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organic compounds
Butyl 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, C15H17BrO4S, the methylsulfinyl O atom and the methyl substituents lie on opposite sides of the plane through the benzofuran fragment. The is stabilized by π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.698 (4) Å], and by C—H⋯π interactions between a methylene H atom of the butyl group and the benzene ring of the benzofuran system. Additionally, the exhibits weak intermolecular C—H⋯O contacts. The butyl group is disordered over two positions, with site-occupancy factors, from of 0.720 (8) and 0.280 (8).
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/S1600536808043985/tk2347sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808043985/tk2347Isup2.hkl
77% 3-Chloroperoxybenzoic acid (148 mg, 0.66 mmol) was added in small portions to a stirred solution of butyl 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (214 mg, 0.6 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 separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by δ 0.92 (t, J = 7.32 Hz, 3H), 1.31–1.41 (m, 2H), 1.59–1.67 (m, 2H), 3.07 (s, 3H), 4.04 (s, 2H), 4.15 (t, J = 6.6 Hz, 2H), 7.39 (d, J = 8.8 Hz, 1H), 7.49 (dd, J = 8.8 Hz and J = 2.2 Hz, 1H), 8.11 (d, J = 1.84 Hz, 1H); EI—MS 374 [M+2], 372 [M+].
(hexane-ethyl acetate, 1:2 v/v) to afford (I) as a colorless solid [yield 80%, m.p. 381–382 K; Rf = 0.65 (hexane-ethyl acetate, 1;2 v/v)]. Single crystals were obtained by evaporation of an acetone solution of (I). 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 aryl-, 0.97 Å for methylene-, and 0.96 Å for methyl-H atoms, and with Uiso(H) = 1.2Ueq(C) for the aryl- and methylene-H atoms, and 1.5Ueq(C) for methyl-H atoms. The butyl group was found to be disordered over two positions and modelled with site-occupancy factors, from
of 0.720 (8) (C11A–C14A)) and 0.280 (8) (C11B–C14B). The displacement ellipsoids of part B part were restrained using command ISOR (0.01), both sets of C atoms were restrained using the command DELU, and the C—C distances were restrained to 1.480 (2) Å using command DFIX.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).C15H17BrO4S | Z = 2 |
Mr = 373.26 | F(000) = 380 |
Triclinic, P1 | Dx = 1.522 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.420 (1) Å | Cell parameters from 3446 reflections |
b = 10.255 (1) Å | θ = 2.6–27.0° |
c = 10.306 (1) Å | µ = 2.66 mm−1 |
α = 97.503 (2)° | T = 298 K |
β = 99.711 (2)° | Block, colorless |
γ = 108.678 (2)° | 0.40 × 0.40 × 0.30 mm |
V = 814.55 (15) Å3 |
Bruker SMART CCD diffractometer | 3179 independent reflections |
Radiation source: fine-focus sealed tube | 2645 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 10.0 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ϕ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | k = −12→12 |
Tmin = 0.353, Tmax = 0.451 | l = −12→12 |
6560 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)] = 0.033 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0442P)2 + 0.2004P] where P = (Fo2 + 2Fc2)/3 |
3179 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.30 e Å−3 |
64 restraints | Δρmin = −0.50 e Å−3 |
C15H17BrO4S | γ = 108.678 (2)° |
Mr = 373.26 | V = 814.55 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.420 (1) Å | Mo Kα radiation |
b = 10.255 (1) Å | µ = 2.66 mm−1 |
c = 10.306 (1) Å | T = 298 K |
α = 97.503 (2)° | 0.40 × 0.40 × 0.30 mm |
β = 99.711 (2)° |
Bruker SMART CCD diffractometer | 3179 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 2645 reflections with I > 2σ(I) |
Tmin = 0.353, Tmax = 0.451 | Rint = 0.017 |
6560 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 64 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.30 e Å−3 |
3179 reflections | Δρmin = −0.50 e Å−3 |
229 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br | −0.42599 (4) | 0.24082 (3) | 0.12584 (3) | 0.06775 (14) | |
S | 0.32177 (9) | 0.58854 (7) | 0.45871 (6) | 0.04988 (17) | |
O1 | 0.3033 (2) | 0.46045 (17) | 0.07725 (15) | 0.0442 (4) | |
O2 | 0.7594 (3) | 0.8276 (2) | 0.2120 (2) | 0.0686 (6) | |
O3 | 0.5174 (3) | 0.8291 (2) | 0.2711 (2) | 0.0721 (6) | |
O4 | 0.2197 (3) | 0.4784 (2) | 0.52321 (18) | 0.0618 (5) | |
C1 | 0.2665 (3) | 0.5195 (2) | 0.2849 (2) | 0.0413 (5) | |
C2 | 0.0997 (3) | 0.4347 (2) | 0.2012 (2) | 0.0401 (5) | |
C3 | −0.0682 (3) | 0.3882 (3) | 0.2186 (2) | 0.0447 (5) | |
H3 | −0.0941 | 0.4108 | 0.3010 | 0.054* | |
C4 | −0.1944 (3) | 0.3070 (3) | 0.1078 (3) | 0.0472 (6) | |
C5 | −0.1604 (4) | 0.2716 (3) | −0.0175 (3) | 0.0509 (6) | |
H5 | −0.2500 | 0.2159 | −0.0889 | 0.061* | |
C6 | 0.0052 (3) | 0.3188 (3) | −0.0354 (2) | 0.0478 (6) | |
H6 | 0.0307 | 0.2966 | −0.1181 | 0.057* | |
C7 | 0.1318 (3) | 0.4008 (2) | 0.0749 (2) | 0.0414 (5) | |
C8 | 0.3827 (3) | 0.5320 (2) | 0.2067 (2) | 0.0417 (5) | |
C9 | 0.5701 (3) | 0.6117 (3) | 0.2310 (3) | 0.0460 (6) | |
H9A | 0.6150 | 0.5767 | 0.1586 | 0.055* | |
H9B | 0.6281 | 0.5959 | 0.3140 | 0.055* | |
C10 | 0.6090 (3) | 0.7675 (3) | 0.2403 (3) | 0.0506 (6) | |
C11A | 0.8140 (8) | 0.9810 (14) | 0.2252 (11) | 0.087 (3) | 0.720 (8) |
H11A | 0.8117 | 1.0245 | 0.3139 | 0.104* | 0.720 (8) |
H11B | 0.7375 | 1.0053 | 0.1590 | 0.104* | 0.720 (8) |
C12A | 0.9913 (6) | 1.0302 (6) | 0.2033 (6) | 0.0749 (16) | 0.720 (8) |
H12A | 1.0207 | 1.1232 | 0.1821 | 0.090* | 0.720 (8) |
H12B | 1.0036 | 0.9664 | 0.1307 | 0.090* | 0.720 (8) |
C13A | 1.1021 (6) | 1.0324 (8) | 0.3331 (7) | 0.098 (2) | 0.720 (8) |
H13A | 1.0712 | 1.0833 | 0.4050 | 0.117* | 0.720 (8) |
H13B | 1.0766 | 0.9366 | 0.3464 | 0.117* | 0.720 (8) |
C14A | 1.2899 (7) | 1.0964 (9) | 0.3450 (10) | 0.134 (3) | 0.720 (8) |
H14A | 1.3499 | 1.0967 | 0.4330 | 0.202* | 0.720 (8) |
H14B | 1.3173 | 1.1911 | 0.3309 | 0.202* | 0.720 (8) |
H14C | 1.3243 | 1.0429 | 0.2788 | 0.202* | 0.720 (8) |
C11B | 0.806 (2) | 0.973 (3) | 0.183 (2) | 0.070 (5) | 0.280 (8) |
H11C | 0.7231 | 1.0153 | 0.2025 | 0.084* | 0.280 (8) |
H11D | 0.8138 | 0.9721 | 0.0903 | 0.084* | 0.280 (8) |
C12B | 0.9768 (19) | 1.049 (2) | 0.275 (3) | 0.127 (7) | 0.280 (8) |
H12C | 0.9614 | 1.0361 | 0.3645 | 0.153* | 0.280 (8) |
H12D | 1.0003 | 1.1475 | 0.2746 | 0.153* | 0.280 (8) |
C13B | 1.1377 (19) | 1.0231 (18) | 0.2628 (16) | 0.087 (5) | 0.280 (8) |
H13C | 1.1320 | 0.9270 | 0.2622 | 0.105* | 0.280 (8) |
H13D | 1.1884 | 1.0601 | 0.1915 | 0.105* | 0.280 (8) |
C14B | 1.207 (3) | 1.117 (2) | 0.3964 (16) | 0.124 (6) | 0.280 (8) |
H14D | 1.3305 | 1.1547 | 0.4133 | 0.186* | 0.280 (8) |
H14E | 1.1729 | 1.0655 | 0.4643 | 0.186* | 0.280 (8) |
H14F | 1.1634 | 1.1931 | 0.3985 | 0.186* | 0.280 (8) |
C15 | 0.2192 (5) | 0.7173 (3) | 0.4576 (3) | 0.0679 (8) | |
H15A | 0.0971 | 0.6710 | 0.4266 | 0.102* | |
H15B | 0.2615 | 0.7788 | 0.3987 | 0.102* | |
H15C | 0.2442 | 0.7710 | 0.5468 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.04457 (17) | 0.0686 (2) | 0.0882 (3) | 0.01726 (14) | 0.01642 (15) | 0.01369 (16) |
S | 0.0507 (4) | 0.0625 (4) | 0.0376 (3) | 0.0229 (3) | 0.0092 (3) | 0.0067 (3) |
O1 | 0.0471 (9) | 0.0509 (10) | 0.0400 (9) | 0.0212 (8) | 0.0158 (7) | 0.0093 (7) |
O2 | 0.0515 (11) | 0.0466 (11) | 0.1135 (17) | 0.0178 (9) | 0.0256 (11) | 0.0246 (11) |
O3 | 0.0637 (13) | 0.0590 (12) | 0.1004 (16) | 0.0315 (11) | 0.0233 (12) | 0.0072 (11) |
O4 | 0.0721 (13) | 0.0801 (14) | 0.0466 (10) | 0.0348 (11) | 0.0218 (9) | 0.0265 (9) |
C1 | 0.0462 (13) | 0.0449 (13) | 0.0361 (12) | 0.0191 (10) | 0.0103 (10) | 0.0099 (10) |
C2 | 0.0474 (13) | 0.0399 (12) | 0.0393 (12) | 0.0203 (10) | 0.0129 (10) | 0.0123 (10) |
C3 | 0.0474 (13) | 0.0471 (13) | 0.0471 (14) | 0.0220 (11) | 0.0160 (11) | 0.0146 (11) |
C4 | 0.0448 (13) | 0.0421 (13) | 0.0588 (15) | 0.0192 (11) | 0.0119 (11) | 0.0135 (11) |
C5 | 0.0537 (15) | 0.0468 (14) | 0.0504 (14) | 0.0221 (12) | 0.0019 (12) | 0.0044 (11) |
C6 | 0.0561 (15) | 0.0515 (14) | 0.0400 (13) | 0.0261 (12) | 0.0099 (11) | 0.0061 (11) |
C7 | 0.0449 (13) | 0.0420 (12) | 0.0440 (12) | 0.0211 (10) | 0.0134 (10) | 0.0117 (10) |
C8 | 0.0462 (13) | 0.0441 (13) | 0.0399 (12) | 0.0209 (10) | 0.0111 (10) | 0.0112 (10) |
C9 | 0.0447 (13) | 0.0512 (14) | 0.0480 (14) | 0.0215 (11) | 0.0144 (11) | 0.0132 (11) |
C10 | 0.0463 (14) | 0.0517 (15) | 0.0531 (15) | 0.0191 (12) | 0.0068 (11) | 0.0085 (12) |
C11A | 0.072 (4) | 0.059 (4) | 0.137 (7) | 0.029 (3) | 0.019 (4) | 0.032 (5) |
C12A | 0.075 (3) | 0.044 (2) | 0.105 (4) | 0.013 (2) | 0.022 (3) | 0.028 (3) |
C13A | 0.072 (3) | 0.080 (4) | 0.117 (5) | 0.002 (3) | 0.004 (3) | 0.024 (4) |
C14A | 0.077 (4) | 0.120 (5) | 0.175 (7) | −0.001 (4) | 0.024 (4) | 0.018 (5) |
C11B | 0.072 (7) | 0.040 (8) | 0.096 (9) | 0.008 (5) | 0.016 (6) | 0.034 (7) |
C12B | 0.110 (8) | 0.109 (10) | 0.162 (12) | 0.054 (8) | −0.005 (7) | 0.028 (9) |
C13B | 0.085 (7) | 0.086 (8) | 0.089 (8) | 0.028 (6) | 0.022 (6) | 0.012 (6) |
C14B | 0.122 (10) | 0.135 (10) | 0.109 (9) | 0.053 (8) | 0.012 (7) | 0.000 (7) |
C15 | 0.087 (2) | 0.0654 (19) | 0.0637 (18) | 0.0394 (17) | 0.0291 (16) | 0.0087 (15) |
Br—C4 | 1.899 (3) | C11A—H11A | 0.9700 |
S—O4 | 1.491 (2) | C11A—H11B | 0.9700 |
S—C1 | 1.762 (2) | C12A—C13A | 1.489 (2) |
S—C15 | 1.794 (3) | C12A—H12A | 0.9700 |
O1—C7 | 1.370 (3) | C12A—H12B | 0.9700 |
O1—C8 | 1.376 (3) | C13A—C14A | 1.482 (2) |
O2—C10 | 1.319 (3) | C13A—H13A | 0.9700 |
O2—C11A | 1.471 (14) | C13A—H13B | 0.9700 |
O2—C11B | 1.50 (3) | C14A—H14A | 0.9600 |
O3—C10 | 1.199 (3) | C14A—H14B | 0.9600 |
C1—C8 | 1.355 (3) | C14A—H14C | 0.9600 |
C1—C2 | 1.444 (3) | C11B—C12B | 1.481 (2) |
C2—C3 | 1.391 (3) | C11B—H11C | 0.9700 |
C2—C7 | 1.396 (3) | C11B—H11D | 0.9700 |
C3—C4 | 1.380 (4) | C12B—C13B | 1.483 (2) |
C3—H3 | 0.9300 | C12B—H12C | 0.9700 |
C4—C5 | 1.396 (4) | C12B—H12D | 0.9700 |
C5—C6 | 1.376 (4) | C13B—C14B | 1.481 (2) |
C5—H5 | 0.9300 | C13B—H13C | 0.9700 |
C6—C7 | 1.380 (3) | C13B—H13D | 0.9700 |
C6—H6 | 0.9300 | C14B—H14D | 0.9600 |
C8—C9 | 1.486 (3) | C14B—H14E | 0.9600 |
C9—C10 | 1.511 (4) | C14B—H14F | 0.9600 |
C9—H9A | 0.9700 | C15—H15A | 0.9600 |
C9—H9B | 0.9700 | C15—H15B | 0.9600 |
C11A—C12A | 1.482 (2) | C15—H15C | 0.9600 |
O4—S—C1 | 106.92 (12) | C11A—C12A—H12A | 110.8 |
O4—S—C15 | 105.78 (14) | C13A—C12A—H12A | 110.8 |
C1—S—C15 | 98.46 (13) | C11A—C12A—H12B | 110.8 |
C7—O1—C8 | 106.62 (17) | C13A—C12A—H12B | 110.8 |
C10—O2—C11A | 115.2 (3) | H12A—C12A—H12B | 108.9 |
C10—O2—C11B | 120.0 (10) | C14A—C13A—C12A | 115.7 (6) |
C11A—O2—C11B | 16.2 (11) | C14A—C13A—H13A | 108.4 |
C8—C1—C2 | 107.4 (2) | C12A—C13A—H13A | 108.4 |
C8—C1—S | 123.77 (19) | C14A—C13A—H13B | 108.4 |
C2—C1—S | 128.70 (18) | C12A—C13A—H13B | 108.4 |
C3—C2—C7 | 119.5 (2) | H13A—C13A—H13B | 107.4 |
C3—C2—C1 | 135.8 (2) | C13A—C14A—H14A | 109.5 |
C7—C2—C1 | 104.6 (2) | C13A—C14A—H14B | 109.5 |
C4—C3—C2 | 116.8 (2) | H14A—C14A—H14B | 109.5 |
C4—C3—H3 | 121.6 | C13A—C14A—H14C | 109.5 |
C2—C3—H3 | 121.6 | H14A—C14A—H14C | 109.5 |
C3—C4—C5 | 123.2 (2) | H14B—C14A—H14C | 109.5 |
C3—C4—Br | 118.51 (19) | O2—C11B—C12B | 104 (2) |
C5—C4—Br | 118.29 (19) | O2—C11B—H11C | 111.1 |
C6—C5—C4 | 120.2 (2) | C12B—C11B—H11C | 111.1 |
C6—C5—H5 | 119.9 | O2—C11B—H11D | 111.1 |
C4—C5—H5 | 119.9 | C12B—C11B—H11D | 111.1 |
C5—C6—C7 | 116.8 (2) | H11C—C11B—H11D | 109.0 |
C5—C6—H6 | 121.6 | C11B—C12B—C13B | 125 (2) |
C7—C6—H6 | 121.6 | C11B—C12B—H12C | 106.1 |
O1—C7—C6 | 125.9 (2) | C13B—C12B—H12C | 106.1 |
O1—C7—C2 | 110.7 (2) | C11B—C12B—H12D | 106.1 |
C6—C7—C2 | 123.5 (2) | C13B—C12B—H12D | 106.1 |
C1—C8—O1 | 110.7 (2) | H12C—C12B—H12D | 106.3 |
C1—C8—C9 | 133.3 (2) | C14B—C13B—C12B | 83.6 (14) |
O1—C8—C9 | 115.9 (2) | C14B—C13B—H13C | 114.7 |
C8—C9—C10 | 112.3 (2) | C12B—C13B—H13C | 114.7 |
C8—C9—H9A | 109.1 | C14B—C13B—H13D | 114.7 |
C10—C9—H9A | 109.1 | C12B—C13B—H13D | 114.7 |
C8—C9—H9B | 109.1 | H13C—C13B—H13D | 111.8 |
C10—C9—H9B | 109.1 | C13B—C14B—H14D | 109.5 |
H9A—C9—H9B | 107.9 | C13B—C14B—H14E | 109.5 |
O3—C10—O2 | 124.3 (3) | H14D—C14B—H14E | 109.5 |
O3—C10—C9 | 124.9 (3) | C13B—C14B—H14F | 109.5 |
O2—C10—C9 | 110.8 (2) | H14D—C14B—H14F | 109.5 |
O2—C11A—C12A | 107.2 (8) | H14E—C14B—H14F | 109.5 |
O2—C11A—H11A | 110.3 | S—C15—H15A | 109.5 |
C12A—C11A—H11A | 110.3 | S—C15—H15B | 109.5 |
O2—C11A—H11B | 110.3 | H15A—C15—H15B | 109.5 |
C12A—C11A—H11B | 110.3 | S—C15—H15C | 109.5 |
H11A—C11A—H11B | 108.5 | H15A—C15—H15C | 109.5 |
C11A—C12A—C13A | 104.5 (6) | H15B—C15—H15C | 109.5 |
O4—S—C1—C8 | −136.3 (2) | C2—C1—C8—O1 | −0.3 (3) |
C15—S—C1—C8 | 114.3 (2) | S—C1—C8—O1 | 176.29 (16) |
O4—S—C1—C2 | 39.5 (2) | C2—C1—C8—C9 | 175.7 (2) |
C15—S—C1—C2 | −69.9 (2) | S—C1—C8—C9 | −7.8 (4) |
C8—C1—C2—C3 | −177.6 (3) | C7—O1—C8—C1 | −0.3 (2) |
S—C1—C2—C3 | 6.1 (4) | C7—O1—C8—C9 | −177.00 (19) |
C8—C1—C2—C7 | 0.7 (3) | C1—C8—C9—C10 | −73.0 (3) |
S—C1—C2—C7 | −175.63 (18) | O1—C8—C9—C10 | 102.8 (2) |
C7—C2—C3—C4 | 1.4 (3) | C11A—O2—C10—O3 | 2.1 (6) |
C1—C2—C3—C4 | 179.5 (2) | C11B—O2—C10—O3 | −15.4 (11) |
C2—C3—C4—C5 | −0.3 (3) | C11A—O2—C10—C9 | −176.9 (5) |
C2—C3—C4—Br | −179.94 (16) | C11B—O2—C10—C9 | 165.7 (10) |
C3—C4—C5—C6 | −0.5 (4) | C8—C9—C10—O3 | 24.4 (4) |
Br—C4—C5—C6 | 179.14 (18) | C8—C9—C10—O2 | −156.7 (2) |
C4—C5—C6—C7 | 0.1 (4) | C10—O2—C11A—C12A | 174.3 (5) |
C8—O1—C7—C6 | −179.6 (2) | C11B—O2—C11A—C12A | −74 (4) |
C8—O1—C7—C2 | 0.8 (2) | O2—C11A—C12A—C13A | −78.9 (8) |
C5—C6—C7—O1 | −178.5 (2) | C11A—C12A—C13A—C14A | −172.1 (9) |
C5—C6—C7—C2 | 1.1 (4) | C10—O2—C11B—C12B | 128.1 (15) |
C3—C2—C7—O1 | 177.69 (19) | C11A—O2—C11B—C12B | 51 (3) |
C1—C2—C7—O1 | −0.9 (2) | O2—C11B—C12B—C13B | 69 (3) |
C3—C2—C7—C6 | −1.9 (3) | C11B—C12B—C13B—C14B | −171 (3) |
C1—C2—C7—C6 | 179.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12A—H12A···Cgi | 0.97 | 2.78 | 3.698 (5) | 158 |
C5—H5···O3ii | 0.93 | 2.55 | 3.405 (3) | 153 |
C9—H9B···O4iii | 0.97 | 2.30 | 3.248 (3) | 167 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H17BrO4S |
Mr | 373.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.420 (1), 10.255 (1), 10.306 (1) |
α, β, γ (°) | 97.503 (2), 99.711 (2), 108.678 (2) |
V (Å3) | 814.55 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.66 |
Crystal size (mm) | 0.40 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.353, 0.451 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6560, 3179, 2645 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.089, 1.14 |
No. of reflections | 3179 |
No. of parameters | 229 |
No. of restraints | 64 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.50 |
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 |
C12A—H12A···Cgi | 0.97 | 2.78 | 3.698 (5) | 158 |
C5—H5···O3ii | 0.93 | 2.55 | 3.405 (3) | 153 |
C9—H9B···O4iii | 0.97 | 2.30 | 3.248 (3) | 167 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z+1. |
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
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This work is related to our previous communications on the synthesis and structure of alkyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. 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). Herein, we describe the crystal structure of the title compound, (I).
The benzofuran unit is essentially planar, with a mean deviation of 0.012 (2) Å from the least-squares plane defined by the nine constituent atoms. The butyl group is disordered over two positions with site-occupancy factors of 0.720 (8) (for atoms labelled B) and 0.280 (8) (B) in Fig. 1. The molecular packing is stabilized by intermolecular π—π interactions: the Cg···Cgii distance is 3.698 (4) Å, where Cg is the centroid of the C2–C7 ring, symmetry code as in Fig. 2. The molecular packing is further stabilized by C—H···π interactions between the methylene-H and the benzene ring of the benzofuran system, with a C12A—H12A···Cgi separation of 2.78 Å, Table 1; Cg is the centroid of the C2–C7 benzene ring. In addition, weak intermolecular C—H···O contacts are observed, Table 1. One C-H···O contact occurs between a benzene-H and the O3-oxygen, and a second between a methylene-H and the O4-oxygen atom.