—H12B | 108.7 |
C6—C5—H5 | 120.1 | H12A—C12—H12B | 107.6 |
C4—C5—H5 | 120.1 | C12—C13—H13A | 109.5 |
C7—C6—C5 | 117.1 (2) | C12—C13—H13B | 109.5 |
C7—C6—H6 | 121.5 | H13A—C13—H13B | 109.5 |
C5—C6—H6 | 121.5 | C12—C13—H13C | 109.5 |
O1—C7—C6 | 125.9 (2) | H13A—C13—H13C | 109.5 |
O1—C7—C2 | 110.5 (2) | H13B—C13—H13C | 109.5 |
C6—C7—C2 | 123.6 (2) | S—C14—H14A | 109.5 |
C1—C8—O1 | 111.0 (2) | S—C14—H14B | 109.5 |
C1—C8—C9 | 133.2 (2) | H14A—C14—H14B | 109.5 |
O1—C8—C9 | 115.7 (2) | S—C14—H14C | 109.5 |
C8—C9—C10 | 112.2 (2) | H14A—C14—H14C | 109.5 |
C8—C9—H9A | 109.2 | H14B—C14—H14C | 109.5 |
O4—S—C1—C8 | −134.5 (2) | C3—C2—C7—O1 | 178.3 (2) |
C14—S—C1—C8 | 115.5 (2) | C1—C2—C7—O1 | −1.2 (3) |
O4—S—C1—C2 | 40.5 (3) | C3—C2—C7—C6 | −1.8 (4) |
C14—S—C1—C2 | −69.5 (3) | C1—C2—C7—C6 | 178.8 (2) |
C8—C1—C2—C3 | −178.6 (3) | C2—C1—C8—O1 | 0.0 (3) |
S—C1—C2—C3 | 5.7 (4) | S—C1—C8—O1 | 175.96 (17) |
C8—C1—C2—C7 | 0.7 (3) | C2—C1—C8—C9 | 175.7 (3) |
S—C1—C2—C7 | −174.95 (19) | S—C1—C8—C9 | −8.3 (4) |
C7—C2—C3—C4 | 1.3 (4) | C7—O1—C8—C1 | −0.7 (3) |
C1—C2—C3—C4 | −179.5 (3) | C7—O1—C8—C9 | −177.3 (2) |
C2—C3—C4—C5 | 0.6 (4) | C1—C8—C9—C10 | −73.6 (4) |
C2—C3—C4—Br | 179.65 (18) | O1—C8—C9—C10 | 102.0 (3) |
C3—C4—C5—C6 | −2.0 (4) | C11—O2—C10—O3 | −1.5 (5) |
Br—C4—C5—C6 | 178.9 (2) | C11—O2—C10—C9 | 179.2 (3) |
C4—C5—C6—C7 | 1.5 (4) | C8—C9—C10—O3 | 24.7 (4) |
C8—O1—C7—C6 | −178.8 (2) | C8—C9—C10—O2 | −156.0 (2) |
C8—O1—C7—C2 | 1.2 (3) | C10—O2—C11—C12 | 166.2 (4) |
C5—C6—C7—O1 | −179.7 (2) | O2—C11—C12—C13 | −62.0 (6) |
C5—C6—C7—C2 | 0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···Cg1i | 0.97 | 3.02 | 3.720 (3) | 130 |
C12—H12B···Cg2i | 0.97 | 2.90 | 3.826 (3) | 161 |
C3—H3···O4ii | 0.93 | 2.54 | 3.424 (3) | 159 |
C5—H5···O3iii | 0.93 | 2.58 | 3.430 (4) | 152 |
C9—H9B···O4iv | 0.97 | 2.37 | 3.321 (3) | 167 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C14H15BrO4S |
Mr | 359.23 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.4538 (6), 9.8823 (7), 10.3231 (7) |
α, β, γ (°) | 72.358 (1), 81.200 (1), 65.443 (1) |
V (Å3) | 747.16 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.90 |
Crystal size (mm) | 0.60 × 0.50 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.187, 0.556 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3932, 2593, 2359 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.097, 1.07 |
No. of reflections | 2593 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.62, −0.38 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···Cg1i | 0.97 | 3.02 | 3.720 (3) | 130.0 |
C12—H12B···Cg2i | 0.97 | 2.90 | 3.826 (3) | 161.1 |
C3—H3···O4ii | 0.93 | 2.54 | 3.424 (3) | 158.7 |
C5—H5···O3iii | 0.93 | 2.58 | 3.430 (4) | 152.1 |
C9—H9B···O4iv | 0.97 | 2.37 | 3.321 (3) | 167.1 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+2. |
References
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o2250. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o2397. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a part of our ongoing research on the synthesis and structure of alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, we have recently described the crystal structures of isopropyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008a) and methyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008b). Here we report the crystal structure of the title compound, propyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Fig. 1).
The benzofuran unit is essentially planar, with a mean deviation of 0.013 (2) Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (Fig. 2) is stabilized by intermolecular π–π stacking interactions between the benzene rings of neighbouring molecules. Via this interaction the molecules form slightly slipped π-stacked inversion symmetric dimers, with a centroid–centroid distance Cg1···Cg1iii of 3.695 (4) Å between the benzene rings of neighbouring molecules. (Cg is the centroid of the C2–C7 benzene ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions; one between the hydrogen of the C11-methylene group and the benzene ring of the benzofuran unit, with a C11—H11B···Cg1i separation of 3.02 Å, and a second between the hydrogen of the C12-methylene group and the furan ring of the benzofuran unit, with a C12—H12B···Cg2i separation of 2.90 Å (Table 1 and Fig. 2; Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively, symmetry code as in Fig. 2). In addition, three weak intermolecular C—H···O hydrogen bonds in the structure were observed (Table 1 and Fig. 3); one between the hydrogen on benzene ring and the oxygen of the S═O unit (C3—H3···O4ii), a second between the hydrogen on benzene ring and the oxygen of the C═O unit (C5—H5···O3iii), and a third between the hydrogen of the C9–methylene group and the S═O unit (C9—H9B···O4iv), respectively.