Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702716X/gk2078sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702716X/gk2078Isup2.hkl |
CCDC reference: 654919
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.107
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.17 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 = 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 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
3-Chloroperbenzoic acid (77%, 471 mg, 2.1 mmol) was added in small portions to a stirred solution of 5-ethyl-2-methyl-3-methylsulfanyl-1-benzofuran (412 mg, 2.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 2hrs, 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 column chromatography (ethyl acetate) to afford the title compound as a colorless solid [yield 92%, m.p. 361–362 K; Rf = 0.30 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of title compound (I) in acetone at room temperature.
All H atoms were geometrically located in ideal positions and refined using a riding model, with C—H = 0.93 Å for aromatic H atoms and C—H = 0.96 Å for methyl H atoms, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms, and Uiso(H) = 1.5Ueq(C) for methyl H atoms.
As part of our continuing work related to the synthesis and structure of 2-methyl-3-methylsulfinyl-1-benzofuran derivatives, the crystal structures of 5-bromo-2-methyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007a) and 2,5-dimethyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007b) have been reported. Here we present the molecular and crystal structure of the title compound (Fig. 1).
The benzofuran ring system is essentially planar, with a mean deviation of 0.003 Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (Fig. 2) is stabilized by two different π···π interactions within each stack of molecules; one between the furan ring (Cg1) and an adjacent benzene ring(Cg2ii) {distance; 3.639 (3) Å} of benzofuran unit, and a second between the furan ring (Cg1) and an adjacent furan ring (Cg1i) of benzofuran unit {distance; 3.604 (3) Å}. The crystal packing (Fig. 2) is further stabilized by CH2—H···π interactions between the 2-methyl group and the benzene ring of benzofuran unit, with a C11—H11B···Cg2i separation of 2.75 Å (Fig. 2 and Table 1; Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2—C7 benzene ring, respectively; symmetry codes as in Fig. 2).
For crystal structures of isomeric compounds, see: Choi et al. (2007a,b).
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.
C12H14O2S | Z = 2 |
Mr = 222.29 | F(000) = 236 |
Triclinic, P1 | Dx = 1.347 Mg m−3 |
Hall symbol: -P_1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0314 (6) Å | Cell parameters from 2853 reflections |
b = 8.7673 (7) Å | θ = 2.5–28.2° |
c = 8.9017 (7) Å | µ = 0.27 mm−1 |
α = 97.740 (1)° | T = 173 K |
β = 108.721 (1)° | Block, colorless |
γ = 107.289 (1)° | 0.52 × 0.43 × 0.25 mm |
V = 548.17 (7) Å3 |
Bruker SMART CCD diffractometer | 2009 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 26.0°, θmin = 2.5° |
Detector resolution: 10.00 pixels mm-1 | h = −9→6 |
φ and ω scans | k = −10→10 |
3074 measured reflections | l = −8→10 |
2107 independent 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0502P)2 + 0.4774P] where P = (Fo2 + 2Fc2)/3 |
2107 reflections | (Δ/σ)max < 0.001 |
138 parameters | Δρmax = 0.83 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C12H14O2S | γ = 107.289 (1)° |
Mr = 222.29 | V = 548.17 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.0314 (6) Å | Mo Kα radiation |
b = 8.7673 (7) Å | µ = 0.27 mm−1 |
c = 8.9017 (7) Å | T = 173 K |
α = 97.740 (1)° | 0.52 × 0.43 × 0.25 mm |
β = 108.721 (1)° |
Bruker SMART CCD diffractometer | 2009 reflections with I > 2σ(I) |
3074 measured reflections | Rint = 0.034 |
2107 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.83 e Å−3 |
2107 reflections | Δρmin = −0.38 e Å−3 |
138 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 | ||
S | 0.31899 (6) | 0.70982 (6) | 0.72234 (5) | 0.02583 (17) | |
O1 | 0.38885 (18) | 0.59991 (16) | 1.14540 (15) | 0.0242 (3) | |
O2 | 0.1366 (2) | 0.73454 (19) | 0.64848 (18) | 0.0352 (4) | |
C1 | 0.3101 (2) | 0.6141 (2) | 0.8823 (2) | 0.0205 (4) | |
C2 | 0.1751 (2) | 0.4623 (2) | 0.8850 (2) | 0.0207 (4) | |
C3 | 0.0173 (2) | 0.3325 (2) | 0.7693 (2) | 0.0239 (4) | |
H3 | −0.0237 | 0.3312 | 0.6563 | 0.029* | |
C4 | −0.0790 (3) | 0.2043 (2) | 0.8232 (2) | 0.0268 (4) | |
C5 | −0.0168 (3) | 0.2090 (2) | 0.9904 (3) | 0.0300 (4) | |
H5 | −0.0840 | 0.1211 | 1.0249 | 0.036* | |
C6 | 0.1394 (3) | 0.3372 (2) | 1.1079 (2) | 0.0290 (4) | |
H6 | 0.1804 | 0.3395 | 1.2212 | 0.035* | |
C7 | 0.2314 (3) | 0.4610 (2) | 1.0499 (2) | 0.0229 (4) | |
C8 | 0.4327 (2) | 0.6902 (2) | 1.0395 (2) | 0.0217 (4) | |
C9 | −0.2488 (3) | 0.0602 (3) | 0.7007 (3) | 0.0362 (5) | |
H9A | −0.3121 | −0.0072 | 0.7612 | 0.043* | |
H9B | −0.3392 | 0.1034 | 0.6329 | 0.043* | |
C10 | −0.1996 (3) | −0.0496 (3) | 0.5889 (3) | 0.0372 (5) | |
H10A | −0.1121 | −0.0949 | 0.6549 | 0.045* | |
H10B | −0.1401 | 0.0154 | 0.5261 | 0.045* | |
H10C | −0.3148 | −0.1403 | 0.5132 | 0.045* | |
C11 | 0.5995 (3) | 0.8462 (2) | 1.1159 (2) | 0.0280 (4) | |
H11A | 0.6144 | 0.9046 | 1.0319 | 0.042* | |
H11B | 0.7127 | 0.8208 | 1.1659 | 0.042* | |
H11C | 0.5816 | 0.9160 | 1.2005 | 0.042* | |
C12 | 0.3148 (3) | 0.5425 (3) | 0.5772 (2) | 0.0316 (4) | |
H12A | 0.1921 | 0.4523 | 0.5380 | 0.047* | |
H12B | 0.4148 | 0.5027 | 0.6306 | 0.047* | |
H12C | 0.3351 | 0.5818 | 0.4842 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0286 (3) | 0.0238 (3) | 0.0230 (3) | 0.00662 (19) | 0.00919 (19) | 0.00760 (18) |
O1 | 0.0256 (7) | 0.0238 (7) | 0.0184 (6) | 0.0071 (5) | 0.0049 (5) | 0.0038 (5) |
O2 | 0.0410 (8) | 0.0373 (8) | 0.0302 (7) | 0.0218 (7) | 0.0088 (6) | 0.0119 (6) |
C1 | 0.0197 (8) | 0.0210 (8) | 0.0207 (8) | 0.0071 (7) | 0.0075 (7) | 0.0054 (7) |
C2 | 0.0195 (8) | 0.0210 (8) | 0.0230 (9) | 0.0090 (7) | 0.0081 (7) | 0.0062 (7) |
C3 | 0.0198 (8) | 0.0252 (9) | 0.0240 (9) | 0.0072 (7) | 0.0064 (7) | 0.0044 (7) |
C4 | 0.0202 (9) | 0.0229 (9) | 0.0358 (10) | 0.0060 (7) | 0.0124 (8) | 0.0029 (8) |
C5 | 0.0331 (10) | 0.0240 (9) | 0.0391 (11) | 0.0087 (8) | 0.0221 (9) | 0.0103 (8) |
C6 | 0.0378 (11) | 0.0285 (10) | 0.0255 (9) | 0.0125 (8) | 0.0163 (8) | 0.0104 (8) |
C7 | 0.0227 (9) | 0.0212 (9) | 0.0238 (9) | 0.0081 (7) | 0.0084 (7) | 0.0036 (7) |
C8 | 0.0203 (8) | 0.0215 (9) | 0.0236 (9) | 0.0085 (7) | 0.0083 (7) | 0.0045 (7) |
C9 | 0.0252 (10) | 0.0297 (10) | 0.0444 (12) | 0.0011 (8) | 0.0127 (9) | 0.0018 (9) |
C10 | 0.0373 (12) | 0.0297 (10) | 0.0337 (11) | 0.0051 (9) | 0.0091 (9) | 0.0011 (9) |
C11 | 0.0232 (9) | 0.0232 (9) | 0.0287 (10) | 0.0048 (8) | 0.0045 (8) | 0.0007 (7) |
C12 | 0.0353 (11) | 0.0366 (11) | 0.0245 (10) | 0.0148 (9) | 0.0126 (8) | 0.0062 (8) |
S—O2 | 1.495 (2) | C6—C7 | 1.383 (3) |
S—C1 | 1.758 (2) | C6—H6 | 0.9500 |
S—C12 | 1.804 (2) | C8—C11 | 1.484 (3) |
O1—C8 | 1.374 (2) | C9—C10 | 1.514 (3) |
O1—C7 | 1.385 (2) | C9—H9A | 0.9900 |
C1—C8 | 1.359 (3) | C9—H9B | 0.9900 |
C1—C2 | 1.454 (2) | C10—H10A | 0.9800 |
C2—C7 | 1.393 (3) | C10—H10B | 0.9800 |
C2—C3 | 1.397 (3) | C10—H10C | 0.9800 |
C3—C4 | 1.400 (3) | C11—H11A | 0.9800 |
C3—H3 | 0.9500 | C11—H11B | 0.9800 |
C4—C5 | 1.400 (3) | C11—H11C | 0.9800 |
C4—C9 | 1.515 (3) | C12—H12A | 0.9800 |
C5—C6 | 1.391 (3) | C12—H12B | 0.9800 |
C5—H5 | 0.9500 | C12—H12C | 0.9800 |
O2—S—C1 | 108.54 (9) | C1—C8—C11 | 133.31 (17) |
O2—S—C12 | 106.41 (9) | O1—C8—C11 | 115.67 (15) |
C1—S—C12 | 99.54 (9) | C10—C9—C4 | 113.45 (17) |
C8—O1—C7 | 106.28 (13) | C10—C9—H9A | 108.9 |
C8—C1—C2 | 107.40 (16) | C4—C9—H9A | 108.9 |
C8—C1—S | 121.09 (14) | C10—C9—H9B | 108.9 |
C2—C1—S | 131.20 (14) | C4—C9—H9B | 108.9 |
C7—C2—C3 | 119.36 (17) | H9A—C9—H9B | 107.7 |
C7—C2—C1 | 104.43 (16) | C9—C10—H10A | 109.5 |
C3—C2—C1 | 136.21 (17) | C9—C10—H10B | 109.5 |
C2—C3—C4 | 118.64 (17) | H10A—C10—H10B | 109.5 |
C2—C3—H3 | 120.7 | C9—C10—H10C | 109.5 |
C4—C3—H3 | 120.7 | H10A—C10—H10C | 109.5 |
C3—C4—C5 | 119.79 (17) | H10B—C10—H10C | 109.5 |
C3—C4—C9 | 120.04 (18) | C8—C11—H11A | 109.5 |
C5—C4—C9 | 120.17 (18) | C8—C11—H11B | 109.5 |
C6—C5—C4 | 122.62 (17) | H11A—C11—H11B | 109.5 |
C6—C5—H5 | 118.7 | C8—C11—H11C | 109.5 |
C4—C5—H5 | 118.7 | H11A—C11—H11C | 109.5 |
C7—C6—C5 | 115.92 (18) | H11B—C11—H11C | 109.5 |
C7—C6—H6 | 122.0 | S—C12—H12A | 109.5 |
C5—C6—H6 | 122.0 | S—C12—H12B | 109.5 |
C6—C7—O1 | 125.44 (17) | H12A—C12—H12B | 109.5 |
C6—C7—C2 | 123.67 (18) | S—C12—H12C | 109.5 |
O1—C7—C2 | 110.88 (15) | H12A—C12—H12C | 109.5 |
C1—C8—O1 | 111.02 (16) | H12B—C12—H12C | 109.5 |
O2—S—C1—C8 | −117.99 (16) | C5—C6—C7—C2 | 0.3 (3) |
C12—S—C1—C8 | 130.99 (16) | C8—O1—C7—C6 | −179.47 (18) |
O2—S—C1—C2 | 54.83 (19) | C8—O1—C7—C2 | 0.01 (19) |
C12—S—C1—C2 | −56.18 (19) | C3—C2—C7—C6 | 0.0 (3) |
C8—C1—C2—C7 | −0.05 (19) | C1—C2—C7—C6 | 179.51 (17) |
S—C1—C2—C7 | −173.62 (14) | C3—C2—C7—O1 | −179.53 (15) |
C8—C1—C2—C3 | 179.4 (2) | C1—C2—C7—O1 | 0.03 (19) |
S—C1—C2—C3 | 5.8 (3) | C2—C1—C8—O1 | 0.1 (2) |
C7—C2—C3—C4 | −0.3 (3) | S—C1—C8—O1 | 174.41 (12) |
C1—C2—C3—C4 | −179.69 (19) | C2—C1—C8—C11 | 179.73 (19) |
C2—C3—C4—C5 | 0.4 (3) | S—C1—C8—C11 | −5.9 (3) |
C2—C3—C4—C9 | −179.01 (17) | C7—O1—C8—C1 | −0.04 (19) |
C3—C4—C5—C6 | −0.2 (3) | C7—O1—C8—C11 | −179.78 (15) |
C9—C4—C5—C6 | 179.24 (18) | C3—C4—C9—C10 | 68.7 (3) |
C4—C5—C6—C7 | −0.2 (3) | C5—C4—C9—C10 | −110.7 (2) |
C5—C6—C7—O1 | 179.69 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···Cgi | 0.98 | 2.75 | 3.532 (3) | 137 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C12H14O2S |
Mr | 222.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 8.0314 (6), 8.7673 (7), 8.9017 (7) |
α, β, γ (°) | 97.740 (1), 108.721 (1), 107.289 (1) |
V (Å3) | 548.17 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.52 × 0.43 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3074, 2107, 2009 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.107, 1.06 |
No. of reflections | 2107 |
No. of parameters | 138 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.83, −0.38 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···Cgi | 0.98 | 2.75 | 3.532 (3) | 137 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
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As part of our continuing work related to the synthesis and structure of 2-methyl-3-methylsulfinyl-1-benzofuran derivatives, the crystal structures of 5-bromo-2-methyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007a) and 2,5-dimethyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007b) have been reported. Here we present the molecular and crystal structure of the title compound (Fig. 1).
The benzofuran ring system is essentially planar, with a mean deviation of 0.003 Å from the least-squares plane defined by the nine constituent atoms. The molecular packing (Fig. 2) is stabilized by two different π···π interactions within each stack of molecules; one between the furan ring (Cg1) and an adjacent benzene ring(Cg2ii) {distance; 3.639 (3) Å} of benzofuran unit, and a second between the furan ring (Cg1) and an adjacent furan ring (Cg1i) of benzofuran unit {distance; 3.604 (3) Å}. The crystal packing (Fig. 2) is further stabilized by CH2—H···π interactions between the 2-methyl group and the benzene ring of benzofuran unit, with a C11—H11B···Cg2i separation of 2.75 Å (Fig. 2 and Table 1; Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2—C7 benzene ring, respectively; symmetry codes as in Fig. 2).