organic compounds
5-Bromo-2,4,6-trimethyl-3-(3-methylphenylsulfinyl)-1-benzofuran
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, C18H17BrO2S, the dihedral angle between the mean plane of the benzofuran ring system and the benzene ring is 68.58 (4)°. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds into inversion dimers. These dimers are linked by C—H⋯O hydrogen bonds and π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.783 (1) Å], forming a three-dimensional network. In addition, the stacked molecules exhibit inversion-related S⋯O contacts [3.153 (1) Å] involving the sulfinyl groups.
CCDC reference: 990682
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2011). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2013) and for a review of carbonyl–carbonyl interactions, see: Allen et al. (1998).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); 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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 990682
10.1107/S1600536814005352/bx2455sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005352/bx2455Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005352/bx2455Isup3.cml
3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-bromo-2,4,6-trimethyl-3-(3-methylphenylsulfanyl)-1-benzofuran (397 mg, 1.1 mmol) in dichloromethane (35 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by
(hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 469–470 K; Rf = 0.52 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.95 Å for methyl H atoms. Uiso (H) = 1.2Ueq (C) for aryl and 1.5Ueq (C) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-97's command AFIX 137 (Sheldrick, 2008).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C18H17BrO2S | Z = 2 |
Mr = 377.29 | F(000) = 384 |
Triclinic, P1 | Dx = 1.570 Mg m−3 |
Hall symbol: -P 1 | Melting point = 469–470 K |
a = 6.2336 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.0353 (2) Å | Cell parameters from 8866 reflections |
c = 12.9149 (2) Å | θ = 3.0–28.4° |
α = 69.384 (1)° | µ = 2.71 mm−1 |
β = 76.421 (1)° | T = 173 K |
γ = 76.799 (1)° | Block, colourless |
V = 797.84 (2) Å3 | 0.35 × 0.34 × 0.28 mm |
Bruker SMART APEXII CCD diffractometer | 4023 independent reflections |
Radiation source: rotating anode | 3702 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.031 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.4°, θmin = 1.7° |
ϕ and ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −14→14 |
Tmin = 0.462, Tmax = 0.746 | l = −17→17 |
14962 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)] = 0.026 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0354P)2 + 0.3061P] where P = (Fo2 + 2Fc2)/3 |
4023 reflections | (Δ/σ)max = 0.001 |
203 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
C18H17BrO2S | γ = 76.799 (1)° |
Mr = 377.29 | V = 797.84 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.2336 (1) Å | Mo Kα radiation |
b = 11.0353 (2) Å | µ = 2.71 mm−1 |
c = 12.9149 (2) Å | T = 173 K |
α = 69.384 (1)° | 0.35 × 0.34 × 0.28 mm |
β = 76.421 (1)° |
Bruker SMART APEXII CCD diffractometer | 4023 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3702 reflections with I > 2σ(I) |
Tmin = 0.462, Tmax = 0.746 | Rint = 0.031 |
14962 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.36 e Å−3 |
4023 reflections | Δρmin = −0.49 e Å−3 |
203 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 | ||
Br1 | 0.62873 (3) | 0.900826 (16) | 0.403993 (14) | 0.03223 (7) | |
S1 | 0.75692 (6) | 0.51077 (3) | 0.11568 (3) | 0.01987 (9) | |
O1 | 0.27755 (19) | 0.45708 (11) | 0.37436 (9) | 0.0241 (2) | |
O2 | 0.99335 (19) | 0.51170 (11) | 0.12084 (10) | 0.0265 (2) | |
C1 | 0.5810 (3) | 0.51004 (14) | 0.24439 (12) | 0.0196 (3) | |
C2 | 0.5305 (2) | 0.59855 (14) | 0.31119 (12) | 0.0190 (3) | |
C3 | 0.6265 (3) | 0.69926 (14) | 0.31564 (12) | 0.0195 (3) | |
C4 | 0.5100 (3) | 0.76127 (15) | 0.39418 (13) | 0.0219 (3) | |
C5 | 0.3111 (3) | 0.72874 (16) | 0.46735 (13) | 0.0244 (3) | |
C6 | 0.2268 (3) | 0.62354 (17) | 0.46533 (13) | 0.0252 (3) | |
H6 | 0.0964 | 0.5954 | 0.5154 | 0.030* | |
C7 | 0.3399 (3) | 0.56176 (15) | 0.38791 (12) | 0.0214 (3) | |
C8 | 0.4262 (3) | 0.42809 (15) | 0.28649 (12) | 0.0221 (3) | |
C9 | 0.8457 (3) | 0.73299 (16) | 0.24263 (14) | 0.0242 (3) | |
H9A | 0.8171 | 0.8110 | 0.1782 | 0.036* | |
H9B | 0.9253 | 0.6592 | 0.2159 | 0.036* | |
H9C | 0.9372 | 0.7506 | 0.2863 | 0.036* | |
C10 | 0.1860 (3) | 0.80420 (19) | 0.54665 (16) | 0.0341 (4) | |
H10A | 0.0587 | 0.7619 | 0.5938 | 0.051* | |
H10B | 0.1318 | 0.8943 | 0.5033 | 0.051* | |
H10C | 0.2863 | 0.8054 | 0.5943 | 0.051* | |
C11 | 0.3854 (3) | 0.31944 (16) | 0.25548 (14) | 0.0270 (3) | |
H11A | 0.2470 | 0.3462 | 0.2240 | 0.041* | |
H11B | 0.3713 | 0.2422 | 0.3224 | 0.041* | |
H11C | 0.5108 | 0.2979 | 0.1995 | 0.041* | |
C12 | 0.6482 (3) | 0.67448 (14) | 0.03546 (12) | 0.0198 (3) | |
C13 | 0.7999 (3) | 0.75067 (15) | −0.04158 (12) | 0.0225 (3) | |
H13 | 0.9557 | 0.7183 | −0.0474 | 0.027* | |
C14 | 0.7230 (3) | 0.87472 (16) | −0.11039 (14) | 0.0275 (3) | |
C15 | 0.4952 (3) | 0.92001 (17) | −0.09772 (15) | 0.0329 (4) | |
H15 | 0.4411 | 1.0057 | −0.1425 | 0.039* | |
C16 | 0.3449 (3) | 0.84324 (19) | −0.02136 (15) | 0.0337 (4) | |
H16 | 0.1893 | 0.8765 | −0.0144 | 0.040* | |
C17 | 0.4195 (3) | 0.71802 (17) | 0.04509 (14) | 0.0272 (3) | |
H17 | 0.3168 | 0.6635 | 0.0959 | 0.033* | |
C18 | 0.8835 (4) | 0.9564 (2) | −0.19860 (17) | 0.0443 (5) | |
H18A | 0.8480 | 0.9733 | −0.2729 | 0.066* | |
H18B | 1.0366 | 0.9092 | −0.1953 | 0.066* | |
H18C | 0.8703 | 1.0399 | −0.1850 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04364 (12) | 0.02725 (10) | 0.03175 (10) | −0.01115 (8) | −0.00252 (8) | −0.01557 (7) |
S1 | 0.02068 (18) | 0.01787 (17) | 0.02010 (17) | −0.00149 (13) | −0.00020 (13) | −0.00790 (13) |
O1 | 0.0248 (6) | 0.0267 (6) | 0.0223 (5) | −0.0103 (5) | 0.0007 (4) | −0.0087 (4) |
O2 | 0.0194 (5) | 0.0287 (6) | 0.0292 (6) | 0.0009 (4) | −0.0019 (4) | −0.0109 (5) |
C1 | 0.0212 (7) | 0.0183 (6) | 0.0185 (6) | −0.0026 (5) | −0.0023 (5) | −0.0058 (5) |
C2 | 0.0199 (7) | 0.0189 (7) | 0.0174 (6) | −0.0019 (5) | −0.0029 (5) | −0.0054 (5) |
C3 | 0.0205 (7) | 0.0181 (6) | 0.0187 (6) | −0.0028 (5) | −0.0033 (5) | −0.0047 (5) |
C4 | 0.0260 (8) | 0.0195 (7) | 0.0216 (7) | −0.0031 (6) | −0.0054 (6) | −0.0076 (6) |
C5 | 0.0247 (8) | 0.0268 (8) | 0.0220 (7) | 0.0008 (6) | −0.0034 (6) | −0.0113 (6) |
C6 | 0.0215 (7) | 0.0319 (8) | 0.0213 (7) | −0.0058 (6) | 0.0009 (6) | −0.0093 (6) |
C7 | 0.0226 (7) | 0.0215 (7) | 0.0199 (7) | −0.0058 (6) | −0.0030 (6) | −0.0054 (5) |
C8 | 0.0253 (8) | 0.0212 (7) | 0.0190 (7) | −0.0041 (6) | −0.0039 (6) | −0.0052 (5) |
C9 | 0.0231 (7) | 0.0237 (7) | 0.0269 (7) | −0.0071 (6) | 0.0008 (6) | −0.0106 (6) |
C10 | 0.0325 (9) | 0.0390 (10) | 0.0318 (9) | 0.0002 (8) | 0.0010 (7) | −0.0204 (8) |
C11 | 0.0324 (9) | 0.0236 (8) | 0.0282 (8) | −0.0094 (7) | −0.0055 (7) | −0.0085 (6) |
C12 | 0.0223 (7) | 0.0191 (7) | 0.0180 (6) | −0.0024 (6) | −0.0027 (5) | −0.0069 (5) |
C13 | 0.0242 (8) | 0.0235 (7) | 0.0213 (7) | −0.0064 (6) | −0.0022 (6) | −0.0084 (6) |
C14 | 0.0363 (9) | 0.0243 (8) | 0.0239 (7) | −0.0107 (7) | −0.0056 (7) | −0.0061 (6) |
C15 | 0.0436 (11) | 0.0230 (8) | 0.0299 (8) | 0.0011 (7) | −0.0140 (8) | −0.0047 (6) |
C16 | 0.0266 (9) | 0.0370 (10) | 0.0324 (9) | 0.0061 (7) | −0.0082 (7) | −0.0097 (7) |
C17 | 0.0226 (8) | 0.0304 (8) | 0.0253 (8) | −0.0026 (6) | −0.0018 (6) | −0.0071 (6) |
C18 | 0.0531 (13) | 0.0348 (10) | 0.0388 (10) | −0.0213 (9) | −0.0083 (9) | 0.0051 (8) |
Br1—C4 | 1.9073 (15) | C9—H9C | 0.9800 |
S1—O2 | 1.4934 (12) | C10—H10A | 0.9800 |
S1—C1 | 1.7619 (15) | C10—H10B | 0.9800 |
S1—C12 | 1.8024 (15) | C10—H10C | 0.9800 |
S1—O2i | 3.1527 (12) | C11—H11A | 0.9800 |
O1—C8 | 1.3694 (19) | C11—H11B | 0.9800 |
O1—C7 | 1.3770 (18) | C11—H11C | 0.9800 |
C1—C8 | 1.361 (2) | C12—C13 | 1.387 (2) |
C1—C2 | 1.457 (2) | C12—C17 | 1.387 (2) |
C2—C7 | 1.393 (2) | C13—C14 | 1.392 (2) |
C2—C3 | 1.401 (2) | C13—H13 | 0.9500 |
C3—C4 | 1.393 (2) | C14—C15 | 1.385 (3) |
C3—C9 | 1.508 (2) | C14—C18 | 1.505 (2) |
C4—C5 | 1.405 (2) | C15—C16 | 1.381 (3) |
C5—C6 | 1.390 (2) | C15—H15 | 0.9500 |
C5—C10 | 1.510 (2) | C16—C17 | 1.386 (2) |
C6—C7 | 1.375 (2) | C16—H16 | 0.9500 |
C6—H6 | 0.9500 | C17—H17 | 0.9500 |
C8—C11 | 1.479 (2) | C18—H18A | 0.9800 |
C9—H9A | 0.9800 | C18—H18B | 0.9800 |
C9—H9B | 0.9800 | C18—H18C | 0.9800 |
O2—S1—C1 | 111.08 (7) | C5—C10—H10A | 109.5 |
O2—S1—C12 | 106.70 (7) | C5—C10—H10B | 109.5 |
C1—S1—C12 | 96.91 (7) | H10A—C10—H10B | 109.5 |
O2—S1—O2i | 78.25 (6) | C5—C10—H10C | 109.5 |
C1—S1—O2i | 169.73 (6) | H10A—C10—H10C | 109.5 |
C12—S1—O2i | 83.97 (5) | H10B—C10—H10C | 109.5 |
C8—O1—C7 | 106.60 (12) | C8—C11—H11A | 109.5 |
C8—C1—C2 | 107.12 (13) | C8—C11—H11B | 109.5 |
C8—C1—S1 | 118.68 (12) | H11A—C11—H11B | 109.5 |
C2—C1—S1 | 133.04 (11) | C8—C11—H11C | 109.5 |
C7—C2—C3 | 119.45 (14) | H11A—C11—H11C | 109.5 |
C7—C2—C1 | 104.27 (13) | H11B—C11—H11C | 109.5 |
C3—C2—C1 | 136.25 (14) | C13—C12—C17 | 121.63 (14) |
C4—C3—C2 | 115.39 (14) | C13—C12—S1 | 117.57 (12) |
C4—C3—C9 | 123.20 (13) | C17—C12—S1 | 120.62 (12) |
C2—C3—C9 | 121.37 (13) | C12—C13—C14 | 119.71 (15) |
C3—C4—C5 | 125.00 (14) | C12—C13—H13 | 120.1 |
C3—C4—Br1 | 117.82 (11) | C14—C13—H13 | 120.1 |
C5—C4—Br1 | 117.18 (11) | C15—C14—C13 | 118.57 (16) |
C6—C5—C4 | 118.23 (14) | C15—C14—C18 | 120.73 (16) |
C6—C5—C10 | 119.23 (15) | C13—C14—C18 | 120.69 (17) |
C4—C5—C10 | 122.54 (15) | C16—C15—C14 | 121.38 (16) |
C7—C6—C5 | 117.29 (14) | C16—C15—H15 | 119.3 |
C7—C6—H6 | 121.4 | C14—C15—H15 | 119.3 |
C5—C6—H6 | 121.4 | C15—C16—C17 | 120.44 (17) |
C6—C7—O1 | 124.56 (14) | C15—C16—H16 | 119.8 |
C6—C7—C2 | 124.45 (14) | C17—C16—H16 | 119.8 |
O1—C7—C2 | 110.98 (13) | C16—C17—C12 | 118.19 (16) |
C1—C8—O1 | 110.99 (13) | C16—C17—H17 | 120.9 |
C1—C8—C11 | 133.49 (15) | C12—C17—H17 | 120.9 |
O1—C8—C11 | 115.50 (14) | C14—C18—H18A | 109.5 |
C3—C9—H9A | 109.5 | C14—C18—H18B | 109.5 |
C3—C9—H9B | 109.5 | H18A—C18—H18B | 109.5 |
H9A—C9—H9B | 109.5 | C14—C18—H18C | 109.5 |
C3—C9—H9C | 109.5 | H18A—C18—H18C | 109.5 |
H9A—C9—H9C | 109.5 | H18B—C18—H18C | 109.5 |
H9B—C9—H9C | 109.5 | ||
O2—S1—C1—C8 | −136.06 (12) | C8—O1—C7—C2 | −1.35 (16) |
C12—S1—C1—C8 | 113.02 (13) | C3—C2—C7—C6 | 4.5 (2) |
O2—S1—C1—C2 | 58.06 (17) | C1—C2—C7—C6 | −177.07 (15) |
C12—S1—C1—C2 | −52.85 (16) | C3—C2—C7—O1 | −176.74 (13) |
C8—C1—C2—C7 | −1.46 (16) | C1—C2—C7—O1 | 1.73 (16) |
S1—C1—C2—C7 | 165.60 (13) | C2—C1—C8—O1 | 0.71 (17) |
C8—C1—C2—C3 | 176.62 (17) | S1—C1—C8—O1 | −168.54 (10) |
S1—C1—C2—C3 | −16.3 (3) | C2—C1—C8—C11 | 179.18 (16) |
C7—C2—C3—C4 | −4.3 (2) | S1—C1—C8—C11 | 9.9 (2) |
C1—C2—C3—C4 | 177.88 (16) | C7—O1—C8—C1 | 0.35 (17) |
C7—C2—C3—C9 | 173.53 (14) | C7—O1—C8—C11 | −178.42 (13) |
C1—C2—C3—C9 | −4.3 (3) | O2—S1—C12—C13 | 25.77 (14) |
C2—C3—C4—C5 | 0.9 (2) | C1—S1—C12—C13 | 140.27 (12) |
C9—C3—C4—C5 | −176.88 (15) | O2—S1—C12—C17 | −158.95 (13) |
C2—C3—C4—Br1 | −179.31 (10) | C1—S1—C12—C17 | −44.45 (14) |
C9—C3—C4—Br1 | 2.9 (2) | C17—C12—C13—C14 | 0.8 (2) |
C3—C4—C5—C6 | 2.7 (2) | S1—C12—C13—C14 | 176.07 (12) |
Br1—C4—C5—C6 | −177.13 (12) | C12—C13—C14—C15 | 1.6 (2) |
C3—C4—C5—C10 | −176.77 (15) | C12—C13—C14—C18 | −176.88 (16) |
Br1—C4—C5—C10 | 3.4 (2) | C13—C14—C15—C16 | −2.1 (3) |
C4—C5—C6—C7 | −2.7 (2) | C18—C14—C15—C16 | 176.39 (18) |
C10—C5—C6—C7 | 176.80 (15) | C14—C15—C16—C17 | 0.1 (3) |
C5—C6—C7—O1 | −179.40 (14) | C15—C16—C17—C12 | 2.3 (3) |
C5—C6—C7—C2 | −0.8 (2) | C13—C12—C17—C16 | −2.8 (2) |
C8—O1—C7—C6 | 177.44 (15) | S1—C12—C17—C16 | −177.85 (13) |
Symmetry code: (i) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1ii | 0.95 | 2.50 | 3.4478 (19) | 172 |
C11—H11A···O2iii | 0.98 | 2.36 | 3.244 (2) | 150 |
Symmetry codes: (ii) −x, −y+1, −z+1; (iii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.95 | 2.50 | 3.4478 (19) | 171.8 |
C11—H11A···O2ii | 0.98 | 2.36 | 3.244 (2) | 149.8 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z. |
References
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As a part of our continuing study of 5-bromo-2,4,6-trimethyl-1-benzofuran derivatives containing phenylsulfinyl (Choi et al., 2008) and 4-fluorophenylsulfinyl (Choi et al., 2011) substituents in the 3-position, we report herein on the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.027 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-methylphenyl ring is essentially planar, with a mean deviation of 0.011 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-methylphenyl ring is 68.58 (4)°.
In the crystal structure (Fig. 2), molecules are linked via pairs of C–H···O hydrogen bonds into inversion dimers (Table 1). These dimers are further packed by C—H···O hydrogen bonds (Table 1) and π···π interactions between the benzene rings of neighbouring molecules, with a Cg1···Cg1iv distance of 3.783 (1) Å and an interplanar distance of 3.402 (1) Å resulting in a slippage of 1.655 (1) Å (Cg1 is the centroid of the C2–C7 benzene ring), forming a three-dimensional network. In addition, the crystal packing (Fig. 2) exhibits a sulfinyl–sulfinyl interaction (Choi et al., 2013) interpreted as similar to a type II carbonyl–carbonyl interaction (Allen et al. 1998), with S1···O2iii and O2iii···S1 distance of 3.153 (1) Å.